US2015274756A1PendingUtilityA1
4-amino-6-(heterocyclic)picolinates and 6-amino-2-(heterocyclic)pyrimidine-4-carboxylates and their use as herbicides
Est. expiryMar 15, 2033(~6.7 yrs left)· nominal 20-yr term from priority
Inventors:Joseph D. EckelbargerJeffrey B. EppStephen Craig FieldsLindsey G. FischerNatalie C. GiampietroKatherine A. GuenthenspbergerChristian T. LoweJeff PetkusJoshua RothNorbet M. SatchiviPaul R. SchmitzerThomas L. SiddallNick X. Wang
C07D 403/04C07D 413/04A01N 43/52A01N 43/78A01N 43/54A01N 55/00A01N 43/80A01N 43/76C07D 417/04C07D 409/04C07D 401/04A01N 43/647A01N 43/40A01N 43/56C07D 405/04C07F 7/0803A01N 43/12C07D 213/79C07D 213/803
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Claims
Abstract
4-Amino-6-(heterocyclic)picolinic acids and their derivatives; 6-amino-2-(heterocyclic)pyrimidine-4-carboxylates and their derivatives; and methods of using the same as herbicides.
Claims
exact text as granted — not AI-modified1 - 32 . (canceled)
33 . A compound of the Formula (I):
wherein
X is N or CY, wherein Y is hydrogen, halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, or C 1 -C 3 haloalkylthio;
R 1 is OR 1″ or NR 1″ R 1′″ , wherein R 1′ is hydrogen, C 1 -C 8 alkyl, or C 7 -C 10 arylalkyl, and R 1″ and R 1′″ are independently hydrogen, C 1 -C 12 alkyl, C 3 -C 12 alkenyl, or C 3 -C 12 alkynyl;
R 2 is halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, cyano, or a group of the formula —CR 17 ═CR 18 —SiR 19 R 20 R 21 , wherein R 17 is hydrogen, F, or Cl; R 18 is hydrogen, F, Cl, C 1 -C 4 alkyl, or C 1 -C 4 haloalkyl; and R 19 , R 20 , and R 21 are independently C 1 -C 10 alkyl, C 3 -C 6 cycloalkyl, phenyl, substituted phenyl, C 1 -C 10 alkoxy, or OH;
R 3 and R 4 are independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbamyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 trialkylsilyl, C 1 -C 6 dialkylphosphonyl, or R 3 and R 4 taken together with N is a 5- or 6-membered saturated ring, or R 3 and R 4 taken together represent ═CR 3′ (R 4′ ), wherein R 3′ and R 4′ are independently hydrogen, C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1 -C 6 alkoxy or C 1 -C 6 alkylamino, or, R 3′ and R 4′ taken together with ═C represent a 5- or 6-membered saturated ring;
A is one of groups A1 to A36
R 5 is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, OH, or CN;
R 6 , R 6′ , and R 6″ are independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino or C 2 -C 4 haloalkylamino, OH, CN, or NO 2 ;
R 7 and R 7′ are independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, or phenyl;
R 8 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbamyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 trialkylsilyl, or phenyl;
or an N-oxide or agriculturally acceptable salt thereof,
with the proviso that the compound is not a compound of Formula (I):
wherein
X is N, CH, CF, CCl, or CBr;
R 1 is OR 1′ , wherein R 1′ is hydrogen or C 1 -C 4 alkyl;
R 2 is chlorine;
R 3 and R 4 are hydrogen;
A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, or A20;
R 5 is hydrogen, halogen, OH, amino, CN, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 alkylamino, or cyclopropyl;
R 6 , R 6′ , and R 6″ are independently hydrogen, halogen, OH, NH 2 , CN, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, cyclopropyl, or vinyl;
R 7 and R 7′ are independently hydrogen, halogen, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, cyclopropyl, or C 1 -C 3 alkylamino, or phenyl; and
R 8 is hydrogen, C 1 -C 3 alkyl, phenyl, or C 1 -C 3 alkylcarbonyl;
or an N-oxide or agriculturally acceptable salt thereof.
