Isothiazoline compounds for combating invertebrate pests

Abstract

The present invention relates to isothiazoline compounds of formula I ##STR00001## wherein the variables are as defined in the claims or the description, which are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes, and to a method for producing them. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.

Claims

1. A compound of formula I ##STR00088## wherein A is a group A.sup.1 or A.sup.3; wherein A.sup.1 is selected from the group consisting of —C(═NR.sup.6)R.sup.8, and —S(O).sub.nR.sup.9; A.sup.3 is a group of following formula: ##STR00089## wherein # denotes the bond to the aromatic ring of formula (I); B.sup.1, B.sup.2 and B.sup.3 are each independently selected from the group consisting of N and CR.sup.2, with the proviso that at most two of B.sup.1, B.sup.2 and B.sup.3 are N; G.sup.1, G.sup.2, G.sup.3 and G.sup.4 are each independently selected from the group consisting of N and CR.sup.4, with the proviso that at most two of G.sup.1, G.sup.2, G.sup.3 and G.sup.4 are N; R.sup.1 is CF.sub.3; each R.sup.2 is independently selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, —SCN, —SF.sub.5, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, wherein the four last mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more radicals R.sup.8, —Si(R.sup.12).sub.3, —OR.sup.9, —S(O).sub.nR.sup.9, —NR.sup.10aR.sup.10b, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R.sup.11, and a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring containing 1, 2, 3 or 4 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO.sub.2, as ring members, where the heteromono- or heterobicyclic ring may be substituted by one or more radicals R.sup.11; R.sup.3a, R.sup.3b are each independently selected from the group consisting of hydrogen, halogen, hydroxyl, —CO.sub.2R.sup.3d, C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-haloalkyl, C.sub.2-C.sub.3-alkenyl, C.sub.2-C.sub.3-alkynyl, C.sub.1-C.sub.3-alkoxy, C.sub.1-C.sub.3-haloalkoxy, C.sub.1-C.sub.3-alkylthio, C.sub.1-C.sub.3-haloalkylthio, C.sub.1-C.sub.3-alkylsulfonyl and C.sub.1-C.sub.3-haloalkylsulfonyl; or R.sup.3a and R.sup.3b together form a group ═O, ═C(R.sup.3c).sub.2, ═NOH or ═NOCH.sub.3; each R.sup.3c is independently selected from the group consisting of hydrogen, halogen, CH.sub.3 and CF.sub.3; R.sup.3d is selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl and C.sub.1-C.sub.3-alkyloxy-C.sub.1-C.sub.3-alkyl-; each R.sup.4 is independently selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, —SCN, —SF.sub.5, C.sub.1-C.sub.6-alkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R.sup.8, C.sub.3-C.sub.8-cycloalkyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R.sup.8, C.sub.2-C.sub.6-alkenyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R.sup.8, C.sub.2-C.sub.6-alkynyl which may be partially or fully halogenated and/or may be substituted by one or more radicals R.sup.8, —Si(R.sup.12).sub.3, —OR.sup.9, —S(O)R.sup.9, —NR.sup.10aR.sup.10b, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R.sup.11, and a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring containing 1, 2, 3 or 4 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO.sub.2, as ring members, where the heteromonocyclic or heterobicyclic ring may be substituted by one or more radicals R.sup.11; each R.sup.5 is independently selected from the group consisting of hydrogen, C.sub.1-C.sub.10-alkyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.2-C.sub.10-alkenyl, C.sub.2-C.sub.10-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted with one or more substituents R.sup.8, and —S(O).sub.nR.sup.9, each R.sup.6 is independently selected from the group consisting of hydrogen, cyano, C.sub.1-C.sub.10-alkyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.2-C.sub.10-alkenyl, C.sub.2-C.sub.10-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more substituents R.sup.8, —OR.sup.9, —NR.sup.10aR.sup.10b, —S(O).sub.nR.sup.9, —C(═O)NR.sup.10aN(R.sup.10aR.sup.10b), —Si(R.sup.12).sub.3, —C(═O)R.sup.8, phenyl which may be substituted with 1, 2, 3, 4, or 5 substituents R.sup.11, and a 3-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring containing 1, 2, 3 or 4 heteroatoms or heteroatom groups independently selected from the group consisting of N, O, S, NO, SO and SO.sub.2, as ring members, where the heteromonocyclic or heterobicyclic ring may be substituted with one or more substituents R.sup.11; or R.sup.5 and R.sup.6, together with the nitrogen atom to which they are bound, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, where the ring may further contain 1, 2, 3 or 4 heteroatoms or heteroatom-containing groups selected from the group consisting of O, S, N, SO, SO.sub.2, C═O and C═S as ring members, wherein the heterocyclic ring may be substituted with 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of halogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, wherein the aliphatic or cycloaliphatic moieties in the twelve last-mentioned radicals may be substituted by one or more radicals R.sup.8, and phenyl which may be substituted with 1, 2, 3, 4 or 5 substituents R.sup.11; or R.sup.5 and R.sup.6 together form a group ═C(R.sup.8).sub.2, ═S(O).sub.m(R.sup.9).sub.2, ═NR.sup.10a or ═NOR.sup.9; R.sup.7a, R.sup.7b are each independently selected from the group consisting of hydrogen, halogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.2-C.sub.6-alkenyl and C.sub.2-C.sub.6-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more radicals R.sup.8; each R.sup.8 is independently selected from the group consisting of cyano, azido, nitro, —SCN, —SF.sub.5, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, where the cycloaliphatic moieties in the two last-mentioned radicals may be substituted by one or more radicals R.sup.13; —Si(R.sup.12).sub.3, —OR.sup.9, —OSO.sub.2R.sup.9, —S(O).sub.nR.sup.9, —N(R.sup.10a)R.sup.10b, —C(═O)N(R.sup.10a)R.sup.10b, —C(═S)N(R.sup.10a)R.sup.10b, —C(═O)OR.sup.9, phenyl, optionally substituted with 1, 2, 3, 4 or 5 substituents R.sup.16, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO.sub.2, as ring members, where the heterocyclic ring is optionally substituted with one or more substituents R.sup.16, or two R.sup.8 present on the same carbon atom of an alkyl, alkenyl, alkynyl or cycloalkyl group together form a group ═O, ═C(R.sup.13).sub.2; ═S; ═S(O).sub.m(R.sup.15).sub.2, ═S(O).sub.mR.sup.15N(R.sup.14a)R.sup.14b, ═NR.sup.10a, ═NOR.sup.9; or ═NN(R.sup.10a)R.sup.10b; or two radicals R.sup.8, together with the carbon atoms of an alkyl, alkenyl, alkynyl or cycloalkyl group which they are bonded to, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring, where the heterocyclic ring comprises 1, 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO.sub.2, as ring members, and where the carbocyclic or heterocyclic ring is optionally substituted with one or more substituents R.sup.16; and R.sup.8 as a substituent on a cycloalkyl ring is additionally selected from the group consisting of C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl and C.sub.2-C.sub.6-haloalkynyl, where the aliphatic moieties in these six radicals may be substituted by one or more radicals R.sup.13; and R.sup.8 in the groups —C(═NR.sup.6)R.sup.8, —C(═O)R.sup.8 and ═C(R.sup.8).sub.2 is additionally selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl and C.sub.2-C.sub.6-haloalkynyl, where the aliphatic moieties in the six last-mentioned radicals may be substituted by one or more radicals R.sup.13; each R.sup.9 is independently selected from the group consisting of hydrogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-cycloalkyl-C.sub.1-C.sub.4-alkyl-, C.sub.3-C.sub.8-halocycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, where the aliphatic and cycloaliphatic moieties in the nine last-mentioned radicals may be substituted by one or more radicals R.sup.13, —C.sub.1-C.sub.6-alkyl-C(═O)OR.sup.15, —C.sub.1-C.sub.6-alkyl-C(═O)N(R.sup.14a)R.sup.14b, —C.sub.1-C.sub.6-alkyl-C(═S)N(R.sup.14a)R.sup.14b, —C.sub.1-C.sub.6-alkyl-C(═NR.sup.14)N(R.sup.14a)R.sup.14b, —Si(R.sup.12).sub.3, —S(O).sub.nR.sup.15, —S(O).sub.nN(R.sup.14a)R.sup.14b, —N(R.sup.10a)R.sup.10b, —N═C(R.sup.13).sub.2, —C(═O)R.sup.13, —C(═O)N(R.sup.14a)R.sup.14b, —C(═S)N(R.sup.14a)R.sup.14b, —C(═O)OR.sup.15, phenyl, optionally substituted with one or more substituents R.sup.16; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO.sub.2, as ring members, where the heterocyclic ring is optionally substituted with one or more substituents R.sup.16; and R.sup.9 in the groups —S(O).sub.nR.sup.9 and —OSO.sub.2R.sup.9 is additionally selected from the group consisting of C.sub.1-C.sub.6-alkoxy and C.sub.1-C.sub.6-haloalkoxy; R.sup.10a, R.sup.10b are selected independently from one another from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, where the aliphatic and cycloaliphatic moieties in the eight last-mentioned radicals may be substituted by one or more radicals R.sup.13; —C.sub.1-C.sub.6-alkyl-C(═O)OR.sup.15, —C.sub.1-C.sub.6-alkyl-C(═O)N(R.sup.14a)R.sup.14b, —C.sub.1-C.sub.6-alkyl-C(═S)N(R.sup.14a)R.sup.14b, —C.sub.1-C.sub.6-alkyl-C(═NR.sup.14)N(R.sup.14a)R.sup.14b, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio, —S(O).sub.nR.sup.15, —S(O).sub.nN(R.sup.14a)R.sup.14b, —C(═O)R.sup.13, —C(═O)OR.sup.15, —C(═O)N(R.sup.14a)R.sup.14b, —C(═S)R.sup.13, —C(═S)SR.sup.15, —C(═S)N(R.sup.14a)R.sup.14b, —C(═NR.sup.14)R.sup.13; phenyl, optionally substituted with 1, 2, 3 or 4, substituents R.sup.16; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1, 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO.sub.2, as ring members, where the heterocyclic ring is optionally substituted with one or more substituents R.sup.16; or R.sup.10a and R.sup.10b form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO.sub.2, as ring members, where the heterocyclic ring optionally carries one or more substituents selected from halogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, phenyl, optionally substituted with 1, 2, 3, 4 or 5 substituents R.sup.16, and a 3-, 4-, 5-, 6,- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO.sub.2, as ring members, where the heterocyclic ring optionally carries one or more substituents R.sup.16; or R.sup.10a and R.sup.10b together form a group ═C(R.sup.13).sub.2, ═S(O).sub.m(R.sup.15).sub.2, ═S(O).sub.mR.sup.15N(R.sup.14a)R.sup.14b, ═NR.sup.14 or ═NOR.sup.15; R.sup.11 is independently selected from the group consisting of halogen, cyano, azido, nitro, —SCN, —SF.sub.5, C.sub.1-C.sub.10-alkyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.2-C.sub.10-alkenyl, C.sub.2-C.sub.10-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted with one or more radicals R.sup.8, —OR.sup.9, —NR.sup.10aR.sup.10b, —S(O).sub.nR.sup.9, —Si(R.sup.12).sub.3; phenyl, optionally substituted with 1, 2, 3, 4, or 5 substituents selected independently from R.sup.16; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated aromatic heterocyclic ring comprising 1, 2, 3 or 4 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO.sub.2, as ring members, where the heterocyclic ring is optionally substituted with one or more substituents selected independently from R.sup.16; or two R.sup.11 present on the same ring carbon atom of a saturated or partially unsaturated heterocyclic ring may together form a group ═O, ═C(R.sup.13).sub.2; ═S; ═S(O).sub.m(R.sup.15).sub.2; ═S(O).sub.mR.sup.15N(R.sup.14a)R.sup.14b, —NR.sup.14, —NOR.sup.15, or ═NN(R.sup.14a)R.sup.14b; or two R.sup.11 bound on adjacent ring atoms form together with the ring atoms to which they are bound a saturated 3-, 4-, 5-, 6-, 7-, 8- or 9-membered ring, wherein the ring may contain 1 or 2 heteroatoms or heteroatom groups selected from O, S, N, NR.sup.14, NO, SO and SO.sub.2 and/or 1 or 2 groups selected from C═O, C═S and C═NR.sup.14 as ring members, and wherein the ring may be substituted by one or more radicals selected from the group consisting of halogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, phenyl which may be substituted by 1, 2, 3, 4 or 5 radicals R.sup.16, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO.sub.2, as ring members, where the heterocyclic ring may be substituted by one or more radicals R.sup.16; each R.sup.12 is independently selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkoxy-C.sub.1-C.sub.6-alkyl, and phenyl, optionally substituted with 1, 2, 3, 4, or 5 substituents R.sup.16; each R.sup.13 is independently selected from the group consisting of cyano, nitro, —OH, —SH, —SCN, —SF.sub.5, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, C.sub.3-C.sub.8-cycloalkyl which may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 radicals selected from C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.4-cycloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy and oxo; phenyl, benzyl, phenoxy, where the phenyl moiety in the three last-mentioned radicals may be unsubstituted or carry 1, 2, 3, 4 or 5 substituents R.sup.16; and a 3-, 4-, 5-, 6-, or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO.sub.2, as ring members, where the heterocyclic ring may be substituted by 1, 2 or 3 substituents R.sup.16; or two R.sup.13 present on the same carbon atom of an alkyl, alkenyl, alkynyl or cycloalkyl group may together be ═O, ═CH(C.sub.1-C.sub.4-alkyl), ═C(C.sub.1-C.sub.4-alkyl)C.sub.1-C.sub.4-alkyl, ═N(C.sub.1-C.sub.6-alkyl) or ═NO(C.sub.1-C.sub.6-alkyl); and R.sup.13 as a substituent on a cycloalkyl ring is additionally selected from the group consisting of C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl and C.sub.2-C.sub.6-alkynyl, wherein the three last-mentioned aliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 substituents selected from CN, C.sub.3-C.sub.4-cycloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy and oxo; and R.sup.13 in the groups ═C(R.sup.13).sub.2, —N═C(R.sup.13).sub.2, —C(═O)R.sup.13, —C(═S)R.sup.13 and —C(═NR.sup.14)R.sup.13 is additionally selected from the group consisting of hydrogen, halogen, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl and C.sub.2-C.sub.6-alkynyl, wherein the three last-mentioned aliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 radicals selected from CN, C.sub.3-C.sub.4-cycloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy and oxo; each R.sup.14 is independently selected from the group consisting of hydrogen, cyano, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, wherein the three last-mentioned aliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 radicals selected from oxo, CN, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-alkylsulfinyl, C.sub.1-C.sub.4-alkylsulfonyl, C.sub.3-C.sub.4-cycloalkyl which may be substituted by 1 or 2 substituents selected from halogen and cyano; C.sub.3-C.sub.8-cycloalkyl which may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 radicals selected from oxo C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-alkylsulfinyl, C.sub.1-C.sub.4-alkylsulfonyl, C.sub.3-C.sub.4-cycloalkyl, C.sub.3-C.sub.4-cycloalkyl-C.sub.1-C.sub.4-alkyl-, where the cycloalkyl moiety in the two last-mentioned radicals may be substituted by 1 or 2 substituents selected from halogen and cyano; phenyl, benzyl, pyridyl, phenoxy, wherein the cyclic moieties in the four last-mentioned radicals may be unsubstituted or carry 1, 2 or 3 substituents selected from halogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy and (C.sub.1-C.sub.6-alkoxy)carbonyl; and a 3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1 or 2 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO.sub.2, as ring members, where the heterocyclic ring is optionally substituted with one or more substituents R.sup.16; R.sup.14a and R.sup.14b, independently of each other, have one of the meanings given for R.sup.14; or R.sup.14a and R.sup.14b, together with the nitrogen atom to which they are bound, form a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain 1 or 2 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO.sub.2, as ring members, where the heterocyclic ring optionally carries one or more substituents selected from halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkoxy; or R.sup.14a and R.sup.14 or R.sup.14b and R.sup.14, together with the nitrogen atoms to which they are bound in the group —C(═NR.sup.14)N(R.sup.14a)R.sup.14b, form a 3-, 4-, 5-, 6- or 7-membered partially unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain 1 or 2 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO.sub.2, as ring members, where the heterocyclic ring optionally carries one or more substituents selected from halogen, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkoxy; each R.sup.15 is independently selected from the group consisting of hydrogen, cyano, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, wherein the three last-mentioned aliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 radicals selected from C.sub.3-C.sub.4-cycloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-alkylsulfinyl, C.sub.1-C.sub.4-alkylsulfonyl and oxo; C.sub.3-C.sub.8-cycloalkyl which may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 radicals selected from C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.4-cycloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-alkylsulfinyl, C.sub.1-C.sub.4-alkylsulfonyl and oxo; phenyl, benzyl, pyridyl and phenoxy, wherein the four last-mentioned radicals may be unsubstituted, partially or fully halogenated and/or carry 1, 2 or 3 substituents selected from C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy and (C.sub.1-C.sub.6-alkoxy)carbonyl; each R.sup.16 is independently selected from the group consisting of halogen, nitro, cyano, —OH, —SH, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl; C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, wherein the three last-mentioned aliphatic radicals may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 radicals selected from C.sub.3-C.sub.4-cycloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy and oxo; C.sub.3-C.sub.8-cycloalkyl which may be unsubstituted, partially or fully halogenated and/or may carry 1 or 2 radicals selected from C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.4-cycloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy and oxo; phenyl, benzyl, pyridyl and phenoxy, wherein the four last mentioned radicals may be unsubstituted, partially or fully halogenated and/or carry 1, 2 or 3 substituents selected from C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy and (C.sub.1-C.sub.6-alkoxy)carbonyl; or two R.sup.16 present together on the same atom of a saturated or partially unsaturated ring may be ═O, ═S, ═N(C.sub.1-C.sub.6-alkyl), ═NO(C.sub.1-C.sub.6-alkyl), ═CH(C.sub.1-C.sub.4-alkyl) or ═C(C.sub.1-C.sub.4-alkyl)C.sub.1-C.sub.4-alkyl; or two R.sup.16 on two adjacent carbon atoms form together with the carbon atoms they are bonded to a 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated ring, wherein the ring may contain 1 or 2 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO.sub.2, as ring members, and wherein the ring optionally carries one or more substituents selected from halogen, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy and C.sub.1-C.sub.4-haloalkoxy; each n is independently 0, 1 or 2; and each m is independently 0 or 1; an N-oxide, stereoisomer or agriculturally or veterinarily acceptable salt thereof.

