Pesticidal 1-arylpyrazoles

Details Pesticidal 1-arylpyrazoles Pesticidal 1-arylpyrazoles

2000-11-17

2002-05-28

Fan, Jane (Department: 1625)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C546S275400

Reexamination Certificate

active

06395760

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The invention relates to new derivatives of 1-arylpyrazoles which have some valuable properties either as pesticides or as intermediates to make other pesticides. The invention further pertains to compositions of said compounds and methods, using said compounds either as intermediates to make other pesticides, or for the control of arthropod pests, in particular to the application of said compounds or compositions in agricultural methods of use or for animal protection, particularly as pesticides, for controlling arthropods.
2. Description of the Related Art
International Patent Publication No. WO 87/03781 and European Patent Publication Nos. 0295117, 0154115, 0201852 describe insecticidal 1-(substituted phenyl)pyrazoles. Other prior art is also found in the text of these patent applications or the patents issued therefrom.
International Patent Publication Nos. WO 93/06089 and WO 94/21606 also describe insecticidal 1-(4-SF
5
substituted phenyl) heterocycles which may be pyrroles as well as imidazoles or pyrazoles. The teaching of these patents is not substantially different from International Patent Publication No. WO 87/03781 or from European Patent Publication No. 0295117 as far as pyrazoles are concerned.
Various pesticidal pyrazoles have been disclosed in various patents or patent applications: European 0418016, 0403309, 0352944; U.S. Pat. Nos. 5,104,994, 5,079,370, 5,047,550, 5,232,940, 4,810,720, 4,804,675, 5,306,694, 4,614,533, 5,187,185, 5,223,525; WO 93/06089, 94/21606.
Due to the many existing pests and crops and conditions of attacks of crops by pests, there is a need for further novel pesticidal compounds.
OBJECTS AND SUMMARY OF THE INVENTION
It is an object of the present invention to provide new pesticidal compounds of the 1-arylpyrazole family together with processes for their preparation.
A second object of the present invention is to provide pesticidal compositions and pesticidal methods of use of the pesticidal pyrazole compounds against arthropods, especially insects, particularly in agricultural or horticultural crops, forestry, veterinary medicine or livestock husbandry, or in public health.
A third object of the present invention is to provide very active compounds, with broad spectrum pesticidal activity, as well as compounds with selective special activity, e.g., aphicidal, miticidal, foliar insecticidal, soil insecticidal, systemic, antifeeding or pesticidal activity via seed treatment.
These and other objects, which are met in whole or in part by the instant invention, shall become readily apparent from the description of the invention which follows.
This invention embraces novel chemical compounds having an insecticidal, miticidal, nematocidal or anthelminthic activity.
The invention relates to compounds having the general formula (I):
wherein:
R
31
and R
32
may individually be OR
20
, S(O)
n
R
20
, or N(R
20
)(R
21
); or R
31
and R
32
may also connect to form O[C(R
22
)(R
23
)]
m
O, S(O)
n
[C(R
22
)(R
23
)]
m
S(O)
a
, O(CH
2
)
m
S(O)
n
, O[C(R
22
)(R
23
)]
m
(NR
20
), S(O)
n
[C(R
22
)(R
23
)]
m
(NR
20
), NR
21
[C(R
22
)(R
23
)]
m
NR
20
, NR
21
[C(O)(CH
2
)
m
]NR
20
;
m is an integer from 1 to 5;
when m is greater than one, the groups [C(R
22
)(R
23
)] may be the same or different;
R
20
, R
21
may individually be H, alkyl, aryl, benzyl, allyl, propargyl;
R
22
, R
23
may individually be H; halogen; OH; NH
2
; COOR
20
; C(O)NH
2
; C(O)N(R
20
)(R
21
); C(S)NH
2
; OC(O)N(R
20
)(R
21
); CN; NO
2
; C(S)N(R
20
)(R
21
); alkyl which may optionally be substituted with OH, NH
2
, halogen, CN, NO
2
, COOR
20
, C(O)NH
2
, C(S)NH
2
; S(O)
b
alkyl; alkoxy; S(O)
c
R
20
;
R
4
is R
26
; S(O)
d
R
26
; S(═R
27
)(═NR
28
)R
26
;
R
26
is alkyl optionally substituted with one or more halogen which may be the same or different;
R
5
is NH
2
