Selective herbicides on the basis of a substituted...

Details Selective herbicides on the basis of a substituted... Selective herbicides on the basis of a substituted...

2002-03-26

2003-11-18

Clardy, S. Mark (Department: 1616)

Plant protecting and regulating compositions

Antidotes

Hetero ring containing antidote

C504S107000, C504S274000

Reexamination Certificate

active

06649565

ABSTRACT:

FIELD OF THE INVENTION
The invention relates to novel selective herbicidal active compound combinations comprising, on the one hand, 2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-propoxy-2,4-dihydro-3H-1,2,4-triazol-3-one and/or its salts, in particular its sodium salt, and, on the other hand, at least one compound which improves crop plant compatibility and which can be used particularly successfully for the selective control of weeds in various crops of useful plants.
BACKGROUND OF THE INVENTION
Substituted phenylsulphonylaminocarbonyl-triazolinones are known as effective herbicides (cf., for example, EP-A 507 171). However, the activity of these compounds and/or their compatibility with crop plants are not entirely satisfactory under all conditions.
Furthermore, active compound combinations of substituted phenylsulphonylaminocarbonyl-triazolinones and other herbicidally active compounds for obtaining a synergistic effect (cf. DE-A 196 388 87) have been disclosed. However, the use properties of these combination products are likewise not entirely satisfactory under all conditions. The combination of a 2-(2-trifluoromethoxy-phenylsulphonylaminocarbonyl)-4-methyl-5-methoxy-3H-1,2,4-triazol-3-one with certain safeners has been also described in the EP-A 931 456.
DETAILED DESCRIPTION OF THE INVENTION
Surprisingly, it has now been found that 2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-propoxy-2,4-dihydro-3H-1,2,4-triazol-3-one and/or its salts, when used together with the compounds described further below which improve crop plant compatibility (safener/antidotes) prevent damage to the crop plants extremely well and can be used particularly advantageously as a broad-spectrum combination preparation for the selective control of weeds in crops of useful plants, such as, for example, in cereals.
The present invention provides selective herbicidal compositions, characterized in that they comprise an active compound combination comprising
(a) 2-(2-methoxycarbonyl-phenylsulphonylaminocarbonyl)-4-methyl-5-propoxy-2,4-dihydro-3H-1,2,4-triazol-3-one of the formula (I)
and/or one or more salts of the compound of the formula (I), in particular the sodium salt, and
(b) at least one crop plant compatibility-improving compound from the following group of compounds:
&agr;-(1,3-dioxolan-2-yl-methoximino)-phenylacetonitrile (oxabetrinil), &agr;-(cyano-methoximino)-phenylacetonitrile (cyometrinil), 4-chloro-N-(1,3-dioxolan-2-yl-methoxy)-&agr;-trifluoro-acetophenone oxime (fluxofenim), 4,6-dichloro-2-phenyl-pyrimidine (fenclorim), 4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzox-azine (benoxacor), 1-methyl-hexyl 5-chloro-quinoxaline-8-oxyacetate (clo-quintocet), 2,2-dichloro-N-(2-oxo-2-(2-propenylamino)-ethyl)-N-(2-propenyl)-acetamide (DKA-24), 1,8-naphthalic anhydride, ethyl 1-(2,4-dichloro-phenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate (fenchlorazol-ethyl), phenylmethyl 2-chloro-4-trifluoromethyl-thiazole-5-carboxylate (flurazole), 3-dichloroacetyl-5-(2-furanyl)-2,2-dimethyl-oxazolidine (furilazole, MON-13900), 4-dichloroacetyl-1-oxa-4-aza-spiro[4.5]-decane (AD-67), 2-dichloro-methyl-2-methyl-1,3-dioxolane (MG-191), 2,2-dichloro-N-(1,3-dioxolan-2-yl-methyl)-N-(2-propenyl)-acetamide (PPG-1292), 2,2-dichloro-N,N-di-2-propenyl-acetamide (dichlormid), N-(4methyl-phenyl)-N′-(1-methyl-1-phenyl-ethyl)-urea (dymron), 1-dichloroacetyl-hexahydro-3,3,8a-trimethylpyrrolo[1,2-a]-pyrimidin-6(2H)-one (BAS-145138), N-(2-methoxy-benzoyl)-4-(methylamino-carbonylamino)-benzenesulphonamide and/or the compounds below, defined by general formulae