2. The compound as claimed in claim 1, where A is A.sup.1 and A.sup.1 is —C(═NR.sup.6)R.sup.8.

3. The compound as claimed in claim 2, where R.sup.6 in —C(═NR.sup.6)R.sup.8 is selected from hydrogen, cyano, C.sub.3-C.sub.8-cycloalkyl, C.sub.2-C.sub.10-alkenyl, C.sub.2-C.sub.10-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals each independently may be partially or fully halogenated and/or may be substituted with 1, 2, 3, 4, 5 or 6 substituents R.sup.8; —OR.sup.9 and —NR.sup.10aR.sup.10b.

4. The compound as claimed in claim 3, where R.sup.6 in —C(═NR.sup.6)R.sup.8 is selected from —OR.sup.9 and —NR.sup.10aR.sup.10b.

5. The compound as claimed in claim 2, where R.sup.9 is selected from hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl and C.sub.2-C.sub.6-haloalkynyl.

6. The compound as claimed in claim 2, where R.sup.6 in —C(═NR.sup.6)R.sup.8 is —NR.sup.10aR.sup.10b, where R.sup.10a and R.sup.10b, independently of each other, are selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.1-C.sub.6-haloalkylcarbonyl, —C(═O)OR.sup.15, —C(═O)N(R.sup.14a)R.sup.14b, —C(═S)N(R.sup.14a)R.sup.14b, phenyl which is optionally substituted with 1, 2, 3 or 4, substituents R.sup.16, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1, 2, 3 or 4 heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO.sub.2, as ring members, where the heterocyclic ring is optionally substituted with one or more substituents R.sup.16; or R.sup.10a and R.sup.10b form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO.sub.2, as ring members, where the heterocyclic ring optionally carries one or more substituents selected from halogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl and C.sub.2-C.sub.6-haloalkynyl.

7. The compound as claimed in claim 6, where R.sup.10a is selected from hydrogen, C.sub.1-C.sub.6-alkyl and C.sub.1-C.sub.6-haloalkyl; and R.sup.10b is selected from C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.1-C.sub.6-haloalkylcarbonyl, —C(═O)OR.sup.15, —C(═O)N(R.sup.14a)R.sup.14b, —C(═S)N(R.sup.14a)R.sup.14b, phenyl which is optionally substituted with 1, 2, 3 or 4, substituents R.sup.16, and a 5- or 6-membered heteroaromatic ring comprising 1, 2 or 3 heteroatoms selected from N, O and S, as ring members, where the heteroaromatic ring is optionally substituted with one or more substituents R.sup.16.

8. The compound as claimed in claim 6, where R.sup.14a is selected from hydrogen, C.sub.1-C.sub.6-alkyl and C.sub.1-C.sub.6-haloalkyl; and R.sup.14b is selected from hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-halocycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl-, C.sub.1-C.sub.6-alkyl substituted with a CN group, C.sub.1-C.sub.6-alkoxyl, C.sub.1-C.sub.6-haloalkoxy, phenyl which is optionally substituted with 1, 2, or 3, substituents each independently selected from the group consisting of halogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, and C.sub.1-C.sub.4-haloalkoxy; and a heterocyclic ring selected from rings of formulae E-1 to E-34 and E-43 to E-51 ##STR00090## ##STR00091## ##STR00092## ##STR00093## ##STR00094## ##STR00095## ##STR00096## wherein k is 0, 1, 2 or 3, n is 0, 1 or 2; and each R.sup.16 is independently selected from the group consisting of halogen, cyano, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-haloalkylthio, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-halocycloalkyl, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-haloalkenyl, C.sub.2-C.sub.4-alkynyl and C.sub.2-C.sub.4-haloalkynyl; or two R.sup.16 present on the same carbon atom of a saturated ring may form together ═O or ═S.

9. The compound as claimed in claim 4, where R.sup.6 in —C(═NR.sup.6)R.sup.8 is —NR.sup.10aR.sup.10b, where R.sup.10a and R.sup.10b, independently of each other, are selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, C.sub.1-C.sub.6-alkylcarbonyl, C.sub.1-C.sub.6-haloalkylcarbonyl, —C(═O)N(R.sup.14a)R.sup.14b, —C(═S)N(R.sup.14a)R.sup.14b, phenyl which is optionally substituted with 1, 2, 3 or 4, substituents R.sup.16, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1, 2, 3 or 4 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO.sub.2, as ring members, where the heterocyclic ring is optionally substituted with one or more substituents R.sup.16; or R.sup.10a and R.sup.10b form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, wherein the heterocyclic ring may additionally contain one or two heteroatoms or heteroatom groups selected from N, O, S, NO, SO and SO.sub.2, as ring members, where the heterocyclic ring optionally carries one or more substituents selected from halogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl and C.sub.2-C.sub.6-haloalkynyl.

10. The compound as claimed in claim 9, where R.sup.10a is selected from hydrogen, C.sub.1-C.sub.6-alkyl and C.sub.1-C.sub.6-haloalkyl; and R.sup.10b is selected from —C(═O)N(R.sup.14a)R.sup.14b, —C(═S)N(R.sup.14a)R.sup.14b, phenyl which is optionally substituted with 1, 2, 3 or 4, substituents R.sup.16, and a 5- or 6-membered heteroaromatic ring comprising 1, 2 or 3 heteroatoms selected from the group consisting of N, O and S, as ring members, where the heteroaromatic ring is optionally substituted with one or more substituents R.sup.16.

11. The compound as claimed in claim 9, where R.sup.14a is selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl and C.sub.1-C.sub.6-haloalkyl; and R.sup.14b is selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-halocycloalkyl, C.sub.1-C.sub.6-alkyl substituted with a CN group, phenyl which is optionally substituted with 1, 2, or 3, substituents each independently selected from the group consisting of halogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy and (C.sub.1-C.sub.6-alkoxy)carbonyl; and a heterocyclic ring selected from rings of formulae E-1 to E-34 and E-43 to E-51 ##STR00097## ##STR00098## ##STR00099## ##STR00100## ##STR00101## ##STR00102## ##STR00103## ##STR00104## wherein k is 0, 1, 2 or 3, n is 0, 1 or 2; and each R.sup.16 is independently selected from the group consisting of halogen, cyano, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-haloalkylthio, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-halocycloalkyl, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-haloalkenyl, C.sub.2-C.sub.4-alkynyl and C.sub.2-C.sub.4-haloalkynyl; or two R.sup.16 present on the same carbon atom of a saturated ring may form together ═O or ═S.

12. The compound as claimed in claim 2, where R.sup.8 in —C(═NR.sup.6)R.sup.8 as a meaning for A.sup.1 is selected from hydrogen and NR.sup.10aR.sup.10b.

13. The compound as claimed in claim 1, where A is A.sup.3 and in A.sup.3R.sup.7a and R.sup.7b are independently of each other selected from hydrogen, C.sub.1-C.sub.4-alkyl and C.sub.1-C.sub.4-haloalkyl.

14. The compound as claimed in claim 1, where in A.sup.3 R.sup.5 is selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted with one or more substituents R.sup.8; and R.sup.6 is selected from hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, wherein the four last-mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more substituents R.sup.8, —OR.sup.9, —NR.sup.10aR.sup.10b, —S(O).sub.nR.sup.9, —C(═O)NR.sup.10aN(R.sup.10aR.sup.10b), —C(═O)R.sup.8, and a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or maximally unsaturated heteromonocyclic or heterobicyclic ring containing 1, 2, 3 or 4 heteroatoms or heteroatom groups independently selected from N, O, S, NO, SO and SO.sub.2, as ring members, where the heteromonocyclic or heterobicyclic ring may be substituted with one or more substituents R.sup.11; or R.sup.5 and R.sup.6, together with the nitrogen atom to which they are bound, form a 3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring, where the ring may further contain 1, 2, 3 or 4 heteroatoms or heteroatom-containing groups selected from the group consisting of O, S, N, SO, SO.sub.2, C═O and C═S as ring members, wherein the heterocyclic ring may be substituted with 1, 2, 3, 4 or 5 substituents independently selected from the group consisting of halogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-haloalkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.2-C.sub.6-haloalkynyl, wherein the aliphatic or cycloaliphatic moieties in the twelve last-mentioned radicals may be substituted by one or more radicals R.sup.8, and phenyl which may be substituted with 1, 2, 3, 4 or 5 substituents R.sup.11; or R.sup.5 and R.sup.6 together form a group ═C(R.sup.8).sub.2, ═S(O).sub.m(R.sup.9).sub.2, ═NR.sup.10a or ═NOR.sup.9.

15. The compound as claimed in claim 14, where R.sup.5 is selected from the group consisting of hydrogen, C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.3-alkynyl, —CH.sub.2—CN and C.sub.1-C.sub.6-alkoxy-methyl; and R.sup.6 is —C(═O)R.sup.8.

16. The compound as claimed in claim 14, where R.sup.8 is selected from the group consisting of C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, where the aliphatic and cycloaliphatic moieties in the four last-mentioned radicals may be substituted by one or more radicals R.sup.13; —OR.sup.9, —S(O).sub.nR.sup.9, —N(R.sup.10a)R.sup.10b, phenyl, optionally substituted with 1, 2, 3, 4 or 5 substituents R.sup.16, and a 3-, 4-, 5- or 6-membered saturated, partially unsaturated or maximally unsaturated heterocyclic ring comprising 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO and SO.sub.2, as ring members, where the heterocyclic ring is optionally substituted with one or more substituents R.sup.16.

17. The compound as claimed in claim 16, where R.sup.8 is selected from the group consisting of C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkyl, C.sub.1-C.sub.4-alkyl substituted by one radical R.sup.13, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, —N(R.sup.10a)R.sup.10b, phenyl which is optionally substituted with 1, 2, 3, 4 or 5 substituents each independently selected from the group consisting of halogen, cyano, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-haloalkylthio, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-halocycloalkyl, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-haloalkenyl, C.sub.2-C.sub.4-alkynyl and C.sub.2-C.sub.4-haloalkynyl; and a heterocyclic ring selected from rings of formulae E-1 to E-51, ##STR00105## ##STR00106## ##STR00107## ##STR00108## ##STR00109## wherein k is 0, 1, 2 or 3, n is 0, 1 or 2; R.sup.10a and R.sup.10b, independently of each other, are selected from the group consisting of hydrogen, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl and C.sub.3-C.sub.6-cycloalkyl; and R.sup.13 is selected from CN, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-haloalkoxy, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-haloalkylthio, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-haloalkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylsulfonyl and a heterocyclic ring selected from rings of formulae E-1 to E-51; and each R.sup.16 as a substituent on heterocyclic rings of formulae E-1 to E-51 is independently selected from the group consisting of halogen, cyano, nitro, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio, C.sub.1-C.sub.4-haloalkylthio, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-halocycloalkyl, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-haloalkenyl, C.sub.2-C.sub.4-alkynyl and C.sub.2-C.sub.4-haloalkynyl; or two R.sup.16 present on the same carbon atom of a saturated heterocyclic ring may form together ═O or ═S.

18. The compound as claimed in claim 14, where R.sup.5 and R.sup.6 are hydrogen.

19. The compound as claimed in claim 1, where B.sup.1, B.sup.2 and B.sup.3 are CR.sup.2.

20. The compound as claimed in claim 19, where B.sup.1 and B.sup.3 are CR.sup.2, where R.sup.2 is not hydrogen, and B.sup.2 is CR.sup.2.

21. The compound as claimed in claim 1, where R.sup.2 is selected from the group consisting of hydrogen, halogen, cyano, azido, nitro, —SCN, —SF.sub.5, C.sub.3-C.sub.8-cycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, wherein the four last mentioned aliphatic and cycloaliphatic radicals may be partially or fully halogenated and/or may be substituted by one or more radicals R.sup.8, —OR.sup.9, —S(O).sub.nR.sup.9 and —NR.sup.10aR.sup.10b.

22. The compound as claimed in claim 21, where R.sup.2 is selected from the group consisting of hydrogen, halogen and C.sub.1-C.sub.2-haloalkyl.

23. The compound as claimed in claim 1, where G.sup.1, G.sup.2, G.sup.3 and G.sup.4 are CR.sup.4; or G.sup.1, G.sup.3 and G.sup.4 are CR.sup.4 and G.sup.2 is N; or G.sup.2, G.sup.3 and G.sup.4 are CR.sup.4 and G.sup.1 is N.

24. The compound as claimed in claim 23, where G.sup.1, G.sup.3 and G.sup.4 are CH and G.sup.2 is CR.sup.4.

25. The compound as claimed in claim 23, where G.sup.1 is N or CH, G.sup.3 and G.sup.4 are CH and G.sup.2 is CR.sup.4.

26. The compound as claimed in claim 1, where R.sup.4 is selected from the group consisting of hydrogen, halogen, cyano, C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl, C.sub.3-C.sub.5-cycloalkyl, C.sub.3-C.sub.5-halocycloalkyl, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-haloalkenyl, C.sub.2-C.sub.4-alkynyl, C.sub.2-C.sub.4-haloalkynyl, C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.4-haloalkoxy, C.sub.1-C.sub.4-alkylthio and C.sub.1-C.sub.4-haloalkylthio.

27. The compound as claimed in claim 1, where R.sup.3a and R.sup.3b are selected, independently of each other, from hydrogen and halogen.

28. An agricultural composition comprising at least one compound of the formula I, as defined in claim 1, a stereoisomer thereof or at least one agriculturally acceptable salt thereof, and at least one inert liquid and/or solid agriculturally acceptable carrier.

29. A veterinary composition comprising at least one compound of the formula I, as defined in claim 1, a stereoisomer thereof and/or at least one veterinarily acceptable salt thereof, and at least one inert liquid and/or solid veterinarily acceptable carrier.

30. A method for controlling invertebrate pests which method comprises treating the pests, their food supply, their habitat or their breeding ground or a plant, plant propagation material, soil, area, material or environment in which the pests are growing or may grow, or the materials, plants, plant propagation material, soils, surfaces or spaces to be protected from invertebrate pest attack or infestation with a pesticidally effective amount of at least one imine compound of the formula I as defined in claim 1, a stereoisomer thereof and/or at least one agriculturally acceptable salt thereof.

31. The method as claimed in claim 30, for protecting plants from attack or infestation by invertebrate pests, which method comprises treating the plants with a pesticidally effective amount of at least one compound of the formula I, a stereoisomer thereof and/or at least one agriculturally acceptable salt thereof.

32. The method as claimed in claim 30, for protecting plant propagation material and/or the plants which grow therefrom from attack or infestation by invertebrate pests, which method comprises treating the plant propagation material with a pesticidally effective amount of at least one compound of the formula I, a stereoisomer thereof and/or at least one agriculturally acceptable salt thereof.

33. Plant propagation material treated with at least one compound of the formula I as defined in claim 1, a stereoisomer thereof and/or at least one agriculturally acceptable salt thereof.

Description

EXAMPLES

(1) The present invention is now illustrated in further details by the following examples, without imposing any limitation thereto.

Preparation Examples

(2) Compounds can be characterized e.g. by coupled High Performance Liquid Chromatography/mass spectrometry (HPLC/MS), by .sup.1H-NMR and/or by their melting points.

(3) Analytical HPLC column:

(4) Method A: Analytical UPLC column: RP-18 column Chromolith Speed ROD, 50×4.6 mm, from Merck KgaA, Germany). Elution: acetonitrile+0.1% trifluoroacetic acid (TFA)/water+0.1% trifluoroacetic acid (TFA) in a ratio of from 5:95 to 95:5 in 5 minutes at 40° C. Flow: 1.8 mL/min. MS-method: ESI positive.

