Insecticidal biphenylthiohydrazides

Details Insecticidal biphenylthiohydrazides Insecticidal biphenylthiohydrazides

1998-12-03

2001-06-05

Killos, Paul J. (Department: 1623)

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

C564S074000, C514S599000, C514S602000

Reexamination Certificate

active

06242647

ABSTRACT:

BACKGROUND OF THE INVENTION
Significant global economic losses in major agronomic crop production are caused by the damage and infestation of insect and acarid pests. Crop reduction due to said pests, for example, in cotton and peanuts, can range as high as 39% and 78%, respectively. Pest infestation can result in lower yields, lower crop quality, reduced consumption, increased perishability, increased risk of disease, higher processing cost, higher transportation cost and increased market prices. Therefore, new and effective insect and acarid control agents and crop protection methods are a continuing global need.
It is thus an object of this invention to provide N-biphenylthiohydrazone derivatives which are effective agents for the control of pestiferous insects and especially, acarina.
It is another object of this invention to provide a method for the protection of growing and harvested crops from the harmful and deleterious effects caused by insects and especially, acarid pests.
It is a further object of this invention to provide insecticidal and acaricidal compositions for use in the methods of the invention.
SUMMARY OF THE INVENTION
The present invention provides novel N-biphenylhydrazone compounds of formula I
wherein
R is hydrogen,
C
1
-C
10
alkyl optionally substituted with one or more halogen,
C
3
-C
6
cycloalkyl,
C
1
-C
4
alkoxy,
C
1
-C
4
haloalkoxy,
(C
1
-C
4
-alkyl)SO
x
,
(C
1
-C
4
haloalkyl)SO
y
,
phenyl optionally substituted with one to three halogen,
C
1
-C
4
alkyl,
C
1
-C
4
haloalkyl,
C
1
-C
4
alkoxy,
C
1
-C
4
haloalkoxy,
(C
1
-C
4
alkyl)SO
x
,
(C
1
-C
4
haloalkyl)SO
y
,
NO
2
or CN groups, or
phenoxy optionally substituted with one to three halogen,
C
1
-C
4
alkyl,
C
1
-C
4
haloalkyl,
C
1
-C
4
alkoxy,
C
1
-C
4
haloalkoxy,
(C
1
-C
4
alkyl)SO
x
,
(C
1
-C
4
haloalkyl)SO
y
,
NO
2
or CN groups;
C
3
-C
12
cycloalkyl optionally substituted with one or more halogens,
C
1
-C
6
alkyl,
C
1
-C
4
haloalkyl,
C
1
-C
4
alkoxy,
C
1
-C
4
haloalkoxy,
(C
1
-C
4
alkyl)SO
x
,
(C
1
-C
4
haloalkyl)SO
x
,
phenyl optionally substituted with one to three halogen,
C
1
-C
4
alkyl
C
1
-C
4
haloalkyl,
C
1
-C
4
alkoxy,
C
1
-C
4
haloalkoxy,
NO
2
or CN groups, or
phenoxy optionally substituted with one to three halogen,
C
1
-C
4
alkyl,
C
1
-C
4
haloalkyl,
C
1
-C
4
alkoxy,
C
1
-C
4
haloalkoxy,
NO
2
or CN groups; or
phenyl optionally substituted with one or more halogen,
C
1
-C
4
alkyl,
C
1
-C
4
haloalkyl,
C
1
-C
4
alkoxy,
C
1
-C
4
haloalkoxy,
NO
2
or CN groups;
with the proviso that when R is phenyl, then m must be 1 or 2;
R
1
is R
12
,
C
1
-C
10
alkyl optionally substituted with one or more halogen,
hydroxy,
phenyl optionally substituted with one or more halogen,
C
1
-C
4
alkyl,
C
1
-C
4
haloalkyl,
C
1
-C
4
alkoxy,
C
1
-C
4
haloalkoxy,
NO
2
or CN groups,
C
1
-C
4
alkoxy,
C
1
-C
4
haloalkoxy,
(C
1
-C
4
alkyl)SO
x
,
CONR
8
R
9
,
CO
2
R
10
,
R
12
,
C
3
-C
6
cycloalkyl optionally substituted with one to three halogen,
C
1
-C
4
alkyl,
C
1
-C
4
haloalkyl,
C
1
-C
4
alkoxy,
C
1
-C
4
haloalkoxy,
NO
2
or CN groups,
phenyl optionally substituted with one or more halogen,
C
1
-C
4
alkyl,
C
1
-C
4
haloalkyl,
C
1
-C
4
alkoxy,
C
1
-C
4
haloalkoxy,
NO
2
or CN groups, or
pyridyl optionally substituted with one or more halogen,
C
1
-C
4
alkyl,
C
1
-C
4
haloalkyl,
C
1
-C
4
alkoxy,
C
1
-C
4
haloalkoxy,
NO
2
or CN groups;
C
2
-C
10
alkenyl optionally substituted with one or more halogen,
hydroxy,
C
1
-C
4
alkoxy,
C
1
C
4
alkyl)SO
x
,
CONR
8
R
9
,
CO
2
R
10
,
R
11
,
R
12
,
C
3
-C
6
cycloalkyl optionally substituted with one to three halogen,
C
1
-C
4
alkyl,
C
1
-C
4
halo-alkyl,
C
1
-C
4
alkoxy,
C
1
-C
4
haloalkoxy,
NO
2
or CN groups,
phenyl optionally substituted with one or more halogen,
C
1
-C
4
alkyl,
C
1
-C
4
haloalkyl,
C
1
-C
4
alkoxy,
C
1
-C
4
haloalkoxy,
NO
2
or CN groups, or
pyridyl optionally substituted with one or more halogen,
