AR085645A1 - HERBICIDE PIRIMIDINONE DERIVATIVES - Google Patents

HERBICIDE PIRIMIDINONE DERIVATIVES

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Publication number
AR085645A1
AR085645A1 ARP120100774A ARP120100774A AR085645A1 AR 085645 A1 AR085645 A1 AR 085645A1 AR P120100774 A ARP120100774 A AR P120100774A AR P120100774 A ARP120100774 A AR P120100774A AR 085645 A1 AR085645 A1 AR 085645A1
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AR
Argentina
Prior art keywords
alkyl
cycloalkyl
phenyl
alkoxyalkyl
haloalkyl
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ARP120100774A
Other languages
Spanish (es)
Inventor
Patrick Ryan Kovacs
Atul Puri
William Louis Patzoldt
Kanu Maganbhai Patel
Thomas Paul Selby
Brenton Edmund Taggi
Original Assignee
Du Pont
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Priority claimed from PCT/US2011/027737 external-priority patent/WO2012033548A2/en
Application filed by Du Pont filed Critical Du Pont
Publication of AR085645A1 publication Critical patent/AR085645A1/en

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Abstract

Composiciones herbicidas y métodos de control.Reivindicación 1: Un compuesto seleccionado de la fórmula (1), N-óxidos y sales de estos caracterizado porque, X es CH; Y es C(O); A es un radical seleccionado del grupo que consiste en las fórmulas (A-1) a (A-7); B1 y B3 son, independientemente cada uno, un radical seleccionado del grupo que consiste en las fórmulas (C-1) y (C-2); B2 es un radical seleccionado del grupo que consiste en las fórmulas (C-3) a (C-7); R1 es fenilo, fenilsulfonilo, -W1(fenilo), -W1(S-fenilo), -W1(SO2-fenilo), -W2(SO2CH2-fenilo) o -W2(SCH2-fenilo), cada uno sustituido opcionalmente en los miembros del anillo con hasta cinco sustituyentes seleccionados de R21; o -G o -W2G; o ciano, hidroxi, amino, -C(=O)OH, -C(=O)NHCN, -C(=O)NHOH, -SO2NH2, -SO2NHCN, -SO2NHOH, -NHCHO, alquilo C1-10, alquenilo C2-10, alquinilo C2-10, haloalquilo C1-10, haloalquenilo C2-10, haloalquinilo C2-12, cicloalquilo C3-12, halocicloalquilo C3-12, alquilcicloalquilo C4-14, cicloalquilalquilo C4-14, cicloalquilcicloalquilo C6-18, halocicloalquilalquilo C4-14, alquilcicloalquilalquilo C5-16, cicloalquenilo C3-12, halocicloalquenilo C3-12, alcoxialquilo C2-12, alcoxialquenilo C3-12, alquilcicloalquilo C4-14, alcoxicicloalquilo C4-14, cicloalcoxialquilo C4-14, cicloalcoxialcoxialquilo C5-14, alcoxialcoxialquilo C3-14, alquiltioalquilo C2-12, alquilsulfinilalquilo C2-12, alquilsulfonilalquilo C2-12, alquilaminoalquilo C2-12, dialquilaminoalquilo C3-14, haloalquilaminoalquilo C2-12, cicloalquilaminoalquilo C4-14, alquilcarbonilo C2-12, haloalquilcarbonilo C2-12, cicloalquilcarbonilo C4-14, alcoxicarbonilo C2-12, cicloalcoxicarbonilo C4-16, cicloalquilalcoxicarbonilo C5-14, alquilaminocarbonilo C2-12, dialquilaminocarbonilo C3-14, cicloalquilaminocarbonilo C4-14, cianoalquilo C2-9, hidroxialquilo