TW200900398A - 3-cyano-4-triazolyl phenylisoxazoline invertebrate pest control agents - Google Patents

Abstract

Disclosed are compounds of Formula 1, N□ oxides, and salts thereof, wherein R1 is F, Cl, Br, cyano, CF3, OCF2H, OCF3 or OCH2CF3; R2 is H, F, Cl, Br, CH3, cyano, CF3, OCF2H, OCF3 or OCH2CF3; and R3 is H, F, Cl, Br or CF3. Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound or a composition of the invention.

Description

200900398 IX. INSTRUCTIONS: [Technical field to which the invention pertains] The present invention relates to agronomic or forestry, N-oxides, salts and compositions thereof, for use in certain environments, for example, for controlling limbs Move ', in the art of Chen Yi and non-agricultural. 'Invertebrate harmful animal side [previous technique] Controlling invertebrate harmful animals to obtain high-yield harmful vertebrae for the cultivation and storage of crops... Contains ^ 9 . The initial damage of Chen F can lead to significant production: consumption The cost of the increase. The control of invertebrate pests is also important in crops, ornamental plants, seedlings, _ _ food, fiber and glutinous products, livestock, households, turf, wood, and public and animal health. Many products for these purposes are sold, and (iv) new compounds are needed 'which are more efficient, less costly, less toxic, environmentally safer or have different sites of action. Japanese a Kaimu Japanese Patent No. 2007-1 6017 reveals a singular oxazoline derivative as an insecticide

Wherein 'in particular, Al, A2 and A3 are each independently C or N; G1 is a benzene ring; G2 is an N-linked heterocyclic ring; and X is a halogen. The isoxazoline of the present invention is not explicitly disclosed in this publication. 130845.doc 200900398 SUMMARY OF THE INVENTION The present invention relates to /^ oxides and salts, and all enantiomers thereof, the use of N-: compositions thereof and their control of invertebrate pests

Wherein CF3, OCF2H, 〇CF3 or cyano, CF3, ocf#, R system F, Cl, Br, cyano, 〇CH2CF3; R2 Η, F, Cl, Br, CH3 OCF3 or 〇ch2cf3; and R3 H, F, Cl, Br or CF3. The invention also relates to the use of the compounds of the formula (including all enantiomers), their N-oxides and salts, and compositions comprising the same, and for controlling invertebrate pests as described above, and furthermore The condition herein is that if R is C1 and R2 is Η or C1, then R3 is F, Br or CF3; and if R1 is Br and r2 is Η or C1, then R3 is F, C1 or CF3. The invention also provides other components comprising a compound of formula 1, an N-oxide or salt thereof, and at least one selected from the group consisting of surfactants, solid diluents, and liquid diluents. In one embodiment, the invention also provides a composition for controlling an invertebrate pest comprising a biologically effective amount of a compound of formula 1, an N-oxide or salt thereof, and at least one selected from the group consisting of a surfactant, a solid 130B45 .doc 200900398 Other components of the bulk diluent and liquid diluent composition, the composition optionally further comprising a biologically effective amount to the main v ~ other biologically active compound or reagent. The present invention further provides a spray composition for controlling a roll-free vertebrate-free pest animal, which comprises a biologically effective amount, a compound of formula 1, a bismuth-oxide or salt thereof, or a composition thereof, and a propellant . Tai Lian, this month also provides bait composition for controlling invertebrate harmful animals, 坌 会,, 3 3 biologically effective amount of the compound of formula 1, its N-oxide or salt or above. ^ The composition of the invention, one or more food materials, an attractant (if necessary), and (as needed) a quenching agent. The present invention further provides a trapping device for controlling an invertebrate pest, comprising the reclining composition and an outer shell adapted to receive the lure composition, wherein the shell has at least one opening sized to allow invertebrate (four)_self The position of the outer tube allows the invertebrate pest to reach the bait composition through the opening and wherein the outer casing is also adapted to be placed in or near an activity site that may or is known to the invertebrate pest. The present invention provides a method of controlling an invertebrate pest comprising comprising contacting a non-vertebral pest or an environment thereof with a biologically effective amount of a compound of the formula i, an antioxidant or salt thereof (e.g., as a composition described herein). The present invention is also directed to a compound of formula 1 wherein the invertebrate pest or its environment and combination of the composition comprises a biologically effective amount of a compound of the formula::::: or a dish and a species selected from a surfactant, a solid diluent diluent 1 group of his group 々 ... "human Μ + 曰 π < eight his group injury, the side composition as needed additionally contains at least one other biologically active compound or reagent in biological effectiveness. 130845.doc 200900398 The present invention also provides A method of protecting a seed from invertebrate pests, comprising contacting the seed with a biologically effective amount of a compound of the formula, a vitamin oxide salt (9), for example as a composition described herein. The invention also relates to treated seeds The invention further provides a method of protecting an animal from invertebrate parasitic harmful animals, comprising administering to the animal a parasiticidally effective amount of a conjugate, a N-oxide or a salt thereof (eg, as described herein) [Composition] [Embodiment] ^The words used in the text, including "("comprises",, (10) state, such as "burn" package ("includes", "including"), ""("has","ha~"),"including"("contains" or "containing") or any other variation thereof is intended to cover non-exclusive "including". For example, a composition, mixture, process, method, article, or device that comprises a plurality of elements is not necessarily limited to such elements, but may include those not specifically listed or inherent to the composition, mixture process, method, article, or device In addition, unless expressly stated to the contrary, "or" means inclusive, or, rather than exclusive or "." For example, condition A or B may be by any of the following Proposition to satisfy that .A is true (or exists) and b is false (or non-existent), a is false (or does not exist) and B is true (or exists), and both eight and eight are true (or exist The same indefinite article "a" or "an" or "an" or "an" or "an" or "an" or "an" or "an" ('V· or "an") should be considered The singular forms of the elements or components also include the plural. The term "invertebrate pests, including as harmful 130845.doc -10- 200900398 Animals are economically important for arthropods, gastropods and nematodes. The term arthropods includes insects, mites, spiders, scorpions, crickets, millipedes, ball worms and integrated worms. The term "gastropod" includes yak, cockroach and other stalk (Styl〇mmat〇ph〇ra) animals. The term "helium" includes all worms such as: aphids, canine heartworm, and nematodes (Nematoda), trematodes (Temat〇 (ja)), and echinoderms "Acanthocephala" and aphids (Cest〇da). In the context of this disclosure, "invertebrate pest control" means inhibiting the occurrence of invertebrate pests (including death, reduced feeding) And/or mating interference) and related words have similar definitions. “Agricultural” refers to, for example, the production of field crops for food and fiber and includes cultivation of the following crops: corn, soybeans and other beans, rice , cereals (such as wheat, oats, barley, rye, rice, maize), leafy colza (such as chicory, cabbage, vegetables, and other canola crops), and strong vegetables (such as tomatoes, peppers, Eggplant, cruciferous and gourd), horse bell, sweet potato, grape, cotton: ^, tree fruit (such as pear fruit, stone fruit and citrus berry (strawberry, cherry) and other specialty crops (such as canola, sunday) Po, withdrawal of plucking) The term "non-agronomic" refers to fields other than field crops, such as horticultural crops (such as greenhouse plants, nursery or ornamental plants that are not grown in the field), residential, agricultural, commercial and industrial structures, turf (eg pastures, pastures). , golf course, lawn, 遂; 私士日#, „早什 linkage% 4), wood products, storage products, compound agroforestry and vegetation management, Bahrain 1 〇, Shangyu rice, public health ( That is, human) and animal health (ie, domesticated animals such as pets, livestock, and poultry, uncultivated animals such as wild animals). 130845.doc • 11 - 200900398 The compounds of the present invention can be mapped to understand the '-enantiomer The body is relatively close to the child. Those who are familiar with this technology, Fu Yardian, should be prepared for other enantiomers or when they are widely distributed with other enantiomers. In addition, they are familiar with this technology: they may be beneficial. The surgeon knows how to isolate and selectively prepare the enantiomers. -, Η 匕 σ can be present in the mixture or as a single enantiomer.

/ Learners of this technology can understand that there are nitrogen-containing heterocyclic ring-shaped oxides, because nitrogen needs to be oxidized to oxides by lone pair electrons; those skilled in the art can understand that they can form bismuth oxides. These nitrogen-containing heterocycles. The synthesis of heterorubbery-oxides is well known to those skilled in the art and includes the oxidation of heterocycles with peroxyacids such as peroxyacetic acid and m-chloroperbenzoic acid (MCPBA). Hydrogen peroxide, alkyl hydroperoxide such as t-butyl hydroperoxide, sodium perborate, and bis-epoxyethane such as dimethyl dioxirane. Such methods for preparing N-oxides have been extensively described and reviewed in the literature 'see, for example, TL Gilchrist, Cow/?r Coffee (10). ve Orgam'c Office...~❿, Volume 7, page 748_75, sv [Calculation, Pergamon press; M, Tisler and Β stanovnik «

Comprehensive Heterocyclic Chemistry, Vol. 3, No. H2Q ‘A·J. Boulton and A. McKillop, ed., pergamoll press; M. R. Grimmett and B. R. T. Keene, (10) &

Heterocyclic Chemistry > Volume 43, pages 149-161, A. R Katritzky, ed., Academic Press; M. Tisler and B.

Stanovnik, Advances in Heterocyclic Chemistry > Volume 9, pages 285-291, A. R. Katritzky and A. J. Boulton, ed., 130845.doc 12 200900398

Academic Press ; and G. w. η. cheeseman and Ε· S. G Werst’mk, Advances in Heterocyclic Chemistry, vol. 22, pp. 390-392, edited by A. R. Katritzky and A. J. Boulton,

Academic Press ° Those skilled in the art will understand that because the salt of a chemical compound is in equilibrium with its corresponding non-salt form in the environment and under the conditions of life, the salt has the same bioavailability as the non-salt form. Therefore, a wide variety of salts of the compound of formula 1 can be used to control invertebrate pests. The salt of the compound of the formula 1 includes an acid addition salt formed with an inorganic or organic acid such as r.', the like: hydrobromic acid, hydrochloric acid, lithospermic acid, phosphoric acid, sulfuric acid, acetic acid, butyric acid, fumaric acid, Lactic acid, maleic acid, malonic acid, oxalic acid, propionic acid, salicylic acid, tartaric acid, 4-nonylbenzene acid or valeric acid. Thus, the present invention includes a compound selected from the group consisting of Formula 1, its N-oxide and suitable salts. Embodiments of the invention described in the Summary of the Invention include (wherein Formula 1 used in the following examples includes its N-oxides and salts): f Example 1. A compound of Formula 1, wherein R1 is C1 and R2 is Η or C1 And R3 is F, Br or CF3; and if R1 is Br and R2 is Η or C1, then R3 is F, C1 or CF3. " Example 2. A compound of formula 1 wherein R1 is F, Cl, Br, CF3, ocf2h or ocf3. Embodiment 3. The compound of Embodiment 2 wherein R1 is ci, Br, CF3 or OCF3. Embodiment 4. The compound of Embodiment 3 wherein R1 is CM, Br or CF3. Embodiment 5. The compound of Embodiment 4 wherein R1 is Cl. 130845.doc -13.200900398 Embodiment 6. The compound of Embodiment 4 wherein Ri is Br. Embodiment 7. The compound of Embodiment 4 wherein Ri is cf3. Embodiment 8. A compound of formula 1 wherein r2 is η, f, Cl, Br, CH3 or cyano. Embodiment 9. The compound of Embodiment 8, wherein r2 is η, F or C1. Embodiment 10 The compound of Embodiment 8, wherein r2 is ch3. Embodiment 11. The compound of Embodiment 8, wherein r2 is cyano. Embodiment 12. The compound of Embodiment 9, wherein R2 is ρ. Embodiment 13. The compound of Embodiment 9, wherein r2 is c1. Embodiment 14 The compound of Embodiment 8 wherein r2 is b r. Embodiment 1 5. The compound of Embodiment 9, wherein r2 is η. Embodiment 16_Compound of Formula 1 'R3 is η, F, Cl, Br or CF3. Embodiment 17. The compound of Embodiment 16, wherein r3 is η, ci, Br gas CF3. Embodiment 1 8. The compound of Embodiment 1 wherein R3 is hydrazine, Cl or Br. Embodiment 19. The compound of Embodiment 18 wherein R3 is η. Embodiment 20. The compound of Embodiment 16, wherein R3 is F. Embodiment 21. The compound of Embodiment 1 wherein r3 is c1. Embodiment 22. The compound of Embodiment 18 wherein R3 is Br. Embodiment 23. The compound of Embodiment 17, wherein the rule 3 is (: 173. Embodiments of the invention (including the above-described embodiment U3 and any of the other embodiments described herein) may be combined in any manner, and the variables in the examples The expression is not only a compound of the formula 1 but also a starting compound and an intermediate compound which can be used for the preparation of the hydrazine compound. Furthermore, embodiments of the invention include the above-described examples of the invention as described in the above-mentioned Examples. Any of the other embodiments and any combination thereof belong to the compositions and methods of the present invention. The combination of Example 1-23 is illustrated by the following: Example A. A compound of Formula 1, wherein R1 is Cl, Br, CF3 Or OCF3; R2 is Η, F, Cl or CH3; and R3 is Η, CM, Br or CF3; if R1 is Cl and R2 is H or Ci, then "for plant B^CF3; and if R1 is Br And R2 is H or CH, then R3 is F, C^CF3. Specific examples include a U compound selected from the group consisting of 5-[5-(3-stain-4,5-dichlorophenyl)· 4,5-Dihydro-5-(trifluoromethyl)_3_isooctyl]-2-(1//-ΐ,2,4-triazol-1-yl)benzonitrile, 5-[5-( 3,5-dichloro-4- Phenyl)_4 <5 - & ^ , a}, 虱-5-(diindolyl)-3-isoxazolyl]-2-(1/Μ, 2,4-triazole _; U-based benzonitrile, and 5 [4,5-dihydro-5-(trifluoromethyl)-5-[3-(trifluoromethyl)phenyl]isoindolyl]-2-(1//- 1,2,4-triazole-fluorenyl-benzonitrile. The value of the compound of the present invention, which is characterized by favorable metabolism and/or activity of harmful animals. The agronomic invertebrates should pay particular attention to the system. Due to the importance of the helmet, the invention is implemented, the scope of the animal control and the economy to protect the crops from the ridgeless, and the vertebral harmful animals due to the roads. Damage or damage caused by animals. Since the compound of the present invention can also be protected against compound, sex or systemicity in the plant X-existing field, its composition of the compound is directly connected to 130845.doc •15-200900398 Or other plant parts. Also a class of attention, a composition of the present invention, comprising a compound of the above examples and any of the other embodiments described herein, and any combination thereof, and at least - silk A丄± Species Other components of the group consisting of a free surfactant, a solid diluent diluent, and such compositions may be additionally packaged with other biologically active compounds or reagents as needed. A composition for controlling a vertebrate vertebrate animal comprising a biologically effective amount of the above-described embodiments, and any other embodiments of any of the embodiments described herein, and any combination thereof, and at least one selected from the group consisting of surface active (four), (d), and (d) A group of diluents, other components 'These compositions additionally comprise at least a biologically effective amount of other biologically active compounds or agents, as needed. Embodiments of the invention additionally comprise a method of controlling a vertebrate pest comprising contacting an invertebrate pest or an environment thereof with a biologically effective amount of a compound (10) of any of the above embodiments as described herein. Embodiments of the invention also include compositions comprising any of the compounds of the above examples in the form of a soil-soaked liquid formulation. Embodiments of the present invention further comprise a method of treating a harmful animal, comprising contacting the soil with a liquid composition in the form of a soil infiltrant, the liquid composition comprising a biologically effective amount of a compound of any of the above embodiments . Human embodiments of the invention also include a spray set for controlling invertebrate pests. The article 'comprises a biologically effective amount of any of the compounds of the above examples and the propellant. Embodiments of the invention additionally include a temperate conjugate for controlling an invertebrate pest, comprising a biologically effective amount of any of the above-described embodiments, a compound, one or more food materials, (as needed Use an attractant, and (if needed) a moisturizer. Embodiments of the invention also include a device for controlling an invertebrate pest, #includes the bait composition and an outer casing adapted to receive the bait composition, wherein the outer casing has at least one opening sized to permit invertebrate pests from outside the outer shell The location is such that the invertebrate pest can reach the bait composition through the opening, and wherein the outer casing is also adapted to be placed in or near an active or known activity site of the invertebrate pest.

Embodiments of the invention also include methods of protecting seeds from damage by invertebrate pests, "including contacting the seed with a biologically effective amount of a compound of the above embodiments. Embodiments of the invention also include methods of protecting an animal from invertebrate parasitic harmful animals, comprising administering to the animal a parasiticidally effective amount of any of the compounds of the above examples. The hydrazine compound can be prepared using - or a variety of the methods and variations described in Scheme w below. Unless otherwise stated, the following formula is mutated; the definitions of R'R2 and R3 are as defined above in the Summary of the Invention. . The compound of formula 1 can be prepared by addition of a compound of formula 2 with a oxidized nitrile ring derived from the formula 3, as described in Scheme 1. In the method of Shibugu, Tusi, the brick is treated with a gasifying agent such as sodium hypochlorite, chlorochloroarene, or chloramine to obtain an oxazinium chloride intermediate. This in situ generated procedure 2 styrene reacts to form a hydrazine ring addition product. B, , _ , J H, and σ 崤 such as pyridine or diethylamine. The ten solvent includes tetrahydrogen bitrate, _ 匕 、, dioxane, dioxane, and fluorene. Usually, the anti- Τ Τ 久 久 久 介于 介于 介于 。 。 。 。 。 。 。 。 Using olefin cycloaddition oxidized nitrile Ά Decoration ^ Wang Xu detailed 130845.doc -17. 200900398 辻 · in the chemical literature (see for example, 1982, (5, 508-509 and Tetrahedron 2000, 56, 1057-1064 ) = Option 1

As shown in Scheme 2, the compound of formula i can also be prepared by directly replacing the fluoride from the aromatic fluoride of formula 4 with a triazole (5). The reaction is usually carried out in the presence of an inorganic base such as sodium hydride or potassium carbonate with a polar aprotic solvent such as dimethyl hydrazine or iV or dimethylacetamide. The method of Scheme 2 is described in Step F of Synthesis Example 1.

