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PESTICIDAL COMPOUNDS

20230157287 · 2023-05-25

    Inventors

    Cpc classification

    International classification

    Abstract

    The present application relates to the compounds of formula (I), and the N-oxides, stereoisomers, tautomers and agriculturally or veterinarily acceptable salts thereof wherein the variables are defined in the claims. The compounds of formula (I), as well as the N-oxides, stereoisomers tautomers and agriculturally or veterinarily acceptable salts thereof are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The application 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.

    ##STR00001##

    Claims

    1. A compound of the formula I ##STR00227## wherein A is N or CR.sup.A; B.sup.1 is N or CR.sup.B1; D is N or CR.sup.D; E is N or CR.sup.E; wherein at least one of the A, B.sup.1, E, and D is N; and when A and D are N, B.sup.1 is CR.sup.B1; B.sup.2 is N or CR.sup.B2; B.sup.3 is N or CR.sup.B3; B.sup.4 is N or CR.sup.B4; provided that at least one of the B.sup.2, B.sup.3, and B.sup.4 is other than N; R.sup.A, R.sup.D, R.sup.B1, and R.sup.E independently of each other are H, halogen, N.sub.3, OH, CN, NO.sub.2, —SCN, —SF.sub.5, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyl, tri-C.sub.1-C.sub.6-alkylsilyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkoxy, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkyl-C.sub.3-C.sub.6-cycloalkoxy, which moieties are unsubstituted or substituted with halogen, C(═O)—OR.sup.a, NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylene-NR.sup.bR.sup.c, O—C.sub.1-C.sub.6-alkylene-NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylene-CN, NH—C.sub.1-C.sub.6-alkylene-NR.sup.bR.sup.c, C(═O)—NR.sup.bR.sup.c, C(═O)—R.sup.d, SO.sub.2NR.sup.bR.sup.c, or S(═O).sub.mR.sup.e, phenyl, phenoxy, phenylcarbonyl, phenylthio, or —CH.sub.2-phenyl, wherein the phenyl rings are unsubstituted or substituted with R.sup.f; R.sup.B2, R.sup.B3, and R.sup.B4 independently of each other are H, halogen, N.sub.3, OH, CN, NO.sub.2, —SCN, —SF.sub.5, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyl, tri-C.sub.1-C.sub.6-alkylsilyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkoxy, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkyl-C.sub.3-C.sub.6-cycloalkoxy, which moieties are unsubstituted or substituted with halogen, C(═O)—OR.sup.a, NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylene-NR.sup.bR.sup.c, O—C.sub.1-C.sub.6-alkylene-NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylene-CN, NH—C.sub.1-C.sub.6-alkylene-NR.sup.bR.sup.c, C(═O)—NR.sup.bR.sup.c, C(═O)—R.sup.d, SO.sub.2NR.sup.bR.sup.c, or S(═O).sub.mR.sup.e, phenyl, phenoxy, phenylcarbonyl, phenylthio, or —CH.sub.2-phenyl, wherein the phenyl rings are unsubstituted or substituted with R.sup.f; Q is —C(R.sup.4R.sup.5)—O—, —C(═O)—O—, —S(═O).sub.m—C(R.sup.7R.sup.8)—, —N(R.sup.2)—S(═O).sub.m—, —N(R.sup.2)—, C(R.sup.9R.sup.10)—, —C(═O)—C(R.sup.19R.sup.20)—, —N(R.sup.2)—, μN(R.sup.2)—C(═O)—, —N(R.sup.2)—C(═S)—, —C(R.sup.13R.sup.14)—C(R.sup.15R.sup.16)—, —N═C(X)—, —N(R.sup.2)—C(═NR)—, or —C(R.sup.7)═C(R.sup.18)—; wherein Ar is bound to either side of Q; m is 0, 1, or 2; X is H, halogen, SR.sup.7, OR.sup.8, or N(R.sup.8).sub.2; R is H, CN, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, or C.sub.3-C.sub.6-cycloalkyl, which moieties are unsubstituted or substituted with halogen, OR.sup.8, N(R.sup.3).sub.2; R.sup.3 is H, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl; R.sup.2 is H, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, which moieties are unsubstituted or substituted with halogen C(═O)—OR.sup.a, C.sub.1-C.sub.6-alkylene-NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylene-CN, C(═O)—NR.sup.bR.sup.c, C(═O)—R.sup.d, SO.sub.2NR.sup.bR.sup.c, S(═O).sub.mR.sup.e, phenyl, or —CH.sub.2-phenyl, wherein the phenyl rings are unsubstituted or substituted with R.sup.f; R.sup.4, R.sup.5, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.13, R.sup.14, R.sup.15, R.sup.16, R.sup.17, R.sup.18, R.sup.19, R.sup.20 are, identical or different, H, halogen, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, which moieties are unsubstituted or substituted with