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US 5,849,768 AGranted
.alpha.-unsaturated amines, their production and use
AssigneeTakeda Chemical Industries, Ltd.
InventorsIsao Minamida, Koichi Iwanaga, Tetsuo Okauchi
Life of this patent
Estimating the term…
Abstract
.alpha.-Unsaturated amines of the formula: ##STR1## wherein X.sup.1 and X.sup.2 are such that one is an electron-attracting group with the other being a hydrogen atom or an electron-attracting group; R.sup.1 is a group attached through a nitrogen atom; R.sup.2 is a hydrogen atom or a group attached through a carbon, nitrogen or oxygen atom; n is an integer equal to 0, 1 or 2; A is a heterocyclic group or a cyclic hydrocarbon group, and salts thereof and their agrochemical use as insecticidal and/or miticidal agents are described.
Claims18
A compound of the formula ##STR123## wherein one of X.sup.1 and X.sup.2 is an electron-attracting group with the other being a hydrogen atom or an electron-attracting group, the electron-attracting groups being cyano, nitro, C.sub.1-4 alkoxycarbonyl, hydroxycarbonyl, phenoxycarbonyl, naphthyloxycarbonyl, C.sub.1-4 alkylsulfonyl which can be substituted with halogen, aminosulfonyl, di-C.sub.1-4 alkoxyphosphoryl, C.sub.1-4 alkylcarbonyl which can be substituted with halogen, C.sub.1-4 alkylsulfonylthiocarbamoyl, carbamoyl, or heterocycleoxycarbonyl wherein the heterocycle moiety is defined below as group D;
- or
- wherein one of X.sup.1 and X.sup.2 is a halogen atom;
- R.sup.1 is --NR.sup.3 R.sup.4 which is attached through its nitrogen atom;
- R.sup.3 is a hydrogen atom, a C.sub.1-6 alkyl group, a phenyl group, a naphthyl group, a C.sub.7-9 phenylalkyl group, a C.sub.1-4 alkanoyl, a benzoyl group, a naphthoyl group, a C.sub.1-4 alkoxy-carbonyl group, a phenoxycarbonyl group, a naphthoxycarbonyl group, a phenylsulfonyl group, a naphthylsulfonyl group, a C.sub.1-4 alkylsulfonyl group, a di-C.sub.1-4 alkoxyphosphoryl group, a C.sub.1-4 alkoxy group, a hydroxy group, an amino group, a di-C.sub.1-4 alkylamino group, a C.sub.1-4 alkanoylamino group, a C.sub.1-4 alkoxycarbonylamino group, a C.sub.1-4 alkylsulfonylamino group, a di-C.sub.1-4 alkoxyphosphorylamino group, a C.sub.7-9 phenylalkyloxy group or a C.sub.1-4 alkoxy-carbonyl-C.sub.1-4 alkyl group;
- R.sup.4 is a hydrogen atom, or a C.sub.1-4 alkyl, C.sub.3-6 cycloalkyl, C.sub.2-4 alkenyl, C.sub.3-6 cycloalkenyl or C.sub.2-4 alkynyl group which can optionally be substituted by 1 to 3 substituents selected from hydroxyl, C.sub.1-4 alkoxy, halogen, di-C.sub.1-4 alkylamino, C.sub.1-4 alkylthio, C.sub.1-3 alkylcarbonylamino, C.sub.1-4 alkylsulfonylamino, tri-C.sub.1-4 alkylsilyl and pyridyl or thiazolyl which can be optionally substituted with a halogen atom, or R.sup.3 and R.sup.4 can, taken together with the adjacent nitrogen atom, constitute a pyrrolidino, methylpiperazino, morpholino, or piperidino group,
- R.sup.2 is:
- (i) a C.sub.1-4 alkylcarbonyl, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.3-6 cycloalkyl, phenyl, naphthyl, C.sub.7-9 phenylalkyl or 3- or 4-pyridyl group which can be substituted by 1 to 3 substituents selected from the group consisting of a C.sub.1-4 alkylthio group, a C.sub.1-4 alkoxy group, a mono-C.sub.1-4 alkylamino group, a di-C.sub.1-4 alkylamino group, a C.sub.1-4 alkoxy-carbonyl group, a C.sub.1-4 alkylsulfonyl group, a halogen atom and a C.sub.1-4 alkanoyl group, or
