Hydrazine oxoacetamide derivative and insecticide

Details Hydrazine oxoacetamide derivative and insecticide Hydrazine oxoacetamide derivative and insecticide

2001-04-19

2002-06-04

Gerstl, Robert (Department: 1626)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Ester doai

C514S614000, C558S047000, C564S151000

Reexamination Certificate

active

06399659

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a hydrazine oxoacetamide derivative or a salt thereof and a process for producing it, as well as use thereof as a pesticide, particularly, an insecticide.
2. Description of the Background
Several compounds have been known which are connected with a hydrazine oxoacetamide derivative and which have an insecticidal activity. Examples of these compounds include the compounds having the following Formulae (II) to (IV) disclosed in
the specification of U.S. Pat. No. 4,394,387:
(shown as Compound No. 255)
(shown as Compound No. 230), and
(shown as Compound No. 257).
A compound having the following Formula (V) is described in Japanese Patent (J.P.) Kokai No. Hei 10-67732:
A compound having the following Formula (VI) is described in International Publication (WO) No. 97/11050:
A compound having the following formula (VII) is described in EP 742202:
However, the insecticidal activity of these compounds is not always high, and investigations have been made for the purpose of finding a compound having a higher insecticidal activity.
SUMMARY OF THE INVENTION
Accordingly, one object of the present invention is to provide a hydrazine oxoacetamide derivative or a salt thereof having an insecticidal activity higher than those of the ordinary insecticides.
A particular object of the present invention is to provide a hydrazine oxoacetamide derivative or a salt thereof having an excellent insecticidal effect on harmful insects of Lepidoptera and Coleoptera and also soil insect pests.
The present invention relates to a hydrazine oxoacetamide derivative having the following formula or a salt thereof:
wherein
R
1
represents a chlorine atom or a bromine atom,
Y represents an oxygen atom or a methylene group, and when Y is an oxygen atom, p is 2 and when Y is a methylene group, p is 0,
R
2
represents a trifluoromethyl group,
R
3
represents a hydrogen atom or a methyl group,
R
4
represents a hydrogen atom or a methyl group, and
R
5
represents a methyl group, an ethyl group, an n-propyl group, a cyclopropyl group, an allyl group or a propargyl group.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
After intensive investigations on various hydrazine oxoacetamide derivatives in a wide range made for the purpose of developing compounds having an insecticidal activity higher than the activities of conventional hydrazine oxoacetamide derivatives, the inventors have found a new compound which is related to the conventional hydrazine oxoacetamide derivatives, which is represented by Formula (I) given above, and which has a high insecticidal activity. The present invention has been completed on the basis of this finding.
The hydrazine oxoacetamide derivative of the present invention is represented by the above Formula (I). The hydrazine oxoacetamide derivative of the present invention may be in the form of a geometrical isomer of syn- type and anti- type. The geometrical isomer may be in its pure form or a mixture of them. A salt of a hydrazine oxoacetamide derivative is also included in the present invention.
The salt is, for example, a salt with an alkali metal such as sodium and potassium and also with an alkaline earth metal such as magnesium and calcium.
Examples of the hydrazine oxoacetamide derivatives of the present invention include those compounds shown in the following Tables 1 and 2.
TABLE 1
(I)

