WO2012034957A1

WO2012034957A1 - Pesticidal pyrroline n-oxide derivatives

Info

Publication number: WO2012034957A1
Application number: PCT/EP2011/065704
Authority: WO
Inventors: Tetsuya Murata; Hidetoshi Kishikawa; Hidekazu Watanabe; Eiichi Shimojo; Teruyuki Ichihara; Masashi Ataka; Katsuhiko Shibuya; Tadashi Ishikawa; Ulrich Görgens
Original assignee: Bayer Cropscience Ag
Priority date: 2010-09-15
Filing date: 2011-09-12
Publication date: 2012-03-22
Also published as: JP2012062267A

Abstract

Pyrroline N-oxide derivative that is useful as a pesticidal compound represented by Formula (I), and a pesticide and an agent for controlling animal parasites which contain the pyrroline N-oxide derivative as an active ingredient.

Description

Pesticidal pyrroline N-oxide derivatives

The present invention relates to novel pyrroline N-oxide derivatives, and pesticides and an animal parasite-controlling agent that contain the pyrroline N-oxide derivative as an active ingredient.

In Patent documents 1 to 3, nitrogen-containing heterocyclic compounds having a pesticidal activity are disclosed ([Patent document 1] = WO2009/072621; [Patent document 2] = WO2009/097992, and [Patent document 3] = WO2009/112275).

Since ecological and economic demands on modern plant treatment agents are continually increasing, particularly in respect to the amount applied, residue formation, selectivity, toxicity and favourable production methodology, and also because, for example, resistance problems can occur, there is the ongoing task to develop new plant treatment agents that at least in certain areas are able to demonstrate advantages over known agents.

Inventors of the present invention extensively studied to develop novel compounds which are highly effective as pesticides and have a broad spectrum of use. As a result, the inventors found that the novel pyrroline N-oxide derivatives represented by the following Formula (I) have a high activity, a broad spectrum of use and safety, and also are effective against pests that are resistant to an organic phosphorous agent or a carbamate agent.

Thus, the invention is directed to pyrroline N-oxide derivatives represented by the following Formula

(i);

wherein

T is one of followin groups (Tl) to (T4) or a group (T5)

wherein in group (T5) A¹, A² and A³ are C-Y or nitrogen;

G is halogen (fluorine chlorine, bromine, or iodine), or a saturated or unsaturated 5- or 6-membered heterocyclic group which may be substituted; by halogen, d-12 alkyl, cyano, Ci_i₂ alkoxy-carbonyl or carbox preferably G is selected among the following 5- membered heterocycles Gl to G9,

wherein (Z) is halog en, Ci-12 or

d-ehaloalkyl, cyano, Ci-12 or d-e&lkoxy-carbonyl or carboxy, and k is 0, 1 , 2, 3, or 4, preferably (Z) is CN, N0₂, or halogen, and k is 0, 1 or 2; (k = 0 means that the heterocycle is not substituted) R IS d-12 alkyl or Ci-12 haloalkyl which is optionally substituted;

R¹ is hydrogen, amino, hydroxy, cyano, Ci_i₂ alkoxy, Ci_i₂ alkyl-carbonylamino, Ci_i₂ alkylimino, Ci_i₂ alkyl, d-8 cycloalkyl, C₂_₆ alkenyl, C₂_₆ alkynyl, d_i₂ alkyl-carbonyl, CH₂-R⁶, C(=0)R⁶ or C(=S)R⁶, and among the definitions of R¹, each group from d-12 alkoxy to Ci_i₂ alkyl-carbonyl is optionally substituted; R² is hydrogen, cyano, carbonyl, thiocarbonyl, C_M2 alkyl-carbonyl, C_M2 alkyl -thiocarbonyl, C_M2 haloalkyl-carbonyl, d-12 haloalkyl-thiocarbonyl, d-12 alkyl-aminocarbonyl, d-12 alkylamino- thiocarbonyl, C₂_₂₄ dialkylamino-carbonyl, C₂_₂₄ dialkylamino-thiocarbonyl, d-₁₂ alkoxyamino- carbonyl, d-₁₂ alkoxyamino-thiocarbonyl, d-12 alkoxy-carbonyl, d-₁₂ alkoxy-thiocarbonyl, d-12 alkylthio-carbonyl, d-₁₂ alkylthio-thiocarbonyl, d-₁₂ alkylsulfonyl, d-₁₂ haloalkylsulfonyl, d-8 cycloalkyl-carbonyl, C ₂_₆ alkenyl-carbonyl, C₂_₆ alkynyl -carbonyl, d_₈ cycloalkyl-Ci_₄ alkyl- carbonyl, d-12 alkylthio-Ci_i₂ alkyl-carbonyl, d-₁₂ alkylsulfmyl-Ci_i₂ alkyl-carbonyl, d-12 alkylsulfonyl-Ci_i₂ alkyl-carbonyl, d-₁₂ alkyl-carbonyl-d_i₂ alkyl-carbonyl, C₃_g cycloalkylamino- carbonyl, C₂_₆ alkenylamino-carbonyl, C₂_₆ alkynylamino-carbonyl, C(=0)R⁶ or C(=S)R⁶, and among the definitions of R², each group from d-12 alkyl-carbonyl to C₂_₆ alkynylamino-carbonyl is optionally substituted;

R¹ and R² may form, together with the nitrogen atom to which they are bonded, a 3- to 6-membered heterocycle, and the heterocycle may be substituted with X as defined below, oxo, thioxo, or nitroimino; R³ is hydrogen, cyano, Ci_i₂ alkyl which is optionally substituted or d_i₂ haloalkyl which is optionally substituted;

R⁴ is hydrogen, d-₁₂ alkyl, d-₁₂ alkyl-carbonyl, or d-₁₂ alkoxy-carbonyl;

R⁶ is phenyl which is optionally substituted or a 5- to 6-membered heterocyclic group which is optionally substituted;

B is C-X, C-H or N;

j is 1 or 2;

m is 0 to 4;

n is 0 to 2;

X is halogen, nitro, cyano, Ci_i₂ alkyl, d-₁₂ alkoxy, Ci_i₂ haloalkyl, d-₁₂ haloalkoxy, Ci_i₂ alkylthio, Ci_ i₂ alkylsulfinyl, d-₁₂ alkylsulfonyl, d-₁₂ haloalkylthio, Ci_i₂ haloalkylsulfinyl, d-₁₂ haloalkylsulfonyl, acylamino, Ci_i₂ alkoxy-carbonylamino, C_M2 haloalkoxy-carbonylamino, Ci_i₂ alkoxyimino, Ci_i₂ haloalkoxyimino, Ci_i₂ alkyl sulfonylamino, sulfur pentafluoride, hydroxy, mercapto or amino, and among the definitions of X, each group from d-₁₂ alkyl to C_M2 alkylsulfonylamino is optionally substituted;

Y is hydrogen, halogen, nitro, hydroxy, mercapto, cyano, amino, C_M2 alkyl, d-₁₂ haloalkyl, C₃_₈ cycloalkyl, C₃_₈ cyclohaloalkyl, d-₁₂ alkoxy, C_M2 haloalkoxy, Ci_i₂ alkylthio, Ci_i₂ alkylsulfinyl, Ci_i₂ alkylsulfonyl, d-₁₂ haloalkylthio, C_M2 haloalkylsulfinyl, d-₁₂ haloalkylsulfonyl, d-₁₂ alkyl sulfonyloxy, Ci_i₂ haloalkylsulfonyloxy, Ci_i₂ alkylaminosulfonyl, d-₁₂ haloalkylaminosulfonyl, C₂_₂₄ dialkylaminosulfonyl, C₂_₂₄ di-haloalkyl-aminosulfonyl, d-₁₂ alkylamino, C₂_₂₄ dialkylamino, acylamino, C_M2 alkoxy-carbonylamino, Ci_i₂ haloalkoxy- carbonylamino, Ci_i₂ alkylsulfonylamino, Ci_i₂ haloalkylsulfonylamino, C₃_₃₆ trialkylsilyl, Ci_i₂ alkoxyimino, Ci_i₂ haloalkoxyimino, C_M2 alkoxyimino-Ci_i₂ alkyl, d-₁₂ haloalkoxyimino-Ci_i₂ alkyl, d-₁₂ alkylsulfinylimino, Ci_i₂ alkylsulfinylimino-Ci_i₂ alkyl, d-₁₂ alkylsulfinylimino-Ci_i₂ alkyl-carbonyl, d-₁₂ alkylsulfoxyimino, Ci_i₂ alkylsulfoxyimino-Ci_i₂ alkyl, d-₁₂ alkoxy-carbonyl, Ci_i₂ alkyl-carbonyl, aminocarbonyl, d-₁₂ alkylamino-carbonyl, amino-thiocarbonyl, d-₁₂ alkylamino-thiocarbonyl, C₂_₂₄ dialkyliminocarbonyl or C₂_₂ dialkylamino-thiocarbonyl;

Z¹, Z² and Z³ each independently represent CR⁷R⁸, C=0, C=N-OR⁹, N-R⁹, S(0)„, S=N-R⁹, or S(0)=N- R⁹, with the proviso that Z¹, Z² and Z³ do not simultaneously represent CR⁷R⁸;

R⁷ and R⁸ each independently represent hydrogen, halogen, d-₁₂ alkyl which may be substituted or d-₁₂ haloalkyl which may be substituted; and

R⁹ is hydrogen, cyano, nitro, C_M2 alkyl, d-₁₂ haloalkyl, C₃_₈ cycloalkyl-Ci_₆ alkyl, d-₁₂ alkyl-carbonyl, Ci-₁₂ haloalkyl-carbonyl, Ci_i₂ alkoxy-carbonyl, Ci_i₂ haloalkoxy-carbonyl, Ci_i₂ alkylsulfonyl, Ci_ 1₂ haloalkylsulfonyl, C₆_i₀ aryl-Ci_₆ alkyl or heteroaryl-Ci_₆ alkyl, among the definitions of R⁹, each group from d-₁₂ alkyl to Ci_i₂ haloalkylsulfonyl is optionally substituted, and the aryl moiety in C₆_io aryl-Ci-₆ alkyl and the heteroaryl moiety in heteroaryl-Ci_₆ alkyl may be substituted with one to three groups selected from a group consisting of halogen, cyano, nitro, Ci_i₂ alkyl, d_i₂ haloalkyl, d-₁₂ alkoxy, Ci_i₂ haloalkoxy and C_M2 alkoxy-carbonyl, among the definitions, each group from d-₁₂ alkyl to C_M2 alkoxy-carbonyl is optionally substituted.

For the descriptions herein below, unless specifically described otherwise, definition of each symbol in Formula has the same meaning as those described above.

The compounds having Formula (I) of the invention can be prepared according to the following methods.

Preparation method (a): A method of reducing the compounds represented by the following Formula (II) with a metal hydride.

Preparation method (b): A method for the preparation of compounds of Formula (I), wherein T is Tl, G is a heterocyclic group; and Y is a halogen, which method comprises reacting the compounds represented by the following Formula (III) with the compounds represented by the following Formula (IV) in the presence of a base in an inert solvent.

Preparation method (c): A method for the preparation of compounds of Formula (I), wherein T is Tl, G is a heterocyclic group, and Y is cyano; comprising reacting the compounds represented by the following Formula (V) with a cyanation agent.

The compounds having Formula (I) of the invention have a pesticidal activity, and therefore can be used as a pesticide.

In the present specification, the term "alkyl" represents linear or branched Ci_i₂ alkyl such as methyl, ethyl, n- or iso-propyl, n-, iso-, sec- or tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl or n-dodecyl, preferably Ci_₆ alkyl, and more preferably Ci_₄ alkyl.

In addition, examples of an alkyl moiety included in each groups as a part of constitution, can be those described above for the "alkyl".

The term "acylamino" represents, for example, alkylcarbonylamino, cyclopropylcarbonylamino, and benzoylamino. Herein, for the alkyl moiety, those having the same meaning as described in the above for the "alkyl" can be exemplified.

The term "halogen" and a halogen moiety included in each group substituted with a halogen represent fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine.

The term "cycloalkyl" represents C₃_₈ cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl, preferably C₃_₇ cycloalkyl, and more preferably C₃_₆ cycloalkyl.

The term "alkenyl" represents C₂_₆ alkenyl, preferably C₂_₄ alkenyl, such as vinyl, allyl, 1-propenyl, or 1- (or 2- or 3-) butenyl, more preferably C₂_₃ alkenyl.

The term "alkynyl" represents C₂_₆ alkynyl, preferably C₂_₄ alkynyl, such as ethynyl, propargyl, 1- propynyl, butan-3-ynyl or pentan-4-ynyl, more preferably C₂_₃ alkynyl.

The term "aryl" represents a C₆.₁₂ aromatic hydrocarbon group, for example, phenyl, naphthyl or biphenyl, preferably a C₆_i₀ aromatic hydrocarbon group, and more preferably a C₆ aromatic hydrocarbon group, phenyl.

The term "arylalkyl" represents, for example, benzyl or phenethyl.

"Heterocycle" represents a saturated or unsaturated 5- or 6-membered heterocyclic ring group comprising at least one of N, O and S as a hetero atom, and also represents a fused heterocyclic ring group which may be benzo-fused.

Specific examples of the heterocycle or heterocyclic group include furyl, thienyl, pyrrolyl, isoxazolyl, pyrazolyl, oxazolyl, oxathiaxolyl, imidazolyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, benzoxazolyl, and quinolyl.

The term "heteroaryl" represents an unsaturated 5- or 6-membered heterocyclic group which contains a heteroatom in addition to carbon atoms in the ring structure, and specific examples thereof include furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, triazolyl, pyridyl, pyrazyl, pyridazyl, pyrimidyl, and triazinyl.

As for the substituent for substituting a group which "is optionally substituted," ones selected from nitro, cyano, hydroxy, mercapto, isocyano, cyanato, isothiocyanato, carboxy, carbamoyl, aminosulfonyl, monoalkylamino, dialkylamino, N-alkylcarbonylamino, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, SF₅, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, cycloalkenyloxy, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, aryloxycarbonyl, alkylcarbonyl, alkylthio, alkenylthio, cycloalkenylthio, alkynylthio, alkylsulfinyl, alkylsulfinyl including an isomer, alkylsulfonyl, monoalkylaminosulfonyl, dialkylaminosulfonyl, alkylphosphinyl, alkylphosphonyl, alkylphosphinyl including an isomer, alkylphosphinyl including an isomer, N-alkyl-aminocarbonyl, N,N-dialkyl- aminocarbonyl, N-alkylcarbonyl-aminocarbonyl, N-alkylcarbonyl-N-alkylaminocarbonyl, aryl, aryloxy, benzyl, benzyloxy, benzylthio, arylthio, arylamino, benzylamino, trialkylsilyl, alkoxyalkyl, alkylthioalkyl, alkylthioalkoxy, alkoxyalkoxy, phenethyl, benzyloxy, haloalkyl, haloalkoxy, haloalkylthio, haloalkylcarbonyl, haloalkoxycarbonyl, haloalkoxyalkoxy, haloalkoxyalkylthio, haloalkoxyalkylcarbonyl or haloalkoxyalkyl, cycloalkylaminocarbonyl, alkylsulfinylimino, alkylsulfonylimino, alkoxyimino, and a heterocyclic group are included.

Compounds of Formula (I) are preferred wherein

T is one of the followin groups (Tl) to T4) or (T5):

wherein in group (T5) A¹, A² and A³ are C-Y or nitrogen;

G is halogen, in particular fluorine, or the following heterocycle G6

G6 wherein (Z) is CN, N0₂, halogen, and k is 0, 1 or 2; more preferably (Z) is halogen and k is 0 or 1; R is Ci-6 alkyl or Ci_₆ haloalkyl which is optionally substituted; preferably R is Ci_₄ alkyl or Ci_₄ haloalkyl which is optionally substituted; more preferably R is CF₃;

R¹ is hydrog en, amino, hydroxy, cyano, Ci_6 alkoxy, Ci_6 alkyl-carbonylamino, Ci_6 alkylimino, Ci_6 alkyl, C₃_₇ cycloalkyl, C₂_ alkenyl, C₂_ alkynyl, Ci_₆ alkyl-carbonyl, CH₂-R⁶, C(=0)R⁶ or C(=S)R⁶, and among the definitions of R¹, each group from Ci_₆ alkoxy to Ci_₆ alkyl-carbonyl is optionally substituted; preferably R¹ is hydrogen, amino, hydroxy, cyano, Ci_₄ alkoxy, Ci_₄ alkyl- carbonylamino, Ci-4 alkylimino, Ci_₄ alkyl, C₃_₆ cycloalkyl, C₂_₃ alkenyl, C₂_₃ alkynyl, Ci_₄ alkyl- carbonyl, CH₂-R⁶, C(=0)R⁶ or C(=S)R⁶, and among the definitions of R¹, each group from Ci-₄ alkoxy to Ci_ alkyl-carbonyl is optionally substituted; more preferably R¹ is hydrogen;

R² is hydrogen, cyano, carbonyl, thiocarbonyl, Ci_₆ alkyl-carbonyl, Ci_₆ alkyl-thiocarbonyl, Ci_₆ haloalkyl-carbonyl, Ci_₆ haloalkyl-thiocarbonyl, Ci_₆ alkyl-aminocarbonyl, Ci_₆ alkylamino- thiocarbonyl, C₂_i₂ dialkylamino-carbonyl, C₂_i₂ dialkylamino-thiocarbonyl, Ci_₆ alkoxyamino- carbonyl, Ci_₆ alkoxyamino-thiocarbonyl, Ci_₆ alkoxy-carbonyl, Ci_₆ alkoxy-thiocarbonyl, Ci_₆ alkylthio-carbonyl, Ci_₆ alkylthio-thiocarbonyl, Ci_₆ alkylsulfonyl, Ci_₆ haloalkylsulfonyl, C₃_₇ cycloalkyl-carbonyl, C₂_ alkenyl-carbonyl, C₂_₆ alkynyl -carbonyl, C₃_₇ cycloalkyl-Ci_ alkyl- carbonyl, Ci-6 alkylthio-Ci-6 alkyl-carbonyl, Ci_₆ alkylsulfmyl-Ci_₆ alkyl-carbonyl, Ci_₆ alkylsulfonyl-Ci-6 alkyl-carbonyl, Ci_₆ alkyl-carbonyl-Ci_₆ alkyl-carbonyl, C₃_₇ cycloalkylamino- carbonyl, C₂_ alkenylamino-carbonyl, C₂_ alkynylamino-carbonyl, C(=0)R⁶ or C(=S)R⁶, and among the definitions of R², each group from Ci_₆ alkyl-carbonyl to C₂_ alkynylamino-carbonyl is optionally substituted; preferably R² is hydrogen, cyano, carbonyl, thiocarbonyl, Ci_ alkyl- carbonyl, Ci-4 alkyl-thiocarbonyl, Ci_ haloalkyl-carbonyl, Ci_ haloalkyl-thiocarbonyl, Ci_ alkyl- aminocarbonyl, Ci-4 alkylamino-thiocarbonyl, C₂_₈ dialkylamino-carbonyl, C₂_₈ dialkylamino- thiocarbonyl, Ci-4 alkoxyamino-carbonyl, Ci_ alkoxyamino-thiocarbonyl, Ci_ alkoxy-carbonyl, Ci-4 alkoxy-thiocarbonyl, Ci_ alkylthio-carbonyl, Ci_ alkylthio-thiocarbonyl, Ci_ alkylsulfonyl, Ci-4 haloalkylsulfonyl, C₃_₆ cycloalkyl-carbonyl, C₂_₃ alkenyl-carbonyl, C₂_₃ alkynyl-carbonyl, C₃_₆ cycloalkyl-Ci_ alkyl-carbonyl, Ci_ alkylthio-Ci_ alkyl-carbonyl, Ci_ alkylsulfmyl-Ci_ alkyl- carbonyl, Ci-4 alkylsulfonyl-Ci_ alkyl-carbonyl, Ci_ alkyl-carbonyl-Ci_ alkyl-carbonyl, C₃_₆ cycloalkylamino-carbonyl, C₂_₃ alkenylamino-carbonyl, C₂_₃ alkynylamino-carbonyl, C(=0)R⁶ or C(=S)R⁶, and among the definitions of R², each group from Ci- alkyl-carbonyl to C₂_₃ alkynylamino-carbonyl is optionally substituted; more preferably R² is Ci_ alkyl-carbonyl, C₃_₆ cycloalkyl-carbonyl, or Ci_ alkoxy-carbonyl;

R¹ and R² may form, together with a nitrogen atom to which they are bonded, a 3- to 6-membered heterocycle, and the heterocycle may be substituted with X as described below, oxo, thioxo or nitroimino; R³ is hydrogen, cyano, Ci_₆ alkyl which is optionally substituted or Ci_₆ haloalkyl which is optionally substituted; preferably R³ is hydrogen, cyano, Ci_₄ alkyl which is optionally substituted or Ci_₄ haloalkyl which is optionally substituted; more preferably R³ is hydrogen, or Ci_₄ alkyl

R⁴ is hydrogen, Ci_₆ alkyl, Ci_₆ alkyl-carbonyl or Ci_₆ alkoxy-carbonyl; preferably R⁴ is hydrogen, Ci_₄ alkyl, Ci_ alkyl-carbonyl or Ci_ alkoxy-carbonyl; more preferably R⁴ is hydrogen

R⁶ is phenyl which is optionally substituted or a 5- to 6-membered heterocyclic group which is optionally substituted; preferably R⁶ is phenyl which is optionally substituted or a 5- to 6- membered heterocyclic group which is optionally substituted,

B is C-X, with X being halogen (in particular chlorine), or C-H, or N; preferably C-X, with X being chlorine or C-H; j is 1 or 2; preferably j is 1; m is 0, 1, 2, 3 or 4; n is 0, 1 or 2;

X is halogen, nitro, cyano, Ci_₆ alkyl, Ci_₆ alkoxy, Ci_₆ haloalkyl, Ci_₆ haloalkoxy, Ci_₆ alkylthio, Ci_₆ alkylsulfinyl, Ci_₆ alkylsulfonyl, Ci_₆ haloalkylthio, Ci_₆ haloalkylsulfinyl, Ci_₆ haloalkylsulfonyl, acylamino, Ci_₆ alkoxy-carbonylamino, Ci_₆ haloalkoxy-carbonylamino, Ci_₆ alkoxyimino, Ci_₆ haloalkoxyimino, Ci_₆ alkylsulfonylamino, sulfur pentafluoride, hydroxy, mercapto or amino, among the definitions of X, each group from Ci_₆ alkyl to Ci_₆ alkylsulfonylamino is optionally substituted; preferably X is halogen, nitro, cyano, Ci_ alkyl, Ci_ alkoxy, Ci_ haloalkyl, Ci_ haloalkoxy, Ci_ alkylthio, Ci_ alkylsulfinyl, Ci_ alkylsulfonyl, Ci_ haloalkylthio, Ci_ haloalkylsulfinyl, Ci_ haloalkyl sulfonyl, acylamino, Ci_ alkoxy-carbonylamino, Ci_ haloalkoxy- carbonylamino, Ci-4 alkoxyimino, Ci_ haloalkoxyimino, Ci_ alkylsulfonylamino, sulfur pentafluoride, hydroxy, mercapto or amino, and among the definitions of X, each group from Ci_ alkyl to Ci_ alkylsulfonylamino is optionally substituted; more preferably X is CF₃ and/or halogen (in particular chlorine);

Y is hydrogen, halogen, nitro, hydroxy, mercapto, cyano, amino, Ci_₆ alkyl, Ci_₆ haloalkyl, C₃_₇ cycloalkyl, C₃_₇ cyclohaloalkyl, Ci_₆ alkoxy, Ci_₆ haloalkoxy, Ci_₆ alkylthio, Ci_₆ alkylsulfinyl, Ci_₆ alkylsulfonyl, Ci_₆ haloalkylthio, Ci_₆ haloalkylsulfinyl, Ci_₆ haloalkylsulfonyl, Ci_₆ alkylsulfonyloxy, Ci_₆ haloalkylsulfonyloxy, Ci_₆ alkylaminosulfonyl, Ci_₆ haloalkylaminosulfonyl, C₂-n dialkylaminosulfonyl, C₂-n di-haloalkyl-aminosulfonyl, Ci_₆ alkylamino, C₂-n dialkylamino, acylamino, Ci_₆ alkoxy-carbonylamino, Ci_₆ haloalkoxy- carbonylamino, Ci-6 alkylsulfonylamino, Ci_₆ haloalkylsulfonylamino, C₃_ig trialkylsilyl, Ci_₆ alkoxyimino, Ci_₆ haloalkoxyimino, Ci_₆ alkoxyimino-Ci_₆ alkyl, Ci_₆ haloalkoxyimino-Ci_₆ alkyl, Ci-6 alkylsulfinylimino, Ci_₆ alkylsulfinylimino-Ci_₆ alkyl, Ci_₆ alkylsulfinylimino-Ci_₆ alkyl- carbonyl, Ci_₆ alkylsulfoxyimino, Ci_₆ alkylsulfoxyimino-Ci_₆ alkyl, Ci_₆ alkoxy-carbonyl, Ci_₆ alkyl-carbonyl, aminocarbonyl, Ci_₆ alkylamino-carbonyl, amino-thiocarbonyl, Ci_₆ alkylamino- thiocarbonyl, C₂-₁₂ dialkyliminocarbonyl or C₂-₁₂ dialkylamino-thiocarbonyl; preferably Y is hydrogen, halogen, nitro, hydroxy, mercapto, cyano, amino, Ci_₄ alkyl, Ci_₄ haloalkyl, C₃_₆ cycloalkyl, C₃_₆ cyclohaloalkyl, Ci_₄ alkoxy, Ci_₄ haloalkoxy, Ci_ alkylthio, Ci_ alkylsulfinyl, Ci_ alkylsulfonyl, Ci_ haloalkylthio, Ci_ haloalkylsulfinyl, Ci_ haloalkylsulfonyl, Ci_ alkylsulfonyloxy, Ci_ haloalkylsulfonyloxy, Ci_ alkylaminosulfonyl, Ci_ haloalkylaminosulfonyl, C₂-8 dialkylaminosulfonyl, C₂-8 di-haloalkyl-aminosulfonyl, Ci_ alkylamino, C₂-8 dialkylamino, acylamino, Ci_ alkoxy-carbonylamino, Ci_ haloalkoxy- carbonylamino, Ci_ alkylsulfonylamino, Ci_ haloalkylsulfonylamino, C₃_i₂ trialkylsilyl, Ci_ alkoxyimino, Ci_ haloalkoxyimino, Ci_ alkoxyimino-Ci_ alkyl, Ci_ haloalkoxyimino-Ci_ alkyl, Ci-4 alkylsulfinylimino, Ci_ alkylsulfmylimino-Ci_ alkyl, Ci_ alkylsulfinylimino-Ci_ alkyl- carbonyl, Ci-4 alkylsulfoxyimino, Ci_₄ alkylsulfoxyimino-Ci_ alkyl, Ci_ alkoxy-carbonyl, Ci_ alkyl-carbonyl, aminocarbonyl, Ci_ alkylamino-carbonyl, amino-thiocarbonyl, Ci_ alkylamino- thiocarbonyl, C₂-8 dialkyliminocarbonyl or C₂-8 dialkylamino-thiocarbonyl; more preferably Y is hydrogen, Ci_ alkyl, cyano, and/or halogen (in particular chlorine or bromine);

Z¹, Z² and Z³ each independently represent CR⁷R⁸ (in particular CH₂), C=0, C=N-OR⁹, N-R⁹, S(0)„, S=N-R⁹ or S(0)=N-R⁹, with the proviso that Z¹, Z² and Z³ do not simultaneously represent CR⁷R⁸; preferably Z¹, and Z³ stand for CH₂, while Z³ stands for S;

R⁷ and R⁸ each independently are hydrogen, halogen, Ci_₆ or Ci_ alkyl which may be substituted or Ci_₆ or Ci-4 haloalkyl which may be substituted; preferably stand for hydrogen and

R⁹ is hydrogen, cyano, nitro, Ci_₆ alkyl, Ci_₆ haloalkyl, C₃_₇ cycloalkyl-Ci_ alkyl, Ci_₆ alkyl-carbonyl, Ci-6 haloalkyl-carbonyl, Ci_₆ alkoxy-carbonyl, Ci_₆ haloalkoxy-carbonyl, Ci_₆ alkylsulfonyl, Ci_₆ haloalkylsulfonyl, C₆_i₀ aryl-Ci_ alkyl or heteroaryl-Ci_ alkyl, among the definitions of R⁹, each group from Ci_₆ alkyl to Ci_₆ haloalkylsulfonyl is optionally substituted, and the aryl moiety in C₆_io aryl-Ci_ alkyl and the heteroaryl moiety in heteroaryl-Ci_ alkyl may be substituted with one to three groups selected from a group consisting of halogen, cyano, nitro, Ci_₆ alkyl, Ci_₆ haloalkyl, Ci-6 alkoxy, Ci_₆ haloalkoxy and Ci_₆ alkoxy-carbonyl, among the definitions, each group from Ci-6 alkyl to Ci_₆ alkoxy-carbonyl is optionally substituted; preferably R⁹ is hydrogen, cyano, nitro, Ci-4 alkyl, Ci_ haloalkyl, C₃_₆ cycloalkyl-Ci_₂ alkyl, Ci_ alkyl-carbonyl, Ci_ haloalkyl-carbonyl, Ci-4 alkoxy-carbonyl, Ci_ haloalkoxy-carbonyl, Ci_ alkylsulfonyl, Ci_ haloalkylsulfonyl, C₆_i₀ aryl-Ci-₂ alkyl or heteroaryl-Ci_₂ alkyl, among the definitions of R⁹, each group from Ci_ alkyl to Ci-4 haloalkylsulfonyl is optionally substituted, and the aryl moiety in C₆_i₀ aryl-Ci_₂ alkyl and the heteroaryl moiety in heteroaryl-Ci_₂ alkyl may be substituted with one to three groups selected from a group consisting of halogen, cyano, nitro, Ci_₄ alkyl, Ci_₄ haloalkyl, Ci_₄ alkoxy, Ci_₄ haloalkoxy and Ci_ alkoxy-carbonyl, among the definitions, each group from Ci_ alkyl to Ci_ alkoxy-carbonyl is optionally substituted. Among the compounds of Formula (I) compounds having one of the following Formulas (I-l) to (1-4) are preferred:

Each compound having Formula (I) according to the invention has an asymmetric carbon atom, and the compounds of the invention specified by Formula (I) include an optical isomer.

When l-(3-bromo-4-fluorophenyl)-4,4,4-trifluoro-3-(nitromethyl)-3-(3,4,5-trichlorophenyl)butan-l-one is used as a reaction material and reduced by sodium borohydride, Preparation method (a) is expressed by the

When 5 -(3 -bromo-4-fluorophenyl)-3 -(3 ,4,5 -trichlorophenyl)-3 -(trifluoromethyl)-3 ,4-dihydro-2H-pyrrol- 1 -oxide and lH-l,2,4-triazole are used as reaction materials, Preparation method (b) is expressed by the following reaction scheme.

When 1 - {2-bromo-4-[ 1 -oxide-3 -(3 ,4,5 -trichlorophenyl)-3 -(trifluoromethyl)-3 ,4-dihydro-2H-pyrrol-5 - yl]-phenyl}-lH-l,2,4-triazole and zinc cyanide are used as reaction materials, Preparation method (c) is expres

The compounds having Formula (II) in Preparation method (a) are the compounds that have been described in international patent application PCT/EP2011/055639 or in its priority application Japanese Patent Application No. 2010-92182.

Examples of the metal hydride compound which is used in Preparation method (a) include sodium borohydride, and lithium aluminum hydride.

The reaction of Preparation method (a) may be carried out in the presence of an appropriate diluent, and examples of the diluent which can be used include aliphatic, alicyclic, and aromatic hydrocarbons (they may be also chlorinated depending on specific cases) such as pentane, hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, 1 ,2- dichloroethane, chlorobenzene, and dichlorobenzene; ethers such as ethyl ether, methylethyl ether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF), and diethylene glycol dimethyl ether (DGM); ketones such as acetone, methylethyl ketone (MEK), methyl-isopropyl ketone, and methylisobutyl ketone (MIBK); nitriles such as acetonitrile, propionitrile, and acrylonitrile; alcohols such as methanol, ethanol, isopropanol, butanol, and ethylene glycol; esters such as ethyl acetate, and amyl acetate; acid amides such as dimethyl formamide (DMF), dimethylacetamide (DMA), N-methylpyrrolidone, l,3-dimethyl-2-imidazolidinone, and hexamethylphosphoric triamide (HMPA); sulfones and sulfoxides such as dimethyl sulfoxide (DMSO) and sulfolane; and bases such as pyridine.