- (ii) a C.sub.1-4 alkoxy, C.sub.3-6 cycloalkoxy, C.sub.2-4 alkenyloxy, C.sub.3-6 cycloalkenyloxy, ethynyloxy, phenoxy, naphthoxy, thienyloxy or hydroxyl group which can have 1 to 3 substituents selected from the group consisting of halogen and phenyl, or
- (iii) the group --NR.sup.3 R.sup.4 which is attached through its nitrogen atom, or
- (iv) hydrogen;
- n is an integer equal to 0, 1 or 2, and
- A.sup.0 is a 2-, 3- or 4-pyridyl which can have 1 to 5 substituents as defined below as the substitutents to the heterocyclic group defined as the group D;
- wherein the group D can be a heterocyclic group selected from the group consisting of 2- or 3-thienyl, 2- or 3-furyl, 2- or 3-pyrrolyl, 2-, 3- or 4-pyridyl, 2-, 4- or 5-oxazolyl, 2-, 4- or 5-thiazolyl, 3-, 4- or 5-pyrazolyl, 2-, 4- or 5-imidazolyl, 3-, 4- or 5-isoxazolyl, 3-, 4- or 5-isothiazolyl, 3- or 5-(1,2,4-oxadiazolyl), 1,3,4-oxadiazolyl, 3- or 5-(1,2,4-thiadiazolyl), 1,3,4-thiadiazolyl, 4- or 5-(1,2,3-thiadiazolyl), 1,2,5-thiadiazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1H- or 2H-tetrazolyl, N-oxido-2-, 3- or 4-pyridyl, 2-, 4- or 5-pyrimidinyl, N-oxido-2-, 4- or 5-pyrimidinyl, 3- or 4-pyridazinyl, pyrazinyl, N-oxido-3- or 4-pyridazinyl, benzofuryl, benzothiazolyl, benzoxazolyl, triazinyl, oxotriazinyl, tetrazolo 1,5-b!pyridazinyl, triazolo4,5-b!pyridazinyl, oxoimidazinyl, dioxotriazinyl, pyrrolidinyl, piperidinyl, pyranyl, thiopyranyl, 1,4-oxazinyl, morpholinyl, 1,4-thiazinyl, 1,3-thiazinyl, piperazinyl, benzimidazolyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, indolizinyl, quinolizinyl, 1,8-naphthyridinyl, purinyl, pteridinyl, dibenzofuranyl, carbazolyl, acridinyl, phenanthridinyl, phenazinyl, phenothiazinyl and phenoxazinyl groups, each of which can have 1 to 5 substituents selected from the group consisting of
- (i) a C.sub.1-4 alkyl,
- (ii) C.sub.3-6 cycloalkyl,
- (iii) phenyl, naphthyl,
- (iv) C.sub.1-4 alkoxy,
- (v) C.sub.3-6 cycloalkyloxy,
- (vi) phenoxy, naphthyloxy,
- (vii) C.sub.7-12 phenylalkyloxy,
- (viii) C.sub.1-4 alkylthio,
- (ix) C.sub.3-6 cycloalkylthio,
- (x) phenylthio, naphthylthio,
- (xi) C.sub.7-12 phenylalkylthio,
- (xii) mono-C.sub.1-4 alkylamino,
- (xiii) di-C.sub.1-4 alkylamino,
- (xiv) C.sub.3-6 cycloalkylamino,
- (xv) anilino,
- (xvi) C.sub.7-12 phenylalkylamino,
- (xvii) halogen
- (xviii) C.sub.1-4 alkoxycarbonyl,
- (xix) phenoxycarbonyl,
- (xx) C.sub.3-6 cycloalkyloxycarbonyl,
- (xxi) C.sub.7-12 phenylalkyloxycarbonyl,
- (xxii) C.sub.1-5 alkanoyl,
- (xxiii) C.sub.1-15 alkanoyloxy,
- (xxiv) carbamoyl, N-methylcarbamoyl, N,N-dimethylcarbamoyl, N-ethylcarbamoyl, N,N-diethylcarbamoyl, N-phenylcarbamoyl, pyrrolidinocarbamoyl, piperidinocarbamoyl, piperazinocarbamoyl, morpholinocarbamoyl, N-benzylcarbamoyl,
- (xxv) N-methylcarbamoyloxy, N,N-dimethylcarbamoyloxy, N-ethylcarbamoyloxy, N-benzylcarbamoyloxy, N,N-dibenzylcarbamoyloxy, N-phenylcarbamoyloxy,
- (xxvi) C.sub.1-4 alkanoylamino,
- (xxvii) benzamido,
- (xxviii) C.sub.1-4 alkoxycarbonylamino,
- (xxix) C.sub.7-12 phenylalkyloxycarbonyl,
- (xxx) methanesulfonylamino, ethanesulfonylamino, butanesulfonylamino,benzenesulfonylamino,toluenesulfonylamino, naphthalenesulfonylamino, trifluoromethanesulfonylamino, 2-chloroethanesulfonylamino, 2,2,2-trifluoromethanesulfonylamino,
- (xxxi) pyrrolidinyl, pyrrolyl, pyrazolyl, imidazolyl, furyl, thienyl, oxazolyl, isoxazolyl, isothiazolyl, thiazolyl, piperidinyl, pyridyl, piperazinyl, pyrimidinyl, pyranyl, tetrahydropyranyl, tetrahydrofuryl, indolyl, quinolyl, 1,3,4-oxadiazolyl, thieno2,3-dlpyridyl, 1,2,3-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1,3,4-triazolyl, tetrazolyl, 4,5-dihydro-1,3-dioxazolyl, tetrazolo1,5-b!pyridazinyl, benzothiazolyl, benzoxazoiyl, benzimidazolyl, benzothienyl,
