Sumitomo Chemical Company, Limited

Toru Haga

Eiki Nagano

Ryo Sato

Kouichi Morita

Masayuki Enomoto

Ryo Yoshida

Shunichi Hashimoto

Tetsuya Shiozaki

Masayuki Takase

Junya Takahashi

Masaharu Sakaki

A 3-methylthiopropanal is produced by a method comprising the step of supplying an acrolein and a methyl mercaptan together or sequentially with an acidic compound and a basic compound into a reaction system to react the acrolein with the methyl mercaptan, wherein the basic compound is used in an amount of about 0.3 mol or less per mol of the acidic compound. In accordance with the present invention, a 3-methylthiopropanal with high quality is produced while suppressing the production of by-products having high boiling points.

Method for producing 3-methylthiopropanal

The present invention provides a process for producing 2-hydroxy-4-methylthiobutyric acid comprising the following steps (1) to (4):

Process for producing 2-hydroxy-4-methylthiobutyric acid

A compound of the formula: ##STR1## wherein X is an oxygen atom or a sulfur atom, Y is a hydrogen atom or a fluorine atom, Z is a methylene group or a group of the formula: N--R.sub.5 (in which R.sub.5 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.7 alkenyl group, a C.sub.3 -C.sub.7 alkynyl group, a halo(C.sub.2 -C.sub.6)alkyl group or a C.sub.1 -C.sub.6 alkoxycarbonylmethyl group), R.sub.1 is a hydrogen atom, a C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.7 alkenyl group, a C.sub.3 -C.sub.7 alkynyl group, a halo(C.sub.2 -C.sub.6)alkyl group, a halo(C.sub.3 -C.sub.7)alkenyl group, a cyano(C.sub.1 -C.sub.6)alkyl group, a C.sub.1 -C.sub.6 alkoxy(C.sub.1 -C.sub.6)alkyl group or a C.sub.1 -C.sub.6 alkoxycarbonylmethyl group, R.sub.2 is a hydrogen atom or a C.sub.1 -C.sub.6 alkyl group; R.sub.3 and R.sub.4 are, the same or different, each is a hydrogen atom or a C.sub.1 -C.sub.6 alkyl group; n is an integer of 0 or 1, which is useful as a herbicide.

N-phenylimides, and their production and use

A compound of the formula: ##STR1## wherein R is a C.sub.1 -C.sub.5 alkyl group, a C.sub.3 -C.sub.4 alkenyl group, a C.sub.3 -C.sub.4 alkynyl group, a C.sub.1 -C.sub.2 alkoxy (C.sub.1 -C.sub.2) alkyl group, a C.sub.1 -C.sub.2 alkylthio (C.sub.1 -C.sub.2) alkyl group or a mono- or polyfluoro-(C.sub.1 -C.sub.3) group, X is a C.sub.1 -C.sub.4 alkylene group which may be substituted with at least one methyl or a --OCH.sub.2 -- group and n is an integer of 0, 1 or 2, which is useful as a herbicide.

Benzothiazolones, and their production and use

A compound of the formula: ##STR1## wherein R is a C.sub.1 -C.sub.5 alkyl group, a C.sub.3 -C.sub.5 alkenyl group, a C.sub.3 -C.sub.5 alkynyl group or a C.sub.3 -C.sub.7 cycloalkyl group, which is useful as a herbicide.

Benzotriazoles, and their production and use

A compound of the formula: ##STR1## wherein R.sup.1 is a C.sub.1 -C.sub.6 alkyl group, a C.sub.3 -C.sub.7 alkenyl group, a C.sub.3 -C.sub.7 alkynyl group, a halo(C.sub.1 -C.sub.5)alkyl group, a halo(C.sub.3 -C.sub.4) alkenyl group, a halo(C.sub.3 -C.sub.4)alkynyl group, a C.sub.1 -C.sub.4 alkoxy(C.sub.1 -C.sub.2)alkyl group, a C.sub.1 -C.sub.2 alkylthio(C.sub.1 -C.sub.2)alkyl group and R.sup.2 is a hydrogen atom or a methyl group, which is useful as a herbicide.

Process of preparing tetrahydroindazolyl-benzoxazines

Tetrahydroindazolyl-benzoxazines, their production and use

A compound of the formula: ##STR1## wherein R is a C.sub.1 -C.sub.5 alkyl group, a C.sub.3 -C.sub.4 alkenyl group, a C.sub.3 -C.sub.4 alkynyl group, a C.sub.1 -C.sub.2 alkoxy(C.sub.1 -C.sub.2)alkyl group, a C.sub.1 -C.sub.2 alkylthio(C.sub.1 -C.sub.2)alkyl group or a mono- or polyfluoro(C.sub.1 -C.sub.3)alkyl group, X is a C.sub.1 -C.sub.4 alkylene group which may be substituted with at least one methyl or a --OCH.sub.2 -- group and n is an integer of 0, 1 or 2, which is useful as a herbicide.