halogen, C(═O)—OR.sup.a, C.sub.1-C.sub.6-alkylene-NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylene-CN, C(═O)—NR.sup.bR.sup.c, C(═O)—R.sup.d, SO.sub.2NR.sup.bR.sup.c, S(═O).sub.mR.sup.e, phenyl, or —CH.sub.2-phenyl, wherein the phenyl rings are unsubstituted or substituted with R.sup.f; Ar is phenyl or 5- or 6-membered hetaryl or 1,3-benzodioxole, which are unsubstituted or substituted with R.sup.Ar, wherein R.sup.Ar is halogen, N.sub.3, OH, CN, NO.sub.2, —SCN, —SF.sub.5, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyl, tri-C.sub.1-C.sub.6-alkylsilyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkoxy, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, which moieties are unsubstituted or substituted with halogen, C(═O)—OR.sup.a, NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylene-NR.sup.bR.sup.c, O—C.sub.1-C.sub.6-alkylene-NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylene-CN, NH—C.sub.1-C.sub.6-alkylene-NR.sup.bR.sup.c, C(═O)—NR.sup.bR.sup.c, C(═O)—R.sup.d, SO.sub.2NR.sup.bR.sup.c, or S(═O).sub.mR.sup.e, phenyl, phenoxy, phenylcarbonyl, phenylthio or —CH.sub.2-phenyl, wherein phenyl rings are unsubstituted or substituted with R.sup.f; R.sup.1 is a moiety of formula Y—Z-T-R.sup.11 or Y—Z-T-R.sup.12; wherein Y is —CR.sup.ya═N—, wherein the N is bound to Z; —NR.sup.yc—C(═O)—, wherein C(═O) is bound to Z; or —NR.sup.yc—C(═S)—, wherein C(═S) is bound to Z; Z is a single bond; —NR.sup.zc—C(═O)—, wherein C(═O) is bound to T; —NR.sup.zc—C(═S)—, wherein C(═S) is bound to T; —N═C(S—R.sup.za)—, wherein T is bound to the carbon atom; —O—C(═O)—, wherein T is bound to the carbon atom; or —NR.sup.zc—C(S—R.sup.za)═, wherein T is bound to the carbon atom; Provided that when Y is —NR.sup.yc—C(═O)— or —NR.sup.yc—C(═S)—, then Z is other than a single bond; T is O, N or N—R.sup.T; R.sup.11 is C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-alkyl-C.sub.3-C.sub.6-cycloalkoxy, which moieties are unsubstituted or substituted with halogen, C.sub.1-C.sub.6-alkylene-NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylene-CN, C(═O)—NR.sup.bR.sup.c, C(═O)—R.sup.d, aryl, aryl-carbonyl, aryl-C.sub.1-C.sub.4-alkyl, aryloxy-C.sub.1-C.sub.4-alkyl, hetaryl, carbonyl-hetaryl, hetaryl-C.sub.1-C.sub.4-alkyl or hetaryloxy-C.sub.1-C.sub.4-alkyl, wherein the phenyl and hetaryl rings are unsubstituted or substituted with R.sup.g and wherein the hetaryl is a 5- or 6-membered monocyclic hetaryl or a 8-, 9- or 10-membered bicyclic hetaryl; R.sup.12 is a radical of the formula A.sup.1; ##STR00228## wherein # indicates the point of attachment to T; R.sup.121, R.sup.122, R.sup.123 are, identical or different, H, halogen, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyloxy, C.sub.2-C.sub.6-alkynyloxy, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.1-C.sub.6-alkylcarbonlyoxy, C.sub.1-C.sub.6-alkenylcarbonlyoxy, C.sub.3-C.sub.6-cycloalkylcarbonlyoxy, which moieties are unsubstituted or substituted with halogen, or NR.sup.bR.sup.c, or one of R.sup.121, R.sup.122, R.sup.123 may also be oxo; R.sup.124 is H, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkoxy, or C.sub.2-C.sub.6-alkenyloxy, which moieties are unsubstituted or substituted with halogen; and where R.sup.ya is H, halogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkyl-C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkyl-C.sub.3-C.sub.6-cycloalkoxy, which moieties are unsubstituted or substituted with halogen, C(═O)—OR.sup.a, C.sub.1-C.sub.6-alkylene-NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylene-CN, C(═O)—NR.sup.bR.sup.c, C(═O)—R.sup.d, SO.sub.2NR.sup.bR.sup.c, S(═O).sub.mR.sup.e, phenyl, or —CH.sub.2-phenyl, wherein the phenyl rings are unsubstituted or substituted with R.sup.f; R.sup.yc, R.sup.zc are, identical or different, H, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.4-alkyl-C.sub.1-C.sub.6-alkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkyl-C.sub.3-C.sub.6-cycloalkyl, or C.sub.1-C.sub.4-alkyl-C.sub.3-C.sub.6-cycloalkoxy, which moieties are unsubstituted or substituted with halogen; R.sup.T is H, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.4-alkyl-C.sub.1-C.sub.6-alkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cyclo-alkoxy-C.sub.1-C.sub.4-alkyl, which moieties are unsubstituted or substituted with