Condensed heterocylic compounds and herbicides containing them

A condensed heterocyclic compound of general formula I

• wherein T is carbon and the bond between T and A is a double bond, the bond between A and Y is a single bond, and Y is oxygen;
• A is C—R141 wherein R141 is hydrogen;
• R1 is hydrogen, halogen, C1-C3 alkyl, C1-C3 haloalkyl, hydroxymethyl, nitro, or cyano;
• R2 is hydrogen, halogen, C1-C11, alkyl C1-C11 haloalkyl, hydroxymethyl, nitro, cyano, —N(R9)R19, —OR11, —SR12, —SO2R13, —COX, —COOR14, —CON(R15)R16, —COOR17, —C(R26)═NOR19, —C(R27)═C(R21)R22, or —OH(R23)—CH(R24)R25;
• R3 is hydrogen, halogen, C1-C11 alkyl, C1-C11 haloalkyl, hydroxymethyl, nitro, cyano, —N(R59)R60, —OR61, —SR62, —SO2R63, —COX, —COOR64, —CON(R65)R66, —COR67, —C(R76)═CR69, —C(R77)═C(R71)R72, or —CH(R73)—CH(R74)R75;
• R4 is hydrogen, halogen, C1-C3, alkyl, C1-C3 haloalkyl, hydroxymethyl, nitro, or cyano;
• wherein X is chlorine or bromine;
• R9 and R59 are independently hydrogen, C1-C5 alkyl, (C1-C5 alkyl)carbonyl, or (C1-C5 alkoxy) carbonyl;
• R10, R11, and R12 are independently hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 halocycloalkyl, C3-C10 cycloalkyl C1-C3 alkyl, C3-C10 alkenyl, C3-C10 haloalkenyl, C3-C10 alkynyl, C3-C10 haloalkynyl, cyano C1-C6 alkyl, (C1-C5 alkyl)carbonyl, (C1-C5 haloalkyl)carbonyl, (C3-C10 cycloalkyl)carbonyl, (C1-C5 alkyl)carbonyl C1-C5 alkyl, (C1-C5 haloalkyl)carbonyl C1-C5 alkyl, hydroxy C1-C5 alkyl, C1-C5 alkoxy C1-C5 alkyl, C1-C5 alkylthio C1-C5 alkyl, (C1-C5 alkoxy)carbonyl, carboxy C1-C5 alkyl, (C1-C10 alkoxy)carbonyl C1-C5 alkyl, (C1-C10 haloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl, —C(R43) (R44)—C(═O)ON(R45)R46, —C(R47) (R48)—CON(R49)R50, —CH2—C(R56)═N—OR55, —CHMe—C(R58)═NOR57, (C3-C10 alkenoxy)carbonyl C1-C5 alkyl, (C3-C10 alkynoxy)carbonyl C1-C5 alkyl, phenoxycarbonyl, benzyloxycarbonyl, carboxy (C1-C5 alkoxy)carbonyl C1-C5 alkyl, (C1-C10 alkoxy)carbonyl (C1-C5 alkoxy)carbonyl C1-C5 alkyl, (C1-C10 haloalkoxy)carbonyl (C1-C5 alkoxy)carbonyl C1-C5 alkyl, (C3-C10 cycloalkoxy)carbonyl (C1-C5 alkoxy)carbonyl C1-C5 alkyl, (C3-C10 alkenoxy)carbonyl(C1-C5 alkoxy)carbonyl C1-C5 alkyl, (C3-C10 alkynoxy)carbonyl(C1-C5 alkoxy)carbonyl C1-C5 alkyl, carboxy(C1-C5 alkyl)carbonyl, (C1-C10 alkoxy)carbonyl(C1-C5 alkyl)carbonyl, (C1-C10 haloalkoxy)carbonyl (C1-C5 alkyl)carbonyl, C1-C5 alkylsulfonyl, C1-C5 haloalkylsulfonyl, —SO2N(R51)R52, —CON(R53)R54, optionally substituted benzyl, or optionally substituted phenyl;
• R60, R61, and R62 are independently hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 halocycloalkyl, C3-C10 cycloalkyl C1-C3 alkyl, C3-C10 alkenyl, C3-C10 haloalkenyl, C3-C10 alkynyl, C3-C10 haloalkynyl, cyano C1-C6 alkyl, (C1-C5 alkyl)carbonyl, (C1-C5 haloalkyl)carbonyl, (C3-C10 cycloalkyl)carbonyl, (C1-C5 alkyl)carbonyl C1-C5 alkyl, (C1-C5 haloalkyl)carbonyl C1-C5 alkyl, hydroxy C1-C5 alkyl, C1-C5 alkoxy C1-C5 alkyl, C1-C5 alkylthio C1-C5 alkyl, C1-C6 alkoxy)carbonyl, carboxy C1-C5 alkyl, (C1-C10 alkoxy)carbonyl C1-C5 alkyl, (C1-C10 haloalkoxy carbonyl C1-C5 alkyl, (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl, —C(R163)(R164)—C(═O)ON(R165)R166, —C(R167)(R168)—CON(R169)R170, —CH2—C(═NOR175)R176, —CHMe—C(═NOR177)R178, (C3-C10 alkenoxy)carbonyl C1-C5 alkyl, (C3-C10 alkynoxy)carbonyl