Patent ID: 6124297
Filing Date: 2000-09-26
Classification: A01N,C07C,C07D,C07F

Abstract:
A method of combatting insects or mites, comprising administering an effective dose of 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; orwherein one of X.sup.1 and X.sup.2 is a halogen atom; orwherein X.sup.1 and X.sup.2 can join together with the adjacent carbon atom to form a ring of the formula ##STR124## 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 heterocyclic group defined below as the group D, 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 heterocycleoxycarbonyl group wherein the heterocycle moiety is defined below as the group D, 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 a heterocyclic group defined below as the group D, 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, a heterocycleoxy group, wherein the heterocycle moiety is defined below as the group D, 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, andA.sup.0 is a substituted or unsubstituted heterocyclic group defined below as group D, provided that A.sup.0 is not a moiety selected from the group consisting of 2-, 3-, or 4-pyridyl and 2-, 4- or 5-thiazolyl;wherein the group D is a moiety 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, triazolo[4,5-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 group, any 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, thieno[2,3-d]pyridyl, 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, tetrazolo[1,5-b]pyridazinyl, benzothiazolyl, benzoxazolyl, 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-trichioroethoxycarbonylmethoxyimino, 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-butyldinethylsilyl, 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.