Thioamides and amides for controlling animal pests
10385012 ยท 2019-08-20
Assignee
Inventors
- Sebastian Soergel (Ludwigshafen, DE)
- Pascal Bindschaedler (Roemerberg, DE)
- Matthias Pohlman (Freinsheim, DE)
- Ralph Paulini (Cary, NC)
Cpc classification
C07C327/44
CHEMISTRY; METALLURGY
C07C255/57
CHEMISTRY; METALLURGY
A01N41/12
HUMAN NECESSITIES
C07C255/61
CHEMISTRY; METALLURGY
A01N53/00
HUMAN NECESSITIES
International classification
C07C255/61
CHEMISTRY; METALLURGY
A01N41/12
HUMAN NECESSITIES
A01N53/00
HUMAN NECESSITIES
C07C255/57
CHEMISTRY; METALLURGY
C07C327/44
CHEMISTRY; METALLURGY
Abstract
The invention relates to the use of a compound of formula (I) ##STR00001##
or a salt thereof for combating animal pests,
where the symbols and indices are defined in the specification.
Claims
1. A method for combating invertebrate animal pests which attack plants, which method comprises contacting the pests, breeding ground, food supply, plant, seed, soil, area, material or environment in which the pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from animal attack or infestation with a pesticidally effective amount of at least one compound of formula (I) ##STR00115## or a salt thereof, wherein Y is phenyl unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents R.sup.5; or naphthyl unsubstituted or substituted with 1, 2, 3, 4, 5, 6 or 7 substituents R.sup.5; Q is phenyl unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents R.sup.6; C.sub.3 -C.sub.8 cycloalkyl unsubstituted or substituted with one or more substituents R.sup.6; C.sub.3-C.sub.8 cycloalkenyl unsubstituted or substituted with one or more substituents R.sup.6; or a 6-membered aromatic heterocyclic ring containing 1, 2, 3 or 4 nitrogen atoms in the ring, wherein the aforementioned ring is unsubstituted or substituted with 1, 2, 3 or 4 substituents R.sup.6; R.sup.1 is selected from the group consisting of hydrogen, halogen, cyano, hydroxy, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-cycloalkenyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyloxy, C.sub.1-C.sub.6-alkylthio, (C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with 1, 2 or 3 substituents R.sup.7; R.sup.2 is hydrogen or halogen; or R.sup.1 and R.sup.2 form together with the carbon atom to which they are attached a methylene group or a cyclopropyl group; R.sup.3 is selected from the group consisting of hydrogen, halogen, cyano, hydroxy, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-cycloalkenyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyloxy, C.sub.1-C.sub.6-alkylthio, (C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with 1, 2 or 3 substituents R.sup.7; R.sup.4 is hydrogen or halogen; or R.sup.3 and R.sup.4 form together with the carbon atom to which they are attached a methylene group or a cyclopropyl group; each R.sup.5, R.sup.6 is independently selected from the group consisting of halogen, cyano, azido, nitro, SCN, SF.sub.5, C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, wherein the carbon atoms of the aforementioned aliphatic radicals are unsubstituted or substituted with one or more R.sup.a; C.sub.3-C.sub.8 cycloalkyl or C.sub.3-C.sub.8 cycloalkenyl, wherein the carbon atoms of the aforementioned cycloaliphatic radicals are unsubstituted or substituted with one or more R.sup.b; phenyl unsubstituted or substituted with up to 5 R.sup.c; a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO, SO.sub.2, wherein the aforementioned ring is unsubstituted or substituted with up to 5 R.sup.d; Si(R.sup.e).sub.3, OR.sup.f, SR.sup.f, OS(O).sub.xR.sup.h, S(O).sub.xR.sup.h, N(R.sup.i).sub.2, N(R.sup.i)C(O)R.sup.m, OC(O)R.sup.m, C(O)R.sup.m, C(O)OR.sup.f, C(NR.sup.i)R.sup.m, C(S)R.sup.m; or two R.sup.5 on two adjacent carbon atoms present on one phenyl ring are together a bridge selected from the group consisting of CH.sub.2CH.sub.2CH.sub.2CH.sub.2, NCHCHCH, CHNCHCH, NCHNCH, NCHCHN, OCH.sub.2CH.sub.2CH.sub.2, OCHCHCH.sub.2, CH.sub.2OCH.sub.2CH.sub.2, OCH.sub.2CH.sub.2O, OCH.sub.2OCH.sub.2, CH.sub.2CH.sub.2CH.sub.2, CHCHCH.sub.2, CH.sub.2CH.sub.2O, CHCHO, CH.sub.2OCH.sub.2, CH.sub.2C(O)O, C(O)OCH.sub.2, O(CH.sub.2)O, SCH.sub.2CH.sub.2CH.sub.2, SCHCHCH.sub.2, CH.sub.2SCH.sub.2CH.sub.2, SCH.sub.2CH.sub.2S, SCH.sub.2SCH.sub.2, CH.sub.2CH.sub.2S, CHCHS, CH.sub.2SCH.sub.2, CH.sub.2C(S)S, C(S)SCH.sub.2, S(CH.sub.2)S, CH.sub.2CH.sub.2NR.sup.K, CH.sub.2CHN, CHCHNR.sup.K, OCHN, SCHN and form together with the carbon atoms the two R.sup.5 are bonded to a 5- or 6-membered partially unsaturated or aromatic carbocyclic or heterocyclic ring, wherein the ring is unsubstituted or substituted with 1 or 2 substituents selected from the group consisting of O, OH, CH.sub.3, OCH.sub.3, halogen, halomethyl and halomethoxy; each R.sup.7 is independently selected from the group consisting of halogen, cyano, hydroxy, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-cycloalkenyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyloxy, C.sub.1-C.sub.6-alkylthio, (C.sub.1-C.sub.6-alkoxy)carbonyl, OSi(R.sup.e).sub.3, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted, partially or fully halogenated and/or oxygenated; R.sup.aa is C(S)N(R.sup.cc).sub.2, C(NR.sup.dd)SR.sup.ee, or C(O)N(R.sup.ff).sub.2; R.sup.bb is C(S)N(R.sup.cc).sub.2, C(NR.sup.dd)SR.sup.ee, C(O)N(R.sup.ff).sub.2, or CN; each R.sup.cc 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.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.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, C.sub.1-C.sub.6-alkylthio-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkylthio-C.sub.1-C.sub.6-alkyl; each R.sup.dd 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.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.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, C.sub.1-C.sub.6-alkylthio-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkylthio-C.sub.1-C.sub.6-alkyl; each R.sup.ee is independently selected from the group consisting of cyano, 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.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, C.sub.1-C.sub.6-alkylthio-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkylthio-C.sub.1-C.sub.6-alkyl; each R.sup.ff 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.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.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, C.sub.1-C.sub.6-alkylthio-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkylthio-C.sub.1-C.sub.6-alkyl; each R.sup.a is independently selected from the group consisting of halogen, cyano, azido, nitro, SCN, SF.sub.5, 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-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, 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, C.sub.1-C.sub.6-alkyl-C.sub.3-C.sub.8-cycloalkyl, Si(R.sup.e).sub.3, OR.sup.A, SR.sup.A, OSO.sub.2R.sup.B, S(O).sub.xR.sup.B, S(O).sub.xN(R.sup.D).sub.2, N(R.sup.D).sub.2, C(O)N(R.sup.D).sub.2, C(S)N(R.sup.D).sub.2, C(O)OR.sup.A, phenyl unsubstituted or substituted with up to 5 R.sup.E; a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO.sub.2, wherein the aforementioned ring is unsubstituted or substituted with up to 5 R.sup.E, or two R.sup.a present on one carbon atom are together O, C(R.sup.F).sub.2, NR.sup.D, NOR.sup.A, NNR.sup.D, or two R.sup.a form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring together with the carbon atoms the two R.sup.a are bonded to; each R.sup.b is independently selected from the group consisting of halogen, cyano, azido, nitro, SCN, SF.sub.5, 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-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, 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, C.sub.1-C.sub.6-alkyl-C.sub.3-C.sub.8-cycloalkyl, Si(R.sup.G).sub.3, OR.sup.H, SR.sup.H, OSO.sub.2R.sup.J, S(O).sub.xR.sup.J, S(O).sub.xN(R.sup.K).sub.2, N(R.sup.K).sub.2, C(O)N(R.sup.K).sub.2, C(S)N(R.sup.K).sub.2, C(O)OR.sup.H, or two R.sup.b present on one carbon atom are together O, C(R.sup.L).sub.2, NR.sup.K, NOR.sup.H, NNR.sup.K, or two R.sup.b form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring together with the carbon atoms the two R.sup.b are bonded to; each R.sup.c is independently selected from the group consisting of halogen, cyano, azido, nitro, SCN, SF.sub.5, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R.sup.M; Si(R.sup.G).sub.3, OR.sup.H, SR.sup.H, OS(O).sub.xR.sup.J, S(O).sub.xR.sup.J, S(O).sub.xN(R.sup.K).sub.2, N(R.sup.K).sub.2, C(O)R.sup.N, C(O)OR.sup.H, C(NR.sup.K)R.sup.N, C(O)N(R.sup.K).sub.2, C(S)N(R.sup.K).sub.2; each R.sup.d is independently selected from the group consisting of halogen, cyano, azido, nitro, SCN, SF.sub.5, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R.sup.M; Si(R.sup.G).sub.3, OR.sup.H, SR.sup.H, OS(O).sub.xR.sup.J, S(O).sub.xR.sup.J, S(O).sub.xN(R.sup.K).sub.2, N(R.sup.K).sub.2, C(O)R.sup.N, C(O)OR.sup.H, C(NR.sup.K)R.sup.N, C(O)N(R.sup.K).sub.2, C(S)N(R.sup.K).sub.2, or two R.sup.d present on one atom of a saturated or partially unsaturated heterocyclic ring are together O, C(R.sup.L).sub.2; NR.sup.K, NOR.sup.H or NNR.sup.K; each R.sup.e is independently 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 alkoxyalkyl, 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 haloalkoxyalkyl, phenyl, a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO.sub.2; each R.sup.f is independently selected from the group consisting of hydrogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R.sup.M; Si(R.sup.e).sub.3, S(O).sub.xR.sup.B, S(O).sub.xN(R.sup.D).sub.2, N(R.sup.D).sub.2, NC(R.sup.F).sub.2, C(O)R.sup.Q, C(O)N(R.sup.D).sub.2, C(S)N(R.sup.D).sub.2, C(O)OR.sup.A, phenyl, a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO.sub.2; each R.sup.h is independently selected from the group consisting of hydrogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio, C.sub.3-C.sub.8-cycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R.sup.M; N(R.sup.D).sub.2, NC(R.sup.F).sub.2, C(O)R.sup.Q, C(O)N(R.sup.D).sub.2, C(S)N(R.sup.D).sub.2, C(O)OR.sup.A, phenyl, a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO.sub.2; each R.sup.i is independently selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio, C.sub.3-C.sub.8-cycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R.sup.M; S(O).sub.xR.sup.B, S(O).sub.xN(R.sup.D).sub.2, C(O)R.sup.S, C(O)OR.sup.A, C(O)N(R.sup.D).sub.2, C(S)R.sup.S, C(S)SR.sup.A, C(S)N(R.sup.D).sub.2, C(NR.sup.D)R.sup.S, phenyl unsubstituted or substituted with up to 5 R.sup.E; a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO.sub.2, wherein the aforementioned ring is unsubstituted or substituted with up to 5 R.sup.E, or two R.sup.i on one nitrogen atom are together a C.sub.2-C.sub.7 alkylene chain and form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or aromatic ring, wherein the alkylene chain may contain 1 or 2 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO.sub.2, and wherein the alkylene chain is unsubstituted or substituted with 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.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; each R.sup.m is independently selected from the group consisting of hydrogen, SCN, SF.sub.5, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio, C.sub.3-C.sub.8-cycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R.sup.M; Si(R.sup.e).sub.3, OR.sup.A, SR.sup.A, OSO.sub.2R.sup.B, N(R.sup.D).sub.2, C(O)N(R.sup.D).sub.2, C(S)N(R.sup.D).sub.2, C(O)OR.sup.A, phenyl unsubstituted or substituted with up to 5 R.sup.E; a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO.sub.2, wherein the aforementioned ring is unsubstituted or substituted with up to 5 R.sup.E; each R.sup.A is independently selected from the group consisting of hydrogen, cyano, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, 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, C.sub.3-C.sub.8-cycloalkyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4 alkoxy; phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are 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.B 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, 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, C.sub.3-C.sub.8-cycloalkyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4 alkoxy; phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are 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.D 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-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio, 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, C.sub.3-C.sub.8-cycloalkyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4-alkoxy; phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are 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.D on one nitrogen atom are together a C.sub.2-C.sub.6 alkylene chain and form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, or 7-membered saturated, partially unsaturated or aromatic ring, wherein the alkylene chain may contain 1 or 2 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO.sub.2, and wherein the alkylene chain is unsubstituted or substituted with halogen, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy; each R.sup.E is independently selected from the group consisting of 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-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio, 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 four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4-alkoxy, or two R.sup.E present on one atom of a saturated or partially unsaturated heterocyclic ring are together O, 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; each R.sup.F is independently selected from the group consisting of C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.6 cycloalkyl, C.sub.1-C.sub.4 alkoxyalkyl, phenyl and benzyl; each R.sup.G is independently 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 alkoxyalkyl, 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.1-C.sub.6 haloalkoxyalkyl; each R.sup.H is independently selected from the group consisting of hydrogen, cyano, C.sub.1-C.sub.6-alkyl sulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, 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 radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4 alkoxy; each R.sup.J 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, 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 radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4 alkoxy; each R.sup.K 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-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio, 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 radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4-alkoxy; each R.sup.L is independently selected from the group consisting of C.sub.1-C.sub.4 alkyl and C.sub.1-C.sub.4 alkoxyalkyl; each R.sup.M is independently selected from the group consisting of halogen, cyano, azido, 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-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio, 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, C.sub.3-C.sub.8-cycloalkyl, C.sub.1-C.sub.6-alkyl-C.sub.3-C.sub.8-cycloalkyl, wherein the five last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4 alkoxy, or two R.sup.M present on one carbon atom are together 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); each R.sup.N is independently selected from the group consisting of hydrogen, 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-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio, 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 radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4 alkoxy; each R.sup.Q is independently selected from the group consisting of hydrogen, 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-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio, 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, C.sub.3-C.sub.8-cycloalkyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4 alkoxy; phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are 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.S is independently selected from the group consisting of hydrogen, 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-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio, 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, C.sub.3-C.sub.8-cycloalkyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4 alkoxy; phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are 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, (C.sub.1-C.sub.6-alkoxy)carbonyl, (C.sub.1-C.sub.6-alkyl)amino and di-(C.sub.1-C.sub.6-alkyl)amino; p is 0 or 1; x is 1 or 2.
