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US 5,403,816 AGranted
Picolinic acid derivative and herbicidal composition
AssigneesKumiai Chemical Industry Co., Ltd., Ihara Chemical Industry Co., Ltd.
InventorsFumiaki Takabe, Yoshihiro Saito, Masatoshi Tamaru, Shigehiko Tachikawa, Ryo Hanai
Life of this patent
Estimating the term…
Abstract
3-Pyrimidinyloxy-substituted picolinic acid derivatives of the formula ##STR1## and their salts are useful as herbicides against annual and perennial gramineous and broadleaf weeds while exhibiting low phytotoxicity to desired crop plants.
Claims8
A picolinic acid derivative of the formula:
- ##STR204## wherein each of R.sup.1 and R.sup.2 is an alkoxy group;
- X.sup.1 is a group of the formula ##STR205## wherein R.sup.3 is a hydrogen atom, an alkyl group, a haloalkyl group, an alkoxyalkyl group, an alkenyl group, an alkynyl group, an alkylcarbonyl group, a benzyloxycarbonyl group or a phenylsulfonyl group;
- and
- R.sup.4 is a haloalkyl group, an alkoxyalkyl group, an alkoxyalkyloxyalkyl group, an alkoxycarbonylalkyl group, a benzyloxyalkyl group, an alkyloxyoxyalkyl group, a phenoxyalkyl group, a dialkylaminoalkyl group, a cyanoalkyl group, an alkoxy group, a cycloalkyl group, an alkenyl group (which may be substituted at one or more positions by a halogen atom or a cyano group), an alkynyl group, a phenylalkyl group (which may be the same or different, and substituted at one or more positions by a halogen atom, an alkyl group, an alkoxy group, a nitro group or a cyano group), a cycloalkylcarbonyl group, a haloalkylcarbonyl group, an alkoxyalkylcarbonyl group, a cyanoalkylcarbonyl group, a phenoxyalkylcarbonyl group, a phenylalkylcarbonyl group, a halophenylalkylcarbonyl group, a benzoyl group (which is substituted by an alkyl group, a haloalkyl group, a halogen atom, an alkoxy group, a cyano group or a nitro group), a furylcarbonyl group, a pyridylcarbonyl group, a pyrrolylcarbonyl group, a thienylcarbonyl group, an alkenylcarbonyl group, a phenylalkenylcarbonyl group, a hydroxycarbonylalkenylcarbonyl group, an alkoxycarbonylalkylcarbonyl group, an alkoxyalkoxycarbonyl group, a monoalkylaminocarbonyl group, a dialkylaminocarbonyl group, a phenylaminocarbonyl group, a benzylaminocarbonyl group, a halobenzylaminocarbonyl group, an alkoxycarbonyl group, a haloalkoxycarbonyl group, a benzyloxycarbonyl group, an alkenyloxycarbonyl group, an alkynyloxycarbonyl group, an alkylsulfonyl group, a haloalkylsulfonyl group, a benzylsulfonyl group which may be substituted by an alkoxycarbonyl group, a phenylsulfonyl group which may be substituted by an alkoxycarbonyl group, a halophenylsulfonyl group, an alkyl(thiocarbonyl) group, a haloalkyl(thiocarbonyl) group, a benzyl(thiocarbonyl) group, a halobenzyl(thiocarbonyl) group, an alkenyl(thiocarbonyl) group, an alkynyl(thiocarbonyl) group which may be substituted by a cyano group, an alkylamino(thiocarbonyl) group, a phenylamino(thiocarbonyl) group, a dialkylamino(thiocarbonyl) group, a benzyloxy group or a group of the formula ##STR206## wherein each of R.sup.5 and R.sup.6 which may be the same or different, is a hydrogen atom, an alkyl group or an alkoxycarbonyl group, or R.sup.5 and R.sup.6 form together with the adjacent nitrogen atom a morpholino group;
- or
- R.sup.3 and R.sup.4 form together with the adjacent nitrogen atom, an azido group, an isothiocyanate group, a phthalimide group, a maleimide group, a succinimido group, a pyrrolidinyl group, a piperidino group, a pyrrolyl group, a morpholino group, a group of the formula ##STR207## wherein n is 0 or 1, and m is 1 or 2, or X.sup.1 is a group of the formula ##STR208## wherein each of R.sup.7 and R.sup.8 which may be the same or different, is a hydrogen atom, an alkyl group, a dialkylamino group, an amino group, an alkylthio group, a phenyl group or a benzyl group;
- and
- R.sup.9 is a hydrogen atom, an alkyl group, an alkenyl group, a benzyl group, an alkali metal atom, an alkaline earth metal atom or an organic amine cation;
- or a salt thereof, wherein said alkyl and alkoxy groups are C.sub.1-5 linear or branched alkyl and alkoxy groups, said alkenyl and alkynyl groups are C.sub.2-6 alkenyl and alkynyl groups, said cycloalkyl groups are C.sub.3-6 cycloalkyl groups, said alkylideneamino groups are C.sub.3-12 alkylideneamino groups, and said cycloalkylideneamino groups are C.sub.3-8 cycloalkylideneamino groups.
6 more elements
A picolinic acid derivative of the formula:
- ##STR209## wherein each of R.sup.1 and R.sup.2 is an alkoxy group, X.sup.2 is an amino group, an alkylamino group or a dialkylamino group, and W is COOR.sup.10, COSR.sup.11, or CON(R.sup.12)(R.sup.13), wherein R.sup.10 is a phenyl group (which may be substituted by a halogen atom or a methyl group), a benzyloxyalkyl group, an alkylideneamino group, a cycloalkylideneamino group or a dialkylamino group, R.sup.11 is an alkyl group or a phenyl group, and each of R.sup.12 and R.sup.13 which may be the same or different, is a hydrogen atom, an alkylsulfonyl group, an alkoxyalkyl group, an alkyl group, a benzyloxy group or an alkoxy group, or R.sup.12 and R.sup.13 form together with the adjacent nitrogen atom, an imidazolyl group;
- or a salt thereof,
- wherein said alkyl and alkoxy groups are C.sub.1-5 linear or branched alkyl and alkoxy groups, said alkenyl and alkynyl groups are C.sub.2-6 alkenyl and alkynyl groups, said cycloalkyl groups are C.sub.3-8 cycloalkyl groups, said alkylideneamino groups are C.sub.3-12 alkylideneamino groups, and said cycloalkylideneamino groups are C.sub.3-8 cycloalkylideneamino groups.
A picolinic acid derivative of the formula:
- ##STR210## wherein each of R.sup.1 and R.sup.2 is an alkoxy group, X.sup.2 is an amino group, an alkylamino group or a dialkylamino group, Y is a methylene group which may be substituted by a cyano group, or a carbonyl group, and R.sup.14 is a hydrogen atom or an alkyl group;
- or a salt thereof,
- wherein said alkyl and alkyl groups are C.sub.1-5 linear or branched alkyl and alkoxy groups.
A picolinic acid derivative of the formula:
- ##STR211## wherein each of R.sup.1 and R.sup.2 is an alkoxy group, X.sup.3 is a dialkylamino group, Z is a group of the formula R.sup.+ A.sup.- wherein R.sup.+ is a cation selected from the group consisting of an alkyl group, an acyl group and an alkylsulfonyl group, and A.sup.- is an anion of the conjugate base, and R.sup.15 is an alkyl group;
- or a salt thereof,
- wherein said alkyl and alkoxy groups are C.sub.1-5 linear or branched alkyl and alkoxy groups and said acyl group is a C.sub.2-8 acyl group.
Dependencies are inferred from the claim text.