Agro-kanesho Co., Ltd.

Tosoh Corporation

Toyo Soda Manufacturing Co., Ltd.

Toyo Soda Mfg. Co., Ltd.

Kanesho Co., Ltd.

Agro-kenesho Co., Ltd.

Mikio Ito

Seigo Koura

Yuji Nonaka

Akira Nakanishi

Shinzo Someya

Kenji Tsuzuki

Hiroyuki Watanabe

Sinzo Someya

Rokuro Akahira

Yoichi Kitamura

Takumi Kagawa

Yasuaki Hanasaki

Takumi Tokunaga

Takashi Morooka

Syunji Aman

Kazuaki Tsukuda

Processes for producing optically active ester derivatives are disclosed. According to the present invention an optically active aryloxyphenoxy propionate derivative is produced by reacting a chlorinated heterocyclic aromatic compound with (2R)-2-(4-hydroxyphenoxy)propionic acid tetrahydrofurfuryl ester in an anhydrous solvent in the presence of a base. According to the present invention, an optically active propionate derivative of the formula [I] ##STR1## (wherein R represents hydrogen or 3-chloro-5-trifluoromethyl-2-pyridyl group) is produced by reacting a corresponding optically active methyl propionate derivative with tetrahydrofurfuryl alcohol, or by reacting a corresponding optically active propionic acid derivative with tetrahydrofurfuryl alcohol, or by reacting (2S)-tetrahydrofurfuryl 2-chloropropionate with a corresponding phenol derivative in specific conditions.

Process of producing optically active propionic acid ester derivatives

Disclosed is a novel compound of the formula [I]: ##STR1## (wherein R.sup.1 is H or CH.sub.3, R.sup.2 is H or C.sub.1 -C.sub.4 alkyl), furylmethyl group, tetrahydrofuryl group 2-tetrahydropyranylmethyl group or tetrahydrofurfuryl group which may be substituted with methyl group. The compound has strong herbicidal effect against the weeds belonging to the Family Gramineae.

Phenoxypropionic acid ester derivatives

Disclosed is a tetrahydrophthalimide derivative of the formula (I): ##STR1## wherein X.sup.1 and X.sup.2, the same or different, represent halogen, hydrogen or trifluoromethyl; R represents ##STR2## (wherein R.sup.1 and R.sup.2, the same or different, represent hydrogen or methyl, R.sup.3 represents 2-tetrahydrofurfuryl or 3-methyl-1,2,4-oxadiazol-5-yl), ##STR3## (wherein R.sup.4 is hydrogen or methyl, R.sup.5 is methyl or benzyl), ##STR4## (wherein R.sup.6 represents hydrogen or methyl, R.sup.7 is halogen or C.sub.1 -C.sub.4 alkyl), ##STR5## (wherein R.sup.8 is hydrogen, acyl or arylalkyl), cyano, or --CH.sub.2 OR.sup.9 (wherein R.sup.9 is hydrogen, acetyl, halophenyl, C.sub.1 -C.sub.4 tetrahydrophthalimide derivative of the present invention is useful as a herbicide.

Tetrahydrophthalimide derivative and herbicide composition containing

Disclosed is novel hexahydrophthalic anilide derivatives and herbicide compositions comprising the derivatives. The hexahydrophthalic anilide derivatives of this invention are represented by the formula [I], [II] or [III]. ##STR1## (wherein R.sup.1 represents non-substituted or substituted phenyl, R.sup.2 represents hydrogen or C.sub.1 -C.sub.4 alkyl, R.sup.3 represents C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkenyl) ##STR2## (wherein R.sup.4 and R.sup.5, the same or different, represent C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkenyl or C.sub.1 -C.sub.4 alkynyl, provided R.sup.4 and R.sup.5 are not C.sub.1 -C.sub.4 alkyl simultaneously) ##STR3## (wherein X.sup.1 and X.sup.2, the same or different, represent halogen, Y represents oxygen or sulfur, R.sup.6 represents C.sub.1 -C.sub.6 straight or cyclic alkyl which may be substituted with oxygen, R.sup.7 represents hydrogen or methyl, R.sup.8 represents cyano, C.sub.1 -C.sub.3 alkyl, C.sub.2 or C.sub.3 alkenyl, C.sub.2 -C.sub.4 alkynyl, C.sub.3 -C.sub.6 alkynyl which is substituted with methoxy, CONHR.sup.9 (wherein R.sup.9 represents aromatic sulfonyl) or azole heterocyclic ring)