- (xxxii) heterocyclethio, heterocycleoxy, heterocycleamino or heterocyclecarbonylamino group which is derived by attachment of any of heterocyclic groups (xxxi) to the S, O, N atom or the carbonylamino group,
- (xxxiii) di-C.sub.1-4 alkylphosphinothioylamino,
- (xxxiv) methoxyimino, ethoxyimino, 2-fluoroethoxyimino, carboxymethoxyimino, 1-carboxy-1-methylethoxyimino, 2,2,2-trichloroethoxycarbonylmethoxyimino, 1-(2,2,2-trichloroethoxycarbonyl)-1-methylethoxyimino, (2-aminothiazol-4-yl)methoxyimino, (1H-imidazol-4-yl)methoxyimino,
- (xxxv) C.sub.1-4 alkylsulfonyloxy,
- (xxxvi) benzenesulfonyloxy, toluenesulfonyloxy,
- (xxxvii) diphenylphosphinothioylamino,
- (xxxviii) thiocarbamoylthio, N-methylthiocarbamoylthio, N,N-dimethylthiocarbamoylthio, N-ethylthiocarbamoylthio, N-benzylthiocarbamoylthio, N,N-dibenzylthiocarbamoylthio, N-phenylthiocarbamoylthio,
- (xxxix) trimethylsilyloxy, t-butyldimethylsilyloxy, t-butyldiphenylsilyloxy, dimethylphenylsilyloxy,
- (xL) trimethylsilyl, t-butyidimethylsilyl, t-butyldiphenylsilyl, dimethylphenylsilyl,
- (xLi) C.sub.1-4 alkylsulfinyl,
- (xLii) phenylsulfinyl, naphthylsulfinyl,
- (xLiii) C.sub.1-4 alkylsulfonyl,
- (xLiv) benzenesulfonyl, toluenesulfonyl,
- (xLv) C.sub.1-4 alkoxy-carbonyloxy,
- (xLvi) halo-C.sub.1-4 alkyl,
- (xlvii) halo-C.sub.1-4 alkoxy, halo-C.sub.1-4 alkylthio, halo-C.sub.1-4 alkylsulfinyl, halo-C.sub.1-4 alkylsulfonyl,
- (xLviii) cyano, nitro, hydroxyl, carboxyl, sulfo, phosphono,
- (xLix) C.sub.1-4 alkyloxysulfonyl,
- (L) phenoxysulfonyl, tolyloxysulfonyl,
- (Li) C.sub.7-12 phenylalkyloxysulfonyl and
- (Lii) di-C.sub.1-4 alkyloxyphosphoryl group, with the proviso that when R.sup.2 is a hydrogen atom, R.sup.1 is a group of the formula:
- ##STR124## wherein R.sup.3a is a hydrogen atom, C.sub.1-4 alkyl, C.sub.7-9 phenylalkyl or C.sub.1-4 alkanoyl and R.sup.4a is a hydrogen atom, C.sub.1-4 alkyl, C.sub.1-4 alkoxy-C.sub.1-4 alkyl, (di-C.sub.1-4 alkylamino)-C.sub.1-4 alkyl, tri-C.sub.1-4 alkylsilyl-C.sub.1-4 alkyl, C.sub.2-4 alkenyl, or pyridyl- or thiazolyl-C.sub.1-2 alkyl wherein pyridyl or thiazolyl moiety may optionally be substituted with a halogen atom, or R.sup.3a and R.sup.4a taken together with the adjacent nitrogen atom constitute pyrrolidino, and A.sup.0 is pyridyl which may optionally be substituted with a halogen, C.sub.1-4 alkyl, C.sub.1-4 alkylthio or C.sub.1-4 alkoxy, or a salt thereof.
63 more elements
A compound of the formula ##STR128## wherein, A is pyridyl which can be substituted by halogen;
- R.sub.2 is hydrogen or C.sub.1-4 alkyl;
- R.sub.3 is hydrogen, C.sub.1-5 alkyl or benzyl;
- R.sub.4 is hydrogen, C.sub.1-5 alkyl or C.sub.3-7 cycloalkyl, or R.sub.3 and R.sub.4 can, taken together with the adjacent nitrogen atom, constitute a pyrrolidinyl group or a piperazinyl group which can be N'-methyl substituted.
An insecticidal/miticidal composition which comprises an effective amount of a compound of the formula ##STR129## wherein, A is pyridyl which can be substituted by halogen;
- R.sub.2 is hydrogen or C.sub.1-4 alkyl;
- R.sub.3 is hydrogen, C.sub.1-5 alkyl or benzyl;
- R.sub.4 is hydrogen, C.sub.1-5 alkyl or C.sub.3-7 cycloalkyl, or R.sub.3 and R.sub.4 can, taken together with the adjacent nitrogen atom, constitute a pyrrolidinyl group or a piperazinyl group which can be N'-methyl substituted.
