Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...
Reexamination Certificate
1999-03-26
2002-03-19
Jones, Dwayne C. (Department: 1614)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Nitrogen containing other than solely as a nitrogen in an...
C514S617000, C514S625000, C564S161000, C564S218000
Reexamination Certificate
active
06359009
ABSTRACT:
BACKGROUND OF THE INVENTION
Insect pests destroy growing and harvested crops. In the United States, agronomic crops must compete with thousands of those pests. In particular, soil-dwelling Coleoptera such as southern corn rootworm, northern corn rootworm, western corn rootworm and Mexican corn rootworm are especially devastating to crops such as corn.
In spite of the commercial insecticides available today, damage to crops, both growing and harvested, caused by insect pests still occurs. Accordingly, there is ongoing research to create new and more effective insecticidal agents.
Certain N-substituted-2,2,4-trimethyl-3-oxovaleramide compounds are described in Czech. patent number 148,911; Collect. Czech. Chem. Commun., 36(5), pp. 1995-2004 (1971); Journal of Organic Chemistry, 26, pp. 4340-4344 (1961); Journal of Organic Chemistry, 27, pp. 60-64 (1962); and U.S. Pat. No. 3,072,724. However, no insecticidal utility is described for those compounds.
It is, therefore, an object of the present invention to provide compounds which are effective for the control of insect pests.
It is also an object of the present invention to provide a method for the control of insect pests.
It is a further object of this invention to provide a method for the protection of growing and harvested crops from damage caused by insect attack and infestation.
These and other objects of the present invention will become more apparent from the detailed description thereof set forth below.
SUMMARY OF THE INVENTION
The present invention comprises substituted anilide compounds which are useful as insecticidal agents. Those compounds are also useful for protecting plants from damage caused by insect attack and infestation.
The insecticidal substituted anilide compounds of the present invention have the structural formula I
wherein
Y is halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy, nitro or cyano;
R is hydrogen,
C
1
-C
4
alkyl optionally substituted with one C
1
-C
4
alkoxy group, or
benzoyl optionally substituted with one or more groups independently selected from halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy, nitro and cyano groups;
R
1
is C
1
-C
4
alkyl and R
2
is C
1
-C
4
alkyl, halogen or hydrogen, or R
1
and R
2
may be taken together with the carbon atom to which they are attached to form a cyclopropyl ring;
X is
O or S(O)
n
;
n is an integer of 0, 1 or 2;
R
3
is C
3
-C
6
cycloalkyl, or
C
1
-C
6
alkyl optionally substituted with one phenyl ring wherein the phenyl ring is optionally substituted with one or more groups independently selected from halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy, nitro and cyano groups;
R
4
is hydrogen, C
1
-C
8
alkyl, C
1
-C
8
haloalkyl, C
1
-C
6
acyl, C
1
-C
6
haloacyl, C
1
-C
4
alkoxymethyl, C
3
-C
6
cycloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl or S(O)
n
R
5
; and
R
5
is C
1
-C
4
alkyl or C
1
-C
4
haloalkyl; and the optical isomers, tautomers, agriculturally acceptable salts and agriculturally acceptable metal chelates thereof.
This invention also comprises compositions containing those compounds and methods for using those compounds and compositions. Advantageously, it has been found that the substituted anilide compounds of the present invention, and compositions containing them, are useful for the control of insect pests. The compounds of this invention are also useful for the protection of plants from damage caused by insect attack and infestation.
DETAILED DESCRIPTION OF THE INVENTION
The present invention provides a method for the control of insect pests which comprises contacting said pests, or their food supply, habitat or breeding grounds with a pesticidally effective amount of a substituted anilide compound of formula I.
The present invention also provides a method for the protection of growing plants from attack or infestation by insect pests which comprises applying to the foliage of the plants, or to the soil or water in which they are growing or are to be grown, a pesticidally effective amount of a substituted anilide compound of formula I.
Insecticidal substituted anilide compounds of the present invention have the structural formula I
wherein R, R
1
, R
2
, R
3
, X and Y are as described hereinabove for formula I.
