Pesticidal 1-arylpyrazoles

Details Pesticidal 1-arylpyrazoles Pesticidal 1-arylpyrazoles

2000-05-26

2002-06-11

Ramsuer, Robert W. (Department: 1626)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

C548S367400

Reexamination Certificate

active

06403628

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to 3-acetyl-1-aryl-pyrazole derivatives useful in the control of insects, nematodes or helminths, and to compositions containing the same. The method of the invention particularly relates to the application of the 1-arylpyrazole derivatives under conditions where some worker exposure is likely to occur. The invention also relates to a new and improved method of control of insects, nematodes or helminths, using an insecticidally active material having a 1-phenyl pyrazole group therein and is particularly useful for the control of aphids.
2. Description of the Related Art
The control of insects, nematodes or helminths by means of active material having a 1-arylpyrazole group therein has been described by many patents or patent applications such as International Patent Publication No. WO 93/06089 (and the equivalent U.S. Pat. No. 5,451,598), WO 94/21606 and WO 87/03781 as well as in European Patent Publication Numbers 0295117, 659745, 679650, 201852 and 412849, German Patent No. DE19511269 and U.S. Pat. No. 5,232,940.
The first object of the instant invention is to provide an improved level of safety to the user and the environment in the methods of control of insects, nematodes or helminths. All pesticides are generally more or less hazardous, and it is always desirable to lower the potential hazards which might exist even if these are quite low and acceptable for normal uses. Thus it is an object of the instant invention to develop a method of control wherein the potential hazards are lowered by comparison with the known and existing methods, even if these existing hazards are low and acceptable.
A second object of the invention is to lower the hazards for working people in such methods of use. A third object of the present invention is to lower the hazards for working people in such methods of use when a substantial exposure might occur.
A fourth object of the present invention is to provide a new and better method of control of aphids. The control of aphids by many insecticidally active materials is known but these insect species are capable of extremely rapid population growth with a substantial and higher risk of resistance developing to pesticides than occurs for other insect species. Thus it is highly desirable to be able to introduce new methods of control using pesticides other than those used up to now. It is an object of the instant invention to provide a method of control using insecticidally active material of the 1-phenyl pyrazole type which has a high efficiency, and if possible, a better efficiency than the methods known up to now.
A fifth object of the present invention is to provide new 1-phenylpyrazole derivatives which possess improved systemic aphicidal activity compared to known compounds. These compounds possess excellent properties in controlling cotton leaf aphid (
Aphis gossypii
) and greenbug (
Schizaphis graminum
) in systemic applications.
These and other objects of the invention shall become readily apparent from the description of the present invention which follows, and are achieved in whole or in part by the invention.
SUMMARY OF THE INVENTION
This invention provides an improvement in a method of control of insects by means of application of an insecticidally active ingredient having a 1-arylpyrazole group to a locus where insects are present or expected to be present, said application being made under conditions whereby an exposure of mammalian species, especially a substantial exposure, may occur, the improvement whereby the said active ingredient has a 3-acetyl substituent on the pyrazole ring. The method of control of the invention is particularly suitable when there may be an exposure to working people.
The invention also provides a method of control of insects by means of application of an insecticidally active ingredient having a 1-arylpyrazole group to a locus where aphids insects are present or expected to be present, the improvement whereby the said active ingredient has a 3-acetyl substituent on the pyrazole ring.
Practically the applications according to the inventions are using an active ingredient of formula (I):
wherein:
R
1
is S(O)
m
R
5
;
R
2
is selected from a hydrogen atom, a halogen atom —NR
6
R
7
, —S(O)
n
R
8
, C(O)R
8
, C(O)OR
9
, alkyl, haloalkyl, —OR
9
, or —N═C(R
10
)(R
11
);
R
3
is selected from a halogen atom or the hydrogen atom;
R
4
is selected from a halogen atom, haloalkyl, haloalkoxy, —S(O)
p
CF
3
, or —SF
5
;
R
5
is alkyl or haloalkyl;
R
6
and R
7
are independently selected from a hydrogen atom, alkyl, haloalkyl, —C(O) R
8
, C(O)OR
8
, —S(O)
q
CF
3
; the alkyl portions of which are optionally substituted by one or more R
12
; or R
6
and R
7
are joined so as together form a divalent radical having 4 to 6 atoms in the chain, this divalent radical being alkylene, alkyleneoxyalkylene or alkyleneaminoalkylene, preferably to form a morpholine, pyrrolidine, piperidine or piperazine ring;
R
8
is alkyl or haloalkyl;
R
9
is selected from alkyl, haloalkyl or the hydrogen atom;
R
10
is selected from R
9
or alkoxy;
R
11
is alkyl or haloalkyl; or is selected from phenyl or heteroaryl that is optionally substituted by one or more groups selected from hydroxy, halogen, alkoxy, —S(O)
r
R
8
, cyano, R
8
or combinations thereof;
R
12
is selected from cyano, nitro, alkoxy, haloalkoxy, —S(O)
s
-alkyl, —S(O)
s
-haloalkyl, C(O)-alkyl, C(O)-haloalkyl, C(O)O-alkyl, C(O)O-haloalkyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, hydroxy, aminosulfonyl, alkylaminosulfonyl or dialkylaminosulfonyl;
X is selected from the nitrogen atom, or the radical C—R
13
;
R
13
is a halogen atom; and
m, n, p, q, r and s represent, independently of one another, the values zero, one or two;
or a pesticidally acceptable salt thereof.
By the term “pesticidally acceptable salts” is meant salts the anions and cations of which are known and accepted in the art for the formation of pesticidally acceptable salts. Preferably such salts are water soluble. Suitable acid addition salts formed from compounds of formula (I) containing an amine group, include salts with inorganic acids for example hydrochlorides, phosphates, sulfates and nitrates, and salts with organic acids for example acetates. Suitable salts formed with bases from compounds of formula (I) containing a carboxylic acid group, include alkali metal (for example sodium or potassium) salts, ammonium salts and organic amine (for example diethanolamine or morpholine) salts.
DETAILED DESCRIPTION OF THE INVENTION
Unless otherwise specified alkyl and alkoxy groups have from one to four carbon atoms. The haloalkyl and haloalkoxy groups likewise preferably have one to four carbon atoms. The various individual aliphatic hydrocarbon moieties, that is, radicals and portions thereof (for example the alkyl moiety of alkylaminocarbonyl and alkylaminosulfonyl) have up to four carbon atoms in the chain.
The haloalkyl and haloalkoxy groups can bear one or more halogen atoms.
The term heteroaryl refers to a five to seven membered heterocyclic ring containing from one to four heteroatoms selected from nitrogen, oxygen and sulfur.
The term halogen means F, Cl, Br or I. 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.
R
2
is preferably an amino group, which is unsubstituted or which bears one or two substituents selected from the group consisting of alkyl, —C(O) R
8
and —C(O)OR
8
; the alkyl portions of which are optionally substituted by one or more R
12
.
R
3
is preferably a halogen atom; especially preferred is a chlorine atom; R
4
is preferably selected from a halogen atom, haloalkyl, haloalkoxy, or —SF
5
; especially preferred are CF
3
—, CF
3
O— and —SF
5
.
R
5
is preferably methyl, ethyl or propyl.
A particularly preferred group of compounds of general formula (I) because of their systemic aphicidal properties are those wherein:
R
2
is NR
6
R
7
;
R
3
is ha

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