Mitsui Toatsu Chemicals, Incorporated

Kengo Oda

Makoto Nishida

Takatoshi Udagawa

Koichi Moriyasu

Yuji Enomoto

Naoki Sato

Takeo Yoshimoto

Satoshi Numata

Kanji Tomiya

Yoshikata Hojo

Kiyoshi Nakatani

Masaaki Ura

Shiro Shiraishi

Tsutomu Ishii

Kenji Kodaka

Keiichi Igarashi

Hajime Tachibana

Yukiharu Fukushi

Tsuneo Inoue

Akira Hosono

Akie Fujiwara

Masami Oyamada

Takashi Fujita

Tohru Miura

Masatoshi Gohbara

Kiyoshi Arai

Junko Watanabe

Teruhiko Toyama

Yutaka Kubota

Yasunobu Funakoshi

Harumichi Aoki

Joh Miki

Tutomu Ishii

Miura Tohru

Nakatani Kiyoshi

Sachiko Hibi

Masao Hayashi

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)

1-(3-Substituted benzyl)-3-halogeno-4-(1-halogenoalkyl)-2-pyrrolidinones of the general formula (I): ##STR1## where X represents a hydrogen atom or halogen atom, Y and Z each represents a chlorine atom or bromine atom, and R represents an alkyl group with 2 to 4 carbon atoms, are herbicides useful in rice paddy fields to control weeds therein, especially Echinochloa crusgalli and can be produced subjecting the corresponding 3-dihalogeno compounds to dehalogenation to remove one of the halogen atoms or by cyclizing a 2,2-dihalogenoacetamide derivative represented by the general formula (II) under the presence of an appropriate catalyst; ##STR2## in which X, Y, Z and R respectively have the same meanings as described above.

1-(3-substituted benzyl)-3-halogeno-4-(1-halogeno-alkyl)-2-pyrrolidinone

Novel 3-substituted phenyl-2-isoxazoline-5-carboxylic acids or esters thereof. These compounds have excellent properties as plant growth regulators.

Isoxazoline derivatives and plant growth regulators

The present invention relates to novel aromatic alkane derivatives represented by the following general formula (I): ##STR1## wherein Ar stands for a substituted or unsubstituted phenyl or naphtyl group, R.sup.1 stands for a methyl, ethyl or isopropyl group and R.sup.2 stands for a hydrogen atom or a methyl group, or R.sup.1 and R.sup.2 together with the carbon to which they are attached jointly represent a substituted or unsubstituted cycloalkyl group, and R.sup.3 stands for a fundamental group of an alcohol which is usually used in a form of R.sup.3 OH as to natural or synthetic pyrethroids, and also to processes for the preparation of these compounds and the uses of these compounds. These compounds of the present invention have excellent insecticidal and acaricidal activities while the toxicities of these compounds are very low.

1,4-diaryl alkane derivatives having insecticidal and acaricidal activity

The present invention relates to novel aromatic alkane derivatives represented by the following general formula (I): ##STR1## wherein Ar stands for a substituted or unsubstituted phenyl or naphthyl group, R.sup.1 stands for a methyl, ethyl or isopropyl group and R.sup.2 stands for a hydrogen atom or a methyl group, or R.sup.1 and R.sup.2 together with the carbon to which they are attached jointly represent a substituted or unsubstituted cycloalkyl group and R.sup.3, stands for a fundamental group of an alcohol which is usually used in a form of R.sup.3 OH as to natural or synthetic pyrethroids, and also to the uses of these compounds. These compounds of the present invention have excellent insecticidal and acaricidal activities while the toxicities of these compounds are very low.

Certain aryl-alkane-2-pyridyloxy-phenyl derivatives having insecticidal

The present invention relates to 2-arylethyl ether or thioether derivatives represented by the following general formula [I]: ##STR1## wherein Ar stands for an aryl group, R.sup.1 stands for straight or branched chain alkyl group of 1 to 6 carbons, R.sup.2 stands for a hydrogen atom, or a methyl or ethyl group, R.sup.3 stands for a halogen atom, or a methyl or methoxyl group, R.sup.4 stands for a hydrogen or halogen atom, or a lower alkyl or lower alkoxy group, and n is an integer of 1 or 2 with the proviso that when n is 2, the groups R.sup.4 may be the same or different, and Y stands for an oxygen or sulfur atom, and also to processes for the preparation of these ethers or thioethers and a use of these ethers or thioethers. These compounds of the present invention have excellent insecticidal and acaricidal activities while the toxicity of these compounds are very low.

2-aryl-ethyl ether derivatives and insecticidal and acaricidal agents

A 2-fluoroethoxy-substituted benzene derivative represented by the general formula ##STR1## wherein X represents an oxygen or sulfur atom, R.sup.1 and R.sup.2 represent a hydrogen atom or a lower alkyl group, n represents 0 or 1, and A represents a group of the general formula ##STR2## in which R.sup.3 and R.sup.4 represent a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a lower alkylthio group, a lower haloalkyl group, a lower haloalkylthio group or a methylenedioxy group, R.sup.5 and R.sup.6 represent a hydrogen atom or a lower alkyl group, and p and m represent 0 or 1. This compound is useful as an active ingredient of insecticidal and acaricidal agents, and can be produced by reacting a compound of the general formula ##STR3## with a compound of the general formula

2-Fluoroethoxy-substituted benzene derivatives

Novel diphenyl ether hydrazine derivatives, particularly 2-nitro-5 (nucleus-substituted phenoxy) phenylhydrazine derivatives are provided. They are useful as a selective herbicide having a high herbicidal acitivity and residual efficacy.

Diphenyl ether derivatives and herbicides containing same

Novel diphenyl ether compounds of the general formula: ##STR1## wherein X represents a hydrogen atom or a nitro group, process for preparing the same and diphenyl ethers of the general formula: ##STR2## wherein R represents a hydrogen atom, or substituted or unsubstituted alkyl group, alkenyl group or alkynyl group, and Y represents an oxygen atom, a sulfur atom, or the group ##STR3## wherein R' is defined as R above by reacting 2-chloro-4-trifluoromethylphenyl-3,4-dinitrophenyl ether with a compound of the general formula:

Diphenyl ethers

Novel diphenyl ether compounds of the general formula: ##STR1## wherein X represents a hydrogen atom or a nitro group, process for preparing the same and diphenyl ethers of the general formula: ##STR2## wherein R represents a hydrogen atom, or substituted or unsubstituted alkyl group, alkenyl group or alkynyl group, and Y represents an oxygen atom, a sulfur atom, or the group ##STR3## wherein R' is defined as R above, by reacting 2-chloro-4-trifluoromethylphenyl-3,4-dinitrophenyl ether with a compound of the general formula:

Process for preparing diphenyl ethers

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Kanagawa, Japan

Kengo Oda