Patent ID: 6156700
Filing Date: 2000-12-05
Classification: A01N,C07D,C07F

Abstract:
A compound having the structural formula ##STR548## wherein R is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, benzyl, OR.sub.4 or NR.sub.5 R.sub.6 ;R.sub.1 and R.sub.2 are each independently hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 haloalkenyl, C.sub.3 -C.sub.6 alkynyl, OR.sub.7, S(O).sub.n R.sub.8 or NR.sub.9 R.sub.10 ;R.sub.3 is halogen or A.sub.2 R.sub.11 ;X is hydrogen, halogen or C.sub.1 -C.sub.4 alkyl;X.sub.1 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy;Z is O or S(O).sub.m ;Y is halogen, cyano, R.sub.12, X.sub.2 R.sub.12, X.sub.3 R.sub.12, X.sub.2 X.sub.3 R.sub.12 or X.sub.3 X.sub.2 R.sub.12 ;X.sub.2 is O, S(O).sub.p or NR.sub.13 ;X.sub.3 is --C(.dbd.A.sub.3)--, --C(.dbd.NOR.sub.14)-- or --C(.dbd.N--NR.sub.13 R.sub.50);R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.11 and R.sub.14 are each independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.2 -C.sub.8 alkoxyalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl or benzyl;R.sub.12 is hydrogen,a C.sub.1 -C.sub.8 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.5 -C.sub.6 cycloalkenyl or C.sub.2 -C.sub.8 alkynyl group, wherein each group is optionally substituted with any combination of one to six halogen atoms, one to three C.sub.1 -C.sub.20 alkoxy groups optionally substituted with one C.sub.1 -C.sub.8 alkoxy, benzyloxy or C.sub.1 -C.sub.6 alkylthio group, one or two C.sub.1 -C.sub.10 haloalkoxy groups, one or two NR.sub.15 R.sub.16 groups, one to three S(O).sub.q R.sub.17 groups, one or two cyano groups, one or two C.sub.3 -C.sub.7 cycloalkyl groups, one thiocyano group, one O(SO.sub.2)R.sub.17 group, one O(NO.sub.2) group, one or two C(O)R.sub.18 groups, one or two CO.sub.2 R.sub.19 groups, one or two C(O)SR.sub.19 groups, one or two C(O)NR.sub.20 R.sub.21 groups, one to three X.sub.4 R.sub.22 groups, one or two P(O)(OR.sub.23).sub.2 groups, one or two Si(R.sub.24).sub.3 groups,one 4- to 10-membered monocyclic or fused bicyclic heterocyclic ring optionally substituted with any combination of one or two oxo groups, one or two thioxo groups, one to three halogen atoms, one to three C.sub.1 -C.sub.4 alkyl groups, one to three C.sub.1 -C.sub.4 haloalkyl groups, one to three C.sub.1 -C.sub.4 alkoxy groups, one to three C.sub.1 -C.sub.4 haloalkoxy groups or one or two X.sub.4 R.sub.22 groups,one quaternary organic ammonium group, orone or two phenyl groups wherein each phenyl group is independently optionally substituted with any combination of one to three halogen atoms, one to three C.sub.1 -C.sub.6 alkyl groups, one to three C.sub.1 -C.sub.6 alkoxy groups, one C.sub.3 -C.sub.7 cycloalkyl group, one C.sub.1 -C.sub.4 haloalkyl group, one C.sub.1 -C.sub.4 alkylthio group, one cyano group, one nitro group, one C(O)R.sub.25 group, one CO.sub.2 R.sub.26 group or one X.sub.5 R.sub.27 group,phenyl optionally substituted with any combination of one to three halogen atoms, one to three C.sub.1 -C.sub.4 alkyl groups, one to three C.sub.1 -C.sub.4 alkoxy groups, one C.sub.3 -C.sub.6 cycloalkyl group, one C.sub.1 -C.sub.4 haloalkyl group, one C.sub.1 -C.sub.4 alkylthio group, one cyano group, one nitro