halogen, C(═O)—OR.sup.a, C.sub.1-C.sub.6-alkylene-NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylene-CN, C(═O)—NR.sup.bR.sup.c, C(═O)—R.sup.d, SO.sub.2NR.sup.bR.sup.c, S(═O).sub.mR.sup.e, phenyl, or —CH.sub.2-phenyl, wherein the phenyl rings are unsubstituted or substituted with R.sup.f; R.sup.zc together with R.sup.T if present, may form C.sub.1-C.sub.6-alkylene or a linear C.sub.2-C.sub.6-alkenylene group, where in the linear C.sub.1-C.sub.6-alkylene and the linear C.sub.2-C.sub.6-alkenylene a CH.sub.2 moiety may be replaced by a carbonyl or a C═N—R′ and/or wherein 1 or 2 CH.sub.2 moieties may be replaced by 0 or S and/or wherein the linear C.sub.1-C.sub.6-alkylene and the linear C.sub.2-C.sub.6-alkenylene may be unsubstituted or substituted with R.sup.h; R.sup.za is H, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyl, tri-C.sub.1-C.sub.6-alkylsilyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.4-alkyl-C.sub.1-C.sub.6-alkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkyl-C.sub.3-C.sub.6-cycloalkoxy, C.sub.1-C.sub.4-alkyl-C.sub.3-C.sub.6-cycloalkyl, which moieties are unsubstituted or substituted with halogen, C.sub.1-C.sub.6-alkylene-NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylene-CN, C(═O)—NR.sup.bR.sup.c, C(═O)—R.sup.d, phenyl, phenylcarbonyl, or —CH.sub.2-phenyl, wherein the phenyl rings are unsubstituted or substituted with R.sup.f; R.sup.za together with R.sup.T if present, may form C.sub.1-C.sub.6-alkylene or a linear C.sub.2-C.sub.6-alkenylene group, where in the linear C.sub.1-C.sub.6-alkylene and the linear C.sub.2-C.sub.6-alkenylene a CH.sub.2 moiety may be replaced by a carbonyl or a C═N—R′ and/or wherein 1 or 2 CH.sub.2 moieties may be replaced by O or S and/or wherein the linear C.sub.1-C.sub.6-alkylene and the linear C.sub.2-C.sub.6-alkenylene may be unsubstituted or substituted with R.sup.h; R.sup.a, R.sup.b and R.sup.c are, identical or different, H, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, which moieties are unsubstituted or substituted with halogen, C.sub.1-C.sub.6-alkylene-CN, phenyl, or —CH.sub.2-phenyl, wherein the phenyl rings are unsubstituted or substituted with R.sup.f; R.sup.d is H, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cyclo-alkoxy-C.sub.1-C.sub.4-alkyl, which moieties are unsubstituted or substituted with halogen, phenyl, or —CH.sub.2-phenyl, wherein the phenyl rings are unsubstituted or substituted with R.sup.f; R.sup.e is C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, which moieties are unsubstituted or substituted with halogen, phenyl and —CH.sub.2-phenyl, wherein the phenyl rings are unsubstituted or substituted with R.sup.f; R.sup.f is halogen, N.sub.3, OH, CN, NO.sub.2, —SCN, —SF.sub.5, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyl, tri-C.sub.1-C.sub.6-alkylsilyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkoxy, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxyx-C.sub.1-C.sub.4-alkyl, which moieties are unsubstituted or substituted with halogen, C(═O)—OR.sup.a, NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylene-NR.sup.bR.sup.c, O—C.sub.1-C.sub.6-alkylene-NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylene-CN, NH—C.sub.1-C.sub.6-alkylene-NR.sup.bR.sup.c, C(═O)—NR.sup.bR.sup.c, C(═O)—R.sup.d, SO.sub.2NR.sup.bR.sup.c, or S(═O).sub.mR.sup.e; R.sup.g is halogen, N.sub.3, OH, CN, NO.sub.2, —SCN, —SF.sub.5, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyl, tri-C.sub.1-C.sub.6-alkylsilyl, C.sub.2-C.sub.6-alkynyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.6-alkoxy-C.sub.1-C.sub.4-alkoxy, C.sub.3-C.sub.6-cycloalkyl, C.sub.3-C.sub.6-cycloalkoxy, C.sub.3-C.sub.6-cycloalkyl-C.sub.1-C.sub.4-alkyl, C.sub.3-C.sub.6-cycloalkoxy-C.sub.1-C.sub.4-alkyl, which moieties are unsubstituted or substituted with halogen, C(═O)—OR.sup.a, NR.sup.bR.sup.c, C.sub.1-C.sub.6-alkylene-NR.sup.bR.sup.c, O—C.sub.1-C.sub.6-alkylene-NR.sup.bR.sup.c, C.sub.0-C.sub.6-alkylene-CN, NH—C.sub.1-C.sub.6-alkylene-NR.sup.bR.sup.c, C(═O)—NR.sup.bR.sup.c, C(═O)—R.sup.d, SO.sub.2NR.sup.bR.sup.c, or S(═O).sub.mR.sup.e; R.sup.h is halogen, OH, C.sub.1-C.sub.6-alkyl, C.sub.3-C.sub.6-cycloalkyl, or CN; and the N-oxides, stereoisomers, tautomers, and agriculturally or veterinarily acceptable salts thereof.

