Idemitsu Kosan Company, Limited

Kazufumi Nakamura

Ichiro Nasuno

Masashi Sakamoto

Kazuyoshi Koike

Mitsuru Shibata

Izumi Terada

Masahiro Nishii

Hidetoshi Koga

Ryoichi Adachi

Kazuyuoshi Koike

Masatoshi Uemura

Masahiro Yoshida

Takashi Mitsuyama

Misako Yoshikawa

Aromatic carboxylic acid bicyclic sulfur compounds

A triketone derivative represented by the following formula or a salt thereof:

Triketone derivatives

The present invention relates to pyrazole derivatives of the formula (I), wherein R.sup.1, R.sup.2, X.sup.1, X.sup.2, X.sup.3, X.sup.4, X.sup.5, X.sup.6, X.sup.7, X.sup.8, p and n are as defined on claim 1, or a salt thereof, and herbicides containing them as active ingredients.

Pyrazole derivatives

The present invention relates to pyrazole derivatives of the formula (I), ##STR1## wherein R.sup.1, R.sup.2, X.sup.1, X.sup.2, X.sup.3, X.sup.4, X.sup.5, X.sup.6, X.sup.7, X.sup.8, p and n are as defined on claim 1, or a salt thereof, and herbicides containing them as active ingredients.

An aromatic carboxylic acid bicyclic sulfur compound of the following formula: ##STR1## wherein X.sup.1 is selected from the group consisting of C.sub.1 to C.sub.4 alkyl, halogen, C.sub.1 to C.sub.4 haloalkyl, C.sub.2 to C.sub.4 alkoxyalkyl, C.sub.1 to C.sub.4 alkoxy and C.sub.1 to C.sub.4 haloalkoxy; each of X.sup.2 and X.sup.3 is independently selected from the group consisting of hydrogen, C.sub.1 to C.sub.4 alkyl and C.sub.1 to C.sub.4 haloalkyl; X.sup.4 is selected from the group consisting of hydrogen, halogen, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 haloalkyl and C.sub.1 to C.sub.4 alkoxy; each of X.sup.5, X.sup.6, X.sup.7 and X.sup.8 is independently hydrogen or C.sub.1 to C.sub.4 alkyl; the bond between X.sup.2 and X.sup.5 is saturated or unsaturated; the bond between X.sup.5 and X.sup.7 is saturated or unsaturated; p is an integer of 0 or 1; and n is an integer of 0, 1 or 2; or a salt thereof.

A triketone compound of the following formula: ##STR1## wherein Y.sup.1 is C.sub.1 to C.sub.4 alkyl, a halogen or a C.sub.1 to C.sub.4 haloalkyl; each of Y.sup.2 and Y.sup.3 is independently C.sub.1 to C.sub.4 alkyl; Y.sup.4 is hydrogen, C.sub.1 to C.sub.4 alkyl or a halogen; n is 0, 1 or 2; p is 0 or 1; each of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 is independently hydrogen, C.sub.1 to C.sub.4 alkyl or phenyl; or when p is 1, either R.sup.1 or R.sup.2 and either R.sup.3 or R.sup.4 optionally bond to each other to form an intramolecular double bond; and X is a group of the formula ##STR2## in which each of R.sup.5 and R.sup.6 is independently a hydrogen atom, a C.sub.1 to C.sub.4 alkyl group or a phenyl group. The triketone compound is useful as a herbicide to control a broad range of upland weeks at a low dosage without causing phytotoxicity on corn.

A bicyclic sulfur compound of the following formula: ##STR1## wherein X.sup.1 is selected from the group consisting of C.sub.1 -C.sub.4 alkyl, halogen, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkoxyalkyl, C.sub.1 -C.sub.4 alkoxy and C.sub.1 -C.sub.4 haloalkoxy; each of X.sup.2 and X.sup.3 is independently selected from the group consisting of hydrogen, C.sub.1 -C.sub.4 alkyl and C.sub.1 -C.sub.4 haloalkyl; X.sup.4 is selected from the group consisting of hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl and C.sub.1 -C.sub.4 alkoxy; each of X.sup.5, X.sup.6, X.sup.7 and X.sup.8 is independently hydrogen or C.sub.1 -C.sub.4 alkyl; or X.sup.2 and X.sup.5 can combine to form an unsaturated double bond; or X.sup.5 and X.sup.7 can combine to form an unsaturated bond; p is an integer of 0 or 1; and n is an integer of 0, 1 or 2; or a salt thereof.

Herbicide composition comprising 4-(benzothiopyran-6-carbonyl) pyrazoles

The present invention relates to a process for the production of a biguanide derivative useful as an intermediate for triazine-type herbicides, in which the biguanide derivative can be produced at high yields by reacting a phenoxyalkylamine salt with dicyandiamide in a solvent containing a paraffinic hydrocarbon having 8 to 15 carbon atoms, or by reacting a free phenoxylakylamine with a hydrogen halide in a solvent containing a paraffinic hydrocarbon having 8 to 15 carbon atoms and reacting the resultant a phenoxyalkylamine salt with dicyandiamide in the same solvent without isolating the phenoxyalkylamine salt.

Process for producing biguanide derivative

A process for producing a triazine derivative of the formula (III), ##STR1## wherein R.sup.1 is a C.sub.1 -C.sub.4 alkyl group, n is an integer of O to 2, R.sup.2 is hydrogen or a C.sub.1 -C.sub.2 alkyl group, and X is a halogen atom, which comprises reacting a biguanide derivative of the formula, ##STR2## wherein R.sup.1 and n are as defined in the formula (III), and X' is a halogen atom, with a halocarboxylic acid ester of the formula, ##STR3## wherein R.sup.2 and X are as defined in the formula (III), and R.sup.3 is a C.sub.1 -C.sub.4 alkyl group, in the presence of a base, wherein a dehydrating agent is present in the reaction system, and processes for producing 2-fluoroisobutyric acid ester as an intermediate compound for the production of the triazine derivative.

Process for producing triazine compounds

A 2-fluoroisobutyric acid ester can be obtained at a high yield in one pot by reacting a 2-hydroxyisobutyric acid ester with fluorosulfuric acid in the absence or presence of a hydrogen fluoride source, or by reacting a 2-hydroxyisobutyric acid ester with chlorosulfuric acid in the presence of a hydrogen fluoride source.

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Sodegaura, Japan

Kazufumi Nakamura