Scenario 2

As shown in Scheme 3, the formula 3 can be prepared by reacting the aldehyde of the formula 6 with an aldehyde of the formula 6 at an equilibrium of the formula 6 (夂 _ > see for example 厶

Lett. 1997, 7(21), 2813-2818). τ ^ , ‘J镨 is commercially available from Fang Xing 2, 3-cyano-4-fluorobenzaldehyde (7) and dialdehyde. And the reaction of -1 (5) to prepare the scheme 3 of formula 6

As shown in Scheme 4, palladium commercially available as 2-bromo-3,3,3-trifluoropropene (1 fluorene) with an aryl boronic acid of the formula 9 and a boronic ester (wherein the Ra is η or an alkyl group) Catalytic coupling to prepare styrene of formula 2. The general procedure for this reaction is described in /. CTzem. 1999, 95, 167-170. Many boric acid and boric acid esters are available on the market. Alternatively, the cyclic dioxane oxime of formula 9 can be prepared from the commercially available substituted benzene of formula 8 by the method described in step B of J2002, 3182-3184 and Synthesis Example 1 (wherein two Ra are together C (CH3) 2C (CH3) 2). 130845.doc -19- 200900398 Scheme 4

catalyst

Wherein Ra is a hydrazine or an alkyl group

It will be appreciated that certain of the reagents and reaction conditions described above for the preparation of the compounds of Formula 1 may be incompatible with certain functional groups present in the intermediates. The incorporation of a protecting/deprotecting sequence or functional group interconversion into the synthesis in these examples can be helpful in obtaining the desired product. The use and selection of protecting groups is evident to those skilled in the art of chemical synthesis (see, for example, Greene, τ. w.; Wuts, PGM Grow/?*? k Orgam.c, Second Edition; Wiley: New York, 1991). Those skilled in the art will appreciate that in some instances, as shown in any of the individual schemes, it may be necessary to carry out other conventional synthetic procedures not described in detail after introduction of a given reagent to complete the synthesis of the compound of Formula 1. It will also be apparent to those skilled in the art that a combination of the steps set forth in the above schemes may be carried out in an order different than that provided for the particular order in which the compound of formula 1 is provided. Those skilled in the art will appreciate that various electrophilic, nucleophilic, free radical, organometallic, oxidative, and reduction reactions can be performed on the compounds and intermediates of Formula 1 described herein to add substituents or modifications. A substituent is present. It is not necessary to repeat the above description. It is believed that those skilled in the art can use the above-described disclosures to illuminate the present invention 130845.doc -20- 200900398. The following synthesizing examples should be considered as merely illustrative and not limiting in any way. The procedures in the following synthetic examples are used for & integration into each step of the transformation, and the starting compounds for each of the two steps may not require the specific preparation process already illustrated by other procedures or steps in the procedure. To prepare. Except for the chromatographic solvent mixture, unless otherwise stated, the percentages are by weight. Parts and percentages of the chromatographic solvent mixture are by volume unless otherwise stated. 4 NMR spectroscopy is reported as a low magnetic field from ppm of tetradecyl decane; "s,, sound refers to a single peak, "d" means a doublet, "t" means three peaks,,, q" means four peaks ,,,μ means multiple peaks. Synthesis Example 1 Preparation of 5-[5-(3,5-dioxa-4-fluorophenyl)-4,5-dihydro-5-(trifluorofyl)_3_isoxazolyl]-2-(l// -l,2,4-triazol-1-yl)benzonitrile_j^2,6-bis(1-methylethyl)_τγ·(2-pyridylmethylene)aniline~ is equipped with Dean-Stark In a round bottom flask of the separator, 2,6-diisopropylaniline (8.27 g, 46.7 mmol) was added to a solution of 2-pyridinepyridine (5.0 g, 46.7 mmol) in toluene (2 mL). A catalytic amount of p-toluenesulfonic acid (0.10 g) was then added. The reaction mixture was heated to reflux and kept for 8 hours to remove water as an azeotrope. The reaction mixture was then washed once with water (1 mL) and the toluene was removed at low pressure. The residue was purified by EtOAc EtOAc (EtOAc) NMR (CDC10 δ 8.72_8.73 (m5 1H), 8.31 (s, 1H), 8.27 (d, 1H), 7.84 (t, 1H), 7.38-7.42 (m, 1H), 7.12-7.18 (m, 3H ), 2.974 (q, 2H), 1.17 (d, 12 130845.doc 21 200900398 Η). Step Β: Preparation of 2-(3,5_diox-4-fluorophenyl M, 4, s, 5_4 Methyl _ ___1,3,2-dioxaboron will be 4,4,4,,4,,5,5,5,,5,-octamethyl[2,2,·dihi-dioxaborazole] (10.0 g, 39.4 mmol), 2,6-bis(1-methylethyl)_1(2-pyridinylene) aniline (0.40 g, 1.5 mmol), and dioxane double [(1,25,6) _1,5-cyclooctadiene] Diterpene (0,50 g, 1. 〇 added to heptane mL) in 1,3·dichloro-2-fluorobenzene (10.0 g, 6〇· 6 mm 〇 1) solution. The reaction mixture changed from yellow to forest green to brick red in the first minute. The reaction mixture was heated to reflux and maintained for 18 h. Then the mixture was made in ethyl acetate @曰 and water. The mixture was partitioned, and the aqueous extract was washed twice with ethyl acetate. The organic extracts were combined, dried with EtOAc EtOAc EtOAc. Solid residue to provide solid The title compound ( Π.0 g). NMR (CDC: 13;) δ 7.72 (d, 2H), 1.33 (s, 12H). Preparation of Μ-di-hexane-2-fluoro(trifluoromethyl) Vinyl]Benzene 2__(35_二气_4_fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaboron in a 200 mL Fisher-Portei sealed tube (11 〇g, 37 8 mm 〇 1) and 2_ Han-3,3,3-difluoropropene (8.0 g, 45.7 mmol) was added to tetrahydrofuran (3 〇 mL), ethylene glycol diethyl ether (3 〇 mL) And a mixture of 4 Μ aqueous potassium hydroxide solution (3 〇 mL), followed by the addition of tetrakis(triphenylphosphine)palladium (〇) (264 mg, 〇229 mmol). The reaction mixture was heated to 75 ° C for 6 h. The reaction mixture was then partitioned between water and water and the aqueous layer was separated and washed twice with ether. The combined organic layers were dried with EtOAc and concentrated at low pressure. The residual oily solid was purified by flash-eluting elution to give the title compound (8 33 g) as a crude oil.] H nmr δ 7.40 (d, 2 Η), 6.04 (s, 1H), 5.79 (Sj 1H) Preparation of 2_fluoro-5-oxime (竺^-amino)methyl]benzonitrile__ Hydroxylamine (10. 0 mL, 50% by weight aqueous solution, 152 〇 _〇1) was added to a solution of 4-fluoro-3-phenylbenzaldehyde (15 8 i4 g, 106.13 mm 〇l) in ethanol (200 mL). The reaction mixture was stirred vigorously for 3 h at room temperature. The volatiles were evaporated to dryness under reduced pressure to give an oily aqueous liquid which was partitioned between ethyl acetate and water. The aqueous extract was washed twice with ethyl acetate. The organic extracts were combined, dried with MgSO 4 and evaporated. The residual solid was purified by chromatography eluting with EtOAc EtOAc (EtOAc) iH NMR (dms〇_d6) δ 11.53 (s, 1H), 9.71 (s, 1H), 8.16 (s, 1H), 7.53 (t, 1H), 7.44 (m, 1H). Step E: Preparation of 5-[5-(3,5-dioxa-4-fluorophenyl)-4,5-dihydro-5-(trifluoro-methyl)-3-isoxazolyl-2- Fluorobenzonitrile __ An aqueous solution of sodium hypochlorite (5 〇 mL) was added to 2-fluoro-5-[(hydroxyimino)methyl] quinonitrile (2.0 g, 12.2 mmol), 1,3-diox-2- A solution of fluoro-5-[1-(trifluoromethyl)ethenyl]benzene (4.0 g, 15.4 mmol) and tetrahydrofuran (50 mL). The reaction changed from yellow to pale and then turned yellow-green. The reaction mixture was stirred at room temperature for 3 h and then partitioned between ethyl acetate and water. The aqueous extract was extracted twice with EtOAc and dried over EtOAc EtOAc. The residual waxy oil was purified by chromatography eluting with ethyl acetate/hexane to afford the title compound (1.1 g). 'H NMR (CDC13) δ 7·97 (m,1H), 7.91 (d, 1H), 7.55 (d, 2H), 7.31 (t, 1H), 4.05 (d, 1H), 3.66 (d, 1H) . Step F: Preparation of 5-丨5-(3,5-dioxa-4-fluorophenyl)_4,5-dihydro-^(trifluoro-indolyl)-3-isoxyl rabbit-di-2-(1) Ugly-1,2,4·triazol-1-yl) nitrite 5-[5-(3,5-dioxa-4-fluorophenyl)_4,5-dihydro-5-(trifluoromethyl) >3_isox. Sodium]-2-fluorobenzonitrile (1.08 g, 2.56 mmol) was added to acetonitrile (2〇)

In a mixture of potassium carbonate (800 mg, 5.79 111 〇1〇1) and 1,2,4-triazole (5 〇〇 mg, 7.25 mmol) in mL). The reaction mixture was then stirred vigorously at 8 (rc) for 18 h. then the reaction mixture was applied to silica gel and solvent was removed at low pressure to afford a free-flowing solid which was diluted with ethyl acetate/hexane to afford melting. The title compound (36, 2 mg) in the form of a beige solid in the form of a beige solid. NMR (CDC13) δ 8.90 (s, 1 Η), 8.22 (s, 1H), 8.08-8.12 (m , 2H), 7.93 (d, 1H), 7.59 (d, 2H), 4.13 (d, 1H), 3.74 (d, 1H). Synthesis Example 2 Preparation of 5-[4,5-dihydro_5-(3 , 4,5_trisylphenyl)_5_(trimethylmethyl)mother isoindole]-2-(l//-l,2,4-tris-7-yl)benzonitrile step A : Preparation of 4,4,5,5•tetramethyl-2-indole, 4,5 tri-phenylene), _2___oxygen, M,4|,4,,5,5,5,, 5,·································丨.5 mmol) and two gas double [[1,2,5,6 Miao I]·cyclooctane dilute] two silver (0.50 g, U mm is added to the deposit in Geng Shao (10) called 130845.doc -24 - 1,2,3-trichlorobenzene (7.50 g, 41·3 mm〇1) solution in 200900398 The reaction mixture changed from yellow to forest green to brick red in the first minute. The reaction mixture was heated to reflux and maintained for 18 h. The reaction mixture was then partitioned between water and water with acetic acid. The ethyl ester was washed twice with the aqueous extract. The combined organic layers were dried with EtOAc EtOAc (EtOAc) The title compound (8.85 g). NMR (CDeiJ δ human 74 〇 2 Η), 1.32 (s, 12 Η). r' . 乞^8 : _ gas _s-丨 1-(trifluoromethyl) Benzene 4 4 5,5-tetramethyl-2-(3,4,5-triphenyl)-1,3,2-dioxaboron in a 200 mL Fisher-P〇rter sealed tube 8.85 g, 28 8 mm 〇 1) and 2_ bromo-3,3,3-difluoropropene (8.0 g, 45.7 mmol) were added to tetrahydroanion (3 〇 mL), ethyl alcohol monoethyl ether (30 mL) Adding tetrakis(triphenylphosphine)|bar (〇) (264 mg, 0 229 mmol) to a mixture of 4 Μ aqueous potassium hydroxide (3 〇 mL). The reaction mixture was heated to 75 ° C and kept 6 h. The reaction I mixture was then partitioned between ether and water' and the aqueous phase was washed twice with ether. use

The MgS〇4 was dried over a combined organic layer and concentrated under reduced pressure. The residual oily solid was purified to give the title compound (5.47 g) as an oil. NMR (CDC10 δ 7.46 Cs, 2H), 6.05 (s, 1H), 5.82 (s, 1H). Step C: Preparation of 5-[4,5-dihydro-5-(3,4,5-trichlorophenyl)-5(trifluoromethyl)-3-isoxazolyl]-2-fluorobenzonitrile_ A solution of sodium hypogasate (50 mL) was added to 2-fluoro-5-[(hydroxyimino)methyl]benzonitrile (2.0 g, 12.2 mmol, used for Example 1, step d), 1, 2, 3-三130845.doc -25- 200900398 Ingeniously-[1-(trifluoromethyl)vinyl]benzene (4·〇g, 144 curry 1) and tetrachloropyran (5〇mL) in solution . The reaction mixture changed color from yellow to orange and then turned yellow-green. The reaction mixture was allowed to stand for 3 h at room temperature. The reaction mixture was then partitioned between ethyl acetate and water, and the aqueous extract was washed twice with ethyl acetate. The ffiMgS〇4 was dried over the combined organic layers and concentrated at low pressure. The residual ptery oil was purified by chromatography on silica gel eluting with EtOAc (EtOAc). NMR (CDC13) δ 8.16-8.17 (m, iH), 7.97-7.99 (m, 1H), 7-93 (d, 1H), 7.62 (s, 2H), 7.32 (t, 1H), 4.07 (d, 1H), 3.68 (d, 1H). Step D: Preparation of M4,5-dihydro-S_(3,4,5-trisphenyl)_5_(trifluoromethyl-Hi3-isoxazolyl)-2- (1 ugly-1,2,4-triazole 4-yl)benzonitrile 5-[4,5-dihydro-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl) _3_Isooxazolyl]-2-fluorobenzonitrile (561 mg, 1.28 mmol) was added to potassium carbonate (800 mg, 5 79 111111〇1) and 1,24 triazole in acetonitrile (2 mL) (5 〇〇mg, 7.25 mmol) in a mixture. Then the reaction mixture was vigorously stirred at 8 Torr for 8 h and then the reaction mixture was added to the crushed rubber and the solvent was removed at low pressure to provide free flow. The title compound (the compound of the invention) (49.1 mg) was obtained as a beige solid. NMR (CDC13) δ 8.90 (s) , 1Η), 8.22 (s, 1H), 8.08-8.12 (m, 2H), 7.94 (d, 1H), 7.65 (s, 2H), 4.13 (d, 1H), 3.74 (d, 1H). Synthesis Example 3 Preparation of 5-[4,5-dihydro-5-(trifluoromethyl)_5_[3_(trifluoromethyl) Base]_3_ 130845.doc -26· 200900398 Isoxazolyl]-2-(1//-1,2,4-triazol-1-yl)benzonitrile Step A : Preparation of 1-(trifluoromethyl )-3-[1-(Trifluoromethyl)vinyl 1 stupid_---____ 3-trifluorodecylphenyl borate (5.0 g, 26·3 mmol) in a 200 mL Fisher-Porter sealed tube And 2-bromo-3,3,3-trifluoro-propene (8.0 g, 45.7 mmol) was added to tetrahydrofuran (3 〇mL), ethylene glycol diethyl ether (3 〇mL) and 4 Μ aqueous potassium hydroxide solution ( In a mixture of 3 〇 mL), then add tetrakis(triphenylphosphine) (0) (264 mg, 0.229 mmol). Heat the reaction mixture to 75 〇 and hold for 6 h. Then let the reaction mixture be in ether and water The mixture was partitioned and the aqueous extract was washed twice with ether. The combined organic layers were dried with EtOAc (EtOAc) The title compound (4 24 g) was obtained as an oil. 4 NMR (CDC13) δ 7·70 (s, 1H), 7.64 (t, 1H), 7.46-7.55 (m, 2H), 6.06 (s, 1H), 5.84 (s, 1H). Step B: Preparation of 5-[4,5-di-argon-5-(trifluoromethyl)-5-[3_(trifluoromethyl)-yl]-3-isoxazolyl]-2-fluorobenzonitrile _ Aqueous sodium hypochlorite (50 mL) was added to 2-fluoro-5-[(hydroxyimino)methyl]benzonitrile (2 〇g, 12 2 claws, from Example 1 'step in tetrahydrofuran mL) D), a solution of 1-(trifluoromethyl(trifluoromethyl)ethenyl]benzene (4·24 g, 17,7 mm〇i). The reaction mixture changed from yellow to orange to yellow-green. The mixture was stirred at room temperature for 3 h. The reaction mixture was partitioned between ethyl acetate and water, and the aqueous extract was washed twice with ethyl acetate. The combined organic layer was dried with <RTIgt; The residue was purified by chromatography eluting with EtOAc EtOAc (EtOAc) CDCI3) δ 8.16-8.17 (m, 1Η), 7.97-7.99 (m, 1H), 7.93 (d, 1H), 7.62 (s, 2H), 7.32 (t, 1H), 4.07 (d, 1H), 3.68 (d, 1H). Step C: Preparation of 5-indole-4,5-dihydro-5-(trifluoromethyl)-5-[3-(trifluoromethyl) _ 3-[isooxazolyl]-2-(1-,1,2,4-triazol-1-yl)benzonitrile. 5-[4,5-Dihydro-5-(trifluoromethyl) -5-[3-(Trifluoromethyl)phenyl]-3-iso- oxalyl]_2-fluorobenzonitrile (286 mg, 0.7 1 mmol) was added to acetonitrile (20 mL) Potassium carbonate (800 mg, 5.79 mmol) and 1,2,4-tris. (500 mg, 7.25 mmol) in a mixture. The reaction mixture was then vigorously removed at 8 Torr for 18 h. Adding to the oxime gum and removing the solvent at a low pressure to provide a free-flowing solid, which is eluted with ethyl acetate/hexane to give the title compound as a beige solid at a melting point of 131-132 ° C. Compound) (131.8 mg). *H NMr (CDci3) δ 8 89 (s,1H), (s,1H), 8.〇9-8.13 (m,2H),7.93 (d,ih),7 88 ( s,ih), 7.82 (d,1H),7·73 (d,1H), 7.63 (t,1H),4 i7 (d,ih),3 79 [(d,lH). The compounds in the table below can be prepared by procedures and methods known in the art.

845 845 845 845 845 845 845 H ocf2h Cl HF Cl F ocf2h Cl FF Cl Cl ocf2h Cl Cl F Cl Br ocf2h Cl Br F Cl cf3 ocf2h Cl cf3 F Br H ocf2h Br HF Br F ocf2h Br FF Br Cl ocf2h Br Cl F Br Br ocf2h Br Br F Br Cf3 ocf2h Br cf3 F CN H ocf2h CN HF CN F ocf2h CN FF CN Cl ocf2h CN Cl F CN Br ocf2h CN Br F CN cf3 ocf2h CN cf3 F CF3 H ocf2h cf3 HF cf3 F ocf2h cf3 FF cf3 Cl ocf2h cf3 Cl 130845. Doc -29- 200900398 R1 R2 R3 F CF3 Br F CF3 CF3

F CH3 H

F CH3 F F CH3 Cl F CH3 Br F CH3 CF3

F OCF2H H

F OCF2H F f F OCF2H Cl i F OCF2H Br F OCF2H CF3

F OCF3 H

F OCF3 F F OCF3 Cl F OCF3 Br F OCF3 CF3

F OCH2CF3 H

F OCH2CF3 F ( F OCH2CF3 Cl F OCH2CF3 Br F OCH2CF3 CF3

Cl Η H

Cl H F " Cl H Cl

Cl H Br

Cl H CF3

Cl F H

Cl F F

Cl F Cl R1 R2 R3 OCF2H cf3 Br OCF2H cf3 cf3 OCF2H ch3 H OCF2H ch3 F OCF2H ch3 Cl OCF2H ch3 Br OCF2H ch3 cf3 OCF2H ocf2h H OCF2H ocf2h F OCF2H ocf2h Cl ocf2h ocf2h Br ocf2h ocf2h cf3 OCF2H OCF3 H ocf2h OCF3 F ocf2h OCF3 Cl ocf2h OCF3 Br ocf2h OCF3 cf3 OCF2H OCH2CF3 H OCF2H OCH2CF3 F OCF2H OCH2CF3 Cl ocf2h OCH2CF3 Br ocf2h OCH2CF3 cf3 ocf3 HH OCF3 HF OCF3 H Cl 0CF3 H Br OCF3 H cf3 OCF3 FH OCF3 FF OCF3 F Cl 130845.doc -30- 200900398 R1 R2 R3 R1 R2 R3 Cl F Br OCF3 F Br Cl F cf3 〇CF3 F cf3 Cl Cl H 〇CF3 Cl H Cl Cl F 〇CF3 Cl F Cl Cl Cl 〇CF3 Cl Cl Cl Cl Br 〇CF3 Cl Br Cl Cl cf3 OCF3 Cl cf3 Cl Br H 〇CF3 Br H Cl Br F OCF3 Br F Cl Br Cl 〇CF3 Br Cl Cl Br Br 〇CF3 Br Br Cl Br cf3 OCF3 Br cf3 Cl CN H OCF3 CN H Cl CN F OCF3 CN F Cl CN Cl 〇CF3 CN Cl Cl CN Br 〇CF3 CN Br Cl CN cf3 OCF3 CN cf3 Cl cf3 H OCF3 cf3 H Cl cf3 F 〇CF3 cf3 F Cl cf3 Cl 〇CF3 cf3 Cl Cl cf3 Br OCF3 cf3 Br Cl cf3 cf3 OCF3 cf3 cf3 Cl Ch3 H 〇CF3 ch3 H Cl c H3 F OCF3 ch3 F Cl ch3 Cl 〇CF3 ch3 Cl Cl ch3 Br OCF3 ch3 Br Cl ch3 cf3 〇CF3 ch3 cf3 Cl ocf2h H 〇CF3 ocf2h H Cl ocf2h F OCF3 ocf2h F Cl ocf2h Cl 〇CF3 ocf2h Cl 130845.doc -31 - 200900398 R1 R2 R3 R1 R2 R3 Cl OCF2H Br 〇CF3 OCF2H Br Cl ocf2h cf3 OCF3 ocf2h cf3 Cl OCF3 H OCF3 ocf3 H Cl OCF3 F OCF3 OCF3 F Cl OCF3 Cl 〇CF3 OCF3 Cl Cl OCF3 Br ocf3 0CF3 Br Cl 〇CF3 cf3 〇CF3 OCF3 cf3 Cl OCH2CF3 H OCF3 OCH2CF3 H Cl OCH2CF3 F OCF3 OCH2CF3 F Cl OCH2CF3 Cl OCF3 OCH2CF3 Cl Cl OCH2CF3 Br OCF3 OCH2CF3 Br Cl OCH2CF3 cf3 OCF3 OCH2CF3 cf3 Br HH OCH2CF3 HH Br HF OCH2CF3 HF Br H Cl OCH2CF3 H Cl Br H Br OCH2CF3 H Br Br H cf3 OCH2CF3 H cf3 Br FH OCH2CF3 FH Br FF OCH2CF3 FF Br F Cl OCH2CF3 F Cl Br F Br OCH2CF3 F Br Br F cf3 OCH2CF3 F cf3 Br Cl H och2cf3 Cl H Br Cl F OCH2CF3 Cl F Br Cl Cl OCH2CF3 Cl Cl Br Cl Br OCH2CF3 Cl Br Br Cl cf3 OCH2CF3 Cl cf3 Br Br H och2cf3 Br H Br Br F OCH2CF3 Br F Br Br Cl OCH2CF3 Br Cl 130845.doc -32- 200900398

