INSECTICIDAL COMPOUNDS

Abstract

Compounds of formula (I), wherein the substituents are as defined in claim 1, and the agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of those compounds, and their uses as insecticides.

##STR00001##

Claims

1. A compound of formula (I), ##STR00032## wherein A.sup.1, A.sup.2, A.sup.3 and A.sup.4 are, independently of one another, C—H, C—R.sup.5 or N; R.sup.1 is selected from —(C.sub.0-C.sub.4alkyl)-C(═O)—C.sub.3-C.sub.6cycloalkyl, —(C.sub.0-C.sub.4alkyl)-O—C(═O)—C.sub.3-C.sub.6cycloalkyl, —(C.sub.0-C.sub.4alkyl)-O—C.sub.3-C.sub.6cycloalkyl, —R.sup.1aOR.sup.1aOR.sup.1b, —R.sup.1aOC(═O)R.sup.1b, —R.sup.1aOC(═O)OR.sup.1b, —R.sup.1aN(R.sup.1c)C(═O)OR.sup.1b, —R.sup.1aOC(═O)N(R.sup.1b)(R.sup.1c), —R.sup.1aC(═O)N(R.sup.1b)(R.sup.1c) and —S—C(═O)OR.sup.1b; R.sup.1a is —(CR.sup.1dR.sup.1e).sub.n—; R.sup.1b and R.sup.1c are independently selected from H and C.sub.1-C.sub.4alkyl, wherein each alkyl group is unsubstituted or substituted with one to three halogen atoms or with a cyano group; R.sup.1d and R.sup.1e are independently selected from H and C.sub.1-C.sub.4alkyl; n is selected from 1, 2, 3 and 4; R.sup.2 is hydrogen, halogen, cyano, C.sub.1-C.sub.8alkyl or C.sub.1-C.sub.8alkyl substituted by one to three R.sup.6a, C.sub.1-C.sub.8haloalkyl or C.sub.1-C.sub.8haloalkyl substituted by one to three R.sup.6a, C.sub.1-C.sub.8alkoxy or C.sub.1-C.sub.8alkoxy substituted by one to three R.sup.6a, C.sub.3-C.sub.8cycloalkyl or C.sub.3-C.sub.8cycloalkyl substituted by one to three R.sup.6b, C.sub.3-C.sub.8cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO.sub.2, or C.sub.3-C.sub.8cycloalkyl-C.sub.1-C.sub.8alkyl, C.sub.3-C.sub.8cycloalkyl-C.sub.1-C.sub.8alkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO.sub.2, or C.sub.3-C.sub.8cycloalkyl-C.sub.1-C.sub.8haloalkyl, C.sub.2-C.sub.8alkenyl or C.sub.2-C.sub.8alkenyl substituted by one to three R.sup.6a, C.sub.2-C.sub.8haloalkenyl or C.sub.2-C.sub.8haloalkenyl substituted by one to three R.sup.6a, C.sub.2-C.sub.8alkynyl, C.sub.2-C.sub.8haloalkynyl, phenyl, phenyl substituted by one to three R.sup.7, phenyl-C.sub.1-C.sub.4alkyl, phenyl-C.sub.1-C.sub.4alkyl wherein the phenyl moiety is substituted by one to three R.sup.7, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R.sup.7, 5-6 membered heteroaryl-C.sub.1-C.sub.4alkyl or 5-6 membered heteroaryl-C.sub.1-C.sub.4alkyl wherein the heteroaryl moiety is substituted by one to three R.sup.7, —NH(R.sup.8), —N(R.sup.8)(R.sup.9), —OR.sup.10, —SR.sup.10, —S(O)R.sup.10, —S(O).sub.2R.sup.10, COR.sup.10, COOR.sup.10; R.sup.3 is C.sub.1-C.sub.8haloalkyl; R.sup.4 is phenyl or phenyl substituted by one to three R.sup.6b or pyridine or pyridine substituted by one to three R.sup.6b; R.sup.5 is independently halogen, cyano, nitro, C.sub.1-C.sub.8alkyl, C.sub.3-C.sub.8cycloalkyl, C.sub.1-C.sub.8haloalkyl, C.sub.2-C.sub.8alkenyl, C.sub.2-C.sub.8haloalkenyl, C.sub.2-C.sub.8alkynyl, C.sub.2-C.sub.8haloalkynyl, C.sub.1-C.sub.8alkoxy, C.sub.1-C.sub.8haloalkoxy, or C.sub.1-C.sub.8alkoxycarbonyl-, or two R.sup.5 on adjacent carbon atoms together form a —CH═CH—CH═CH— bridge or a —N═CH—CH═CH— bridge; each R.sup.6a is independently halogen, cyano, nitro, amino, hydroxy, oxo, C.sub.1-C.sub.8alkylamino, hydroxyimino, C.sub.1-C.sub.8alkyloxyimino, di-C.sub.1-C.sub.8alkylamino, C.sub.1-C.sub.8alkoxy, acetyloxy, formyloxy, C.sub.1-C.sub.8haloalkoxy, C.sub.1-C.sub.4alkylthio or