group, one C(O)R.sub.25 group, one CO.sub.2 R.sub.26 group, one X.sub.4 R.sub.22 group, one CH.dbd.CHR.sub.22 group, one CH.sub.2 CH(R.sub.28)R.sub.22 group or one N(R.sub.29)SO.sub.2 R.sub.30 group, orindan optionally substituted with any combination of one or two halogen atoms, one or two C.sub.1 -C.sub.4 alkyl groups, one C.sub.1 -C.sub.4 alkoxy group, one C.sub.1 -C.sub.4 haloalkyl group, one C.sub.1 -C.sub.4 alkylthio group, one cyano group, one nitro group, one C(O)R.sub.25 group, one CO.sub.2 R.sub.26 group, one X.sub.4 R.sub.22 group, one CH.dbd.CHR.sub.22 group, one CH.sub.2 CH(R.sub.28)R.sub.22 group or one N(R.sub.29)SO.sub.2 R.sub.30 group,and when R.sub.12 and R.sub.13 are taken together with the nitrogen atom to which they are attached, they form a 5- to 12-membered monocyclic or fused bicyclic, heterocyclic ring optionally substituted with one or more groups independently selected from halogen, cyano, nitro, amino, hydroxyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylsulfonyl or X.sub.4 R.sub.22 groups;R.sub.13 is hydrogen, C.sub.1 -C.sub.8 alkoxyalkyl, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, benzyl, OR.sub.23, cyano, SO.sub.2 R.sub.51 or one 5- to 12-membered monocyclic or fused bicyclic heterocyclic ring optionally substituted with one or more groups independently selected from halogen, cyano, nitro, amino, hydroxyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 haloalkoxy, and when R.sub.13 and R.sub.12 are taken together with the nitrogen atom to which they are attached, they form a 5- to 12-membered monocyclic or fused bicyclic, heterocyclic ring optionally substituted with one or more groups independently selected from halogen, cyano, nitro, amino, hydroxyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylsulfonyl or X.sub.4 R.sub.22 groups;R.sub.28 is halogen;R.sub.22 and R.sub.27 are each independently hydrogen, Si(R.sub.31).sub.3, C(O)NR.sub.35 R.sub.36, C(O)R.sub.33, SO.sub.2 R.sub.47,C.sub.1 -C.sub.20 alkyl substituted with one hydroxyl, benzyloxy, nitro, OC(O)R.sub.33, C.sub.1 -C.sub.6 alkoxy, CO.sub.2 R.sub.32, C(O)R.sub.33, C(A.sub.4 R.sub.34).sub.2, C(O)NR.sub.35 R.sub.36, C(O)ON.dbd.CR.sub.37 R.sub.38, P(O)(OH)NH.sub.2, P(O)(OH)(OR.sub.23), C(O)NR.sub.35 OR.sub.23, cyano or 2-dioxolanyl group,one phenyl, dihydrofuranone or furanone ring wherein each ring is optionally substituted with any combination of one to three halogen atoms, one to three C.sub.1 -C.sub.4 alkyl groups, one to three C.sub.1 -C.sub.4 haloalkyl groups, one to three C.sub.1 -C.sub.4 alkoxy groups or one to three C.sub.1 -C.sub.4 haloalkoxy groups, orone 5- to 12-membered monocyclic or fused bicyclic, heterocyclic ring optionally substituted with one or more groups independently selected from halogen, cyano, nitro, amino, hydroxyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy or C.sub.1 -C.sub.4 haloalkylsulfonyl groups,C.sub.3 -C.sub.20 alkenyl optionally substituted with one to three halogen atoms, one hydroxyl group, one C.sub.1 -C.sub.6 alkoxy, CO.sub.2 R.sub.32, C(O)R.sub.33, C(A.sub.4 R.sub.34).sub.2, C(O)NR.sub.35 R.sub.36, C(O)ON.dbd.CR.sub.37 R.sub.38, C(O)NR.sub.35 OR.sub.23, cyano or 2-dioxolanyl group, or one phenyl, dihydrofuranone or