WO2005058037A1

WO2005058037A1 - Picolinylpyrazoles as herbicides

Info

Publication number: WO2005058037A1
Application number: PCT/EP2004/014112
Authority: WO
Inventors: Christoph Lüthy; Andrew Edmunds; Renaud Beaudegnies; Sebastian Wendeborn; Jürgen Schaetzer; William Lutz
Original assignee: Syngenta Participations Ag
Priority date: 2003-12-12
Filing date: 2004-12-10
Publication date: 2005-06-30

Abstract

Compounds of formula (I) wherein the substituents are as defined in claim 1, and agronomically acceptable salts/N-oxides/isomers/enantiomers of those compounds are suitable for use as herbicides.

Description

PICOLINYLPYRAZO ES AS HERBICIDES

The present invention relates to novel, herbicidally active picolinoylpyrazoles, to processes for their preparation, to compositions comprising those compounds, and to their use in controlling weeds, especially in crops of useful plants, or in inhibiting plant growth.

Certain herbicidally active derivatives of picolinic acids disubstituted in the 3,5-position are known, such as, for example from EP-A-0316491 , the 3,5-substituted picolinoyl derivatives of 1 ,3-cyclohexanediones substituted in the 2-position and from JP 54009279 the 3,5- substituted picolinoyl derivatives of 2,4-dihydro-3-pyrazolones substituted in the 4-position. EP-A-1 286985 also discloses certain substituted nicotinoylpyrazoles.

It has now been found that picolinoylpyrazoles that are substituted in the 5,6-position of the pyridine and unsubstituted in the 3,4-position of the pyridine exhibit excellent herbicidal and growth-inhibiting properties.

The present invention accordingly relates to compounds of formula I

wherein

R_! is -L₁₀-R_4> -Ln-XrRs, -NR₆R₇, -X₂-R₈ or

L_2> L₄, L-₆ and L₈ are each independently of the others CrC₄alkylene which may be substituted once, twice or three times by CrC₄alkyl, halogen or by C C₄alkoxy and to which ]-C alkylene group there may additionally be spirocyclically bound a C₂-C₅alkylene group, and wherein that C₂-C₅alkylene group may in turn be interrupted once or twice by oxygen, sulfur, sulfinyl or by sulfonyl and/or substituted by CrC₄alkyl or by Cι-C alkoxy; L₃, L₅₎ L and L₉ are each independently of the others C C₄alkylene which may be substituted once, twice or three times by CrC alkyl, halogen or by C C alkoxy; R₂ is halogen, CrC₄haloalkyl, cyano, C C₃haloalkoxy, C C₄alkylthio, C C₄alkylsulfinyl, C C alkylsulfonyl, C C₄haloalkylthio, CrC₄haloalkylsulfinyl or C C₄haloalkylsulfonyl; L₁₀ is a direct bond or a d-C₆alkylene, C₂-C₆alkenylene or C₂-C₆alkynylene group which may be substituted once, twice or three times by O|-C₆alkyl, halogen, hydroxy, C C₆aIkoxy, C₃-C₆cycloalkyloxy, d-Cealkoxy-d-Cealkoxy, d-Cealkoxy-d-Cealkoxy-d-Cealkoxy or by C₁-C₂alkylsulfonyloxy;

R₄ is halogen, cyano, rhodano, d-Cealkoxycarbonyl, C₃-C₆alkenyloxycarbonyl, C₃-C₆alkynyl- oxycarbonyl, benzyloxycarbonyl, C(O)NR₂5aR26a, formyl, d-C₆alkylcarbonyl, d-C₆haloalkyl- carbonyl, Cι-C₄alkoxy-d-C₄alkylcarbonyl, d-dalkoxy-d-dalkoxy-d-dalkylcarbonyl, N- (CrC alkyl)-d-C₄alkylsulfonylamino-CrC₄alkylcarbonyl, d-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆- haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, C₃-C₆cycloalkyl, d-C₆alkylsulfonyloxy or phenyl- sulfonyloxy, wherein the phenyl groups may be substituted by one or more d-C₆alkyl, d-C₆- haloalkyl, Cι-C₆alkoxy, Cι-C₆haloalkoxy, halogen, cyano, hydroxy or nitro groups; or R₄ is a three- to ten-membered, monocyclic or fused bicyclic ring system which may be aromatic, saturated or partially saturated and which may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, and wherein the ring system may contain not more than 2 oxygen atoms and not more than two sulfur atoms, and each ring system may itself be substituted once, twice or three times by d-C₆alkyl, d-Cβhaloalkyl, d-C₄alkoxy- d-C₂alkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, d-C₆alkoxy, hydroxy, d-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, d-C₆alkylthio, d-C₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅alkoxy- alkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C cyanoalkylthio, C C₆alkyl- sulfinyl, CrC₆haloalkylsulfinyl, CrC₆alkylsulfonyl, d-C₆haloalkylsulfonyl, aminosulfonyl, d-Caalkylaminosulfonyl, di(CrC₂alkyl)aminosulfonyl, di(C C alkyl)amino, halogen, cyano, nitro, phenyl or by benzylthio, and wherein phenyl and benzylthio may in turn be substituted on the phenyl ring by d-C₃alkyl, d-C₃haloalkyl, Cι-C₃alkoxy, d-C₃haloalkoxy, halogen, cyano or by nitro, and wherein the substituent on the nitrogen in the heterocyclic ring are other than halogen; or R₄ is hydrogen when L₁₀ is a C C₆alkylene group which may be substituted once, twice or three times by d-C₆alkyl or by halogen; or when L₁₀ is a C₂-C₆alkenylene or C₂-C₆alkynylene group which may be substituted once, twice or three times by d-Cealkyl, halogen, hydroxy, d-C₆alkoxy, C₃-C₆cycloalkyloxy, d-Cβalkoxy-d-Cealkoxy, Ci-Cealkoxy-d-Cealkoxy-Ci-Ce- alkoxy or by C C₂alkylsulfonyloxy;

R₂₅a is hydrogen, d-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-C alkyl, C C₄haloalkyl, C C₃alkoxy, Cι-C₃haloalkoxy, Cι-C₃alkylthio, C C₃alkylsulfinyl, C C₃alkylsulfonyl, C C₃haloalkylthio, cyano, nitro, Cι-C₄alkoxycarbonyl or by d-C alkylcarbonylamino; R_26a is hydrogen, CrCealkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R_25a together with R_26a and the respective N atom to which they are bonded form a carbo- cyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-C₄alkyl, C C₄haloalkyl, C C₃alkoxy, d-C₃- haloalkoxy, d-C₃alkylthio, d-C₃alkylsulfinyl, C C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, Cι-C₄alkoxycarbonyl or by Cι-C₄alkylcarbonylamino;

Ln is a Cι-C₆alkylene, C₂-C₆alkenylene or C₂-C₆alkynylene group which may be substituted once, twice or three times by halogen, hydroxy, d-C₆alkoxy, C₃-C₆cycloalkyloxy, d-C₆- alkoxy-d-C₆alkoxy, CrC₆alkoxy-CrC₆alkoxy-CrC₆alkoxy or by C C₂alkylsulfonyloxy; Xi is oxygen, -OC(O)-, -C(O)-, -C(=NR_14a)-, -C(O)O-, -C(O)NR_14b-, -OC(O)O-, -N(R₁₀)-O-, -O-NRn-, thio, sulfinyl, sulfonyl, -SO NR₁₂-, -NR₁₃SO₂-, -N(SO₂Rι_4c)-, -N(R_14d)C(O)- or -NR₁₄-;

R₁₀, R₁₁, R₁₂, Ri3. Rub, Rι₄d and R are each independently of the others hydrogen, CrC₆alkyl, d-C₆haloalkyl, CrCealkoxycarbonyl, d-C₆alkylcarbonyl, CrC₆alkoxy-CrC₆alkyl, or d-Cealkoxy-CrCealkyl substituted by CrC₆alkoxy, or benzyl or phenyl, wherein phenyl and benzyl may in turn be substituted once, twice or three times by CrC₆alkyl, d-C₆halo- alkyl, CrC₆alkoxy, d-Cehaloalkoxy, halogen, cyano, hydroxy or by nitro; R_14a is hydroxy, d-C₆alkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy or benzyloxy; is C C₆alkyl;

R₅ is hydrogen or a CrC₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl or C₃-C₆cycloalkyl group which may be substituted once, twice or three times by chlorine, bromine, iodine, hydroxy, amino, formyl, nitro, cyano, mercapto, C C₆alkoxy, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, C₃-C₆cycloalkyl, halo-substituted C₃-C₆cycloalkyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, CrC₆haloalkoxy, C₃-C₆haloalkenyloxy, cyano-CrC₆alkoxy, d-C₆alkoxy- C C₆alkoxy, CrC₆alkoxy-CrC₆alkoxy-CrC₆alkoxy, CrC₆alkylthio-CrC₆alkoxy, CrC₆alkyl- sulfinyl-CrC₆alkoxy, CrC₆alkylsulfonyl-CrC₆alkoxy, CrC₆alkoxycarbonyl-CrC₆alkoxy, d-Cealkoxycarbonyl, CrC₆alkylcarbonyl, phenylcarbonyl, CrC₆alkyIthio, CrC₆alkylsulfinyl, d-C₆alkylsulfonyl, CrC₆haloalkylthio, CrC₆haloalkylsulfinyl, CrC₆haloalkylsulfonyl, benzyloxy, benzylthio, benzylsulfinyl, benzylsulfonyl, CrC₆alkylamino, di(CrC₆alkyl)amino, Ri₅aC(X₂₃)N(R_18a)-, R_16aN(R_17a)C(X₂₄)-, R_16bN(R_17b)C(X₂₅)NR_18b-, R₁₅cSO₂N(R_18c)-, Ri₆cN(Rι₇c)C(X₂₆)O-, Ri_5bC(X₂₇)O-, R₁₉R₂₀C=NO-, R₁₅S(O)₂O-, R₁₆N(R₁₇)SO₂-, rhodano, phenyl, phenoxy, phenylthio, phenylsulfinyl or by phenylsulfonyl or which may be substituted from one to seventeen times by fluorine; wherein the phenyl- or benzyl-containing groups may in turn be substituted by one or more CrCealkyl, CrC₆haloalkyl, CrC₆alkoxy, d-C-ehaloalkoxy, halogen, cyano, hydroxy or nitro groups; i₅a, Rιβb and R_15c are hydrogen, CrC₆alkyl, C₂-C₈alkenyl, C₃-C₆cycloalkyl, phenyl, benzyl, CrC₆alkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy or benzyloxy, wherein the phenyl groups may be substituted once, twice or three times by CrC₆alkyl, CrC₆haloalkyl, d-C₆alkoxy, CrC₆haloalkoxy, halogen, cyano, hydroxy or by nitro;

Rιea, i₆b and R_18c are hydrogen, CrC₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, C₃-C₆cycloalkyl or phenyl, wherein phenyl may be substituted once, twice or three times by CrC₆alkyl, CrC₆haloalkyl, CrC₆alkoxy, CrC₆haloalkoxy, halogen, cyano, hydroxy or by nitro; Ri₇a, i7b, i7c_> Risa, ιsb and R_18c are hydrogen, CrC₈alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; X₂₃, X₂₄, X25, X26 and X₂₇ are oxygen or sulfur;

R₁₅, R₁₆. R₁₇, R₁₉ and R₂o are each independently of the others hydrogen, CrC₆alkyl, d-Cehaloalkyl, CrCealkoxycarbonyl, d-C₆alkylcarbonyl, CrCealkoxy-CrCealkyl, or CrC₆alkoxy-CrC₆alkyl substituted by d-C₆alkoxy, or benzyl or phenyl, wherein phenyl and benzyl may in turn be substituted once, twice or three times by CrC₆alkyl, CrC₆haloalkyl, d-C₆alkoxy, d-Cehaloalkoxy, halogen, cyano, hydroxy or by nitro; or R₅ is a three- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic, saturated or partially saturated and may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, and wherein the ring system is bound to the substituent Xi directly or via a d-C alkylene, C₂-C₄alkenylene, C₂-C₄alkynylene, -N(R₁₈)-CrC₄alkylene, -O-d-C₄alkylene, -S-d-C₄alkylene, -S(O)-d-C₄alkylene or -SO₂-C C₄alkylene chain, wherein the ring system may not be interrupted by -C(=O)-, -C(=S)-, -C(=NR_5a)-, -N(=O)-, -S(=O)- or by -SO₂-, and each ring system may contain not more than 2 oxygen atoms and not more than two sulfur atoms, and the ring system itself may be substituted once, twice or three times by CrC₆alkyl, d-Cehaloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, d-C₆alkoxy, hydroxy, d-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, CrC₆alkylthio, CrC₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆- alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄- cyanoalkylthio, CrC₆alkylsulfinyl, CrC₆haloalkylsulfinyl, CrC₆alkylsulfonyl, CrC₆haloalkyl- sulfonyl, aminosulfonyl, CrC₂alkylaminosulfonyl, di(CrC₂alkyl)aminosulfonyl, di(C C₄alkyl)- amino, halogen, cyano, nitro, phenyl or by benzylthio, wherein phenyl and benzylthio may in turn be substituted on the phenyl ring by C C₃alkyl, C C₃haloalkyl, d-C₃aIkoxy, d-C₃- haloalkoxy, halogen, cyano or by nitro, and wherein the substituents on the nitrogen in the heterocyclic ring are other than halogen;

R_5a is CrC₆alkyl, hydroxy, CrC₆alkoxy, cyano or nitro;

R₁₈ is hydrogen, CrC₆alkyl, d-C₆haloalkyl, CrCealkoxycarbonyl, CrC₆alkylcarbonyl,

CrC₆alkoxy-CrC₆alkyl, or CrC₆alkoxy-CrC₆alkyl substituted by CrC₆alkoxy, or benzyl or phenyl, wherein phenyl and benzyl may in turn be substituted once, twice or three times by

CrC₆alkyl, d-Cehaloalkyl, CrC₆alkoxy, CrC₆haloalkoxy, halogen, cyano, hydroxy or by nitro;

R₆ is hydrogen, d-Cealkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, d-Cehaloalkyl, hydroxy, CrC₆alkoxy,

-C(O)R_19a or -C(S)R₂₀a;

Rι_9a and R_20a are each independently of the other hydrogen, d-C₆alkyl, C₃-C₆cycloalkyl, phenyl, benzyl, heteroaryl, CrC₆alkoxy, C₃-C₆alkenyloxy, benzyloxy, CrC₄alkylthio or a group NR21R22;

R₂₁ and R₂₂ are each independently of the other hydrogen, d-C₆alkyl, C₃-C₆alkenyl,

C₃-C₆alkynyl or phenyl, and wherein phenyl, benzyl, benzyloxy and heteroaryl in R_19a, R_20aι

R₂₁ and R₂₂ may be substituted once, twice or three times by halogen, d-dalkyl, d-C₄halo- alkyl, d-C₃alkoxy, CrC₃haloalkoxy, d-C₃alkylthio, d-C₃alkylsulfinyl, CrC₃alkylsulfonyl,

CrC₃haloalkylthio, cyano, nitro, d-C alkoxycarbonyl or by d-C₄alkylcarbonylamino; or R₂ι together with R ₂ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, C C alkyl, d-C₄haloalkyl, CrC₃alkoxy, d-C₃haloalkoxy, d-C₃alkylthio, d-C₃alkylsulfinyl, C C₃alkylsulfonyl, CrC₃haloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by d-C₄alkylcarbonylamino; or R₆ is -L₂-X -R₂₄; wherein

X₄ is oxygen, -NR₂₃-, -S-, -S(O)- or -S(O)₂-;

R₂₃ is hydrogen, CrC₆alkoxy, d-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or is phenyl which may be substituted once, twice or three times by halogen, d-C₄alkyl, d-C₄haloaikyl, d-C₃- alkoxy, C_rC₃haloalkoxy, C C₃alkylthio, Crdalkylsulfinyl, d-C₃alkylsulfonyl, C C₃halo- alkylthio, cyano, nitro, CrC₄alkoxycarbonyl or by Crdalkylcarbόnylamino;

R₂₄ is hydrogen or a CrC₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group, which groups may be substituted once, twice or three times by halogen, hydroxy, CrC₆alkoxy, C_rC₃alkoxy-

C C₃alkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, CrC₆alkylthio, CrC₆alkylsulfinyl, C C₆- alkylsulfonyl, cyano, C(X₅)NR₂5R26_> C₃-C₆cycloalkyl, phenyl, phenoxy or by 5- or 6-membered heteroaryl or heteroaryloxy, wherein heteroaryl or heteroaryloxy may in turn be interrupted once by oxygen or by sulfur or once, twice or three times by nitrogen and may be bonded to the CrC₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group either via a C atom or via a N atom, and wherein the phenyl- and heteroaryl-containing groups may be substituted once, twice or three times by halogen, d-C₄alkyl, d-C haloalkyl, d-C₃alkoxy, CrC₃haloalkoxy, d-C₃alkylthio, Crdalkylsulfinyl, d-C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by d-C₄alkylcarbonylamino; or R₂₄ is C(O)-R₇₄ or C(S)-R₇₅;

X₅ is oxygen or sulfur;

R₂₅ is hydrogen, d-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-C alkyl, d-C₄haloalkyl, CrC₃alkoxy, d-C₃halo- alkoxy, Cι-C₃alkylthio, C C₃alkylsulfinyl, d-C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro,

CrC₄alkoxycarbonyl or by d-C₄alkylcarbonylamino;

R₂₆ is hydrogen, CrC₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₂₅ together with R₂₆ and the respective N atom to which they are bonded form a carbo- cyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-C alkyl, d-C₄haloalkyl, d-C₃alkoxy, d-C₃haloalkoxy, d-C₃alkylthio, d-C₃alkylsulfinyl, d-C₃alkylsulfonyl, CrC₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by CrC₄alkylcarbonylamino; or R₆ is -L₃-R₂₇;

R₂₇ is formyl, CrC₆alkylcarbonyl, C₃-C₆cycloalkylcarbonyl, benzoyl, CrCealkoxycarbonyl, cyano, C(X₆)NR₂₈R_29l phenyl or heteroaryl, wherein benzoyl and phenyl may be substituted once, twice or three times by halogen, d-C₄alkyl, d-C₄haloalkyl, d-C₃alkoxy, d-C₃halo- alkoxy, d-C₃alkylthio, d-C₃alkylsulfinyl, CrC₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by d-C₄aIkylcarbonylamino; and wherein heteroaryl may be substituted once, twice or three times by halogen, d-C alkyl, d-C₄haloalkyl, d-C₃alkoxy, d-C₃haloalkoxy, CrC₃alkylthio, CrC₃alkylsulfinyl, d-C₃alkyl- sulfonyl, d-C₃haloalkylthio, cyano, nitro or by d-C₄alkoxycarbonyl; or R₂₇ is C₃-C₆cycloalkyl or C₅-C₆cycloalkenyl each of which may in turn be substituted once, twice or three times by d-C₄alkyl, halogen or by C_rC alkoxy;

X₆ is oxygen or sulfur;

R₂₈ is hydrogen, d-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-C₄alkyl, d-C₄haloalkyl, d-C₃alkoxy, C C₃halo- alkoxy, d-C₃alkylthio, C C₃alkylsulfinyl, C C₃alkylsulfonyl, C C₃haloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by d-C₄alkylcarbonylamino;

R₂₉ is hydrogen, Cι-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₂₈ together with R₂₉ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-C alkyl, d-dhaloalkyl, d-C₃alkoxy, d-C₃haloalkoxy, Cι-C₃alkylthio, C C₃alkylsulfinyl, d-C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by CrC₄alkylcarbonylamino;

R₇ is hydrogen, CrC₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, d-Cehaloalkyl, C₃-C₆cycloalkyl, phenyl, benzyl, heteroaryl, C(X₇)R₃₀ or NR₃₃R₃₄, wherein phenyl, benzyl and heteroaryl may be substituted once, twice or three times by halogen, d-C₄alkyl, d-C₄haloalkyl, d-C₃- alkoxy, CrC₃haloalkoxy, d-C₃alkylthio, CrC₃alkylsulfinyl, d-C₃alkylsulfonyl, CrC₃halo- alkylthio, cyano, nitro, d-C alkoxycarbonyl or by d-dalkylcarbonylamino;

X₇ is oxygen or sulfur;

R₃₀ is hydrogen, d-C₆alkyl, C₃-C₆cycloalkyl, phenyl, heteroaryl, CrC₆alkoxy, C₃-C₆alkenyl- oxy, benzyloxy, d-C₄alkylthio or a group NR₃₁R₃₂;

R₃ι and R₃₃ are each independently of the other hydrogen, -Cβalkyl, C₃-C₆alkenyl or

C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-C₄alkyl, d-C₄haloalkyl, C C₃alkoxy, d-C₃haloalkoxy, d-C₃alkylthio, d-C₃alkylsulfinyl, d-C₃alkylsulfonyl, CrC₃haloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by d-C₄alkyl- carbonylamino;

R₃₂ and R₃₄ are each independently of the other hydrogen, CrCealkyl, C₃-C₆alkenyl or

C₃-C₆alkynyl; or R₃ι together with R₃₂ or R₃₃ together with R^, in each case with the respective N atom to which they are bonded, form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-C₄alkyl, d-C haloalkyl, d-C₃alkoxy, d-C₃haloalkoxy, d-C₃alkylthio, d-C₃alkylsulfinyl, C C₃alkyl- sulfonyl, d-C₃haloalkylthio, cyano, nitro, C C₄alkoxycarbonyl or by d-C₄alkylcarbonyl- amino; or R₇ is -U-X8-R35; wherein

X₈ is oxygen, -NR₃₆-, -S-, -S(O)- or -S(O)₂-;

R₃₆ is hydrogen, CrC₆alkoxy, CrC₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or is phenyl which may be substituted once, twice or three times by halogen, d-C alkyl, d-C₄haloalkyl, d-C₃- alkoxy, d-C₃haloalkoxy, d-C₃alkylthio, C C₃alkylsulfinyl, CrC₃alkylsulfonyl, C C₃halo- alkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by C C₄alkylcarbonylamino; R₃₅ is hydrogen or a d-Cealkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group, which groups may be substituted once, twice or three times by halogen, hydroxy, d-C₆alkoxy, d-C₃alkoxy- d-C₃alkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, CrC₆alkylthio, CrC₆alkylsulfinyl, d-C₆- alkylsulfonyl, cyano, C(X₉)NR₃₇R₃₈₎ C₃-C₆cycloalkyl, phenyl, phenoxy or by 5- or 6-membered heteroaryl or heteroaryloxy, wherein heteroaryl or heteroaryloxy may in turn be interrupted once by oxygen or by sulfur or once, twice or three times by nitrogen and may be bonded to the Cι-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group either via a C atom or via a N atom, and wherein the phenyl- and heteroaryl-containing groups may be substituted once, twice or three times by halogen, d-C₄alkyl, d-dhaloalkyl, d-C₃alkoxy, C C₃haloalkoxy, d-C₃alkyl- thio, d-C₃alkylsulfinyl, d-C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, C C alkoxy- carbonyl or by CrC₄alkylcarbonylamino; X₉ is oxygen or sulfur;

R₃₇ is hydrogen, Cι-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-C₄alkyl, d-C₄haloalkyl, C C₃alkoxy, d-C₃halo- alkoxy, Cι-C₃alkylthio, d-C₃alkylsulfinyl, C C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by d-C₄alkylcarbonylamino; R₃₈ is hydrogen, d-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₃₇ together with R₃₈ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-C₄alkyl, d-C₄haloalkyl, d-C₃alkoxy, d-C₃haloalkoxy, CrC₃alkylthio, C C₃alkylsulfinyl, CrC₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by d-dalkylcarbonylamino; or R₇ is -L₅-R₃₉;

R₃₉ is formyl, CrC₆alkylcarbonyl, C₃-C₆cycloalkylcarbonyl, benzoyl, CrC₆alkoxycarbonyl, cyano, C(Xι₀)NR₄₀R ι, phenyl or heteroaryl, wherein benzoyl and phenyl may be substituted once, twice or three times by halogen, C C₄alkyl, d-C₄haIoalkyl, C C₃alkoxy, C C₃halo- alkoxy, d-C₃alkylthio, d-C₃alkylsulfinyl, CrC₃alkylsulfonyl, CrC₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-C₄alkylcarbonylamino; and wherein heteroaryl may be substituted once, twice or three times by halogen, d-C₄alkyl, CrC₄haloalkyl, C C₃alkoxy, Cι-C₃haloalkoxy, CrC₃alkylthio, d-C₃alkylsulfinyl, d-C₃alkyl- sulfonyl, d-C₃haloalkylthio, cyano, nitro or by d-C₄alkoxycarbonyl; or R₃₉ is C₃-C₆cycloalkyl or C₅-C₆cycloalkenyl each of which may in turn be substituted once, twice or three times by d-C₄alkyl, halogen or by d-C₄alkoxy; X₁₀ is oxygen or sulfur;

R₄₀ is hydrogen, d-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-C₄alkyl, d-C haloalkyl, d-C₃alkoxy, d-C₃halo- alkoxy, d-C₃alkylthio, CrC₃alkylsulfinyl, d-C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-C₄alkoxycarbonyI or by d-C₄alkylcarbonylamino; R₄ is hydrogen, d-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R^ together with R₄₁ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-C₄alkyl, d-C haloalkyl, d-C₃alkoxy, d-C₃- haloalkoxy, d-C₃alkylthio, d-C₃alkylsulfinyl, d-C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-C alkoxycarbonyl or by CrC₄alkylcarbonylamino; or R₆ and R₇ together with the nitrogen atom to which they are bonded form a carbocyclic 3- to 7-membered, saturated or partially saturated or unsaturated monocyclic or bicyclic ring system which may be interrupted once by oxygen, once by sulfur, from one to three times by nitrogen and/or substituted once, twice or three times by halogen, d-C₄alkyl, d-C₄haloalkyl, d-C₃alkoxy, C C₃haloalkoxy, CrC₃alkylthio, d-C₃alkylsulfinyl, d-C₃alkylsulfonyl, d-C₃- haloalkylthio, cyano, nitro or by d-C₄alkoxycarbonyl; wherein each ring system may not be interrupted by -C(=O)-, -C(=S)-, -C(=NR_5a)-, -N(=O)-, -S(=O)- or by -SO₂-; R_5a is CrC₆alkyl, hydroxy, CrC₆alkoxy, cyano or nitro; X₂ is oxygen, -NR₄₂-, sulfur, -S(O)- or -S(O)₂-;

R₄₂ is hydrogen, d-Cealkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, CrC₆haloalkyl, C₃-C₆cycloalkyl, phenyl, heteroaryl, C(Xn)R₄₃ or NR₄₆R₄₇; Xn is oxygen or sulfur;

R^ is hydrogen, d-C₆alkyl, C₃-C₆cycloalkyl, phenyl, heteroaryl, CrC₆alkoxy, C₃-C₆alkenyl- oxy, benzyloxy, C C₄alkylthio or a group

R^ and R₄₆ are each independently of the other hydrogen, CrC₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-C₄alkyl, C_rC₄haloalkyl, C C₃alkoxy, d-C₃haloalkoxy, C C₃alkylthio, C C₃alkylsulfinyl, C_rC₃alkylsulfonyl, CrC₃haloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by d-dalkyl- carbonylamino;

R^ and R₄₇ are each independently of the other hydrogen, CrC₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or Rψj together with R^ or R^ together with R₄₇, in each case with the respective N atom to which they are bonded, form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-C₄alkyl, d-C₄haloalkyl, CrC₃alkoxy, C C₃haloalkoxy, d-C₃alkylthio, C C₃alkylsulfinyl, C C₃alkyl- sulfonyl, d-C₃haloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by d-C₄alkylcarbonyl- amino; or R₄₂ is wherein