C1-10, cicloalquenilalquilo C4-14, haloalcoxialquilo C2-12, alcoxihaloalquilo C2-12, haloalcoxihaloalquilo C2-12, halocicloalcoxialquilo C4-14, cicloalqueniloxialquilo C4-14, halocicloalqueniloxialquilo C4-14, dialcoxialquilo C3-14, alcoxialquilcarbonilo C3-14, alcoxicarbonilalquilo C3-14, haloalcoxicarbonilo C2-12, alcoxi C1-10, haloalcoxi C1-10, cicloalcoxi C3-12, halocicloalcoxi C3-12, cicloalquilalcoxi C4-14, alqueniloxi C2-10, haloalqueniloxi C2-10, alquiniloxi C2-10, haloalquiniloxi C3-10, alcoxialcoxi C2-12, alquilcarboniloxi C2-12, haloalquilcarboniloxi C2-12, cicloalquilcarboniloxi C4-14, alquilcarbonilalcoxi C3-14, alquiltio C1-10, haloalquiltio C1-10, cicloalquiltio C3-12, alquilsulfinilo C1-10, haloalquilsulfinilo C1-10, alquilsulfonilo C1-10, haloalquilsulfonilo C1-10, cicloalquilsulfonilo C3-12, alquilcarboniltio C2-12, alquil(tiocarbonil)tio C2-12, cicloalquilsulfinilo C3-12, alquilaminosulfonilo C1-10, dialquilaminosulfonilo C2-12, alquilamino C1-10, dialquilamino C2-12, haloalquilamino C1-10, halodialquilamino C2-12, cicloalquilamino C3-12, alquilcarbonilamino C2-12, haloalquilcarbonilamino C2-12, alquilsulfonilamino C1-10, haloalquilsulfonilamino C1-10 o cicloalquil(alquil)amino C4-14; W1 es alquileno C1-6, alquenileno C2-6 o alquinileno C2-6; W2 es alquileno C1-6; R2 es fenilo o -W3(fenilo), cada uno sustituido opcionalmente en los miembros del anillo con hasta cinco sustituyentes seleccionados de R21; o -G o -W4G; o H, ciano, hidroxi, amino, nitro, -CHO, -C(=O)OH, -C(=O)NH2, -C(=S)NH2, -C(=O)NHCN, -C(=O)NHOH, -SH, -SO2NH2, -SO2NHCN, -SO2NHOH, -SF5, -NHCHO, -NHNH2, -NHOH, -NHCN, -NHC(=O)NH2, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, haloalquenilo C2-6, haloalquinilo C2-6, cicloalquilo C3-8, halocicloalquilo C3-8, alquilcicloalquilo C4-10, cicloalquilalquilo C4-10, cicloalquilcicloalquilo C6-14, halocicloalquilalquilo C4-10, alquilcicloalquilalquilo C5-12, cicloalquenilo C3-8, halocicloalquenilo C3-8, alcoxialquilo C2-8, alcoxialquenilo C3-10, cicloalcoxialquilo C4-10, alcoxialcoxialquilo C3-10, alquiltioalquilo C2-8, alquilsulfinilalquilo C2-8, alquilsulfonilalquilo C2-8, alquilaminoalquilo C2-8, dialquilaminoalquilo C3-10, haloalquilaminoalquilo C2-8, cicloalquilaminoalquilo C4-10, alquilcarbonilo C2-8, haloalquilcarbonilo C2-8, cicloalquilcarbonilo C4-10, alcoxicarbonilo C2-8, cicloalcoxicarbonilo C4-10, cicloalquilalcoxicarbonilo C5-12, alquilaminocarbonilo C2-8, dialquilaminocarbonilo C3-10, cicloalquilaminocarbonilo C4-10, cianoalquilo C2-5, hidroxialquilo C1-6, cicloalquenilalquilo C4-10, haloalcoxialquilo C2-8, alcoxihaloalquilo C2-8, haloalcoxihaloalquilo C2-8, halocicloalcoxialquilo C4-10, cicloalqueniloxialquilo C4-10, halocicloalqueniloxialquilo C4-10, dialcoxialquilo C3-10, alcoxialquilcarbonilo C3-10, alcoxicarbonilalquilo C3-10, haloalcoxicarbonilo C2-8, alcoxi C1-6, haloalcoxi C1-6, cicloalcoxi