R1 R2 R3 R1 R2 Br Br Br OCH2CF3 Br Br Br cf3 OCH2CF3 Br Br CN H OCH2CF3 CN Br CN F OCH2CF3 CN Br CN Cl och2cf3 CN Br CN Br och2cf3 CN Br CN cf3 OCH2CF3 CN Br cf3 H OCH2CF3 cf3 Br cf3 F och2cf3 cf3 Br cf3 Cl OCH2CF3 cf3 Br cf3 Br OCH2CF3 cf3 Br cf3 cf3 OCH2CF3 cf3 Br ch3 H OCH2CF3 ch3 Br ch3 F och2cf3 ch3 Br ch3 Cl och2cf3 ch3 Br ch3 Br och2cf3 ch3 Br ch3 cf3 OCH2CF3 ch3 Br ocf2h H OCH2CF3 ocf2h Br ocf2h F och2cf3 ocf2h br ocf2h Cl OCH2CF3 OCF2H br ocf2h br OCH2CF3 ocf2h br ocf2h cf3 och2cf3 ocf2h br ocf3 H och2cf3 ocf3 br OCF3 F och2cf3 OCF3 br 0CF3 Cl och2cf3 OCF3 br OCF3 br och2cf3 OCF3 br OCF3 cf3 och2cf3 OCF3 br OCH2CF3 H OCH2CF3 och2cf br OCH2CF3 F OCH2CF3 och2cf Br OCH2CF3 Cl och2cf3 OCH2CF 130845.doc -33- 200900398 f R1 R2 R3 R1 R2 Br OCH2CF3 Br OCH2CF3 OCH2CF Br OCH2CF3 cf3 OCH2CF3 OCH2CF cf3 HH cyanohydrazine cf3 HF cyanohydrazine cf3 H Cl cyanohydrazine cf3 H Br cyanoguanidine Cf3 H cf3 cyanoguanidine cf3 FH cyano F cf3 FF cyano F cf3 F Cl cyano F cf3 F Br cyano F cf3 F cf3 cyano F cf3 Cl H cyano C1 cf3 Cl F cyano C1 cf3 Cl Cl cyano C1 cf3 Cl Br cyano C1 cf3 Cl cf3 cyano C1 cf3 Br H cyano Br cf3 Br F cyanide Base Br cf3 Br Cl Cyano Br cf3 Br Br Cyano Br cf3 Br cf3 Cyano Br cf3 CN H Cyano CN cf3 CN F Cyano CN cf3 CN Cl Cyano CN cf3 CN Br Cyano CN cf3 CN cf3 Cyano CN Cf3 cf3 H cyano cf3 cf3 cf3 F cyano cf3 cf3 cf3 Cl cyano cf3 130845.doc -34- 200900398 R1 R2 R3 R1 R2 R3 cf3 cf3 Br cyano cf3 Br cf3 cf3 cf3 cyano cf3 cf3 cf3 ch3 H cyano Ch3 H cf3 ch3 F cyano ch3 F cf3 ch3 Cl cyano ch3 Cl cf3 ch3 Br cyano ch3 Br cf3 ch3 cf3 cyano ch3 cf3 cf3 ocf2h H cyano ocf2h H cf3 ocf2h F cyano OCF2H F cf3 ocf2h Cl cyano OCF2H Cl cf3 ocf2h Br cyano ocf2h Br cf3 ocf2h cf3 cyano ocf2h cf3 cf3 ocf3 H cyano ocf3 H cf3 ocf3 F cyano OCF3 F cf3 ocf3 Cl aryl OCF3 Cl cf3 OCF3 Br cyano OCF3 Br cf3 OCF3 cf3 cyano OCF3 cf3 Cf3 OCH2CF3 H cyano OCH2CF3 H cf3 OCH2CF3 F cyano OCH2CF3 F cf3 och2cf3 Cl cyano OCH2CF3 Cl cf3 OCH2CF3 Br cyano och2cf3 Br cf3 OCH2CF3 cf3 cyano och2cf3 cf3 formulation / use

The compounds of the present invention are generally useful as an invertebrate pest control active ingredient in a composition (i.e., a formulation) having at least one other component selected from the group consisting of surfactants, solid diluents, and liquid diluents. Used as a carrier. The formulation or combination should be selected in accordance with the physical characteristics of the active ingredient, the mode of application, and environmental factors such as soil type, humidity and temperature. 130845.doc -35- 200900398. Suitable formulations include liquid and solid compositions. The liquid compositions include solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions), and the like, which can be thickened into gels as needed. The general types of aqueous liquid compositions are soluble concentrates, suspension concentrates, capsule suspensions, concentrated emulsions, microemulsions, and pure liquids. Typical types of non-aqueous liquid compositions are emulsifiable concentrates, microemulsifiable concentrates, dispersible concentrates, and oily dispersions. The general type of solid composition is dust, powder, granules, granules, pellets, pastilles, lozenges, filled films (including seed coatings), and the like, which can have water dispersibility (" wettable Sex or water soluble. Films and coatings formed from film forming solutions or flowable suspensions are especially useful for treating seeds. The active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; The overall formulation of the active ingredient can be controlled by embedding or delaying the release of the active ingredient. It can be emulsified (:= the advantages of both the ritual heart and the dry granule formulation. The high strength composition is mainly used as the middle of further blending. The liquid can be diffused into a suitable medium in the 喑霰 彡 彡 # 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 The volume may be between about a few thousand liters per hectare, but more typically between about 10 and hundreds of liters per liter + VA negative. The smog formulation can be in the tank, with water or another pick笹 笹 笹 且 且 且 且Mix, apply on empty ground, or apply to the cultivation medium of the plant, 'plant. The liquid formulation can be directly metered into the drip filed in the drip irrigation system or metered into the ditch during sowing 130845.doc - 36- 200900398 In the tank. Liquid and solid can be applied to crops or other seeds that require vegetative growth. As a seed treatment before sowing, the whole plant absorption method is used to protect the developing roots and other underground. Plant parts and/or leaves.: The formulation usually contains active ingredients, diluents and surfactants in an effective range of up to 100% by weight.

Water-dispersible and water-soluble granules, troches and powdery oily dispersions, suspensions, emulsions, solutions (including emulsifiable concentrates) Dust particles and granules High-strength compositions Weight percent active ingredient 0.001-90 Thinner 0-99.999 Surfactant 0-15 1-50 40-99 0-50 1-25 70-99 0-5 0.001-99 5-99.999 0-15 90-99 0-10 0-2 Solid diluents include, for example, clay (eg bentonite, montmorillonite, active

White clay and kaolin), gypsum, cellulose, titanium dioxide, zinc oxide starch, dextrin, sugar (such as lactose, sucrose), cerium oxide, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate and hydrogencarbonate Sodium, and sodium sulfate. Typical solid diluents are described in Watkins et al., i/α«〇/

Insecticide Dust Diluents and Carriers, Second Edition, T)〇r\and

Books, Caldwell, New Jersey. Liquid diluents include, for example, water, 7V, iV-dimethylalkaneamine (eg, iV, 7\A-dimethylguanamine), limonene, dimethyl sulfoxide, JV-alkylpyrrolidone (e.g., iV·methyl ° ratio σ each ketone), ethylene glycol, triethylene glycol 'propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffin wax (example 130845.doc -37- 200900398 Such as paraffin oil, normal paraffin, isoparaffin, alkyl stray, burnt oil, triacetin, sorbitol, glycerin, aromatic _ e malon, dearomatized aliphatic compound, alkyl benzene, alkane Ketones, ketones (eg, scorpion, 2-glyoxime 1, isophorone, and 4-pyridyl-4-methyl J-saponin), acetates (eg, acetic acid) Isoamyl ester, hexyl acetate, hexahydrate, octyl acetate, decyl acetate, tridecyl acetate and isoamyl acetate are the other types (eg, calcined lactate, two) Monoesters and γ-butyrolactones ^, ^ and alcohols (which may be linear, branched, saturated or unsaturated), such as formazan, ethanol, n-propanol, isopropyl , n-butanol, isobutanol, n-hexanol, n-octanol, n-octanol, nonanol, isodecyl alcohol, isostearyl alcohol, cetyl alcohol, lauryl alcohol, tridecyl alcohol, oleyl alcohol, cyclohexyl Alcohol, tetrahydrofurfuryl alcohol, diacetone alcohol and benzyl alcohol. Liquid diluents may also include glycerides of saturated or unsaturated fatty acids (usually C C22) such as plant oils and fruit oils (eg, eucalyptus oil, oyster sauce , linseed oil, sesame oil, corn (maize) oil, peanut oil, hollyhock oil, grape seed oil, safflower oil, cottonseed oil, soybean oil, rapeseed oil, 'coconut oil and palm kernel oil), animal fat For example, tallow, lard, lard, cod liver oil, fish oil), and mixtures thereof. Liquid diluents also include alkylated fatty acids (eg, methylated, hexaylated, taucosylated), wherein the fatty acid can be derived from plants and It is obtained by hydrolysis of animal-derived glycerides and can be purified by distillation. Typical liquid diluents are described in PCT (3), Heart/νπβ, Second Edition, Interseience, New γ〇Α, Η%. Solid and liquid compositions typically include - or multiple surfaces The active agent. When added to a liquid, the surfactant (also known as 〃 surface active test I30845.doc -38-200900398 agent) generally changes (most often reduces) the surface tension of the liquid. According to the surfactant molecule Surfactants can be used as wetting agents, dispersing agents, emulsifiers or defoamers. Hydrophilic and lipophilic groups can be classified as nonionic, anionic or cationic. Can be used in the present invention. Nonionic surfactants in the composition include, but are not limited to, alkoxylated alcohols, such as alkoxylated alcohols based on natural or synthetic alcohols (which may be branched or linear) and Alcohols are prepared with ethylene oxide, propylene oxide, butylene oxide or mixtures thereof; ethoxylated amines, alkanolamines and ethoxylated alkanolamines; alkoxylated triglycerides, For example, ethoxylated soybean oil, castor oil and rapeseed oil; alkoxylated alkylphenols, such as ethoxylated octyl expectation, ethoxylated oxime base, ethoxylated diterpene and B Oxidized dodecylphenol (from phenol to ethylene oxide, propylene oxide, ring a butane or a mixture thereof; a block polymer prepared from ethylene oxide or propylene oxide and a reverse block polymer prepared from propylene oxide and a terminal block thereof; ethoxylated fatty acid; Oxylated fatty esters and oils; ethoxylated oxime esters; ethoxylated tristyrylphenols (including those prepared from ethylene oxide, cyclopropane, butylene oxide or mixtures thereof); Acid esters, glycerol cool lanolin derivatives, polyethoxylated vinegars, such as polyethoxylated sorbitan fatty acid esters, polyethoxylated fatty acid sorbitol esters, and ethoxylated fatty acid glycerol Ester; other sorbitol derivatives, such as sorbitol esters; polymeric surfactants such as random copolymers, block copolymers, alkyd resins, polyethylene glycol (polyethylene glycol) resins, grafts Polymerization (iv) Comb polymer and star polymer; polyethylene glycol (polyethylene glycol); polyethylene glycol fatty acid ester; anthrone-based surfactant; and sugar derivatives, such as cane = 130845.doc - 39« 200900398 Vinegar, alkyl polyglycosides and alkyl polysaccharides.

Useful anionic surfactants include, but are not limited to, alkyl aryl sulfonic acids and salts thereof; carboxylated alcohols or ethoxylated alkyl phenols; diphenyl sulfonate derivatives; lignin and lignin derivatives , for example, lignosulfonate; maleic acid or succinic acid or its anhydride; olefin sulfonate; phosphate ester, such as alkoxylated alcohol phosphate, alkoxylated alkyl phenol phosphate and ethoxylate Styrene-based phosphate; protein-based surfactant; sarcosine derivative; styryl ether ether sulfate; sulfate and sulfonate of oil and fatty acid; sulfate of ethoxylated alkyl phenol And sulfonate; sulfate of alcohol; sulfuric acid vinegar of ethoxylated alcohol; sulfonate of amine and decylamine, such as #, alkyl oxosulfonate; benzene, cumene, toluene, xylene, And decyl sulphonate of succinyl and tridecyl benzene; sulfonate of condensed naphthalene; sulfonate of naphthalene and alkylnaphthalene; sulfonate of sulphate; sulfosuccinyl amide And sulfosuccinates and derivatives thereof such as dialkyl sulfosuccinates. Useful cationic surfactants include, but are not limited to, decylamine and ethoxylated decylamine; amines such as nonylalkylpropane diamine, tripropylene triamine and dipropylene tetramine, and ethoxylated amines, B Oxidized diamines and propoxylated amines (prepared from amines with ethylene bromide, propylene oxide, butylene oxide or mixtures thereof); amine salts such as amine acetate and diamine salts; quaternary ammonium Salts such as quaternary ammonium salts, ethoxylated quaternary ammonium salts and diquaternary ammonium salts; and amine oxides such as oxygen=alkyl dimethylamine and bis(2-hydroxyethyl)alkylamine oxide . Mixtures of nonionic and anionic surfactants or mixtures of nonionic disc cationic surfactants can also be used in the compositions of the present invention. Nonionic, anionic, and cationic surfactants and their recommended uses 130845.doc -40- 200900398 are disclosed in various public references, including McCMic/^〇h 5/(10)///ea cmd, annual US and International Edition, McCutche〇n, s

Division Publishing, The Manufacturing Confectioner Publishing Company; Sisely and Wood, Less C/opWz.ac?/dgewh, Chemical Publ., New York, 1964; and A. S Davidson and B. Milwidsky, Deiergewii, 7th Edition, John Wiley and Sons, New York, 1987 ° The compositions of the present invention may also contain certain formulation auxiliaries and additives known to those skilled in the art as a formulation aid (some of which may also be considered as solids Thinner, liquid diluent or surfactant). These blending aids and additives can be controlled: pH (buffer), foaming during processing (antifoaming agent such as polyorganosiloxane), sedimentation of active ingredients (suspension), viscosity (thixotropy thickener) ), microbial growth (antimicrobial) in the container, product; east knot (antifreeze), color (dye/pigment dispersant), wash away (film former or adhesive), evaporation (anti-evaporation agent), and others Formulation properties. Film formers include, for example, polyvinyl acetate, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymers, polyvinyl alcohol, polyvinyl alcohol copolymers, and the like. Examples of blending aids and additives include those listed in the following documents: McCutcheon’s Volume 2·· Functional Materials, Nianliang International and North American Edition, published by McCutcheon’s Division, The

Manufacturing Confectioner Publishing; and pct publication WO 03/024222. The compound of formula 1 and any other active ingredient are incorporated into the compositions of the invention 130845.doc • 41 · 200900398 by dissolving the active ingredient in a solvent or by grinding in a liquid or dry diluent. Solutions (including emulsifiable concentrates) can be prepared by simply mixing the ingredients. If the solvent to be used as the liquid composition of the emulsifiable concentrate is water-immiscible, the emulsifier is usually added after dilution with water to emulsify the solvent containing the active ingredient. The active ingredient slurry having a particle size of at most 2, 〇〇〇 μϊη may be subjected to wet grinding using a medium grinding to obtain particles having an average diameter of less than 3 μηη. The aqueous slurry can be made into a final suspension concentrate (see, e.g., U.S. Patent No. 3,060,084) or further processed by spray drying to form water dispersible granules. Dry formulations typically require a dry milling process which produces an average particle size in the range of 2 to 10 μηι. Dust and powder can be prepared by blending and (usually) grinding (e.g., using a hammer mill or a fluid energy mill). Granules and granules can be prepared by spraying the active material onto a shaped particulate carrier or by agglomeration techniques. See Browning, "Agglomeration", Chemical Five %' December 1967, pp. 147-48, Perry j C/zemzca/, 4th edition, McGraw-Hill,

New York, 1963, pp. 8-57 and below, and WO 91/13546. Granules can be prepared as described in U.S. Patent No. 4,172,7. The water-dispersible and water-soluble granules can be prepared as taught in U.S. Patent No. 4,144,050, U.S. Patent No. 3,920,442, and German Patent No. 3,246,493. Tablets can be prepared as taught in U.S. Patent No. 5,180,587, U.S. Patent No. 5,232,701, and U.S. Patent No. 5,208,030. The film can be prepared as taught in U.S. Patent No. 2,095,558 and U.S. Patent No. 3,299,566. For additional information on blending techniques, see T. S. Woods, "The Formulator5 s Toolbox - Product Forms for Modern 130845.doc 42· 200900398

Agriculture" 1 Pesticide Chemistry and Bioscience, The C/za/Zenge, T. Brooks and T. R. Roberts, Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120-133 page. See also U.S. Patent No. 3,235,361, column 6, column 16, column 7, column 19, and example 10-41; U.S. Patent No. 3,309,192, column 5, column 43 to column 7, column 62 and Examples 8, 12, 15, 39, 41, 52, 53 , 58 , 132 , 138-140 ' 162-164, 166 ' 167 and 169-182; U.S. Patent No. 2,891,855, column 3, column 66 to Column 5, column 17 and examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, New

York, 1961, pp. 81-96; Hance et al, Feei/ Cowiro/, 8th ed., Blackwell Scientific Publications, Oxford, \9 迖 9 \ Anti Developments in formulation technology, PJB Publications, Richmond, UK, 2000. In the following examples, all percentages are by weight and all formulations are prepared in a conventional manner. The compound number refers to the compound in the index table A. Needless to say, it is believed that those skilled in the art can fully practice the invention using the above. Therefore, the following examples are to be considered as illustrative only and not limiting in any way. Thus, Compound 1 of Example A-oxime can be substituted with any other compound of the present invention (e.g., Compound 9 or 13 in Index Table A). Percentages are by weight unless otherwise stated. 130845.doc -43- 200900398

Example A High Strength Concentrate Compound 1 98.5% Gasified Silicone 0.5% Synthetic Amorphous Fine Ceria 1.0%

Example B Wettable Powder Compound 1 65.0% Dodecylphenol Polyglycol Ether 2.0%

Sodium lignosulfonate 4.0% sodium bismuth aluminide 6.0% montmorillonite (fake burnt) 23.0%

Example C Granules Compound 1 10.0% Activated clay particles (low volatile matter, 90.0% 0.71/0.30 mm; U.S.S. No. 25-50 mesh)

Example D Extrusion of granules Compound 1 25.0% anhydrous sodium sulfate 10.0% Calcium lignin sulfonate 5.0% Sodium alkylnaphthalene sulfonate 1.0% Calcium/magnesium bentonite 5 9.0%

Example E Emulsifiable concentrate Compound 1 10.0% Polyoxyethylene sorbitol hexaoleate 20.0% C6-C10 fatty acid vinegar 70.0% 130845.doc -44- 200900398 Microemulsion

Example F Compound 1 Polyvinylpyrrolidone-vinyl acetate copolymer Alkylpolyglycoside Monooleic acid glycerin vinegar Water 5.0% 3 0.0% 3 0.0% 15.0% 20.0%