34 . The compound of claim 33 , wherein
X is CY, wherein Y is C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, or C 1 -C 3 haloalkylthio; R 1 is OR 1′ or NR 1″ R 1′″ , wherein R 1′ is hydrogen, C 1 -C 8 alkyl, or C 7 -C 10 arylalkyl, and R 1″ and R 1′″ are independently hydrogen, C 1 -C 12 alkyl, C 3 -C 12 alkenyl, or C 3 -C 12 alkynyl; R 2 is halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, cyano, or a group of the formula —CR 17 ═CR 18 —SiR 19 R 20 R 21 , wherein R 17 is hydrogen, F, or Cl; R 18 is hydrogen, F, Cl, C 1 -C 4 alkyl, or C 1 -C 4 haloalkyl; and R 19 , R 20 , and R 21 are independently C 1 -C 10 alkyl, C 3 -C 6 cycloalkyl, phenyl, substituted phenyl, C 1 -C 10 alkoxy, or OH; R 3 and R 4 are independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbamyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 trialkylsilyl, C 1 -C 6 dialkylphosphonyl, or R 3 and R 4 taken together with N is a 5- or 6-membered saturated ring, or R 3 and R 4 taken together represent ═CR 3′ (R 4′ ), wherein R 3′ and R 4′ are independently hydrogen, C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1 -C 6 alkoxy or C 1 -C 6 alkylamino, or, R 3′ and R 4′ taken together with ═C represent a 5- or 6-membered saturated ring; A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31, A32, A33, A34, A35, or A36; R 5 is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, OH, or CN; R 6 , R 6′ , and R 6″ are independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino or C 2 -C 4 haloalkylamino, OH, CN, or NO 2 ; R 7 and R 7′ are independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, or phenyl; R 8 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbamyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 trialkylsilyl, or phenyl; or an N-oxide or agriculturally acceptable salt thereof.
35 . The compound of claim 33 , wherein
X is N or CY, wherein Y is hydrogen, halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, or C 1 -C 3 haloalkylthio; R 1 is OR 1′ or NR 1″ R 1′″ , wherein R 1′ is C 5 -C 8 alkyl, or C 7 -C 10 arylalkyl, and R 1″ and R 1′″ are independently hydrogen, C 1 -C 12 alkyl, C 3 -C 12 alkenyl, or C 3 -C 12 alkynyl; R 2 is halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, cyano, or a group of the formula —CR 17 ═CR 18 —SiR 19 R 20 R 21 , wherein R 17 is hydrogen, F, or Cl; R 18 is hydrogen, F, Cl, C 1 -C 4 alkyl, or C 1 -C 4 haloalkyl; and R 19 , R 20 , and R 21 are independently C 1 -C 10 alkyl, C 3 -C 6 cycloalkyl, phenyl, substituted phenyl, C 1 -C 10 alkoxy, or OH; R 3 and R 4 are independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbamyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 trialkylsilyl, C 1 -C 6 dialkylphosphonyl, or R 3 and R 4 taken together with N is a 5- or 6-membered saturated ring, or R 3 and R 4 taken together represent ═CR 3′ (R 4′ ), wherein R 3′ and R 4′ are independently hydrogen, C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1 -C 6 alkoxy or C 1 -C 6 alkylamino, or, R 3′ and R 4′ taken together with ═C represent a 5- or 6-membered saturated ring; A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31, A32, A33, A34, A35, or A36; R 5 is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, OH, or CN; R 6 , R 6′ , and R 6″ are independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino or C 2 -C 4 haloalkylamino, OH, CN, or NO 2 ; R 7 and R 7′ are independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, or phenyl; R 8 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbamyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 trialkylsilyl, or phenyl; or an N-oxide or agriculturally acceptable salt thereof.
36 . The compound of claim 33 , wherein
X is N or CY, wherein Y is hydrogen, halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, or C 1 -C 3 haloalkylthio; R 1 is OR 1′ or NR 1″ R 1′″ “, wherein R 1′ is hydrogen, C 1 -C 8 alkyl, or C 7 -C 10 arylalkyl, and R” and R 1′″ are independently hydrogen, C 1 -C 12 alkyl, C 3 -C 12 alkenyl, or C 3 -C 12 alkynyl; R 2 is F, Br, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, cyano, or a group of the formula —CR 17 ═CR 18 —SiR 19 R 20 R 21 , wherein R 17 is hydrogen, F, or Cl; R 18 is hydrogen, F, Cl, C 1 -C 4 alkyl, or C 1 -C 4 haloalkyl; and R 19 , R 20 , and R 21 are independently C 1 -C 10 alkyl, C 3 -C 6 cycloalkyl, phenyl, substituted phenyl, C 1 -C 10 alkoxy, or OH; R 3 and R 4 are independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbamyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 trialkylsilyl, C 1 -C 6 dialkylphosphonyl, or R 3 and R 4 taken together with N is a 5- or 6-membered saturated ring, or R 3 and R 4 taken together represent ═CR 3′ (R 4′ ), wherein R 3′ and R 4′ are independently hydrogen, C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1 -C 6 alkoxy or C 1 -C 6 alkylamino, or, R 3′ and R 4′ taken together with ═C represent a 5- or 6-membered saturated ring; A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31, A32, A33, A34, A35, or A36; R 5 is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, OH, or CN; R 6 , R 6′ , and R 6″ are independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino or C 2 -C 4 haloalkylamino, OH, CN, or NO 2 ; R 7 and R 7′ are independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, or phenyl; R 8 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbamyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 trialkylsilyl, or phenyl; or an N-oxide or agriculturally acceptable salt thereof.
