Toyo Soda Manufacturing Co., Ltd.

Toyo Soda Mfg. Co., Ltd.

(zaidanhojin) Sagami Chemical Research Center

Ajinomoto Co., Ltd.

Sagami Chemical Research Center

Agro-kanesho Co., Ltd.

Tosoh Corporation

Kanesho Co., Ltd.

Sagami Chem. Rsch. Cntr.

Agro-kenesho Co., Ltd.

Yuji Nonaka

Akira Nakanishi

Kiyotaka Oyama

Keiichi Kihara

Mikio Ito

Shinzo Someya

Hideo Morinaka

Heijiro Satoh

Seigo Koura

Shigeaki Nishimura

Kenji Tsuzuki

Yoshikazu Isowa

Muneki Ohmori

Tetsuya Ichikawa

Kaoru Mori

Tetsuo Takematsu

Masashige Kubo

Rokuro Akahira

Takeshi Uwotani

Mitsuyuki Hashihama

Makoto Konnai

Hideo Takeda

Katsumi Sugiyama

Hiroko Sato

Toshio Hironaka

Mitsuyuki Murakami

Yasuhiro Oda

Takeshi Uotani

Tsutomu Hashimoto

Konnai, Makoto

Kazuo Iwata

Kazuaki Tsukuda

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

Fungicidal composition comprising a fungicidally effective amount of the N-pyridylcarbamate derivative having the formula (I) as an active ingredient: ##STR1## wherein X is 2-naphthyl, 5-indanyl, 5,6,7,8-tetrahydro-2-naphthyl, 1,4-methano-1,2,3,4-tetrahydro-6-naphthyl, 1,4-ethano-1,2,3,4,-tetrahydro-6-naphthyl, 2-quinolyl, or a phenyl group having one or two of the same or different substituents selected from the group of halogen atom, lower alkyl, lower alkenyl, lower alkoxy, lower alkenyloxy, halogenated lower alkyl, lower alkylthio, lower alkyl-sulfonyl, lower alkylamino, nitro, and methylenedioxy; Y is an oxygen atom or a sulfur atom; Z is lower alkyl group; W is pyridyl group having one or two of the same substituents selected from the group of lower alkyl, lower alkoxy, lower alkenyloxy, and lower alkylamino, and biologically inert carriers has excellent fungicidal activity against a variety of molds, and can be used to protect plants from fungal infections.

Fungicidal methods containing N-pyridylcarbamates

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

3-tert-Butyl-4-halophenols which are useful as intermediates for preparing compounds having medical or agricultural activities.

Tert-Butyl-halophenols

An antifungal composition comprising an effective amount of carbamate derivative having the formula (I): ##STR1## where X is 2-naphthyl, 5-indanyl, 5,6,7,8-tetrahydro-2-naphthyl, 1,4-methano-1,2,3,4-tetrahydro-6-naphthyl, 1,4-ethano-1,2,3,4-tetrahydro-6-naphthyl, 2-quinolyl, or a phenyl group having one or two of the same or different substituents selected from the group of halogen atom, lower alkyl, lower alkenyl, lower alkoxy, lower alkenyloxy, halogenated lower alkyl, lower alkylthio, lower alkylsulfonyl, lower alkylamino, nitro, and methylenedioxy;

Antifungal 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.

Propionic acid derivatives and herbicides employing them

The invention provides a novel and efficient method for the elimination of protecting groups, e.g. benzyloxycarbonyl group, from a protected amino acid, peptide or derivative thereof having at least one functional group protected by a protecting group, e.g. a lower alkyl ester of N-benzyloxycarbonyl-.alpha.-L-aspartyl-L-phenylalanine by catalytic hydrogen reduction to produce free amino acid, peptide or derivative thereof. In contrast to the conventional procedures in which the reaction is carried out in a solvent dissolving both the starting compound and the product compound or a solvent dissolving the starting compound but not dissolving the product compound, the inventive method utilizes a binary two-phase reaction medium composed of water and an organic solvent not freely miscible with water such as toluene. The reaction takes place in the organic phase containing the starting compound dissolved and the catalyst dispersed therein whereas the reaction product which is water-soluble is smoothly and successively transferred into the aqueous phase so that advantages are obtained in the unexpectedly high yield of the product as well as in the easiness of handling the reaction mixture after completion of the reaction.

Method for reductive elimination of protecting groups

Carbamate derivatives represented by the general formula (I); ##STR1## wherein X is 2-naphthyl, 5-indanyl, 5,6,7,8-tetrahydro-2-naphthyl, 1,4-methano-1,2,3,4-tetrahydro-6-naphthyl, 1,4-ethano-1,2,3,4-tetrahydro-6-naphthyl, 2-quinolyl, or substituted phenyl,

Aryl N-alkyl-N-(pyridyl or pyrimidyl) carbamate

Herbicides containing thiocarbamate derivatives represented by the general formula (I) as an active ingredient ##STR1## wherein X is 5-indanyl, 5,6,7,8-tetrahydro-2-naphthyl, 1,4-methano-1,2,3,4-tetrahydro-6-naphthyl, 1,4-ethano-1,2,3,4-tetrahydro-6-naphthyl, or substituted phenyl,

Herbicides

Addition compounds have the formula ##STR1## wherein R.sub.1 represents an aliphatic oxycarbonyl group, benzyloxycarbonyl group which can have nuclear substituents or benzoyl, aromatic sulfonyl or aromatic sulfinyl group; R.sub.2 represents methyl, isopropyl, isobutyl, isoamyl or benzyl group; R.sub.3 represents a lower alkoxyl, benzyloxy or benzhydryloxy group and n represents 1 or 2. The addition compounds are produced by reacting an N-substituted monoaminodicarboxylic acid having the formula ##STR2## with an amino carboxlic acid ester having the formula in an aqueous medium in the presence of a protease and reacting the resulting dipeptide ester with the amino carboxylic acid ester and separating the addition compound. The addition compounds can be decomposed into the constituent dipeptide esters and amino acid esters by the action of an acid.

Addition compound of dipeptide derivative and amino acid derivative

A method for purifying an .alpha.-L-aspartyl-L- phenylalanine lower alkyl ester containing impurities. The .alpha.-L-aspartyl-L-phenylalanine lower alkyl ester is brought into contact with a Cl-type anion exchange resin in an aqueous medium to have the impurities adsorbed by the anion exchange resin. The impurities contained in the .alpha.-L-aspartyl-L-phenylalanine lower ester, particularly diketopiperazine and .alpha.-L-aspartyl-L-phenylalanine are selectively and easily removed. The desired matter thus can be easily recovered and disposal of waste liquid, etc. can also be carried out without difficulty.

Method for purifying .alpha.- L-aspartyl-L-phenylalanine lower alkyl

An improvement in a method for manufacturing dipeptides from an N-substituted aspartic acid and a phenylalanine lower alkyl ester. The two starting materials are allowed to react with each other in the presence of an immobilized metallo-proteinase in an organic solvent immiscible with water. The enzyme can be recovered for reuse thereof. The loss of materials due to the hydrolysis of the phenylalanine lower alkyl ester is reduced, so that use of the phenylalanine lower alkyl ester in a nearly stoichiometric quantity suffices for the reaction to ensure an improved yield and reduction in cost of industrial production.

Growing community of inventors

Tokuyama, Japan

Yuji Nonaka