(5) Method B: Analytical UPLC column: Phenomenex Kinetex 1.7 μm XB-C18 100A; 50×2.1 mm from Phenomenex, Germany. Elution: acetonitrile+0.1% trifluoroacetic acid (TFA)/water+0.1% trifluoroacetic acid (TFA) in a ratio from 5:95 to 100:0 in 1.5 min at 60° C. Flow: 0.8 mL/min to 1 mL/min in 1.5 min. MS-method: ESI positive.

(6) 1H-NMR, respectively .sup.13C-NMR: The signals are characterized by chemical shift (ppm, δ [delta]) vs. tetramethylsilane, respectively CDCl.sub.3 for .sup.13C-NMR, by their multiplicity and by their integral (relative number of hydrogen atoms given). The following abbreviations are used to characterize the multiplicity of the signals: m=multiplett, q=quartett, t=triplett, d=doublet and s=singulett.

(7) Abbreviations used are: h for hour(s), min for minute(s), r.t./room temperature for 20-25° C., THF for tetrahydrofuran, OAc for acetate.

C.1 Compound Examples 1

(8) Compound examples 1-1 to 1-20 correspond to compounds of formula C.1:

(9) ##STR00082##
wherein R.sup.2a, R.sup.2b, R.sup.2c, R.sup.4, and R.sup.6 of each synthesized compound is defined in one row of table C.1 below.

(10) The compounds were synthesized in analogy to Synthesis Example S.1.

(11) TABLE-US-00002 TABLE C.1 HPLC-MS: Method, R.sub.t (min) & [M + H].sup.+ Ex. R.sup.2a, R.sup.2b, R.sup.2c R.sup.4 R.sup.6 or 1H-NMR 1-1 Cl, H, Cl CH.sub.3 NHC(═O)—NHCH.sub.2CF.sub.3 A 4.052 557.0 1-2 Cl, H, Cl CH.sub.3 NHC(═O)—NHCH.sub.3 A 4.420 489.1 1-3 Cl, H, Cl CH.sub.3 NHC(═O)—NH- 1H NMR (400 MHz, CDCl.sub.3): δ 9.5 (cyclopropyl) (s, 1H), 8.0 (s, 1H), 7.8 (d, 1H), 7.7- 7.5 (m, 2H), 7.4 (s, 1H), 7.3 (s, 2H), 6.2 (s, 1H), 4.2 (d, 1H), 3.8 (d, 1H), 2.8-2.7 (m, 1H), 2.5 (s, 3H), 2.0-0.5 (m, 4H) 1-4 Cl, H, Cl CH.sub.3 NHC(═O)—NHCH.sub.2- B 1.681 531.0 (cyclopropyl) 1-5 Cl, H, Cl CH.sub.3 NHC(═O)—NHCH.sub.2CH.sub.3 B 1.681 503.2 1-6 Cl, H, Cl CH.sub.3 NHC(═O)—NH.sub.2 A 4.065 474.9 1-7 Cl, H, Cl Cl NHC(═O)—NHCH.sub.3 B 1.446 509.0 1-8 Cl, H, Cl Cl NHC(═O)—NHCH.sub.2CF.sub.2H B 1.475 560.9 1-9 Cl, H, Cl Cl NHC(═O)—NHCH.sub.2CF.sub.3 B 1.502 578.9 1-10 Cl, H, Cl Cl NHC(═O)—NHCH.sub.2CH.sub.3 B 1.319 523.0 1-11 Cl, H, Cl Cl NH-(2-pyridyl) A 3.891 530.9 1-12 Cl, H, Cl Cl NHC(═O)—OCH.sub.3 B 1.471 512.1 1-13 Cl, H, Cl Cl NHC(═O)—NHOCH.sub.3 1H NMR (400 MHz, CDCl.sub.3): δ 8.5- 8.2 (m, 2H), 8.2 (s, 1H), 8.0 (d, 1H), 7.8 (s, 1H), 7.7 (d, 1H), 7.4 (s, 1H), 7.3 (s, 2H), 4.2 (d, 1H), 3.8-3.9 (m, 4H) 1-14 Cl, H, Cl Cl NHC(═S)—NHCH.sub.3 B 1.509 527.1 1-15 Cl, H, Cl Cl NHC(═O)—CH.sub.2CH.sub.3 A 4.466 509.9 1-16 Cl, H, Cl Cl N(CH.sub.3).sub.2 B 1.687 480.1 1-17 Cl, Cl, Cl OCH.sub.3 NHC(═O)—NHCH.sub.3 B 1.448 540.8 1-18 Cl, Cl, Cl OCH.sub.3 NHC(═O)—NHCH.sub.2CF.sub.3 B 1.503 608.9 1-19 Cl, Cl, Cl OCH.sub.3 NHC(═O)—NHCH.sub.2CCH B 1.459 564.8 1-20 Cl, H, Cl Cl OH 1H NMR (400 MHz, CDCl.sub.3): δ 8.5 s, 1H), 7.9 (d, 1H, 7.8 (s, 1H), 7.6 d, 1H), 7.5 (s, 1H, 7.4 (s, 1H), 7.3 s, 2H), 4.2 (d, 1H, 3.8 (d, 1H)

C.2 Compound Examples 2

(12) Compound examples 2-1 to 2-233 correspond to compounds of formula C.2:

(13) ##STR00083##
wherein R.sup.2a, R.sup.2b, R.sup.2c, R.sup.4, and Y of each synthesized compound is defined in one row of table C.2 below.

(14) The compounds were synthesized in analogy to Synthesis Example S.2.