C3-8, halocicloalcoxi C3-8, cicloalquilalcoxi C4-10, alqueniloxi C2-6, haloalqueniloxi C2-6, alquiniloxi C2-6, haloalquiniloxi C3-6, alcoxialcoxi C2-8, alquilcarboniloxi C2-8, haloalquilcarboniloxi C2-8, cicloalquilcarboniloxi C4-10, alquilcarbonilalcoxi C3-10, alquiltio C1-6, haloalquiltio C1-6, cicloalquiltio C3-8, alquilsulfinilo C1-6, haloalquilsulfinilo C1-6, alquilsulfonilo C1-6, haloalquilsulfonilo C1-6, cicloalquilsulfonilo C3-8, trialquilsililo C3-8, cicloalqueniloxi C3-8, halocicloalqueniloxi C3-8, haloalcoxialcoxi C2-8, alcoxihaloalcoxi C2-8, haloalcoxihaloalcoxi C2-8, alcoxicarbonilalcoxi C3-10, alquil(tiocarbonil)oxi C2-8, alquilcarboniltio C2-8, alquil(tiocarbonil)tio C2-8, cicloalquilsulfinilo C3-8, alquilaminosulfonilo C1-6, dialquilaminosulfonilo C2-8, halotrialquilsililo C3-10, alquilamino C1-6, dialquilamino C2-8, haloalquilamino C1-6, halodialquilamino C2-8, cicloalquilamino C3-8, alquilcarbonilamino C2-8, haloalquilcarbonilamino C2-8, alquilsulfonilamino C1-6, haloalquilsulfonilamino C1-6 o cicloalquil(alquil)amino C4-10; o R1 y R2 se toman conjuntamente con los átomos a los que están unidos para formar un anillo de 5, 6 ó 7 miembros insaturado, parcialmente insaturado o totalmente insaturado junto con miembros que consisten en hasta 2 átomos de oxígeno, 2 átomos de nitrógeno o 2 átomos de azufre o hasta dos grupos -S(O)-, -S(O)2-, -C(O)- sustituidos opcionalmente en los miembros de átomos de carbono del anillo seleccionados de halógeno, ciano, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, cicloalquilo C3-8 y alcoxialquilo C2-8; y fenilo sustituido opcionalmente con hasta 5 sustituyentes seleccionados de ciano, nitro, halógeno, alquilo C1-6, alcoxi C1-6 y haloalcoxi C1-6; y sustituido opcionalmente en los miembros de nitrógeno del anillo seleccionados de H y alquilo C1-6; y fenilo sustituido opcionalmente con hasta 5 sustituyentes seleccionados de ciano, nitro, halógeno, alquilo C1-6, alcoxi C1-6 y haloalcoxi C1-6; W3 es alquileno C1-6, alquenileno C2-6 o alquinileno C2-6; W4 es alquileno C1-6; R3 es H, halógeno, ciano, hidroxi, -O-M+, amino, nitro, -CHO, -C(=O)OH, -C(=O)NH2, -C(=S)NH2, -SH, -SO2NH2, -CO2NHCN, -SO2NHOH, -OCN, -SCN, -SF5, -NHNH2, -NHOH, -N=C=O, -N=C=S, alcoxi C1-6, haloalcoxi C1-6, cicloalcoxi C3-8, halocicloalcoxi C3-8, cicloalquilalcoxi C4-10, alqueniloxi C2-6, haloalqueniloxi C2-6, alquiniloxi C2-6, haloalquiniloxi C3-6, alcoxialcoxi C2-8, alquilcarboniloxi C2-8, haloalquilcarboniloxi C2-8, cicloalquilcarboniloxi C4-10, alquilcarbonilalcoxi C3-10, alquiltio C1-6, haloalquiltio C1-6, cicloalquiltio C3-8, alquilsulfinilo C1-6, haloalquilsulfinilo C1-6, alquilsulfonilo C1-6, haloalquilsulfonilo C1-6, cicloalquilsulfonilo C3-8, alquilsulfoniloxi C1-6, alquilamino C1-6, dialquilamino C2-8, haloalquilamino C1-6, halodialquilamino C2-8, cicloalquilamino C3-8, alquilcarbonilamino C2-8, haloalquilcarbonilamino