, alkylamino where the alkyl may be substituted with NO
2
, halogen, CN, alkoxycarbonyl, OH, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or carbamoyl; or R
5
is a radical having the formula:
wherein
R
4
, R
12
, R
13
, R
14
, R
15
, Z and R
33
are identical to R
4
, R
12
, R
13
, R
14
, R
15
, Z and R
33
, respectively, in formula (I) above;
R
27
is NR
28
, O or a lone pair of electrons;
R
28
is selected from H; C
1
-C
6
alkyl; C
1
-C
6
haloalkyl; COR
24
; S(O)
e
R
24
; COOR
24
; C(O)N(R
20
)(R
21
); C(O)SR
24
; C(S)OR
24
; SO
2
NR
20
R
21
; P(O)
q
(R
20
)(R
21
); P(O)
q
(OR
20
)(OR
21
); C(═NR
20
)NR
20
R
21
; C(═NR
20
)(OR
21
); C(S)N(R
20
)(R
21
); C(O)C(O)R
20
; C(O)C(O)OR
20
; C(O)C(O)NR
20
R
21
; and C(O)NR
20
SO
2
R
21
;
q is 0 or 1;
R
24
is alkyl optionally substituted with NO
2
, CN, halogen, alkoxy, amino, alkoxycarbonyl or OH;
Z is N or C—R
16
;
R
12
, R
13
, R
14
, R
15
and R
16
may individually be H; halogen; SF
5
; CN; NO
2
; R
25
; S(O)
f
R
25
; OH; OR
25
; N(R
36
)(R
37
); CON(R
25
)(R
37
); N
3
(azido);
R
36
and R
37
may individually be H, alkyl;
R
25
may be alkyl optionally substituted with one or more halogen which may be the same or different;
R
33
is C
1
to C
3
alkyl, optionally substituted by one or more halogen, NO
2
, alkoxy, CN, COOH, COO-alkyl, C(O)NH
2
; and
n, a, b, c, d, e and f, which are the same or different, are each 0, 1 or 2; and pesticidally acceptable salts thereof.
DETAILED DESCRIPTION OF THE INVENTION AND PREFERRED EMBODIMENTS
The stereoisomers, e.g. diastereomers and optical isomers, having the formula (I) are included in the invention as well.
In this description, the term ‘alkyl’ when unqualified generally means a straight- or branched-chain alkyl having from one to six carbon atoms. The term ‘aryl’ means C
6
-C
10
aryl, e.g. phenyl or naphthyl, optionally bearing one or more substituents selected from the group consisting of halogen, C
1
-C
6
alkyl, C
1
-C
6
alkoxy, CN, NO
2
, C
1
-C
6
haloalkyl and C
1
-C
6
haloalkoxy.
Preferred compounds of formula (I) include those wherein R
13
and R
15
are or halogen; R
12
is halogen; R
16
is H or halogen; and/or R
14
is halogen, SF5, R
25
, S(O)
f
R
25
or OR
25
. Compounds in which R
12
is chlorine, R
13
and R
15
are H, R
14
is CF
3
, and Z is C—Cl, are especially preferred.
Compounds of formula (I) wherein R
4
is S(O)
d
R
26
and Z is C—R
16
are also referred.
The symbol m is preferably 2, 3 or 4, more preferably 2 or 3, most preferably 2.
Other preferred compounds of formula (I) are those wherein:
R
26
is CH
3
or CH
2
CH
3
; Z is C—R
16
; R
13
and R
15
are H; R
12
is halogen; R
16
is H or halogen; R
14
is CF
3
, OCF
3
or SF
5
; and/or R
33
is CH
3
.
Still most preferred compounds of formula (I) are those wherein:
R
31
and R
32
may individually be OCH
3
; OC
2
H
5
; SCH
3
; SC
2
H
5
; R
31
and R
32
may also connect to form OCH
2
CH
2
O; O(CH
2
)
3
O; S(CH
2
)
2
S; S(O)(CH
2
)
2
S; S(O)(CH
2
)
2
S(O); S(O)
2
(CH
2
)
2
S(O); S(O)
2
(CH
2
)
2
S(O)
2
; S(CH
2
)
2
O; S(O)(CH
2
)
2
O; S(O)
2
(CH
2
)
2
O; O(CH
2
)[CH(CH
2
OH)]O; O(CH
2
)[C(CH
2
OH)(CH
2
OH)]O; OCH(COOCH
3
)CH(COOCH
3
)O; OCH(COOC
2
H
5
)CH(COOC
2
H
5
)O; OCH
2
C(COOCH
3
)(COOCH
3
)CH
2
O; OCH
2
C(COOC
2
H
5
)(COOC
2
H
5
)CH
2
O; OCH
2
CH(CH
3
)O; SCH
2
CH
2
NH; OCH
2
CH(CH
2
CH
2
OH)O; OCH
2
C(CH
2
OH)
2
CH
2
O; OCH
2
CH(CH
2
SCH
3
)O; or OCH
2
CH(CH
2
SOCH
3
)O; particularly when R
4
is S(O)
d
R
26
; R
26
is CH
3
or CH
2
CH
3
; Z is C—R
16
; R
13
and R
15
are H; R
12
is halogen; R
16
is H or halogen; R
14
is CF
3
, OCF
3
or SF
5
; and R
33
is CH
3
.
Preferably, the compounds of formula (I) have one or more of the following features:
R
12
is halogen;
X is C—C1;
R
13
and R
15
are H;
R
14
is CF
3
or SF
5
;
R
5
is NH
2
, CH
3
NH, or CH
3
CH
2
NH;
R
4
is CH
3
S(O), CH
3
S(O)
2
or CH
3
S;
R
31
and R
32
are OCH
3
or connect to form OCH
2
CH
2
O; OCH
2
CH(CH
3
)O; S(CH
2
)
2
S; S(O)(CH
2
)
2
S; S(O)(CH
2
)
2
S(O); S(O)
2
(CH
2
)
2
S(O)
2
; O(CH
2
)[CH(CH
2
OH)]O; SCH
2
CH
2
NH; O(CH
2
)CH(CH
2
SCH
3
)O; O(CH
2
)CH(CH
2
SOCH
3
).
Compounds of the gener

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