(15) TABLE-US-00003 TABLE C.2 HPLC-MS: Method, R.sub.t (min) & [M + H].sup.+ Ex. R.sup.2a, R.sup.2b, R.sup.2c R.sup.4 Y or 1H-NMR 2-1 Cl, H, Cl CH.sub.3 NHCH.sub.2C(═O)—NHCH.sub.2CF.sub.3 A 4.242 572.0 2-2 Cl, H, Cl CH.sub.3 NHCH.sub.2C(═O)— B 1.348 530.1 NHCH.sub.2(cyclopropyl) 2-3 Cl, H, Cl CH.sub.3 NHCH.sub.2-(2-F—C.sub.6H.sub.4) B 1.521 541.0 2-4 Cl, H, Cl CH.sub.3 NHCH.sub.2-(2-pyridyl) B 1.167 525.9 2-5 Cl, H, Cl CH.sub.3 NH-(3-thiethanyl) B 1.473 506.8 2-6 Cl, H, Cl CH.sub.3 NHCH.sub.2CF.sub.3 B 1.487 515.0 2-7 Cl, H, Cl CH.sub.3 NHCH.sub.2-(4-(OCH.sub.3)—C.sub.6H.sub.4) B 1.508 554.9 2-8 Cl, H, Cl CH.sub.3 NHCH.sub.2-(3-(OCH.sub.3)—C.sub.6H.sub.4) B 1.518 553.1 2-9 Cl, H, Cl CH.sub.3 NHCH.sub.2-(2-thienyl) B 1.511 530.7 2-10 Cl, H, Cl CH.sub.3 NHCH.sub.2-(cyclopropyl) B 1.491 487.1 2-11 Cl, H, Cl CH.sub.3 NH-(1-oxo-thiethan-3-yl) B 1.307 521.1 2-12 Cl, H, Cl CH.sub.3 NHCH.sub.2-(4-thiazolyl) B 1.396 530.0 2-13 Cl, H, Cl CH.sub.3 NH-(1,1-dioxo-thiethan-3-yl) A 4.172 537.0 2-14 Cl, H, Cl CH.sub.3 H B 1.526 418.0 2-15 Cl, H, Cl CH.sub.3 NHCH.sub.2—C.sub.6H.sub.5 B 1.501 523.3 2-16 Cl, H, Cl CH.sub.3 OCH.sub.3 B 1.596 448.0 2-17 Cl, H, Cl F OH 1H NMR (400 MHz, CDCl.sub.3): δ 8.2-8.0 (m, 1H), 7.7-7.5 (m, 2H), 7.4 (s, 1H), 7.3 (s, 2H), 4.2 (d, 1H), 3.9 (d, 1H) 2-18 Cl, H, Cl F NHCH.sub.2C(═O)—NHCH.sub.2CF.sub.3 B 1.397 576.2 2-19 Cl, H, Cl F NHCH.sub.2-(2-pyridyl) B 1.207 528.2 2-20 Cl, H, Cl F NH-(3-thiethanyl) B 1.479 509.1 2-21 Cl, H, Cl F NHCH.sub.2CF.sub.3 B 1.478 519.2 2-22 Cl, H, Cl F OCH.sub.3 B 1.544 452.2 2-23 Cl, H, Cl F NH-(1,1-dioxo-thiethan-3-yl) B 1.361 541.2 2-24 Cl, H, Cl Cl OCH.sub.3 B 1.583 470.0 2-25 Cl, H, Cl Cl OH 1H NMR (400 MHz, CDCl.sub.3): δ 8.1-8.0 (m, 1H), 7.9 (s, 1H), 7.8- 7.7 (m, 1H), 7.4 (s, 1H), 7.3 (s, 2H), 4.2 (d, 1H), 3.9 (d, 1H) 2-26 Cl, H, Cl Cl NHCH.sub.2-(2-pyridyl) B 1.194 544.0 2-27 Cl, H, Cl Cl NHCH.sub.2C(═O)—NHCH.sub.2CF.sub.3 B 1.397 594.0 2-28 Cl, H, Cl Cl NH-(3-thiethanyl) B 1.460 526.9 2-29 Cl, H, Cl Cl NHCH.sub.2CF.sub.3 B 1.462 536.8 2-30 Cl, H, Cl Cl NH-(1-oxo-thiethan-3-yl) B 1.310 543.0 2-31 Cl, H, Cl Cl pyrrolidin-1-yl B 1.514 509.1 2-32 Cl, H, Cl Cl NHCH.sub.2-(4-thiazolyl) B 1.412 552.0 2-33 Cl, H, Cl F NH-(1-oxo-thiethan-3-yl) B 1.304 526.9 2-34 Cl, H, Cl F pyrrolidin-1-yl B 1.473 492.9 2-35 Cl, H, Cl Cl NHCH.sub.2-(3-pyridyl) B 1.162 545.9 2-36 Cl, H, Cl Cl H 1H NMR (400 MHz, CDCl.sub.3): δ 10.5 (s, 1H), 8.0 (d, 1H), 7.8 (s, 1H), 7.7 (d, 1H), 7.4 (s, 1H), 7.3 (s, 2H), 4.2 (d, 1H), 3.9 (d, 1H) 2-37 Cl, H, Cl Cl NHCH.sub.2-(4-pyridyl) B 1.150 544.2 2-38 Cl, H, Cl Cl NH—C.sub.6H.sub.5 B 1.508 530.9 2-39 Cl, H, Cl Cl NHCH.sub.2-(6-Cl-pyrid-3-yl) B 1.447 580.0 2-40 Cl, H, Cl Cl NH-(1,1-dioxo-thiethan-3-yl) B 1.196 557.0 2-41 Cl, H, Cl F NHCH.sub.2-(4-thiazolyl) B 1.396 534.0 2-42 Cl, H, Cl Cl NH-(3-pyridyl) B 1.202 531.9 2-43 Cl, H, Cl CH.sub.3 NHCH.sub.2-(3,3-difluoro- B 1.466 537.3 cyclobut-1-yl) 2-44 Cl, H, Cl Cl NH-(2-pyridyl) B 1.429 531.8 2-45 Cl, H, Cl Cl NH-(4-pyridyl) B 1.170 532.0 2-46 Cl, H, Cl CH.sub.3 NH—CH.sub.2-(2-nitrophenyl) B 1.485 568.3 2-47 Cl, H, Cl Cl N(CH.sub.3)—CH.sub.2-(2-pyridyl) B 1.314 560.0 2-48 Cl, H, Cl Cl NHCH.sub.2-(4-pyrimidyl) B 1.343 546.8 2-49 Cl, H, Cl Cl N(CH.sub.2CH.sub.3)—CH.sub.2-(2- B 1.338 573.8 pyridyl) 2-50 Cl, H, Cl Cl NHCH.sub.2-(2-pyrimidyl) B 1.374 547.4 2-51 Cl, H, Cl CH.sub.3 NHCH.sub.2-(cyclobutyl) B 1.511 501.1 2-52 Cl, H, Cl CH.sub.3 NHCH.sub.2-(cyclopentyl) B 1.546 516.8 2-53 Cl, H, Cl CH.sub.3 NHCH.sub.2-(2-pyrazinyl) B 1.353 525.0 2-54 Cl, H, Cl CH.sub.3 NHCH.sub.2-(3-pyridyl) B 1.128 524.3 2-55 Cl, H, Cl CH.sub.3 NHCH.sub.2-(4-pyridyl) B 1.130 524.2 2-56 Cl, H, Cl CH.sub.3 NH-(2-pyridyl) B 1.351 510.3 2-57 Cl, H, Cl CH.sub.3 NH-(3-pyridyl) B 1.183 510.3 2-58 Cl, H, Cl CH.sub.3 NH-(4-pyridyl) B 1.174 510.3 2-59 Cl, H, Cl CH.sub.3 NHCH.sub.2-(2-pyrimidyl) B 1.355 525.3 2-60 Cl, H, Cl CH.sub.3 NHCH.sub.2-(4-pyrimidyl) B 1.331 525.3 2-61 Cl, H, Cl CH.sub.3 NH—C.sub.6H.sub.5 B 1.514 509.3 2-62 Cl, H, Cl CH.sub.3 N(CH.sub.3)—CH.sub.2-(2-pyridyl) B 1.274 538.3 2-63 Cl, H, Cl CH.sub.3 N(CH.sub.2CH.sub.3)—CH.sub.2-(2- B 1.305 552.3 pyridyl) 2-64 Cl, H, Cl CH.sub.3 N(CH.sub.2CCH)—CH.sub.2-(2- B 1.331 562.3 pyridyl) 2-65 Cl, H, Cl CH.sub.3 N(CH.sub.3)—CH.sub.2-(4-thiazolyl) B 1.438 544.3 2-66 Cl, H, Cl CH.sub.3 N(CH.sub.3)—OCH.sub.3 B 1.448 477.0 2-67 Cl, H, Cl CH.sub.3 NH—CH.sub.2-(2-oxazolyl) B 1.363 514.1 2-68 Cl, H, Cl CH.sub.3 NH-(3-oxetanyl) B 1.223 489.1 2-69 Cl, H, Cl CH.sub.3 pyrrolidin-1-yl B 1.463 487.3 2-70 Cl, H, Cl CH.sub.3 azetidin-1-yl B 1.422 474.8 2-71 Cl, H, Cl CH.sub.3 NH-cyclobutyl B 1.467 487.0 2-72 Cl, H, Cl CH.sub.3 NH—CH.sub.2-(3-isoxazolyl) B 1.383 514.1 2-73 Cl, H, Cl CH.sub.3 N(CH.sub.2CH.sub.3)—CH.sub.2-(4- B 1.467 558.2 thiazolyl) 2-74 Cl, H, Cl CH.sub.3 NHCH.sub.2-(2-thiazolyl) B 1.380 530.2 2-75 Cl, H, Cl CH.sub.3 aziridin-1-yl B 1.502 459.2 2-76 Cl, H, Cl CH.sub.3 morpholino B 1.408 503.0 2-77 Cl, H, Cl CH.sub.3 thiazolidin-3-yl B 1.476 505.1 2-78 Cl, H, Cl CH.sub.3 thiomorpholino B 1.489 519.0 2-79 Cl, H, Cl CH.sub.3 1,1-dioxo-1,4-thiazinan-4- B 1.356 551.2 yl 2-80 Cl, H, Cl CH.sub.3 1-piperidyl B 1.533 501.3 2-81 Cl, H, Cl CH.sub.3 NH-[1-cyano-cycloprop-1- B 1.391 498.0 yl] 2-82 Cl, H, Cl CH.sub.3 NH-(cyclopropyl) B 1.409 473.0 2-83 Cl, H, Cl CH.sub.3 NHCH.sub.2CF.sub.2H B 1.418 497.0 2-84 Cl, H, Cl CH.sub.3 NHCH.sub.2CH.sub.2CF.sub.3 B 1.460 529.0 2-85 Cl, H, Cl CH.sub.3 NHCH.sub.2-[1-cyano- B 1.392 512.1 cycloprop-1-yl] 2-86 Cl, H, Cl CH.sub.3 NHCH.sub.2CH.sub.3 B 1.245 461.0 2-87 Cl, H, Cl CH.sub.3 NHCH.sub.3 B 1.359 447.0 2-88 Cl, H, Cl CH.sub.3 NHCH.sub.2CCH B 1.396 471.0 2-89 Cl, H, Cl CH.sub.3 NHCH.sub.2CH═CH.sub.2 B 1.423 473.0 2-90 Cl, H, Cl CH.sub.3 NHCH.sub.2CH.sub.2CF═CF.sub.2 B 1.477 541.0 2-91 Cl, H, Cl CH.sub.3 NHCH(CH.sub.3).sub.2 B 1.445 475.0 2-92 Cl, H, Cl CH.sub.3 NHCH.sub.2C(CH.sub.3).sub.3 B 1.529 504.8 2-93 Cl, H, Cl CH.sub.3 NHCH.sub.2CH.sub.2CH.sub.3 B 1.445 475.4 2-94 Cl, H, Cl CH.sub.3 NHCH.sub.2CH(CH.sub.3).sub.2 B 1.487 489.0 2-95 Cl, H, Cl CH.sub.3 NHCH.sub.2CN B 1.365 472.0 2-96 Cl, H, Cl CH.sub.3 NHCH(CF.sub.3).sub.2 B 1.546 583.0 2-97 Cl, H, Cl CH.sub.3 NHCH.sub.2CH.sub.2SCH.sub.2CH.sub.3 B 1.476 521.0 2-98 Cl, H, Cl CH.sub.3 NHC(CH.sub.3).sub.2CH.sub.2SCH.sub.3 B 1.534 535.1 2-99 Cl, H, Cl CH.sub.3 NHCH(CH.sub.3)CF.sub.3 B 1.481 529.3 2-100 Cl, H, Cl CH.sub.3 NH-(3,3-difluoro-cyclobut- B 1.451 523.3 1-yl 2-101 Cl, H, Cl CH.sub.3 NHCH.sub.2-(1,2,3-thiadiazol- B 1.386 532.7 4-yl) 2-102 Cl, H, Cl CH.sub.3 NHCH.sub.2-(1,3,4-thiadiazol- B 1.334 531.0 2-yl) 2-103 Cl, H, Cl CH.sub.3 N═S[CH(CH.sub.3).sub.2].sub.2 B 1.355 549.3 2-104 Cl, H, Cl CH.sub.3 N═S(CH.sub.2CH.sub.3).sub.2 B 1.308 521.3 2-105 Cl, H, Cl CH.sub.3 NHCH.sub.2-[2,2-dichloro- B 1.510 557.2 cycloprop-1-yl] 2-106 Cl, H, Cl CH.sub.3 NHCH.sub.2-(1- B 1.120 527.3 methylimidazol-2-yl) 2-107 Cl, H, Cl CH.sub.3 NHCH.sub.2-(5-oxazolyl) B 1.349 514.3 2-108 Cl, H, Cl CH.sub.3 NHCH.sub.2CH.sub.2SCH.sub.3 B 1.544 507.0 2-109 Cl, H, Cl CH.sub.3 NHCH(CH.sub.3)CH.sub.2SCH.sub.3 B 1.551 521.0 2-110 Cl, H, Cl CH.sub.3 NHCH.sub.2-(2-Cl—C.sub.6H.sub.4) B 1.533 557.0 2-111 Cl, H, Cl CH.sub.3 NHCH.sub.2-(2-OCH.sub.3 C.sub.6H.sub.4) B 1.501 557.0 2-112 Cl, H, Cl CH.sub.3 NHCH(CH.sub.3)CH.sub.2SO.sub.2CH.sub.3 B 1.340 553.0 2-113 Cl, H, Cl CH.sub.3 1-oxo-1,4-thiazinan-4-yl B 1.279 535.0 2-114 Cl, H, Cl CH.sub.3 N(CH.sub.2CN) CH.sub.2-(2- B 1.392 564.9 pyridyl) 2-115 Cl, H, Cl CH.sub.3 NHCH.sub.2-(1-CH.sub.3-pyrazol-3-yl) B 1.368 527.3 2-116 Cl, H, Cl CH.sub.3 NHCH.sub.2-(2-CH.sub.3-pyrazol-3-yl) B 1.364 527.3 2-117 Cl, H, Cl CH.sub.3 NHCH.sub.2-(1-CH.sub.3-imidazol- B 1.124 527.3 4-yl) 2-118 Cl, H, Cl CH.sub.3 NHCH.sub.2-(4-oxazolyl) B 1.361 514.3 2-119 Cl, H, Cl CH.sub.3 NHCH.sub.2-(2-oxetanyl) B 1.376 503.3 2-120 Cl, H, Cl CH.sub.3 NH-(3-tetrahydrofuranyl) B 1.358 503.0 2-121 Cl, H, Cl CH.sub.3 NH-[(2-pyridyl)cycloprop-1-yl] B 1.234 550.1 2-122 Cl, Cl, Cl CH.sub.3 OC(CH.sub.3).sub.3 1H NMR (400 MHz, CDCl.sub.3): δ 7.8 (d, 1H), 7.6-7.5 (m, 1H), 7.4 (s, 2H), 4.2 (d, 1H), 3.9 (d, 1H), 2.6 (s, 3H), 1.6 (s, 9H) 2-123 Cl, H, Cl CH.sub.3 NHCH.sub.2-(2-SCH.sub.3—C.sub.6H.sub.4) B 1.539 569.5 2-124 Cl, H, Cl CH.sub.3 NHCH.sub.2CH.sub.2SO.sub.2CH.sub.3 B 1.323 539.4 2-125 Cl, H, Cl CH.sub.3 NHCH.sub.2-(2-SO.sub.2CH.sub.3—C.sub.6H.sub.4) B 1.435 601.5 2-126 Cl, Cl, Cl CH.sub.3 NH-(1,1-dioxo-thiethan-3-yl) B 1.389 571.9 2-127 Cl, Cl, Cl CH.sub.3 NHCH.sub.2C(═O)—NHCH.sub.2CF.sub.3 B 1.439 606.8 2-128 Cl, Cl, Cl CH.sub.3 NHCH.sub.2-(2-pyridyl) B 1.251 558.8 2-129 Cl, H, Cl CH.sub.3 NH-[(1R)-(2-pyridyl)eth-1-yl] B 1.233 538.3 2-130 Cl, H, Cl CH.sub.3 NH-[(1S)-(2-pyridyl)eth-1-yl] B 1.221 538.3 2-131 Cl, Cl, Cl CH.sub.3 NHCH.sub.2CF.sub.3 B 1.500 549.7 2-132 Cl, Cl, Cl CH.sub.3 NHCH.sub.2-(4-thiazolyl) B 1.426 564.9 2-133 Cl, Cl, Cl CH.sub.3 NH-(3-thiethanyl) B 1.492 539.0 2-134 Cl, H, Cl CH.sub.3 NHCH.sub.2-(3-pyridazinyl) B 1.302 525.3 2-135 Cl, H, Cl CH.sub.3 NHCH.sub.2-(4-isoxazolyl) B 1.376 514.2 2-136 Cl, H, Cl CH.sub.3 NHCH.sub.2-(5-thiazolyl) B 1.354 530.3 2-137 Cl, Cl, Cl SCH.sub.3 NHCH.sub.2-(2-pyridyl) B 1.243 592.1 2-138 Cl, Cl, Cl SCH.sub.3 NHCH.sub.2CF.sub.3 B 1.500 581.1 2-139 Cl, Cl, Cl SCH.sub.3 NH-(1,1-dioxo-thiethan-3-yl) B 1.403 605.1 2-140 Cl, Cl, Cl SCH.sub.3 NHCH.sub.2C(═O)—NHCH.sub.2CF.sub.3 B 1.434 640.0 2-141 Cl, Cl, Cl SCH.sub.3 NHCH.sub.2-(4-thiazolyl) B 1.442 598.0 2-142 Cl, Cl, Cl SCH.sub.3 NHCH.sub.2-(2-thiazolyl) B 1.444 598.0 2-143 Cl, Cl, Cl CH.sub.3 NHCH.sub.2-(2-thiazolyl) B 1.449 566.1 2-144 Cl, H, Cl CH.sub.3 NHCH(CH.sub.3)C(═O)— B 1.402 586.2 NHCH.sub.2CF.sub.3 2-145 Cl, H, Cl CH.sub.3 NHCH.sub.2C(═O)—NHCH.sub.2CH.sub.3 B 1.326 518.2 2-146 Cl, H, Cl CH.sub.3 NHCH.sub.2C(═O)— B 1.362 532.2 NHCH(CH.sub.3).sub.2 2-147 Cl, H, Cl CH.sub.3 NHCH.sub.2C(═O)—NHCH.sub.3 B 1.281 504.2 2-148 Cl, H, Cl CH.sub.3 NHCH.sub.2C(═O)— B 1.355 532.3 NHCH.sub.2CH.sub.2CH.sub.3 2-149 Cl, H, Cl CH.sub.3 NHCH.sub.2-(1,3-dioxolan-2-yl) B 1.368 519.2 2-150 Cl, Cl, Cl Cl NHCH.sub.2-(2-pyridyl) B 1.245 580.1 2-151 Cl, Cl, Cl Cl NHCH.sub.2-(2-pyrimidyl) B 1.433 581.1 2-152 Cl, Cl, Cl Cl NHCH.sub.2-(2-thiazolyl) B 1.450 586.1 2-153 Cl, Cl, Cl Cl NHCH.sub.2C(═O)—NHCH.sub.2CF.sub.3 B 1.440 628.1 2-154 Cl, Cl, Cl Cl NHCH.sub.2CF.sub.3 B 1.508 571.1 2-155 Cl, Cl, Cl Cl NH-(1,1-dioxo-thiethan-3-yl) 1H NMR (400 MHz, CDCl.sub.3): δ 7.8 (s, 1H), 7.8-7.6 (m, 2H), 7.4 (s, 2H), 7.1 (d, 1H), 5.0-4.8 (m, 1H), 4.7-4.6 (m, 2H), 4.2 (d, 1H), 4.2-4.0 (m, 2H), 3.9 (d, 1H) 2-156 Cl, H, Cl CH.sub.3 OH B 1.419 434.1 2-157 Cl, Cl, Cl CH.sub.3 OH B 1.472 470.1 2-158 Cl, Cl, Cl SCH.sub.3 OH B 1.466 500.1 2-159 Cl, Cl, Cl Cl OH B 1.477 490.0 2-160 Cl, F, Cl CH.sub.3 OC(CH.sub.3).sub.3 B 1.678 508.2 2-161 Cl, F, Cl CH.sub.3 OH B 1.417 454.0 2-162 Cl, F, Cl CH.sub.3 NHCH.sub.2C(═O)—NHCH.sub.2CF.sub.3 B 1.373 590.2 2-163 Cl, F, Cl CH.sub.3 NH-(1,1-dioxo-thiethan-3-yl) B 1.344 555.2 2-164 Cl, F, Cl CH.sub.3 NHCH.sub.2-(2-pyridyl) B 1.190 542.3 2-165 Cl, F, Cl CH.sub.3 NHCH.sub.2CF.sub.3 B 1.451 533.3 2-166 Cl, F, Cl CH.sub.3 NHCH.sub.2-(2-thiazolyl) B 1.391 548.1 2-167 Cl, Cl, Cl OCH.sub.3 OC(CH.sub.3).sub.3 B 1.651 542.2 2-168 Cl, Cl, Cl OCH.sub.3 OH B 1.424 484.2 2-169 Cl, Cl, Cl OCH.sub.3 NHCH.sub.2C(═O)—NHCH.sub.2CF.sub.3 B 1.434 624.1 2-170 Cl, Cl, Cl OCH.sub.3 NH-(1,1-dioxo-thiethan-3-yl) B 1.410 589.1 2-171 Cl, Cl, Cl OCH.sub.3 NHCH.sub.2-(2-pyridyl) B 1.245 574.1 2-172 Cl, Cl, Cl OCH.sub.3 NHCH.sub.2-(2-thiazolyl) B 1.469 580.1 2-173 Cl, Cl, Cl OCH.sub.3 NHCH.sub.2CH.sub.2CF.sub.3 B 1.537 579.1 2-174 Cl, H, CF.sub.3 CH.sub.3 OC(CH.sub.3).sub.3 B 1.657 524.3 2-175 Cl, Cl, Cl H OC(CH.sub.3).sub.3 B 1.687 512.1 2-176 Cl, H, CF.sub.3 CH.sub.3 OH B 1.413 468.2 2-177 Cl, Cl, Cl H OH B 1.435 456.1 2-178 Cl, H, Cl CH.sub.3 NHNH-(2-pyridyl) B 1.153 525.2 2-179 Cl, H, Cl CH.sub.3 NHN(CH.sub.3)-(2-pyridyl) B 1.201 539.2 2-180 Cl, H, Cl CH.sub.3 NHCH.sub.2CH.sub.2CH.sub.2CH.sub.3 B 1.480 489.2 2-181 Cl, H, CF.sub.3 CH.sub.3 NHCH.sub.2C(═O)—NHCH.sub.2CF.sub.3 B 1.358 606.3 2-182 Cl, H, CF.sub.3 CH.sub.3 NHCH.sub.2-(2-pyridyl) B 1.185 558.4 2-183 Cl, H, CF.sub.3 CH.sub.3 NH-(1,1-dioxo-thiethan-3-yl) B 1.343 571.2 2-184 Cl, H, CF.sub.3 CH.sub.3 NHCH.sub.2-(2-thiazolyl) B 1.384 564.2 2-185 Cl, H, CF.sub.3 CH.sub.3 NHCH.sub.2CH.sub.2CF.sub.3 B 1.450 563.2 2-186 Cl, Cl, Cl H NHCH.sub.2C(═O)—NHCH.sub.2CF.sub.3 B 1.393 594.2 2-187 Cl, Cl, Cl H NH-(1,1-dioxo-thiethan-3-yl) 1H NMR (400 MHz, CDCl.sub.3): δ 8.1-7.7 (m, 4H), 7.4 (s, 2H), 6.9- 6.8 (m, 1H), 5.0-4.8 (m, 1H), 4.8-4.6 (m, 2H), 4.2 (d, 1H), 4.2-4.0 (m, 2H), 3.9 (d, 1H) 2-188 Cl, Cl, Cl H NHCH.sub.2-(2-pyridyl) B 1.211 544.1 2-189 Cl, Cl, Cl H NHCH.sub.2-(2-thiazolyl) B 1.409 552.1 2-190 Cl, Cl, Cl H NHCH.sub.2CH.sub.2CF.sub.3 B 1.470 550.3 2-191 Cl, H, Cl CH.sub.3 NHCH.sub.2-(6-CF.sub.3-pyrid-2-yl) B 1.310 592.3 2-192 Cl, H, Cl CH.sub.3 NHNHC(═O)—NHCH.sub.2CF.sub.3 B 1.317 573.3 2-193 Cl, H, Cl CH.sub.3 NH-(2- B 1.335 517.2 oxotetrahydrofuran-3-yl) 2-194 Cl, H, Cl CH.sub.3 OCH.sub.2-(2-pyridyl) B 1.420 525.3 2-195 Cl, H, Cl CH.sub.3 NH-[2-oxo-1-(2,2,2- B 1.388 598.2 trifluoroethyl)pyrrolidin-3-yl] 2-196 Cl, H, Cl CH.sub.3 OCH.sub.2CH.sub.2CF.sub.3 B 1.593 530.2 2-197 Cl, H, Cl CH.sub.3 NH-(2-pyrazinyl) B 1.421 511.2 2-198 Cl, H, Cl CH.sub.3 NH.sub.2 B 1.310 433.2 2-199 Cl, H, Cl CH.sub.3 NHCH═NOCH.sub.3 B 1.459 490.3 2-200 Cl, H, Cl CH.sub.3 NH-(1-acetylazetidin-3-yl) B 1.284 530.3 2-201 Cl, H, Cl CH.sub.3 NH-(1-methyl-2-oxo- B 1.296 530.3 pyrrolidin-3-yl) 2-202 Cl, H, Cl CH.sub.3 NHCH.sub.2CH.sub.2OH A 3.705 477.0 2-203 Cl, H, Cl CH.sub.3 NHCH.sub.2CH.sub.2OCH.sub.2CH.sub.3 A 4.141 505.0 2-204 Cl, H, Cl CH.sub.3 NHCH.sub.2CH.sub.2OCH.sub.2CF.sub.3 A 4.277 559.0 2-205 Cl, H, Cl CH.sub.3 NH2 B 1.398 434.2 2-206 Cl, H, Cl CH.sub.3 NHCH.sub.2CH.sub.2OCH.sub.3 B 1.353 491.4 2-207 Cl, H, Cl CH.sub.3 NHCH(CH.sub.3)CH.sub.2OCH.sub.3 B 1.393 505.3 2-208 Cl, H, Cl CH.sub.3 NHCH.sub.2CH.sub.2CH.sub.2CF.sub.3 B 1.459 543.0 2-209 Cl, H, Cl CH.sub.3 NHCH.sub.2CF.sub.2CF.sub.3 B 1.494 565.2 2-210 Cl, H, Cl CH.sub.3 NHCH.sub.2CH.sub.2SCF.sub.3 B 1.487 561.4 2-211 Cl, H, Cl CH.sub.3 NHCH.sub.2CH.sub.2OCF.sub.3 B 1.447 545.3 2-212 Cl, H, Cl CH.sub.3 N(CH.sub.3)—CH.sub.2C(═O)— B 1.377 586.4 NHCH.sub.2CF.sub.3 2-213 Cl, H, Cl SCH.sub.3 NHCH.sub.2CF.sub.3 B 1.444 547.1 2-214 Cl, H, Cl SCH.sub.3 pyrrolidin-1-yl B 1.463 519.2 2-215 Cl, H, Cl SCH.sub.3 NHCH.sub.2-(2-pyridyl) B 1.200 556.2 2-216 Cl, H, Cl SCH.sub.3 NHCH.sub.2C(═O)—NHCH.sub.2CF.sub.3 B 1.369 604.2 2-217 Cl, H, Cl SCH.sub.3 NHCH.sub.2-(2-pyrimidyl) B 1.346 557.2 2-218 Cl, H, Cl SCH.sub.3 NHCH.sub.2-(2-thiazolyl) B 1.371 564.0 2-219 Cl, H, Cl SCH.sub.3 NH-(1,1-dioxo-thiethan-3-yl) B 1.331 569.2 2-220 Cl, H, Cl SCH.sub.3 NH-(3-thiethanyl) B 1.425 538.9 2-221 Cl, H, Cl CH.sub.3 NHCH.sub.2C(═O)— B 1.319 528.4 NHCH.sub.2CCH 2-222 Cl, H, Cl CH.sub.3 NHCH.sub.2C(═O)—N(CH.sub.3)— B 1.402 586.4 CH.sub.2CF.sub.3 2-223 Cl, H, Cl CH.sub.3 NH-(4-CF.sub.3-thiazol-2-yl) B 1.407 584.4 2-224 Cl, Cl, Cl CH.sub.3 NHCH.sub.2-(2-pyrimidyl) B 1.397 561.1 2-225 Cl, F, Cl CH.sub.3 NHCH.sub.2-(2-pyrimidyl) B 1.340 543.2 2-226 Cl, H, Cl CH.sub.3 NHCH.sub.2-(5-Cl-pyrid-2-yl) B 1.400 560.1 2-227 Cl, H, CF.sub.3 CH.sub.3 NHCH.sub.2-(2-pyrimidyl) B 1.382 559.2 2-228 Cl, H, Cl CH.sub.3 NHNH-(2-pyrimidyl) B 1.341 526.2 2-229 Cl, H, Cl CH.sub.3 NH-(5-pyrimidyl) B 1.382 511.0 2-230 Cl, H, Cl CH.sub.3 NH-(2-pyrimidyl) B 1.349 511.0 2-231 Cl, H, Cl CH.sub.3 NHCH═NOCH.sub.2CF.sub.3 B 1.527 557.9 2-232 Cl, H, Cl CH.sub.3 NHNHC(═O)— B 1.318 555.4 NHCH.sub.2CHF.sub.2 2-233 Cl, H, Cl CH.sub.3 NHCH.sub.2C(═O)—NHCH.sub.2CN B 1.300 529.3 2-234 Cl, H, Cl CH.sub.3 NH-(3-oxo-isoxazolidin-4-yl) B 1.282 519.9