For hydrogentaion, the reaction of Preparation method (a) is preferably carried out in the presence of nickel chloride. Preparation method (a) can be carried out over a substantially wide range of temperatures. It may be generally carried out at a temperature between about -10°C and about 80°C, preferably between about 0°C and about 50°C. Furthermore, the reaction is preferably carried out under normal pressure . However, it may be carried out under reduced or elevated pressure.

In carrying out Preparation method (a), for example, by a reaction of 1 mole of the compound having Formula (II) and 0.5 mole of nickel (II) chloride hexahydrate with 3 moles of sodium borohydride in a mixture solvent of methanol and dioxane, the target compound having Formula (I) can be obtained.

The compound having Formula (III) in Preparation method (b) can be synthesized according to the above Preparation method (a).

The compound having Formula (IV) is well known as a heterocyclic compound. Examples of the compound having Formula (IV) include lH-l,2,4-triazole, lH-l,2,3-triazole, pyrazole, and lH-l,2,3,4-tetrazole.

The reaction of Preparation method (b) may be carried out in the presence of an appropriate diluent, and examples of the diluent which can be used include aliphatic, alicyclic, and aromatic hydrocarbons (it may be also chlorinated depending on specific cases) such as pentane, hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, 1 ,2- dichloroethane, chlorobenzene, and dichlorobenzene; ethers such as ethyl ether, methylethyl ether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF), and diethylene glycol dimethyl ether (DGM); ketones such as acetone, methylethyl ketone (MEK), methyl-isopropyl ketone, and methylisobutyl ketone (MIBK); nitriles such as acetonitrile, propionitrile, and acrylonitrile; alcohols such as methanol, ethanol, isopropanol, butanol, and ethylene glycol; esters such as ethyl acetate, and amyl acetate; acid amides such as dimethyl formamide (DMF), dimethylacetamide (DMA), N-methylpyrrolidone, l ,3-dimethyl-2-imidazolidinone, and hexamethylphosphoric triamide (HMPA); sulfones and sulfoxides such as dimethyl sulfoxide (DMSO) and sulfolane; and bases such as pyridine.

Preparation method (b) can be carried out using a base, for example, alkali metal bases such as sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium acetate, potassium acetate, sodium methoxide, sodium ethoxide, and potassium tert-butoxide; lithium hydride ; and organic base s such as triethylamine, diisopropylethylamine, tributylamine, N- methylmorpholine, N,N-dimethylaniline, Ν,Ν-diethylaniline, 4-tert-butyl-N,N-dimethylaniline, pyridine, picoline, lutidine, diazabicycloundecene, diazabicyclooctane, and imidazole. The reaction of the Preparation method (b) can be carried out over a substantially wide range of temperatures. It may be generally carried out at a temperature between about -80°C and about 200°C, preferably between -10°C and about 100°C. Furthermore, the reaction is preferably carried out under normal pressure. However, it may be carried out under reduced or elevated pressure. The reaction time is 0.1 to 72 hours and preferably 1 to 24 hours.

In carrying out Preparation method (b), for example, by a reaction of the compound having Formula (IV) in an amount of 1 molar or a slightly excessive amount with respect to 1 molar of the compound having Formula (III) in a diluent, for example DMF, the target compound having Formula (I) can be obtained.

The compound having Formula (V) in Preparation method (c) can be synthesized according to the above Preparation method (b).

Examples of the cyanation agent used in Preparation method (c) include zinc cyanide and copper cyanide.

The reaction of Preparation method (c) may be carried out in the presence of an appropriate diluent, and examples of the diluent which can be used include aliphatic, alicyclic, and aromatic hydrocarbons (it may be also chlorinated depending on specific cases) such as pentane, hexane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene, dichloromethane, chloroform, carbon tetrachloride, 1,2- dichloroethane, chlorobenzene, and dichlorobenzene; ethers such as ethyl ether, methylethyl ether, isopropyl ether, butyl ether, dioxane, dimethoxyethane (DME), tetrahydrofuran (THF), and diethylene glycol dimethyl ether (DGM); ketones such as acetone, methylethyl ketone (MEK), methyl-isopropyl ketone, and methylisobutyl ketone (MIBK); nitriles such as acetonitrile, propionitrile, and acrylonitrile; alcohols such as methanol, ethanol, isopropanol, butanol, and ethylene glycol; esters such as ethyl acetate, and amyl acetate; acid amides such as dimethyl formamide (DMF), dimethylacetamide (DMA), N-methylpyrrolidone, l,3-dimethyl-2-imidazolidinone, and hexamethylphosphoric triamide (HMPA); sulfones and sulfoxides such as dimethyl sulfoxide (DMSO) and sulfolane; and bases such as pyridine.

Preparation method (c) is preferably carried out in the presence of a transition metal catalyst. Examples of the transition metal catalyst include a palladium complex and the representative examples include tetraki s (triphenylpho sphine) palladium , tris (benzylideneacetone) dipalladium , and bis(benzylideneacetone) palladium.

The reaction of the Preparation method (c) can be carried out over a substantially wide range of temperatures. It may be generally carried out at a temperature between about -80°C and about 200°C, preferably between -10°C and about 100°C. Furthermore, the reaction is preferably carried out under normal pressure. However, it may be carried out under reduced or elevated pressure. The reaction time is 0.1 to 72 hours and preferably 1 to 24 hours.

In carrying out Preparation method (c), for example, by a reaction of zinc cyanide in an amount of 1 molar or a slightly excessive amount thereof with respect to 1 mole of the compound having Formula (V) in a diluent, for example DMF, in the presence of a catalytic amount of tetrakis(triphenylphosphine) palladium, the target compound having Formula (I) can be obtained.

The compounds having Formula (I) of the invention exhibit a strong pesticidal effect, and therefore can be used as pesticides. Furthermore, the compounds of the invention exhibit a strong controlling effect against noxious insects without causing any damages on crop plants that are cultivated. Therefore, the compounds of the invention can be used for controlling a wide variety of pests including, for example, harmful sucking insects, chewing insects and other plant parasitic pests, stored grain insects, hygienic pests, etc., and can be applied to control and eradicate these pests. Examples of pests are as follows. As an insect, Coleoptera, for example Callosobruchus chinensis, Sitophilus zeamais, Tribolium castaneum, Epilachna vigintioctomaculata, Agriotes fuscicollis, Anomala rufocuprea, Leptinotarsa decemlineata, Diabrotica spp., Monochamus alternatus, Lissorhoptrus oryzophilus, Lyctus bruneus and Aulacophora femoralis; Lepidoptera, for example, Lymantria dispar, Malacosoma neustria, Pieris rapae, Spodoptera litura, Mamestra brassicae, Chilo suppressalis, Pyrausta nubilalis, Ephestia cautella, Adoxophyes orana, Carpocapsa pomonella, Agrotisfucosa, Galleria mellonella, Plutella maculipennis, Heliothis virescens and Phyllocnistis citrella; Hemiptera, for example, Nephotettix cincticeps, Nilaparvata lugens, Pseudococcus comstocki, Unapsis yanonensis, Myzus persicas, Aphis pomi, Aphis gossypii, Rhopalosiphum pseudobrassicas, Stephanitis nashi, Nezara spp., Trialeurodes vaporariorm and Psylla spp.; Thysanoptera, for example, Thrips palmi and Franklinella occidental; Orthoptera, for example, Blatella germanica, Periplaneta americana, Gryllotalpa Africana and Locusta migratoria migratoriodes; Isoptera, for example, Reticulitermes speratus and Coptotermes formosanus; Diptera, for example, Musca domestica, Aedes aegypti, Hylemia platura, Culex pipiens, Anopheles sinensis, Culex tritaeniorhynchus and Liriomyza torifolii are included.

As Acarina, for example, Tetranychus cinnabarinus, Tetranychus urticae, Panonychus citri, Aculops pelekassi and Tarsonemus spp are included.

As nematodes, for example, Meloidogyne incognita, Bursaphelenchus lignicolus Mamiya et Kiyohara, Aphelenchoides besseyi, Heterodera glycines and Pratylenchus spp are included.

The compounds of the present invention have good tolerance in plants and low toxicity to warm-blooded animals. Further, as being well received by an environment, the compounds of the present invention are appropriate for the protection of plants and plant parts.

With application of the compounds of the present invention, both crop yield and quality of harvested products may be improved. In addition, the compounds of the present invention are suitable for protection of preserved products and materials and for a hygiene field, in terms of controlling harmful animals, in particular insects, spider-like animals, helminth, nematodes and mollusks that are encountered in agriculture, horticulture, veterinary medicine, forest, garden and entertainment facilities. The compounds of the present invention can be preferably used as agents for protecting plants. The compounds of the present invention have an activity for normal sensitive species or resistant species, and for all over or several growth stages thereof. In particular, the harmful organisms mentioned above include the followings.

As Anoplura (Phthiraptera), for example, Damalinia spp., Haematopinus, Linognathus spp., Pediculus spp. and Trichodectes spp are included.

As Arachnida, for example, Acarus siro, Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri, Eutetranyctus spp., Eriophyes spp., Hemitarsonemus spp., Hyalomma spp ., Ixodes spp ., Latrodectus mactans, Metatetranychus spp., Oligonychus spp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp. and Vasates lycopersici are included.

As Bivalva, for example, Dreissena spp is included.

As Chilopoda, for example, Geophilus spp. and Scutigera spp are included.

As Coleoptera, for example, Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp., Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., Anthrenus spp., Apogonia spp., Atomaria spp., Attagenus spp., Bruchidius obtectus, Bruchus spp., Ceuthorhynchus spp., Cleonus mendicus, Conoderus spp., Cosmopolites spp., Costelytra zealandica, Curculio spp., Cryptorhynchus lapathi, Dermestes spp., Diabrotica spp., Epilachna spp., Faustinus cubae, Gibbium psylloides, Heteronychus arator, Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lachnosterna consanguinea, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus, Lixus spp., Lyctus spp., Meligethes aeneus, Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchus sulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Popillia japonica, Premnotrypes spp., Psylliodes chrysocephala, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., Sphenophorus spp., Sternechus spp., Symphyletes spp., Tenebrio molitor, Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp. and Zabrus spp are included.

As Collembola, for example, Onychiurus armatus is included.

As Dermaptera, for example, Forficula auricularia is included.

As Diplopoda, for example, Blaniulus guttulatus is included. As Diptera, for example, Aedes spp., Anopheles spp., Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata, Chrysomyia spp., Cochliomyia spp., Cordylobia anthropophaga, Culex spp., Cuterebra spp., Dacus oleae, Dermatobia hominis, Drosophila spp., Fannia spp., Gastrophilus spp., Hylemyia spp., Hyppobosca spp., Hypoderma spp., Liriomyza spp., Lucilia spp., Musca spp., Nezara spp., Oestrus spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Stomoxys spp., Tabanus spp., Tannia spp., Tipula paludosa andWohlfahrtia spp are included.

As Gastropoda, for example, Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp. and Succinea spp are included.

As helminthes, for example, Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp., Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medeinensis, Echinococcus granulosus, Echinococcus multiocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp., Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa loa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp., Strongyloides fuelleborni, Strongyloides stercoralis, Stronyloides spp., Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichuria) and Wuchereria bancrofti are included.

Further, Protozoa, such as Eimeria, can be controlled by the compound of the present invention. As Heteroptera, for example, Anasa tristis, Antestiopsis spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp ., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus,spp., Euschistus spp., Eurygaster spp., Heliopeltis spp., Horchias nobiellus, Leptocorisa spp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae, Nezara spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., Psallus seriatus, Pseudacysta persea, Rhodonius spp., Sahlbergella singularis, Scotinophora spp., Stephanitis nashi, Tibraca spp. and Triatoma spp are included.

As Homoptera, for example, Acyrthosipon spp., Aeneolamia spp., gonoscena spp., Aleurodes spp., Aleurolobus barodensis), Aleurothrixus spp ., Amrasca spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri, Aphis spp., Arboridia apicalis, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani, Bemisia spp., Brachycaudus helichrysii, Brachycolus spp., Brevicoryne brassicae, Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., Chryptomyzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp., Diaspis spp., Doralis spp., Drosicha spp., Dysaphis spp., Dysmicoccus spp., Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelis bilobatus, Geococcus coffeae, Homalodisca coagulata, Hyalopterus arundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi, Macrosiphum spp., Mahanarva fimbriolata, Melanaphis sacchari, Metcalfiella spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettix spp., Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Parabemisia myricae, Paratorioza spp., Parlatoria spp., Pemphigus spp., Peregrinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp., Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Psylla spp., Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesda gigas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp., Scaphoides titanus, Schizaphis graminum, Selenaspidus articulatus, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis spp ., Toxoptera spp ., Trialeurodes vaporariorum, Trioza spp., Typhlocyba spp., Unaspis spp. and Viteus vitifolii are included.

As Hymenoptera, for example, Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis) and Vespa spp are included.

As Isopoda, for example, Armadillidium vulgare, Oniscus asellus and Porcellio scaber are included. As Isoptera, for example, Reticulitermes spp. and Odontotermes spp are included.

As Lepidoptera, for example, Acronicta major, Aedia leucomelas, Agrotis spp., Alabama argillacea, Anticarsia spp., Barathra brassicae, Bucculatrix thurberiella, Bupalus piniarius, Cacoecia podana, Capua reticulana, Carpocapsa pomonella, Cheimatobia brumata, Chilo spp., Choristoneura fumiferana, Clysia ambiguella, Cnaphalocerus spp., Earias insulana, Ephestia kuehniella, Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Helicoverpa spp., Heliothis spp., Hofmannophila pseudospretella, Homona magnanima, Hyponomeuta padella, Laphygma spp., Lithocolletis blancardella, Lithophane antennata, Loxagrotis albicosta, Lymantria spp., Malacosoma neustria, Mamestra brassicae, Mocis repanda, Mythimna separata, Oria spp., Oulema oryzae, Panolis flammea, Pectinophora gossypiella, Phyllocnistis citrella, Pieris spp., Plutella xylostella, Prodenia spp., Pseudaletia spp., Pseudoplusia includens, Pyrausta nubilalis, Spodoptera spp., Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana and Trichoplusia spp are included.

As Orthoptera, for example, Acheta domesticus, Blatta orientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta Americana and Schistocerca gregaria are included.

As Siphonaptera, for example, Ceratophyllus spp. and Xenopsylla cheopis are included. As Symphyla, for example, Scutigerella immaculate is included. As Thynsanoptera, for example, Baliothrips biformis, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni and Thrips spp are included.

As Thysanura, for example, Lepisma saccharina is included. As plant parasitic nematodes, for example, Anguina spp., Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Ditylenchus dipsaci, Globodera spp., Heliocotylenchus spp., Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, Rotylenchus spp., Trichodorus spp., Tylenchorhynchus spp., Tylenchulus spp., Thlenchulus semipenetrans and Xiphinema spp. are included.

Additionally to above mentioned, the active compounds according to the invention, in combination with good plant tolerance and favourable toxicity to warm-blooded animals and being tolerated well by the environment, are suitable for protecting plants and plant organs, for increasing harvest yields, for improving the quality of the harvested material and for controlling animal pests, in particular insects, arachnids, helminths, nematodes and molluscs, which are encountered in agriculture, in horticulture, in animal husbandry, in forests, in gardens and leisure facilities, in protection of stored products and of materials, and in the hygiene sector. They can be preferably employed as plant protection agents. They are active against normally sensitive and resistant species and against all or some stages of development. The abovementioned pests include: pests from the phylum Arthropoda, especially from the class Arachnida, for example, Acarus spp., Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., Bryobia graminum, Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., Epitrimerus pyri, Eutetranychus spp., Eriophyes spp ., Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus spp., Loxosceles spp., Metatetranychus spp., Neutrombicula autumnalis, Nuphersa spp., Oligonychus spp., Ornithodorus spp., Ornithonyssus spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp., Steneotarsonemus spinki, Tarsonemus spp., Tetranychus spp., Trombicula alfreddugesi, Vaejovis spp., Vasates lycopersici;

from the class Chilopoda, for example, Geophilus spp., Scutigera spp.;

from the order or the class Collembola, for example, Onychiurus armatus;

from the class Diplopoda, for example, Blaniulus guttulatus; from the class Insecta, e.g. from the order Blattodea, for example, Blattella asahinai, Blattella germanica, Blatta orientalis, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta spp., Supella longipalpa; from the order Coleoptera, for example, Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp., Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., Attagenus spp., Bruchidius obtectus, Bruchus spp., Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., Chaetocnema spp., Cleonus mendicus, Conoderus spp., Cosmopolites spp., Costelytra zealandica, Ctenicera spp., Curculio spp., Cryptolestes ferrugineus, Cryptorhynchus lapathi, Cylindrocopturus spp., Dermestes spp., Diabrotica spp., Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epilachna spp., Epitrix spp., Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Hellula undalis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp ., Lema spp ., Leptinotarsa decemlineata, Leucoptera spp ., Lissorhoptrus oryzophilus, Lixus spp., Luperodes spp., Lyctus spp., Megascelis spp., Melanotus spp., Meligethes aeneus, Melolontha spp., Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorrhynchus spp., Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllophaga helleri, Phyllotreta spp., Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., Sitophilus oryzae, Sphenophorus spp., Stegobium paniceum, Sternechus spp ., Symphyletes spp ., Tanymecus spp., Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp.; from the order Diptera, for example, Aedes spp., Agromyza spp., Anastrepha spp., Anopheles spp., Asphondylia spp., Bactrocera spp., Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina, Ceratitis capitata, Chironomus spp ., Chrysomyia spp ., Chrysops spp., Chrysozona pluvialis, Cochliomyia spp., Contarinia spp., Cordylobia anthropophaga, Cricotopus sylvestris, Culex spp., Culicoides spp., Culiseta spp., Cuterebra spp., Dacus oleae, Dasyneura spp., Delia spp., Dermatobia hominis, Drosophila spp ., Echinocnemus spp., Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp., Liriomyza spp., Lucilia spp., Lutzomyia spp., Mansonia spp., Musca spp., Oestrus spp., Oscinella frit, Paratanytarsus spp., Paralauterborniella subcincta, Pegomyia spp., Phlebotomus spp., Phorbia spp., Phormia spp., Piophila casei, Prodiplosis spp., Psila rosae, Rhagoletis spp., Sarcophaga spp., Simulium spp., Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp.; from the order Heteroptera, for example, Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., Eurygaster spp., Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptocorisa varicornis, Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae, Monalonion atratum, Nezara spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.; from the order Homoptera, for example, Acizzia acaciaebaileyanae, Acizzia dodonaeae, Acizzia uncatoides, Acrida turrita, Acyrthosipon spp., Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Allocaridara malayensis, Amrasca spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri, Aphis spp., Arboridia apicalis, Arytainilla spp., Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp., Calligypona marginata, Cameocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris rosea, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., Cryptomyzus ribis, Cryptoneossa spp., Ctenarytaina spp., Dalbulus spp., Dialeurodes citri, Diaphorina citri, Diaspis spp., Drosicha spp., Dysaphis spp., Dysmicoccus spp., Empoasca spp., Eriosoma spp., Erythroneura spp., Eucalyptolyma spp., Euphyllura spp., Euscelis bilobatus, Ferrisia spp., Geococcus coffeae, Glycaspis spp., Heteropsylla cubana, Heteropsylla spinulosa, Homalodisca coagulata, Hyalopterus arundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi, Macrosiphum spp., Macrosteles facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettix spp., Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp ., Orthezia praelonga, Oxya chinensis, Pachypsylla spp ., Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp., Peregrinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp., Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Psyllopsis spp., Psylla spp., Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp., Scaphoideus titanus, Schizaphis graminum, Selenaspidus articulatus, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Siphoninus phillyreae, Tenalaphara malayensis, Tetragonocephela spp., Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., Trialeurodes vaporariorum, Trioza spp., Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.; from the order Hymenoptera, for example, Acromyrmex spp., Athalia spp., Atta spp., Diprion spp. Hoplocampa spp., Lasius spp., Monomorium pharaonis, Sirex spp., Solenopsis invicta, Tapinoma spp., Urocerus spp., Vespa spp., Xeris spp.; from the order Isopoda, for example, Armadillidium vulgare, Oniscus asellus, Porcellio scaber; from the order Isoptera, for example, Coptotermes spp., Cornitermes cumulans, Cryptotermes spp., Incisitermes spp., Microtermes obesi, Odontotermes spp., Reticulitermes spp.; from the order Lepidoptera, for example, Achroia grisella, Acronicta major, Adoxophyes spp., Aedia leucomelas, Agrotis spp ., Alabama spp ., Amyelois transitella, Anarsia spp ., Anticarsia spp., Argyroploce spp., Barathra brassicae, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp., Choristoneura spp., Clysia ambiguella, Cnaphalocerus spp., Cnaphalocrocis medinalis, Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., Dalaca noctuides, Diaphania spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp., Epinotia spp., Epiphyas postvittana, Etiella spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., Hedylepta spp., Helicoverpa spp., Heliothis spp., Hofmannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., Lithocolletis spp., Lithophane antennata, Lobesia spp., Loxagrotis albicosta, Lymantria spp., Lyonetia spp., Malacosoma neustria, Maruca testulalis, Mamstra brassicae, Melanitis leda, Mocis spp., Monopis obviella, Mythimna separata, Nemapogon cloacellus, Nymphula spp., Oiketicus spp., Oria spp., Orthaga spp., Ostrinia spp., Oulema oryzae, Panolis flammea, Parnara spp., Pectinophora spp., Perileucoptera spp., Phthorimaea spp., Phyllocnistis citrella, Phyllonorycter spp., Pieris spp., Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella, Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., Scirpophaga spp., Scirpophaga innotata, Scotia segetum, Sesamia spp., Sesamia inferens, Sparganothis spp., Spodoptera spp., Spodoptera praefica, Stathmopoda spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thermesia gemmatalis, Tinea cloacella, Tinea pellionella, Tineola bisselliella, Tortrix spp., Trichophaga tapetzella, Trichoplusia spp., Tryporyza incertulas, Tuta absoluta, Virachola spp.; from the order Orthoptera or Saltatoria, for example, Acheta domesticus, Dichroplus spp., Gryllotalpa spp., Hieroglyphus spp., Locusta spp., Melanoplus spp., Schistocerca gregaria; from the order Phthiraptera, for example, Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Ptirus pubis, Trichodectes spp.; from the order Psocoptera for example Lepinatus spp., Liposcelis spp.; from the order Siphonaptera, for example, Ceratophyllus spp., Ctenocephalides spp., Pulex irritans, Tunga penetrans, Xenopsylla cheopsis; from the order Thysanoptera, for example, Anaphothrips obscurus, Baliothrips biformis, Drepanothrips reuteri, Enneothrips flavens, Frankliniella spp . , Heliothrips spp . , Hercinothrips femoralis, Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamomi, Thrips spp.; from the order Zygentoma (=Thysanura), for example, Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class Symphyla, for example, Scutigerella spp.; pests from the phylum Mollusca, especially from the class Bivalvia, for example, Dreissena spp., and from the class Gastropoda, for example, Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp.; animal pests from the phylums Plathelminthes and Nematoda, for example, Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp., Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp., Heterakis spp., Hymenolepis nana, Hyostrongulus spp ., Loa Loa, Nematodirus spp., Oesophagostomum spp ., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp., Strongyloides fuelleborni, Strongyloides stercoralis, Stronyloides spp., Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti; phytoparasitic pests from the phylum Nematoda, for example, Aphelenchoides spp., Bursaphelenchus spp ., Ditylenchus spp., Globodera spp., Heterodera spp ., Longidorus spp ., Meloidogyne spp., Pratylenchus spp . , Radopholus spp . , Trichodorus spp . , Tylenchulus spp . , Xiphinema spp . , Helicotylenchus spp., Tylenchorhynchus spp., Scutellonema spp., Paratrichodorus spp., Meloinema spp., Paraphelenchus spp ., Aglenchus spp., Belonolaimus spp ., Nacobbus spp., Rotylenchulus spp., Rotylenchus spp., Neotylenchus spp., Paraphelenchus spp., Dolichodorus spp., Hoplolaimus spp., Punctodera spp., Criconemella spp., Quinisulcius spp., Hemicycliophora spp., Anguina spp., Subanguina spp., Hemicriconemoides spp., Psilenchus spp., Pseudohalenchus spp., Criconemoides spp., Cacopaurus spp. It is furthermore possible to control organisms from the subphylum Protozoa, especially from the order Coccidia, such as Eimeria spp.

Any kind of plant and plant part can be treated according to the present invention. In the present invention, a plant should be understood as all plants and plant populations including desirable and undesirable wild plants or crop plants (including naturally-occurring crop plants) and the like. As for the crop plants, they can be plants which are obtainable by conventional methods of breeding modified varieties and optimization methods, or biotechnological methods and genetic engineering methods, or by combination of these methods, and they include transgenic plants. In addition, plant varieties which are either protected or not protected by a plant breeder are also included. Plant parts should be understood as all parts and organs of a plant that are present above or under ground. Examples thereof include shoots, leaves, flowers and roots, etc. Specific examples thereof include a leaf, a needle, a stem, a trunk, a flower, a fruit, a fruit body, a seed, a root, a tuber and an underground tuber, etc. The plant parts also include a harvested material and a material which propagates sexually or asexually, for example, a cutting, a tuber, an underground tuber, a side branch and a seed. Treatment of plants and plant parts with the active compounds according to the present invention can be carried out directly or by using conventional methods such as impregnation, spray, evaporation, particularization, dispersion, coating and injection, or for a propagating material, especially for a seed, by coating it with one or more of the compounds, so that the compounds are applied to their surroundings, habitat environment, or preservation place. The compounds of the present invention have a penetrating activity and this means that the compounds can penetrate a plant body and can migrate from the underground part to the above- ground part of a plant. As it has been described above, according to the present invention, all plants and parts thereof can be treated. According to a preferred embodiment for carrying out the invention, wild plant species and plant mutants, or those obtained by traditional plant breeding methods such as hybridization or protoplast fusion, and parts thereof are treated. According to a more preferred embodiment for carrying out the invention, transgenic plants and plant varieties (genetically modified organisms) obtained by conventional methods in appropriate combination with genetic engineering methods, and parts thereof are treated. The terms "parts", "parts of a plant" and "plant parts" are as defined above. Still more preferably, for each specific case, plants of plant varieties that are commercially available or currently in use are treated according to the present invention. Plant varieties are understood as plants having new characteristics ("traits") obtained by conventional breed improvements, introduction of mutation or recombinant DNA techniques. They can be plant varieties, biotypes or genotypes. Depending on plant species or plant varieties, their habitat and growth condition (soil, weather, growth period, nutrition, etc.), the treatment according to the present invention may have a supra-additive ("synergy") effect. Thus, for example, exceeding an expected effect, it is possible to obtain several effects including reduction of application rate and/or broadening of an activity spectrum, and/or increased activity of the material and composition that can be used according to the present invention, improvement of plant growth, enhancement of tolerance to high or low temperature, enhancement of tolerance to drought, moisture or salt contained in soil, improvement of a flowering property, simplification of harvest methods, accelerated maturation, increased harvest amount, improvement of quality and/or nutritional value of harvest products, and improvement of preservation stability and/or processability of harvested products. The preferable transgenic plants or plant varieties (obtainable by genetic engineering methods) treated according to the present invention include all kinds of plant having genetic materials that can provide the plants with very advantageous and useful traits based on genetic modifications. Examples of such traits include improvement of plant growth, enhancement of tolerance to high or low temperature, enhancement of tolerance to drought, moisture or salt contained in soil, improvement of a flowering property, simplification of harvest methods, accelerated maturation, increased harvest amount, improvement of quality and/or nutritional value of harvest products, and improvement of preservation stability and/or processability of harvested products. Further examples in which such traits are particularly more emphasized include improved protection of plants against harmful animals and harmful microorganisms such as insect, tick, plant pathogenic fungus, bacteria and/or virus, and improved tolerance of plants against compounds having certain type of herbicidal activities. Examples of the transgenic plant include grain crops (barley, rice), corn, soybean, potato, sugar beet, tomato, bean and other modified plant species, useful plants such as cotton, tobacco, rape seed, and fruit plants (fruits like an apple, a pear, a citrus fruit and other fruit-bearing plants like a grape). In particular, corn, soybean, potato, cotton, tobacco and rape seed are important. As for the traits considered to be important, improved plant defense based on toxins produced by plants, in particular based on the toxins produced by plants with an action of genetic materials derived from Bacillus thuringiensis (for example, genes including CrylA(a), CrylA(b), CrylA(c), CryllA, CrylllA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF, and combination thereof), against insects, spider-like animals, nematodes, slugs, and snails (herein below, referred to as "Bt plant") can be mentioned. Other traits considered to be important include improved plant defense against fungus, bacteria and virus, based on systemic acquired resistance (SAR), systemin, phytoallexin, elicitor, resistance gene and the corresponding protein and toxin expressed from the gene. Further, particularly important traits are improved tolerance of plants to a certain kind of an active compound having a herbicidal activity, such as imidazolinone, sulfonyl urea, glyphosate or phosphinotricine (e.g., "PTA" gene). Genes which can endow desired traits to a subject can also be present in combination each other in a transgenic plant. Examples of the "Bt plant" include modified varieties of corn, modified varieties of cotton and modified varieties of potato that are commercially available under the trade names of YIELD GARD^(R) (for example, corn, cotton, soybean), KnockOut^(R) (for example, corn), StarLink^(R) (for example, corn), Bollgard^(R) (cotton), Nucotn^(R) (cotton) and New Leaf ^R) (potato), respectively. Examples of the plant having resistance to herbicides include modified varieties of corn, modified varieties of cotton and modified varieties of potato that are commercially available under the trade names of Roundup Ready^(R) (resistance to glyphosate, for example, corn, cotton, soybean), Liberty Link^(R) (resistance to phosphinotricine, for example rape seed), IMI^(R) (resistance to imidazolinones) and STS^(R) (resistance to sulfonylurea, for example, corn), respectively. Examples of the plant having resistance to herbicides (i.e., the plant obtained by conventional breeding methods to have resistance to herbicides) also include modified varieties, for example those that are commercially available under the trade name of Clearfield^(R) (for example, corn). Of course, these descriptions are also applied to plant varieties which have already had genetic traits or will have genetic traits to be developed in future. Such plant varieties will be developed and/or on the market in future.

Additionally to above mentione, according to the invention all plants and plant parts can be treated. By plants is meant all plants and plant populations such as desirable and undesirable wild plants, cultivars and plant varieties (whether or not protectable by plant variety or plant breeder's rights). Cultivars and plant varieties can be plants obtained by conventional propagation and breeding methods which can be assisted or supplemented by one or more biotechnological methods such as by use of double haploids, protoplast fusion, random and directed mutagenesis, molecular or genetic markers or by bioengineering and genetic engineering methods. By plant parts is meant all above ground and below ground parts and organs of plants such as shoot, leaf, blossom and root, whereby for example leaves, needles, stems, branches, blossoms, fruiting bodies, fruits and seed as well as roots, tubers, corms and rhizomes are listed. Crops and vegetative and generative propagating material, for example cuttings, corms, rhizomes, tubers, runners and seeds also belong to plant parts.

Among the plants that can be protected by the method according to the invention, mention may be made of major field crops like corn, soybean, cotton, Brassica oilseeds such as Brassica napus (e.g. canola), Brassica rapa, B. juncea (e.g. mustard) and Brassica carinata, rice, wheat, sugarbeet, sugarcane, oats, rye, barley, millet, triticale, flax, vine and various fruits and vegetables of various botanical taxa such as Rosaceae sp. (for instance pip fruit such as apples and pears, but also stone fruit such as apricots, cherries, almonds and peaches, berry fruits such as strawberries), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (for instance banana trees and plantings), Rubiaceae sp. (for instance coffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (for instance lemons, oranges and grapefruit) ; Solanaceae sp. (for instance tomatoes, potatoes, peppers, eggplant), Liliaceae sp., Compositiae sp. (for instance lettuce, artichoke and chicory - including root chicory, endive or common chicory), Umbelliferae sp. (for instance carrot, parsley, celery and celeriac), Cucurbitaceae sp. (for instance cucumber - including pickling cucumber, squash, watermelon, gourds and melons), Alliaceae sp. (for instance onions and leek), Cruciferae sp. (for instance white cabbage, red cabbage, broccoli, cauliflower, brussel sprouts, pak choi, kohlrabi, radish, horseradish, cress, Chinese cabbage), Leguminosae sp. (for instance peanuts, peas and beans beans - such as climbing beans and broad beans), Chenopodiaceae sp. (for instance mangold, spinach beet, spinach, beetroots), Malvaceae (for instance okra), Asparagaceae (for instance asparagus); horticultural and forest crops; ornamental plants; as well as genetically modified homologues of these crops.

