Kureha Kagaku Kogyo Kabushiki Kaisha

Kureha Kagaku Kogyo K.k.

Hideo Arabori

Shiro Yamazaki

Hiroyasu Shinkawa

Takafumi Shida

Takeo Watanabe

Masato Arahira

Keigo Satake

Katsumichi Aoki

Yoichi Kanda

Aiko Murakami

Yohichi Kanda

Satoru Kumazawa

Tsuneaki Chida

Susumu Shimizu

Tsutomu Sato

Yoshikazu Kubota

Isao Ichinose

Susumu Shimizue

Takeo Watanave

An N-(substituted amino)imide derivative represented by the formula (I) is a novel compound which can be utilized as an effective ingredient of herbicidal compositions. ##STR1## wherein, R.sup.1 is hydrogen atom, C.sub.1 -C.sub.4 alkyl group, C.sub.7 -C.sub.9 aralkyl group, C.sub.1 -C.sub.4 haloalkyl group, (C.sub.1 -C.sub.4 alkyl)carbonyl group or (C.sub.1 -C.sub.4 alkyl)sulfonyl group;

N-(substituted amino)imide derivatives, preparation process thereof, and

This invention is to provide an N-(substituted amino)pyrrole derivative represented by the formula (I): which is used as an effective ingredient of herbicidal compositions: ##STR1## wherein R.sup.2, R.sup.3, R.sup.4 and R.sup.5 is independently hydrogen atom halogen atom, C.sub.1 -C.sub.4 alkyl group, (C.sub.1 -C.sub.4 alkyl)carbonyl group, (C.sub.3 -C.sub.6 cycloalkyl)carbonyl group, (C.sub.1 -C.sub.4 haloalkyl)carbonyl group, (C.sub.3 -C.sub.5 alkenyl)carbonyl group, benzoyl group which may be substituted with 1-3 halogen atoms and/or C.sub.1 -C.sub.4 alkyl groups, N,N-[(di-C.sub.1 -C.sub.4 alkyl)amino]carbonyl group, (C.sub.1 -C.sub.4 alkoxy)carbonyl group, etc., X.sup.1 and X.sup.2 are independently hydrogen atom, halogen atom, C.sub.1 -C.sub.4 alkyl group, C.sub.1 -C.sub.4 alkoxy group, etc., and Z is nitrogen atom or CH.

N-(substituted amino) pyrrole derivatives preparation process thereof,

This invention is to provide an N-(substituted amino)pyrrole derivative represented by the formula (I): which is used as an effective ingredient of herbicidal compositions: ##STR1## wherein R.sup.2, R.sup.3, R.sup.4 and R.sup.5 is independently hydrogen atom, halogen atom, C.sub.1 -C.sub.4 alkyl group, (C.sub.1 -C.sub.4 alkyl)carbonyl group, (C.sub.3 -C.sub.6 cycloalkyl) carbonyl group, (C.sub.1 -C.sub.4 haloalkyl)carbonyl group, (C.sub.3 -C.sub.5 alkenyl)carbonyl group, benzoyl group which may be substituted with 1-3 halogen atoms and/or C.sub.1 -C.sub.4 alkyl groups, N,N-[(di-C.sub.1 -C.sub.4 alkyl)amino]carbonyl group, (C.sub.1 -C.sub.4 alkoxy)carbonyl group, etc., X.sup.1 and X.sup.2 are independently hydrogen atom, halogen atom, C.sub.1 -C.sub.4 alkyl group, C.sub.1 -C.sub.4 alkoxy group, etc., and Z is nitrogen atom or CH.

N-(substituted amino)pyrrole derivatives, and herbicidal compositions

Phenyl (1,3,5-triazin-2-yl)carbamates of the formula (I): ##STR1## wherein R.sup.1 is H, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, R.sup.2 and R.sup.3 are independently H, halogen atom, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.2 -C.sub.4 alkoxyalkyl or NR.sup.7 R.sup.8 (R.sup.7, R.sup.8 : H or C.sub.1 -C.sub.4 alkyl, independently), and R.sup.4, R.sup.5 and R.sup.6 are independently H, halogen atom, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, are prepared by reacting a 2-amino-1,3,5-triazine of the formula (II): ##STR2## with a diphenyl carbonate of the formula (III): ##STR3## in the presence of an alkali metal hydride in an acrotic polar solvent. An parotic polar solvent mixture of the phenyl (1,3,5-triazin-2-yl)carbamate of the formula (I) and an alkali metal phenoxide is also disclosed.

