Herbicidal composition

Details Herbicidal composition Herbicidal composition

2000-07-06

2002-04-23

Clardy, S. Mark (Department: 1616)

Plant protecting and regulating compositions

Antidotes

Hetero ring containing antidote

C504S110000

Reexamination Certificate

active

06376424

ABSTRACT:

The present invention relates to new selectively herbicidal compositions to combat grasses and weeds in crops of cultivated plants, especially in crops of cereals and rice which comprise a herbicide and a safener (antidote) and which protect the cultivated plants but not the weeds against the phytotoxic effect of the herbicide, and to the use of this composition for weed control in crops of cultivated plants.
When applying herbicides, the cultivated plants may also suffer severe damage owing to factors that include the concentration of the herbicide and the mode of application, the cultivated plant itself, the nature of the soil, and the climatic conditions such as exposure to light, temperature and rainfall.
To counteract this problem and similar ones, the proposal has already been made to use different compounds as safeners which are able to antagonise the harmful action of the herbicide on the cultivated plant, i.e. to protect the cultivated plant while leaving the herbicidal action on the weeds to be controlled virtually unimpaired. It has, however, been found that the proposed safeners often have a very specific action with respect not only to the cultivated plants but also to the herbicide, and in some cases also subject to the mode of application, i.e. a specific safener will often be suitable only for a specific cultivated plant and a specific class of herbicide or a specific herbicide. Compounds are known for example from WO 97/18712 which protect crop plants against the phytotoxic effect of specific herbicides. It has now been found that compounds of formula IIa
wherein the substituents are as defined hereinafter, are suitable for the protection of crop plants against the phytotoxic effect of a compound of formula I
Accordingly, the invention provides a selective herbicidal composition comprising, in addition to customary inert formulation assistants such as carriers, solvents and wetting agents, a mixture of
a) a herbicidally effective amount of a herbicide of formula I
 and
b) to antagonise the herbicide, an antidotally effective amount of a safener of formula IIa
 wherein
R
32
is hydrogen, C
1
-C
8
alkyl or C
1
-C
8
alkyl substituted by C
1
-C
6
alkoxy or C
3
-C
6
alkenyloxy and
X
1
is hydrogen or chlorine; or of formula IIb
wherein E is nitrogen or methine;
R
38
is C
1
-C
4
alkyl;
R
39
is —CCl
3
, phenyl or phenyl substituted by halogen, and
R
40
and R
41
independently of one another are hydrogen or halogen;
or of formula IIc
wherein R
27
and R
28
independently of one another are hydrogen or halogen, and
R
29
, R
30
and R
31
independently of one another are C
1
-C
4
alkyl; or of formula IId
wherein A
2
is a
 group, R
35
and R
36
independently of one another are hydrogen, C
1
-C
8
alkyl, C
3
-C
8
cycloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkinyl,
 or C
1
-C
4
alkyl substituted by C
1
-C
4
alkoxy or
 or R
35
and R
36
together form a C
4
-C
6
alkylene bridge, which may be broken by oxygen, sulfur, SO, SO
2
, NH or —N(C
1
-C
4
alkyl)-; R
37
is hydrogen or C
1
-C
4
alkyl;
R
33
is hydrogen, halogen, cyano, trifluoromethyl, nitro, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
1
-C
4
alkylthio, C
1
-C
4
alkylsulfinyl, C
1
-C
4
alkylsulfonyl, —COORj, —CONR
k
R
m
, —COR
n
, —SO
2
NR
k
R
m
or —OSO
2
—C
1
-C
4
alkyl;
R
g
is hydrogen, halogen, cyano, nitro, C
1
-C
4
alkyl, C
1
-C
4
halogenalkyl, C
1
-C
4
alkylthio, C
1
-C
4
alkylsulfinyl, C
1
-C
4
alkylsulfonyl, —COORj, —CONR
k
R
m
, —COR
n
, —SO
2
NR
k
R
m
—OSO
2
—C
1
-C
4
alkyl, C
1
-C
6
alkoxy, or C
1
-C
6
alkoxy substituted by C
1
-C
4
alkoxy or halogen, C
3
-C
6
alkenyloxy, or C
3
-C
6
alkenyloxy substituted by halogen, or C
3
-C
6
alkinyloxy, or R
33
and R
34
together form a C
3
-C
4
alkylene bridge, which may be substituted by halogen or C
1
-C
4
alkyl, or they form a C
3
-C
4
alkenylene bridge, which may be substituted by halogen or C
1
-C
4
alkyl, or they form a C
4
