Fused-benzene derivatives useful as herbicides

Details Fused-benzene derivatives useful as herbicides Fused-benzene derivatives useful as herbicides

2001-07-05

2003-06-03

Rao, Deepak R. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S225000, C544S051000, C544S052000, C544S105000

Reexamination Certificate

active

06573218

ABSTRACT:

BACKGROUND OF THE UNION
1. Field of the Invention
The present invention relates to novel fused-benzene derivatives, their salts and compositions, intermediates, a process for producing them, and their use as herbicides.
2. Description of the Related Art
U.S. Pat. No. 4,859,229 discloses the herbicidal utility of uracil derivatives, in which the phenyl ring of the described compounds did not have any 2,6-disubsutitutions. Recently WO98/38188 and WO99/31091 disclosed benzoxazole and benzothiazole derivatives which have potent herbicidal activity in preemergence and postemergence applications.
The formula is;
wherein;
Q is uracil and D is either oxygen or sulfur. U.S. Pat. No. 5,169,431 disclosed benzofuran or benzothiophene type derivatives with Q as uracil and D is carbon. WO97/29105 disclosed benzofuran derivatives with Q as uracil and D is oxygen. WO93/14073 disclosed substituted dihydrobenzofuran type compounds with Q as uracil or triazine derivatives and D is carbon. U.S. Pat. No. 5,521,147 disclosed dihydrobenzofuran, dihydrobenzopyran and dihydrobenzofuran-3-one type derivatives with Q as uracil and D or M is oxygen. EP. 0,271,170 disclosed dihydrobenzofuran and dihydrobenzopyran derivatives where Q is many kinds of heterocycles and D or M is carbon. WO95/33746 disclosed cyclic sulfonamide derivatives where Q is many kinds of heterocycles including uracil and D is carbon. U.S. Pat. No. 5,346,881 disclosed benzodioxin or benzodioxole derivatives where Q is uracil, M is oxygen. JP 09301973 disclosed 2H-chromene type derivatives with Q is many kinds of heterocycles including uracil and M is oxygen. WO97/12886 disclosed benzisoxazole or benzisoxazolidinone derivatives where Q is many kinds of heterocycles including uracil and D is oxygen.
WO97/42188 disclosed indole type derivatives with Q as uracil and D or U isnitrogen. Despite the broad coverage of these patents, the general structure of the present invention has not been described.
The specific fused-benzene compounds of the formula (Ia) and (Ib) mentioned below are novel and can be used to effectively control a variety of broad or grassy leaf plant species.
SUMMARY OF THE INVENTION
The invention delineates a method for the control of undesired vegetation in a plantation crop by the application to the locus of the crop an effective amount of a compound described herein. The present application describes certain herbicidal fused benzene derivatives of the formula (Ia) and (Ib) including all geometric, tautomeric and stereo isomers, and their salts, as well as compositions containing them and methods of preparation for these compounds. (Ia) (Ib)
in which
X, Y are independent of each other and are represented by hydrogen, halogen, cyano, nitro, (C
1-4
)alkyl, (C
1-4
)alkoxy, (C
1-4
)haloalkyl or (C
1-4
)haloalkoxy;
A is oxygen, nitrogen, NR
1
, CR
3
, CR
3
R
4
, S(O)
n
*, C(═O), C(═S) or C(═NR
1
);
D is nitrogen or NR
2
;
M is CR
5
, CR
5
R
6
, nitrogen, NR
2
, S(O)
n
*, C(═O), C(═S) or C(═NR
2
);
When A is oxygen, M is nitrogen, NR
2
, S(O)
n
*, C(═O), C(═S) or C(═NR
2
);
E and L are independent of each other and may be selected from CR
7
, CR
8
, CR
7
R
8
, oxygen, nitrogen, NR
7
, S(O)
n
*, C(═O), C(═S), C(═NR
7
) or CNR
7
R
8
;
U is CR
9
, oxygen, nitrogen, NR
2
, S(O)
n
*, C(═O), C(═S) or C(═NR
2
);
When U is CR
9
, E is nitrogen;
R
1
and R
2
are independent of each other and may be selected from the group consisting of hydrogen, (C
1-6
)alkyl, (C
2-6
)alkenyl, (C
2-6
)alkynyl, (C
1-6
)alkylcarbonyl, (C
-6
)cycloalkylcarbonyl, (C
1-6
)haloalkylcarbonyl, (C
1-6
)alkoxycarbonyl, arylcarbonyl and heteroarylcarbonyl,
where any of these groups may be optionally substituted with one or more of the following groups consisting of halogen, hydroxy, cyano, nitro, amino, caboxyl, (C
1-6
)alkyl, (C
1-6
)haloalkyl, (C
1-6
)alkylcarbonyl, (C
1-6