Example G seed imaginary compound 1

Polyvinylpyrrolidone-vinyl acetate copolymer montanic acid wax lignosulfonate calcium polyoxyethylene/polyoxypropylene block copolymer stearyl alcohol (POE 20) polyorganosiloxane dye red dye water 20.00% 5.00% 5.00% 1.00% 1.00% 2.00% 0.20% 0.05% 65.75% Examples 肥料 Fertilizer rods · Compound 1 Pyrrolidinone-styrene copolymer 1 6_Ethoxylated tristyrylbenzene talc Corn starch Nitrophoska® Permanent 15- 9-15 Slow Release Fertilizer (BASF) Kaolin Water The compound of the present invention is resistant to a variety of invertebrate harmful 2.50% 4.8 0% 2.30% 0.80% 5.00% 36.00% 38.00% 10.60% Animal activity. 130845.doc -45- 200900398 Includes invertebrates that inhabit various environments, such as = leaves, roots, soil, harvested crops or other food, buildings (4) leaves, stems, flowers:: real;: sacral animals, Feed on leafy liquids or tissues, and thus cause (1 material, fabric fiber or moving = t, forest, greenhouse crops, ornamental plants, nursery crops, storage 2 = or: dimensional products, or residential or other Damage or susceptibility of the structure or its contents, or harmful to animal health or public health. It is understood that not all compounds are equally effective and equally effective. All compounds and compositions of the invention can be Agronomically used to protect field crops from invertebrate pests, and to protect other horticultural crops and plants from plant invertebrates (4): This uses include conservation of crops and other plants (ie agronomy and non-agronomy) The second factor = contains genetic material that is introduced by genetic engineering (ie, transgenic) to provide favorable traits. Examples of such traits include: tolerance to, harmful to plant-feeding animals For example, insects, worms, spiders, nematodes, phytopathogenic fungi, bacteria, and viruses) high iup ma Μ tolerance to adverse growth conditions (eg, =, or low soil moisture, and high salinity), Increased rate or seed set rate, increased harvest yield, faster maturity, higher quality and/or nutritional value harvested, or improved product harvested: by engineering characteristics. Transgenic plants can be altered to exhibit multiple traits Examples of plants that provide traits by red-course or mutagenesis include Table 130845.doc • 46- 200900398 Variants of corn, cotton, soybean and potato that are currently inoculated with Bacillus thuringiensis toxins (eg YIELD GARD®, KNOCKOUT) ®, STARLINK®, BOLLGARD®, NuCOTN® and NEWLEAF®) and herbicide variants of corn, cotton, soybean and rapeseed (eg ROUNDUP READY®, LIBERTY LINK®, IMI®, STS® and CLEARFIELD®), and performance A ketamine transferase (GAT) to provide a herbicide resistant to glyphosate herbicide, or a crop containing the HRA gene, which provides resistance to herbicides that inhibit acetate lactate synthase (ALS) The compounds and compositions of the present invention may act synergistically with traits introduced by genetic engineering or altered by mutagenesis, thereby enhancing the phenotypic expression or efficiency of the trait or enhancing the control of the invertebrate pests of the compounds and compositions of the present invention. In particular, the compounds and compositions of the present invention can synergistically interact with phenotypic expression of proteins or other natural products that are toxic to invertebrate pests to provide superaddition control of such pests. The phytonutrients, such as a fertilizer composition, may also optionally be included, comprising at least one phytonutrient selected from the group consisting of nitrogen, phosphorus, potassium, sulfur, mom, town, iron, copper, butterfly, sage, and 4 mesh. Of note is a composition comprising at least one fertilizer composition comprising at least one phytonutrient selected from the group consisting of nitrogen, phosphorus, potassium 'sulfur, calcium and magnesium. Further compositions of the invention comprising at least one phytonutrient may be in liquid or solid form. Of note are solid formulations in the form of granules, sticks or lozenges. A solid formulation comprising a fertilizer composition can be prepared by mixing a compound or composition of the invention with a fertilizer composition and formulating the ingredients, and then preparing the formulation by methods such as granulation or extrusion 130845.doc-47 - 200900398 Do not or can be prepared by the following methods: Do not spray a solution or suspension of the compound or composition of the present invention in a volatile agent to a dimensionally stable mixture (for example, On a fertilizer composition in the form of granules, sticks or spinners, and then evaporating the solvent. : The use of the agricultural θ is to control invertebrate harmful animals in areas other than the fields of crop plants. Non-agronomic uses of the compounds and compositions of the present invention include the control of invertebrate pests in healthy cereals, legumes and other foods, and in foods such as clothing and carpets. The compounds of the invention and combinations & u agronomic uses also include control of invertebrate pests in ornamental plants, in forests, in courtyards, along railroad crossings, and on grasses such as lawns, golf courses and pastures. Non-agronomic uses of the compounds and compositions of the present invention also include control of invertebrate pests in dwellings and other buildings that may be occupied by humans and/or companion animals, on farms' specialty farms, zoos or other animals. The non-agricultural use of the compounds and compositions of the present invention also includes the control of pests such as termites which can damage wood or other structural materials used in the construction of (4). :: Ming: The non-agronomic use of the compounds and compositions also includes the protection of humans by invertebrate pests that control the transmission of infectious diseases and the control of the animal parasites, including control of parasites to the shoulders of host animals, The inferior parasites of the armpits, abdomen, and inner thighs are parasitic to the internal body of the host animal (eg, stomach, intestine, lung, static, lymphoid tissue). Harmful animals that transmit extracorporeal parasitism or disease include μ, upper, ^ ^ ^ including (for example) 螨, 蜱, 虱, mosquitoes, flies, mites and fleas. Internal parasites include big heartworm, worm and snail Insects I30845.doc -48- 200900398 The compounds and compositions are suitable for systemic and/or non-systemic control of the invasion or infection of parasites in animals. The compounds and compositions of the invention are particularly useful for combating the spread of ectoparasites or A pest of the disease. The compounds and compositions of the present invention are suitable for combating parasites that invade the following animals: agricultural animals such as cattle, mutton, goats, horses, pigs, donkeys, croons, buffalo, rabbits, hens, fires Chickens, ducks, geese and bees; pet animals and paid animals such as dogs, cats, pet birds and ornamental fish; and so-called experimental animals such as hamsters, guinea pigs, rats and mice. By resisting these parasites, death The rate and performance degradation (in terms of meat, milk, wool, hide, egg, honey, etc.) is reduced, so application of a composition comprising a compound of the invention allows for more economical and simple animal feeding management. Examples of non-agronomic invertebrate pests include the prints of Lepidoptera, larvae and adults, such as the armyworm, the cutworm, the ruler, and the heliothine in the Noctuidae family. (for example, the pink stem borer (Sesamia inferens Walker), the corn stalk borer (nonagrioides Lefebvre), and the southern army worm) (Spodoptera eridania Cramer), fall armyworm (Spodoptera fugiperda JE Smith) ' (beet armyworm) (Spodoptera exigua

Hubner), cotton leafworm (Spodoptera littoralis Boisduval), yellowstriped armyworm {Spodoptera ornithogalli Guen6e), black cutworm (Calendula nobile 130845) .doc -49- 200900398

f \

Hufnagel)), velvetbean caterpillar (Anticarsia gemmatalis Hiibner), green fruitworm (Lithophane antennata Walker), cabbage army worm {Barathra brassicae Linnaeus), Soybean Soybean looper) (PseMdop/Mha /«c/wden·? Walker), cabbage looper (m. HUbner), tobacco budworm (Wresce budworm) )); from the genus Pyryidae, aphids, tubeworms, larvae, pen worms, cabbage caterpillars, and skeletonizers (eg European corn borer)

Hiibner), navel orangeworm (Amyelois Walker), corn root webworm (Crambus caliginosellus Clemens), grasshopper (sod webworm) (Pyralidae: Οα/w (eg rice cut leaf field) (sod worm) (//erpe'ogra/wwa Walker)), sugarcane stem borer (Chilo infuscatellus Snellen), tobacco small borer (Neoleucinodes elegantalis)

Guende), green leafroller (Cnap/za/ocerw·?, grape leaffolder (Deswna /'wweM/k Hiibner), melon worm (melon worm) Diap/zam'o m'hWb Stoll)), cabbage center grub {Helluala hydralis Guenee), yellow stem borer (Scirpophaga kceriw/like Walker), early shoot aphid (early shoot) Borer) {Scirpophaga infuscatellus Snellen) '白130845.doc •50- 200900398 white stem borer (drilling white rice / (ποίαίβ Walker)), sugar cane white wolf moth (top sh〇〇t borer) (Scirpophaga nivella Fabricius), dark-headed rice borer (Chilo polychrysus Meyrick), cabbage cluster caterpillar (CroczWomza English); leaf curl in Tortricidae Insects, green worms, seed worms, and fruit worms (eg, c〇dling moth porno(10)//a Linnaeus), grape berry moth (grape berry moth) Grape fruit worm main moth (five rti/opka Clemens)), pear Oriental fruit moth (Grapholita molesta Busck), citrus false codling moth (Cryptophlebia / ewcoireia Meyrick), citrus borer awraHhima Lima), red tape leaf moth ( Redbanded leafroller) {Argyrotaenia velutinana Walker), obliquebanded leafroller (Chor/Wcmewra rowceana Harris), apple light brown apple moth (five/?//?/2 less) ^ posiWiiana Walker), European grape berry moth (female scorpion moth (five wpoecz/z'a <3wZ>kwe//a Htibner)), apple bud leaf moth (apple) Budemos pyrusana Kearfott, Dutch omnivorous leafroller {Platynota stultana Walsingham) 'barred fruit-tree tortrix {Pandemis cerasana Hiibner), brown brown tortrix (Pawc/ewb /zepara/ia Denis &Schiffermiiller)); and many other economically important 13845.doc -51 - 200900398 lepidoptera (eg diamondback moth xylost) Ella Linnaeus) Pink bollworm {Pectinophora gossypiella Saunders), gypsy moth {Lymantria dispar Linnaeus), peach fruit borer (Carposina niponensis Walsingham), singular bud moth (peach Twig borer) (dwarha Zeller), potato tuberworm (Phthorimaea operculella Zeller) 'spotted teniform leafminer (1"/2〇<:〇// 6 out of blancardella F abricius), Asiatic apple leafminer Matsumura, rice leaffolder Edwards, apple leafminer (Lewcopiera Zeller), and Blattodea Among the eggs, nymphs and adults, including from the genus Blattellidae and Blattidae (eg oriental cockroach (·β/αίίβ orfeWa/b Linnaeus), Asia Asian cockroach (German Mizukubo), German cockroach {Blattella germanica Linnaeus) 'brownbanded cockroach' (Supella longipalpa Fabri) Cius), American cockroach (Periplaneta americana Linnaeus), brown cockroach

Burmeister), Madeira cockroach Fabricius), smoky brown cockroach {Periplaneta fuliginosa Service), Australian Cockroach BYiplciYiQtci 130845.doc •52- 200900398 australasiae Fabr.), Lobster cockroach (iVawp/zoeia cherecz Olivier) and smooth cockroach {Symploce pallens Stephens); marks of the genus Coleoptera, leaf, fruit, root, food and Foam tissue larvae and adults, including elephants from the genus Anthribidae, Bruchidae, and Curculionidae (eg boll weevil (Mexican boll weevil) «山·? Boheman)), rice water weevil (Lissorhoptrus oryzophilus Kuschel), granary weevil (57iop/n7w·? granarz.ws Linnaeus), rice weevil («S /iop/n'/M·? Linnaeus), annual bluegrass weevil {Listronotus maculicollis Dietz), bluegrass billbug (Sp/zewop/zorws parvulus Gyllenhal), hunting 0 Hunting billbug (Sphenophorus venatus vestitus), Denver billbug («Sp/zenop/zorM·? cz.cai in Fahraeus); Flea, Cucumber in Chrysomelidae Leafhopper, rootworm, leaf beetle, horse chestnut leafhopper, and leaf miner (eg Colorado potato beetle [Leptinotarsa decemlineata Say), western corn rootworm (corn root) Vergifera virgifera LeConte))); Scarabs and other beetles from Scarabaeidae (eg Japanese beetle (Po/?"/z_a Newman), Oriental beetle (Oriental beetle) Jnoma/a orientalis Waterhouse, Oriental Axor Golden Tortoise (Sxowa/a 130845.doc •53- 200900398 (Waterhouse) Baraud), Northern Masked Chafer {Cyclocephala borealis Arrow), South As a masked chafer (Cyclocephala immaculata Olivier or C. /wWi/ar Bland), dung beetle, and white grub (Aphodius spp.), Black turfgrass ataenius (A taenius spretulus Haldeman), June June green turtle (green June beetle) «ίίίίαα Linnaeus, Asiatic garden beetle (Maladera castanea Arrow) ' i ^ / June May/June beetle (Gypsum beetle) and European chafer (Rhizotrogus majalis Razoumowsky); from the skin of Dermestidae; Golden worm from Elialidae; small locust from Scolytidae and flour ticks from Tenebrionidae. In addition, agronomic and non-agronomic pests include: eggs of the Dermaptera, adult and larvae, including from the genus Forficulidae (eg European earwig (Forficula auricularia Linnaeus), ® ^ (black earwig) (C/ze/boc/zes mor/o Fabricius)); eggs of Hemiptera and Homoptera, immature, adult and nymphs For example, from the herbaceous mites of the family Miridae, the monument from Cicadidae, the leaf mites from the genus Cicadellidae (for example, the genus genus (five), from the bed bugs (five w/joascra spp.) Cimicidae bed bugs (such as temperate bed bugs (C/mex /eciw/aWws Linnaeus)), from the genus Fulgoroidae and Delphacidae, from the horned family 130845.doc -54 - 200900398 (Membracidae) horned owl, wood JL from Psyllidae, powdery wind from Aleyrodidae, worm from Aphididae, _ root tumor finance (卩1^ 11〇乂614(1&6) grape root nodules, powder from the family Pseudococcidae From the genus Coccidae, Diaspididae and Margarodidae, the net from the genus Tingidae, from the genus Pentatomidae, the larvae For example, hairy chinch bug /n'riws Montandon) and southern chinch bug /zm/arb Barber) and other species of seed from Lygaeidae (seed bug) It comes from the pearl of Cercopidae, the squash of the genus Coreidae, and the red carp and cotton scorpion from the family Pyrrhocoridae. Also included are eggs of Acari (worm), larvae, nymphs and adults, such as the leaf worms of the family Tetranychidae and red spiders (such as the European red mite). (Apple full claw worm w/mz· Koch)), two spotted spider mite (Tetranychus urticae Koch) 'McDaniel mite (Te/ra «less c/zw·? McGregor))葡萄 短 中 螨 螨 螨 螨 螨 螨 螨 T T T T ci ci ci ci T ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci ci Aphids, which play an important role in human and animal health, are the dust mites in the Epidermoptidae family, the snails in the Dem〇dicidae, and the Glycyphagidae. The genus of the genus Ixodidae (commonly known as the hard palate) (eg deer Uck 130845.doc -55- 200900398 sca/jw/arb Say), Australia's ruthenium hard monument (Australian Paralysis tick) (full ring hard 蜱 / zo / ocyc / w · ? Neumann)), American (American dog tick) {Dermacentor variabilis Say), Ji ^ (lo Ne star tick) {Amblyomma americanum Linnaeus)) and the genus Argaidae (commonly known as soft palate) (eg relapsing fever tick (Ornithodoros turicata) 'common fowl tick (Argas radiatus)); Psoroptidae, Pyemotidae, and Sarcopteridae, 瞒 瞒 and acne; Orthoptera eggs, adult and immature Including ticks, mites and ticks (such as migratory ticks (such as Melanoplus sanguinipes Fabricius, M_ Thomas), American grasshoppers (such as americana Drury), deserts Desert locust (Sc/z/siocerca gregarz.a Forskal), migratory locust (Locw«sia mz'graiorz.a Linnaeus), bush locust (bad belly adenine) (Zowocerws spp.), house cricket (Jc/zeia c/omesiz'cwj· Linnaeus), mole cricket (eg tawny mole cricket) (•ScapieWscws Wckw Scudder) and southern aunt (southern mole cr Icket) (iScapierkcws Giglio-Tos))); eggs of the Diptera, adult and immature, including leaf miners (eg ZwWomyza spp., such as the genus Serpentine) Vegetable leafminer) (hWomyza deduction "vae Blanchard)), cockroach, fruit fly (Tephritidae), eye fly (eg rye stalk fly (asci(10)//α/Hi 130845.doc -56- 200900398

Linnaeus)), 蛆U maggot, housefly (such as housefly (M like domestic) Linnaeus), summer temple rope (such as summer rope (10) Linnaeus, French ink (Stein), Rope (such as the reins of Linnaeus), autumn rope, horn rope, 颂 (such as the golden spp.), 43 43⁄4 genus (corpse / zorm / a SPP.), and other moss fly (muscoid fly) Harmful animals, horse rainbow: (for example, genus (ΓαΖ)απΜ·5 spp.), skin rope (such as stomach genus spp.) 'Oesirws spp.), cowhide (such as cowhide) //•ypoi/erwa SPP.)), deer rope (eg, genus (C/zrpo;^ spp·)), sheep reins (eg, silk/argon fly (Me/op/zagw·? Linnaeus)) and Other Brachycera, mosquitoes (eg Aedes spp.), Anopheles (dwop/ze/a spp.), Culex (Cw/ex spp.), black flies (eg protozoa) Genus (ProWmM/z_ww spp.), genus (*S7mw" Mw spp.), cockroach, sand rope, cockroach, and other Nematocera; Thysanoptera eggs, adult And immature bodies, including onion thrips (77zri'j^ ia6acz· Lindeman), flowers Flower thrips (flowers, 15 genus {Frankliniella spp.), and other leaf-hopper hummers; insects of the Hymenoptera, including ants of the Formicidae, including Florida woodworking ants ( Florida carpenter ant) {Camponotus floridanus Buckley), red carpenter ant {Camponotus ferrugineus Fabricius), % (black carpenter ant) {Camponotus pennsylvanicus De Geer) 'white-footed ant' (Technomyrmex albipes fr. Smith), big headed ant (PAez'i/o/e sp.), black-headed ant (ghost 130845.doc -57· 200900398 ant) (Tapinoma melanocephalum Fabricius) ; :3⁄4: old ant (Pharaoh ant ) (pharaonis Linnaeus)) Little fire ant (Wasmannia auropunctata Roger), tropical fire ant gemhaia Fabricius, red imported fire ant (iSo/ewopds Buren) , Argentine ant (Iridomyrmex humilis Mayr), crazy ant {Paratrechina longicornis Latreille), pavement ant (TeiramoWMm caaph) Ww Linnaeus)), cornfield ant (Forster) and odorous house ant (!Ta/?z'"i?wa Say). Other Hymenoptera include bees (including wood bees), bumblebees, wasps, bees, and larvae (S. ssp.); genus (Cep/zMS spp,)); isoptera ( Isoptera) insect pests include the termite family (Termitidae) (eg, Macroerime·? sp.), Obibiosme?

Rambur)), Kalotermitidae (eg, C. elegans sp.), and Rhinotermitidae (eg, Reticulitermes sp.) Termites in the sp.), i/eieroiermes Hagen, eastern subterranean termite (yellow-breasted termites/7ανζ·;αα), western subterranean termite (western subterranean termite) Reticulitermes hesperus Banks) > Formosan subterranean termite (Coptotermes Shiraki), West Indian dry wood termite (West Indian 130845.doc • 58 · 200900398 drywood termite) {Incisitermes immigrans Snyder) 'Ml y}' White Sacrifice ( Powder post termite) 厶reWs Walker), drywood termite (/nczWierwes Light), southerland subterranean termite {Reticulitermes virginicus Banks), western drywood termite (Incisitermes minor Hagen) 'Tree arboreal termites (such as the termite genus (TVaswi/iermes sp.) and others of economic importance) Termites; insect pests of Thysanura, such as silverfish (Lepisma «sacc/jarka Linnaeus) and firebrat (Thermobia domestica Packard); insect pests of Mallophaga Including head louse (Pediculus humanus capitis De Geer), body louse (human body (Pe mountain · cw / ms / zwmaww · Linnaeus)), chicken body (chicken body (also: dog biting louse (TWc/2〇i/ecie«s· cam··? De Geer), fluff louse (de Geer) ), sheep body wind (sheep body louse) (5<9Wco/a ovb Schrank) short-nosed cattle louse {Haematopinus Nitzsch), long-nosed cattle louse (Zkogwai/zws Wiw&quot Linnaeus) and other e-attacks or animals that attack humans or animals and chew-type parasitic mites; insects of the Siphonoptera include oriental rat flea (Xenopsylla cheopis Rothschild), Cat flea (Ctenocephalides felis Bouche), canine (dog Flea) 130845.doc -59- 200900398 {Ctenocephalides canis Curtis), hen flea (Ceraiop/z less // w Schrank), sticktight flea (Echidnophaga gallinacea Westwood), human flea (Pw/ex /rrU training i Linnaeus) and other mites that afflict mammals and birds. Other arthropod pests covered include: spiders in the Araneae, such as the brown recluse spider (Ζοχσίπ/α mc/mm Gertsch & Mulaik) and the black widow spider ) (Red-backed widow spider (Z^r〇Aci-like mactans)

Fabricius)), and Scutigeromorpha's butterfly litigation, such as house centipede (Scwiigera coleoptrata Linnaeus). The compounds of the present invention are also active against Nemat〇da, Cestoda, Trematoda, and Acanthocephala members, including Strongylida, Ascaridida. ), economically important members of the genus Xyurida, Rhabditida, Spirurida, and Enoplida, such as, but not limited to, economically important industrial pests ( That is, the root-knot nematode (from the root-knot nematode, the root rot nematode (the corpse ~ root rot nematode, the genus Nematode (TWMo and rw), etc.) and animal and human health harmful animals (ie all economically Important flukes, mites, and nematodes, such as the genus Nematodes (xSYrowg/WiS, canine bowworms in dogs (4), scorpion worms (i...like contortus) in sheep, owe The idiom of the line 'Dirofilaria, the leaves of the horse, the naked head mites (Knowledge (4), anti-incitement I30845.doc -60. 200900398, Aepai/ca Linnaeus), etc.) Lepidoptera pests (eg cotton leaf argz7) /acea Htibner) (cotton leaf worm), fruit tree yellow moth