tri-(C.sub.1-C.sub.4alkyl)silyl; each R.sup.6b is independently halogen, cyano, nitro, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8haloalkyl, amino, C.sub.1-C.sub.8alkylamino, di-C.sub.1-C.sub.8alkylamino, hydroxyl, C.sub.1-C.sub.4alkylthio, C.sub.1-C.sub.8alkoxy or C.sub.1-C.sub.8haloalkoxy; R.sup.7 is independently halogen, cyano, nitro, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8haloalkyl, C.sub.1-C.sub.8alkoxy, or C.sub.1-C.sub.8haloalkoxy; R.sup.8 and R.sup.9 are independently hydrogen, cyano, C.sub.1-C.sub.8alkyl or C.sub.1-C.sub.8alkyl substituted by one to three R.sup.6a, C.sub.1-C.sub.8alkoxy, C.sub.1-C.sub.8haloalkoxy, C.sub.1-C.sub.8haloalkoxy substituted by one to three R.sup.6a, C.sub.1-C.sub.8alkoxy substituted by one to three R.sup.6a, C.sub.1-C.sub.8haloalkyl or C.sub.1-C.sub.8haloalkyl substituted by one to three R.sup.6a, C.sub.3-C.sub.8cycloalkyl or C.sub.3-C.sub.8cycloalkyl substituted by one to three R.sup.6b, C.sub.3-C.sub.8cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO.sub.2, or C.sub.3-C.sub.8cycloalkyl-C.sub.1-C.sub.8alkyl, C.sub.3-C.sub.8cycloalkyl-C.sub.1-C.sub.8alkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO.sub.2, or C.sub.3-C.sub.8cycloalkyl-C.sub.1-C.sub.8haloalkyl, C.sub.2-C.sub.8alkenyl or C.sub.2-C.sub.8alkenyl substituted by one to three R.sup.6a, C.sub.2-C.sub.8haloalkenyl or C.sub.2-C.sub.8haloalkenyl substituted by one to three R.sup.6a, C.sub.2-C.sub.8alkynyl, C.sub.2-C.sub.8haloalkynyl, phenyl, phenyl substituted by one to three R.sup.7, phenyl-C.sub.1-C.sub.4alkyl, phenyl-C.sub.1-C.sub.4alkyl wherein the phenyl moiety is substituted by one to three R.sup.7, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R.sup.7, 5-6 membered heteroaryl-C.sub.1-C.sub.4alkyl or 5-6 membered heteroaryl-C.sub.1-C.sub.4alkyl wherein the heteroaryl moiety is substituted by one to three R.sup.7, or R.sup.8 and R.sup.9 together with the nitrogen atom can be linked through a C.sub.3-C.sub.8alkylene chain, a C.sub.3-C.sub.8alkylene chain substituted by one to three R.sup.6b or a C.sub.3-C.sub.8alkylene chain, where one carbon atom is replaced by O, S, S(O) or SO.sub.2; R.sup.10 is hydrogen, cyano, C.sub.1-C.sub.8alkyl or C.sub.1-C.sub.8alkyl substituted by one to three R.sup.6a, C.sub.1-C.sub.8haloalkyl or C.sub.1-C.sub.8haloalkyl substituted by one to three R.sup.6a, C.sub.3-C.sub.8cycloalkyl or C.sub.3-C.sub.8cycloalkyl substituted by one to three R.sup.6b, C.sub.3-C.sub.8cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO.sub.2, or C.sub.3-C.sub.8cycloalkyl-C.sub.1-C.sub.8alkyl, C.sub.3-C.sub.8cycloalkyl-C.sub.1-C.sub.8alkyl where one carbon atom in the cycloalkyl group is replaced by O, S, S(O) or SO.sub.2, or C.sub.3-C.sub.8cycloalkyl-C.sub.1-C.sub.8haloalkyl, C.sub.2-C.sub.8alkenyl or C.sub.2-C.sub.8alkenyl substituted by one to three R.sup.6a, C.sub.2-C.sub.8haloalkenyl or C.sub.2-C.sub.8haloalkenyl substituted by one to three R.sup.6a, C.sub.2-C.sub.8alkynyl, C.sub.2-C.sub.8haloalkynyl, phenyl, phenyl substituted by one to three R.sup.7, phenyl-C.sub.1-C.sub.4alkyl, phenyl-C.sub.1-C.sub.4alkyl wherein the phenyl moiety is substituted by one to three R.sup.7, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R.sup.7, 5-6 membered heteroaryl-C.sub.1-C.sub.4alkyl or 5-6 membered heteroaryl-C.sub.1-C.sub.4alky 1 wherein the heteroaryl moiety is substituted by one to three R.sup.7; or an agrochemically acceptable salt, tautomer or N-oxide thereof.

