ISOXAZOLINE-SUBSTITUTED BENZAMIDES AND ANALOGUES AS INSECTICIDES

Abstract

The present invention relates to compounds of formula (I) wherein A.sup.1, A.sup.2, A.sup.3, A.sup.4, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and n are as defined in claim 1; or a tautomer, isomer, enantiomer, salt or N-oxide thereof; to intermediates for preparing compounds of formula (I), to compositions comprising them and to methods of using them to combat and control insect, acarine, nematode and mollusc pests.

##STR00001##

Claims

1. A compound of formula (I) ##STR00042## wherein A.sup.1, A.sup.2, A.sup.3 and A.sup.4 are independently of one another CH, CR.sup.5, or nitrogen; R.sup.1 is hydrogen, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8alkylcarbonyl-, C.sub.1-C.sub.8alkoxy, C.sub.1-C.sub.8alkoxy-C.sub.1-C.sub.8alkyl or C.sub.1-C.sub.8alkoxycarbonyl-; R.sup.2 is C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8alkyl substituted by one to three R.sup.6a, C.sub.1-C.sub.8haloalkyl, C.sub.1-C.sub.8haloalkyl substituted by one to three R.sup.6a, C.sub.3-C.sub.8cycloalkyl, 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, 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, C.sub.3-C.sub.8cycloalkyl-C.sub.1-C.sub.8haloalkyl, C.sub.2-C.sub.8alkenyl, C.sub.2-C.sub.8alkenyl substituted by one to three R.sup.6a, C.sub.2-C.sub.8haloalkenyl, 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, 5-6 membered heteroaryl-C.sub.1-C.sub.4alkyl wherein the heteroaryl moiety is substituted by one to three R.sup.7, N(R.sup.8)(R.sup.9), halogen or OR.sup.10; R.sup.3 is C.sub.1-C.sub.8haloalkyl; R.sup.4 is aryl, aryl substituted by one to three R.sup.7, heteroaryl or heteroaryl substituted by one to three R.sup.7; 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?CHCH?CH bridge or a NCHCH?CHbridge; R.sup.6a is independently cyano, nitro, amino, C.sub.1-C.sub.8alkylamino, N,NC.sub.1-C.sub.8dialkylamino, hydroxy, C.sub.1-C.sub.8alkoxy, or C.sub.1-C.sub.8haloalkoxy; R.sup.6b is independently halogen, cyano, nitro, oxo, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8haloalkyl, amino, C.sub.1-C.sub.8alkylamino, N,NC.sub.1-C.sub.8dialkylamino, hydroxyl, C.sub.1-C.sub.8alkoxy, C.sub.1-C.sub.8haloalkoxy, phenyl, phenyl substituted by one to three R.sup.7, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R.sup.7; 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, C.sub.1-C.sub.8haloalkoxy; R.sup.8 and R.sup.9 are independently hydrogen, cyano, cyano-C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8alkyl substituted by one to three R.sup.6a, C.sub.2-C.sub.8alkenyl, C.sub.2-C.sub.8alkenyl 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, C.sub.1-C.sub.8haloalkyl substituted by one to three R.sup.6a, C.sub.3-C.sub.8cycloalkyl, C.sub.3-C.sub.8cycloalkyl substituted by one to three R.sup.6a, C.sub.3-C.sub.8cycloalkyl where one carbon atom is replaced by O, S, S(O) or SO.sub.2, 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, C.sub.3-C.sub.8cycloalkyl-C.sub.1-C.sub.8haloalkyl, C.sub.2-C.sub.8alkenyl, C.sub.2-C.sub.8alkenyl substituted by one to three R.sup.6a, C.sub.2-C.sub.8haloalkenyl, 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, 5-6 membered heteroaryl-C.sub.1-C.sub.4alkyl wherein the heteroaryl moiety is substituted by one to three R.sup.7, S(O)R.sup.10, S(O).sub.2R.sup.10, COR.sup.10, COOR.sup.10, 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.6 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, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8alkyl substituted by one to three R.sup.6a, C.sub.1-C.sub.8haloalkyl, C.sub.1-C.sub.8haloalkyl substituted by one to three R.sup.6a, C.sub.3-C.sub.8cycloalkyl, 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, 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, C.sub.3-C.sub.8cycloalkyl-C.sub.1-C.sub.8haloalkyl, C.sub.2-C.sub.8alkenyl, C.sub.2-C.sub.8alkenyl substituted by one to three R.sup.6a, C.sub.2-C.sub.8haloalkenyl, 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; n is 1 or 2; or a tautomer, isomer, enantiomer, salt or N-oxide thereof.