Process for the preparation of phenyl (1,3,5-triazin-2-yl)carbamates

Disclosed herein are N-substituted-3-(nitrogen-containing 5-membered ring)benzenesulfonamide derivatives of the formula (I): ##STR1## R.sup.1 is H, Cl, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.4 alkoxycarbonyl; Z is CH or N; X.sup.1 is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxyl or Cl; and X.sup.2 is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxyl, a process for the preparation thereof, and herbicidal compositions containing the N-substituted-3-(nitrogen-containing 5-membered ring)benzenesulfonamide derivatives as active ingredients.

N-substituted-3-(nitrogen-containing 5-membered ring)-benzenesulfonamide

Disclosed herein are N-substituted-3-(substituted hydrazino)benzenesulfonamide derivatives of the formula (I): ##STR1## wherein R.sup.1 and CF.sub.3, COOH or CCl=CClCOOH, R.sup.2 is H, Cl, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.4 alkoxycarbonyl; Z is CH or N; X.sup.1 is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxyl or Cl; and X.sup.2 is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxyl, a process for the preparation thereof, and herbicidal compositions containing the N-substituted-3-(substituted hydrazino)benzenesulfonamide derivatives as active ingredients.

N-substituted-3-(substituted hydrazino)-benzenesulfonamides

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 are N-substituted-3-[(2,3-dimethylmaleimido)amino]benzenesulfonamide derivatives of the formula (I): ##STR1## wherein R is Cl, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.4 alkoxycarbonyl; Z is CH or N; X.sup.1 is Cl or C.sub.1 -C.sub.3 alkoxyl; and X.sup.2 is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxyl, a process for the preparation thereof, and herbicidal compositions containing the N-substituted-3-[(2,3-dimethylmaleimido)amino]benzenesulfonamide derivatives as active ingredients.

N-substituted-3-( (2,3-dimethylmaleimido)amino)-benzenesulfonamide

Disclosed herein are N-substituted-3-(nitrogen-containing 5-membered ring)benzenesulfonamide derivatives of the formula (I): ##STR1## R.sup.1 is H, Cl, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.4 alkoxycarbonyl; Z is CH or N; X.sup.1 is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxyl or Cl; and X.sup.2 is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxyl, a process for the preparation thereof, and herbicidal compositions containing the N-substituted-3-(nitrogen-containing 5-membered ring)-benzenesulfonamide derivatives as active ingredients.

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 N-substituted-3-(substituted hydrazino)benzenesulfonamide derivatives of the formula (I): ##STR1## wherein R.sup.1 is CF.sub.3, COOH or CCl.dbd.CClCCOOH, R.sup.2 is H, Cl, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.4 alkoxycarbonyl; Z is CH or N; X.sup.1 is C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxyl or Cl; and X.sup.2 is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxyl, a process for the preparation thereof, and herbicidal compositions containing the N-substituted-3-(substituted hydrazino)benzenesulfonamide derivatives as active ingredients.

N-substituted-3-(substituted hydrazino)-benzenesulfonamide derivatives,

Disclosed herein are N-substituted-3-[(2,3-dimethylmaleimido) amino]benzenesulfonamide derivatives of the formula (I): ##STR1## wherein R is Cl, C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.4 alkoxycarbonyl; Z is CH or N; X.sup.1 is Cl or C.sub.1 -C.sub.3 alkoxy; and X.sup.2 is C.sub.1 -C.sub.3 alkyl or C.sub.1 -C.sub.3 alkoxyl, a process for the preparation thereof, and herbicidal compositions containing the N-substituted-3-[(2,3-dimethylmaleimido) amino]benzenesulfonamide derivatives as active ingredients.

N-substituted-3-[(2,3-dimethylmaleimido)amino)]-benzenesulfonamide

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.

Growing community of inventors

Iwaki, Japan

Hideo Arabori