Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1999-09-24
2002-08-13
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
06432997
ABSTRACT:
The present invention relates to novel 1-arylpyrazole hydroxylamines, hydrazines, and compositions containing them. The invention particularly pertains to compositions of said compounds and methods and use of said compounds for the control of arthropod, nematode, helminth or protozoan pests, in particular to the application of said compounds or compositions in agricultural methods of use, particularly as pesticides, for controlling arthropods, especially insects by systemic action.
The control of insects, nematodes or helminths by means of an active ingredient having a 1-arylpyrazole group therein has been described in such patent applications such as International Patent Publication No. WO 93/06089, WO 94/21606 and WO 87/03781 as well as in European Patent Publication Numbers 0295117, 659745, 679650, 201852 and 412849, German Patent No. DE 19511269 and U.S. Pat. No. 5,232,940.
Other compounds are disclosed in WO 92/13451, Aug. 20 1992, to Schering Agrochemicals Ltd., which describes 5-chloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(4,5-1H-pyrazole as an intermediate, also with activity against a single species
Lucilia sericata,
sleep blow fly.
This Schering reference appears to be the only reference describing 1-arylpyrazole-oxime compounds as insecticides.
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, plant nematodes, or helminth or protozoan pests, 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 and nematicidal, systemic, antifeeding or pesticidal activity via seed treatment.
A fourth object of the present invention is to provide compounds with substantially enhanced and more rapid activity, especially against insects and more particularly insects in their larval stages.
A fifth object of the present invention is to provide compounds with greatly improved (greater and faster) penetration into pest species when topically applied and thus provide enhanced movement of the compounds to the pesticidal site(s) of action within the pest.
Another object of the present invention is to provide compounds with high activity and improved safety to the user and the environment.
These and other objects of the invention shall become readily apparent from the detailed description of the present invention.
These objects are met in whole or in part by the instant invention.
The present invention provides arylpyrazoles of formula (I):
wherein:
A is —O— or —NR
8
;
Y is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, —S(O)
m
R
10
, —P(O)R
11
R
12
, —P(S)R
12
, —Si(R
13
)(R
14
)(R
15
), —C(O)R
9
, —C(S)R
9
, cyano or nitro;
R
1
is substituted or unsubstituted alkyl or substituted or unsubstituted aryl;
R
2
is —S(O)
n
R
16
or alkyl or haloalkyl;
R
3
is hydrogen, halogen, —C(O)R
17
, —S(O)
p
R
18
, alkyl, haloalkyl, —OR
19
, —N═C(R
20
)(R
21
),alkenyl, —NR
22
R
23
, 1H-pyrrol-1-yl, 1H-pyrazol-1-yl, or —CH═NOH;
R
4
, R
5
and R
7
are independently selected from hydrogen, halogen or alkyl;
R
6
is halogen, haloalkyl, haloalkoxy, —S(O)
q
R
24
or SF
5
;
R
8
is hydrogen or substituted or unsubstituted alkyl;
R
9
is hydrogen, substituted or unsubstituted alkyl of C
1
to C
20
, substituted or unsubstituted aryl, —OR
25
, —NR
26
R
27
, or and —SR
28
;
R
10
is substituted or unsubstituted alkyl or substituted or unsubstituted aryl;
R
11
and R
12
are independently selected from alkoxy and thioalkoxy;
R
13
, R
14
and R
15
are independently selected from alkyl, haloalkyl and aryl;
R
16
is alkyl, alkenyl, alkynyl, or C
3
-C
6
cycloalkyl each of which is optionally substituted by one or more halogen;
R
17
is hydrogen, alkyl, alkoxy or thioalkoxy;
R
18
is alkyl, haloalkyl or aryl;
R
19
and R
20
are independently selected from hydrogen, alkyl and haloalkyl;
R
21
is alkyl, alkoxy or phenyl each of which is optionally substituted by one or more groups selected from hydroxy, halogen, alkoxy, —CN, alkyl, —S(O)
s
-alkyl;
R
22
and R
23
are independently selected from hydrogen, NH
2
, —S(O)
r
R
29
, —C(O)R
30
, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl and alkynyl; or R
22
and R
23
may form together a divalent alkylene radical which may be interrupted by one or more heteroatoms, preferably selected from oxygen, nitrogen and sulfur;
R
24
is haloalkyl;
R
25
and R
28
are independently selected from substituted or unsubstituted alkyl and substituted and unsubstituted aryl;
R
26
and R
27
are independently selected from hydrogen, substituted or unsubstituted alkyl and substituted or unsubstituted aryl; R
26
and R
27
may form together a divalent alkylene radical which may be interrupted by one or more heteroatoms preferably selected from oxygen, nitrogen and sulfur;
R
29
is substituted or unsubstituted alkyl;
R
30
is hydrogen, alkyl, haloalkyl, aryl, alkenyl, —OR
31
, —SR
31
, or —NR
32
R
33
;
R
31
is alkyl or haloalkyl;
R
32
and R
33
are independently selected from hydrogen, alkyl, haloalkyl and aryl;
Z is hydrogen, substituted or unsubstituted alkyl, —S(O)
t
R
34
, —C(O)R
35
, —P(O)R
36
R
37
, —P(S)R
36
R
37
, cyano or nitro;
R
34
is substituted or unsubstituted alkyl or substituted or unsubstituted aryl;
R
35
is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, —OR
38
, —NR
39
R
40
or —SR
41
;
R
36
and R
37
are independently selected from alkoxy, haloalkoxy, thioalkoxy and haiothioalkoxy;
R
38
and R
41
are independently selected from substituted or unsubstituted alkyl, or substituted or unsubstituted aryl;
R
39
and R
40
are independently selected from hydrogen, substituted or unsubstituted alkyl and substituted or unsubstituted aryl; or R
39
and R
40
may form together a divalent alkylene radical which may be interrupted by one or more heteroatoms preferably selected from oxygen, nitrogen and sulfur;
m, n, p, q, r, s, and t independently represent zero, one or two;
M is C-halo, C—CH
3
, C—CH
2
F, C—CH
2
Cl, C—NO
2
, or N;
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 by 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) include alkali metal (for example sodium or potassium) salts, ammonium salts and organic amine (for example diethanolamine or morpholine) salts.
Preferably by the term “substituted” is meant substituted by one or more of the following substituents: halogen, hydroxy, alkoxy, alkylthio, cyano, carboxy, alkyl, haloalkyl, —C(O)alkyl, —C(O)O-alkyl, —C(O)NH
2
, —C(O)NH-alkyl, —C(O)N(alkyl)
2
, aryl, nitro, azido, amino, alkylamino, dialkylamino, alkylsulfenyl, alkylsulfinyl, alkylsulfonyl, aryloxy, arylthio, alkylcarbonylamino, alkylcarbonyloxy, or aryloxycarbonyl.
Unless otherwise specified, alkyl groups and moieties including them have from one to six, preferably one to four, carbon atoms, alkenyl groups have from two to six, preferably two to four, carbon atoms, and alkynyl groups have from three to six, preferably three to four carbon atoms. By the term “aryl” is meant mono or polycyclic aromatic moieties includin
Finnegan Henderson Farabow Garrett & Dunner L.L.P.
Ramsuer Robert W.
Rhone-Poulenc Inc.
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