2. The method of claim 1, wherein Y is phenyl unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents R.sup.5; or naphthyl unsubstituted or substituted with 1 or 2 substituents R.sup.5; Q is phenyl unsubstituted or substituted with 1, 2, 3 or 4 substituents R.sup.6; cyclohexyl unsubstituted or substituted with 1 or 2 substituents R.sup.6; cyclopentyl unsubstituted or substituted with 1 or 2 substituents R.sup.6; or a 6-membered aromatic heterocyclic ring containing 1, 2 or 3 nitrogen atoms in the ring, wherein the aforementioned ring is unsubstituted or substituted with 1, 2, 3 or 4 substituents R.sup.6; R.sup.1 is selected from the group consisting of H, halogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl or (C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the five radicals last mentioned are unsubstituted or substituted with 1, 2 or 3 substituents selected from halogen, cyano, hydroxy, OSi(C.sub.1-C.sub.6-alkyl).sub.3, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-alkoxy and (C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the six radicals last mentioned are unsubstituted or partially or fully halogenated; R.sup.2 is selected from the group consisting of H and halogen; or R.sup.1 and R.sup.2 form together with the carbon atom to which they are attached a methylene group; R.sup.3 is selected from the group consisting of H, halogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl or (C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the five radicals last mentioned are unsubstituted or substituted with 1, 2 or 3 substituents selected from halogen, cyano, hydroxy, OSi(C.sub.1-C.sub.6-alkyl).sub.3, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-alkoxy and (C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the six radicals last mentioned are unsubstituted or partially or fully halogenated; R.sup.4 is selected from the group consisting of H and halogen; or R.sup.3 and R.sup.4 form together with the carbon atom to which they are attached a methylene group; R.sup.5 is selected from the group consisting of halogen, cyano, SF.sub.5, tri-(C.sub.1-C.sub.4)silyl-C.sub.2-C.sub.4-alkynyl, (C.sub.1-C.sub.6-alkyl)aminocarbonyl, di-(C.sub.1-C.sub.6-alkyl)aminocarbonyl, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl, phenyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, (C.sub.1-C.sub.6-alkoxy)carbonyl, (C.sub.1-C.sub.6-alkyl)amino, di-(C.sub.1-C.sub.6-alkyl)amino, (C.sub.1-C.sub.6-alkyl)carbonyl or (C.sub.1-C.sub.6-alkyl)carbonyloxy, wherein the 14 radicals last mentioned are unsubstituted or substituted with one or more substituents selected from halogen, cyano, C.sub.1-C.sub.4-alkyl-C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl and C.sub.1-C.sub.6-alkoxy, wherein the five radicals last mentioned are unsubstituted or partially or fully halogenated; or two R.sup.5 on two adjacent carbon atoms present on one phenyl ring are together a bridge selected from NCHCHCH, NCHCHN, OCH.sub.2CH.sub.2O, O(CH.sub.2)O and form together with the carbon atoms the two R.sup.5 are bonded to a 5- or 6-membered partially unsaturated or aromatic heterocyclic ring, wherein the ring is unsubstituted; R.sup.6 is selected from the group consisting of halogen, nitro, cyano, SF.sub.5, tri-(C.sub.1-C.sub.4)silyl-C.sub.2-C.sub.4-alkynyl, 2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl, (C.sub.1-C.sub.6-alkyl)aminocarbonyl, di-(C.sub.1-C.sub.6-alkyl)aminocarbonyl, dimethylcarbamoylsulfanyl, morpholine-4-carbonyl, acetamido, pyridyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl, phenyl, C.sub.1-C.sub.6-alkoxy, C.sub.3-C.sub.6-cycloalkoxy, phenoxy, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, (C.sub.1-C.sub.6-alkoxy)carbonyl, (C.sub.1-C.sub.6-alkyl)amino, di-(C.sub.1-C.sub.6-alkyl)amino, (C.sub.1-C.sub.6-alkyl)carbonyl or (C.sub.1-C.sub.6-alkyl)carbonyloxy, wherein the 16 radicals last mentioned are unsubstituted or substituted with one or more substituents selected from halogen, cyano, C.sub.1-C.sub.4-alkyl-C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl and C.sub.1-C.sub.6-alkoxy, wherein the five radicals last mentioned are unsubstituted or partially or fully halogenated; R.sup.aa is selected from the group consisting of C(S)N(R.sup.cc).sub.2 and C(O)N(R.sup.ff).sub.2; R.sup.bb is CN; each R.sup.cc is independently selected from the group consisting of hydrogen, C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-alkynyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.2-alkyl; each R.sup.ff is independently selected from the group consisting of hydrogen, C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-alkynyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.2-alkyl; p is 0 or 1.
3. The method of claim 1, wherein R.sup.1 is selected from the group consisting of H, Me, Et, iPr, cPr, CH.sub.2CN, CF.sub.3, CHF.sub.2, CH.sub.2F, CH.sub.2CH.sub.2F, CH.sub.2CHF.sub.2, CH.sub.2CF.sub.3, CN, halogen, CH.sub.2OH, CH.sub.2OMe, CH.sub.2OEt, CO.sub.2Me, CO.sub.2Et, CH.sub.2CO.sub.2Me, CH.sub.2CO.sub.2Et, CH.sub.2OSi(Me).sub.3 and CH.sub.2OSi(Et).sub.3.
4. The method of claim 1, wherein R.sup.3 is selected from the group consisting of H, Me, Et, iPr, cPr, CH.sub.2CN, CF.sub.3, CHF.sub.2, CH.sub.2F, CH.sub.2CH.sub.2F, CH.sub.2CHF.sub.2, CH.sub.2CF.sub.3, CN, halogen, CH.sub.2OH, CH.sub.2OMe, CH.sub.2OEt, CO.sub.2Me, CO.sub.2Et, CH.sub.2CO.sub.2Me, CH.sub.2CO.sub.2Et, CH.sub.2OSi(Me).sub.3 and CH.sub.2OSi(Et).sub.3.
5. The method of claim 1, wherein R.sup.5 is selected from the group consisting of halogen, Me, Et, iPr, cPr, OMe, OEt, OiPr, ethynyl, (trimethylsilyl)ethynyl, vinyl, Ph, CN, CF.sub.3, OCF.sub.3, SF.sub.5, CHF.sub.2, OCHF.sub.2, SMe, S(O)Me, S(O).sub.2Me, SCF.sub.3, S(O)CF.sub.3, S(O).sub.2CF.sub.3, SCHF.sub.2, S(O)CHF.sub.2, S(O).sub.2CHF.sub.2, CO.sub.2Me, CO.sub.2Et, C(O)Me, OAc, C(O)NHMe, C(O)NMe.sub.2, CH.sub.2OMe and CH.sub.2OEt; or two R.sup.5 on two adjacent carbon atoms present on one phenyl ring are together a bridge selected from the group consisting of NCHCHCH, NCHCHN, OCH.sub.2CH.sub.2O, O(CH.sub.2)O and form together with the carbon atoms the two R.sup.5 are bonded to a 5- or 6-membered partially unsaturated or aromatic heterocyclic ring, wherein the ring is unsubstituted.
6. The method of claim 1, wherein R.sup.6 is selected from the group consisting f halogen, Me, Et, iPr, cPr, tBu, OMe, OEt, OnPr, OiPr, OtBu, OPh, ethynyl, (trimethylsilyl)ethynyl, vinyl, Ph, NO.sub.2, CN, CF.sub.3, OCF.sub.3, SF.sub.5, CHF.sub.2, OCHF.sub.2, SMe, S(O)Me, S(O).sub.2Me, SCF.sub.3, S(O)CF.sub.3, S(O).sub.2CF.sub.3, SCHF.sub.2, S(O)CHF.sub.2, S(O).sub.2CHF.sub.2, CO.sub.2Me, CO.sub.2Et, CO.sub.2iPr, C(O)Me, OAc, C(O)NHMe, C(O)NMe.sub.2, CH.sub.2OMe, CH.sub.2OEt, fluoromethyl, 2,2,2-trifluoroethyl, 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl, 2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl, dimethoxymethyl, chloro(difluoro)methoxy, 2,2,2-trifluoroethoxy, 2,2-difluorocyclopropoxy, tert-butylsulfanyl, dimethylcarbamoylsulfanyl, morpholine-4-carbonyl, acetamido, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrrol-1-yl, pyrazol-1-yl, imidazol-1-yl and 1,2,4-triazol-1-yl.