X₁₂ is oxygen, -NR₄₉-, -S-, -S(O)- or -S(O)₂-;

R₄₉ is hydrogen, CrC₆alkoxy, CrC₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or is phenyl which may be substituted once, twice or three times by halogen, d-C₄alkyl, d-C₄haloalkyl, d-C₃- alkoxy, d-C₃haloalkoxy, C C₃alkylthio, C C₃alkylsulfinyl, d-C₃alkylsulfonyl, C C₃halo- alkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by Cι-C alkylcarbonylamino;

R^ is a d-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group, which groups may be substituted once, twice or three times by halogen, hydroxy, CrC₆alkoxy, CrC₃alkoxy-d-C₃alkoxy,

C₃-C₆alkenyloxy, C₃-Cealkynyloxy, CrC₆alkylthio, d-C₆alkylsulfinyl, CrC₆alkylsulfonyl, cyano, C(X ₃)NR₅₀R₅i, C₃-C₆cycloalkyl, phenyl, phenoxy or by 5- or 6-membered heteroaryl or heteroaryloxy, wherein heteroaryl or heteroaryloxy may in turn be interrupted once by oxygen or by sulfur or once, twice or three times by nitrogen and may be bonded to the

CrC₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group either via a C atom or via a N atom, and wherein the phenyl- and heteroaryl-containing groups may be substituted once, twice or three times by halogen, d-C₄alkyl, d-C₄haloalkyl, d-C₃alkoxy, Cι-C₃haloalkoxy, C C₃alkyl- thio, d-C₃alkylsulfinyl, d-C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-C₄alkoxy- carbonyl or by d-C₄alkylcarbonylamino;

X₁₃ is oxygen or sulfur;

R₅₀ is hydrogen, CrC₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-C₄alkyl, d-C₄haloalkyl, C C₃alkoxy, CrC₃halo- alkoxy, d-C₃alkylthio, d-C₃alkylsulfinyl, CrC₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro,

C C₄alkoxycarbonyl or by d-C alkylcarbonylamino;

R₅₁ is hydrogen, d-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₅₀ together with R₅₁ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-C₄alkyl, d-C₄haloalkyl, d-C₃alkoxy,

C C₃haloalkoxy, d-C₃alkylthio, C C₃alkylsulfinyl, C C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by d-C alkylcarbonylamino;

R₅₂ is formyl, CrC₆alkylcarbonyl, C₃-C₆cycloalkyIcarbonyl, benzoyl, CrCealkoxycarbonyl, cyano, CCX JNRssR^, phenyl or heteroaryl, wherein benzoyl and phenyl may be substituted once, twice or three times by halogen, C C₄alkyl, C C₄haloalkyl, d-C₃alkoxy, C C₃halo- alkoxy, CrC₃alkylthio, Cι-C₃alkylsulfinyl, d-C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by Cι-C alkylcarbonylamino; and wherein heteroaryl may be substituted once, twice or three times by halogen, CrC₄alkyl, d-C₄haloalkyl, d-C₃alkoxy, C C₃haloalkoxy, CrC₃alkylthio, C C₃alkylsulfinyl, d-C₃alkyl- sulfonyl, d-C₃haloalkylthio, cyano, nitro or by CrC alkoxycarbonyl; or R₅₂ is C₃-C₆cycloalkyl or C₅-C₆cycloalkenyl each of which may in turn be substituted once, twice or three times by d-C alkyl, halogen or by d-C alkoxy; X is oxygen or sulfur;

R₅₃ is hydrogen, CrC₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-C₄alkyi, d-C haloalkyl, d-C₃alkoxy, d-C₃halo- alkoxy, CrC₃alkylthio, d-C₃alkylsulfinyl, d-C₃alkylsulfonyl, CrC₃haloalkylthio, cyano, nitro, CrC alkoxycarbonyl or by d-C₄alkylcarbonylamino; R₅₄ is hydrogen, CrC₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₅₃ together with R^ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-C₄alkyl, d-C haloalkyl, d-C₃alkoxy, d-C₃- haloalkoxy, d-C₃alkylthio, CrC₃alkylsulfinyl, d-C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-C alkoxycarbonyl or by d-C₄alkylcarbonylamino;

R₈ is hydrogen or a Cϊ-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group, which groups may be substituted once, twice or three times by halogen, hydroxy, d-C₆alkoxy, d-C₃alkoxy- C C₃alkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, CrC₆alkylthio, CrC₆alkylsulfinyl, d-C₆- alkylsulfonyl, cyano, C(Xι₅)NR₅₅R₅₆, C₃-C₆cycloalkyl, phenyl, phenoxy or by 5- or 6- membered heteroaryl or heteroaryloxy, and wherein heteroaryl or heteroaryloxy may in turn be interrupted once by oxygen or by sulfur or once, twice or three times by nitrogen and may be bonded to the CrC₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group either via a C atom or via a N atom, and wherein the phenyl- and heteroaryl-containing groups may be substituted once, twice or three times by halogen, d-C₄alkyl, d-C₄haloalkyl, d-C₃alkoxy, d-C₃haloalkoxy, CrC₃alkylthio, d-C₃alkylsulfinyl, d-C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, Cι-C alkoxycarbonyl or by d-dalkylcarbonylamino; X₁₅ is oxygen or sulfur; R₅₅ is hydrogen, d-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, C C₄alkyl, d-C₄haloalkyl, C C₃alkoxy, C C₃halo- alkoxy, CrC₃alkylthio, d-C₃alkylsulfinyl, C C₃alkylsulfonyl, C C₃haloalkylthio, cyano, nitro,

Cι-C₄alkoxycarbonyl or by d-C alkylcarbonylamino;

R₅₆ is hydrogen, CrC₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₅₅ together with R₅₆ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, C C₄alkyl, d-C₄haloalkyl, d-C₃alkoxy, d-C₃haloalkoxy, d-C₃alkylthio, d-C₃alkylsulfinyl, d-C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by CrC₄alkylcarbonylamino; or R₈ is cyano, C(O)-R₇₆ or C(S)-R₇₇;

X₃ is oxygen, -NR₅₇-, sulfur, -S(O)- or -S(O)₂-;

R₅₇ is hydrogen, Cι-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, CrC₆haloalkyl, C₃-C₆cycloalkyl, phenyl, heteroaryl, C(Xι₆)R₅₈ or NR₆ιR₆₂;

X₁₆ is oxygen or sulfur;

R₅₈ is hydrogen, CrC₆alkyl, C₃-C₆cycloalkyl, phenyl, heteroaryl, d-C₆alkoxy, C₃-C₆alkenyl- oxy, benzyloxy, d-C₄alkylthio or a group NR₅₉R₆o;

R₅₉ and R₆ι are each independently of the other hydrogen, CrC₆alkyl, C₃-C₆alkenyl or

C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-C₄alkyl, d-C₄haloalkyl, CrC₃alkoxy, CrC₃haloalkoxy, d-C₃alkylthio, C C₃alkylsulfinyl, d-C₃alkylsulfonyl, C C₃haloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by d-C alkyl- carbonylamino;

R₆₀ and R₆₂ are each independently of the other hydrogen, CrC₆alkyl, C₃-C₆alkenyl or

C₃-C₆alkynyl; or R₅₉ together with R₆₀ or R₆ι together with R₆₂, in each case with the respective N atom to which they are bonded, form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-C₄alkyl, d-C₄haloalkyl, d-C₃alkoxy, d-C₃haloalkoxy, d-C₃alkylthio, CrC₃alkylsulfinyl, d-C₃alkyl- sulfonyl, CrC₃haloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by C C₄alkylcarbonyl- amino; or R₅ is -L₈-X₁₇-R₆₃; wherein

X₁₇ is oxygen, -NR₆ -₎ -S-, -S(O)- or -S(O)₂-;

R^ is hydrogen, d-C₆alkoxy, CrC₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or is phenyl which may be substituted once, twice or three times by halogen, C C₄alkyl, d-C₄haloalkyl, d-C₃- alkoxy, d-C₃haloalkoxy, d-C₃alkylthio, C C₃alkylsulfinyl, d-C₃alkylsulfonyl, C C₃haIo- alkylthio, cyano, nitro, d-C alkoxycarbonyl or by d-C₄alkylcarbonylamino;

R₆₃ is a CrC₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group, which groups may be substituted once, twice or three times by halogen, hydroxy, CrC₆alkoxy, CrC₃alkoxy-d-C₃alkoxy,

C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, CrC₆alkylthio, CrC₆alkylsulfinyl, CrC₆alkylsulfonyl, cyano, C(X₁₈)NR₆₅R6₆. C₃-C₆cycloalkyl, phenyl, phenoxy or by 5- or 6-membered heteroaryl or heteroaryloxy, wherein heteroaryl or heteroaryloxy may in turn be interrupted once by oxygen or by sulfur or once, twice or three times by nitrogen and may be bonded to the

CrCealkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group either via a C atom or via a N atom, and wherein the phenyl- and heteroaryl-contaϊning groups may be substituted once, twice or three times by halogen, C C₄alkyl, d-C₄haloalkyl, d-C₃alkoxy, d-C₃haloalkoxy, C C₃alkyl- thio, d-C₃alkylsulfinyl, d-C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-C₄alkoxy- carbonyl or by d-C₄alkylcarbonylamino;

X₁₈ is oxygen or sulfur;

R₆₅ is hydrogen, d-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-C₄haloalkyl, d-C₃alkoxy, d-C₃halo- alkoxy, d-C₃alkylthio, d-C₃alkylsulfinyl, C C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by CrC₄alkylcarbonylamino;

R₆₆ is hydrogen, CrC₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₆₅ together with R₆₆ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, C C₄alkyl, d-C₄haloalkyl, C C₃alkoxy, d-C₃haloalkoxy, d-C₃alkylthio, d-C₃alkylsulfinyl, C C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by d-C₄alkylcarbonylamino; or R₅₇ is -L₉-R₆₇;

R₆ is formyl, CrC₆alkylcarbonyl, C₃-C₆cycloalkylcarbonyl, benzoyl, d-C₆alkoxycarbonyl, cyano, C(Xι₉)NR₆₈R₆₉, phenyl or heteroaryl, wherein benzoyl and phenyl may be substituted once, twice or three times by halogen, d-dalkyl, d-C₄haloalkyl, d-C₃alkoxy, d-C₃halo- alkoxy, d-C₃alkylthio, d-C₃alkylsulfinyl, C C₃alkylsulfonyl, CrC₃haloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by d-C₄alkylcarbonylamino; and wherein heteroaryl may be substituted once, twice or three times by halogen, d-C₄alkyl,

CrC₄haloalkyl, d-C₃alkoxy, C C₃haloalkoxy, C C₃alkylthio, d-C₃alkylsulfinyl, d-C₃alkyl- sulfonyl, CrC₃haloalkylthio, cyano, nitro or by d-C₄alkoxycarbonyl; or R₆ is C₃-C₆cycloalkyl or C₅-C₆cycloalkenyl each of which may in turn be substituted once, twice or three times by d-C alkyl, halogen or by C C₄alkoxy; X₁₉ is oxygen or sulfur;

R₆₈ is hydrogen, C C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-C haloalkyl, d-C₃alkoxy, C C₃halo- alkoxy, d-C₃alkylthio, C_rC₃alkylsulfinyl, C C₃alkylsulfonyl, CrC₃haloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by d-C alkylcarbonylamino R₆₉ is hydrogen, d-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₆₈ together with R₆₉ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, C C₄alkyl, d-C₄haloalkyl, d-C₃alkoxy, d-C₃haloalkoxy, d-C₃alkylthio, d-C₃alkylsulfinyl, d-C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by d-dalkylcarbonylamino; L_t is CrC alkylene which may be substituted once, twice or three times by d-C₄alkyl, halogen or by d-dalkoxy and to which d-C₄alkylene group there may be spirocyclically bound a further C -C₅alkylene group which may in turn be interrupted once or twice by oxygen, sulfur, sulfinyl or by sulfonyl and/or substituted by d-C₄alkyl or by d-C alkoxy; or is d-C₄alkylene which may be substituted once, twice or three times by d-C₄alkyl, halogen or by d-C alkoxy, and wherein a carbon atom of that d-C alkylene group together with R₉ or with R₇₀ forms, by means of a further C₂-C₈alkylene chain, a ring system which may additionally be interrupted once or twice by oxygen, sulfur, sulfinyl or by sulfonyl and/or substituted by d-C₄alkyl or by d-C₄alkoxy; R₉ is a group -X20-R70, wherein X₂₀ is oxygen, -NR₇r, -S-, -S(O)- or -S(O)₂-;

R₇₁ is hydrogen or a d-Cealkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group, which groups may be substituted once, twice or three times by halogen, hydroxy, CrC₆alkoxy, d-C₃alkoxy- d-C₃alkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, d-C₆alkylthio, CrC₆alkylsulfinyl, d-C₆- alkylsulfonyl, cyano, C(X₂ι)NR₇₂R ₃, C₃-C₆cycloalkyl, phenyl, phenoxy or by 5- or 6- membered heteroaryl or heteroaryloxy, wherein heteroaryl or heteroaryloxy may in turn be interrupted once by oxygen or by sulfur or once, twice or three times by nitrogen and may be bonded to the CrC₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group either via a C atom or via a N atom, and wherein the phenyl- and heteroaryl-containing groups may be substituted once, twice or three times by halogen, d-dalkyl, C C₄haloalkyl, C C₃alkoxy, d-C₃haloalkoxy, d-C₃alkylthio, C C₃alkylsulfinyl, C C₃alkylsulfonyl, d-C₃haloalkyIthio, cyano, nitro, Crdalkoxycarbonyl or by d-C₄alkylcarbonylamino; X₂₁ is oxygen or sulfur;

R₇₂ is hydrogen, CrC₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-C₃alkoxy, C C₃halo- alkoxy, CrC₃alkylthio, d-C₃alkylsulfinyl, CrC₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-C₄alkylcarbonylamino; R₇₃ is hydrogen, d-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₇₂ together with R₇₃ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-C₄haloalkyl, d-C₃alkoxy, d-C₃haloalkoxy, C C₃alkylthio, C C₃alkylsulfinyl, d-C₃alkylsulfonyl, C C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-C₄alkylcarbonylamino; R₇₀ is hydrogen or a Crdalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group, which groups may be substituted once, twice or three times by halogen, hydroxy, CrC₆alkoxy, d-C₃alkoxy- d-C₃alkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, CrC₆alkylthio, d-C₆alkylsulfinyl, d-C₆- alkylsulfonyl, cyano, C(X _5a)NR_55aR_56a, C₃-C₆cycloalkyl, phenyl, phenoxy or by 5- or 6- membered heteroaryl or heteroaryloxy, and wherein heteroaryl or heteroaryloxy may in turn be interrupted once by oxygen or by sulfur or once, twice or three times by nitrogen and may be bonded to the CrC₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group either via a C atom or via a N atom, and wherein the phenyl- and heteroaryl-containing groups may be substituted once, twice or three times by halogen, d-C₄alkyl, d-C haloalkyl, d-C₃alkoxy, d-C₃haloalkoxy, d-C₃alkylthio, d-C₃alkylsulfinyl, d-C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-C alkoxycarbonyl or by d-dalkylcarbonylamino; X_15a is oxygen or sulfur; _55a is hydrogen, d-Cealkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-C₄alkyl, d-dhaloalkyl, d-C₃alkoxy, d-C₃haloalkoxy, d-C₃alkylthio, d-C₃alkylsulfinyl, d-C₃alkylsulfonyl, C C₃haloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by Cι-C₄alkylcarbonylamino; R_56a is hydrogen, CrC₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R_55a together with R_56a and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-C₃alkoxy, d-C₃haloalkoxy, d-C₃alkylthio, CrC₃alkylsulfinyl, C C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by d-dalkylcarbonylamino; or R₇₀ is d-Cι₀alkylideneimino, (phenyl-C C₄alkylidene)imino, or phenyl, wherein phenyl may be substituted once, twice or three times by halogen, C C₄alkyl, d-C₄haloalkyl, C C₃- alkoxy, C C₃haloalkoxy, C C₃alkylthio, CrC₃alkylsulfinyl, C C₃alkylsulfonyl, d-dhalo- alkylthio, cyano, nitro, C C₄alkoxycarbonyl or by d-C₄alkylcarbonylamino; or R₇₀ is cyano, C(O)-R₇₈ or C(S)-R₇₉; or R₉ is formyl, CrC₆alkylcarbonyl, C₃-C₆cycloalkylcarbonyl, benzoyl, CrCealkoxycarbonyl, cyano, C(X₃5)NR₁₂5Ri2e, phenyl or heteroaryl, wherein benzoyl and phenyl may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-C₃alkoxy, d-C₃haloalkoxy, d-C₃alkylthio, C C₃alkylsulfinyl, d-C₃alkylsulfonyl, C C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by Crdalkylcarbonylamino; and wherein heteroaryl may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, C C₃alkoxy, d-C₃haloalkoxy, d-C₃alkylthio, C C₃alkylsulfinyl, C C₃alkyl- sulfonyl, Cι-C₃haloalkylthio, cyano, nitro or by d-dalkoxycarbonyl; or R₉ is C₃-C₆cycloalkyl or C₅-C₆cycloalkenyl each of which may in turn be substituted once, twice or three times by d-dalkyl, halogen or by C C₄alkoxy;

X₃₅ is oxygen or sulfur;

R₁25 is hydrogen, Crdalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-C₃alkoxy, d-C₃haloalkoxy, d-dalkylthio, d-C₃alkylsulfinyl, d-C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; ₁₂₆ is hydrogen, d-Cealkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₁₂₅ together with R₁₂₆ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-me'mbered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-C₃haloalkoxy, d-C₃alkylthio, Crdalkylsulfinyl, d-dalkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by d-dalkylcarbonylamino;

R74, R75, R76, R77, R78 and R₇₉ are each independently of the others hydrogen, Cι-C₆alkyl,

C₃-C₆cycloalkyl, phenyl, benzyl, heteroaryl, Crdalkoxy, C₃-C₆alkenyloxy, benzyloxy,

C C alkylthio or NR₁₂₇R₁₂₈, wherein phenyl, benzyl or heteroaryl may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, C C₃alkoxy, d-dhaloalkoxy, d-C₃alkylthio, d-C₃alkylsulfinyl, d-C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino;

R127 is hydrogen, d-Cealkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-C₃alkoxy, d-C₃haloalkoxy, d-C₃alkylthio, d-C₃alkylsulfinyl, CrC₃alkylsulfonyl, C C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by CrC₄alkylcarbonylamino;

R₁₂₈ is hydrogen,drC₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or Ri₂₇ together with R₁₂₈ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-C₃alkoxy, d-C₃haloalkoxy, d-C₃alkylthio, C_rC₃alkylsulfinyl, d-C₃alkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino;

R₈₀ and R₈ι are each independently of the other hydrogen, d-dalkyl, cyclopropyl, allyl or propargyl;

X₂₂ is hydroxy, O^'M⁺ wherein M⁺ is an alkali metal cation or ammonium cation, or is halogen, d-C₁₂alkylthio, Crd₂alkylsulfinyl, Crd₂alkylsulfonyl, CrC₁₂haloalkylthio, d-C₁₂halo- alkylsulfinyl, CrC₁ haloalkylsulfonyl, CrC₆alkoxy-CrC₆alkylthio, CrC₆alkoxy-CrC₆alkyl- sulfinyl, CrC₆alkoxy-CrC₆alkylsulfonyl, C₃-C₁₂alkenylthio, C₃-C₁₂alkynylthio, d-dalkoxy- carbonyl-d-dalkylthio, CrC alkoxycarbonyl-d-C₄alkylsulfinyl, d-dalkoxycarbonyl-d-d- alkylsulfonyl, d-C^alkylsulfonyloxy, phenylsulfonyloxy, d-C₈alkoxy, d-C₈alkenyloxy, d-C₈- alkynyloxy, d-C₈haloalkoxy, benzyloxy or benzoylmethoxy, wherein the phenyl-containing groups may be substituted once or more than once by R₈₂;

R₈₂ is halogen, d-C₃alkyl, CrC₃haloalkyl, hydroxy, CrC₃alkoxy, d-C₃haloalkoxy, cyano or nitro; and also to agronomically acceptable salts, tautomers, isomers and enantiomers of those compounds.

The alkyl groups in the substituent definitions may be straight-chained or branched and are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl and octyl and branched isomers thereof. Alkoxy, alkylthio, alkenyl and alkynyl radicals are derived from the mentioned alkyl radicals. The alkenyl and alkynyl groups may be mono- or poly-unsaturated, in which case an allenyl group and a mixed alkene-alkynyl group are also included.

Alkoxy groups are accordingly methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec- butoxy, isobutoxy, tert-butoxy. Alkylthio groups and oxidised forms thereof preferably have a chain length of from 1 to 3 carbon atoms; preference is given to, for example, methylthio, ethylthio, n-propylthio and isopropylthio; especially methyl- and ethyl-thio. Alkylsulfinyl is, for example, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl or isopropylsulfinyl, and alkylsulfonyl is preferably methylsulfonyl, ethylsulfonyl, propylsulfonyl or isopropylsulfonyl; preferably methylsulfonyl or ethylsulfonyl.

Halogen is generally fluorine, chlorine, bromine or iodine; preferably fluorine, chlorine or bromine. Halo-substituted alkyl groups, that is to say haloalkyl groups, preferably have a chain length of from 1 to 6 carbon atoms. d-C₄Haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoro- ethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1 ,1-difluoro-2,2,2-trichloroethyl, 2,2,2- trichloroethyl, 1 ,1 ,2,2-tetrafluoroethyl, 2,2,3,3-tetrafluoropropyl, 2,2,3,3,3-pentafluoropropyl or 2,2,3,4,4,4-hexafluorobutyl; preferably fluoromethyl, difluoromethyl, difluorochloromethyl, dichlorofluoromethyl, trifluoromethyl, 2-chloroethyl, 2,2,2-trifluoroethyl, 2,2,3,3-tetrafluoropropyl or 2,2,3,3,3-pentafluoropropyl.

As haloalkenyl groups, alkenyl groups substituted once or more than once by halogen are suitable, halogen being especially fluorine or chlorine, for example 2,2-difluoro-1-methylvinyl, 3-fluoropropenyl, 3-chloropropenyl, 3-bromopropenyl, 2,3,3-trifluoropropenyl, 2,3,3-trichloro- propenyl or 4,4,4-trif luoro-but-2-en-1 -yl. As haloalkynyl, for example alkynyl groups substituted once or more than once by halogen are suitable, halogen being bromine or iodine or also fluorine or chlorine, for example 3-fluoropropynyl, 3-chloropropynyl, 3-bromopropynyl, 3,3,3-trif luoropropynyl or 4,4,4-trif luoro-but-2-yn-1 -yl. The same is also correspondingly true for halogen in association with other definitions such as haloalkoxy, haloalkylthio, haloalkyl- sulfinyl, haloalkylsulfonyl or halophenyl.

The definition of R₄ or R₅ as a three- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic, partially saturated or fully saturated and which may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, and wherein the ring system is bound to the substituent -i either directly or via a d-dalkylene, C₂-C₄alkenylene, C₂-C₄alkynylene, -N(R₁₈)-d-C₄alkylene, -O-C_rC alkylene, -S-d-C₄alkylene, -S(O)-CrC aIkylene or -SO₂-d-C₄alkylene group, and each ring system may contain not more than 2 oxygen atoms and not more than two sulfur atoms, and the ring system may itself be substituted, is to be understood in the context of the present invention as meaning, for example, phenyl, naphthyl, indenyl, cyclopentenyl, cyclohexenyl or C₃-C₈cycloalkyl, C₃-C₆oxacycloalkyl, C₂-C₅dioxacycloalkyl or similar ring systems, such as especially aromatic five- or six-membered heteroaryl groups containing from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, and partially or fully saturated three- to six-membered ring systems which especially contain 1 or 2 oxygen atoms, such as, for example, oxiranyl, oxetan-3-yl, tetrahydrofuran-3-yl, tetrahydropyran-2-yl, 1 ,3-dioxacyclopent-2-yl, 1 ,3-dioxa- cyclopent-4-yl, 1 ,3-dioxacyclohex-2-yl, 1 ,3-dioxacyclohex-5-yl or cis- and/or trans-1 ,3-dioxa- 4,5-dimethyl-cyclopent-2-yl, or fully saturated three- to six-membered ring systems that contain 1 or 2 sulfur atoms, such as, for example, 1 ,3-oxathio-cyclopent-2-yl, tetrahydro- thien-2-yl, 1 ,3-oxathio-cyclopent-2-yl or 1 ,3-dithiacyclopent-2-yl.

Heteroaryl, such as, for example, in the definition of R₆, R₇, R₈ or R₉ or in the case of a five- or six-membered, monocyclic or fused bicyclic, aromatic ring system R₄ or R₅, is understood to be especially an aromatic 5- or 6-membered heteroaryl group bonded via a carbon atom, which group may be interrupted once by oxygen, once by sulfur and/or once, twice or three times by nitrogen, for example 1 -methyl-1 H-pyrazol-3-yl, 1 -ethyl-1 H-pyrazol-3-yl, 1-propyl- 1 H-pyrazol-3-yl, 1 H-pyrazol-3-yl, 1 ,5-dimethyl-1 H-pyrazol-3-yl, 4-chloro-1 -methyl-1 H-pyrazol- 3-yl, 3-isoxazolyl, 5-methyl-3-isoxazolyl, 3-methyl-5-isoxazolyl, 5-isoxazolyl, 1 H-pyrrol-2-yl, 1 - methyl-1 H-pyrrol-2-yl, 1 -methyl-1 H-pyrrol-3-yl, 2-furyl, 5-methyl-2-furyl, 3-furyl, 5-methyl-2- thienyl, 2-thienyl, 3-thienyl, 1 -methyl-1 H-imidazol-2-yl, 1 H-imidazol-2-yl, 1 -methyl-1 H-imid- azol-4-yl, 1 -methyl-1 H-imidazol-5-yl, 4-methyl-2-oxazolyl, 5-methyl-2-oxazolyl, 2-oxazolyl, 2- methyl-5-oxazolyl, 2-methyl-4-oxazolyl, 4-methyl-2-thiazolyl, 5-methyl-2-thiazolyl, 2-thiazolyl, 2-methyl-5-thiazolyl, 2-methyl-4-thiazolyl, 3-methyl-4-isothiazolyl, 3-methyl-5-isothiazolyl, 5- methyl-3-isothiazolyl, 1 -methyl-1 H-1 ,2,3-triazol-4-yl, 2-methyl-2H-1 ,2,3-triazol-4-yl, 4-methyl- 2H-1 ,2,3-triazol-2-yl, 1 -methyl-1 H-1 ,2,4-triazol-3-yl, 1 ,5-dimethyl-1 H-1 ,2,4-triazol-3-yl, 4,5- dimethyl-4H-1 ,2,4-triazol-3-yl, 4-methyl-4H-1 ,2,4-triazol-3-yl, 5-methyl-1 ,2,3-oxadiazol-4-yl, 1 ,2,3-oxadiazol-4-yl, 3-methyl-1 ,2,4-oxadiazol-5-yl, 5-methyl-1 ,2,4-oxadiazol-3-yl, 5-methyl- 1 ,2,3-thiadiazol-4-yl, 1 ,2,3-thiadiazol-4-yl, 3-methyl-1 ,2,4-thiadiazol-5-yl, 5-methyl-1 ,2,4- thiadiazol-3-yl, 4-methyl-1 ,2,5-thiadiazol-3-yl, 5-methyl-1 ,3,4-thiadiazol-2-yl, 2-pyridyl, 6- methyl-2-pyridyl, 4-pyridyl, 3-pyridyl, 6-methyl-3-pyridazinyl, 5-methyl-3-pyridazinyl, 3-pyrid- azinyl, 4,6-dimethyl-2-pyrimidinyl, 4-methyl-2-pyrimidinyl, 2-pyrimidinyl, 2-methyl-4-pyrimid- inyl, 2-chloro-4-pyrimidinyl, 2,6-dimethyl-4-pyrimidinyl, 4-pyrimidinyl, 2-methyl-5-pyrimidinyl, 6-methyl-2-pyrazinyl, 2-pyrazinyl, 4,6-dimethyl-1 ,3,5-triazin-2-yl, 4,6-dichloro-1 ,3,5-triazin-2- y|, 1 ,3,5-triazin-2-y|, 4-methyl-1 ,3,5-triazin-2-yl, 3-methyl-1 ,2,4-triazin-5-yl or 3-methyl-1 ,2,4- triazin-6-yl. A heteroaryl group bonded via the N atom is understood to be, for example, 1 H- pyrrol-1-yl, 1H-pyrazol-1-yl, 3-methyl-1H-pyrazol-1-yl, 3,5-dimethyl-1H-pyrazol-1-yl, 3- trif luoromethyl-1 H-pyrazol-1 -yl, 3-methyl-1 H-1 ,2,4-triazol-1 -yl, 5-methyl-1 H-1 ,2,4-triazol-1 -yl or 4H-1 ,2,4-triazol-4-yl.

