Compositions and methods for controlling insects which...

Details Compositions and methods for controlling insects which... Compositions and methods for controlling insects which...

2000-09-13

2002-12-10

Robinson, Allen J. (Department: 1616)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

C514S404000

Reexamination Certificate

active

06492357

ABSTRACT:

FIELD OF THE INVENTION
This invention is generally in the area of compositions and methods for controlling insects which damage rice and other crops. More particularly, this invention relates to pesticidal compositions comprising ethiprole and indoxacarb or structurally related compounds, and methods for using the compositions to treat rice crops for pests such as
Nilaparvata lugens
(brown planthoppers),
Cnaphalocrocis medinalis
(rice leaf rollers), and Nephotettix spp. (rice leaf hoppers), for example,
Nephotettix cincticeps
(green leaf hopper), the most common insects which attack rice crops.
BACKGROUND OF THE INVENTION
Rice crops are often attacked by pests such as Nephotettix spp. (rice leaf hoppers), such as
Nephotettix cincticeps
(green leaf hopper),
Nilaparvata lugens
(brown planthoppers) and
Cnaphalocrocis medinalis
(rice leaf rollers). Significant research efforts have been carried out to develop insecticidal compositions useful for controlling these pests.
It is very difficult to control insect pests which belong to Homoptera such as planthoppers, leafhoppers, aphids and whiteflies because of their specific ecological and physiological character traits and also due to the rapid development of drug-resistant insects. There are currently few methods to effectively control such insect pests.
U.S. Pat. No. 5,082,860 to Karrer, et al. discloses using ethyl 2-[4-(3,5-difluorophenoxy)phenoxy]ethylcarbamate to control cicadas which damage rice crops. However, it is unclear whether the carbamate is useful in treating green leaf hoppers, brown planthoppers and rice leaf rollers.
Frequently, several insecticides are effective against one or more of the above insects, but not all of them. Accordingly, the use of a single insecticide is often insufficient to protect crops of useful plants adequately against pests. For example, indoxacarb is not particularly effective against brown planthoppers, but is active against green leaf hoppers and rice leaf rollers.
It would be advantageous to provide new compositions and methods for controlling cicadas and other insects which damage rice and other crops. The present invention provides such compositions and methods.
SUMMARY OF THE INVENTION
Compositions and methods for controlling insect populations, in particular, insects which attack rice crops, are disclosed. The compositions include one or more compounds from the Formula 1A and one or more compounds from the formulas 1B-G, and optionally but preferably include a suitable carrier.
The compounds of Formula IA-G are intended to include all geometric and stereoisomers, agriculturally suitable salts thereof, agricultural compositions containing them and their use for the control of insects in both agronomic and non-agronomic uses. The term “compounds” will be understood to include all such isomers and salts thereof.
E is selected from the group H and C
1
-C
3
alkyl; or
Y is selected from the group H; C
1
-C
6
alkyl, benzyl; C
2
-C
6
alkoxyalkyl; C
2
-C
6
alkenyl; C
2
-C
6
alkynyl; C
1
-C
6
alkyl optionally substituted by halogen, C
1
-C
3
alkoxy, C
1
-C
3
haloalkoxy, —CN, —NO
2
, S(O)
r
R
32
, COR
32
, CO
2
R
32
, phenyl optionally substituted by halogen, —CN, C
1
-C
2
haloalkyl and C
1
-C
2
haloalkoxy; C
3
-C
6
cycloalkyl; C
3
-C
6
cyclohaloalkyl; C
3
-C
6
cycloalkylalkyl; —CHO; C
2
-C
6
alkylcarbonyl; C
2
-C
6
alkoxycarbonyl; C
2
-C
6
haloalkylcarbonyl; COR
36
; CO
2
R
36
; C
1
-C
6
alkylthio; C
1
-C
6
haloalkylthio; phenylthio; R
12
OC(O)N(R
13
)S— and R
14
(R
15
)NS—;
R
1
and R
2
are independently selected from the group H, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
2
-C
6
alkenyl, C
2
-C
6
haloalkenyl, C
2
-C
6
alkynyl, C
3
-C
6
haloalkynyl, C
2
-C
6
alkylthioalkyl, C
2
-C
6
alkylthioalky, C
1
-C
6
nitroalkyl, C
2
-C
6
cyanoalkyl, C
3
-C
8
alkoxycarbonylalkyl, C
3
-C
6
cycloalkyl, C