2. The compound according to claim 1, wherein A.sup.1 is CR.sup.5 and A.sup.2, A.sup.3 and A.sup.4 are each CH, wherein R.sup.5 is as defined in claim 1.

3. The compound according to either claim 1, wherein R.sup.1 is hydrogen, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8alkylcarbonyl- or C.sub.1-C.sub.8alkoxycarbonyl-.

4. The compound according claim 1, wherein R.sup.2 is 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, 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, halogen or N(R.sup.8)(R.sup.9) wherein R.sup.8, R.sup.9, R.sup.6a and R.sup.6b are as defined in claim 1.

5. The compound according to claim 1, wherein R.sup.3 is C.sub.1-C.sub.4haloalkyl.

6. The compound according to claim 1, wherein R.sup.4 is phenyl or phenyl substituted by one to three R.sup.7; wherein R.sup.7 is independently halogen, cyano, 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.

7. The compound according to claim 1, wherein A.sup.1 is CR.sup.5 and A.sup.2, A.sup.3 and A.sup.4 are each CH; R.sup.1 is hydrogen, methyl, ethyl, methylcarbonyl-, or methoxycarbonyl; R.sup.2 is C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8alkyl substituted by one to three R.sup.6a, C.sub.2-C.sub.8alkenyl, C.sub.2-C.sub.8alkynyl, C.sub.3-C.sub.8cycloalkyl, C.sub.1-C.sub.8haloalkyl, di-C.sub.1-C.sub.8alkylamino, C.sub.1-C.sub.4alkylamino, fluoro, aryl, aryl substituted by one to three R.sup.6b, 5-6 membered heteroaryl or 5-6 membered heteroaryl substituted by one to three R.sup.6b; R.sup.3 is C.sub.1-C.sub.4haloalkyl; R.sup.4 is aryl or aryl substituted by one to three R.sup.6a; and n is 2; wherein R.sup.5 is halogen or 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; R.sup.6a is independently cyano, halogen, nitro, C.sub.1-C.sub.4alkoxy, or C.sub.1-C.sub.4haloalkoxy; and R.sup.6 is independently halogen, cyano, nitro, C.sub.1-C.sub.4alkyl, or C.sub.1-C.sub.4haloalkyl, C.sub.1-C.sub.4alkoxy, or C.sub.1-C.sub.4haloalkoxy.

8. The compound according to claim 1, wherein A.sup.1 is CR.sup.5 and A.sup.2, A.sup.3 and A.sup.4 are each CH; R.sup.1 is hydrogen; R.sup.2 is C.sub.1-C.sub.4alkyl, C.sub.1-C.sub.4alkyl substituted by one to three R.sup.6a, C.sub.2-C.sub.4alkenyl, C.sub.2-C.sub.4alkynyl, C.sub.3-C.sub.5cycloalkyl, C.sub.1-C.sub.4haloalkyl, di-C.sub.1-C.sub.4alkylamino, C.sub.1-C.sub.4alkylamino, fluoro, 1-3 halo-substituted phenyl, or 5-6 membered heteroaryl; R.sup.1 is chlorodifluoromethyl or trifluoromethyl; R.sup.4 is 3,5-bis-(trifluoromethyl)-phenyl, 3-chloro-5-trifluoromethyl-phenyl, 3-bromo-5-trifluoromethyl-phenyl, 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,4-dichloro-phenyl, 3-trifluoromethyl-phenyl, 4-bromo-3,5-dichlorophenyl, 3,5-dichloro-4-fluoro phenyl or 3,4,5-trichloro-phenyl; and n is 2; wherein R.sup.5 is bromo, chloro, fluoro, cyano, nitro, methyl, ethyl, trifluoromethyl, cyclopropyl, or vinyl; R.sup.6a is independently fluoro, cyano, nitro, methoxy, difluoromethoxy or trifluoromethoxy; and R.sup.6 is independently bromo, chloro, fluoro, cyano, nitro methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy.