C1-C5 alkyl, phenoxycarbonyl, benzyloxycarbonyl, carboxy(C1-C5 alkoxy)carbonyl C1-C5 alkyl, (C1-C10 alkoxy)carbonyl (C1-C5 alkoxy)carbonyl C1-C5 alkyl, (C1-C10 haloalkoxy)carbonyl (C1-C5 alkoxy)carbonyl C1-C5 alkyl, (C3-C10 cycloalkoxy)carbonyl (C1-C5 alkoxy)carbonyl C1-C5 alkyl, (C3-C10 alkenoxy)carbonyl(C1-C5 alkoxy)carbonyl C1-C5 alkyl, (C3-C10 alkynoxy)carbonyl (C1-C5 alkoxy)carbonyl C1-C5 alkyl, carboxy(C1-C5 alkyl)carbonyl, (C1-C10 alkoxy)carbonyl(C1-C5 alkyl)carbonyl, (C1-C10 haloalkoxy)carbonyl(C1-C5 alkyl)carbonyl, C1-C5 alkylsulfonyl, C1-C5 haloalkylsulfonyl, —SO2N(R171)R172, —CON(R173)R174, optionally substituted benzyl, or optionally substituted phenyl;
• wherein R43, R44, R163, and R164 are independently hydrogen, halogen, C1-C5 alkyl, or C1-C5 haloalkyl;
• R45, R46, R165, and R166 are independently hydrogen, C1-C5 alkyl, C1-C5 haloalkyl, C3-C8 cycloalkyl, C3-C6 alkenyl, or C3-C6 alkynyl;
• or R45 and R46 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated rind, or R165 and R166 may be combined at their ends to form together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring;
• R47, R48, R167, and R168 are independently hydrogen, halogen, C1-C5 alkyl, or C1-C5 haloalkyl;
• R49, R50, R169, and R170 are independently hydrogen, C1-C5 alkyl, C1-C5 haloalkyl, C3-C8 cycloalkyl, C3-C6 alkenyl, or C3-C6 alkynyl;
• or R49 and R50 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring, or R169 and R170 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring;
• P51, R52, R171 and R172 are independently hydrogen, C1-C5 alkyl C1-C5 haloalkyl, C3-C8 cycloalkyl, C3-C6 alkenyl;
• or C3-C6 alkynyl;
• or R51 and R52 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring, or R171 and 172 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring;
• R53, R54, R173, and R174 are independently hydrogen, C1-C5 alkyl, C1-C5 haloalkyl, C3-C8 cycloalkyl, C3-C6 alkynyl, or C3-C6 alkynyl;
• or R53 and R54 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring, or R173 and R174 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring;
• R55, R57, R175, and R177 are independently hydrogen or C1-C3 alkyl;
• R56, R58, R176, and R178 are independently hydrogen, C1-C5 alkyl, (C1-C5 alkoxy)carbonyl, (C1-C5 haloalkoxy)carbonyl, (C3-C5 cycloalkoxy)carbonyl, (C3-C5 alkenoxy)carbonyl, or (C3-C5 alkynoxy)carbonyl;
• R13 is hydroxy, chlorine, C1-C10 alkyl, C1-C10 haloalkyl, carboxy C1-C5 alkyl, (C1-C10 alkoxy)carbonyl, C1-C5 alkyl, (C1-C10 haloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl, —N(R79)R80, or —OR81;
• R63 hydroxy, chlorine, C1-C10 alkyl, C1-C10 haloalkyl, carboxy C1-C5 alkyl, (C1-C10 alkoxy)carbonyl, C1-C5 alkyl, (C1-C10 haloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl, —N(R179)R180, or —OR181;
• wherein R79 and R179 are independently hydrogen, C1-C5 alkyl, C1-C5 haloalkyl, C3-C8 cycloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, carboxy C1-C5 alkyl, (C1-C10 alkoxy)carbonyl C1-C5 alkyl, (C1-C10 haloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 cycloalkoxy)carbonyl, C1-C5 alkyl, or (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl;
• R80 and R180 are independently hydrogen, C1-C5 alkyl, C1-C5 haloalkyl, C3-C8 cycloalkyl, C3-C6 alkenyl, or C3-C6 alkynyl;