An insecticidal/miticidal composition which comprises an effective amount of a compound of the formula ##STR130## wherein one of X.sup.1 and X.sup.2 is an electron-attracting group with the other being a hydrogen atom or an electron-attracting group, the electron-attracting groups being cyano, nitro, C.sub.1-4 alkoxycarbonyl, hydroxycarbonyl, phenoxycarbonyl, naphthyloxycarbonyl, C.sub.1-4 alkylsulfonyl which can be substituted with halogen, aminosulfonyl, di-C.sub.1-4 alkoxyphosphoryl, C.sub.1-4 alkylcarbonyl which can be substituted with halogen, C.sub.1-4 alkylsulfonylthiocarbamoyl, carbamoyl, or heterocycleoxycarbonyl wherein the heterocycle moiety is defined below as group D;
- or
- wherein one of X.sup.1 and X.sup.2 is a halogen atom;
- R.sup.1 is --NR.sup.3 R.sup.4 which is attached through its nitrogen atom;
- R.sup.3 is a hydrogen atom, a C.sub.1-6 alkyl group, a phenyl group, a naphthyl group, a C.sub.7-9 phenylalkyl group, a C.sub.1-4 alkanoyl, a benzoyl group, a naphthoyl group, a C.sub.1-4 alkoxy-carbonyl group, a phenoxycarbonyl group, a naphthoxycarbonyl group, a phenylsulfonyl group, a naphthylsulfonyl group, a C.sub.1-4 alkylsulfonyl group, a di-C.sub.1-4 alkoxyphosphoryl group, a C.sub.1-4 alkoxy group, a hydroxy group, an amino group, a di-C.sub.1-4 alkylamino group, a C.sub.1-4 alkanoylamino group, a C.sub.1-4 alkoxy-carbonylamino group, a C.sub.1-4 alkylsulfonylamino group, a di-C.sub.1-4 alkoxyphosphorylamino group, a C.sub.7-9 phenylalkyloxy group or a C.sub.1-4 alkoxy-carbonyl-C.sub.1-4 alkyl group;
- R.sup.4 is a hydrogen atom, or a C.sub.1-4 alkyl, C.sub.3-6 cycloalkyl, C.sub.2-4 alkenyl, C.sub.3-6 cycloalkenyl or C.sub.2-4 alkynyl group which can optionally be substituted by 1 to 3 substituents selected from hydroxyl, C.sub.1-4 alkoxy, halogen, di-C.sub.1-4 alkylamino, C.sub.1-4 alkylthio, C.sub.1-3 alkylcarbonylamino, C.sub.1-4 alkylsulfonylamino, tri-C.sub.1-4 alkylsilyl and pyridyl or thiazolyl which can be optionally substituted with a halogen atom, or R.sup.3 and R.sup.4 can, taken together with the adjacent nitrogen atom, constitute a pyrrolidino, methylpiperazino, morpholino, or piperidino group,
- R.sup.2 is:
- (i) a C.sub.1-4 alkylcarbonyl, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.3-6 cycloalkyl, phenyl, naphthyl, C.sub.7-9 phenylalkyl or 3- or 4-pyridyl group which can be substituted by 1 to 3 substituents selected from the group consisting of a C.sub.1-4 alkylthio group, a C.sub.1-4 alkoxy group, a mono-C.sub.1-4 alkylamino group, a di-C.sub.1-4 alkylamino group, a C.sub.1-4 alkoxy-carbonyl group, a C.sub.1-4 alkylsulfonyl group, a halogen atom and a C.sub.1-4 alkanoyl group, or
- (ii) a C.sub.1-4 alkoxy, C.sub.3-6 cycloalkoxy, C.sub.2-4 alkenyloxy, C.sub.3-6 cycloalkenyloxy, ethynyloxy, phenoxy, naphthoxy, thienyloxy or hydroxyl group which can have 1 to 3 substituents selected from the group consisting of halogen and phenyl, or
- (iii) the group --NR.sup.3 R.sup.4 which is attached through its nitrogen atom, or
- (iv) hydrogen;
- n is an integer equal to 0, 1 or 2, and
- A.sup.0 is a 2-, 3- or 4-pyridyl which can have 1 to 5 substituents as defined below as the substituents to the heterocyclic group defined as the group D;