    2. The compound of formula I according to claim 1, wherein A is N.

    3. The compound of formula I according to claim 1, wherein A and D are N.

    4. The compound of formula I according to claim 1, wherein B.sup.1 is N.

    5. The compound of formula I according to claim 1, wherein B.sup.1 and D are N.

    6. The compound of formula I according to claim 1, wherein E and D are N.

    7. The compound of formula I according to claim 1, wherein Q is —C(R.sup.4R.sup.5)—O—, —N(R.sup.2)—C(R.sup.9R.sup.10)—, —N(R.sup.2)—, —N(R.sup.2)—C(═O)—, —N═C(X)—, or —N(R.sup.2)—C(═NR)—; wherein Ar is bound to either side of Q.

    8. The compound of formula I according to claim 1, wherein R.sup.1 are formulas YZT-1 to YZT-9, custom-character wherein denotes attachment to the remaining part of the compound; ##STR00229## wherein R.sup.11, R.sup.12, R.sup.T, R.sup.ya, R.sup.yc, R.sup.za and R.sup.zc are as defined in claim 1.

    9. The compound of formula I according to claim 1, wherein Ar is a formula Ar-1 to Ar-22 ##STR00230## ##STR00231## ##STR00232##

    10. A composition, comprising a compound of formula I according to claim 1, an N-oxide or an agriculturally acceptable salt thereof, and a further active substance.

    11. A method for combating or controlling invertebrate pests, comprising contacting said pest or its food supply, habitat or breeding grounds with a pesticidally effective amount of at least one compound according to claim 1.

    12. A method for protecting growing plants from attack or infestation by invertebrate pests, which method comprises contacting a plant, or soil or water wherein the plant is growing, with a pesticidally effective amount of at least one compound according to claim 1.

    13. A seed comprising a compound according to claim 1, or the enantiomers, diastereomers or salts thereof, in an amount of from 0.1 g to 10 kg per 100 kg of seed.

    14. (canceled)

    15. A method for treating or protecting an animal from infestation or infection by invertebrate pests comprising bringing the animal in contact with a pesticidally effective amount of at least one compound of the formula I according to claim 1, a stereoisomer thereof and/or at least one veterinarily acceptable salt thereof.

    Description

    EXAMPLES

    Synthesis Examples

    [4584] With appropriate modification of the starting materials, the procedures as described in the preparation examples below were used to obtain further compounds of formula I. The compounds obtained in this manner are listed in the table C that follows, together with physical data.

    [4585] 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.

    [4586] Analytical HPLC—Method 1: Agilent Eclipse Plus C18, 50×4.6 mm, ID 5 μm; Elution: A=10 mM Amm. Formate (0.1% Formic Acid), B=Acetonitrile (0.1% Formic Acid), Flow=1.2 ml/min. at 30° C.; Gradient: 10% B to 100% B=3 min, hold for 1 min, 1 min-10% B. Run Time=5.01 min.

    [4587] Analytical HPLC—Method 2: Kinetex XB C18 1,7μ 50×2.1 mm; A=Water+0.1% TFA, B=Acetonitrile, Flow=0.8 ml/min-1.0 ml/min in 1.5 min. at 60° C.; Gradient: 5% B to 100% B=1.5 min.

    [4588] Preparative HPLC—Method 3: SunFire C18 5 μm, 50×100 mm; A=Water+2% TFA, B=Acetonitrile, Flow=128 ml/min; Gradient Narrow A: 1% B to 20% in 7.50 min, from 7.50 min to 7.60 min to 96% solvent B.

    [4589] Preparative HPLC—Method 4: SunFire C18 5 μm, 50×100 mm; A=Water+2% TFA, B=Acetonitrile, Flow=128 ml/min; Gradient LM-Narrow F: 50% B in 7.50 min, 95% to 97% from 7.50 min to 11.0 min.

    [4590] .sup.1H-NMR: The signals are characterized by chemical shift (ppm, 6 [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=multiplet, q=quartet, t=triplet, d=doublet and s=singlet.

    [4591] Abbreviations used are: d for day(s), h for hour(s), min for minute(s), r.t./room temperature for 20-25° C., Rt for retention time; DMSO for dimethyl sulfoxide, OAc for acetate, EtOAc for ethyl acetate.

    Example C-5

    N-[2-[4-[(E)-[(Z)-[3-(2-isopropyl-5-methyl-phenyl)-4-oxo-thiazolidin-2-ylidene]hydrazono]methyl]phenyl]pyrimidin-4-yl]-4-(trifluoromethyl)benzamide (C-5)

    Step 1: 4-(4-aminopyrimidin-2-yl)benzaldehyde

    [4592] A solution of 2-chloropyrimidin-4-amine (1.500 g), (4-formylphenyl)boronic acid (2.328 g), cesium fluoride (1.935 g), palladium acetate (0.130 g), triphenylphosphine-3,3′,3″-trisulfonic acid trisodium salt (0.645 g) in acetonitrile/water (1:3, 22 mL) was set under argon atmosphere. The reaction mixture was stirred for 16 h at 100° C. The reaction mixture was cooled down and water was added. The resulting precipitate was filtered and subjected to silica gel flash column chromatography, eluting with a gradient of EtOAc and cyclohexane to obtain the title compound as a solid (2.00 g). HPLC/MS (method 2): Rt: 0.551 min; m/z=199.9 (M+1).sup.+.

    Step 2: N-[2-(4-formylphenyl)pyrimidin-4-yl]-4-(trifluoromethyl)benzamide

    [4593] To solution of 4-(4-aminopyrimidin-2-yl)benzaldehyde (0.700 g) in pyridine (20 mL) 4-(trifluoromethyl)benzoyl chloride (0.832 g) was added at 0° C. After stirring 16 h at room temperature, ethyl acetate (20 mL) was added. The resulting precipitate was was subjected to silica gel flash column chromatography eluting with a gradient of EtOAc and methanol to obtain the title compound as a solid (0.400 g). HPLC/MS (method 2): Rt: 1.143 min; m/z=371.9 (M+1).sup.+.