2. The compound of formula (I) according to claim 1, wherein A.sup.1 is C—R.sup.5; A.sup.2 is C—H; A.sup.3 is C—H; and A.sup.4 is C—H, wherein R.sup.5 is halogen, cyano, nitro, C.sub.1-C.sub.8alkyl, C.sub.3-C.sub.8cycloalkyl, C.sub.1-C.sub.8haloalkyl, or C.sub.2-C.sub.8alkenyl.

3. The compound of formula (I) according to claim 1, wherein R.sup.2 is halogen, C.sub.1-C.sub.4alkyl, C.sub.3-C.sub.5cycloalkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.4alkoxy, C.sub.1-C.sub.4haloalkoxy or di-C.sub.1-C.sub.4alkylamino, C.sub.1-C.sub.4alkylthio, C.sub.1-C.sub.4alkyloxycarbonyl.

4. The compound of formula (I) according to claim 1, wherein R.sup.2 is C.sub.1-C.sub.4alkoxy.

5. The compound of formula (I) according to claim 1, wherein R.sup.1 is selected from —(C.sub.0-C.sub.4alkyl)-C(═O)—C.sub.3-C.sub.6cycloalkyl, —(C.sub.0-C.sub.4alkyl)-O—C(═O)—C.sub.3-C.sub.6cycloalkyl, —R.sup.1aOC(═O)R.sup.1b, —R.sup.1aOC(═O)OR.sup.1b, —R.sup.1aN(R.sup.1c)C(═O)OR.sup.1b and —R.sup.1aOC(═O)N(R.sup.1b)(R.sup.1c).