The definition of as d-C₄alkylene which may be substituted once, twice or three times by d-dalkyl, halogen or by d-dalkoxy, wherein a carbon atom of the chain forms together with R₉ a C₂-C₆alkylene chain which may be interrupted once or twice by oxygen, sulfur, sulfinyl or by sulfonyl and may be substituted by d-dalkyl or by d-dalkoxy, is to be understood in the context of the present invention as being, for example, the following cyclic C₂-C₆alkylene groups: C₃-C₆oxacycloalkyl, C₂-C₅dioxacycloalkyl, C₃-C₆oxacycloalkyl- Crdalkyl, C₃-C₆dioxacycloalkyl-CrC₂alkyl or similar oxygen- or sulfur-containing groups, especially a C₃-C₆cycloalkyl group interrupted once or twice by oxygen, such as, for example, oxetan-3-yl, tetrahydrofuran-3-yl, tetrahydropyran-2-yl, 1,3-dioxacyclohex-4-yl, or

wherein in each case the marked 'C atom is bonded to X₃; or oxiranyl-methyl, 3-oxetanyl- methyl, tetrahydrofuran-3-yl-methyl, tetrahydrofuran-2-yl-methyl, 1 ,3-dioxacyclopent-3-yl- methyl, 1 ,3-dioxa-4,5-dimethyl-cyclopent-3-yl-methyl,

^■CH ₂-<J ^,o» ?

or a C₃-C₆cycloalkyl group interrupted once or twice by sulfur, e.g. 1 ,3-oxathio-cyclopent-2- yl, tetrahydrothien-2-yl-methyl, 1 ,3-oxathio-cyclopent-2-yl-methyl, 1 ,3-dithiacyclopent-2-yl-

methyl,

, wherein in each case the marked 'C atom is bonded to Xv

The definition of NR₆R₇ wherein R₆ together with R₇ and the common N atom forms a carbocyclic 3- to 7-membered, saturated or partially saturated monocyclic or bicyclic ring system is to be understood as meaning, for example, morpholino (=morpholin-4-yl), cis- and/or trans-2,6-dimethylmorpholin-4-yl, thiomorpholin-4-yl, N-methyl-piperidin-1 -yl, 1 H- pyrrol-1-yI, 1H-pyrazol-1-yl, 3-methyl-1H-pyrazol-1-yl, 3,5-dimethyl-1 H-pyrazol-1 -yl, 3- trifluoromethyl-1 H-pyrazol-1 -yl, 3-methyl-1 H-1 ,2,4-triazol-1-yl, 5-methyl-1 H-1 ,2,4-triazol-1-yl, 4H-1 ,2,4-triazol-4-yl, or groups according to the formulae

wherein in each case the marked 'N atom is bonded to the picolinyl group.

The definition of , L₂, L , L₆ and L₈ as d-C₄alkylene, to which d-dalkylene group there may be spirocyclically bound a C₂-C₅alkylene group, is to be understood as meaning, for example, a d-C₃alkylene chain that contains a cyclopropyl group or that is substituted by a 1 ,3-dioxolan-2-yl group, such as, for example,

, wherein in each case the marked 'C atom represents the left-hand side valence of the definitions containing the respective substituent L. For example, in -X₃-l_rR₉ the marked 'C atom is linked to the substituent X₃. In general, such alkylene chains, for example d-dalkylene for U and U, can also be substituted by one or more d-C₃alkyl groups, especially by methyl groups. Such alkylene chains and the alkylene groups interrupted by oxygen or by sulfur are preferably unsubstituted. Preferably, groups containing C₃-C₆cycloalkyl, oxiranyl, oxetanyl, C₃-C₅oxa- cycloalkyl, C₃-C₅thiacycloalkyl, C₃-C₄dioxacycloalkyl, C₃-C₄dithiacycloalkyl or C₃-C₄oxathia- cycloalkyl are also unsubstituted.

In the case that a chemical group is substituted more than once by substituents listed in a list of substituents, such as for example L₂ in the meaning of C C₄alkylene which is substituted twice or three times by d-dalkyl, halogen or by d-dalkoxy, said chemical group can be substituted by different substituents from said list of substituents. The same applies mutatis mutandis for ring systems that are substituted more than once, such as for example R₅ in the meaning of a three- to ten-membered ring system, which is substituted twice or three times by d-Cealkyl, d-C₆haloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, d-dalkoxy, hydroxy, d-Cehaloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, Crdalkylthio, CrC₆haloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆- alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄- cyanoalkylthio, CrC₆alkylsulfinyl, d-C₆haloalkylsulfinyl, CrC₆alkylsulfonyl, d-C₆haloalkyl- sulfonyl, aminosulfonyl, CrC₂alkylaminosulfonyl, di(CrC₂alkyl)aminosulfonyl, di(d-dalkyl)- amino, halogen, cyano, nitro, phenyl or by benzylthio.

The compounds of formula I may occur in various tautomeric forms, as shown by way of example for compounds of formula I wherein X₂₂ is hydroxy by formulae I', I", I'" and I"", the form I" being preferred as isolated form.

When there is a C=C or C=N double bond in compounds of formula I, such as, especially, in the group R^ the compounds of formula I may, when asymmetry exists, be in the Ε' or in the 'Z' form. If a further asymmetric centre is present, for example an asymmetric carbon atom in the group R^ chiral 'R' and 'S' forms may also occur. The present invention accordingly includes also all those stereoisomeric and tautomeric forms of the compound of formula I.

The invention relates also to the salts which the compounds of formula I are able to form preferably with amines, alkali metal and alkaline earth metal cations or quaternary ammonium bases. Suitable salt formers are described, for example, in WO 98/41089. Among the alkali metal and alkaline earth metal hydroxides as salt formers, special mention may be made of the hydroxides of lithium, sodium, potassium, magnesium and calcium, but especially the hydroxides of sodium and potassium. Examples of amines suitable for ammonium salt formation include ammonia as well as primary, secondary and tertiary CrC₁₈alkylamines, d-dhydroxyalkylamines and C₂-C₄alkoxyalkylamines, for example methylamine, ethylamine, n-propylamine, isopropyl- amine, the four butylamine isomers, n-amylamine, isoamylamine, n-hexylamine, heptyl- amine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecyl- amine, octadecylamine, methyl-ethylamine, methyl-isopropylamine, methyl-hexylamine, methyl-nonylamine, methyl-pentadecylamine, methyl-octadecylamine, ethyl-butylamine, ethyl-heptylamine, ethyl-octylamine, hexyl-heptylamine, hexyl-octylamine, dimethylamine, diethylamine, di-n-propylamine, diisopropylamine, di-n-butylamine, di-n-amylamine, diisoamylamine, dihexylamine, diheptylamine, dioctylamine, ethanolamine, n-propanolamine, isopropanolamine, N,N-diethanolamine, N-ethylpropanolamine, N-butylethanolamine, allylamine, n-butenyl-2-amine, n-pentenyl-2-amine, 2,3-dimethylbutenyl-2-amine, dibutenyl- 2-amine, n-hexenyl-2-amine, propylenediamine, trimethylamine, triethylamine, tri-n- propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine, tri-sec-butylamine, tri-n- amylamine, methoxyethylamine and ethoxyethylamine; heterocyclic amines, for example pyridine, quinoline, isoquinoline, morpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine; primary arylamines, for example anilines, methoxyanilines, ethoxyanilines, o-, m- and p-toluidines, phenylenediamines, benzidines, naphthylamines and o-, m- and p- chloroanilines; but especially triethylamine, isopropylamine and diisopropylamine.

Preferred quaternary ammonium bases suitable for salt formation correspond, for example, to the formula [⁺N(R_aR_bR_cR_d) OH] wherein R_a, R_b, R₀ and R_d are each independently of the others d-dalkyl. Other suitable tetraalkylammonium bases with other anions can be obtained, for example, by anion exchange reactions.

In preferred compounds of formula I: a) R₈₀ is methyl, ethyl, isopropyl or propargyl; b) R₈₁ is hydrogen or methyl; c) X₂₂ is hydroxy, a salt of formula O^"M⁺ wherein M is an agronomically acceptable metal cation or ammonium cation, or d-dalkylsulfonyloxy, tosyloxy, especially hydroxy; d) R₂ is chlorine, bromine, cyano, trifluoromethyl, difluoromethyl, difluorochloromethyl, difluoromethoxy, trifluoromethoxy, trifluoroethoxy, difluoromethylthio, trifluoromethylthio, trifluoroethylthio, methylthio, ethylthio, methylsulfonyl or ethylsulfonyl, especially trifluoromethyl; or e) Ri is a group NR₆R₇, a group -X₂-R₈ wherein X₂ is -O- or -NR₄₂-, or a group -X₃-L Rg wherein X₃ is -O- or -NR₅₇-.

In an especially preferred group of compounds of formula I f) R₁ is a group -X₃-L R₉ wherein X₃ is oxygen; g) l_ι is a methylene or ethylene chain which may be substituted by methyl, ethyl, methoxy or by ethoxy, special emphasis being given to those compounds wherein R, as -X₃-L R₉ is the side chain -O-L O-R₇₀ wherein R₇₀ is d-C₃alkyl, allyl, propargyl, d-dalkoxy-Ci-dalkyl or C(O)-R₇₈ and R₇₈ is NR₁₂₇Rι₂₈; h) Ri as -X₃-LrRθ is the group -O-L X2o-R7o wherein X₂₀ is especially oxygen and a carbon atom of the chain U together with R ₀ forms a C₂-C₆alkylene chain which may be interrupted once by oxygen and substituted once or twice by methyl; i) R is -X₃-L X2o-R7o wherein R₇₀ is C(O)NR₇₂R ₃; j) R is the group -O-l_rN(R₇₁)C(O)R₇₈ wherein R₇₁ is especially hydrogen and R₇₈ is especially d-dalkyl, cyclopropyl, phenyl, d-dalkoxy, methylamino or dimethylamino.

In a further especially preferred group of compounds of formula I k) R_! is a group NR₆R₇ or a group -X₃-L Rg wherein X₃ is -NR₅₇- and wherein is a methylene or ethylene chain which may be substituted by methyl, ethyl, methoxy or by ethoxy, and of that group of compounds of formula I special mention should be made of those wherein NR₆R₇ is a heterocyclic group selected from morpholin-4-yl, pyrazol-1-yl and

1 ,2,4-triazoM -yl, and wherein those groups may be substituted by methyl, trifluoromethyl, methoxy or by ethoxy;

I) Ri NR₆R7 wherein R₇ is C(X₇)R₃₀; and preferably R₆ is methyl or ethyl; X₇ is oxygen; and

R₃₀ is d-dalkyl, C₃-C₆cycloalkyl or phenyl.

Also preferred are compounds of formula I wherein at least one of the linking members X₃ and X₂₀ is oxygen; preferably both substituents are oxygen.

L, is preferably an unsubstituted d-C₃alkylene chain or a dalkylene chain substituted once by methyl.

In another outstanding group of compounds m) R is a group -L-n-XrRs wherein L-n is d-C₂alkylene which may be substituted by methyl, ethyl, methoxy or by ethoxy, especially unsubstituted methylene; n) Ri is a group -Ln-X Rs wherein X, is oxygen, -C(O)-, -C(=NR_14a)-, -C(O)O-, -C(O)NR_14b-, sulfur, sulfonyl, -NR₁₃SO₂-, -N(SO₂Rι_4c)- or -NR₁₄- wherein R₁₄ is d-dalkoxycarbonyl or d-Cealkylcarbonyl, X being especially oxygen or -N(SO Rι_4c)-; o) Ri is a group -Ln-XrRs wherein R₅ is CrC₆alkylene which may be substituted by halogen, cyano, d-C₄alkoxy, d-dalkoxycarbonyl, C₂-C alkenyl, C₂-C₄haloalkenyl, C₂-C - alkynyl, C₃-C₆cycloalkyl, C₃-C₄alkenyloxy, C₃-C₄alkynyloxy, d-C₄haloalkoxy, C₃-C halo- alkenyloxy, cyano-C C₃alkoxy or by d-dalkoxy-d-dalkoxy; R₅ being especially d-dalkyl, C₃-C₄alkenyl or C₃-C₄alkynyl, or being CrC₃alkylene which is substituted from one to three times by fluorine, once or twice by chlorine, once or twice by methoxy or by ethoxy, once by cyano, allyloxy, propargyloxy, difluoromethoxy, trifluoromethoxy, methoxyethoxy or by C₃-C₆cycloalkyl; p) Ri is a group -Ln-Xι-R₅ wherein R₅ is phenyl, C₃-C₆cycloalkyl or a three- to six- membered monocyclic ring system which may be aromatic, saturated or partially saturated and contains from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, wherein phenyl or the ring system is bound to the substituent X₁ directly or via a d-C₂alkylene group, and each ring system contains not more than 2 oxygen atoms and not more than two sulfur atoms, and wherein the ring system itself may be substituted from one to four times by d-dalkyl or by halogen and/or once by d-C₃alkoxy, d-dhaloalkoxy, allyloxy, propargyloxy, d-dalkylthio or by d-C₃alkylsulfonyl; R₅ being especially phenyl, C₃-C₆cycloaIkyl or a three- to six-membered monocyclic, saturated ring system which contains 1 or 2 oxygen atoms, and wherein phenyl or the ring system is bound to the substituent Xi either directly or via a d-C₂alkylene group, and wherein preferably the ring system itself is unsubstituted or may be substituted from one to four times by d-C₃alkyl and/or once by methoxy or by ethoxy.

In a very especially preferred group of compounds of formula I wherein q) R is a group -Lπ-XrRs, the bidentate linking member -L_ι Xr is preferably -CH₂O-, -CH₂CH₂O- or -CH₂N(SO₂CH₃)-. Compounds of formula I wherein -Ln-X Rs is CH₂OCH₂CH₂OCH₃, CH₂OCH₂CH₂OCH₂CH₃, CH₂OCH₂CF₃, CH₂OCH₂CH=CH₂, CH₂OCH₂C≡CH, CH₂OCH₂C≡CCH₃, CH₂OCH₂CH₂C≡CH, CH₂OCH₂C≡N, CH₂OCH₂CH₂C≡N, CH₂OCH₂CH₂CH₂OCH₃,

CH₂OCH₂CH₂OCF₃, CH₂OCH₂CH₂CH₂θCF₃,

CH₂N(SO₂CH₃)CH₃, CH2N(SO₂CH₃)CH₂CH₃, CH₂N(SO₂CH₃)CH₂CF₃ or CH₂N(SO₂CH₃)CH₂CH₂θCH₃ are of very special interest.

In a final outstanding group of compounds r) Ri is a group -L₁₀-R wherein L₁₀ is a direct bond or is a d-C₃alkylene or C₂-C₃alkenylene group which may be substituted from one to three times by halogen, methyl, ethyl, methoxy or by ethoxy; especially a direct bond or an unsubstituted d-C₂alkylene chain;

R is a group -L₁₀-R wherein R₄ is halogen or cyano, or is a d-dalkyl group which may be substituted by halogen, methoxy or by ethoxy, or is a three- to six-membered monocyclic ring system which may be saturated, partially saturated or unsaturated and may contain 1 or 2 hetero atoms selected from nitrogen, oxygen and sulfur and may itself be substituted by methyl or methoxy or by methoxymethyl; R-i is especially fluorine, chlorine, bromine, cyano, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, methoxymethyl, ethoxymethyl, tetrahydro- furan-2-yl, tetrahydrofuran-3-yl, 1 ,3-dioxolan-2-yl, 1 ,3-dioxolan-4-yl, (2-methyl-[1 ,3]dioxolan- 2-yl), tetrahydropyran-2-yl, 4,5-dihydro-isoxazol-5-yl, 4,5-dihydro-isoxazol-5-yl or (3-methyl- 4,5-dihydro-isoxazol-5-yl).

Further groups of compounds of formula I that should be given special mention are those wherein X_1f X₂ and X₃ are sulfur, sulfinyl or sulfonyl.

In addition, very special mention should be made of a group of compounds wherein Ri is -L11-X1-R5, -NR₆R₇, -X₂-R₈, -X₃-L Rg, d-dhaloalkyl, C₂-C₆haloalkenyl, C₂-C₆halo- alkynyl or halogen; l_₂, U, L-₆ and L₈ are each independently of the others d-dalkylene which may be substituted once, twice or three times by d-dalkyl, halogen or by d-dalkoxy and to which d-C₄alkylene group there may additionally be spirocyclically bound a C₂-C₅alkylene group, and wherein that C₂-C₅alkylene group may in turn be interrupted once or twice by oxygen, sulfur, sulfinyl or by sulfonyl and/or substituted by d-dalkyl or by d-dalkoxy; L₃, L₅, L₇ and L₉ are each independently of the others d-dalkylene which may be substituted once, twice or three times by d-dalkyl, halogen or by d-dalkoxy; R₂ is halogen, d-dhaloalkyl, cyano, C C₃ha!oalkoxy, d-C₄alkylthio, C C₄alkylsulfinyl, d-C₄alkylsulfonyl, d-dhaloalkylthio, C C₄haloalkylsulfinyl or d-dhaloalkylsulfonyl; L₁₁ is a d-dalkylene, C₂-C₆alkenylene or C₂-C₆alkynylene group which may be substituted once, twice or three times by halogen, hydroxy, d-dalkoxy, C₃-C₆cycloalkyloxy, d-C₆- alkoxy-d-dalkoxy, CrCealkoxy-d-Cealkoxy-Ci-Cealkoxy or by d-C₂alkylsulfonyloxy; is oxygen, -OC(O)-, -C(O)-, -C(=NR_14a)-, -C(O)O-, -C(O)NR_14b-, -OC(O)O-, -N(R₁₀)-O-, -O-NRn-, thio, sulfinyl, sulfonyl, -SO₂NR₁₂-, -NR₁₃SO₂-, -N(SO₂Rι _o)-, -N(R_14d)C(O)- or -NR₁₄-;

R₁0. R11. R12, R₁3, Ri4b.

and R₁₄ are each independently of the others hydrogen, d-dalkyl, d-dhaloalkyl, CrCealkoxycarbonyl, d-dalkylcarbonyl, CrC₆alkoxy-CrC₆alkyl, or CrCealkoxy-CrCealkyl substituted by d-dalkoxy, or benzyl or phenyl, wherein phenyl and benzyl may in turn be substituted once, twice or three times by d-dalkyl, CrCehaloalkyl, d-dalkoxy, d-dhaloalkoxy, halogen, cyano, hydroxy or by nitro; R_{1 a} is hydroxy, d-dalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy or benzyloxy; R_14c is CrC₆alkyl;

R₅ is hydrogen or d-dalkyl, or is a d-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl or C₃-C₆cyclo- alkyl group which is substituted once, twice or three times by halogen, hydroxy, amino, formyl, nitro, cyano, mercapto, carbamoyl, d-C₆alkoxy, C₂-C₆alkenyl, C₂-C₆haloalkenyl, d-dalkynyl, C₂-C₆haloalkynyl, C₃-C₆-cycloalkyl, halo-substituted C₃-C₆cycloalkyl, C₃-C₆- alkenyloxy, C₃-C₆alkynyloxy, CrC₆haloalkoxy, C₃-C₆haloalkenyloxy, cyano-d-C₆alkoxy, d -C₆alkoxy-d -C₆alkoxy, Ci -C₆alkoxy-Cι -C₆alkoxy-d -C₆alkoxy, Cι -C₆alkylthio-d -C₆alkoxy, Crdalkylsulfinyl-Crdalkoxy, CrC₆alkylsulfonyl-CrC₆alkoxy, d-dalkoxycarbonyl- d-C₆alkoxy, CrCealkoxycarbonyl, d-dalkylcarbonyl, d-dalkylthio, CrC₆alkylsulfinyl, d-C₆alkylsulfonyl, CrC₆haloalkylthio, d-dhaloalkylsulfinyl, CrC₆haloalkylsulfonyl, benzyloxy, benzylthio, benzylsulfinyl, benzylsulfonyl, CrC₆alkylamino, di(CrC₆alkyl)amino, R₁₉R₂₀C=NO-, R₁₅S(O)₂O-, R₁₆N(R₁₇)SO₂-, rhodano, phenyl, phenoxy, phenylthio, phenylsulfinyl or by phenylsulfonyl; wherein the phenyl- or benzyl-containing groups may in turn be substituted by one or more d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, halogen, cyano, hydroxy or nitro groups;

R₁₅. Rιe, i7, ₁₉ and R₂o are each independently of the others hydrogen, d-dalkyl, d-dhaloalkyl, d-dalkoxycarbonyl, d-dalkylcarbonyl, Crdalkoxy-d-dalkyl, or Crdalkoxy-Crdalkyl substituted by d-dalkoxy, or benzyl or phenyl, wherein phenyl and benzyl may in turn be substituted once, twice or three times by d-dalkyl, d-dhaloalkyl, CrC₆alkoxy, d-dhaloalkoxy, halogen, cyano, hydroxy or by nitro; or R₅ is a three- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic, saturated or partially saturated and may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, and wherein the ring system is bound to the substituent X directly or via a d-dalkylene, C₂-C₄alkenylene, C₂-C₄alkynylene, -N(R₁₈)-d-C₄alkylene, -S(O)-Crdalkylene or -SO₂-CrC₄alkylene chain, wherein each ring system may not be interrupted by -C(=O)-, -C(=S)-, -C(=NR_5a)-, -N(=O)-, -S(=O)- or by -SO₂-, and each ring system may contain not more than 2 oxygen atoms and not more than two sulfur atoms, and the ring system itself may be substituted once, twice or three times by d-C₆alkyl, CrCehaloalkyl, C₂-C₈alkenyl, C₂-C₆haloalkenyI, C₂-C₆alkynyl, C₂-C₆haloalkynyl, d-dalkoxy, hydroxy, d-dhaloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, d-dalkylthio, d-dhaloalkyl- thio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅- acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C cyanoalkylthio, CrC₆alkylsulfinyl, CrC₆haloalkylsulfinyl, CrC₆alkylsulfonyl, CrC₆haloalkylsulfonyl, aminosulfonyl, d-dalkyl- aminosulfonyl, di(CrC₂alkyl)aminosulfonyl, di(Cι-C₄alkyl)amino, halogen, cyano, nitro, phenyl or by benzylthio, wherein phenyl and benzylthio may in turn be substituted on the phenyl ring by d-dalkyl, C C₃haloalkyl, d-dalkoxy, d-C₃haloalkoxy, halogen, cyano or by nitro, and wherein the substituents on the nitrogen in the heterocyclic ring are other than halogen;

R_5a is CrC₆alkyl, hydroxy, d-dalkoxy, cyano or nitro;

R₁₈ is hydrogen, d-dalkyl, d-dhaloalkyl, d-dalkoxycarbonyl, d-dalkylcarbonyl, d-dalkoxy-d-Cealkyl, or CrCealkoxy-CrCealkyl substituted by d-dalkoxy, or benzyl or phenyl, wherein phenyl and benzyl may in turn be substituted once, twice or three times by CrC₆alkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, halogen, cyano, hydroxy or by nitro; R₆ is hydrogen, d-dalkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, d-Cehaloalkyl, hydroxy, d-dalkoxy,

-C(O)R_19a or -C(S)R₂o_a;

R_19a and R_20a are each independently of the other hydrogen, d-dalkyl, C₃-C₆cycloalkyl, phenyl, heteroaryl, d-dalkoxy, C₃-C₆alkenyloxy, benzyloxy, d-C₄alkylthio or a group

C₃-C₆alkynyl or phenyl, and wherein phenyl may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-C₃alkoxy, d-C₃haloalkoxy, C C₃alkylthio, d-d- alkylsulfinyl, C C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; or R₂₁ together with R₂₂ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, C C₄alkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-C₃alkylsulfinyl, CrC₃alkylsulfonyl, CrC₃haloalkylthio, cyano, nitro, d-Q₄alkoxycarbonyl or by d-dalkylcarbonylamino; or R₆ is -L₂-X₄-R₂₄; wherein t is oxygen, -NR₂₃-, -S-, -S(O)- or -S(O)₂-;

R₂₃ is hydrogen, d-dalkoxy, Crdalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or is phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, C C₃alkylthio, d-C₃alkylsulfinyl, d-dalkylsulfonyl, d-dhalo- alkylthio, cyano, nitro, CrC₄alkoxycarbonyl or by d-C₄alkylcarbonylamino; R₂₄ is hydrogen or a d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group, which groups may be substituted once, twice or three times by halogen, hydroxy, d-dalkoxy, d-dalkoxy- d-dalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, d-C₆alkylthio, CrC₆alkylsulfinyl, d-d- alkylsulfonyl, cyano, C(X₅)NR2₅R26, C₃-C₆cycloalkyl, phenyl, phenoxy or by 5- or 6-membered heteroaryl or heteroaryloxy, wherein heteroaryl or heteroaryloxy may in turn be interrupted once by oxygen or by sulfur or once, twice or three times by nitrogen and may be bonded to the d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group either via a C atom or via a N atom, and wherein the phenyl- and heteroaryl-containing groups may be substituted once, twice or three times by halogen, d-C₄alkyl, d-C₄haloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-C₃alkylsulfinyl, d-dalkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; or R₂₄ is C(O)-R₇₄ or C(S)-R₇₅; X₅ is oxygen or sulfur;

R₂₅ is hydrogen, Crdalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, C C₄haloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; R₂₆ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₂₅ together with R₂₆ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, C_rC₄alkyi, d-C haloalkyl, d-dalkoxy, d-C₃haloalkoxy, d-C₃alkylthio, C C₃alkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, C C₄alkoxycarbonyl or by d-dalkylcarbonylamino; or R₆ is -L₃-R₂₇; R₂₇ is formyl, d-dalkylcarbonyl, C₃-C₆cycloalkylcarbonyl, benzoyl, CrCealkoxycarbonyl, cyano, C(X₆)NR28R29, phenyl or heteroaryl, wherein benzoyl and phenyl may be substituted once, twice or three times by halogen, d-dalkyl, d-C₄haloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, C C₃alkylsulfinyl, d-C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-C alkylcarbonylamino; and wherein heteroaryl may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-C₃haloalkoxy, d-dalkylthio, C C₃alkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro or by d-dalkoxycarbonyl; or R₂₇ is d-dcycloalkyl or C₅-C₆cycloalkenyl each of which may in turn be substituted once, twice or three times by d-dalkyl, halogen or by d-dalkoxy; X₆ is oxygen or sulfur;

R₂₈ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; R₂₉ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₂₈ together with R₂₉ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, Crdalkylthio, d-C₃alkylsulfinyl, C C₃alkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by C C₄alkylcarbonylamino; R₇ is hydrogen, d-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, d-dhaloalkyl, C₃-C₆cycloalkyl, phenyl, heteroaryl, C(X₇)R₃₀ or NR₃₃R₃₄; X₇ is oxygen or sulfur;

