Selective herbicidal composition

Details Selective herbicidal composition Selective herbicidal composition

1997-03-17

2003-05-27

Pak, John (Department: 1616)

Plant protecting and regulating compositions

Antidotes

Hetero ring containing antidote

C504S130000, C504S149000, C504S342000

Reexamination Certificate

active

06569806

ABSTRACT:

The present invention relates to a selective herbicidal composition for controlling grasses and weeds in crops of cultivated plants, especially in crops of maize, which composition comprises a herbicide and a safener (antidote) and protects the cultivated plants, but not the weeds, from the phytotoxic action of the herbicide, and to the use of said composition, or of the combination of herbicide and safener, for controlling weeds 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 species-specific action, not only with respect 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.
It has now been found that certain chloro- and dichloroacetamides are suitable for protecting cultivated plants from the phytotoxic action of the compound a RS,1′S(−)N-(1′-methyl-2′-methoxyethyl)-N-chloracetyl-2-ethyl-6-methylaniline of formula I
wherein R
0
is methyl or ethyl.
Accordingly, the invention provides a selective herbicidal composition comprising, in addition to conventional inert formulation assistants such as carriers, solvents and wetting agents, as active component, a mixture of
a) a herbicidally effective amount of a compound of formula I
wherein R
0
is methyl or ethyl, and
b) to antagonise the herbicide, an antidotally effective amount of a compound of formula II as safener
R—CHYCl  (II)
wherein R is a radical of formula
 wherein
R
33
and R
34
are each independently of the other C
1
-C
6
alkyl or C
2
-C
6
alkenyl; or R
33
and R
34
, taken together, are
R
35
and R
36
are each independently of the other hydrogen or C
1
-C
6
alkyl;
or R
33
and R
34
, taken together, are
R
37
and R
38
are each independently of the other C
1
-C
4
alkyl, or R
37
and R
38
, taken together, are —(CH
2
)
5
—;
R
39
is hydrogen, C
1
-C
4
alkyl or
or R
33
and R
34
, taken together, are
and R
40
, R
41
, R
42
, R
43
, R
44
, R
45
, R
46
, R
47
, R
48
, R
49
, R
50
, R
51
, R
52
, R
54
and R
55
are each independently of one another hydrogen or C
1
-C
4
alkyl,
or R is a radical of formula
or R is a radical of formula
 wherein R
1
, R
2
, R
3
and
R
4
are each independently of one another hydrogen, C
1
-C
4
alkyl, C
1
-C
4
alkoxy or C
1
-C
4
haloalkyl, R
5
, R
6
, R
7
and R
8
are each independently of one another hydrogen, C
1
-C
4
alkyl or C
1
-C
4
haloalkyl, or R is a radical of formula
 wherein R
9
is C
1
-C
4
alkyl or halogen, R
10
is halogen,
R
11
and R
12
are each independently of the other hydrogen or C
1
-C
4
alkyl, and Q is C
1
-C
4
alkylene or alkyl-substituted C
1
-C
4
alkylene,
or R is a radical of formula
 wherein R
14
is hydrogen, halogen, C
1
-C
4
alkyl, dioxymethylene, C
1
-C
4
alkoxy, C
2
-C
4
alkenyloxy, C
2
-C
4
alkynyloxy or cyano-C
1
-C
4
alkyl, P is C
1
-C
4
alkyl, C
2
-C
4
alkenyl, C
2
-C
4
alkynyl, C
3
-C
8
cycloalkyl, C
1
-C
4
alkoxy-C
1
-C
4
alkyl, C
2
-C
4
alkenoxy-C
1
-C
4
alkyl, C
2
-C
4
alkynoxy-C
1
-C
4
alkyl, C
1
-C
4
alkylthio-C
1
-C
4
alkyl, C
2
-C
4
alkenylthio-C
1
-C
4
alkyl, C
2
-C
4
alkynylthio-C
1
-C
4
alkyl, C
1
-C
4
alkylsulfinyl-C
1
-C
4
alkyl, C
1
-C
4
alkylsulfonyl-C
1
-C
4
alkyl, halo-C
1
-C
4
alkyl, cyano-C
1
-C
4
alkyl, 2,2-di-C
1
-C
4
alkoxy-C
1
-C
4
alkyl, 1,3-dioxolan-2-yl-C
1
-C
4
alkyl, 1,3-dioxolan-4-yl-C
1
-C
4
alkyl, 2,2-di-C
1
-C
4
alkyl-1,3-dioxolan-4-yl-C
1
-C
4
alkyl, 1,3-dioxan-2-yl-C
1
-C
4
alkyl, 2-benzopyranyl-C
1
-C
4
alkyl, C
1
-C
4
alkoxycarbonyl or C
2
-C
4
alkenyloxycarbonyl or tetrahydrofurfuryl-C
1
-C
4
alkyl, the group P-X is also halo-C