Hexahydrophthalic anilide derivatives

Disclosed is a novel compound of the formula [I]: ##STR1## wherein A represents ##STR2## (wherein X is H or Cl) ##STR3## Z represents ##STR4## (wherein R.sup.1 is H or CH.sub.3, R.sup.2 is H or C.sub.1 -C.sub.4 alkyl), furylmethyl group, tetrahydrofuryl group 2-tetrahydropyranylmethyl group or tetrahydrofurfuryl group which may be substituted with methyl group. The compound has strong herbicidal effect against the weeds belonging to the Family Gramineae.

Phenoxypropionic acid ester derivatives as herbicides

A propionic acid thiol ester derivative having the formula: ##STR1## wherein R.sub.1 is a cyano group, a trifluoromethyl group, a halogen atom or a nitro group,

Certain-2-pyridyloxy-phenoxy-propionic acid-s-thiazolin-2-yl and

1,2,4-oxadiazole derivatives having selective herbicidal action in controlling broad leaf weeds and cyperaceous weeds without causing phytotoxicity to geraminous crop plants having the formula: ##STR1## wherein A is a methine group or a nitrogen atom; R.sub.1 is a chlorine atom or a methyl group; when A is a methine group, R.sub.2 is a hydrogen atom if R.sub.1 is a methyl group, and a hydrogen atom or a methyl group if R.sub.1 is a chlorine atom, and when A is a nitrogen atom, R.sub.2 is a hydrogen atom; R.sub.3 is a hydrogen atom, an alkyl group having from 1 to 11 carbon atoms, a benzyl group unsubstituted or substituted by chlorine or methoxy; a phenoxymethyl group unsubstituted or substituted by chlorine or methyl, or a lower alkoxyalkyl group.

1,2,4-oxadiazole derivatives, and selective herbicidal compositions

A hydroxyacetic acid amide derivative having the formula: ##STR1## wherein each of R and R.sub.1 which may be the same or different, is an alkyl, alkenyl, alkynyl or alkoxyalkyl group having from 1 to 4 carbon atoms, provided that R and R.sub.1 are not simultaneously alkyl groups.

Hydroxyacetic acid amide derivatives, and herbicidal compositions

A propionic acid thiol ester derivative having the formula: ##STR1## wherein R.sub.1 is a cyano group, a trifluoromethyl group, a halogen atom or a nitro group, R.sub.2 is a hydrogen atom, a halogen atom or a cyano group, R.sub.3 is a thiazolin-2-yl group or a benzothiazol-2-yl group, and A is a methine group or a nitrogen atom.

Propionic acid thiol ester derivatives and herbicidal compositions

Novel compounds in the form of 2-[4-(4-cyanophenoxy)-phenoxy]-propionic or acetic acid amide derivatives and selective herbicides containing the same as an active ingredient.

Herbicidal 2-[4-(4-cyanophenoxy)-phenoxy]-alkanoic acid amides

Propionic acid derivatives represented by the formula (I) ##STR1## wherein X indicates an oxygen atom or a sulfur atom, Y indicates a hydrogen atom or a halogen atom, R.sub.1 and R.sub.2 are the same or different group, indicating an alkyl group, alkenyl group, alkynyl group, cycloalkyl group, lower alkoxy group, lower alkoxyalkyl group, phenyl group, respectively, or R.sub.1 and R.sub.2 may form a heterocyclic group together with a nitrogen atom bonding to said R.sub.1 and R.sub.2, and herbicidal compositions employing them.

Growing community of inventors

Tokuyama, Japan

Mikio Ito