• or R79 and R80 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- or 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring;
• or R179 and R180 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- or 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring;
• and R81 and R181 are independently C1-C5 alkyl, C1-C5 haloalkyl, C3-C8 cycloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, carboxy C1-C5 alkyl, (C1-C10 alkoxy)carbonyl C1-C5 alkyl, (C1-C10 haloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl, or (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl;
• R14 is hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 halocycloalkyl, C3-C10 cycloalkyl C1-C3 alkyl, C3-C10 alkenyl, C3-C10 haloalkenyl, C3-C10 alkynyl, C3-C10 haloalkynyl, carboxy C1-C5 alkyl, (C1-C10 alkoxy)carbonyl C1-C5 alkyl, (C1-C10 haloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 alkenoxy) carbonyl C1-C5 alkyl, (C3-C10 alkynoxy)carbonyl C1-C5 alkyl, —N(R82)R83, optionally substituted benzyl, or optionally substituted phenyl;
• R64 is hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 halocycloalkyl, C3-C10 cycloalkyl C1-C3 alkyl, C3-C10 alkenyl, C3-C10 haloalkenyl, C3-C10 alkynyl, C3-C10 haloalkynyl, carboxy C1-C5 alkyl, (C1-C10 alkoxy)carbonyl C1-C5 alkyl, (C1-C10 haloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 alkenoxy)carbonyl C1-C5 alkyl, (C3-C10 alkynoxy)carbonyl C1-C5 alkyl, —N(R182)R183, optionally substituted benzyl, or optionally substituted phenyl;
• wherein R82 and R182 are independently hydrogen, C1-C5 alkyl, C1-C5 haloalkyl, C3-C8 cycloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, carboxy C1-C5 alkyl, (C1-C10 alkoxy)carbonyl C1-C5 alkyl, (C1-C10 haloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl, or (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl;
• R83 sand R183 are independently hydrogen, C1-C5 alkyl, C1-C5 haloalkyl, C3-C8 cycloalkyl, C3-C6 alkenyl, or C3-C6 alkynyl;
• or R82 and R83 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring;
• or R182 and R183 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring;
• R15 and R65 are independently hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 cycloalkyl C1-C3 alkyl, C3-C10 alkenyl, C3-C10 alkynyl, cyano C1-C6 alkyl, carboxy C1-C5 alkyl, (C1-C10 alkoxy)carbonyl C1-C5 alkyl, optionally substituted benzyl, or optionally substituted phenyl;
• R16 and R56 are independently hydrogen, C1-C10 alkyl, or C1-C10 haloalkyl;
• or R15 and R16 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring;
• or R65 and R66 may be, combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring;
• R17, R26, R27, R67, R76, and R77 are independently hydrogen, cyano, C1-C10 alkyl, C1-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 cycloalkyl C1-C3 alkyl, (C1-C6 alkoxy)carbonyl, or (C1-C6 alkoxy)carbonylmethyl;
• R19 and R69 are independently hydrogen, C1-C10 alkyl, C1-C10 haloalkyl, C3-C10 cycloalkyl, C3-C10 halocycloalkyl, C3-C10 cycloalkyl C1-C3 alkyl, C3-C10 alkenyl, C3-C10 haloalkenyl, C3-C10 alkynyl, C3-C10 haloalkynyl, cyano C1-C6 alkyl, carboxy C1-C5 alkyl, (C1-C10 alkoxy)carbonyl C1-C5 alkyl, (C1-C10 haloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl, or (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl;
