Herbicidal synergistic composition, and method of...

Details Herbicidal synergistic composition, and method of... Herbicidal synergistic composition, and method of...

2002-01-29

2003-01-28

Pryor, Alton (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

Plural active ingredients

Reexamination Certificate

active

06511941

ABSTRACT:

The present invention relates to a novel herbicidal synergistic composition which comprises a combination of herbicidally active ingredients suitable for the selective control of weeds in crops of useful plants, for example in rice crops.
The invention furthermore relates to a method of controlling weeds in crops of useful plants, and to the use of this novel composition for this purpose.
The compound of formula I
is herbicidally active, as described in, for example, WO 91/05781.
The following compounds of formulae II to V are also known as herbicides, and some of them are commercially available:
a) Compounds of formula II
 in which
A is a group
X is —O—, —CH
2
— or —NH—;
Y is CH
3
or OCH
3
;
E is CH or N;
m in the case of the groups A1 and A4 is the number 0 or 1 and in the case of the groups A2, A5 and A3 the number 0, are known, for example, from The Pesticide Manual, Tenth Edition, The British Crop Protection Council, Cambridge, pages 85, 211, 701, 873 and 1005, and from EP-A-0 342 569, U.S. Pat. No. 5,009,699 and U.S. Pat. No. 4,746,353.
b) Compounds of formula ll
 in which
B is —CH
2
Cl, —C
2
H
5
, —S—CH
2
CH
3
,
R
2
is hydrogen, CH
3
, C
2
H
5
or —(CH
2
)
2
OCH
2
CH
2
CH
3
;
R
3
is —CH(CH
3
)—CH(CH
3
)
2
,
or
R
2
and R
3
together are —(CH
2
)
6
— are known, for example, from The Pesticide Manual, Tenth Edition, The British Crop Protection Council, Cambridge, pages 399, 649, 706, 828 and 845.
c) Compounds of formula IV
 in which
z is
are known, for example, from The Pesticide Manual, Tenth Edition, The British Crop Protection Council, Cambridge, pages 870 and 1045, and from U.S. Pat. No. 4,894,085.
d) Compounds of formula V
in which
are known, for example, from The Pesticide Manual, Tenth Edition, The British Crop Protection Council, Cambridge, pages 620 and 621.
Surprisingly, it has now emerged that a combination of variable quantities of the active ingredients, i.e. of the active ingredient of formula I with at least one of the active ingredients of formulae II to V displays a synergistic action which is capable of controlling most of the weeds preferably found in crops of useful plants both pre- and post-emergence without seriously harming the useful plant.
In accordance with the present invention, we therefore propose a novel synergistic composition for the selective control of weeds which comprises, as active ingredient, the compound of formula I
and a synergistically active amount of at least one active ingredient selected from among the compounds of formula II
 in which
X is —O—, —CH
2
— or —NH—;
Y is CH
3
or OCH
3
;
E is CH or N;
m in the case of the groups A1 and A4 is the number 0 or 1 and in the case of the groups A2, A5 and A3 the number 0, and
of formula III
 in which
R
2
is hydrogen, CH
3
, C
2
H
5
or —(CH
2
)
2
OCH
2
CH
2
CH
3
;
R
2
and R
3
together are —(CH
2
)
6
—; and
of formula IV
in which
of formula V
in a mixture with each other,
in addition to customary inert formulation auxiliaries. It is highly surprising that the combination of the active ingredient of formula I with at least one of the active ingredients of formulae II to V exceeds the additive action on the weeds to be controlled which is to be expected in principle and thus widens the limits of action of the individual compound in particular in two respects:
On the one hand, the rates of application of the individual compounds I and II to V are lower while the activity remains the same. On the other hand, the composition according to the invention allows a high degree of weed control to be achieved even where the individual substances are no longer agronomically useful in the range of low rates of application. This results in a considerably widened spectrum of weeds and in an additional increase in selectivity for the crops of useful plants, as is necessary and desirable in the case of unintentional overdosing with active ingredient. Moreover, the composition according to the invention permits more flexibility with subsequent crops while retaining outstanding control of the weeds in useful plants.