6. The compound of formula (I) according to claim 1, wherein R.sup.3 is C.sub.1-C.sub.4haloalkyl.

7. The compound of formula (I) according to claim 1, wherein R.sup.4 is phenyl or phenyl substituted by one to three R.sup.6b R.sup.6b independently is halogen, cyano, nitro, C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.4alkoxy, or C.sub.1-C.sub.4haloalkoxy; more preferably bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy and trifluoromethoxy

8. The compound of formula (I) according to claim 1 represented by the compound of formula (Ia) ##STR00033## wherein R.sup.1 is selected from —(C.sub.0-C.sub.4alkyl)-C(═O)—C.sub.3-C.sub.6cycloalkyl, —(C.sub.0-C.sub.4alkyl)-O—C(═O)—C.sub.3-C.sub.6cycloalkyl, —(C.sub.0-C.sub.4alkyl)-O—C.sub.3-C.sub.6cycloalkyl, —R.sup.1aOR.sup.1aOR.sup.1b, —R.sup.1aOC(═O)R.sup.1b, —R.sup.1aOC(═O)OR.sup.1b, —R.sup.1aN(R.sup.1c)C(═O)OR.sup.1b, —R.sup.1aOC(═O)N(R.sup.1b)(R.sup.1c), —R.sup.1aC(═O)N(R.sup.1b)(R.sup.1c) and —S—C(═O)OR.sup.1b; R.sup.1a is —(CR.sup.1dR.sup.1e).sub.n—; R.sup.1b and R.sup.1c are independently selected from H and C.sub.1-C.sub.4alkyl, wherein each alkyl group is unsubstituted or substituted with one to three halogen atoms or with a cyano group; R.sup.1d and R.sup.1e are independently selected from H and C.sub.1-C.sub.4alkyl; n is selected from 1, 2, 3 and 4.

9. The compound of claim 8 wherein R.sup.1 is selected from —(C.sub.0-C.sub.4alkyl)-C(═O)—C.sub.3-C.sub.6cycloalkyl, —(C.sub.0-C.sub.4alkyl)-O—C(═O)—C.sub.3-C.sub.6cycloalkyl, —R.sup.1aOC(═O)R.sup.1b, —R.sup.1aOC(═O)OR.sup.1b, —R.sup.1aN(R.sup.1c)C(═O)OR.sup.1b and —R.sup.1aOC(═O)N(R.sup.1b)(R.sup.1c).

10. A compound of formula (Int-I) ##STR00034## wherein A.sup.1, A.sup.2, A.sup.3, A.sup.4, R.sup.1 and R.sup.2 are as defined in claim 1 and X.sup.B is a halogen, such as bromo, or X.sup.B is cyano, formyl, CH═N—OH or acetyl; or a salt or N-oxide thereof.

11. A compound of formula (Int-II) ##STR00035## wherein A.sup.1, A.sup.2, A.sup.3, A.sup.4, R.sup.1 and R.sup.2 are as defined in claim 1 and X.sup.C is CH.sub.2-halogen, CH═C(R.sup.3)R.sup.4 or CH.sub.2C(OH)(R.sup.3)R.sup.4 wherein R.sup.3 and R.sup.4 are as defined for a compound of formula (I); or a salt or N-oxide thereof.

12. A compound of formula (Int-III) ##STR00036## wherein R.sup.1 and R.sup.2 are as defined in claim 1; or a salt or N-oxide thereof; or a compound of formula (Int-IV) ##STR00037## wherein A.sup.1, A.sup.2, A.sup.3, A.sup.4, R.sup.1, R.sup.3 and R.sup.4 are as defined in claim 1, or a salt or N-oxide thereof.

13. The compound of claim 12, wherein the compound is the compound of formula (Int-IV).

14. A pesticidal composition, which comprises at least one compound of formula (I) according to claim 1 or, where appropriate, a tautomer thereof, in each case in free form or in agrochemically utilizable salt form, as active ingredient.

15. A method for controlling pests, which comprises applying a composition according to claim 14 to the pests or their environment with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practised on the human or animal body.

16. The compound of claim 12, wherein the compound is the compound of formula (Int-III).

Description

PREPARATORY EXAMPLES

[0214] “Mp” means melting point in ° C. Free radicals represent methyl groups. .sup.1H NMR measurements were recorded on a Brucker 400 MHz spectrometer, chemical shifts are given in ppm relevant to a TMS standard. Spectra measured in deuterated solvents as indicated.