C2-8, alquilsulfonilamino C1-6 o haloalquilsulfonilamino C1-6; o benciloxi, feniloxi, bencilcarboniloxi, fenilcarboniloxi, fenilsulfoniloxi, bencilsulfoniloxi, feniltio, benciltio, fenilsulfinilo, bencilsulfinilo, fenilsulfonilo o bencilsulfonilo, cada uno sustituido opcionalmente en los miembros del anillo con hasta cinco sustituyentes seleccionados de R21; M+ es un catión de metal alcalino o un catión de amonio; R4, R5, R6 y R7 son, independientemente cada uno, H, halógeno, hidroxi, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, alcoxi C1-6, haloalcoxi C1-6, cicloalcoxi C3-8 o halocicloalcoxi C3-8; o fenilo o bencilo, cada uno sustituido opcionalmente en los miembros del anillo con hasta cinco sustituyentes seleccionados de R21; R8 es H, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, haloalquenilo C2-6, haloalquinilo C2-6, cicloalquilo C3-8 o halocicloalquilo C3-8; o bencilo sustituido opcionalmente en los miembros del anillo con hasta cinco sustituyentes seleccionados de R21; R9 es H, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, haloalquenilo C2-6, haloalquinilo C2-6, cicloalquilo C3-8, halocicloalquilo C3-8, alquilcicloalquilo C4-10, cicloalquilalquilo C4-10, cicloalquilcicloalquilo C6-14, halocicloalquilalquilo C4-10, alquilcicloalquilalquilo C5-12, cicloalquenilo C3-8, halocicloalquenilo C3-8, alcoxialquilo C2-8, cicloalcoxialquilo C4-10, alcoxialcoxialquilo C3-10 o alquiltioalquilo C2-8; R10 es H, halógeno, ciano, hidroxi, amino, nitro, SH, -SO2NH2, -SO2NHCN, -SO2NHOH, -OCN, -SCN, -SF5, -NHCHO, -NHNH2, -N3, -NHOH, -NHCN, -NHC(=O)NH2, -N=C=O, -N=C=S, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, haloalquenilo C2-6, haloalquinilo C2-6, cicloalquilo C3-8, halocicloalquilo C3-8, alquilcicloalquilo C4-10, cicloalquilalquilo C4-10, cicloalquilcicloalquilo C6-14, halocicloalquilalquilo C4-10, alquilcicloalquilalquilo C5-12, cicloalquenilo C3-8, halocicloalquenilo C3-8, alcoxialquilo C2-8, cicloalcoxialquilo C4-10, alcoxialcoxialquilo C3-10 o alquiltioalquilo C2-8; R11 es H, halógeno, ciano, hidroxi, amino, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, haloalquenilo C2-6, haloalquinilo C2-6, cicloalquilo C3-8, halocicloalquilo C3-8, alquilcicloalquilo C4-10, cicloalquilalquilo C4-10, halocicloalquilalquilo C4-10, alquilcicloalquilalquilo C5-12, cHerbicidal compositions and control methods. Claim 1: A compound selected from the formula (1), N-oxides and salts thereof characterized in that, X is CH; Y is C (O); A is a radical selected from the group consisting of formulas (A-1) to (A-7); B1 and B3 are, independently each, a radical selected from the group consisting of formulas (C-1) and (C-2); B2 is a radical selected from the group consisting of formulas (C-3) to (C-7); R1 is phenyl, phenylsulfonyl, -W1 (phenyl), -W1 (S-phenyl), -W1 (SO2-phenyl), -W2 (SO2CH2-phenyl) or -W2 (SCH2-phenyl), each optionally