C.3 Compound Examples 3

(16) Compound examples 3-1 to 3-28 correspond to compounds of formula C.3:

(17) ##STR00084##
wherein R.sup.2a, R.sup.2b, R.sup.2c, R.sup.4, R.sup.5 and R.sup.6 of each synthesized compound is defined in one row of table C.3 below.

(18) The compounds were synthesized in analogy to Synthesis Example S.3.

(19) TABLE-US-00004 TABLE C.3 R.sup.2a, HPLC-MS: R.sup.2b, Method, R.sub.t (min) Ex. R.sup.2c R.sup.4 R.sup.5 R.sup.6 and [M + H].sup.+ 3-1 Cl, H, CH.sub.3 H C(═O)CH.sub.2SCH.sub.2CH.sub.3 B 1.503 521.1 Cl 3-2 Cl, H, CH.sub.3 C.sub.2H.sub.5 H B 1.142 447.3 Cl 3-3 Cl, H, CH.sub.3 C.sub.2H.sub.5 C(═O)CH.sub.2SCH.sub.2CH.sub.3 A 4.639 549.0 Cl 3-4 Cl, H, CH.sub.3 C.sub.2H.sub.5 C(═O)-(cyclopropyl) A 4.547 515.0 Cl 3-5 Cl, H, CH.sub.3 C.sub.2H.sub.5 C(═O)CH.sub.2SO.sub.2CH.sub.3 A 4.214 567.0 Cl 3-6 Cl, H, Cl H H B 1.085 440.8 Cl 3-7 Cl, H, Cl H C(═O)CH.sub.2SCH.sub.2CH.sub.3 B 1.511 542.9 Cl 3-8 Cl, H, Cl H C(═O)CH.sub.2SO.sub.2CH.sub.3 B 1.376 560.9 Cl 3-9 Cl, H, Cl H C(═O) (cyclopropyl) B 1.461 508.9 Cl 3-10 Cl, H, Cl C.sub.2H.sub.5 C(═O)CH.sub.2CF.sub.3 B 1.555 579.2 Cl 3-11 Cl, H, Cl C.sub.2H.sub.5 C(═O)CH.sub.3 B 1.513 511.1 Cl 3-12 Cl, H, Cl C.sub.2H.sub.5 C(═O)C.sub.2H.sub.5 B 1.560 525.1 Cl 3-13 Cl, H, Cl C.sub.2H.sub.5 C(═O)-pyrid-3-yl B 1.395 574.1 Cl 3-14 Cl, H, Cl C.sub.2H.sub.5 C(═O)-pyrid-2-yl B 1.534 574.1 Cl 3-15 Cl, H, Cl C.sub.2H.sub.5 C(═O)-2,3- B 1.601 609.2 Cl difluorophenyl 3-16 Cl, H, Cl C.sub.2H.sub.5 C(═O)C.sub.6H.sub.5 B 1.598 573.1 Cl 3-17 Cl, H, Cl C.sub.2H.sub.5 C(═O)-(cyclopropyl) B 1.566 537.1 Cl 3-18 Cl, H, Cl C.sub.2H.sub.5 C(═O)CH.sub.2SO.sub.2CH.sub.3 B 1.455 589.1 Cl 3-19 Cl, H, Cl C.sub.2H.sub.5 C(═O)CH.sub.2SCH.sub.2CH.sub.3 B 1.596 571.0 Cl 3-20 Cl, H, Cl C.sub.2H.sub.5 C(═O)CH.sub.2SCF.sub.3 B 1.603 611.0 Cl 3-21 Cl, H, Cl H C(═O)C.sub.2H.sub.5 B 1.430 497.2 Cl 3-22 Cl, H, Cl H C(═O)NHCH.sub.2CF.sub.3 B 1.424 566.2 Cl 3-23 Cl, H, Cl H C(═O)CH.sub.3 B 1.379 481.1 Cl 3-24 Cl, H, Cl H C(═O)CH.sub.2CF.sub.3 B 1.462 551.2 Cl 3-25 Cl, H, Cl C.sub.2H.sub.5 C(═O)CH(CH.sub.3).sub.2 B 1.591 537.2 Cl 3-26 Cl, H, Cl H C(═O)NHCH.sub.2CH.sub.3 B 1.399 512.1 Cl 3-27 Cl, H, Cl H C(═O)CH(CH.sub.3).sub.2 B 1.497 509.2 Cl 3-28 Cl, H, Cl C.sub.2H.sub.5 C(═O)-(1,1- B 1.495 601.2 Cl dioxothietan-3-yl)

C.4 Compound Examples 4

(20) Compound example 4-1 corresponds to compounds of formula C.4:

(21) ##STR00085##
wherein R.sup.2a, R.sup.2b, R.sup.2c, R.sup.4, and A.sup.4 of each synthesized compound is defined in one row of table C.4 below.

(22) Compound 4-1 was synthesized in analogy to Synthesis Example S.2. The starting material (2-(1,2,4-triazol-1-yl)-5-[(Z)-4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-2-enoyl]benzonitrile) was prepared in analogy to the method described in EP-A-2172462.

(23) TABLE-US-00005 TABLE C.4 HPLC-MS: Method, R.sub.t (min) Ex. R.sup.2a, R.sup.2b, R.sup.2c —R.sup.4 A.sup.4 and [M + H].sup.+ 4-1 Cl, Cl, Cl —CN 1,2,4-triazol-1-yl B 1.463 504.1

C.5 Compound Examples 5

(24) Compound examples 5-1 to 5-15 correspond to compounds of formula C.5:

(25) ##STR00086##
wherein R.sup.2a, R.sup.2b, R.sup.2c, R.sup.3a, G.sup.1, R.sup.4a, R.sup.4b, and Y of each synthesized compound is defined in one row of table C.5 below.

(26) Compounds 5-1 to 5-3 were synthesized in analogy to Synthesis Example S.4.

(27) Compounds 5-4 to 5-15 were synthesized in analogy to Synthesis Example S.2.

(28) TABLE-US-00006 TABLE C.5 HPLC-MS: Method, R.sub.t (min) & [M + H].sup.+ Ex. R.sup.2a, R.sup.2b, R.sup.2c R.sup.3a G.sup.1 R.sup.4a R.sup.4b Y or .sup.1H-NMR 5-1 Cl, H, Cl F CH H CH.sub.3 NHCH.sub.2C(═O)—NHCH.sub.2CF.sub.3 B 1.364 590.2 5-2 Cl, H, Cl F CH H CH.sub.3 NHCH.sub.2-(2-pyridyl) B 1.192 543.9 5-3 Cl, H, Cl F CH H CH.sub.3 NH-(1,1-dioxo-thiethan-3-yl) 1H NMR (400 MHz, CDCl.sub.3): δ 7.8-7.7 (m, 2H), 7.5-7.4 (m, 2H), 7.3 (s, 2H), 6.5 (d, 1H), 6.3 (d, 1H, CHF), 5.0-4.8 (m, 1H), 4.7- 4.5 (m, 2H), 4.1-3.9 (m, 2H), 2.5 (s, 3H) 5-4 Cl, Cl, Cl H N H CH.sub.3 NHCH.sub.2C(═O)—NHCH.sub.2CF.sub.3 B 1.432 608.8 5-5 Cl, Cl, Cl H N H CH.sub.3 NHCH.sub.2-(2-pyridyl) B 1.254 559.2 5-6 Cl, Cl, Cl H N H CH.sub.3 NHCH.sub.2-(2-pyrimidyl) B 1.396 561.8 5-7 Cl, Cl, Cl H N H CH.sub.3 NH-(1,1-dioxo-thiethan-3-yl) B 1.376 573.7 5-8 Cl, Cl, Cl H N H CH.sub.3 NHCH.sub.2CH.sub.2CF.sub.3 B 1.504 563.9 5-9 Cl, Cl, Cl H CCH.sub.3 CH.sub.3 H OCH.sub.3 1H NMR (400 MHz, CDCl.sub.3): δ 7.7 (s, 2H), 7.4 (s, 2H), 4.0 (d, 1H), 3.9 (s, 3H), 3.6 (d, 1H), 2.3 (s, 6H) 5-10 Cl, Cl, Cl H CCH.sub.3 CH.sub.3 H NHCH.sub.2C(═O)—NHCH.sub.2CF.sub.3 B 1.445 621.8 5-11 Cl, Cl, Cl H CCH.sub.3 CH.sub.3 H NHCH.sub.2-(2-pyridyl) B 1.256 574.1 5-12 Cl, Cl, Cl H CCH.sub.3 CH.sub.3 H NHCH.sub.2CF.sub.3 B 1.512 564.9 5-13 Cl, Cl, Cl H CCH.sub.3 CH.sub.3 H NHCH.sub.2-(2-thiazolyl) B 1.447 579.8 5-14 Cl, Cl, Cl H CCH.sub.3 CH.sub.3 H NHCH.sub.2-(2-pyrimidyl) B 1.415 574.8 5-15 Cl, Cl, Cl H CCH.sub.3 CH.sub.3 H NH-(1,1-dioxo-thiethan-3-yl) B 1.436 585.1

C.6 Compound Examples 6

Intermediates

(29) Intermediates 6-1 to 6-7 correspond to compounds of formula C.6:

(30) ##STR00087##
wherein R.sup.2a, R.sup.2b, R.sup.2c, R.sup.4, and YY of each synthesized compound is defined in one row of table C.6 below.

(31) TABLE-US-00007 HPLC-MS: Method, R.sub.t (min) & [M + H].sup.+ Ex. R.sup.2a, R.sup.2b, R.sup.2c R.sup.4 YY or 1H-NMR 6-1 Cl, H, Cl CH.sub.3 Br 1H NMR (400 MHz, CDCl.sub.3): δ 7.7-7.5 (m, 2H), 7.5- 7.3 (m, 2H), 7.3 (s, 2H), 4.2 (d, 1H), 3.8 (d, 1H), 2.4 (s, 3H) 6-2 Cl, H, Cl Cl Br B 1.676 489.8 6-3 Cl, H, Cl F Br 1H NMR (400 MHz, CDCl.sub.3): δ 7.7-7.5 (m, 2H), 7.5- 7.3 (m, 2H), 7.3 (s, 2H), 4.2 (d, 1H), 3.8 (d, 1H) 6-4 Cl, H, Cl Cl CH.sub.2OH 1H NMR (400 MHz, CDCl.sub.3): δ 7.8 (s, 1H), 7.7-7.5 (m, 2H), 7.4 (s, 1H), 7.3, (s, 2H), 4.8 (s, 2H), 4.2 (d, 1H), 3.8 (d, 1H), 1.7 (br. s, 1H) 6-5 Cl, Cl, Cl OCH.sub.3 CH.sub.2OH 1H NMR (400 MHz, CDCl.sub.3): δ 7.5-7.4 (m, 3H), 7.3 (d, 1H), 7.2 (d, 1H), 4.7 (s, 2H), 4.2 (d, 1H), 3.9 (s, 3H), 3.8 (d, 1H) 6-6 Cl, H, Cl Cl CH.sub.2N.sub.3 1H NMR (400 MHz, CDCl.sub.3): δ 7.8 (s, 1 H), 7.7 (d, 1H), 7.5 (d, 1H), 7.4 (s, 1H), 7.3, (s, 2H), 4.5 (s, 2H), 4.2 (d, 1H), 3.8 (d, 1H) 6-7 Cl, H, Cl CH.sub.3 CH.sub.2OH 1H NMR (400 MHz, CDCl.sub.3): δ 7.7-7.5 (m, 2H), 7.5 (d, 1H), 7.4 (s, 1H), 7.3, (s, 2H), 4.7 (s, 2H), 4.2 (d, 1H), 3.8 (d, 1H), 2.4 (s, 3H), 1.7 (br. s, 1H)

Synthesis Example S.1

1-[(E)-[4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-phenyl]methyleneamino]-3-ethyl-urea

(32) (Compound example 1-5; compound of formula IA, wherein R.sup.2a and R.sup.2c are Cl, R.sup.2 is H, R.sup.4 is methyl and A is A.sup.1=—CH(═N—NH—C(═O)—NH—CH.sub.2CH.sub.3).

Step 1: 1-(4-Bromo-3-methyl-phenyl)-3-(3,5-dichlorophenyl)-3-sulfanyl-butan-1-one

(33) 1-(4-Bromo-3-methyl-phenyl)-3-(3,5-dichlorophenyl)but-2-en-1-one (21.5 g, 4:1-mixture of E/Z-isomers) in CH.sub.2Cl.sub.2 (400 mL) was treated with triethylamine (68 mL). At 0° C., gaseous hydrogen sulfide (H.sub.2S) was bubbled through the solution for 10 min. The mixture was stirred for another 20 min at 0° C., and then diluted with CH.sub.2Cl.sub.2 (300 mL). The organic layer was washed with 6% aqueous hydrochloric acid (300 mL), dried (MgSO.sub.4), filtered, and concentrated.

(34) The product was obtained as a yellowish oil (23.1 g, 99.7%).

(35) HPLC-MS (method B): 1.557 min, M=472.90.

Step 2: 3-(4-Bromo-3-methyl-phenyl)-5-(3,5-dichlorophenyl)-5-methyl-4H-isothiazole

(36) At −15° C., the product of step 1 (23 g) in CH.sub.2Cl.sub.2 (400 mL) was treated with triethylamine (27.1 mL) and with a solution of hydroxylamine-O-sulfonic acid (“HOSA”, 6.23 g) in water (10 mL). The reaction was warmed to 0° C. and stirred at 0° C. for 45 min, and then diluted with CH.sub.2Cl.sub.2 (400 mL). The organic layer was washed with saturated aqueous NH.sub.4Cl solution (3×), dried (MgSO.sub.4), and filtered. To the obtained solution, acid washed molecular sieves (AW 300, 150 g) were added and the mixture was stirred vigorously for 90 min at room temperature. Then, the molecular sieves were filtered off, and the filtrate concentrated to afford a residue that was purified by flash chromatography on silica gel (ethyl acetate/cyclohexane). The obtained pale yellow solid (19.5 g) was titurated with hexanes (3×) to afford the product as a white solid (15.6 g, 68%).