9. A compound of formula (I) according to claim 1 represented by the compounds of formula (Ib) ##STR00043## wherein R.sup.a is hydrogen, halogen, cyano, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8haloalkyl, or C.sub.1-C.sub.8haloalkoxy; R.sup.b is hydrogen, halogen, cyano, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8haloalkyl, or C.sub.1-C.sub.8haloalkoxy; R.sup.c is hydrogen, halogen, cyano, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8haloalkyl, or C.sub.1-C.sub.8haloalkoxy; R.sup.5 is halogen, cyano, C.sub.1-C.sub.8alkyl, C.sub.3-C.sub.8cycloalkyl, C.sub.1-C.sub.8haloalkyl, C.sub.2-C.sub.8alkenyl; R.sup.d is S(O).sub.2R.sup.2; R.sup.2 is 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, 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, N(R.sup.8)(R.sup.9), C.sub.1-C.sub.4alkylamino, fluoro; 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; R.sup.6a is independently C.sub.1-C.sub.8alkoxy, or C.sub.1-C.sub.8haloalkoxy; R.sup.6b is independently oxo, amino, C.sub.1-C.sub.8alkylamino, N,NC.sub.1-C.sub.8dialkylamino, C.sub.1-C.sub.8alkoxy, C.sub.1-C.sub.8haloalkoxy, phenyl, phenyl substituted by one to three R.sup.7, 5-6 membered heteroaryl or 5-6 membered heteroaryl substituted by one to three R.sup.7; R.sup.7 is independently halogen, cyano, 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, C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8alkyl substituted by one to three R.sup.6a, C.sub.2-C.sub.8alkenyl or C.sub.2-C.sub.8alkenyl substituted by one to three R.sup.6a, 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, S(O).sub.2R.sup.10; R.sup.10 is hydrogen, cyano-C.sub.1-C.sub.8alkyl, C.sub.1-C.sub.8alkyl or C.sub.1-C.sub.8alkyl substituted by one to three R.sup.6a, phenyl, phenyl substituted by one to three R.sup.7, 5-6 membered heteroaryl, 5-6 membered heteroaryl substituted by one to three R.sup.7.

10. A compound of formula (Int-I) ##STR00044## wherein A.sup.1, A.sup.2, A.sup.3, A.sup.4, R.sup.1 and R.sup.2, am as defined for a compound of formula (I) according to claim 1 and X.sup.B is a leaving group, or X.sup.B is cyano, formyl, CH?NOH or acetyl; or a tautomer, isomer, enantiomer, salt or N-oxide thereof; or a compound of formula (Int-II) ##STR00045## wherein A.sup.1, A.sup.2, A.sup.3, A.sup.4, R.sup.1 and R.sup.2, are as defined for a compound of formula (I) according to any one of claims 1 to 9 and X.sup.C is CH.sub.2-halogen, CHC(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) according to claim 1; or a tautomer, isomer, enantiomer, salt or N-oxide thereof; or a compound of formula (Int-III) ##STR00046## wherein R.sup.1 and R.sup.2, are as defined for a compound of formula (I) according to claim 1; or a tautomer, isomer, enantiomer, salt or N-oxide thereof.

11. A method of combating and/or controlling an invertebrate animal pest which comprises applying to the pest, to a locus of the pest, or to a plant susceptible to attack by the pest a pesticidally effective amount of a compound of formula (I) as defined in claim 1.

12. 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.

13. A method for controlling pests, which comprises applying a composition according to claim 12 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.

14. A method for the protection of plant propagation material from the attack by pests, which comprises treating the propagation material or the site, where the propagation material is planted, with a composition according to claim 12.

15. Plant propagation material treated with the pesticidal composition described in claim 12.

Description

BIOLOGICAL EXAMPLES

[0491] These Examples illustrate the pesticidal/insecticidal properties of compounds of formula (I). Tests were performed as follows:

[0492] Diabrotica Balteata (Corn Root Worm)

[0493] Maize sprouts placed onto an agar layer in 24-well microtiter plates were treated with aqueous test solutions prepared from 10000 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.