    Step 3: Synthesis of N-[2-[4-[(E)-[(2-isopropyl-5-methyl-phenyl)carbamothioylhydrazono]methyl]phenyl]pyrimidin-4-yl]-4-(trifluoromethyl)benzamide

    [4594] To a solution of N-[2-(4-formylphenyl)pyrimidin-4-yl]-4-(trifluoromethyl)benzamide (0.200 g) in ethanol (5 mL) 1-amino-3-(2-isopropyl-5-methyl-phenyl)thiourea (0.135 g) was added. The reaction mixture was stirred for 5 h at reflux temperature and subsequently stirred for 16 h at room temperature. The reaction mixture was cooled down and the resulting precipitate was filtered and washed with cold ethanol to obtain the title compound as a solid (0.170 g). HPLC/MS (method 2): Rt: 1.457 min; m/z=577.0 (M+1).sup.+. 1H NMR (400 MHz, Acetone-d6) δ 10.80 (s, 1H), 10.48 (s, 1H), 9.65 (s, 1H), 8.86 (d, J=5.5 Hz, 1H), 8.49 (d, J=8.5 Hz, 2H), 8.34 (s, 1H), 8.34-8.30 (m, 2H), 8.25 (d, J=5.6 Hz, 1H), 8.02 (d, J=8.5 Hz, 2H), 7.93 (d, J=8.2 Hz, 2H), 7.30-7.19 (m, 2H), 7.13-7.08 (m, 1H), 3.21 (hept, J=7.0 Hz, 1H), 2.31 (s, 3H), 1.23 (d, J=6.9 Hz, 6H).

    Step 4, example C-5: N-[2-[4-[(E)-[(Z)-[3-(2-isopropyl-5-methyl-phenyl)-4-oxo-thiazolidin-2-ylidene]hydrazono]methyl]phenyl]pyrimidin-4-yl]-4-(trifluoromethyl)benzamide

    [4595] N-[2-[4-[(E)-[(2-isopropyl-5-methyl-phenyl)carbamothioylhydrazono]methyl]phenyl]pyrimidin-4-yl]-4-(trifluoromethyl)benzamide (0.100 g) and methyl 2-bromoacetate (0.03 mL) were dissolved in ethanol (3.0 mL) and stirred for and stirred for 4 h at reflux temperature. After stirring 16 h at room temperature, the resulting precipitate was filtered and washed with cold ethanol to obtain the title compound as a solid (0.090 g). HPLC/MS (method 2): Rt: 1.488 min; m/z=617.2 (M+1).sup.+.

    Example C-12

    N-[6-[4-[(E)-[(2Z)-2-(2-isopropylphenyl)imino-4-oxo-thiazolidin-3-yl]iminomethyl]phenyl]pyrimidin-4-yl]-4-(trifluoromethoxy)benzamide (C-12)

    Step 1: 4-(6-aminopyrimidin-4-yl)benzaldehyde

    [4596] A solution of 6-chloropyrimidin-4-amine (3.500 g), (4-formylphenyl)boronic acid (4.456 g), cesium fluoride (4.514 g), palladium acetate (0.288 g), triphenylphosphine-3,3′,3″-trisulfonic acid trisodium salt (0.921 g) in acetonitrile/water (1:3, 100 mL) was set under argon atmosphere. The reaction mixture was stirred for 72 h at 100° C. The reaction mixture was cooled down and methanol was added. The resulting precipitate was removed and the filtrate was concentrated. Methanol was added and the resulted precipitate was subjected to preparative HPLC (Method 3) to obtain the title compound as a solid (2.50 g). HPLC/MS (method 2): Rt: 0.509 min; m/z=199.9 (M+1).sup.+. 1H NMR (400 MHz, DMSO-d6) δ 10.10 (s, 1H), 8.65 (d, J=1.0 Hz, 1H), 8.15-8.06 (m, 4H), 7.97 (s, 2H), 7.02 (d, J=1.0 Hz, 1H).

    Step 2: N-[6-(4-formylphenyl)pyrimidin-4-yl]-4-(trifluoromethoxy)benzamide

    [4597] To solution of 4-(6-aminopyrimidin-4-yl)benzaldehyde (1.200 g) in pyridine (30 mL) 4-(trifluoromethyl)benzoyl chloride (1.550 g) was added at 0° C. After stirring 16 h at room temperature, ethyl acetate was added and the mixture was extracted with brine. The organic phase was dried over sodium sulfate, and the residue obtained was subjected to silica gel flash column chromatography eluting with a gradient of EtOAc and cyclohexane to obtain the title compound as a solid (0.370 g). HPLC/MS (method 2): Rt: 1.22 min; m/z=387.8 (M+1).sup.+. 1H NMR (500 MHz, Methanol-d4) δ 10.10 (s, 1H), 8.99 (d, J=1.2 Hz, 1H), 8.86 (d, J=1.3 Hz, 1H), 8.35-8.30 (m, 2H), 8.16-8.07 (m, 4H), 7.46 (d, J=8.4 Hz, 2H), 7.39-7.34 (m, 2H).