A compound of the formula: ##STR1## wherein R is a C.sub.2 -C.sub.3 alkyl group, a C.sub.3 -C.sub.4 alkenyl group, or a C.sub.3 -C.sub.4 alkynyl group, and X is a chlorine or bromine atom, is disclosed. These compounds are useful as intermediates in the production of herbicidal 3-chlorotetrahydroindazoles.

2-fluoro-4-halo-5-marcapto-phenyl-hydrazines

A compound of the formula: ##STR1## wherein A is a nitrogen-containing group selected from the group consisting of --NO.sub.2, --NH.sub.2, --N.dbd.C(NH.sub.2)--S--, and --NH--CO--S; X is a fluorine atom or a chlorine atom; and R.sup.2 is a t-butyl group or a 1-methylcyclopropyl group. These compounds are useful as intermediates in the production of herbicidal benzothiazolone compounds.

Intermediates for the production of benzotriazoles

A compound of the formula: ##STR1## wherein R.sub.1 is a hydrogen atom, a fluorine atom or a methyl group and R.sub.2 is as C.sub.1 -C.sub.3 alkyl group, a C.sub.1 -C.sub.5 alkoxy group, a chloro(C.sub.2 -C.sub.4)alkoxy group, a dichloro(C.sub.2 -C.sub.4)alkoxy group, a cyclo(C.sub.3 -C.sub.7)alkoxy group, a phenoxy group, a C.sub.1 -C.sub.5 alkylthio group or a di(C.sub.1 -C.sub.5)alkylamino group, which is useful as a herbicide.

2-Substituted phenyl-4,5,6,7-tetrahydro-2H-isoindole-1,3-diones, and

A compound of the formula: ##STR1## wherein R is a C.sub.1 -C.sub.5 alkyl group, a C.sub.3 -C.sub.5 alkenyl group, a C.sub.3 -C.sub.5 alkynyl group or a C.sub.1 -C.sub.3 alkoxy(C.sub.1 -C.sub.3)alkyl group, X is a nitrogen atom or a methine group and Y is a sulfur atom or an oxygen atom, which is useful as a herbicide.

Benzothiazolylazolidines, and their production and use

A compound of the formula: ##STR1## wherein R is a hydrogen atom, a C.sub.1 -C.sub.5 alkyl group, a C.sub.3 -C.sub.4 alkenyl group, a C.sub.3 -C.sub.4 alkynyl group, a halo(C.sub.1 -C.sub.4)alkyl group, a halo(C.sub.3 -C.sub.4)alkenyl group, a halo(C.sub.3 -C.sub.4)alkynyl group, a C.sub.1 -C.sub.2 alkoxy(C.sub.1 -C.sub.2) alkyl group, a C.sub.1 -C.sub.2 alkoxy(C.sub.1 -C.sub.2)alkoxy(C.sub.1 -C.sub.2)alkyl group, a cinnamyl group, a cyano(C.sub.1 -C.sub.3)alkyl group, a carboxy(C.sub.1 -C.sub.3)alkyl group, a C.sub.1 -C.sub.5 alkoxycarbonyl(C.sub.1 -C.sub.3)alkyl group, a halo(C.sub.1 -C.sub.5)alkoxycarbonyl(C.sub.1 -C.sub.3)alkyl group, a C.sub.1 -C.sub.2 alkoxyalkoxycarbonyl(C.sub. 1 -C.sub.3)alkyl group, a C.sub.1 -C.sub.2 alkoxy (C.sub.1 -C.sub.2)alkoxycarbonyl(C.sub.1 -C.sub.3)alkyl group, a C.sub.1 -C.sub.5 alkoxycarbonyl(C.sub.1 -C.sub.2)-alkoxycarbonyl(C.sub.1 -C.sub.3)alkyl group, a cyclo(C.sub.3 -C.sub.6)alkoxycarbonyl(C.sub.1 -C.sub.3)alkyl group, a C.sub.1 -C.sub.5 alkylaminocarbonyl(C.sub.1 -C.sub.3)alkyl group or a di-(C.sub.1 -C.sub.5)alkylaminocarbonyl(C.sub.1 -C.sub.3)alkyl group and A is an amino group or a nitro group, is disclosed. These compounds are useful as intermediates in the synthetic of benzothiazolone herbicides.

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Takarazuka, Japan

Toru Haga