Herbicidal 3-heterocyclic substituted benzisothiazole and...

Details Herbicidal 3-heterocyclic substituted benzisothiazole and... Herbicidal 3-heterocyclic substituted benzisothiazole and...

2001-04-17

2004-03-16

Shah, Mukund J. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S310000, C548S207000

Reexamination Certificate

active

06706663

ABSTRACT:

BACKGROUND OF THE INVENTION
Weeds cause tremendous global economic losses by reducing crop yields and lowering crop quality. World-wide, agronomic crops must compete with hundreds of weed species.
In spite of the commercial herbicides available today, damage to crops caused by weeds still occurs. Accordingly, there is ongoing research to create more effective and/or more selective herbicidal agents.
Certain benzisoxazole and benzisothiazole herbicidal agents are described in U.S. Pat. Nos. 5,484,763 and 5,523,278. Those patents generically disclose benzisoxazole and benzisothiazole compounds that are substituted in the 3-position with a variety of substituents, none of which are heterocycles. In addition, those patents do not disclose that their compounds are useful for the selective control of weeds in the presence of crops such as corn, soybeans, wheat and transplanted rice.
Surprisingly, it has now been found that benzisoxazole and bensizothazole compounds in which the 3-position is substituted by an optionally substituted heterocycle are more effective and more selective herbicidal agents than expected.
Therefore it is an object of this invention to provide 3-heterocyclic substituted benzisoxazole and benzisothiazole compounds which are highly effective for the control of undesirable plant species.
It is also an object of this invention to provide intermediate compounds useful in the manufacture of said compounds.
It is a further object of the invention to provide a method for the selective control of undesirable plant species in the presence of crops.
These and other objects and features of the invention will become more apparent from the detailed description thereof set forth below.
SUMMARY OF THE INVENTION
The present invention provides compounds of formula I
wherein
Q is selected from
R is halogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
7
cycloalkyl, C
2
-C
6
alkenyl, C
2
-C
6
haloalkenyl, C
3
-C
6
alkynyl, cyano, benzyl, OH, NH
2
, C
2
-C
6
cyanoalkyl and when R and R
1
are taken together with the other atoms to which they are attached, they represent a four to seven-membered ring optonally interrupted by oxygen, sulfur or nitrogen and optionally substituted with one to three methyl groups or one or more halogen atoms;
R
1
is hydrogen, halogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
7
cycloalkyl, C
2
-C
6
alkenyl, C
2
-C
6
haloalkenyl, C
3
-C
6
alkynyl, cyano, benzyl, OH, NH
2
, C
2
-C
6
cyanoalkyl and when R and R
1
are taken together with the other atoms to which they are attached, they represent a four to seven-membered ring optionally interrupted by oxygen, sulfur or nitrogen and optionally substituted with one to three methyl groups or one or more halogen atoms;
R
2
and R
3
are each independently hydrogen, halogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
7
cycloalkyl, C
2
-C
6
alkenyl, C
2
-C
6
haloalkenyl, C
3
-C
6
alkynyl, OR
8
, S(O)
m
R
9
or NR
10
R
11
and when R
2
and R
3
are taken together with the atoms to which they are attached, they represent a four to seven-membered saturated or unsaturated ring optionally interupted by oxygen, sulfur or nitrogen and optionally substituted with one to three methyl groups or one or more halogen atoms;
R
4
, R
6
and R
7
are each independently hydrogen, halogen or C
1
-C
6
alkyl;
R
5
is hydrogen, halogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
7
cycloalkyl, C
3
-C
6
alkenyl, C
2
-C
6
haloalkenyl, C
3
-C
6
alkynyl, OR
12
or SR
13
;
R
8
, R
9
, R
12
, R
13
, and R
14
are each independently hydrogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
2
-C
6
alkenyl, C
2
-C
6
haloalkenyl, C
3
-C
6
alkynyl, C
3
-C
7
cycloalkyl, C
2
-C
6
cyanoalkyl, benzyl or (subst)phenyl;
R
10
is hydrogen, C
1
-C
6
alkyl, (subst.)benzyl or (subst.)phenyl, C
1
-C
6
haloalkyl;
R
11
is C
1
-C
6
alkyl, C
1
-C
6