- wherein the group D can be a heterocyclic group selected from the grouP consisting of 2- or 3-thienyl, 2- or 3-furyl, 2- or 3-pyrrolyl, 2-, 3- or 4-pyridyl, 2-, 4- or 5-oxazolyl, 2-, 4- or 5-thiazolyl, 3-, 4- or 5-pyrazolyl, 2-, 4-or 5-imidazolyl, 3-, 4- or 5-isoxazolyl, 3-, 4- or 5-isothiazolyl, 3- or 5-(1,2,4-oxadiazolyl), 1,3,4-oxadiazolyl, 3- or 5-(1,2,4-thiadiazolyl), 1,3,4-thiadiazolyl, 4- or 5-(1,2,3-thiadiazolyl), 1,2,5-thiadiazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1H- or 2H-tetrazolyl, N-oxido-2-, 3- or 4-pyridyl, 2-, 4- or 5-pyrimidinyl, N-oxido-2-, 4- or 5-pyrimidinyl, 3- or 4-pyridazinyl, pyrazinyl, N-oxido-3- or 4-pyridazinyl, benzofuryl, benzothiazolyl, benzoxazolyl, triazinyl, oxotriazinyl, tetrazolo 1,5-b!pyridazinyl, triazolo4,5-b!pyridazinyl, oxoimidazinyl, dioxotriazinyl, pyrrolidinyl, piperidinyl, pyranyl, thiopyranyl, 1,4-oxazinyl, morpholinyl, 1,4-thiazinyl, 1,3-thiazinyl, piperazinyl, benzimidazolyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, indolizinyl, quinolizinyl, 1,8-naphthyridinyl, purinyl, pteridinyl, dibenzofuranyl, carbazolyl, acridinyl, phenanthridinyl, phenazinyl, phenothiazinyl and phenoxazinyl groups, each of which can have 1 to 5 substituents selected from the group consisting of
- (i) a C.sub.1-4 alkyl,
- (ii) C.sub.3-6 cycloalkyl,
- (iii) phenyl, naphthyl,
- (iv) C.sub.1-4 alkoxy,
- (v) C.sub.3-6 cycloalkyloxy,
- (vi) phenoxy, naphthyloxy,
- (vii) C.sub.7-12 phenylalkyloxy,
- (viii) C.sub.1-4 alkylthio,
- (ix) C.sub.3-6 cycloalkylthio,
- (x) phenylthio, naphthylthio,
- (xi) C.sub.7-12 phenylalkylthio,
- (xii) mono-C.sub.1-4 alkylamino,
- (xiii) di-C.sub.1-4 alkylamino,
- (xiv) C.sub.3-6 cycloalkylamino,
- (xv) anilino,
- (xvi) C.sub.7-12 phenylalkylamino,
- (xvii) halogen
- (xviii) C.sub.1-4 alkoxycarbonyl,
- (xix) phenoxycarbonyl,
- (xx) C.sub.3-6 cycloalkyloxycarbonyl,
- (xxi) C.sub.7-12 phenylalkyloxycarbonyl,
- (xxii) C.sub.1-5 alkanoyl,
- (xxiii) C.sub.1-15 alkanoyloxy,
- (xxiv) carbamoyl, N-methylcarbamoyl, N,N-dimethylcarbamoyl, N-ethylcarbamoyl, N,N-diethylcarbamoyl, N-phenylcarbamoyl, pyrrolidinocarbamoyl, piperidinocarbamoyl, piperazinocarbamoyl, morpholinocarbamoyl, N-benzylcarbamoyl,
- (xxv) N-methylcarbamoyloxy, N,N-dimethylcarbamoyloxy, N-ethylcarbamoyloxy, N-benzylcarbamoyloxy, N,N-dibenzylcarbamoyloxy, N-phenylcarbamoyloxy,
- (xxvi) C.sub.1-4 alkanoylamino,
- (xxvii) benzamido,
- (xxviii) C.sub.1-4 alkoxycarbonylamino,
- (xxix) C.sub.7-12 phenylalkyloxycarbonyl,
- (xxx) methanesulfonylamino, ethanesulfonylamino, butanesulfonylamino, benzenesulfonylamino, toluenesulfonylamino, naphthalenesulfonylamino, trifluoromethanesulfonylamino, 2-chloroethanesulfonylamino, 2,2,2-trifluoromethanesulfonylamino,
- (xxxi) pyrrolidinyl, pyrrolyl, pyrazolyl, imidazolyl, furyl, thienyl, oxazolyl, isoxazolyl, isothiazolyl, thiazolyl, piperidinyl, pyridyl, piperazinyl, pyrimidinyl, pyranyl, tetrahydropyranyl, tetrahydrofuryl, indolyl, quinolyl, 1,3,4-oxadiazolyl, thieno2,3-dlpyridyl, 1,2,3-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1,3,4-triazolyl, tetrazolyl, 4,5-dihydro-1,3-dioxazolyl, tetrazolo1,5-b!pyridazinyl, benzothiazolyl, benzoxazoiyl, benzimidazolyl, benzothienyl,
- (xxxii) heterocyclethio, heterocycleoxy, heterocycleamino or heterocyclecarbonylamino group which is derived by attachment of any of heterocyclic groups (xxxi) to the S, O, N atom or the carbonylamino group,
- (xxxiii) di-C.sub.1-4 alkylphosphinothioylamino,
