Kureha Kagaku Kogyo Kabushiki Kaisha

Takafumi Shida

Shiro Yamazaki

Hiroyasu Shinkawa

Takeo Watanabe

Hideo Arabori

Keigo Satake

Katsumichi Aoki

Satoru Kumazawa

Yoichi Kanda

Yohichi Kanda

Tsuneaki Chida

Yoshikazu Kubota

Isao Ichinose

Susumu Shimizu

Youichi Kanda

Masashi Ohtsuru

Susumu Shimizue

Takeo Watanave

Disclosed herein are the derivative of benzyl ether represented by the formula (I) ##STR1## which is useful as an intermediate compound of the derivatives of 1,5-diphenyl-1H-1,2,4- triazole-3-carboxamide represented by the formula (II), ##STR2## wherein R is a straight-chain alkyl group having 1 to 10 carbon atoms which is non-substituted or substituted with 1 to 19 fluorine atoms, a branched alkyl group having 3 to 10 carbon atoms which is non-substituted or substituted with 1 to 19 fluorine atoms, a cyclic alkyl group having 3 to 10 carbon atoms, an alkyl group having 1 to 3 carbon atoms which is substituted with an alicyclic structure having 3 to 7 carbon atoms, a phenyl group or an aralkyl group having 7 to 9 carbon atoms; X.sup.1 is a halogen or an alkyl group having 1 to 3 carbon atoms; X.sup.2 is a hydrogen, a halogen or an alkyl group having 1 to 3 carbon atoms; Y.sup.1 is a hydrogen or a fluorine; Y.sup.2 is a hydrogen or a fluorine; and Z is a nitro group or an amino group.

Benzylether derivatives

Disclosed herein is a derivative of 1,5-diphenyl-1H-1,2,4-triazole-3-carboxamide represented by the following formula (I): ##STR1## wherein R represents an alkyl group of 2 to 10 carbon atoms, which is substituted by fluorine atom(s), and X represents a hydrogen atom or a fluorine atom, a process for producing the derivative and a herbicidal compositions containing the derivative of 1,5-diphenyl-1H-1,2,4-triazole-3-carboxamide as an active ingredient.

Derivative of 1,5-diphenyl-1H-1,2,4-triazole-3-carboxamide, herbicidal

Disclosed herein is a derivative of 1,5-diphenyl-1H-1,2,4-triazole-3-carboxamide represented by the following formula (I): ##STR1## wherein R represents an alkyl group of 2 to 10 carbon atoms, which is substituted by fluorine atom(s), and X represents a hydrogen atom or a fluorine atom, a process for producing the derivative and herbicidal compositions containing the derivative of 1,5-diphenyl-1H-1,2,4-triazole-3-carboxamide as an active ingredient.

Derivative of 1,5-diphenyl-1H-1,2-triazole-3-carboxamide, herbicidal

Disclosed herein are a benzyl ether compound represented by the general formula (I): ##STR1## wherein R represents a branched alkyl group of 4 to 8 carbon atoms, a cycloalkyl group of 4 to 8 carbon atoms, an alkyl group of 1 to 3 carbon atoms having an alicyclic group of 3 to 7 carbon atoms, an aralkyl group of 7 to 9 carbon atoms, an alkyl group of 2 to 4 carbon atoms having an alkoxy group of 1 to 4 carbon atoms, an unsaturated alkyl group of 3 to 6 carbon atoms, a straight-chain alkyl group of 2 to 8 carbon atoms which has been substituted by 1 to 15 fluorine atoms, or a branched alkyl group of 3 to 8 carbon atoms which has been substituted by 1 to 15 fluorine atoms, and X represents a nitro group or an amino group, provided that when X is a nitro group, R is neither an aralkyl group nor an ethyl group substituted by fluorine atom(s), a process for producing the same.