Walker) (fruit tree leaf roller), A Linnaeus (European leaf roller) and other yellow-moth (Jrc/n·/^) species, rice dimorphic filling (C/n7o swpprewat/z'i Walker) (rice stem borer), Cnaphalocrosis medinalis Guen6e (rice leaf roller), corn root knot worm, CVam^ws ieierreZ/ws Zincken (bluegrass webworm) , apple moth, cotton moth like insulana Boisduval) (spiny bollworm), Eijrz'as Fabricius (spotted bollworm), buddha (//e// Coverpa armigera Htibner), American bollworm, /e//coverpa zea Boddie (corn earworm), tobacco budworm, rice cut leaf moth , Cc^eha Denis & Schiffermtiller (grass leaf worm), cotton red worm, chre/Za Stainton (citrus leafminer), large white butterfly (corpse / erh Linnaeus) (large white butterfly), cabbage butterfly (household ra/me Linnaeus) (small white butterfly), Moth

Linnaeus), diamondback moth, litura Fabricius, tobacco catworm Rope (rw/ijr 130845.doc -61 - 200900398

Meyrick) (tomato leafminer)) exhibits particularly high activity. The compounds of the present invention also have significant activity against Homoptera members, including: Acyrthosiphon pisum Harris (pea aphid), Aphis craccivora Koch (cowpea aphid), , W, {Aphis /αόαβ Scopoli (black bean aphid), cotton aphid (melon aphid), apple money /?owz· De Geer (apple aphid), volume leaf (Jp/n) • spkaeco/a

Patch) (, spirea aphid), potato long must (Jw/acorAww so/am· Kaltenbach) (f〇xgl〇ve aphid), strawberry nails (C/zaeios/ p/ion/ragae/o/H Cockerell) (strawberry aphid), wheat double-tailed owl (Ζ)ζ·ΜΓίφ/π·ί noxia Kurdjumov/Mordvilko) (Russian wheat aphid), rose red frequency fruit ^ {Dysaphis plantaginea Paaserini) (rosy apple aphid) 'Eriosoma lanigerum Hausmann (woolly apple aphid), Tao Dawei Cai (//ya/opierM·? Geoffroy) (mealy plum aphid), Radish Cai Kaltenbach) (turnip aphid), Maiopo/op/n'wm dirrhodum Walker (cereal aphid), potato long tube wealth (Macrosiphum euphorbiae Thomas) (potato aphid), Cai Zhaocai ( Myzus persicae Sulzer) (peach-potato aphid, green peach aphid), lettuce (iVascmoWa ribisnigri Mosley) (lettuce aphid), worm (denter ewp/n'gM·? spp.) (root aphid) And ag (Gall aphid), corn spill Fitch (corn leaf aphid), He Gu Yi Guan Cai _ρα · 130845.doc -62- 200900398

Linnaeus) (bird cherry-oat aphid) 'Sc/π'ζίφ/π··? graminum Rondani (greenbug), Φ- ^ {Sitobion avenae Fabricius) (English grain aphid), 苜蓿 斑(mact/aia Buckton) (spotted alfalfa aphid), Toxoptera aurantii Boyer de Fonscolombe (black citrus aphid), and the big orange kitrus (brown citrus aphid); the ball is spp·) (adelgid) ;Phylloxera devastatrix Pergande (pecan phylloxera); Bemisia tabaci Gennadius (tobacco whitefly, sweetpotato whitefly), silver leaf powder wind ar exhausted;?"/b/z'z· Bellows &amp Perring) (silverleaf whitefly), citrus whitefly (Dialeurodes chW Ashmead) (citrus whitefly) and greenhouse powder wind (Trialeurodes vaporariorum Westwood) (greenhouse whitefly); potato leafhopper / a6ae Harris) (potato leafhopper), gray fly wind ( Zvaoi/e/p/mjc Fallen) (smaller brown planthopper), / 毙 leafhopper (Macro/eWes quadrilineatus Forbes) (aster leafhopper), Daqing Yehui

Uhler) (green leafhopper), Nephotettix nigropictus Stal (rice leafhopper), brown wind (TW/aparvaia lugens Stal) (brown planthopper), S. ^ ^{Peregrinus maidis Ashmead) (corn planthopper), white-backed planthopper, white-backed planthopper, Sogaioc/es οηϋο/α Muir (rice delphacid), white leaf bee/?omar /a 130845.doc -63 - 200900398

McAtee) (white apple leafhopper), genus genus (five spp.) (grape leafh〇pper); seventeen years Mag (Magicidada septendecim Linnaeus) (periodical cicada); (/cer_ya pwrc/zah Maskell) (cottony cushion scale), Pear-toothed Shield

Comstock) (San Jose scale); citrus meal A (Planococcus citri Risso) (citrus mealybug); Pswdococcws spp. (other whitefly complex); pear hibiscus (Cacop less / /a Foerster) (pear psylla), persimmon (7>/〇za Ashmead) (persimmon psylla) ° The compounds of the invention are also active against Hemiptera members, including: Acrosternum hilare Say (green stink bug) ), pumpkin green J# (dnasa De Geer) (squash bug), 蝽 蝽 leucopterus leucopterus Say) (chinch bug), temperate bed bug, cotton net culture (C*or_y//zMca Fabricius) (cotton lace bug), S blind wall modeWa Distant) (tomato bug), cotton red wasp (Dysdercus suturellus Herrich-Schaffer) (cotton stainer) > brown stinky bee (five wc/zhiws πΓνΜ·? Say) (brown stink bug), a shackle {Euchistus Variolarius Pali sot de Beauvois) (one-spotted stink bug), Grapicosi/zeiws spp. (species long-breeding complex), leaf-foot pine plugging (·Lepiog/oj^Ms corcw/ws Say) (leaf-footed pine seed bug), American pasture blindness/heo/arb Palisot de Beauvois) (t Arnished plant bug) ' Southern bee (Nezara viridula

Linnaeus) (southern green stink bug), rice brown 蝽 130845.doc -64- 200900398 pugnax Fabricius) (rice stink bug), large malaysian wall {Oncopeltus fasciatus Dallas) (large milkweed bug), cotton® 匕 blind culture {Pseudatomoscelis seriatus Reuter) (cotton fleahopper). Other insects controlled by the compounds of the present invention include the pteridoptera (e.g., western flower thrips), the platycodon

Moulton) (citrus thrips), big and Lima (Sericoi/zr/ps

Beach) (soybean thrips) and onion thrips (onion thrips); and coleoptera (eg Colorado potato leafhopper, mexican bean vizr/vesi/j· Mulsant) (Mexican bean beetle) and taro Insects, Artemisia or Nematodes should be noted that some modern classification systems divide Homoptera into suborders of the Hemiptera. Values are noted for the use of the compounds of the present invention for controlling silver leaf whitefly. It is worth noting that the compounds of the invention are useful for controlling the application of Western flower thrips. It is worth noting that the compounds of the invention are useful for controlling the application of the potato leafhopper. Notable is the use of the compounds of the invention for controlling corn planthoppers. Values are noted for the use of the compounds of the invention for controlling cotton. It is worth noting that the compound of the present day and month is used for the application of __. It is worth noting that the compounds of the invention are useful for controlling the use of Plutella xylostella. It is worth noting that the compounds of the invention are useful for controlling the application of the autumn moth. The compound of the present invention can also be worm-eating u', other biologically active compounds or test pieces 1J (including insecticides, chlorpyrifos sputum W, snails, bactericides, mites) 130845.doc •65· 200900398 Insecticide weeding], herbicide safeners, growth regulators (eg insect insect inhibitors and rooting stimulants), chemical sterilants, chemical pheromones, insect repellent J attractants, information A mixture of vegetarians, cobiotics, other biologically active compounds or entomopathogenic bacteria, viruses or fungi to form a multi-component pesticide that provides even more clothing and non-agronomic applications. The invention is therefore also directed to a group comprising a biologically effective amount! The compound, its oxime-oxide or ^ and at least one other biologically active compound or agent effective and may additionally comprise at least one surfactant, solid diluent or liquid diluent. For the mixtures of the invention, other biologically active compounds or agents may be formulated with the compounds of the invention comprising a compound of formula 1 to form a premix, or other biologically active compounds or agents may be combined with a compound of the invention comprising: The two formulations are combined separately and applied prior to administration (eg, in a spray tank). Other biologically active compounds or agents that are less useful in the compositions of the present invention may be selected from invertebrate pest control agents having different modes of action or different chemical classes, including macrolides, neonicotinoids, Okbar Amine ((10) topamine) receptor ligand, ryanodine receptor agonist, nanochannel modulator, chitin synthesis inhibitor, sand #母素(一.toxin) mimic, mitochondrial electron transport inhibitor , cholinergic enzyme inhibitor, cyclopamine insecticide, ecdysone inhibitor, GABA (Y. Aminobutyric acid)-regulated gas ion channel blocker, juvenile hormone mimic, lipid f biosynthesis inhibitor And biological agents (including nuclear polyhedrosis virus (NPV), members of the genus Bacillus, encapsulated Suyun golden buds. Endotoxin: and /, his naturally occurring or genetically modified insecticidal virus. 130845.doc - 66 - 200900398, notable for other biologically active compounds or agents selected from the group consisting of pyrethroids, urethanes, neonicotinoids, neuronal sodium channel barriers Broken agent, insecticidal macrolide, γ-Aminobutyric acid antagonizes urinary and juvenile hormone mimics, Bacillus thuringiensis members, Bacillus thuringiensis δ_endotoxins, and naturally occurring or genetically modified viral insecticides. Examples of such biologically active compounds or agents with which the compounds may be formulated are: insecticides such as abamectin, acephate, acetamiprid, acetamiprid ( Acetoprole), amid flumet (s_j 955), avermectin, azadirachtin, azinphos-methyl, bifenthHn, bifen Bifenazate, bistriflur〇n, buprofezin 'carbafuran', carb〇furan, cartap, chlorfenapyr, kefulong (chi〇rfiuazuron), chlorantraniliprole (DPX-E2Y45), chlorpyrifos, thiodoniasone, chromafenzide, christinidin, butadiene Cyfiumet〇fen), cyfluthrin, /3 - Sai Fanning, cyhal〇thrin, γ_ 赛洛子,赛/宁宁, cypermethrin, cyromazine, deitainethrin, Defence Diafenthiuron, diazjnon, dieldrin, diflubenzuron, dimefluthrin, dimethoate, din〇tefuran , Daifenolan, 130845.doc -67- 200900398 Emamectin, endosulfan, esfenvalerate, ethiprole, fenothiocarb , fenoXycarb, fenpropathrin, fenvalerate, fipr〇nil, flonicamid, flubendiamide, vassin (flucythrinate), tau-fluvalinate, flufenerim (UR-50701), flufenoxuron, fonophos, hafenfenzide, six Hexaflumuron, hydramethylnon, imidacloprid, 引多Indoxacarb, isofenphos, lufenuron, malathion, metaflumizone, metaldehyde, methamidophos, methidathion , methodomyl, methoprene, methoxychlor, metofluthrin, monocrotophos, methoxyfenozide, enebenzimid ( Nitenpyram), nithiazine, novaluron, noviflumuron (XDE-007), oxamyl, parathion, thiobarbarone, hundred Permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, fenfluthrin (profluthrin), protrifenbute, pymetrozine, pyrafluprole, pyrethrin, pyridinium 130845.doc -68 - 200900398 (pyridalyl) , fluoroquino (pyrifluquinazon), bipro (py) Riprole), pyripramine (pyripr0Xyfen), rotenone (r〇ten〇ne), ryanodine, spinetoram, spinosad, spirodiclofen, spirothyroid Ester (Spir〇mesifen) (BSN 2060), spirotetramat, sulprofos, tebufenozide, teflubenzuron, tefluthrin, TOEFL Terbufos, tetrachlorvinphos, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tolfenpyrad , tramomethrin, triazamate, trichlorfon and triflumuron; fungicides such as acibenzolar, aldimorph, Amisuibrom, azaconazole, azoXyStrobin, benalaxyl benomyl, benthiavalicarb, isopropyl basics Flica, binomial 'biphenyl, white catan Bittertanol, blasticidin-S, Bordeaux mixture (three bases of copper sulfate), boscalid/nicobifen, bromuconazole, thymosin Bupirimate, buthiobate, carboxin, carpropamid, captafol, captan, carbendazim, Gas anisole (chl〇roneb), chlorothalonil, chlozolinate, kehui sal. 130845.doc -69- 200900398 (clotrimazole), copper oxychloride, such as copper sulfate and hydroxide Copper salts such as copper, cyazofamid, cyflunamid, cymoxanil, Cyproconaz〇ie, cyprodinil, and dichlofluanid , diclocymet, diclomezine, dicloran, diethofencarb, difenac. Sitting (difenoconazole), dimethomorph, dimoxystrobin, fine. Diniconazole, diniconazole-M white powder (dinocap), discostrobin, dithianon, dodemorph, dodine, econazole, Etaconazole, edifenphos, epoxiconazole, ethaboxam, ethirimol, ethridiazole, famoxadone , fenamidone, fenarimol, fenbukang. Sitting (fenbuconazole), fencaramid, fenfuram, fenhexamide, fenoxanil, fenpiclonil, fenbupidine (fenbutidine) Fenpropidin), fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferfurazoate, ferimzone , fluazinam, fludioxonil, flumetover, fluopicolide, flu1xastrobin, fluquinconazole , flusilazole, flusulfamide, flutolanil, flurifaol, 130845.doc -70· 200900398 folfet, fossett (fosetyl-aluminum), fuberidazole, furalaxyl, furametapyr, hexaconazole, hymexazole, guazatine, Imazalil, imibenconazole, imipenem iminoctadine), Ionian

Iodicarb, ipoconaz〇le, iprobenfos, ipr〇dione, iprovalicarb, isoconazole, aficione Isoprothiolane), kasugamycin, kresoxim-methyl, mancozeb, mandipropamid, manneip, mepanipyrim > High-performance mefenoxam, mepronil, metalaxyl, metconazole, methasulfocarb, metiram, and methamphinol Metominostrobin) / fenominostrobin, mepanipyrim, metrafenone. Miconazole, myclobutanil, neo asozin (ferric methanearsonate), nuarimol, octhiminone, ou 〇furace, orysastrobin, oxadixyl, oxolinic acid, oxpoconazole, oxycarboxin, bucksin Paclobutrazol), penconazole, pencycuron, penthiopyrad 'perfurazoate, phosphonic acid, benzoquinone, biting benzene 130845.doc 200900398 methotrexate (picobenzamid ), pic〇XyStr〇bin, polyoxin, probenazole, prochloraz, pr0Cymid〇ne, propamocarb ), pppanmoca hydrochloride, pr〇pic〇naz〇le, propineb, pr〇qUinazid, prothioconazole, 派拉克史宾宾(pyraci〇str〇bin), pryazophos, pyrife Nox), pyrimethanil, pyrifenox, pyrolnitrine, pyroquii〇n, quinconazole, quinoxime (qUinoxyfen), quintozene, silthiofam, simeconazole, spiroxamine, streptomycin, sulphur, tebuconazole, tesque Techrazene, tecloftalam, tecnazene, tetraconazole, thiabendazole, thifluzamide, thiophanate, methyl More chlorpyrifos, thiram, tiadinil, tolclofos-methyl, tolyfluanid, triadimefon, triadimenol, bacterium Triarimol, 17m0 sitting triazoxide, tridemorph, trimoprhamide tricyclazole, trifloxystrobin, triforine, three Triticonazole, uniconazole, virgin (validamycin), 克克宁 I30845.doc -72- 200900398 (vinclozolin), 乃奈浦 (zineb), 益稳(ziram), and °zoxamide; nematicidal agent such as aldike (aldicarb) ), immicyafos, oxamyl and phenoline (fe_namiphos); bactericides such as streptomycin; acaricides such as amitraz, snails (chinomethionat), B. chlorobenzilate, cyhexatin, dicofol, dienochlor, etodox, etoxazole (fenazaquin), fenbutatin oxide, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridaben, and debufen (tebufenpyrad); and biological agents, including entomopathogenic bacteria' such as Bacillus thuringiensis Bacillus subtilis c-like mountain A subsp·, Bacillus thuringiensis Kultstack subsp. subsp. and Bacillus thuringiensis (eg Cellcap, MPV, MPVII); entomopathogenic fungi' Such as green muscardine fungUS; and entomopathogenic mothers, including baculovirus, nuclear polyhedrosis virus (NPV), such as the American cotton bollworm (/ / e /; coverpa zea) nuclear polyhedrosis virus (HzNpv), Celery genus (AfNPV); and granulomatosis (GV), such as the codling moth granule virus (CpGV). / The compounds of the invention and compositions thereof can be applied to plants which, in particular, are 'transformed into shells which can be rendered toxic to invertebrate pests (e.g., Bacillus thuringiensis g δ_ endotoxin) . The effect of the application of the present invention, the control compound of the vertebrate harmful animal, and the expressed toxin protein I30845.doc • 73· 200900398 may be synergistic. General references for this % of agricultural protective agents (ie insecticides, fungicides, nematicides, insecticides, herbicides and biological agents) include 77ze Pesi/cz.t/e 'di version 13' CDS Tomlin Edit, British

Crop Protection Council, Farnham, Surrey, U.K., 2003 and 77ze Price οΡαίζϋ Mflnwa/, 2nd Edition ’ Edited by L. G. Copping, British

Crop Protection Council, Farnham, Surrey, U.K., 2001. r Notable is a composition of the invention wherein at least one other biologically active compound or agent is selected from the group consisting of abamectin, homophosphorus, acequinocyl, arsenic, acetamidine Nitrocarbonitrile, arrinathrin, dexamethasone, flumethetamine, amoxicillin, avermectin, azadirachtin, acesulfame, diphenanthrene, bifenfene, bistrifluridine, Borate, buffing, carbaryl, carbofuran, bataan, carzol, chlorpyrifos, kefenabine, kefuron, chlorfenapyr, taosson, methyl taosson, Ethyl sterol, cofino, clofentezin, cotinine, butaflurane, cyprofen, ru-saiconing, cylonine, r-cylonin, λ-sailo Ning, Xi Man Dan, Sai Ning Ning, Sai Ning Ning, Yu-Sai Ning Ning, Xi Luo Mei Qin, De Mei Mei Ning, Dai Fen Xi Long, Da Lisong, Kai Le San, Die's Agent, In addition to Qi Ling, Fufulong, tetrafluthrin, dimehypo, dasong, datnam, dainfin, iman meiding, an murder, yifen huali, yipupu Etfinin (etGfenpr〇x): estoxazole, phenylphosphine, fentanzide, fenbuxene, phenylthiocarb, fenoxacil, fenprozin, fenfluster, fenfluramine, fepney, Gasbitus amide, flubendiamide, vinevine sin, sulphate, τ_fuhuali, Dun (four) um, qifen 130845.doc -74· 200900398 / Long, ground insect structure, annihilation (formetanate ), fosthiazate, hafen, hexaprox, dexamethasone, hydroxyxanthene, emisaces, idadamine, chlorhexidine, insecticidal soap, iso-phosphorus, lufen Long, marathon, fluorinated, polyacetaldehyde, damascus, dexamethasone, methiodicarb, nadine, oxime, methoxychlor, methoxyfen, metinine, ya Sulindene, nitenpyram, nitric thiocyanamide, Novartis, polyurea, eugenin, balason, thiobarathon, ubiquitin, furosemone, yubisong, fenshen, blessing Misetan, Bigep, Bufson, Trifluthrin, Rhodamine, Proudate, Bimezhuoxin, Bifipu #, pyrethrin, bisabene, acetamiprid, fluoroquine Comprehensive, Bishop, Bepsey Fen, fish vine _ 'Lani base, cyprodinil, spinosad, quaternary ketone brewing (one -), snail snail brewing, snail turtle, killing Pusson, Debufen carrying Sandup Ratio, Defulong, sulphate _, tofusone, chlorpyrifos, tetramethrin, sigh*, & to Tai,, insects, sesame, thiophene, insecticide, Imidazolamide, Taixuaning, = Ke cage 丨 一 — 阿 阿 阿 阿 阿 阿 阿 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 二 阿 阿 阿 阿 阿 阿 阿 阿 阿 阿 阿 阿 阿 阿 阿 阿 阿 阿 阿 阿 阿 阿Body virus, encapsulated Bacillus thuringiensis, endotoxin, baculovirus, entomopathogenic bacteria', bacteria. Two-spot disease and insect pathogens are also noteworthy for the composition of the present invention, wherein one active compound or reagent is composed of 、, and one other organism W is selected from the group consisting of the following composition, Amiqu, Auntie μι /巳果丁,亚乌芙菌素,印苦楝子净,巴丹,氯虫胺,克芬', Bi T, Bufenbao, β寒姑你宴比比,陶斯松,柯尼丁,赛Prosperous, β-赛福宁,赛洛宁J 挟 __赛洛宁' Sai Ning, Xiluo Meiqin, 130845.doc •75· 200900398 De Than Mei Ning, Dield's agent, creation table Tenan, Dai Lilan, Iman Meiding, Anshang., Yifen Huali, Ishihe, and Zhizhi # — can be Japanese sulphur, fenox, fensine, fensini, and fluorine Insectamine, flufensulfonate, hexaflurane, hydroxymethyl: etadamine: 引多克, 鲁芬隆, 美氟综, 纳奈得, methoxyphyllin, oxyfluoride, nitenpyram , thiocyanamide, Novartis, European killing, than Metso Qin, pyrethrum exaggerated ^ Yu Jing Bida Ben, acetamiprid, and puxixi. Phytophthora ring, amine sputum, spirulina, snail ester, debufen, mites, food