The method of treatment according to the invention can be used in the treatment of genetically modified organisms (GMOs), e.g. plants or seeds. Genetically modified plants (or transgenic plants) are plants of which a heterologous gene has been stably integrated into genome. The expression "heterologous gene" essentially means a gene which is provided or assembled outside the plant and when introduced in the nuclear, chloroplastic or mitochondrial genome gives the transformed plant new or improved agronomic or other properties by expressing a protein or polypeptide of interest or by downregulating or silencing other gene(s) which are present in the plant (using for example, antisense technology, cosuppression technology or RNA interference - RNAi - technology). A heterologous gene that is located in the genome is also called a transgene. A transgene that is defined by its particular location in the plant genome is called a transformation or transgenic event.

Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also result in superadditive ("synergistic") effects. Thus, for example, reduced application rates and/or a widening of the activity spectrum and/or an increase in the activity of the active compounds and compositions which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, bigger fruits, larger plant height, greener leaf color, earlier flowering, higher quality and/or a higher nutritional value of the harvested products, higher sugar concentration within the fruits, better storage stability and/or processability of the harvested products are possible, which exceed the effects which were actually to be expected.

At certain application rates, the active compound combinations according to the invention may also have a strengthening effect in plants. Accordingly, they are also suitable for mobilizing the defense system of the plant against attack by unwanted microorganisms. This may, if appropriate, be one of the reasons of the enhanced activity of the combinations according to the invention, for example against fungi. Plant- strengthening (resistance-inducing) substances are to be understood as meaning, in the present context, those substances or combinations of substances which are capable of stimulating the defense system of plants in such a way that, when subsequently inoculated with unwanted microorganisms, the treated plants display a substantial degree of resistance to these microorganisms. In the present case, unwanted microorganisms are to be understood as meaning phytopathogenic fungi, bacteria and viruses. Thus, the substances according to the invention can be employed for protecting plants against attack by the abovementioned pathogens within a certain period of time after the treatment. The period of time within which protection is effected generally extends from 1 to 10 days, preferably 1 to 7 days, after the treatment of the plants with the active compounds. Plants and plant cultivars which are preferably to be treated according to the invention include all plants which have genetic material which impart particularly advantageous, useful traits to these plants (whether obtained by breeding and/or biotechnological means).

Plants and plant cultivars which are also preferably to be treated according to the invention are resistant against one or more biotic stresses, i.e. said plants show a better defense against animal and microbial pests, such as against nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and/or viroids.

Examples of nematode resistant plants are described in e.g. US Patent Application Nos 1 1/765,491, 1 1/765,494, 10/926,819, 10/782,020, 12/032,479, 10/783,417, 10/782,096, 1 1/657,964, 12/192,904, 11/396,808, 12/166,253, 12/166,239, 12/166, 124, 12/166,209, 1 1/762,886, 12/364,335, 1 1/763,947, 12/252,453, 12/209,354, 12/491,396 or 12/497,221.

Plants and plant cultivars which may also be treated according to the invention are those plants which are resistant to one or more abiotic stresses. Abiotic stress conditions may include, for example, drought, cold temperature exposure, heat exposure, osmotic stress, flooding, increased soil salinity, increased mineral exposure, ozone exposure, high light exposure, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients, shade avoidance.

Plants and plant cultivars which may also be treated according to the invention, are those plants characterized by enhanced yield characteristics. Increased yield in said plants can be the result of, for example, improved plant physiology, growth and development, such as water use efficiency, water retention efficiency, improved nitrogen use, enhanced carbon assimilation, improved photosynthesis, increased germination efficiency and accelerated maturation. Yield can furthermore be affected by improved plant architecture (under stress and non-stress conditions), including but not limited to, early flowering, flowering control for hybrid seed production, seedling vigor, plant size, internode number and distance, root growth, seed size, fruit size, pod size, pod or ear number, seed number per pod or ear, seed mass, enhanced seed filling, reduced seed dispersal, reduced pod dehiscence and lodging resistance. Further yield traits include seed composition, such as carbohydrate content, protein content, oil content and composition, nutritional value, reduction in anti-nutritional compounds, improved processability and better storage stability.

Plants that may be treated according to the invention are hybrid plants that already express the characteristic of heterosis or hybrid vigor which results in generally higher yield, vigor, health and resistance towards biotic and abiotic stresses). Such plants are typically made by crossing an inbred male-sterile parent line (the female parent) with another inbred male-fertile parent line (the male parent). Hybrid seed is typically harvested from the male sterile plants and sold to growers. Male sterile plants can sometimes (e.g. in corn) be produced by detasseling, i.e. the mechanical removal of the male reproductive organs (or males flowers) but, more typically, male sterility is the result of genetic determinants in the plant genome. In that case, and especially when seed is the desired product to be harvested from the hybrid plants it is typically useful to ensure that male fertility in the hybrid plants is fully restored. This can be accomplished by ensuring that the male parents have appropriate fertility restorer genes which are capable of restoring the male fertility in hybrid plants that contain the genetic determinants responsible for male-sterility. Genetic determinants for male sterility may be located in the cytoplasm. Examples of cytoplasmic male sterility (CMS) were for instance described in Brassica species. However, genetic determinants for male sterility can also be located in the nuclear genome. Male sterile plants can also be obtained by plant biotechnology methods such as genetic engineering. A particularly useful means of obtaining male-sterile plants is described in WO 89/10396 in which, for example, a ribonuclease such as barnase is selectively expressed in the tapetum cells in the stamens. Fertility can then be restored by expression in the tapetum cells of a ribonuclease inhibitor such as barstar.

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may be treated according to the invention are herbicide-tolerant plants, i.e. plants made tolerant to one or more given herbicides. Such plants can be obtained either by genetic transformation, or by selection of plants containing a mutation imparting such herbicide tolerance.

Herbicide-resistant plants are for example glyphosate-tolerant plants, i.e. plants made tolerant to the herbicide glyphosate or salts thereof. Plants can be made tolerant to glyphosate through different means. For example, glyphosate-tolerant plants can be obtained by transforming the plant with a gene encoding the enzyme 5 -enolpyruvylshikimate-3 -phosphate synthase (EPSPS). Examples of such EPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonella typhimurium (Comai et al., 1983, Science 221, 370-371), the CP4 gene of the bacterium Agrobacterium sp. (Barry et al., 1992, Curr. Topics Plant Physiol. 7, 139-145), the genes encoding a Petunia EPSPS (Shah et al., 1986, Science 233, 478-481), a Tomato EPSPS (Gasser et al., 1988, J. Biol. Chem. 263, 4280-4289), or an Eleusine EPSPS (WO 01/66704). It can also be a mutated EPSPS . Glyphosate-tolerant plants can also be obtained by expressing a gene that encodes a glyphosate oxido-reductase enzyme. Glyphosate-tolerant plants can also be obtained by expressing a gene that encodes a glyphosate acetyl transferase enzyme. Glyphosate- tolerant plants can also be obtained by selecting plants containing naturally-occurring mutations of the above-mentioned genes. Plants expressing EPSPS genes that confer glyphosate tolerance are described. Plants comprising other genes that confer glyphosate tolerance, such as decarboxylase genes, are described.

Other herbicide resistant plants are for example plants that are made tolerant to herbicides inhibiting the enzyme glutamine synthase, such as bialaphos, phosphinothricin or glufosinate. Such plants can be obtained by expressing an enzyme detoxifying the herbicide or a mutant glutamine synthase enzyme that is resistant to inhibition . One such efficient detoxifying enzyme is an enzyme encoding a phosphinothricin acetyltransferase (such as the bar or pat protein from Streptomyces species). Plants expressing an exogenous phosphinothricin acetyltransferase are described.

Further herbicide-tolerant plants are also plants that are made tolerant to the herbicides inhibiting the enzyme hydroxyphenylpyruvatedioxygenase (HPPD). HPPD is an enzyme that catalyzes the reaction in which para-hydroxyphenylpyruvate (HPP) is transformed into homogentisate. Plants tolerant to HPPD- inhibitors can be transformed with a gene encoding a naturally-occurring resistant HPPD enzyme, or a gene encoding a mutated or chimeric HPPD enzyme as described in WO 96/38567, WO 99/24585, WO 99/24586, WO 2009/144079, WO 2002/046387, or US 6,768,044. Tolerance to HPPD -inhibitors can also be obtained by transforming plants with genes encoding certain enzymes enabling the formation of homogentisate despite the inhibition of the native HPPD enzyme by the HPPD-inhibitor. Such plants and genes are described in WO 99/34008 and WO 02/36787. Tolerance of plants to HPPD inhibitors can also be improved by transforming plants with a gene encoding an enzyme having prephenate deshydrogenase (PDH) activity in addition to a gene encoding an HPPD-tolerant enzyme, as described in WO 2004/024928. Further, plants can be made more tolerant to HPPD-inhibitor herbicides by adding into their genome a gene encoding an enzyme capable of metabolizing or degrading HPPD inhibitors, such as the CYP450 enzymes shown in WO 2007/103567 and WO 2008/150473.

Still further herbicide resistant plants are plants that are made tolerant to acetolactate synthase (ALS) inhibitors . Known AL S-inhibitors include , for example, sulfonylurea, imidazolinone , triazolopyrimidines, pryimidinyoxy(thio)benzoates, and/or sulfonylaminocarbonyltriazolinone herbicides. Different mutations in the ALS enzyme (also known as acetohydroxyacid synthase, AHAS) are known to confer tolerance to different herbicides and groups of herbicides, as described for example in Tranel and Wright (2002, Weed Science 50:700-712). The production of sulfonylurea-tolerant plants and imidazolinone-tolerant plants is described. Other imidazolinone-tolerant plants are also described. Further sulfonylurea- and imidazolinone-tolerant plants are also described.

Other plants tolerant to imidazolinone and/or sulfonylurea can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or mutation breeding as described for example for soybeans in U.S. Patent 5,084,082, for rice in WO 97/41218, for sugar beet in U.S. Patent 5,773,702 and WO 99/057965, for lettuce in U.S. Patent 5, 198,599, or for sunflower in WO 01/065922. Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are insect-resistant transgenic plants, i.e. plants made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such insect resistance. An "insect-resistant transgenic plant", as used herein, includes any plant containing at least one transgene comprising a coding sequence encoding:

1) an insecticidal crystal protein from Bacillus thuringiensis or an insecticidal portion thereof, such as the insecticidal crystal proteins listed by Crickmore et al. (1998, Microbiology and Molecular Biology Reviews, 62: 807-813), updated by Crickmore et al. (2005) at the Bacillus thuringiensis toxin nomenclature, online at: http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/), or insecticidal portions thereof, e.g., proteins of the Cry protein classes CrylAb, Cry lAc, CrylB, Cryl C, CrylD, CrylF, Cry2Ab, Cry3Aa, or Cry3Bb or insecticidal portions thereof (e.g. EP 1999141_and WO 2007/107302), or such proteins encoded by synthetic genes as e.g. described in US Patent Application No 12/249,016; or

2) a crystal protein from Bacillus thuringiensis or a portion thereof which is insecticidal in the presence of a second other crystal protein from Bacillus thuringiensis or a portion thereof, such as the binary toxin made up of the Cry34 and Cry35 crystal proteins (Moellenbeck et al. 2001, Nat. Biotechnol. 19: 668-72; Schnepf et al. 2006, Applied Environm. Microbiol. 71, 1765-1774) or the binary toxin made up of the CrylA or CrylF proteins and the Cry2Aa or Cry2Ab or Cry2Ae proteins (US Patent Appl. No. 12/214,022 and EP 08010791.5); or

3) a hybrid insecticidal protein comprising parts of different insecticidal crystal proteins from Bacillus thuringiensis, such as a hybrid of the proteins of 1) above or a hybrid of the proteins of 2) above, e.g., the CrylA.105 protein produced by corn event MON89034 (WO 2007/027777); or 4) a protein of any one of 1) to 3) above wherein some, particularly 1 to 10, amino acids have been replaced by another amino acid to obtain a higher insecticidal activity to a target insect species, and/or to expand the range of target insect species affected, and/or because of changes introduced into the encoding DNA during cloning or transformation, such as the Cry3Bbl protein in corn events MON863 or MON88017, or the Cry3A protein in corn event MIR604; or 5) an insecticidal secreted protein from Bacillus thuringiensis or Bacillus cereus, or an insecticidal portion thereof, such as the vegetative insecticidal (VIP) proteins listed at: http://www.lifesci.sussex.ac.uk/home/Neil Crickmore/Bt/vip.html. e .g . , proteins from the VIP3Aa protein class; or

6) a secreted protein from Bacillus thuringiensis or Bacillus cereus which is insecticidal in the presence of a second secreted protein from Bacillus thuringiensis or B. cereus, such as the binary toxin made up of the VIP1A and VIP2A proteins (WO 94/21795); or

7) a hybrid insecticidal protein comprising parts from different secreted proteins from Bacillus thuringiensis or Bacillus cereus, such as a hybrid of the proteins in 1) above or a hybrid of the proteins in 2) above; or

8) a protein of any one of 5) to 7) above wherein some, particularly 1 to 10, amino acids have been replaced by another amino acid to obtain a higher insecticidal activity to a target insect species, and/or to expand the range of target insect species affected, and/or because of changes introduced into the encoding DNA during cloning or transformation (while still encoding an insecticidal protein), such as the VIP3Aa protein in cotton event COT102; or

9) a secreted protein from Bacillus thuringiensis or Bacillus cereus which is insecticidal in the presence of a crystal protein from Bacillus thuringiensis, such as the binary toxin made up of VIP3 and CrylA or CrylF (US Patent Appl. No. 61/126083 and 61/195019), or the binary toxin made up of the VIP3 protein and the Cry2Aa or Cry2Ab or Cry2Ae proteins (US Patent Appl. No. 12/214,022 and EP 08010791.5).

10) a protein of 9) above wherein some, particularly 1 to 10, amino acids have been replaced by another amino acid to obtain a higher insecticidal activity to a target insect species, and/or to expand the range of target insect species affected, and/or because of changes introduced into the encoding DNA during cloning or transformation (while still encoding an insecticidal protein)

Of course, an insect-resistant transgenic plant, as used herein, also includes any plant comprising a combination of genes encoding the proteins of any one of the above classes 1 to 10. In one embodiment, an insect-resistant plant contains more than one transgene encoding a protein of any one of the above classes 1 to 10, to expand the range of target insect species affected when using different proteins directed at different target insect species, or to delay insect resistance development to the plants by using different proteins insecticidal to the same target insect species but having a different mode of action, such as binding to different receptor binding sites in the insect.

An "insect-resistant transgenic plant", as used herein, further includes any plant containing at least one transgene comprising a sequence producing upon expression a double-stranded RNA which upon ingestion by a plant insect pest inhibits the growth of this insect pest.

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are tolerant to abiotic stresses. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such stress resistance. Particularly useful stress tolerance plants include:

1) plants which contain a transgene capable of reducing the expression and/or the activity of poly(ADP- ribose) polymerase (PARP) gene in the plant cells or plants. 2) plants which contain a stress tolerance enhancing transgene capable of reducing the expression and/or the activity of the PARG encoding genes of the plants or plants cells.

3) plants which contain a stress tolerance enhancing transgene coding for a plant-functional enzyme of the nicotineamide adenine dinucleotide salvage synthesis pathway including nicotinamidase, nicotinate phosphoribosyltransferase, nicotinic acid mononucleotide adenyl transferase, nicotinamide adenine dinucleotide synthetase or nicotine amide phosphorybosyltransferase.

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention show altered quantity, quality and/or storage-stability of the harvested product and/or altered properties of specific ingredients of the harvested product such as : 1) transgenic plants which synthesize a modified starch, which in its physical-chemical characteristics, in particular the amylose content or the amylose/amylopectin ratio, the degree of branching, the average chain length, the side chain distribution, the viscosity behaviour, the gelling strength, the starch grain size and/or the starch grain morphology, is changed in comparison with the synthesised starch in wild type plant cells or plants, so that this is better suited for special applications.

2) transgenic plants which synthesize non starch carbohydrate polymers or which synthesize non starch carbohydrate polymers with altered properties in comparison to wild type plants without genetic modification. Examples are plants producing polyfructose, especially of the inulin and levan-type, plants producing alpha- 1,4-glucans, plants producing alpha- 1,6 branched alpha- 1,4-glucans, plants producing alternan.

3) transgenic plants which produce hyaluronan.

4) transgenic plants or hybrid plants, such as onions with characteristics such as 'high soluble solids content', 'low pungency' (LP) and/or 'long storage' (LS).

Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as cotton plants, with altered fiber characteristics. Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered fiber characteristics and include: a) Plants, such as cotton plants, containing an altered form of cellulose synthase genes.

b) Plants, such as cotton plants, containing an altered form of rsw2 or rsw3 homologous nucleic acids Plants, such as cotton plants, with increased expression of sucrose phosphate synthase.

c) Plants, such as cotton plants, with increased expression of sucrose Plants, such as cotton plants, wherein the timing of the plasmodesmatal gating at the basis of the fiber cell is altered, e.g. through downregulation of fiber-selective -l,3-glucanase.

d) Plants, such as cotton plants, having fibers with altered reactivity, e.g. through the expression of N-acetylglucosaminetransferase gene including nodC and chitin synthase genes.

Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as oilseed rape or related Brassica plants, with altered oil profile characteristics. Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered oil profile characteristics and include: a) Plants, such as oilseed rape plants, producing oil having a high oleic acid content

b) Plants such as oilseed rape plants, producing oil having a low linolenic acid content

c) Plant such as oilseed rape plants, producing oil having a low level of saturated fatty acids Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as potatoes which are virus-resistant, e.g. against potato virus Y (event SY230 and SY233 from Tecnoplant, Argentina), which are disease resistant, e.g. against potato late blight (e.g. RB gene), which show a reduction in cold- induced sweetening ( carrying the Nt-Inhh, IIR-INV gene) or which possess a dwarf phenotype (Gene A-20 oxidase).

Plants or plant cultivars (that can be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as oilseed rape or related Brassica plants, with altered seed shattering characteristics. Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered seed shattering characteristics and include plants such as oilseed rape plants with delayed or reduced seed shattering.

Particularly useful transgenic plants which may be treated according to the invention are plants containing transformation events, or combination of transformation events, that are the subject of petitions for non-regulated status, in the United States of America, to the Animal and Plant Health Inspection Service (APHIS) of the United States Department of Agriculture (USDA) whether such petitions are granted or are still pending. At any time this information is readily available from APHIS (4700 River Road Riverdale , MD 20737, U SA) , for instance on its internet site (URL http://www.aphis.usda.gov/brs/not_reg.html). On the filing date of this application the petitions for nonregulated status that were pending with APHIS or granted by APHIS were those containing the following information:

Petition: the identification number of the petition. Technical descriptions of the transformation events can be found in the individual petition documents which are obtainable from APHIS, for example on the APHIS website, by reference to this petition number. These descriptions are herein incorporated by reference.

Extension of Petition: reference to a previous petition for which an extension is requested.

Institution: the name of the entity submitting the petition.

Regulated article: the plant species concerned.

Transgenic phenotype: the trait conferred to the plants by the transformation event.

Transformation event or line: the name of the event or events (sometimes also designated as lines or lines) for which nonregulated status is requested.

APHIS documents: various documents published by APHIS in relation to the Petition and which can be requested with APHIS.

Additional particularly useful plants containing single transformation events or combinations of transformation events are listed for example in the databases from various national or regional regulatory agencies (see for example http://gmoinfo.jrc.it/gmp_browse.aspx and http://cera- gmc.org/index.php?evidcode=&hstIDXCode=&gType=&AbbrCode=&atCode=&stCode=&coIDCode= &action=gm_crop_database&mode=Submit) .

The plants mentioned above can be particularly advantageously treated with the compounds of the present invention at appropriate concentration.

In particular, the follwing conventional or GMO-plants as well as their seeds or their propargation materialcan be treated with the compound according to the invention: cotton, corn, maize, soybean, wheat, barley, oil seed rape, tobacco, banana, vine, rice, cereals, fruits and vegetables (such as aubergine, pome fruit, stone fruit, soft fruit, cucumber, pear, bell pepper, melons, cabbage, potato, apple) and turf.

Further, in a veterinary medicine field, the novel compounds of the present invention can be effectively used against various harmful animal parasites (endo- and ectoparasites), for example, insects and helminths. Examples of such harmful animal parasites include the harmful organisms as follows. As insects, there are for example, Gasterophilus spp., Stomoxys spp., Trichodectes spp., Rhodnius spp., Ctenocephalides canis, Cimx lectularius, Ctenocephalides felis, Lucilia cuprina and the like. As Acarina, there are for example, Ornithodoros spp., Ixodes spp., Boophilus spp. and the like.

In a field of veterinary, i.e., in a veterinary medicine field, the active compounds of the present invention show an activity against parasites, in particular endoparasites and ectoparasites . The term "endoparasites" especially include helminths such as tapeworms, nematodes, and trematodes and protozoas such as coccidian. Ectoparasites include, typically and also preferably, arthropods, in particular, insects such as fly (biting fly and sucking fly), larva of parasitic fly, louse, pubic louse, bird louse, and flea, and mites of Acarina such as hard tick or soft tick, sarcoptic mite, chigger mite and bird mite.

These parasites include the followings. As Anoplurida, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp. and Solenopotes spp ., and specific examples thereof include Linognathus setosus, Linognathus vituli, Linognathus ovillus, Linognathus oviformis, Linognathus pedalis, Linognathus stenopsis, Haematopinus asini macrocephalus, Haematopinus eurysternus, Haematopinus suis, Pediculus humanus capitis, Pediculus humanus corporis, Phylloera vastatrix, Phthirus pubis and Solenopotes capillatus are included.

As Mallophagida, Amblycerina and Ischnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Wemeckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp. and Felicola spp., and specific examples include Bovicola bovis, Bovicola ovis, Bovicola limbata, Damalina bovis, Trichodectes canis, Felicola subrostratus, Bovicola caprae, Lepikentron ovis) and Wemeckiella equi are included.

As Diptera, Nematocerina and Brachycerina, for example, Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Odagmia spp., Wilhelmia spp., Hybomitora spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.) and Rhinoestrus spp., Tipula spp. and specific examples include Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles gambiae, Anopheles maculipennis, Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Fannia canicularis, Sarcophaga carnaria, Stomoxys calcitrans, Tipula paludosa, Lucilia cuprina, Lucilia sericata, Simulium reptans, Phlebotomus papatasi, Phlebotomus longipalpis, Odagmia omata, Wilhelmia equina, Boophthora erythrocephala, Tabanus bromius, Tabanus spodopterus, Tabanus atratus, Tabanus sudeticus, Hybomitra ciurea, Chrysops caecutiens, Chrysops relictus, Haematopota pluvialis, Haematopota italica, Musca autumnalis, Musca domestica, Haematobia irritans irritans, Haematobia irritans exigua, Haematobia stimulans, Hydrotaea irritans, Hydrotaea albipuncta, Chrysomya chloropyga, Chrysomya bezziana, Oestrus ovis, Hypoderma bovis, Hypoderma lineatum, Przhevalskiana silenus, Dermatobia hominis, Melphagus ovinus, Lipoptena capreoli, Lipoptena cervi, Hippobosca variegata, Hippobosca equina, Gasterophilus intestinalis, Gasterophilus haemorroidalis, Gasterophilus inermis, Gasterophilus nasalis, Gasterophilus nigricomis), Gasterophilus pecorum) and Braulra coeca are included.

As Siphonapterida, for example, Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp. and Ceratophyllus spp., and specific examples include Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans and Xenopsylla cheopsis are included.

As Heteropterida, for example, Cimex spp., Triatoma spp., Rhodnius spp. and Panstrongylus spp are included. As Blattarida, for example, Blatta orientalis, Periplaneta americana, Blattela germanica) and Supella spp., for example, Supella longipalpa are included.

As Acari (Acarina), and Metastigmata and Mesostigmata, for example, Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Dermanyssus spp., Rhipicephalus spp.)(original genus of heteroxenous mites), Ornithonyssus spp., Pneumonyssus spp., Raillietia spp., Stemostoma spp., Varroa spp. and Acarapis spp., and specific examples include Argas persicus, Argas reflexus, Ornithodorus moubata, Otobius megnini, Rhipicephalus(Boophilus)microplus, Rhipicephalus(Boophilus)decoloratus, Rhipicephalus(Boophilus)annulatus, Rhipicephalus(Boophilus)calceratus, Hyalomma annatolicum, Hyalomma aegypticum, Hyalomma marginatum, Hyalomma transiens, Rhipicephalus evertsi, Ixodes ricinus, Ixodes hexagonus, Ixodes canisuga, Ixodes pilosus, Ixodes rubicundus, Ixodes scapularis, Ixodes holocyclus, Haemaphysalis concinna, Haemaphysalis punctata, Haemaphysalis cinnabarina, Haemaphysalis otophila, Haemaphysalis leachi, Haemaphysalis longicorni, Dermacentor marginatus, Dermacentor reticulatus, Dermacentor pictus, Dermacentor albipictus, Dermacentor andersoni, Dermacentor variabilis, Hyalomma mauritanicum, Rhipicephalus sanguineus, Rhipicephalus bursa, Rhipicephalus appendiculatus, Rhipicephalus capensis, Rhipicephalus turanicus, Rhipicephalus zambeziensis, Amblyomma americanum, Amblyomma variegatum, Amblyomma maculatum, Amblyomma hebraeum, Amblyomma cajennense, Dermanyssus gallinae, Ornithonyssus bursa, Ornithonyssus sylviarum and Varroa jacobsoni) are included.

As Actinedida (Prostigmata) and Acaridida (Astigmata), for example, Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp.) and Laminosioptes spp., and examples thereof include Cheyletiella yasguri, Cheyletiella blakei, Demodex canis, Demodex bovis, Demodex ovis, Demodex caprae, Demodex equi, Demodex caballi, Demodex suis, Neotrombicula autumnalis, Neotrombicula desaleri, Neoschongastia xerothermobia, Trombicula akamushi, Otodectes cynotis, Notoedres cati, Sarcoptis canis, Sarcoptes bovis, Sarcoptes ovis, Sarcoptes rupicaprae(=S. caprae, Sarcoptes equi, Sarcoptes suis, Psoroptes ovis, Psoroptes cuniculi, Psoroptes equi, Chorioptes bovis, Psoergates ovis, Pneumonyssoidic mange, Pneumonyssoides caninum and Acarapis woodi are included. The active compounds of the present invention are also suitable for controlling arthropods, helminths and protozoas which attack an animal. The animal includes an agricultural livestock like a cow, a sheep, a goat, a horse, a pig, a donkey, a camel, a buffalo, a rabbit, a chicken, a turkey, a duck, a goose, a nursery fish, a honey bee and the like. In addition, the animal also includes a pet (i.e., companion animal) like a dog, a cat, a pet bird, an aquarium fish and the like and an animal known as a test animal like a hamster, a guinea pig, a rat, a mouse and the like.

With the control of these arthropods, helminths and/or protozoas by using the active compounds of the present invention, death ratio of the host animal is reduced, productivity (for obtaining meat, milk, wool, leather, eggs and honey, etc.) and health of the host animal are expected to be improved, and also economically more favorable and convenient breeding of the animal can be achieved.

For example, (when applicable) it is preferable that blood mixing from a host via parasites is inhibited or interrupted. In addition, control of parasite can be useful for inhibiting transfer of infectious factors.

The term "control" used in the present specification in relation to a veterinary field means that the active compounds of the present invention are effective for reducing the occurrence of parasites in the animal infected with each parasite to a harmless level. More specifically, the term "control" used in the present specification means that the active compounds of the present invention are effective for eradicating each parasite or for inhibiting its growth or proliferation.

In general, when used for an animal treatment, the compounds of the present invention can be directly applied. Preferably, the compounds of the present invention are applied as pharmaceutical compositions which may contain vehicles and/or auxiliary agents that are known in the field and pharmaceutically acceptable.

In a veterinary medicine field and livestock farming, the active compounds can be applied (administered) in various known ways, such as via enteral administration in form of a tablet, a capsule, a drink, a syrup, a granule, a paste, a bolus and a feed stuff, or a suppository; via parenteral administration based on injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implant, intranasal administration, etc.; by administration on skin in form of impregnation, liquid impregnation, spray, pouring on, spotting on, washing and powder spray; or with an aid of an molded article containing the active compounds, such as a neck tag, an ear tag, a tail tag, a leg tag, a horse rein, an identification tag, etc. The active compounds also can be prepared as shampoo, an appropriate preparation usable in aerosol, or as an unpressurized spray, for example a pump spray and a sprayer.

When used for livestock, poultry, pet and the like, the active compounds of the present invention can be prepared as a formulation containing them in an amount of 1 to 80 % of weight (for example, powder, wettable preparation (WP), an emulsion, an emulsified concentrate (EC), a flowable, a homogenous solution and a suspension concentrate (SC)), and then can be applied directly or after dilution (for example, 100 to 10,000 times dilution), or they can be also applied as impregnation solution.

When used in a field of veterinary medicine, the active compounds of the present invention can be used in combination with appropriate synergists such as acaricides, pesticides, anti-helminth agents or anti- protozoa agents or with other active compounds.

In the present invention, the compounds which have a pesticidal activity against the harmful pests encompassing all of the above are also referred to as insecticides.

When used as insecticides, the active compounds of the present invention can be prepared in a common preparation form. Such a preparation form may include, for example, a solution, an emulsion, wettable powder, granulated wettable powder, a suspension, powder, a foam, a paste, a tablet, a granule, an aerosol, a natural or synthetic agent impregnated with the active compounds, a microcapsule, a coating agent for seeds, a formulation equipped with a combustion device (the combustion device can be a smoke or fog cartridge, a can or a coil, etc.) and ULV (cold mist, warm mist), and the like. These formulations may be prepared by methods known per se. For example, they can be prepared by mixing the active compounds together with spreading agents, i.e. liquid diluents or carriers; liquefied gas diluents or carriers; solid diluents or carriers, and, optionally, with surfactants i.e. emulsifiers and/or dispersants and/or foam-forming agents.

When water is used as a spreading agent, for example, organic solvents may be used as auxiliary solvents. The liquid diluents or carriers may include, for example, aromatic hydrocarbons (e.g. xylene, toluene, alkylnaphthalene etc.), chlorinated aromatic or chlorinated aliphatic hydrocarbons (e.g. chlorobenzenes, ethylene chlorides, methylene chlorides etc .), aliphatic hydrocarbons (e .g . cyclohexanes) or paraffins (e.g. mineral oil fractions), alcohols (e.g. butanol, glycol and ethers or esters thereof, etc.), ketones (e.g. acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone etc.), strong polar solvents (e.g. dimethylformamide, dimethylsulfoxide etc.), water and the like. The liquefied gas dilution agents or carriers may include those present as gas at atmospheric temperature and by evaporation, for example, butane, propane, nitrogen gas, carbon dioxide, and an aerosol propellant such as halogenated hydrocarbons. Examples of the solid dilution agents include ground natural minerals (for example, kaolins, clay, talc, chalk, quartz, attapulgite, montmorillonite, diatomaceous earth, etc.) and finely-ground synthetic minerals (for example, highly dispersed silicic acid, alumina and silicate, etc.) and the like.

Examples of the solid carriers for granules may include finely pulverized and sifted rocks (for example, calcite, marble, pumice, sepiolite and dolomite, etc.), synthetic granules of inorganic or organic powders, and fine granules of organic materials (for example, sawdust, coconut shells, corn cobs and tobacco stalks, etc.) and the like. Examples of the emulsifiers and/or blowing agents may include nonionic and anionic emulsifiers (for example, polyoxyethylene fatty acid esters, polyoxyethylene fatty acid alcohol ethers (for example, alkylaryl polyglycol ether), alkyl sulfonates, alkyl sulfates and aryl sulfonates), and albumin hydrolysates and the like. Examples of the dispersants include lignin sulfite waste liquor and methylcellulose. Fixing agents may also be used in the formulation (powder, granule and emulsion). Examples of the fixing agents may include carboxymethyl cellulose, natural or synthetic polymers (for example, gum arabic, polyvinyl alcohol and polyvinyl acetate, etc.). Colorants may also be used. Examples of the colorants may include inorganic pigments (for example, iron oxide, titanium oxide and Prussian blue, etc .), organic dyes (for example, Alizarin dyes, azo dyes or metal phthalocyanine dyes), and further, trace elements such as salts of iron, manganese, boron, copper, cobalt, molybdenum or zinc. In general, the formulation may include the above active components in an amount of 0.1 to 95% by weight, preferably 0.5 to 90% by weight.