)alkylcarbonyloxy, (C
1-6
)haloalkylcarbonyl, (C
1-6
)haloalkylcarbonyloxy, (C
1-6
)alkoxy, (C
1-6
)alkoxycarbonyl, aminocarbonyl, (C
1-6
)alkylaminocarbonyl, (C
1-6
)haloalkoxy, (C
1-6
)haloalkoxycarbonyl, (C
1-6
)alkylsulfonyl, (C
1-6
)haloalkylsulfonyl, aryl, heteroaryl and (C
3-7
)cycloalkyl, R
3
, R
4
, R
5
, R
6
, R
7
, R
8
and R
9
are independent of each other and may be selected from the group consisting of hydrogen, halogen, hydroxy, mercapto, amino, cyano, nitro, (C
1-6
)alkyl, (C
1-6
)haloalkyl, (C
1-6
)alkoxy, (C
1-6
)haloalkoxy, (C
1-6
)alkoxyalkyl, (C
2-6
)alkynyl ,(C
2-6
)alkenyl, aryl, heteroaryl, aryloxy, heteroaryloxy, (C
3-6
)cycloalkyl, (C
3-6
)cyclocarbonyl, carboxy, (C
1-6
)alkylcarbonyl, arylcarbonyl, (C
1-3
)haloalkylcarbonyl, (C
1-6
)alkylcarbonyloxy, (C
1-6
)haloalkylcarbonyloxy, (C
1-6
)alkoxycarbonyl, (C
1-6
)haloalkoxycarbonyl, (C
1-6
)alkylthiocarbonyl, (C
1-6
)haloalkylthiocarbonyl, (C
1-6
)alkoxythiocarbonyl, (C
1-6
)haloalkoxythiocarbonyl, (C
1-6
)alkylamino, arylsulfonylamino, arylamino, (C
1-6
)alkylthio, arylthio, (C
2-6
)alkenylthio, (C
2-6
)alkynylthio, (C
1-6
)alkylsulfinyl, (C
2-6
)alkenylsulfinyl, (C
2-6
)alkynylsulfinyl, (C
1-6
)alkylsulfonyl, (C
2-6
)alkenylsulfonyl, (C
2-6
)alkynylsulfonyl, arylsulfonyl, where any of these groups may be optionally substituted with one or one more of the following group consisting of halogen, hydroxy, mercapto, cyano, nitro, amino, caboxy, (C
1-6
)alkyl, (C
1-6
)haloalkyl, (C
1-6
)alkylcarbonyl, (C
1-6
)alkylcarbonyloxy, (C
1-6
)haloalkylcarbonyl, (C
1-6
)haloalkylcarbonyloxy, (C
1-6
)alkoxy, (C
1-6
)alkoxycarbonyl, aminocarbonyl, (C
1-6
)alkylaminocarbonyl, (C
1-6
)haloalkoxy, (C
1-6
)haloalkoxycarbonyl, (C
1-6
)alkylsulfonyl, (C
1-6
)haloalkylsulfonyl, aryl, haloaryl, alkoxyaryl, aryoxy, arylthio, haloaryloxy, heteroaryl, heteroaryloxy and (C
3-7
)cycloalkyl;
n* is represent an integer from 0 to 2;
Q is selected from;
 wherein
A
1
and A
2
are independently oxygen or sulfur;
R
10
is hydrogen, halogen, cyano, nitro, formyl, (C
1-4
)alkyl, (C
1-4
)haloalkyl, amino, (C
1-4
)alkylamino, (C
1-4
)haloalkylamino, (C
1-4
)alkoxyamino, (C
1-4
)haloalkoxyamino, (C
1-4
)alkylcarbonyl, (C
1-4
)haloalkylcarbonyl, (C
1-4
)haloalkoxycarbonyl, (C
1-4
)alkylcabonylamino, (C
1-4
)haloalkylcarbonylamino, (C
1-4
)alkoxycarbonylamino, (C
1-4
)haloalkoxycarbonylamino, (C
1-6
)alkoxyalkyl, (C
1-6
)haloalkoxyalkyl, (C
1-6
)alkylthio, (C
1-4
)haloalkylthio, (C
2-6
)alkenyl, (C
2-4
)haloalkenyl, (C
2-6
)alkynyl or (C
2-6
)haloalkynyl;
R
11
, R
12
and R
18
are independent of each other and may be selected from the group consisting of hydrogen, halogen, cyano, (
1-4
)alkyl, (
1-4
)haloalkyl, (C
1-4
)alkoxy, (C
1-4
)haloalkoxy, (C
2-6
)alkenyl, (C
2-6
)haloalkenyl, hydroxy or amino which may be optionally substituted with (C
1-4
)alkyl and (C
1-4
)haloalkyl;
R
13
and R
14
are independent of each other and may be selected from the group consisting of hydrogen, halogen, (C
1-3
)alkyl, (C
1-3
)haloalkyl, hydroxy, (C
1-3
)alkoxy, (C
1-3
)haloalkoxy, cyano, nitro, amino or (C
1-6
)alkylamino,
When R
13
and R
14
are taken together with the atoms to which they are attached, they represent a three to seven membered substituted or unsubstituted ring optionally containing oxygen, S(O)
n
*** or nitrogen with following optional substitutions, one to three halogen, cyano, nitro, hydroxy, amino, carbonyl, (C
1-6
)alkyl, (C
1-6
)haloalkyl, (C
1-6
)alkylcarbonyl, (C
1-6
)alkylcarbonyloxy, (C
1-6
)haloalkylcarbonyl, (C
1-6
)haloalkylcarbonyloxy, (C
1-6
)alkoxy, (C
1-6
)alkoxycarbonyl, aminocarbonyl, (C
1-6
)alkylaminocarbonyl, (C
1-6
)haloalkoxy, (C
1-6
)haloalkoxycarbonyl, (C
1-6
)alkylsulfonyl. (C
1-6
)haloalkylsulfonyl, aryl, heteroaryl or (C
3-7
)cycloalkyl;
G is nitrogen or CR
16
,
G′ is NR
15
, oxygen, S(O)
n
*** or CR
16
R
17
,
G″ is nitrogen, CR
16
, NR15 oxygen, S(O)
n
. . . or CR
16
R
17
R
15
may be selected from the group consisting of hydrogen, (C
1-6
)alkyl, (C
1-6
)alkylcarbonyl, (C
1-6
)haloalkylcarbonyl, arylcarbonyl and heteroarylcarbonyl; where any of these groups may be optionally substituted with one or more of the following groups

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