7. The method of claim 1, wherein Y is phenyl unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents R.sup.5; or naphthyl unsubstituted or substituted with 1 substituent R.sup.5; Q is phenyl unsubstituted or substituted with 1, 2 or 3 substituents R.sup.6; cyclohexyl unsubstituted or substituted with 1 substituent R.sup.6; or a 6-membered aromatic heterocyclic ring containing 1, 2 or 3 nitrogen atoms in the ring, wherein the aforementioned ring is unsubstituted or substituted with 1, 2 or 3 substituents R.sup.6; R.sup.1is selected from the group consisting of H, Me, Et, CN, CH.sub.2CN, CH.sub.2CF.sub.3, halogen, CH.sub.2OH, CH.sub.2OMe, CH.sub.2OEt, CH.sub.2CO.sub.2Me, CH.sub.2CO.sub.2Et, CH.sub.2OSi(Me).sub.3 and CH.sub.2OSi(Et).sub.3; R.sup.2 is selected from the group consisting of H and halogen; R.sup.3 is selected from the group consisting of H, Me, Et, CN, CH.sub.2CN, CH.sub.2CF.sub.3, halogen, CH.sub.2OH, CH.sub.2OMe, CH.sub.2OEt, CH.sub.2CO.sub.2Me, CH.sub.2CO.sub.2Et, CH.sub.2OSi(Me).sub.3 and CH.sub.2OSi(Et).sub.3; R.sup.4 is selected from the group consisting of H and halogen; R.sup.5 is selected from the group consisting of halogen, cyano, tri-(C.sub.1-C.sub.4)silyl-C.sub.2-C.sub.4-alkynyl, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl, phenyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio and (C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the eight radicals last mentioned are unsubstituted or partially or fully halogenated; or two R.sup.5 on two adjacent carbon atoms present on one phenyl ring are together a bridge selected from the group consisting of NCHCHCH, NCHCHN, OCH.sub.2CH.sub.2O, O(CH.sub.2)O and form together with the carbon atoms the two R.sup.5 are bonded to a 5- or 6 -membered partially unsaturated or aromatic heterocyclic ring, wherein the ring is unsubstituted; R.sup.6 is selected from the group consisting of halogen, nitro, cyano, tri-(C.sub.1-C.sub.4)silyl-C.sub.2-C.sub.4-alkynyl, 2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl, dimethoxymethyl, dimethylcarbamoylsulfanyl, morpholine-4-carbonyl, acetamido, pyridyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl, phenyl, C.sub.1-C.sub.6-alkoxy, C.sub.3-C.sub.6-cycloalkoxy, phenoxy, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfonyl and (C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the eleven radicals last mentioned are unsubstituted or partially or fully halogenated; R.sup.aa is C(S)N(R.sup.cc).sub.2; R.sup.bb is CN; each R.sup.cc is independently selected from the group consisting of H, Me, Et, propargyl, allyl, CH.sub.2OMe, CH.sub.2OEt; p is 0 or 1.
8. The method of claim 1, wherein R.sup.5 is selected from the group consisting of halogen, Me, OMe, CN, CF.sub.3, OCF.sub.3 and ethynyl.
9. The method of claim 1, wherein R.sup.6 is selected from the group consisting of halogen, Me, OMe, CN, CF.sub.3, OCF.sub.3 and ethynyl.
10. The method of claim 1, wherein Y is phenyl unsubstituted or substituted with 1, 2 or 3 substituents R.sup.5; Q is phenyl unsubstituted or substituted with 1 or 2 substituents R.sup.6; pyridyl, pyrimidinyl, pyrazinyl or pyridazinyl, wherein the four rings last mentioned are unsubstituted or substituted with 1 or 2 substituents R.sup.6; R.sup.1 is selected from the group consisting of H, F, Me, Et, CN, CH.sub.2CN and CH.sub.2OMe; R.sup.2 is H; R.sup.5 is selected from the group consisting of F, Cl, Br and CF.sub.3; R.sup.6 is selected from the group consisting of F, ethynyl and CF.sub.3; R.sup.aa is C(S)NH.sub.2; R.sup.bb is CN; p is 0.
11. The method of claim 1, wherein R.sup.1 is H.
12. The method of claim 1, wherein R.sup.3 is H.
13. The method of claim 1, wherein p is 0.
14. The method of claim 1, wherein Q is phenyl unsubstituted or substituted with one or more R.sup.6.
15. The method of claim 1, wherein Q is pyridyl or pyrimidinyl, wherein the aforementioned rings are unsubstituted or substituted with one or more R.sup.6.
16. The method of claim 1, wherein R.sup.cc is H when R.sup.bb is CN.
17. The method of claim 1, wherein R.sup.aa is C(S)NH.sub.2 or C(O)NH.sub.2.
18. The method of claim 1, wherein R.sup.bb is CN.
19. The method of claim 1, wherein R.sup.aa is C(S)NH.sub.2 and R.sup.bb is CN.
20. The method of claim 1, wherein R.sup.1 and R.sup.2 are H and p is 0.
21. A method for protecting crops from attack or infestation by invertebrate animal pests, which comprises contacting the crop with a pesticidally effective amount of at least one compound of formula (I) of formula (I) ##STR00116## wherein Y is phenyl unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents R.sup.5; or naphthyl unsubstituted or substituted with 1, 2, 3, 4, 5, 6 or 7 substituents R.sup.5; Q is phenyl unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents R.sup.6; C.sub.3-C.sub.8 cycloalkyl unsubstituted or substituted with one or more substituents R.sup.6; C.sub.3-C.sub.8 cycloalkenyl unsubstituted or substituted with one or more substituents R.sup.6; 6-membered aromatic heterocyclic ring containing 1, 2, 3 or 4 nitrogen atoms in the ring, wherein the aforementioned ring is unsubstituted or substituted with 1, 2, 3 or 4 substituents R.sup.6; R.sup.1 is selected from the group consisting of hydrogen, halogen, cyano, hydroxy, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-cycloalkenyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyloxy, C.sub.1-C.sub.6-alkylthio, (C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with 1, 2 or 3 substituents R.sup.7; R.sup.2 is hydrogen or halogen; or R.sup.1 and R.sup.2 form together with the carbon atom to which they are attached a methylene group or a cyclopropyl group; R.sup.3 is selected from the group consisting of hydrogen, halogen, cyano, hydroxy, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-cycloalkenyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyloxy, C.sub.1-C.sub.6-alkylthio, (C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with 1, 2 or 3 substituents R.sup.7; R.sup.4 is hydrogen or halogen; or R.sup.3 and R.sup.4 form together with the carbon atom to which they are attached a methylene group or a cyclopropyl group; each R.sup.5, R.sup.6 is independently selected from the group consisting of halogen, cyano, azido, nitro, SCN, SF.sub.5, C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, wherein the carbon atoms of the aforementioned aliphatic radicals are unsubstituted or substituted with one or more R.sup.a; C.sub.3-C.sub.8 cycloalkyl or C.sub.3-C.sub.8 cycloalkenyl, wherein the carbon atoms of the aforementioned cycloaliphatic radicals are unsubstituted or substituted with one or more R.sup.b; phenyl unsubstituted or substituted with up to 5 R.sup.c; a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO, SO.sub.2, wherein the aforementioned ring is unsubstituted or substituted with up to 5 R.sup.d; Si(R.sup.e).sub.3, OR.sup.f, SR.sup.f, OS(O).sub.xR.sup.h, S(O).sub.xR.sup.h, N(R.sup.i).sub.2, N(R.sup.i)C(O)R.sup.m, OC(O)R.sup.m, C(O)R.sup.m, C(O)OR.sup.f, C(NR.sup.i)R.sup.m, C(S)R.sup.m; or two R.sup.5 on two adjacent carbon atoms present on one phenyl ring are together a bridge selected from the group consisting of CH.sub.2CH.sub.2CH.sub.2CH.sub.2, NCHCHCH, CHNCHCH, NCHNCH, NCHCHN, OCH.sub.2CH.sub.2CH.sub.2, OCHCHCH.sub.2, CH.sub.2OCH.sub.2CH.sub.2, OCH.sub.2CH.sub.2O, OCH.sub.2OCH.sub.2, CH.sub.2CH.sub.2CH.sub.2, CHCHCH.sub.2, CH.sub.2CH.sub.2O, CHCHO, CH.sub.2OCH.sub.2, CH.sub.2C(O)O, C(O)OCH.sub.2, O(CH.sub.2)O, SCH.sub.2CH.sub.2CH.sub.2, SCHCHCH.sub.2, CH.sub.2SCH.sub.2CH.sub.2, SCH.sub.2CH.sub.2S, SCH.sub.2SCH.sub.2, CH.sub.2CH.sub.2S, CHCHS, CH.sub.2SCH.sub.2, CH.sub.2C(S)S, C(S)SCH.sub.2, S(CH.sub.2)S, CH.sub.2CH.sub.2NR.sup.K, CH.sub.2CHN, CHCHNR.sup.K, OCHN, SCHN and form together with the carbon atoms the two R.sup.5 are bonded to a 5- or 6-membered partially unsaturated or aromatic carbocyclic or heterocyclic ring, wherein the ring is unsubstituted or substituted with 1 or 2 substituents selected from the group consisting of O, OH, CH.sub.3, OCH.sub.3, halogen, halomethyl and halomethoxy; each R.sup.7 is independently selected from the group consisting of halogen, cyano, hydroxy, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-cycloalkenyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyloxy, C.sub.1-C.sub.6-alkylthio, (C.sub.1-C.sub.6-alkoxy)carbonyl, OSi(R.sup.e).sub.3, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted, partially or fully halogenated and/or oxygenated; R.sup.aa is C(S)N(R.sup.cc).sub.2, C(NR.sup.dd)SR.sup.ee, or C(O)N(R.sup.ff).sub.2; R.sup.bb is C(S)N(R.sup.cc).sub.2, C(NR.sup.dd)SR.sup.ee, C(O)N(R.sup.ff).sub.2, or CN; each R.sup.cc 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.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.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, C.sub.1-C.sub.6-alkylthio-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkylthio-C.sub.1-C.sub.6-alkyl; each R.sup.dd 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.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.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, C.sub.1-C.sub.6-alkylthio-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkylthio-C.sub.1-C.sub.6-alkyl; each R.sup.ee is independently selected from the group consisting of cyano, 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.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, C.sub.1-C.sub.6-alkylthio-C.sub.1-C.sub.6-alkyl, C.sub.1-.sub.6-haloalkylthio-C.sub.1-C.sub.6-alkyl; each R.sup.ff 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.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.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, C.sub.1-C.sub.6-alkylthio-C.sub.1-C.sub.6-alkyl, C.sub.1-.sub.6-haloalkylthio-C.sub.1-C.sub.6-alkyl; each R.sup.a is independently selected from the group consisting of halogen, cyano, azido, nitro, SCN, SF.sub.5, 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-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, 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, C.sub.1-C.sub.6-alkyl-C.sub.3-C.sub.8-cycloalkyl, Si(R.sup.e).sub.3, OR.sup.A, SR.sup.A, OSO.sub.2R.sup.B, S(O).sub.xR.sup.B, S(O).sub.xN(R.sup.D).sub.2, N(R.sup.D).sub.2, C(O)N(R.sup.D).sub.2, C(S)N(R.sup.D).sub.2, C(O)OR.sup.A, phenyl unsubstituted or substituted with up to 5 R.sup.E; a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO.sub.2, wherein the aforementioned ring is unsubstituted or substituted with up to 5 R.sup.E, or two R.sup.a present on one carbon atom are together O, C(R.sup.F).sub.2, NR.sup.D, NOR.sup.A, NNR.sup.D, or two R.sup.a form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring together with the carbon atoms the two R.sup.a are bonded to; each R.sup.b is independently selected from the group consisting of halogen, cyano, azido, nitro, SCN, SF.sub.5, 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-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, 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, C.sub.1-C.sub.6-alkyl-C.sub.3-C.sub.8-cycloalkyl, Si(R.sup.G).sub.3, OR.sup.H, SR.sup.H, OSO.sub.2R.sup.J, S(O).sub.xR.sup.J, S(O).sub.xN(R.sup.K).sub.2, N(R.sup.K).sub.2, C(O)N(R.sup.K).sub.2, C(S)N(R.sup.K).sub.2, C(O)OR.sup.H, or two R.sup.b present on one carbon atom are together O, C(R.sup.L).sub.2, NR.sup.K, NOR.sup.H, NNR.sup.K, or two R.sup.b form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring together with the carbon atoms the two R.sup.b are bonded to; each R.sup.c is independently selected from the group consisting of halogen, cyano, azido, nitro, SCN, SF.sub.5, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R.sup.M; Si(R.sup.G).sub.3, OR.sup.H, SR.sup.H, OS(O).sub.xR.sup.J, S(O).sub.xR.sup.J, S(O).sub.xN(R.sup.K).sub.2, N(R.sup.K).sub.2, C(O)R.sup.N, C(O)OR.sup.H, C(NR.sup.K)R.sup.N, C(O)N(R.sup.K).sub.2, C(S)N(R.sup.K).sub.2; each R.sup.d is independently selected from the group consisting of halogen, cyano, azido, nitro, SCN, SF.sub.5, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R.sup.M; Si(R.sup.G).sub.3, OR.sup.H, SR.sup.H, OS(O).sub.xR.sup.J, S(O).sub.xR.sup.J, S(O).sub.xN(R.sup.K).sub.2, N(R.sup.K).sub.2, C(O)R.sup.N, C(O)OR.sup.H, C(NR.sup.K)R.sup.N, C(O)N(R.sup.K).sub.2, C(S)N(R.sup.K).sub.2, or