Substituted methylene pyrazolinones and the herbicidal use...

Details Substituted methylene pyrazolinones and the herbicidal use... Substituted methylene pyrazolinones and the herbicidal use...

2001-02-28

2002-10-15

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C548S364400, C504S253000, C504S219000, C546S202000, C546S196000, C540S603000

Reexamination Certificate

active

06465395

ABSTRACT:

BACKGROUND OF THE INVENTION
Weeds cause tremendous global economic losses by reducing crop yields and lowering crop quality. Worldwide, agronomic crops must compete with a vast variety of weed species. Although there are a number of commercial herbicides available, crop safety and efficacy over a broad spectrum of weed species remain challenges in modern agronomic practice. Accordingly there is an ongoing need to discover and develope more crop-selective and broader spectrum herbicidal agents.
Thiochroman- and dihydrobenzothiophene-hydroxypyrazole derivatives and their herbicidal use are described in U.S. Pat. No. 5,607,898 and WO 97/08164. However, thiochroman and dihydrobenzothiophene substituted methylene pyrazolinone compounds and their use as broad-spectrum, crop-selective herbicides are not described therein.
Therefore, it is an object of this invention to provide highly effective broad spectrum herbicidal methylene pyrazolinone compounds.
It is also an object of this invention to provide a method for the control of a broad spectrum of undesirable plant species.
It is a further object of this invention to provide a method for the selective control of undesirable plant species in the presence of a crop.
These and other objects and features of the invention will become more apparent from the detailed description thereof set forth hereinbelow.
SUMMARY OF THE INVENTION
The present invention provides thiochroman-and dihydrobenzothiophene-substituted methylene pyrazolinone compounds of formula I
wherein
m is zero or 1;
R
1
, R
2
, R
3
and R
4
are each independently H, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl or C
2
-C
4
alkoxyalkyl;
R
5
is C
1
-C
3
alkyl, C
3
-C
4
alkenyl or C
3
-C
4
haloalkenyl;
R
6
is H, halogen, CN, C
1
-C
4
alkyl, C
2
-C
4
alkenyl, C
1
-C
4
alkoxyalkyl or C
1
-C
4
alkoxycarbonyl;
X is CR
7
R
8
, CHOR
9
, C═NOR
10
, C═NNR
16
R
17
, C═O or C(OR
9
)
2
;
R
7
is H, C
1
-C
4
alkyl or C
1
-C
4
haloalkyl;
R
8
is H, C
1
-C
4
alkyl, C
2
-C
4
alkenyl, C
2
-C
4
alkynyl or C
1
-C
4
alkoxyalkyl;
R
9
and R
10
are each independently H or C
1
-C
6
alkyl optionally substituted with one or more C
2
-C
6
alkenyl, C
2
-C
6
alkynyl, C
1
-C
6
haloalkyl or C
3
-C
6
cycloalkyl groups;
Y is O, S, SO or SO
2
;
Z is H, halogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
2
-C
4
alkoxyalkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkoxy;
p is an integer of 1, 2 or 3;
G is OR
11
, OCH
2
COR
11
, SCH
2
COR
11
, OCN
2
CSR
11
, SCH
2
CSR
11
, OCOR
11
, SCOR
11
, OCSR
11
, SCSR
11
, S(O)
n
R
12
, NR
13
R
14
, P(O) (OR
15
)
2
, halogen, CN, SCN,
n is zero, 1 or 2;
R
11
and R
12
are each independently 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
haloalkynyl, C
1
-C
6
alkoxyalkyl, benzyl optionally substituted with one to three halogen, C
1
-C
6
alkyl, C
1
-C
6
alkoxy or C
1
-C
6
haloalkyl groups or phenyl optionally substituted with one to three halogen, C
1
-C
6
alkyl, C
1
-C
6
alkoxy or C
1
-C
6
haloalkyl groups;
R
13
and R
14
are each independently H, C
1
-C
6
alkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl, or R
13
and R
14
may be taken together with the atom to which they are attached to represent a four- to seven-membered ring optionally interrupted by oxygen, sulfur, or nitrogen and optionally substituted with one to three halogen or C
1
-C
6
alkyl groups;
R
15
is C
1
-C
6
alkyl;
R
16
is H or C
1
-C
6
alkyl;
R
17
is H, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
2
-C
6
alkoxycarbonyl, C
2
-C
6
alkylcarbonyl, COR
18
or phenyl optionally substituted with one to three C
1
-C
3
alkyl, halogen, CN or NO
2
groups, or R
16
and R
17
may be taken together to represent ═C(C
1
-C
3
alkyl)
2
;
R
18
is phenyl optionally substituted with one to three C
1
-C
3
alkyl, halogen, CN or NO
2
groups, or a 5-to 6-membered aromatic heterocyclic ring optionally substituted with one to three C
1
-C
3
alkyl, halogen, CN or NO
2
groups;
M is a transition metal or an alkaline-earth metal; and
q is an integer of 1, 2 or 3; or the geometric or optically active isomers thereof.
The present invention also provides herbicidal compositions and methods and a process to prepare a compound of formula I.


REFERENCES:
patent: 5607898 (1997-03-01), Nakamura et al.
patent: 2333234 (1999-11-01), None
patent: WO 97/08164 (1997-03-01), None
patent: WO 98/35954 (1998-08-01), None
patent: WO 99/26930 (1999-06-01), None
patent: WO 99/59991 (1999-11-01), None
patent: WO-99/59991 (1999-11-01), None

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