1
-C
4
alkyl, X is O, S, SO or SO
2
, n is 1, 2 or 3, A is a C
1
-C
8
hydrocarbon radical or a C
1
-C
8
hydrocarbon radical which is substituted by alkoxy, alkylthio, fluoro, cyano or haloalkyl, and R
13
is hydrogen, a C
1
-C
5
hydrocarbon radical or a C
1
-C
5
hydrocarbon radical which is substituted by alkoxy, polyalkoxy, halogen, cyano or trifluoromethyl;
C
3
-C
8
cycloalkyl, C
1
-C
4
alkyl-C
3
-C
8
cycloalkyl, di-C
1
-C
4
alkoxy-C
1
-C
4
alkyl, 1,3-dioxolan-2-yl-C
1
-C
4
alkyl, 1,3-dioxolan-4-yl-C
1
-C
4
alkyl, 1,3-dioxan-2-yl-C
1
-C
4
alkyl, furyl-C
1
-C
4
alkyl, tetrahydrofuryl-C
1
-C
4
alkyl, or a radical of formula —NHCO
2
R
01
, —CH
2
CO
2
R
01
, —CH(CH
3
)CO
2
R
01
or —CH(R
02
)—C(R
03
)═NOR
04
, wherein R
01
is methyl, ethyl, propyl, isopropyl or allyl, R
02
and R
03
are each hydrogen or C
1
-C
4
alkyl, and R
04
is hydrogen, C
1
-C
4
alkyl, C
2
-C
4
alkenyl or C
2
-C
4
alkynyl, or R is a radical of formula (H
5
C
2
O)
2
P(O)CH
2
NHCO— or
 wherein R
15
and R
16
are each independently of the other hydroxyl, C
1
-C
4
alkyl, aryl, C
1
-C
4
alkoxy, C
2
-C
4
alkenyloxy, C
2
-C
4
alkynyloxy, C
2
-C
4
haloalkoxy, C
2
-C
8
alkoxyalkoxy, C
1
-C
4
cyanoalkoxy, C
1
-C
4
phenylalkoxy or aryloxy or aryloxy which is substituted by halogen, cyano, nitro or C
1
-C
4
alkoxy, R
17
is hydrogen, C
1
-C
4
alkyl or phenyl, or phenyl which is substituted by halogen, cyano, nitro or C
1
-C
4
alkoxy, R
18
is hydrogen, or C
1
-C
4
alkyl, R
19
is hydrogen or a radical of formula —COCX
1
X
2
—R
06
, or an alkenoyl radical which contains 2 to 4 carbon atoms in the alkenyl moiety and which is substituted by halogen, and X
1
and X
2
are each independently of the other hydrogen or halogen, or is a radical of formula —COOR
07
or —COR
08
or a C
1
-C
4
alkyl, C
2
-C
4
alkenyl or C
1
-C
4
phenylalkyl radical which may be substituted at the phenyl ring by halogen, cyano, nitro or C
1
-C
4
alkoxy, and R
20
is hydrogen, C
1
-C
4
alkyl, C
2
-C
4
alkenyl or C
2
-C
4
alkynyl, R
06
is hydrogen, halogen or C
1
-C
6
alkyl, R
07
is C
1
-C
4
alkyl, C
1
-C
4
phenylalkyl or C
1
-C
4
phenylalkyl which is substituted in the phenyl moiety by halogen, cyano, nitro or C
1
-C
4
alkoxy, and R
08
is C
1
-C
4
alkyl, C
2
-C
4
alkenyl, C
2
-C
4
alkynyl, phenyl, C
1
-C
4
phenylalkyl or C
1
-C
4
phenylalkyl which is substituted in the phenyl moiety by halogen, cyano, nitro or C
1
-C
4
alkoxy,
or R is a radical of formula
or of formula
 wherein R
21
is methyl, ethyl, propyl, 1-methylethyl, 2-propenyl, 2-butenyl, 1,1-dimethyl-2-propenyl, 2-propynyl or 2-methyl-2-propynyl, and R
22
, R
23
, R
24
and R
25
are each independently of one another hydrogen or methyl,
and Y is chloro, or
Y is hydrogen if R is a radical of formula (H
5
C
2
O)
2
P(O)CH
2
NHCO—.
The alkyl groups cited in connection with the compounds of formula II may be straight-chain or branched and are typically methyl, ethyl, propyl, butyl, pentyl and hexyl, as well as branched isomers thereof. Suitable alkenyl radicals are derived from the aforementioned alkyl radicals. Aryloxy is most suitably phenyl and naphthoxy. Hydrocarbon radicals will be understood as meaning monovalent or divalent, saturated or unsaturated straight-chain or branched, or saturated or unsaturated cyclic radicals of carbon and hydrogen, typically alkyl, cycloalkyl, alkenyl, alkynyl, cycloalkenyl and phenyl.
The invention further relates to the use of the novel composition for controlling weeds and grasses in crops of cultivated plants, in particular maize.
Preferred compounds of formula II for use in the novel composition are those wherein R is a radical of formula
wherein R
33
and R
34
together are
R
37
and R
38
are each independently of the other C

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