The active compounds represented by the Formula (I) of the present invention can be provided as mixtures with other active compounds such as pesticides, poison baits, sterilizing agents, acaricidal agents, nematocides, fungicides, growth regulating agents, and herbicides in a form of commercially useful Formulation or an application form modified from Formulation thereof. Herein, examples of the insecticide include organic phosphorus agents, carbamate agents, carboxylate agents, chlorinated hydrocarbon agents, neonicotinoide insecticides and insecticidal substances produced from organisms.

The active ingredients specified herein by their "common name" are known and described, for example, in the Pesticide Manual ("The Pesticide Manual", 14th Ed., British Crop Protection Council 2006) or can be searched in the internet (e.g. http://www.alanwood.net/pesticides).

( 1) Acetylcholinesterase (AChE) inhibitors, for example carbamates, e.g. Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC, and Xylylcarb; or organophosphates, e.g. Acephate, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Cadusafos, Chlorethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos/DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Disulfoton, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Heptenophos, Imicyafos, Isofenphos, Isopropyl 0-(methoxyaminothio- phosphoryl) salicylate, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion, Parathion-methyl, Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimiphos-methyl, Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Triclorfon, and Vamidothion. (2) GABA-gated chloride channel antagonists, for example cyclodiene organochlorines, e.g. Chlordane and Endosulfan; or phenylpyrazoles (fiproles), e.g. Ethiprole and Fipronil.

(3) Sodium channel modulators / voltage-dependent sodium channel blockers, for example pyrethroids, e.g. Acrinathrin, Allethrin, d-cis-trans Allethrin, d-trans Allethrin, Bifenthrin, Bioallethrin, Bioallethrin S-cyclopentenyl isomer, Bioresmethrin, Cycloprothrin, Cyfluthrin, beta-Cyfluthrin, Cyhalothrin, lambda-Cyhalothrin, gamma-Cyhalothrin, Cypermethrin, alpha-Cypermethrin, beta-Cypermethrin, theta-Cypermethrin, zeta-Cypermethrin, Cyphenothrin [(lR)-trans isomers], Deltamethrin, Empenthrin [(EZ)-(IR) isomers), Esfen valerate, Etofenprox, Fenpropathrin, Fenvalerate, Flucythrinate, Flumethrin, tau-Fluvalinate, Halfenprox, Imiprothrin, Kadethrin, Permethrin, Phenothrin [( lR)-trans isomer), Prallethrin, Pyrethrine (pyrethrum), Resmethrin, Silafluofen, Tefluthrin, Tetramethrin, Tetramethrin [(1R) isomers)], Tralomethrin, and Transfluthrin; or DDT; or Methoxychlor.

(4) Nicotinic acetylcholine receptor (nAChR) agonists, for example neonicotinoids, e.g. Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Thiacloprid, and Thiamethoxam; or Nicotine.

(5) Nicotinic acetylcholine receptor (nAChR) allosteric activators, for example spinosyns, e.g. Spinetoram and Spinosad.

(6) Chloride channel activators, for example avermectins/milbemycins, e.g. Abamectin, Emamectin benzoate, Lepimectin, and Milbemectin.

(7) Juvenile hormone mimics, for example juvenile hormon analogues, e.g. Hydroprene, Kinoprene, and Methoprene; or Fenoxycarb; or Pyriproxyfen. (8) Miscellaneous non-specific (multi-site) inhibitors, for example alkyl halides, e.g. Methyl bromide and other alkyl halides; or Chloropicrin; or Sulfuryl fluoride; or Borax; or Tartar emetic.

(9) Selective homopteran feeding blockers, e.g. Pymetrozine; or Flonicamid.

(10) Mite growth inhibitors, e.g. Clofentezine, Hexythiazox, and Diflovidazin; or Etoxazole.

(11) Microbial disrupters of insect midgut membranes, e.g. Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, and BT crop proteins: CrylAb, CrylAc, CrylFa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Abl .

(12) Inhibitors of mitochondrial ATP synthase, for example Diafenthiuron; or organotin miticides, e.g. Azocyclotin, Cyhexatin, and Fenbutatin oxide; or Propargite; or Tetradifon.

( 13) Uncouplers of oxidative phoshorylation via disruption of the proton gradient, for example Chlorfenapyr, DNOC, and Sulfluramid.

( 14) Nicotinic acetylcholine receptor (nAChR) channel blockers, for example Bensultap, Cartap hydrochloride, Thiocyclam, and Thiosultap-sodium.

(15) Inhibitors of chitin biosynthesis, type 0, for example Bistrifluron, Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Teflubenzuron, and Triflumuron.

(16) Inhibitors of chitin biosynthesis, type 1, for example Buprofezin.

(17) Moulting disrupters, for example Cyromazine.

(18) Ecdysone receptor agonists, for example Chromafenozide, Halofenozide, Methoxyfenozide, and Tebufenozide.

(19) Octopamine receptor agonists, for example Amitraz.

(20) Mitochondrial complex III electron transport inhibitors, for example Hydramethylnon; or Acequinocyl; or Fluacrypyrim.

(21) Mitochondrial complex I electron transport inhibitors, for example METI acaricides, e .g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, and Tolfenpyrad; or Rotenone

(Derris).

(22) Voltage-dependent sodium channel blockers, e.g. Indoxacarb; or Metaflumizone.

(23) Inhibitors of acetyl CoA carboxylase, for example tetronic and tetramic acid derivatives, e.g. Spirodiclofen, Spiromesifen, and Spirotetramat. (24) Mitochondrial complex IV electron transport inhibitors, for example phosphines, e.g. Aluminium phosphide, Calcium phosphide, Phosphine, and Zinc phosphide; or Cyanide.

(25) Mitochondrial complex II electron transport inhibitors, for example Cyenopyrafen.

(28) Ryanodine receptor modulators, for example diamides, e.g. Chlorantraniliprole and Flubendiamide.

Further active ingredients with unknown or uncertain mode of action, for example Amidoflumet, Azadirachtin, Benclothiaz, Benzoximate, Bifenazate, Bromopropylate, Chinomethionat, Cryolite, Cyantraniliprole (Cyazypyr), Cyflumetofen, Dicofol, Diflovidazin, Fluensulfone, Flufenerim, Flufiprole, Fluopyram, Fufenozide, Imidaclothiz, Iprodione, Meperfluthrin, Pyridalyl, Pyrifluquinazon, Tetramethylfluthrin, and iodomethane; furthermore products based on Bacillus firmus (including but not limited to strain CNCM 1-1582, such as, for example,VOTiVO™, BioNem) or one of the following known active compounds : 3-bromo-N-{2-bromo-4-chloro-6-[( 1 -cyclopropylethyl)carbamoyl]phenyl} - 1 - (3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamide (known from WO2005/077934), 4-{[(6- bromopyridin-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one (known from WO2007/115644), 4- {[(6-fluoropyridin-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-o n e ( k n o w n f r o m WO2007/115644), 4-{[(2-chloro-l,3-thiazol-5-yl)memyl](2-fluoroemyl)amino}furan-2(5H)-one (known from WO2007/115644), 4-{[(6-chloφyridin-3-yl)memyl](2-fluoroe1hyl)amino}furan-2(5H)-one (known f r o m W O 2 0 0 7 / 1 1 5 6 4 4 ) , F l u p y r a d i f u r o n e , 4-{[(6-chlor-5-fluoropyridin-3- yl)methyl](methyl)amino}furan-2(5H)-one (known from WO2007/115643), 4-{[(5,6-dichloropyridin-3- yl)methyl](2-fluoroethyl)amino}furan-2(5H)-one (known from WO2007/115646), 4-{[(6-chloro-5- fluoropyridin-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-one (known from WO2007/ 1 15643), 4- {[(6-chloropyridin-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-one (known from EP-A-0 539 588), 4- {[(6-chloφyridin-3-yl)methyl](methyl)amino}furan-2(5H)-one (known from EP-A-0 539 588), { [l-(6- chloropyridin-3-yl)ethyl](methyl)oxido- ⁴-sulfanylidene}cyanamide (known from WO2007/149134) and its diastereomers {[(lR)-l-(6-chloropyridin-3-yl)ethyl](methyl)oxido- ⁴-sulfanylidene}cyanamide (A) and {[(lS)-l-(6-chloropyridin-3-yl)ethyl](methyl)oxido- ⁴-sulfanylidene}cyanamide (B) (also known from WO2007/149134) as well as Sulfoxaflor and its diastereomers [(R)-methyl(oxido){(lR)-l- [6-(trifluoromethyl)pyridin-3 -yl] ethyl} - ⁴-sulfanylidene]cyanamide (A 1 ) and [(S)-methyl(oxido) { ( 1 S)- l-[6-(trifluoromethyl)pyridin-3-yl]ethyl}- ⁴-sulfanylidene]cyanamide (A2), referred to as group of diastereomers A (known from WO2010/074747, WO2010/074751), [(R)-methyl(oxido){(lS)-l-[6- (trifluoromethyl)pyridin-3 -yl] ethyl} - ⁴-sulfanylidene] cyanamide (B 1 ) and [(S)-methyl(oxido) { ( 1 R)- 1 - [6-(trifluoromethyl)pyridin-3-yl]ethyl}- ⁴-sulfanylidene]cyanamide (B2), referred to as group of diastereomers B (also known from WO2010/074747, WO2010/074751), and 1 l-(4-chloro-2,6- dimethylphenyl)-12-hydroxy-l,4-dioxa-9-azadispiro[4.2.4.2]tetradec-l 1-en-lO-o n e ( k n o w n fr o m WO2006/089633), 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-l-azaspiro[4.5]dec-3-en-2- one (known from WO2008/06791 1), l-{2-fluoro-4-methyl-5-[(2,2,2-trifluorethyl)sulfinyl]phenyl}-3- (trifluoromethyl)-lH-l,2,4-triazol-5-amine (known from WO2006/043635), [(3S,4aR,12R,12aS, 12bS)- 3-[(cyclopropylcarbonyl)oxy]-6, 12-dihydroxy-4, 12b-dimethyl-l l-oxo-9-(pyridin-3-yl)- 1 ,3 ,4,4a,5 ,6,6a, 12, 12a, 12b-decahydro-2H, 1 lH-benzo [fjpyrano [4,3 -b]chromen-4-yl]methyl

cyclopropanecarboxylate (known from WO2008/066 153 ), 2-cyano-3-(difluoromethoxy)-N,N- dimethylbenzenesulfonamide (known from WO2006/056433), 2-cyano-3-(difluoromethoxy)-N- methylbenzenesulfonamide (known from WO2006/ 100288), 2-cyano-3-(difluoromethoxy)-N- ethylbenzenesulfonamide (known from WO2005/035486), 4-(difluoromethoxy)-N-ethyl-N-methyl-l,2- benzothiazol-3 -amine 1, 1-dioxide (known from WO2007/057407), N-[l-(2,3-dimethylphenyl)-2-(3,5- dimethylphenyl)ethyl]-4,5-dihydro-l,3-thiazol-2-amine (known from WO2008/104503), { l'-[(2E)-3-(4- chlorophenyl)prop-2-en- 1 -yl] -5 -fluorospiro [indole-3 ,4'-piperidin] - 1 (2H)-yl} (2-chloropyridin-4- yl)methanone (known from WO2003/106457), 3-(2,5-dimethylphenyl)-4-hydroxy-8-methoxy-l,8- diazaspiro[4.5]dec-3-en-2-one (known from WO2009/049851), 3-(2,5-dimethylphenyl)-8-methoxy-2- oxo-1, 8-diazaspiro[4.5]dec-3-en-4-yl ethyl carbonate (known from WO2009/049851), 4-(but-2-yn-l- yloxy)-6-(3,5-dimethylpiperidin-l-yl)-5-fluoropyrimidine (known from WO2004/099160), (2,2,3, 3,4,4,5, 5-octafluoropentyl)(3, 3, 3-trifluoropropyl)malononitrile (known from WO2005/063094), (2,2,3, 3,4,4,5, 5-octafluoropentyl)(3,3,4,4,4-pentafluorobutyl)malononitrile (known from WO2005/063094), 8-[2-(cyclopropylmethoxy)-4-(trifluoromethyl)phenoxy]-3-[6-(trifluoromethyl)pyrid- azin-3-yl]-3-azabicyclo[3.2.1]octane (known from WO2007/040280), Flometoquin, PF1364 (CAS- Reg.No. 1204776-60-2) (known from JP2010/018586), 5-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)- 4,5-dihydro-l,2-oxazol-3-yl]-2-(lH-l,2,4-triazol-l-yl)benzonitrile (known from WO2007/075459), 5- [5 -(2-chloropyridin-4-yl)-5 -(trifluoromethyl)-4,5 -dihydro- 1 ,2-oxazol-3 -yl] -2-( 1H- 1 ,2,4-triazol- 1 - yl)benzonitrile (known from WO2007/075459), 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5- dihydro-l,2-oxazol-3-yl]-2-methyl-N-{2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl}benzamide (known from WO2005/085216), 4-{[(6-chloropyridin-3-yl)methyl](cyclopropyl)amino}-l,3-oxazol-2(5H)-one, 4-{[(6-chloropyridin-3-yl)methyl](2,2-difluoroethyl)amino}-l,3-oxazol-2(5H)-o n e , 4-{[(6- chloropyridin-3 -yl)methyl] (ethyl)amino} - 1 ,3 -oxazol-2(5H)-one, 4- { [(6-chloropyridin-3 - yl)methyl](methyl)amino}-l,3-oxazol-2(5H)-one (all known from WO2010/005692), NNI-0711 (known from WO2002/096882), l-acetyl-N-[4-(l,l,l,3,3,3-hexafluoro-2-methoxypropan-2-yl)-3- isobutylphenyl]-N-isobutyryl-3,5-dimethyl-lH-pyrazole-4-c arboxamide (known from WO2002/096882), methyl 2-[2-({[3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazol-5-yl]carbonyl}amino)- 5-chloro-3-methylbenzoyl]-2-methylhydrazinecarboxylate (known from WO2005/085216), methyl 2-[2- ( { [3 -bromo- 1 -(3 -chloropyridin-2-yl)- lH-pyrazol-5 -yljcarbonyl} amino)-5 -cyano-3 -methylbenzoyl] -2- ethylhydrazinecarboxylate (known from WO2005/085216), methyl 2-[2-({[3-bromo-l-(3-chloropyridin- 2-yl)- lH-pyrazol-5 -yljcarbonyl } amino)-5 -cyano-3 -methylbenzoyl] -2-methylhydrazinecarboxylate (known from WO2005/085216), methyl 2-[3,5-dibromo-2-({[3-bromo-l-(3-chloropyridin-2-yl)-lH- pyrazol-5-yl]carbonyl}amino)benzoyl]-l,2-diethylhydrazinecarboxylate (known from WO2005/085216), methyl 2-[3,5-dibromo-2-({ [3-bromo-l -(3-chloropyridin-2-yl)-lH-pyrazol-5- yl]carbonyl}amino)benzoyl]-2-ethylhydrazinecarboxylate (known from WO2005/085216), (5RS,7RS;5RS,7SR)-l-(6-chloro-3-pyridylmethyl)-l,2,3,5,6,7-hexahydro-7-methyl-8-nitro-5- propoxyimidazo[l,2-a]pyridine (known from WO2007/101369), 2-{6-[2-(5-fluoropyridin-3-yl)-l,3- thiazol-5-yl]pyridin-2-yl}pyrimidine (known from WO2010/006713), 2-{6-[2-(pyridin-3-yl)-l,3- thiazol-5-yl]pyridin-2-yl}pyrimidine (known from WO2010/006713), l-(3-chloropyridin-2-yl)-N-[4- cyano-2-methyl-6-(methylcarbamoyl)phenyl] -3 - { [5 -(trifluoromethyl)- lH-tetrazol- 1 -yljmethyl } - 1H- pyrazole-5-carboxamide (known from WO2010/069502), l-(3-chloropyridin-2-yl)-N-[4-cyano-2- methyl-6-(methylcarbamoyl)phenyl] -3 - { [5 -(trifluoromethyl)-2H-tetrazol-2 -yljmethyl } - lH-pyrazole-5 - carboxamide (known from WO2010/069502), N-[2-(tert-butylcarbamoyl)-4-cyano-6-methylphenyl]-l- (3 -chloropyridin-2-yl)-3 - { [5 -(trifluoromethyl)- lH-tetrazol- 1 -yl]methyl } - lH-pyrazole-5 -carboxamide (known from WO 2010/069502 ) , N-[2-(tert-butylcarbamoyl)-4-cyano-6-methylphenyl]-l-(3- chloropyridin-2-yl)-3-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]methyl}-lH-pyrazole-5-carboxamide (known from WO2010/069502), (lE)-N-[(6-chloropyridin-3-yl)methyl]-N'-cyano-N-(2,2- difluoroethyl)ethanimidamide (known from WO2008/009360), N-[2-(5-amino-l,3,4-thiadiazol-2-yl)-4- chloro-6-methylphenyl]-3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazole-5-carboxamide (known from CN102057925), and methyl 2-[3,5-dibromo-2-({ [3-bromo-l-(3-chloropyridin-2-yl)-lH-pyrazol-5- yl]carbonyl}amino)benzoyl]-2-ethyl-l-methylhydrazinecarboxylate (known from WO2011/049233).

Fungicides which can be used in a combination according to the invention are the following:

( 1) Inhibitors of the ergosterol biosynthesis, for example aldimorph, azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, dodemorph, dodemorph acetate, epoxiconazole, etaconazole, fenarimol, fenbuconazole, fenhexamid, fenpropidin, fenpropimorph, fluquinconazole, flurprimidol, flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole, imazalil, imazalil sulfate, imibenconazole, ipconazole, metconazole, myclobutanil, naftifine, nuarimol, oxpoconazole, paclobutrazol, pefurazoate, penconazole, piperalin, prochloraz, propiconazole, prothioconazole, pyributicarb, pyrifenox, quinconazole, simeconazole, spiroxamine, tebuconazole, terbinafine, tetraconazole, triadimefon, triadimenol, tridemorph, triflumizole, triforine, triticonazole, uniconazole, uniconazole-p, viniconazole, voriconazole, l-(4- chlorophenyl)-2-( 1H- 1 ,2,4-triazol- 1 -yl)cycloheptanol, methyl 1 -(2,2-dimethyl-2,3 -dihydro- lH-inden- 1 - yl)-lH-imidazole-5-c a r b o x y l a t e , N '-{5-(difluoromethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]- phenyl}-N-ethyl-N-methylimidoformamide, N-ethyl-N-methyl-N'-{2-methyl-5-(trifluoromethyl)-4-[3- (trimethylsilyl)propoxy]phenyl}imidoformamide and 0-[l-(4-methoxyphenoxy)-3,3-dimethylbutan-2- yl] lH-imidazole-l-carbothioate.

(2) inhibitors of the respiratory chain at complex I or II, for example bixafen, boscalid, carboxin, diflumetorim, fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr, furmecyclox, isopyrazam (mixture of syn-epimeric racemate 1RS,4SR,9RS and anti-epimeric racemate 1RS,4SR,9SR), isopyrazam (anti-epimeric racemate 1RS,4SR,9SR), isopyrazam (anti-epimeric enantiomer 1R,4S,9S), isopyrazam (anti-epimeric enantiomer 1S,4R,9R), isopyrazam (syn epimeric racemate 1RS,4SR,9RS), isopyrazam (syn-epimeric enantiomer 1R,4S,9R), isopyrazam (syn-epimeric enantiomer 1 S,4R,9S), mepronil, oxycarboxin, penflufen, penthiopyrad, sedaxane, thifluzamide, l-methyl-N-[2-(l,l,2,2- tetrafluoroethoxy)phenyl]-3-(trifluoromethyl)-lH-pyrazole-4-c a r b o x a m i d e , 3 -(difluoromethyl)- 1- methyl -N-[2-( 1 , 1 ,2,2-tetrafluoroethoxy)phenyl] - 1 H-pyrazole-4-carboxamide, 3 -(difluoromethyl)-N-[4- fluoro-2-( 1 , 1 ,2,3 ,3 ,3 -hexafluoropropoxy)phenyl] - 1 -methyl- lH-pyrazole-4-c arb o x am i d e , N-[ 1 -(2,4- dichlorophenyl)- 1 -methoxypropan-2-yl]-3 -(difluoromethyl)- 1 -methyl- lH-pyrazole-4-carboxamide, 5,8- difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine, N- [9-(dichloromethylene)- 1 ,2,3 ,4-tetrahydro- 1 ,4-methanonaphthalen-5 -yl] -3 -(difluoromethyl)- 1 -methyl- lH-pyrazole-4-carboxamide, N-[( 1 S,4R)-9-(dichloromethylene)- 1 ,2,3,4-tetrahydro- 1 ,4-methanon- aphthalen-5 -yl] -3-(difluoromethyl)- 1 -methyl- lH-pyrazole-4-carboxamide and N-[( lR,4S)-9- (dichloromethylene)- 1 ,2,3 ,4-tetrahydro- 1 ,4-methanonaphthalen-5 -yl] -3 -(difluoromethyl)- 1 -methyl- 1H- pyrazole-4-carboxamide.

(3) inhibitors of the respiratory chain at complex III, for example ametoctradin, amisulbrom, azoxystrobin, cyazofamid, coumethoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin, famoxadone, fenamidone, fenoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyribencarb, triclopyricarb, trifloxystrobin, (2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4- yl]oxy}phenyl)-2-(methoxyimino)-N-methylethanamide, (2E)-2-(methoxyimino)-N-methyl-2-(2- {[({(lE)-l-[3 -(trifluoromethyl)phenyl] ethylidene} amino)oxy]methyl}phenyl)ethanamide, (2E)-2- (methoxyimino)-N-methyl-2-{2-[(E)-({ l-[3-(trifluoromethyl)phenyl]ethoxy}imi- no)methyl]phenyl}ethana m i d e , ( 2 E )-2-{2-[({[(lE)-l-(3-{[(E)-l-fluoro-2- phenylethenyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethan- amide, (2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2- (methoxyimino)-N-methylethanamide, 2-chloro-N-( 1 , 1 ,3-trimethyl-2,3-dihydro- lH-inden-4-yl)pyridine- 3-c a r b o x a m i d e , 5-methoxy-2-methyl-4-(2-{[({(lE)-l-[3-(trifluoromethyl)phenyl]ethyl- idene}amino)oxy]methyl}phenyl)-2,4-dihydro-3H-l,2,4-triazol-3-one, methyl (2E)-2-{2-

[({cyclopropyl[(4-methoxyphenyl)imino]methyl}sulfanyl)methyl]phenyl}-3-methoxyprop-2-enoate, N- (3-ethyl-3,5,5-trimethylcyclohexyl)-3-(formylamino)-2-hydroxybenzamide, 2-{2-[(2,5-dimethylphen- oxy)methyl]phenyl}-2-methoxy-N-methylacetamide and (2R)-2-{2-[(2,5-dimethylphen- oxy)methyl]phenyl } -2-methoxy-N-methylacetamide .

(4) Inhibitors of the mitosis and cell division, for example benomyl, carbendazim, chlorfenazole, diethofencarb, ethaboxam, fluopicolide, fuberidazole, pencycuron, thiabendazole, thiophanate-methyl, thiophanate, zoxamide, 5-chloro-7-(4-methylpiperidin-l-yl)-6-(2,4,6-trifluorophenyl)[l,2,4]triazolo[l,5- a]pyrimidine and 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine.

(5) Compounds capable to have a multisite action, for example bordeaux mixture, captafol, captan, chlorothalonil, copper hydroxide, copper naphthenate, copper oxide, copper oxychloride, copper(2+) sulfate, dichlofluanid, dithianon, dodine, dodine free base, ferbam, fluorofolpet, folpet, guazatine, guazatine acetate, iminoctadine, iminoctadine albesilate, iminoctadine triacetate, mancopper, mancozeb, maneb, metiram, metiram zinc, oxine-copper, propamidine, propineb, sulphur and sulphur preparations including calcium polysulphide, thiram, tolylfluanid, zineb and ziram.

(6) Compounds capable to induce a host defence, for example acibenzolar-S-methyl, isotianil, probenazole and tiadinil.

(7) Inhibitors of the amino acid and/or protein biosynthesis, for example andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim, pyrimethanil and 3-(5- fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-l-yl)quinoline.

(8) Inhibitors of the ATP production, for example fentin acetate, fentin chloride, fentin hydroxide and silthiofam. (9) Inhibitors of the cell wall synthesis, for example benthiavalicarb, dimethomorph, flumorph, iprovalicarb, mandipropamid, polyoxins, polyoxorim, validamycin A and valifenalate.

( 10) Inhibitors of the lipid and membrane synthesis, for example biphenyl, chloroneb, dicloran, edifenphos, etridiazole, iodocarb, iprobenfos, isoprothiolane, propamocarb, propamocarb hydrochloride, prothiocarb, pyrazophos, quintozene, tecnazene and tolclofos-methyl. (11) Inhibitors of the melanine biosynthesis, for example carpropamid, diclocymet, fenoxanil, phthalide, pyroquilon, tricyclazole and 2,2,2-trifluoroethyl {3-methyl-l-[(4-methylbenzoyl)amino]butan-2- yl} carbamate.

(12) Inhibitors of the nucleic acid synthesis, for example benalaxyl, benalaxyl-M (kiralaxyl), bupirimate, clozylacon, dimethirimol, ethirimol, furalaxyl, hymexazol, metalaxyl, metalaxyl-M (mefenoxam), ofurace, oxadixyl and oxolinic acid.

(13) Inhibitors of the signal transduction, for example chlozolinate, fenpiclonil, fludioxonil, iprodione, procymidone, quinoxyfen and vinclozolin.

(14) Compounds capable to act as an uncoupler, for example binapacryl, dinocap, ferimzone, fluazinam and meptyldinocap. (15) Further compounds, for example benthiazole, bethoxazin, capsimycin, carvone, chinomethionat, pyriofenone (chlazafenone), cufraneb, cyflufenamid, cymoxanil, cyprosulfamide, dazomet, debacarb, dichlorophen, diclomezine, difenzoquat, difenzoquat methylsulphate, diphenylamine, ecomate, fenpyrazamine, flumetover, fluoroimide, flusulfamide, flutianil, fosetyl-aluminium, fosetyl-calcium, fosetyl-sodium, hexachlorobenzene, irumamycin, methasulfocarb, methyl isothiocyanate, metrafenone, mildiomycin, natamycin, nickel dimethyldithiocarbamate, nitrothal-isopropyl, octhilinone, oxamocarb, oxyfenthiin, pentachlorophenol and salts, phenothrin, phosphorous acid and its salts, propamocarb- fosetylate, propanosine-so dium , p roquinazid , pyrim orph, (2 E)-3-(4-tert-butylphenyl)-3-(2- chloropyridin-4-yl)- 1 -(morpholin-4-yl)prop-2-en- 1 -one, (2Z)-3 -(4-tert-butylphenyl)-3 -(2-chloropyridin- 4^1)-1-^ο ηοϋη-4^1)ρΓορ-2-εη-1-οηε, pyrrolnitrine, tebufloquin, tecloftalam, tolnifanide, triazoxide, trichlamide, zarilamid, (3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2- yl}carbonyl)amino]-6-methyl-4,9-dioxo-l,5-dioxonan-7-y 1 2-methylpropanoate, l-(4-{4-[(5R)-5-(2,6- difluorophenyl)-4,5-dihydro-l,2-oxazol-3-yl]-l,3-thiazol-2-yl}piperidin-l-yl)-2-[5-methyl-3- (trifluoromethyl)- lH-pyrazol- 1 -yl]ethanone, 1 -(4-{4-[(5 S)-5-(2,6-difluorophenyl)-4,5-dihydro- 1 ,2- oxazol-3 -yl] - 1 ,3-thiazol-2-yl}piperidin- 1 -yl)-2- [5 -methyl-3 -(trifluoromethyl)- lH-pyrazol- 1 -yl]ethanone,

1- (4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-l,2-oxazol-3-yl]-l,3-thiazol-2-yl}piperidin-l-yl)-2-[5- methyl-3 -(trifluoromethyl)- lH-pyrazol- 1 -yl] ethanone, 1 -(4-methoxyphenoxy)-3 ,3 -dimethylbutan-2-yl lH-imidazole-l-carboxylate, 2,3,5,6-tetrachloro-4-(methylsulfonyl)pyridine, 2,3-dibutyl-6- chlorothieno[2,3-d]pyrimidin-4(3H)-o n e , 2 , 6-dimethyl-lH,5H-[l,4]dithiino[2,3-c:5,6-c']dipyrrole- l,3,5,7(2H,6H)-tetrone, 2-[5-methyl-3-(trifluoromethyl)-lH-pyrazol-l-yl]-l-(4-{4-[(5R)-5-phenyl-4,5- dihydro- 1 ,2-oxazol-3-yl]- 1 ,3-thiazol-2-yl}piperidin- 1 -yl)ethanone, 2-[5-methyl-3 -(trifluoromethyl)- 1H- pyrazol-l-yl]-l-(4-{4-[(5S)-5-phenyl-4,5-dihydro-l,2-oxazol-3-yl]-l,3-thiazol-2-yl}piperidin-l- yl)ethanone, 2-[5-methyl-3-(trifluoromethyl)-lH-pyrazol-l-yl]-l-{4-[4-(5-phenyl-4,5-dihydro-l,2- oxazol-3-yl)-l,3-thiazol-2-yl]piperidin-l-yl}ethanone, 2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, 2- chloro-5-[2-chloro-l-(2,6-difluoro-4-methoxyphenyl)-4-methyl-lH-imidazol-5-y l ] p y r i d i n e , 2- phenylphenol and salts, 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-l-yl)quinoline, 3,4,5- trichloropyridine-2,6-dicarbonitrile, 3-[5-(4-chlorophenyl)-2,3-dimethyl-l,2-oxazolidin-3-yl]pyridine, 3- chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, 4-(4-chlorophenyl)-5-(2,6- difluorophenyl)-3,6-dimethylpyridazine, 5-amino-l,3,4-thiadiazole-2-th i o 1 , 5-chloro-N'-phenyl-N'- (prop-2-yn- 1 -yl)thiophene-2-sulfonohydrazide, 5 -fluoro-2- [(4-fluorobenzyl)oxy]pyrimidin-4-amine, 5 - fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, 5-methyl-6-octyl[l,2,4]triazolo[l,5-a]pyrimidin-7- amine, ethyl (2Z)-3-amino-2-cyano-3-phenylprop-2-enoate, N'-(4-{[3-(4-chlorobenzyl)-l,2,4-thiadiazol- 5 -yl] oxy } -2,5 -dimethylphenyl)-N-ethyl-N-methylimidoformamide, N-(4-chlorobenzyl)-3 -[3 -methoxy-4- (prop-2-yn-l-yloxy)phenyl]propanamide, N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2- yn-l-yloxy)phenyl]propanamide, N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloropyridine-3- carboxamide, N- [ 1 -(5 -bromo-3 -chloropyridin-2-yl)ethyl] -2,4-dichloropyridine-3 -carboxamide, N-[ 1 -(5 - bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodopyridine-3-c a rb o x a m i d e , N-{(E)-[(cyclopropyl- methoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide, N-{(Z)- [(cyclopropylmemoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide, N'- {4-[(3 -tert-butyl-4-cyano- 1 ,2-thiazol-5 -yl)oxy] -2-chloro-5 -methylphenyl } -N-ethyl-N- m e t h y l i m i d o f o r m a m i d e , N-methyl-2-(l-{[5-methyl-3-(trifluoromethyl)-lH-pyrazol-l- yl]acetyl}piperidin-4-yl)-N-( 1 ,2,3,4-tetrahydronaphthalen- 1 -yl)- 1 ,3-thiazole-4-carboxamide, N-methyl-

2- (l-{[5-methyl-3-(trifluoromethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-yl)-N-[(lR)-l,2,3,4- tetrahydronaphthalen- 1 -yl] - 1 ,3 -thiazole-4-carboxamide , N-methyl-2-( 1 - { [5 -methyl-3 -(trifluoromethyl)- lH-pyrazol- 1 -yl]acetyl}piperidin-4-yl)-N-[( 1 S)- 1 ,2,3,4-tetrahydronaphthalen- 1 -yl]- 1 ,3-thiazole-4- c a r b o x a m i d e , p e n t y l { 6-[({[(l-methyl-lH-tetrazol-5- yl)(phenyl)methylidene]amino} oxy)methyl]pyridin-2-yl} carbamate, phenazine- 1-carboxylic acid, quinolin-8-ol, quinolin-8-ol sulfate (2: 1) and tert-butyl {6-[({[(l-methyl-lH-tetrazol-5- yl)(phenyl)methylene] amino } oxy)methyl] pyridin-2-yl } carbamate . (16) Further compounds, for example l-methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl-2- yl]-lH-pyrazole-4-carboxamide, N-(4'-chlorobiphenyl-2-yl)-3-(difluoromethyl)-l-methyl-lH-pyrazole- 4-carboxamide, N-(2',4'-dichlorobiphenyl-2-yl)-3 -(difluoromethyl)- 1 -methyl- lH-pyrazole-4- carboxamide, 3 -(difluoromethyl)- 1 -methyl-N- [4'-(trifluoromethyl)biphenyl-2-yl] - lH-pyrazole-4- carboxamide, N-(2',5'-difluorobiphenyl-2-yl)-l-methyl-3-(trifluoromethyl)-lH-pyrazole-4-carboxamide, 3-(difluoromethyl)-l-methyl-N-[4'-(prop-l-yn-l-yl)biphenyl-2-yl]-lH-pyrazole-4-c a r b o x am i d e , 5- fluoro- 1 ,3-dimethyl-N-[4'-(prop- 1 -yn- 1 -yl)biphenyl-2-yl]- lH-pyrazole-4 -carboxamide, 2-chloro-N-[4'- (prop- 1 -yn- 1 -yl)biphenyl-2-yl]pyridine-3 -carboxamide, 3 -(difluoromethyl)-N-[4'-(3 ,3 -dimethylbut- 1 - yn- 1 -yl)biphenyl-2-yl] - 1 -methyl- lH-pyrazole-4-carboxamide, N-[4'-(3 ,3 -dimethylbut- 1 -yn- 1 - yl)biphenyl-2-yl]-5-fluoro-l,3-dimethyl-lH-pyrazole-4-carboxamide, 3-(difluoromethyl)-N-(4'- ethynylbiphenyl-2-yl)-l-methyl-lH-pyrazole-4-carboxamide, N-(4'-ethynylbiphenyl-2-yl)-5-fluoro-l,3- dimethyl-lH-pyrazole-4-carboxamide, 2-chloro-N-(4'-ethynylbiphenyl-2-yl)pyridine-3-carboxamide, 2- chloro-N-[4'-(3 ,3 -dimethylbut- 1 -yn- 1 -yl)biphenyl-2-yl]pyridine-3 -c arb oxam i de , 4-(difluoromethyl)-2- methyl-N-[4'-(trifluoromethyl)biphenyl-2-yl]-l,3-thiazole-5-carboxamide, 5-fluoro-N-[4'-(3-hydroxy-3- methylbut-l-yn-l-yl)biphenyl-2-yl]-l,3-dimethyl-lH-pyrazole-4-c a r b o x a m i d e , 2-chloro-N-[4'-(3- hydroxy-3 -methylbut- 1 -yn- 1 -yl)biphenyl-2-yl]pyridine-3 -carb oxami de , 3 -(difluoromethyl)-N-[4'-(3 - methoxy-3 -methylbut- 1 -yn- 1 -yl)biphenyl-2-yl] - 1 -methyl- lH-pyrazole-4-carboxamide, 5 -fluoro-N-[4'- (3 -methoxy-3 -methylbut- 1 -yn- 1 -yl)biphenyl-2-yl] - 1 ,3 -dimethyl- lH-pyrazole-4 -carboxamide, 2-chloro- N-[4'-(3 -methoxy-3 -methylbut- 1 -yn- 1 -yl)biphenyl-2-yl]pyridine-3 -carboxamide, (5 -bromo-2-methoxy- 4-methylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl)methanone, N-[2-(4-{[3-(4-chlorophenyl)prop- 2-yn-l-yl]oxy}-3-methoxyphenyl)ethyl]-N2-( m e t h y l s u l f o n y l ) v a l i n a m i d e , 4-oxo-4-[(2- phenylethyl)amino]butanoic acid and but-3-yn-l-yl {6-[({[(Z)-(l-methyl-lH-tetrazol-5- yl)(phenyl)methylene]amino} oxy)methyl]pyridin-2-yl} carbamate.