[0215] The following LC-MS methods were used to characterize the compounds:

Example 1: Preparation of [[4-[(5S)-5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-benzoyl]-(3-ethoxy-4,5-dihydroisoxazol-5-yl)amino]methyl ethyl carbonate (Compound A8)

[0216] ##STR00020##

[0217] Under a nitrogen atmosphere, a stirred mixture of 4-[(5S)-5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-(3-ethoxy-4,5-dihydroisoxazol-5-yl)-2-methyl-benzamide (200 mg) in N,N-dimethylformamide (1.82 mL) was cooled to 0° C. After 5 min, sodium hydride (0.022 g, 60% suspension in oil) was added and the reaction mixture was allowed to warm up and to stir at ambient temperature. After 30 min, chloromethyl ethyl carbonate (0.104 g) was added and the reaction mixture was stirred for 2.5 hours. The reaction mixture was carefully quenched with water and diluted with ethyl acetate. The aqueous layer was extracted twice with ethyl acetate and the combined organic layers were washed once with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give a crude product which was purified by Combiflash chromatography (eluent: gradient Cyclohexane/Ethyl acetate 1:0 to 70:30), to give 82 mg of the desired product A8 as a mixture of rotamers. .sup.1H NMR (400 MHz, CDCl.sub.3) δ ppm 7.47-7.65 (m, 4H) 7.32 (br s, 1H) 6.09-6.78 (m, 1H) 4.86-5.98 (m, 2H) 4.04-4.33 (m, 5H) 3.69 (br d, 1H) 2.99-3.60 (m, 2H) 2.36 (s, 3H) 1.22-1.42 (m, 6H). .sup.19F NMR (377 MHz, CDCl.sub.3) δ ppm −79.43 and −79.48 (m, 3 F)-113.54 (s, 1 F).

[0218] The other examples were prepared in a similar manner using the appropriate intermediates.