- (xxxiv) methoxyimino, ethoxyimino, 2-fluoroethoxyimino, carboxymethoxyimino, 1-carboxy-1-methylethoxyimino, 2,2,2-trichloroethoxycarbonylmethoxyimino, 1-(2,2,2-trichloroethoxycarbonyl)-1-methylethoxyimino, (2-aminothiazol-4-yl)methoxyimino, (1H-imidazol-4-yl)methoxyimino,
- (xxxv) C.sub.1-4 alkylsulfonyloxy,
- (xxxvi) benzenesulfonyloxy, toluenesulfonyloxy,
- (xxxvii) diphenylphosphinothioylamino,
- (xxxviii) thiocarbamoylthio, N-methylthiocarbamoylthio, N,N-dimethylthiocarbamoylthio, N-ethylthiocarbamoylthio, N-benzylthiocarbamoylthio, N,N-dibenzylthiocarbamoylthio, N-phenylthiocarbamoylthio,
- (xxxix) trimethylsilyloxy, t-butyldimethylsilyloxy, t-butyldiphenylsilyloxy, dimethylphenylsilyloxy,
- (xL) trimethylsilyl, t-butyidimethylsilyl, t-butyldiphenylsilyl, dimethylphenylsilyl,
- (xLi) C.sub.1-4 alkylsulfinyl,
- (xLii) phenylsulfinyl, naphthylsulfinyl,
- (xLiii) C.sub.1-4 alkylsulfonyl,
- (xLiv) benzenesulfonyl, toluenesulfonyl,
- (xLv) C.sub.1-4 alkoxy-carbonyloxy,
- (xLvi) halo-C.sub.1-4 alkyl,
- (xlvii) halo-C.sub.1-4 alkoxy, halo-C.sub.1-4 alkylthio, halo-C.sub.1-4 alkylsulfinyl, halo-C.sub.1-4 alkylsulfonyl,
- (xLviii) cyano, nitro, hydroxyl, carboxyl, sulfo, phosphono,
- (xLix) C.sub.1-4 alkyloxysulfonyl,
- (L) phenoxysulfonyl, tolyloxysulfonyl,
- (Li) C.sub.7-12 phenylalkyloxysulfonyl and
- (Lii) di-C.sub.1-4 alkyloxyphosphoryl group, with the proviso that when R.sup.2 is a hydrogen atom, R.sup.1 is a group of the formula:
- ##STR131## wherein R.sup.3a is a hydrogen atom, C.sub.1-4 alkyl, C.sub.7-9 phenylalkyl or C.sub.1-4 alkanoyl and R.sup.4a is a hydrogen atom, C.sub.1-4 alkyl, C.sub.1-4 alkoxy-C.sub.1-4 alkyl, (di-C.sub.1-4 alkylamino)-C.sub.1-4 alkyl, tri-C.sub.1-4 alkylsilyl-C.sub.1-4 alkyl, C.sub.2-4 alkenyl, or pyridyl- or thiazolyl-C.sub.1-2 alkyl wherein pyridyl or thiazolyl moiety may optionally be substituted with a halogen atom, or R.sup.3a and R.sup.4a taken together with the adjacent nitrogen atom constitute pyrrolidino, and A.sup.0 is pyridyl which may optionally be substituted with a halogen, C.sub.1-4 alkyl, C.sub.1-4 alkylthio or C.sub.1-4 alkoxy, or a salt thereof.
63 more elements
A method of combatting insects or mites which comprises administering an effective dose of a compound of the formula ##STR132## wherein one of X.sup.1 and X.sup.2 is an electron-attracting group with the other being a hydrogen atom or an electron-attracting group, the electron-attracting groups being cyano, nitro, C.sub.1-4 alkoxycarbonyl, hydroxycarbonyl, phenoxycarbonyl, naphthyloxycarbonyl, C.sub.1-4 alkylsulfonyl which can be substituted with halogen, aminosulfonyl, di-C.sub.1-4 alkoxyphosphoryl, C.sub.1-4 alkylcarbonyl which can be substituted with halogen, C.sub.1-4 alkylsulfonylthiocarbamoyl, carbamoyl, or heterocycleoxycarbonyl wherein the heterocycle moiety is defined below as group D;
- or
- wherein one of X.sup.1 and X.sup.2 is a halogen atom;
- R.sup.1 is --NR.sup.3 R.sup.4 which is attached through its nitrogen atom;
- R.sup.3 is a hydrogen atom, a C.sub.1-6 alkyl group, a phenyl group, a naphthyl group, a C.sub.7-9 phenylalkyl group, a C.sub.1-4 alkanoyl, a benzoyl group, a naphthoyl group, a C.sub.1-4 alkoxy-carbonyl group, a phenoxycarbonyl group, a naphthoxycarbonyl group, a phenylsulfonyl group, a naphthylsulfonyl group, a C.sub.1-4 alkylsulfonyl group, a di-C.sub.1-4 alkoxyphosphoryl group, a C.sub.1-4 alkoxy group, a hydroxy group, an amino group, a di-C.sub.1-4 alkylamino group, a C.sub.1-4 alkanoylamino group, a C.sub.1-4 alkoxycarbonylamino group, a C.sub.1-4 alkylsulfonylamino group, a di-C.sub.1-4 alkoxyphosphorylamino group, a C.sub.7-9 phenylalkyloxy group or a C.sub.1-4 alkoxy-carbonyl-C.sub.1-4 alkyl group;