alkenyl, C
3
-C
6
alkynyl, C
3
-C
7
cycloalkyl, C
1
-C
6
haloalkyl, benzyl, (subst.)phenyl or S(O)
n
R
14
;
R
88
is cyano, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, 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 or C
1
-C
4
haloalkylsulfonyl;
R
89
is hydrogen, cyano, halogen, C
1
-C
4
alkyl or C
1
-C
4
halolakyl;
n is an integer of 0, 1 or 2;
A, A
1
and A
2
are each independently oxygen or sulfur;
X is hydrogen, halogen or C
1
-C
4
alkyl;
X
1
is hydrogen, halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
1
-C
4
alkoxy or, C
1
-C
4
haloalkoxy;
V is OH, halogen, C
1
-C
4
alkoxy or C
1
-C
4
alkylthio;
Y is an optionally substituted heterocyclic three to seven-membered ring containing one to four heteroatoms selected from oxygen, sulfur or nitrogen;
Z is O or S(O)
m
;
m is an integer of 0, 1 or 2; and
the optical isomers and diastereomers thereof.
Also provided are intermediate compounds useful in the preparation of the herbicidal formula I compounds.
The present invention further provides herbicidal compositions, and methods.
DETAILED DESCRIPTION OF THE INVENTION
Surprisingly, it has now been found that the Formula I compounds of the invention demonstrate increased weed control and enhanced crop selectivity. The formula I compounds of the present invention are particularly useful for the selective control of undesirable plant species in the presence of cereal crops such as corn, wheat and rice and in the presence of leguminous crops such as soybeans.
Preferred compounds of the invention are those compounds of formula I wherein
Q is Q
7
or Q
24
;
R is C
1
-C
6
alkyl, C
2
-C
6
alkenyl, C
3
-C
6
alkynyl or NH
2
;
R
2
is C
1
-C
6
alkyl or C
1
-C
6
haloalkyl;
R
3
is hydrogen;
Y is selected from
wherein
R
15
, R
18
, R
20
and R
21
are each independently hydrogen, C
1
-C
8
alkyl, C
1
-C
8
haloalkyl, C
1
-C
8
alkoxy, C
1
-C
8
thioalkyl, halogen, nitro, cyano, hydroxy, C
2
-C
6
alkenyl, C
3
-C
6
alkynyl, C
2
-C
6
haloalkenyl, C
3
-C
8
cycloalkyl or R
20
and the carbon on Y to which R
20
is attached may form an exocyclic double bond or when R
20
and R
21
are attached to the same carbon of Y
25
, R
20
, R
21
and the carbon to which they are bonded may form a three- to six-membered heterocyclic ring;
R
16
is hydrogen, halogen, C
1
-C
8
alkyl optionally substituted with C(O)R
22
, CO
2
R
23
, X
2
R
24
, S(O)
m
alkyl, NR
86
R
87
, C
1
-C
8
haloalkyl, C(O)R
25
, CO
2
R
26
, X
3
R
27
, CH═CHR
28
, C
3
-C
8
cycloalkyl, N(R
29
)SO
2
R
30
, (subst.) phenyl, or when R
15
and R
16
are attached to adjacent carbon atoms, they may be taken together with the atoms to which they are attched to form a six-membered ring;
R
17
is hydrogen, C
1
-C
8
alkyl, C
2
-C
8
alkenyl, C
3
-C
6
alkynyl, C(O)R
25
, or(subst.)benzyl;
R
19
, R
29
, R
33
, R
34
, R
35
, R
37
, R
38
, R
39
, R
42
, R
43
, R
44
, R
46
, R
47
, R
48
, R
50
R
51
R
52
R
53
, R
55
, R
56
, R
57
, R
60
, R
61
, R
62
, R
64
, R
65
, R
66
, R
69
, R
70
, R
71
, R
73
, R
74
, R
75
, R
76
, R
80
, R
85
and R
86
are each independently hydrogen, OH, C
1
-C
8
alkyl, C
1
-C
4
alkoxy, C
3
-C
8
cycloalkyl, C
2
-C
8
alkenyl, C
3
-C
6
alkynyl, (subst.) benzyl or (subst.) phenyl;
R
23
, R
26
, R
31
, R
40
, R
49
, R
58
, R
67
, and R
79
are each independently hydrogen, C
1
-C
8
alkyl, C
1
-C
8
haloalkyl, C
3
-C
8
cycloalkyl, C
3
-C
8
halocycloalkyl, C
2
-C
8
alkenyl, C
2
-C
8
haloalkenyl, C
5
-C
8
cycloalkenyl, C
5
-C
8
halocycloalkenyl, C
3
-C
8
alkynyl, C
3
-C
8
haloalkynyl, (subst.)benzyl, (subst.) phenyl, furfuryl, pyridyl, thienyl, an alkali metal, alkaline earth metal, manganese, copper, zinc, cobalt, silver, nickel ammonium or organic ammonium cation;
R
22
, R
25
, R
32
, R
36
, R
41
, R
45
, R
54
, R
59
, R
63
, R
68
, R
72
, R
77
, R
78
, R
81
, and R
87
are each independently hydrogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
2
-C
6
alkenyl, C
2
-C
6
haloalkenyl, C
2
-C
6
alkynyl, C
3
-C
7
cycloalkyl, C
1
-C
4
cyanoalkyl, benzyl or (subsz.)phenyl;
R
24
, R
27
, and R
28
are each independently hydrogen,
C
1
-C
10
alkyl optionally substituted with one to six halogens, one C
1
-C
6
alkoxy group, CO
2
R
31
, C(O)R
32
, C(OR
33
)
2
, C

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