Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2002-08-28
2004-11-16
Balasubramanian, Venkataraman (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C514S243000, C544S182000, C544S183000, C544S184000
Reexamination Certificate
active
06818641
ABSTRACT:
BACKGROUND OF THE INVENTION
This invention relate's to certain carboxanilides, 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 which are more effective, less costly, less toxic, environmentally safer or have different modes of action.
SUMMARY OF THE INVENTION
This invention is directed to compounds of Formula I including all geometric and stereoisomers, N-oxides, and agriculturally suitable salts thereof, agricultural compositions containing them and their use to control arthropods in agronomic and nonagronomic environments
wherein:
A is H;
E is H or C
1
-C
3
alkyl; or
A and E can be taken together to form —CH
2
—, —CH
2
CH
2
—, —O—, —S—, —S(O)—, —S(O)
2
—, —NR
8
—, —OCH
2
—, —SCH
2
—, —N(R
8
)CH
2
—, substituted —CH
2
— and substituted —CH
2
CH
2
—, the substituents on each carbon independently selected from 1-2 halogen and 1-2 methyl;
G is selected from the group consisting of
W is N or CR
4
;
X is CR
5
R
6
, O, S, NR
7
or a direct bond, provided that when W is N, then X is other than a direct bond;
Y is H, C
1
-C
6
alkyl, C
2
-C
6
alkenyl, C
2
-C
6
alkynyl, C
1
-C
3
alkylsulfonyl, C
3
-C
6
cycloalkyl, C
3
-C
6
cycloalkylalkyl, NR
9
R
10
, N═CR
11
R
12
, OR
7
, COR
13
, CO
2
R
14
or C
1
-C
6
alkyl substituted by at least one group selected from halogen, C
1
-C
3
alkoxy, CN, NO
2
, S(O)
r
R
15
, COR
13
, CO
2
R
14
and optionally substituted phenyl;
Z is O or S;
each R
1
and R
2
is independently selected from the group consisting of C
1
-C
6
haloalkyl, C
2
-C
6
haloalkenyl, halogen, CN, NO
2
, OR
16
, S(O)
r
R
15
, OS(O)
2
R
15
, CO
2
R
14
, C(O)R
13
, C(O)NR
9
R
10
, SO
2
NR
9
R
10
, SF
5
, optionally substituted phenyl and optionally substituted benzyl; 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—;
R
3
is selected from the group consisting of J, C(R
17
)═N—O—R
18
, 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
14
, C(O)R
13
, C(O)NR
9
R
10
, C(S)NR
9
R
10
, C(S)R
13
, C(S)SR
13
, CN, and optionally substituted phenyl; 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
13
, CO
2
R
14
and optionally substituted phenyl; or R
3
is C
1
-C
6
alkyl substituted with a group selected from C(O)NR
9
R
10
, COR
13
, CO
2
R
14
, S(O)
m
R
15
, SCN, CN, C
1
-C
2
haloalkoxy, SiR
19
R
20
R
21
, NR
9
R
10
, NO
2
, OC(O)R
13
, —P(O)(OR
22
)
2
, optionally substituted phenyl, and J;
J is a nonaromatic 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, optionally containing one carbonyl moiety and optionally substituted;
R
4
, R
5
and R
6
are each independently H or C
1
-C
4
alkyl;
each R
7
is independently H, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
2
-C
4
alkenyl, C
2
-C
4
alkynyl, C
1
-C
4
alkoxy, SO
2
NR
9
R
10
, SO
2
R
13
, COR
9
, CONR
9
R
10
, CO
2
R
13
, optionally substituted phenyl or optionally substituted benzyl;
each R
8
is independently H, C
1
-C
4
alkyl, C
1
-C
4
alkoxyalkyl, CO
2
R
13
, SO
2
R
13
, or optionally substituted benzyl;
each R
9
and each R
11
is independently H, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl or optionally substituted phenyl;
each R
10
and each R
12
is independently H or C
1
-C
4
alkyl; or
each pair of R
9
and R
10
when attached to the same atom or each pair of R
11
and R