- R.sup.4 is a hydrogen atom, or a C.sub.1-4 alkyl, C.sub.3-6 cycloalkyl, C.sub.2-4 alkenyl, C.sub.3-6 cycloalkenyl or C.sub.2-4 alkynyl group which can optionally be substituted by 1 to 3 substituents selected from hydroxyl, C.sub.1-4 alkoxy, halogen, di-C.sub.1-4 alkylamino, C.sub.1-4 alkylthio, C.sub.1-3 alkylcarbonylamino, C.sub.1-4 alkylsulfonylamino, tri-C.sub.1-4 alkylsilyl and pyridyl or thiazolyl which can be optionally substituted with a halogen atom, or R.sup.3 and R.sup.4 can, taken together with the adjacent nitrogen atom, constitute a pyrrolidino, methylpiperazino, morpholino, or piperidino group,
- R.sup.2 is:
- (i) a C.sub.1-4 alkylcarbonyl, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.3-6 cycloalkyl, phenyl, naphthyl, C.sub.7-9 phenylalkyl or 3- or 4-pyridyl group which can be substituted by 1 to 3 substituents selected from the group consisting of a C.sub.1-4 alkylthio group, a C.sub.1-4 alkoxy group, a mono-C.sub.1-4 alkylamino group, a di-C.sub.1-4 alkylamino group, a C.sub.1-4 alkoxy-carbonyl group, a C.sub.1-4 alkylsulfonyl group, a halogen atom and a C.sub.1-4 alkanoyl group, or
- (ii) a C.sub.1-4 alkoxy, C.sub.3-6 cycloalkoxy, C.sub.2-4 alkenyloxy, C.sub.3-6 cycloalkenyloxy, ethynyloxy, phenoxy, naphthoxy, thienyloxy or hydroxyl group which can have 1 to 3 substituents selected from the group consisting of halogen and phenyl, or
- (iii) the group --NR.sup.3 R.sup.4 which is attached through its nitrogen atom, or
- (iv) hydrogen;
- n is an integer equal to 0, 1 or 2, and
- A.sup.0 is a 2-, 3- or 4-pyridyl which can have 1 to 5 substituents as defined below as the substituents to the heterocyclic group defined as the group D;
- wherein the group D can be a heterocyclic group selected from the group consisting of 2- or 3-thienyl, 2- or 3-furyl, 2- or 3-pyrrolyl, 2-, 3- or 4-pyridyl, 2-, 4- or 5-oxazolyl, 2-, 4- or 5-thiazolyl, 3-, 4- or 5-pyrazolyl, 2-, 4- or 5-imidazolyl, 3-, 4- or 5-isoxazolyl, 3-, 4- or 5-isothiazolyl, 3- or 5-(1,2,4-oxadiazolyl), 1,3,4-oxadiazolyl, 3- or 5-(1,2,4-thiadiazolyl), 1,3,4-thiadiazolyl, 4- or 5-(1,2,3-thiadiazolyl), 1,2,5-thiadiazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1H- or 2H-tetrazolyl, N-oxido-2-, 3- or 4-pyridyl, 2-, 4- or 5-pyrimidinyl, N-oxido-2-, 4- or 5-pyrimidinyl, 3- or 4-pyridazinyl, pyrazinyl, N-oxido-3- or 4-pyridazinyl, benzofuryl, benzothiazolyl, benzoxazolyl, triazinyl, oxotriazinyl, tetrazolo 1,5-b!pyridazinyl, triazolo4,5-b!pyridazinyl, oxoimidazinyl, dioxotriazinyl, pyrrolidinyl, piperidinyl, pyranyl, thiopyranyl, 1,4-oxazinyl, morpholinyl, 1,4-thiazinyl, 1,3-thiazinyl, piperazinyl, benzimidazolyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, indolizinyl, quinolizinyl, 1,8-naphthyridinyl, purinyl, pteridinyl, dibenzofuranyl, carbazolyl, acridinyl, phenanthridinyl, phenazinyl, phenothiazinyl and phenoxazinyl groups, each of which can have 1 to 5 substituents selected from the group consisting of
- (i) a C.sub.1-4 alkyl,
- (ii) C.sub.3-6 cycloalkyl,
- (iii) phenyl, naphthyl,
- (iv) C.sub.1-4 alkoxy,
- (v) C.sub.3-6 cycloalkyloxy,
- (vi) phenoxy, naphthyloxy,
- (vii) C.sub.7-12 phenylalkyloxy,
- (viii) C.sub.1-4 alkylthio,
- (ix) C.sub.3-6 cycloalkylthio,