Benzyl ether compound and process for producing the same

Disclosed herein is a 4,5-dihydro-1H-1,2,4-triazole-3-carboxamide derivative represented by the formula (I): ##STR1## wherein R represents a straight-chain alkyl group having 1 to 10 carbon atoms which is non-substituted or substituted with 1 to 19 fluorine atoms or a branched alkyl group having 3 to 10 carbon atoms which is non-substituted or substituted with 1 to 19 fluorine atoms; X.sup.1 represents a halogen atom or an alkyl group having 1 to 3 carbon atoms; X.sup.2 represents hydrogen atom, a halogen atom or an alkyl group having 1 to 3 carbon atoms; Y.sup.1 represents hydrogen atom or fluorine atom; and Y.sup.2 represents hydrogen atom or fluorine atom. The derivatives of the formula (I) have high herbicidal activities and also show a excellent selectivity in their actions for killing weeds alone while doing any practical harm to the crops such as rice, wheat and corn.

4,5-dihydro-1H-1,2,4-triazole-3-carboxamide derivatives and herbicidal

Disclosed herein is a derivative of 1,5-diphenyl-1H-1,2,4-triazole-3-carboxamide represented by the formula (I): ##STR1## wherein R is a straight-chain alkyl group having 1 to 10 carbon atoms which is non-substituted or substituted with 1 to 19 fluorine atoms, a branched alkyl group having 3 to 10 carbon atoms which is non-substituted or substituted with 1 to 19 fluorine atoms, a cyclic alkyl group having 3 to 10 carbon atoms, an alkyl group having 1 to 3 carbon atoms which is substituted with an alicyclic structure having 3 to 7 carbon atoms, a phenyl group or an aralkyl group having 7 to 9 carbon atoms; X.sup.1 is a halogen or an alkyl group having 1 to 3 carbon atoms; X.sup.2 is a hydrogen, a halogen or an alkyl group having 1 to 3 carbon atoms; Y.sup.1 is a hydrogen or a fluorine; and Y.sup.2 is a hydrogen or a fluorine, and the herbicidal compositions containing said derivatives as active ingredient therefor. The derivative of 1,5-diphenyl-1H-1,2,4-triazole-3-carboxamide represented by the formula (I) of the present invention is the compound having high herbicidal activity and also showing excellent selectivity for killing weeds alone without doing any serious harm to the crops such as rice, wheat and corn.

1,5-diphenyl-1H-1,2,4-triazole-3-carboxamide derivatives and herbicidal

Disclosed herein is a phenylhydrazone derivative of oxamide represented by the formula (I): ##STR1## wherein R.sup.1 is straight-chain alkyl group having 2 to 10 carbon atoms, branched alkyl group or cyclic alkyl group having 3 to 10 carbon atoms, alkyl group having 1 to 3 carbon atoms which is substituted with an alicyclic structure having 3 to 7 carbon atoms, phenyl group, halogen-substituted phenyl group, aralkyl group having 7 to 9 carbon atoms, alkenyl group having 3 to 6 carbon atoms, alkyl group having 2 to 4 carbon atoms which is substituted with alkoxy group having 1 to 4 carbon atoms, or alkyl group having 2 to 10 carbon atoms which is substituted with 1 to 19 fluorine atoms; and R.sup.2 is hydrogen, fluorine, chlorine, methyl group or methoxy group, and a herbicidal composition containing the derivative as active ingredient. The phenylhydrazone derivative of oxamide represented by the formula (I) of the present invention shows a high herbicidal activity and also have an excellent selectivity allowing killing of weeds alone without doing any practical harm to the crops such as rice, wheat and corn.

Phenylhydrazone derivative of oxamide and herbicidal composition

Disclosed herein are a derivative of 1,5-diphenyl-1H-1,2,4-triazole-3-carboxamide represented by the formula (I): ##STR1## wherein R.sup.1 represents a straight-chain alkyl group of 2 to 10 carbon atoms; a branched-chain alkyl group or cycloalkyl group of 3 to 10 carbon atoms; a (cycloalkyl)alkyl group of 4 to 10 carbon atoms; a non-substituted- or halogen-substituted phenyl group; an aralkyl group of 7 to 9 carbon atoms; an alkenyl group of 3 to 6 carbon atoms or an alkyl group of 2 to 10 carbon atoms, which has been substituted by 1 to 19 fluorine atoms, and R.sup.2 represents a fluorine atom, a chlorine atom, a methyl group or a methoxy group and a herbicidal composition containing the derivative represented by the formula (I) as an active ingredient.