37 . The compound of claim 33 , wherein
X is N or CY, wherein Y is hydrogen, halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, or C 1 -C 3 haloalkylthio; R 1 is OR 1′ or NR 1″ R 1′″ , wherein R 1′ is hydrogen, C 1 -C 8 alkyl, or C 7 -C 10 arylalkyl, and R 1″ and R 1′″ are independently hydrogen, C 1 -C 12 alkyl, C 3 -C 12 alkenyl, or C 3 -C 12 alkynyl; R 2 is halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, cyano, or a group of the formula —CR 17 ═CR 18 —SiR 19 R 20 R 21 , wherein R 17 is hydrogen, F, or Cl; R 18 is hydrogen, F, Cl, C 1 -C 4 alkyl, or C 1 -C 4 haloalkyl; and R 19 , R 20 , and R 21 are independently C 1 -C 10 alkyl, C 3 -C 6 cycloalkyl, phenyl, substituted phenyl, C 1 -C 10 alkoxy, or OH; R 3 and R 4 are independently C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbamyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 trialkylsilyl, C 1 -C 6 dialkylphosphonyl, or R 3 and R 4 taken together with N is a 5- or 6-membered saturated ring, or R 3 and R 4 taken together represent ═CR 3′ (R 4′ ), wherein R 3′ and R 4′ are independently hydrogen, C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1 -C 6 alkoxy or C 1 -C 6 alkylamino, or, R 3′ and R 4′ taken together with ═C represent a 5- or 6-membered saturated ring; A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, A20, A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31, A32, A33, A34, A35, or A36; R 5 is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, OH, or CN; R 6 , R 6′ , and R 6″ are independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino or C 2 -C 4 haloalkylamino, OH, CN, or NO 2 ; R 7 and R 7′ are independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, or phenyl; R 8 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbamyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 trialkylsilyl, or phenyl; or an N-oxide or agriculturally acceptable salt thereof.
38 . The compound of claim 33 , wherein
X is N or CY, wherein Y is hydrogen, halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, or C 1 -C 3 haloalkylthio; R 1 is OR 1′ or NR 1″ R 1′″ , wherein R 1′ is hydrogen, C 1 -C 8 alkyl, or C 7 -C 10 arylalkyl, and R 1″ and R 1′″ are independently hydrogen, C 1 -C 12 alkyl, C 3 -C 12 alkenyl, or C 3 -C 12 alkynyl; R 2 is halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, cyano, or a group of the formula —CR 17 ═CR 18 —SiR 19 R 20 R 21 , wherein R 17 is hydrogen, F, or Cl; R 18 is hydrogen, F, Cl, C 1 -C 4 alkyl, or C 1 -C 4 haloalkyl; and R 19 , R 20 , and R 21 are independently C 1 -C 10 alkyl, C 3 -C 6 cycloalkyl, phenyl, substituted phenyl, C 1 -C 10 alkoxy, or OH; R 3 and R 4 are independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbamyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 trialkylsilyl, C 1 -C 6 dialkylphosphonyl, or R 3 and R 4 taken together with N is a 5- or 6-membered saturated ring, or R 3 and R 4 taken together represent ═CR 3′ (R 4′ ), wherein R 3′ and R 4′ are independently hydrogen, C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1 -C 6 alkoxy or C 1 -C 6 alkylamino, or, R 3′ and R 4′ taken together with ═C represent a 5- or 6-membered saturated ring; A is A21, A22, A23, A24, A25, A26, A27, A28, A29, A30, A31, A32, A33, A34, A35, or A36; R 5 is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, OH, or CN; R 6 , R 6′ , and R 6″ are independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino or C 2 -C 4 haloalkylamino, OH, CN, or NO 2 ; R 7 and R 7′ are independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, or phenyl; R 8 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbamyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 trialkylsilyl, or phenyl; or an N-oxide or agriculturally acceptable salt thereof.