R₃₀ is hydrogen, d-dalkyl, C₃-C₆cycloalkyl, phenyl, heteroaryl, d-dalkoxy, C₃-C₆alkenyl- oxy, benzyloxy, d-dalkylthio or a group NR₃₁R₃₂;

R₃ι and R₃₃ are each independently of the other hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, C C₃alkoxy, C C₃haloalkoxy, d-dalkylthio, d-C₃alkylsulfinyl, d-C₃alky!sulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino;

R₃₂ and R₃₄ are each independently of the other hydrogen, d-dalkyl, C₃-C₆alkenyl or d-dalkynyl; or R₃ι together with R₃₂ or R₃₃ together with R₃ , in each case with the respective N atom to which they are bonded, form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, C C₃alkoxy, d-dhaloalkoxy, d-C₃alkylthio, d-dalkylsulfinyl, d-C₃alkyl- sulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; or R₇ is -L₄-X₈-R₃₅; wherein X₈ is oxygen, -NR₃₆-, -S-, -S(O)- or -S(O)₂-;

R₃₆ is hydrogen, Crdalkoxy, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or is phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, Crdhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-C₃alkylthio, d-dalkylsulfinyl, d-C₃alkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-C₄alkylcarbonylamino; R₃₅ is hydrogen or a d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group, which groups may be substituted once, twice or three times by halogen, hydroxy, d-dalkoxy, d-dalkoxy- d-dalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, d-dalkylthio, Crdalkylsulfinyl, d-dalkylsulfonyl, cyano, C(X₉)NR₃₇R₃₈, C₃-C₆cycloalkyl, phenyl, phenoxy or by 5- or 6-membered heteroaryl or heteroaryloxy, wherein heteroaryl or heteroaryloxy may in turn be interrupted once by oxygen or by sulfur or once, twice or three times by nitrogen and may be bonded to the d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group either via a C atom or via a N atom, and wherein the phenyl- and heteroaryl-containing groups may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, Crdhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, C_rC₄alkoxy- carbonyl or by Crdalkylcarbonylamino; X₉ is oxygen or sulfur;

R₃₇ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, C C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; R₃₈ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₃₇ together with R₃₈ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-C₃alkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; or R₇ is -L₅-R₃₉;

R₃₉ is formyl, d-dalkylcarbonyl, C₃-C₆cycloalkylcarbonyl, benzoyl, CrC₆alkoxycarbonyl, cyano, C(X₁₀)NR₄₀R₄ι, phenyl or heteroaryl, wherein benzoyl and phenyl may be substituted once, twice or three times by halogen, d-dalkyl, C C₄haloalkyl, C C₃alkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; and wherein heteroaryl may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-C₃alkoxy, d-C₃haloalkoxy, d-dalkylthio, d-C₃alkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro or by d-dalkoxycarbonyl; or R_3g is C₃-dcycloalkyl or C₅-C₆cycloalkenyl each of which may in turn be substituted once, twice or three times by Crdalkyl, halogen or by d-C₄alkoxy; X₁₀ is oxygen or sulfur;

R₄₀ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, Crdalkylsulfinyl, d-dalkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; R₄ι is hydrogen, Crdalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R^ together with R₄₁ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-C haloalkyl, d-C₃alkoxy, d-dhaloalkoxy, C C₃alkylthio, d-dalkylsulfinyl, C C₃alkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-C₄alkylcarbonylamino; or R₆ and R₇ together with the nitrogen atom to which they are bonded form a carbocyclic 3- to 7-membered, saturated or partially saturated or unsaturated monocyclic or bicyclic ring system which may be interrupted once by oxygen, once by sulfur, from one to three times by nitrogen and/or substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-C₃alkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-d- haloalkylthio, cyano, nitro or by d-dalkoxycarbonyl; wherein each ring system may not be interrupted by-C(=O)-, -C(=S)-, -C(=NR_5a)-, -N(=O)-, -S(=O)- or by -SO₂-; Rεa is d-C₆alkyl, hydroxy, d-dalkoxy, cyano or nitro; X₂ is oxygen, -NR₄₂-, sulfur, -S(O)- or -S(O)₂-;

R₄₂ is hydrogen, d-dalkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, d-Cehaloalkyl, C₃-C₆cycloalkyl, phenyl, heteroaryl, C(Xn)R₄₃ or NR₄₆R₄₇; Xn is oxygen or sulfur; R₄₃ is hydrogen, d-dalkyl, C₃-C₆cycloalkyl, phenyl, heteroaryl, d-C₆alkoxy, C₃-C₆alkenyl- oxy, benzyloxy, d-C₄alkylthio or a group

R_ΨI and R₄₆ are each independently of the other hydrogen, CrCealkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, C C₃alkylthio, d-C₃alkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino;

R₄₅ and R₄₇ are each independently of the other hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-dalkynyl; or Rφi together with R^ or R ₆ together with R₄₇, in each case with the respective N atom to which they are bonded, form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, C C₃haloalkoxy, d-dalkylthio, d-C₃alkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; or R₄₂ is -Le-X^-R^; wherein X₁₂ is oxygen, -NR₄₉-, -S-, -S(O)- or -S(O)₂-;

R₄₉ is hydrogen, d-dalkoxy, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or is phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-C₃alkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-C₄alkylcarbonylamino; R₄₈ is a CrC₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group, which groups may be substituted once, twice or three times by halogen, hydroxy, d-dalkoxy, d-dalkoxy-Crdalkoxy, C₃-dalkenyloxy, C₃-C₆alkynyloxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, cyano, C(X₁₃)NR₅oR₅ι, C₃-C₆cycloalkyl, phenyl, phenoxy or by 5- or 6-membered heteroaryl or heteroaryloxy, wherein heteroaryl or heteroaryloxy may in turn be interrupted once by oxygen or by sulfur or once, twice or three times by nitrogen and may be bonded to the d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group either via a C atom or via a N atom, and wherein the phenyl- and heteroaryl-containing groups may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-C₃haloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkyisulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; X₁₃ is oxygen or sulfur; R₅₀ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-C₄haloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-C₄alkylcarbonylamino; R₅₁ is hydrogen, Crdalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₅₀ together with R₅₁ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, C C₃alkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, C C₃alkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; or R₄₂ is -L₇-R₅₂;

R₅₂ is formyl, d-dalkylcarbonyl, C₃-C₆cycloalkylcarbonyl, benzoyl, d-dalkoxycarbonyl, cyano, C(Xι )NR₅₃R₅₄, phenyl or heteroaryl, wherein benzoyl and phenyl may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-C₃alkylsulfinyl, d-C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-C₄alkylcarbonylamino; and wherein heteroaryl may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-C₃haloalkylthio, cyano, nitro or by d-dalkoxycarbonyl; or R₅₂ is C₃-C₆cycloalkyl or d-dcycloalkenyl each of which may in turn be substituted once, twice or three times by d-dalkyl, halogen or by d-C₄alkoxy; Xι₄ is oxygen or sulfur;

R₅₃ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, C C₃alkylthio, d-dalkylsulfinyl, d-C₃alkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; R^ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₅₃ together with R^ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-C haloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, C_rC₃alkylsulfinyl, d-C₃alkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-C₄alkylcarbonylamino;

R₈ is hydrogen or a d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group, which groups may be substituted once, twice or three times by halogen, hydroxy, d-C₆alkoxy, d-dalkoxy- d-C₃alkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, CrC₆alkylthio, CrC₆alkylsulfinyl, d-C₆- alkylsulfonyl, cyano, C(X₁₅)NR₅₅R₅₆, C₃-C₆cycloalkyl, phenyl, phenoxy or by 5- or 6- membered heteroaryl or heteroaryloxy, and wherein heteroaryl or heteroaryloxy may in turn be interrupted once by oxygen or by sulfur or once, twice or three times by nitrogen and may be bonded to the d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group either via a C atom or via a N atom, and wherein the phenyl- and heteroaryl-containing groups may be substituted once, twice or three times by halogen, d-dalkyl, Cι-C₄haloalkyl, d-dalkoxy, d-dhaloalkoxy, d-C₃alkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; X₁₅ is oxygen or sulfur;

R₅₅ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-C₄haloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, C C₃alkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; R₅₆ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₅₅ together with R₅₆ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-C₃haloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-C₃alkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; or R₈ is C(O)-R₇₆ or C(S)-R₇₇; X₃ is oxygen, -NR₅₇-, sulfur, -S(O)- or -S(O)₂-;

R₅₇ is hydrogen, CrCealkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, d-dhaloalkyl, C₃-C₆cycloalkyl, phenyl, heteroaryl, C(X₁₆)R5₈ or NR₆ιR₆2; X₁₆ is oxygen or sulfur;

R₅₈ is hydrogen, d-Cealkyl, C₃-C₆cycloalkyl, phenyl, heteroaryl, d-dalkoxy, C₃-C₆alkenyl- oxy, benzyloxy, d-C₄alkylthio or a group NR₅₉R₆₀;

R₅₉ and R₆ι are each independently of the other hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino;

Reo and R₆₂ are each independently of the other hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-dalkynyl; or R₅₉ together with R₆₀ or R₆ι together with R₆₂, in each case with the respective N atom to which they are bonded, form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, C C₃alkoxy, d-dhaloalkoxy, d-dalkylthio, C C₃alkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; or R₅₇ is -L₈-X₁₇-R₆₃; wherein X₁₇ is oxygen, -NR₆₄-, -S-, -S(O)- or -S(O)₂-;

R_M is hydrogen, d-dalkoxy, CrCealkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or is phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-C₃alkylthio, d-C₃alkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; R₆₃ is a d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group, which groups may be substituted once, twice or three times by halogen, hydroxy, d-dalkoxy, CrC₃alkoxy-d-C₃alkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, cyano, C(Xι₈)NR₆₅R_66> C₃-C₆cycloalkyl, phenyl, phenoxy or by 5- or 6-membered heteroaryl or heteroaryloxy, wherein heteroaryl or heteroaryloxy may in turn be interrupted once by oxygen or by sulfur or once, twice or three times by nitrogen and may be bonded to the CrC₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group either via a C atom or via a N atom, and wherein the phenyl- and heteroaryl-containing groups may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-C₃alkoxy, d-C₃haloalkoxy, d-dalkylthio, d-dalkylsulfinyl, C C₃alkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; X₁₈ is oxygen or sulfur;

R₆₅ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-C₃alkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; R₆₆ is hydrogen, d-Cealkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₆₅ together with R₆₆ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, C C₃alkylthio, d-dalkylsulfinyl, d-C₃alkylsulfonyl, C C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonyiamino;

R₆7 is formyl, d-dalkylcarbonyl, C₃-C₆cycloalkylcarbonyI, benzoyl, C C₆alkoxycarbonyl, cyano, C(Xιg)NR₆₈R₆₉, phenyl or heteroaryl, wherein benzoyl and phenyl may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-C₃alkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; and wherein heteroaryl may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-C₃alkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro or by d-dalkoxycarbonyl; or R₆ is C₃-C₆cycloalkyl or C₅-C₆cycloalkenyl each of which may in turn be substituted once, twice or three times by d-dalkyl, halogen or by C C₄alkoxy; X₁₉ is oxygen or sulfur;

R₆₈ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-C haloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino R₆g is hydrogen, d-Cealkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₆₈ together with R₆₉ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; Li is d-dalkylene which may be substituted once, twice or three times by d-dalkyl, halogen or by C C₄alkoxy and to which d-dalkylene group there may be spirocyclically bound a further C₂-C₅alkylene group which may in turn be interrupted once or twice by oxygen, sulfur, sulfinyl or by sulfonyl and may be substituted by d-dalkyl or by d-dalkoxy; or l_ι is d-dalkylene which may be substituted once, twice or three times by d-dalkyl, halogen or by d-dalkoxy, wherein a carbon atom of that d-dalkylene chain together with R₉ or with R ₀ forms a further C₂-C₆alkylene chain which may be interrupted once or twice by oxygen, sulfur, sulfinyl or by sulfonyl and may be substituted by d-dalkyl or by d-dalkoxy; R₉ is a group -X₂o-R₇o, wherein X₂₀ is oxygen, -NR₇₁-, -S-, -S(O)- or -S(O)₂-;

R₇₁ is a d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group, which groups may be substituted once, twice or three times by halogen, hydroxy, d-dalkoxy, CrC₃aikoxy-d-C₃alkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, CrC₆alkylthio, d-C₆alkylsulfinyl, CrC₆alkylsulfonyl, cyano, C(X₂ι)NR₇₂R₇₃, C₃-C₆cycloalkyl, phenyl, phenoxy or by 5- or 6-membered heteroaryl or heteroaryloxy, wherein heteroaryl or heteroaryloxy may in turn be interrupted once by oxygen or by sulfur or once, twice or three times by nitrogen and may be bonded to the d-Cealkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group either via a C atom or via a N atom, and wherein the phenyl- and heteroaryl-containing groups may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, C C₃haloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; X₂₁ is oxygen or sulfur;

R₇ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; R₇₃ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₇₂ together with R₇₃ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-C₃alkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, C C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino;

R₇₀ is hydrogen, d-dalkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, C(O)-R₇₈, C(S)-R₇₉ or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, C C₃alkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-C₄alkylcarbonylamino; or R₉ is formyl, d-dalkylcarbonyl, C₃-C₆cycloalkylcarbonyl, benzoyl, CrCealkoxycarbonyl, cyano, C(X₃₅)NRι₂₅Rι₂₆, phenyl or heteroaryl, wherein benzoyl and phenyl may be substituted once, twice or three times by halogen, d-dalkyl, d-C₄haloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by d-dalkylcarbonylamino; and wherein heteroaryl may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, C C₃alkoxy, d-dhaloalkoxy, d-dalkylthio, d-C₃alkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro or by C C₄alkoxycarbonyl; or R₉ is C₃-C₆cycloalkyl or d-C₆cycloalkenyl each of which may in turn be substituted once, twice or three times by d-dalkyl, halogen or by d-dalkoxy; X₃₅ is oxygen or sulfur;

R₁25 is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-C₃alkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by d-dalkylcarbonylamino;

Ri2β is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₁₂₅ together with Rι₂₆ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-C alkylcarbonylamino;

R7₄, R75, R76, R77, R78 and R₇₉ are each independently of the others hydrogen, d-dalkyl,

C₃-C₆cycloalkyl, phenyl, heteroaryl, d-dalkoxy, C₃-C₆alkenyloxy, d-dalkylthio or

R₁₂₇ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-C₃alkoxy, d-dhaloalkoxy, d-dalkylthio, d-C₃alkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by d-dalkylcarbonylamino;

R₁₂₈ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₁₂₇ together with R₁₂₈ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-C₃alkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino;

X₂₂ is hydroxy, O^"M⁺ wherein M⁺ is an alkali metal cation or ammonium cation, or is halogen,

CrCι₂alkylthio, Crd₂alkylsulfinyl, d-d₂alkylsulfonyl, Crd₂haloalkylthio, Crd₂halo- alkylsulfinyl, CrC₁₂haloalkylsulfonyl, Crdalkoxy-CrC₆alkylthio, Crdalkoxy-d-dalkyl- sulfinyl, d-dalkoxy-Crdalkylsulfonyl, C₃-C₁₂alkenylthio, C₃-Cι₂alkynylthio, d-dalkoxy- carbonyl-Cι-C₄alkylthio, CrC₄alkoxycarbonyl-CrC₄alkylsulfinyl, d-dalkoxycarbonyl-d-d- alkylsulfonyl, d-Cι₂alkylsulfonyloxy, phenylsulfonyloxy, CrC₈alkoxy, d-dalkenyloxy, d-C₈- alkynyloxy, d-C₈haloalkoxy, benzyloxy or benzoylmethoxy, wherein the phenyl-containing groups may be substituted once or more than once by R₈₂; R₈₂ is halogen, d-C₃alkyl, C C₃haloalkyl, hydroxy, d-dalkoxy, C C₃haloalkoxy, cyano or nitro; and also Examples 1.009, 1.010, 1.033 to 1.045, 1.094, 1.101 to 1.115, 1.158 to 1.161 ,

1.163 to 1.174, 1.191 , 1.194, 1.197 to 1.203.

The compounds of formula I can be prepared by means of processes that are known perse and are described, for example, in EP-A-352 543, EP-A-344775, US 6,211 ,403 und EP-A-1 286985.

Compounds of formula I can be prepared, for example, by a) converting a compound of formula lla

wherein R^ and R₂ are as defined hereinbefore, into a compound of formula lib

wherein Yi is a leaving group, e.g. halogen, cyano, acyloxy or phenoxy which may be substituted by an electron-withdrawing group, e.g. halogen, trifluoromethyl, nitro, cyano, d-dalkylcarbonyl, d-C₄alkoxycarbonyl or d-C₄alkylsulfonyl, or the like, and then reacting that compound in the presence of a base, e.g. triethylamine, Hϋnig's base, sodium hydrogen carbonate or potassium carbonate, with a pyrazole of formula III

wherein R₈₀ and R₈₁ are as defined hereinbefore and X₂₂ is hydroxy or O^"M⁺ wherein M⁺ is as defined hereinbefore, and then treating the reaction mixture in the presence of the base used, e.g. triethylamine or di(isopropyl)ethylamine, with the aid of a cyanide-containing catalyst, e.g. acetone cyanohydrin, trimethylsilyl cyanide, copper cyanide, sodium cyanide or potassium cyanide, or by means of fluoride ions, e.g. potassium fluoride, or by means of dimethylaminopyridine; or

b) converting a compound of formula Xllla

(Xllla),

wherein Ri and R₂ are as defined hereinbefore and Y is halogen or trifluoromethane- sulfonyloxy, under carbonylation conditions at elevated pressure and elevated temperature in the presence of a palladium catalyst having suitable ligands, e.g. PdCI₂(PPh₃)2, Pd(PPh₃)₄₎ Pd (dba)₃, Pd(CH₃CN)₂(PPh₃) or Pd(OAc)₂, and optionally in the presence of a further auxiliary catalyst, e.g. triphenylphosphine, tri(tert-butyl)phosphine, (Ph₃)₂PCH₂CH₂P(Ph₃)2 or (Ph₃)₂PCH₂CH₂CH₂P(Ph₃)2, and in the presence of a base, e.g. triethylamine, and optionally further adjuvants, e.g. LiCI or Li₂CO₃, using carbon monoxide and a pyrazole of formula III

or the tautomeric form of a pyrazole of formula Ilia

wherein R₈₀ and R₈₁ are as defined hereinbefore and X^ is hydroxy, into a compound of formula Xla

and/or its isomeric form Xlb

wherein R^ R₂, R₈₀ und R₈ι are as defined hereinbefore, and then treating that compound with the aid of a cyanide-containing catalyst, e.g. acetone cyanohydrin, trimethylsilyl cyanide, copper cyanide, sodium cyanide or potassium cyanide, in the presence of a trialkylamine base, e.g. triethylamine, to obtain a compound of formula I; or

c) when X₂ or X₃ is oxygen or sulfur, reacting a compound of formula la

wherein R^ R₂, R₈₀, Rsι and X₂₂ are as defined hereinbefore and X₂ is oxygen or sulfur, in the presence of a suitable base, e.g. potassium carbonate, anhydrous sodium hydroxide or sodium hydride, with an alkylating agent of formula IVa or IVb

Y₂-R₈ (IVa) or Y₂-LrRg (IVb),

wherein R₈ is an unsubstituted or substituted d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group, and Rg and l_ι are as defined hereinbefore, and Y₂ is a leaving group such as chlorine, bromine, iodine, mesyloxy or tosyloxy; or

d) when X₂ or X₃ is oxygen, reacting a compound of formula la

wherein R_1f R₂, R₈₀, Rβi and X22 are as defined hereinbefore and X₂ is oxygen, in the presence of a bis-diaza-alkoxycarboxylate of formula ROC(O)-N=C=N-COOR or a bis-diaza- alkylcarbamoyl of formula RNHC(O)-N=C=N-C(O)NHR, wherein R is a d-dalkyl or C₅-C₆- cycloalkyl group, and a phosphine, e.g. triphenylphosphine or tri(tert-butyl)phosphine, with an alcohol of formula Va or Vb

HO-R₈ (Va) or HO-L R₉ (Vb),

wherein R₈ is an unsubstituted or substituted d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group, and R₉ and are as defined hereinbefore; or

e) reacting a compound of formula lb

wherein R^ R , R₈o, Rsι and X^ are as defined hereinbefore and K^ is a leaving group, e.g. halogen or alkylsulfonyl, in the presence of a base, e.g. potassium tert-butanolate, sodium amylate, sodium hydride, dry sodium or potassium hydroxide, or an amine, e.g. triethylamine, Hϋnig's base or dimethylaminopyridine, with an alcohol or a mercaptan of formula Vc or Vd

HX₂-R₈ (Vc) or HXs-U-Rβ (Vd),

wherein R₈ is an unsubstituted or substituted d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group, and L-i and Rg are as defined hereinbefore, and X₂ or X₃ is oxygen or sulfur, or with an amine of formula Ve or VI

HNR57- 1-R9 (Ve) or HNR₆R₇ (VI),

wherein L₁₍ R₆, R₇, R₉ and R₅₇ are as defined hereinbefore; or

f) reacting a compound of formula lc

wherein R_{1 (} R₂, R₈₀, Rsι and X₂₂ are as defined hereinbefore and K₂ is a group capable of appropriate functionalisation -L₁₀-K₂o, -L_H-X₁-K₂₁, -X₂-K₂₂, -X₃-LrK₂₃ wherein l_ι₀, L-n, Li, X^ X₂ and X₃ are as defined hereinbefore and K₂₀, K₂ι, K₂₂ and K₂₃ are a functionalisation group, e.g. hydroxy, chlorine, bromine, iodine, mesyloxy, tosyloxy, formyl or carbonyl, either with an appropriate alkylating agent of formula VII or Vila

Y₃-R₉ (VII) or Y₃-X₂₀-R7o (Vila),

or with a ketalisation agent or a nucleophilic reagent of formula VIII

or its salt of formula Villa

M⁺ -X₂₀-R7o (Villa),

wherein R₉, R₇₀ and X₂o are as defined hereinbefore and Y₃ is a leaving group such as bromine, iodine, tosyloxy or d-dalkylsulfonyloxy, and M⁺ is a metal cation of an alkali metal base, such as lithium, sodium or potassium, optionally in the presence of an additional base, e.g. potassium carbonate, or, in the case of ketalisation of a carbonyl function, in the presence of an additional acid, e.g. p-toluenesulfonic acid, trifluoroacetic acid or sulfuric acid; or

g) when Ri is -L₁₀-R₄ or -Lπ-XrRs wherein L₁₀ or L is especially an unsubstituted or substituted d-dalkenylene or a C₂-C₆alkynylene group and R₄, when L₁0 is a direct bond, is especially a five- to ten-membered, monocyclic or fused bicyclic ring system which may be aromatic or partially saturated and which may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, reacting a compound of formula Id

wherein R^ R₂, R₈₀, R₈ι and X are as defined hereinbefore and K₃ is a group capable of functionalisation, such as chlorine, bromine, iodine or trifluoromethylsulfonyloxy, by means of a -C-C- linking Suzuki, Stilie, Sonogashira or Heck reaction, in the presence of a noble metal catalyst having suitable ligands, e.g. PdCI₂(PPh₃)₂, Pd(PPh₃)₄, Pd₂(dba)₃, Pd(CH₃CN)₂(PPh₃)₂, Pd(OAc)₂, Rh, Cu, CuCI or Cul, and in the presence of a base, e.g. triethylamine, Hunig's base, sodium tert-butanolate, potassium tert-butanolate, sodium carbonate, potassium carbonate, caesium carbonate, potassium fluoride or caesium fluoride, and optionally further adjuvants, e.g. LiCI or Li₂CO₃, or an additional auxiliary catalyst, e.g. triphenylphosphine, tri(tert-butyl)phosphine, (Ph₃)₂PCH₂CH₂P(Ph₃)₂ or (Ph₃)₂PCH₂CH₂CH₂P(Ph₃)2, with a boronic acid, e.g. of formula Xa or Xb

(HO)₂B-L₁₀-R₄ (Xa) or (HOfeB-Ln-XrRβ (Xb),

or with a tin compound of formula Xc or Xd

R_eR_fRgSn-L₁₀-R₄ (Xc) or ReRfRgSn-Ln-XrRs (Xd),

or with an ethynyl compound of formula Xe or Xf having a functionality in accordance with R^

H-C≡C-L_10b-R (Xe) or H-C≡C-L_11b-X R₅ (Xf),

or with a vinyl compound of formula Xg or Xh having a functionality in accordance with R^

H-CH=CH-L_10a-R₄ (Xg) or H-CH=CH-L_11a-X R₅ (Xh),

wherein L₁₀, Ln, R₄, R₅ and X^ are as defined hereinbefore, R_e, R_f and R_g are each independently of the others d-dalkyl and L _0a, Lι_0b, _11a and L_11b are appropriate subgroups of the groups L₁₀ and L-π, such as especially a direct bond or a d-dalkylene group which may be substituted once, twice or three times by CrCealkyl, halogen, hydroxy, d-dalkoxy or by d-dalkoxy-d-dalkoxy; or h) for the preparation of compounds of formula I wherein the substituent definitions include sulfinyl or sulfonyl groups, treating a compound of formula I wherein the corresponding substituent definitions include thio groups with an oxidising agent, e.g. peracetic acid, trifluoroperacetic acid, m-chloro-perbenzoic acid, hydrogen peroxide, sodium perbromate, sodium iodate, sodium hypochloride, chlorine or bromine.

In addition, compounds of formula I wherein X₂₂ is other than hydroxy or halogen can be prepared, in accordance with conversion methods generally known from the literature, by nucleophilic substitution reactions of chlorides of formula I wherein X₂₂ is chlorine, which can be obtained from compounds of formula I wherein X₂₂ is hydroxy, likewise in accordance with known methods, by reaction with a chlorinating agent, such as phosgene, thionyl chloride or oxalyl chloride. In that process, for example, mercaptans, thiophenols or heterocyclic thiols are reacted in the presence of a base, e.g. 5-ethyl-2-methylpyridine, diisopropylethylamine, triethylamine, sodium hydrogen carbonate, sodium acetate or potassium carbonate. Furthermore, compounds of formula I wherein the substituent X₂₂ is a mercapto group can be oxidised in analogy to known standard methods, for example using peracids, e.g. meta- chloroperbenzoic acid (m-CPBA) or peracetic acid, to form the corresponding sulfoxides and/or suifones of formula I. In the process, the degree of oxidation at the sulfur atom (-S(O)- or -SO₂-) can be controlled by the amount of oxidising agent.

In the case of process a), as a result of reaction of a pyrazole of formula III with an acid of formula lla in the presence of a suitable coupling reagent, e.g. dicyclohexylcarbodiimide, N- ethyl-N'-(3-dimethylamino-propyl)-carbodiimide (EDC), 2-chloro-1 -methyl-pyridinium iodide or N,N-dimethyl-(1-chloro-2-methyl-propen)amine, or as a result of reaction of a pyrazole of formula III with an activated form of the acid, e.g. an acid chloride, of formula lib, wherein Y^ is chlorine, in the presence of a base, e.g. triethylamine, Hunig's base or potassium carbonate, there is obtained a corresponding enol ester compound of formula Xla and/or Xib

wherein R^ R₂, R₈o, Rsι and X₂₂ are as defined hereinbefore, which may then either be rearranged directly in situ by adding catalytic amounts of cyanide ions, e.g. from about 1 % to about 15 % acetone cyanohydrin, to form the compound of formula I, or may first be isolated and purified and then, in a second step, rearranged in the presence of catalytic amounts of a cyanide source, e.g. from about 0.1 % to about 5 % potassium cyanide ions or from about 0.5 % to about 10 % acetone cyanohydrin, and a fresh amount of a trialkylamine base, e.g. from about 0.1 to about 3 equivalents of triethylamine, preferably from 1 to about 1.4 equivalents, to form the compound of formula I, as shown above using the exemplified formulae Xla and Xlb to form compounds of formula I. This process may be shown in general terms in Reaction scheme 1 using the example of the preparation of compounds of formula I.