two R.sup.d present on one atom of a saturated or partially unsaturated heterocyclic ring are together O, C(R.sup.L).sub.2; NR.sup.K, NOR.sup.H or NNR.sup.K; each R.sup.e is independently 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 alkoxyalkyl, 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 haloalkoxyalkyl, phenyl, a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO.sub.2, each R.sup.f is independently selected from the group consisting of hydrogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R.sup.M; Si(R.sup.e).sub.3, S(O).sub.xR.sup.B, S(O).sub.xN(R.sup.D).sub.2, N(R.sup.D).sub.2, NC(R.sup.F).sub.2, C(O)R.sup.Q, C(O)N(R.sup.D).sub.2, C(S)N(R.sup.D).sub.2, C(O)OR.sup.A, phenyl, a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO.sub.2; each R.sup.h is independently selected from the group consisting of hydrogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio, C.sub.3-C.sub.8-cycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R.sup.M; N(R.sup.D).sub.2, NC(R.sup.F).sub.2, C(O)R.sup.Q, C(O)N(R.sup.D).sub.2, C(S)N(R.sup.D).sub.2, C(O)OR.sup.A, phenyl, a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO.sub.2; each R.sup.i is independently selected from the group consisting of hydrogen, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio, C.sub.3-C.sub.8-cycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R.sup.M; S(O).sub.xR.sup.B, S(O).sub.xN(R.sup.D).sub.2, C(O)R.sup.S, C(O)OR.sup.A, C(O)N(R.sup.D).sub.2, C(S)R.sup.S, C(S)SR.sup.A, C(S)N(R.sup.D).sub.2, C(NR.sup.D)R.sup.S, phenyl unsubstituted or substituted with up to 5 R.sup.E; a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO.sub.2, wherein the aforementioned ring is unsubstituted or substituted with up to 5 R.sup.E, or two R.sup.i on one nitrogen atom are together a C.sub.2-C.sub.7 alkylene chain and form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or aromatic ring, wherein the alkylene chain may contain 1 or 2 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO.sub.2, and wherein the alkylene chain is unsubstituted or substituted with 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.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; each R.sup.m is independently selected from the group consisting of hydrogen, SCN, SF.sub.5 , C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio, C.sub.3-C.sub.8-cycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R.sup.M; Si(R.sup.e).sub.3, OR.sup.A, SR.sup.A, OSO.sub.2R.sup.B, N(R.sup.D).sub.2, C(O)N(R.sup.D).sub.2, C(S)N(R.sup.D).sub.2, C(O)OR.sup.A, phenyl unsubstituted or substituted with up to 5 R.sup.E; a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO.sub.2, wherein the aforementioned ring is unsubstituted or substituted with up to 5 R.sup.E; each R.sup.A is independently selected from the group consisting of hydrogen, cyano, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, 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, C.sub.3-C.sub.8-cycloalkyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4 alkoxy; phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are 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.B 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, 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, C.sub.3-C.sub.8-cycloalkyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4 alkoxy; phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are 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.D 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-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio, 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, C.sub.3-C.sub.8-cycloalkyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4-alkoxy; phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are 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.D on one nitrogen atom are together a C.sub.2-C.sub.6 alkylene chain and form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, or 7-membered saturated, partially unsaturated or aromatic ring, wherein the alkylene chain may contain 1 or 2 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO.sub.2, and wherein the alkylene chain is unsubstituted or substituted with halogen, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy; each R.sup.E is independently selected from the group consisting of 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-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio, 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 four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4-alkoxy, or two R.sup.E present on one atom of a saturated or partially unsaturated heterocyclic ring are together O, 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; each R.sup.F is independently selected from the group consisting of C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.6 cycloalkyl, C.sub.1-C.sub.4 alkoxyalkyl, phenyl and benzyl; each R.sup.G is independently 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 alkoxyalkyl, 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.1-C.sub.6 haloalkoxyalkyl; each R.sup.H is independently selected from the group consisting of hydrogen, cyano, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, trimethylsilyl, trimethylsilyl, 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 radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4 alkoxy; each R.sup.J 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, 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 radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4 alkoxy; each R.sup.K 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-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio, 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 radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4-alkoxy; each R.sup.L is independently selected from the group consisting of C.sub.1-C.sub.4 alkyl and C.sub.1-C.sub.4 alkoxyalkyl; each R.sup.M is independently selected from the group consisting of halogen, cyano, azido, 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-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio, 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, C.sub.3-C.sub.8-cycloalkyl, C.sub.1-C.sub.6-alkyl-C.sub.3-C.sub.8-cycloalkyl, wherein the five last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4 alkoxy, or two R.sup.M present on one carbon atom are together 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); each R.sup.N is independently selected from the group consisting of hydrogen, 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-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio, 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 radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4 alkoxy; each R.sup.Q is independently selected from the group consisting of hydrogen, 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-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio, 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, C.sub.3-C.sub.8-cycloalkyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4 alkoxy; phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are 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.S is independently selected from the group consisting of hydrogen, 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-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio, 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, C.sub.3-C.sub.8-cycloalkyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4 alkoxy; phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are 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, (C.sub.1-C.sub.6-alkoxy)carbonyl, (C.sub.1-C.sub.6-alkyl)amino and di-(C.sub.1-C.sub.6-alkyl)amino; p is 0 or 1; x is 1 or 2; or a salt thereof.
22. A method for protecting seeds from soil insects and the seedlings roots and shoots from soil and foliar insects, which comprises contacting the seeds before sowing and/or after pregermination with at least one compound of formula (I) ##STR00117## wherein Y is phenyl unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents R.sup.5; or naphthyl unsubstituted or substituted with 1, 2, 3, 4, 5, 6 or 7 substituents R.sup.5; Q is phenyl unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents R.sup.6; C.sub.3-C.sub.8 cycloalkyl unsubstituted or substituted with one or more substituents R.sup.6; C.sub.3-C.sub.8 cycloalkenyl unsubstituted or substituted with one or more substituents R.sup.6; or a 6-membered aromatic heterocyclic ring containing 1, 2, 3 or 4 nitrogen atoms in the ring, wherein the aforementioned ring is unsubstituted or substituted with 1, 2, 3 or 4 substituents R.sup.6; R.sup.1 is selected from the group consisting of hydrogen, halogen, cyano, hydroxy, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-cycloalkenyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyloxy, C.sub.1-C.sub.6-alkylthio, (C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with 1, 2 or 3 substituents R.sup.7; R.sup.2 is hydrogen or halogen; or R.sup.1 and R.sup.2 form together with the carbon atom to which they are attached a methylene group or a cyclopropyl group; R.sup.3 is selected from the group consisting of hydrogen, halogen, cyano, hydroxy, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-cycloalkenyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyloxy, C.sub.1-C.sub.6-alkylthio, (C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with 1, 2 or 3 substituents R.sup.7; R.sup.4 is hydrogen or halogen; or R.sup.3 and R.sup.4 form together with the carbon atom to which they are attached a methylene group or a cyclopropyl group; each R.sup.5, R.sup.6 is independently selected from the group consisting of halogen, cyano, azido, nitro, SCN, SF.sub.5, C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, wherein the carbon atoms of the aforementioned aliphatic radicals are unsubstituted or substituted with one or more R.sup.a; C.sub.3-C.sub.8 cycloalkyl or C.sub.3-C.sub.8 cycloalkenyl, wherein the carbon atoms of the aforementioned cycloaliphatic radicals are unsubstituted or substituted with one or more R.sup.b; phenyl unsubstituted or substituted with up to 5 R.sup.c; a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from the group consisting of N, O, S, NO, SO ,SO.sub.2, wherein the aforementioned ring is unsubstituted or substituted with up to 5 R.sup.d; Si(R.sup.e).sub.3, OR.sup.f, SR.sup.f, OS(O).sub.xR.sup.h, S(O).sub.xR.sup.h, N(R.sup.i).sub.2, N(R.sup.i)C(O)R.sup.m, OC(O)R.sup.m, C(O)R.sup.m, C(O)OR.sup.f, C(NR.sup.i)R.sup.m, C(S)R.sup.m; or two R.sup.5 on two adjacent carbon atoms present on one phenyl ring are together a bridge selected from the group consisting of CH.sub.2CH.sub.2CH.sub.2CH.sub.2, NCHCHCH, CHNCHCH, NCHNCH, NCHCHN, OCH.sub.2CH.sub.2CH.sub.2, OCHCHCH.sub.2, CH.sub.2OCH.sub.2CH.sub.2, OCH.sub.2CH.sub.2O, OCH.sub.2OCH.sub.2, CH.sub.2CH.sub.2CH.sub.2, CHCHCH.sub.2, CH.sub.2CH.sub.2O, CHCHO, CH.sub.2OCH.sub.2, CH.sub.2C(O)O, C(O)OCH.sub.2, O(CH.sub.2)O, SCH.sub.2CH.sub.2CH.sub.2, SCHCHCH.sub.2, CH.sub.2SCH.sub.2CH.sub.2, SCH.sub.2CH.sub.2S, SCH.sub.2SCH.sub.2, CH.sub.2CH.sub.2S, CHCHS, CH.sub.2SCH.sub.2, CH.sub.2C(S)S, C(S)SCH.sub.2, S(CH.sub.2)S, CH.sub.2CH.sub.2NR.sup.K, CH.sub.2CHN, CHCHNR.sup.K, OCHN, SCHN and form together with the carbon atoms the two R.sup.5 are bonded to a 5- or 6-membered partially unsaturated or aromatic carbocyclic or heterocyclic ring, wherein the ring is unsubstituted or substituted with 1 or 2 substituents selected from the group consisting of O, OH, CH.sub.3, OCH.sub.3, halogen, halomethyl and halomethoxy; each R.sup.7 is independently selected from the group consisting of halogen, cyano, hydroxy, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-cycloalkenyl, C.sub.1-C.sub.6-alkoxy, C.sub.2-C.sub.6-alkenyloxy, C.sub.1-C.sub.6-alkylthio, (C.sub.1-C.sub.6-alkoxy)carbonyl, OSi(R.sup.e).sub.3, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted, partially or fully halogenated and/or oxygenated; R.sup.aa is C(S)N(R.sup.cc).sub.2, C(NR.sup.dd)SR.sup.ee, or C(O)N(R.sup.ff).sub.2; R.sup.bb is C(S)N(R.sup.cc).sub.2, C(NR.sup.dd)SR.sup.ee, C(O)N(R.sup.ff).sub.2, or CN; each R.sup.cc 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.