_ 塞美索占, thiodac, insecticidal, tyrosin, arsenic, insecticidal, Bacillus thuringiensis, subspecies, Bacillus thuringiensis, Kurstack subspecies, nuclear polyhedrosis virus And encapsulated S. sinensis δ_ endotoxin. For embodiments in which the various mixing partners are used, the weight ratio of the various mixing partners (total) to the formula Ht is typically between about 1.3000 and about 3000:1. The magical finder is a weight ratio between about 13 〇〇 and about 300.1 (e.g., a ratio between about 1:3 () and about valence ^). Those skilled in the art can readily achieve a bioavailable amount of the active ingredient required for biological activity in a desired range via simple experimentation. Obviously, the range of invertebrate pests controlled by these other components is greater than that controlled by the compound of Formula 1 . In some cases, the incorporation of a compound of the invention of the invention with other biologically active (especially invertebrate pest control) compounds or agents (i.e., active ingredients) results in an additive (i.e., production) effect. People always (4) effectively reduce the amount of active ingredients released in the environment while effectively controlling harmful animals. If the I spinal harmful animal control active ingredient produces a synergistic effect at the application rate, this is obtained. J30845.doc - 76· 200900398

The agronomically satisfactory level of I.,, and the control of harmful animals in the vertebrae reduces the cost of crop production and reduces the environmental burden. ! Group 4 may have a combination of a compound of formula i and at least one active ingredient. It is particularly noteworthy; where =:, the sexual composition and the formula W have no 丄 = circumference and not η: in the case of 'with at least one similar control and different treatment sites and traitors ^ ' , ',,, and the control of active ingredients in animals with vertebrae can be particularly advantageous. Thus, the compositions of the present invention may additionally comprise a biologically effective amount of at least one other invertebrate pest control active ingredient' which has similar control ranges and different sites of action. Contacting a plant or a two-part site genetically modified to exhibit an invertebrate pest animal compound (e.g., a protein) with a biologically effective amount of a compound of the invention also provides a greater range of plant protection and facilitates resistance management. The following is a list of specific combinations of hydrazine compounds with other invertebrate pest control agents which illustrate the mixtures, compositions and methods of the invention. The first in Table A lists specific invertebrate pest control agents (eg, in the first column, abametine). The second block of Table A lists the mode of action (if known) or chemical classification of the invertebrate pest control agent. The third barrier of Table A lists examples of the weight ratio range relative to the hydrazine compound, its N-oxide or salt at the application rate of the invertebrate pest control agent (for example, abamidine by weight relative to The compound of Formula 1 is "5〇:1 to 1:5〇"). Thus, for example, the first row of Table A specifically discloses that the combination of the compound of Formula 1 and abametine can be administered in a weight ratio of 50 丨 to 〇 5 。. The remaining rows of Table A are similarly understood. Also notably, Table A lists specific combinations of the compound of Formula 1 with other invertebrate pest control agents 130845.doc • 77-200900398, which illustrate the mixtures, compositions and methods of the present invention, and Table A includes the respective application rates. Other embodiments of the lower weight ratio range.

Table A Invertebrate Pest Control Agent Mode of Action or Chemical Classification Typical Weight Ratio Abametine Macrolide 50:1 to 1:50 Sub-exterminology New Test 150:1 to 1:200 Ami Qukes Okbar Amine receptor ligand 200:1 to 1:100 avermectin macrolide 50:1 to 1:50 Azadirachtin ecdysone agonist 100:1 to 1:120 /5- Sai Fanning Channel Modulator 150:1 to 1:200 Phenfenin Channel Regulator 100:1 to 1:10 Buphinjing Chitin Synthetic Inhibitor 500:1 to 1:50 Badan Silkworm Toxin Analog 100:1 to 1 :200 chlorantranin ryanolide receptor ligand 100:1 to 1:120 kefenatin mitochondrial electron transport inhibitor 300:1 to 1:200 Tausson cholinesterase inhibitor 500:1 to 1:200 Nikonin New Test 100:1 to 1:400 Safranine Channel Conditioner 150:1 to 1:200 Seronine Channel Conditioner 150:1 to 1:200 Safranine Channel Conditioner 150 :1 to 1:200 sirmimethine chitin synthesis inhibitor 400:1 to 1:50 Demetrinium channel regulator 50:1 to 1:400 Didar cycloolefin pesticide 200:1 To 1:100 Datnam Neonicotin 150:1 to 1:200 wearing Finnish acute skin inhibitor 150:1 to 1:200 Immanmilol macrolide 50:1 to 1:10 Anti-cyclophane insecticide 200:1 to 1 :100 130845.doc -78- 200900398 Invertebrate Pest Control Agent Mode of Action or Chemical Classification Typical Weight Ratio Ivanide Sodium Channel Modulator --------- 100:1 to 1:400 ISHIP GAB Α-regulated chloride channel blocker 200:1 to 1:1 phenyl thiosulfide 150:1 to 1:2 〇〇 谨 谨 西 保 保 保 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 500 Regina channel modulator 150:1 to 1:2〇〇Fipney GABA-regulated chloride channel blocker 150:1 to 1:1 〇〇 flufenidamide 200:1 to 1:1〇〇 Flurfluramine indole receptor ligand 100:1 to 1:120 Fluorene quinone chitin synthesis inhibitor 200:1 to hexafluoron chitin synthesis inhibitor 300: lJLh50~ hydroxyxanthene mitochondrial electron transport inhibition 150:1 to etadamin new final test 1000:1 to 1:1000 lead multi-killer channel regulator 200:1 to 1:50 λ-cylonine channel regulator 50:1 to 1:250 Rhodamine 曱 chitin synthesis inhibition 500:1 to US Fluoride* Comprehensive 200:1 to 1:200 Natto Bile Acetase Inhibitor 500:1 to 1:100 Metoclopramide Juvenile Hormone 500:1 to 1:100 Oxyfluorone Ecdysone-loaded agonist ------------- 50:1 to 1:50 dilute sigma nicotinamide neonicotinine '^ 150:1 to 1:200 nitric acid In the test 150:1 to 1:200 Novartis chitin synthesis inhibition 500:1 to 1:150 Ou to kill the test SI _ inhibitor 200:1 to 1:200 than Metso Qin. - ---- 200: 1 to 1:100 pyrethrina channel modulating agent 1 〇〇: 1 to 1:10 200:1 to 1:100 200:1 to 1:100 bismuth mitochondrial electron transfer a bite worm shouting ~~ ~___ ---_ 130845.doc -79- 200900398 Invertebrate Pest Control Agent Mode of Action or Chemical Classification Typical Weight Ratio Piscifi Proximity Analogs 500:1 to 1:100 Lenny Tester Ligand 100:1 to 1:120 cyprodinil macrolide 150:1 to 1:100 Sinistera macrolide 500:1 to 1:10 Spirulina lipid biosynthesis inhibitor 200:1 Up to 1:200 snail ester lipid biosynthesis inhibitor 200:1 to 1:200 Agonist 500:1 to 1:250 σ Respiroid neonicotinoid 100:1 to 1:200 Semesodin-like neonicotinine 1250:1 to 1:1000 thioglycocholic esterase inhibitor 500:1 To 1:400 Insecticidal 150:1 to 1:100 Tymone Channel Modulator 150:1 to 1:200 Tri-Azuramide Esterase Inhibitor 250:1 to 1:100 Insecticidal Chitin Synthetic inhibitor 200:1 to 1:100 Bacillus thuringiensis biological reagent 50:1 to 1:10 Bacillus thuringiensis δ-endotoxin biological reagent 50:1 to 1:10 ΝΡ V (eg Gemstar) biological reagent 50:1 to 1:10 Examples of an invertebrate pest control agent (such as an insecticide and an insecticidal agent) mixed with a compound of the present invention include a nanochannel modulator, such as Phenfenin, Safranine, Xeronine, λ-赛Luoning, Sai Fanning, β-Sai Fu Ning, De Meimining, Tetrafenthrin, Effin Chemical, Fenhua Li, Yin Duo Ke, Meitin, Trifluthrin, Pyrethrum And chloramphenicol; cholinesterase inhibitors, such as Taosson, Na Nad, Ou, thiophene and San Azamei; new tests, such as sub-kill, cotinine, Dart South, EDTA, ene, nicotinamide, thiabendazole and semexole; insecticidal macrolide, 130845.doc •80- 200900398

For example, side amine, spinosad, abamectin, avermectin and immanmetine; GABA (T-aminobutyric acid) regulated gas ion channel blockers, such as Anzufen, Ishi universal fee Puni; chitin synthesis inhibitors, such as buffing, sirmimethine, flufenron, hexaflurane, riffin, Novartis, polyurea and insecticide; juvenile hormone mimics, for example Wearing Finnish, fenoxoc, oxime and bepexifene; octopamine receptor ligands, such as ampicix ecdysone agonists, such as azadirachtin, saponin; Receptor ligands, such as lanoni, amine back inner needle II = (eg, chlorfenapyr (see U.S. Patent No. 6,747, 〇 47, pcT publication WO 2003/0155 18 and WO 2004/067528) and flubendiles Indoleamine (see U.S. Patent No. 6,6G3,044)); Nereistoxin mimics, such as Bataan; mitochondrial electron transport inhibitors such as kefenabine, m-methylidene and bisabene; lipid synthesis inhibitors , for example, spiroxene and spirodecyl ester; cyclodiene insecticides, such as dieldrin; butaflurane; phenylthiocarb; fluramide; Comprehensive; than Flipru; biting insects and sews; Bibulu; 匕美卓秦; snail B S曰, and slaves. Examples of biological agents to be mixed with the compounds of the present invention include nuclear polyhedrosis viruses such as HzNPV &AfNpv; Bacillus thuringiensis

And encapsulated Bacillus thuringiensis delta-endotoxin, such as Cellcap, MPV and MPVII 'u & natural, existing & genetically modified viral insecticides, including the genus Bacul〇viridae family Members and insectivorous fungi. Of note, the compositions of the present invention wherein at least one other biologically active compound or agent is selected from the invertebrate pest control agents listed in Table A above. The weight ratio of a compound (including a compound of formula 1, its N-oxide or salt) to other vertebrate-free 130845.doc -81 - 200900398 vertebrate pest control agents is usually between 1〇〇〇:1 and ι:ι〇〇〇 Between 500:1 and 1:5〇〇 in one embodiment, between 250:1 and 1:200 in another embodiment and 1〇〇:1 in another embodiment Between 1:50. Examples of specific compositions comprising a compound of formula 1 (compound number refers to a compound in index table a) and other invertebrate pest control agents are listed in Table B below.