Reaction scheme 1 : activating agent: la) e.g. (COCI)₂

(lla) (lib) Y₁₌CI

(Xlb) (Xla) (I), wherein X₂₂=OH

In a preferred process for the preparation of compounds of formula la

wherein R_{1 ;} R₂, R₈₀, R₈ι and X₂₂ are as defined hereinbefore and X₂ is oxygen or sulfur and which are used as starting materials in process variants c) and d), for example, either a compound of formula le

wherein Ri, R₂, R₈o, Rβi and X₂₂ are as defined hereinbefore and K₄ is a cleavable group, such as methoxy when X₂ is oxygen, or is a disulfide bridge of a dimeric compound le, is reacted in the presence of an ether-cleaving reagent, e.g. boron trichloride, boron tribromide, aluminium trichloride, sodium methylmercaptide, sodium ethylmercaptide or trimethylsilyl iodide, or a compound of formula le wherein _t is benzyloxy or dimeric disulfide is reduced catalytically in the presence of hydrogen.

The compounds of formula If used in process variants c), d), e), f) and g)

wherein Ri, R₂, R₈o, Rsι and X₂₂ are as defined hereinbefore and Ko is a sub-group of

capable of functionalisation, as defined especially in accordance with the meanings of K_1; K₂, Ks and/or K* above, such as especially fluorine, chlorine, bromine, iodine, hydroxy, methylthio, methylsulfonyl, bromomethyl, hydroxymethyl, formyl, methylcarbonyl, 2- hydroxyethoxy, 2-bromoethoxy, benzyloxy or dimeric disulfide, can likewise be prepared in accordance with process variant a) or in accordance with process variant b) from the corresponding compounds of formula XII or XIII

wherein Ko, R2 and Y₄ are as defined hereinbefore and Y is d-dalkoxy, benzyloxy, hydroxy, fluorine, chlorine, cyano or phenoxy which may be substituted by an electron-withdrawing group, e.g. halogen, trifluoromethyl, nitro, cyano, d-dalkylcarbonyl, d-dalkoxycarbonyl or d-dalkylsulfonyl, Y being especially C C alkoxy, benzyloxy, hydroxy, chlorine or cyano; and Ko being especially hydroxy (corresponding to formula la wherein X₂ is oxygen), K^ wherein K₁ is, for example, halogen or methylsulfonyl (corresponding to formula lb), K₃ wherein K₃ is, for example, chlorine, bromine or iodine (corresponding to formula Id), Ki wherein l^ is, for example, methylthio, benzyloxy or methoxy (corresponding to formula le), or a disulfide bridge of a dimeric compound XII or XIII (corresponding to formula le wherein X₂ is sulfur), aa) by reacting the compound in question with a pyrazole of formula III

wherein X is hydroxy or O^"M⁺ and R₈₀, R₈₁ and M⁺ are as defined hereinbefore, or bb) by reacting a hydroxy or mercapto compound of formula la

wherein R,, R₂, R₈₀, R₈₁ and X₂₂ are as defined hereinbefore and X₂ is oxygen or sulfur, in accordance with process variant c) with an appropriate alkylating agent of formula IVc

Y₂-L K₂₃ (IVc), or cc) in accordance with process variant d) with the appropriate alcohol of formula Vf

HO-U-K_JB (Vf),

or dd) in accordance with process variant e) by treating a compound of formula lb

wherein R^ R₂, Rso, Rsi and X22 are as defined hereinbefore and K₁ is halogen or alkylsulfonyl, with an alcohol or mercaptan of formula Vg or Vh

HK, (Vg) or HX₃-LrK₂₃ (Vh),

or with an amine of formula Vic

HNR₆-LrK₂₃ (Vic),

wherein K| is methoxy or methylthio and X₃ is oxygen or sulfur, and K₂₃, L,, R₆ and Y₂ are as defined hereinbefore.

The starting materials of formula lla

and of formula lib

wherein R^ R₂ and Y₁ are as defined hereinbefore, and also compounds of formula lid

wherein Y₀ is d-dalkoxy, benzyloxy or phenoxy which may be unsubstituted or substituted by an electron-withdrawing group such as halogen, trifluoromethyl, nitro, cyano, d-dalkylcarbonyl, d-dalkoxycarbonyl or d-dalkylsulfonyl, which are used as starting materials in the preparation of compounds of formula lla, can be prepared analogously to known methods, as described e.g. in EP-A-0 353 187, by converting a compound of formula XIII

wherein R₂ is as defined hereinbefore, Ko is hydrogen, methoxy, methylthio, methylsulfonyl, halogen or another group R that is stable in this process, and Y₄ is chlorine, bromine or trifluoromethylsulfonyloxy, under carbonylation conditions at elevated pressure and elevated temperatures in the presence of a palladium catalyst having suitable ligands, e.g. PdCI₂(PPh₃)₂, Pd(PPh₃)₄, Pd(CH₃CN)₂(PPh₃)2, Pd₂(dba)₃ or Pd(OAc)₂, and optionally in the presence of an auxiliary catalyst, e.g. triphenylphosphine, tri(tert-butyl)phosphine, (Ph₃)₂PCH₂CH₂P(Ph₃)₂ or (Ph₃)₂PCH₂CH₂CH₂P(Ph₃)₂, and in the presence of a base, e.g. triethylamine, using carbon monoxide and an alcohol of formula IX

Ro-OH (IX)

wherein R₀ is d-dalkyl, benzyl or phenyl which may be unsubstituted or substituted by an electron-withdrawing group such as halogen, trifluoromethyl, nitro, cyano, d-dalkylcarbonyl, d-dalkoxycarbonyl or d-dalkylsulfonyl, into a compound of formula Xlla

wherein Ko, R₂ and Y₀ are as defined hereinbefore, and then converting that compound in known conversion reactions, e.g. hydrolysis, addition and/or substitution reactions and subsequent hydrolysis, into the compound of formula XII or of formula II

wherein Ko, Ri and R₂ are as defined hereinbefore and Y is d-dalkoxy, benzyloxy, hydroxy, fluorine, chlorine, bromine, cyano or phenoxy which may be unsubstituted or substituted by an electron-withdrawing group, e.g. halogen, trifluoromethyl, nitro, cyano, d-dalkylcarbonyl, d-dalkoxycarbonyl or d-dalkylsulfonyl.

For example, a compound of formula XI I lb

(Xlllb),

wherein R and Y₄ are as defined hereinbefore, can be converted by carbonylation or by means of a Grignard reaction and CO₂ into a compound of formula Xllb

wherein R₂ and Y₀ are as defined hereinbefore, which is then converted in the presence of an oxidising agent, e.g. hydrogen peroxide or the hydrogen peroxide/urea adduct in the presence of trifluoroacetic anhydride, into an N-oxido compound of formula XV

wherein R₂ and Y₀ are as defined hereinbefore, which is then either a) reacted in the presence of phosphorus oxychloride or trifluoroacetic anhydride to form a hydroxy compound of formula XI lc

or b) when a suitable nucleophile of formula Vi is used

HR_T (Vi)

or when a nucleophile of formula Vlb is used

HNR₆C(O)R₃₀ (Vlb),

wherein R^ R₆, R₃o are as defined hereinbefore, converted in the presence of an activating reagent, e.g. oxalyl chloride or trifluoroacetic anhydride, and optionally in the presence of an acid-binding agent, e.g. triethylamine or Hϋnig's base, directly into the compounds of formula lid

wherein R^ R₂ and Y₀ are as defined hereinbefore and R₁ is especially also a group -NR C(O)R_30> which can then be converted in accordance with a) for the isolation of an intermediate of formula XI lc by known and general conversion methods such as halogena- tion, e.g. by means of dichlorophenyl phosphate, further nucleophilic reactions with alcohols, mercaptans or amines of formula

HXs-L Rβ (V) or HNR₆R₇ (VI),

wherein X₃, L|, R₆, R₇, R₉ are as defined hereinbefore, as described above under process conditions c) to h) into compounds of formula XII or of formula II

wherein K_Q, R,, R₂ and Y are as defined hereinbefore.

The starting materials of formula lid

wherein R^ is a group -X₂-R₈ or -X₃-l_rR₉, X2 and X₃ are oxygen, and l_ι, R₂, R₉ and Y₀ are as defined hereinbefore, and R₈ is an unsubstituted or substituted d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group, can also be prepared either by treating a compound of formula XI Id

wherein R₂ and Y₀ are as defined hereinbefore, and X₂ is oxygen or sulfur, in accordance with process variant c) in the presence of a suitable base with an alkylating agent of formula

Y₂-R₈ (IVa) or Y₂-LrR₉ (IVb),

wherein Li, R₉ and Y₂ are as defined hereinbefore and R₈ is an unsubstituted or substituted Cι-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group; or by reacting a compound of formula Xlld

wherein R₂ and Y₀ are as defined hereinbefore and X₂ is oxygen, in accordance with process variant d) in the presence of a bis-diaza-alkoxycarboxylate of formula ROC(O)-N=C=N- COOR or a bis-diaza-alkylcarbamoyl of formula RNHC(O)-N=C=N-C(O)NHR, wherein R is a d-dalkyl or C₅-C₆cycloalkyl group, and simultaneously in the presence of a phosphine, e.g. triphenylphosphine or tri(tert-butyl)phosphine, with an alcohol of formula

HO-R₈ (Va) or HO-L R₉ (Vb),

wherein R₈ is an unsubstituted or substituted d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group, and R₉ and U are as defined hereinbefore, respectively.

The reaction described in accordance with process variant d) is generally known as a Mitsunobu reaction and is especially suitable for the preparation of those compounds of formulae I and lid wherein R^ is a group -X -R_8l -Xs-U-Rg or -X LrX2o-R7o and X₂ and X₃ are oxygen and R₈ and l_ι are a d-dalkylene group branched in the a/pfra-position or substituted in that position by halogen or by alkoxy, or together with R₉ or with R₇₀ forms, by means of a further d-dalkylene chain, a 3- to 6-membered ring system.

Furthermore, the starting materials of formula lid

wherein Ri is a group -L₁₀-R₄ or -L-n-X s and wherein L₁₀ and Ln are especially an unsubstituted or substituted C -C₆alkenylene or a C₂-C₆alkynylene group and R₄, when L₁₀ is a direct bond, is especially a five- to ten-membered, monocyclic or fused bicyclic ring system which may be aromatic or partially saturated, and which may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, and R₂, Rs, Xi and Y₀ are as defined hereinbefore, can advantageously be prepared by reacting a compound of formula XI le

wherein R₂ and Y₀ are as defined hereinbefore, and Ks is group capable of further functionalisation, such as chlorine, bromine, iodine or trifluoromethylsulfonyloxy, in accordance with process variant g) by means of a -C-C- linking Suzuki, Stille, Sonogashira or Heck reaction, in the presence of a noble metal catalyst having suitable ligands, e.g. PdCI₂(PPh₃)₂, Pd(PPh₃)₄, Pd₂(dba)₃, Pd(CH₃CN)₂(PPh₃)₂, Pd(OAc)₂, Rh, Cu, CuCI or Cul, and in the presence of a base, e.g. triethylamine, Hϋnig's base, sodium tert-butanolate, potassium tert-butanolate, sodium carbonate, potassium carbonate, caesium carbonate, potassium fluoride or caesium fluoride, and optionally further adjuvants, e.g. LiCI or Li₂CO₃, or an additional auxiliary catalyst, e.g. triphenylphosphine, tri(tert-butyl)phosphine, (Ph₃)₂PCH2CH₂P(Ph₃)2 or (Ph₃)2PCH2CH₂CH₂P(Ph₃)₂, with a boronic acid, e.g. of formula Xa or Xb

(HO)₂B-L₁₀-R (Xa) or (HO^B-Ln-X Rs (Xb),

or with a tin compound of formula Xc or Xd

R_eRfRgSn-L₁₀-R₄ (Xc) or ReRfRgSn-Ln-Xi-Rs (Xd),

or with an ethynyl compound of formula Xe or Xf having a functionality in accordance with Ri

H-C≡C-L_10b-R₄ (Xe) or H-C≡C-L_11b-X R₅ (Xf),

or with a vinyl compound of formula Xg or Xh having a functionality in accordance with R_n

H-CH=CH-L_10a-R₄ (Xg) or H-CH=CH-L_11a-X R₅ (Xh),

and wherein Lι₀, Ln, R₄, R₅ and Xi are as defined hereinbefore, R_e, R_f and R_g are each independently of the others d-dalkyl and L_10a, L_10b, L_11a and L are appropriate subgroups of the groups L₁₀ and Lπ, such as especially a direct bond or a d-dalkylene group which may be substituted once, twice or three times by d-Cealkyl, halogen, hydroxy, d-dalkoxy or by d-C₃alkoxy-Cι-C₃alkoxy, and wherein the reagents Xg and Xh can in addition each result in one or more regio-isomeric products, for example

Those process sequences are described in greater detail in Reaction schemes 2 to 5 below.

Reaction scheme 2:

(XIII) Y₄=CI (lib) Y₁₌CI

Reaction scheme 3:

(Xillb) Y₄=CI (Xlla) (XV)

cat.: e.g. 18-crown-6 (Xllc) solv.: e.g. CH₃CN (lid) R₁=X₂-R₈ =X₃-L₁-R₉

Reaction scheme 4:

or (Xllc) (Xlla) Ko=CI HNR₆R₇ (VI) (lid) R₁=X₃-L₁-R₉ or -C-C- linkage =NR₆R₇ by means of Suzuki, Stille, Heck ^=L10^"R or Sonogashira reaction

Reaction scheme 5:

(XV) (lid) R₁₌NR₆C(O)R₃₀ (lla) R₁₌NR₆C(O)R₃₀

The compounds of formulae XII and Xllf

wherein K₀, K₂ and R₂ are as defined hereinbefore and Y is accordingly Y₀, hydroxy or Y^ which are used as starting materials in the preparation of compounds of general formulae If and especially lc, can likewise be prepared in accordance with the generally known methods or in accordance with the preparation processes c) to h) given above for formulae I and lie.

The compounds of formula II used as starting materials

wherein R^ and R₂ are as defined hereinbefore and Y is d-C₄alkoxy, benzyloxy, hydroxy, fluorine, chlorine, bromine, cyano or phenoxy which may be unsubstituted or substituted by an electron-withdrawing group, e.g. halogen, trifluoromethyl, nitro, cyano, d-dalkylcarbonyl, d-dalkoxycarbonyl or d-dalkylsulfonyl, are novel and the present Application relates also to the use thereof in the preparation of compounds of formula I.

The compounds of formula III used as starting materials

or the tautomeric pyrazolones of formula Ilia

wherein X₂₂ is hydroxy or O^'M⁺, and M⁺, R₈₀ and R₈₁ are as defined hereinbefore, are generally known, or they can be prepared in accordance with known methods.

The starting materials of formulae IVa, IVb, IVc, V, Va, Vb, Vc, Vd, Ve, Vf, Vg, Vh, Vi, VI, Via, Vlb, Vic, VII, Vila, VIM, Villa, IX, Xa, Xb, Xc, Xd, Xe, Xf, Xg, Xh, Xllla, Xlllb are likewise generally known or they can be prepared analogously to known methods.

All the reactions according to the preparation processes a) to h) for forming compounds of formula I and also intermediates of formula II are advantageously carried out in aprotic and inert organic solvents. Such solvents are hydrocarbons, e.g. benzene, toluene, xylene or cyclohexane, chlorinated hydrocarbons, e.g. dichloromethane, chloroform, tetrachloro- methane or chlorobenzene, ethers, e.g. diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetrahydrofuran or dioxane, nitriles, e.g. acetonitrile or propionitrile, and amides, e.g. N,N-dimethylformamide, diethylformamide or N-methyl- pyrrolidinone. The temperatures in those reactions are preferably from -20°C to +120°C. When the reactions are exothermic, they can usually be carried out at room temperature. In order to shorten the reaction time or also in order to initiate the reaction, the reaction mixture may, where appropriate, be heated briefly up to its boiling point. Relatively new application techniques such as ultrasound and the use of microwaves are also highly suitable. It is often possible, especially when using microwaves, for the reaction times to be substantially reduced at relatively mild temperatures of from about 100°C to about 150°C. The reaction times can likewise be shortened by adding a suitable base as reaction catalyst. Suitable bases are, especially, tertiary amines such as trimethylamine, triethylamine, quinuclidine, 1 ,4-diazabicyclo[2.2.2]octane, 1 ,5-diazabicyclo[4.3.0]non-5-ene and 1 ,5-diazabicyclo[5.4.0]- undec-7-ene. However, it is also possible to use inorganic bases, such as hydrides, e.g. sodium or calcium hydride, hydroxides, e.g. dry sodium or potassium hydroxide, carbonates, e.g. sodium or potassium carbonate, or hydrogen carbonates, e.g. sodium or potassium hydrogen carbonate.

In accordance with process a), preparation of the compounds of formulae I, If, and II, lib and XII, wherein Yi and Y are chlorine, is carried out using a chlorinating agent, e.g. oxalyl chloride, thionyl chloride, phosgene, (1 -chloro-2-methyl-propenyl)-dimethyl-amine, phosphorus pentachloride, phosphorus oxychloride or dichlorophosphate, preferably using oxalyl chloride. The reaction is preferably carried out in an inert, organic solvent, for example in an aliphatic, halogenated aliphatic, aromatic or halogenated aromatic hydrocarbon, e.g. n-hexane, benzene, toluene, xylenes, dichloromethane, 1 ,2-dichloroethane or chloro- benzene, at reaction temperatures in the range from -20°C up to the reflux temperature of the reaction mixture, preferably at about 40-100°C, and in the presence of a catalytic amount of N,N-dimethylformamide. It can also, where appropriate, be carried out directly in the chlorinating agent used, without additional solvent.

The end products of formula I can be isolated in conventional manner by concentrating or evaporating off the solvent and can be separated and purified by recrystallising or by triturating the solid residue in solvents in which they are not readily soluble, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons, or by distillation or by means of column chromatography or by means of HPLC techniques using a suitable eluant.

The person skilled in the art will also be familiar with the order in which the reactions should be performed in order to avoid subsidiary reactions as far as possible. Unless synthesis is specifically aimed at the isolation of pure isomers, the product may be obtained in the form of a mixture of two or more isomers, e.g. chiral centres in the case of alkyl groups or cis/trans isomerism in the case of alkenyl groups or Ε' or 'Z' forms. All those isomers can be separated using methods known perse, e.g. chromatography or fractional crystallisation, or, by specifically controlling the reactions, a desired form can be produced in a relatively high concentration or in pure form.

The compounds of formula I according to the invention can be used as herbicides in unmodified form, that is to say as obtained in the synthesis, but they are generally formulated in various ways, using formulation adjuvants such as carriers, solvents and surface-active substances, to form herbicidal compositions. The formulations can be in various physical forms, e.g. in the form of dusting powders, gels, wettable powders, water- dispersible granules, water-dispersible tablets, effervescent tablet compacts, emulsifiable concentrates, micro-emulsifiable concentrates, oil-in-water emulsions, aqueous dispersions, dispersions in oil, suspoemulsions, water-soluble concentrates (having water or a water- miscible organic solvent as carrier), impregnated polymer films, or in other forms that are known, for example from the Manual on Development and Use of FAO Specifications for Plant Protection Products, 5th Edition, 1999. Those formulations either can be used directly or are diluted before use. The dilutions can be produced using, for example, water, liquid fertilisers, micro-nutrients, biological organisms, oil or solvents.

The formulations can be produced, for example, by mixing the active ingredient with the formulation adjuvants to obtain compositions in the form of finely divided solids, granules, spherules, solutions, dispersions or emulsions. The active ingredients can also be formulated with other adjuvants, such as finely divided solids, mineral oils, organic solvents, water, surface-active substances or combinations thereof. The active ingredients can also be contained in very fine microcapsules consisting of a polymer. Microcapsules contain the active ingredients in a porous carrier. This enables active ingredients to be released into the surroundings in controlled amounts. Microcapsules usually have a diameter of from 0.1 to 500 microns. They contain active ingredient in an amount of about from 25 to 95 % by weight of the capsule weight. The active ingredients can be present in the form of a monolithic solid, in the form of fine particles in solid or liquid dispersion or in the form of a suitable solution. The encapsulating membranes comprise, for example, natural and synthetic gums, cellulose, styrene-butadiene copolymers, polyacrylonitrile, polyacrylate, polyester, polyamides, polyureas, polyurethane or chemically modified polymers and starch xanthates or other polymers known in this context to the person skilled in the art. Alternatively, it is possible for very fine microcapsules to be formed wherein the active ingredient is present in the form of finely divided particles in a solid matrix of a base substance, but in that case the microcapsules are not encapsulated.

The formulation adjuvants that are suitable for producing the compositions according to the invention are known perse. As liquid carriers there may be used: water, toluene, xylene, petroleum ether, vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acid anhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl esters of acetic acid, diacetone alcohol, 1 ,2-dichloro- propane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethylformamide, dimethyl sulfoxide, 1 ,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidinone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1 ,1-trichloroethane, 2-heptanone, alpha- pinene, d-limonene, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol acetate, glycerol diacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobomyl acetate, isooctane, isophorone, isopropylbenzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxy- propanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG400), propionic acid, propylene glycol, propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylenesulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, ethanol, isopropanol, and alcohols of higher molecular weight such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, etc., ethylene glycol, propylene glycol, glycerol, N-methyl-2-pyrrolidinone, and the like. Water is generally the carrier of choice for dilution of the concentrates. Suitable solid carriers are, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, chalk, calcium carbonate, bentonite, calcium montmorillonite, cottonseed husks, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin and similar substances such as are described, for example, in CFR 180.1001. (c) & (d).

A large number of surface-active substances can advantageously be used both in solid and in liquid formulations, especially in those which can be diluted with a carrier before application. Surface-active substances can be anionic, cationic, non-ionic or polymeric, and they can be used as emulsifying agents, wetting agents or suspension agents or for other purposes. Typical surface-active substances include, for example, salts of alkyl sulfates, e.g. diethanolammonium lauryl sulfate; salts of alkylarylsulfonates, e.g. calcium dodecylbenzene- sulfonate; addition products of alkylphenols and alkylene oxides, e.g. nonylphenol ethoxylates; addition products of alcohols and alkylene oxides, e.g. tridecylalcohol ethoxylates; soaps, e.g. sodium stearate; salts of alkylnaphthalenesulfonates, e.g. sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, e.g. sodium di(2-ethyl- hexyl)sulfosuccinate; sorbitol esters, e.g. sorbitol oleate; quaternary amines, e.g. lauryl trimethyiammonium chloride, polyethylene glycol esters of fatty acids, e.g. polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono- and di-alkyl phosphate esters; and also further substances described, for example, in "McCutcheon's Detergents and Emulsifiers Annual" MC Publishing Corp., Ridgewood New Jersey, 1981. Further adjuvants which can usually be used in herbicidal formulations include crystallisation inhibitors, viscosity-modifying substances, suspension agents, dyes, antioxidants, foaming agents, light-absorbing agents, mixing adjuvants, anti-foams, complex-formers, neutralising or pH-modifying substances and buffers, corrosion inhibitors, fragrances, wetting agents, take-up enhancers, micro-nutrients, plasticisers, glidants, lubricants, dispersants, thickening agents, antifreeze agents, microbicidal agents, and also liquid and solid fertilisers.

The formulations may also comprise additional active substances, e.g. further herbicides, herbicide safeners, plant growth regulators, fungicides or insecticides.

The compositions according to the invention may additionally include an additive comprising an oil of vegetable or animal origin, a mineral oil, alkyl esters thereof or mixtures of such oils and oil derivatives. The amounts of oil additive used in the composition according to the invention are generally from 0.01 to 10 %, based on the spray mixture. For example, the oil additive can be added to the spray tank in the desired concentration after the spray mixture has been prepared. Preferred oil additives comprise mineral oils or an oil of vegetable origin, for example rapeseed oil, olive oil or sunflower oil, emulsified vegetable oil, such as AMIGO® (Rhόne-Poulenc Canada Inc.), alkyl esters of oils of vegetable origin, for example the methyl derivatives, or an oil of animal origin, such as fish oil or beef tallow. A preferred additive contains as active components, for example, essentially 80 % by weight alkyl esters of fish oils and 15 % by weight methylated rapeseed oil, and also 5 % by weight of customary emulsifiers and pH modifiers.

Especially preferred oil additives comprise alkyl esters of C₈-C₂₂ fatty acids, the methyl derivatives of Cι₂-Cι₈ fatty acids, for example the methyl esters of lauric acid, palmitic acid and oleic acid, being especially important. Those esters are known as methyl laurate (CAS- 111-82-0), methyl palmitate (CAS-112-39-0) and methyl oleate (CAS- 112-62-9). A preferred fatty acid methyl ester derivative is Emery® 2230 and 2231 (Cognis GmbH). These and other oil derivatives are also known from the Compendium of Herbicide Adjuvants, 5th Edition, Southern Illinois University, 2000.

The application and action of the oil additives can be further improved by combining them with surface-active substances, such as non-ionic, anionic or cationic surfactants. Examples of suitable anionic, non-ionic and cationic surfactants are listed on pages 7 and 8 of WO g7/34485. Preferred surface-active substances are anionic surfactants of the dodecylbenzylsulfonate type, especially the calcium salts thereof, and also non-ionic surfactants of the fatty alcohol ethoxylate type. Special preference is given to ethoxylated C12-C₂2 fatty alcohols having a degree of ethoxylation of from 5 to 40. Examples of commercially available surfactants are the Genapol types (Clariant AG). Also preferred are silicone surfactants, especially polyalkyl-oxide-modified heptamethyltrisiloxanes, which are commercially available, for example, as Silwet L-77®, and also perfluorinated surfactants. The concentration of surface-active substances in relation to the total additive is generally from 1 to 30 % by weight. Examples of oil additives that consist of mixtures of oils or mineral oils or derivatives thereof with surfactants are Edenor ME SU®, Turbocharge® (Zeneca Agro, CA) and Actipron® (BP Oil UK Limited, GB).

Where appropriate, the mentioned surface-active substances can also be used alone, that is to say without oil additives, in the formulations.

The addition of an organic solvent to the oil additive/surfactant mixture can also bring about a further enhancement of action. Suitable solvents are, for example, Solvesso® (ESSO) and Aromatic Solvent® (Exxon Corporation). The concentration of such solvents can be from 10 to 80 % by weight of the total weight. Such oil additives, which are present in admixture with solvents, are described, for example, in US-A-4,834,908. A commercially available oil additive known therefrom is known by the name MERGE® (BASF Corporation). A further oil additive that is preferred according to the invention is SCORE® (Syngenta Crop Protection Canada).

In addition to the oil additives listed above, it is also possible, for the purpose of enhancing the action of the compositions according to the invention, to add formulations of alkyl pyrrolidones (e.g. Agrimax®) to the spray mixture. Formulations of synthetic latices, such as, for example, polyacrylamide, polyvinyl compounds or poly-1 -p-menthene (e.g. Bond®, Courier® or Emerald®), can also be used for the purpose. Solutions comprising propionic acid, for example Eurogkem Pen-e-trate®, can also be admixed as action-enhancing agents with the spray mixture. The herbicidal formulations generally contain from 0.1 to 99 % by weight, especially from 0.1 to 95 % by weight, of compound of formula I and from 1 to 99.9 % by weight of a formulation adjuvant which preferably contains from 0 to 25 % by weight of a surface-active substance. Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ dilute formulations.