furanone ring wherein each ring is optionally substituted with any combination of one to three halogen atoms, one to three C.sub.1 -C.sub.4 alkyl groups, one to three C.sub.1 -C.sub.4 haloalkyl groups, one to three C.sub.1 -C.sub.4 alkoxy groups or one to three C.sub.1 -C.sub.4 haloalkoxy groups,C.sub.5 -C.sub.8 cycloalkenyl optionally substituted with one hydroxyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, CO.sub.2 R.sub.32, C(O)R.sub.33, C(A.sub.4 R.sub.34).sub.2, C(O)NR.sub.35 R.sub.36, C(O)ON.dbd.CR.sub.37 R.sub.38, C(O)NR.sub.35 OR.sub.23, cyano or 2-dioxolanyl group, or one phenyl, dihydrofuranone or furanone ring wherein each ring is optionally substituted with any combination of one to three halogen atoms, one to three C.sub.1 -C.sub.4 alkyl groups, one to three C.sub.1 -C.sub.4 alkoxy groups or one to three C.sub.1 -C.sub.4 haloalkoxy groups,C.sub.3 -C.sub.10 alkynyl optionally substituted with one hydroxyl, C.sub.1 -C.sub.6 alkoxy, CO.sub.2 R.sub.32, C(O)R.sub.33, C(A.sub.4 R.sub.34).sub.2, C(O)NR.sub.35 R.sub.36, C(O)ON.dbd.CR.sub.37 R.sub.38, C(O)NR.sub.35 OR.sub.23, cyano or 2-dioxolanyl group, or one phenyl, dihydrofuranone or furanone ring wherein each ring is optionally substituted with any combination of one to three halogen atoms, one to three C.sub.1 -C.sub.4 alkyl groups, one to three C.sub.1 -C.sub.4 haloalkyl groups, one to three C.sub.1 -C.sub.4 alkoxy groups or one to three C.sub.1 -C.sub.4 haloalkoxy groups,phenyl optionally substituted with any combination of one to three halogen atoms, one to three C.sub.1 -C.sub.6 alkyl groups, one to three C.sub.1 -C.sub.6 alkoxy groups, one C.sub.1 -C.sub.4 haloalkyl group, one C.sub.1 -C.sub.4 haloalkoxy group, one cyano group, one nitro group, one NR.sub.39 R.sub.40 group or one C(O)R.sub.33 group,benzyl optionally substituted on the phenyl ring with any combination of one to three halogen atoms, one to three C.sub.1 -C.sub.6 alkyl groups, one to three C.sub.1 -C.sub.6 alkoxy groups, one C.sub.1 -C.sub.4 haloalkyl group, one C.sub.1 -C.sub.4 haloalkoxy group, one cyano group, one nitro group, one NR.sub.39 R.sub.40 group or one C(O)R.sub.33 group, ora 4- to 10-membered heterocyclic ring optionally substituted with any combination of one or two oxo groups, one or two thioxo groups, one to three halogen atoms, one to three C.sub.1 -C.sub.4 alkyl groups, one to three C.sub.1 -C.sub.4 haloalkyl groups, one to three C.sub.1 -C.sub.4 alkoxy groups or one to three C.sub.1 -C.sub.4 haloalkoxy groups;R.sub.15 and R.sub.20 are each independently hydrogen,a C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.2 -C.sub.6 alkenyl or C.sub.2 -C.sub.6 alkynyl group wherein each group is optionally substituted with one CO.sub.2 R.sub.42 group,benzyl optionally substituted with any combination of one to three halogen atoms, one to three C.sub.1 -C.sub.4 alkyl groups, one to three C.sub.1 -C.sub.4 haloalkyl groups, one to three C.sub.1 -C.sub.4 alkoxy groups or one to three C.sub.1 -C.sub.4 haloalkoxy groups,phenyl optionally substituted with any combination of one to three halogen atoms, one to three C.sub.1 -C.sub.4 alkyl groups, one to three C.sub.1 -C.sub.4 haloalkyl groups, one to three C.sub.1 -C.sub.4 alkoxy groups, one