Exemplary of halogen hereinabove are fluorine, chlorine, bromine and iodine. The terms “C
1
-C
4
haloalkyl”, “C
1
-C
8
haloalkyl”, “C
1
-C
4
haloalkoxy” and “C
1
-C
6
haloacyl” are defined as a C
1
-C
4
alkyl group, a C
1
-C
8
alkyl group, a C
1
-C
4
alkoxy group and a C
1
-C
6
acyl group substituted with one or more halogen atoms, respectively. Agriculturally acceptable salts of formula I compounds include, but are not limited to, acid addition salts formed from acids such as hydrochloric acid, sulfuric acid and phosphoric acid, and basic salts such as pyridine salts, alkali metal salts and alkaline earth metal salts. In addition, formula I compounds wherein X is
may form chelates with boron, transition metals such as copper and zinc, and lanthanide metals.
Advantageously, it has been found that the substituted anilide compounds of the present invention are especially useful for the control of soil-dwelling Coleoptera pests such as southern corn rootworms, northern corn rootworms, western corn rootworms, and Mexican corn rootworms.
Preferred formula I compounds of the present invention are those wherein
Y is halogen or C
1
-C
4
haloalkyl;
R is hydrogen,
C
l
-C
4
alkyl optionally substituted with one C
1
-C
4
alkoxy group, or
benzoyl optionally substituted with one or more groups independently selected from halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy, nitro and cyano groups;
R
1
and R
2
are each independently C
1
-C
4
alkyl;
X is
O or S(O)
n
;
n is an integer of 1 or 2;
R
3
is C
1
-C
6
alkyl; and
R
4
is C
6
-C
8
alkyl, C
1
-C
6
acyl, C
1
-C
4
alkoxymethyl, C
3
-C
6
alkenyl or C
3
-C
6
alkynyl.
More preferred insecticidal agents of the present invention are those wherein
Y is Cl or trifluoromethyl;
R is hydrogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxymethyl, or
benzoyl optionally substituted with one or more groups independently selected from halogen,
C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups;
R
1
and R
2
are methyl;
X is
O or S(O)
n
;
n is an integer of 1 or 2;
R
3
is isopropyl or tert-butyl; and
R
4
is C
1
-C
4
alkyl, C
2
-C
6
acyl, C
1
-C
4
alkoxymethyl, allyl or propargyl.
Most preferred substituted anilide compounds of this invention are those wherein
Y is Cl or trifluoromethyl;
R is hydrogen, C
1
-C
4
alkyl or C
1
-C
4
alkoxymethyl;
R
1
and R
2
are methyl;
X is
R
3
is isopropyl; and
R
4
is C
2
-C
6
acyl.
Formula I compounds of this invention which are particularly effective for the control of soil-dwelling Coleoptera pests include
&agr;,&agr;,&agr;-trifluoro-2,2,4-trimethyl-3-oxo-p-valerotoluidide;
&agr;,&agr;,&agr;-trifluoro-2-(isopropylsulfinyl)-2-methyl-p-propionotoluidide;
4′-chloro-3-hydroxy-2,2,4-trimethylvaleranilide, acetate (ester);
&agr;,&agr;,&agr;-trifluoro-N,2,2,4-tetramethyl-3-oxo-p-valerotoluidide; and
N-(ethoxymethyl)-&agr;,&agr;,&agr;-trifluoro-2,2,4-trimethyl-3-oxo-p-valerotoluidide, among others.
Novel substituted anilide compounds of the present invention have the structural formula I
wherein R, R
1
, R
2
, R
3
, X and Y are as described hereinabove for formula I provided that Y cannot be methyl or methoxy when X is
R is hydrogen, R
1
and R
2
are methyl, and R
3
is isopropyl.
Formula I compounds wherein X is C(O) may be prepared, as shown in Flow Diagram I, by reacting a substituted aniline of formula II with an acid chloride of formula III in the presence of a base.
Certain substituted anilide compounds wherein R is other than hydrogen may be prepared, as shown in Flow Diagram II, by reacting a formula I compound wherein R is hydrogen with an electrophile of formula IV in the presence of a base.
Formula I compounds wherein X is O may be prepared, as shown in Flow Diagram III, by reacting a substituted aniline
Barnes Keith Douglas
Diehl Robert Eugene
Kameswaran Venkataraman
Luo Tatao
Treacy Michael Frank
BASF - Aktiengesellschaft
Jones Dwayne C.
LandOfFree
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