Mitsui Toatsu Chemicals, Incorporated

Satoshi Numata

Kenji Kodaka

Kiyoshi Nakatani

Takatoshi Udagawa

Shirou Shiraishi

Michihiko Nakaya

Tsuneo Inoue

Tsutomu Ishii

Masatoshi Gohbara

Kengo Oda

Hajime Tachibana

Katsutoshi Kinoshita

Koichi Ebihara

Eiichi Yamada

Teruo Yuasa

Teruhiko Toyama

Yukiharu Fukushi

Shiro Shiraishi

Masayuki Ooka

Masahiko Nakamura

Teruyuki Nagata

Yoshio Morimoto

Mitsumasa Umemoto

Tsutomu Takase

Tamotsu Asano

Yutaka Kubota

Tutomu Nishizawa

Noboru Yamazaki

Akira Hosono

Toshio Itakura

Kouji Kitajima

Nakatani Kiyoshi

Noboro Yamazaki

Shiroh Shiraishi

Novel dialkoxymethylimidazolidine derivatives of the formula (1) ##STR1## are described. Also, a preparation process of the derivatives and insecticidal compositions comprising the same are set forth. In addition, novel intermediate compounds of the formula (2) useful in preparing the derivatives of the formula (1) are also described along with their preparation process ##STR2##

Dialkoxymethylimidazolidine derivatives

Herein disclosed are novel imidazolidine derivatives of the formula (I) and intermediates of the formula (II) ##STR1## wherein each R represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a halogen atom, an alkoxy group having from 1 to 6 carbon atoms, a methylenedioxy group, an alkylthio group having from 1 to 4 carbon atoms, a haloalkyl group having from 1 to 2 carbon atoms, a haloalkoxy group having from 1 to 4 carbon atoms, an alkylcarbonyl group having from 1 to 6 carbon atoms, an alkoxycarbonyl.group having from 1 to 6 carbon atoms, a hydroxy group, a cyano group, a nitro group, an alkylamino group having from 1 to 8 carbon atoms, a phenyl group, a phenoxy group, a benzyl group or a halopyridylmethyloxy group, and n is an integer of from 1 to 3, ##STR2## wherein R and n have, respectively, the same meanings as defined above. Processes for preparing the compounds of the formulas (I) and (II) are also described. Moreover, insecticidal compositions comprising an effective amount of the derivative (I) are described.

Imidazolidine derivatives, preparation thereof, insecticides containing

Novel dialkoxymethylimidazolidine derivatives of the formula (1) ##STR1## are described. Also, a preparation process of the derivatives and insecticidal compositions comprising the same are set forth. In addition, novel intermediate compounds of the formula (2) useful in preparing the derivatives of the formula(1) are also described along with their preparation process ##STR2##

Dialkoxymethylimidazolidine derivatives, preparation thereof,

Novel tetrahydro-1,3,5-thiadiazin-4-ones of the following general formula (I) or their salts which are useful as an insecticidal and acaricidal agent. ##STR1## In the formula, each of R.sup.1 and R.sup.2 represents a halogen atom or a C.sub.1 -C.sub.4 alkyl group; R.sup.3 represents a halogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.3 -C.sub.6 cycloalkyl group, a C.sub.1 -C.sub.4 alkoxy group, an acetyl group, a phenoxy group, a halo-substituted phenoxy group, a benzyl group, a benzyloxy group, a phenylcarbonyl group, a C.sub.1 -C.sub.4 haloalkyloxy group, a C.sub.1 -C.sub.4 haloalkyloxymethyl group, a C.sub.2 -C.sub.4 haloalkenyloxy group, a C.sub.1 -C.sub.4 haloalkylthio group, a C.sub.1 -C.sub.4 haloalkylthiomethyl group, a C.sub.2 -C.sub.4 haloalkenylthio group, a C.sub.1 -C.sub.8 haloalkyl group, a C.sub.2 -C.sub.8 haloalkenyl group, a C.sub.1 -C.sub.8 alkyloxycarbonyl group, a substituted phenoxycarbonyl group, or a substituted pyridyloxy group; m represents 0, 1, 2 or 3; and n represents 0, 1, 2 or 3. These novel thiadiazines are produced by reacting a compound of general formula (II) ##STR2## wherein R.sup.1 and m are as defined above, with a compound of general formula (III) ##STR3## wherein R.sup.2, R.sup.3 and n are as defined above.

Thiadiazines, and insecticidal and acaricidal preparations

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

A difluorobromomethyoxyphenyl derivative of the general formula ##STR1## wherein A represents an oxygen atom or a methylene group, and Y represents a hydrogen or fluorine atom. A miticide comprising the above derivative as an active ingredient is also provided.