to three C.sub.1 -C.sub.4 haloalkoxy groups, one CO.sub.2 R.sub.26 group,C(O)R.sub.43, orCO.sub.2 R.sub.42 ;R.sub.16 and R.sub.21 are each independently hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.3 -C.sub.7 cycloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.3 -C.sub.7 cycloalkenyl, C.sub.2 -C.sub.6 alkynyl, P(O)(OR.sub.44).sub.2, SO.sub.2 R.sub.45, C(O)R.sub.46,benzyl optionally substituted with any combination of one to three halogen atoms, one to three C.sub.1 -C.sub.4 alkyl groups, one to three C.sub.1 -C.sub.4 haloalkyl groups, one to three C.sub.1 -C.sub.4 alkoxy groups, one to three C.sub.1 -C.sub.4 haloalkoxy groups or one X.sub.4 R.sub.22 group, orphenyl optionally substituted with any combination of one to three halogen atoms, one to three C.sub.1 -C.sub.4 alkyl groups, one to three C.sub.1 -C.sub.4 haloalkyl groups, one to three C.sub.1 -C.sub.4 alkoxy groups, one to three C.sub.1 -C.sub.4 haloalkoxy groups or one X.sub.4 R.sub.22 group;R.sub.17, R.sub.18, R.sub.25, R.sub.30, R.sub.33, R.sub.45 and R.sub.51 are each independently NR.sub.46 R.sub.48, --N.dbd.CR.sub.46 R.sub.48, C.sub.1 -C.sub.8 alkyl optionally substituted with one C.sub.1 -C.sub.6 alkoxy, thiophene or furan group, C.sub.1 -C.sub.6 haloalkyl, C.sub.3 -C.sub.8 cycloalkyl, CO.sub.2 R.sub.23, C.sub.2 -C.sub.6 alkenyl optionally substituted with phenyl,benzyl optionally substituted with any combination of one to three halogen atoms, one to three C.sub.1 -C.sub.4 alkyl groups, one to three C.sub.1 -C.sub.4 haloalkyl groups, one to three C.sub.1 -C.sub.4 alkoxy groups, one to three C.sub.1 -C.sub.4 haloalkoxy groups, one nitro group, one cyano group or one X.sub.4 R.sub.22 group,phenyl optionally substituted with any combination of one to three halogen atoms, one to three C.sub.1 -C.sub.4 alkyl groups, one to three C.sub.1 -C.sub.4 haloalkyl groups, one to three C.sub.1 -C.sub.4 alkoxy groups, one to three C.sub.1 -C.sub.4 haloalkoxy groups, one nitro group, one cyano group or one X.sub.4 R.sub.22 group, ora 5- to 12-membered monocyclic or fused bicyclic, heterocyclic ring optionally substituted with one or more groups independently selected from halogen, cyano, nitro, amino, hydroxyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylsulfonyl or X.sub.4 R.sub.22 groups;R.sub.19 and R.sub.26 are each independently hydrogen, C.sub.1 -C.sub.20 alkyl, C.sub.1 -C.sub.8 haloalkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.3 -C.sub.7 halocycloalkyl, C.sub.3 -C.sub.20 alkenyl, C.sub.3 -C.sub.8 haloalkenyl, C.sub.5 -C.sub.8 cycloalkenyl, C.sub.5 -C.sub.8 halocycloalkenyl, C.sub.3 -C.sub.8 alkynyl, C.sub.3 -C.sub.8 haloalkynyl, Si(R.sub.41).sub.3, benzyl, phenyl, furfuryl, pyridyl, thienyl, oximino or an alkali metal, alkaline earth metal, manganese, copper, zinc, cobalt, silver, nickel, ammonium or organic ammonium cation;R.sub.32 is hydrogen,Si(R.sub.47).sub.3,di(C.sub.1 -C.sub.4 alkyl)imino,C.sub.1 -C.sub.20 alkyl optionally substituted with one CO.sub.2 R.sub.48, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.6 thioalkyl, C.sub.2 -C.sub.20 alkoxyalkoxy, phenyl, OSi(R.sub.47).sub.3, OC(O)R.sub.33, C.sub.3 -C.sub.7 cycloalkyl or di(C.sub.1 -C.sub.4 alkyl)imino group,C.sub.1 -C.sub.15 