[0494] 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, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A27, A28, A29, A30, A31, A32, A33, A34, A35, A36, A37, A38, A39, A40, A41, A42, A43, A44, A45, A46, A48, A49, A50, A51, A52, A53, A54, A55, A57, A58, A59, A60, A61, A62, A63, A64, A65, A66, A67, A68, A69, A70, A71, A72, A73, A74, A75, A76, A77, A78, A79, A80, A81, A82, A83, A84, A85, A86, A87, A88, A89, A90, A91, A92, A93, A94, A95, A96, A97, A98, A99, A100, A101, A102, A103, A104, A105, A106, A107, A108, A109, A110, A111, A112, A113, A114, A115, A116, A117, A118, A119, A120, A121, A122, A123, A124, A125, A126, A127, A128, A129, A130, A131, A132, A133, A134, A135, A136, A137, A138, A139, A140, A141, A142, A143, A144, A145, A146, A147, A148, A149, A150, A151, A152, A153, A154, A155, A156, A157, A158, A159, A160, A161, A162, A163, A164, A165, A166, A167, A168, A169, A170, A171, A172, A173, A174, A176, A178, A179, A180, A181, A182, A183, A184, A185, A186, A187, A188, A189, A190, A192, A194, A195, A196, A197, A198, A199, A200, A201, A202, A203, A204, A205, A206, A207, A208, A209, A210, A211, A212, A213, A214, A215, A216, A217, A218, A219, A220, A221, A222, A223, A224, A225, A226, A227, A228, A229, A230, A231, A232, A233, A236, A237, A239.

[0495] Euschlstus Heros (Neotropical Brown Stink Bug)

[0496] Soybean leaves on agar in 24-well microtiter plates were sprayed with aqueous test solutions prepared from 10000 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.

[0497] 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:

A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A17, A18, A19, A20, A26, A27, A33, A34, A35, A36, A37, A38, A39, A40, A41, A42, A43, A44, A45, A46, A48, A49, A50, A52, A54, A57, A58, A59, A60, A61, A62, A63, A64, A65, A66, A67, A68, A69, A70, A71, A72, A73, A74, A75, A76, A77, A78, A79, A80, A81, A82, A83, A84, A85, A86, A87, A88, A89, A90, A91, A92, A93, A94, A95, A96, A97, A98, A99, A100, A101, A102, A103, A104, A105, A106, A107, A108, A109, A110, A111, A112, A113, A114, A115, A116, A117, A118, A119, A120, A121, A122, A123, A124, A125, A126, A127, A128, A129, A130, A131, A132, A133, A134, A135, A136, A137, A138, A139, A140, A141, A142, A143, A144, A145, A146, A147, A148, A149, A150, A151, A152, A153, A154, A155, A156, A157, A158, A159, A160, A161, A162, A163, A164, A165, A166, A167, A168, A169, A172, A173, A174, A176, A178, A179, A180, A181, A183, A184, A185, A186, A187, A188, A189, A190, A192, A194, A195, A196, A197, A198, A199, A200, A201, A202, A203, A204, A205, A206, A207, A209, A210, A211, A212, A213, A214, A215, A216, A217, A218, A219, A220, A221, A223, A224, A225, A226, A227, A228, A229, A230, A231, A232, A233, A236, A239

[0498] Myzus persicae (Green Peach Aphid): Feeding/Contact Activity

[0499] Sunflower leaf discs were placed onto agar in a 24-well microtiter plate and sprayed with aqueous test solutions prepared from 10000 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.

[0500] The following compounds resulted in at least 80% mortality at an application rate of 200 ppm:

A1, A3, A4, A5, A6, A7, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A27, A28, A29, A30, A31, A32, A33, A34, A35, A36, A37, A38, A39, A40, A41, A42, A43, A44, A45, A50, A59, A61, A62, A63, A64, A65, A66, A67, A68, A69, A70, A71, A72, A73, A74, A75, A76, A77, A78, A79, A80, A81, A82, A83, A84, A85, A86, A87, A90, A91, A93, A95, A96, A97, A98, A99, A100, A101, A103, A104, A105, A106, A107, A108, A109, A111, A112, A113, A114, A115, A116, A117, A118, A119, A120, A121, A122, A123, A124, A125, A126, A127, A128, A129, A130, A131, A132, A133, A134, A135, A136, A137, A138, A139, A140, A141, A142, A143, A144, A145, A146, A147, A148, A149, A150, A151, A152, A153, A154, A155, A156, A157, A158, A159, A161, A162, A164, A166, A168, A169, A172, A173, A174, A178, A180, A181, A183, A184, A185, A186, A187, A188, A189, A192, A196, A197, A198, A200, A204, A205, A206, A207, A208, A209, A210, A211, A212, A213, A214, A215, A216, A217, A218, A219, A220, A223, A226, A228, A229, A230, A231, A232, A233.

[0501] Plutella Xylostella (Diamond Back Moth)

[0502] 24-well microtiter plates with artificial diet were treated with aqueous test solutions prepared from 10000 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.