alkadienylene bridge, which may be substituted by halogen or C
1
-C
4
alkyl;
R
34
and R
h
independently of one another are hydrogen, halogen, C
1
-C
4
alkyl, trifluoromethyl, C
1
-C
6
alkoxy, C
1
-C
6
alkylthio or —COORj;
R
c
is hydrogen, halogen, nitro, C
1
-C
4
alkyl or methoxy; R
d
is hydrogen, halogen, nitro, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
1
-C
4
alkylthio, C
1
-C
4
alkylsulfinyl, C
1
-C
4
alkylsulfonyl, —COOR
j
or CONR
k
R
m
;
R
e
is hydrogen, halogen, C
1
-C
4
alkyl, —COOR
j
, trifluoromethyl or methoxy, or R
d
and R
e
together form a C
3
-C
4
alkylene bridge;
R
f
is hydrogen, halogen or C
1
-C
4
alkyl;
R
x
and R
y
independently of one another are hydrogen, halogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy, C
1
-C
4
alkylthio, —COOR
38
, trifluoromethyl, nitro or cyano;
R
j
, R
k
and R
m
independently of one another are hydrogen or C
1
-C
4
alkyl; or
R
k
and R
m
together form a C
4
-C
6
alkylene bridge, which may be broken by oxygen, NH or —N(C
1
-C
4
alkyl)—;
R
n
is C
1
-C
4
alkyl, phenyl, or phenyl substituted by halogen, C
1
-C
4
alkyl, methoxy, nitro or trifluoromethyl;
R
38
is hydrogen, C
1
-C
10
alkyl, C
1
-C
4
alkoxy-C
1
-C
4
alkyl, C
1
-C
4
alkylthio-C
1
-C
4
alkyl, di-C
1
-C
4
alkylamino-C
1
-C
4
alkyl, halogen-C
1
-C
8
alkyl, C
2
-C
8
alkenyl, halogen-C
2
-C
8
alkenyl, C
3
-C
8
alkinyl, C
3
-C
7
cycloalkyl, halogen-C
3
-C
7
-cycloalkyl, C
1
-C
8
alkylcarbonyl, allylcarbonyl, C
3
-C
7
cycloalkylcarbonyl, benzoyl which is unsubstituted or substituted on the phenyl ring up to three times identically or differently by halogen, C
1
-C
4
alkyl, halogen-C
1
-C
4
alkyl, halogen-C
1
-C
4
alkoxy or C
1
-C
4
alkoxy; or furoyl, thienyl; or C
1
-C
4
alkyl substituted by phenyl, halogenphenyl, C
1
-C
4
alkylphenyl, C
1
-C
4
alkoxyphenyl, halogen-C
1
-C
4
alkylphenyl, halogen-C
1
-C
4
alkoxyphenyl, C
1
-C
6
alkoxycarbonyl, C
1
-C
4
alkoxy-C
1
-C
8
alkoxycarbonyl, C
3
-C
8
alkenyloxycarbonyl, C
3
-C
8
alkinyloxycarbonyl, C
1
-C
8
alkylthiocarbonyl, C
3
-C
8
alkenylthiocarbonyl, C
3
-C
8
alkinylthiocarbonyl, carbamoyl, mono-C
1
-C
4
alkylaminocarbonyl, di-C
1
-C
4
alkylaminocarbonyl; or phenylaminocarbonyl, which is unsubstituted or substituted on the phenyl ring up to three times identically or differently by halogen, C
1
-C
4
alkyl, halogen-C
1
-C
4
alkyl, halogen-C
1
-C
4
alkoxy or C
1
-C
4
alkoxy, or once by cyano or nitro, or dioxolan-2-yl which is unsubstituted or substituted by one or two C
1
-C
4
alkyl radicals, or dioxan-2-yl, which is unsubstituted or substituted by one or two C
1
-C
4
alkyl radicals, or C
1
-C
4
alkl which is substituted by cyano, nitro, carboxyl or C
1
-C
8
alkylthio-C
1
-C
8
alkoxycarbonyl; or a compound of formula IIf
wherein R
56
and R
57
independently of one another are C
1
-C
6
alkyl or C
2
-C
6
alkenyl; or R
56
and R
57
together are
R
58
and R
59
independently of one another are hydrogen or C
1
-C
6
alkyl; or R
56
and R
57
together are
R
60
and R
61
independently of one another are C
1
-C
4
alkyl, or R
46
and R
47
together are —(CH
2
)
6
—;
R
62
is hydrogen, C
1
-C
4
alkyl or
 or R
56
and R
57
together are
R
63
, R
64
, R
65
, R
66
, R
67
, R
68
, R
69
, R
70
, R
71
, R
72
, R
73
, R
74
, R
75
, R
76
, R
77
, and R
78
independently of one another are hydrogen or C
1
-C
4
alkyl;
or a compound of formula IIg
wherein R
79
is hydrogen or chlorine and R
80
is cyano or trifluoromethyl, or a compound of formula IIh
wherein R
81
is hydrogen or methyl, or of formula IIj
wherein R
82
is hydrogen, C
1
-C
4
alkyl, C
1
-C
4
alkyl substituted by C
1
-C
4
alkyl-X
2
— or C
1
-C
4
halogenal-X
2
—, C
1
-C
4
halogenalkyl, nitro, cyano, —COOR
85
, —NR
86
R
87
, —SO
2
NR
88
R
89
or —CONR
90
R
91
;
R
83
is hydrogen, halogen, C
1
-C
4
alkyl, trifluoromethyl, C
1
-C
4
alkoxy or C
1
-C
4
halogenalkoxy;
R
84
is hydrogen, halogen or C
1
-C
4
alkyl;
U, V, W
1
and Z
4
independently of one another are oxygen, sulfur, C(R
92
)R
93
, carbonyl, NR
94
, a
 group, wherein R
102
is C
2
-C
4
alkenyl or C
2
-C
4
alkinyl; subject to the proviso that a) at least one of the ring members U, V, W
1
or Z
4
is carbonyl, and a ring member adjacent to this or these ri

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