Mitsui Chemicals, Inc.

Mitsui Toatsu Chemicals, Incorporated

Kanji Tomiya

Hiroyuki Katsuta

Koichi Moriyasu

Kenji Kodaka

Yukihiro Yoshikawa

Yuji Yanase

Shunichi Inami

Junro Kishi

Naofumi Tomura

Osamu Takahashi

Kengo Oda

Seiichi Ishii

Hideo Kawashima

Harumichi Aoki

Shingo Matsuo

Makoto Nishida

Yasunaga Iwasaki

Sadafumi Koda

Hideyuki Akieda

Makoto Suzuki

Kei Yoshida

Tohru Miura

Akira Matsubara

Hitoshi Shimotori

Kiyoshi Arai

Itaru Yamamoto

Mikio Kumakura

Toshio Kitashima

Masami Oyamada

Akie Fujiwara

Miura Tohru

Mitsuhiro Sakaguchi

Osamu Mizuno

Sachiko Hibi

Toshio Kitajima

Hideo Kawasima

A compound represented by the formula (1) which is useful as an agricultural fungicide or an intermediate thereof can be obtained by reacting a compound of the general formula (2) with a compound of the general formula (3) in the presence of an acid and reducing the resulted reaction mixture.

Process for preparing 2-alkyl-3-aminothiophene derivative and 3-aminothiophene derivative

A compound represented by the formula (1) which is useful as an agricultural fungicide or an intermediate thereof can be obtained by reacting a compound of the general formula (2) with a compound of the general formula (3) in the presence of an acid and reducing the resulting reaction mixture.

A 5-aminopyrazole-4-carboxylate derivative represented by the formula (1) is prepared by reacting a compound represented by the formula (2) with a hydrazine compound represented by the formula (3) or hydrate, hydrochloride, hydrobromide or sulfate of the same according to the reaction formula (C):

5-aminopyrazole-4-carboxylate derivative and process for preparing the same

A substituted anilide derivative represented by the formula (2): ##STR1## wherein A and B are methyl, and X is a hydrogen atom. The substituted anilide can be used to prepare a substituted carboxanilide derivative that exhibits a disease control effect against Botrytis cinerea, Powdery mildew, Pyricularia oryzae of rice plant and other various plant diseases, is excellent in residual effect, has activity against strains that are resistant to conventional chemicals, is safe for crops, and thus is useful as a plant disease control agent.

Substituted anilide derivative

A substituted carboxanilide derivative represented by the formula (1): ##STR1## wherein A is a hydrogen atom or methyl, B is a methyl or ethyl, and Het is 1-methyl-3-substituted-4-pyrazolyl or 2-methyl-4-substituted-5-triazoyl group, exhibits a disease control effect against Botrytis cinerea, Powdery mildew, Pyricularia oryzae of rice plant and other various plant diseases, is excellent in residual effect, has also activity against resistant strain for conventional chemicals, particularly exerts control effects against Botrytis cinerea at a lower dosage as compared with a prior art, is also safe for crops, and thus is useful as a plant control agent.

Substituted carboxanilide derivative and plant disease control agent

A novel substituted thiophene derivatives represented by the formula (1) in the invention: ##STR1## wherein R is a straight or branched alkyl group having 3-12 carbon atoms, straight or branched halogenoalkyl group having 3-12 carbon atoms, straight or branched alkenyl group having 3-10 carbon atoms, straight or branched halogenoalkenyl group having 3-10 carbon atoms, or cycloalkyl group having 3-10 carbon atoms, the cycloalkyl group being unsubstituted or substituted with an alkyl group having 1-4 carbon atoms, R and --NHCOAr are adjacent to each other, and Ar is a heterocyclic group; have excellent control activity on various plant disease such as Gray mold, Powdery mildew, Blast and Rust, and are useful as a plant disease control agent due to outstanding residual effect on Botrytis cinerea and excellent effect on Gibberella zeae.