All named mixing partners of the classes (1) to (16) can, if their functional groups enable this, optionally form salts with suitable bases or acids.

Herbicidal components which can be used in combination with the active compounds according to the invention in mixed Formulations or in tank mix are, for example, known active compounds as they are described in, for example, Weed Research 26, 441-445 (1986), or "The Pesticide Manual", 15th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2006, and the literature cited therein, and which for example act as inhibitor of acetolactate synthase, acetyl-CoA-carboxylase, cellulose-synthase, enolpyruvylshikimat-3-phosphat-synthase, glutamin-synthetase, p- hydroxyphenylpyruvat-dioxygenase, phytoendesaturase, photosystem I, photosystem II and/or protoporphyrinogen-oxidase.

Examples of active compounds which may be mentioned as herbicides or plant growth regulators which are known from the literature and which can be combined with the compounds according to the invention are the following (compounds are either described by "common name" in accordance with the International Organization for Standardization (ISO) or by chemical name or by a customary code number), and always comprise all applicable forms such as acids, salts, ester, or modifications such as isomers, like stereoisomers and optical isomers. As an example at least one applicable from and/or modifications can be mentioned: acetochlor, acibenzolar, acibenzolar-S-methyl, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, aminocyclopyrachlor, aminocyclopyrachlor-methyl, aminocyclopyrachlor-potassium, aminopyralid, amitrole, ammoniumsulfamat, ancymidol, anilofos, asulam, atrazine, azafenidin, azimsulfuron, aziprotryn, beflubutamid, benazolin, benazolin-ethyl, bencarbazone, benfluralin, benfuresate, bensulide, bensulfuron, bensulfuron-methyl, bentazone, benzfendizone, benzobicyclon, benzofenap, benzofluor, benzoylprop, bicyclopyrone, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromuron, buminafos, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chloramben, chlorazifop, chlorazifop-butyl, chlorbromuron, chlorbufam, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol- methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlormequat-chlorid, chlornitrofen, chlorophthalim, chlorthal-dimethyl, chlorotoluron, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clethodim, clodinafop, clodinafop-propargyl, clofencet, clomazone, clomeprop, cloprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cyclanilide, cycloate, cyclosulfamuron, cycloxydim, cycluron, cyhalofop, cyhalofop-butyl, cyperquat, cyprazine, cyprazole, 2,4-D, 2,4-DB, daimuron/dymron, dalapon, daminozide, dazomet, n-decanol, desmedipham, desmetryn, detosyl-pyrazolate (DTP), diallate, dicamba, dichlobenil, dichlorprop, dichlorprop-P, diclofop, diclofop- methyl, diclofop-P -methyl, diclosulam, diethatyl, diethatyl-ethyl, difenoxuron, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dikegulac-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin, dimetrasulfuron, dinitramine, dinoseb, dinoterb, diphenamid, dipropetryn, diquat, diquat-dibromide, dithiopyr, diuron, DNOC, eglinazine-ethyl, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethephon, ethidimuron, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-5331, i . e . N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-lH-tetrazol-l-yl]-phenyl]- ethansulfonamide, F-7967, i . e . 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-lH-benzimidazol-4-yl]-l- methyl-6-(trifluoromethyl)pyrimidin-2,4(lH,3H)-dione, fenoprop, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fentrazamide, fenuron, flamprop, flamprop-M- isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, fluazolate, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet (thiafluamide), flufenpyr, flufenpyr-ethyl, flumetralin, flumetsulam, flumiclorac, flumiclorac- pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, fluoroglycofen-ethyl, flupoxam, flupropacil, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, flurenol, flurenol- butyl, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flu rimidol, flurtamone, fluthiacet, fluthiacet-methyl, fluthiamide, fomesafen, foramsulfuron, forchlorfenuron, fosamine, furyloxyfen, gibberellinic acid, glufosinate, glufosinate-ammonium, glufosinate-P, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-isopropylammonium, H-9201 , i .e . 0-(2,4-dimethyl-6- nitrophenyl)-0-ethyl-isopropylphosphoramidothioate, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxy fop-methyl, haloxyfop-P -methyl, hexazinone, HW-02, i.e. l-(dimethoxyphosphoryl)-ethyl-(2,4- dichlorophenoxy)acetate, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazosulfuron, inabenfide, indanofan, indaziflam, indol-3-ylacetic acid (IAA), 4-indol-3-ylbutyric acid (IBA), iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron- sodium, ioxynil, ipfencarbazone, isocarbamid, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, KUH-043, i.e. 3-({[5-(difluoromethyl)-l-methyl-3- (trifluoromethyl)-lH-pyrazol-4-yl]methyl}sulphonyl)-5,5-dimethyl-4,5-dihydro-l,2-oxazole, karbutilate, ketospiradox, lactofen, lenacil, linuron, maleic hydrazide, MCPA, MCPB, MCPB-methyl, -ethyl, and - sodium, mecoprop, mecoprop-sodium, mecoprop-butotyl, mecoprop-P-butotyl, mecoprop-P- dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-potas sium , mefenacet, mefluidide, mepiquat-chlorid, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazasulfuron, methazole, methiopyrsulfuron, methiozolin, methoxyphenone, methyldymron, 1-methylcyclopropen, methylisothiocyanat, metobenzuron, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monalide, monocarbamide, monocarbamide-dihydrogensulphate, monolinuron, monosulfuron, monosulfuron ester, monuron, MT-128, i.e. 6-chloro-N-[(2E)-3- chloroprop-2-en-l-yl]-5-methyl-N-phenylpyridazin-3-am i n e , M T-5950, i.e. N-[3-chloro-4-(l- methylethyl)-phenyl]-2-methylpentanamide, NGGC-011, naproanilide, napropamide, naptalam, NC-310, i.e. 4-(2,4-dichlorobenzoyl)-l-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrophenolat-sodium (mixture of isomers), nitrofluorfen, nonanoic acid, norflurazon, orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paclobutrazol, paraquat, paraquat-dichloride, pelargonic acid (nonanoic acid), pendimethalin, pendralin, penoxsulam, pentanochlor, pentoxazone, perfluidone, pethoxamid, phenisopham, phenmedipham, phenmedipham-ethyl, picloram, picolinafen, pinoxaden, piperophos, pirifenop, pirifenop-butyl, pretilachlor, primisulfuron, primisulfuron-methyl, probenazole, profluazol, procyazine, prodiamine, prifluraline, profoxydim, prohexadione, prohexadione-calcium, prohydrojasmone, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfalin, prosulfocarb, prosulfuron, prynachlor, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop -ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, secbumeton, sethoxydim, siduron, simazine, simetryn, SN-106279, i.e. methyl-(2R)-2-({7-[2-chloro-4-(trifluoromethyl)phenoxy]-2-naphthyl}oxy)propanoate, sulcotrione, sulfallate (CDEC), sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosate (glyphosate-trimesium), sulfosulfuron, SW-065, SYN-523, SYP-249, i.e. l-ethoxy-3 -methyl- 1-oxobut- 3-en-2-yl-5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e . l-[7-fluoro-3-oxo-4- (prop-2-yn- 1 -yl)-3 ,4-dihydro-2H- 1 ,4-benzoxazin-6-yl] -3 -propyl-2-thioxoimidazolidin-4,5 -dione, tebutam, tebuthiuron, tecnazene, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton, terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazafluron, thiazopyr, thidiazimin, thidiazuron, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiocarbazil, topramezone, tralkoxydim, triafamone, triallate, triasulfuron, triaziflam, triazofenamide, tribenuron, tribenuron-methyl, trichloroacetic acid (TCA), triclopyr, tridiphane, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifluralin, triflusulfuron, triflusulfuron-methyl, trimeturon, trinexapac, trinexapac-ethyl, tritosulfuron, tsitodef, uniconazole, uniconazole-P, vernolate, ZJ-0862, i.e. 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl } aniline, as we ll as the following compounds:

Further, the active compounds of Formula (I) of the present invention can present in a Formulation or use form as a mixed agent with synergists. Examples of the Formulation or use form are those commercially useful. The synergists per se need not be active but can enhance the activity of the active compounds. The amount of the compounds of the present invention in commercially useful application form may vary over a broad range. The concentration of the active compounds of the Formula (I) of the present invention for actual use may be, for example, between 0.0000001 and 100% by weight, preferably between 0.00001 and 1% by weight. The compounds of the Formula (I) of the present invention can be used according to any common methods suitable for each application form.

Additionally to above mentioned, the present invention further provides Formulations, and application forms prepared from them, as crop protection agents and/or pesticidal agents, such as drench, drip and spray liquors, comprising at least one of the active compounds of the invention. The application forms may comprise further crop protection agents and/or pesticidal agents, and/or activity-enhancing adjuvants such as penetrants, examples being vegetable oils such as, for example, rapeseed oil, sunflower oil, mineral oils such as, for example, liquid paraffins, alkyl esters of vegetable fatty acids, such as rapeseed oil or soybean oil methyl esters, or alkanol alkoxylates, and/or spreaders such as, for example, alkylsiloxanes and/or salts, examples being organic or inorganic ammonium or phosphonium salts, examples being ammonium sulphate or diammonium hydrogen phosphate, and/or retention promoters such as dioctyl sulpho succinate or hydroxypropylguar polymers and/or humectants such as glycerol and/or fertilizers such as ammonium, potassium or phosphorous fertilizers, for example.

Examples of typical Formulations include water-soluble liquids (SL), emulsifiable concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS); these and other possible types of Formulation are described, for example, by Crop Life International and in Pesticide Specifications, Manual on development and use of FAO and WHO specifications for pesticides, FAO Plant Production and Protection Papers - 173, prepared by the FAO/WHO Joint Meeting on Pesticide Specifications, 2004, ISBN: 9251048576. The Formulations may comprise active agrochemical compounds other than one or more active compounds of the invention.

The Formulations or application forms in question preferably comprise auxiliaries, such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, frost protectants, biocides, thickeners and/or other auxiliaries, such as adjuvants, for example. An adjuvant in this context is a component which enhances the biological effect of the Formulation, without the component itself having a biological effect. Examples of adjuvants are agents which promote the retention, spreading, attachment to the leaf surface, or penetration.

These Formulations are produced in a known manner, for example by mixing the active compounds with auxiliaries such as, for example, extenders, solvents and/or solid carriers and/or further auxiliaries, such as, for example, surfactants. The Formulations are prepared either in suitable plants or else before or during the application.

Suitable for use as auxiliaries are substances which are suitable for imparting to the Formulation of the active compound or the application forms prepared from these Formulations (such as, e.g., usable crop protection agents, such as spray liquors or seed dressings) particular properties such as certain physical, technical and/or biological properties.

Suitable extenders are, for example, water, polar and nonpolar organic chemical liquids, for example from the classes of the aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, if appropriate, may also be substituted, etherified and/or esterified), the ketones (such as acetone, cyclohexanone), esters (including fats and oils) and (poly)ethers, the unsubstituted and substituted amines, amides, lactams (such as N- alkylpyrrolidones) and lactones, the sulphones and sulphoxides (such as dimethyl sulphoxide).

If the extender used is water, it is also possible to employ, for example, organic solvents as auxiliary solvents . Essentially, suitable liquid solvents are : aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and also their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulphoxide, and also water.

In principle it is possible to use all suitable solvents. Suitable solvents are, for example, aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes, for example, chlorinated aromatic or aliphatic hydrocarbons, such as chlorobenzene, chloroethylene or methylene chloride, for example, aliphatic hydrocarbons, such as cyclohexane, for example, paraffins, petroleum fractions, mineral and vegetable oils, alcohols, such as methanol, ethanol, isopropanol, butanol or glycol, for example, and also their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, for example, strongly polar solvents, such as dimethyl sulphoxide, and water.

All suitable carriers may in principle be used. Suitable carriers are in particular: for example, ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes and/or solid fertilizers. Mixtures of such carriers may likewise be used. Carriers suitable for granules include the following: for example, crushed and fractionated natural minerals such as calcite, marble, pumice, sepiolite, dolomite, and also synthetic granules of inorganic and organic meals, and also granules of organic material such as sawdust, paper, coconut shells, maize cobs and tobacco stalks.

Liquefied gaseous extenders or solvents may also be used. Particularly suitable are those extenders or carriers which at standard temperature and under standard pressure are gaseous, examples being aerosol propellants, such as halogenated hydrocarbons, and also butane, propane, nitrogen and carbon dioxide.

Examples of emulsifiers and/or foam-formers, dispersants or wetting agents having ionic or nonionic properties, or mixtures of these surface-active substances, are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic esters, taurine derivatives (preferably alkyltaurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols, and derivatives of the compounds containing sulphates, sulphonates and phosphates, examples being alkylaryl polyglycol ethers, alkyl sulphonates, alkyl sulphates, arylsulphonates, protein hydrolysates, lignin-sulphite waste liquors and methylcellulose. The presence of a surface-active substance is advantageous if one of the active compounds and/or one of the inert carriers is not soluble in water and if application takes place in water.

Further auxiliaries that may be present in the Formulations and in the application forms derived from them include colorants such as inorganic pigments, examples being iron oxide, titanium oxide, Prussian Blue, and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and nutrients and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

Stabilizers, such as low-temperature stabilizers, preservatives, antioxidants, light stabilizers or other agents which improve chemical and/or physical stability may also be present. Additionally present may be foam-formers or defoamers. Furthermore, the Formulations and application forms derived from them may also comprise, as additional auxiliaries, stickers such as carboxymethylcellulose, natural and synthetic polymers in powder, granule or latex form, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids. Further possible auxiliaries include mineral and vegetable oils. There may possibly be further auxiliaries present in the Formulations and the application forms derived from them. Examples of such additives include fragrances, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetrants, retention promoters, stabilizers, sequestrants, complexing agents, humectants and spreaders. Generally speaking, the active compounds may be combined with any solid or liquid additive commonly used for Formulation purposes. Suitable retention promoters include all those substances which reduce the dynamic surface tension, such as dioctyl sulphosuccinate, or increase the viscoelasticity, such as hydroxypropylguar polymers, for example. Suitable penetrants in the present context include all those substances which are typically used in order to enhance the penetration of active agrochemical compounds into plants. Penetrants in this context are defined in that, from the (generally aqueous) application liquor and/or from the spray coating, they are able to penetrate the cuticle of the plant and thereby increase the mobility of the active compounds in the cuticle. This property can be determined using the method described in the literature (Baur et al., 1997, Pesticide Science 51, 131-152). Examples include alcohol alkoxylates such as coconut fatty ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters such as rapeseed or soybean oil methyl esters, fatty amine alkoxylates such as tallowamine ethoxylate (15), or ammonium and/or phosphonium salts such as ammonium sulphate or diammonium hydrogen phosphate, for example. The Formulations preferably comprise between 0.00000001% and 98% by weight of active compound or, with particular preference, between 0.01% and 95% by weight of active compound, more preferably between 0.5% and 90% by weight of active compound, based on the weight of the Formulation.

Additionally, to before said, the amount of the compounds of the present invention in commercially useful application form may vary over a broad range. The concentration of the active compounds of the present invention for actual use may be, for example, between 0.0000001 and 100% by weight, preferably between 0.00001 and 1% by weight.

The compounds of the present invention can be used according to any common methods suitable for each application form. The compounds of the invention, when used against hygienically noxious organisms and other noxious organisms that accompany a stored product, have effective stability against alkaline substances present in lime materials. In addition, they have excellent residual efficacies in woods and soils.

Herein below, the present invention is exemplified in view of the following Examples. However, it is not intended for the invention to be limited to the Examples.

[Examples] Synthetic example 1 (synthesis of a reaction material)

Lithium hydride (0.1 g) was added to tetrahydrofuran solution (50 mL) of 2,2,2-trifluoro-l-(3,4,5- trichlorophenyl)ethanone (4.0 g) and l-(3-bromo-4-fluorophenyl) ethanone (1.5 g) followed by reflux under heating for 8 hours. The mixture was diluted with t-butyl methyl ether and washed with sodium hydrogen carbonate solution and brine. The organic layer was dried over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate / hexane) to obtain l-(3-bromo-4-fluorophenyl)-4,4,4-trifluoro-3-(3,4,5- trichlorophenyl)but-2-en- 1 -one (2.6g) .

¹H-NMR(CDCl₃)5:7.23-7.34(4H,m), 7.79-7.82(lH,m), 8.03-8.08(lH,m) Synthetic example 2 (synthesis of a reaction material)

To the acetonitrile solution (50 mL) of l-(3-bromo-4-fluorophenyl)-4,4,4-trifluoro-

3-(3,4,5-trichlorophenyl)bute-2-en-l-one (2.0 g) and nitromethane (0.4 g), diazabicycloundecene (0.7 g) was added and stirred at room temperature for 10 hours. The mixture was diluted with t-butyl methyl ether and washed 3 times with brine. The organic layer was dried over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure . The residue was purified by column chromatography (ethyl acetate / hexane) to obtain l-(3-bromo-4-fluorophenyl)-4,4,4-trifluoro-3- (nitromethyl)-3-(3,4,5-trichlorophenyl)butan-l-one (1.6g).

¹H-NMR(CDC1₃) δ: 4.02(2H, dd), 5.49(2H, dd), 7.25-7.32(3H, m), 7.92-7.95(lH,m), 8.18-8.20(1H, m) Synthetic example 3 (synthesis of the compound of the invention)

Under argon atmosphere, l-(3-bromo-4-fluorophenyl)-4,4,4-trifluoro-3-(nitromethyl)-3-(3,4,5- trichlorophenyl)butan-l-one (0.25 g) and nickel (II) chloride hexahydrate (0.06 g) were dissolved in a mixture solution of methanol (20 mL) and dioxane (4 mL). Under ice cooling, sodium borohydride (0.06 g) was added and the reaction solution was stirred for 1 hour. The mixture was diluted with t-butyl methyl ether and washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure. The residue was purified by column chrom atog raphy (ethyl acetate / hexane ) to o btain 5-(3-bromo-4-fluorophenyl)-3-(3,4,5- trichlorophenyl)-3 -(trifluoromethyl)-3 ,4-dihydro-2H-pyrrole 1 -oxide (0.2g) .

¹H-NMR(CDC1₃) δ: 3.76(2H, dd), 4.77(2H, dd), 7.22(2H, d), 7.39(2H, s), 8.31-8.34(1H, m), 8.60- 8.63(1H, m) Synthetic example 4 (synthesis of the compound of the invention)

Ν,Ν-dimethylformamide solution (20 mL) of 5-(3-bromo-4-fluorophenyl)-

3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrole 1-oxide (0.65 g), lH-l,2,4-triazole (0.1 g), and potassium carbonate (0.2 g) were stirred at 80°C for 3 hours. The mixture was diluted with t-butyl methyl ether and washed 3 times with brine. The organic layer was dried over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate / hexane) to obtain l-{2-bromo-4-[l-oxide-3-(3,4,5- trichlorophenyl)-3 -(trifluoromethyl)-3 ,4-dihydro-2H-pyrrol-5 -yljphenyl} - 1H- 1 ,2,4-triazole (0.5g) . ¹H-NMR(CDC1₃) δ: 3.82(2H, dd), 4.82(2H, dd), 7.41(2H, s), 7.67(1H, d), 8.16( 1H, s), 8.38(1H, dd), 8.62(1H, s), 8.83(1H, d)

Synthetic example 5 (synthesis of the compound of the invention)

Under argon atmosphere, N-dimethylformamide solution (20 mL) of l-{2-bromo-4-[l-oxide-3-(3,4,5- trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]-phenyl}-lH-l,2,4-triazole (0.5 g), zinc cyanide (0.1 g), and tetrakistriphenylphophine palladium (0.05 g) were stirred at 80°C for 4 hours. The mixture was diluted with t-butyl methyl ether and washed 3 times with brine. The organic layer was dried over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate / hexane) to obtain 5-[l-oxide-3-(3,4,5- trichlorophenyl)-3 -(trifluoromethyl)-3 ,4-dihydro-2H-pyrrol-5 -yl-2-( 1H- 1 ,2,4-triazole- 1 -y 1) benzonitrile (0.3g).

¹H-NMR(DMSO-d₆) δ: 4.06 (2H, dd), 4.91(2H, dd), 7.88(2H, s), 8.07(1H, d), 8.40(1H, s), 8.94(2H, d) 9.28(1H, s) Synthetic example 6 (synthesis of reaction material)

Lithium hydride (0.05 g) was added to tetrahydrofuran solution (20 mL) of 2,2,2-trifluoro-l-(3,4,5- trichlorophenyl)ethanone (1.0 g) and (5-acetyl-2,3-dihydro-lH-inden-l-yl) carbamate (0.5 g) followed by reflux under heating for 8 hours. The mixture was diluted with t-butyl methyl ether and washed with saturated sodium hydrogen carbonate solution and brine. The organic layer was dried over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate / hexane) to obtain tert-butyl {5-[4,4,4-trifluoro-3-(3,4,5- trichlorophenyl)but-2-enoyl] -2,3 -dihydro- 1 H-inden- 1 -yl } carbamate . ¹H-NMR(CDC1₃) δ: 1H-NMR(CDC1₃) δ: 1.49(9H, s), 1.71-1.83(1H, m), 2.55-2.59(lH, m), 2.84- 2.90(2H,m), 4.77-5.08(2H,m), 7.21-7.27(2H,m), 7.72(1H, s), 8.05-8.05(3H, m)

Synthetic example 7 (synthesis of reaction material)

To the Ν,Ν-dimethylformamide solution (50 mL) of tert-butyl {5-[4,4,4-trifluoro-3-(3,4,5- trichlorophenyl)but-2-enoyl]-2,3-dihydro-lH-inden-l-yl}carbamate (2.0 g) and nitromethane (0.45 g), diazabicycloundecene (0.6 g) was added, and stirred at a room temperature for 10 hours. The mixture was diluted with t-butyl methyl ether and washed 3 times with brine. The organic layer was dried over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate / hexane) to obtain tert-butyl {5-[4,4,4-trifluoro-3- (nitromethyl)-3-(3,4,5-trichlorophenyl)-butanoyl]-2,3-dihydro-lH-inden-l-yl}carbamate (1.0g).

¹H-NMR(CDC1₃) δ: 1H-NMR(CDC1₃) δ: 1.50(9H, s), 1.85-1.93(1H, m), 2.64-2.67(lH, m), 2.90- 3.02(2H, m), 4.06(2H, dd), 4.77-4.81(lH, m), 5.23-5.26(lH, m), 5.53(2H, dd), 7.33(2H, s), 7.46(1H, d), 7.82-7.85(2H, m) Synthetic example 8 (synthesis of the compound of the invention)

Under argon atmosphere, tert-butyl {5-[4,4,4-trifluoro-3-(nitromethyl)-3-(3,4,5-trichlorophenyl)- butanoyl]-2,3-dihydro-lH-inden-l-yl}carbamate ( 1.0 g) and nickel (II) chloride hexahydrate (0.2 g) were dissolved in a mixture solution of methanol (20 mL) and dioxane (4 mL). Under ice cooling, sodium borohydride (0.2 g) was added and the reaction solution was stirred for 1 hour. The mixture was diluted with t-butyl methyl ether and washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate / hexane) to obtain tert-butyl {5-[l-oxide-3-(3,4,5- trichlorophenyl)-3 -(trifluoromethyl)-3 ,4-dihydro-2H-pyrrol-5 -yl] -2,3 -dihydro- lH-inden- 1 -yl} carbamate (0.66g).

¹H-NMR(CDC1₃) δ: 1.50(9H,s), 1.80-1.83(1H, m), 2.60-2.63(lH, m), 2.83-3.00(2H, m), 3.78(2H, dd), 4.76(3H,dd), 5.21(1H, brs), 7.41-7.43(3H, m), 8.01-8.06(1H, m), 8.36(1H, d)

Synthetic example 9 (synthesis of the compound of the invention)

Tert-buty 1 { 5-[l-oxide-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl]-2,3- dihydro-lH-inden-l-yl} carbamate (0.5 g) was dissolved in methylene chloride (20 mL), and then added with trifluoroacetic acid (1.5 g). After stirring at a room temperature for 3 hours, the solvent was distilled off under reduced pressure and the residues were dissolved in t-butyl methyl ether. After washing with a saturated aqueous solution of sodium hydrogen carbonate and a brine, the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residues were dissolved in tetrahydrofuran (10 mL), added with propionic anhydride (0.13 g) and pyridine (0.7 g), and stirred at a room temperature for 3 hours. The mixture was diluted with t-butyl methyl ether and washed with brine. The organic layer was dried over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate / hexane) to obtain N-{5-[l-oxide-3-(3,4,5-trichlorophenyl) -3-(trifluoromethyl)-3,4- dihydro-2H-pyrrol-5 -yl] -2,3 -dihydro- 1 H-inden- 1 -yl } propaneamide .

^!H-NMRtacetone-de) δ: 1.80(3H, t), 1.79-1.85(1H, m), 2.21(2H, q), 2.43-2.48(lH, m), 2.83-2.90(2H, m), 4.04(2H, dd), 4.87(2H, dd), 5.42-5.44(lH, m), 7.29-7.37(2H, m), 7.80(2H, s), 8.23-8.35(2H, m)

The compounds obtained by the method in the same manner as the above Synthetic example are listed in the following table. Among the compounds of the above Synthetic example, the compounds of the present invention are also described in the following tables.

If in Table 1 in the last column (Z)_k stands for H, this means that the respective heterocycle is not substituted i.e. k is 0).

