Pesticidal compounds and compositions

Details Pesticidal compounds and compositions Pesticidal compounds and compositions

2001-03-02

2002-10-01

McKane, Joseph K. (Department: 1626)

Plant protecting and regulating compositions

Antidotes

Hetero ring containing antidote

C514S341000, C514S406000, C546S275400, C548S364100, C504S106000

Reexamination Certificate

active

06458744

ABSTRACT:

BACKGROUND OF THE INVENTION
1. FIELD OF THE INVENTION
The invention relates to new 4-thiomethylpyrazole compounds, related compounds, compositions containing them, processes for their preparation, and their use for the control of arthropod pests (especially insects) and nematodes.
2. DESCRIPTION OF THE RELATED ART
Pesticidal N-arylpyrazoles are described in the art, for example, in EP 0234119, EP 0511845, EP 0352944 and EP 0295117.
SUMMARY OF THE INVENTION
The present invention provides a compound of formula (I):
wherein:
Q is a group (A1) or (A2):
W is N or CR
6
;
—X
1
—X
2
—X
3
— is —CF
2
CF
2
O—, —CF
2
OCF
2
— or —OCF
2
O—;
R
1
is alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, cycloalkylalkyl or —(CH
2
)
m
R
7
; or is naphthyl optionally substituted by alkyl, haloalkyl, halogen, NO
2
, alkoxy, haloalkoxy or R
8
S(O)
p
;
R
2
is hydrogen, halogen or optionally substituted amino;
R
3
and R
6
are each independently hydrogen or halogen;
R
4
is hydrogen or haloalkyl;
R
5
is hydrogen, halogen, haloalkyl, haloalkoxy, —S(O)
p
CF
3
or SF
5
;
R
7
is phenyl or a five to seven membered heteroaromatic ring having from one to four heteroatoms which are the same or different selected from nitrogen, oxygen and sulfur, which ring is optionally substituted by R
9
;
R
8
is alkyl or haloalkyl;
R
9
is alkyl, haloalkyl, halogen, CN, NO
2
, R
10
O, R
8
S(O)
p
, C(O)R
8
, C(O)OR
10
or NR
10
R
11
; or when R
7
is phenyl two adjacent R
9
groups together form a —CF
2
OCF
2
— or —OCF
2
O— group;
R
10
and R
11
are each independently hydrogen, alkyl or haloalkyl; and
m, n and p each independently have the value zero, one or two;
or an agriculturally acceptable salt thereof.
The compounds of formula (I) and the agriculturally acceptable salts thereof as defined above possess valuable pesticidal properties. The compounds of the invention show improved pesticidal activity in comparison with known compounds.
The invention also encompasses any stereoisomer, enantiomer or geometric isomer, or mixture thereof, of the compounds of formula (I).
By the term “agriculturally acceptable salts” is meant salts the cations or anions of which are known and accepted in the art for the formation of salts for agricultural or horticultural use. Suitable salts with bases include alkali metal (e.g. sodium and potassium), alkaline earth metals (e.g. calcium and magnesium), ammonium and amine (e.g. diethanolamine, triethanolamine, octylamine, morpholine and dioctylmethylamine) salts. Suitable acid addition salts, e.g. formed by compounds of formula (I) containing an amino group, include salts with inorganic acids, for example hydrochlorides, sulfates, phosphates and nitrates and salts with organic acids for example acetic acid.
DETAILED DESCRIPTION OF THE INVENTION
Unless otherwise specified, alkyl, acyl and alkoxy groups (or portions thereof) are straight- or branched- chain and have from one to ten (preferably one to six) carbon atoms.
Cycloalkyl groups have from three to six carbon atoms in the ring and are optionally substituted by alkyl or halogen.
Alkenyl and alkynyl groups or portions thereof are straight- or branched-chain and have from two to eight (preferably two to four) carbon atoms.
The term “halo” before the name of a radical means that this radical is partially or completely halogenated, that is to say, substituted by F, Cl, Br, or I, in any combination, preferably by F or Cl. The term “halogen” means F, Cl, Br or I.
A preferred embodiment of the invention comprises a compound of formula (I) wherein Q, R
1
and n are as defined above and R
2
is —NR
12
R
13
or —N═C(R
10
)(R
14
), wherein:
R
12
and R
13
are independently selected from hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, —C(O)R
15
and C(O)OR
15
; or R
12
and R
13