Substituted thiophene derivative and plant disease control agent

The substituted thiophene derivative of the invention which is represented by the general formula (1) has a broad disease spectrum for a pathogenic fungus of various crops, exhibits an excellent controlling effect on disease such as gray mold, powdery mildew and rust in particular, and is also effective for a resistant fungus of conventional fungicides which has become a serious problem, and consequently is useful for an agricultural and horticultural fungicide. ##STR1##

Substituted thiophene derivative and agricultural and horticultural

A herbicidal composition is here disclosed which exerts an excellent herbicidal activity and which is harmless to paddy rice. A 1-[1-methyl-1-(substituted phenyl)ethyl]-4,5-dimethyl-3-(substituted phenyl)-3-pyrroline-2-one derivative represented by the formula (I) ##STR1## (wherein X is a chlorine atom, fluorine atom or bromine atom; Y is a hydrogen atom, fluorine atom, chlorine atom or methoxy group; Z is a hydrogen atom, fluorine atom, bromine atom or chlorine atom; and Q is a hydrogen atom or fluorine atom) is a novel compound, and the herbicidal composition containing this compound as a herbicidally active ingredient has the strong activity and high selectivity as the herbicidal composition for paddy fields.

3-pyrroline-2-one derivatives and herbicidal compositions containing same

A 3-azabicyclo[3.1.0]hexane-2-one derivative represented by the following formula (I), and a herbicidal composition containing the same as a herbicidally active ingredient: ##STR1## (wherein X is a halogen atom, an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms or a haloalkyl group having 1 to 3 carbon atoms; Y is a halogen atom or an alkyl group having 1 to 3 carbon atoms; R.sub.1 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms; R.sub.2 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms; m is an integer of 0 to 3; n is an integer of 0 to 2; and when m is 2 or 3, the groups represented by X may be identical or different, and when n is 2, the groups represented by Y may be identical or different).

3-azabicyclo[3.1.0]hexane-2-one derivatives and herbicidal compositions

The present invention is directed to a method for preparing 3,4-trans-4-ethyl-1,3-disubstituted (substituted phenyl)pyrrolidine-2-one represented by the formula (1) ##STR1## which comprises the steps of dissolving 4-ethyl-1,3-disubstituted (substituted phenyl)-3-pyrroline-2-one in an inert solvent, and then reducing the same with sodium boron hydride in the presence of methanol.

Method for preparing pyrrolidine derivatives

4-Ethyl-3-(phenyl)-1-(3-trifluoromethylphenyl)-2-pyrrolidinones and corresponding compounds bearing a p-substituent on the 1-position phenyl group and/or a substituent on the 3-position phenyl group exhibit selective herbicidal activities against various weeds which cause problems in rice or upland fields, even at extremely low application rates. They can be prepared by reductive dehalogenation of a corresponding .alpha.-haloethyl substituted pyrrolidinone or reductive cyclization of a corresponding N-2-butenyl-N-(substituted phenyl)-haloacetyl-3-trifluoromethylaniline.

4-ethyl-3-(substituted

A 3,4-cis isomer of 4-ethyl-1-(substituted phenyl)-3-substituted phenyl)pyrrolidin-2-one, when reacted with a base, can be effectively convered into a 3,4-trans isomer thereof which has a high herbicidal activity useful as an effective ingredient for a herbicidal composition. Furthermore, 3,4-trans-4-ethyl-1-(substituted phenyl)-3-(substituted phenyl)pyrrolidin-2-one compounds represented by the formula (III) ##STR1## (wherein R.sup.2 is an isopropyl group, and X is a fluorine atom, chlorine atom or bromine atom substituted at the 3-position, or fluorine atoms substituted at the 3- and 4-positions or the 3- and 5-positions) have an extremely excellent activity particularly as a herbicidally active ingredient of the herbicidal composition for rice paddy fields.

3,4-trans-4-ethyl-1-(substituted phenyl)-3- (substituted phenyl)

A novel 1,2-dithiol-3-thione derivative which has an immunomodulating property, which is expressed by the formula (I): ##STR1## wherein R denotes hydrogen, halogen, lower alkoxy group, lower alkyl group, amino group, lower alkyl-substituted amino group or lower alkoxycarbonyl group.

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Chiba-ken, Japan

Kanji Tomiya