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.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, C.sub.1-C.sub.6-alkylthio-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkylthio-C.sub.1-C.sub.6-alkyl; each R.sup.dd 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.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.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, C.sub.1-C.sub.6-alkylthio-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkylthio-C.sub.1-C.sub.6-alkyl; each R.sup.ee is independently selected from the group consisting of cyano, 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.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, C.sub.1-C.sub.6-alkylthio-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkylthio-C.sub.1-C.sub.6-alkyl; each R.sup.ff 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.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.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, C.sub.1-C.sub.6-alkylthio-C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-haloalkylthio-C.sub.1-C.sub.6-alkyl; each R.sup.a is independently selected from the group consisting of halogen, cyano, azido, nitro, SCN, SF.sub.5, 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-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, 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, C.sub.1-C.sub.6-alkyl-C.sub.3-C.sub.8-cycloalkyl, Si(R.sup.e).sub.3, OR.sup.A, SR.sup.A, OSO.sub.2R.sup.B, S(O).sub.xR.sup.B, S(O).sub.xN(R.sup.D).sub.2, N(R.sup.D).sub.2, C(O)N(R.sup.D).sub.2, C(S)N(R.sup.D).sub.2, C(O)OR.sup.A, phenyl unsubstituted or substituted with up to 5 R.sup.E; a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO.sub.2, wherein the aforementioned ring is unsubstituted or substituted with up to 5 R.sup.E, or two R.sup.a present on one carbon atom are together O, C(R.sup.F).sub.2, NR.sup.D, NOR.sup.A, NNR.sup.D, or two R.sup.a form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring together with the carbon atoms the two R.sup.a are bonded to; each R.sup.b is independently selected from the group consisting of halogen, cyano, azido, nitro, SCN, SF.sub.5, 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-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, 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, C.sub.1-C.sub.6-alkyl-C.sub.3-C.sub.8-cycloalkyl, Si(R.sup.G).sub.3, OR.sup.H, SR.sup.H, OSO.sub.2R.sup.J, S(O).sub.xR.sup.J, S(O).sub.xN(R.sup.K).sub.2, N(R.sup.K).sub.2, C(O)N(R.sup.K).sub.2, C(S)N(R.sup.K).sub.2, C(O)OR.sup.H, or two R.sup.b present on one carbon atom are together O, C(R.sup.L).sub.2, NR.sup.K, NOR.sup.H, NNR.sup.K, or two R.sup.b form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring together with the carbon atoms the two R.sup.b are bonded to; each R.sup.c is independently selected from the group consisting of halogen, cyano, azido, nitro, SCN, SF.sub.5, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R.sup.M; Si(R.sup.G).sub.3, OR.sup.H, SR.sup.H, OS(O).sub.xR.sup.J, S(O).sub.xR.sup.J, S(O).sub.xN(R.sup.K).sub.2, N(R.sup.K).sub.2, C(O)R.sup.N, C(O)OR.sup.H, C(NR.sup.K)R.sup.N, C(O)N(R.sup.K).sub.2, C(SN(R.sup.K).sub.2; each R.sup.d is independently selected from the group consisting of halogen, cyano, azido, nitro, SCN, SF.sub.5, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.8-cycloalkyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R.sup.M; Si(R.sup.G).sub.3, OR.sup.H, SR.sup.H, OS(O).sub.xR.sup.J, S(O).sub.xR.sup.J, S(O).sub.xN(R.sup.K).sub.2, N(R.sup.K).sub.2, C(O)R.sup.N, C(O)OR.sup.H, C(NR.sup.K)R.sup.N, C(O)N(R.sup.K).sub.2, C(S)N(R.sup.K).sub.2, or two R.sup.d present on one atom of a saturated or partially unsaturated heterocyclic ring are together O, C(R.sup.L).sub.2; NR.sup.K, NOR.sup.H or NNR.sup.K; each R.sup.e is independently 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 alkoxyalkyl, 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 haloalkoxyalkyl, phenyl, a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO.sub.2; each R.sup.f is independently selected from the group consisting of hydrogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R.sup.M; Si(R.sup.e).sub.3, S(O).sub.xR.sup.B, S(O).sub.xN(R.sup.D).sub.2, N(R.sup.D).sub.2, NC(R.sup.F).sub.2, C(O)R.sup.Q, C(O)N(R.sup.D).sub.2, C(S)N(R.sup.D).sub.2, C(O)OR.sup.A, phenyl, a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO.sub.2; each R.sup.h is independently selected from the group consisting of hydrogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1C.sub.6-alkylthio, C.sub.3-C.sub.8-cycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R.sup.M; N(R.sup.D).sub.2, NC(R.sup.F).sub.2, C(O)R.sup.Q, C(O)N(R.sup.D).sub.2, C(S)N(R.sup.D).sub.2, C(O)OR.sup.A, phenyl, a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO.sub.2; each R.sup.i is independently selected from the group consisting of hydrogen, C.sub.1C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1C.sub.6-alkylthio, C.sub.3-C.sub.8-cycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R.sup.M; S(O).sub.xR.sup.B, S(O).sub.xN(R.sup.D).sub.2, C(O)R.sup.S, C(O)OR.sup.A, C(O)N(R.sup.D).sub.2, C(S)R.sup.S, C(S)SR.sup.A, C(S)N(R.sup.D).sub.2, C(NR.sup.D)R.sup.S, phenyl unsubstituted or substituted with up to 5 R.sup.E; a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO.sub.2, wherein the aforementioned ring is unsubstituted or substituted with up to 5 R.sup.E; or two R.sup.i on one nitrogen atom are together a C.sub.2-C.sub.7 alkylene chain and form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially unsaturated or aromatic ring, wherein the alkylene chain may contain 1 or 2 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO.sub.2, and wherein the alkylene chain is unsubstituted or substituted with 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.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; each R.sup.m is independently selected from the group consisting of hydrogen, SCN, SF.sub.5, C.sub.1-C.sub.6-alkyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio, C.sub.3-C.sub.8-cycloalkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, wherein the carbon atoms of the aforementioned aliphatic or cycloaliphatic radicals are unsubstituted or substituted with one or more R.sup.M; Si(R.sup.e).sub.3, OR.sup.A, SR.sup.A, OSO.sub.2R.sup.B, N(R.sup.D).sub.2, C(O)N(R.sup.D).sub.2, C(S)N(R.sup.D).sub.2, C(O)OR.sup.A, phenyl unsubstituted or substituted with up to 5 R.sup.E; a 3-, 4-, 5-, 6- or 7-membered saturated, partially unsaturated or aromatic heterocyclic ring containing 1, 2 or 3 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO.sub.2, wherein the aforementioned ring is unsubstituted or substituted with up to 5 R.sup.E; each R.sup.A is independently selected from the group consisting of hydrogen, cyano, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, 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, C.sub.3-C.sub.8-cycloalkyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4 alkoxy; phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are 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.B 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, 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, C.sub.3-C.sub.8-cycloalkyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4 alkoxy; phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are 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.D 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-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio, 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, C.sub.3-C.sub.8-cycloalkyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4-alkoxy; phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are 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.D on one nitrogen atom are together a C.sub.2-C.sub.6 alkylene chain and form together with the nitrogen atom they are bonded to a 3-, 4-, 5-, 6-, or 7-membered saturated, partially unsaturated or aromatic ring, wherein the alkylene chain may contain 1 or 2 heteroatoms or heteroatom groups selected from N, O, S, NO, SO, SO.sub.2, and wherein the alkylene chain is unsubstituted or substituted with halogen, C.sub.1-C.sub.4-haloalkyl, C.sub.1-C.sub.4-alkoxy or C.sub.1-C.sub.4-haloalkoxy; each R.sup.E is independently selected from the group consisting of 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-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio, 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 four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4-alkoxy, or two R.sup.E present on one atom of a saturated or partially unsaturated heterocyclic ring are together O, 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; each R.sup.F is independently selected from the group consisting of C.sub.1-C.sub.4 alkyl, C.sub.1-C.sub.6 cycloalkyl, C.sub.1-C.sub.4 alkoxyalkyl, phenyl and benzyl; each R.sup.G is independently 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 alkoxyalkyl, 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.1-C.sub.6 haloalkoxyalkyl; each R.sup.H is independently selected from the group consisting of hydrogen, cyano, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, 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 radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4 alkoxy; each R.sup.J 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, 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 radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4 alkoxy; each R.sup.K 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-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio, 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 radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4-alkoxy; each R.sup.L is independently selected from the group consisting of C.sub.1-C.sub.4 alkyl and C.sub.1-C.sub.4 alkoxyalkyl; each R.sup.M is independently selected from the group consisting of halogen, cyano, azido, 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-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio, 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, C.sub.3-C.sub.8-cycloalkyl, C.sub.1-C.sub.6-alkyl-C.sub.3-C.sub.8-cycloalkyl, wherein the five last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4 alkoxy, or two R.sup.M present on one carbon atom are together 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); each R.sup.N is independently selected from the group consisting of hydrogen, 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-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio, 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 radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4 alkoxy; each R.sup.Q is independently selected from the group consisting of hydrogen, 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-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio, 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, C.sub.3-C.sub.8-cycloalkyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4 alkoxy; phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are 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.S is independently selected from the group consisting of hydrogen, 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-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, C.sub.1-C.sub.6-haloalkylthio, 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, C.sub.3-C.sub.8-cycloalkyl, wherein the four last mentioned radicals are unsubstituted, partially or fully halogenated and/or oxygenated and/or carry 1 or 2 radicals selected from C.sub.1-C.sub.4 alkoxy; phenyl, benzyl, pyridyl, phenoxy, wherein the four last mentioned radicals are 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, (C.sub.1-C.sub.6-alkoxy)carbonyl, (C.sub.1-C.sub.6-alkyl)amino and di-(C.sub.1-C.sub.6-alkyl)amino; p is 0 or 1; x is 1 or 2; or a salt thereof.