The rates of application of compounds of formula I may vary within wide limits and depend on the nature of the soil, the method of application (pre- or post-emergence; seed dressing; application to the seed furrow; no tillage application etc.), the crop plant, the weed or grass to be controlled, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop. The compounds of formula I according to the invention are generally applied at a rate of from 1 to 2000 g/ha.

The invention relates also to a method of selectively controlling grasses and weeds in crops of useful plants, which comprises treating the useful plants or the area of cultivation or locus thereof with the compounds of formula I.

The weeds to be controlled may be either monocotyledonous or dicotyledonous weeds, such as, for example, Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola and Veronica.

As crops of useful plants in which the composition according to the invention can be used there come into consideration especially cereals, cotton, soybeans, sugar beet, sugar cane, plantation crops, rape, maize and rice. Crops are to be understood as including those which have been made tolerant to herbicides or classes of herbicides (e.g. ALS-, GS-, EPSPS- and HPPD-inhibitors) by means of conventional breeding or genetic engineering methods. An example of a crop that has been made tolerant by conventional breeding methods to, for example, imidazolinones such as imazamox is Clearfield® summer rape (canola). Examples of crops made tolerant to herbicides by genetic engineering methods are maize varieties resistant to, for example, glyphosate or glufosinate, which are commercially available under the trade names RoundupReady® and LibertyLink®. Useful plants are to be understood as expressly including pest-resistant and/or fungus- resistant transgenic useful plants.

In the context of the present invention, pest-resistant transgenic crop plants are to be understood as being those which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria, especially those of the genus Bacillus.

Toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins, for example insecticidal proteins from Bacillus cereus or Bacillus popliae; or insecticidal proteins from Bacillus thuringiensis, such as δ-endotoxins, e.g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl) or Cryθc, or vegetative insecticidal proteins (VIP), e.g. VIP1 , VIP2, VIP3 or VIP3A; or insecticidal proteins of bacteria-colonising nematodes, for example Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophilus; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins and other insect-specific neurotoxins; toxins produced by fungi, such as Streptomycetes toxins; plant lectins, such as pea lectins, barley lectins or snowdrop lectins; agglutinins; proteinase inhibitors, such as trypsine inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luff in, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroidoxidase, ecdysteroid-UDP-glycosyl-transf erase, cholesterol oxidases, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers, such as blockers of sodium or calcium channels, juvenile hormone esterase, diuretic hormone receptors, stilbene synthase, bibenzyl synthase, chitinases and glucanases.

In the context of the present invention there are to be understood by δ-endotoxins, for example CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl) or Cryθc, or vegetative insecticidal proteins (VIP), for example VIP1, VIP2, VIP3 or VIP3A, expressly also hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are produced recombinantly by a new combination of different domains of those proteins (see, for example, WO 02/15701). An example of a truncated toxin is a truncated CrylA(b), which is expressed in Bt11 maize of Syngenta Seeds SAS, as described hereinbelow. In the case of modified toxins, one or more amino acids of the naturally occurring toxin is/are replaced. In such amino acid replacements, preferably non-naturally present protease recognition sequences are inserted into the toxin, such as, for example, in the case of CrylllA055, a cathepsin-D- recognition sequence is inserted into a CrylllA toxin (see WO 03/018810).

Examples of such toxins or transgenic plants capable of synthesising such toxins are disclosed, for example, in EP-A-0374753, WO 93/07278, WO 95/34656, EP-A-0427529, EP-A-451 878 and WO 03/052073.

The processes for the preparation of such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. Cryl-type deoxyribonucleic acids and their preparation are known, for example, from WO 95/34656, EP-A-0367474, EP-A-0401 979 and WO 90/13651.

The toxin contained in the transgenic plants provides the plants with tolerance to harmful insects. Such insects can occur in any taxonomic group of insects, but are especially commonly found in beetles (Coleoptera), two-winged insects (Diptera) and butterflies (Lepidoptera).

The following harmful insects from different taxonomic groups are especially common in maize crops: Ostrinia nubilalis, European corn borer Agrotis ipsilon, black cutworm Helicoverpa zea, corn earworm Spodoptera frugiperda, fall armyworm Diatraea grandiosella, southwestern corn borer Elasmopalpus lignosellus, lesser cornstalk borer Diatraea saccharalis, sugarcane borer Diabrotica virgifera virgifera, western corn rootworm Diabrotica longicornis barberi, northern corn rootworm Diabrotica undecimpunctata hόwardi, southern corn rootworm Melanotus spp., wireworms Cyclocephala borealis, northern masked chafer (white grub) Cyclocephala immaculate, southern masked chafer (white grub) Popillia japonica, Japanese beetle Chaetocnema pulicaria, corn flea beetle Sphenophorus maidis, maize billbug Rhopalosiphum maidis, corn leaf aphid Anuraphis maidiradicis, corn root aphid Blissus leucopterus leucopterus, chinch bug Melanoplus femurrubrum, red-legged grasshopper Melanoplus sanguinipes, migratory grasshopper Hylemya platura, seedcorn maggot Agromyza parvicornis, corn blotch leafminer Anaphothrips obscurus, grass thrips Solenopsis milesta, thief ant Tetranychus urticae, two-spotted spider mite

Transgenic plants containing one or more genes that code for an insecticidal resistance and express one or more toxins are known and some of them are commercially available. Examples of such plants are: YieldGard® (maize variety that expresses a CrylA(b) toxin); YieldGard Rootworm® (maize variety that expresses a CrylllB(bl) toxin); YieldGard Plus® (maize variety that expresses a CrylA(b) and a CrylllB(bl) toxin); Starlink® (maize variety that expresses a Cry9(c) toxin); Herculex I® (maize variety that expresses a CrylF(a2) toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety that expresses a CrylA(c) toxin); Bollgard I® (cotton variety that expresses a CrylA(c) toxin); Bollgard II® (cotton variety that expresses a CrylA(c) and a CryllA(b) toxin); VIPCOT® (cotton variety that expresses a VIP toxin); NewLeaf® (potato variety that expresses a CrylllA toxin); NatureGard® and Protecta®.

Further examples of such transgenic crops are:

1. Bt11 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated CrylA(b) toxin. Bt11 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium. 2. Bt176 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR 96/05/10. Genetically modified Zea mays which has been rendered resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a CrylA(b) toxin. Bt176 maize also transgenically expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.

3. MIR604 Maize from Syngenta Seeds SAS, Chemin de I'Hobit 27, F-31 790 St. Sauveur, France, registration number C/FR/96/05/10. Maize which has been rendered insect-resistant by transgenic expression of a modified CrylllA toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-D-protease recognition sequence. The preparation of such transgenic maize plants is described in WO 03/018810.

4. MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/DE/02/9. MON 863 expresses a CrylllB(bl) toxin and has resistance to certain Coleoptera insects.

5. IPC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/ES/96/02.

6. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C/NL/00/10. Genetically modified maize for the expression of the protein Cry1 F for achieving resistance to certain Lepidoptera insects and of the PAT protein for achieving tolerance to the herbicide glufosinate ammonium.

7. NK603 MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C/GB/02/M3/03. Consists of conventionally bred hybrid maize varieties by crossing the genetically modified varieties NK603 and MON 810. NK603 x MON 810 Maize transgenically expresses the protein CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts tolerance to the herbicide Roundup® (contains glyphosate), and also a CrylA(b) toxin obtained from Bacillus thuringiensis subsp. kurstaki which brings about tolerance to certain Lepidoptera, including the European corn borer.

Transgenic crops of insect-resistant plants are also described in BATS (Zentrum fur Biosicherheit und Nachhaltigkeit, Zentrum BATS, Clarastrasse 13, 4058 Basel, Switzerland) Report 2003, (http://bats.ch). In the context of the present invention, fungus-resistant transgenic crop plants are to be understood as being those which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising antipathogenic substances having a selective action, such as, for example, the so-called "pathogenesis-related proteins" (PRPs, see e.g. EP-A-0 392225). Examples of such antipathogenic substances and transgenic plants capable of synthesising such antipathogenic substances are known, for example, from EP-A-0392225, WO 95/33818 and EP-A-0353 191. The methods of producing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.

Antipathogenic substances which can be expressed by such transgenic plants include, for example, ion channel blockers, such as blockers for sodium and calcium channels, for example the viral KP1 , KP4 or KP6 toxins; stilbene synthases; bibenzyl synthases; chitinases; glucanases; the so-called "pathogenesis-related proteins" (PRPs; see e.g. EP-A-0392225); antipathogenic substances produced by microorganisms, for example peptide antibiotics or heterocyclic antibiotics (see e.g. WO 95/33818) or protein or polypeptide factors involved in plant pathogen defence (so-called "plant disease resistance genes", as described in WO 03/000906).

In the context of the present invention, pest-resistant and/or fungus-resistant transgenic useful plants include expressly those useful plants which, in addition to pest-resistance and/or fungus-resistance, also possess herbicide tolerance. Of the group of herbicide- tolerant useful plants, preference is given according to the invention to those having tolerance to glyphosate, glufosinate ammonium, ALS (acetolactate synthase) inhibitors, e.g. sulfonylureas, for example primisulfuron, prosulfuron and trifloxysulfuron, or bromoxynil, such as Bt11 maize or Herculex I® maize.

Areas of cultivation are areas of land on which the crop plants are already growing and also areas of land on which it is intended to grow those crop plants.

The following Examples further illustrate, but do not limit, the invention. Preparation Examples:

Example P1 : Preparation of 1 -oxy-5-trifluoromethyl-pyridine-2-carboxylic acid ethyl ester: 197 g (2.1 mol) of hydrogen peroxide in the form of the urea adduct are stirred into a solution of 132 g (0.6 mol) of 5-trifluoromethyl-pyridine-2-carboxylic acid ethyl ester in 1000 ml of 1 ,2- dichloroethane. 346 g (1.65 mol) of trifluoroacetic anhydride are then added over 2.5 hours at a temperature of -10°C, with cooling (CO₂/acetone bath). The reaction mixture is then stirred for a further 2 hours at a temperature of 0°C and then for 12 hours at ambient temperature. The reaction mixture is then poured into ice-water and adjusted to pH 6-7 with 30 % sodium hydroxide solution. The mixture is extracted several times with 1 ,2-dichloro- ethane, dried over sodium sulfate and concentrated to dryness by evaporation. The residue is chromatographed on silica gel (eluant: ethyl acetate / hexane 1 :4). 98.4 g of 1-oxy-5- trifluoromethyl-pyridine-2-carboxylic acid ethyl ester (m.p. 64.5 to 65°C) are obtained.

Example P2: Preparation of 6-hvdroxy-5-trifluoromethyl-pyridine-2-carboxylic acid ethyl ester:

450 ml of trifluoroacetic anhydride are added dropwise to a mixture of 77.6 g (0.33 mol) of 1-oxy-5-trifluoromethyl-pyridine-2-carboxylic acid ethyl ester in 900 ml of dimethylformamide at a temperature of 0°C over 3.5 hours. The mixture is then heated to a temperature of from 45 to 50°C and is stirred for a further 2.5 hours. The reaction mixture is then concentrated under reduced pressure (2.5 kPa). The still oily residue is poured into ice-water and adjusted to pH 5.5 with 30 % sodium hydroxide solution. The crystallised product which precipitates out is filtered off, washed neutral with water and dried in a vacuum cabinet at a temperature of 80°C. 61.6 g (79.4 %) of 6-hydroxy-5-trifluoromethyl-pyridine-2-carboxylic acid ethyl ester (m.p. 141-141.5°C) are obtained.

Example P3: Preparation of 6-chloro-5-trifluoromethyl-pyridine-2-carboxylic acid ethyl ester: 16.5 g (70 mmol) of 6-hydroxy-5-trif luoromethyl-pyridine-2-carboxylic acid ethyl ester in 20 ml of phenyl dichlorophosphate are heated in a small pressure reactor for 30 minutes at a temperature of 170°C. The cooled reaction mixture is taken up in ethyl acetate, washed once with cold sodium chloride solution, dried over sodium sulfate and then concentrated. To remove phosphate-containing constituents, the residue that remains behind is filtered over a silica gel column using a mixture of ethyl acetate / hexane 1 :4 and is then concentrated to dryness by evaporation. 16.2 g (91.3 %) of 6-chloro-5-trif luoromethyl-pyridine-2-carboxylic acid ethyl ester are obtained in the form of an oil; ¹H NMR (CDCI₃): 8.17, m, 2H; 4.52, q, 2H; 1.44, t, 3H.

Example P4: Preparation of 6-(morpholin-4-yl)-5-trifluoromethyl-pyridine-2-carboxylic acid ethyl ester:

6.45 g (25 mmol) of 6-chloro-5-trifluoromethyl-pyridine-2-carboxylic acid ethyl ester are heated at a temperature of 110°C for 1 hour in the presence of 5.5 g (63 mmol) of morpho- line and a catalytic amount of 4-N,N-dimethylaminopyridine in 50 ml of N-methylpyrrolidone. The reaction mixture is then adjusted to pH 4 with dilute hydrochloric acid, extracted with ethyl acetate, dried over magnesium sulfate and then concentrated. In order to remove polar subsidiary products, the residue is filtered through a small amount of silica gel and then concentrated to dryness by evaporation, yielding 7.08 g of 6-(morpholin-4-yl)-5-trifluoro- methyl-pyridine-2-carboxylic acid ethyl ester in the form of an oil; H NMR (CDCI₃): 7.97, d, 1H; 7.68, d, 1H; 4.42, q, 2H; 3.83, m, 4H; 3.40, m, 4H; 1.42, t, 3H.

Example P5: Preparation of 6-(morpholin-4-yl)-5-trifluoromethyl-pyridine-2-carboxylic acid: 7 g (23 mmol) of 6-(morpholin-4-yl)-5-trifluoromethyl-pyridine-2-carboxylic acid ethyl ester are added to a mixture of 30 ml of dioxane and 25 ml of water in the presence of 1.55 g of potassium hydroxide and the reaction mixture is stirred at ambient temperature for 30 minutes. The reaction mixture is then acidified to pH 3 and extracted with ethyl acetate, dried over sodium sulfate and concentrated slightly. Addition of hexane causes 6-(morpholin- 4-yl)-5-trif luoromethyl-pyridine-2-carboxylic acid to precipitate out: m.p.: 116-117°C; yield 93.2 %.

Example P6: Preparation of 6-(morpholin-4-yl)-5-trifluoromethyl-pyridine-2-carboxylic acid chloride:

0.83 g (3 mmol) of 6-(morpholin-4-yl)-5-trifluoromethyl-pyridine-2-carboxylic acid and 0.46 g

(3.6 mmol) of oxalyl chloride in 10 ml of dichloromethane are heated at boiling temperature for 15 minutes in the presence of a drop of dimethylformamide. The clear, yellowish solution is then concentrated by evaporation, yielding 6-(morpholin-4-yl)-5-trifluoromethyl-pyridine-2- carboxylic acid chloride in the form of a crystalline product; m.p. 72-73°C. Example P7: Preparation of 6-(acetyl-methyl-amino)-5-trifluoromethyl-pyridine-2-carboxylic acid ethyl ester:

At a temperature of 0°C, with cooling, a solution of 1.46 g (11.5 mmol) of oxalyl chloride in 5 ml of dichloromethane is added dropwise to a solution of 0.84 g (11.5 mmol) of N-methyl- acetamide and 2.45 g (22.9 mmol) of lutidine in 40 ml of dichloromethane. After 20 minutes' stirring, 2.45 g (10.4 mmol) of 1-oxy-5-trifluoromethyl-pyridine-2-carboxylic acid ethyl ester dissolved in 5 ml of dichloromethane are added. The reaction mixture is allowed to rise to ambient temperature and then heated at boiling temperature for 1 hour. The reaction mixture is then extracted with water against dichloromethane, dried over MgSO₄ and then concentrated by evaporation. The resulting residue is purified by column chromatography (eluant: ethyl acetate / hexane 3:7), 6-(acetyl-methyl-amino)-5-trifluoromethyl-pyridine-2-carboxylic acid ethyl ester being isolated as main component; m.p. 145-145.5°C.

Example P8: Preparation of 6-(H .31dioxolan-2-ylmethoxy)-5-trifluoromethyl-pyridine-2- carboxylic acid ethyl ester:

1.88 g (8 mmol) of 6-hydroxy-5-trifluoromethyl-pyridine-2-carboxylic acid ethyl ester and 1.47 g (8 mmol) of 2-bromomethyl-1 ,3-dioxolane in 30 ml of acetonitrile are heated at reflux temperature in the presence of 1.22 g (8.8 mmol) of potassium carbonate and catalytic amounts of potassium iodide and 18-crown-6 for 6 hours. The reaction mixture is then extracted with ethyl acetate against water and dilute acid at pH 3, dried over sodium sulfate and concentrated by evaporation. After chromatographic separation of the residue (eluant: ethyl acetate / hexane 15:85), 6-([1,3]dioxolan-2-ylmethoxy)-5-trifluoromethyl-pyridine-2- carboxylic acid ethyl ester is obtained in the form of an oil; ¹H NMR (CDCI₃): 8.00, d, 1 H; 7.76, d, 1 H; 1.40, t, 1 H; 4.61 , d, 2H; 4.42, q, 2H; 4.09, m, 2H; 3.93, m, 2H; 1.42, t, 3H.

Example P9: Preparation of 6-(tetrahvdro-furan-3-yloxy)-5-trifluoromethyl-pyridine-2- carboxylic acid ethyl ester:

2.35 g (10 mmol) of 6-hydroxy-5-trifluoromethyl-pyridine-2-carboxylic acid ethyl ester dissolved in 30 ml of dimethoxyethane are treated dropwise in the presence of 3.93 g (15 mmol) of triphenylphosphine with a solution of 2.53 g (14.5 mmol) of azodicarboxylic acid diethyl ester (DEAD), the temperature being maintained at a maximum of 35°C by means of an ice bath. After one hour's stirring at ambient temperature, the reaction mixture is concentrated by evaporation and the reaction product that remains behind is purified using a short silica gel column (eluant: ethyl acetate / hexane 1 :4). 2.85 g (93.4 %) of 6-(tetrahydrofuran- 3-yloxy)-5-trifluoromethyl-pyridine-2-carboxylic acid ethyl ester are obtained (m.p.: 45- 45.5°C).

Example P10: 6-Methyl-5-trifluoromethyl-pyridinecarboxylic acid ethyl ester: 6.9 g (6 mmol) of tetrakis(triphenylphosphine)paliadium and 8.3 g (66 mmol) of 2,4,6-tri- methyl-cyclotriboroxane are added to a solution of 15.2 g (60 mmol) of 6-chloro-5-trifluoro- methyl-pyridinecarboxylic acid ethyl ester and 33.1 g (0.24 mol) of potassium carbonate in 150 ml of dioxane and the mixture is heated for 2.5 hours at reflux temperature. The end point of the reaction is determined by thin-layer chromatography. The reaction mixture is poured into ice-water and is adjusted to pH 5 with concentrated hydrochloric acid. To separate off solid constituents, a filtration aid (e.g. Hyflo®) is added and filtered off and the product is extracted with ethyl acetate. The organic extract, dried over sodium sulfate, is concentrated to dryness by evaporation and purified by chromatography on silica gel (eluant: ethyl acetate / hexane 7.5:92.5). 11.28 g (87.8 %) of 6-methyl-5-trifluoromethyl-pyridine- carboxylic acid ethyl ester are obtained in the form of an oil; ¹H NMR (CDCI₃): 8.05, "s", 2H; 4.48, q, 2H; 2.31 , 2, 3H; 1.42, t, 3H.

Example P11 : 6-Bromomethyl-5-trif luoromethyl-pyridine-2-carboxylic acid ethyl ester: 1 g (4.3 mmol) of 6-methyl-5-trifluoromethyl-pyridine-2-carboxylic acid ethyl ester and 0.92 g of N-bromo-succinimide are dissolved in 20 ml of carbon tetrachloride. A catalytic amount of aza.aza-diisobutyronitrile is added and the mixture is heated at reflux temperature using a light source (200 Watt). The reaction product is filtered off and purified using an HPLC technique (eluant: ethyl acetate/hexane 1 :4). 6-Bromomethyl-5-trifluoromethyl-pyridine-2- carboxylic acid ethyl ester is so obtained; ¹H NMR (CDCI₃): 6.14, "s", 2H; 4.78, s, 2H; 4.49, q, 2H; 1.45, t, 3H.

Example P12: 6-(2-Methoxy-ethoxymethyl)-5-trifluoromethyl-pyridine-2-carboxylic acid: 0.6 g (2 mmol) of 6-bromomethyl-5-trifluoromethyl-pyridine-2-carboxylic acid ethyl ester, dissolved in 3 ml of tetrahydrofuran, is introduced into a solution of 0.25 g (5.8 mmol) of sodium hydride (55 % dispersion in oil) in 10 ml of dry tetrahydrofuran. The mixture is stirred for 2 hours at ambient temperature. The end point of the reaction is determined by means of thin-layer chromatography. Water is added to the reaction mixture. After hydrolysis of the ester group is complete (again demonstrated by means of thin-layer chromatography), the organic constituents of the reaction mixture are extracted with diethyl ether and discarded. The aqueous phase is adjusted to pH 2 with hydrochloric acid and extraction with ethyl acetate is carried out; the organic phase is dried over sodium sulfate and then concentrated to dryness by evaporation. 6-(2-Methoxy-ethoxymethyl)-5-trifluoromethyl-pyridine-2- carboxylic acid is so obtained; ¹H NMR (CDCI₃): 8.26, d, 1H; 8.17, d, 1H; 7.3, b, OH; 4.96, s, 2H; 3.91 , m, 2H; 3.71, m, 2H; 3.48, s, 3H.

Example P13: 4-(6-Diethylamino-5-trif luoromethyl-pyridine-2-carbonv0-2-methyl-2,4-dihydro- pyrazol-3-one:

0.28 g (1 mmol) of 6-diethylamino-5-trifluoromethyl-pyridine-2-carboxylic acid choride, freshly prepared with oxalyl chloride, is added to a solution of 0.135 g (1 mmol) of the hydrochloride of 2-methyl-2H-pyrazol-3-ol and 0.35 g of triethylamine (3.5 mmol) in 15 ml of acetonitrile. The mixture is stirred at ambient temperature for half an hour. 2 drops of acetone cyanohydrin are added and the mixture is stirred for 16 hours. The reaction mixture is taken up in ethyl acetate and washed with dilute hydrochloric acid at pH 3. The volume of the organic phase is concentrated and chromatographed on silica gel (eluant: ethyl acetate / methanol / triethylamine 85:10:5). In order to free the end product, the resulting triethylammonium salt of 4-(6-diethylamino-5-trifluoromethyl-pyridine-2-carbonyl)-2-methyl-2,4-dihydro-pyrazol-3- one (M⁺ = HN⁺Et₃) is taken up in 20 ml of ethyl acetate, washed again with dilute hydrochloric acid at pH 3 and dried over sodium sulfate. The volume of the organic phase is concentrated again. By addition of n-hexane, 4-(6-diethylamino-5-trifluoromethyl-pyridine-2- carbonyl)-2-methyl-2,4-dihydro-pyrazol-3-one is obtained in the form of a crystalline solid (m.p. 70-70.5°C).

Example P14: 5-Trifluoromethyl-6-vinyl-pyridine-2-carboxylic acid ethyl ester: 3 g (11.8 mmol) of chloro-5-trifluoromethyl-pyridine-2-carboxylic acid ethyl ester are dissolved in degassed dioxane, and 4.13 g (13.02 mmol) of tributylvinyltin are added. After the addition of 273 mg (0.236 mmol) of Pd(Ph₃P) , the reaction mixture is stirred for 20 hours at 95°C. The reaction mixture is concentrated and is chromatographed on silica gel (eluant: ethyl acetate / isohexane 1 :5). 2 g of 5-trifluoromethyl-6-vinyl-pyridine-2-carboxy!ic acid ethyl ester are obtained. ¹H NMR (CDCI₃): 8.07(d), J=8.3Hz,1H; 8.034(d), J=8.3Hz, 1H; 7.06- 7.18(m), Jab=16.6Hz, Jac=10.5Hz, 1Ha; 6.77(dd), Jba=16.6 Hz, Jbc=2Hz, 1 Hb; 5.74(dd), Jca=10.5 Hz, Jcb= 2Hz, 1 Hc; 4.487(q), 2H; 1.455(t), 3H.

Example P15: 6-(1-Ethoxy-vinyl)-5-trifluoromethyl-pyridine-2-carboxylic acid ethyl ester: 1.6 g (6.31 mmol) of chloro-5-trifluoromethyl-pyridine-2-carboxylic acid ethyl ester are dissolved in 32 ml of degassed dioxane, and 2.5 g (6.92 mmol) of 1-ethoxy-1 -tributylvinyltin are added. After the addition of 146 mg (0.126 mmol) of Pd(Ph₃P)₄, the reaction mixture is stirred for 20 hours at 95°C. The reaction mixture is concentrated and is chromatographed on silica gel (eluant: ethyl acetate / isohexane 1 :5). 0.9 g of 6-(1-ethoxy-vinyl)-5-trifluoro- methyl-pyridine-2-carboxylic acid ethyl ester are obtained. ¹H NMR (CDCI₃): 8.148(s), 2H, 4.732(d), Jab=3Hz, 1 Ha; 4.509(d), Jba= 3Hz, 1Hb; 4.497(q), CH₂O (ester); 2H, 3.952(q), CH₂O (ether), 2H, 1.436(t), CH₃ (ester), 3H; 1.376(t), CH₃ (ether), 3H.

By that means it is possible, for example, also for the compounds of formula I listed in the following Table to be prepared, those compounds that are defined as an oil, resin, wax or (amorphous) solid at least having been characterised in pure form by means of ¹H NMR (nuclear resonance spectroscopy) and/or MS (mass spectrometry).

In general, substituents Ri are bonded to the pyridyl ring by way of the free valence at the atom on the left-hand side of the substituent R^ as in the case, for example, of compound 1.001. In that compound, the substituent R₁ = OCH₂OCH₃ is bonded to the pyridyl ring by way of the free valence of the oxygen atom on the left-hand side of the substituent. In individual cases, the linking atom is, in addition, marked by means of an apostrophe, as in the case, for example, of compound no. 1.142.

In the case of cyclic substituents R^ that are bonded directly to the pyridyl ring, the ring atom of the cyclic substituent Ri linked to the pyridyl is given special emphasis by means of an

apostrophe,

where the linkage site is located at the nitrogen atom denoted by 'N.