12
when attached to the same atom independently can be taken together as —CH
2
CH
2
CH
2
—, —CH
2
CH
2
CH
2
CH
2
—, —CH
2
CH
2
CH
2
CH
2
CH
2
— or —CH
2
CH
2
OCH
2
CH
2
—, each of which is optionally and independently substituted with 1 or 2 CH
3
groups;
each R
13
and each R
15
is independently H, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl or optionally substituted phenyl;
each R
14
is independently H, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl or optionally substituted benzyl;
R
16
is 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
alkylthioalkyl, 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, optionally substituted phenyl and optionally substituted benzyl;
R
17
is selected from the group consisting of H, Cl, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
1
-C
2
thioalkyl and CN;
R
18
is selected from the group consisting of H, C
1
-C
4
alkyl, C
2
-C
3
alkylcarbonyl and C
2
-C
3
alkoxycarbonyl;
R
19
and R
20
are each independently C
1
-C
3
alkyl;
R
21
is selected from the group consisting of H, C
1
-C
3
alkyl and optionally substituted phenyl;
each R
22
is independently H or C
1
-C
4
alkyl;
each m and n are independently 1 to 3; and
r is 0, 1 or 2.
DETAILS OF THE INVENTION
In the above recitations, the term “alkyl”, used either alone or in compound words such as “alkylthio” or “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, i-propyl, or the different butyl, pentyl or hexyl isomers. The term “1-2 alkyl” indicates that one or two of the available positions for that substituent may be alkyl which are independently selected. “Alkenyl” includes straight-chain or branched alkenes such as ethenyl, 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. “Alkenyl” also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. “Alkynyl” includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. “Alkynyl” can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl. “Alkoxy” includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. “Alkoxyalkyl” denotes alkoxy substitution on alkyl. Examples of “alkoxyalkyl” include CH
3
OCH
2
, CH
3
OCH
2
CH
2
, CH
3
CH
2
OCH
2
, CH
3
CH
2
CH
2
CH
2
OCH
2
and CH
3
CH
2
OCH
2
CH
2
. “Alkylthio” includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers. “Alkylthioalkyl” denotes alkylthio substitution on alkyl. Examples of “alkylthioalkyl” include CH
3
SCH
2
, CH
3
SCH
2
CH
2
, CH
3
CH
2
SCH
2
, CH
3
CH
2
CH
2
CH
2
SCH
2
and CH
3
CH
2
SCH
2
CH
2
. “Alkylsulfinyl” includes both enantiomers of an alkylsulfinyl group. Examples of “alkylsulfinyl” include CH
3
S(O), CH
3
CH
2
S(O), CH
3
CH
2
CH
2
S(O), (CH
3
)
2
CHS(O) and the different butylsulfinyl, pentylsulfinyl and hexylsulfinyl isomers. Examples of “alkylsulfonyl” include CH
3
S(O)
2
, CH
3
CH
2
S(O)
2
, CH
3
CH
2
CH
2
S(O)
2
, (CH
3
)
2
CHS(O)
2
and the different butylsulfonyl, pentylsulfonyl and hexylsulfinyl isomers. “Cyanoalkyl” denotes an alkyl group substituted with one cyano group. Examples of “cyanoalkyl” include NCCH
2
, NCCH
2
CH
2
and CH
3
CH(CN)CH
2
. “Cycloalkyl” includes, for example, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. Examples of“cycloalkylalkyl” include cyclopropylmethyl, cyclopentylethyl, and other cycloalkyl moieties bonded to straight-chain or branched alkyl groups. Examples of “cycloalkylalkoxy” include cyclopropylmethoxy
Balasubramanian Venkataraman
E. I. du Pont de Nemours and Company
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