Table B Mixture No. Compound No. and Invertebrate Pest Control Agent Mixture No. Compound No. and Invertebrate Pest Control Agent A-1 1 and Abammetine B-1 2 and Abam η1'' A-2 1 and灭培B-2 2 and yamidine A-3 1 and amitripr B-3 2 and amitripty A-4 1 and avermectin B-4 2 and avermectin A-5 1 And azadirachtin B-5 2 and Indomethacin A-6 1 and /5 - Sai Fanning B-6 2 and Xinsai Funing A-7 1 and Bifenin B-7 2 and Bifennin A-8 1 and buffing net B-8 2 and buffing net A-9 1 and bataan B-9 2 and bataan A-10 1 and lactobacillus B-10 2 and amphotericin A-11 1 Kevinaby B-11 2 and Kyle Nabi A-12 1 and Taosson B-12 2 and Taosson A-13 1 and Cotinidine B-13 2 and Cotinidine A-14 1 and Sai Fanning B -14 2 and Sai Fanning A-15 1 and Xeronine B-15 2 and Xeronine A-16 1 and Sai Ning B-16 2 and Sai Ning 130845.doc -82- 200900398 Mix No. Compound No. And invertebrate pest control mixture number Compound number and invertebrate pest control agent A-17 1 and cilostazol-17 2 and cilostazol A-18 1 and dextran -18-2 and dexamenin A-19 1 And dieldrin Β-19 2 and dieldrin A-20 1 and Datnam Β-20 2 and Datnam A-21 1 and Dairy Β-21 2 and Dai A-22 1 and Imanmi Ding Hao-22 2 and Imam Meiding A-23 1 and Anita Panyu-23 2 and Anshen A-24 1 and Effing Chemicals-24 2 and Effing Chemical A-25 1 and Iraq希普Β-25 2 and Ishipu A-26 1 and benzothiovir -26 2 and phenylthiocarba A-27 1 and fenoxicam -27 2 and fenoxik A-28 1 and Fenicide Β-28 2 and Fenhua Li A-29 1 and Fipney Β-29 2 and Fipney A-30 1 and flunicarbamide Β-30 2 and flufenidamide A-31 1 and fluoride 1 insect amidoxime-31 2 and avermectin A-32 1 and flufenazone-32 2 and flufenazone A-33 1 and hexaprolon-33 2 and hexaflulon A-34 1 and Hydroxymethyl sulphate-34 2 and hydroxyxanthene A-35 1 and EDTA Β-35 2 and EDTA A-36 1 and 引多杀克Β-36 2 and 引多Killer A-37 1 and λ-赛洛宁Β-37 2 and λ-赛洛宁 A-38 1 and LufenlongΒ-38 2 and Lufenlong A-39 1 and US Fluoride-39 2 And fluorinated A-40 1 and Nadine Β-40 2 and Nadine A-41 1 and methoxyproline-41 2 and oxaprost A-42 1 and 曱 芬 Β Β -42 2 and oxime phenone A-43 1 and nitenpyramidine 43-43 2 and acetophenone 130845.doc -83- 200900398 mixture number compound number and invertebrate pest control mixture mixture number compound number and invertebrate Harmful animal control agent A-44 1 and thiocyanate B-44 2 and thiocyanamide A-45 1 and Novartis B-45 2 and Novartis A-46 1 and Euro killer B-46 2 and Europe Killing A-47 1 and Metso Qin B-47 2 and Metso Qin A-48 1 and pyrethrin B-48 2 and pyrethrin A-49 1 and Bidaben B-49 2 Daben A-50 1 and bituminous propyl ether B-50 2 and. Acetone C-scale A-51 1 and bepexifene B-51 2 and bepexifene A-52 1 and Lenny B-52 2 and Lenny A-53 1 and lactamidine B-53 2 and cyprodinil A-54 1 and spinosad B-54 2 and spinosad A-55 1 and spiroxene B-55 2 and spiroxene A-56 1 and spiro sulphate B -56 2 and snail ester A-57 1 and Debu B-57 2 and Debufen A-58 1 and 嗟虫琳 B-58 2 and 嗟虫琳 A-59 1 and Semeso B-59 2 and Semenso A-60 1 and thiotica B-60 2 and thiotica A-61 1 and insecticidal single B-61 2 and insecticidal single A-62 1 and Taining B-62 2 and Taining Ning A-63 1 and San Azome B-63 2 and San Azamei A-64 1 and insecticidal B-64 2 and insecticidal A-65 1 and Bacillus thuringiensis B-65 2 and Bacillus thuringiensis A-66 1 and Bacillus thuringiensis δ-endotoxin B-66 2 and Bacillus thuringiensis δ-endotoxin A-67 1 and NPV (eg Gemstar) B-67 2 and NPV (eg Gemstar) 130845.doc •84- 200900398 Mixture number compound number and invertebrate pest control agent Mixture number compound number and invertebrate pest control agent C-1 9 and abamectin D-1 10 and abamidine C-2 9 and subctomy D-2 10 and subctomy C-3 9 and Amiqu D-3 10 and Amiqu C-4 9 and avermectin D-4 10 and avermectin C-5 9 and azadirachtin D-5 10 and azadirachtin C -6 9 and β-赛福宁 D-6 10 and /5- Sai Fanning C-7 9 and Bifennin D-7 10 and Bifennin C-8 9 and Bufenjing D-8 10 and Bufenjing C- 9 9 and Bataan D-9 10 and Bataan C-10 9 and chlorfenapyr D-10 10 and chlorfenapyr C-11 9 and kefenafen D-11 10 and kefenabine C- 12 9 and Dossson D-12 10 and Dossson C-13 9 and Cotinidine D-13 10 and Cotinidine C-14 9 and Sai Fanning D-14 10 and Sai Fanning C-15 9 and Xeron D-15 10 and Xeroning C-16 9 and Sai Ning D-16 10 and Sai Ning C-17 9 and Xiluomei Qin D-17 10 and Xiluomei Qin C-18 9 and Demeimei Ning D-18 10 and Detaminin C-19 9 and dieldrin D-19 10 and dieldrin C-20 9 and Datnan D-20 10 and Tenan C-21 9 and Dai-Finnish D-21 10 and Dai-Finnish C-22 9 and Imam-Med D-22 10 and Imam-Ming C-23 9 and An-Dan Fan D-23 10 and An Yu Fan C-24 9 and Effin Chemicals D-24 10 and Effin Chemicals C-25 9 and ISHIP D-25 10 and ISHIP C-26 9 and Phenylsulfide D-26 10 and Phenylthiocarb C-27 9 and Fenocchio D-27 10 and Fenoxax I30845.doc -85 - 200900398 Mixture No. Compound No. and Invertebrate Pest Control Agent Mixture No. Compound No. and Invertebrate Pest Control C-28 9 Fenhua Li D-28 10 and Fenhua Li C-29 9 and Fipney D-29 10 and Fipney C-30 9 and fluramide D-30 10 and gas. Ascorbic acid C-31 9 and flufenic acid amine D-31 10 and flufenic acid C-32 9 and flufenalin D-32 10 and flufenacil C-33 9 and hexavallon D-33 10 And hexafluorone C-34 9 and hydroxyxanthene D-34 10 and hydroxyxanthene C-35 9 and edetamine D-35 10 and edetamine C-36 9 and lead chlorpyrifos D-36 10 and Introduction of C-37 9 and λ-Xelonine D-37 10 and λ-赛洛宁 C-38 9 and Lufenlong D-38 10 and Lufenlong C-39 9 and US Fluoride D- 39 10 and US Fluoride C-40 9 and Nadine D-40 10 and Nadine C-41 9 and Metoproline D-41 10 and Oxygen Proline C-42 9 and Oxygen Fen -42 10 and methoxyfen-loaded C-43 9 and carbamide D-43 10 and dilute 17-fixed amine C-44 9 and thiocyanate D-44 10 and thiocyanamide C-45 9 and Novartis D-45 10 and Novartis C-46 9 and Eurozone D-46 10 and Europharm C-47 9 and Metso Qin D-47 10 and Metso Qin C-48 9 and pyrethrin D-48 10 and avermectin C-49 9 and Bida D-49 10 and Bida Ben C-50 9 and. Fixed insects and mystery D-50 10 and . Acetone C-51 9 and bepexifene D-51 10 and bepexifene C-52 9 and Lenny D-52 10 and Lenny C-53 9 and cyprodinil D-53 10 and cyprodinil C-54 9 and spinosad D-54 10 and spinosad 130845.doc -86- 200900398 mixture number compound number and invertebrate pest control mixture mixture number compound number and invertebrate pest control Agent C-55 9 and spirulina D-55 10 and spiroxene C-56 9 and spironolactone D-56 10 and snail ester C-57 9 and Debufen D-57 10 And Debufen C-58 9 and D-Sermine D-58 10 and Insecticide C-59 9 and Semenso D-59 10 and Semenso C-60 9 and Sultan D- 60 10 and thiotica C-61 9 and insecticidal D-61 10 and insecticidal single C-62 9 and Tai-ning D-62 10 and Tai-ning C-63 9 and three Azamei D-63 10 and three Azamei C-64 9 and insecticidal D-64 10 and insecticidal C-65 9 and Suyun Golden Spore D-65 10 and Bacillus thuringiensis C-66 9 and Suyun Golden Spore D-66 10 and Suyun Golden Spore Δ-endotoxin δ-endotoxin C-67 9 and NPV (eg Gemstar) D-67 10 and NPV (eg Gemstar) E-1 13 and abamectin E-35 13 and edamine E-2 13 and Yam Pei E-36 13 and Yin Duo Ke E-3 13 and Amiqu E-37 13 and λ- Xeronine E-4 13 and avermectin E-38 13 and Lufenlong E-5 13 and azadirachtin E-39 13 and US fluoride* comprehensive E-6 13 and cold-Sai Fu Ning E-40 13 and Na Nai E-7 13 and Bifenin E-41 13 and Oxygen Lin E-8 13 and Bufenjing E-42 13 and Xenoxyfen E-9 13 and Bataan E-43 13 and nitenpyram E-10 13 and chlorfenapyr E-44 13 and nitric oxide Cyanamide E-11 13 and Kefnerabine E-45 13 and Novartis 130845.doc •87- 200900398 Mixture No. Compound No. and Invertebrate Pest Control Agent Mixture No. Compound No. and Invertebrate Pest Control Agent E-12 13 and Taosson E-46 13 and Ou Emei E-13 13 and Cotinidine E-47 13 and Metso Qin E-14 13 and Sai Fanning E-48 13 and pyrethrin E-15 13洛宁 E-49 13 and Bida E-16 13 and Sai Ning E-50 13 and sigma sigma E-17 13 and semexime E-51 13 and bepexifine E-18 13 and dexamethanin E-52 13 and Lenny E-19 13 and dieldrin E-53 13 and cyprodinil E-20 13 and Datnam E-54 13 and the promise of killing E-21 13 and wearing Finnish E-55 13 and snail II Kefen E-22 13 and Imammetine E-56 13 and spironolactone E-23 13 and Angufan E-57 13 and Debufen E-24 13 and Effin Chemical E-58 13 And 嗟虫琳 E-25 13 and Ishipu E-59 13 and Semenso E-26 13 and benzosulfide E-60 13 and thiotica E-27 13 and fenocyl E-61 13 and Insecticidal E-28 13 and Fenhua Lee E-62 13 and Taining E-29 13 and Fipney E-63 13 and San Azamei E-30 13 and flunifluendamide E-64 13 And insecticidal E-31 13 and flufenic acid amine E-65 13 and Bacillus thuringiensis E-32 13 and flufensulfon E-66 13 and Bacillus thuringiensis δ-endotoxin E-33 13 and hexaflulon D -67 13 and NPV (eg Gemstar) E-34 13 and the specific mixtures listed in Table B are usually in accordance with Table A. Combined ratio of 1 130845.doc -88- 200900398 compound with other invertebrate pest agent. A method of controlling an invertebrate pest in an agronomic and non-agronomic application is: applying a biologically effective amount of the compound of the invention, usually in the form of a composition, to the environment in which the pest is exposed (including agronomic and/or non-agronomic infestation) In place, applied to the protected area, or applied directly to the pest to be controlled. 13 The present invention therefore includes a method of controlling a beneficial vertebrate pest in an agronomic and/or non-agronomic application comprising contacting an invertebrate pest or an environmental disk thereof with a biologically effective amount of - or a plurality of compounds of the invention, or with at least one The composition of the compound is contacted or contacted with a composition comprising at least one such compound and a biologically effective amount of at least one other biologically active compound or agent. Examples of suitable compositions comprising a compound of the invention and a biologically effective amount of at least one potent biologically active compound or agent include granular compositions wherein the other active compound forms the same particles as the compound of the invention or separates from the particles of the compound of the invention. Particles. For contact with a compound or composition of the invention to protect field crops from invertebrate pests, the compound or composition is typically applied to the crop seeds prior to sowing, applied to the leaves of the crop plants (eg, leaves, stems, Apply to soil or other growth medium on flowers, fruits, or before or after crop planting. One example of a contact method is a spray method. Alternatively, the particulate composition comprising the compound of the invention may be applied to plant leaves or earthworms. The plant can also be contacted with a composition comprising a compound of the invention to effectively deliver the compound of the invention via plant absorption. The composition is used as a liquid formulation. I30845.doc -89 - 200900398 soil soaking agent, applied to the soil. It is applied by a granular formulation, a nursery box treatment agent or a transplanted plant infusion. It is noted that the compositions of the present invention are in the form of a soil-soaked liquid formulation. It is also worth noting that the control of invertebrates is there. The animal is intended to include contacting the invertebrate pest or its environment with a biologically effective amount of a compound of the invention, or with a composition comprising a biologically effective amount of the compound. It is also worth noting that in this method the environment is soil and the composition is applied to the soil as a soil soaking formulation. It is also worthwhile; the idea is also effective when the compound of the present invention is topically applied to the affected part. Other methods of contact include direct or residual spray, aerial spray, gel, seed coating, microencapsulation, whole plant absorption, seduce, ear hooks, bolus, nebulizer 'fumigant, aerosol The compounds or compositions of the invention are applied in a manner that is dusty and in many pots. One embodiment of the contacting method is a dimensionally stable fertilizer granule, stick or lozenge comprising a compound or composition of the invention. The compounds of the invention may also be impregnated into materials useful in the manufacture of invertebrate control devices, such as insect screens. The compounds of the invention may also be treated with a seed to protect the seed from invertebrate pests. In the context of the present disclosure and the scope of the claims, treating a seed means contacting the seed with a biologically effective amount of a compound of the invention. The compound is typically formulated as a composition of the invention. This protects the seed from the soil without ridges. The roots of the seedlings from the sprouting seed development and its::::: Seed treatment can also be carried out by the transfer of the compound of the present invention or the third active adult plant. Silk can be treated on seed = type of seed, including white Gan '" find the insect to all. From the plants that can be genetically transformed to express the special 130845.doc -90- 200900398 traits. Toxic proteins (such as Su Di; include those that exhibit toxic effects on invertebrates or herbicide resistance (eg, licorice = bacillus toxin), and their resistance to phosphatidylcholine (d) 'A method which provides one of the methods for seed treatment, which is to sown seeds (ie, as a formulated composition) for the okara cutting) to spray or seed the seeds. Film forming agent or binder. Therefore, the present invention seed coating composition usually comprises a biologically effective amount of a compound, a straight N-oxide or a salt, a film former or a binder. The seed can be coated by the following method : Will be flowable The float concentrate is sprayed directly into the rolling bed of the seed and then the seed is dried. Alternatively, other blending types (eg, wetted powders, solutions, suspoemulsions, emulsifiable concentrates, and emulsions in water) can be sprayed To the seed. This method is especially useful for applying a film coat to a seed. A variety of coating machines and methods are available to those skilled in the art. Suitable methods include those listed in the following documents: P. Kosters et al. W Treatment: Progress and Prospects, 1994 BCPC Mongraph No. 57 ' and the references listed therein. Treated seeds are usually treated with about 〇, 1 g to 1 kg / 100 kg of seed (ie about 0.0001 to 1% by weight before treatment) The amount of the seed comprises a compound of the invention. The flowable suspension formulated for seed treatment typically comprises from about 0.5% to about 70% active ingredient, from about 0.5% to about 30% film-forming binder, from about 0.5% to about 20%. % dispersant, 0 to about 5% thickener, 0 to about 5% pigment and/or dye, 0 to about 2% antifoaming agent, antimony to about 1% preservative, and 0 to about 75% volatile liquid Diluent. 130845.doc 91 200900398 The compound of the present invention can be used. a trapping composition for the consumption of harmful animals in the spine or for use in devices such as traps, traps, and the like. Such an inducer may be in the form of particles comprising (4) a component of a biologically effective amount. 1 compound, its N-oxide or salt; (b) one or more food materials '(optional) (4) attractant, and (optionally selected) (4) or a variety of a-protective agents. Or a bait composition comprising about 0.0G1-5% active ingredient, about (4) food material and/or attractant, and (optionally) about W moisturizer; which can control the soil at a very low application rate (4) The harmful animals of the spine, especially at the lethal dose of the active ingredient, are controlled by exposure to the ancient contact. Certain food materials can be used both as a source of food and as an attractant. Food materials include carbohydrates, proteins, and lipids. This is a must for food. Examples of food materials are plant flour, sugar, yogurt, animal fat, vegetable oil, acid y yeast extract and milk solids. Examples of attractants are fragrances and mites for 丨ry (eg fruit or plant extracts, camphor, or other animal or plant group ^^^^) ghouts or known to attract targets... Other reagents. Examples of m humectants (ie, humidity retainers) are diols and other polyols, green b \m ' from sorbitol. Notably, the method of the bait composition is used to control at least one invertebrate selected from the group consisting of ants, ants, and mites. animal. The device for controlling the invertebrate harmful person 可^ may comprise the bait group of the present invention: the material and the material are received and the composition is less than one opening, the size of which allows the helmet to ride too far through the opening to make the ridgeless: : The position of the pest outside the outer casing, wherein the outer casing is also suitable for placement in or near the ridgeless == to the enthalpy (four) and the active or known activity of the D animal 130845.doc -92. 200900398. The present sigma sigma may not be administered with other adjuvants, but most commonly the formulation will contain _ or more active ingredients and suitable carriers, diluents and surface agents! · Oysters ‘and the end use covered by the end can be combined with food. An application method comprises spraying an aqueous dispersion or a refined oil solution of the compound of the present invention. Combinations with spray oils, spray oil concentrates, spreading adhesives, adjuvants, other solvents, and synergists such as piperonyl butoxide typically enhance the efficacy of the compound. For non-agronomic applications, sprays can be applied by means of a spray container such as a can, bottle or other container by means of a pump or by releasing it from a pressurized container, such as a pressurized aerosol spray can. These spray compositions can take various forms such as sprays, mists, foaming agents, (iv) or mist. Thus, such spray compositions may additionally include propellants, foaming agents, and the like, as the case may be. Notably, a spray composition comprising a biologically effective amount of a compound or composition of the invention and a carrier is included. An example of such a spray composition comprises a biologically effective amount of a compound or composition of the invention and a propellant. Representative propellants include, but are not limited to, methane, ethane, propane, butane, isobutane, butene, pentane, isopentane, neopentane, pentene, hydrofluorocarbons, fluorocarbons, Dimethyl, and the above mixture. It is noted that the spray composition (and the method of using the spray composition dispensed from the spray container) is used to control at least one invertebrate pest selected from the group consisting of: a mosquito 'black fly, Fly, fly, horse, bee, wasp, bumblebee, monument, insect, spider, nano, and the like, including individuals or combinations thereof. Non-agronomic applications include the protection of animals (specifically vertebrates, more specifically 130845.doc •93- 200900398 and s thermophilic vertebrate (eg mammals or birds), and most specifically mammals) from invertebrate parasitic harmful animal damage This is carried out by administering to the animal to be protected an effective (i.e., biologically effective) amount of a compound of the invention (usually in the form of a composition formulated for medical use). Accordingly, a value is directed to a method of protecting an animal comprising administering to the animal a parasiticidally effective amount of a compound of the invention. In the context of the present disclosure and the scope of the patent application, the term "parasiticidal" and "parasiticidal" refers to an observable effect of invertebrate parasitic harmful animals that protect animals from harmful animal damage. Parasiticidal effects generally refer to reducing the presence or activity of a target invertebrate parasitic animal. Such effects on harmful animals include necrosis, death, growth retardation, reduced motility or reduced ability to remain on or in the host animal, reduced feeding and inhibition of reproduction. These effects on invertebrate parasitic animals can provide control (including prevention, reduction or elimination) of parasitic invasion or infection of the animal. Examples of injecting a parasiticidally effective amount of a compound of the present invention into an invertebrate parasitic pest controlled by an animal to be protected include ectoparasites (arthropods, mites, etc.) and endoparasites (worms, for example Nematodes, flukes, mites, spines, etc.). In particular, the compounds of the present invention are effective against ectoparasites, including: flies, such as stagnation flies, (10) 5) (h〇rn ny), ticks, genus (black flies), Gypsophila (G/〇如仙 spp) (tsetse flies), head flies (four) to call, autumn fly, face fly, housefly, sweat fly heart; (sweat fly) , genus (horse), cowhide rope (opened, silkworm (// outside • then / (6) price), silky green fly (z (10) · - 130845.doc -94 - 200900398 ser / caia), red copper green rope ( Imcz·"(green blowfly), genus (Ca/Z^p/zora spp_) (blowfly), genus Fusarium (/Vofop/zormz'a spp.), sheep mad rope (Oesirws oWs) ( Nasal botfly), genus (Cw//co/i/e*s· spp.) (midge), horsefly, horse's stomach (Gastrophilus instestinalis), red-tailed flies {Gastrophilus haemorrhoidalis) Fiber {Gastrophilus eas/z's), chaos 'eg cattle black chaos (βον/co/a [Dawa/zWoj 6ovz)), Ma Babes (·δονζ·οο/α, 驴 blood, 彖 杂 乱 乱(Fe/z'co/α •swZjroWraiws), Spinig I I messed up {Hete Rodoxus spiniger), Jjgnonathus setosus, stagnation of scorpion; sheep sling, such as sheep reins; locusts, such as itch (Pwrop such as spp.), 疥螨 (1Saa〇p, 牛济癣 ( C/2〇rz·印如6〇νζ\〇, horse Demodex 〜 (~ Qingxin; c is called, 螨 螨 (CheyietieUa s Yang), cat + perforated 疥癣螽 (N〇t〇edres Cati)'s genus (7> 〇-α spp.) and deafness (〇w(10)α(10)_ mite); 蜱, such as genus (/χ〇ί/βί spp), burdock (such as 心SPP· ), Fantou genus (intestine spp.), flower genus such as coffee _ SPP ·), genus genus chia (10) (10) spp.), genus genus (the heart of the spp.) and blood genus (/ / (10) speaks wonderfully μ...spp); and fleas such as meerkats and canines. Non-agronomic applications in veterinary medicine are carried out by conventional means, for example, by means of a key, capsule, drink or veterinary drug. Formulations, granules, pastes, pills (boU), feeding procedures, or suppository forms are administered by enteral feeding; or by parenteral administration 'for example by injection (including muscle 130845.doc - 95- 200900398 internal, intraperitoneal) Planting: by nasal injection or impregnation in the form of a material (4): dipping, washing, coating a powder, or applying to a smaller area of an animal: by containing a compound or composition of the invention Items such as neck π tail straps, limb straps or reins are used. Typically, the present invention provides a parasite composition comprising a compound of formula i, which is a cerium-oxide or a mixture of a plurality of medicinal or veterinary acceptable carriers, which carriers comprise reference to a given route of administration (eg, Oral, topical or parenteral administration such as injection) and excipients and auxiliaries selected according to standard practice methods. In addition, the 'suitable carrier system, based on the composition, or the plurality of activities, produces a known phase (including factors such as stability and water content of ρΗ). Therefore, it is worth noting that animals are protected from invertebrate reproduction. A composition for animal damage, comprising a parasiticidally effective amount of a compound of the invention and at least one carrier. For parenteral administration (including intravenous, intramuscular, and subcutaneous injection), the compounds of the present invention may be formulated as suspensions, solutions or emulsions in oily or aqueous vehicles and may contain, for example, suspending agents, stabilizers, and / or an auxiliary agent such as a dispersant. The pharmaceutical composition for injection comprises an aqueous solution of the active ingredient (for example a salt of the active compound) in a water-soluble form, preferably in a physiologically compatible buffer, which comprises other excipients known in the art of pharmaceutical formulation. Or additives. For oral administration in the form of a solution (the form most suitable for absorption), emulsions, suspensions, pastes, gels, capsules, lozenges, boluses, powders, granules, rumen retention agents and feed/water/dishes And, the compound of the present invention can be formulated with an adhesive/filler suitable for oral administration of a composition, such as a saccharide (e.g., lactose, glace, mannitol, sorbus), which is known from the art of 130845.doc-96-200900398. Sugar alcohol), temple powder (such as maize powder, wheat glutinous rice powder, rice porridge powder 'potato starch), cellulose and derivatives (such as methyl cellulose, carboxymethyl cellulose, cellulose), protein Derivatives (such as zein, gelatin), and synthetic polymers (such as polyvinyl alcohol, polyvinylpyrrolidone). If necessary, it can be added, a lubricant (such as magnesium stearate), a disintegrant (4) crosslinked pyrrolidone, agar, alginic acid) and a dye or pigment. Pastes and gels often also contain binders (e.g., gum arabic, alginic acid, bentonite, cellulose, xanthan gum, colloidal magnesium aluminum silicate) to help the composition remain in contact with the oral cavity and are not easily discharged. If the parasiticidal composition is in the form of a feed concentrate, the carrier is typically selected from a performance feed, a feed cereal or a protein concentrate. In addition to the parasiticidal active ingredient, the compositions comprising the feed concentrate may comprise additives which promote the health or growth of the animal, improve the meat quality of the animal being slaughtered or may be used for animal feeding management. Such additives may include, for example, vitamins, antibiotics, chemotherapeutic agents, bacteriostatic agents, fungistatic agents, anticoccidial agents, and hormones. The compounds of the present invention have been found to possess advantageous pharmacokinetic and pharmacodynamic properties which provide systemic availability from oral administration and ingestion. Thus, the compounds of the present invention which are effective in killing parasites in the bloodstream after protection of the animal for ingestion protect the treated animals from blood-sucking harmful animals such as fleas, ticks and ticks. Thus, it is noted that the composition is a composition for protecting an animal from invertebrate parasitic animal damage. It is in a form for oral administration (ie, in addition to a parasitic effective amount of a compound of the present invention, comprising one or more selected from Applicable to the carrier of 130845.doc -97- 200900398 oral and feed concentrate carriers and fillers). Uses: The formulations are usually in the form of powders, creams, ... sprays, lotions, foaming agents, pastes, aerosols, ointments, creams or gels. More generally, the 'local formulation is a water soluble solution, - may be in the form of a diluted concentrate prior to use. Suitable for use in a pest composition comprising a compound of the invention and/or a plurality of parts:: = when applied to the surface of the animal in a line or point form (ie, "point" treatment), the active ingredient is applied along the surface of the animal. The migration covers its large: "knife or all outer surface areas. Therefore, in particular, the treated animals are protected from invertebrate and savage animal feeding such as cockroaches, fleas and cockroaches which feed on the epidermis of the animal. Thus, formulations for topical concentration often contain at least one organic solvent to facilitate delivery and/or penetration of the active ingredient into the skin of the animal. Solvents which are generally used as carriers in such formulations include propylene glycol, paraffin wax, perfumery compounds, esters such as isopropyl myristate, ethers, and alcohols such as ethanol and n-propanol. The rate of application required to achieve effective control (ie, 'biologically effective amount') depends on various factors, such as the type of invertebrate to be controlled, the life cycle of the harmful animal 'life stage, its large +, the injury must be ever greater,' Location, season, host crop or feeding characteristics, mating characteristics, ambient humidity, temperature 'and the like. The application rate in 2Γ1~sex/ha is sufficient to control the right pocket in the Chen Yisheng system. Harmful animals, but as low as 〇〇〇〇1 public capacity is enough, or maybe Thunder _ ancient; 5; 〇 1, 、, ^ to return to 8 s. ha. For non-agronomic applications. 'Efficient use can be Within the scope of (4) _ square meters, _❹ 〇"mg/m2 may be sufficient, or may require 15 J J30845.doc -98- 200900398 Those skilled in the art can easily determine the degree of control required for invertebrate pests. The biologically effective amount required. Typically for veterinary use, the guanidine compound, its N-oxide or salt is administered to an animal intended to protect against invertebrate parasitic pests in a parasiticidally effective amount. The effective amount of parasiticidal is the amount of active ingredient required to achieve an observable effect of reducing the presence or activity of the target invertebrate parasitic animal. Those skilled in the art should understand that the effective dose of parasiticidal can be based on the following factors.