Table 1 : Compounds of formula IA

Ex. No. Rso Rβi Ri R₂ Physical properties 1.001 CH₂CH₃ H OCH₂OCH₃ CF₃ 1.002 CH₂CH₃ H OCH₂OCH₂CH₃ CF₃ 1.003 CH₂CH₃ H OCH₂CH₂OCH₃ CF₃ m.p. g3-94°C

Ex. No. R₈₀ Rsι i R2 Physical properties

1.077 CH₃ H CF₃ m.p.: 128-129°C

1.080 CH₂CH₃ CH₃ / \ CF₃ 'N O \_V 1.081 CH₃ H CF₃ m.p.: 165-166°C

1.083 CH₂CH₃ H .. OF, CF₃ m.p. 129-130°C

Ex. No. Rso Rsι Ri 2 Physical properties

1.090 CH₃ H N(CH₃)C(O)H CF₃ 1.091 CH₃ H N(CH₃)C(O)CH₃ CF₃ m.p. 138-139°C 1.092 CH₂CH₃ H N(CH₃)C(O)CH₂CH₃ CF₃ 1.093 CH₂CH₃ H N(CH₃)C(O)-phenyl CF₃ 1.094 CH₃ H N(CH₃)C(O)-benzyl CF₃ 1.095 CH₃ H N(CH₂CH₃)C(O)CH₃ CF₃ 1.096 CH₃ H N(CH₃)₂ CF₃ m.p.: 103-104°C 1.097 CH₃ H N(CH₂CH₃)₂ CF₃ m.p.: 70-71 °C, [P13] 1.098 CH₃ H N(CH₃)C(O)-phenyl CF₃ amorphous crystals 1.099 CH₃ CH₃ N(CH₃)C(O)-benzyl CF₃ m.p.: 202-204°C 1.100 CH₃ H N(CH₃)C(O)CH₂CH₃ CF₃ m.p.:134-135°C 1.101 CH₃ H CH₂OH CF₃ 1.102 CH₃ H CH₂CI CF₃ 1.103 CH₃ H CH₂Br CF₃ 1.104 CH₃ H CH₂OSO₂CH₃ CF₃ 1.105 CH₃ H CH₂OC(O)CH₃ CF₃ Ex. No. Rso βi i R₂ Physical properties 1.106 CH₃ H CH₂OC(O)C(CH₃)₃ CF₃ 1.107 CH₃ H CH₂OC(O)-phenyl CF₃ 1.108 CH₃ H CH₂OC(O)OCH₂CH₃ CF₃ 1.109 CH₃ H CH₂OCH₃ CF₃ 1.110 CH₃ H CH₂OCH₂CH₀) CF₃ 1.112 CH₃ H CH₂CH₂OCH₃ CF₃ 1.113 CH₃ H CH₂CH₂OCH₂CH₃ CF₃ 1.114 CH₃ H CH₂CH₂CH₂OCH₃ CF₃ 1.115 CH₃ H CH(CH₃)CH₂OCH₃ CF₃ 1.116 CH₃ H CH₂OCH₂CH=CH₂ CF₃ 1.117 CH₃ H CH₂OCH₂C≡CH CF₃ 1.118 CH₃ H CH₂θCH₂C≡CCH₃ CF₃ 1.119 CH₃ H CH₂OCH₂CH₂C≡CH CF₃ 1.120 CH₃ H CH₂OCH₂CH₂C≡CCH₃ CF₃ 1.121 CH₃ H CH₂O-benzyl CF₃ 1.122 CH₃ H CH₂OCH₂CF₃ CF₃ 1.123 CH₃ H CH₂OCH₂CH₂F CF₃ 1.124 CH₃ H CH₂OCH₂CH₂CI CF₃ 1.125 CH₃ H CH₂OCH₂CH₂Br CF₃ 1.126 CH₃ H CH₂OCH₂CH₂C≡N CF₃ 1.127 CH₃ H CH₂OCH₂C≡N CF₃ 1.128 CH₃ H CH₂OCH₂OCH₃ CF₃ 1.129 CH₃ H CH₂OCH₂OCH₂CH₃ CF₃ 1.130 CH₃ H CH₂OCH₂CH₂OH CF₃ 1.131 CH₃ H CH₂OCH₂CH₂OCH₃ CF₃ resin 1.132 CH₃ H CH₂θCH₂CH₂OCH₂CH₃ CF₃ 1.133 CH₃ H CH₂OCH₂CH₂CH₂θCH₃ CF₃ 1.134 CH₃ H CH₂OCH(CH₃)CH₂OCH₃ CF₃ 1.135 CH₃ H CH₂OCH₂CH₂OCH₂CH=CH₂ CF₃ 1.136 CH₃ H CH₂OCH₂CH₂OCH₂C≡CH CF₃ 1.137 CH₃ H CH₂OCH₂CH₂O-benzyl CF₃ 1.138 CH₃ H CH₂OCH₂CH₂ON=C(CH₃)₂ CF₃ Ex. No. Rso R₈ι Ri ^R2 Physical properties 1.139 CH₃ H CH₂OCH₂CH₂OCH₂CH₂OCH₃ CF₃ 1.140 CH₃ H CH₂OCH₂CH(OCH₃)₂ CF₃ 1.141 CH₃ H CH₂OCH₂CH(OCH₂CH₃)₂ CF₃

Ex. No. R 80 *81 Ri Physical properties

1.205 CH₃ H CF₃ solid

1.206 CH₃ H CF₃ solid

1.207 CH₃ H phenyl CF₃ 1.208 CH₃ H C(O)CH₃ CF₃ 1.209 CH₃ H C(O)CH₂OCH₃ CF₃ 1.210 CH₃ H C(O)CH₂OCH₂CH₂OCH₃ CF₃ 1.211 CH₃ H C(O)CH₂N(SO₂CH₃)CH₃ CF₃ 1.212 CH₃ H OCH₂CH₃ CF₃ solid 1.213 CH₂CH₃ H OCH₂CH₃ CF₃ m.p. 123-124°C 1.214 CH₃ H CH₃ CF₃ m.p. 125-126°C 1.215 CH₂CH₃ H CH₃ CF₃ m.p. 92-93°C 1.216 CH₃ H OCH₂CH(OCH₃)₂ CF₃ solid 1.217 CH₃ H CF₃ solid

1.219 CH₂CH₃ H CF₃

Ex. No. ^80 Ri 81 Ri Physical properties 1.221 CH₂CH₃ H CF₃ ^•c⁷^ V°

1.228 CH₃ H 4-CF₃-phenyl CF₃ 1.229 CH₃ H 4-MeO-phenyl CF₃ 1.230 CH₃ H C(OCH2CH₂CH₂CH₃)=CH2 CF₃ 1.232 CH₃ H CH₂CH₂OCH₂CH₂CH₂CH₃ CF₃ 1.233 CH₃ H CH₂O-phenyl CF₃ 1.234 CH₃ H CH₂NHSO₂-phenyl CF₃ 1.235 CH₃ H CH₂N(SO₂CH₃)-cyclopropyl CF₃ 1.237 CH₃ H CH₂N(SO₂CH₂CH₃)-phenyl CF₃ 1.238 CH₃ H CH₂NHC(O)-c rclopropyl CF₃ Ex. No. R 80 R; 81 Ri Physical properties 1.239 CH₃ H CF₃ isomer A (cis or trans), crystalline solid

1.240 CH, H CF₃ isomer B (cis or trans), crystalline solid

Table Z1 : Intermediates of formula II

Ex. No. i Physical properties Z1.001 OH OCH₂OCH₃ CF₃ Z1.002 OH OCH₂OCH₂CH₃ CF₃ Z1.003 OH OCH₂CH₂OCH₃ CF₃ m.p.: 66-67°C Z1.004 OH OCH₂CH₂OCH₂CH₃ CF₃ Z1.005 OH OCH₂CH₂CH₂OCH₃ CF₃ Z1.006 OH OCH(CH₃)CH₂OCH₃ CF₃ Z1.007 OH OCH₂CH₂OCH₂CH=CH₂ CF₃ Z1.008 OH OCH₂CH₂OCH₂C≡CH CF₃ Z1.009 OH OCH₂CH₂O-benzyl CF₃ Z1.010 OH OCH₂CH₂ON=C(CH₃)₂ CF₃ m.p.: 106-107°C Z1.011 OH OCH₂CH₂OCH₂CH₂OCH₃ CF₃ Z1.012 OH OCH₂CH(OCH₃)₂ CF₃ m.p.: 53-54°C Z1.013 OH OCH₂CH(OCH₂CH₃)₂ CF₃ Z1.014 OH CF₃ amorphous

Ex. No. Y Ri R₂ Physical properties

Z1.021 OH °- CF₃ m.p.: 124-125°⁽

Z1.022 OH CF₃ waxy ^Ό^ °

Z1.023 OH O-benzyl CF₃ m.p.: 96-97°C

Z1.024 OH OCH₂CH₂SCH₃ CF₃

Z1.025 OH OCH₂CH₂SCH₂CH₃ CF₃

Z1.026 OH OCH₂CH₂S(O)₂CH₃ CF₃

Z1.027 OH OCH₂CH₂S(O)₂CH₂CH₃ CF₃

Z1.028 OH SCH₂CH₂OCH₃ CF₃

Z1.029 OH SCH₂CH₂OCH₂CH₃ CF₃

Z1.030 OH OCH₂CH₂OC(O)CH₃ CF₃

Ex. No. Ri Physical properties

Z1.064 OH NHCH₂CH₂OH CF₃

Z1.065 OEt NHCH₂CH₂OCH₃ CF₃ oil

Z1.066 OH NHCH(CH₃)CH₃OCH₃ CF₃

Z1.067 OH NHCH₂CH(OCH₃)₂ CF₃

Z1.068 OH NHCH₂CH(OCH₂CH₃)₂ CF₃

Z1.070 OH NHCH₂C(O)OCH₃ CF₃

Z1.071 OH NHCH(CH₃)C(O)OCH₃ CF₃

Z1.072 OH NHCH₂C(O)OCH₂CH₃ CF₃

Z1.073 OH NHCH(CH₃)C(O)OCH₂CH₃ CF₃

Z1.074 OH CF₃ m.p.: 115-116°C, [P5]

Z1.075 OH CH CF₃ / N O \ /

Z1.076 OH CF₃ m.p.: 127-128°C

Ex. No. Ri Physical properties

Z1.080 OH CF₃ m.p.: 103-104°C

Z1.082 OH CF₃ amorphous

Z1.086 OH N(CH₃)C(O)H CF₃

Z1.087 OH N(CH₃)C(O)CH₃ CF₃ m.p.: 164-165°C

Z1.088 OH N(CH₃)C(O)CH₂CH₃ CF₃ m.p.: 76-77°C

Z1.089 OH N(CH₃)C(O)-phenyl CF₃ m.p.: 137-138°C

Z1.090 OH N(CH₃)C(O)-benzyl CF₃ m.p.: 154-156°C

Z1.091 OH N(CH₂CH₃)C(O)CH₃ CF₃

Z1.092 OH OH CF₃ m.p.: 220°C

Z1.093 OH Cl CF₃ m.p.: 166-167°C

Z1.094 OH OCH₃ CF₃ m.p.: 139-140°C

Z1.095 OH OCH₂CH₃ CF₃ m.p.: 112-114°C

Z1.096 OH OCH₂CF₃ m.p.: 133-134°C

Ex. No. Y Ri R₂ Physical properties

Z1.097 OEt OH CF₃ m.p.: 141-142°C, [P2]

Z1.098 OEt SCH₃ CF₃ oil

Z1.099 OEt OCH₃ CF₃ m.p.: 71-73°C

Z1.100 OEt OCH₂CF₃ CF₃ oil

Z1.101 OEt Cl CF₃ oil, [P3]

Z1.102 OEt CH₃ CF₃ oil, [P10]

Z1.103 OEt CH₂Br CF₃ oil, [P11]

Z1.104 OEt CHBr₂ CF₃

Z1.105 OEt C(=O)H CF₃

Z1.106 OH CH₂OH CF₃

Z1.107 OEt CH₂CI CF₃

Z1.108 OEt CH₂OSO₂CH₃ CF₃

Z1.109 OH CH₂OC(O)CH₃ CF₃

Z1.110 OH CH₂OC(O)C(CH₃)₃ CF₃

Z1.111 OH CH₂OC(O)-phenyl CF₃

Z1.112 OH CH₂OC(O)OCH₂CH₃ CF₃

Z1.113 OH CH₂OCH₃ CF₃

Z1.114 OH CH₂OCH₂CH₃ CF₃

Z1.115 OH CH₂CH₂OCH₃ CF₃

Z1.116 OH CH₂CH₂OCH₂CH₃ CF₃

Z1.117 OH CH₂CH₂CH₂OCH₃ CF₃

Z1.118 OH CH(CH₃)CH₂OCH₃ CF₃

Z1.119 OH CH₂OCH₂CH=CH₂ CF₃

Z1.120 OH CH₂OCH₂C≡CH CF₃

Z1.121 OH CH₂OCH₂C≡CCH₃ CF₃

Z1.122 OH CH₂OCH₂CH₂C≡CH CF₃

Z1.123 OH CH₂OCH₂CH₂C=CCH₃ CF₃

Z1.124 OH CH₂O-benzyl CF₃

Z1.125 OH CH₂OCH₂CF₃ CF₃

Z1.126 OH CH₂OCH₂CH₂F CF₃

Z1.127 OH CH₂OCH₂CH₂CI CF₃

Z1.128 OH CH₂OCH₂CH₂Br CF₃

Z1.129 OH CH₂OCH₂CH₂C≡N CF₃ Ex. No. Ri Physical properties

Z1.130 OH CH₂OCH₂C≡N CF₃

Z1.131 OH CH₂OCH₂OCH₃ CF₃

Z1.132 OH CH₂OCH₂OCH₂CH₃ CF₃

Z1.133 OH CH₂OCH₂CH₂OH CF₃

Z1.134 OH CH₂OCH₂CH₂OCH₃ CF₃ waxy crystals, [P12]

Z1.135 OH CH₂OCH₂CH₂OCH₂CH₃ CF₃

Z1.136 OH CH₂OCH₂CH₂CH₂θCH₃ CF₃

Z1.137 OH CH₂OCH(CH₃)CH₂OCH₃ CF₃

Z1.139 OH CH₂θCH₂CH₂OCH₂C≡CH CF₃

Z1.140 OH CH₂θCH₂CH₂O-benzyl CF₃

Z1.141 OH CH₂OCH₂CH₂ON=C(CH₃)₂ CF₃

Z1.142 OH CH₂OCH₂CH₂OCH₂CH₂OCH₃ CF₃

Z1.143 OH CH₂OCH₂CH(OCH₃)2 CF₃

Z1.144 OH CH₂OCH₂CH(OCH₂CH₃)₂ CF₃

Ex. No. Y Rj Rg Physical properties

Z1.155 OH CH₂OCH₂CH₂SCH₃ CF₃ Z1.156 OH CH₂OCH₂CH₂SCH₂CH₃ CF₃ Z1.157 OH CH₂OCH₂CH₂S(O)₂CH₃ CF₃ Z1.158 OH CH₂OCH₂CH₂S(O)₂CH₂CH₃ CF₃ Z1.159 OH CH₂SCH₂CH₂OCH₃ CF₃ Z1.160 OH CH₂SCH₂CH₂OCH₂CH₃ CF₃ Z1.161 OH CH₂OCH₂CH₂OC(O)CH₃ CF₃ Z1.162 OH CH₂OCH₂CH₂OC(O)-phenyl CF₃ Z1.163 OH CH₂OCH₂CH₂OC(O)OCH₂CH₃ CF₃ Z1.164 OH CH₂θCH₂CH₂OC(O)NHCH₂CH₃ CF₃ Z1.165 OH CH2OCH2CH2NH2 CF₃ Z1.166 OH CH₂OCH₂CH₂NHC(O)CH₃ CF₃ Z1.167 OH CH₂OCH₂CH₂NHC(O)CH₂CH₃ CF₃ Z1.168 OH CH₂OCH₂CH2NHC(O)CH(CH₃)2 CF₃ Z1.169 OH CH₂OCH₂CH₂NHC(O)-cyclopropyl CF₃ Z1.170 OH CH₂OCH₂CH₂NHC(O)C(CH₃)₃ CF₃

Ex. No. Ri Physical properties

Z1.220 OH CH₃ C≡N m.p. 157-158°C Z1.221 OH CF₃ Cl m.p. 127-129°C

Z1.223 OEt CF₃ oil, [P4]

Z1.224 Cl CF₃ m.p. 72-73°C, [P6]

Z1.225 OEt N(CH₃)C(O)CH₃ CF₃ m.p. 145-145.5°C, [P7]

Z1.229 OH CF₃ amorphous solid

Z1.232 OH CF₃ solid

Ex. No. Y Ri R₂ Physical properties

Z1.233 OH CF₃ amorphous solid

Z1.235 OEt CF₃ oil, isomer I

CF₃ oil, isomer II

Z1.237 OEt CH=CH₂ CF₃ oil

Z1.238 OEt C(OCH₂CH₃)=CH₂ CF₃ oil

Z1.239 OEt C(OCH₂CH₂CH₂CH₃)=CH2 CF₃

Z1.240 OEt CH=CHOCH₂CH₃ CF₃

Z1.241 OEt CH=CHOCH₂CH₂CH₂CH₃ CF₃

Z1.242 OEt C(O)CH₂Br CF₃ oil

Z1.243 OEt C(O)CH₂OH CF₃ oil

Z1.245 OH CH₂CH₂OCH₂CH₂CH CH₃ CF₃

Z1.246 OH CH₂O-phenyl CF₃

Z1.247 OH CH₂NHSO₂-phenyl CF₃

Z1.248 OH CH₂N(SO₂CH₃)-cyclopropyl CF₃

Z1.249 OH CH₂N(SO₂CH₂CH₃)-phenyl CF₃

Z1.250 OH CH₂NHC(O)-cyclopropyl CF₃

Z1.251 OH CH₂NHC(O)-phenyl CF₃ Biological Examples

Example B1 : Herbicidal action prior to emergence of the plants (pre-emergence action) Monocotyledonous and dicotyledonous test plants are sown in standard soil in pots or seed trays. Immediately after sowing, the test compounds, in the form of an aqueous suspension (prepared from a wettable powder (Example F3, b) according to WO 97/34485) or in the form of an emulsion (prepared from an emulsifiable concentrate (Example F1 , c) according to WO 97/34485), are applied by spraying in a concentration of 250 g/ha. The test plants are then grown in a greenhouse under optimum conditions. After a test duration of 4 weeks, the test is evaluated in accordance with a scale of eleven ratings (10 = total damage, 0 = no action). Ratings of from 10 to 7 (especially from 10 to 8) indicate very good to good herbicidal action.

Table B1 : Pre-emergence action:

Ex. No. g/ha Panicum Digitaria Echinochloa Amaranthus Chenopodium Stellaria 1.075 250 9 9 7 9 9 9 1.081 250 10 10 7 0 8 8

Example B2: Post-emergence herbicidal action

Monocotyledonous and dicotyledonous test plants are cultivated in a greenhouse in standard soil in plastic pots and, at the 4- to 6-leaf stage, are sprayed with an aqueous suspension of the test compounds of formula I prepared from a 25 % wettable powder (Example F3, b) according to WO 97/34485) or with an emulsion of the test compounds of formula I prepared from a 25 % emulsifiable concentrate (Example F1 , c) according to WO 97/34485), corresponding to concentrations of 125 and 250 g of active ingredient per hectare (500 litres of water per ha). The test plants are then grown on in the greenhouse under optimum conditions. After a test duration of about 18 days, the test is evaluated in accordance with a scale of eleven ratings (10 = total damage, 0 = no action). Ratings of from 10 to 7 (especially from 10 to 8) indicate very good to good herbicidal action. The compounds of formula I generally exhibit a strong herbicidal action in this test. Table B2: Post-emergence action Ex. No. g/ha Panicum Echino- Euphorbia Xanthium Amaranthus Cheno- Steilaria chloa podium 1.003 250 9 9 6 8 8 10 8 1.021 250 8 8 9 4 7 7 7 1.073 250 9 9 9 4 9 8 7 1.075 250 7 7 5 7 8 10 9 1.077 250 7 8 7 5 5 10 7 1.081 250 8 3 8 7 7 10 9 1.100 250 8 6 7 7 8 9 8

In a different test arrangement, Examples according to Table B3 on selected test plants likewise exhibit good to very good post-emergence action.

Table B3: Post-emergence action

Ex. No. g/ha Digitaria Amaranthus Solanum Nasturtium Steilaria 1.096 250 4 8 8 9 8 1.097 250 4 9 9 9 9 1.131 250 8 5 10 6 7 1.194 250 6 8 8 10 8 1.205 250 8 5 9 10 5 1.215 250 3 6 9 10 8

Claims

What is claimed is:

1. A compound of formula

wherein

Ri is -Lιo-R , -L11-X1-R51 -NRβR₇, -X₂-R8 or -X₃-L-|-Rg;

L₂, U, L₆ and L₈ are each independently of the others CrC₄alkylene which may be substituted once, twice or three times by C|-C₄alkyl, halogen or by Cι-C₄alkoxy and to which Cι-C alkylene group there may additionally be spirocyclically bound a C₂-C₅alkylene group, and wherein that C₂-C₅alkylene group may in turn be interrupted once or twice by oxygen, sulfur, sulfinyl or by sulfonyl and/or substituted by CrC₄alkyl or by d-C₄alkoxy; L₃, l_₅, L₇ and L₉ are each independently of the others d-C alkylene which may be substituted once, twice or three times by CrC alkyl, halogen or by CrC₄alkoxy; R₂ is halogen, Cι-C₄haloalkyl, cyano, CrC₃haloalkoxy, CrC alkylthio, CrC^lkylsulfinyl, C C₄alkylsulfonyl, C C₄haloalkylthio, C C₄haloalkylsulfinyl or d-Cihaloalkylsulfonyl; L₁₀ is a direct bond or a CrC₆alkylene, C₂-C₆alkenylene or C₂-C₆alkynylene group which may be substituted once, twice or three times by CrC₆alkyl, halogen, hydroxy, C C₆alkoxy, C₃-C₆cycloalkyloxy, CrC₆alkoxy-CrC₆alkoxy, Ci-Cβalkoxy-C Cealkoxy-C Cealkoxy or by C₁-C₂alkylsulfonyloxy;

R₄ is halogen, cyano, rhodano, Cι-C₆alkoxycarbonyl, C₃-C₆alkenyloxycarbonyl, C₃-C₆alkynyl- oxycarbonyl, benzyloxycarbonyl, C(O)NR_25aR_26a, formyl, CrC₆alkylcarbonyl, Cι-C₆haloalkyl- carbonyl, d-C^lkoxy-CrC^lkylcarbonyl, d-C^lkoxy-CrC^lkoxy-Ci-C^lkylcarbonyl, N- (Cι-C₄alkyl)-CrC₄alkylsulfonylamino-CrC₄alkylcarbonyl, CrC₆haloalkyl, C₂-C₆alkenyl, C₂-C₆- haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, C₃-C₆cycloalkyl, Cι-C₆alkylsulfonyloxy or phenylsulfonyloxy, wherein the phenyl groups may be substituted by one or more CrC₆alkyl, Cι-C₆- haloalkyl, d-Cβalkoxy, CrC₆haloalkoxy, halogen, cyano, hydroxy or nitro groups; or R₄ is a three- to ten-membered, monocyclic or fused bicyclic ring system which may be aromatic, saturated or partially saturated and which may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, and wherein the ring system may contain not more than 2 oxygen atoms and not more than two sulfur atoms, and each ring system may itself be substituted once, twice or three times by d-C₆alkyl, d-C₆haloalkyl, C C₄alkoxy- d-C₂alkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, d-C₆alkoxy, hydroxy, d-C₆haloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, d-C₆alkylthio, d-Cehaloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆alkynylthio, C₂-C₅alkoxy- alkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄cyanoalkylthio, d-C₆alkyl- sulfinyl, CrC₆haloalkylsulfinyl, d-C₆alkylsulfonyl, d-Cehaloalkylsulfonyl, aminosulfonyl, Cι-C₂alkylaminosulfonyl, di(d-C₂alkyl)aminosulfonyl, di(d-C₄alkyl)amino, halogen, cyano, nitro, phenyl or by benzylthio, and wherein phenyl and benzylthio may in turn be substituted on the phenyl ring by C C₃alkyl, d-C₃haloalkyl, Cι-C₃alkoxy, d-C₃haloalkoxy, halogen, cyano or by nitro, and wherein the substituents on the nitrogen in the heterocyclic ring are other than halogen; or R₄ is hydrogen when L₁₀ is a d-C₆alkylene group which may be substituted once, twice or three times by CrCealkyl or by halogen; or when L₁₀ is a C₂-C₆alkenylene or C₂-C₆alkynylene group which may be substituted once, twice or three times by d-C₆alkyl, halogen, hydroxy, CrC₆alkoxy, C₃-C₆cycloalkyloxy, d-Cealkoxy-d-Cealkoxy, Ci-Cealkoxy-CrCealkoxy-CrCe- alkoxy or by d-C₂alkylsulfonyloxy;

R _5a is hydrogen, d-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, C C₄alkyl, d-C₄haloalkyl, d-C₃alkoxy, d-C₃haloalkoxy, d-C₃alkylthio, d-C₃alkylsulfinyl, CrC₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-C alkoxycarbonyl or by CrC alkylcarbonylamino; R≥βa is hydrogen, CrC₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R _5a together with R_26a and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, C C alkyl, d-C haloalkyl, d-C₃alkoxy, d-C₃- haloalkoxy, d-C₃alkylthio, d-C₃alkylsulfinyl, C_rC₃alkylsulfonyl, Cι-C₃haloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by d-C₄alkylcarbonylamino;

L₁₁ is a CrC₆alkylene, C₂-C₆alkenylene or C₂-C₆alkynylene group which may be substituted once, twice or three times by halogen, hydroxy, d-C₆alkoxy, C₃-C₆cycloalkyloxy, d-C₆- alkoxy-CrC₆alkoxy, d-Cealkoxy-d-Cealkoxy-CrCealkoxy _or by d-C₂alkylsulfonyloxy; Xi is oxygen, -OC(O)-, -C(O)-, -C(=NR_14a)-, -C(O)O-, -C(O)NR_14b-, -OC(O)O-, -N(R₁₀)-O-, -O-NR_ι , thio, sulfinyl, sulfonyl, -SO₂NR₁₂-, -NRι₃SO₂-, -N(SO₂R_14o)-, -N(R_14d)C(O)- or -NR₁₄-;

Rio, R₁1. R₁₂. Ri3. Ri4b» Rι₄d and R₁₄ are each independently of the others hydrogen, d-Cealkyl, d-C₆haloalkyl, d-C₆alkoxycarbonyl, CrC₆alkylcarbonyl, C Cealkoxy-C Ce lkyl, or d-Cealkoxy-d-Cealkyl substituted by CrC₆alkoxy, or benzyl or phenyl, wherein phenyl and benzyl may in turn be substituted once, twice or three times by CrC₆alkyl, d-C₆halo- alkyl, d-C₆alkoxy, d-C₆haloalkoxy, halogen, cyano, hydroxy or by nitro; is hydroxy, d-C₆alkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy or benzyloxy; Ruo is CrCealkyl;

R₅ is hydrogen or a d-C₈alkyl, C₃-C₈alkenyl or C₃-C₈alkynyl or C₃-C₆cycloalkyl group which may be substituted once, twice or three times by chlorine, bromine, iodine, hydroxy, amino, formyl, nitro, cyano, mercapto, CrC₆alkoxy, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, C₃-C₆cycloalkyl, halo-substituted C₃-C₆cycloalkyl, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, CrC₆haloalkoxy, C₃-C₆haloalkenyloxy, cyano-CrC₆alkoxy, CrC₆alkoxy- C_rC₆alkoxy, d-Cealkoxy-d-Cealkoxy-CrCealkoxy, d-Cealkylthio-CrCealkoxy, Cι-C₆alkyl- sulfinyl-CrC₆alkoxy, d-Cealkylsulfonyl-d-Cealkoxy, CrC₆alkoxycarbonyl-CrC₆alkoxy, CrC₆alkoxycarbonyl, CrC₆alkylcarbonyl, phenylcarbonyl, CrC₆alkylthio, CrC₆alkylsulfinyl, d-C₆alkylsulfonyl, CrC₆haloalkylthio, d-C₆haloalkylsulfinyl, d-C₆haloalkylsulfonyl, benzyloxy, benzylthio, benzylsulfinyl, benzylsulfonyl, d-C₆alkylamino, di(CrC₆alkyl)amino, Rι_5aC(X₂₃)N(R_18a)-, Ri_6aN(Ri_7a)C(X₂₄)-, Rι_6bN(Rι_7b)C(X₂₅)NR_18b-, Rι₅cSO₂N(R_18c)-, RieoN(Ri_7c)C(X₂₆)O-, Ri_5bC(X₂₇)O-, R₁₉R₂₀C=NO-, R₁₅S(O)₂O-, R₁₆N(R₁₇)SO₂-, rhodano, phenyl, phenoxy, phenylthio, phenylsulfinyl or by phenylsulfonyl or which may be substituted from one to seventeen times by fluorine; wherein the phenyl- or benzyl-containing groups may in turn be substituted by one or more CrC₆aIkyl, d-C₆haloalkyl, d-C₆alkoxy, CrC₆haloalkoxy, halogen, cyano, hydroxy or nitro groups;