3
-C
6
halocycloalkyl, halogen, —CN, —N
3
, —SCN, —NO
2
, —OR
17
, —SR
17
, —S(O)R
17
, —S(O)
2
R
17
, —OC(O)R
17
, —OS(O)
2
R
17
, —CO
2
R
17
, —C(O)R
17
, —C(O)NR
17
R
18
, —SO
2
NR
17
R
18
, —NR
17
R
18
, —NR
18
C(O)R
17
, —OC(O)NHR
17
, —NR
18
C(O)NHR
17
, —NR
18
SO
2
R
17
, phenyl optionally substituted with 1 to 3 substituents independently selected from W, and benzyl optionally substituted with 1 to 3 substituents independently selected from W; or when m or n is 2, (R
1
)
2
can be taken together, or (R
2
)
2
can be taken together as —OCH
2
O—, —OCF
2
O—, —OCH
2
CH
2
O—, —CH
2
C(CH
3
)
2
O—, —CF
2
CF
2
O or —OCF
2
CF
2
O— to form a cyclic bridge; provided that when R
1
or R
2
is S(O)R
17
, S(O)
2
R
17
, OC(O)R
17
or OS(O)
2
R
17
then R
17
is other than H;
R
3
is selected from the group H, J, —N
3
, —NO
2
, halogen, —N(R
22
)R
23
, C(R
34
)═N—O—R
35
, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
2
-C
6
alkenyl, C
2
-C
6
haloalkenyl, C
2
-C
6
alkynyl, C
2
-C
6
alkoxylalkyl, C
3
-C
8
alkoxycarbonylalkyl, —CO
2
R
17
, —OR
19
, —C(O)R
17
, —C(O)NR
17
R
18
, —C(S)NR
17
R
18
, —C(S)R
17
, —C(S)SR
17
, —CN, —Si(R
28
)(R
29
)R
27
, —SR
27
, —S(O)R
27
, —SO
2
R
27
, —P(O)(OR
27
)
2
, phenyl, phenyl substituted with (R
16
)
p
, benzyl and benzyl substituted with 1 to 3 substituents independently selected from W; or R
3
is C
2
-C
6
epoxyalkyl optionally substituted with a group selected from C
1
-C
3
alkyl, —CN, —C(O)R
24
, —CO
2
R
24
and phenyl optionally substituted with W; or R
3
is C
1
-C
6
alkyl substituted with a group selected from —C(O)N(R
25
)R
26
, —C(O)R
25
, —SR
27
, —S(O)R
27
, —SO
2
R
27
, —SCN, —CN, C
1
-C
2
haloalkoxy, —Si(R
28
)(R
29
)R
30
, N(R
22
)R
23
, ONO
2
, —OC(O)R
25
, —P(O)(OR
27
)
2
and J;
J is selected from the group saturated, partially unsaturated or aromatic 5- or 6-membered heterocyclic ring, bonded through carbon or nitrogen, containing 1-4 heteroatoms independently selected from the group consisting of 0-2 oxygen, 0-2 sulfur and 0-4 nitrogen, this substituent optionally containing one carbonyl and optionally substituted with one or more members selected from W;
R
4
is selected from the group H, C
1
-C
4
alkyl, COR
20
and C
2
-C
4
alkoxycarbonyl; or
R
12
is C
1
-C
6
alkyl;
R
13
is C
1
-C
4
alkyl;
R
14
and R
15
are independently C
1
-C
4
alkyl; or
R
14
and R
15
can be taken together as —CH
2
CH
2
CH
2
CH
2
CH
2
— or —CH
2
CH
2
OCH
2
CH
2
—;
R
16
is selected from the group C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
2
-C
6
alkenyl, C
2
-C
6
haloalkenyl, C
2
-C
6
alkynyl, C
3
-C
6
haloalkynyl, C
2
-C
6
alkoxyalkyl, C
2
-C
6
alkylthioalky, C
1
-C
6
nitroalkyl, C
2
-C
6
cyanoalkyl, C
3
-C
8
alkoxycarbonylalkyl, C
3
-C
6
cycloalkyl, C
3
-C
6
halocycloalkyl, halogen, CN, N
3
, SCN NO
2
, OR
17
, SR
17
, S(O)R
17
, S(O)
2
R
17
, OC(O)R
17
, OS(O)
2
R
17
, CO
2
R
17
, C(O)R
17
, C(O)N R
17
R
18
, SO
2
N R
17
R
18
, N R
18
C(O)R
17
, OC(O)NH R
17
, N R
18
C(O)NH R
17
, N R
18
SO
2
R
17
, phenyl optionally substituted with 1 to 3 substituents independently selected from W, and benzyl optionally substituted with 1 to 3 substituents independently selected from W; or when p is 2, (R
16
)
2
can be taken together as —OCH
2
O—, —OCF
2
O—, —OCH
2
CH
2
O—, —CH
2
C(CH
3
)
2
O—, —CF
2
CF
2
O or —OCF
2
CF
2
O— to from a cyclic bridge; provided that when R
16
is S(O)R
17
, S(O)
2
R
17
, OC(O)R
17
or OS(O)
2
R
17
then R
17
is other than H;
R
17
is selected from the group H, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
2
-C
6
alkenyl, C
2
-C
6
haloalkenyl, C
2
-C
6
alkynyl, C
3
-C
6
haloalkynyl, C
2
-C
6
alkoxyalkyl, C
2
-C
6
alkylthioal, C
1
-C
6
nitroalkyl, C
2
-C
6
cyanoalkyl, C
3
-C
8
alkoxycarbonylalkyl, C
3
-C
6
cycloalkyl, C
3
-C
6
halocycloalkyl, and optionally substituted phenyl and benzyl wherein the substituents are 1 to 3 substituents independently selected from W;
R
18
is selected from the group H and C
1
-C
4
alkyl; or
R
17
and R
18
, when attached to the same atom, can be taken together as —(CH
2
)
4
—, —(CH
2
)
5
—, or —CH
2
CH
2
OCH
2
CH
2
—;
R
19
is selected from the group H, C
1
-C
4
alkyl, C
2
-C
4
alkenyl, C
2
-C
4
alkynyl, C
2
-C
4
alkylcarbo

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