    Step 3, example C-12: N-[6-[4-[(E)-[(2Z)-2-(2-isopropylphenyl)imino-4-oxo-thiazolidin-3-yl]iminomethyl]phenyl]pyrimidin-4-yl]-4-(trifluoromethoxy)benzamide

    [4598] N-[6-(4-formylphenyl)pyrimidin-4-yl]-4-(trifluoromethoxy)benzamide (0.100 g) and (2E)-3-amino-2-(2-isopropylphenyl)imino-thiazolidin-4-one (0.071 g) were dissolved in acetic acid (5.0 mL) and stirred for 16 h at room temperature. The mixture was extracted with EtOAc and water. The organic phase was dried over sodium sulfate, and the residue obtained was subjected to preparative HPLC (Method 4) to obtain the title compound as a solid (0.036 g). HPLC/MS (method 2): Rt: 1.489 min; m/z=619.2 (M+1)+. 1H NMR (400 MHz, Chloroform-d) b 8.98 (s, 1H), 8.95 (d, J=1.2 Hz, 1H), 8.84 (d, J=1.2 Hz, 1H), 8.31 (s, 1H), 8.21-8.17 (m, 2H), 8.04-8.00 (m, 2H), 7.89-7.84 (m, 2H), 7.50-7.47 (m, 2H), 7.40-7.31 (m, 3H), 7.17 (dt, J=7.8, 1.0 Hz, 1H), 4.02 (d, J=1.7 Hz, 2H), 2.82 (h, J=6.8 Hz, 1H), 1.23 (t, J=6.9 Hz, 6H).

    Example C-13

    4-(trifluoromethoxy)-N-[6-[4-[(E)-[(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl]oxyiminomethyl]phenyl]pyrimidin-4-yl]benzamide (C-13)

    [4599] N-[6-(4-formylphenyl)pyrimidin-4-yl]-4-(trifluoromethoxy)benzamide (0.100 g) and O-[(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl]hydroxylamine (0.086 g) were dissolved in ethanol (5.0 mL) and stirred for 4 h at 80° C. and then 16 h at room temperature. The mixture was extracted with EtOAc and brine. The organic phase was dried over sodium sulfate, and the residue obtained was subjected to silica gel flash column chromatography eluting with a gradient of EtOAc and cyclohexane to obtain the title compound as a solid (0.060 g). HPLC/MS (method 2): Rt: 1.344 min; m/z=591 (M+1)+. 1H NMR (400 MHz, Chloroform-d) b 9.46 (s, 1H), 8.88 (dd, J=26.4, 1.2 Hz, 2H), 8.19 (d, J=3.5 Hz, 2H), 8.09-8.03 (m, 2H), 7.76 (d, J=8.4 Hz, 2H), 7.39-7.35 (m, 2H), 5.68 (d, J=2.0 Hz, 1H), 3.76 (dd, J=3.3, 2.0 Hz, 1H), 3.69 (dq, J=9.4, 6.1 Hz, 1H), 3.57 (s, 3H), 3.55 (s, 3H), 3.54 (s, 3H), 3.53-3.44 (m, 2H), 3.21 (t, J=9.4 Hz, 1H), 1.32 (d, J=6.2 Hz, 3H).

    [4600] By analogous procedures to the procedures described above for example C-5, C-12, C-13 the examples of formula I as listed in Table C were prepared.