The herbicide mixture according to the invention can be used against a large number of agronomically important weeds, such as Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Phaseolus, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola, Veronica and Heterantera.
The compositions according to the invention are suitable for all application methods conventionally used in agriculture, for example pre-emergence application, post-emergence application and seed dressing.
The herbicide mixture according to the invention is preferably suitable for controlling weeds in crops of useful plants such as cereals, oilseed rape, sugar beet, sugar cane, plantation crops, maize, soya beans and, in particular, rice.
Crops are also to be understood as those which have been made tolerant to herbicides or classes of herbicides by conventional plant-breeding or genetic engineering methods.
The active ingredient combination according to the invention comprises the active ingredient of formula I and one or more of the active ingredients of formulae II to V in any mixing ratio, as a rule with an excess of one over the other component. Preferred mixing ratios between the active ingredient of formula I and the components of formulae II to V are between 1:100 und 100:1, in particular between 1:10 and 10:1.
Preferred compositions according to the invention comprise a compound of formula I
and a synergistically active amount of either a compound of formula II
 in which
X is —O—, —CH
2
— or —NH—;
Y is CH
3
or OCH
3
;
E is CH or N;
 and
m in the case of the groups A1 and A4 is the number 0 or 1 and in the case of the groups A2 and A3 is the number 0; or
of formula III
 in which
R
2
is hydrogen, CH
3
, C
2
H
5
or —(CH
2
)
2
OCH
2
CH
2
CH
3
;
R
2
and R
3
together are —(CH
2
)
6
—; or
of formula IV
 in which
Z is
of formula V
 in which
in addition to customary inert formulation auxiliaries.
Preferred compositions according to the invention comprise a compound of formula II in which
if X is —CH
2
— and m is the number 1, or A is a group
if m is the number zero; and Y is in addition to the compound of formula I.
Other preferred synergistic compositions are those which comprise a compound of formula III selected from the group consisting of
2-(1,3-benzothiazol-2-yloxy)-N-methylacetanilide,
3′,4′-dichloropropionanilide,
2-chloro-2′,6′-diethyl-N-(2-propoxyethyl)acetanilide and
S-ethyl azepan-1-carbothioate,
in addition to the compound of formula I.
Especially preferred compositions comprise a synergistically active amount of the active ingredient butyl (R)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propionate or of the active ingredient methyl 2-[(4,6-dimethoxypyrimidin-2-yl)oxy]-6-[1-(methoxyimino)ethyl]benzoate or the corresponding carboxylic acid, in addition to the compound of formula I.
A very especially preferred composition comprises a synergistically active amount of the active ingredients 2-chloro-2′,6′-diethyl-N-(2-propoxyethyl)acetanilide (pretilachlor) and ethyl 5-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-1-methylpyrazole-4-carboxylate (NC-311) in addition to the compound of formula I.
Synergistic active ingredient mixtures which have proved very especially effective are combinations of the compound of formula I with the compounds of Tables 1 to 4.
TABLE 1
Preferred compounds of formula II:
(II)

Comp.No.
A
X
m
E
Y
1.1
CH
2
1
CH
OCH
3

1.2
—
0
CH
OCH
3

1.3
—
0
N
OCH
3

1.4
—
0
N
CH
3

1.5
—
0
N
CH
3

1.6
—
0
CH
OCH
3

1.7
O
1
CH
OCH
3

1.8
NH
1
CH
OCH
3

1.9
—
0
CH
OCH
3

1.10
—
0
CH
OCH
3
TABLE 2
Preferred compounds of formula III:
(III)

Comp.
No.
B
R
2
R
3
2.1
CH
3

2.2
—C
2
H
5
H

2.3
ClCH
2
—
—(CH
2
)
2
OCH
2
CH
2
CH
3

2.4
—S—CH
2
CH
3
—(CH
2
)
6
—

2.5
—C
2
H
5
—CH

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