USOO5612358A
United States Patent [191
[11]
Ishimitsu et al.
[45] Date of Patent:
[54]
PYRIDINE COMPOUDS WHICH HAVE
USEFUL INSECTIClDAL ACTIVITY
[75] Inventors: Keiichi Ishimitsu, Kanagawa;
Haruhito Ohishi, Saitama; Renpei
I-Iatano; Jun Mitsui, both of
5,612,358
Patent Number:
*Mar. 18, 1997
Chemical Abstracts, vol. 115(9), Abstract No. 92,085a, p.
745, Sep. 2, 1991.
Primary Examiner-Zinna Northington Davis
Attorney, Agent, or Firm—Joseph C. Mason, Jr.; Louise A.
Foutch
Kanagawa; Junji Suzuki, Toyama;
[57]
Tomio Yamada; Nobuo Takakusa,
both of Kanagawa, all of Japan
An insecticidal compound of the formula
ABSTRACT
[73] Assignee: Nippon Soda Co., Ltd., Tokyo, Japan
[ *]
Notice:
The term of this patent shall not extend
beyond the expiration date of Pat. No.
5,304,566.
[21] Appl. No.: 117,470
[22] Filed:
Sep. 7, 1993
wherein
A completes a 5 or 6 membered aromatic ring selected from
Related U.S. Application Data
the group pyridyl, pyridyl substituted with C1_5alkyl,
C1_5haloalkyl,
[63]
Continuation of Ser. No. 700,165, Jul. 9, 1991, Pat. No.
5,304,566.
[30]
Foreign Application Priority Data
0m. 6,
Dec. 27,
Mar. 9,
May 2,
Jul. 26,
[51]
[52]
1989
1989
1990
1990
1990
[JP]
[JP]
[JP]
[JP]
[JP]
.................................. .. 2259966
C1_5alkylthio,
phenoxy
or
C1_5dialkylamin0, pyrazinyl, pyrazinyl substituted with
C1_5alkyl or halogen, pyrazolyl substitited with C,_5alkyl,
with halogen or C1_5alky1;
clksalkylthio, C1_5alkylsulfonyl, cyano, halogen, phe
noxy, or clwsdialkylarnino;
Field of Search ................................... .. 546/286, 300,
546/311, 329, 332, 334, 338; 514/344,
345, 352, 357
References Cited
PUBLICATIONS
Hackh’s Chemical Dictionary, p. 62, 1969.
Del Corona et al, Boll. Chim. Farm, vol. 118 (11), pp.
661-666 (1979).
halogen,
R1 is hydrogen or C1_5alkyl, C,_5haloalkyl, C1_5alkoxy,
Japan
Int. Cl.6 ....................... .. C07D 213/36; A01N 43/36
U.S. Cl. ........................ .. 514/357; 546/286; 546/300;
[56]
cyano,
pyridazyl substituted with halogen, or thiazolyl substituted
Japan
546/311; 546/329; 546/332; 546/334; 546/338;
514/344; 514/345; 514/352
[58]
C1_5alk0xy,
C1_5alkylsulfonyl,
X is substituted or unsubstituted C1_3alkylene or
C1_3alkylidene;
R2
is
hydrogen,
monoalkylcarbarnoyl,
C,_5dialkylcarbamoyl, C1_5alkoyl, C1_5alkyl substi
tuted with halogen, C1_5alkoxy, C1_5alkylthio,
C1_5alkoxycarbonyl,
cyano,
aryl,
haloaryl,
C1_5alkoxyaryl, furyl, thienyl, pyridyl, halopyridyl,
thiazolyl or halothiazolyl, C2_5alkyenyl, Czisalkynyl,
C3_6cycloalkyl, aryl, or the radical
—Y—R5
and an insecticidal acceptable salt thereof.
7 Claims, N0 Drawings
5,612,358
1
2
PYRIDINE COMPOUDS WHICH HAVE
USEFUL INSECTICIDAL ACTIVITY
been developed and put to practical use as insecticides over
many years. These insecticides have played a very great role
This is a continuation of application Ser. No. 07/700,165
?led on Jul. 9, 1991 now US. Pat. No. 5,304,566.
for the improvement of agricultural production. However, in
recent years some of these insecticides are regulated on their
use because of problems such as environmental pollution
DESCRIPTION OF RELATED ART
The present invention relates to new amine derivatives,
the processes for the production thereof and insecticides
containing the said derivatives as effective compounds.
BACKGROUND ART
A large number of chemicals, for example, organophos
due to residue or accumulation, or cause infestation of
resistant insect pests as a result of long-term use. Therefore,
there is a need to develop new chemicals which have
excellent insecticidal characteristics over various types of
insect pests including these resistant insect pests and which
can be used safely.
The following compound is known as the isomer com
phorus compounds such as parathion and malathion and 15
carbamate compounds such as carbaryl and methomyl, have
pound of this invention, which has no insecticidal activity.
5,612,358
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