39 . The compound of claim 33 , wherein
X is N or CY, wherein Y is hydrogen, halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, or C 1 -C 3 haloalkylthio; R 1 is OR 1′ or NR 1″ R 1′″ , wherein R 1′ is hydrogen, C 1 -C 8 alkyl, or C 7 -C 10 arylalkyl, and R 1″ and R 1′″ are independently hydrogen, C 1 -C 12 alkyl, C 3 -C 12 alkenyl, or C 3 -C 12 alkynyl; R 2 is halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, cyano, or a group of the formula —CR 17 ═CR 18 —SiR 19 R 20 R 21 , wherein R′ 7 is hydrogen, F, or Cl; le is hydrogen, F, Cl, C 1 -C 4 alkyl, or C 1 -C 4 haloalkyl; and R 19 , R 20 , and R 21 are independently C 1 -C 10 alkyl, C 3 -C 6 cycloalkyl, phenyl, substituted phenyl, C 1 -C 10 alkoxy, or OH; R 3 and R 4 are independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbamyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 trialkylsilyl, C 1 -C 6 dialkylphosphonyl, or R 3 and R 4 taken together with N is a 5- or 6-membered saturated ring, or R 3 and R 4 taken together represent ═CR 3′ (R 4′ ), wherein R 3′ and R 4′ are independently hydrogen, C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1 -C 6 alkoxy or C 1 -C 6 alkylamino, or, R 3′ and R 4′ taken together with ═C represent a 5- or 6-membered saturated ring; A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, or A20; R 5 is C 4 alkyl, C 1 -C 4 haloalkyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, C 4 alkylamino, or C 2 -C 4 haloalkylamino; R 6 , R 6′ , and R 6″ are independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino or C 2 -C 4 haloalkylamino, OH, CN, or NO 2 ; R 7 and R 7′ are independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, or phenyl; R 8 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbamyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 trialkylsilyl, or phenyl; or an N-oxide or agriculturally acceptable salt thereof.
40 . The compound of claim 33 , wherein
X is N or CY, wherein Y is hydrogen, halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, or C 1 -C 3 haloalkylthio; R 1 is OR 1′ or NR 1″ R 1′″ , wherein R 1′ is hydrogen, C 1 -C 8 alkyl, or C 7 -C 10 arylalkyl, and R 1″ and R 1′″ are independently hydrogen, C 1 -C 12 alkyl, C 3 -C 12 alkenyl, or C 3 -C 12 alkynyl; R 2 is halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, cyano, or a group of the formula —CR 17 ═CR 18 —SiR 19 R 20 R 21 , wherein R 17 is hydrogen, F, or Cl; R 18 is hydrogen, F, Cl, C 1 -C 4 alkyl, or C 1 -C 4 haloalkyl; and R 19 , R 20 , and R 21 are independently C 1 -C 10 alkyl, C 3 -C 6 cycloalkyl, phenyl, substituted phenyl, C 1 -C 10 alkoxy, or OH; R 3 and R 4 are independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbamyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 trialkylsilyl, C 1 -C 6 dialkylphosphonyl, or R 3 and R 4 taken together with N is a 5- or 6-membered saturated ring, or R 3 and R 4 taken together represent ═CR 3′ (R 4′ ), wherein R 3′ and R 4′ are independently hydrogen, C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1 -C 6 alkoxy or C 1 -C 6 alkylamino, or, R 3′ and R 4′ taken together with ═C represent a 5- or 6-membered saturated ring; A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, A18, A19, or A20; R 5 is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, OH, or CN; R 6 , R 6′ , and R 6″ are independently C 4 alkyl, C 1 -C 4 haloalkyl, halocyclopropyl, C 3 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, C 1 -C 4 alkylamino or C 2 -C 4 haloalkylamino, or NO 2 ; R 7 and R 7′ are independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, or phenyl; R 8 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbamyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 trialkylsilyl, or phenyl; or an N-oxide or agriculturally acceptable salt thereof.
