1- (3-Heterocyclylphenyl) isothiourea, -isourea, -guanidine...

Details 1- (3-Heterocyclylphenyl) isothiourea, -isourea, -guanidine... 1- (3-Heterocyclylphenyl) isothiourea, -isourea, -guanidine...

1999-08-04

2001-10-16

Shah, Mukund J. (Department: 1613)

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

C544S309000, C544S311000, C544S315000, C544S316000, C504S136000

Reexamination Certificate

active

06303783

ABSTRACT:

BACKGROUND OF THE INVENTION
Weeds cause tremendous global economic losses by reducing crop yields and lowering crop quality. In the United States alone, 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 new and more effective herbicides.
JP 07304759-A and DE 3505432-A describe certain iminothiazolone derivatives which are useful as herbicidal agents. However, none of the compounds described in those applications are substituted with the 3-heterocyclylphenyl group of the present invention.
U.S. Pat. No. 3,287,466 describes certain 3-alkyl-4-imino-5-(arylimino)-2-thiazolidinone compounds which are useful as herbicidal agents. However, the arylimino groups of those compounds are not substituted with the heterocyclyl groups of this invention.
It is therefore an object of the present invention to provide compounds which are highly effective for controlling undesirable plant species.
It is also an object of the present invention to provide methods for controlling undesirable plant species.
These and other objects of the present invention will become more apparent from the detailed description thereof set forth below.
SUMMARY OF THE INVENTION
The present invention describes 1-(3-heterocyclylphenyl)isothiourea, -isourea, -guanidine and -amidine compounds which are useful as herbicidal agents.
The 1-(3-heterocyclylphenyl)isothiourea, -isourea, -guanidine and -amidine compounds of the present invention have the structural formula I
wherein
X and Y are each independently hydrogen, halogen, nitro, cyano, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl or S(O)
m
R
1
;
R is hydrogen,
a C
1
-C
8
alkyl, C
3
-C
7
cycloalkyl, C
3
-C
8
alkenyl, C
5
-C
7
-cycloalkenyl or C
3
-C
8
alkynyl group, wherein each group is optionally substituted with any combination of one to six halogen atoms, one or two cyano groups, one or two nitro groups, one or two C(W)R
2
groups, one or two C(W)OR
3
groups, one or two C(W)NR
4
R
5
groups, one or two P(V) (OR
6
)
2
groups, one or two OR
7
groups, one or two SR
8
groups, one or two NR
9
R
10
groups, one or two OC(W)R
11
groups, one or two NR
12
S(O)
n
R
13
groups, one or two C(W)NR
12
S(O)
n
R
13
groups,
one 4- to 10-membered heterocyclic ring optionally substituted with any combination of one or two oxo groups, one or two thioxo groups, one to three halogen atoms, one to three nitro groups, one to three cyano groups, one to three C
1
-C
4
alkyl groups, one to three C
1
-C
4
haloalkyl groups, one to three C
1
-C
4
alkoxy groups, one to three C
1
-C
4
haloalkoxy groups, one or two C
2
-C
6
-alkoxyalkyl groups, one or two C
2
-C
6
haloalkoxyalkyl groups, one or two C(O)OR
14
groups, one or two C(O)R
14
groups, one to three C
3
-C
6
alkoxycarbonylalkyl groups, one to three C
3
-C
6
haloalkoxycarbonylalkyl groups, one to three C
3
-C
6
alkylcarbonyalkyl groups, one to three C
3
-C
6
haloalkylcarbonylalkyl groups, one or two NR
15
S(O)
p
R
16
groups or one or two C(W)NR
15
S(O)
p
R
16
groups, or
one phenyl group optionally substituted with any combination of one to three halogen atoms, one to three nitro groups, one to three cyano groups, one to three C
1
-C
4
alkyl groups, one to three C
1
-C
4
haloalkyl groups, one to three C
1
-C
4
alkoxy groups, one to three C
1
-C
4
haloalkoxy groups, one or two C
2
-C
6
alkoxyalkyl groups, one or two C
2
-C
6−
haloalkoxyalkyl groups, one or two C(O)OR
14
groups, one or two C(O)R
14
groups, one to three C
3
-C
6
alkoxycarbonylalkyl groups, one to three C
3
-C
6
haloalkoxycarbonylalkyl groups, one to three C
3
-C
6
alkylcarbonylalkyl groups, one to three C
3
-C
6
haloalkylcarbonylalkyl groups one or two NR
15
S(O)
p
R
16
groups or one or two C(W)NR
15
S(O)
p
R
16
groups,