(37) HPLC-MS (method B): 1.697 min, M=469.90.

Step 3: Methyl 4-[5-(3,5-dichlorophenyl)-5-methyl-4H-isothiazol-3-yl]-2-methyl-benzoate

(38) The product of step 2 (14.6 g) in methanol/THF (63 mL/6 mL) was treated with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (“Pd(dppf)Cl.sub.2”, 5.08 g), Pd(OAc).sub.2 (0.42 g), NaOAc (3.7 g). The reaction was subsequently pressurized twice with N.sub.2 (3.5 bar) and three times with carbon monoxide (5 bar). Then, the mixture was pressurized with carbon monoxide (7.5 bar) and heated at 80° C. (internal temperature) for 13 h. Thereby, the carbon monoxide pressure was adjusted several times back to 7.5 bar. Then, the reaction was cooled to room temperature, filtered over celite (CH.sub.2Cl.sub.2) and subsequently filtered over a plug of silica gel. The product was obtained as a pale yellow foam (13.1 g, 89%).

(39) HPLC-MS (method A): 3.974 min, M=566.00.

Step 4: [4-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-phenyl]methanol

(40) To a solution of the product of step 3 (4.9 g) in CH.sub.2Cl.sub.2 (100 mL) at 0° C. was added a solution of DIBAL-H in toluene (1.5 M, 16 mL). The resulting solution was stirred at 0° C. for 90 min and quenched by adding MeOH (10 mL). A saturated solution of Rochelle's salt (potassium sodium tartrate, CAS 304-59-6) (100 mL) was added, followed by vigorous stirring at r.t. for 2 h. Then, CH.sub.2Cl.sub.2 (300 mL) was added, and the organic layer was washed with water, dried (Na.sub.2SO.sub.4), filtered, and concentrated to afford a residue that was purified by flash chromatography on silica gel (ethyl acetate/hexanes).

(41) The product was obtained as pale yellow solid (3.45 g, 75%).

(42) HPLC-MS (methode A): 4.390 min, M=419.95.

Step 5: 4-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methylbenzaldehyde

(43) To a solution of the product of step 1 (1 g) in CH.sub.2Cl.sub.2 (40 mL) at r.t. was added DessMartin-Periodane (CAS 87413-09-0) (1.11 g). The reaction was stirred overnight, filtered and concentrated. The residue was purified by flash chromatography on silica gel (ethyl acetate/cyclohexane). The product was obtained as a viscous oil (0.81 g, 81%).

(44) HPLC-MS (method A): 4.036 min, M=417.90.

Step 6: 1-[(E)-[4-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-phenyl]methyleneamino]-3-ethyl-urea

(45) A solution of the product of step 2 (0.15 g) and 1-ammonium-3-ethyl urea hydrochloride (60 mg) in EtOH (4 mL) and acetic acid (0.14 mL) was stirred at 70° C. overnight, and concentrated. The residue was purified by flash chromatography on silica gel (ethyl acetate/cyclohexane). The product was obtained as a pale yellow foam (0.10 g, 55%).

(46) HPLC-MS (method B): 1.484 min, M=505.0.

Synthesis Example S.2

4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4H-isothiazol-3-yl]-2-methyl-N-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]benzamide

(47) (Compound example 2-1; compound of formula IA, wherein R.sup.2a and R.sup.2c are Cl, R.sup.2 is H, R.sup.4 is methyl and A is A.sup.2=—C(═O)—NH—CH.sub.2—C(═O)—NH—CH.sub.2CF.sub.3)

Step 1: 4-[5-(3,5-dichlorophenyl)-5-methyl-4H-isothiazol-3-yl]-2-methyl-benzoic acid

(48) To a solution of methyl 4-[5-(3,5-dichlorophenyl)-5-methyl-4H-isothiazol-3-yl]-2-methyl-benzoate (=the product of step 3 of example 1) (2.4 g) in THF (50 mL) was added a solution of LiOH (0.51 g) in water (50 mL). The reaction was stirred for 16 h at room temperature, then diluted with water (300 mL) and washed with CH.sub.2Cl.sub.2 (3×). The aqueous phase was acidified with aqueous 1 M HCl to pH 1-2 and extracted with CH.sub.2Cl.sub.2 (3×). The combined organic layers were washed with water, dried (Na.sub.2SO.sub.4), filtered, and concentrated. The product was obtained as a pale yellow solid (2.24 g, 96%).

(49) HPLC-MS (method A): 4.458 min, M=433.95.

Step 2: 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4H-isothiazol-3-yl]-2-methyl-N-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]benzamide

(50) To a solution of the product of step 1 (2.2 g), [2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]ammonium chloride (1.22 g) and bromotripyrrolidinophosphonium hexafluorophosphate (“PyBroP”, 2.95 g) in CH.sub.2Cl.sub.2 (100 mL) at room temperature was added N,N-diisopropylethylamine (3.53 mL). The reaction was stirred at room temperature for 16 h, then concentrated and redissolved in ethyl acetate (200 mL). The organic layer was washed with 5% aqueous HCl (2×) and 5% aqueous K.sub.2CO.sub.3 (2×), dried (Na.sub.2SO.sub.4), filtered, and concentrated to afford a residue that was purified by flash chromatography on silica gel (ethyl acetate/cyclohexane). The product was obtained as amorphous white foam (2.45 g, 84%).

(51) HPLC-MS (method A): 4.045 min, M=572.00.

Synthesis Example S.3

N-[[4-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-phenyl]methyl]-N-ethyl-2-ethylsulfanyl-acetamide

(52) (Compound example 3-3; compound of formula IA, wherein R.sup.2a and R.sup.2c are Cl, R.sup.2 is H, R.sup.4 is methyl and A is A.sup.3=—CH.sub.2—N(CH.sub.2CH.sub.3)—C(═O)—CH.sub.2SCH.sub.2CH.sub.3).

Step 1: N—[[4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-phenyl]methyl]ethanamine

(53) To a solution of [4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-phenyl]methanol (i.e. the product of example 1, step 4) (1.5 g) in CH.sub.2Cl.sub.2 (50 mL) was added triethylamine (0.75 mL) and methansulfonylchloride (0.63 g) at r.t. The reaction was stirred at r.t. overnight, then diluted with ethyl acetate (200 mL), and washed with water (3×), dried (Na.sub.2SO.sub.4), filtered, and concentrated to afford the crude mesylate (1.19 g) that was re-dissolved in acetonitrile (30 mL) and treated with a solution of ethylamine in THF (2 M, 8.8 mL). The reaction was stirred overnight at r.t. The residue was taken up in ethyl acetate and washed with 5% aqueous potassium carbonate solution (3×), dried (Na.sub.2SO.sub.4), filtered, and concentrated to afford the product as a solid (0.98 g, 59%).

(54) HPLC-MS (method B): 1.139 min, M=447.3.

Step 2: N—[[4-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-phenyl]methyl]-N-ethyl-2-ethylsulfanyl-acetamide

(55) To a solution of the product of step 1 (0.30 g), (ethylthio)acetic acid (0.10 g) and bromotripyrrolidinophosphonium hexafluorophosphate (“PyBroP”, 0.39 g) in CH.sub.2Cl.sub.2 (20 mL) at r.t. was added N,N-diisopropylethylamine (0.47 mL). The reaction was stirred at r.t. for 16 h, then concentrated to afford a residue that was purified by flash chromatography on silica gel (ethyl acetate/cyclohexane). The product was obtained as amorphous foam (330 mg, 90%).

(56) HPLC-MS (method A): 4.639 min, M=549.00.

Synthesis Example S.4

4-[5-(3,5-dichlorophenyl)-4-fluoro-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-N-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]benzamide

(57) (Compound example 5-1; compound of formula C.5, wherein R.sup.2a and R.sup.2c are Cl, R.sup.2b is H, R.sup.3a is F, G is CH, R.sup.4a is H, R.sup.4b is methyl and Y is —NHCH.sub.2—C(═O)—NHCH.sub.2CF.sub.3).

Step 1: tert-butyl 4-[5-(3,5-dichlorophenyl)-4-fluoro-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-benzoate

(58) To a solution of [tert-butyl 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-benzoate (prepared from “tert-butyl 4-[(Z)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-but-2-enoyl]-2-methyl-benzoate” in analogy to Synthesis Example S.1, step 1 and step 2) (2.55 g) in THF (40 mL) under nitrogen at −78° C. was added LiHMDS (5.7 mL, 1M solution in THF) and the mixture was stirred for 1.5 h at −78° C. Then, N-fluorobenzenesulfonimide (“NFSI”, 2.1 g) was added at −78° C. in one portion and the mixture was stirred at −78° C. for another 2 h. Then, the reaction was quenched with saturated aqueous NH.sub.4Cl solution. EtOAc was added and the organic layer was washed with water (3×), dried (Na.sub.2SO.sub.4), filtered, and concentrated to afford a residue that was purified by flash chromatography on silica gel (ethyl acetate/cyclohexane). The product was obtained as yellow oil (1.65 g, 62%).

(59) 1H NMR (400 MHz, CDCl.sub.3, signals of major diastereomer): δ 7.9 (d, 1H), 7.7-7.6 (m, 2H), 7.5 (s, 1H), 7.4 (s, 2H), 6.4 (d, 1H, CHF), 2.6 (s, 3H), 1.6 (s, 9H).

Step 2: 4-[5-(3,5-dichlorophenyl)-4-fluoro-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-benzoic acid

(60) To a solution of the product of step 1 (0.36 g) in CH.sub.2Cl.sub.2 (20 mL) at 0° C. was added trifluoroacetic acid (“TFA”, 10 mL), and the mixture was stirred at r.t. overnight. Then, the reaction was concentrated, azeotroped with CH.sub.2Cl.sub.2 (5×) and triturated with petroleum ether/EtOAc (40:1) to obtain the product as a pale yellow solid (0.28 g, 87%).

(61) 1H NMR (400 MHz, d6-DMSO, signals of major diastereomer): δ 8.0-7.8 (m, 4H), 7.7 (s, 2H), 7.5 (d, 1H, CHF), 2.6 (s, 3H).

Step 3: 4-[5-(3,5-dichlorophenyl)-4-fluoro-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-N-[2-oxo-2-(2,2,2-trifluoroethylamino)ethyl]benzamide

(62) To a solution of the product of step 2 (0.25 g) in toluene/CH.sub.2Cl.sub.2 (1:1, 20 mL) was added N,N-dimethylformamide (“DMF”, 1 drop) and oxalyl chloride (0.14 mL). The reaction was stirred overnight, concentrated, and azeotroped with CH.sub.2Cl.sub.2 (5×). The obtained residue (0.26 g) was dissolved in THF (30 mL) and added to a solution of 2-amino-N-(2,2,2-trifluoroethyl)acetamide hydrochloride and triethylamine (0.22 g) in THF (30 mL). The reaction was stirred overnight, filtered and concentrated to afford a residue that was purified by flash chromatography on silica gel (ethyl acetate/cyclohexane). The product was obtained as amorphous foam (0.13 g, 40%).

(63) HPLC-MS (method B): 1.364 min, M=590.2.

(64) II. Evaluation of Pesticidal Activity:

(65) The activity of the compounds of formula I of the present invention can be demonstrated and evaluated by the following biological test.

(66) B.1 Cotton Aphid (Aphis gossypii)

(67) The active compounds were formulated in cyclohexanone as a 10,000 ppm solution supplied in tubes. The tubes were inserted into an automated electrostatic sprayer equipped with an atomizing nozzle and they served as stock solutions for which lower dilutions were made in 50% acetone:50% water (v/v). A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01% (v/v).

(68) Cotton plants at the cotyledon stage were infested with aphids prior to treatment by placing a heavily infested leaf from the main aphid colony on top of each cotyledon.

(69) Aphids were allowed to transfer overnight to accomplish an infestation of 80-100 aphids per plant and the host leaf was removed. The infested plants were then sprayed by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood, removed from the sprayer, and then maintained in a growth room under fluorescent lighting in a 24-hr photoperiod at 25° C. and 20-40% relative humidity. Aphid mortality on the treated plants, relative to mortality on untreated control plants, was determined after 5 days.

(70) In this test, the compounds 2-4, 2-10, 2-12, 2-15, 2-19, 2-26, 2-27, 2-28, 2-29, 2-31, 2-32, 2-35, 2-37, 2-38, 2-42, 2-43, 2-47, 2-48, 2-49, 2-50, 2-53, 2-57, 2-59, 2-62, 2-63, 2-65, 2-68, 2-71, 2-72, 2-73, 2-74, 2-75, 2-82, 2-83, 2-86, 2-88, 2-93, 2-99, 2-109, 2-118, 2-137, 2-138, 2-142, 2-143, 2-145, 2-149, 2-150, 2-151, 2-152, 2-153, 2-162, 2-163, 2-164, 2-166, 2-171, 2-178, 2-182, 2-183, 2-185, 2-195, 2-199, 3-11, and 3-12 at 100 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

(71) B.2 Cowpea Aphid (Aphis craccivora)

(72) Potted cowpea plants colonized with approximately 100-150 aphids of various stages were sprayed after the pest population had been recorded. Population reduction was assessed after 24, 72, and 120 hours.

(73) In this test, the compounds 1-13, 2-1, 2-2, 2-4, 2-8, 2-9, 2-10, 2-11, 2-12, 2-15, 2-19, 2-26, 2-28, 2-32, 2-33, 2-34, 2-35, 2-36, 2-38, 2-47, 2-51, 2-54, 2-55, 2-59, 2-69, 2-137, 2-142, 2-150, 2-151, 2-152, 2-162, 2-164, 2-165, 2-166, 2-178, 2-180, 2-181, 2-182, 2-184, 2-185, 2-197, 2-199, 2-200, 2-215, 2-217, 2-218, 2-220, 2-223, 2-224, 2-225, 2-227, 3-1, 3-2, 3-8, 3-9, 3-11, 3-12, 3-21, 3-23, 4-1, and 5-2 at 500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

(74) B.3 Diamond Back Moth (Plutella xylostella)

(75) Leaves of Chinese cabbage were dipped in test solution and air-dried. Treated leaves were placed in petri dished lined with moist filter paper. Mortality was recorded 24, 72, and 120 hours after treatment.

(76) In this test, the compounds 1-1, 1-2, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1-11, 1-12, 1-13, 1-15, 2-1, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-11, 2-12, 2-13, 2-15, 2-18, 2-19, 2-20, 2-21, 2-22, 2-23, 2-26, 2-27, 2-28, 2-29, 2-30, 2-31, 2-32, 2-33, 2-34, 2-35, 2-36, 2-37, 2-38, 2-39, 2-40, 2-41, 2-42, 2-43, 2-44, 2-45, 2-46, 2-47, 2-48, 2-49, 2-50, 2-51, 2-52, 2-53, 2-54, 2-55, 2-56, 2-57, 2-58, 2-59, 2-60, 2-61, 2-62, 2-63, 2-64, 2-65, 2-66, 2-67, 2-68, 2-69, 2-70, 2-71, 2-72, 2-73, 2-74, 2-75, 2-76, 2-77, 2-78, 2-80, 2-81, 2-82, 2-83, 2-84, 2-85, 2-86, 2-87, 2-88, 2-89, 2-90, 2-91, 2-92, 2-93, 2-94, 2-95, 2-96, 2-97, 2-98, 2-99, 2-100, 2-101, 2-102, 2-103, 2-104, 2-105, 2-106, 2-107, 2-108, 2-109, 2-111, 2-112, 2-114, 2-115, 2-116, 2-117, 2-118, 2-119, 2-120, 2-121, 2-123, 2-124, 2-125, 2-126, 2-127, 2-128, 2-129, 2-130, 2-131, 2-132, 2-133, 2-134, 2-135, 2-136, 2-137, 2-138, 2-139, 2-140, 2-141, 2-142, 2-143, 2-144, 2-145, 2-146, 2-147, 2-148, 2-149, 2-150, 2-151, 2-152, 2-153, 2-154, 2-155, 2-162, 2-163, 2-164, 2-165, 2-166, 2-169, 2-170, 2-171, 2-172, 2-173, 2-178, 2-179, 2-180, 2-181, 2-182, 2-183, 2-184, 2-185, 2-186, 2-188, 2-189, 2-190, 2-191, 2-192, 2-193, 2-194, 2-195, 2-197, 2-198, 2-199, 2-200, 2-201, 2-202, 2-203, 2-204, 2-206, 2-207, 2-208, 2-209, 2-210, 2-211, 2-212, 2-213, 2-214, 2-215, 2-216, 2-217, 2-218, 2-219, 2-220, 2-221, 2-222, 2-223, 2-224, 2-225, 2-226, 2-227, 3-1, 3-2, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9, 3-10, 3-11, 3-12, 3-13, 3-14, 3-16, 3-17, 3-18, 3-19, 3-20, 3-21, 3-22, 3-23, 3-24, 3-25, 3-26, 3-27, 4-1, 5-1, 5-2, 5-3, 5-4, 5-5, 5-6, 5-7, and 5-8 at 500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

(77) B.4 Green Peach Aphid (Myzus persicae)

(78) For evaluating control of green peach aphid (Myzus persicae) through systemic means the test unit consisted of 96-well-microtiter plates containing liquid artificial diet under an artificial membrane.