TABLE-US-00004 .sup.19F NMR δ ppm (377 MHz in CDCl.sub.3, Com- .sup.1H NMR δ ppm (400 unless pound MHz in CDCl.sub.3, unless indicated number IUPAC name Structure indicated otherwise) otherwise) A1  N-(cyclopropanecarbonyl)-4- [(5S)-5-(3,5-dichloro-4- fluoro-phenyl)-5- (trifluoromethyl)-4H- isoxazol-3-yl]-N-(3-ethoxy- 4,5-dihydroisoxazol-5-yl)-2- methyl-benzamide [00021] 7.59 (d, 3 H) 7.49- 7.54 (m, 2 H) 6.57- 6.64 (m, 1 H) 4.16- 4.30 (m, 2 H) 4.09 (d, 1 H) 3.69 (d, 1 H) 3.24- 3.39 (m, 2 H) 2.52 (s, 3 H) 1.48-1.54 (m, 1 H) 1.37 (t, 3 H) 0.83-1.10 (m, 2 H) 0.57-0.75 (m, 2 H) −79.53 and −79.54 (m, 3 F) −113.39 (s, 1 F) A2  [[4-[(5S)-5-(3,5-dichloro-4- fluoro-phenyl)-5- (trifluoromethyl)-4H- isoxazol-3-yl]-2-methyl- benzoyl]-(3-ethoxy-4,5- dihydroisoxazol-5- yl)amino]methyl 2- methylpropanoate [00022] 7.24-7.65 (m, 5 H) 6.74-4.84 (m, 3 H) 4.13-4.26 (m, 2 H) 4.09 (dd, 1 H) 3.63- 3.76 (m, 1 H) 2.91- 3.58 (m, 2 H) 2.41- 2.70 (m, 1 H) 2.36 (s, 3 H) 1.30-1.40 (m, 3 H) 1.04-1.28 (m, 6 H) −79.38 and −79.58 (m, 3 F) −113.56 (s, 1 F) A3  [[4-[(5S)-5-(3,5-dichloro-4- fluoro-phenyl)-5- (trifluoromethyl)-4H- isoxazol-3-yl]-2-methyl- benzoyl]-(3-ethoxy-4,5- dihydroisoxazol-5- yl)amino]methyl 2,2- dimethylpropanoate [00023] 7.59 (d, 2 H) 7.52 (m, 2 H) 7.20-7.35 (m, 1 H) 4.95-6.85 (m, 3 H) 4.14-4.25 (m, 2 H) 4.09 (dd, 1 H) 3.69 (d, 1 H) 3.53 (br dd, 1 H) 3.01 (br s, 1 H) 2.35 (s, 3 H) 1.35 (t, 3 H) 1.12- 1.27 (m, 9 H) −79.37 and −79.48 (m, 3 F) −113.58 (s, 1 F) A4  methyl N-[[[4-[(5S)-5-(3,5- dichloro-4-fluoro-phenyl)-5- (trifluoromethyl)-4H- isoxazol-3-yl]-2-methyl- benzoyl]-(3-ethoxy-4,5- dihydroisoxazol-5- yl)amino]methyl]-N-methyl- carbamate [00024] .sup.1H NMR (400 MHz, acetone) δ ppm 7.81 (d, 2 H) 7.65-7.73 (m, 2 H) 7.30-7.45 (m, 1 H) 5.17-6.07 (m, 2 H) 4.38-4.46 (m, 1 H) 4.27 (dd, 1 H) 4.02- 4.16 (m, 2 H) 3.67 (br m, 3 H) 2.70-3.49 (m, 6 H) 2.27-2.42 (m, 3 H) 1.28 (br t, 3 H) .sup.19F NMR (377 MHz, acetone) δ ppm −80.37 and −80.40 (m, 3 F) −116.32 (s, 1 F) A5  [[4-[(5S)-5-(3,5-dichloro-4- fluoro-phenyl)-5- (trifluoromethyl)-4H- isoxazol-3-yl]-2-methyl- benzoyl]-(3-ethoxy-4,5- dihydroisoxazol-5- yl)amino]methyl N,N- dimethylcarbamate [00025] 7.28-7.63 (m, 5 H) 6.57-6.81 and 5.06- 6.04 (m, 3 H) 4.21 (q, 2 H) 4.09 (dd, 1 H) 3.69 (dd, 1 H) 3.12-3.58 (m, 1 H) 2.82-3.07 (m, 7 H) 2.36 (s, 3 H) 1.35 (t, 3 H) −79.34 and −79.41 (m, 3 F) −113.58 (s, 1 F) A6  [[4-[(5S)-5-(3,5-dichloro-4- fluoro-phenyl)-5- (trifluoromethyl)-4H- isoxazol-3-yl]-2-methyl- benzoyl]-(3-ethoxy-4,5- dihydroisoxazol-5- yl)amino]methyl methyl carbonate [00026] 7.30-7.70 (m, 5 H) 6.50-6.79 and 5.05- 5.84 (m, 3 H) 4.21 (q, 2 H) 4.03-4.13 (m, 1 H) 3.62-3.91 (m, 4 H) 2.95-3.60 (m, 2 H) 2.36 (s, 3 H) 1.36 (t, 3 H) −79.42 and −79.47 (m, 3 F) −113.51 (s, 1 F) A7  [[4-[(5S)-5-(3,5-dichloro-4- fluoro-phenyl)-5- (trifluoromethyl)-4H- isoxazol-3-yl]-2-methyl- benzoyl]-(3-ethoxy-4,5- dihydroisoxazol-5- yl)amino]methyl cyclopropanecarboxylate [00027] 7.29-7.67 (m, 5 H) 6.65-6.83 and 5.02- 6.11 (m, 3 H) 4.15- 4.27 (m, 2 H) 4.09 (dd, 1 H) 3.69 (d, 1 H) 2.94- 3.59 (m, 2 H) 2.36 (s, 3 H) 1.55-1.48 (m, 1 H) 1.37 (br t, 3 H) 1.09- 0.83 (m, 4 H) −79.38 and −79.55 (m, 3 F) −113.55 (s, 1 F) A8  [[4-[(5S)-5-(3,5-dichloro-4- fluoro-phenyl)-5- (trifluoromethyl)-4H- isoxazol-3-yl]-2-methyl- benzoyl]-(3-ethoxy-4,5- dihydroisoxazol-5- yl)amino]methyl ethyl carbonate [00028] 7.47-7.65 (m, 4 H) 7.32 (br s, 1 H) 6.09- 6.78 (m, 1 H) 4.86- 5.98 (m, 2 H) 4.04- 4.33 (m, 5 H) 3.69 (br d, 1 H) 2.99-3.60 (m, 2 H) 2.36 (s, 3 H) 1.22- 1.42 (m, 6 H) −79.43 and −79.48 (m, 3 F) −113.54 (s, 1 F) A9  [[4-[(5S)-5-(3,5-dichloro-4- fluoro-phenyl)-5- (trifluoromethyl)-4H- isoxazol-3-yl]-2-methyl- benzoyl]-(3-ethoxy-4,5- dihydroisoxazol-5- yl)amino]methyl isopropyl carbonate [00029] 7.48-7.64 (m, 4 H) 7.28-7.40 (m, 1 H) 5.53-6.85 (m, 1 H) 4.62-5.45 (m, 3 H) 4.04-4.27 (m, 3 H) 3.69 (br d, 1 H) 2.91- 3.57 (m, 2 H) 2.35 (s, 3 H) 1.21-1.44 (m, 9 H) −79.44 and −79.48 (m, 3 F) −113.54 (s, 1 F) A10 [[4-[(5S)-5-(3,5-dichloro-4- fluoro-phenyl)-5- (trifluoromethyl)-4H-isoxazol-3- yl]-2-methyl-benzoyl]-(3-ethoxy- 4,5-dihydroisoxazol-5- yl)amino]methyl propanoate [00030] 7.46-7.67 (m, 4 H) 7.25- 7.32 (m, 1 H) 6.73 (br s) and 4.94-6.19 (m, 3 H) 4.15-4.26 (m, 2 H) 4.05- 4.15 (m, 1 H) 3.69 (br d, 1 H) 3.34-3.60 (m) and 2.93-3.17 (m, 2 H) 2.16- 2.48 (m, 5 H) 1.36 (br t, 3 H) 1.05-1.22 (m, 3 H) −79.46 (m, 3 F) −113.55 (s, 1 F) A11 [[4-[(5S)-5-(3,5-dichloro-4- fluoro-phenyl)-5- (trifluoromethyl)-4H-isoxazol-3- yl]-2-methyl-benzoyl]-(3-ethoxy- 4,5-dihydroisoxazol-5- yl)amino]methyl acetate [00031] 7.48-7.66 (m, 4 H) 7.25- 7.32 (m, 1 H) 6.72 (br s) and 4.94-6.13 (m, 3 H) 4.21 (br d, 2 H) 4.09 (dd, 1 H) 3.69 (d, 1 H) 3.35- 3.60 (m) and 2.91-3.16 (m, 2 H) 2.36 (s, 3 H) 1.91- 2.23 (m, 3 H) 1.37 (br t, 3 H) −79.45 (m, 3 F) −113.54 (s, 1 F)

