Pyrimidinone derivatives and herbicides containing them

Details Pyrimidinone derivatives and herbicides containing them Pyrimidinone derivatives and herbicides containing them

1998-09-04

2001-02-20

Shah, Mukund J. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S203000, C544S311000, C544S312000, C544S313000, C544S314000

Reexamination Certificate

active

06191070

ABSTRACT:

FILED OF INVENTION
The present invention relates to pyrimidinone derivatives and their use.
OBJECT OF THE INVENTION
It is an object of the present invention to provide compounds with excellent herbicidal activity.
SUMMARY OF THE INVENTION
The present inventors have intensively studied to seek out various compounds with excellent herbicidal activity. As a result, they have found that pyrimidinone derivatives of the general formula as depicted below have excellent herbicidal activity, thereby completing the present invention.
Thus the present invention provides pyrimidinone derivatives of the general formula:
(hereinafter referred to as the present compound(s))
wherein:
R
1
is hydrogen or C
1
-C
3
alkyl;
R
2
is C
1
-C
3
haloalkyl;
R
3
is nitrogen or CH;
G is any group of the general formula:
wherein:
E
1
, E
2
, E
3
, E
4
, E
5
, E
6
, E
7
, E
8
, E
9
, E
10
, E
11
, and E
12
are independently hydrogen or C
1
-C
3
alkyl; and
Q is any group of the general formula:
wherein:
X is hydrogen or halogen;
Y is halogen, nitro, cyano, or trifluoromethyl;
Z
1
is oxygen, sulfur, NH, or CH
2
;
n is 0 or 1;
R
4
is hydrogen or C
1
-C
3
alkyl;
R
5
is hydrogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, (C
3
-C
8
cycloalkyl) C
1
-C
6
alkyl, C
3
-C
6
alkenyl, C
3
-C
6
haloalkenyl, C
3
-C
6
alkynyl, C
3
-C
6
haloalkynyl, cyano C
1
-C
6
alkyl, C
1
-C
4
alkoxy C
1
-C
4
alkyl, C
1
-C
3
alkoxy C
1
-C
3
alkoxy C
1
-C
3
alkyl, carboxy C
1
-C
6
alkyl, (C
1
-C
6
alkoxy)carbonyl C
1
-C
6
alkyl, {(C
1
-C
4
alkoxy) C
1
-C
4
alkoxy}carbonyl C
1
-C
6
alkyl, (C
3
-C
8
cycloalkoxy)carbonyl C
1
-C
6
alkyl, C
1
-C
4
alkylthio C
1
-C
4
alkyl, hydroxy C
1
-C
6
alkyl, —CH
2
CON(R
12
)R
13
, —CH
2
COON(R
12
)R
13
, —CH(C
1
-C
4
alkyl)CON(R
12
)R
13
, or —CH(C
1
-C
4
alkyl)COON(R
12
)R
13
,
wherein:
R
12
and R
13
are independently hydrogen, C
1
-C
6
alkyl, C
3
-C
8
cycloalkyl, C
1
-C
6
haloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl, cyano C
1
-C
6
alkyl, C
1
-C
4
alkoxy C
1
-C
4
alkyl, C
1
-C
4
alkylthio C
1
-C
4
alkyl, carboxy C
1
-C
6
alkyl, (C
1
-C
6
alkoxy)carbonyl C
1
-C
6
alkyl, (C
3
-C
8
cycloalkoxy)carbonyl C
1
-C
6
alkyl, (C
1
-C
6
alkyl)carbonyloxy C
2
-C
6
alkyl, (C
1
-C
6
alkyl)carbonylamino C
2
-C
6
alkyl, hydroxy C
2
-C
6
alkyl, optionally substituted benzyl, optionally substituted phenyl, or {(C
1
-C
4
alkoxy) C
1
-C
4
alkyl}carbonyl C
1
-C
6
alkyl, or R