Table

Ex. No. X¹ B X² R A¹ A² A⁴ G (Z)_k

1-1 CI C-H CI CF₃ C-H C-H C-H F -

1-2 CI C-H CI CF₃ C-H C-H C-H Gl H

1-3 CI C-H CI CF₃ C-H C-H C-H G2 H

1-4 CI C-H CI CF₃ C-H C-H C-H G2 4-F

1-5 CI C-H CI CF₃ C-H C-H C-H G2 4-Cl

1-6 CI C-H CI CF₃ C-H C-H C-H G2 4-Br

1-7 CI C-H CI CF₃ C-H C-H C-H G2 4-CN

1-8 CI C-H CI CF₃ C-H C-H C-H G2 4-NG-2

1-9 CI C-H CI CF₃ C-H C-H C-H G3 H

1-10 CI C-H CI CF₃ C-H C-H C-H G4 H

1-11 CI C-H CI CF₃ C-H C-H C-H G5 H Ex. No. X¹ B X² R A¹ A² A⁴ G (Z)_k

1-12 CI C-H CI CF₃ C-H C-H C-H G6 H

1-13 CI C-H CI CF₃ C-H C-H C-H G7 H

1-14 CI C-H CI CF₃ C-H C-H C-H G8 H

1-15 CI C-H CI CF₃ C-H C-H C-H G9 H

1-16 CI C-H CI CF₃ C-H C-H C-H F -

1-17 CI C-H CI CF₃ C-H C-H C-Cl Gl H

1-18 CI C-H CI CF₃ C-H C-H C-Cl G2 H

1-19 CI C-H CI CF₃ C-H C-H C-Cl G2 4-F

1-20 CI C-H CI CF₃ C-H C-H C-Cl G2 4-Cl

1-21 CI C-H CI CF₃ C-H C-H C-Cl G2 4-Br

1-22 CI C-H CI CF₃ C-H C-H C-Cl G2 4-CN

1-23 CI C-H CI CF₃ C-H C-H C-Cl G2 4-NO2

1-24 CI C-H CI CF₃ C-H C-H C-Cl G3 H

1-25 CI C-H CI CF₃ C-H C-H C-Cl G4 H

1-26 CI C-H CI CF₃ C-H C-H C-Cl G5 H

1-27 CI C-H CI CF₃ C-H C-H C-Cl G6 H

1-28 CI C-H CI CF₃ C-H C-H C-Cl G7 H

1-29 CI C-H CI CF₃ C-H C-H C-Cl G8 H

1-30 CI C-H CI CF₃ C-H C-H C-Cl G9 H

1-31 CI C-H CI CF₃ C-H C-H C-Br F -

1-32 CI C-H CI CF₃ C-H C-H C-Br Gl H

1-33 CI C-H CI CF₃ C-H C-H C-Br G2 H

1-34 CI C-H CI CF₃ C-H C-H C-Br G2 4-F

1-35 CI C-H CI CF₃ C-H C-H C-Br G2 4-Cl

1-36 CI C-H CI CF₃ C-H C-H C-Br G2 4-Br

1-37 CI C-H CI CF₃ C-H C-H C-Br G2 4-CN

1-38 CI C-H CI CF₃ C-H C-H C-Br G2 4-NO2

1-39 CI C-H CI CF₃ C-H C-H C-Br G3 H

1-40 CI C-H CI CF₃ C-H C-H C-Br G4 H

1-41 CI C-H CI CF₃ C-H C-H C-Br G5 H

1-42 CI C-H CI CF₃ C-H C-H C-Br G6 H

1-43 CI C-H CI CF₃ C-H C-H C-Br G7 H

1-44 CI C-H CI CF₃ C-H C-H C-Br G8 H

1-45 CI C-H CI CF₃ C-H C-H C-Br G9 H

1-46 CI C-H CI CF₃ C-H C-H C-N0₂ F - Ex. No. X¹ B X² R A¹ A² A⁴ G (Z)_k

1-47 CI C-H CI CF₃ C-H C-H C-N0₂ Gl H

1-48 CI C-H CI CF₃ C-H C-H C-NO2 G2 H

1-49 CI C-H CI CF₃ C-H C-H C-NO2 G2 4-F

1-50 CI C-H CI CF₃ C-H C-H C-NO2 G2 4-Cl

1-51 CI C-H CI CF₃ C-H C-H C-NO2 G2 4-Br

1-52 CI C-H CI CF₃ C-H C-H C-NO2 G2 4-CN

1-53 CI C-H CI CF₃ C-H C-H C-NO2 G2 4-NO2

1-54 CI C-H CI CF₃ C-H C-H C-NO2 G3 H

1-55 CI C-H CI CF₃ C-H C-H C-NO2 G4 H

1-56 CI C-H CI CF₃ C-H C-H C-NO2 G5 H

1-57 CI C-H CI CF₃ C-H C-H C-NO2 G6 H

1-58 CI C-H CI CF₃ C-H C-H C-NO2 G7 H

1-59 CI C-H CI CF₃ C-H C-H C-NO2 G8 H

1-60 CI C-H CI CF₃ C-H C-H C-NO2 G9 H

1-61 CI C-H CI CF₃ C-H C-H C-CN F -

1-62 CI C-H CI CF₃ C-H C-H C-CN Gl H

1-63 CI C-H CI CF₃ C-H C-H C-CN G2 H

1-64 CI C-H CI CF₃ C-H C-H C-CN G2 4-F

1-65 CI C-H CI CF₃ C-H C-H C-CN G2 4-Cl

1-66 CI C-H CI CF₃ C-H C-H C-CN G2 4-Br

1-67 CI C-H CI CF₃ C-H C-H C-CN G2 4-CN

1-68 CI C-H CI CF₃ C-H C-H C-CN G2 4-NO2

1-69 CI C-H CI CF₃ C-H C-H C-CN G3 H

1-70 CI C-H CI CF₃ C-H C-H C-CN G4 H

1-71 CI C-H CI CF₃ C-H C-H C-CN G5 H

1-72 CI C-H CI CF₃ C-H C-H C-CN G6 H

1-73 CI C-H CI CF₃ C-H C-H C-CN G7 H

1-74 CI C-H CI CF₃ C-H C-H C-CN G8 H

1-75 CI C-H CI CF₃ C-H C-H C-CN G9 H

1-76 CF₃ C-H H CF₃ C-H C-H C-H F -

1-77 CF₃ C-H H CF₃ C-H C-H C-H Gl H

1-78 CF₃ C-H H CF₃ C-H C-H C-H G2 H

1-79 CF₃ C-H H CF₃ C-H C-H C-H G2 4-F

1-80 CF₃ C-H H CF₃ C-H C-H C-H G2 4-Cl

1-81 CF₃ C-H H CF₃ C-H C-H C-H G2 4-Br Ex. No. X¹ B X² R A¹ A² A⁴ G (Z)_k

1-82 CF₃ C-H H CF₃ C-H C-H C-H G2 4-CN

1-83 CF₃ C-H H CF₃ C-H C-H C-H G2 4-N0₂

1-84 CF₃ C-H H CF₃ C-H C-H C-H G3 H

1-85 CF₃ C-H H CF₃ C-H C-H C-H G4 H

1-86 CF₃ C-H H CF₃ C-H C-H C-H G5 H

1-87 CF₃ C-H H CF₃ C-H C-H C-H G6 H

1-88 CF₃ C-H H CF₃ C-H C-H C-H G7 H

1-89 CF₃ C-H H CF₃ C-H C-H C-H G8 H

1-90 CF₃ C-H H CF₃ C-H C-H C-H G9 H

1-91 CF₃ C-H H CF₃ C-H C-H C-H F -

1-92 CF₃ C-H H CF₃ C-H C-H C-Cl Gl H

1-93 CF₃ C-H H CF₃ C-H C-H C-Cl G2 H

1-94 CF₃ C-H H CF₃ C-H C-H C-Cl G2 4-F

1-95 CF₃ C-H H CF₃ C-H C-H C-Cl G2 4-Cl

1-96 CF₃ C-H H CF₃ C-H C-H C-Cl G2 4-Br

1-97 CF₃ C-H H CF₃ C-H C-H C-Cl G2 4-CN

1-98 CF₃ C-H H CF₃ C-H C-H C-Cl G2 4-NO2

1-99 CF₃ C-H H CF₃ C-H C-H C-Cl G3 H

1-100 CF₃ C-H H CF₃ C-H C-H C-Cl G4 H

1-101 CF₃ C-H H CF₃ C-H C-H C-Cl G5 H

1-102 CF₃ C-H H CF₃ C-H C-H C-Cl G6 H

1-103 CF₃ C-H H CF₃ C-H C-H C-Cl G7 H

1-104 CF₃ C-H H CF₃ C-H C-H C-Cl G8 H

1-105 CF₃ C-H H CF₃ C-H C-H C-Cl G9 H

1-106 CF₃ C-H H CF₃ C-H C-H C-Br F -

1-107 CF₃ C-H H CF₃ C-H C-H C-Br Gl H

1-108 CF₃ C-H H CF₃ C-H C-H C-Br G2 H

1-109 CF₃ C-H H CF₃ C-H C-H C-Br G2 4-F

1-110 CF₃ C-H H CF₃ C-H C-H C-Br G2 4-Cl

1-111 CF₃ C-H H CF₃ C-H C-H C-Br G2 4-Br

1-112 CF₃ C-H H CF₃ C-H C-H C-Br G2 4-CN

1-113 CF₃ C-H H CF₃ C-H C-H C-Br G2 4-NO2

1-114 CF₃ C-H H CF₃ C-H C-H C-Br G3 H

1-115 CF₃ C-H H CF₃ C-H C-H C-Br G4 H

1-116 CF₃ C-H H CF₃ C-H C-H C-Br G5 H Ex. No. X¹ B X² R A¹ A² A⁴ G (Z)_k

1-117 CF₃ C-H H CF₃ C-H C-H C-Br G6 H

1-118 CF₃ C-H H CF₃ C-H C-H C-Br G7 H

1-119 CF₃ C-H H CF₃ C-H C-H C-Br G8 H

1-120 CF₃ C-H H CF₃ C-H C-H C-Br G9 H

1-121 CF₃ C-H H CF₃ C-H C-H C-N0₂ F -

1-122 CF₃ C-H H CF₃ C-H C-H C-NO2 Gl H

1-123 CF₃ C-H H CF₃ C-H C-H C-NO2 G2 H

1-124 CF₃ C-H H CF₃ C-H C-H C-NO2 G2 4-F

1-125 CF₃ C-H H CF₃ C-H C-H C-NO2 G2 4-Cl

1-126 CF₃ C-H H CF₃ C-H C-H C-NO2 G2 4-Br

1-127 CF₃ C-H H CF₃ C-H C-H C-NO2 G2 4-CN

1-128 CF₃ C-H H CF₃ C-H C-H C-NO2 G2 4-NO2

1-129 CF₃ C-H H CF₃ C-H C-H C-NO2 G3 H

1-130 CF₃ C-H H CF₃ C-H C-H C-NO2 G4 H

1-131 CF₃ C-H H CF₃ C-H C-H C-NO2 G5 H

1-132 CF₃ C-H H CF₃ C-H C-H C-NO2 G6 H

1-133 CF₃ C-H H CF₃ C-H C-H C-NO2 G7 H

1-134 CF₃ C-H H CF₃ C-H C-H C-NO2 G8 H

1-135 CF₃ C-H H CF₃ C-H C-H C-NO2 G9 H

1-136 CF₃ C-H H CF₃ C-H C-H C-CN F -

1-137 CF₃ C-H H CF₃ C-H C-H C-CN Gl H

1-138 CF₃ C-H H CF₃ C-H C-H C-CN G2 H

1-139 CF₃ C-H H CF₃ C-H C-H C-CN G2 4-F

1-140 CF₃ C-H H CF₃ C-H C-H C-CN G2 4-Cl

1-141 CF₃ C-H H CF₃ C-H C-H C-CN G2 4-Br

1-142 CF₃ C-H H CF₃ C-H C-H C-CN G2 4-CN

1-143 CF₃ C-H H CF₃ C-H C-H C-CN G2 4-NO2

1-144 CF₃ C-H H CF₃ C-H C-H C-CN G3 H

1-145 CF₃ C-H H CF₃ C-H C-H C-CN G4 H

1-146 CF₃ C-H H CF₃ C-H C-H C-CN G5 H

1-147 CF₃ C-H H CF₃ C-H C-H C-CN G6 H

1-148 CF₃ C-H H CF₃ C-H C-H C-CN G7 H

1-149 CF₃ C-H H CF₃ C-H C-H C-CN G8 H

1-150 CF₃ C-H H CF₃ C-H C-H C-CN G9 H

1-151 CF₃ C-H CF₃ CF₃ C-H C-H C-H F - Ex. No. X¹ B X² R A¹ A² A⁴ G (Z)_k

1-152 CF₃ C-H CF₃ CF₃ C-H C-H C-H Gl H

1-153 CF₃ C-H CF₃ CF₃ C-H C-H C-H G2 H

1-154 CF₃ C-H CF₃ CF₃ C-H C-H C-H G2 4-F

1-155 CF₃ C-H CF₃ CF₃ C-H C-H C-H G2 4-Cl

1-156 CF₃ C-H CF₃ CF₃ C-H C-H C-H G2 4-Br

1-157 CF₃ C-H CF₃ CF₃ C-H C-H C-H G2 4-CN

1-158 CF₃ C-H CF₃ CF₃ C-H C-H C-H G2 4-N0₂

1-159 CF₃ C-H CF₃ CF₃ C-H C-H C-H G3 H

1-160 CF₃ C-H CF₃ CF₃ C-H C-H C-H G4 H

1-161 CF₃ C-H CF₃ CF₃ C-H C-H C-H G5 H

1-162 CF₃ C-H CF₃ CF₃ C-H C-H C-H G6 H

1-163 CF₃ C-H CF₃ CF₃ C-H C-H C-H G7 H

1-164 CF₃ C-H CF₃ CF₃ C-H C-H C-H G8 H

1-165 CF₃ C-H CF₃ CF₃ C-H C-H C-H G9 H

1-166 CF₃ C-H CF₃ CF₃ C-H C-H C-H F -

1-167 CF₃ C-H CF₃ CF₃ C-H C-H C-Cl Gl H

1-168 CF₃ C-H CF₃ CF₃ C-H C-H C-Cl G2 H

1-169 CF₃ C-H CF₃ CF₃ C-H C-H C-Cl G2 4-F

1-170 CF₃ C-H CF₃ CF₃ C-H C-H C-Cl G2 4-Cl

1-171 CF₃ C-H CF₃ CF₃ C-H C-H C-Cl G2 4-Br

1-172 CF₃ C-H CF₃ CF₃ C-H C-H C-Cl G2 4-CN

1-173 CF₃ C-H CF₃ CF₃ C-H C-H C-Cl G2 4-NO2

1-174 CF₃ C-H CF₃ CF₃ C-H C-H C-Cl G3 H

1-175 CF₃ C-H CF₃ CF₃ C-H C-H C-Cl G4 H

1-176 CF₃ C-H CF₃ CF₃ C-H C-H C-Cl G5 H

1-177 CF₃ C-H CF₃ CF₃ C-H C-H C-Cl G6 H

1-178 CF₃ C-H CF₃ CF₃ C-H C-H C-Cl G7 H

1-179 CF₃ C-H CF₃ CF₃ C-H C-H C-Cl G8 H

1-180 CF₃ C-H CF₃ CF₃ C-H C-H C-Cl G9 H

1-181 CF₃ C-H CF₃ CF₃ C-H C-H C-Br F -

1-182 CF₃ C-H CF₃ CF₃ C-H C-H C-Br Gl H

1-183 CF₃ C-H CF₃ CF₃ C-H C-H C-Br G2 H

1-184 CF₃ C-H CF₃ CF₃ C-H C-H C-Br G2 4-F

1-185 CF₃ C-H CF₃ CF₃ C-H C-H C-Br G2 4-Cl

1-186 CF₃ C-H CF₃ CF₃ C-H C-H C-Br G2 4-Br Ex. No. X¹ B X² R A¹ A² A⁴ G (Z)_k

1-187 CF₃ C-H CF₃ CF₃ C-H C-H C-Br G2 4-CN

1-188 CF₃ C-H CF₃ CF₃ C-H C-H C-Br G2 4-NO2

1-189 CF₃ C-H CF₃ CF₃ C-H C-H C-Br G3 H

1-190 CF₃ C-H CF₃ CF₃ C-H C-H C-Br G4 H

1-191 CF₃ C-H CF₃ CF₃ C-H C-H C-Br G5 H

1-192 CF₃ C-H CF₃ CF₃ C-H C-H C-Br G6 H

1-193 CF₃ C-H CF₃ CF₃ C-H C-H C-Br G7 H

1-194 CF₃ C-H CF₃ CF₃ C-H C-H C-Br G8 H

1-195 CF₃ C-H CF₃ CF₃ C-H C-H C-Br G9 H

1-196 CF₃ C-H CF₃ CF₃ C-H C-H C-N0₂ F -

1-197 CF₃ C-H CF₃ CF₃ C-H C-H C-NO2 Gl H

1-198 CF₃ C-H CF₃ CF₃ C-H C-H C-NO2 G2 H

1-199 CF₃ C-H CF₃ CF₃ C-H C-H C-NO2 G2 4-F

1-200 CF₃ C-H CF₃ CF₃ C-H C-H C-NO2 G2 4-Cl

1-201 CF₃ C-H CF₃ CF₃ C-H C-H C-NO2 G2 4-Br

1-202 CF₃ C-H CF₃ CF₃ C-H C-H C-NO2 G2 4-CN

1-203 CF₃ C-H CF₃ CF₃ C-H C-H C-NO2 G2 4-NO2

1-204 CF₃ C-H CF₃ CF₃ C-H C-H C-NO2 G3 H

1-205 CF₃ C-H CF₃ CF₃ C-H C-H C-NO2 G4 H

1-206 CF₃ C-H CF₃ CF₃ C-H C-H C-NO2 G5 H

1-207 CF₃ C-H CF₃ CF₃ C-H C-H C-NO2 G6 H

1-208 CF₃ C-H CF₃ CF₃ C-H C-H C-NO2 G7 H

1-209 CF₃ C-H CF₃ CF₃ C-H C-H C-NO2 G8 H

1-210 CF₃ C-H CF₃ CF₃ C-H C-H C-NO2 G9 H

1-211 CF₃ C-H CF₃ CF₃ C-H C-H C-CN F -

1-212 CF₃ C-H CF₃ CF₃ C-H C-H C-CN Gl H

1-213 CF₃ C-H CF₃ CF₃ C-H C-H C-CN G2 H

1-214 CF₃ C-H CF₃ CF₃ C-H C-H C-CN G2 4-F

1-215 CF₃ C-H CF₃ CF₃ C-H C-H C-CN G2 4-Cl

1-216 CF₃ C-H CF₃ CF₃ C-H C-H C-CN G2 4-Br

1-217 CF₃ C-H CF₃ CF₃ C-H C-H C-CN G2 4-CN

1-218 CF₃ C-H CF₃ CF₃ C-H C-H C-CN G2 4-NO2

1-219 CF₃ C-H CF₃ CF₃ C-H C-H C-CN G3 H

1-220 CF₃ C-H CF₃ CF₃ C-H C-H C-CN G4 H

1-221 CF₃ C-H CF₃ CF₃ C-H C-H C-CN G5 H Ex. No. X¹ B X² R A¹ A² A⁴ G (Z)_k

1-222 CF₃ C-H CF₃ CF₃ C-H C-H C-CN G6 H

1-223 CF₃ C-H CF₃ CF₃ C-H C-H C-CN G7 H

1-224 CF₃ C-H CF₃ CF₃ C-H C-H C-CN G8 H

1-225 CF₃ C-H CF₃ CF₃ C-H C-H C-CN G9 H

1-226 Br C-H Br CF₃ C-H C-H C-H F -

1-227 Br C-H Br CF₃ C-H C-H C-H Gl H

1-228 Br C-H Br CF₃ C-H C-H C-H G2 H

1-229 Br C-H Br CF₃ C-H C-H C-H G2 4-F

1-230 Br C-H Br CF₃ C-H C-H C-H G2 4-Cl

1-231 Br C-H Br CF₃ C-H C-H C-H G2 4-Br

1-232 Br C-H Br CF₃ C-H C-H C-H G2 4-CN

1-233 Br C-H Br CF₃ C-H C-H C-H G2 4-N0₂

1-234 Br C-H Br CF₃ C-H C-H C-H G3 H

1-235 Br C-H Br CF₃ C-H C-H C-H G4 H

1-236 Br C-H Br CF₃ C-H C-H C-H G5 H

1-237 Br C-H Br CF₃ C-H C-H C-H G6 H

1-238 Br C-H Br CF₃ C-H C-H C-H G7 H

1-239 Br C-H Br CF₃ C-H C-H C-H G8 H

1-240 Br C-H Br CF₃ C-H C-H C-H G9 H

1-241 Br C-H Br CF₃ C-H C-H C-H F -

1-242 Br C-H Br CF₃ C-H C-H C-Cl Gl H

1-243 Br C-H Br CF₃ C-H C-H C-Cl G2 H

1-244 Br C-H Br CF₃ C-H C-H C-Cl G2 4-F

1-245 Br C-H Br CF₃ C-H C-H C-Cl G2 4-Cl

1-246 Br C-H Br CF₃ C-H C-H C-Cl G2 4-Br

1-247 Br C-H Br CF₃ C-H C-H C-Cl G2 4-CN

1-248 Br C-H Br CF₃ C-H C-H C-Cl G2 4-NO2

1-249 Br C-H Br CF₃ C-H C-H C-Cl G3 H

1-250 Br C-H Br CF₃ C-H C-H C-Cl G4 H

1-251 Br C-H Br CF₃ C-H C-H C-Cl G5 H

1-252 Br C-H Br CF₃ C-H C-H C-Cl G6 H

1-253 Br C-H Br CF₃ C-H C-H C-Cl G7 H

1-254 Br C-H Br CF₃ C-H C-H C-Cl G8 H

1-255 Br C-H Br CF₃ C-H C-H C-Cl G9 H

1-256 Br C-H Br CF₃ C-H C-H C-Br F - Ex. No. X¹ B X² R A¹ A² A⁴ G (Z)_k

1-257 Br C-H Br CF₃ C-H C-H C-Br Gl H

1-258 Br C-H Br CF₃ C-H C-H C-Br G2 H

1-259 Br C-H Br CF₃ C-H C-H C-Br G2 4-F

1-260 Br C-H Br CF₃ C-H C-H C-Br G2 4-Cl

1-261 Br C-H Br CF₃ C-H C-H C-Br G2 4-Br

1-262 Br C-H Br CF₃ C-H C-H C-Br G2 4-CN

1-263 Br C-H Br CF₃ C-H C-H C-Br G2 4-NO2

1-264 Br C-H Br CF₃ C-H C-H C-Br G3 H

1-265 Br C-H Br CF₃ C-H C-H C-Br G4 H

1-266 Br C-H Br CF₃ C-H C-H C-Br G5 H

1-267 Br C-H Br CF₃ C-H C-H C-Br G6 H

1-268 Br C-H Br CF₃ C-H C-H C-Br G7 H

1-269 Br C-H Br CF₃ C-H C-H C-Br G8 H

1-270 Br C-H Br CF₃ C-H C-H C-Br G9 H

1-271 Br C-H Br CF₃ C-H C-H C-N0₂ F -

1-272 Br C-H Br CF₃ C-H C-H C-NO2 Gl H

1-273 Br C-H Br CF₃ C-H C-H C-NO2 G2 H

1-274 Br C-H Br CF₃ C-H C-H C-NO2 G2 4-F

1-275 Br C-H Br CF₃ C-H C-H C-NO2 G2 4-Cl

1-276 Br C-H Br CF₃ C-H C-H C-NO2 G2 4-Br

1-277 Br C-H Br CF₃ C-H C-H C-NO2 G2 4-CN

1-278 Br C-H Br CF₃ C-H C-H C-NO2 G2 4-NO2

1-279 Br C-H Br CF₃ C-H C-H C-NO2 G3 H

1-280 Br C-H Br CF₃ C-H C-H C-NO2 G4 H

1-281 Br C-H Br CF₃ C-H C-H C-NO2 G5 H

1-282 Br C-H Br CF₃ C-H C-H C-NO2 G6 H

1-283 Br C-H Br CF₃ C-H C-H C-NO2 G7 H

1-284 Br C-H Br CF₃ C-H C-H C-NO2 G8 H

1-285 Br C-H Br CF₃ C-H C-H C-NO2 G9 H

1-286 Br C-H Br CF₃ C-H C-H C-CN F -

1-287 Br C-H Br CF₃ C-H C-H C-CN Gl H

1-288 Br C-H Br CF₃ C-H C-H C-CN G2 H

1-289 Br C-H Br CF₃ C-H C-H C-CN G2 4-F

1-290 Br C-H Br CF₃ C-H C-H C-CN G2 4-Cl

1-291 Br C-H Br CF₃ C-H C-H C-CN G2 4-Br Ex. No. X¹ B X² R A¹ A² A⁴ G (Z)_k

1-292 Br C-H Br CF₃ C-H C-H C-CN G2 4-CN

1-293 Br C-H Br CF₃ C-H C-H C-CN G2 4-N0₂

1-294 Br C-H Br CF₃ C-H C-H C-CN G3 H

1-295 Br C-H Br CF₃ C-H C-H C-CN G4 H

1-296 Br C-H Br CF₃ C-H C-H C-CN G5 H

1-297 Br C-H Br CF₃ C-H C-H C-CN G6 H

1-298 Br C-H Br CF₃ C-H C-H C-CN G7 H

1-299 Br C-H Br CF₃ C-H C-H C-CN G8 H

1-300 Br C-H Br CF₃ C-H C-H C-CN G9 H

1-301 CI C-Cl CI CF₃ C-H C-H C-H F -

1-302 CI C-Cl CI CF₃ C-H C-H C-H Gl H

1-303 CI C-Cl CI CF₃ C-H C-H C-H G2 H

1-304 CI C-Cl CI CF₃ C-H C-H C-H G2 4-F

1-305 CI C-Cl CI CF₃ C-H C-H C-H G2 4-Cl

1-306 CI C-Cl CI CF₃ C-H C-H C-H G2 4-Br

1-307 CI C-Cl CI CF₃ C-H C-H C-H G2 4-CN

1-308 CI C-Cl CI CF₃ C-H C-H C-H G2 4-NO2

1-309 CI C-Cl CI CF₃ C-H C-H C-H G3 H

1-310 CI C-Cl CI CF₃ C-H C-H C-H G4 H

1-311 CI C-Cl CI CF₃ C-H C-H C-H G5 H

1-312 CI C-Cl CI CF₃ C-H C-H C-H G6 H

1-313 CI C-Cl CI CF₃ C-H C-H C-H G7 H

1-314 CI C-Cl CI CF₃ C-H C-H C-H G8 H

1-315 CI C-Cl CI CF₃ C-H C-H C-H G9 H

1-316 CI C-Cl CI CF₃ C-H C-H C-H F -

1-317 CI C-Cl CI CF₃ C-H C-H C-Cl Gl H

1-318 CI C-Cl CI CF₃ C-H C-H C-Cl G2 H

1-319 CI C-Cl CI CF₃ C-H C-H C-Cl G2 4-F

1-320 CI C-Cl CI CF₃ C-H C-H C-Cl G2 4-Cl

1-321 CI C-Cl CI CF₃ C-H C-H C-Cl G2 4-Br

1-322 CI C-Cl CI CF₃ C-H C-H C-Cl G2 4-CN

1-323 CI C-Cl CI CF₃ C-H C-H C-Cl G2 4-NO2

1-324 CI C-Cl CI CF₃ C-H C-H C-Cl G3 H

1-325 CI C-Cl CI CF₃ C-H C-H C-Cl G4 H

1-326 CI C-Cl CI CF₃ C-H C-H C-Cl G5 H Ex. No. X¹ B X² R A¹ A² A⁴ G (Z)_k

1-327 CI C-Cl CI CF₃ C-H C-H C-Cl G6 H

1-328 CI C-Cl CI CF₃ C-H C-H C-Cl G7 H

1-329 CI C-Cl CI CF₃ C-H C-H C-Cl G8 H

1-330 CI C-Cl CI CF₃ C-H C-H C-Cl G9 H

1-331 CI C-Cl CI CF₃ C-H C-H C-Br F -

1-332 CI C-Cl CI CF₃ C-H C-H C-Br Gl H

1-333 CI C-Cl CI CF₃ C-H C-H C-Br G2 H

1-334 CI C-Cl CI CF₃ C-H C-H C-Br G2 4-F

1-335 CI C-Cl CI CF₃ C-H C-H C-Br G2 4-Cl

1-336 CI C-Cl CI CF₃ C-H C-H C-Br G2 4-Br

1-337 CI C-Cl CI CF₃ C-H C-H C-Br G2 4-CN

1-338 CI C-Cl CI CF₃ C-H C-H C-Br G2 4-NO2

1-339 CI C-Cl CI CF₃ C-H C-H C-Br G3 H

1-340 CI C-Cl CI CF₃ C-H C-H C-Br G4 H

1-341 CI C-Cl CI CF₃ C-H C-H C-Br G5 H

1-342 CI C-Cl CI CF₃ C-H C-H C-Br G6 H

1-343 CI C-Cl CI CF₃ C-H C-H C-Br G7 H

1-344 CI C-Cl CI CF₃ C-H C-H C-Br G8 H

1-345 CI C-Cl CI CF₃ C-H C-H C-Br G9 H

1-346 CI C-Cl CI CF₃ C-H C-H C-N0₂ F -

1-347 CI C-Cl CI CF₃ C-H C-H C-NO2 Gl H

1-348 CI C-Cl CI CF₃ C-H C-H C-NO2 G2 H

1-349 CI C-Cl CI CF₃ C-H C-H C-NO2 G2 4-F

1-350 CI C-Cl CI CF₃ C-H C-H C-NO2 G2 4-Cl

1-351 CI C-Cl CI CF₃ C-H C-H C-NO2 G2 4-Br

1-352 CI C-Cl CI CF₃ C-H C-H C-NO2 G2 4-CN

1-353 CI C-Cl CI CF₃ C-H C-H C-NO2 G2 4-NO2

1-354 CI C-Cl CI CF₃ C-H C-H C-NO2 G3 H

1-355 CI C-Cl CI CF₃ C-H C-H C-NO2 G4 H

1-356 CI C-Cl CI CF₃ C-H C-H C-NO2 G5 H

1-357 CI C-Cl CI CF₃ C-H C-H C-NO2 G6 H

1-358 CI C-Cl CI CF₃ C-H C-H C-NO2 G7 H

1-359 CI C-Cl CI CF₃ C-H C-H C-NO2 G8 H

1-360 CI C-Cl CI CF₃ C-H C-H C-NO2 G9 H

1-361 CI C-Cl CI CF₃ C-H C-H C-CN F - Ex. No. X¹ B X² R A¹ A² A⁴ G (Z)_k

1-362 CI C-Cl CI CF₃ C-H C-H C-CN Gl H

1-363 CI C-Cl CI CF₃ C-H C-H C-CN G2 H

1-364 CI C-Cl CI CF₃ C-H C-H C-CN G2 4-F

1-365 CI C-Cl CI CF₃ C-H C-H C-CN G2 4-Cl

1-366 CI C-Cl CI CF₃ C-H C-H C-CN G2 4-Br

1-367 CI C-Cl CI CF₃ C-H C-H C-CN G2 4-CN

1-368 CI C-Cl CI CF₃ C-H C-H C-CN G2 4-N0₂

1-369 CI C-Cl CI CF₃ C-H C-H C-CN G3 H

1-370 CI C-Cl CI CF₃ C-H C-H C-CN G4 H

1-371 CI C-Cl CI CF₃ C-H C-H C-CN G5 H

1-372 CI C-Cl CI CF₃ C-H C-H C-CN G6 H

1-373 CI C-Cl CI CF₃ C-H C-H C-CN G7 H

1-374 CI C-Cl CI CF₃ C-H C-H C-CN G8 H

1-375 CI C-Cl CI CF₃ C-H C-H C-CN G9 H

1-376 CI N CI CF₃ C-H C-H C-H F -

1-377 CI N CI CF₃ C-H C-H C-H Gl H

1-378 CI N CI CF₃ C-H C-H C-H G2 H

1-379 CI N CI CF₃ C-H C-H C-H G2 4-F

1-380 CI N CI CF₃ C-H C-H C-H G2 4-Cl

1-381 CI N CI CF₃ C-H C-H C-H G2 4-Br

1-382 CI N CI CF₃ C-H C-H C-H G2 4-CN

1-383 CI N CI CF₃ C-H C-H C-H G2 4-NO2

1-384 CI N CI CF₃ C-H C-H C-H G3 H

1-385 CI N CI CF₃ C-H C-H C-H G4 H

1-386 CI N CI CF₃ C-H C-H C-H G5 H

1-387 CI N CI CF₃ C-H C-H C-H G6 H

1-388 CI N CI CF₃ C-H C-H C-H G7 H

1-389 CI N CI CF₃ C-H C-H C-H G8 H

1-390 CI N CI CF₃ C-H C-H C-H G9 H

1-391 CI N CI CF₃ C-H C-H C-H F -

1-392 CI N CI CF₃ C-H C-H C-Cl Gl H

1-393 CI N CI CF₃ C-H C-H C-Cl G2 H

1-394 CI N CI CF₃ C-H C-H C-Cl G2 4-F

1-395 CI N CI CF₃ C-H C-H C-Cl G2 4-Cl

1-396 CI N CI CF₃ C-H C-H C-Cl G2 4-Br Ex. No. X¹ B X² R A¹ A² A⁴ G (Z)_k

1-397 CI N CI CF₃ C-H C-H C-Cl G2 4-CN

1-398 CI N CI CF₃ C-H C-H C-Cl G2 4-NO2

1-399 CI N CI CF₃ C-H C-H C-Cl G3 H

1-400 CI N CI CF₃ C-H C-H C-Cl G4 H

1-401 CI N CI CF₃ C-H C-H C-Cl G5 H

1-402 CI N CI CF₃ C-H C-H C-Cl G6 H

1-403 CI N CI CF₃ C-H C-H C-Cl G7 H

1-404 CI N CI CF₃ C-H C-H C-Cl G8 H

1-405 CI N CI CF₃ C-H C-H C-Cl G9 H