C
1
-C
4
alkyl,
C
1
-C
4
haloalkyl,
C
1
-C
4
alkoxy,
C
1
-C
4
haloalkoxy,
NO
2
or CN groups;
C
2
-C
10
alkynyl optionally substituted with one or more halogen,
hydroxy,
C
1
-C
4
alkoxy,
(C
1
-C
4
alkyl)SO
x
,
CONR
8
R
9
,
CO
2
R
10
,
R
11
,
R
12
,
C
3
-C
6
cycloalkyl optionally substituted with one to three halogen,
C
1
-C
4
alkyl,
C
1
-C
4
halo-alkyl,
C
1
-C
4
alkoxy,
C
1
-C
4
haloalkoxy,
NO
2
or CN groups,
phenyl optionally substituted with one or more halogen,
C
1
-C
4
alkyl,
C
1
-C
4
haloalkyl,
C
1
-C
4
alkoxy,
C
1
-C
4
haloalkoxy,
NO
2
or CN groups, or
pyridyl optionally substituted with one or more halogen,
C
1
-C
4
alkyl,
C
1
-C
4
haloalkyl,
C
1
-C
4
alkoxy,
C
1
-C
4
haloalkoxy,
NO
2
or CN groups; or
C
3
-C
12
cycloalkyl optionally substituted with one or more halogen,
hydroxy,
C
1
-C
4
alkoxy,
(C
1
-C
4
alkyl)SO
x
,
CONR
8
R
9
,
CO
2
R
10
,
R
11
,
R
12
,
C
3
-C
6
cycloalkyl optionally substituted with one to three halogen,
C
1
-C
4
alkyl,
C
1
-C
4
halo-alkyl,
C
1
-C
4
alkoxy,
C
1
-C
4
haloalkoxy,
NO
2
or CN groups,
phenyl optionally substituted with one or more halogen,
C
1
-C
4
alkyl,
C
1
-C
4
haloalkyl,
C
1
-C
4
alkoxy,
C
1
-C
4
haloalkoxy,
NO
2
or CN groups, or
pyridyl optionally substituted with one or more halogen,
C
1
-C
4
alkyl,
C
1
-C
4
haloalkyl,
C
1
-C
4
alkoxy,
C
1
-C
4
haloalkoxy,
NO
2
or CN groups;
phenyl optionally substituted with one or more halogen,
C
1
-C
4
alkyl,
C
1
-C
4
haloalkyl,
C
1
-C
4
alkoxy,
C
1
-C
4
haloalkoxy,
NO
2
or CN groups, or
pyridyl optionally substituted with one or more halogen,
C
1
-C
4
alkyl,
C
1
-C
4
haloalkyl,
C
1
-C
4
alkoxy,
C
1
-C
4
haloalkoxy,
NO
2
or CN groups;
R
2
is hydrogen or C
1
-C
4
alkyl;
R
3
, R
4
, R
5
, R
6
, and R
7
are each independently hydrogen, halogen, CN, NO
2
, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, or phenyl optionally substituted with one to three halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy, (C
1
-C
4
alkyl)SO
x
, (C
1
-C
4
haloalkyl)SO
y
, NO
2
or CN groups,
with the proviso that at least one of R
3
, R
4
, R
5
, R
6
or R
7
must be phenyl optionally substituted with one to three halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy, (C
1
-C
4
alkyl)SO
x
, (C
1
-C
4
haloalkyl)SO
x
, NO
2
or CN groups;
x and y are each independently 0, 1 or 2;
m is an integer of 0, 1 or 2;
R
8
, R
9
and R
10
are each independently hydrogen or C
1
-C
4
alkyl;
R
11
is NR
13
R
14
,
R
12
is
R
13
, R
14
, and R
15
are each independently hydrogen or C
1
-C
4
alkyl;
X is O, S or NR
15
;
R
16
is hydrogen, halogen or C
1
-C
4
alkyl;
r is an integer of 0 or 1;
p and q are each independently an integer of 0, 1, 2, or 3 with the proviso that only one of p, q, or r can be 0 and with the further proviso that the sum of p+q+r must be 4, 5 or 6; and
x is an integer of 0, 1 or 2; or
the acid addition salts thereof.
Also provided are methods and compositions for the control of insect and acarid pests and for the protection of growing and harvested crops from attack and infestation thereby.
DETAILED DESCRIPTION OF THE INVENTION
A wide variety of insects and acarina cause great economic loss by damaging or destroying agricultural crops and horticultural and pharmaceutical plants; by aiding in the spread and development of bacteria, fungi and viruses that produce diseases of plants; and by destroying or lowering the value of stored foods, other products and possessions. Insect and acarid attack and infestation cause some of the farmers' greatest problems the world over. The need for alternative and effective insect and acarid control is a global concern.
It has now been found that the N-biphenylthiohydrazone compounds of formula I are highly effective agents for the control of a wide variety of insect and, particularly, acarid pests. As such, these compounds can be used to advantage to combat mites of the species
Tetranychus uriticae
(Koch). Moreover, compounds of the present invention have been found to exhibit good activity against mite species which have developed resistance to existing commercial acaricides.
Advantageously, compounds of formula I not only possess acaricidal activity but

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