12
and R
13
are taken together to form trimethylene, tetramethylene, pentamethylene, ethyleneoxyethylene, or ethylenethioethylene;
and
B is hydrogen, halogen, nitro, cyano, chlorosulfonyl, OR
10
, SR
10
, SO
2
OR
21
, N(R
12
)R
13
,SO
2
N(R
12
)R
13
,NR
12
(COR
9
), NR
12
(SO
2
R
28
), N(SO
2
R
28
)(SO
2
R
29
), N(SO
2
R
28
)(COR
9
), NHCOOR
11
, CONR
12
R
13
, CSNR
12
R
13
, COR
30
, CR
23
═CR
24
COR
30
, CR
23
═CR
24
CON(R
12
)R
13
, CH
2
CHWCON(R
12
)R
13
, CR
30
═NOR
31
, CR
30
═NN(R
12
)R
13
,CR
30
(Z
2
R
32
)
2
, OCO
2
R
32
, OCOR
32
, COOR
22
, CH
2
OR
10
, CR
23
═CR
24
COOR
25
, or CH
2
CHWCOOR
25
,
wherein:
R
12
and R
13
are as defined above;
W is hydrogen, chlorine, or bromine;
Z
2
is oxygen or sulfur;
R
9
is hydrogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
8
cycloalkyl, or C
3
-C
6
alkenyl;
R
11
is hydrogen, C
1
-C
6
alkyl, C
3
-C
8
cycloalkyl, or C
3
-C
6
alkenyl;
R
28
and R
29
are independently C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, or phenyl;
R
30
is hydrogen, C
1
-C
6
alkyl, C
3
-C
6
alkenyl, or C
3
-C
6
alkynyl;
R
31
is hydrogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
haloalkenyl, C
3
-C
6
alkynyl, cyano C
1
-C
6
alkyl, C
2
-C
8
alkoxyalkyl, C
2
-C
8
alkylthioalkyl, carboxy C
1
-C
6
alkyl, (C
1
-C
6
alkoxy)carbonyl C
1
-C
6
alkyl, (C
3
-C
8
cycloalkoxy)-carbonyl C
1
-C
6
alkyl, or {(C
1
-C
4
alkoxy) C
1
-C
4
alkoxy}carbonyl C
1
-C
6
alkyl;
R
32
is hydrogen, C
1
-C
6
alkyl, C
3
-C
8
cycloalkyl, or C
3
-C
6
alkenyl;
R
10
is hydrogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
8
cycloalkyl, benzyl, C
3
-C
6
alkenyl, C
3
-C
6
haloalkenyl, C
3
-C
6
alkynyl, C
3
-C
6
haloalkynyl, cyano C
1
-C
6
alkyl, C
1
-C
4
alkoxy C
1
-C
4
alkyl, C
1
-C
4
alkylthio C
1
-C
4
alkyl, carboxy C
1
-C
6
alkyl, (C
1
-C
8
alkoxy)carbonyl C
1
-C
6
alkyl, (C
1
-C
6
haloalkoxy)-carbonyl C
1
-C
6
alkyl, {(C
1
-C
4
alkoxy) C
1
-C
4
alkoxy}carbonyl C
1
-C
6
alkyl, (C
3
-C
8
cycloalkoxy)carbonyl C
1
-C
6
alkyl, (C
3
-C
8
cycloalkyl) C
1
-C
6
alkoxycarbonyl C
1
-C
6
alkyl, —CH
2
COON—(R
12
)R
13
,—CH(C
1
-C
4
alkyl)COON(R
12
)R
13
,—CH
2
CON(R
12
)R
13
, —CH(C
1
-C
4
alkyl)CON(R
12
)R
13
(wherein R
12
and R
13
are as defined above), C
2
-C
6
alkenyloxycarbonyl C
1
-C
6
alkyl, C
3
-C
6
haloalkenyloxycarbonyl C
1
-C
6
alkyl, C
3
-C
6
alkynyloxycarbonyl C
1
-C
6
alkyl, C
3
-C
6
haloalkynyloxycarbonyl C
1
-C
6
alkyl, (C
1
-C
6
alkylthio)carbonyl C
1
-C
6
alkyl, (C
1
-C
6
haloalkylthio)-carbonyl C
1
-C
6
alkyl, (C
3
-C
6
alkenylthio)carbonyl C
1
-C
6
alkyl, (C
3
-C
6
haloalkenylthio)carbonyl C
1
-C
6
alkyl, (C
3
-C
6
alkynylthio)carbonyl C
1
-C
6
alkyl, (C
3
-C
6
haloalkynylthio)carbonyl C
1
-C
6
alkyl, (C
3
-C
8
cycloalkylthio)carbonyl C
1
-C
6
alkyl, (C
3
-C
8
cyclohaloalkylthio)carbonyl C
1
-C
