Guanidine derivatives their production and insecticides

An insecticidal composition comprising a guanidine derivative of the formula (I):

• ##STR65## wherein R.sup.1 is an optionally substituted homocyclic or heterocyclic ring selected from the group consisting of C.sub.3-8 cycloalkyl, C.sub.3-8 cycloalkenyl, C.sub.6-14 aryl, 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, benzoimidazolyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, indolizinyl, quinolizinyl, 1,8-naphthyridinyl, purinyl, pteridinyl, dibenzofuranyl, carbazolyl, acridinyl, phenanthridinyl, phenazinyl, phenothiazinyl and phenoxazinyl, the homocyclic and the heterocyclic rings optionally being substituted with up to 5 substituents selected from the group consisting of C.sub.1-15 alkyl, C.sub.3-10 cycloalkyl, C.sub.2-10 alkenyl, C.sub.2-10 alkynyl, C.sub.3-10 cycloalkenyl, C.sub.6-10 aryl, C.sub.7-10 aralkyl, nitro, hydroxy, mercapto, oxo, thioxo, cyano, carbamoyl, carboxyl, C.sub.1-4 alkoxycarbonyl, sulfo, halogen, C.sub.1-4 alkoxy, C.sub.6-10 aryloxy, C.sub.1-4 alkylthio, C.sub.6-10 arylthio, C.sub.1-4 alkylsulfinyl, C.sub.6-10 arylsulfinyl, C.sub.1-4 alkylsulfonyl, C.sub.6-10 arylsulfonyl, amino, C.sub.2-6 acylamino, mono- or di-C.sub.1-4 alkylamino, C.sub.3-6 cycloalkylamino, C.sub.6-10 arylamino, C.sub.2-4 acyl, C.sub.6-10 arylcarbonyl, and a 5- or 6-membered heterocyclic group having 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen, wherein when the substituent is the C.sub.6-10 aryl, C.sub.7-10 aralkyl, C.sub.3-10 cycloalkyl, C.sub.3-10 cycloalkenyl, C.sub.6-10 aryloxy, C.sub.6-10 arylthio, C.sub.6-10 arylsulfinyl, C.sub.6-10 arylsulfonyl, C.sub.6-10 arylamino or heterocyclic group, the substituent may be further substituted by 1 to 5 of halogen, hydroxy, C.sub.1-4 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.6-10 aryl, C.sub.1-4 alkoxy, phenoxy, C.sub.1-4 alkylthio, or phenylthio, and when the substituent is C.sub.1-15 alkyl, C.sub.2-10 alkenyl, C.sub.2-10 alkynyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, C.sub.1-4 alkylsulfinyl, C.sub.1-4 alkylsulfonyl, amino, mono- or di-C.sub.1-4 alkylamino, C.sub.3-6 cycloalkylamino or C.sub.6-10 arylamino, the substituent may be further substituted by 1 to 5 of halogen, hydroxy, C.sub.1-4 alkoxy or C.sub.1-4 alkylthio,
• R.sup.2 is hydrogen or an optionally substituted hydrocarbon selected from the group consisting of C.sub.1-15 alkyl, C.sub.3-10 cycloalkyl, C.sub.2-10 alkenyl, C.sub.2-10 alkynyl, C.sub.3-10 cycloalkenyl, C.sub.6-10 aryl or C.sub.7-10 aralkyl, each of which may be unsubstituted or substituted by one to five of the groups mentioned as substituents of R.sup.1,
• R.sup.3 is an amino group represented by the formula:
• ##STR66## wherein R.sup.4 and R.sup.5 are, the same or different, a hydrogen atom or an optionally substituted hydrocarbon group or both R.sup.4 and R.sup.5 are combined with the adjacent nitrogen atom to form a cyclic amino group, the hydrocarbon group being selected from the group consisting of C.sub.1-15 alkyl, C.sub.3-10 cycloalkyl, C.sub.2-10 alkenyl, C.sub.2-10 alkynyl, C.sub.3-10 cycloalkenyl, C.sub.6-10 aryl and C.sub.7-10 aralkyl, the substituent of the hydrocarbon group being selected from the group consisting of those mentioned in said substituents of R.sup.1, and the cyclic amino group being selected from the group consisting of aziridino, azetidino, pyrrolidino, morpholino and thiomorpholino,
• n is 0 or 1, and
• X is nitro, cyano or trifluoroacetyl,
• provided that when n is 0, R.sup.1 is an optionally substituted heterocyclic group, or
• provided that when X is nitro, R.sup.1 is an optionally substituted homocyclic or heterocyclic group as defined above, n is 0 or 1, R.sup.2 is a substituted C.sub.1-4 alkyl or optionally substituted C.sub.5-15 alkyl, C.sub.3-10 cycloalkyl, C.sub.2-10 alkenyl, C.sub.2-10 alkynyl, C.sub.3-10 cycloalkenyl, C.sub.6-10 aryl or C.sub.7-10 aralkyl group, the substituents of group R.sup.2 being selected from the group consisting of those mentioned as substituents of R.sup.2 above, and R.sup.3 is as defined above, or
• provided that when X is nitro, R.sup.1 is an optionally substituted homocyclic or heterocyclic group as defined above, n is 0 or 1, R.sup.2 is a hydrogen atom or C.sub.1-4 alkyl, R.sup.3 is a group represented by the formula:
• ##STR67## wherein one of R.sup.4 and R.sup.5 is a hydrogen atom or an optionally substituted hydrocarbon group selected from the group consisting of C.sub.1-15 alkyl, C.sub.3-10 cycloalkyl, C.sub.2-10 alkenyl, C.sub.2-10 alkynyl, C.sub.3-10 cycloalkenyl, C.sub.6-10 aryl and C.sub.7-10 aralkyl, the substituent of the hydrocarbon group being selected from the group consisting of those mentioned as substituents of R.sup.1, and the other is a substituted C.sub.1-4 alkyl or an optionally substituted hydrocarbon group selected from the group consisting of C.sub.5-15 alkyl, C.sub.3-10 cycloalkyl, C.sub.2-10 alkenyl, C.sub.2-10 alkynyl, C.sub.3-10 cycloalkenyl, C.sub.6-10 aryl and C.sub.7-10 aralkyl, the substituent of the C.sub.1-4 alkyl and of the hydrocarbon group being selected from the group consisting of those mentioned as substituents of R.sup.1, or both R.sup.4 and R.sup.5 are combined with the adjacent nitrogen atom to form a cyclic amino group selected from the group consisting of aziridino, azetidino, pyrrolidino, morpholino and thiomorpholino, or
• provided that when X is cyano, R.sup.1 is 2-chloro-5-thiazolyl, n is 1, R.sup.2 is hydrogen, and R.sup.3 is methylamino,
• or a salt thereof, and a carrier or diluent.