Derivative of 1,5-diphenyl-1H-1,2,4-triazole-3-carboxamide and

Disclosed herein are a derivative of dihydrotriazole represented by the general formula (I): ##STR1## wherein R.sup.1 represents an amino group, lower alkoxy group, or lower alkyl amino group, R.sup.2 represents a hydrogen atom, halogen atom, or lower alkyl group and R.sup.3 represents a hydrogen atom, lower alkyl group, benzyl group, furyl group, phenyl group or phenyl group substituted with a halogen atom, hydroxyl group, carboxyl group, methoxycarbonyl group, lower alkyl group or lower alkoxy group, and a herbicidal composition containing as an active ingredient at least one of the derivatives of dihydrotriazole.

Derivatives of dihydrotriazole, and herbicidal compositions containing

Disclosed herein are a derivative of 4,5-dihydro-1H-1,2,4-triazole-3-carboxamide represented by the formula (Io): ##STR1## wherein R.sup.1 represents a hydrogen atom, a halogen atom, an alkyl group of 1 to 3 carbon atoms or an alkoxy group of 1 to 3 carbon atoms, R.sup.2 represents a hydrogen atom or a halogen atom and R represents a straight-chain alkyl group of 1 to 8 carbon atoms, a branched-chain alkyl group of 3 to 8 carbon atoms, a cycloalkyl group of 3 to 8 carbon atoms, a (cycloalkyl)alkyl group of 4 to 8 carbon atoms, an alkenyl group of 3 to 8 carbon atoms, an alkynyl group of 3 to 8 carbon atoms, an alkoxyalkyl group of 3 to 8 carbon atoms, a phenyl group, an aralkyl group of 7 to 9 carbon atoms, a phenyl group substituted by halogen atom(s) or an alkyl group of 2 to 8 carbon atoms which is substituted by fluorine atom(s), an intermediate for producing the derivative and a herbicidal composition containing the derivative as an active ingredient.

Derivative of 4,5-dihydro-1H-1,2,4-triazole-3-carboxamide, and

A 1,2,4-triazole-3-carboxamide compound represented by the formula (I): ##STR1## wherein R represents a straight-chain or branched-chain saturated (C.sub.2 -C.sub.10)alkyl group which is unsubstituted or substituted by fluorine atom(s); a cyclic saturated (C.sub.3 -C.sub.10)alkyl group which is unsubstituted or substituted by fluorine atom(s); a straight-chain, branched-chain or cyclic unsaturated (C.sub.3 -C.sub.10)-alkyl group which is unsubstituted or substituted by fluorine atom(s); a group represented by the formula (II): ##STR2## wherein R.sup.1 represents a halogen atom, a (C.sub.1 -C.sub.3)alkyl group, a (C.sub.1 -C.sub.3)alkoxy group or a fluorine-substituted (C.sub.1 -C.sub.3)alkyl group, m is an integer of from 0 to 5 and n is 0 or 1; a straight-chain or branched-chain saturated (C.sub.1 -C.sub.8)alkoxy(C.sub.2 14 C.sub.10)alkyl group; a straight-chain or branched-chain unsaturated (C.sub.1 -C.sub.8)alkoxy(C.sub.2 -C.sub.10)alkyl group; a phenoxy(C.sub.2 -C.sub.6)alkyl group; an aralkoxy(C.sub.2 1-C.sub.6)alkyl group; a phenoxy(C.sub.2 -C.sub.6)alkyl group having phenyl group(s) substituted by halogen atom(s) or (C.sub.1 -C.sub.3)alkyl group(s); an aralkoxy(C.sub.2 -C.sub.6)alkyl group having phenyl group(s) substituted by halogen atom(s) or (C.sub.1 -C.sub.3)alkyl group(s); a [(C.sub.1 -C.sub.8)alkoxy(C.sub.2 -C.sub.10)alkoxy](C.sub.2 -C.sub.10)alkyl group; or a group represented by the formula (III): ##STR3## wherein p is an integer of from 1 to 8, a process for producing the same compound, and a herbicidal composition containing the 1,2,4-triazole-3-carboxamide compound as an active ingredient.

