Insecticidal anthranilamides

Details Insecticidal anthranilamides Insecticidal anthranilamides

2002-08-28

2004-06-08

Davis, Zinna Northington (Department: 1625)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

C514S365000, C514S372000, C514S374000, C514S378000, C514S383000, C514S396000, C514S406000, C514S438000, C514S461000, C548S200000, C548S214000, C548S236000, C548S248000, C548S255000, C548S266800, C548S335500, C548S374100, C549S029000, C549S429000, C546S275400

Reexamination Certificate

active

06747047

ABSTRACT:

BACKGROUND OF THE INVENTION
This invention relates to certain anthranilamides, their N-oxides, agriculturally suitable salts and compositions, and methods of their use as arthropodicides in both agronomic and nonagronomic environments.
The control of arthropod pests is extremely important in achieving high crop efficiency. Arthropod damage to growing and stored agronomic crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of arthropod pests in forestry, greenhouse crops, ornamentals, nursery crops, stored food and fiber products, livestock, household, and public and animal health is also important. Many products are commercially available for these purposes, but the need continues for new compounds that are more effective, less costly, less toxic, environmentally safer or have different modes of action.
NL 9202078 discloses N-acyl anthranilic acid derivatives of Formula i as insecticides
wherein, inter alia,
X is a direct bond;
Y is H or C
1
-C
6
alkyl;
Z is NH
2
, NH(C
1
-C
3
alkyl) or N(C
1
-C
3
alkyl)
2
; and
R
1
through R
9
are independently H, halogen, C
1
-C
6
alkyl, phenyl, hydroxy, C
1
-C
6
alkoxy or C
1
-C
7
acyloxy.
SUMMARY OF THE INVENTION
This invention pertains to a method for controlling arthropods comprising contacting the arthropods or their environment with an arthropodicidally effective amount of a compound of Formula 1, its N-oxide or agriculturally suitable salts
wherein
A and B are independently O or S;
each J is independently a phenyl or naphthyl group substituted with 1 to 2 R
5
and optionally substituted with 1 to 3 R
6
;
or each J is independently a 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system wherein each ring or ring system is optionally substituted with 1 to 4 R
7
;
n is 1 to 4;
R
1
is H; or C
1
-C
6
alkyl, C
2
-C
6
alkenyl, C
2
-C
6
alkynyl or C
3
-C
6
cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO
2
, hydroxy, C
1
-C
4
alkoxy, C
1
-C
4
alkylthio, C
1
-C
4
alkylsulfinyl, C
1
-C
4
alkylsulfonyl, C
2
-C
4
alkoxycarbonyl C
1
-C
4
alkylamino, C
2
-C
8
dialkylamino and C
3
-C
6
cycloalkylamino; or
R
1
is C
2
-C
6
alkylcarbonyl, C
2
-C
6
alkoxycarbonyl, C
2
-C
6
alkylaminocarbonyl, C
3
-C
8
dialkylaminocarbonyl or C(═A)J;
R
2
is H, C
1
-C
6
alkyl, C
2
-C
6
alkenyl, C
2
-C
6
alkynyl, C
3
-C
6
cycloalkyl, C
1
-C
4
alkoxy, C
1
-C
4
alkylamino, C
2
-C
8
dialkylamino, C
3
-C
6
cycloalkylamino, C
2
-C
6
alkoxycarbonyl or C
2
-C
6
alkylcarbonyl;
R
3
is H; G; C
1
-C
6
alkyl, C
2
-C
6
alkenyl, C
2
-C
6
alkynyl, C
3
-C
6
cycloalkyl, each optionally substituted with one or more substituents selected from the group consisting of halogen, G, CN, NO
2
, hydroxy, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy, C
1
-C
4
alkylthio, C
1
-C
4
alkylsulfinyl, C
1
-C
4
alkylsulfonyl, C
2
-C
6
alkoxycarbonyl, C
2
-C
6
alkylcarbonyl, C
3
-C
6
trialkylsilyl, and a phenyl, phenoxy or 5- or 6-membered heteroaromatic ring, each ring optionally substituted with one to three substituents independently selected from the group consisting of C
1
-C
4
alkyl, C
2
-C
4
alkenyl, C
2
-C
4
alkynyl, C
3
-C
6
cycloalkyl, C
1
-C
4
haloalkyl, C
2
-C
4
haloalkenyl, C
2
-C
4
haloalkynyl, C
3
-C
6
halocycloalkyl, halogen, CN, NO
2
, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy, C
1
-C
4
alkylthio, C
1
-C
4
alkylsulfinyl, C
1
-C
4
alkylsulfonyl, C
1
-C
4
alkylamino, C
2
-C
8
dialkylamino, C
3
-C
6
cycloalkylamino, C
3
-C
6
(alkyl)cycloalkylamino, C
2
-C
4
alkylcarbonyl, C
2
-C
6
alkoxycarbonyl, C
2
-C
6
alkylaminocarbonyl, C
3
-C
8
dialkylaminocarbonyl and C
3
-C
6
trialkylsilyl; C
1
-C
4
alkoxy; C
1
-C
4
alkylamino; C
2
-C
8
dialkylamino; C
3
-C
6
cycloalkylamino; C