23. The method of claim 21, wherein Y is phenyl unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents R.sup.5; or naphthyl unsubstituted or substituted with 1 or 2 substituents R.sup.5; Q is phenyl unsubstituted or substituted with 1, 2, 3 or 4 substituents R.sup.6; cyclohexyl unsubstituted or substituted with 1 or 2 substituents R.sup.6; cyclopentyl unsubstituted or substituted with 1 or 2 substituents R.sup.6; or a 6-membered aromatic heterocyclic ring containing 1, 2 or 3 nitrogen atoms in the ring, wherein the aforementioned ring is unsubstituted or substituted with 1, 2, 3 or 4 sub stituents R.sup.6; R.sup.1 is selected from the group consisting of H, halogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl or (C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the five radicals last mentioned are unsubstituted or substituted with 1, 2 or 3 substituents selected from halogen, cyano, hydroxy, OSi(C.sub.1-C.sub.6-alkyl).sub.3, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-alkoxy and (C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the six radicals last mentioned are unsubstituted or partially or fully halogenated; R.sup.2 is selected from the group consisting of H and halogen; or R.sup.1 and R.sup.2 form together with the carbon atom to which they are attached a methylene group; R.sup.3 is selected from the group consisting of H, halogen, cyano, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl or (C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the five radicals last mentioned are unsubstituted or substituted with 1, 2 or 3 substituents selected from halogen, cyano, hydroxy, OSi(C.sub.1-C.sub.6-alkyl).sub.3, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-alkoxy and (C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the six radicals last mentioned are unsubstituted or partially or fully halogenated; R.sup.4 is selected from the group consisting of H and halogen; or R.sup.3 and R.sup.4 form together with the carbon atom to which they are attached a methylene group; R.sup.5 is selected from the group consisting of halogen, cyano, SF.sub.5, tri-(C.sub.1-C.sub.4)silyl-C.sub.2-C.sub.4-alkynyl, (C.sub.1-C.sub.6-alkyl)aminocarbonyl, di-(C.sub.1-C.sub.6-alkyl)aminocarbonyl, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl, phenyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, (C.sub.1-C.sub.6-alkoxy)carbonyl, (C.sub.1-C.sub.6-alkyl)amino, di-(C.sub.1-C.sub.6-alkyl)amino, (C.sub.1-C.sub.6-alkyl)carbonyl or (C.sub.1-C.sub.6-alkyl)carbonyloxy, wherein the 14 radicals last mentioned are unsubstituted or substituted with one or more substituents selected from halogen, cyano, C.sub.1-C.sub.4-alkyl-C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl and C.sub.1-C.sub.6-alkoxy, wherein the five radicals last mentioned are unsubstituted or partially or fully halogenated; or two R.sup.5 on two adjacent carbon atoms present on one phenyl ring are together a bridge selected from NCHCHCH, NCHCHN, OCH.sub.2CH.sub.2O, O(CH.sub.2)O and form together with the carbon atoms the two R.sup.5 are bonded to a 5- or 6-membered partially unsaturated or aromatic heterocyclic ring, wherein the ring is unsubstituted; R.sup.6 is selected from the group consisting of halogen, nitro, cyano, SF.sub.5, tri-(C.sub.1-C.sub.4)silyl-C.sub.2-C.sub.4-alkynyl, 2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl, (C.sub.1-C.sub.6-alkyl)aminocarbonyl, di-(C.sub.1-C.sub.6-alkyl)aminocarbonyl, dimethylcarbamoylsulfanyl, morpholine-4-carbonyl, acetamido, pyridyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl, phenyl, C.sub.1-C.sub.6-alkoxy, C.sub.3-C.sub.6-cycloalkoxy, phenoxy, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfinyl, C.sub.1-C.sub.6-alkylsulfonyl, (C.sub.1-C.sub.6-alkoxy)carbonyl, (C.sub.1-C.sub.6-alkyl)amino, di-(C.sub.1-C.sub.6-alkyl)amino, (C.sub.1-C.sub.6-alkyl)carbonyl or (C.sub.1-C.sub.6-alkyl)carbonyloxy, wherein the 16 radicals last mentioned are unsubstituted or substituted with one or more substituents selected from halogen, cyano, C.sub.1-C.sub.4-alkyl-C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl and C.sub.1-C.sub.6-alkoxy, wherein the five radicals last mentioned are unsubstituted or partially or fully halogenated; R.sup.aa is selected from the group consisting of C(S)N(R.sup.cc).sub.2 and C(O)N(R.sup.ff).sub.2; R.sup.bb is CN; each R.sup.cc is independently selected from the group consisting of hydrogen, C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-alkynyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.2-alkyl; each R.sup.ff is independently selected from the group consisting of hydrogen, C.sub.1-C.sub.4-alkyl, C.sub.2-C.sub.4-alkenyl, C.sub.2-C.sub.4-alkynyl, C.sub.3-C.sub.6-cycloalkyl, C.sub.1-C.sub.4-alkoxy-C.sub.1-C.sub.2-alkyl; p is 0 or 1.
24. The method of claim 21, wherein R.sup.1 is selected from the group consisting of H, Me, Et, iPr, cPr, CH.sub.2CN, CF.sub.3, CHF.sub.2, CH.sub.2F, CH.sub.2CH.sub.2F, CH.sub.2CHF.sub.2, CH.sub.2CF.sub.3, CN, halogen, CH.sub.2OH, CH.sub.2OMe, CH.sub.2OEt, CO.sub.2Me, CO.sub.2Et, CH.sub.2CO.sub.2Me, CH.sub.2CO.sub.2Et, CH.sub.2OSi(Me).sub.3 and CH.sub.2OSi(Et).sub.3.
25. The method of claim 21, wherein R.sup.3 is selected from the group consisting of H, Me, Et, iPr, cPr, CH.sub.2CN, CF.sub.3, CHF.sub.2, CH.sub.2F, CH.sub.2CH.sub.2F, CH.sub.2CHF.sub.2, CH.sub.2CF.sub.3, CN, halogen, CH.sub.2OH, CH.sub.2OMe, CH.sub.2OEt, CO.sub.2Me, CO.sub.2Et, CH.sub.2CO.sub.2Me, CH.sub.2CO.sub.2Et, CH.sub.2OSi(Me).sub.3 and CH.sub.2OSi(Et).sub.3.
26. The method of claim 21, wherein R.sup.5 is selected from the group consisting of halogen, Me, Et, iPr, cPr, OMe, OEt, OiPr, ethynyl, (trimethylsilyl)ethynyl, vinyl, Ph, CN, CF.sub.3, OCF.sub.3, SF.sub.5, CHF.sub.2, OCHF.sub.2, SMe, S(O)Me, S(O).sub.2Me, SCF.sub.3, S(O)CF.sub.3, S(O).sub.2CF.sub.3, SCHF.sub.2, S(O)CHF.sub.2, S(O).sub.2CHF.sub.2, CO.sub.2Me, CO.sub.2Et, C(O)Me, OAc, C(O)NHMe, C(O)NMe.sub.2, CH.sub.2OMe and CH.sub.2OEt; or two R.sup.5 on two adjacent carbon atoms present on one phenyl ring are together a bridge selected from the group consisting of NCHCHCH, NCHCHN, OCH.sub.2CH.sub.2O, O(CH.sub.2)O and form together with the carbon atoms the two R.sup.5 are bonded to a 5- or 6-membered partially unsaturated or aromatic heterocyclic ring, wherein the ring is unsubstituted.
27. The method of claim 21, wherein R.sup.6 is selected from the group consisting of halogen, Me, Et, iPr, cPr, tBu, OMe, OEt, OnPr, OiPr, OtBu, OPh, ethynyl, (trimethylsilyl)ethynyl, vinyl, Ph, NO.sub.2, CN, CF.sub.3, OCF.sub.3, SF.sub.5, CHF.sub.2, OCHF.sub.2, SMe, S(O)Me, S(O).sub.2Me, SCF.sub.3, S(O)CF.sub.3, S(O).sub.2CF.sub.3, SCHF.sub.2, S(O)CHF.sub.2, S(O).sub.2CHF.sub.2, CO.sub.2Me, CO.sub.2Et, CO.sub.2iPr, C(O)Me, OAc, C(O)NHMe, C(O)NMe.sub.2, CH.sub.2OMe, CH.sub.2OEt, fluoromethyl, 2,2,2 trifluoroethyl, 1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl, 2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl, dimethoxymethyl, chloro(difluoro)methoxy, 2,2,2-trifluoroethoxy, 2,2 difluorocyclopropoxy, tert-butylsulfanyl, dimethylcarbamoylsulfanyl, morpholine-4-carbonyl, acetamido, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrrol-1-yl, pyrazol-1-yl, imidazol-1-yl and 1,2,4-triazol-1-yl.
28. The method of claim 21, wherein Y is phenyl unsubstituted or substituted with 1, 2, 3, 4 or 5 substituents R.sup.5; or naphthyl unsubstituted or substituted with 1 substituent R.sup.5; Q is phenyl unsubstituted or substituted with 1, 2 or 3 substituents R.sup.6; cyclohexyl unsubstituted or substituted with 1 substituent R.sup.6; or a 6-membered aromatic heterocyclic ring containing 1, 2 or 3 nitrogen atoms in the ring, wherein the aforementioned ring is unsubstituted or substituted with 1, 2 or 3 substituents R.sup.6; R.sup.1 is selected from the group consisting of H, Me, Et, CN, CH.sub.2CN, CH.sub.2CF.sub.3, halogen, CH.sub.2OH, CH.sub.2OMe, CH.sub.2OEt, CH.sub.2CO.sub.2Me, CH.sub.2CO.sub.2Et, CH.sub.2OSi(Me).sub.3 and CH.sub.2OSi(Et).sub.3; R.sup.2 is selected from the group consisting of H and halogen; R.sup.3 is selected from the group consisting of H, Me, Et, CN, CH.sub.2CN, CH.sub.2CF.sub.3, halogen, CH.sub.2OH, CH.sub.2OMe, CH.sub.2OEt, CH.sub.2CO.sub.2Me, CH.sub.2CO.sub.2Et, CH.sub.2OSi(Me).sub.3 and CH.sub.2OSi(Et).sub.3; R.sup.4 is selected from the group consisting of H and halogen; R.sup.5 is selected from the group consisting of halogen, cyano, tri-(C.sub.1-C.sub.4)silyl-C.sub.2-C.sub.4-alkynyl, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl, phenyl, C.sub.1-C.sub.6-alkoxy, C.sub.1-C.sub.6-alkylthio and (C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the eight radicals last mentioned are unsubstituted or partially or fully halogenated; or two R.sup.5 on two adjacent carbon atoms present on one phenyl ring are together a bridge selected from the group consisting of NCHCHCH, NCHCHN, OCH.sub.2CH.sub.2O, O(CH.sub.2)O and form together with the carbon atoms the two R.sup.5 are bonded to a 5- or 6-membered partially unsaturated or aromatic heterocyclic ring, wherein the ring is unsubstituted; R.sup.6 is selected from the group consisting of halogen, nitro, cyano, tri-(C.sub.1-C.sub.4)silyl-C.sub.2-C.sub.4-alkynyl, 2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl, dimethoxymethyl, dimethylcarbamoylsulfanyl, morpholine-4-carbonyl, acetamido, pyridyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, C.sub.1-C.sub.6-alkyl, C.sub.2-C.sub.6-alkenyl, C.sub.2-C.sub.6-alkynyl, C.sub.3-C.sub.6-cycloalkyl, phenyl, C.sub.1-C.sub.6-alkoxy, C.sub.3-C.sub.6-cycloalkoxy, phenoxy, C.sub.1-C.sub.6-alkylthio, C.sub.1-C.sub.6-alkylsulfonyl and (C.sub.1-C.sub.6-alkoxy)carbonyl, wherein the eleven radicals last mentioned are unsubstituted or partially or fully halogenated; R.sup.aa is C(S)N(R.sup.cc).sub.2; R.sup.bb is CN; each R.sup.cc is independently selected from the group consisting of H, Me, Et, propargyl, allyl, CH.sub.2OMe, CH.sub.2OEt; p is 0 or 1.
29. The method of claim 21, wherein R.sup.5 is selected from the group consisting of halogen, Me, OMe, CN, CF.sub.3, OCF.sub.3 and ethynyl.
30. The method of claim 21, wherein R.sup.6 is selected from the group consisting of halogen, Me, OMe, CN, CF.sub.3, OCF.sub.3 and ethynyl.
Description
EXAMPLES
A. Preparation Examples
(1) With appropriate modification of the starting materials, the procedures given in the synthesis examples below were used to obtain further compounds II and Ill. The compounds obtained in this manner are listed in the tables that follow, together with physical data.
(2) The products shown below were characterized by NMR spectroscopy.
(3) Procedure for the preparation of II-1:
(4) ##STR00111##
Preparation of ethyl 2-cyano-2-phenylacetate (Ex-1)
(5) A mixture of iodobenzene (4.08 g, 21.6 mmol), ethyl cyanoacetate (4.52 g, 40 mmol), potassium carbonate (11.0 g, 79.8 mmol) and copper(I)iodide (0.38 g, 2.0 mmol) in anhydrous dimethyl sulfoxide (50 mL) was stirred at 120 C. for 20 h under nitrogen atmosphere. The resulting reaction mixture was then poured into HCl (2N, 100 mL), and extracted with methyl t-butyl ether (3100 mL). The combined organic layers were washed with brine (50 mL), dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 9:1 hexanes/EtOAc) to afford ethyl 2-cyano-2-phenylacetate (Ex-1, 2.8 g, 76%) as pale yellow oil.