1-406 CI N CI CF₃ C-H C-H C-Br F -

1-407 CI N CI CF₃ C-H C-H C-Br Gl H

1-408 CI N CI CF₃ C-H C-H C-Br G2 H

1-409 CI N CI CF₃ C-H C-H C-Br G2 4-F

1-410 CI N CI CF₃ C-H C-H C-Br G2 4-Cl

1-411 CI N CI CF₃ C-H C-H C-Br G2 4-Br

1-412 CI N CI CF₃ C-H C-H C-Br G2 4-CN

1-413 CI N CI CF₃ C-H C-H C-Br G2 4-NO2

1-414 CI N CI CF₃ C-H C-H C-Br G3 H

1-415 CI N CI CF₃ C-H C-H C-Br G4 H

1-416 CI N CI CF₃ C-H C-H C-Br G5 H

1-417 CI N CI CF₃ C-H C-H C-Br G6 H

1-418 CI N CI CF₃ C-H C-H C-Br G7 H

1-419 CI N CI CF₃ C-H C-H C-Br G8 H

1-420 CI N CI CF₃ C-H C-H C-Br G9 H

1-421 CI N CI CF₃ C-H C-H C-N0₂ F -

1-422 CI N CI CF₃ C-H C-H C-NO2 Gl H

1-423 CI N CI CF₃ C-H C-H C-NO2 G2 H

1-424 CI N CI CF₃ C-H C-H C-NO2 G2 4-F

1-425 CI N CI CF₃ C-H C-H C-NO2 G2 4-Cl

1-426 CI N CI CF₃ C-H C-H C-NO2 G2 4-Br

1-427 CI N CI CF₃ C-H C-H C-NO2 G2 4-CN

1-428 CI N CI CF₃ C-H C-H C-NO2 G2 4-NO2

1-429 CI N CI CF₃ C-H C-H C-NO2 G3 H

1-430 CI N CI CF₃ C-H C-H C-NO2 G4 H

1-431 CI N CI CF₃ C-H C-H C-NO2 G5 H Ex. No. X¹ B X² R A¹ A² A⁴ G (Z)_k

1-432 CI N CI CF₃ C-H C-H C-N0₂ G6 H

1-433 CI N CI CF₃ C-H C-H C-NO2 G7 H

1-434 CI N CI CF₃ C-H C-H C-NO2 G8 H

1-435 CI N CI CF₃ C-H C-H C-NO2 G9 H

1-436 CI N CI CF₃ C-H C-H C-CN F -

1-437 CI N CI CF₃ C-H C-H C-CN Gl H

1-438 CI N CI CF₃ C-H C-H C-CN G2 H

1-439 CI N CI CF₃ C-H C-H C-CN G2 4-F

1-440 CI N CI CF₃ C-H C-H C-CN G2 4-Cl

1-441 CI N CI CF₃ C-H C-H C-CN G2 4-Br

1-442 CI N CI CF₃ C-H C-H C-CN G2 4-CN

1-443 CI N CI CF₃ C-H C-H C-CN G2 4-NO2

1-444 CI N CI CF₃ C-H C-H C-CN G3 H

1-445 CI N CI CF₃ C-H C-H C-CN G4 H

1-446 CI N CI CF₃ C-H C-H C-CN G5 H

1-447 CI N CI CF₃ C-H C-H C-CN G6 H

1-448 CI N CI CF₃ C-H C-H C-CN G7 H

1-449 CI N CI CF₃ C-H C-H C-CN G8 H

1-450 CI N CI CF₃ C-H C-H C-CN G9 H

1-451 CF₃ N CF₃ CF₃ C-H C-H C-H F -

1-452 CF₃ N CF₃ CF₃ C-H C-H C-H Gl H

1-453 CF₃ N CF₃ CF₃ C-H C-H C-H G2 H

1-454 CF₃ N CF₃ CF₃ C-H C-H C-H G2 4-F

1-455 CF₃ N CF₃ CF₃ C-H C-H C-H G2 4-Cl

1-456 CF₃ N CF₃ CF₃ C-H C-H C-H G2 4-Br

1-457 CF₃ N CF₃ CF₃ C-H C-H C-H G2 4-CN

1-458 CF₃ N CF₃ CF₃ C-H C-H C-H G2 4-NO2

1-459 CF₃ N CF₃ CF₃ C-H C-H C-H G3 H

1-460 CF₃ N CF₃ CF₃ C-H C-H C-H G4 H

1-461 CF₃ N CF₃ CF₃ C-H C-H C-H G5 H

1-462 CF₃ N CF₃ CF₃ C-H C-H C-H G6 H

1-463 CF₃ N CF₃ CF₃ C-H C-H C-H G7 H

1-464 CF₃ N CF₃ CF₃ C-H C-H C-H G8 H

1-465 CF₃ N CF₃ CF₃ C-H C-H C-H G9 H

1-466 CF₃ N CF₃ CF₃ C-H C-H C-H F - Ex. No. X¹ B X² R A¹ A² A⁴ G (Z)_k

1-467 CF₃ N CF₃ CF₃ C-H C-H C-Cl Gl H

1-468 CF₃ N CF₃ CF₃ C-H C-H C-Cl G2 H

1-469 CF₃ N CF₃ CF₃ C-H C-H C-Cl G2 4-F

1-470 CF₃ N CF₃ CF₃ C-H C-H C-Cl G2 4-Cl

1-471 CF₃ N CF₃ CF₃ C-H C-H C-Cl G2 4-Br

1-472 CF₃ N CF₃ CF₃ C-H C-H C-Cl G2 4-CN

1-473 CF₃ N CF₃ CF₃ C-H C-H C-Cl G2 4-NO2

1-474 CF₃ N CF₃ CF₃ C-H C-H C-Cl G3 H

1-475 CF₃ N CF₃ CF₃ C-H C-H C-Cl G4 H

1-476 CF₃ N CF₃ CF₃ C-H C-H C-Cl G5 H

1-477 CF₃ N CF₃ CF₃ C-H C-H C-Cl G6 H

1-478 CF₃ N CF₃ CF₃ C-H C-H C-Cl G7 H

1-479 CF₃ N CF₃ CF₃ C-H C-H C-Cl G8 H

1-480 CF₃ N CF₃ CF₃ C-H C-H C-Cl G9 H

1-481 CF₃ N CF₃ CF₃ C-H C-H C-Br F -

1-482 CF₃ N CF₃ CF₃ C-H C-H C-Br Gl H

1-483 CF₃ N CF₃ CF₃ C-H C-H C-Br G2 H

1-484 CF₃ N CF₃ CF₃ C-H C-H C-Br G2 4-F

1-485 CF₃ N CF₃ CF₃ C-H C-H C-Br G2 4-Cl

1-486 CF₃ N CF₃ CF₃ C-H C-H C-Br G2 4-Br

1-487 CF₃ N CF₃ CF₃ C-H C-H C-Br G2 4-CN

1-488 CF₃ N CF₃ CF₃ C-H C-H C-Br G2 4-NO2

1-489 CF₃ N CF₃ CF₃ C-H C-H C-Br G3 H

1-490 CF₃ N CF₃ CF₃ C-H C-H C-Br G4 H

1-491 CF₃ N CF₃ CF₃ C-H C-H C-Br G5 H

1-492 CF₃ N CF₃ CF₃ C-H C-H C-Br G6 H

1-493 CF₃ N CF₃ CF₃ C-H C-H C-Br G7 H

1-494 CF₃ N CF₃ CF₃ C-H C-H C-Br G8 H

1-495 CF₃ N CF₃ CF₃ C-H C-H C-Br G9 H

1-496 CF₃ N CF₃ CF₃ C-H C-H C-N0₂ F -

1-497 CF₃ N CF₃ CF₃ C-H C-H C-NO2 Gl H

1-498 CF₃ N CF₃ CF₃ C-H C-H C-NO2 G2 H

1-499 CF₃ N CF₃ CF₃ C-H C-H C-NO2 G2 4-F

1-500 CF₃ N CF₃ CF₃ C-H C-H C-NO2 G2 4-Cl

1-501 CF₃ N CF₃ CF₃ C-H C-H C-NO2 G2 4-Br Ex. No. X¹ B X² R A¹ A² A⁴ G (Z)_k

1-502 CF₃ N CF₃ CF₃ C-H C-H C-N0₂ G2 4-CN

1-503 CF₃ N CF₃ CF₃ C-H C-H C-NO2 G2 4-NO2

1-504 CF₃ N CF₃ CF₃ C-H C-H C-NO2 G3 H

1-505 CF₃ N CF₃ CF₃ C-H C-H C-NO2 G4 H

1-506 CF₃ N CF₃ CF₃ C-H C-H C-NO2 G5 H

1-507 CF₃ N CF₃ CF₃ C-H C-H C-NO2 G6 H

1-508 CF₃ N CF₃ CF₃ C-H C-H C-NO2 G7 H

1-509 CF₃ N CF₃ CF₃ C-H C-H C-NO2 G8 H

1-510 CF₃ N CF₃ CF₃ C-H C-H C-NO2 G9 H

1-511 CF₃ N CF₃ CF₃ C-H C-H C-CN F -

1-512 CF₃ N CF₃ CF₃ C-H C-H C-CN Gl H

1-513 CF₃ N CF₃ CF₃ C-H C-H C-CN G2 H

1-514 CF₃ N CF₃ CF₃ C-H C-H C-CN G2 4-F

1-515 CF₃ N CF₃ CF₃ C-H C-H C-CN G2 4-Cl

1-516 CF₃ N CF₃ CF₃ C-H C-H C-CN G2 4-Br

1-517 CF₃ N CF₃ CF₃ C-H C-H C-CN G2 4-CN

1-518 CF₃ N CF₃ CF₃ C-H C-H C-CN G2 4-NO2

1-519 CF₃ N CF₃ CF₃ C-H C-H C-CN G3 H

1-520 CF₃ N CF₃ CF₃ C-H C-H C-CN G4 H

1-521 CF₃ N CF₃ CF₃ C-H C-H C-CN G5 H

1-522 CF₃ N CF₃ CF₃ C-H C-H C-CN G6 H

1-523 CF₃ N CF₃ CF₃ C-H C-H C-CN G7 H

1-524 CF₃ N CF₃ CF₃ C-H C-H C-CN G8 H

1-525 CF₃ N CF₃ CF₃ C-H C-H C-CN G9 H

1-526 CI C-Cl CF₃ CF₃ C-H C-H C-Br F -

1-527 CI C-Cl CF₃ CF₃ C-H C-H C-Br G6 H

1-528 CF₃ C-F H CF₃ C-H C-H C-Br F -

1-529 CF₃ C-F H CF₃ C-H C-H C-Br G6 H

1-530 CF₃ C-H F CF₃ C-H C-H C-Br F -

1-531 CF₃ C-H F CF₃ C-H C-H C-Br G6 H

1-532 CF₃ N H CF₃ C-H C-H C-Br F -

1-533 CF₃ N H CF₃ C-H C-H C-Br G6 H

1-534 CF₃ N F CF₃ C-H C-H C-Br F -

1-535 CF₃ N F CF₃ C-H C-H C-Br G6 H

1-536 CI C-Cl CI CF₃ C-H N C-Br F - Ex. No. X¹ B X² R A¹ A² A⁴ G (Z)_k

1-537 CI C-Cl CI CF₃ C-H N C-Br G6 H

1-538 CF₃ C-H CF3 CF₃ C-H N C-Br F -

1-539 CF₃ C-H CF3 CF₃ C-H N C-Br G6 H

1-540 CI N CI CF₃ C-H N C-Br F -

1-541 CI N CI CF₃ C-H N C-Br G6 H

1-542 CF₃ N CF3 CF₃ C-H N C-Br F -

1-543 CF₃ N CF3 CF₃ C-H N C-Br G6 H

1-544 CI C-Cl CI CF₃ N C-H C-Br F -

1-545 CI C-Cl CI CF₃ N C-H C-Br G6 H

1-546 CF₃ C-H CF3 CF₃ N C-H C-Br F -

1-547 CF₃ C-H CF3 CF₃ N C-H C-Br G6 H

1-548 CI N CI CF₃ N C-H C-Br F -

1-549 CI N CI CF₃ N C-H C-Br G6 H

1-550 CF₃ N CF3 CF₃ N C-H C-Br F -

1-551 CF₃ N CF3 CF₃ N C-H C-Br G6 H

1-552 CI C-Cl CF₃ CF₃ C-H C-H C-CN F -

1-553 CI C-Cl CF₃ CF₃ C-H C-H C-CN G6 H

1-554 CF₃ C-F H CF₃ C-H C-H C-CN F -

1-555 CF₃ C-F H CF₃ C-H C-H C-CN G6 H

1-556 CF₃ C-H F CF₃ C-H C-H C-CN F -

1-557 CF₃ C-H F CF₃ C-H C-H C-CN G6 H

1-558 CF₃ N H CF₃ C-H C-H C-CN F -

1-559 CF₃ N H CF₃ C-H C-H C-CN G6 H

1-560 CF₃ N F CF₃ C-H C-H C-CN F -

1-561 CF₃ N F CF₃ C-H C-H C-CN G6 H

1-562 CI C-Cl CI CF₃ C-H N C-CN F -

1-563 CI C-Cl CI CF₃ C-H N C-CN G6 H

1-564 CF₃ C-H CF3 CF₃ C-H N C-CN F -

1-565 CF₃ C-H CF3 CF₃ C-H N C-CN G6 H

1-566 CI N CI CF₃ C-H N C-CN F -

1-567 CI N CI CF₃ C-H N C-CN G6 H

1-568 CF₃ N CF3 CF₃ C-H N C-CN F -

1-569 CF₃ N CF3 CF₃ C-H N C-CN G6 H

1-570 CI C-Cl CI CF₃ N C-H C-CN F -

1-571 CI C-Cl CI CF₃ N C-H C-CN G6 H Ex. No. X¹ B X² R A¹ A² A⁴ G (Z)_k

1-572 CF₃ C-H CF3 CF₃ N C-H C-CN F -

1-573 CF₃ C-H CF3 CF₃ N C-H C-CN G6 H

1-574 CI N CI CF₃ N C-H C-CN F -

1-575 CI N CI CF₃ N C-H C-CN G6 H

1-576 CF₃ N CF3 CF₃ N C-H C-CN F -

1-577 CF₃ N CF3 CF₃ N C-H C-CN G6 H

Table 2

Ex.-No. X¹ B X² R Y R¹ R² R³

2-1 CI C-H CI CF₃ CI H H H

2-2 CI C-H CI CF₃ CI H CH₃CO H

2-3 CI C-H CI CF₃ CI H CH₃CH₂CO H

2-4 CI C-H CI CF₃ CI H n-CH₃CH₂CH₂CO H

2-5 CI C-H CI CF₃ CI H cyclo-PrCO H

2-6 CI C-H CI CF₃ CI H cyclo-PrCH₂CO H

2-7 CI C-H CI CF₃ CI H CF₃CH₂CO H

2-8 CI C-H CI CF₃ CI H CH₃SCH₂CO H

2-9 CI C-H CI CF₃ CI H CH₃SOCH₂CO H

2-10 CI C-H CI CF₃ CI H CH₃S0₂CH₂CO H

2-11 CI C-H CI CF₃ CI H CH₃CH₂NHCO H

2-12 CI C-H CI CF₃ CI H CH₃CH₂OC(=0) H

2-13 CI C-H CI CF₃ CI H CH₃OCH₂CH₂CO H

2-14 CI C-H CI CF₃ CI H CH₃OCH(CH₃)CH₂CO H

2-15 CI C-H CI CF₃ CI H tert-BuOC(=0) H

2-16 CI C-H CI CF₃ CI H CH₃S0₂ H

2-17 CF₃ C-H H CF₃ CI H H H

2-18 CF₃ C-H H CF₃ CI H CH₃CH₂CO H

2-19 CF₃ C-H H CF₃ CI H n-CH₃CH₂CH₂CO H

2-20 CF₃ C-H H CF₃ CI H cyclo-PrCO H

Table 3

Ex.-No. X¹ B X² R R¹ R²

3-1 CI C-H CI CF₃ H H ¹

3-2 CI C-H CI CF₃ H HCO ¹

3-3 CI C-H CI CF₃ H CH₃CO ¹

3-4 CI C-H CI CF₃ H CH₃CH₂CO ¹

3-5 CI C-H CI CF₃ H CH₃CH₂CH₂CO ¹

3-6 CI C-H CI CF₃ H cyclo-PrCO ¹

3-7 CI C-H CI CF₃ H cyclo-PrCH₂CO ¹

3-8 CI C-H CI CF₃ H CF₃CH₂CO ¹

3-9 CI C-H CI CF₃ H CH₃SCH₂CO ¹

3-10 CI C-H CI CF₃ H CH₃SOCH₂CO ¹

3-11 CI C-H CI CF₃ H CH₃S0₂CH₂CO ¹

3-12 CI C-H CI CF₃ H CH₃CH₂NHCO ¹

3-13 CI C-H CI CF₃ H CH₃CH₂OC(=0) ¹

3-14 CI C-H CI CF₃ H CH₃OCH₂CH₂CO ¹

3-15 CI C-H CI CF₃ H CH₃OCH(CH₃)CH₂CO ¹

3-16 CI C-H CI CF₃ H tert-BuOC(=0) ¹

Table 4

Ex.-No. X¹ B X² R Y R3 n

4-1 CI C-H CI CF₃ H H 0

4-2 CI C-H CI CF₃ H H 1

4-3 CI C-H CI CF₃ H H 2

4-4 CI C-H CI CF₃ CH₃ H 0

4-5 CI C-H CI CF₃ CH₃ H 1

4-6 CI C-H CI CF₃ CH₃ H 2

4-7 CI C-H CI CF₃ CI H 0

4-8 CI C-H CI CF₃ CI H 1

4-9 CI C-H CI CF₃ CI H 2

4-10 CI C-H CI CF₃ Br H 0

4-11 CI C-H CI CF₃ Br H 1

4-12 CI C-H CI CF₃ Br H 2

4-13 CI C-H CI CF₃ CF₃ H 0

4-14 CI C-H CI CF₃ CF₃ H 1

4-15 CI C-H CI CF₃ CF₃ H 2

4-16 CI C-H CI CF₃ CF₃ H 0

4-17 CI C-H CI CF₃ CF₃ H 1

4-18 CI C-H CI CF₃ CF₃ H 2

4-19 CF₃ C-H H CF₃ CF₃ H 0

4-20 CF₃ C-H H CF₃ CF₃ H 1

4-21 CF₃ C-H H CF₃ CF₃ H 2

4-22 CF₃ C-H H CF₃ CF₃ H 0

4-23 CF₃ C-H H CF₃ CF₃ H 1

4-24 CF₃ C-H H CF₃ CF₃ H 2

4-25 CF₃ C-H H CF₃ CF₃ H 0

4-26 CF₃ C-H H CF₃ CF₃ H 1

4-27 CF₃ C-H H CF₃ CF₃ H 2

4-28 CF₃ C-H H CF₃ CF₃ H 0 Ex.-No. X¹ B X² R Y R3 n

4-29 CF₃ C-H H CF₃ CF₃ H 1

4-30 CF₃ C-H H CF₃ CF₃ H 2

4-31 CF₃ C-H H CF₃ CF₃ H 0

4-32 CF₃ C-H H CF₃ CF₃ H 1

4-33 CF₃ C-H H CF₃ CF₃ H 2

4-34 CF₃ C-H H CF₃ N0₂ H 0

4-35 CF₃ C-H H CF₃ N0₂ H 1

4-36 CF₃ C-H H CF₃ N0₂ H 2

4-37 CF₃ C-H CF₃ CF₃ H H 0

4-38 CF₃ C-H CF₃ CF₃ H H 1

4-39 CF₃ C-H CF₃ CF₃ H H 2

4-40 CF₃ C-H CF₃ CF₃ CH₃ H 0

4-41 CF₃ C-H CF₃ CF₃ CH₃ H 1

4-42 CF₃ C-H CF₃ CF₃ CH₃ H 2

4-43 CF₃ C-H CF₃ CF₃ CI H 0

4-44 CF₃ C-H CF₃ CF₃ CI H 1

4-45 CF₃ C-H CF₃ CF₃ CI H 2

4-46 CF₃ C-H CF₃ CF₃ Br H 0

4-47 CF₃ C-H CF₃ CF₃ Br H 1

4-48 CF₃ C-H CF₃ CF₃ Br H 2

4-49 CF₃ C-H CF₃ CF₃ CF3 H 0

4-50 CF₃ C-H CF₃ CF₃ CF3 H 1

4-51 CF₃ C-H CF₃ CF₃ CF3 H 2

4-52 CF₃ C-H CF₃ CF₃ N0₂ H 0

4-53 CF₃ C-H CF₃ CF₃ N0₂ H 1

4-54 CF₃ C-H CF₃ CF₃ N0₂ H 2

4-55 Br C-H Br CF₃ H H 0

4-56 Br C-H Br CF₃ H H 1

4-57 Br C-H Br CF₃ H H 2

4-58 Br C-H Br CF₃ CH₃ H 0

4-59 Br C-H Br CF₃ CH₃ H 1

4-60 Br C-H Br CF₃ CH₃ H 2

4-61 Br C-H Br CF₃ CI H 0

4-62 Br C-H Br CF₃ CI H 1 Ex.-No. X¹ B X² R Y R3 n

4-63 Br C-H Br CF₃ CI H 2

4-64 Br C-H Br CF₃ Br H 0

4-65 Br C-H Br CF₃ Br H 1

4-66 Br C-H Br CF₃ Br H 2

4-67 Br C-H Br CF₃ CF3 H 0

4-68 Br C-H Br CF₃ CF3 H 1

4-69 Br C-H Br CF₃ CF3 H 2

4-70 Br C-H Br CF₃ N0₂ H 0

4-71 Br C-H Br CF₃ N0₂ H 1

4-72 Br C-H Br CF₃ N0₂ H 2

4-73 CI C-Cl CI CF₃ H H 0

4-74 CI C-Cl CI CF₃ H H 1

4-75 CI C-Cl CI CF₃ H H 2

4-76 CI C-Cl CI CF₃ CH₃ H 0

4-77 CI C-Cl CI CF₃ CH₃ H 1

4-78 CI C-Cl CI CF₃ CH₃ H 2

4-79 CI C-Cl CI CF₃ CI H 0

4-80 CI C-Cl CI CF₃ CI H 1

4-81 CI C-Cl CI CF₃ CI H 2

4-82 CI C-Cl CI CF₃ Br H 0

4-83 CI C-Cl CI CF₃ Br H 1

4-84 CI C-Cl CI CF₃ Br H 2

4-85 CI C-Cl CI CF₃ CF3 H 0

4-86 CI C-Cl CI CF₃ CF3 H 1

4-87 CI C-Cl CI CF₃ CF3 H 2

4-88 CI C-Cl CI CF₃ N0₂ H 0

4-89 CI C-Cl CI CF₃ N0₂ H 1

4-90 CI C-Cl CI CF₃ N0₂ H 2

4-91 CI N CI CF₃ H H 0

4-92 CI N CI CF₃ H H 1

4-93 CI N CI CF₃ H H 2

4-94 CI N CI CF₃ CH₃ H 0

4-95 CI N CI CF₃ CH₃ H 1

4-96 CI N CI CF₃ CH₃ H 2 Ex.-No. X¹ B X² R Y R3 n

4-97 CI N CI CF₃ CI H 0

4-98 CI N CI CF₃ CI H 1

4-99 CI N CI CF₃ CI H 2

4-100 CI N CI CF₃ Br H 0

4-101 CI N CI CF₃ Br H 1

4-102 CI N CI CF₃ Br H 2

4-103 CI N CI CF₃ CF3 H 0

4-104 CI N CI CF₃ CF3 H 1

4-105 CI N CI CF₃ CF3 H 2

4-106 CI N CI CF₃ N0₂ H 0

4-107 CI N CI CF₃ N0₂ H 1

4-108 CI N CI CF₃ N0₂ H 2

4-109 CF₃ N CF₃ CF₃ H H 0

4-110 CF₃ N CF₃ CF₃ H H 1

4-111 CF₃ N CF₃ CF₃ H H 2

4-112 CF₃ N CF₃ CF₃ CH₃ H 0

4-113 CF₃ N CF₃ CF₃ CH₃ H 1

4-114 CF₃ N CF₃ CF₃ CH₃ H 2

4-115 CF₃ N CF₃ CF₃ CI H 0

4-116 CF₃ N CF₃ CF₃ CI H 1

4-117 CF₃ N CF₃ CF₃ CI H 2

4-118 CF₃ N CF₃ CF₃ Br H 0

4-119 CF₃ N CF₃ CF₃ Br H 1

4-120 CF₃ N CF₃ CF₃ Br H 2

4-121 CF₃ N CF₃ CF₃ CF3 H 0

4-122 CF₃ N CF₃ CF₃ CF3 H 1

4-123 CF₃ N CF₃ CF₃ CF3 H 2

4-124 CF₃ N CF₃ CF₃ N0₂ H 0

4-125 CF₃ N CF₃ CF₃ N0₂ H 1

4-126 CF₃ N CF₃ CF₃ N0₂ H 2

4-127 CI C-Cl CF₃ CF₃ CH₃ H 1

4-128 CI C-Cl CF₃ CF₃ CH₃ H 2

4-129 CF₃ C-F H CF₃ CH₃ H 0

4-130 CF₃ C-F H CF₃ CH₃ H 1 Ex.-No. X¹ B X² R Y R3 n

4-131 CF₃ C-H F CF₃ CH₃ H 1

4-132 CF₃ C-H F CF₃ CH₃ H 2

4-133 CF₃ N H CF₃ CH₃ H 0

4-134 CF₃ N H CF₃ CH₃ H 1

4-135 CF₃ N F CF₃ CH₃ H 1

4-136 CF₃ N F CF₃ CH₃ H 2

4-137 CI CI CI CF₃ CH₃ CH₃ 0

4-138 CI CI CI CF₃ CH₃ CH₃ 1

4-139 CI CI CI CF₃ CH₃ CH₃ 2

4-140 CF₃ C-H CF₃ CF₃ CH₃ CH₃ 0

4-141 CF₃ C-H CF₃ CF₃ CH₃ CH₃ 1

4-142 CF₃ C-H CF₃ CF₃ CH₃ CH₃ 2

Table 5

No. IH-NMR

IH-NMR (CDC13) δ: 3.62-3.68 (IH, m), 3.86-3.92 (IH, m), 4.73-4.83 (2H, m), 7.19-7.35

1-31

(3H, m), 7.45-7.46 (IH, m), 8.30-8.40 (IH, m), 8.61-8.64 (IH, m).

IH-NMR (CD CI 3) δ: 3.66-3.71 (IH, m), 3.88-3.94 (IH, m), 4.73-4.83 (2H, m), 7.22-7.40

1-61

(2H, m), 7.46-7.48 (2H, m), 8.60-8.63 (IH, m), 8.76-8.78 (IH, m).

IH-NMR (CD CI 3) δ: 3.72-3.77 (IH, m), 3.94-4.00 (IH, m), 4.80-4.90 (2H, m), 7.25-7.28

1-72 (IH, m), 7.48-7.49 (IH, m), 7.94-8.02 (2H, m), 8.22 (IH, s), 8.64-8.68 (IH, m), 8.92-8.97 (2H, m).

IH-NMR (CDC13) δ: 3.75-3.98 (2H, m), 4.85-4.91 (2H, m), 7.22-7.26 (IH, m), 7.82 (2H, s),

1-181

8.00 (IH, s), 8.32-8.35 (IH, m), 8.63-8.65 (IH, m)

IH-NMR (CDC13) δ: 3.95 (2H, dd), 4.92 (2H, s), 7.35-7.39 (IH, m), 7.87 (2H, s), 8.01 (IH,

1-211

s), 8.62-8.65 (IH, m), 8.82-8.84 (IH, m)

IH-NMR (acetone-d6) δ: 4.30-4.49 (2H, m), 5.03-5.27 (2H, m), 8.04 (IH, d), 8.21-8.24 (2H,

1-222

m), 8.32 (2H, s), 8.97-9.00 (IH, m), 9.07 (2H, d)

IH-NMR (CDC13) δ: 3.76 (2H, dd), 4.77 (2H, dd), 7.22 (2H, d), 7.39 (2H, s), 8.31-8.34 (IH,

1-331

m), 8.60-8.63 (IH, m)

IH-NMR (CDC13) δ: 3.82 (2H, dd), 4.82 (2H, dd), 7.41 (2H, s), 7.67 (IH, d), 8.16 (IH, s),

1-342

8.38 (IH, dd), 8.62 (IH, s), 8.83 (IH, d)

IH-NMR (CD CI 3) δ: 3.60-3.69 (IH, m), 3.86-3.94 (IH, m), 4.73-4.83 (2H, m), 7.22-7.45

1-361

(2H, m), 8.02 (IH, m), 8.30-8.40 (IH, m), 8.61-8.64 (IH, m), 8.75-8.77 (IH, m).

1-372 IH-NMR (DMSO-d6) δ: 4.06 (2H, dd), 4.91 (2H, dd), 7.88 (2H, s), 8.07 (IH, d), 8.40 (IH, s), No. 1H-NMR

8.94 (2H, d), 9.28 (1H, s)

1H-NMR (CDC13) δ: 0.74-0.80 (2H, m), 0.97-01.02 (2H, m), 1.40-1.47 (1H, m), 3.69-3.75

2-28 (1H, m), 3.97-4.04 (1H, m), 4.55-4.57 (2H, m), 4.81-4.92 (2H, m), 6.25-6.29 (1H, m), 7.46- 7.49 (1H, m), 7.82 (2H, s), 8.00-8.05 (2H, m), 8.50-8.51 (1H, m).

1H-NMR (CDC13) δ: 1.18 (3H, t), 2.28 (2H, q), 3.61-3.67 (1H, m), 3.84-3.89 (1H, m), 4.51-

2-46 4.53 (2H, m), 4.75 (2H, br s), 6.25-6.29 (1H, m), 7.41 (2H, s), 7.41-7.45 (1H, m), 7.95-7.98 (1H, m), 8.46 (1H, s).

1H-NMR (CDC13) δ: 0.74-0.80 (2H, m), 0.98-01.02 (2H, m), 1.39-1.47 (1H, m), 3.59-3.65

2-48 (1H, m), 3.85-3.91 (1H, m), 4.56-4.58 (2H, m), 4.70-4.82 (2H, m), 6.17 (lH, br s), 7.40 (2H, s), 7.49-7.51 (1H, m), 8.00-8.03 (1H, m), 8.50-8.52 (1H, m).

1H-NMR (CDC13) δ: 1.15 (3H, t), 1.40-1.47 (3H, d), 2.15-2.26 (2H, m), 3.46-3.58 (2H, m),

2-337 3.70-3.78 (2H, m), 5.05-5.20 (1H, m), 5.58-5.79 (1H, m), 7.18-7.20 (2H, m), 7.21 (3H, m), 7.39-7.42 (2H, m).

1H-NMR (acetone-d6) δ: 1.08 (3H, t), 1.79-1.85 (1H, m), 2.21 (2H, q), 2.43-2.48 (1H, m),

3-72 2.83-2.90 (2H, m), 4.04 (2H, dd), 4.87 (2H, dd), 5.42-5.44 (1H, m), 7.29-7.37 (2H, m), 7.80 (2H, s), 8.23-8.35 (2H, m)

1H-NMR (CDC13) δ: 1.50 (9H, s), 1.80-1.83 (1H, m), 2.60-2.63 (1H, m), 2.83-3.00 (2H, m),

3-84 3.78 (2H, dd), 4.76 (3H, dd), 5.21 (1H, br s), 7.41-7.43 (3H, m), 8.01-8.06 (1H, m), 8.36 (1H, d)

1H-NMR (CDC13) δ: 2.93 (3H, s), 3.39-3.51 (4H, m), 3.62-3.68 (1H, m), 3.87-3.93 (1H, m),

4-76 4.67-4.80 (2H, m), 5.38-5.46 (1H, m), 6.59-6.62 (1H, m), 7.40-7.44 (3H, m), 8.03 ( 1H, s), 8.21-8.24 (lH, m).

The test solutions of Biological test example la, 2a and 3a were prepared as follows:

Solvent: Dimethylformamide, 3 parts by weight

Emulsifier: Polyoxyethylene alkyl phenyl ether, 1 part by weight

To prepare a suitable preparation of active compound, 1 part by weight of the compound of the present invention is mixed with the above-mentioned amount of solvent containing the above-mentioned amount of emulsifier, and the mixture is diluted with water to the desired concentration.

[Biological test example 11 : Test against tobacco cutworm (Spodoptera litura) larvae

Biological test example la: Leaves of sweet potato were immersed in the test solution at the appropriate concentration, and the leaves were dried in air. The leaves were then placed in a petri dish having a diameter of 9 cm, and ten Spodoptera litura at third instar larvae were released therein. The petri dishes were placed in a temperature-controlled chamber at 25 °C. After 2 days and 4 days more sweet potato leaves were added. After 7 days, the number of dead larvae was counted to calculate the insecticidal activity. An insecticidal activity of 100 % means that all larvae were killed, whereas an insecticidal activity of 0 % means that no larva was killed. In the current test, the results of two petri dishes for each treatment were averaged.