    ##STR00088##

    TABLE-US-00004 TABLE C t.sub.R, M.sup.+ Com- (min; pound Ar Q A B.sup.1 D E B.sup.2 B.sup.3 B.sup.4 R.sup.1 /) C-1. [00089]embedded image [00090]embedded image CH CH N N CH CH CH [00091]embedded image 1.427; 563.2 C-2. [00092]embedded image [00093]embedded image CH CH N N CH CH CH [00094]embedded image 1.467; 603 C-3. [00095]embedded image [00096]embedded image CH CH N N CH CH CH [00097]embedded image 1.366; 575 C-4. [00098]embedded image [00099]embedded image CH CH N N CH CH CH [00100]embedded image 1.457; 577 C-5. [00101]embedded image [00102]embedded image CH CH N N CH CH CH [00103]embedded image 1.489; 617 C-6. [00104]embedded image [00105]embedded image CH N N CH CH CH CH [00106]embedded image 1.28; 563.2 C-7. [00107]embedded image [00108]embedded image CH N N CH CH CH CH [00109]embedded image 1.312; 577 C-8. [00110]embedded image [00111]embedded image CH N N CH CH CH CH [00112]embedded image 1.194; 575 C-9. [00113]embedded image [00114]embedded image CH N N CH CH CH CH [00115]embedded image 1.331; 603.2 C-10 [00116]embedded image [00117]embedded image CH N N CH CH CH CH [00118]embedded image 1.371; 617 C-11 [00119]embedded image [00120]embedded image CH N N CH CH CH CH [00121]embedded image 1.34; 603.1 C-12 [00122]embedded image [00123]embedded image N CH N CH CH CH CH [00124]embedded image 1.489; 619.2 C-13 [00125]embedded image [00126]embedded image N CH N CH CH CH CH [00127]embedded image 1.363; 575 C-14 [00128]embedded image [00129]embedded image N CH N CH CH CH CH [00130]embedded image 1.424; 577 C-15 [00131]embedded image [00132]embedded image N CH N CH CH CH CH [00133]embedded image 1.468; 619.1 C-16 [00134]embedded image [00135]embedded image N CH N CH CH CH CH [00136]embedded image 1.469; 603.2 C-17 [00137]embedded image [00138]embedded image N CH N CH CH CH CH [00139]embedded image 1.321; 575 C-18 [00140]embedded image [00141]embedded image N CH N CH CH CH CH [00142]embedded image 1.435; 602.9 C-19 [00143]embedded image [00144]embedded image N CH N CH CH CH CH [00145]embedded image 2.187; 565 C-20 [00146]embedded image [00147]embedded image N CH N CH CH CH CH [00148]embedded image 2.187; 603 C-21 [00149]embedded image [00150]embedded image N CH N CH CH CH CH [00151]embedded image 2.304; 653.55 C-22 [00152]embedded image [00153]embedded image N CH N CH CH CH CH [00154]embedded image 2.219; 566 C-23 [00155]embedded image [00156]embedded image N CH N CH CH CH CH [00157]embedded image 2.325; 606 C-24 [00158]embedded image [00159]embedded image N CH N CH CH CH CH [00160]embedded image 2.261; 604 C-25 [00161]embedded image [00162]embedded image N CH N CH CH CH CH [00163]embedded image 2.261; 576 C-26 [00164]embedded image [00165]embedded image N CH N CH CH CH CH [00166]embedded image 2.251; 560 C-27 [00167]embedded image [00168]embedded image N CH N CH CH CH CH [00169]embedded image 2.219; 577 C-28 [00170]embedded image [00171]embedded image N CH N CH CH CH CH [00172]embedded image 2.368; 616 C-29 [00173]embedded image [00174]embedded image N CH N CH CH CH CH [00175]embedded image 2.432; 561 C-30 [00176]embedded image [00177]embedded image N CH N CH CH CH CH [00178]embedded image 2.42; 618 C-31 [00179]embedded image [00180]embedded image N CH N CH CH CH CH [00181]embedded image 2.432; 633 C-32 [00182]embedded image [00183]embedded image N CH CH CH CH CH CH [00184]embedded image 2.133; 578 C-33 [00185]embedded image [00186]embedded image CH N CH CH CH CH CH [00187]embedded image 2.24; 618 C-34 [00188]embedded image [00189]embedded image CH N CH CH CH CH CH [00190]embedded image 2.091; 562 C-35 [00191]embedded image [00192]embedded image CH N CH CH CH CH CH [00193]embedded image 2.112; 616 C-36 [00194]embedded image [00195]embedded image N CH CH CH CH CH CH [00196]embedded image 2.005; 578 C-37 [00197]embedded image [00198]embedded image N CH CH CH CH CH CH [00199]embedded image 2.283; 567 C-38 [00200]embedded image [00201]embedded image N CH CH CH CH CH CH [00202]embedded image 2.112; 618 C-39 [00203]embedded image [00204]embedded image CH N CH CH CH CH CH [00205]embedded image 1.867; 604 C-40 [00206]embedded image [00207]embedded image N CH N CH CH CH CH [00208]embedded image 2.091; 604 C-41 [00209]embedded image [00210]embedded image N CH CH CH CH CH CH [00211]embedded image 2.219; 616 C-42 [00212]embedded image [00213]embedded image N CH CH CH CH CH CH [00214]embedded image 2.017; 607 C-43 [00215]embedded image [00216]embedded image N CH N CH CH CH CH [00217]embedded image 2.251; 551 C-44 [00218]embedded image [00219]embedded image N CH CH CH CH CH CH [00220]embedded image 2.204; 576 C-45 [00221]embedded image [00222]embedded image N CH CH CH CH CH CH [00223]embedded image 2.2; 561 C-46 [00224]embedded image [00225]embedded image N CH CH CH CH CH CH [00226]embedded image 2.132; 617

    Biological Examples

    [4601] If not otherwise specified, the test solutions are prepared as follows:

    [4602] The active compound is dissolved at the desired concentration in a mixture of 1:1 (vol:vol) distilled water:acetone. The test solution is prepared at the day of use.

    [4603] Test solutions are prepared in general at concentrations of 1000 ppm, 500 ppm, 300 ppm, 100 ppm and 30 ppm (wt/vol).

    [4604] B.1. Boll weevil (Anthonomus grandis)

    [4605] For evaluating control of boll weevil (Anthonomus grandis) the test unit consisted of 96-well-microtiter plates containing an insect diet and 5-10 A. grandis eggs.

    [4606] 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.

    [4607] After application, microtiter plates were incubated at about 25±1° C. and about 75±5% relative humidity for 5 days. Egg and larval mortality was then visually assessed.

    [4608] In this test, the following compounds at 2500 ppm showed over 75% mortality in comparison with untreated controls: C-24, C-25, C-26, C-27, C-28, C-29, C-30, C-31.

    [4609] B.2. Diamond Back Moth (Plutella xylostella)

    [4610] The active compound is dissolved at the desired concentration in a mixture of 1:1 (vol:vol) distilled water:acetone. Surfactant (Alkamuls® EL 620) is added at a rate of 0.1% (vol/vol). The test solution is prepared at the day of use.

    [4611] Leaves of cabbage were dipped in test solution and air-dried. Treated leaves were placed in petri dish enlined with moist filter paper and inoculated with ten 3.sup.rd instar larvae. Mortality was recorded 72 hours after treatment. Feeding damages were also recorded using a scale of 0-100%.

    [4612] In this test, the following compounds at 500 ppm showed over 75% mortality in comparison with untreated controls: C-1, C-2, C-4, C-6, C-7, C-9, C-10, C-11, C-12, C-14, C-15, C-16, C-18, C-19, C-20, C-21, C-22, C-23, C-26, C-27, C-28, C-29, C-30, C-31, C-32, C-33, C-34, C-35, C-36, C-37, C-38, C-40, C-41, C-43, C-44, C-45, C-46.