41 . The compound of claim 33 , wherein
X is N or CY, wherein Y is hydrogen, halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, or C 1 -C 3 haloalkylthio; R 1 is OR 1″ or NR 1″ R 1′″ , wherein R 1′ is hydrogen, C 1 -C 8 alkyl, or C 7 -C 10 arylalkyl, and R 1″ and R 1′″ are independently hydrogen, C 1 -C 12 alkyl, C 3 -C 12 alkenyl, or C 3 -C 12 alkynyl; R 2 is halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, cyano, or a group of the formula —CR 17 ═CR 18 —SiR 19 R 20 R 21 , wherein R 17 is hydrogen, F, or Cl; R 18 is hydrogen, F, Cl, C 1 -C 4 alkyl, or C 1 -C 4 haloalkyl; and R 19 , R 20 , and R 21 are independently C 1 -C 10 alkyl, C 3 -C 6 cycloalkyl, phenyl, substituted phenyl, C 1 -C 10 alkoxy, or OH; R 3 and R 4 are independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbamyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 trialkylsilyl, C 1 -C 6 dialkylphosphonyl, or R 3 and R 4 taken together with N is a 5- or 6-membered saturated ring, or R 3 and R 4 taken together represent ═CR 3′ (R 4′ ), wherein R 3′ and R 4′ are independently hydrogen, C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1 -C 6 alkoxy or C 1 -C 6 alkylamino, or, R 3′ and R 4′ taken together with ═C represent a 5- or 6-membered saturated ring; A is A1, A2, A3, A4, A5, A6, A7, A8, A9, A10, A11, A12, A13, A14, A15, A16, A17, or A18; R 5 is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, OH, or CN; R 6 , R 6′ , and R 6″ are independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino or C 2 -C 4 haloalkylamino, OH, CN, or NO 2 ; R 7 and R 7′ are independently C 4 alkyl, C 1 -C 4 haloalkyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 haloalkoxy, C 1 -C 3 haloalkylthio, amino, C 4 alkylamino, or C 2 -C 4 haloalkylamino; R 8 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbamyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 trialkylsilyl, or phenyl; or an N-oxide or agriculturally acceptable salt thereof.
42 . The compound of claim 33 , wherein
X is N or CY, wherein Y is hydrogen, halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkoxy, C 1 -C 3 alkylthio, or C 1 -C 3 haloalkylthio; R 1 is OR 1′ or NR 1″ R 1′″ , wherein R 1′ is hydrogen, C 1 -C 8 alkyl, or C 7 -C 10 arylalkyl, and R 1″ and R 1′″ are independently hydrogen, C 1 -C 12 alkyl, C 3 -C 12 alkenyl, or C 3 -C 12 alkynyl; R 2 is halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, cyano, or a group of the formula —CR 17 ═CR 18 —SiR 19 R 20 R 21 , wherein R 17 is hydrogen, F, or Cl; R 18 is hydrogen, F, Cl, C 1 -C 4 alkyl, or C 1 -C 4 haloalkyl; and R 19 , R 20 , and R 21 are independently C 1 -C 10 alkyl, C 3 -C 6 cycloalkyl, phenyl, substituted phenyl, C 1 -C 10 alkoxy, or OH; R 3 and R 4 are independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, formyl, C 1 -C 3 alkylcarbonyl, C 1 -C 3 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbamyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 trialkylsilyl, C 1 -C 6 dialkylphosphonyl, or R 3 and R 4 taken together with N is a 5- or 6-membered saturated ring, or R 3 and R 4 taken together represent ═CR 3′ (R 4′ ), wherein R 3′ and R 4′ are independently hydrogen, C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1 -C 6 alkoxy or C 1 -C 6 alkylamino, or, R 3′ and R 4′ taken together with ═C represent a 5- or 6-membered saturated ring; A is A3, A6, A11, A12, A15, A18, A19, or A20; R 5 is hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, OH, or CN; R 6 , R 6′ , and R 6″ are independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino or C 2 -C 4 haloalkylamino, OH, CN, or NO 2 ; R 7 and R 7′ are independently hydrogen, halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyclopropyl, halocyclopropyl, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl, C 2 -C 4 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 3 alkylthio, C 1 -C 3 haloalkylthio, amino, C 1 -C 4 alkylamino, C 2 -C 4 haloalkylamino, or phenyl; R 8 is C 3 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, formyl, C 1 -C 3 haloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 alkylcarbamyl, C 1 -C 6 alkylsulfonyl, or C 1 -C 6 trialkylsilyl; or an N-oxide or agriculturally acceptable salt thereof.
43 . The compound of claim 33 , wherein W is OR 1 .
44 . The compound of claim 33 , wherein X is CF.
45 . The compound of claim 33 , wherein A is A15
46 . The compound of any of claim 33 , wherein R 5 is F.
47 . A herbicidal composition comprising a compound of claim 33 and an agriculturally acceptable adjuvant or carrier.
48 . The composition of claim 47 , further comprising an additional pesticide.
49 . The composition of claim 47 , further comprising a herbicidal safener.
50 . A method of controlling undesirable vegetation which comprises applying to vegetation or an area adjacent the vegetation or applying to soil or water to prevent the emergence or growth of vegetation a compound of claim 33 .
51 . A method of controlling undesirable vegetation which comprises applying to vegetation or an area adjacent the vegetation or applying to soil or water to prevent the emergence or growth of vegetation a herbicidal composition of claim 47 .Join the waitlist — get patent alerts
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