Variations: The species and composition of the invention, the desired parasiticidal effect and duration, the target invertebrate pest species, the animal to be protected, the mode of administration, and the like, and the amount required to achieve a particular result can be determined via simple experimentation. For oral administration to a warm-blooded animal, the daily dose of the compound of the invention, based on the animal body weight, is typically in the range of from about 1 mg/kg to about 1 mg/kg, more typically about 0.5 mg/kg. Up to about 1〇〇mg/kg. For topical (eg, transdermal) administration, the infusion and spray generally comprise from about 〇. 5 to about

Ppm to about 3000 5000 ppm of a compound of the invention, more typically about ppm 〇 The following test demonstrates the control of a compound of the invention against a particular pest. ''Control effectiveness,' indicates inhibition of the development of the helmet (including death) that results in a significant reduction in eating. However, protection from compound extracts is not limited to such species. See Tables A and B for a description of the compounds. The abbreviation .Έχ.,, stands for "Instances" and the following figures show the synthetic synthesis of the prepared compounds|J. 130845.doc -99- 200900398

Index table A

Compound R1 R2 R3 mD ΓΟ 1 Cl H Cl 64-66 2 Br H Br 161-163 3 Br HF 氺4 cf3 H cf3 148-149 5 Cl cf3 H 130-131 6 Cl HF 97-98 7 Cl H Br 氺8 Cf3 HF 氺9 (Ex. 1) Cl F Cl 79-80 10 (Ex. 2) Cl Cl Cl 57-58 11 FFF * 12 cf3 H Br 168-169 13 (Ex. 3) cf3 HH 131-132 14 Br Cl Cl 76-77 15 Cl OCH2CF3 Cl 氺16 Br H ocf3 氺17 cf3 FH 119-120 18 Cl Cyano Cl 106-107 19 Cl CHs Cl 78-79 20 cf3 F Br 氺21 Cl Br Cl 100-101 22 Cl Ch3 Br 51-52 23 Br F Cl 64-65 24 Br ch3 Br 69-70 130845.doc - 100- 200900398 Compound R1 R2 R3 mp f°C) 25 Br Η H * 26 ocf3 Η H 氺27 Cyano Cl Cl氺^ NMR data see index table B ^ Index table 化合物 Compound number WNMR data (use CDC13 solution unless otherwise stated) a 3 δ 8.86 (s, 1H), 8.18 (s, 1H), 8.06-8.09 (m, 2H ), 7.89 (d, 1H), 7.52 (s, 1H), 7.27-7.33 (m, 2H), 4.11 (d, 1H), 3.74 (d, 1H). 7 δ 8.87 (s, 1H), 8.19 (s, 1H), 8.06-8.09 (m, 2H), 7.91 (d, 1H), 7.64 (s, 1H), 7.59 (s, 1H), 7.53 (s, 1H), 4.11 (d, 1H), 3.72 (d, 1H). 8 δ 8.90 (s, 1H), 8.22 (s, 1H), 8.09-8.13 (m, 2H), 7.94 (d, 1H), 7.67 (s, 1H), 7.58 (d, 1H), 7.44 (d, 1H), 4.17 (d, 1H), 3.76 (d, 1H). 11 δ 8.87 (s, 1H), 8.19 (s, 1H), 8.06-8.09 (m, 2H), 7.91 (d, 1H), 7.26 (t, 2H), 4.11 (d, lH), 3.70 (d, 1H). 15 δ 8.87 (s, 1H), 8.19 (s, 1H), 8.04-8.07 (m, 2H), 7.90 (d, 1H), 7.55 (s, 2H), 4.41 (q, 2H), 4.10 (d, 1H), 3.63 (d, 1H). 16 δ 8.90 (s, 1H), 8.21 (s, 1H), 8.08-8.12 (m, 2H), 7.94 (d, 1H), 7.71 (s, 1H), 7·50 (s, 1H), 7.44 ( s, 1H), 4.13 (d, 1H), 3.74 (d, 1H). 20 δ 8.90 (s5 1H), 8.22 (s, 1H), 8.12-8.09 (m, 2H), 8.05 (m, 1H), 7.95 (d, 1H), 7.80 (m, 1H), 4.17 (d, 1H) ), 3.76 (d, 1H). 25 δ 8.86 (s, 1H), 8.21 (s, 1H), 8.12-8.08 (m, 2H), 7.92 (d, 1H), 7.77 (s, 1H), 7.60 (d, 1H), 7.55 (d, 1H), 7.36 (t, 1H), 4.12 (d, 1H), 3.77 (d, 1H). 26 δ 8.86 (s,1H), 8.21 (s,1H), 8.12-8.06 (m, 2H), 7.93 (d,1H), 7.54-7.49 (m, 3H), 7.34 (d,1H), 4.15 ( d, 1H), 3.79 (d, 1H). 27 5 8.93 (s, lH), 8.49(s, 1H), 8.29 (s, 1H), 8.13-8.11 (m5 2H), 8.02 (m, 1H), 7.98 (d, 1H), 4.25 (d, 1H) ), 3.81 (d, 1H). The a 4 NMR data is expressed as a ppm low magnetic field from tetradecyl decane. Coupling is expressed as (s) - single bolus ' (d) - bimodal, (m) - multiplet.

Biological Example of the Invention Test A 130845.doc -101 - 200900398 The test unit for evaluating the control of the leeks is composed of a small open sigma container having a radish plant inside. This unit is pre-invasive by the larvae of the pond, and the larvae are pre-invasive. The larvae are selected from the worms, and the two are placed in the test single open φ Λ early 7^ by the jade unearned shaft powder. After being dispensed into the test unit, the larvae are moved to the test plants. X-77TM Spreader Lo_ containing 1,3- 1 G/° propylene steel '9G% water and 3GG PPm containing aryl aryl polyoxynized free sulphur, diol and isopropanol

The test compound was formulated as a solution of Fs〇am~1# ionic surfactant (Loveland Industries, Inc. Greeley, Col〇rad〇, USA). The formulated compound was applied to the working fluid by means of a SUJ2 sprayer nozzle (Spraying Systems, Inc., Wheaton, Illinois, USA) with a W JJ custom body above the top of each test unit. All experimental compounds in these tests were sprayed with 5 〇 P- and the test was repeated twice. After the spray was formulated with the test compound, each test was dried for 1 h and then the black shield was placed on top. The test piece was kept in the growth chamber at 25 ° C and 70% relative humidity for 6 days. Plant phytoses were then visually evaluated based on the consumed leaves and the pest mortality of each test unit was also counted and calculated. The following compounds of the compound of formula 1 tested provide a very good to excellent degree of control efficacy (20% 〇 or lower or 8% or more mortality): 1, 2, 3, 4, 5, 7, 8, 9, 1 , η, 12, 13, 14, 16, 19, 20, 21, 22, 23, 25, 26 and 27.

Test B The test unit used to evaluate the control of the autumn marching insect (Anopheles sinensis) consists of a small open container with a 4-5 year old corn (maize) plant inside 130845.doc -102- 200900398. This unit (using the core sampler) was pre-infested with 1 0-1 5 day old larvae on an insect feed. Test compounds were formulated as described in Test A and sprayed with 5 〇 PPm and repeated three times. After spraying, the test unit was kept in the growth chamber and the control efficacy in each test unit was assessed as described in Test A. The following compounds of the compound of formula 1 tested provide a very good to an excellent degree of control efficacy (20% or lower food or 80% or higher mortality): 1, 2, 3, 4, 5, 7, 8, 9 , 10, 11, 12, 13, 14, 16, 19, 20, 21, 22, 23, 25 and 26.

Test C The test unit for the control of potato leaf mites via contact and/or systemic evaluation consists of a small open container with 5-6 year old Solai beans (s〇leii匕 in illusory plants (appearing primary leaves). White sand was added to the soil top P and a piece of primary leaves was excised at the application of sputum. The test compound was formulated and sprayed as described in Test A. All experimental compounds in this test were sprayed with =0 ppm _ and the test was repeated Three times. After spraying, let the test unit dry U, then use 5 potato leaves (1) to η-day-old adults). Place the black shield on top of the cylinder. The test unit was identified in the growth chamber at the relative humidity of 19-^(: and 5()·鸠. (4) The control efficacy of each test unit was evaluated visually for the footworm mortality. Provides excellent to excellent control effectiveness (10)% or higher mortality): Bu... "Small Bu ^ 9, 10, 11, 12, 13, 14, 16, 19, 20, 21, 22, 23, 24 , 25 and 26. 130845.doc -103 - 200900398

Test D, the test unit for assessing control of corn (4) via contact and/or systemic means consists of a small open container with a 3 to 4 day old maize plant (ear). White sand was added to the top of the soil prior to application. The test compound was formulated as described in Test A and sprayed at 25 〇 ppm and repeated three times. After the spraying, the test unit was dried for i h, and then it was post-invasive by spreading a 1 〇, corn hopper (18 to 20 day old nymph) to the sand with a salt shaker. Place the black shield on top of the cylinder. The test unit was maintained at 19_2l < t and 5 〇 _7 (d) for 6 days in the growth chamber under humidity. Then, each test was tested visually for the mortality rate of the early insects. The following compounds of the compound of formula 1 tested provide a very good to excellent degree of control efficacy (80% or higher mortality): 1, 3, 8'9, 1 〇, 13, 14, 19, 20, 21, 22 And 25.

Test E The test unit for assessing the control of Western flowering horses via contact and/or systemic means consists of a small open container with a 5-7 day old Solai bean plant inside. The test compound was formulated and sprayed as described in Test A. All experimental compounds in this test 4 were sprayed at 25Q ppm and the test was repeated three times. After spraying, the test unit was allowed to dry for 1 hour, then 22, 27 adult hummers were added to each unit, and then a black shield was placed on top. The test unit was maintained at 25 ° C and 45-55% relative humidity for 6 days. And evaluate the mortality and plant damage rate of each test unit. The following compounds of the compound of formula 1 tested provide a very good to an excellent degree of control efficacy (20% or lower food or 80% or higher mortality): i, ^, 130845.doc -104- 200900398 3, 4. 5, 7, 8, 9, l〇, U 21, 22, 23, 24, 25 and 26 〇 12, 13, 14, 16, 19

Test F The test unit for assessing the control of peach aphid via contact and/or system means consists of a small open container with 12-15 day old radish plants inside. This unit is pre-invasive by removing one leaf from the cultured plant (30-40 aphids on the leaf are placed on the test plant leaf).

The larvae move to the test plants as the leaves dry. After the pre-invasion, cover the soil of the test unit with a layer =. 9 调 Formulation and spray test compounds as described in Test A. All experimental compounds were sprayed at 25 〇 ppm and the test was repeated three times in these tests. After the spray was formulated with the test compound, each test unit was allowed to dry i-h and then the black & screen & cover was placed on top. The I test unit was maintained in the growth chamber for 6 days at 50-inch relative humidity. (iv) Visual evaluation of insect mortality per test unit. The following compounds tested for the phantom compound provide excellent to excellent control efficacy (80% or higher mortality): 1, 2, 〇

Test G is used to assess the control of the control via contact and/or system means. The unit is composed of a small open container with a cotton plant inside it. This unit is like a test! According to the leaf cutting method, 3〇-4 is obtained on one of the leaves. Only insects are pre-invasive and the soil of the test unit is covered with a layer of sand. The test compound was formulated and sprayed at 250 ppm and the test was repeated three times. 130845.doc -105- 200900398 After spraying, the test unit was kept in the growth chamber and visually assessed for insect mortality. The following compounds of the compound of formula 1 tested provide a very good to excellent degree of control efficacy (80% or higher mortality): 1, 2, 3, 7, 8, 9, 1 , 13, 14, 16 19, 20, 21, 22 and 25. Test Η The test unit used to evaluate the control of silver leaf whitefly is composed of 14-21 day old cotton plants grown in r Redi_earth® medium (Sc like company), at least two of which are under the leaves. The second or third instar nymph attacked. The test compound is formulated in no more than 2 mL of acetamidine and then diluted to 25-30 mL with water. The formulated compound was applied at 10 psi (69 kPa) using a flat fan shaped gas assist nozzle (Spraying Systems 122440). The plants were sprayed to overflow on a turntable sprayer (Patent Publication No. EP-1 1 1 〇 61 7-A1). All experimental compounds in this shield were sprayed at 25 〇 ppm and repeated three times. After spraying the test compound, the test unit was subjected to a temperature of 5 〇 6 〇 % relative humidity and a temperature of 281 and 24 hours. (: kept at night temperature for 6 days in the growth chamber. The leaves were then removed and the dead and surviving nymphs were counted to count the percent mortality. The following compounds of the compound of formula 1 tested provided excellent to excellent control efficacy (80% or higher mortality): 13, 14, 16, 19, 20, 21, 22, 25 and 26.

Test I For the evaluation of the control of meerkats, in the amount of 1〇mg/kg to CD-Zhongxiao 130845.doc -106- 200900398 from CharIes River Laboratories, orally dissolved in propylene glycol/glycerol-formaldehyde rats (about 3 0 g 'male, Wilmington, ΜΑ obtained) Test compound in (60:40). About 8 to 16 adult fleas were applied to each mouse 2 hours after oral administration of the test compound. The mortality of the flea was then assessed 48 hours after the flea was applied to the rats. Among the compounds tested, the following compounds produced a mortality rate of 50% or higher: 1, 2, 4, 9, 12, 13, 14, 18 and 25. I30845.doc .107-

Claims (1)

200900398 X. Patent application scope: 1 · A compound selected from the group consisting of a compound of formula 1, an N-oxide or a salt thereof, Wherein R1 is F, Cl, Br, cyano, CF3, OCF2H, 〇CF3 or 〇CH2CF3; R2 is H, F, Cl, Br, CH3, cyano, CF3, 〇 (: Ι72Ή, 〇CF3 or 〇CH2CF3; And R3 is Η, F, Cl, Br or CF3; if R1 is Cl and R2 is H or Cl, then R3 is F, Br or CF3; and if R1 is Br and R2 is H or Cl, then R3 is F, α or CF3 2. A compound of the formula i, wherein R1 is Cl, Br, CF3 or OCF3; R2 is Η, F, Cl or CH3; and r3 is Η, Cl, Br or CF3. A compound according to claim 2 which is hydrogen-5-(trifluoromethyl)-3-iso-5[5-(3,5-dioxa-4-fluorophenyl)-4,5-dihydro- oxine Azyl]~2-(1//-1,2,4-triazol-1-yl)benzonitrile or fluoromethyl)phenyl]-3-iso-5_[4,5-dihydro-5-( Trifluoromethyl)-5-[3-(trioxazolyl]-2-(1//-1,2,4-triazol-1-yl)benzonitrile. 130845.doc 200900398 4·If request 2 a compound which is 5 [5 (3-bromo-4,5-dichlorophenyl)_4,5-dihydro-5-(trifluoromethyl)_3-isoxazolyl]-2-(i/f_i a 2,4-triazol-1-yl)benzonitrile. 5. A composition comprising a compound as claimed and at least one selected from the group consisting of a further component of the group consisting of a surfactant, a solid diluent, and a liquid diluent, the composition optionally further comprising at least one other biologically active compound or agent. 6. A composition for controlling an invertebrate pest, comprising a living being An effective amount of a compound of claim 1 and at least one other component selected from the group consisting of a surfactant, a solid diluent, and a liquid diluent, the composition optionally further comprising a biologically effective amount of at least one other biological activity 7. The compound of claim 6, wherein the at least one other biologically active compound or agent is selected from the group consisting of insecticides: pyrethrum S曰, amino citrate Ester, new class, neuronal sodium channel blocker, sputum, insecticidal macrolide, γ-aminobutyric acid antagonist (GABA), insecticidal urea and juvenile hormone mimic, Bacillus thuringiensis , Bacillus thuringiensis δ_ endotoxin, and a naturally occurring or genetically modified viral insecticide. 8. The composition of claim ,, wherein the at least one other The biologically active compound or agent is selected from the group consisting of abamectin and acephate, acetamiprid, acetoprole, aldicarb, and guanidine. Amidoflumet, amitraz, avermectin 130845.doc 200900398 (avermectin), azadirachtin, azinphos-methyl, bifenthrin, Bifenazate, bistrifluron, buprofezin, carbofuran, cartap, chinomethionat, chlorfenapyr ), chlorfluazuron, chlorantraniliprole, chlorpyrifos 曱 陶 otasson, chlorobenzilate, chromafenozide, clothianidin, Ding Cyflumetofen, cyfluthrin, /5 - Sai Fanning, cyhalothrin, τ - Xeronine, λ-Xelonine, cyhexatin, Sai Ning Cypermethrin), cilostazin (cyromaz Ine), deltamethrin, diafenthiuron, diazinon, dicofol, dieldrin, dienochlor, difus Diflubenzuron), dimefluthrin, dimethoate, dinote fur an, diofenolan, emamectin, endosulfan, Esfenvalerate, ethiprole, and ito. Etoxazole, fenamiphos, fenazaquin, fenbutatin oxide, fenothiocarb, fenoxycarb, fenpropathrin, Fenpyroximate, fenvalerate, fipronil, fipronil 130845.doc 200900398 (flonicamid), il flubendiamide 'flucythrinate ), τ - tau-fluvalinate, flufenerim, flufenoxuron, fonophos 'halofenozide, hexaflumuron, Hexythiazox, hydramethylnon, imicacyfos, imidacloprid, indoxacarb, isofenphos, lufenuron , marathion, metaflumizone, metaldehyde, methamidophos, methidathion, methomyl, metoprene, helium Methoxychlor, methoxyfen Ozide) 'metofluthrin, monocrotophos, nitenpyram, nithiazine, novaluron, noviflumuron, euthion ( Oxamyl), parathion, thiobarathon, permethrin, phorate, phosalone, phosmet, phosphamidon, Pirimicarb, profenofos, profluthrin, propargite, protrifenbute, pymetrozine, pyrafluprole ), pyrethrin, pyridaben, pyridalyl, pyrifluquinazon, pyriprole, beprevene 130845.doc 200900398 ( Pyriproxyfen), rotenone, ryanodine, spinetoram, spinosad, spiridiclofen, spiromesifen, snail Spirotetramat, sulprofos, Tebufenozide, tebufenpyrad, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, thiacloprid , thiamethoxam, thiodicarb, thiosultap-sodium, tolfenpyrad, tralmethrin, triazamate, three Trichlorfon, triflumuron, Bacillus thuringiensis subsp. aizawaz·), Bacillus thuringiensis subsp. kurstaki, Qiandu fish virus, embedding Bacillus thuringiensis δ-endotoxin, baculovirus, entomopathogenic bacteria, entomopathogenic virus and insect pathogens. 9. The composition of claim 8, wherein the at least one other biologically active compound or agent is selected from the group consisting of abamectin, arbutin, amoxicillin, avermectin, azadirachtin , Bifennin, Bufenjing, Bataan, chlorantamine, kefenabine, taosson, konidine, saifuning, beta-saiconing, cylonin, λ-sainin, saining , 西洛美秦, 德美美宁, dieldrin, Datnam, Dai Finnish, Imam Meiding, Anzufen, Efen Finley, Ishipu, Phenylthiocarb, Fenoxax, Fenhua Lee, Fipney, fluramide, flufenamide, flufenamide, six volts 130845.doc 200900398 Long, interesting Jialong, Yida Naide, methoxy ketone, Lu Fenlong, beauty Fluoride, Nahualong, Ouyi, sulphur, sulphate, sulphate, sulphur, sulphur, sulphur, sulphate, bismuth, bismuth, bismuth Insects, sputum, sputum, snail, snail, snail, sputum, sputum, snail, snail, snail, snail, snail, snail, snail Meso, sulphur rod 囷 泽 亚 亚 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 Species, multiple nuclear ^ such as the request of Bacillus 3_ endotoxin. "Composition of Item 6" is a soil type. Heart palpitant ligand form η. - Control of invertebrate harmful animal spray (4) Biologically effective amount as claimed in the item comprising: Compound; and person such as Ming Yong Group 6 (b) propellant A. A composition for controlling invertebrate harmful animals (4) biologically effective amount as claimed, such as compound; 士士§月求项6的组(b) one or more (c) an attractant to be used as needed; and (d) a moisturizer as required. U. A control for invertebrate pests<trapping H pieces (4) a bait composition as claimed in claim 12 and (8) suitable The outer shell of the bait composition is provided with a small opening that is sized to allow the invertebrate to have a position to pass through the opening from the outer position of the squirrel 130845.doc 200900398 /V, such that the invertebrate pest can reach the a composition, and wherein the outer shell is also suitable for placement in or near an active or known activity site of the invertebrate pest. 14. A method of controlling an invertebrate pest comprising: causing the invertebrate pest or Environment and biology An effective amount of a compound as claimed in claim 1. 15. A method of invertebrate pests comprising contacting the invertebrate pest or its environment with a composition as claimed in claim 6. The method of item 15, the method of controlling the cockroach, the ant or the termite, is applied to the soil as a soil soaking agent, and the composition is applied to the soil as a soil soaking compound. , which includes the sputum, the code sacrifice, or the termites and the contact of the request item 。 3. The bait composition in the item of the sacred object is connected to the stalk, the black fly, the scorpion fly, the deer fly, Method of horse foal, bee, yellow, bumblebee, dragonfly, spider, code & work or cockroach, which includes mosquitoes, black flies, cockroach flies, deer pots, bees, hummers, bees, wasps , rhubarb ^ + ^ 碉 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自 自Like the effective amount of the creature, the master 2, such as the owner of the seventh, the month The compound of item 1 is contacted. 20. The method of claim 19, the seed is coated with the compound of claim 1, and the compound is formulated with a compound. The horse comprises a film former or a binder. Combination 21. A compound according to claim 1 which contains the seed before treatment ... about 130845.doc 200900398 0.0001-1%. 22. 23. 24. A protected animal from invertebrate parasitism It contains an effective amount of parasiticidal as long as: animal damage composition 'seed carrier. a compound of minus 1 and at least one of the compositions of claim 22, which is a method for protecting an animal from invertebrate parasitism by means of oral administration, including a method of administering a parasite effective to the animal, . K, as requested by the combination of 130845.doc 200900398 VII. Designated representative map: (1) The representative representative of the case is: (none) (2) The symbolic symbol of the representative figure is simple: 8. If there is a chemical formula in this case, please reveal The chemical formula that best shows the characteristics of the invention: 130845.doc -6-