substituted in the ring members with up to five substituents selected from R21; or -G or -W2G; or cyano, hydroxy, amino, -C (= O) OH, -C (= O) NHCN, -C (= O) NHOH, -SO2NH2, -SO2NHCN, -SO2NHOH, -NHCHO, C1-10 alkyl, C2 alkenyl -10, C2-10 alkynyl, C1-10 haloalkyl, C2-10 haloalkenyl, C2-12 haloalkynyl, C3-12 cycloalkyl, C3-12 halocycloalkyl, C4-14 alkylcycloalkyl, C4-14 cycloalkylalkyl, C4-18 halocycloalkylalkyl -14, C5-16 alkylcycloalkylalkyl, C3-12 cycloalkenyl, C3-12 halocycloalkenyl, C2-12 alkoxyalkyl, C3-12 alkoxyalkenyl, C4-14 alkylcycloalkyl, C4-14 alkoxycycloalkyl, C4-14 cycloalkoxyalkoxyalkyl C3 alkoxyalkyl, C3-12 alkoxyalkyl, C3-12 alkoxyalkyl -14, C2-12 alkylthioalkyl, C2-12 alkylsulfinylalkyl, C2-12 alkylsulfonylalkyl, C2-12 alkylaminoalkyl, C3-12 dialkylaminoalkyl, C2-14 haloalkylaminoalkyl, C2-12 alkylcarbonyl, C2-12 haloalkylcarbonylC2-12 alkylcarbonyl -14, C2-12 alkoxycarbonyl, C4-16 cycloalkoxycarbonyl, C5-14 cycloalkylalkoxycarbonyl, alkylaminocarbo C2-12 nyl, C3-14 dialkylaminocarbonyl, C4-14 cycloalkylaminocarbonyl, C2-9 cyanoalkyl, C1-10 hydroxyalkyl, C4-14 cycloalkenyl alkyl, C2-12 haloalkoxyalkyl, C2-12 alkoxyhaloalkyl, C2-12 haloalkyl, C4xalkyl, C4-12 haloalkyl C4-14 cycloalkenyloxyalkyl, C4-14 halocycloalkenyloxyalkyl, C3-14 dialkoxyalkyl, C3-14 alkoxycarbonyl, C3-14 alkoxycarbonylalkyl, C2-12 haloalkoxycarbonyl, C1-10 alkoxy, C1-10 haloalkoxy, C3-12 cycloalkoxy, C3-12 halocycloalkoxy C4-14 cycloalkylalkoxy, C2-10 alkenyloxy, C2-10 haloalkenyloxy, C2-10 alkynyloxy, C3-10 haloalkyloxy, C2-12 alkoxy alkoxy, C2-12 alkylcarbonyloxy, C4-14 alkylcarbonyloxy, C3-14 alkylcarbonyloxy, C1-10 alkylthio, C1-10 haloalkylthio, C3-12 cycloalkylthio, C1-10 alkylsulfinyl, C1-10 haloalkylsulfinyl, C1-10 alkylsulfonyl, C1-10 haloalkylsulfonyl, C3-12 cycloalkylsulfonyl, C2-12 alkylcarbonylthio, thiocarbonyl thio C2-12, cycloalkylsulf C3-12 inyl, C1-10 alkylaminosulfonyl, C2-12 dialkylaminosulfonyl, C1-10 alkylamino, C2-12 dialkylamino, C1-10 haloalkylamino, C2-12 halodyalkylamino, C3-12 cycloalkylamino, C2-12 alkylcarbonylamino, C2-12 haloalkylcarbonylamino, C1-10 alkyl sulfonylamino, C1-10 haloalkylsulfonylamino or C4-14 cycloalkyl (alkyl) amino; W1 is C1-6 alkylene, C2-6 alkenylene or C2-6 alkynylene; W2 is C1-6 alkylene; R2 is phenyl or -W3 (phenyl), each optionally substituted on the ring members with up to five substituents selected from R21; or -G or -W4G; or H, cyano, hydroxy, amino, nitro, -CHO, -C (= O) OH, -C (= O) NH2, -C (= S) NH2, -C (= O) NHCN, -C (= O) NHOH, -SH, -SO2NH2, -SO2NHCN, -SO2NHOH, -SF5, -NHCHO, -NHNH2, -NHOH, -NHCN, -NHC (= O) NH2, C1-6 alkyl, C2-6 alkenyl, alkynyl C2-6, C1-6 haloalkyl, C2-6 haloalkenyl, C2-6 haloalkynyl, C3-8 cycloalkyl, C3-8 halocycloalkyl, C4-10 alkylcycloalkyl, C4-10 cycloalkylalkyl, C4-10 halocycloalkylalkyl, C4-10 alkylcycloalkylalkyl C5-12, C3-8 cycloalkenyl, C3-8 halocycloalkenyl, C2-8 alkoxyalkyl, C3-10 