Nippon Soda Co., Ltd.

Hidekazu Miyazaki

Shiro Tsubokura

Tadashi Sugiura

Kaoru Noda

Satoru Yanaka

Kengo Suzuki

Hiroshi Sakai

Nobuo Matsui

Atsushi Ogihara

The present invention provides a method for producing a 1H-tetrazole derivative by reacting an azide compound represented by general formula (II) and a cyanide compound represented by general formula (III) in a flow reactor to produce a compound represented by general formula (I) (wherein, Y represents an alkyl group, aryl group, arylalkyl group, substituted silyl group or substituted silylalkyl group, Z represents &#x2014;CO&#x2014;, &#x2014;SO&#x2014; or &#x2014;CRR&#x2014; (wherein, Rand Rrespectively and independently represent a hydrogen atom, alkyl group or unsubstituted or substituted aryl group), p represents 0 or 1, q represents 0 or 1, r represents 0 or 1 (provided that q is 1 in the case p is 0 or r is 0), Rrepresents an alkyl group or hydrogen atom in the case q is 0 or an alkylene group in the case q is 1, and Rrepresents an unsubstituted or substituted aryl group). 

Method for producing 1-H-tetrazole derivative

Disclosed is a compound containing a pyridine ring that can be synthesized in an industrially advantageous manner, and is useful as an intermediate for producing tetrazolyloxime derivatives that exhibit fungicidal activity (wherein Rrepresents a Calkoxy group, Calkoxy-Calkoxy group or the like, Rrepresents a Calkoxycarbonyl group, acetyl group or the like, Z represents a halogen atom, cyano group or the like, X represents a halogen atom, and n represents an integer of 0 to 3), and industrially advantageous production methods for producing 2-substituted amino-6-halomethylpyridine derivatives and tetrazolyloxime derivatives.

Compound containing pyridine ring and method for producing halogenated picoline derivative and tetrazolyloxime derivative

Disclosed is a compound containing a pyridine ring that can be synthesized in an industrially advantageous manner, and is useful as an intermediate for producing tetrazolyloxime derivatives that exhibit fungicidal activity (wherein Rrepresents a Calkoxy group, Calkoxy-Calkoxy group or the like, Rrepresents a Calkoxycarbonyl group, acetyl group or the like, Z represents a halogen atom, cyano group or the like, X represents a halogen atom, and n represents an integer of 0 to 3), and industrially advantageous production methods for producing 2-substituted amino-6-halomethylpyridine derivatives and tetrazolyloxime derivatives. 

A process for producing heterocyclic compounds which are useful as pesticides, drugs, fungicidal materials or intermediates thereof. TosMIC is reacted with an aldehyde or an imino compound: 1) in a solvent mixture of an aprotic solvent with a protic solvent in the presence of a base, 2) in the presence of a phase-transfer catalyst and an inorganic base, or 3) in the presence of an inorganic base. Thus, a desired product can be efficiently obtained using a solution without isolating TosMIC which is irritating and unstable, has a low decomposition point and shows explosivity.

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Takaoka, Japan

Hidekazu Miyazaki