    [4613] B.3 Silverleaf Whitefly (Bemisia argentifolih) (Adults)

    [4614] 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 non-ionic surfactant (Kinetic®) was included in the solution at a volume of 0.01% (v/v).

    [4615] 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.

    [4616] In this test, the following compounds at 300 ppm showed over 75% mortality in comparison with untreated controls: C-25.

    [4617] B.4. Southern Armyworm (Spodoptera eridania), 2nd Instar Larvae

    [4618] 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).

    [4619] 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.

    [4620] In this test, the following compounds at 500 ppm showed over 75% mortality in comparison with untreated controls: C-4, C-7, C-9, C-10, C-11, C-12, C-14, C-15, C-18, C-19, C-20, C-21, C-22, C-23, C-24, C-25, C-26, C-27, C-28, C-30.

    [4621] B.5. Tobacco Budworm (Heliothis virescens)

    [4622] 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.

    [4623] 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.

    [4624] 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.

    [4625] In this test, the following compounds at 2500 ppm showed over 75% mortality in comparison with untreated controls: C-1, C-2, C-4, C-5, C-6, C-7, C-8, C-9, C-10, C-11, C-12, C-13, C-14, C-15, C-18, C-19, C-20, C-21, C-22, C-23, C-24, C-25, C-26, C-27, C-28, C-29, C-30, C-31, C-32, C-33, C-34, C-35, C-36, C-37, C-38, C-39, C-40, C-41, C-42, C-43, C-44, C-45, C-46.

    [4626] B.6. Yellow Fever Mosquito (Aedes aegypti)

    [4627] For evaluating control of yellow fever mosquito (Aedes aegypti) the test unit consisted of 96-well-microtiter plates containing 200 μl of tap water per well and 5-15 freshly hatched A. aegypti larvae. The active compounds were formulated using a solution containing 75% (v/v) water and 25% (v/v) DMSO. Different concentrations of formulated compounds or mixtures were sprayed onto the insect diet at 2.5 μl, using a custom built micro atomizer, at two replications.

    [4628] After application, microtiter plates were incubated at 28+1° C., 80+5% RH for 2 days. Larval mortality was then visually assessed.

    [4629] In this test, the following compounds at 2500 ppm showed over 75% mortality in comparison with untreated controls: C-2, C-4, C-5, C-6, C-7, C-8, C-9, C-10, C-17, C-18, C-20, C-21, C-23, C-24, C-25, C-26, C-27, C-28, C-29, C-30, C-31, C-32, C-33, C-34, C-35, C-36, C-37, C-38, C-39, C-40, C-41, C-42, C-43, C-45, C-46.

    [4630] B.7. Orchid Thrips (Dichromothrips corbetti)

    [4631] Dichromothrips corbetti adults used for bioassay were obtained from a colony maintained continuously under laboratory conditions. For testing purposes, the test compound is diluted in a 1:1 mixture of acetone:water (vol:vol), plus Kinetic® HV at a rate of 0.01% v/v.

    [4632] Thrips potency of each compound was evaluated by using a floral-immersion technique. All petals of individual, intact orchid flowers were dipped into treatment solution and allowed to dry in Petri dishes. Treated petals were placed into individual re-sealable plastic along with about 20 adult thrips. All test arenas were held under continuous light and a temperature of about 28° C. for duration of the assay. After 3 days, the numbers of live thrips were counted on each petal. The percent mortality was recorded 72 hours after treatment.

    [4633] In this test, the following compounds at 500 ppm showed over 75% mortality in comparison with untreated controls: C-6, C-7, C-9, C-10, C-11, C-12, C-14, C-15, C-16, C-18, C-22, C-23, C-24, C-25, C-27, C-28, C-30, C-31, C-33, C-34, C-35, C-36, C-38, C-40, C-41, C-44, C-46.

    [4634] B.9. Western Flower Thrips (Frankliniella occidentalis)

    [4635] The active compounds were formulated by a Tecan liquid handler in 100% cyclohexanone as a 10,000 ppm solution supplied in tubes. The 10,000 ppm solution was serially diluted in 100% cyclohexanone to make interim solutions. These served as stock solutions for which final dilutions were made by the Tecan in 50% acetone:50% water (v/v) into 10 or 20 ml glass vials. A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01% (v/v). The vials were then inserted into an automated electrostatic sprayer equipped with an atomizing nozzle for application to plants/insects.

    [4636] Small (˜2″ in height) cotton plants are sprayed with test compounds at concentrations ranging from 300 to 0.01 ppm in acetone/water through the automated VPS. After drying, cotton leaves are removed and circular leaf discs (˜1 cm diameter) are punched from the treated surface and transferred to clean 20 mL scintillation vials. Ten Western flower thrips (FRANOC) are aspirated into each scintillation vial. The vials with the leaf discs and thrips are kept in an upright incubator at 25° C. and 50% relative humidity with a 14:10 light:dark photoperiod. Each treatment is replicated twice.

    [4637] Thrips mortality is assessed at 2 DAT (days after treatment), counting all thrips both dead and alive. [The average absolute mortality is calculated for each treatment.]

    [4638] In this test, the following compounds at 300 ppm showed over 75% mortality in comparison with untreated controls: C-12, C-15, C-18, C-24, C-27, C-28, C-30.