Shionogi Company Limited

Ichiro Ishizuka

Shinzaburo Sumimoto

Hisajiro Yukinaga

Jitsuo Sugita

Shiro Ueda

Hiroyuki Kai

Akira Takase

Kazuyuki Sasakura

Tsutomu Sugasawa

Akira Murabayashi

Kinya Ide

Yasuo Makisumi

Tatsuo Toyoda

Sumimoto Shinzaburo

Katsuto Okuno

A novel compound useful as an intermediate for synthesizing pesticides and medicine of the formula: ##STR1## in which: R is perfluoroalkyl, R.sup.1 is hydrogen, alkyl or optionally substituted phenyl, or a salt thereof.

3-perfluoroalkyl-5-hydroxyisoxazoles

A fluorinated .beta.-ketonitrile of the formula: ##STR1## in which: R is alkyl having plural fluorines and R.sup.1 is hydrogen or alkyl.

.beta.-ketonitrils

A novel herbicidal compound of the formula: ##STR1## in which R is OH, C.sub.1 -C.sub.3 alkoxy or R.sup.3 -N-R.sup.4 ; R.sub.f is C.sub.1 -C.sub.3 perfluoroalkyl; R.sup.1 is hydrogen, C.sub.1 -C.sub.6 alkyl or optionally substituted phenyl; R.sup.2 is hydrogen or C.sub.1 -C.sub.3 alkyl; n is an integer of 0 to 2; R.sup.3 is hydrogen or C.sub.1 -C.sub.3 alkyl; R.sup.4 is C.sub.1 -C.sub.6 alkyl, optionally substituted phenylalkyl where alkyl contains 1 to 3 carbons or optionally substituted phenyl; or R.sup.3 and R.sup.4 together with the nitrogen atom to which they are attached form a cyclic amino group; or a salt thereof. A process for preparing the compound (I) and a herbicide containing the compound (I) are also disclosed.

3-perfluoroalkyl-5-substituted-oxy-isoxazole derivatives, process for

A novel compound useful as an intermediate for synthesizing pesticides and medicines of the formula: ##STR1## in which: R is alkyl having plural florines; R.sup.1 is hydrogen, alkyl, halogen or optionally substituted phenyl; and R.sup.2 is hydrogen or alkyl, or a salt thereof.

Polyfluoroalkylisoxazolylamines

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-Amino-5-t-butylisoxazole is prepared by reacting pivaloylacetonitrile with hydroxylamine in aqueous medium under basic conditions and treating the reaction products with an acid. The process is economical and industrial.

Process for the production of 3-amino-5-t-butylisoxazole

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

Cyanopinacolone is produced by reacting pinacolone with about 1.0 to about 1.2 molar equivalents of chlorine in methanol and further reacting the resulting monochloropinacolone with about 1.0 to about 1.2 molar equivalents of an alkali metal cyanide in methanol.

Process for the production of cyanopinacolone

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

Osaka, Japan

Ichiro Ishizuka