Difluorobromomethoxyphenyl derivative and miticide comprising said

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

2-Arylpropyl ether or thioether derivatives represented by the following general formula [I]: ##STR1## wherein Ar stands for an aryl group, R stands for a methyl or ethyl group, Y stands for an oxygen or sulfur atom, and B stands for a group represented by the following formula [II]: ##STR2## or the following general formula [III]: ##STR3## wherein Z stands for an oxygen or sulfur atom or a carbonyl or methylene group, R.sup.1 stands for a hydrogen or halogen atom or a lower alkyl group or a lower alkoxy group, and n is an integer of from 1 to 5 with the proviso that when n is 2 or more, the groups R.sup.1 may be the same or different, are produced by reacting a compound represented by the following formula (V): ##STR4## with a compound represented by the following formula (VI):

Process for the preparation of 2-arylpropyl ether or thioether

The present invention relates to a process for producing 3-phenoxybenzyl 2-(4-alkoxyphenyl)-2-methylpropyl ethers having excellent insecticidal and acaricidal activities which are represented by formula (IV): ##STR1## wherein R is a lower alkyl group and X.sub.1 and X.sub.2 are each a hydrogen or fluorine atom, which comprises reacting a 3-halogeno-4-alkoxyneophyl halide represented by the formula (I): ##STR2## wherein Y.sub.1 and Y.sub.2 are each a hydrogen, chlorine or bromine atom, at least one of them being a chlorine or bromine atom, R has the same meaning as above and X is a halogen atom, with a 3-phenoxybenzyl alcohol represented by the formula (II): ##STR3## wherein X.sub.1 and X.sub.2 have the same meaning as above, in the presence of a base to obtain a 3-phenoxybenzyl 2-(4-alkoxy-3-halogenophenyl)-2-methylpropyl ether represented by the formula (III): ##STR4## wherein Y.sub.1, Y.sub.2, R, X.sub.1 and X.sub.2 have the same meaning as above, and then subjecting the product to a hydrodehalogenation reaction, and relates to a process for producing a 3-halogeno-4-alkoxyneophyl halide represented by formula (I), which comprises reacting a 2-halogeno-1-alkoxybenzene represented by formula (V): ##STR5## wherein Y.sub.1 and Y.sub.2 are each a hydrogen, chlorine or bromine atom, at least one of them being a chlorine or bromine atom, and R represents a lower alkyl group, with a methallyl halide in the presence of an acid catalyst at -20.degree. to 50.degree. C.

Process for producing 3-phenoxybenzyl 2-(4-alkoxyphenyl)-2-methylpropyl

Indene compounds of the formula ##STR1## wherein X represents a hydrogen atom, a halogen atom, a hydroxyl group or a methyl group, and y is 0 or an integer of 1 to 3, are produced by either heat-decomposing indene compounds of the formula ##STR2## wherein X and y are as defined, in the presence of an acid or alkaline catalyst; or heat-decomposing isopropenyl phenols of the formula ##STR3## wherein X and y are as defined, or oligomers or polymers thereof in the presence of an acid catalyst. 5-Hydroxy-1,1,3-trimethyl-2-indene corresponding to formula (III) is a novel compound.

Novel indene compound and novel process for producing indene compounds

The present invention relates to 2-arylpropyl ether or thioether derivatives represented by the following general formula [I]: ##STR1## wherein Ar stands for an aryl group, R stands for a methyl or ethyl group, Y stands for an oxygen or sulfur atom, and B stands for a group represented by the following formula [II]: ##STR2## or the following general formula [III]: ##STR3## wherein Z stands for an oxygen or sulfur atom or a carbonyl or methylene group, R.sup.1 stands for a hydrogen or halogen atom or a lower alkyl group or a lower alkoxy group, and n is an integer of from 1 to 5 with the proviso that when n is 2 or more, the groups R.sup.1 may be the same or different, and also to processes for the preparation or these ethers of 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-Arylpropyl ether or thioether derivatives and insecticidal and

Indene compounds of the formula ##STR1## wherein X represents a hydrogen atom, a halogen atom, a hydroxyl group or a methyl group, and

Indene compound and novel process for producing indene compounds

A process for preparing piperonal which comprises the steps of reacting 1,2-methylenedioxybenzene with an N-alkylformanilide and a condensing agent comprising one or more compounds selected from the group consisting of phosgene, phosphorus oxychloride, phosphorus oxybromide, thionyl chloride, thionyl bromide, sulfuryl chloride, sulfuryl bromide, phosphorus trichloride, and phosphorus pentachloride, and then hydrolyzing the resulting reaction product.

Process for preparing piperonal

Unsaturated dimers which contain 2,4-diphenyl-4-methyl-1-pentene as their main component (i.e., in an amount of greater than 95%) are produced by reacting an .alpha.-methylstyrene at a temperature of from 20.degree. to 100.degree.C. in the presence of a sulfonic acid type cation-exchange resin catalyst and in the further presence of a primary or secondary monohydric alcohol containing from 2 to 5 carbon atoms. By this reaction, side products including a saturated dimer of 1,1,3-trimethyl-3-phenylindane, trimers and higher polymers are produced only in an extremely small amount. The unsaturated dimers are very useful as a molecular weight modifier when employed, instead of dodecylmercaptans, for the production of polymers such as an ABS resin, an AS resin, and the like.

Growing community of inventors

Yokohama, Japan

Satoshi Numata