(79) The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were pipetted into the aphid diet, using a custom built pipetter, at two replications.

(80) After application, 5-8 adult aphids were placed on the artificial membrane inside the microtiter plate wells. The aphids were then allowed to suck on the treated aphid diet and incubated at about 23±1° C. and about 50±5% relative humidity for 3 days. Aphid mortality and fecundity was then visually assessed.

(81) In this test, the compounds 1-1, 1-2, 1-3, 1-4, 1-5, 1-7, 1-8, 1-9, 1-10, 1-12, 1-13, 1-14, 1-15, 2-1, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-11, 2-12, 2-13, 2-15, 2-18, 2-19, 2-20, 2-21, 2-23, 2-24, 2-26, 2-27, 2-28, 2-29, 2-30, 2-31, 2-32, 2-33, 2-35, 2-37, 2-38, 2-39, 2-40, 2-41, 2-42, 2-43, 2-44, 2-45, 2-46, 2-47, 2-48, 2-49, 2-51, 2-52, 2-53, 2-54, 2-55, 2-56, 2-57, 2-58, 2-59, 2-60, 2-61, 2-62, 2-63, 2-64, 2-65, 2-66, 2-67, 2-68, 2-69, 2-70, 2-71, 2-72, 2-73, 2-74, 2-75, 2-76, 2-77, 2-81, 2-82, 2-83, 2-84, 2-85, 2-86, 2-87, 2-88, 2-89, 2-90, 2-91, 2-92, 2-93, 2-94, 2-95, 2-96, 2-97, 2-98, 2-99, 2-100, 2-101, 2-102, 2-103, 2-104, 2-105, 2-106, 2-107, 2-108, 2-109, 2-110, 2-111, 2-112, 2-113, 2-114, 2-115, 2-116, 2-117, 2-118, 2-119, 2-120, 2-121, 2-123, 2-124, 2-125, 2-126, 2-127, 2-128, 2-129, 2-130, 2-131, 2-132, 2-133, 2-134, 2-135, 2-136, 2-137, 2-138, 2-139, 2-140, 2-141, 2-142, 2-143, 2-145, 2-146, 2-147, 2-148, 2-149, 2-150, 2-151, 2-152, 2-153, 2-154, 2-155, 2-159, 2-160, 2-162, 2-163, 2-164, 2-165, 2-166, 2-167, 2-168, 2-169, 2-170, 2-171, 2-172, 2-173, 2-177, 2-178, 2-179, 2-180, 2-181, 2-182, 2-183, 2-184, 2-185, 2-186, 2-187, 2-188, 2-189, 2-190, 2-191, 2-192, 2-193, 2-194, 2-195, 2-196, 2-197, 2-199, 2-200, 2-201, 2-202, 2-203, 2-204, 2-206, 2-207, 2-208, 2-209, 2-210, 2-211, 2-215, 2-216, 2-217, 2-218, 2-219, 2-220, 2-221, 2-222, 2-223, 2-224, 2-225, 2-226, 2-227, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9, 3-10, 3-11, 3-12, 3-13, 3-14, 3-16, 3-17, 3-18, 3-19, 3-20, 3-21, 3-22, 3-23, 3-24, 3-25, 3-26, 3-27, 3-28, 4-1, 5-1, 5-2,5-3, 5-4, 5-5, 5-6, 5-7, and 5-8 at 2500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

(82) B.5 Mediterranean Fruitfly (Ceratitis capitata)

(83) For evaluating control of Mediterranean fruitfly (Ceratitis capitata) the test unit consisted of microtiter plates containing an insect diet and 50-80 C. capitata eggs.

(84) The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 5 μl, using a custom built micro atomizer, at two replications.

(85) After application, microtiter plates were incubated at about 28±1° C. and about 80±5% relative humidity for 5 days. Egg and larval mortality was then visually assessed.

(86) In this test, the compounds 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1-11, 1-12, 1-13, 1-14, 2-1, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-11, 2-12, 2-13, 2-15, 2-18, 2-19, 2-20, 2-21, 2-23, 2-26, 2-27, 2-28, 2-29, 2-30, 2-31, 2-32, 2-33, 2-34, 2-35, 2-37, 2-38, 2-39, 2-40, 2-41, 2-42, 2-43, 2-44, 2-45, 2-46, 2-47, 2-48, 2-49, 2-51, 2-52, 2-53, 2-54, 2-55, 2-56, 2-57, 2-58, 2-59, 2-60, 2-61, 2-62, 2-63, 2-64, 2-65, 2-66, 2-67, 2-68, 2-69, 2-70, 2-71, 2-72, 2-73, 2-74, 2-75, 2-76, 2-77, 2-78, 2-80, 2-81, 2-82, 2-83, 2-84, 2-85, 2-86, 2-87, 2-88, 2-89, 2-90, 2-91, 2-92, 2-93, 2-94, 2-95, 2-96, 2-97, 2-98, 2-99, 2-100, 2-101, 2-103, 2-104, 2-105, 2-106, 2-107, 2-108, 2-109, 2-111, 2-112, 2-114, 2-115, 2-116, 2-117, 2-118, 2-119, 2-120, 2-121, 2-123, 2-124, 2-125, 2-126, 2-127, 2-128, 2-129, 2-130, 2-131, 2-132, 2-133, 2-135, 2-138, 2-140, 2-141, 2-142, 2-143, 2-146, 2-147, 2-148, 2-149, 2-150, 2-151, 2-152, 2-153, 2-154, 2-155, 2-162, 2-163, 2-164, 2-165, 2-166, 2-169, 2-170, 2-171, 2-172, 2-178, 2-179, 2-180, 2-181, 2-182, 2-183, 2-184, 2-185, 2-186, 2-187, 2-188, 2-189, 2-190, 2-191, 2-192, 2-194, 2-195, 2-197, 2-198, 2-199, 2-200, 2-201, 2-202, 2-203, 2-206, 2-207, 2-209, 2-212, 2-215, 2-216, 2-217, 2-218, 2-220, 2-221, 2-222, 2-223, 2-224, 2-225, 2-226, 2-227, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9, 3-10, 3-11, 3-12, 3-13, 3-14, 3-16, 3-17, 3-18, 3-19, 3-20, 3-21, 3-22, 3-23, 3-24, 3-25, 3-26, 3-27, 3-28, 4-1, 5-1, 5-2, 5-3, 5-4, and 5-7 at 2500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

(87) B.6 Orchid Thrips (Dichromothrips corbetti)

(88) Dichromothrips corbetti adults used for bioassay were obtained from a colony maintained continuously under laboratory conditions. For testing purposes, the test compound was diluted to a concentration of 500 ppm (wt compound: vol diluent) in a 1:1 mixture of acetone:water (vol:vol), plus 0.01% vol/vol Kinetic® surfactant.

(89) Thrips potency of each compound was evaluated by using a floral-immersion technique. Plastic petri dishes were used as test arenas. All petals of individual, intact orchid flowers were dipped into treatment solution and allowed to dry. Treated flowers were placed into individual petri dishes along with 10-15 adult thrips. The petri dishes were then covered with lids. All test arenas were held under continuous light and a temperature of about 28° C. for duration of the assay. After 4 days, the numbers of live thrips were counted on each flower, and along inner walls of each petri dish. The level of thrips mortality was extrapolated from pre-treatment thrips numbers.

(90) In this test, the compounds 1-1, 1-2, 1-5, 1-7, 1-8, 1-9, 1-10, 1-13 2-1, 2-2, 2-3, 2-4, 2-5,2-6, 2-7, 2-8, 2-9, 2-10, 2-11, 2-12, 2-13, 2-15, 2-18, 2-19, 2-20, 2-21, 2-22, 2-23, 2-26, 2-27, 2-28, 2-29, 2-30, 2-31, 2-33, 2-34, 2-35, 2-37, 2-38, 2-39, 2-40, 2-41, 2-42, 2-43, 2-45, 2-46, 2-47, 2-48, 2-49, 2-50, 2-51, 2-52, 2-53, 2-54, 2-55, 2-56, 2-57, 2-58, 2-59, 2-60, 2-61, 2-62, 2-63, 2-64, 2-65, 2-66, 2-67, 2-68, 2-69, 2-70, 2-71, 2-72, 2-73, 2-74, 2-75, 2-76, 2-77, 2-78, 2-80, 2-81, 2-82, 2-83, 2-84, 2-85, 2-86, 2-87, 2-88, 2-89, 2-90, 2-91, 2-92, 2-93, 2-94, 2-95, 2-96, 2-97, 2-98, 2-99, 2-100, 2-101, 2-102, 2-103, 2-104, 2-105, 2-106, 2-107, 2-108, 2-109, 2-111, 2-112, 2-113, 2-114, 2-115, 2-116, 2-117, 2-118, 2-119, 2-120, 2-121, 2-123, 2-124, 2-125, 2-126, 2-127, 2-128, 2-129, 2-130, 2-131, 2-132, 2-133, 2-134, 2-135, 2-136, 2-137, 2-138, 2-139, 2-140, 2-141, 2-142, 2-143, 2-144, 2-145, 2-146, 2-147, 2-148, 2-149, 2-150, 2-151, 2-152, 2-153, 2-154, 2-155, 2-162, 2-163, 2-164, 2-165, 2-166, 2-169, 2-170, 2-171, 2-172, 2-173, 2-178, 2-179, 2-180, 2-181, 2-182, 2-183, 2-184, 2-185, 2-186, 2-187, 2-188, 2-189, 2-190, 2-192, 2-193, 2-195, 2-197, 2-198, 2-199, 2-200, 2-201, 2-202, 2-203, 2-204, 2-206, 2-207, 2-208, 2-209, 2-210, 2-211, 2-212, 2-213, 2-214, 2-215, 2-216, 2-217, 2-218, 2-219, 2-220, 2-221, 2-222, 2-223, 2-224, 2-225, 2-226, 2-227, 3-1, 3-2, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9, 3-10, 3-11, 3-12, 3-13, 3-14, 3-15, 3-16, 3-17, 3-18, 3-19, 3-20, 3-21, 3-22, 3-23, 3-24, 3-25, 3-26, 3-27, 4-1, 5-1, 5-2, 5-3, 5-4, 5-5, 5-6, 5-7, and 5-8 at 500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

(91) B.7 Rice Green Leafhopper (Nephotettix virescens)

(92) Rice seedlings were cleaned and washed 24 hours before spraying. The active compounds were formulated in 50:50 acetone:water (vol:vol), and 0.1% vol/vol surfactant (EL 620) was added. Potted rice seedlings were sprayed with 5 ml test solution, air dried, placed in cages and inoculated with 10 adults. Treated rice plants were kept at about 28-29° C. and relative humidity of about 50-60%. Percent mortality was recorded after 72 hours.

(93) In this test, the compounds 1-7, 2-1, 2-2, 2-4, 2-5, 2-6, 2-9, 2-10, 2-11, 2-13, 2-15, 2-19, 2-23, 2-26, 2-27, 2-28, 2-29, 2-30, 2-31, 2-32, 2-33, 2-35, 2-37, 2-38, 2-40, 2-41, 2-42, 2-43, 2-45, 2-47, 2-48, 2-49, 2-50, 2-51, 2-52, 2-53, 2-54, 2-55, 2-56, 2-57, 2-58, 2-59, 2-60, 2-61, 2-62, 2-63, 2-64, 2-67, 2-68, 2-69, 2-70, 2-71, 2-72, 2-73, 2-74, 2-81, 2-82, 2-83, 2-84, 2-85, 2-86, 2-88, 2-89, 2-91, 2-93, 2-94, 2-95, 2-97, 2-99, 2-100, 2-101, 2-102, 2-104, 2-107, 2-108, 2-109, 2-112, 2-114, 2-115, 2-116, 2-118, 2-119, 2-120, 2-121, 2-124, 2-126, 2-127, 2-128, 2-129, 2-131, 2-132, 2-133, 2-134, 2-135, 2-136, 2-137, 2-138, 2-139, 2-140, 2-141, 2-142, 2-143, 2-145, 2-146, 2-147, 2-148, 2-149, 2-150, 2-151, 2-152, 2-153, 2-154, 2-155, 2-162, 2-163, 2-164, 2-165, 2-166, 2-170, 2-178, 2-179, 2-180, 2-181, 2-182, 2-183, 2-184, 2-185, 2-193, 2-195, 2-197, 2-199, 2-200, 2-201, 2-203, 2-204, 2-206, 2-207, 2-208, 2-209, 2-210, 2-211, 2-212, 2-213, 2-214, 2-215, 2-216, 2-217, 2-218, 2-219, 2-220, 2-222, 2-224, 2-225, 2-226, 2-227, 3-3, 3-4, 3-6, 3-7, 3-8, 3-10, 3-11, 3-12, 3-17, 3-18, 3-19, 3-21, 3-23, 3-24, 3-25, 3-26, 4-1, 5-2, and 5-3 at 500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

(94) B.8 Silverleaf Whitefly (Bemisia argentifolii)

(95) The active compounds were formulated in cyclohexanone as a 10,000 ppm solution supplied in tubes. The tubes were inserted into an automated electrostatic sprayer equipped with an atomizing nozzle and they served as stock solutions for which lower dilutions were made in 50% acetone:50% water (v/v). A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01% (v/v).

(96) Cotton plants at the cotyledon stage (one plant per pot) were sprayed by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. Each pot was placed into a plastic cup and about 10 to 12 whitefly adults (approximately 3-5 days old) were introduced. The insects were collected using an aspirator and a nontoxic Tygon® tubing connected to a barrier pipette tip. The tip, containing the collected insects, was then gently inserted into the soil containing the treated plant, allowing insects to crawl out of the tip to reach the foliage for feeding. Cups were covered with a reusable screened lid. Test plants were maintained in a growth room at about 25° C. and about 20-40% relative humidity for 3 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the cup. Mortality was assessed 3 days after treatment, compared to untreated control plants.

(97) In this test, the compounds 1-7, 1-9, 1-10, 2-2, 2-3, 2-4, 2-5, 2-10, 2-11, 2-12, 2-13, 2-15, 2-23, 2-26, 2-28, 2-29, 2-31, 2-33, 2-35, 2-37, 2-38, 2-39, 2-40, 2-41, 2-42, 2-43, 2-47, 2-48, 2-49, 2-50, 2-53, 2-57, 2-58, 2-59, 2-62, 2-63, 2-65, 2-66, 2-67, 2-68, 2-71, 2-72, 2-73, 2-74, 2-75, 2-77, 2-81, 2-82, 2-83, 2-84, 2-86, 2-87, 2-88, 2-90, 2-91, 2-92, 2-93, 2-95, 2-96, 2-99, 2-100, 2-109, 2-110, 2-114, 2-115, 2-121, 2-123, 2-128, 2-130, 2-134, 2-136, 2-137, 2-138, 2-139, 2-140, 2-142, 2-143, 2-145, 2-146, 2-148, 2-149, 2-150, 2-151, 2-152, 2-153, 2-154, 2-155, 2-162, 2-163, 2-164, 2-165, 2-166, 2-169, 2-171, 2-172, 2-173, 2-178, 2-179, 2-181, 2-182, 2-183, 2-185, 2-186, 2-188, 2-189, 2-190, 2-195, 2-199, 3-1, 3-4, 3-6, 3-7, 3-9, 3-10, 3-11, 3-12, and 3-19 at 100 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

(98) B.9 Southern Armyworm (Spodoptera eridania)

(99) The active compounds were formulated in cyclohexanone as a 10,000 ppm solution supplied in tubes. The tubes were inserted into an automated electrostatic sprayer equipped with an atomizing nozzle and they served as stock solutions for which lower dilutions were made in 50% acetone:50% water (v/v). A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01% (v/v).

(100) Lima bean plants (variety Sieva) were grown 2 plants to a pot and selected for treatment at the 1.sup.st true leaf stage. Test solutions were sprayed onto the foliage by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. Each pot was placed into perforated plastic bags with a zip closure. About 10 to 11 armyworm larvae were placed into the bag and the bags zipped closed. Test plants were maintained in a growth room at about 25° C. and about 20-40% relative humidity for 4 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the bags. Mortality and reduced feeding were assessed 4 days after treatment, compared to untreated control plants.