alkoxyalkyl, C4-10 cycloalkoxyalkyl, C3-10 alkoxyalkoxyalkyl, C2-8 alkylsulfinylalkyl, C2-8 alkyl, alkylsulfonC2-8alkylalkyl C2-8, C3-10 dialkylaminoalkyl, C2-8 haloalkylaminoalkyl, C4-10 cycloalkylaminoalkyl, C2-8 alkylcarbonyl, C2-8 haloalkylcarbonyl, C4-10 cycloalkylcarbonyl, C4-10 alkoxycarbonyl, C12-10 alkyloxycarbonylcarbonylcarbonylcarbonylcarbonylalkylcarbonylcarbonylcarbonylC5-10 C2-8, dialkyl C3-10 aminocarbonyl, C4-10 cycloalkylaminocarbonyl, C2-5 cyanoalkyl, C1-6 hydroxyalkyl, C4-10 cycloalkenyl alkyl, C2-8 haloalkoxyalkyl, C2-8 alkoxyhaloalkyl, C2-8 haloalkoxyhaloalkyl, cycloalkyl, cycloalkyl, cycloalkyl, cycloalkyl, cycloalkyl, cycloalkyl, cycloalkyl, cycloalkyl, cycloalkyl, cycloalkyl, C 1-10 C4-10 halocycloalkenyloxyalkyl, C3-10 dialkoxyalkyl, C3-10 alkoxyalkylcarbonyl, C3-10 alkoxycarbonylalkyl, C2-8 haloalkoxycarbonyl, C1-6 alkoxy, C3-8 haloalkoxy, C3-8 halocycloalkoxy, C4-8 cycloalkyloxy C2-6 alkenyloxy, C2-6 haloalkenyloxy, C2-6 alkynyloxy, C3-6 haloalkyloxy, C2-8 alkoxyalkoxy, C2-8 alkylcarbonyloxy, C2-10 haloalkylcarbonyloxy, C3-10 alkylcarbonyloxyC3-6 alkyl, C3-10 alkylcarbonyloxy, C1-6 haloalkylthio, C3-8 cycloalkylthio, C1-6 alkylsulfinyl, C1-6 haloalkylsulfinyl, C1-6 alkylsulfonyl, C1-6 haloalkylsulfonyl, C3-8 cycloalkylsulfonyl, C3-8 trialkylsilyl, C3-8 cycloalkenyl, C3-8 haloxyloxy C2-8 haloalkoxyalkoxy, C2 alkoxyhaloalkoxy -8, C2-8 haloalkoxyhaloalkoxy, C3-10 alkoxycarbonylalkoxy, C2-8 alkyl (thiocarbonyl), C2-8 alkylcarbonylthio, C2-8 alkyl (thiocarbonyl) thio C2-8, C1-6 alkylaminosulfonyl, C-6 alkylsulfonyl , C3-10 halotrialkylsilyl, C 1-6 alkylamino, C 2-8 dialkylamino, C 1-6 haloalkylamino, C 2-8 haloalkylamino, C 3-8 cycloalkylamino, C 2-8 alkylcarbonylamino, C 1-6 alkylcarbonylamino, C 1-6 alkylsulfonylamino, C 1-6 alkylsulfonylamino or C4-10 cycloalkyl (alkyl) amino; or R1 and R2 are taken together with the atoms to which they are attached to form an unsaturated, partially unsaturated or totally unsaturated ring of 5, 6 or 7 members together with members consisting of up to 2 oxygen atoms, 2 nitrogen atoms or 2 sulfur atoms or up to two groups -S (O) -, -S (O) 2-, -C (O) - optionally substituted on the ring carbon atoms members selected from halogen, cyano, C1-6 alkyl , C2-6 alkenyl, C2-6 alkynyl, C1-6 haloalkyl, C3-8 cycloalkyl and C2-8 alkoxyalkyl; and phenyl optionally substituted with up to 5 substituents selected from cyano, nitro, halogen, C1-6 alkyl, C1-6 alkoxy and C1-6 haloalkoxy; and optionally substituted on the ring nitrogen members selected from H and C1-6 alkyl; and phenyl optionally substituted with up to 5 substituents selected from cyano, nitro, halogen, C1-6 alkyl, C1-6 alkoxy and C1-6 haloalkoxy; W3 is C1-6 alkylene, C2-6 alkenylene or C2-6 alkynylene; W4 is C1-6 alkylene; R3 is H, halogen, cyano, hydroxy, -O-M +, amino, nitro, -CHO, -C (= O) OH, -C (= O) NH2, -C (= S) NH2, -SH, - SO2NH2, -CO2NHCN, -SO2NHOH, -OCN, -SCN, -SF5, -NHNH2, -NHOH, -N = C = O, -N = C = S, C1-6 alkoxy, C1-6 haloalkoxy, C3- cycloalkoxy 8, C3-8 halocycloalkoxy, C4-10 cycloalkylalkoxy, C2-6 alkenyloxy, C2-6 haloalkyloxy, C2-6 alkynyloxy, C3-6 haloalkyloxy, C2-8 alkoxyalkoxy, C2-8 alkylcarbonyloxyC4-8 cycloalkylcarbonyloxy 10, C3-10 alkylcarbonylalkoxy, C1-6 alkylthio, C1-6 haloalkylthio, C3-8 cycloalkylthio, C1-6 alkylsulfinyl, C1-6 haloalkylsulfinyl, C1-6 alkylsulfonyl, C3-8 cycloalkylsulfonyl, C1-8 alkylsulfonyl, 6, C1-6 alkylamino, C2-8 dialkylamino, C1-6 haloalkylamino, C2-8 halodyalkylamino, C3-8 cycloalkylamino, C2-8 alkylcarbonylamino, C2-8 haloalkylcarbonylamino, C1-6 alkylsulfonylamino or C1-6 haloalkylsilylamino; or benzyloxy, phenyloxy, benzylcarbonyloxy, phenylcarbonyloxy, phenylsulfonyloxy, benzylsulfonyloxy, phenylthio, benzylthio, phenylsulfinyl, benzylsulfinyl, phenylsulfonyl or benzylsulfonyl, each optionally substituted on the ring members with up to five substituents selected from R21; M + is an alkali metal cation or an ammonium cation; R4, R5, R6 and R7 are each independently H, halogen, hydroxy, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 haloalkyl, C1-6 alkoxy, C1-6 haloalkoxy, cycloalkoxy C3-8 or C3-8 halocycloalkoxy; or phenyl or benzyl, each optionally substituted on the ring members with up to five substituents selected from R21; R 8 is H, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 haloalkyl, C 2-6 haloalkenyl, C 2-6 haloalkynyl, C 3-8 cycloalkyl or C 3-8 halocycloalkyl; or optionally substituted benzyl in the ring members with up to five substituents selected from R21; R9 is H, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 haloalkyl, C2-6 haloalkenyl, C2-6 haloalkynyl, C3-8 cycloalkyl, C3-8 halocycloalkyl, C4-10 alkylcycloalkyl, cycloalkylalkyl C4-10, C6-14 cycloalkylcycloalkyl, C4-10 halocycloalkylalkyl, C5-12 alkylcycloalkylalkyl, C3-8 cycloalkenyl, C3-8 halocycloalkenyl, C2-8 alkoxyalkyl, C4-10 alkoxyalkyl or C3-10 alkoxyalkyl; R10 is H, halogen, cyano, hydroxy, amino, nitro, SH, -SO2NH2, -SO2NHCN, -SO2NHOH, -OCN, -SCN, -SF5, -NHCHO, -NHNH2, -N3, -NHOH, -NHCN, - NHC (= O) NH2, -N = C = O, -N = C = S, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 haloalkyl, C2-6 haloalkenyl, C2-6 haloalkynyl , C3-8 cycloalkyl, C3-8 halocycloalkyl, C4-10 alkylcycloalkyl, C4-10 cycloalkylalkyl, C6-14 cycloalkylalkyl, C4-10 halocycloalkylalkyl, C3-8 cycloalkenyl, C3-8 alkoxy-C8-C2-alkenyl, C8-8 -alkyl-alkynyl , C4-10 cycloalkoxyalkyl, C3-10 alkoxyalkoxyalkyl or C2-8 alkylthioalkyl; R11 is H, halogen, cyano, hydroxy, amino, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 haloalkyl, C2-6 haloalkenyl, C2-6 haloalkynyl, C3-8 cycloalkyl, C3- halocycloalkyl 8, C4-10 alkylcycloalkyl, C4-10 cycloalkylalkyl, C4-10 halocycloalkylalkyl, C5-12 alkylcycloalkylalkyl, c

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