Ri₅a, Ri₅ and R_15o are hydrogen, d-C₆alkyl, C₂-C₆alkenyl, C₃-C₆cycloalkyl, phenyl, benzyl, CrC₈alkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy or benzyloxy, wherein the phenyl groups may be substituted once, twice or three times by CrC₆alkyl, CrC₆haloalkyl, CrC₆alkoxy, d-C₆haloalkoxy, halogen, cyano, hydroxy or by nitro;

Rιea, ieb and R_16c are hydrogen, d-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, C₃-C₆cycloalkyl or phenyl, wherein phenyl may be substituted once, twice or three times by d-C₆alkyl, CrC₆haloalkyl, CrC₆alkoxy, CrC₆haloalkoxy, halogen, cyano, hydroxy or by nitro; Ri₇a, i7b, Ri7c, Rιβa, Rie and R_18c are hydrogen, d-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; X23, X₂₄, X25, X26 and X₂₇ are oxygen or sulfur;

R₁5, R₁6, R₁7, R₁9 and R₂o are each independently of the others hydrogen, d-C₆alkyl, d-Cehaloalkyl, CrCealkoxycarbonyl, CrC₆alkylcarbonyl, CrCealkoxy-CrCealkyl, or CrC₆alkoxy-CrC₆alkyl substituted by CrC₆alkoxy, or benzyl or phenyl, wherein phenyl and benzyl may in turn be substituted once, twice or three times by d-Cealkyl, d-C₆haloalkyl, CrC₆alkoxy, d-Cehaloalkoxy, halogen, cyano, hydroxy or by nitro; or R₅ is a three- to ten-membered monocyclic or fused bicyclic ring system which may be aromatic, saturated or partially saturated and may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, and wherein the ring system is bound to the substituent X_! directly or via a d-C alkylene, C₂-C₄alkenylene, C₂-C₄alkynylene, -N(R₁₈)-d-C₄alkylene, -O-d-C₄alkylene, -S-d-C₄alkylene, -S(O)-d-C₄alkylene or -SO₂-d-C₄alkylene chain, wherein the ring system may not be interrupted by -C(=O)-, -C(=S)-, -C(=NR_5a)-, -N(=O)-, -S(=O)- or by -SO₂-, and each ring system may contain not more than 2 oxygen atoms and not more than two sulfur atoms, and the ring system itself may be substituted once, twice or three times by CrC₆alkyl, d-Cehaloalkyl, C₂-C₆alkenyl, C₂-C₆haloalkenyl, C₂-C₆alkynyl, C₂-C₆haloalkynyl, d-C₆alkoxy, hydroxy, d-dshaloalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, mercapto, CrC₆alkylthio, d-Cβhaloalkylthio, C₃-C₆alkenylthio, C₃-C₆haloalkenylthio, C₃-C₆- alkynylthio, C₂-C₅alkoxyalkylthio, C₃-C₅acetylalkylthio, C₃-C₆alkoxycarbonylalkylthio, C₂-C₄- cyanoalkylthio, d-C₆alkylsulfinyl, C C₆haloalkylsulfinyl, CrC₆alkylsulfonyl, d-C₆haloalkyl- sulfonyl, aminosulfonyl, CrC₂alkylaminosulfonyl, di(d-C₂alkyl)aminosulfonyl, di(d-C₄alkyl)- amino, halogen, cyano, nitro, phenyl or by benzylthio, wherein phenyl and benzylthio may in turn be substituted on the phenyl ring by d-C₃alkyl, d-C₃haloalkyl, d-C₃alkoxy, d-dhaloalkoxy, halogen, cyano or by nitro, and wherein the substituents on the nitrogen in the heterocyclic ring are other than halogen; R_5a is CrC₆alkyl, hydroxy, CrC₆alkoxy, cyano or nitro;

R₁₈ is hydrogen, d-C₆alkyl, CrCehaloalkyl, d-C₆alkoxycarbonyl, CrC₆alkylcarbonyl, CrC₆alkoxy-CrC₆alkyl, or CrC₆alkoxy-CrC₆alkyl substituted by CrC₆alkoxy, or benzyl or phenyl, wherein phenyl and benzyl may in turn be substituted once, twice or three times by CrC₆alkyl, CrCehaloalkyl, d-C₆alkoxy, d-C₆haloalkoxy, halogen, cyano, hydroxy or by nitro;

R₆ is hydrogen, CrCealkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, d-Cehaloalkyl, hydroxy, Cι-C₆alkoxy,

-C(O)R_19a or -C(S)R₂o_a;

Rι_9a and R_20a are each independently of the other hydrogen, d-C₆alkyl, C₃-C₆cycloalkyl, phenyl, benzyl, heteroaryl, CrC₆alkoxy, C₃-C₆alkenyloxy, benzyloxy, d-C₄alkylthio or a group NR21R22;

R₂₁ and R₂₂ are each independently of the other hydrogen, CrC₆alkyl, C₃-C₆alkenyl,

C₃-C₆alkynyl or phenyl, and wherein phenyl, benzyl, benzyloxy and heteroaryl in R_19a, R_20a, R21 and R₂₂ may be substituted once, twice or three times by halogen, d-C₄alkyl, d-dhaloalkyl, C C₃alkoxy, d-C₃haloalkoxy, d-C₃alkylthio, CrC₃alkylsulfinyl, d-C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, CrC alkoxycarbonyl or by d-C₄alkylcarbonylamino; or R21 together with R22 and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, C C₄haloalkyl, d-C₃alkoxy, d-C₃haloalkoxy, CrC₃alkylthio, d-C₃alkylsulfinyl, d-C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, C C₄alkoxycarbonyl or by d-C₄alkylcarbonylamino; or R₆ is -L₂-X₄-R₂₄; wherein X₄ is oxygen, -NR₂₃-, -S-, -S(O)- or -S(O)₂-;

R₂₃ is hydrogen, CrC₆alkoxy, CrC₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or is phenyl which may be substituted once, twice or three times by halogen, d-C₄alkyl, d-C haloalkyl, d-dalkoxy, d-C₃haloalkoxy, C C₃alkylthio, C C₃alkylsulfinyl, d-C₃alkylsulfonyl, d-dhalo- alkylthio, cyano, nitro, CrC₄alkoxycarbonyl or by d-C₄alkylcarbonylamino; R₂₄ is hydrogen or a d-Cealkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group, which groups may be substituted once, twice or three times by halogen, hydroxy, d-C₆alkoxy, d-C₃alkoxy- d-C₃alkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, CrC₆alkylthio, CrC₆alkylsulfinyl, d-d- alkylsulfonyl, cyano, C(X₅)NR₂₅R₂₆, C₃-C₆cycloalkyl, phenyl, phenoxy or by 5- or 6-membered heteroaryl or heteroaryloxy, wherein heteroaryl or heteroaryloxy may in turn be interrupted once by oxygen or by sulfur or once, twice or three times by nitrogen and may be bonded to the CrC₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group either via a C atom or via a N atom, and wherein the phenyl- and heteroaryl-containing groups may be substituted once, twice or three times by halogen, d-dalkyl, d-C₄haloalkyl, d-dalkoxy, d-C₃haloalkoxy, d-C₃alkylthio, d-C₃alkylsulfinyl, d-C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; or R₂₄ is C(O)-R₇₄ or C(S)-R₇₅; X₅ is oxygen or sulfur;

R₂₅ is hydrogen, CrC₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, C C₃alkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-C₃alkylsulfonyl, C_rC₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-C₄alkylcarbonylamino; R₂₆ is hydrogen, d-Cealkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₂₅ together with R₂₆ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-C₃alkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; or R₆ is - ₃-R₂₇;

R₂₇ is formyl, d-dalkylcarbonyl, C₃-C₆cycloalkylcarbonyl, benzoyl, CrCealkoxycarbonyl, cyano, C(X6)NR₂₈R₂9, phenyl or heteroaryl, wherein benzoyl and phenyl may be substituted once, twice or three times by halogen, d-dalkyl, d-C₄haloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-C₃alkylsulfinyl, C C₃alkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; and wherein heteroaryl may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-C₃alkoxy, d-dhaloalkoxy, d-C₃alkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-C₃haloalkylthio, cyano, nitro or by d-C₄alkoxycarbonyl; or R₂₇ is C₃-C₆cycloalkyl or C₅-C₆cycloalkenyl each of which may in turn be substituted once, twice or three times by d-dalkyl, halogen or by d-dalkoxy; X₆ is oxygen or sulfur;

R₂₈ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-C₃alkylthio, d-C₃alkylsulfinyl, d-C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-C₄alkylcarbonylamino; R₂₉ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₂₈ together with R₂₉ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-C₃alkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; R₇ is hydrogen, d-dalkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, d-Cehaloalkyl, C₃-C₆cycloalkyl, phenyl, benzyl, heteroaryl, C(X₇)R₃₀ or NR∞R^, wherein phenyl, benzyl and heteroaryl may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-C₃alkylsulfinyl, C C₃alkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-C alkoxycarbonyl or by d-C alkylcarbonylamino; X₇ is oxygen or sulfur;

R₃₀ is hydrogen, d-dalkyl, C₃-C₆cycloalkyl, phenyl, heteroaryl, d-dalkoxy, C₃-C₆alkenyl- oxy, benzyloxy, d-dalkylthio or a group NR₃₁R₃ ; R₃₁ and R₃₃ are each independently of the other hydrogen, Crdalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-C₃alkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by d-dalkylcarbonylamino;

R₃₂ and R₃₄ are each independently of the other hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₃₁ together with R₃₂ or R₃₃ together with R^, in each case with the respective N atom to which they are bonded, form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, C C₃haloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by d-dalkylcarbonylamino; or R₇ is -L₄-X8-R₃₅; wherein X₈ is oxygen, -NR₃₆-, -S-, -S(O)- or -S(O)₂-;

R₃₆ is hydrogen, d-dalkoxy, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or is phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-C₃alkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by d-dalkylcarbonylamino; R₃₅ is hydrogen or a d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group, which groups may be substituted once, twice or three times by halogen, hydroxy, d-dalkoxy, d-dalkoxy- d-dalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, cyano, C(X₉)NR₃₇R₃₈, C₃-C₆cycloalkyl, phenyl, phenoxy or by 5- or 6-membered heteroaryl or heteroaryloxy, wherein heteroaryl or heteroaryloxy may in turn be interrupted once by oxygen or by sulfur or once, twice or three times by nitrogen and may be bonded to the d-Cealkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group either via a C atom or via a N atom, and wherein the phenyl- and heteroaryl-containing groups may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-C₃alkoxy, C C₃haloaikoxy, d-dalkylthio, d-dalkylsulfinyl, d-C₃alkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by Crdalkylcarbonylamino; X₉ is oxygen or sulfur;

R₃₇ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhalo- alkoxy, d-dalkylthio, C C₃alkylsulfinyl, CrC₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; R₃₈ is hydrogen, Crdalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₃₇ together with R₃₈ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-C₃alkoxy, d-dhaloalkoxy, C C₃alkylthio, d-C₃alkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-C₄alkoxycarbonyl or by C C₄alkylcarbonylamino; or R₇ is -L₅-R₃₉;

R₃₉ is formyl, d-dalkylcarbonyl, C₃-C₆cycloalkylcarbonyl, benzoyl, CrCealkoxycarbonyl, cyano, C(X₁₀)NR₄₀R ι, phenyl or heteroaryl, wherein benzoyl and phenyl may be substituted once, twice or three times by halogen, d-dalkyl, C C₄haloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-C₃alkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; and wherein heteroaryl may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-C₃haloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro or by d-dalkoxycarbonyl; or R₃₉ is d-dcycloalkyl or C₅-C₆cycloalkenyl each of which may in turn be substituted once, twice or three times by d-dalkyl, halogen or by d-dalkoxy; X₁₀ is oxygen or sulfur;

R^ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-C₃alkoxy, d-dhaloalkoxy, d-dalkylthio,^" d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; R₄₁ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R ₀ together with R₄₁ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; or R₆ and R₇ together with the nitrogen atom to which they are bonded form a carbocyclic 3- to 7-membered, saturated or partially saturated or unsaturated monocyclic or bicyclic ring system which may be interrupted once by oxygen, once by sulfur, from one to three times by nitrogen and/or substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro or by d-dalkoxycarbonyl; wherein each ring system may not be interrupted by -C(=O)-, -C(=S)-, -C(=NR_5a)-, -N(=O)-, -S(=O)- or by -SO₂-; R_5a is d-C₆alkyl, hydroxy, d-dalkoxy, cyano or nitro; X₂ is oxygen, -NR₄₂-, sulfur, -S(O)- or -S(O)₂-;

R ₂ is hydrogen, C C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, d-Cehaloalkyl, C₃-C₆cycloalkyl, phenyl, heteroaryl, C(X₁₁)R₄₃ or NR^R^; Xn is oxygen or sulfur;

R^ is hydrogen, d-dalkyl, C₃-C₆cycloalkyl, phenyl, heteroaryl, d-dalkoxy, C₃-C₆alkenyl- oxy, benzyloxy, d-C₄alkylthio or a group NR₄₄R₄₅;

R^ and R₄₆ are each independently of the other hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, C C haloalkyl, C C₃alkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino;

R^ and R ₇ are each independently of the other hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₄₄ together with R^ or R ₆ together with R ₇, in each case with the respective N atom to which they are bonded, form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-C₄haloa!kyl, d-C₃alkoxy, d-dhaloalkoxy, d-C₃alkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; or R ₂ is -U-X^-R^; wherein X₁₂ is oxygen, -NR₄₉-, -S-, -S(O)- or -S(O)₂-;

R₄₉ is hydrogen, d-dalkoxy, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or is phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-C₄alkylcarbonylamino; R₄₈ is a CrC₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group, which groups may be substituted once, twice or three times by halogen, hydroxy, d-dalkoxy, CrC₃alkoxy-d-C₃alkoxy, d-dalkenyloxy, C₃-C₆alkynyloxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, cyano, C(X₁₃)NR₅oR₅ι, C₃-C₆cycloalkyl, phenyl, phenoxy or by 5- or 6-membered heteroaryl or heteroaryloxy, wherein heteroaryl or heteroaryloxy may in turn be interrupted once by oxygen or by sulfur or once, twice or three times by nitrogen and may be bonded to the CrC₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group either via a C atom or via a N atom, and wherein the phenyl- and heteroaryl-containing groups may be substituted once, twice or three times by halogen, d-dalkyl, d-C₄haloalkyl, C C₃alkoxy, C C₃haloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; Xι₃ is oxygen or sulfur;

R₅₀ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-C₄haloalkyl, d-C₃alkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; R₅₁ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₅₀ together with R₅₁ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, C C₃alkoxy, d-C₃haloalkoxy, d-C₃alkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; or R₄₂ is -L₇-R₅₂;

R₅₂ is formyl, d-dalkylcarbonyl, C₃-C₆cycloalkylcarbonyl, benzoyl, d-dalkoxycarbonyl, cyano, C(X₁₄)NR₅₃R₅ , phenyl or heteroaryl, wherein benzoyl and phenyl may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, C C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-C₄alkylcarbonylamino; and wherein heteroaryl may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro or by d-dalkoxycarbonyl; or R₅₂ is d-dcycloalky! or C₅-C₆cycloalkenyl each of which may in turn be substituted once, twice or three times by d-dalkyl, halogen or by d-dalkoxy; X is oxygen or sulfur;

R₅₃ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, C C₃alkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, C C₃alkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by C C alkylcarbonylamino; R₅₄ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₅₃ together with R₅ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-C₃alkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino;

R₈ is hydrogen or a d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group, which groups may be substituted once, twice or three times by halogen, hydroxy, d-C₆alkoxy, d-dalkoxy- d-dalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, d-dalkylthio, C_rC₆alkylsulfinyl, d-dalkylsulfonyl, cyano, C(X₁₅)NR₅5R₅6, C₃-C₆cycloalkyl, phenyl, phenoxy or by 5- or 6- membered heteroaryl or heteroaryloxy, and wherein heteroaryl or heteroaryloxy may in turn be interrupted once by oxygen or by sulfur or once, twice or three times by nitrogen and may be bonded to the d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group either via a C atom or via a N atom, and wherein the phenyl- and heteroaryl-containing groups may be substituted once, twice or three times by halogen, d-dalkyl, d-C₄haloalkyl, C C₃alkoxy, C C₃haloalkoxy, d-dalkylthio, d-C₃alkylsulfinyl, C C₃alkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; X₁₅ is oxygen or sulfur;

R₅₅ is hydrogen, -dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-C₃alkoxy, d-dhaloalkoxy, d-C₃alkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; R₅₆ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₅₅ together with R₅₆ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-C₃alkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; or R₈ is cyano, C(O)-R₇₆ or C(S)-R₇₇; X₃ is oxygen, -NR₅₇-, sulfur, -S(O)- or -S(O)₂-;

R₅₇ is hydrogen, d-dalkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, CrCehaloalkyl, C₃-C₆cycloalkyl, phenyl, heteroaryl, C(X₁₆)R₅₈ or NR₆ιR₆2; Xi6 is oxygen or sulfur;

R_s8 is hydrogen, d-dalkyl, C₃-C₆cycloalkyl, phenyl, heteroaryl, d-dalkoxy, C₃-C₆alkenyl- oxy, benzyloxy, d-dalkylthio or a group NRsgReo; R₅₉ and R₆ι are each independently of the other hydrogen, d-dalkyl, C₃-C₆alkenyl or d-dalkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-C₄haloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, C_rC₄alkoxycarbonyl or by d-dalkylcarbonylamino;

R₆₀ and R₆2 are each independently of the other hydrogen, d-Cealkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₅₉ together with R₆₀ or R₆ι together with R₆₂, in each case with the respective N atom to which they are bonded, form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-C₄alkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-C₃alkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, C C₄alkoxycarbonyl or by d-dalkylcarbonylamino; or R₅₇ is -L₈-X ₇-R₆₃; wherein X₁₇ is oxygen, -NR∞-, -S-, -S(O)- or -S(O)₂-;

R₆ is hydrogen, d-dalkoxy, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or is phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; R₆₃ is a d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group, which groups may be substituted once, twice or three times by halogen, hydroxy, d-dalkoxy, CrC₃alkoxy-C C₃alkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, d-dalkylthio, d-dalkylsulfinyl, C C₆alkylsulfonyl, cyano, C(X₁₈)NR₆₅R6₆, C₃-C₆cycloalkyl, phenyl, phenoxy or by 5- or 6-membered heteroaryl or heteroaryloxy, wherein heteroaryl or heteroaryloxy may in turn be interrupted once by oxygen or by sulfur or once, twice or three times by nitrogen and may be bonded to the d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group either via a C atom or via a N atom, and wherein the phenyl- and heteroaryl-containing groups may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-C₃alkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; X₁₈ is oxygen or sulfur;

Res is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, -dalkyl, d-dhaloalkyl, d-dalkoxy, C C₃halo- alkoxy, d-C₃alkylthio, C_rC₃alkylsulfinyl, d-C₃alkylsulfonyl, C C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-C₄alkylcarbonylamino; R₆₆ is hydrogen, Cι-C₆alkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₆5 together with R₆₆ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-C₃alkoxy, d-dhaloalkoxy, d-C₃alkylthio, CrC₃alkylsulfinyl, C C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-C alkylcarbonylamino; or R₅₇ is -L₉-R₆₇;

R₆₇ is formyl, d-dalkylcarbonyl, C₃-C₆cycloalkylcarbonyl, benzoyl, CrCealkoxycarbonyl, cyano, C(X₁₉)NR₆₈Re₉, phenyl or heteroaryl, wherein benzoyl and phenyl may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, C C₃alkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, C C₃alkylsulfonyl, C C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; and wherein heteroaryl may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, C C₃haloalkoxy, d-C₃alkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro or by d-C₄alkoxycarbonyl; or R₆₇ is C₃-C₆cycloalkyl or d-dcycloalkenyl each of which may in turn be substituted once, twice or three times by d-dalkyl, halogen or by C C₄alkoxy; X₁₉ is oxygen or sulfur;

R₆₈ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, C C₃alkoxy, d-dhaloalkoxy, d-dalkylthio,^" d-dalkylsulfinyl, C C₃alkylsulfonyl, C C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; R₆₉ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₆₈ together with R₆₉ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-C₃alkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, C C₃alkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; L| is d-dalkylene which may be substituted once, twice or three times by Crdalkyl, halogen or by d-dalkoxy and to which d-C alkylene group there may be spirocyclically bound a further C₂-C₅alkyiene group which may in turn be interrupted once or twice by oxygen, sulfur, sulfinyl or by sulfonyl and/or substituted by Crdalkyl or by d-dalkoxy; or is d-C₄alkylene which may be substituted once, twice or three times by d-dalkyl, halogen or by d-dalkoxy, and wherein a carbon atom of that d-dalkylene group together with R₉ or with R₇₀ forms, by means of a further C₂-C₆alkylene chain, a ring system which may additionally be interrupted once or twice by oxygen, sulfur, sulfinyl or by sulfonyl and/or substituted by d-dalkyl or by d-dalkoxy; R₉ is a group -X₂o-R₇o. wherein X₂₀ is oxygen, -NR₇ , -S-, -S(O)- or -S(O)₂-;

R₇₁ is hydrogen or a d-Cealkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group, which groups may be substituted once, twice or three times by halogen, hydroxy, d-dalkoxy, d-dalkoxy- d-dalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, cyano, C(X₂ι)NR₇₂R₇₃, C₃-C₆cycloalkyl, phenyl, phenoxy or by 5- or 6- membered heteroaryl or heteroaryloxy, wherein heteroaryl or heteroaryloxy may in turn be interrupted once by oxygen or by sulfur or once, twice or three times by nitrogen and may be bonded to the d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group either via a C atom or via a N atom, and wherein the phenyl- and heteroaryl-containing groups may be substituted once, twice or three times by halogen, d-dalkyl, d-C₄haloalkyl, C C₃alkoxy, d-C₃haloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-da!kylcarbonylamino; X₂₁ is oxygen or sulfur;

R₇₂ is hydrogen, d-Cealkyl, C₃-C_ealkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, Crdalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-C₄alkylcarbonylamino; R₇₃ is hydrogen, d-dalkyl, C₃-C_ealkenyl or C₃-C₆alkynyl; or R₇₂ together with R₇₃ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-daikylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; R₇₀ is hydrogen or a d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group, which groups may be substituted once, twice or three times by halogen, hydroxy, d-dalkoxy, d-dalkoxy- d-dalkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, C C₆alkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, cyano, C(X₁₅a) R₅5a 56a, C₃-C₆cycloalkyl, phenyl, phenoxy or by 5- or 6- membered heteroaryl or heteroaryloxy, and wherein heteroaryl or heteroaryloxy may in turn be interrupted once by oxygen or by sulfur or once, twice or three times by nitrogen and may be bonded to the CrCealkyl, C₃-C₆alkenyl or C₃-C₆alkynyl group either via a C atom or via a N atom, and wherein the phenyl- and heteroaryl-containing groups may be substituted once, twice or three times by halogen, d-dalkyl, d-C₄haloalkyl, d-dalkoxy, d-C₃haloalkoxy, d-dalkylthio, d-C₃alkylsulfinyl, d-dalkylsulfonyl, C C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; X _5a is oxygen or sulfur;

R_δs_a is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, C C₃alkylthio, d-dalkylsuifinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; R_S6a is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R_55a together with R_56a and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, C_rC₃alkylthio, d-C₃alkylsulfinyl, C C₃alkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; or R₇₀ is d-Cioalkylideneimino, (phenyl-Crdalkylidene)imino, or phenyl, wherein phenyl may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-C₃alkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; or R₇₀ is cyano, C(O)-R₇₈ or C(S)-R₇g; or R₉ is formyl, d-dalkylcarbonyl, C₃-C₆cycloalkylcarbonyl, benzoyl, CrCealkoxycarbonyl, cyano, C(X₃₅)NR₁₂5Rι₂₆, phenyl or heteroaryl, wherein benzoyl and phenyl may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-C₃haloalkoxy, C C₃alkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; and wherein heteroaryl may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-C₃alkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro or by d-dalkoxycarbonyl; or R₉ is C₃-C₆cycloalkyl or C₅-C₆cycloalkenyl each of which may in turn be substituted once, twice or three times by d-dalkyl, halogen or by d-dalkoxy; X₃₅ is oxygen or sulfur;

R₁₂₅ is hydrogen, CrCealkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-C₃haloalkoxy, d-dalkylthio, CrC₃alkyIsulfinyl, d-C₃alkylsulfonyl, C C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino;

Ri2β is hydrogen, Crdalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R125 together with R₁₂₆ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, C C₃alkylthio, C_rC₃alkylsulfinyl, d-dalkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; 7₄, R75, 6, R77, R78 and R₇₉ are each independently of the others hydrogen, d-dalkyl,

C₃-C₆cycloalkyl, phenyl, benzyl, heteroaryl, d-dalkoxy, C₃-C₆alkenyloxy, benzyloxy, d-dalkylthio or NR^R^s, wherein phenyl, benzyl or heteroaryl may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-C₃alkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino;

Ri₂₇ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl or phenyl which may be substituted once, twice or three times by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, C C₃alkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino; ₂₈ is hydrogen, d-dalkyl, C₃-C₆alkenyl or C₃-C₆alkynyl; or R₁₂₇ together with R₁₂₈ and the respective N atom to which they are bonded form a carbocyclic 3- to 6-membered ring which may be interrupted by oxygen or by sulfur and/or substituted once, twice or three times by halogen, Crdalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkylthio, d-dalkylsulfinyl, d-C₃alkylsulfonyl, d-C₃haloalkylthio, cyano, nitro, d-dalkoxycarbonyl or by d-dalkylcarbonylamino;

R₈₀ and R₈₁ are each independently of the other hydrogen, -dalkyl, cyclopropyl, allyl or propargyl;

X^ is hydroxy, O^"M⁺ wherein M⁺ is an alkali metal cation or ammonium cation, or is halogen,

C Cι₂alkylthio, CrC₁₂alkylsulfinyl, d-C₁₂alkylsulfonyl, CrC₁₂haloalkylthio, C_rC₁₂halo- alkylsulfinyl, Crd₂haloalkylsulfonyl, CrC₆alkoxy-CrC₆alkylthio, Crdalkoxy-Crdalkyl- sulfinyl, d-dalkoxy-d-dalkylsulfonyl, C₃-d₂alkenylthio, C₃-Cι₂alkynylthio, C_rC₄alkoxy- carbonyl-d-C₄alkylthio, d-dalkoxycarbonyl-d-dalkylsulfinyl, d-dalkoxycarbonyl-d-d- alkylsulfonyl, Crd₂alkylsulfonyloxy, phenylsulfonyloxy, d-dalkoxy, d-dalkenyloxy, d-C₈- alkynyloxy, d-dhaloalkoxy, benzyloxy or benzoylmethoxy, wherein the phenyl-containing groups may be substituted once or more than once by R₈2; R₈₂ is halogen, d-dalkyl, d-C₃haloalkyl, hydroxy, d-dalkoxy, d-dhaloalkoxy, cyano or nitro; or an agronomically acceptable salt, tautomer, isomer or enantiomer of such a compound.

2. A herbicidal composition which, besides comprising formulation adjuvants, comprises a herbicidally effective amount of compound of formula I.

3. A method of controlling grasses and weeds in crops of useful plants, which comprises applying a herbicidally effective amount of a compound of formula I or of a composition comprising such a compound to the plants or the locus thereof.