Heteroaryl azole herbicides

Details Heteroaryl azole herbicides Heteroaryl azole herbicides

1999-09-01

2001-01-09

Shah, Mukund J. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S242000, C504S243000, C504S250000, C504S252000, C504S253000, C544S320000, C544S321000, C544S323000, C544S324000, C546S256000, C546S268100, C546S268400, C546S272400, C546S274100, C546S275400, C546S276100, C546S276400, C546S278400, C546S278700

Reexamination Certificate

active

06172005

ABSTRACT:

BACKGROUND OF THE INVENTION
This invention relates to certain heteroaryl azoles, their N-oxides, agriculturally suitable salts, compositions thereof, and methods of their use for controlling undesirable vegetation.
The control of undesired vegetation is extremely important in achieving high crop efficiency. Achievement of selective control of the growth of weeds especially in such useful crops as rice, soybean, sugar beet, corn (maize), potato, wheat, barley, tomato and plantation crops, among others, is very desirable. Unchecked weed growth in such useful crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of undesired vegetation in noncrop areas 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.
WO 96/06096 discloses herbicidal substituted pyridines of the formula
wherein, inter alia,
R
1
, R
2
, and R
3
are each independently hydrogen, alkyl, alkoxy, cyano, nitro or halogen;
Qa is optionally substituted phenyl, pyrazolyl or pyridyl;
Qb is azolyl;
X is O, S or NR
4
; and
R
4
is H or alkyl.
The heteroaryl azoles of the present invention are not disclosed in this publication.
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, as well as agricultural compositions containing them and a method of their use for controlling undesirable vegetation:
W is N or CR
9
;
X, Y and Z are independently N, CH or CR
9
, provided that only one of X, Y and Z is CR
9
;
Q is O, S(O)
n
or NR
10
;
R
1
and R
2
are independently H, halogen, cyano, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy, C
2
-C
4
alkoxyalkyl, C
3
-C
5
dialkoxyalkyl, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
2
-C
4
alkoxyalkyl, C
3
-C
4
alkenyl, C
3
-C
4
alkynyl, C
3
-C
4
alkenyloxy, C
3
-C
4
alkynyloxy, S(O)
n
R
8
, C
2
-C
4
alkylthioalkyl, C
2
-C
4
alkylsulfonylalkyl, C
1
-C
4
alkylamino or C
2
-C
4
dialkylamino;
R
3
is H, halogen, cyano, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy, C
1
-C
4
haloalkyl, C
2
-C
4
alkoxyalkyl, C
3
-C
4
alkenyl, C
3
-C
4
alkynyl, C
3
-C
4
alkenyloxy, C
3
-C
4
alkynyloxy or S(O)
n
R
8
;
R
4
is halogen, cyano, SF
5
, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy or S(O)
n
R
8
;
R
5
is H, halogen, cyano, SF
5
, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy or S(O)
n
R
8
;
R
6
is H, halogen, cyano, SF
5
, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy or S(O)
n
R
8
;
R
7
is halogen, cyano, SF
5
, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy or S(O)
n
R
8
;
each R
8
is independently C
1
-C
4
alkyl or C
1
-C
4
haloalkcyl;
each R
9
is independently halogen, cyano, C
1
-C
4
alkoxy, C
1
-C
4
haloalkoxy, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
2
-C
4
alkoxyalkyl, C
3
-C
4
alkenyl, C
3
-C
4
alkynyl, C
3
-C
4
alkenyloxy, C
3
-C
4
alkynyloxy or S(O)
n
R
8
;
R
10
is H, C
1
-C
4
alkyl or C
1
-C
4
haloalkyl; and
each n is independently 0, 1 or 2.
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
. “Alkenyloxy” includes straight-chain or branched alkenyloxy moieties. Examples of “alkenyloxy” include H
2
C═CHCH
2
O, (CH
3
)
2
C═CHCH
2
O, (CH
3
)CH═CHCH
2
O, (CH
3
)CH═C(CH
3
)CH
2
O and CH
2
═CHCH
2
CH
2
O. “Alkynyloxy” includes straight-chain or branched alkynyloxy moieties. Examples of “alkynyloxy” include HC≡CCH
2
O, CH
3
C≡CCH
2
O and CH
3
C≡CCH
2
CH
2
O. “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
. “Alkylthioalkoxy” denotes alkylthio substitution on alkoxy. “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 hexylsulfonyl 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
. “Alkylamino”, “dialkylamino”, “alkenylthio”, “alkenylsulfinyl”, “alkenylsulfonyl”, “alkynylthio”, “alkynylsulfinyl”, “alkynylsulfonyl”, and the like, are defined analogously to the above examples.
One skilled in the art will appreciate that not all nitrogen containing heterocycles can form N-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen containing heterocycles which can form N-oxides. One skilled in the art will also recognize that tertiary amines can form N-oxides. Synthetic methods for the preparation of N-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane. These methods for the preparation of N-oxides have been extensively described and reviewed in the literature, see for example: T. L. Gilchrist in
Comprehensive Organic Synthesis,
vol. 7, pp 748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik in
Comprehensive Heterocyclic Chemistry,
vol. 3, pp 18-20, A. J. Boulton and A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keene in
Advances in Heterocyclic Chemistry,
vol. 43, pp 149-161, A. R. Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in
Advances in Heterocyclic Chemistry,
vol. 9, pp 285-291, A. R. Katritzky and A. J. Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G. Werstiuk in
Advances in Heterocyclic Chemistry,
vol. 22, pp 390-392, A. R. Katritzky and A. J. Boulton, Eds., Academic Press.
The term “halogen”, either alone or in compound words such as “haloalkyl”, includes fluorine, chlorine, bromine or iodine. The term “1-2 halogen” indicates that one or two of the available positions for that substituent may be halogen which are independently selected. Further, when used in compound words such as “haloalkyl”, said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” include F
3
C, ClCH
2
, CF
3
CH
2
and CF
3
CCl
2
. The terms “haloalken

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