1,2,4-triazole-3-carboxamide compound and a herbicidal composition

Disclosed herein is herbicidal composition comprising a derivative of 1,2,4-triazole as an active ingredient, represented by the general formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom, a halogen atom or a C.sub.1 -C.sub.2) alkyl group; R.sup.2 represents a hydrogen atom, a halogen atom, a (C.sub.1 -C.sub.2) alkyl group fluoromethyl group (--CH.sub.2 F),3,3,3-trifluoropopyl group, methoxy group, cyano group, methoxymethyl group, methylthio group, methoxycarbonyl group or isopropoxycarbonyl group and R.sup.3 represents a thiocarbamoyl group or a group represented by the general formula (II): ##STR2## wherein R.sup.4 represents a hydrogen atom, a (C.sub.1 -C.sub.2) alkyl group or a hydroxy (C.sub.1 -C.sub.2) alkyl group and R.sup.5 represents a hydrogen atom, a C.sub.1 -C.sub.2) alkyl group, halogeno (C.sub.1 -C.sub.2) alkyl group, hydroxy (C.sub.1 -C.sub.2) alkyl group, cyanomethyl group, acetyl group, halogenoacetyl group, methoxyacetyl group, amino group, phenyl group, methoxy group, hydroxyl group, (C.sub.2 -C.sub.3) alkenyl group, halogeno (C.sub.2 -C.sub.3) alkenyl group, isopropylcarbonyl group, methylthiocarbamoyl group or 2-methoxyethyl group, the proviso that R.sup.2 is not a hydrogen atom, halogen atom or (C.sub.1 -C.sub.2) alkyl group when both of R.sup.4 and R.sup.5 represent hydrogen atoms, and herbicidally acceptable carrier(s) or diluent(s).

Herbicidal composition containing a derivative of 1,2,4-triazole as an

Disclosed herein are a derivative of tetrahydrobenzothiazole represented by the formula (I): ##STR1## wherein R represents a methyl group or ethyl group; R.sup.1 represents a hydrogen atom, a hydroxyl group, methoxy group or O.dbd.=together with R.sup.2 ; R.sup.2 represents a hydrogen atom or O.dbd.=together with R.sup.1 ; and X represents a methylene group, hydroxymethylene group, carbonyl group or --O-- with the proviso that R is not a methyl group when (1) R.sup.1 represents a hydroxyl group or methoxy group and X represents a methylene group or hydroxymethylene group or (2) R.sup.2 represents .dbd.O together with R.sup.1 and X represents a carbonyl group, and a herbicidal composition containing the same as an active ingredient.

Derivatives of tetrahydrobenzothiazole and herbicidal compositions

Disclosed herein are the derivatives of tetrahydrobenzothiazole represented by the general formula (I): ##STR1## wherein R.sup.1 represents a hydrogen atom, a straight-chain alkyl group having 1 to 6 carbon atoms or branched-chain alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms or a phenyl group and R.sup.2 represents a chemical group selected from the group consisting of: ##STR2## wherein R.sup.3 represents a hydrogen atom, a methyl group or an acetyl group and R.sup.4 represents a hydrogen atom, a hydroxyl group, methoxy group or acetoxy group and herbicidal compositions containing at least one of the derivatives of tetrahydrobenzothiazole as an active ingredient.

Derivative of tetrahydrobenzothiazole and herbicidal composition

Disclosed herein are a derivative of tetrahydrobenzothiazole represented by the formula (I): ##STR1## wherein R represents a methyl group, ethyl group or propyl group; R.sup.1 represents a hydrogen atom, a hydroxyl group methoxy group, acetoxy group, propionyloxy group, butylyloxy group, chloroacetoxy group, methoxyacetoxy group, C.sub.1 to C.sub.4 -alkylamino group or di(C.sub.1 to C.sub.4)-alkylamino group, or represents O.dbd.together with R.sup.2 ; R.sup.2 represents a hydrogen atom or represents O.dbd.together with R.sup.1 ; and X represents a methylene group, hydroxymethylene group, carbonyl group or --O--, and a herbicidal composition containing the same as an active ingredient.

Growing community of inventors

Iwaki, Japan

Takafumi Shida