Compound
No.
R
1
Y
p
R
2
R
3
R
4
R
5
1-3
Cl
O
2
CF
3
H
H
CH
3
1-5
Cl
O
2
CF
3
H
H
C
2
H
5
1-7
Cl
O
2
CF
3
H
H
n-C
3
H
7
1-27
Cl
O
2
CF
3
H
H
CH
2
CH═CH
2
1-37
Cl
O
2
CF
3
H
H
CH
2
C≡CH
1-43
Cl
O
2
CF
3
H
H
c-C
3
H
5
1-133
Cl
O
2
CF
3
H
CH
3
CH
3
1-147
Cl
O
2
CF
3
H
CH
3
c-C
3
H
5
1-178
Cl
O
2
CF
3
CH
3
H
CH
3
1-180
Cl
O
2
CF
3
CH
3
H
C
2
H
5
1-182
Cl
O
2
CF
3
CH
3
H
n-C
3
H
7
1-202
Cl
O
2
CF
3
CH
3
H
CH
2
CH═CH
2
1-212
Cl
O
2
CF
3
CH
3
H
CH
2
C≡CH
1-218
Cl
O
2
CF
3
CH
3
H
c-C
3
H
5
1-304
Cl
O
2
CF
3
CH
3
CH
3
CH
3
1-306
Cl
O
2
CF
3
CH
3
CH
3
C
2
H
5
1-308
Cl
O
2
CF
3
CH
3
CH
3
n-C
3
H
7
1-318
Cl
O
2
CF
3
CH
3
CH
3
c-C
3
H
5
1-515
Br
O
2
CF
3
H
H
CH
3
1-517
Br
O
2
CF
3
H
H
C
2
H
5
1-519
Br
O
2
CF
3
H
H
n-C
3
H
7
1-555
Br
O
2
CF
3
H
H
c-C
3
H
5
1-645
Br
O
2
CF
3
H
CH
3
CH
3
1-647
Br
O
2
CF
3
H
CH
3
C
2
H
5
1-649
Br
O
2
CF
3
H
CH
3
n-C
3
H
7
1-672
Br
O
2
CF
3
CH
3
H
CH
3
1-674
Br
O
2
CF
3
CH
3
H
C
2
H
5
1-676
Br
O
2
CF
3
CH
3
H
n-C
3
H
7
1-686
Br
O
2
CF
3
CH
3
CH
3
CH
3
1-688
Br
O
2
CF
3
CH
3
CH
3
C
2
H
5
1-690
Br
O
2
CF
3
CH
3
CH
3
n-C
3
H
7
Note) “n-” indicates --normal--, and “c-” indicates --cyclic--. The same shall apply hereinafter.
TABLE 2
(Formula (I))
Comp.
No.
R
1
Y
p
R
2
R
3
R
4
R
5
2-4
Cl
CH
2
0
CF
3
H
H
CH
3
2-6
Cl
CH
2
0
CF
3
H
H
C
2
H
5
2-8
Cl
CH
2
0
CF
3
H
H
n-C
3
H
7
2-28
Cl
CH
2
0
CF
3
H
H
CH
2
CH═CH
2
2-38
Cl
CH
2
0
CF
3
H
H
CH
2
C≡CH
2-44
Cl
CH
2
0
CF
3
H
H
c-C
3
H
5
2-134
Cl
CH
2
0
CF
3
H
CH
3
CH
3
2-136
Cl
CH
2
0
CF
3
H
CH
3
C
2
H
5
2-138
Cl
CH
2
0
CF
3
H
CH
3
n-C
3
H
7
2-155
Cl
CH
2
0
CF
3
CH
3
H
CH
3
2-157
Cl
CH
2
0
CF
3
CH
3
H
C
2
H
5
2-159
Cl
CH
2
0
CF
3
CH
3
H
n-C
3
H
7
2-163
Cl
CH
2
0
CF
3
CH
3
CH
3
CH
3
2-165
Cl
CH
2
0
CF
3
CH
3
CH
3
C
2
H
5
2-167
Cl
CH
2
0
CF
3
CH
3
CH
3
n-C
3
H
7
2-202
Br
CH
2
0
CF
3
H
H
CH
3
2-204
Br
CH
2
0
CF
3
H
H
C
2
H
5
2-206
Br
CH
2
0
CF
3
H
H
n-C
3
H
7
2-218
Br
CH
2
0
CF
3
H
H
CH
2
CH═CH
2
2-224
Br
CH
2
0
CF
3
H
H
CH
2
C≡CH
2-226
Br
CH
2
0
CF
3
H
H
c-C
3
H
5
Then, the description will be made on the processes for producing the hydrazine oxoacetamide derivative or salts thereof.
Production Process A
The hydrazine oxoacetamide derivatives of the present invention represented by Formula (I) can be easily produced by reacting a compound (VIII) represented by Formula (VIII):
wherein R
1
, Y, p, R
2
and R
3
are the same as defined above, and R
6
represents an alkyl group, preferably a linear or branched alkyl group having 1 to 6 carbon atoms, particularly preferably 1 or 2 carbon atoms; preferred examples thereof being a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, an n-pentyl group, an isopentyl group, an s-pentyl group, a t-pentyl group, a neopentyl group, an n-hexyl group, an isohexyl group, an s-hexyl group, a t-hexyl group and a neohexyl group with a compound (IX) represented by Formula (IX):
wherein R
4
and R
5
are the same as defined above.
Production Process B
The compound represented by Formula (I) can be easily produced by reacting a compound (X) represented by Formula (X):
wherein R
1
, Y, p, R
2
and R
3
are the same as defined above, with a compound (XI) represented by Formula (XI):
wherein X represents a chlorine or bromine atom, and R
4
and R
5
are the same as defined above, in the presence of a base, if necessary.
Production Process C
The compound represented by Formula (I), wherein R
1
, Y, p, R
2
, R
3
, R
4
and R
5
are the same as defined above, can be easily produced by reacting a compound, represented by Formula (IX) wherein at least one of R
3
, R
4
and R
5
represents a hydrogen atom, with a compound (XII) of Formula (XII):
X—R
7
  (XII)
wherein X represents a halogen atom (such as a chlorine atom) and R
7
represents a methyl group, an ethyl group, an n-propyl group, a cyclopropyl group, an allyl group or a propargyl group,
or a compound (XIII) of Formula (XIII):
(R
8
O)
2
SO
2
  (XIII)
wherein R
8
represents a methyl group, an ethyl group or the like as described above, in the presence of a base, if necessary.
As for Production Process A
When the starting materials are, for example, methyl {N′-[(4-chlorophenyl)-(4-trifluoromethanesulfonyloxyphenyl)-methylene]hydrazino}-oxo-acetate and ethylamine, the reaction is shown by the following reaction formula (1):
Reaction formula (1):
Examples of the compounds (VIII) usable as the starting material in the above-described process are shown in Table 3 below.
TABLE 3
Intermediate
No.
R
1
Y
p
R
2
R
3
R
6
Literature
5-2 
Cl
O
2
CF
3
H
CH
3
J.P. Kokai
Hei 10-67732
5-4 
Cl
O
2
CF
3
H
C
2

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