haloalkyl,C.sub.3 -C.sub.8 cycloalkyl optionally substituted with one CO.sub.2 R.sub.48 group,C.sub.3 -C.sub.8 halocycloalkyl,C.sub.3 -C.sub.20 alkenyl optionally substituted with one phenyl group,C.sub.3 -C.sub.15 haloalkenyl,C.sub.5 -C.sub.8 cycloalkenyl,C.sub.5 -C.sub.8 halocycloalkenyl,C.sub.3 -C.sub.20 alkynyl optionally substituted with one phenyl group,C.sub.3 -C.sub.20 haloalkynyl,benzyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy and C.sub.1 -C.sub.4 haloalkoxy groups,phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy and C.sub.1 -C.sub.4 haloalkoxy groups,2-, 3- or 4-pyridyl,2- or 3-furyl,2- or 3-thienyl,2-tetrahydrofuranyl,C.sub.1 -C.sub.4 alkyl substituted with one pyridyl, furyl, thienyl, tetrahydrofuryl, C.sub.3 -C.sub.8 cycloalkyl, dioxane or NR.sub.49 R.sub.50 group, oran alkali metal, alkaline earth metal, manganese, copper, zinc, cobalt, silver, nickel, ammonium or organic ammonium cation;R.sub.34, R.sub.37 and R.sub.38 are each independently C.sub.1 -C.sub.6 alkyl;R.sub.35 and R.sub.49 are each independently hydrogen or C.sub.1 -C.sub.6 alkyl and R.sub.36 and R.sub.50 are each independently hydrogen, cyano, C.sub.1 -C.sub.6 alkyl, SO.sub.2 R.sub.51 or phenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy and C.sub.1 -C.sub.4 haloalkoxy groups, or when R.sub.35 and R.sub.36 or R.sub.49 and R.sub.50 are taken together with the nitrogen atom to which they are attached, they form a 5- to 12-membered monocyclic or fused bicyclic, heterocyclic ring optionally substituted with one or more groups independently selected from halogen, cyano, nitro, amino, hydroxyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy or C.sub.1 -C.sub.4 haloalkylsulfonyl groups;m, n, p and q are each independently an integer of 0, 1 or 2;R.sub.29 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl;R.sub.24, R.sub.31, R.sub.41 and R.sub.47 are each independently C.sub.1 -C.sub.4 alkyl,benzyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy and C.sub.1 -C.sub.4 haloalkoxy groups, orphenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy and C.sub.1 -C.sub.4 haloalkoxy groups;R.sub.23, R.sub.39, R.sub.40, R.sub.42, R.sub.43, R.sub.44, R.sub.46 and R.sub.48 are each independently hydrogen, C.sub.2 -C.sub.6 alkenyl, C.sub.3 -C.sub.8 cycloalkyl,C.sub.1 -C.sub.8 alkyl optionally substituted with one or two C.sub.1 -C.sub.4 alkoxy groups,benzyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy and C.sub.1 -C.sub.4 haloalkoxy groups, orphenyl optionally substituted with one or more groups independently selected from halogen, cyano, nitro, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy and C.sub.1 -C.sub.4 haloalkoxy groups, andwhen R.sub.46 and R.sub.48 are taken together with the atom to which they are attached, they form a 5- to 12-membered monocyclic or fused bicyclic, heterocyclic or cycloalkyl ring optionally substituted with one or more groups independently selected from halogen, cyano, nitro, amino, hydroxyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy or C.sub.1 -C.sub.4 haloalkylsulfonyl groups; andA, A.sub.1, A.sub.2, A.sub.3, A.sub.4, X.sub.4 and X.sub.5 are each independently O or S; andthe optical isomers, diastereomers and/or tautomers thereof.