2
-C
6
alkoxycarbonyl or C
2
-C
6
alkylcarbonyl; or
R
2
and R
3
can be taken together with the nitrogen to which they are attached to form a ring containing 2 to 6 atoms of carbon and optionally one additional atom of nitrogen, sulfur or oxygen, said ring may be optionally substituted with 1 to 4 substituents selected from the group consisting of C
1
-C
2
alkyl, halogen, CN, NO
2
and C
1
-C
2
alkoxy;
G is a 5- or 6-membered nonaromatic carbocyclic or heterocyclic ring, optionally including one or two ring members selected from the group consisting of C(═O), SO or S(O)
2
and optionally substituted with 1 to 4 substituents selected from the group consisting of C
1
-C
2
alkyl, halogen, CN, NO
2
and C
1
-C
2
alkoxy;
each R
4
is independently H, C
1
-C
6
alkyl, C
2
-C
6
alkenyl, C
2
-C
6
alkynyl, C
3
-C
6
cycloalkyl, C
1
-C
6
haloalkyl, C
2
-C
6
haloalkenyl, C
2
-C
6
haloalkynyl, C
3
-C
6
halocycloalkyl, halogen, CN, NO
2
, hydroxy, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy, C
1
-C
4
alkylthio, C
1
-C
4
alkylsulfinyl, C
1
-C
4
alkylsulfonyl, C
1
-C
4
haloalkylthio, C
1
-C
4
haloalkylsulfinyl, C
1
-C
4
haloalkylsulfonyl, C
1
-C
4
alkylamino, C
2
-C
8
dialkylamino, C
3
-C
6
cycloalkylamino, or C
3
-C
6
trialkylsilyl; or
each R
4
is independently phenyl, benzyl or phenoxy, each optionally substituted with C
1
-C
4
alkyl, C
2
-C
4
alkenyl, C
2
-C
4
alkynyl, C
3
-C
6
cycloalkyl, C
1
-C
4
haloalkyl, C
2
-C
4
haloalkenyl, C
2
-C
4
haloalkynyl, C
3
-C
6
halocycloalkyl, halogen, CN, NO
2
, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy, C
1
-C
4
alkylthio, C
1
-C
4
alkylsulfinyl, C
1
-C
4
alkylsulfonyl, C
1
-C
4
alkylamino, C
2
-C
8
dialkylamino, C
3
-C
6
cycloalkylamino, C
3
-C
6
(alkyl)cycloalkylamino, C
2
-C
4
alkylcarbonyl, C
2
-C
6
alkoxycarbonyl, C
2
-C
6
alkylaminocarbonyl, C
3
-C
8
dialkylaminocarbonyl or C
3
-C
6
trialkylsilyl;
each R
5
is independently C
1
-C
6
alkyl, C
2
-C
6
alkenyl, C
2
-C
6
alkynyl, C
3
-C
6
cycloalkyl, C
1
-C
6
haloalkyl, C
2
-C
6
haloalkenyl, C
2
-C
6
haloalkynyl, C
3
-C
6
halocycloalkyl, halogen, CN, CO
2
H, CONH
2
, NO
2
, hydroxy, C
1
-C
6
alkoxy, C
1
-C
6
haloalkoxy, C
1
-C
6
alkylthio, C
1
-C
6
alkylsulfinyl, C
1
-C
6
alkylsulfonyl, C
1
-C
6
haloalkylthio, C
1
-C
6
haloalkylsulfinyl, C
1
-C
6
haloalkylsulfonyl, C
1
-C
6
alkylamino, C
2
-C
12
dialkylamino, or C
3
-C
6
cycloalkylamino, C
2
-C
6
alkylcarbonyl, C
2
-C
6
alkoxycarbonyl, C
2
-C
6
alkylaminocarbonyl, C
3
-C
8
dialkylaminocarbonyl, C
3
-C
6
trialkylsilyl; or
(R
5
)
2
when attached to adjacent carbon atoms can be taken together as —OCF
2
O—, —CF
2
CF
2
O—, or —OCF
2
CF
2
O—;
each R
6
is independently H, halogen, C
1
-C
6
alkyl, C
2
-C
6
alkenyl, C
2
-C
6
alkynyl, C
3
-C
6
cycloalkyl, C
1
-C
4
alkoxy or C
2
-C
4
alkoxycarbonyl; or
each R
6
is independently a phenyl, benzyl, phenoxy, 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, each ring optionally substituted with one to three substituents independently selected from the group consisting of C
1
-C
4
alkyl, C
2
-C
4
alkenyl, C
2
-C
4
alkynyl, C
3
-C
6
cycloalkyl, C
1
-C
4
haloalkyl, C
2
-C
4
haloalkenyl, C
2
-C
4
haloalkynyl, C
3
-C
6
halocycloalkyl, halogen, CN, NO
2
, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy, C
1
-C
4
alkylthio, C
1
-C
4
alkylsulfinyl, C
1
-C
4
alkylsulfonyl, C
1
-C
4
alkylamino, C
2
-C
8
dialkylamino, C
3
-C
6
cycloalkylamino, C
3
-C
6
(alkyl)cycloalkylamino, C
2
-C
4
alkylcarbonyl, C
2
-C
6
alkoxycarbonyl, C
2
-C
6
alkylaminocarbonyl, C
3
-C
8
dialkylaminocarbonyl or C
3
-C
6
trialkylsilyl;
each R
7
is independently H, C
1
-C
6
alkyl, C
2
-C
6
alkenyl, C
2
-C
6
alkynyl, C
3
-C
6
cycloalkyl, C
1
-C
6
haloalkyl, C
2
-C
6
haloalkenyl, C
2
-C
6
haloalkynyl, C
3
-C
6
halocycloalkyl, halogen, CN, CO
2
H, CONH
2
, NO
2
, hydroxy, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy, C
1
-C
4
alkylthio, C
1
-C
4
alkylsulfinyl, C
1
-C
4
alkylsulfonyl, C
1
-C
4
haloalkylthio, C
1
-C
4
haloalkylsulfinyl, C
1
-C
4
haloalkylsulfonyl, C
1
-C
4
alkylamino, C
2
-C
8
dialkylamino, C
3
-C
6
cycloalkylamino, C
2
-C
6
alkylcarbonyl, C
2
-C
6
alkoxycarbonyl, C
2
-C
6
alkylami

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