• R21 and R71 are independently hydrogen, halogen, C1-C3 alkyl, or C1-C3 haloalkyl;
• R22 and R25 are independently carboxy, (C1-C10 alkoxy)carbonyl, (C1-C10 haloalkoxy)carbonyl, (C3-C10 cyrloalkoxy)carbonyl (C3-C10 halocycloalkoxy)carbonyl, carboxy(C1-C5 alkoxy)carbonyl, (C1-C10 alkoxy)carbonyl (C1-C5 alkoxy)carbonyl, (C1-C10 haloalkoxy)carbonyl (C1-C5 alkoxy)carbonyl, (C3-C10 cycloalkoxy)carbonyl (C1-C5 alkoxy)carbonyl, (C3-C10 alkenoxy)carbonyl (C1-C5 alkoxy)carbonyl, (C3-C10 alkynoxy)carbonyl (C1-C5 alkoxy)carbonyl, —CON(R84)R85, or —C(═O)ON(R86)R87;
• R72 and R75 are independently carboxy, (C1-C10 alkoxy)carbonyl, (C1-C10 haloalkoxy)carbonyl, (C3-C10 cycloalkoxy)carbonyl, (C3-C10 halocycloalkoxy)carbonyl, carboxy(C1-C5 alkoxy)carbonyl, (C1-C10 alkoxy)carbonyl (C1-C5 alkoxy) carbonyl, (C1-C10 haloalkoxy)carbonyl (C1-C5 alkoxy)carbonyl, (C3-C10 cycloalkoxy)carbonyl (C1-C5 alkoxy)carbonyl, (C3-C10 alkenoxy)carbonyl (C1-C5 alkoxy)carbonyl, (C3-C10 alkynoxy)carbonyl (C1-C5 alkoxy carbonyl, —CON(R184)R185, or —C(═O)ON(R186)R187;
• wherein R84 and R184 are independently hydrogen, C1-C5 alkyl, C1-C5 haloalkyl, C3-C8 cycloalkyl, C3-C6 alkenyl, (C3-C6 alkynyl, carboxy C1-C5 alkyl, (C1-C10 alkoxy)carbonyl C1-C5 alkyl, (C1-C10 haloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl, or (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl;
• R85 and R185 are independently hydrogen, C1-C5 alkyl, C1-C5 haloalkyl, C3-C8 cycloalkyl, C3-C6 alkenyl, or C3-C6 alkynyl;
• or R84 and R85 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring;
• or R184 and R185 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring containing zero to one oxygen atom or NH group in the ring;
• R86 and R186 are independently hydrogen, C1-C5 alkyl, C1-C5 haloalkyl, C3-C8 cycloalkyl, C3-C6 alkenyl, C3-C6 alkynyl, carboxy C1-C5 alkyl, (C1-C10 alkoxy)carbonyl C1-C5 alkyl, (C1-C10 haloalkoxy)carbonyl C1-C5 alkyl, (C3-C10 cycloalkoxy)carbonyl C1-C5 alkyl, or (C3-C10 halocycloalkoxy)carbonyl C1-C5 alkyl;
• R87 and R187 are independently hydrogen, C1-C5 alkyl, C1-C5 haloalkyl, C3-C8 cycloalkyl, C3-C6 alkenyl, or C3-C6 alkynyl;
• or R86 and R87 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring;
• or R186 and R187 may be combined at their ends to form, together with the adjacent nitrogen atom, a 3- to 7-membered saturated ring;
• R23, R24, R73, and R74 are independently hydrogen, halogen, C1-C3 alkyl, or C1-C3 haloalkyl;
• and
• Q is any one group of Q14, Q15, or Q17 of the general formula:
• wherein:
• in Q14, E25 is hydrogen, C1-C3 alkyl, or halogen;
• E26 is C1-C3 alkyl optionally substituted with halogen;
• E27 is hydrogen, amino, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, or optionally substituted benzyl;
• and D7 is oxygen or sulfur;
• in Q15, E28 is C1-C3 alkyl optionally substituted with halogen;
• E29 is hydrogen, amino, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, or optionally substituted benzyl;
• and Do is oxygen or sulfur;
• and
• in Q17, E32 is C1-C3 alkyl optionally substituted with halogen;
• E33 is hydrogen, halogen, amino, C1-C3 alkyl optionally substituted with halogen, C1-C3 alkoxy optionally substituted with halogen, or C1-C3 alkylthio optionally substituted with halogen;
• and E43 is hydrogen or C1-C3 alkyl optionally substituted with halogen.