# US 2014/0155611 A1 · Compound containing pyridine ring and method for producing halogenated picoline derivative and tetrazolyloxime derivative

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- Number: US 2014/0155611 A1
- Document ID: US20140155611A1
- Status: Published application
- Kind: A1
- Application number: 14/173,323
- Filed: 2014-02-05
- Published: 2014-06-05
- Earliest claimed: 2010-03-12
- Assignees: Nippon Soda Co., Ltd.
- Applicants: Nippon Soda Co., Ltd.
- Inventors: Hidekazu Miyazaki; Satoru Yanaka; Shiro Tsubokura; Tadashi Sugiura; Kaoru Noda; Kengo Suzuki
- Web page: https://patentgrep.com/patent/US20140155611A1

## CPC

- C07D 213/75: Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 405/12: linked by a chain containing hetero atoms as chain links
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

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 R0 represents a C1-6 alkoxy group, C1-6 alkoxy-C1-6 alkoxy group or the like, R1 represents a C1-2 alkoxycarbonyl 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.

## Claims

### Claim 1

A tetrazolyloxime derivative represented by formula (9):
wherein R1C represents an unsubstituted or substituent-containing alkyl group, or an unsubstituted or substituent-containing alkoxy group,
R2C represents an unsubstituted or substituent-containing alkoxycarbonyl group, or an unsubstituted or substituent-containing acyl group,
Z represents a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, a formyl group, a carboxyl group, an unsubstituted or substituent-containing amino group, an unsubstituted or substituent-containing alkyl group, an unsubstituted or substituent-containing alkenyl group, an unsubstituted or substituent-containing alkynyl group, an unsubstituted or substituent-containing aryl group, an unsubstituted or substituent-containing heterocyclic group, OR3, S(O)pR3, COR3 or CO2R3 (wherein R3 represents an unsubstituted or substituent-containing amino group, an unsubstituted or substituent-containing alkyl group, an unsubstituted or substituent-containing alkenyl group, an unsubstituted or substituent-containing alkynyl group, an unsubstituted or substituent-containing aryl group, or an unsubstituted or substituent-containing heterocyclic group, and p represents a number of oxygen atoms in parentheses, and is an integer of 0 to 2),
m represents a number of Z substituents and is an integer of 0 to 3, and when m is 2 or more, a plurality of the Z substituents may be identical to, or different from, each other,
Y represents an unsubstituted or substituent-containing alkyl group,
A represents a halogen atom, an unsubstituted or substituent-containing alkyl group, an unsubstituted or substituent-containing alkoxy group, a cyano group, an unsubstituted or substituent-containing alkylsulfonyl group, a nitro group, or an unsubstituted or substituent-containing aryl group, and
nc represents a number of A substituents and is an integer of 0 to 5, and when nc is 2 or more, a plurality of the A substituents may be identical to, or different from, each other.

### Claim 2

A method for producing a tetrazolyloxime derivative represented by formula (9), the method comprising: a step C1 in which a halogenated picoline derivative represented by formula (7) is reacted with a tetrazolylhydroxyimino derivative represented by formula (8),
wherein R1C represents an unsubstituted or substituent-containing alkyl group, or an unsubstituted or substituent-containing alkoxy group,
R2C represents an unsubstituted or substituent-containing alkoxycarbonyl group, or an unsubstituted or substituent-containing acyl group,
X represents a halogen atom,
Z represents a halogen atom, a cyano group, a nitro group, a hydroxyl group, a thiol group, a formyl group, a carboxyl group, an unsubstituted or substituent-containing amino group, an unsubstituted or substituent-containing alkyl group, an unsubstituted or substituent-containing alkenyl group, an unsubstituted or substituent-containing alkynyl group, unsubstituted or substituent-containing aryl group, unsubstituted or substituent-containing heterocyclic group, OR3, S(O)pR3, COR3 or CO2R3 (wherein R3 represents an unsubstituted or substituent-containing amino group, an unsubstituted or substituent-containing alkyl group, an unsubstituted or substituent-containing alkenyl group, an unsubstituted or substituent-containing alkynyl group, an unsubstituted or substituent-containing aryl group, or an unsubstituted or substituent-containing heterocyclic group, and p represents a number of oxygen atoms in parentheses, and is an integer of 0 to 2),
m represents a number of Z substituents and is an integer of 0 to 3, and when m is 2 or more, a plurality of the Z substituents may be identical to, or different from, each other,
Y represents an unsubstituted or substituent-containing alkyl group,
A represents a halogen atom, an unsubstituted or substituent-containing alkyl group, an unsubstituted or substituent-containing alkoxy group, a cyano group, an unsubstituted or substituent-containing alkylsulfonyl group, a nitro group, or an unsubstituted or substituent-containing aryl group, and
nc represents a number of A substituents and is an integer of 0 to 5, and when nc is 2 or more, a plurality of the A substituents may be identical to, or different from, each other.