are joined together to form a divalent radical having 4 to 6 atoms in the chain, this divalent radical being alkylene, alkyleneoxyalkylene or alkyleneaminoalkylene (preferably forming a morpholine, pyrrolidine, piperidine or piperazine ring);
R
14
is alkoxy or haloalkoxy; or is phenyl optionally substituted by alkyl, haloalkyl, hydroxy, halogen, alkoxy, —S(O)
p
R
8
or CN;
R
15
is alkenyl, haloalkenyl, alkynyl or haloalkynyl; or is alkyl optionally substituted by halogen, alkoxy, C(O)R
8
, C(O)OR
10
, CN, —S(O)
p
R
8
, or CONR
10
R
11
.
Preferred compounds of formula (I) are those in which R
1
is alkyl, haloalkyl, cycloalkyl or naphthyl; or phenyl optionally substituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or NO
2
; or pyridyl optionally substituted by halogen or haloalkyl; or —CH
2
R
7
wherein R
7
is phenyl optionally substituted by halogen, alkyl or alkoxy; or —CH
2
CH
2
R
7
wherein R
7
is phenyl.
Preferred compounds of formula (I) are those in which Q is a group (A1) wherein:
W is N or CR
6
; R
3
and R
6
are each independently hydrogen or halogen; R
4
is hydrogen; and R
5
is halogen, CF
3
, OCF
3
or SF
5
; or wherein:
W is N or CR
6
; R
3
and R
6
are each independently hydrogen or halogen; R
4
is CF
3
; and R
5
is hydrogen.
More preferred compounds of formula (I) are those in which Q is a group (A1) wherein:
W is CR
6
; R
3
is hydrogen or halogen; R
6
is halogen; R
4
is hydrogen; and R
5
is halogen, CF
3
or OCF
3
; or wherein:
W is CR
6
; R
3
is hydrogen; R
6
is halogen; R
4
is CF
3
; and R
5
is hydrogen.
Preferred compounds of formula (I) are those in which R
2
is —NR
12
R
13
or —N═C(R
10
)(R
14
).
More preferred compounds are those in which R
2
is —NR
12
R
13
or —N=C(R
10
)(R
14
), wherein R
12
is hydrogen, alkyl or —C(O)R
15
; R
13
is hydrogen or alkyl; R
10
is hydrogen; R
14
is alkoxy; and R
15
is alkyl.
Yet more preferred compounds are those in which R
2
is —NHR
13
or —N═CH(R
14
); wherein R
13
is hydrogen or alkyl; and R
14
is alkoxy.
Compounds in which R
2
is amino are most preferred.
Compounds in which n is 1 or 2 are also preferred.
A preferred class of compounds of formula (I) are those in which:
R
1
is alkyl, haloalkyl, cycloalkyl or naphthyl; or phenyl optionally substituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or NO
2
; or pyridyl optionally substituted by halogen or haloalkyl; or —CH
2
R
7
wherein R
7
is phenyl optionally substituted by halogen, alkyl or alkoxy; or —CH
2
CH
2
R
7
wherein R
7
is phenyl;
Q is a group (A1) wherein:
W is N or CR
6
; R
3
and R
6
are each independently hydrogen or halogen; R
4
is hydrogen; and R
5
is halogen, CF
3
, OCF
3
or SF
5
; or wherein:
W is N or CR
6
; R
3
and R
6
are each independently hydrogen or halogen; R
4
is CF
3
; and R
5
is hydrogen; and
R
2
is —NR
12
R
13
or —N═C(R
10
)(R
14
); wherein R
12
is hydrogen, alkyl or —C(O)R
15
; R
13
is hydrogen or alkyl; R
10
is hydrogen; R
14
is alkoxy; and R
15
is alkyl.
A further preferred class of compounds of formula (I) are those in which:
R
1
is alkyl, haloalkyl, cycloalkyl or naphthyl; or phenyl optionally substituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or NO
2
; or pyridyl optionally substituted by halogen or haloalkyl; or —CH
2
R
7
wherein R
7
is phenyl optionally substituted by halogen, alkyl or alkoxy; or —CH
2
CH
2
R
7
wherein R
7
is phenyl;
Q is a group (A1) wherein:
W is N or CR
6
; R
3
and R
6
are each independently hydrogen or halogen; R
4
is hydrogen; and R
5
is halogen, CF
3
, OCF
3
or SF
5
; or wherein:
W is N or CR
6
; R
3
and R
6
are each independently hydrogen or halogen; R
4
is CF
3
; and R
5
is hydrogen;
R
2
is —NR
12
R
13
or —N═C(R
10
)(R
14
); wherein R
12
is hydrogen, alkyl or —C(O)R
15
; R
13
is hydrogen or alkyl; R
10
is hydrogen; R
14
is alkoxy; and R
15
is alkyl; and
n is 1 or 2.
A further preferred class of compounds of formula (I) are those in which:
R
1
is alkyl, haloalkyl, cycloalkyl or naphthyl; or phenyl optionally substituted by halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or NO
2
; or pyridyl optionally substituted by halogen or haloalkyl; or —CH
2
R
7
wherein R
7
is phenyl optionally substituted by halogen, alkyl or alkoxy; or —CH
2
CH
2
R

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