Preparation of ethyl 2-cyano-3-(4-ethynylphenyl)-2-phenylpropanoate (Ex-2)
(6) To a stirred ice-cold suspension of sodium hydride (60% in mineral oil, 0.44 g, 18.5 mmol, prewashed with hexanes, 25 mL) in anhydrous DMF (5 mL), a solution of ethyl 2-cyano-2-phenylacetate (Ex-1, 2.02 g, 10.7 mmol) in anhydrous DMF (5 mL) was added dropwise. The mixture was then allowed to warm to room temperature over a period of 1h upon stirring. 1-(Bromomethyl)-4-ethynylbenzene (1.8 g, 18.5 mmol) was added, and the mixture was stirred at room temperature for 4h. After reaction completion (TLC), the mixture was cooled to 0 C., quenched with HCl (2N, 2.0 mL), diluted with water (30 mL), and extracted with methyl t-butyl ether (3100 mL). The combined organic layers were washed with brine (20 mL), dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 9:1 hexanes/EtOAc) to afford ethyl 2-cyano-3-(4-ethynylphenyl)-2-phenylpropanoate (Ex-2, 2.7 g, 96%) as colorless viscous liquid.
Preparation of 2-cyano-3-(4-ethynylphenyl)-2-phenylpropanamide (Ex-3)
(7) A mixture of ethyl 2-cyano-3-(4-ethynylphenyl)-2-phenylpropanoate (Ex-2, 2.6 g, 8.6 mmol) and ammonia in methanol (7N, 50 mL) were stirred at room temperature for 2 days. After reaction completion (TLC), the solvent was removed under reduced pressure, and the residue was purified by column chromatography (silica gel, 7:3 hexanes/EtOAc) to afford 2-cyano-3-(4-ethynylphenyl)-2-phenylpropanamide (Ex-3, 2.0 g, 86%) as off-white solid.
Preparation of 2-cyano-3-(4-ethynylphenyl)-2-phenylpropanethioamide (II-1)
(8) A mixture of 2-cyano-3-(4-ethynylphenyl)-2-phenylpropanamide (0.70 g, 2.55 mmol), P.sub.4S.sub.10 (0.23 g, 0.51 mmol) and hexamethyldisiloxane (1.12 mL, 5.26 mmol) in a mixture of toluene and CH.sub.2Cl.sub.2 (1:1, 10 mL) was stirred and heated at 60 C. for about 12h. When reaction was completed by ca. 80% (TLC) (formation of side products was observed), the mixture was cooled to room temperature, followed by addition of K.sub.2CO.sub.3 (5M aq., 1 mL). The reaction mixture was stirred for 30 min at room temperature and then extracted with ethyl acetate (3100 mL). The combined organic layers were washed with brine (50 mL), dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, hexanes/EtOAc, gradient 8.5:1.5 to 7:3) to afford 2-cyano-3-(4-ethynylphenyl)-2-phenylpropanethioamide (II-1, 0.224 g, 30%) as a purple solid.
(9) TABLE-US-00007 (II)
(10) Procedure for the preparation of III-1 and III-4:
(11) ##STR00113##
Preparation of ethyl 2-cyano-2-(4-fluorophenyl)acetate (Ex-4)
(12) A solution of ethyl 2-cyanoacetate (2.55 g, 0.023 mol) in 250 ml tetrahydrofuran was added dropwise to a stirred and cooled mixture of sodium hydride (1.8 g, 60%, 0.045 mol) in 150 ml tetrahydrofuran. The reaction mixture was stirred for 1 h at room temperature and 1-fluoro-4-iodobenzene (5 g, 0.023 mol) and Pd(PPh.sub.3).sub.4 (1.99 g, 1.7 mmol) were added. The reaction mixture was heated to reflux and stirring was continued for 3.5 h. The mixture was poured on an ice/water mixture (100 g/100 g) and filtered, discarding the formed precipitate. The mother liquor was concentrated, kept at 0 C. overnight and the newly formed precipitate was again filtered off. The mother liquor (pH=11) was then washed with dichloromethane twice. Finally the aqueous layer was acidified with hydrochloric acid (10% aqueous solution) to pH 3.4, extracted with dichloromethane (2300 ml) and the organic layers were washed with brine, dried over anhydrous sodium sulfate and filtered. The solvent was removed under reduced pressure to afford ethyl 2-cyano-2-(4-fluorophenyl)acetate (Ex-4, 4 g, 50.5%).
Preparation of 2-cyano-2-(4-fluorophenyl)-N-methyl-acetamide (Ex-5)
(13) A solution of ethyl 2-cyano-2-(4-fluorophenyl)acetate (Ex-4, 2 g) in 10 mL NH.sub.2CH.sub.3 in THF was heated at reflux overnight. The solvent was removed under reduced pressure and the residue was purified by column chromatography (silica gel, pentane: EtOAc=20:1) to afford 2-cyano-2-(4-fluorophenyl)-N-methyl-acetamide (Ex-5, 1.1 g, 60%).
Preparation of 2-cyano-3-(4-ethynylphenyl)-2-(4-fluorophenyl)-N-methyl-propanamide (III-4)
(14) To a solution of 2-cyano-2-(4-fluorophenyl)-N-methyl-acetamide (Ex-5, 0.2 g, 0.001 mol) in 100 mL anhydrous acetone was added 1-(bromomethyl)-4-ethynyl-benzene (0.2 g, 0.001 mol) and K.sub.2CO.sub.3 (0.3 g, 0.002 mol) at room temperature under N.sub.2, then the reaction was stirred at this temperature overnight. The reaction mixture was filtered and the solvent was removed under reduced pressure. The residue was purified by column chromatography (silica gel, pentane:EtOAc=10:1) to yield 2-cyano-3-(4-ethynylphenyl)-2-(4-fluorophenyl)-N-methylpropanamide (III-4, 0.2 g, 60%).
Preparation of 2-cyano-3-(4-ethynylphenyl)-2-(4-fluorophenyl)-N-methyl-propanethioamide (III-1)
(15) To a solution of 2-cyano-3-(4-ethynylphenyl)-2-(4-fluorophenyl)-N-methyl-propanamide (III-4, 0.1 g, 0.032 mmol) in toluene (6 mL) was added Lawesson's reagent (0.2 g, 0.49 mmol). The mixture was heated in the microwave at 150 C. for 50 min. The solvent was removed under reduced pressure and the residue was purified by column chromatography (silica gel, pentane:EtOAc=8:1) to yield 2-cyano-3-(4-ethynylphenyl)-2-(4-fluorophenyl)-N-methylpropanethioamide (III-1, 0.1 g, 10%).
(16) TABLE-US-00008 (III)
Analytical Data:
(17) TABLE-US-00009 Comp. solvent .sup.1H-NMR-data (400 MHz, in ppm) II-1 (CD.sub.3).sub.2CO 3.60 (s, 1H), 3.98, 3.70 (ABq, 2H), 7.12 (d, 2H), 7.31 (d, 2H), 7.42-7.36 (m, 3H), 7.59-7.54 (m, 2H) II-2* CDCl.sub.3 3.3 (d, 1H), 3.78 (d, 1H), 5.61 (bs, 1H), 6.10 (bs, 1H), 7.11 (t, 2H), 7.26-7.28 (m, 2H), 7.53 (d, 2H), 7.55-7.58 (m, 2H) II-3* CDCl.sub.3 3.08 (s, 1H), 3.25 (d, 1H), 3.71 (d, 1H), 5.51 (bs, 1H), 6.08 (bs, 1H), 7.08-7.12 (m, 4H), 7.39 (d, 2H), 7.54-7.56 (m, 2H) II-4 CDCl.sub.3 3.62 (d, 1H), 4.00 (d, 1H), 7.07-7.12 (m, 2H), 7.23 (d, 2H), 7.49 (d, 2H), 7.52-7.56 (m, 2H) II-5 CDCl.sub.3 3.31 (d, 1H), 3.85 (d, 1H), 6.19 (bs, 1H), 6.27 (bs, 1H), 7.29 (d, 2H), 7.62-7.67 (m, 3H), 7.76 (dd, 1H), 8.55 (d, 1H) II-6 (CD.sub.3).sub.2SO 10.224 (s, 1H), 9.357 (s, 1H), 7.597-7.574 (m, 2H), 7.379- 7.358 (m, 2H), 7.320-7.275 (m, 2H), 7.163-7.143 (m, 2H), 4.164 (s, 1H), 3.918-3.884 (m, 1H), 3.699-3.664 (m, 1H) II-7 CDCl.sub.3 7.541-7.521 (m, 2H), 7.315-7.295 (m, 2H), 7.166-7.151 (m, 2H), 6.896-6.848 (m, 1H), 4.048-4.019 (m, 1H), 3.635-3.600 (m, 1H) II-8 (CD.sub.3).sub.2SO 10.327 (s, 1H), 9.415 (s, 1H), 7.402-7.355 (m, 3H), 7.268- 7.251 (m, 2H), 7.205-7.184 (m, 2H), 4.175 (s, 1H), 3.931- 3.897 (m, 1H), 3.754-3.720 (m, 1H) II-9 (CD.sub.3).sub.2SO 10.342 (s, 1H), 9.378 (s, 1H), 7.499-7.462 (m, 2H), 7.407- 7.387 (m, 2H), 7.214-7.194 (m, 2H), 4.176 (s, 1H), 3.934- 3.898 (m, 1H), 3.745-3.710 (m, 1H) II-10 (CD.sub.3).sub.2SO 10.351 (s, 1H), 9.393 (s, 1H), 7.675-7.654 (m, 2H), 7.513- 7.474 (m, 2H), 7.422-7.402 (m, 2H), 4.006-3.971 (m, 1H), 3.837-3.802 (m, 1H) II-11 CDCl.sub.3 7.822-7.608 (m, 2H), 7.595-7.573 (m, 2H), 7.386-7.366 (m, 1H), 7.264-7.139 (m, 2H), 6.906-6.885 (m, 2H), 4.457-4.355 (m, 1H), 1.666-1.379 (m, 3H) II-12 (CD.sub.3).sub.2SO 10.464 (s, 0.5H), 10.031 (s, 0.5H), 9.664 (s, 0.5H), 9.216 (s, 0.5H), 7.801-7.739 (m, 2H), 7.563-7.526 (m, 2H), 7.416- 7.396 (m, 1H), 7.155-7.139 (m, 2H), 4.506-4.415 (m, 1H), 1.558-1.284 (m, 3H) II-13 (CD.sub.3).sub.2SO 10.476 (s, 0.5H), 10.041 (s, 0.5H), 9.653 (s, 0.5H), 9.197 (s, 0.5H), 7.787-7.733 (m, 3H), 7.577-7.556 (m, 2H), 7.442- 7.375 (m, 2H), 4.487-4.404 (m, 1H), 1.552-1.288 (m, 3H) II-14 CDCl.sub.3 8.836-8.734 (s, 1H), 8.032-7.462 (m, 3H), 7.255-7.234 (m, 1H), 6.927-6.672 (m, 1H), 1.662-1.399 (m, 3H) II-15 CDCl.sub.3 8.824 (s, 0.2H), 8.697 (s, 0.5H), 8.022-7.612 (m, 4H), 7.207-7.136 (m, 1H), 6.906-6.863 (m, 1H), 1.662-1.373 (m, 3H) II-16 CDCl.sub.3 8.818-8.721 (s, 1H), 7.915-7.643 (m, 2H), 7.460-7.359 (m, 2H), 4.710-4.384 (m, 1H), 1.626-1.370 (m, 3H) II-17 CDCl.sub.3 7.575 (d, J = 7.78 Hz, 2 H), 7.350 (d, J = 7.78 Hz, 2 H), 7.210 (d, J = 6.27 Hz, 2 H), 6.885 (t, J = 8.41 Hz, 1 H), 6.145 (br. s., 1 H), 5.545 (br. s., 1 H), 3.804 (d, J = 13.30 Hz, 1 H), 3.292 (d, J = 13.55 Hz, 1 H) II-18 CDCl.sub.3 7.590 (d, J = 7.94 Hz, 2 H), 7.319-7.391 (m, 4 H), 6.167 (br. s., 1 H), 5.449-5.638 (m, 1 H), 3.779 (d, J = 13.67 Hz, 1 H), 3.260 (d, J = 13.67 Hz, 1 H) II-19 (CD.sub.3).sub.2SO 7.912-7.737 (m, 4H), 7.515-7.495 (m, 2 H), 7.378-7.344 (m, 2 H), 7.286-7.267 (m, 1 H), 7.142-7.120 (m, 1 H), 4.186-4.077 (m, 1 H), 1.523-1.507 (d, J = 6.40 Hz, 2 H), 1.132-1.114 (d, J = 7.2 Hz, 1 H) II-20 (CD.sub.3).sub.2SO 8.005-7.959 (d, J = 8.40 Hz, 1 H), 7.729-7.714 (d, J = 6.0 Hz, 1 H), 7.590-7.545 (m, 2 H), 7.380-7.360 (d, J = 8.0 Hz, 1H), 7.248-7.226 (m, 1H), 4.242-4.114 (m, 1 H), 1.503- 1.487 (d, J = 6.40 Hz, 2 H), 1.155-1.137 (d, J = 7.2 Hz, 1 H) II-21 CDCl.sub.3 7.595-7.522 (m, 2H), 7.310-7.285 (m, 1H), 7.200-7.185 (m, 2H), 7.110-7.093 (m, 2H), 7.068-6.911 (m, 1H), 4.054-4.019 (m, 1H), 3.631-3.597 (m, 1H) II-22 CDCl.sub.3 7.629 (s, 1H), 7.363-7.306 (m, 4H), 7.061-7.040 (m, 2H), 4.291-4.241 (m, 1H), 1.613-1.577 (m, 3H) II-23 CDCl.sub.3 7.849 (s, 1H), 7.395-7.261 (m, 4H), 7.171-7.151 (m, 2H), 6.870-6.865 (m, 1H), 3.984-3.950 (m, 1H), 3.840-3.804 (m, 1H) II-24 CDCl.sub.3 7.363-7.270 (m, 3H), 7.192-7.177 (m, 2H), 6.902-6.865 (m, 1H), 6.214 (s, 2H), 5.789 (s, 1H), 3.758-3.724 (m, 1H), 3.561-3.525 (m, 1H) II-25 CDCl.sub.3 7.55 (d, 2H), 7.35 (t, 2H), 2.61 (dd, 1 H), 2.25-2.11 (m, 2H), 2.06-1.81 (m, 4H), 1.79-1.68 (m, 1H), 1.56-0.95 (m, 1H), 1.94-1.28 (m, 2H), 1.20-0.98 (m, 2H) III-1 CD.sub.3OD 7.499-7.466 (m, 2H), 7.288-7.269 (m, 2H), 7.134-7.113 (m, 2H), 7.092-7.007 (m, 2H), 3.935-3.901 (m, 1H), 3.695-3.661 (m, 1H), 3.458 (s, 1H), 3.053 (s, 3H) III-2 CD.sub.3OD 7.320-7.300 (m, 2H), 7.113-7.066 (m, 4H), 6.987-6.965 (m, 1H), 3.945-3.911 (m, 1H), 3.706-3.672 (m, 1H), 3.452 (s, 1H), 3.065 (s, 3H) III-3 CD.sub.3OD 7.343-7.261 (m, 4H), 7.116-7.095 (m, 2H), 3.949-3.915 (m, 1H), 7.092-7.007 (m, 1H), 3.696-3.662 (m, 1H), 3.475 (s, 1H), 3.062 (s, 3H) III-4 CD.sub.3OD 7.525-7.490 (m, 2H), 7.330-7.310 (m, 2H), 7.172-7.084 (m, 4H), 3.733-3.699 (m, 1H), 3.462-3.376 (m, 2H), 2.722 (s, 3H) III-5 CD.sub.3OD 7.357-7.337 (m, 2H), 7.154-7.134 (m, 2H), 7.043-6.999 (m, 1H), 3.752-3.718 (m, 1H), 3.472 (s, 1H), 3.388-3.355 (m, 2H), 2.732 (s, 3H) III-6 CDCl.sub.3 7.443-7.423 (m, 2H), 7.352-7.316 (m, 2H), 7.168-7.148 (m, 2H), 6.219 (s, 1H), 3.736-3.702 (m, 1H), 3.223-3.189 (m, 1H), 3.107 (s, 1H), 2.822 (s, 3H) *measured with 500 MHz