6
alkyl, ((C
3
-C
8
cycloalkyl) C
1
-C
6
alkylthio)carbonyl C
1
-C
6
alkyl, di(C
1
-C
6
alkyl)C═NO carbonyl C
1
-C
6
alkyl, (optionally substituted benzylthio)-carbonyl C
1
-C
6
alkyl, (optionally substituted phenylthio)-carbonyl C
1
-C
6
alkyl, hydroxy C
2
-C
6
alkoxycarbonyl C
1
-C
6
alkyl, (C
1
-C
6
alkyl)carbonyloxy C
2
-C
6
alkoxycarbonyl C
1
-C
6
alkyl, (C
1
-C
6
alkyl)carbonylamino C
2
-C
6
alkoxycarbonyl C
1
-C
6
alkyl, {(C
1
-C
6
alkoxy)carbonyl C
1
-C
6
alkyloxycarbonyl C
1
-C
6
alkyl, hydroxy C
1
-C
6
alkyl, C
1
-C
6
alkoxycarbonyl, C
1
-C
6
haloalkoxycarbonyl, C
3
-C
8
cycloalkoxycarbonyl, C
3
-C
6
alkenyloxycarbonyl, optionally substituted benzyloxycarbonyl, C
1
-C
6
alkylcarbonyl, optionally substituted benzyloxycarbonyl C
1
-C
6
alkyl, optionally substituted phenoxycarbonyl C
1
-C
6
alkyl, optionally substituted furyloxycarbonyl C
1
-C
6
alkyl, optionally substituted furyl C
1
-C
6
alkyloxycarbonyl C
1
-C
6
alkyl, optionally substituted thienyloxycarbonyl C
1
-C
6
alkyl, optionally substituted thienyl C
1
-C
6
alkyloxycarbonyl C
1
-C
6
alkyl, optionally substituted pyrrolyloxycarbonyl C
1
-C
6
alkyl, optionally substituted pyrrolyloxy C
1
-C
6
alkyloxycarbonyl C
1
-C
6
alkyl, optionally substituted imidazoyloxycarbonyl C
1
-C
6
alkyl, optionally substituted imidazoyl C
1
-C
6
alkyloxycarbonyl C
1
-C
6
alkyl, optionally substituted pyrazoyloxycarbonyl C
1
-C
6
alkyl, optionally substituted pyrazoyl C
1
-C
6
alkyloxycarbonyl C
1
-C
6
alkyl, optionally substituted thiazoyloxycarbonyl C
1
-C
6
alkyl, optionally substituted thiazoyl C
1
-C
6
alkyloxycarbonyl C
1
-C
6
alkyl, optionally substituted oxazoyloxycarbonyl C
1
-C
6
alkyl, optionally substituted oxazoyl C
1
-C
6
alkyloxycarbonyl C
1
-C
6
alkyl, optionally substituted isothiazoyloxycarbonyl C
1
-C
6
alkyl, optionally substituted isothiazoyl C
1
-C
6
alkyloxycarbonyl C
1
-C
6
alkyl, optionally substituted isoxazoyloxycarbonyl C—CC alkyl, optionally substituted isoxazoyl C
1
-C
6
alkyloxycarbonyl C
1
-C
6
alkyl, optionally substituted pyridyloxycarbonyl C
1
-C
6
alkyl, optionally substituted pyridyl C
1
-C
6
alkyloxycarbonyl C
1
-C
6
alkyl, optionally substituted pyradinyloxycarbonyl C
1
-C
6
alkyl, optionally substituted pyradinyl C
1
-C
6
alkyloxycarbonyl C
1
-C
6
alkyl, optionally substituted pyriaidinyloxycarbonyl C
1
-C
6
alkyl, optionally substituted pyrimidinyl C
1
-C
6
alkyloxycarbonyl C
1
-C
6
alkyl, optionally substituted yridazinyloxycarbonyl C
1
-C
6
alkyl, optionally substituted pyridazinyl C
1
-C
6
alkyloxycarbonyl C
1
-C
6
alkyl, optionally substituted indolidinyloxycarbonyl C
1
-C
6
alkyl, optionally substituted indolidinyl C
1
-C
6
alkyloxycarbonyl C
1
-C
6
alkyl, optionally substituted

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