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 Phenoxypyridine derivatives

Details
Inventors: Ozawa, Kiyomi; Ishii, Shigeru; Hatanaka, Masataka;
Assignee: Nissan Chemical Industries, Limited (Tokyo, JP)
Primary Examiner: Rotman; Alan L.
Assistant Examiner:
Attorney, Agent or Firm: Oblon, Fisher, Spivak, McClelland & Maier

A phenoxypyridine derivative having the formula (CH.sub.3 COO).sub.n CH.sub.3-n R (I) wherein R represents ##STR1## and n is 1 or 2 is produced by reacting a phenoxypyridine-N-oxide derivative having the formula (CH.sub.3 COO).sub.n-1 CH.sub.4-n R' (III) wherein R' represents ##STR2## and n is 1 or 2 with acetic anhydride. The phenoxypyridine derivatives are especially suitable for producing synthetic pyrethroids having excellent insecticidal and acaricidal activity in high yield and an economical process.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS The inventors have studied and found that novel phenylcyclopropane carboxylic acid derivatives having the formula (V) have excellent insecticidal and acaricidal activities.
##STR4## wherein X represents hydrogen or a halogen atom, C.
sub.
1-5 alkyl group C.
sub.
1-5 alkoxy group, trifluoromethyl, cyclopropyl, tri-lower alkylsilyl, lower alkylthio or cyano; Y represents hydrogen atom, or cyano group; and R is defined above.
The phenylcyclopropane carboxylic acid derivatives are new type synthetic pyrethroids having a phenoxypyridine skeleton and can be produced by the following reactions.
##STR5## wherein X, Y and R are defined above and M represents Na or K; Z represents a halogen atom or a substituted sulfonic acid group.
Thus, it has not been known to provide industrial advantageous processes for producing phenoxypyridinemethanols, cyano(phenoxypyridine)methanol or phenoxypicolinic aldehydes which are used for said reactions.
The following processes have been proposed in Japanese Unexamined Patent Publication No.
112881/1978.
##STR6## In said reactions, the starting material of, methyl 6-chloropicolinate and the reducing agent of sodium borohydride or diisobutyl aluminum hydride are expensive reagents.
In the latter reaction for producing the aldehyde, the reaction is carried out at low temperature such as -50.
degree.
C.
The process for the reaction is not an effective industrial process.
In accordance with the process of the present invention, the object compounds having high purity can be produced by using economical starting materials and the reagents by simple operations in high yield.
The process for producing the novel phenoxypyridine derivatives of the present invention is shown by the reaction formulas (A) and (B).
##STR7## wherein R and n are defined above; and R' represents ##STR8## The process for producing the compound of the present invention will be further illustrated.
In the reaction (A), phenoxypicoline or phenoxypyridinemethanol acetate is used as a starting material and an oxidizing agent used for N-oxide for pyridine derivatives is used



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