a 4- to 10-membered heterocyclic ring optionally substituted with any combination of one or two oxo groups, one or two thioxo groups, one to three halogen atoms, one to three nitro groups, one to three cyano groups, one to three C
1
-C
4
-alkyl groups, one to three C
1
-C
4
haloalkyl groups, one to three C
1
-C
4
alkoxy groups, one to three C
1
-C
4
haloalkoxy groups, one or two C
2
-C
6
alkoxyalkyl groups, one or two C
2
-C
6
haloalkoxyalkyl groups, one or two C(O)OR
14
groups, one or two C(O)R
14
groups, one to three C
3
-C
6
alkoxycarbonylalkyl groups, one to three C
3
-C
6
haloalkoxycarbonylalkyl groups, one to three C
3
-C
6
-alkylcarbonylalkyl groups, one to three C
3
-C
6
haloalkylcarbonylalkyl groups, one or two NR
15
S(O)
p
R
16
groups or one or two C(W)NR
15
S(O)
p
R
16
groups,
phenyl optionally substituted with any combination of one to three halogen atoms, one to three nitro groups, one to three cyano groups, one to three C
1
-C
4
alkyl groups, one to three C
1
-C
4
haloalkyl groups, one to three C
1
-C
4
alkoxy groups, one to three C
1
-C
4
haloalkoxy groups, one or two C
2
-C
6
alkoxyalkyl groups, one or two C
2
-C
6
haloalkoxyalkyl groups, one or two C(O)OR
14
groups, one or two C(O)R
14
groups, one to three C
3
-C
6
alkoxycarbonylalkyl groups, one to three C
3
-C
6
haloalkoxycarbonylalkyl groups, one to three C
3
-C
6
alkylcarbonylalkyl groups, one to three C
3
-C
6
haloalkylcarbonylalkyl groups, one or two NR
15
S(O)
p
R
16
groups or one or two C(W)NR
15
S(O)
p
R
16
groups,
OR
17
,
NR
18
R
19
,
NR
20
S(O)
q
R
21
,
NR
22
C(V)R
23
,
NR
24
P(V)(OR
25
)
2
,
C(V)NR
20
S(O)
q
R
21
,
cyano,
S(O)
q
R
26
,
P(V)(OR
27
)
2
,
C(V)R
28
or
C(V)OR
29
;
W is O, S, NR
30
, NOR
31
or NNR
32
R
33
;
V and Z are each independently O or S;
R
1
and R
14
are each independently C
1
-C
4
alkyl or C
1
-C
4
haloalkyl;
R
2
is hydrogen, C
1
-C
6
alkyl, C
3
-C
7
cycloalkyl, C
1
-C
6
haloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl, C
2
-C
6
alkoxyalkyl, C
2
-C
6
haloalkoxyalkyl, C
3
-C
6
alkoxycarbonylalkyl,
phenyl optionally substituted with any combination of one to three halogen atoms, one to three C
1
-C
4
alkyl groups, one to three C
1
-C
4
haloalkyl groups, one to three C
1
-C
4
alkoxy groups, one to three C
1
-C
4
haloalkoxy groups, one or two C
2
-C
6
alkoxyalkyl groups, one or two C
2
-C
6
haloalkoxyalkyl groups, one or two nitro groups, one or two cyano groups, one NR
15
S(O)
p
R
16
group, one C
2
-C
6
alkoxycarbonyl group, one C
2
-C
6
haloalkoxycarbonyl group, one C
2
-C
6
alkylcarbonyl group, one C
2
-C
6
haloalkylcarbonyl group, one C
3
-C
6
alkoxycarbonylalkyl group, one C
3
-C
6
haloalkoxycarbonylalkyl group, one C
3
-C
6
alkylcarbonylalkyl group or one C
3
-C
6
haloalkylcarbonylalkyl group,
a 4- to 10-membered heterocyclic ring optionally substituted with any combination of one or two oxo groups, one or two thioxo groups, one to three halogen atoms, one to three C
1
-C
4
alkyl groups, one to three C
1
-C
4
haloalkyl groups, one to three C
1
-C
4
alkoxy groups, one to three C
1
-C
4
haloalkoxy groups, one or two C
2
-C
6
alkoxyalkyl groups, one or two C
2
-C
6
haloalkoxyalkyl groups, one or two nitro groups, one or two cyano groups, one NR
15
S(O)
p
R
16
group, one C
2
-C
6
alkoxycarbonyl group, one C
2
-C
6
haloalkoxycarbonyl group, one C
2
-C
6
alkylcarbonyl group, one C
2
-C
6
haloalkylcarbonyl group, one C
3
-C
6
alkoxycarbonylalkyl group, one C
3
-C
6
haloalkoxycarbonylalkyl group, one C
3
-C
6
alkylcarbonylalkyl group or one C
3
-C
6
haloalkylcarbonylalkyl group,
C
1
-C
4
alkyl substituted with one phenyl group wherein the phenyl group is optionally substituted with any combination of one to three halogen atoms, one or two nitro groups, one or two cyano groups, one to three C
1
-C
4
alkyl groups, one to three C
1
-C
4
haloalkyl groups, one to three C
1
-C
4
alkoxy groups or one to three C
1
-C
4
haloalkoxy groups, or
C
1
-C
4
alkyl substituted with one 4- to 10-membered heterocyclic ring wherein the heterocyclic ring is optionally substituted with any combination of one to three halogen atoms, one or two nitro groups, one or two cyano groups, one to three C
1
-C
4
alkyl groups, one to three C
1
-C
4
haloalkyl groups, one to three C
1
-C
4
alkoxy groups or one to three C
1
-C

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