Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-11-29
2002-08-27
Shah, Mukund J. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S272000, C514S274000, C544S309000, C544S311000, C544S312000, C544S314000, C544S319000, C544S321000
Reexamination Certificate
active
06440984
ABSTRACT:
BACKGROUND OF THE INVENTION
Insect and acarid pests destroy growing and harvested crops. In the United States, agronomic crops must compete with thousands of those pests. In particular, tobacco budworms and southern armyworms are especially devastating to crops.
Tobacco budworms cause tremendous economic losses in agronomic crops. In particular, budworms devastate cotton crops by feeding on green bolls. Control of budworms is complicated by their resistance to many common insecticides, including organophosphates, carbamates and pyrethroids.
In spite of the commercial insecticides and acaricides available today, damage to crops, both growing and harvested, caused by insect and acarid pests still occurs. Accordingly, there is ongoing research to create new and more effective insecticidal and acaricidal agents.
Certain pyrimidine compounds are known to possess insecticidal and nematocidal activity (see, e.g., EP 0 506 270). However, none of those compounds are within the scope of the present invention.
It is, therefore, an object of the present invention to provide compounds which are highly effective for the control of insect and acarid pests.
It is also an object of the present invention to provide a method for the control of insect and acarid 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 and acarid attack and infestation.
Those and other objects of the present invention will become more apparent from the detailed description thereof set forth below.
SUMMARY OF THE INVENTION
This application is also related to application Ser. No. 09/273,942, filed Mar. 22, 1999, now U.S. Pat. No. 6,153,619.
The present invention describes aryl pyrimidines which are useful as insecticidal and acaricidal agents. Those compounds are also useful for protecting plants from damage caused by insect and acarid attack and infestation.
The aryl pyrimidines used according to the present invention have the structural formula I
wherein
A and B each independently represent an optionally substituted aryl group;
R
1
represents a hydrogen or halogen atom or an optionally substituted alkyl, alkenyl, alkinyl, alkoxy, alkoxyalkyl, alkoxyalkoxy group; or an alkylthio group, alkylsulphinyl or alkylsulphonyl group, an amino, alkylamino or dialkylamino group or a cyano, nitro, haloalkyl, haloalkoxy, haloalkylthio or SF5 group, one of Y and Z represents N and the other represents CR
2
, in which R
2
has the meaning given for R
1
;
X represents O or NR, in which R represents a hydrogen atom or an alkyl group.
This invention also describes compositions containing those compounds and methods for using those compounds and compositions. Advantageously, it has been found that the pyrimidine compounds of the present invention, and compositions containing them, are useful for the control of insect and acarid pests. The compounds of this invention are also useful for the protection of plants from damage caused by insect and acarid attack and infestation. The pyrimidine compounds are especially useful for the control of tobacco budworms and southern armyworms.
DETAILED DESCRIPTION OF THE INVENTION
The present invention provides a method for the control of insect or acarid pests which comprises contacting said pests or their food supply, habitat or breeding grounds with a pesticidally effective amount of an aryl pyrimidine of formula I.
The present invention also provides a method for the protection of growing plants from attack or infestation by insect or acarid pests which comprises applying to the foliage of the plants, or to the soil or water in which they are growing, a pesticidally effective amount of an aryl pyrimidine compound of formula I.
The aryl pyrimidines of the present invention have the structural formula I
wherein A, B, X, Y, Z and R
1
are as described hereinabove for formula I.
Exemplary of halogen hereinabove are fluorine, chlorine, bromine and iodine.
Preferred formula I aryl pyrimidines of the present invention are those wherein
A and B are each independently phenyl optionally substituted with any combination of from one to three 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 each independently hydrogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
1
-C
4
alkylthio, cyano, nitro, amino, C
1
-C
4
haloalkyl, C
1
-C
4
haloalkoxy or fluorine; and
A is phenyl optionally substituted with any combination of from one to five halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups,
B is phenyl optionally substituted with any combination of from one to three halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups.
More preferred insecticidal and acaricidal agents of the present invention are those wherein
A is phenyl optionally substituted with any combination of from one to three halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy, C
1
-C
4
alkylthio or C
1
-C
4
haloalkoxy groups;
R
1
and R
2
each independently are hydrogen, methyl ethyl, fluoro, chloro, cyano, nitro, amino, thiomethyl or trifluoromethyl;
preferably at least one of R
1
and R
2
is hydrogen; and
A and B are each independently phenyl optionally substituted with any combination of from one to five halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy groups.
The terms “C
1
-C
4
haloalkyl” and “C
1
-C
4
haloalkoxy” are defined as a C
1
-C
4
alkyl group and a C
1
-C
4
alkoxy group substituted with one or more halogen atoms, respectively.
Formula I compounds of this invention which are particularly effective insecticidal agents include the novel compounds of formulae IA and IB:
R
1
and R
2
each independently represents a hydrogen or halogen atom or an alkyl, alkenyl, alkinyl, alkoxy, alkoxyalkyl, alkoxyalkoxy group, alkylthio, alkylsulphinyl or alkylsulphonyl group, an amino, alkylamino or dialkylamino group or a cyano, nitro, haloalkyl, haloalkoxy, haloalkylthio or SF
5
group, A represents a phenyl group being substituted by one or more of the same or different substituents selected from halogen atoms, alkyl, alkoxy, cyano, nitro, haloalkyl, haloalkoxy, alkylthio, haloalkylthio, alkylsulphinyl, alkylsulphonyl and SF
5
groups; and B represents a phenyl group being substituted by one or more of the same or different substituents selected from halogen atoms, alkyl, alkoxy, cyano, nitro, haloalkyl, haloalkoxy, alkylthio, haloalkylthio, alkylsulphinyl, alkylsulphonyl and SF
5
groups;
wherein R
1
and R
2
have the meaning given in claim
1
; A represents a phenyl group being substituted by one or more of the same or different substituents selected from halogen atoms, alkyl, alkoxy, cyano, nitro, haloalkyl, haloalkoxy, alkylthio, haloalkylthio, alkylsulphinyl, alkylsulphonyl and SF
5
groups; and B represents a phenyl group being substituted by one or more of the same or different substituents selected from halogen atoms, alkyl, alkoxy, cyano, nitro, haloalkyl, haloalkoxy, alkylthio, haloalkylthio, alkylsulphinyl, alkylsulphonyl and SF
5
groups.
Particularly preferred are the compounds of formulae IA1 and IA2
in which R
1
and R
2
have the meaning given for formulae IA and IB; and
R
3
through R
8
each independently represent a hydrogen or halogen atom, in particular F or Cl, or a C
1-4
alkyl, in particular methyl or ethyl, a C
1-4
alkoxy, in particular methoxy or ethoxy, a C
1-4
haloalkyl, in particular trifluoromethyl, a C
1-4
haloalkoxy, in particular difluoro- or trifluoromethoxy, a cyano or nitro group.
Preferably at least one of the groups R
3
, R
4
and R
5
is different from a hydrogen atom and at least one of the groups R
6
, R
7
and R
8
is different from a hydrogen atom.
Advantageously, it has been found that the formula I compounds of the present invention are especially useful for the control of tobacco budworms and southern armyworms.
Aryl pyrimidines of the present invention wherein Y is CR
1
and Z is N (formula IA) may be prepared by reacting a compound of formula
Cuccia Salvatore John
Fleming Linda
Wood William Wakefield
Shah Mukund J.
Truong Tamthom N.
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