(101) In this test, the compounds 1-1, 1-2, 1-5, 1-7, 1-8, 1-9, 1-10, 1-11, 1-13, 1-14, 2-1, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-11, 2-12, 2-13, 2-15, 2-18, 2-19, 2-20, 2-21, 2-23, 2-26, 2-27, 2-28, 2-29, 2-30, 2-31, 2-32, 2-33, 2-35, 2-37, 2-38, 2-39, 2-40, 2-41, 2-42, 2-43, 2-44, 2-45, 2-46, 2-47, 2-48, 2-49, 2-50, 2-51, 2-52, 2-53, 2-54, 2-55, 2-56, 2-57, 2-58, 2-59, 2-60, 2-61, 2-62, 2-63, 2-64, 2-65, 2-66, 2-67, 2-68, 2-69, 2-70, 2-71, 2-72, 2-73, 2-74, 2-75, 2-76, 2-77, 2-81, 2-82, 2-83, 2-84, 2-85, 2-86, 2-87, 2-88, 2-89, 2-90, 2-91, 2-92, 2-93, 2-94, 2-95, 2-96, 2-97, 2-98, 2-99, 2-100, 2-101, 2-102, 2-103, 2-104, 2-105, 2-106, 2-107, 2-108, 2-109, 2-110, 2-112, 2-114, 2-115, 2-116, 2-117, 2-118, 2-119, 2-120, 2-121, 2-123, 2-124, 2-125, 2-126, 2-127, 2-128, 2-129, 2-130, 2-131, 2-132, 2-133, 2-134, 2-135, 2-136, 2-137, 2-138, 2-139, 2-140, 2-141, 2-142, 2-143, 2-144, 2-145, 2-146, 2-147, 2-148, 2-149, 2-150, 2-151, 2-152, 2-153, 2-154, 2-155, 2-162, 2-163, 2-164, 2-165, 2-166, 2-169, 2-170, 2-171, 2-172, 2-173, 2-178, 2-179, 2-180, 2-181, 2-182, 2-183, 2-184, 2-185, 2-186, 2-187, 2-188, 2-189, 2-190, 2-191, 2-192, 2-193, 2-195, 2-197, 2-198, 2-199, 2-200, 2-202, 2-203, 2-204, 2-206, 2-207, 2-208, 2-209, 2-210, 2-212, 2-214, 2-216, 2-221, 2-222, 2-224, 2-225, 2-226, 2-227, 3-1, 3-2, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9, 3-10, 3-11, 3-12, 3-13, 3-17, 3-18, 3-19, 3-20, 3-21, 3-22, 3-23, 3-24, 3-25, 3-26, 3-27, 4-1, 5-2, 5-3, 5-6 and 5-7 at 1 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

(102) B.10 Vetch Aphid (Megoura viciae)

(103) For evaluating control of vetch aphid (Megoura viciae) through contact or systemic means the test unit consisted of 24-well-microtiter plates containing broad bean leaf disks.

(104) The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the leaf disks at 2.5 μl, using a custom built micro atomizer, at two replications.

(105) After application, the leaf disks were air-dried and 5-8 adult aphids placed on the leaf disks inside the microtiter plate wells. The aphids were then allowed to suck on the treated leaf disks and incubated at about 23±1° C. and about 50±5% relative humidity for 5 days. Aphid mortality and fecundity was then visually assessed.

(106) In this test, the compounds 1-1, 1-2, 1-3, 1-4, 1-5, 1-7, 1-8, 1-9, 1-10, 1-12, 1-13, 1-15, 2-1, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-11, 2-12, 2-13, 2-15, 2-19, 2-20, 2-21, 2-23, 2-24, 2-26, 2-27, 2-28, 2-29, 2-30, 2-31, 2-32, 2-33, 2-35, 2-36, 2-37, 2-38, 2-39, 2-40, 2-41, 2-42, 2-43, 2-44, 2-45, 2-46, 2-47, 2-48, 2-49, 2-51, 2-52, 2-53, 2-54, 2-55, 2-56, 2-57, 2-58, 2-59, 2-60, 2-61, 2-62, 2-63, 2-64, 2-65, 2-66, 2-67, 2-68, 2-69, 2-70, 2-71, 2-72, 2-73, 2-74, 2-75, 2-77, 2-79, 2-81, 2-82, 2-83, 2-84, 2-85, 2-86, 2-87, 2-88, 2-89, 2-90, 2-91, 2-92, 2-93, 2-94, 2-95, 2-96, 2-97, 2-98, 2-99, 2-100, 2-101, 2-102, 2-104, 2-105, 2-106, 2-107, 2-108, 2-109, 2-110, 2-111, 2-112, 2-114, 2-115, 2-116, 2-117, 2-118, 2-119, 2-120, 2-121, 2-123, 2-124, 2-125, 2-126, 2-127, 2-128, 2-129, 2-130, 2-131, 2-132, 2-133, 2-134, 2-135, 2-136, 2-137, 2-138, 2-139, 2-140, 2-141, 2-142, 2-143, 2-145, 2-146, 2-147, 2-148, 2-149, 2-150, 2-151, 2-152, 2-153, 2-154, 2-155, 2-159, 2-162, 2-163, 2-164, 2-165, 2-166, 2-170, 2-171, 2-172, 2-173, 2-178, 2-179, 2-180, 2-181, 2-182, 2-183, 2-184, 2-185, 2-186, 2-188, 2-189, 2-190, 2-191, 2-192, 2-193, 2-194, 2-195, 2-197, 2-198, 2-199, 2-200, 2-201, 2-202, 2-203, 2-204, 2-206, 2-207, 2-208, 2-209, 2-210, 2-211, 2-213, 2-214, 2-215, 2-216, 2-217, 2-218, 2-219, 2-220, 2-221, 2-222, 2-223, 2-224, 2-225, 2-226, 2-227, 3-6, 3-7, 3-8, 3-9, 3-10, 3-11, 3-12, 3-13, 3-14, 3-16, 3-17, 3-18, 3-19, 3-20, 3-21, 3-22, 3-23, 3-24, 3-25, 3-26, 3-27, 3-28, 4-1, 5-1, 5-2, 5-3, 5-4, 5-5, 5-6, 5-7, and 5-8 at 2500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

(107) B.11 Tobacco Budworm (Heliothis virescens) I

(108) For evaluating control of tobacco budworm (Heliothis virescens) the test unit consisted of 96-well-microtiter plates containing an insect diet and 15-25 H. virescens eggs. The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 10 μl, using a custom built micro atomizer, at two replications.

(109) After application, microtiter plates were incubated at about 28±1° C. and about 80±5% relative humidity for 5 days. Egg and larval mortality was then visually assessed.

(110) In this test, the compounds 1-1, 1-2, 1-3, 1-4, 1-5, 1-7, 1-8, 1-9, 1-10, 1-11, 1-12, 1-13, 1-14, 1-15, 2-1, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-11, 2-12, 2-13, 2-15, 2-17, 2-18, 2-19, 2-20, 2-21, 2-22, 2-23, 2-26, 2-27, 2-28, 2-29, 2-30, 2-31, 2-32, 2-33, 2-34, 2-35, 2-36, 2-37, 2-38, 2-39, 2-40, 2-41, 2-42, 2-43, 2-44, 2-45, 2-46, 2-47, 2-48, 2-49, 2-51, 2-52, 2-53, 2-54, 2-55, 2-56, 2-57, 2-58, 2-59, 2-60, 2-61, 2-62, 2-63, 2-64, 2-65, 2-66, 2-67, 2-68, 2-69, 2-70, 2-71, 2-72, 2-73, 2-74, 2-75, 2-77, 2-78, 2-81, 2-82, 2-83, 2-84, 2-85, 2-86, 2-87, 2-88, 2-89, 2-90, 2-91, 2-92, 2-93, 2-94, 2-95, 2-96, 2-97, 2-98, 2-99, 2-100, 2-101, 2-102, 2-103, 2-104, 2-105, 2-106, 2-107, 2-108, 2-109, 2-110, 2-111, 2-112, 2-114, 2-115, 2-116, 2-117, 2-118, 2-119, 2-120, 2-121, 2-122, 2-123, 2-124, 2-125, 2-126, 2-127, 2-128, 2-129, 2-130, 2-131, 2-132, 2-133, 2-134, 2-135, 2-136, 2-137, 2-138, 2-139, 2-140, 2-141, 2-142, 2-143, 2-147, 2-148, 2-149, 2-150, 2-151, 2-152, 2-153, 2-154, 2-155, 2-156, 2-157, 2-158, 2-160, 2-161, 2-162, 2-163, 2-164, 2-165, 2-166, 2-167, 2-169, 2-170, 2-171, 2-172, 2-173, 2-174, 2-175, 2-177, 2-178, 2-179, 2-180, 2-181, 2-182, 2-183, 2-184, 2-185, 2-186, 2-187, 2-188, 2-189, 2-190, 2-191, 2-192, 2-193, 2-194, 2-195, 2-196, 2-197, 2-198, 2-199, 2-200, 2-201, 2-202, 2-203, 2-204, 2-206, 2-207, 2-208, 2-209, 2-210, 2-211, 2-212, 2-213, 2-215, 2-216, 2-217, 2-218, 2-219, 2-220, 2-221, 2-222, 2-223, 2-224, 2-225, 2-226, 2-227, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9, 3-10, 3-11, 3-12, 3-13, 3-14, 3-15, 3-16, 3-17, 3-18, 3-19, 3-20, 3-21, 3-22, 3-23, 3-24, 3-25, 3-26, 3-27, 3-28, 4-1, 5-1, 5-2, 5-3, 5-4, 5-5, 5-6, 5-7, and 5-8 at 2500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

(111) B.12 Boll Weevil (Anthonomus grandis)

(112) For evaluating control of boll weevil (Anthonomusgrandis) the test unit consisted of 24-well-microtiter plates containing an insect diet and 20-30 A. grandis eggs.

(113) The compounds were formulated using a solution containing 75% v/v water and 25% v/v DMSO. Different concentrations of formulated compounds were sprayed onto the insect diet at 20 μl, using a custom built micro atomizer, at two replications.

(114) After application, microtiter plates were incubated at about 23±1° C. and about 50±5% relative humidity for 5 days. Egg and larval mortality was then visually assessed.

(115) In this test, the compounds 1-1, 1-2, 1-3, 1-4, 1-5, 1-7, 1-8, 1-9, 1-10, 1-11, 1-12, 1-13, 1-14, 1-15, 2-1, 2-2, 2-3, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-11, 2-12, 2-13, 2-15, 2-18, 2-19, 2-20, 2-21, 2-22, 2-23, 2-26, 2-27, 2-28, 2-29, 2-30, 2-31, 2-32, 2-33, 2-34, 2-35, 2-36, 2-37, 2-38, 2-39, 2-40, 2-41, 2-42, 2-43, 2-44, 2-45, 2-46, 2-47, 2-48, 2-49, 2-51, 2-52, 2-53, 2-54, 2-55, 2-56, 2-57, 2-58, 2-59, 2-60, 2-61, 2-62, 2-63, 2-64, 2-65, 2-66, 2-67, 2-68, 2-69, 2-70, 2-71, 2-72, 2-73, 2-74, 2-75, 2-76, 2-77, 2-78, 2-79, 2-80, 2-81, 2-82, 2-83, 2-84, 2-85, 2-86, 2-87, 2-88, 2-89, 2-90, 2-91, 2-92, 2-93, 2-94, 2-95, 2-96, 2-97, 2-98, 2-99, 2-100, 2-101, 2-102, 2-103, 2-104, 2-105, 2-106, 2-107, 2-108, 2-109, 2-110, 2-111, 2-112, 2-113, 2-114, 2-115, 2-116, 2-117, 2-118, 2-119, 2-120, 2-121, 2-123, 2-124, 2-125, 2-126, 2-127, 2-128, 2-129, 2-130, 2-131, 2-132, 2-133, 2-134, 2-135, 2-136, 2-137, 2-138, 2-139, 2-140, 2-141, 2-142, 2-143, 2-145, 2-146, 2-147, 2-148, 2-149, 2-150, 2-151, 2-152, 2-153, 2-154, 2-155, 2-157, 2-158, 2-160, 2-162, 2-163, 2-164, 2-165, 2-166, 2-167, 2-168, 2-169, 2-170, 2-171, 2-172, 2-173, 2-178, 2-179, 2-180, 2-181, 2-182, 2-183, 2-184, 2-185, 2-186, 2-187, 2-188, 2-189, 2-190, 2-191, 2-192, 2-193, 2-194, 2-195, 2-196, 2-197, 2-198, 2-199, 2-200, 2-201, 2-202, 2-203, 2-204, 2-206, 2-207, 2-208, 2-209, 2-210, 2-211, 2-212, 2-213, 2-214, 2-215, 2-216, 2-217, 2-218, 2-219, 2-220, 2-221, 2-222, 2-223, 2-224, 2-225, 2-226, 2-227, 3-3, 3-4, 3-5, 3-6, 3-7, 3-8, 3-9, 3-10, 3-11, 3-12, 3-13, 3-14, 3-15, 3-16, 3-17, 3-18, 3-19, 3-20, 3-21, 3-22, 3-23, 3-24, 3-25, 3-26, 3-27, 3-28, 4-1, 5-1, 5-2, 5-3, 5-4, 5-5, 5-6, 5-7, and 5-8 at 2500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

(116) B.13 Colorado Potato Beetle (Leptinotarsa decemlineata)

(117) The active compounds were formulated in cyclohexanone as a 10,000 ppm solution supplied in tubes. The tubes were inserted into an automated electrostatic sprayer equipped with an atomizing nozzle and they served as stock solutions for which lower dilutions were made in 50% acetone:50% water (v/v). A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01% (v/v).

(118) Eggplants were grown 2 plants to a pot and were selected for treatment at the 1.sup.st true leaf stage. Test solutions were sprayed onto the foliage by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. The treated foliage was then cut and removed from the pot and placed in a 5-inch Petri dish lined with moistened filter paper. Five beetle larvae were introduced into each Petri dish and the dish was covered by a Petri dish lid. Petri dishes were maintained in a growth room at 25° C. and 20-40% relative humidity for 4 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the dishes. Mortality and reduced feeding were assessed 4 days after treatment, compared to untreated control plants.

(119) In this test, the compounds 1-2, 2-1, 2-4, 2-5, 2-6, 2-10, 2-11, 2-12, 2-13, 2-19, 2-20, 2-26, 2-27, 2-28, 2-31, 2-32, 2-33, 2-35, 2-37, 2-38, 2-40, 2-43, 2-49, 2-50, 2-53, 2-57, 2-58, 2-59, 2-61, 2-67, 2-68, 2-71, 2-72, 2-73, 2-74, 2-82, 2-83, 2-88, 2-89, 2-93, 2-108, 2-112, 2-116, 2-118, 2-119, 2-120, 2-124, 2-126, 2-127, 2-128, 2-129, 2-131, 2-132, 2-133, 2-135, 2-137, 2-138, 2-141, 2-143, 2-147, 2-148, 2-149, 2-150, 2-151, 2-153, 2-154, 2-155, 2-162, 2-163, 2-165, 2-170, 2-178, 2-179, 2-180, 2-181, 2-182, 2-185, 2-186, 2-187, 2-193, 2-197, 2-199, 2-200, 3-4, 3-5, 3-7, 3-8, 3-9, 3-17, and 3-18 at 1 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.

(120) B.14 Red Spider Mite (Tetranychus kanzawai)

(121) The active compound was dissolved at the desired concentration in a mixture of 1:1 (v/v) distilled water:acetone. A surfactant (Alkamuls® EL 620) was added at the rate of 0.1% (v/v).

(122) Potted cowpea beans of 7-10 days of age were cleaned with tap water and sprayed with 5 ml of the test solution using air driven hand atomizer. The treated plants were allowed to air dry and afterwards inculated with 20 or more mites by clipping a cassava leaf section with known mite population. Treated plants were placed inside a holding room at about 25-27° C. and about 50-60% relatice humidity.

(123) Mortality was determined by counting the live mites 72 HAT. Percent mortality was assessed after 72 h.

(124) In this test, the compounds 2-1, 2-2, 2-4, 2-5, 2-6, 2-7, 2-8, 2-9, 2-10, 2-12, 2-13, 2-15, 2-26, 2-27, 2-28, 2-29, 2-30, 2-32, 2-37, 2-40, 2-43, 2-48, 2-51, 2-54, 2-55, 2-59, 2-60, 2-68, 2-70, 2-71, 2-72, 2-73, 2-75, 2-77, 2-82, 2-86, 2-97, 2-98, 2-99, 2-100, 2-108, 2-116, 2-118, 2-119, 2-120, 2-124, 2-126, 2-127, 2-128, 2-129, 2-131, 2-132, 2-133, 2-134, 2-135, 2-136, 2-137, 2-138, 2-139, 2-140, 2-141, 2-142, 2-143, 2-145, 2-146, 2-147, 2-148, 2-149, 2-151, 2-153, 2-162, 2-165, 2-166, 2-178, 2-179, 2-180, 2-181, 2-182, 2-183, 2-184, 2-185, 2-186, 2-193, 2-195, 2-199, 2-200, 2-201, 2-202, 2-203, 2-204, 2-206, 2-207, 2-208, 2-209, 2-210, 2-211, 2-213, 2-214, 2-215, 2-216, 2-217, 2-218, 2-219, 2-220, 2-221, 2-222, 2-224, 2-225, 2-226, 3-1, 3-7, 3-8, 3-10, 3-11, 3-12, 3-21, 3-22, 3-23, 3-24, 5-1, 5-2, and 5-3 at 500 ppm, respectively, showed a mortality of at least 75% in comparison with untreated controls.