B. Biological Examples
(18) The activity of the compounds of formula II and III of the present invention could be demonstrated and evaluated in biological tests described in the following.
(19) If not otherwise specified the test solutions are prepared as follows:
(20) 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 and in general at concentrations of ppm (wt/vol).
(21) B.1 Mediterranean Fruitfly (Ceratitis capitata)
(22) 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. 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 l, using a custom built micro atomizer, at two replications. After application, microtiter plates were incubated at about 281 C. and about 805% relative humidity for 5 days. Egg and larval mortality was then visually assessed.
(23) In this test, the compounds II-3, II-4, II-10, II-11, II-12, II-13, II-14, II-15, II-16, II-17, II-18, II-19, II-21, II-22, II-23, II-24, II-25, II-6, II-8, II-9 and III-4, respectively, at 2500 ppm showed a mortality of at least 75% in comparison with untreated controls.
(24) B.2 Green Peach Aphid (Myzus persicae)
(25) 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. 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. 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.
(26) In this test, the compounds II-4, II-10, II-11, II-12, II-13, II-14, II-15, II-16, II-21, II-25, II-8 and II-9, respectively, at a concentration of the test solution of 2500 mg/L showed a mortality of at least 75%.
(27) B.3 Orchid Thrips (Dichromothrips Corbetti)
(28) Dichromothrips corbetti adults used for bioassay are obtained from a colony maintained continuously under laboratory conditions. For testing purposes, the test compound is diluted to a concentration of 300 ppm (wt compound: vol diluent) in a 1:1 mixture of acetone:water (vol:vol), plus 0.01% vol/vol Kinetic surfactant. Thrips potency of each compound is evaluated by using a floral-immersion technique. Plastic petri dishes are used as test arenas. All petals of individual, intact orchid flowers are dipped into treatment solution and allowed to dry. Treated flowers are placed into individual petri dishes along with 10-15 adult thrips. The petri dishes are then covered with lids. All test arenas are held under continuous light and a temperature of about 28 C. for duration of the assay. After 4 days, the numbers of live thrips are counted on each flower, and along inner walls of each petri dish. The level of thrips mortality is extrapolated from pre-treatment thrips numbers.
(29) In this test, the compounds II-4, II-10, II-11, II-12, II-13, II-14, II-15, II-16, II-17, II-18, II-19, II-21, II-22, II-23, II-24, II-6, II-7, II-8, II-9, II-2, II-3, II-4 and III-6, respectively, at 500 ppm showed a mortality of at least 75% in comparison with untreated controls.
(30) B.4 Silverleaf Whitefly (Bemisia argentifolii)
(31) The active compounds were formulated in cyclohexanone as a 10,000 ppm solution supplied in 1.3 ml ABgene tubes. These 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). 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 10 to 12 whitefly adults (approximately 3-5 days old) were introduced. The insects were collected using an aspirator and 0.6 cm, nontoxic Tygon tubing (R-3603) 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 (150-micron mesh polyester screen PeCap from Tetko, Inc.). Test plants were maintained in a growth room at 25 C. and 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.
(32) In this test, the compounds II-1, II-6 and II-7, respectively, at 500 ppm showed a mortality of at least 75% in comparison with untreated controls.
(33) B.5 Southern Armyworm (Spodoptera eridania)
(34) The active compounds were formulated in cyclohexanone as a 10,000 ppm solution supplied in 1.3 ml ABgene tubes. These 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). Lima bean plants (variety Sieva) were grown 2 plants to a pot and selected for treatment at the 1st true leaf stage. Test solutions were sprayed onto the foliage by an automated electro-static 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. Ten to 11 armyworm larvae were placed into the bag and the bags zipped closed. Test plants were maintained in a growth room at 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 bags. Mortality and reduced feeding were assessed 4 days after treatment, compared to untreated control plants.
(35) In this test, the compound II-2 at 500 ppm showed a mortality of at least 75% in comparison with untreated controls.
(36) B.6 Boll Weevil (Anthonomus grandis)
(37) For evaluating control of boll weevil (Anthonomus grandis) the test unit consisted of 24-well-microtiter plates containing an insect diet and 20-30 A. grandis 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 20 l, using a custom built micro atomizer, at two replications. After application, microtiter plates were incubated at about 231 C. and about 505% relative humidity for 5 days. Egg and larval mortality was then visually assessed.
(38) In this test, the compounds II-1, II-3, II-4, II-10, II-11, II-12, II-13, II-14, II-15, II-16, II-17, II-18, II-19, II-20, II-21, II-22, II-23, II-24, II-25, II-6, II-7, II-8, II-9, III-1, III-2, III-3, III-4 and III-5, respectively, at 2500 ppm showed a mortality of at least 75% in comparison with untreated controls.
(39) B.7 Red Spider Mite (Tetranychus kanzawai)
(40) The active compound is dissolved at the desired concentration in a mixture of 1:1 (vol:vol) distilled water:acetone. Add surfactant (Alkamuls EL 620) at the rate of 0.1% (vol/vol). The test solution is prepared at the day of use. 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% relative humidity. Percent mortality was assessed 72 hours after treatment.
(41) In this test, the compounds II-2 and II-11, respectively, at 500 ppm showed a mortality of at least 75% in comparison with untreated controls.
(42) B.8 Rice Brown Plant Hopper (Nilaparvata lugens)
(43) 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.
(44) In this test, the compounds II-3, II-4, II-10, II-11, II-12, II-13, II-14, II-16, II-21, II-22, II-23, II-6, II-7, II-8, II-9, III-2, III-3, III-5 and III-6, respectively, at 500 ppm showed a mortality of at least 75% in comparison with untreated controls.
(45) B.9 Yellow Fever Mosquito (Aedes aegypti)
(46) For evaluating control of yellow fever mosquito (Aedes aegypti) the test unit consisted of 96-well-microtiter plates containing 200 l of tap water per well and 5-15 freshly hatched A. aegypti larvae. The compounds or mixtures were formulated using a solution containing 75% water and 25% DMSO. Different concentrations of formulated compounds or mixtures were sprayed onto the insect diet at 2.5 l, using a custom built micro atomizer, at two replications. After application, microtiter plates were incubated at 281 C., 805% RH for 2 days. Larval mortality was then visually assessed.
(47) In this test, the compounds III-1, II-2, II-3, II-4, II-5, II-10, II-11, II-12, II-13, II-14, II-15, II-16, II-17, II-18, II-19, II-20, II-21, II-22, II-23, II-24, II-25, II-6, II-7, II-8, II-9, III-2 and III-3, respectively, at 2500 ppm showed a mortality of at least 75% in comparison with untreated controls.
(48) B.10 Green Soldier Stink Bug (Nezara viridula)
(49) The active compound is dissolved at the desired concentration in a mixture of 1:1 (vol:vol) distilled water:aceteone. Surfactant (Kinetic HV) is added at a rate of 0.01% (vol/vol). The test solution is prepared at the day of use. Soybean pods were placed in microwavable plastic cups lined with moist filter paper and inoculated with ten 3rd instar N. viridula. Using a hand atomizer, an approximately 2 ml solution is sprayed into each cup. Treated cups were kept at about 28-29 C. and relative humidity of about 50-60%. Percent mortality was recorded after 5 days.
(50) In this test, the compounds II-1, II-3, II-4, II-10, II-11, II-12, II-13, II-14, II-15, II-16 and II-9, respectively, at 500 ppm showed a mortality of at least 75% in comparison with untreated controls.