Shionogi Company Limited

Jitsuo Sugita

Hisajiro Yukinaga

Ichiro Ishizuka

Shinzaburo Sumimoto

Kenji Ikawa

Kanji Ito

N.sup.4 -Phenoxyalkanoylsulfanilamides of the formula: ##STR1## (wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 each independently represents hydrogen, halogen, nitro or lower alkyl, R.sup.5 represents hydrogen or lower alkyl, and R.sup.6 represents hydrogen, lower alkoxycarbonyl, lower alkanoyl or carbamoyl) and alkali metal or alkaline earth metal salt thereof, and a herbicidal composition containing at least one of said N.sup.4 -phenoxyalkanoylsulfanilamides are disclosed.

N.sup.4 -Phenoxyalkanoylsulfanilamides and herbicidal composition

Herbicidal compounds represented by the formula: ##STR1## wherein R is t-butyl; R.sup.1 is hydrogen or methyl; R.sup.2 is alkyl (C.sub.2 to C.sub.6), alkenyl (C.sub.3 to C.sub.4) or cyclopropyl; and X is hydrogen or halogen; and herbicidal compositions containing them.

N-(5-t-Butyl-3-isoxazolyl)alkanamide derivatives and herbicidal

3-Isoxazolylurea derivatives of the formula: ##STR1## (wherein R represents hydrogen, C.sub.1 -C.sub.6 alkyl, or C.sub.6 -C.sub.8 aryl; R.sup.1 represents hydrogen or C.sub.1 -C.sub.6 alkyl; R.sup.2 represents C.sub.1 -C.sub.6 alkyl, C.sub.6 -C.sub.8 aralkyl, or C.sub.6 -C.sub.8 aryl; or ##STR2## represents pyrrolidino, piperidino, morpholino, or 4-alkylpiperazino; X represents hydrogen or halogen; or R and X may optionally form C.sub.3 -C.sub.5 alkylene), are prepared by reacting a carboxamide of the formula: ##STR3## (wherein R and X each is as defined above) with an amine of the formula:

Process for preparing 3-isoxazolylurea derivatives

Isoxazole derivatives represented by the formula: ##STR1## wherein R represents hydrogen, alkyl group, or aryl group, R.sup.1 represents hydrogen, or alkyl group, R.sup.2 represents acyl group, a ##STR2## group [R.sup.3 and R.sup.4 each represent hydrogen, alkyl group, alkenyl group, alkynyl group, aralkyl group, aryl group, alkoxy group, or alkylthio group; or optionally R.sup.3 and R.sup.4 are combined with each other directly or indirectly including another hetero atom (nitrogen, oxygen, or sulfur) to form a nitrogen-containing ring], or a

3-Isoxazolylcarbamate derivatives

Isoxazole derivatives represented by the formula: ##STR1## wherein R represents hydrogen, alkyl group, or aryl group, R.sup.1 represents hydrogen, or alkyl group, R.sup.2 represents acyl group, a ##STR2## group [R.sup.3 and R.sup.4 each represent hydrogen, alkyl group, alkenyl group, alkynyl group, aralkyl group, aryl group, alkoxy group, or alkylthio group; or optionally R.sup.3 and R.sup.4 are combined with each other directly or indirectly including another hetero atom (nitrogen, oxygen, or sulfur) to form a nitrogen-containing ring], or a --CO--Y--R.sup.5 group [R.sup.5 represents alkyl group, alkenyl group, alkynyl group, aralkyl group, or aryl group, and Y represents oxygen, or sulfur], and X represents hydrogen, alkyl group, or halogen, or R and X are optionally combined each other to form an alkylene group, said alkyl group, aralkyl group, and aryl group each being optionally substituted with one or more members selected from halogen, alkyl group, alkoxy group, nitro group, and hydroxy group, are prepared by 11 routes. The isoxazole derivatives are useful as herbicides.

Herbicidal compositions containing 3-isoxazolylurea derivatives

Isoxazole derivatives represented by the formula: ##STR1## wherein R represents hydrogen, alkyl group, or aryl group, R.sup.1 represents hydrogen, or alkyl group, R.sup.2 represents acyl group, a ##STR2## group [R.sup.3 and R.sup.4 each represent hydrogen, alkyl group, alkenyl group, alkynyl group, aralkyl group, aryl group, alkoxy group, or alkylthio group; or optionally R.sup.3 and R.sup.4 are combined with each other directly or indirectly including another hetero atom (nitrogen, oxygen, or sulfur) to form a nitrogen-containing ring], or a --CO--Y--R.sup.5 group [R.sup.5 represents alkyl group, alkenyl group, alkynyl group, aralkyl group, or aryl group, and Y represents oxygen, or sulfur], and X represents hydrogen, alkyl group, or halogen, or R and X are optionally combined each other to form an alkylene group, said alkyl group, aralkyl group, and aryl group each being optionally substituted with one or more members selected from halogen, alkyl group, alkoxy group, nitro group, and hydroxy group, are prepared by eleven routes. The isoxazole derivatives are useful as herbicides.

3-Isoxazolylurea derivatives

3-ALKYLISOXAZOLE DERIVATIVES REPRESENTED BY THE FORMULA: ##STR1## wherein R represents C.sub.3 -C.sub.6 alkyl or C.sub.3 -C.sub.6 cycloalkyl, R.sup.1 represents hydrogen or C.sub.1 -C.sub.6 alkyl, R.sup.2 represents ##STR2## [in which R.sup.3 and R.sup.4 each represent hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.7 alkenyl, C.sub.1 -C.sub.6 alkoxy, C.sub.2 -C.sub.7 alkoxycarbonyl or C.sub.1 -C.sub.6 alkylthio, or ##STR3## represents morpholino, pyrrolidino or piperidino, and Y represents oxygen or sulfur] or --CO--Y--R.sup.5 [in which R.sup.5 represents C.sub.1 -C.sub.6 alkyl and Y is as defined above] and X represents hydrogen, halogen or C.sub.1 -C.sub.6 alkyl, or R and X are combined to form C.sub.3 -C.sub.6 alkylene, being useful as herbicides, are prepared by several routes.

Growing community of inventors

Ikeda, Japan

Jitsuo Sugita