[0503] 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, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A27, A28, A29, A30, A31, A32, A33, A34, A35, A36, A37, A38, A39, A40, A41, A42, A43, A44, A45, A46, A48, A49, A50, A51, A52, A53, A54, A55, A56, A57, A58, A59, A60, A61, A62, A63, A64, A65, A66, A67, A68, A69, A70, A71, A72, A73, A74, A75, A76, A77, A78, A79, A80, A81, A82, A83, A84, A85, A86, A87, A88, A89, A90, A91, A92, A93, A94, A95, A96, A97, A98, A99, A100, A101, A102, A103, A104, A105, A106, A107, A108, A109, A110, A111, A112, A113, A114, A115, A116, A117, A118, A119, A120, A121, A122, A123, A124, A125, A126, A127, A128, A129, A130, A131, A132, A133, A134, A135, A136, A137, A138, A139, A140, A141, A142, A143, A144, A145, A146, A147, A148, A149, A150, A151, A152, A153, A154, A155, A156, A157, A158, A159, A160, A161, A162, A163, A164, A165, A166, A167, A168, A169, A170, A171, A172, A173, A174, A176, A177, A178, A179, A180, A181, A182, A183, A184, A185, A186, A187, A188, A189, A190, A192, A193, A194, A195, A196, A197, A198, A199, A200, A201, A202, A203, A204, A205, A206, A207, A208, A209, A210, A211, A212, A213, A214, A215, A216, A217, A218, A219, A220, A221, A222, A223, A224, A225, A226, A227, A228, A229, A230, A231, A232, A233, A236, A237, A239.

[0504] Spodoptera littoralis (Egyptian Cotton Leaf Worm)

[0505] Cotton leaf discs were placed onto agar in 24-well microtiter plates and sprayed with aqueous test solutions prepared from 10000 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.

[0506] The following compounds resulted in at least 80% control at an application rate of 200 ppm:

A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A27, A28, A29, A30, A31, A32, A33, A34, A35, A36, A37, A38, A39, A40, A41, A42, A43, A44, A45, A46, A47, A48, A49, A50, A51, A52, A53, A54, A55, A56, A57, A58, A59, A60, A61, A62, A63, A64, A65, A66, A67, A68, A69, A70, A71, A72, A73, A74, A75, A76, A77, A78, A79, A80, A81, A82, A83, A84, A85, A86, A87, A88, A89, A90, A91, A92, A93, A94, A95, A96, A97, A98, A99, A100, A101, A102, A103, A104, A105, A106, A107, A108, A109, A110, A111, A112, A113, A114, A115, A116, A117, A118, A119, A120, A121, A122, A123, A124, A125, A126, A127, A128, A129, A130, A131, A132, A133, A134, A135, A136, A137, A138, A139, A140, A141, A142, A143, A144, A145, A146, A147, A148, A149, A150, A151, A152, A153, A154, A155, A156, A157, A158, A159, A160, A161, A162, A163, A164, A165, A166, A167, A168, A169, A170, A171, A172, A173, A174, A175, A176, A177, A178, A179, A180, A181, A182, A183, A184, A185, A186, A187, A188, A189, A190, A192, A193, A194, A195, A196, A197, A198, A199, A200, A201, A202, A203, A204, A205, A206, A207, A208, A209, A210, A211, A212, A213, A214, A215, A216, A217, A218, A219, A220, A221, A222, A223, A224, A225, A226, A227, A228, A229, A230, A231, A232, A233, A236, A237, A238, A239

[0507] Spodoptera littoralis (Egyptian Cotton Leaf Worm)

[0508] Test compounds were applied by pipette from 10000 ppm DMSO stock solutions into 24-well plates and mixed with agar. Lettuce seeds were placed onto the agar and the multi well plate was closed by another plate which contained also agar. After 7 days the compound was absorbed by the roots and the lettuce grew into the lid plate. The lettuce leaves were then cut off into the lid plate. Spodoptera eggs were pipetted through a plastic stencil onto a humid gel blotting paper and the lid plate was closed with it. The samples were assessed for mortality, anti-feedant effect and growth inhibition in comparison to untreated samples 6 days after infestation.