BIOLOGICAL EXAMPLES

[0219] These Examples illustrate the pesticidal/insecticidal properties of compounds of formula (I).

[0220] Tests were performed as follows:

Example B1

[0221] Diabrotica balteata (Corn Root Worm)

[0222] Maize sprouts placed onto an agar layer in 24-well microtiter plates were treated with aqueous test solutions prepared from 10′000 ppm DMSO stock solutions by spraying. After drying, the plates were infested with L2 larvae (6 to 10 per well). The samples were assessed for mortality and growth inhibition in comparison to untreated samples 4 days after infestation.

[0223] The following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm: A1, A2, A3, A4, A5

Example B2

[0224] Euschistus heros(Neotropical Brown Stink Bug) Soybean leaves on agar in 24-well microtiter plates were sprayed with aqueous test solutions prepared from 10′000 ppm DMSO stock solutions. After drying the leaves were infested with N2 nymphs. The samples were assessed for mortality and growth inhibition in comparison to untreated samples 5 days after infestation.

[0225] The following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm: A1, A2, A3, A4, A5, A6, A7

Example B3

[0226] Plutella xylostella (Diamond Back Moth)

[0227] 24-well microtiter plates with artificial diet were treated with aqueous test solutions prepared from 10′000 ppm DMSO stock solutions by pipetting. After drying, Plutella eggs were pipetted through a plastic stencil onto a gel blotting paper and the plate was closed with it. The samples were assessed for mortality and growth inhibition in comparison to untreated samples 8 days after infestation.

[0228] The following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm: A4, A5, A6, A7

Example B4

[0229] Plutella xylostella (Diamond Back Moth)

[0230] 24-well microtiter plates with artificial diet were treated with aqueous test solutions prepared from 10′000 ppm DMSO stock solutions by pipetting. After drying, the plates were infested with L2 larvae (10 to 15 per well). The samples were assessed for mortality and growth inhibition in comparison to untreated samples 5 days after infestation.

[0231] The following compounds gave an effect of at least 80% in at least one of the two categories (mortality or growth inhibition) at an application rate of 200 ppm: A1, A2, A3

Example B5

[0232] Myzus persicae (Green Peach Aphid): Feeding/Contact Activity

[0233] Sunflower leaf discs were placed onto agar in a 24-well microtiter plate and sprayed with aqueous test solutions prepared from 10′000 ppm DMSO stock solutions. After drying, the leaf discs were infested with an aphid population of mixed ages. The samples were assessed for mortality 6 days after infestation.

[0234] The following compounds resulted in at least 80% mortality at an application rate of 200 ppm: A1, A2, A3, A4

Example B6

[0235] Spodoptera littoralis (Egyptian Cotton Leaf Worm)

[0236] Cotton leaf discs were placed onto agar in 24-well microtiter plates and sprayed with aqueous test solutions prepared from 10′000 ppm DMSO stock solutions. After drying the leaf discs were infested with five L1 larvae. The samples were assessed for mortality, anti-feeding effect, and growth inhibition in comparison to untreated samples 3 days after infestation. Control of Spodoptera littoralis by a test sample is given when at least one of the categories mortality, anti-feedant effect, and growth inhibition is higher than the untreated sample.

[0237] The following compounds resulted in at least 80% control at an application rate of 200 ppm: A1, A2, A3, A4, A5, A6, A7

Example B7

[0238] Tetranychus urticae (Two-Spotted Spider Mite): Feeding/Contact Activity

[0239] Bean leaf discs on agar in 24-well microtiter plates were sprayed with aqueous test solutions prepared from 10′000 ppm DMSO stock solutions. After drying the leaf discs were infested with a mite population of mixed ages. The samples were assessed for mortality on mixed population (mobile stages) 8 days after infestation.

[0240] The following compounds resulted in at least 80% mortality at an application rate of 200 ppm: A1, A2, A3, A4, A5

Example B8

[0241] Thrips tabaci (Onion Thrips) Feeding/Contact Activity

[0242] Sunflower leaf discs were placed on agar in 24-well microtiter plates and sprayed with aqueous test solutions prepared from 10′000 ppm DMSO stock solutions. After drying the leaf discs were infested with a thrips population of mixed ages. The samples were assessed for mortality 6 days after infestation.

[0243] The following compounds resulted in at least 80% mortality at an application rate of 200 ppm: A1, A2, A3, A4, A5