In the biological test example la, the compounds Nos. 1-222, 1-372 and 3-72 showed an insecticidal activity of 100% at an active compound concentration of 20 ppm.

Biological test example lb - Spodoptera litura - test (PRODLI) Solvent: 3 parts by weight Dimethylformamide

Emulsifier: 1 part by weight Polyoxyethylene alkyl phenyl ether

In order to make an appropriate formulation of an active compound, 1 part by weight of the active compound is mixed with the above mentioned amount of solvent and emulsifier and the mixture is diluted with water to a prescribed concentration. Ammonium salt or ammonium salt and penetration enhancer in a dosage of lOOOppm are added to the desired concentration if necessary.

Leaves of sweet potato (Ipomoea batatas) are immersed in the test solution of the desired concentration. After drying, the treated leaves are placed in a petri dish and are inoculated with 10 third-instar larvae of the cotton leafworm {Spodoptera litura). After 6 days, mortality in % is determined. 100% means that all the larvae have been killed; 0% means that none of the larvae have been killed. In this test the following compounds showed an insecticidal activity of 100% at an active compound concentration of lOOppm: 1-222, 2-337

In this test the following compounds showed an insecticidal activity of 100% at an active compound concentration of 4ppm: 1-372, 1-72, 2-28, 2-48, 3-72

[Biological test example 21 : Test against two-spotted spider mite (Tetranychus urticae) Biological test example 2a: 50 to 100 adult mites of Tetranychus urticae were inoculated to leaves of kidney bean at two-leaf stage planted in a pot of 6 cm in diameter. After one day, test solution at the appropriate concentration was sprayed thereon in a sufficient amount using a spray gun. After the spraying, the plant pot was placed inside a greenhouse, and after 7 days, the acaricidal activity was calculated. An acaricidal activity of 100 % means that all mites were killed, whereas an acaricidal activity of 0 % means that no mite was killed. In the biological test example 2a, the compound Nos. 1-222, 1-372 and 3-72 showed an acaricidal activity of 100 % at an active compound concentration of 20 ppm.

Biological test example 2b: Two-spotted spider mite (TETRUR)

Solvent: Dimethylformamide, 3 parts by weight Emulsifier: Polyoxyethylene alkyl phenyl ether, 1 part by weight

In order to make an appropriate formulation of an active compound, 1 part by weight of the active compound is mixed with the above mentioned amount of solvent and emulsifier and the mixture is diluted with water to a prescribed concentration. Ammonium salt or ammonium salt and penetration enhancer in a dosage of lOOOppm are added to the desired concentration if necessary. Kidney beans (Phaseolus vulgaris) in the 2-leaf-stage, which are heavily infested with all stages of the two spotted spidermite (Tetranychus urticae), are sprayed with a preparation of the active ingredient of the desired concentration. After 2 days, the acaricidal activity is calculated. An acaricidal activity of 100 % means that all mites have been killed, an acaricidal activity of 0 % means that no mites have been killed. In this test the following compounds showed an acaricidal activity of 98% at an active compound concentration of 5 OOppm: 1-331

In this test the following compounds showed an acaricidal activity of 90% at an active compound concentration of 5 OOppm: 1-31, 1-361

After 6 days, the acaricidal activity is calculated. An acaricidal activity of 100 % means that all mites have been killed, an acaricidal activity of 0 % means that no mites have been killed.

In this test the following compounds showed an acaricidal activity of 90% at an active compound concentration of 5 OOppm: 3-84

In this test the following compounds showed an acaricidal activity of 100% at an active compound concentration of 1 OOppm: 1-222 In this test the following compounds showed an acaricidal activity of 98% at an active compound concentration of 1 OOppm: 2-337

In this test the following compounds showed an acaricidal activity of 100% at an active compound concentration of 20ppm: 1-372, 2-46, 3-72, 4-76

In this test the following compounds showed an acaricidal activity of 98% at an active compound concentration of 20ppm: 1-72, 2-28, 2-48

[Biological test example 31 : Test against cucurbit leaf beetle (Aulacophora femoralis)

Biological test example 3a: Leaves of cucumber were immersed in the test solution at the appropriate concentration, and the leaves were dried in air. The leaves were then put in a plastic cup containing sterilized black soil and five Aulacophora femoralis at second instar larvae were released in the cup. After 7 days, the number of dead larvae was counted, and thus the insecticidal activity was calculated. An insecticidal activity of 100 % means that all larvae were killed, whereas an insecticidal activity of 0 % means that no larva was killed.

In the biological test example 3a, the compounds Nos. 1-222, 1-372 and 3-72 showed an insecticidal activity of 100% at an active compound concentration of 20 ppm.

Biological test example 3b - Aulacophora femoralis - spray- test (AUACFE)

Solvent: 3 parts by weight dimethylformamide

Emulsifier: 1 part by weight polyoxyethylene alkyl phenyl ether

Cucumber seedlings (Cucumis sativus) in the cotyledon stage are treated by being sprayed with the compound solution of the desired concentration. After drying, the treated plantmaterial is put in a testing cup and infested with 5 L2-larvae of the cucurbit leaf beetle {Aulacophora femoralis). After 6 days the number of dead larvae is counted to calculate the insecticidal activity. An insecticidal activity of 100 % means that all larvae have been killed, an insecticidal activity of 0 % means that no larvae have been killed.

In this test the following compounds showed an insecticidal activity of 100% at an active compound concentration of lOOppm: 1-222, 2-337

In this test the following compounds showed an insecticidal activity of 100% at an active compound concentration of 20ppm: 1-372, 1-72, 2-28, 2-46, 2-48, 3-72, 4-76

[Biological test example 41 : Test against Mvzus persicae - spray test (MYZUPE - OP/Carb- resistant) Solvent: 3 parts by weight dimethylformamide

Emulsifier: 1 part by weight polyoxyethylene alkyl phenyl ether

Eggplant seedlings (Solarium melongena) in the 2-leaf stage, which are heavily infected with all instars of the green peach aphid (Myzus persicae), are sprayed with a preparation of the active ingredient of the desired concentration. After 6 days mortality in % is determined. An insecticidal activity of 100 % means that all aphids have been killed, an insecticidal activity of 0 % means that no aphids have been killed.

In this test the following compounds showed an insecticidal activity of 90% at an active compound concentration of 5 OOppm: 1-331

In this test the following compounds showed an insecticidal activity of 98% at an active compound concentration of 1 OOppm: 1-222, 1-72

In this test the following compounds showed an insecticidal activity of 100% at an active compound concentration of 20ppm: 4-76

In this test the following compounds showed an insecticidal activity of 90% at an active compound concentration of 20ppm: 1-372, 1-72, 2-46 [Biological test example 51 ; Test against Boophilus microplus

Biological test example 5a: To produce a suitable preparation of active compound, 10 mg of active compound are dissolved in 0.5 ml solvent (=Dimethyl sulfoxide), and the concentrate is diluted with solvent to the desired concentration.

Five adult engorged female ticks (Boophilus microplus) are injected with compound solution prepared above into the abdomen. Ticks are transferred into replica plates and incubated in a climate chamber for a period of time. After a period of time, mortality of Boophilus microplus in % is determined. 100 % means that all eggs are infertile; 0 % means that all eggs are fertile.

In this biological test example 5a, the compounds Nos. 1-222 and 1-372 showed an insecticidal activity of 100% at an active compound concentration of 100 ppm. Biological test example 5b- Boophilus microplus - test (injection)

To produce a suitable preparation of active compound, 10 mg of active compound are dissolved in 0.5 ml solvent (=Dimethyl sulfoxide), and the concentrate is diluted with solvent to the desired concentration.

Five adult engorged female ticks (Boophilus microplus) are injected with 1 μΐ compound solution into the abdomen. Ticks are transferred into replica plates and incubated in a climate chamber for a period of time. Egg deposition of fertile eggs is monitored. After 7 days, mortality in % is determined. 100 % means that all eggs are infertile; 0 % means that all eggs are fertile.

In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of 20μ§ 3ΐώϊΐ£ΐ1: 1-222, 1-372, 1-72, 2-28, 2-337, 2-46, 2-48, 3-72, 4-76

[Biological test example 61 : Test against Lucilia cuprina

Biological test example 6a: 10 mg active compound is dissolved in 0,5ml dimethyl sulfoxide. Serial dilutions are made to obtain the desired concentrations.

Approximately 20 Lucilia cuprina 1^st instar larvae are transferred into a test tube containing 1 cm³ of minced horse meat and 0.5 ml aqueous dilution of test compound. After 48 hrs, percentages of larval mortality are recorded. 100 % means that all larvae are killed, 0% means that larvae are normally developed after 48 hrs.

In the biological test example 6a, the compounds Nos. 1-222 and 1-372 showed an insecticidal activity of 100% at an active compound concentration of 100 ppm.

Biological test example 6b: Lucilia cuprina (48h) species: Lucilia cuprina 1^st instar larvae (age 24 hrs)

10 mg active compound are dissolved in 0,5 ml dimethylsulfoxid. Serial dilutions are made to obtain the desired rates.

Approximately 20 Lucilia cuprina 1^st instar larvae are transferred into a test tube containing 1 cm³ of minced horse meat and 0.5 ml aqueous dilution of test compound.

After 48 hrs the percentage of larval mortality is recorded. 100 % means that all larvae have been killed, 0 % means that there are normally developed larvae after 48 hrs.

In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of lOOppm: 1-222, 1-372, 1-72, 2-28, 2-337, 2-46, 2-48, 3-72, 4-76 [Biological test example 71 : Test against housefly (Musca domestica)

Biological test example 7a: Prior to the assay, a piece of kitchen sponge is soaked with a mixture of sugar and compound solution prepared as with Biological test example 6 and placed into a container. 10 adults housefly (Musca domestica) are placed into the container and closed with a perforated lid. After 2 days mortality in % is determined. 100 % means that all the flies have been killed; 0 % means that none of the flies have been killed.

In the biological test example 7a, the compounds Nos. 1-222 and 1-372 showed an insecticidal activity of 100% at an active compound concentration of 100 ppm.

Biological test example 7b: Musca domestica - test To produce a suitable preparation of active compound, 10 mg of active compound are dissolved in 0.5 ml solvent (=dimethyl sulfoxide), and the concentrate is diluted with water to the desired concentration.

Prior to the assay, a piece of kitchen sponge is soaked with a mixture of sugar and compound solution and placed into a container. 10 adults (Musca domestica) are placed into the container and closed with a perforated lid. After 2 days mortality in % is determined. 100 % means that all the flies have been killed; 0 % means that none of the flies have been killed.

In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of lOOppm: 1-222, 1-372, 1-72, 2-28, 2-337, 2-46, 2-48, 3-72, 4-76

[Biological test example 81 : Test against cat flea (CTECFE)

Biological test example 8a: To produce a suitable preparation of active compound, 10 mg of active compound are dissolved in 0.5 ml of dimethyl sulfoxide, and the concentrate is diluted with cattle blood to the desired concentration.

Approximately 20 adult unfed cat flea (Ctenocepahlides felis) are placed in flea chambers. The blood chamber, sealed with parafilm on the bottom, are filled with cattle blood supplied with compound solution and placed on top of the flea chamber, so that the fleas are able to suck the blood. The blood chamber is heated to 37 °C whereas the flea chamber is kept at room temperature. After 2 days mortality in % is determined. 100 % means that all the fleas have been killed; 0 % means that none of the fleas have been killed.

In this biological test example 8a, the compounds Nos. 1-222 and 1-372 showed an insecticidal activity of 100% at an active compound concentration of 100 ppm. Biological test example 8b - Ctenocephalides felis - test (CTECFE): To produce a suitable preparation of active compound, 10 mg of active compound are dissolved in 0.5 ml solvent (=dimethyl sulfoxide), and the concentrate is diluted with cattle blood to the desired concentration.

Approximately 20 adult unfed fleas (Ctenocepahlides felis) are placed in flea chambers. The blood chamber, sealed with parafilm on the bottom, are filled with cattle blood supplied with compound solution and placed on top of the flea chamber, so that the fleas are able to suck the blood. The blood chamber is heated to 37 °C whereas the flea chamber is kept at room temperature. After 2 days mortality in % is determined. 100 % means that all the fleas have been killed; 0 % means that none of the fleas have been killed. In this test, for example, the following compounds from the preparation examples showed good activity of 100% at an application rate of lOOppm: 1-222, 1-372, 2-46, 2-48, 4-76

In this test, for example, the following compounds from the preparation examples showed good activity of 95% at an application rate of lOOppm: 3-72

In this test, for example, the following compounds from the preparation examples showed good activity of 90% at an application rate of lOOppm: 1-72, 2-28

In this test, for example, the following compounds from the preparation examples showed good activity of 80% at an application rate of lOOppm: 2-337.

[Biological test example 91 ; Test against Thrips palmi - spravtest (THRIPL) Solvent: Dimethylformamide, 3 parts by weight

Emulsifier: Polyoxyethylene alkyl phenyl ether, 1 part by weight

Cucumber seedlings (Cucumis sativus) are treated by being sprayed with the compound solution of the desired concentration. After drying, pieces of filter paper with about 100 thrips-eggs (Thrips palmi) are attached to the treated plants and covered with a cage to keep 100% humidity.

After 6 days activity in % is evaluated by feeding damage degree. An activity of 100 % means that there is no feeding damage, an activity of 0 % means that there is no difference to the untreated control.

In this test the following compounds showed an insecticidal activity of 98% at an active compound concentration of 500ppm: 3-84 In this test the following compounds showed an insecticidal activity of 100% at an active compound concentration of lOOppm: 1-222, 2-337

In this test the following compounds showed an insecticidal activity of 100% at an active compound concentration of 20ppm: 1-372, 2-46, 2-48, 4-76 In this test the following compounds showed an insecticidal activity of 98% at an active compound concentration of 20ppm: 3-72

In this test the following compounds showed an insecticidal activity of 90% at an active compound concentration of 20ppm: 2-28 Preparation Example 1 (granules): To a mixture containing 10 parts of the compound of the present invention, 30 parts of bentonite (montmorillonite), 58 parts of talc and 2 parts of lignin sulfonate is added 25 parts of water, and the mixture is well kneaded and granulated with 10 to 40 meshes by an extruding granulator and dried at 40 to 50°C to obtain granules.

Preparation Example 2 (granules): 95 parts of clay mineral granules having particle diameter distribution within the range of 0.2 to 2 mm are put into a rotary mixer, and then wetted evenly by spraying of 5 parts of the compound of the present invention together with a liquid diluent under rotating condition and dried at 40 to 50°C to obtain granules.

Preparation Example 3 (emulsion): 30 parts of the compound of the present invention, 55 parts of xylene, 8 parts of polyoxyethylene alkyl phenyl ether and 7 parts of calcium alky lbenzene sulfonate are mixed together to obtain the emulsion.

Preparation Example 4 (wettable agent): 15 parts of the compound of the present invention, 80 parts of a mixture of white carbon (hydrated amorphous silicon oxide fine powder) and powdered clay ( 1 : 5), formalin condensate of 2 parts of sodium alkylbenzenesulfonate and 3 parts of sodium alkylnaphthalenesulfonate are mixed together and the mixture is crushed to obtain a wettable agent. Preparation Example 5 (wettable granules): 20 parts of the compound of the present invention, 30 parts of lignin sodium sulfonate, 15 parts of bentonite and 35 parts of calcined diatomaceous earth powder are well mixed, and after addition of water, the mixture is extruded with a screen of 0.3 mm and dried to obtain wettable granules.

The pyrroline N-oxide derivatives of the present invention have excellent pesticidal activity as shown in the above examples.

Claims

1. Pyrroline N-oxides represented by the following Formula (I);

T i ne of following groups (Tl) to (T4) or a group (T5)

wherein in group (T5) A¹, A² and A³ are C-Y or nitrogen; is halogen, or a saturated or unsaturated 5- or 6-membered heterocyclic group which may be substituted; by halogen, Ci-12 alkyl, cyano, Ci_i₂ alkoxy-carbonyl or carboxy;

IS d-12 alkyl or Ci-12 haloalkyl which is optionally substituted; is hydrogen, amino, hydroxy, cyano, Ci_i₂ alkoxy , Ci_i₂ alkyl-carbonylamino, Ci_i₂ alkylimino, Ci_i₂ alkyl, C₃_g cycloalkyl, C₂_₆ alkenyl, C₂_₆ alkynyl, d_i₂ alkyl-carbonyl, CH₂- Pv⁶, C(=0)Pv⁶ or C(=S)Pv⁶, and among the definitions of R¹, each group from Ci-i₂ alkoxy to Ci-12 alkyl-carbonyl is optionally substituted; is hydrogen, cyano, carbonyl, thiocarbonyl, C_M2 alkyl-carbonyl, C_M2 alkyl-thiocarbonyl, Ci-12 haloalkyl-carbonyl, Ci_i₂ haloalkyl-thiocarbonyl, Ci_i₂ alkyl-aminocarbonyl, Ci_i₂ alkylamino-thiocarbonyl, C₂_₂₄ dialkylamino-carbonyl, C₂_₂₄ dialkylamino-thiocarbonyl, C_M2 alkoxyamino-carbonyl, Ci-i₂ alkoxyamino-thiocarbonyl, Ci-i₂ alkoxy-carbonyl, d_i₂ alkoxy- thiocarbonyl, Ci-i₂ alkylthio-carbonyl, d_i₂ alkylthio-thiocarbonyl, Ci-i₂ alkylsulfonyl, d_i₂ haloalkylsulfonyl, C₃_g cycloalkyl-carbonyl, C ₂_₆ alkenyl-carbonyl, C₂_₆ alkynyl-carbonyl, C₃_g cycloalkyl-Ci-4 alkyl-carbonyl, Ci-i₂ alkylthio-Ci_i₂ alkyl-carbonyl, d_i₂ alkylsulfinyl- - I l l -

Ci-12 alkyl-carbonyl, Ci_i₂ alkylsulfonyl-Ci_i₂ alkyl-carbonyl, Ci_i₂ alkyl-carbonyl-Ci_i₂ alkyl-carbonyl, C₃_g cycloalkylamino-carbonyl, C₂_₆ alkenylamino-carbonyl, C₂_₆ alkynylamino-carbonyl, C(=0)R⁶ or C(=S)R⁶, and among the definitions of R², each group from Ci_i₂ alkyl-carbonyl to C₂_₆ alkynylamino-carbonyl is optionally substituted;

R¹ and R² may form, together with the nitrogen atom to which they are bonded, a 3- to 6- membered heterocycle, and the heterocycle may be substituted with X as defined below, oxo, thioxo, or nitroimino;

R³ is hydrogen, cyano, d-12 alkyl which is optionally substituted or d_i₂ haloalkyl which is optionally substituted;

R⁴ is hydrogen, C_M2 alkyl, C_M2 alkyl-carbonyl, or C_M2 alkoxy-carbonyl;

B is X, C-H or N;

j is 1 or 2;

m is 0 to 4;

n is 0 to 2;

X is halogen, nitro, cyano, d-12 alkyl, d-12 alkoxy, d-12 haloalkyl, d-12 haloalkoxy, d-12 alkylthio, d-12 alkylsulfinyl, d-12 alkylsulfonyl, d-12 haloalkylthio, Ci_i₂ haloalkylsulfinyl, Ci_i₂ haloalkylsulfonyl, acylamino, Ci_i₂ alkoxy-carbonylamino, d-12 haloalkoxy- carbonylamino, Ci_i₂ alkoxyimino, d-12 haloalkoxyimino, Ci_i₂ alkylsulfonylamino, sulfur pentafluoride, hydroxy, mercapto or amino, and among the definitions of X, each group from d_i₂ alkyl to d-12 alkylsulfonylamino is optionally substituted;

Y is hydrogen, halogen, nitro, hydroxy, mercapto, cyano, amino, d-12 alkyl, d-12 haloalkyl, -8 cycloalkyl, d-8 cyclohaloalkyl, d-12 alkoxy, Ci_i₂ haloalkoxy, Ci_i₂ alkylthio, d-12 alkylsulfinyl, d-12 alkylsulfonyl, d-12 haloalkylthio, Ci_i₂ haloalkylsulfinyl, d-12 haloalkylsulfonyl, d-12 alkylsulfonyloxy, Ci_i₂ haloalkylsulfonyloxy, d-12 alkylaminosulfonyl, d-12 haloalkylaminosulfonyl, C₂_₂₄ dialkylaminosulfonyl, C₂_₂₄ di- haloalkyl-aminosulfonyl, d-₁₂ alkylamino, C₂_₂₄ dialkylamino, acylamino, Ci_i₂ alkoxy- carbonylamino, d_i₂ haloalkoxy-carbonylamino, Ci_i₂ alkylsulfonylamino, d-12 haloalkylsulfonylamino, C₃-₃₆ trialkylsilyl, d-12 alkoxyimino, Ci_i₂ haloalkoxyimino, Ci_i₂ alkoxyimino-d_i₂ alkyl, d-₁₂ haloalkoxyimino-Ci_i₂ alkyl, d-12 alkylsulfinylimino, Ci_i₂ alkylsulfinylimino-Ci-i₂ alkyl, d-12 alkylsulfinylimino-Ci_i₂ alkyl-carbonyl, d-₁₂ alkylsulfoxyimino, Ci_i₂ alkylsulfoxyimino-Ci_i₂ alkyl, Ci_i₂ alkoxy-carbonyl, Ci_i₂ alkyl- carbonyl, aminocarbonyl, d_i₂ alkylamino-carbonyl, amino-thiocarbonyl, C_M2 alkylamino- thiocarbonyl, C₂_₂₄ dialkyliminocarbonyl or C₂_₂₄ dialkylamino-thiocarbonyl;

Z¹, Z² and Z³ each independently represent CR⁷R⁸, C=0, C=N-OR⁹, N-R⁹, S(0)„, S=N-R⁹, or S(0)=N-R⁹, with the proviso that Z¹, Z² and Z³ do not simultaneously represent CR⁷R⁸;

R⁷ and R⁸ each independently represent hydrogen, halogen, C_M2 alkyl which may be substituted or Ci_i₂ haloalkyl which may be substituted; and

R⁹ is hydrogen, cyano, nitro, d-₁₂ alkyl, C_M2 haloalkyl, C₃_g cycloalkyl-d-₆ alkyl, d-₁₂ alkyl- carbonyl, d-₁₂ haloalkyl-carbonyl, d-₁₂ alkoxy-carbonyl, d-₁₂ haloalkoxy-carbonyl, d-₁₂ alkylsulfonyl, d-₁₂ haloalkylsulfonyl, d-io aryl-d-₆ alkyl or heteroaryl-d-₆ alkyl, among the definitions of R⁹, each group from d-₁₂ alkyl to Ci_i₂ haloalkylsulfonyl is optionally substituted, and the aryl moiety in d-io aryl-d-₆ alkyl and the heteroaryl moiety in heteroaryl-d-₆ alkyl may be substituted with one to three groups selected from a group consisting of halogen, cyano, nitro, d-₁₂ alkyl, d-₁₂ haloalkyl, d-₁₂ alkoxy, d-₁₂ haloalkoxy and Ci_i₂ alkoxy-carbonyl, among the definitions, each group from d-₁₂ alkyl to Ci_i₂ alkoxy-carbonyl is optionally substituted.

The pyrroline N-oxides according to claim 1, wherein

T is one of the followin groups (Tl) to (T4) or

wherein in group (T5) A¹, A² and A³ are C-Y or nitrogen;

G is fluorine, or the following hetero

G6

wherein (Z) is CN, N0₂, halogen, and k is 0, 1 or 2; R is Ci-6 alkyl or Ci_₆ haloalkyl; is hydrogen, amino, hydroxy, cyano, Ci_₆ alkoxy, Ci_₆ alkyl-carbonylamino, Ci_₆ alkylimino, Ci-6 alkyl, C₃_₇ cycloalkyl, C₂-4 alkenyl, C₂-4 alkynyl, Ci_₆ alkyl-carbonyl, CH₂-R⁶, C(=0)R⁶ or C(=S)R⁶, and among the definitions of R¹, each group from Ci_₆ alkoxy to Ci_₆ alkyl- carbonyl is optionally substituted; is hydrogen, cyano, carbonyl, thiocarbonyl, Ci_₆ alkyl-carbonyl, Ci_₆ alkyl-thiocarbonyl, Ci_₆ haloalkyl-carbonyl, Ci_₆ haloalkyl-thiocarbonyl, Ci_₆ alkyl-aminocarbonyl, Ci_₆ alkylamino- thiocarbonyl, C₂-₁₂ dialkylamino-carb onyl , C₂-₁₂ dialkylamino-thiocarbonyl, Ci_₆ alkoxyamino-carbonyl, Ci_₆ alkoxyamino-thiocarbonyl, Ci_₆ alkoxy-carbonyl, Ci_₆ alkoxy- thiocarbonyl, Ci_₆ alkylthio-carbonyl, Ci_₆ alkylthio-thiocarbonyl, Ci_₆ alkylsulfonyl, Ci_₆ haloalkylsulfonyl, C₃_₇ cycloalkyl-carbonyl, C₂-4 alkenyl-carbonyl, C₂-e alkynyl-carbonyl, C₃_ 7 cycloalkyl-Ci-4 alkyl-carbonyl, Ci_₆ alkylthio-Ci_₆ alkyl-carbonyl, Ci_₆ alkylsulfmyl-Ci_₆ alkyl-carbonyl, Ci_₆ alkylsulfonyl-Ci_₆ alkyl-carbonyl, Ci_₆ alkyl-carbonyl-Ci_₆ alkyl- carbonyl, C3-7 cycloalkylamino-carbonyl, C₂-4 alkenylamino-carbonyl, C₂-4 alkynylamino- carbonyl, C(=0)R⁶ or C(=S)R⁶, and among the definitions of R², each group from Ci_₆ alkyl- carbonyl to C₂-4 alkynylamino-carbonyl is optionally substituted; and R² may form, together with a nitrogen atom to which they are bonded, a 3- to 6-membered heterocycle, and the heterocycle may be substituted with X as described below, oxo, thioxo or nitroimino; is hydrogen, cyano, Ci_₆ alkyl which is optionally substituted or Ci_₆ haloalkyl which is optionally substituted; is hydrogen, Ci_₆ alkyl, Ci_₆ alkyl-carbonyl or Ci_₆ alkoxy-carbonyl; preferably R⁴ is hydrogen, Ci_₄ alkyl, Ci_₄ alkyl-carbonyl or Ci_₄ alkoxy-carbonyl; is phenyl which is optionally substituted or a 5- to 6-membered heterocyclic group which is optionally substituted; preferably R⁶ is phenyl which is optionally substituted or a 5- to 6- membered heterocyclic group which is optionally substituted, is C-X, with X being halogen or C-H, or N;

is 1 or 2;

is 0, 1, 2, 3 or 4;

is 0, 1 or 2;

X is halogen, nitro, cyano, Ci_₆ alkyl, Ci_₆ alkoxy, Ci_₆ haloalkyl, Ci_₆ haloalkoxy, Ci_₆ alkylthio, Ci_₆ alkylsulfinyl, Ci_₆ alkylsulfonyl, Ci_₆ haloalkylthio, Ci_₆ haloalkylsulfinyl, Ci_₆ haloalkylsulfonyl, acylamino, Ci_₆ alkoxy-carbonylamino, Ci_₆ haloalkoxy-carbonylamino, Ci-6 alkoxyimino, Ci_₆ haloalkoxyimino, Ci_₆ alkylsulfonylamino, sulfur pentafluoride, hydroxy, mercapto or amino, among the definitions of X, each group from Ci_₆ alkyl to Ci_₆ alkylsulfonylamino is optionally substituted;

Y is hydrogen, halogen, nitro, hydroxy, mercapto, cyano, amino, Ci_₆ alkyl, Ci_₆ haloalkyl, C₃_₇ cycloalkyl, C₃_₇ cyclohaloalkyl, Ci_₆ alkoxy, Ci_₆ haloalkoxy, Ci_₆ alkylthio, Ci_₆ alkylsulfinyl, Ci_₆ alkylsulfonyl, Ci_₆ haloalkylthio, Ci_₆ haloalkylsulfinyl, Ci_₆ haloalkylsulfonyl, Ci_₆ alkylsulfonyloxy, Ci_₆ haloalkylsulfonyloxy, Ci_₆ alkylaminosulfonyl, Ci_₆ haloalkylaminosulfonyl, C₂-n dialkylaminosulfonyl, C₂-n di- haloalkyl-aminosulfonyl, Ci_₆ alkylamino, C₂-₁₂ dialkylamino, acylamino, Ci_₆ alkoxy- carbonylamino, Ci-6 haloalkoxy-carbonylamino, Ci_₆ alkylsulfonylamino, Ci_₆ haloalkylsulfonylamino, C₃_i₈ trialkylsilyl, Ci_₆ alkoxyimino, Ci_₆ haloalkoxyimino, Ci_₆ alkoxyimino-Ci-6 alkyl, Ci_₆ haloalkoxyimino-Ci_₆ alkyl, Ci_₆ alkylsulfinylimino, Ci_₆ alkylsulfinylimino-Ci-6 alkyl, Ci_₆ alkylsulfinylimino-Ci_₆ alkyl-carbonyl, Ci_₆ alkylsulfoxyimino, Ci_₆ alkylsulfoxyimino-Ci_₆ alkyl, Ci_₆ alkoxy-carbonyl, Ci_₆ alkyl- carbonyl, aminocarbonyl, Ci_₆ alkylamino-carbonyl, amino-thiocarbonyl, Ci_₆ alkylamino- thiocarbonyl, C₂-₁₂ dialkyliminocarbonyl or C₂-₁₂ dialkylamino-thiocarbonyl;

Z¹, Z² and Z³ each independently represent CH₂, C=0, C=N-OR⁹, N-R⁹, S(0)„, S=N-R⁹ or S(0)=N-R⁹, with the proviso that Z¹, Z² and Z³ do not simultaneously represent CR⁷R⁸;

R⁷ and R⁸ each independently are hydrogen, halogen, Ci_₆ or Ci_₄ alkyl which may be substituted or Ci-6 or Ci-4 haloalkyl which may be substituted;

R⁹ is hydrogen, cyano, nitro, Ci_₆ alkyl, Ci_₆ haloalkyl, C₃_₇ cycloalkyl-Ci_₄ alkyl, Ci_₆ alkyl- carbonyl, Ci-6 haloalkyl-carbonyl, Ci_₆ alkoxy-carbonyl, Ci_₆ haloalkoxy-carbonyl, Ci_₆ alkylsulfonyl, Ci_₆ haloalkylsulfonyl, C₆_i₀ aryl-Ci_₄ alkyl or heteroaryl-Ci_₄ alkyl, among the definitions of R⁹, each group from Ci-6 alkyl to Ci_₆ haloalkylsulfonyl is optionally substituted, and the aryl moiety in C₆_i₀ aryl-Ci_₄ alkyl and the heteroaryl moiety in heteroaryl-Ci_ alkyl may be substituted with one to three groups selected from a group consisting of halogen, cyano, nitro, Ci_₆ alkyl, Ci_₆ haloalkyl, Ci_₆ alkoxy, Ci_₆ haloalkoxy and Ci-6 alkoxy-carbonyl, among the definitions, each group from Ci_₆ alkyl to Ci_₆ alkoxy- carbonyl is optionally substituted.

The pyrroline N-oxides according to claim 1 , wherein

T is one of the following group (Tl) to (T4) or

wherein in group (T5) A¹, A² and A³ are C-Y or nitrogen; is fluorine, or the following hetero

G6

wherein (Z) is halogen and k is 0 or 1 ; is CF₃;

hydrogen;

Ci-4 alkyl-carbonyl, C₃_₆ cycloalkyl-carbonyl, or Ci_₄ alkoxy-carbonyl;

is hydrogen, or Ci_₄ alkyl

R⁴ is hydrogen

B is C-Cl or C-H;

j is i ;

m is 0, 1, 2, 3 or 4;

X is CF₃ and/or halogen;

Y is hydrogen, Ci_₄ alkyl, cyano, and/or halogen;

Z¹ and Z³ each are CH₂, and

Z is S.

Use of a compound according to any one of claims 1 to 4 for controlling pests which can damage plants and plant parts and seeds.

Use of a compound according to any one of claims 1 to 4 for the preparation of a pharmaceutical composition.

Pharmaceutical composition comprising one of the compounds according to any one of claims 1 to