[0509] The following compounds gave an effect of at least 80% in at least one of the three categories (mortality, anti-feeding, or growth inhibition) at a test rate of 12.5 ppm:

A1, A5, A6, A8, A10, A11, A12, A13, A16, A19, A20, A21, A22, A23, A24, A25, A27, A28, A30, A31, A32, A33, A34, A35, A36, A37, A38, A39, A40, A41, A42, A44, A45, A48, A52, A57, A59, A61, A62, A63, A64, A65, A66, A67, A68, A69, A70, A72, A73, A75, A76, A78, A81, A82, A87, A90, A91, A95, A97, A98, A105, A107, A108, A109, A111, A112, A113, A114, A115, A116, A117, A118, A119, A120, A121, A122, A123, A125, A126, A127, A128, A130, A131, A132, A133, A134, A135, A136, A137, A138, A139, A140, A141, A142, A143, A144, A145, A146, A147, A155, A158, A159, A160, A236.

[0510] Tetranychus urticae (Two-Spotted Spider Mite): Feeding/Contact Activity

[0511] Bean leaf discs on agar in 24-well microtiter plates were sprayed with aqueous test solutions prepared from 10000 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.

[0512] The following compounds resulted in at least 80% mortality at an application rate of 200 ppm:

A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A27, A28, A29, A30, A31, A32, A33, A34, A35, A36, A37, A38, A39, A40, A41, A42, A43, A44, A45, A46, A48, A49, A50, A51, A52, A53, A54, A55, A57, A58, A59, A60, A61, A62, A63, A64, A65, A66, A67, A68, A69, A70, A71, A72, A73, A74, A75, A76, A77, A78, A79, A80, A81, A82, A83, A84, A85, A86, A87, A88, A89, A90, A91, A92, A93, A94, A95, A96, A97, A98, A99, A100, A101, A102, A103, A104, A105, A106, A107, A108, A109, A110, A111, A112, A113, A114, A115, A116, A117, A118, A119, A120, A121, A122, A123, A124, A125, A126, A127, A128, A129, A130, A131, A132, A133, A134, A135, A136, A137, A138, A139, A140, A141, A142, A143, A144, A145, A146, A147, A148, A149, A150, A151, A152, A153, A154, A155, A156, A157, A158, A159, A160, A161, A162, A163, A164, A165, A166, A167, A168, A169, A170, A171, A172, A173, A174, A176, A178, A179, A180, A181, A182, A183, A184, A185, A186, A187, A188, A189, A190, A192, A193, A194, A195, A196, A197, A198, A199, A200, A201, A202, A203, A204, A205, A206, A207, A208, A209, A210, A211, A212, A213, A214, A215, A216, A217, A218, A219, A220, A221, A222, A223, A224, A225, A226, A227, A228, A229, A230, A231, A232, A233, A236.

[0513] Thrips tabaci (Onion Thrips) Feeding/Contact Activity

[0514] Sunflower leaf discs were placed on agar in 24-well microtiter plates and sprayed with aqueous test solutions prepared from 10000 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.

[0515] The following compounds resulted in at least 80% mortality at an application rate of 200 ppm:

A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A27, A28, A29, A30, A31, A32, A33, A34, A35, A36, A37, A38, A39, A40, A41, A42, A43, A44, A45, A46, A48, A49, A50, A51, A52, A55, A57, A58, A59, A60, A61, A62, A63, A64, A65, A66, A67, A68, A69, A70, A71, A72, A73, A74, A75, A76, A77, A78, A79, A80, A81, A82, A83, A84, A85, A86, A87, A88, A89, A90, A91, A92, A93, A94, A95, A96, A97, A98, A99, A100, A101, A102, A103, A104, A105, A106, A107, A108, A109, A110, A111, A112, A113, A114, A115, A116, A117, A118, A119, A120, A121, A122, A123, A124, A125, A126, A127, A128, A129, A130, A131, A132, A133, A134, A135, A136, A137, A138, A139, A140, A141, A142, A143, A144, A145, A146, A147, A148, A149, A150, A151, A152, A153, A154, A155, A156, A157, A158, A159, A160, A161, A162, A163, A164, A165, A166, A167, A168, A169, A170, A171, A172, A173, A174, A176, A177, A178, A179, A180, A181, A182, A183, A184, A185, A186, A187, A188, A189, A190, A192, A193, A194, A195, A196, A197, A198, A199, A200, A202, A203, A204, A205, A206, A207, A208, A209, A210, A211, A212, A213, A214, A215, A216, A217, A218, A219, A220, A221, A223, A224, A225, A226, A227, A228, A229, A230, A231, A232, A233, A236, A239.