- (x) phenylthio, naphthylthio,
- (xi) C.sub.7-12 phenylalkylthio,
- (xii) mono-C.sub.1-4 alkylamino,
- (xiii) di-C.sub.1-4 alkylamino,
- (xiv) C.sub.3-6 cycloalkylamino,
- (xv) anilino,
- (xvi) C.sub.7-12 phenylalkylamino,
- (xvii) halogen
- (xviii) C.sub.1-4 alkoxycarbonyl,
- (xix) phenoxycarbonyl,
- (xx) C.sub.3-6 cycloalkyloxycarbonyl,
- (xxi) C.sub.7-12 phenylalkyloxycarbonyl,
- (xxii) C.sub.1-5 alkanoyl,
- (xxiii) C.sub.1-15 alkanoyloxy,
- (xxiv) carbamoyl, N-methylcarbamoyl, N,N-dimethylcarbamoyl, N-ethylcarbamoyl, N,N-diethylcarbamoyl, N-phenylcarbamoyl, pyrrolidinocarbamoyl, piperidinocarbamoyl, piperazinocarbamoyl, morpholinocarbamoyl, N-benzylcarbamoyl,
- (xxv) N-methylcarbamoyloxy, N,N-dimethylcarbamoyloxy, N-ethylcarbamoyloxy, N-benzylcarbamoyloxy, N,N-dibenzylcarbamoyloxy, N-phenylcarbamoyloxy,
- (xxvi) C.sub.1-4 alkanoylamino,
- (xxvii) benzamido,
- (xxviii) C.sub.1-4 alkoxycarbonylamino,
- (xxix) C.sub.7-12 phenylalkyloxycarbonyl,
- (xxx) methanesulfonylamino, ethanesulfonylamino, butanesulfonylamino, benzenesulfonylamino, toluenesulfonylamino, naphthalenesulfonylamino, trifluoromethanesulfonylamino, 2-chloroethanesulfonylamino, 2,2,2-trifluoromethanesulfonylamino,
- (xxxi) pyrrolidinyl, pyrrolyl, pyrazolyl, imidazolyl, furyl, thienyl, oxazolyl, isoxazolyl, isothiazolyl, thiazolyl, piperidinyl, pyridyl, piperazinyl, pyrimidinyl, pyranyl, tetrahydropyranyl, tetrahydrofuryl, indolyl, quinolyl, 1,3,4-oxadiazolyl, thieno2,3-dlpyridyl, 1,2,3-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1,3,4-triazolyl, tetrazolyl, 4,5-dihydro-1,3-dioxazolyl, tetrazolo1,5-b!pyridazinyl, benzothiazolyl, benzoxazoiyl, benzimidazolyl, benzothienyl,
- (xxxii) heterocyclethio, heterocycleoxy, heterocycleamino or heterocyclecarbonylamino group which is derived by attachment of any of heterocyclic groups (xxxi) to the S, O, N atom or the carbonylamino group,
- (xxxiii) di-C.sub.1-4 alkylphosphinothioylamino,
- (xxxiv) methoxyimino, ethoxyimino, 2-fluoroethoxyimino, carboxymethoxyimino, 1-carboxy-1-methylethoxyimino, 2,2,2-trichloroethoxycarbonylmethoxyimino, 1-(2,2,2-trichloroethoxycarbonyl)-1-methylethoxyimino, (2-aminothiazol-4-yl)methoxyimino, (1H-imidazol-4-yl)methoxyimino,
- (xxxv) C.sub.1-4 alkylsulfonyloxy,
- (xxxvi) benzenesulfonyloxy, toluenesulfonyloxy,
- (xxxvii) diphenylphosphinothioylamino,
- (xxxviii) thiocarbamoylthio, N-methylthiocarbamoylthio, N,N-dimethylthiocarbamoylthio, N-ethylthiocarbamoylthio, N-benzylthiocarbamoylthio, N,N-dibenzylthiocarbamoylthio, N-phenylthiocarbamoylthio,
- (xxxix) trimethylsilyloxy, t-butyldimethylsilyloxy, t-butyldiphenylsilyloxy, dimethylphenylsilyloxy,
- (xL) trimethylsilyl, t-butyidimethylsilyl, t-butyldiphenylsilyl, dimethylphenylsilyl,
- (xLi) C.sub.1-4 alkylsulfinyl,
- (xLii) phenylsulfinyl, naphthylsulfinyl,
- (xLiii) C.sub.1-4 alkylsulfonyl,
- (xLiv) benzenesulfonyl, toluenesulfonyl,
- (xLv) C.sub.1-4 alkoxy-carbonyloxy,
- (xLvi) halo-C.sub.1-4 alkyl,
- (xlvii) halo-C.sub.1-4 alkoxy, halo-C.sub.1-4 alkylthio, halo-C.sub.1-4 alkylsulfinyl, halo-C.sub.1-4 alkylsulfonyl,
- (xLviii) cyano, nitro, hydroxyl, carboxyl, sulfo, phosphono,
- (xLix) C.sub.1-4 alkyloxysulfonyl,
- (L) phenoxysulfonyl, tolyloxysulfonyl,
- (Li) C.sub.7-12 phenylalkyloxysulfonyl and
- (Lii) di-C.sub.1-4 alkyloxyphosphoryl group, or a salt thereof.
62 more elements
Dependencies are inferred from the claim text.