 in which
R
32
represents hydrogen, C
1
-C
8
-alkyl or C
1
-C
6
-alkoxy- or C
3
-C
6
-alkenyloxy-substituted C
1
-C
8
-alkyl and
X
1
represents hydrogen or chlorine;
or of the formula (IIb)
 in which
E represents nitrogen or methine;
R
38
represents C
1
-C
4
-alkyl;
R
39
represents —CCl
3
, phenyl or halogen-substituted phenyl, and
R
40
and R
41
independently of one another each represent hydrogen or halogen;
or of the formula (IIc)
 in which
R
27
and R
28
independently of one another each represent hydrogen or halogen and
R
29
, R
30
and R
31
independently of one another each represent C
1
-C
4
-alkyl;
or of the formula (IId)
 in which
A
2
represents a group
R
35
and R
36
independently of one another each represents hydrogen, C
1
-C
8
-alkyl, C
3
-C
8
-cycloalkyl, C
3
-C
6
-alkenyl, C
3
-C
6
-alkinyl,
substituted C
1
-C
4
-alkyl; or
R
35
and R
36
together form a C
4
-C
6
-alkylene bridge which may be interrupted by oxygen, sulphur, SO, SO
2
, NH or —N(C
1
-C
4
-alkyl)-;
R
37
represents hydrogen or C
1
-C
4
-alkyl;
R
33
represents hydrogen, halogen, cyano, trifluoromethyl, nitro, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-alkylsulphinyl, C
1
-C
4
-alkylsulphonyl, —COOR
j
, —CONR
k
R
m
, —COR
n
, —SO
2
—NR
k
R
m
or —OSO
2
—C
1
-C
4
-alkyl;
R
g
represents hydrogen, halogen, cyano, nitro, C
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-alkylthio, C
1
-C
4
-alkylsulphinyl, C
1
-C
4
-alkylsulphonyl, —COOR
j
, —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 which is substituted by C
1
-C
4
-alkoxy or halogen, C
3
-C
5
-alkenyloxy or C
3
-C
6
-alkenyloxy which is substituted by halogen, or represents 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 form a C
3
-C
4
-alkenylene bridge which may be substituted by halogen or C
1
-C
4
-alkyl, or form a C3-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 each represent hydrogen, halogen, C
1
-C
4
-alkyl, trifluoromethyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylthio or —COOR
j
;
R
c
represents hydrogen, halogen, nitro, C
1
-C
4
-alkyl or methoxy,
R
d
represents hydrogen, halogen, nitro, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
alkylsulphinyl, C
1
-C
4
alkylsulphonyl, —COOR
j
or CONR
k
R
m
;
R
e
represents hydrogen, halogen, C
1
-C
4
-alkyl, —COOR
j
, trifluoromethyl or methoxy, or
R
d
and Re together form a C
3
-C
4
-alkylene bridge;
R
f
represents hydrogen, halogen or C
1
-C
4
-alkyl;
R
x
and R
y
independently of one another each represent 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 each represent 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 interrupted by oxygen, NH or —N(C
1
-C
4
-alkyl)-;
R
n
represents C
1
-C
4
-alkyl, phenyl or halogen-, C
1
-C
4
-alkyl-, methoxy-, nitro- or trifluoromethyl-substituted phenyl;
R
38
represents 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, halogeno-C
1
-C
8
-alkyl, C
2
-C
8
-alkenyl, halogeno-C
2
-C
8
-alkenyl, C
3
-C
8
-alkinyl, C
3
-C
7
-cycloalkyl, halogeno-C
3
-C
7
-cycloalkyl, C
1
-C
8
-alkylcarbonyl, allylcarbonyl, C
3
-C
7
-cycloalkylcarbonyl, benzoyl, which is unsubstituted or substituted up to three times on the phenyl ring by identical or different substituents from the group consisting of halogen, C
1
-C
4
-alkyl, halogeno-C
1
-C
4
-alkyl, halogeno-C
1
-C
4
-alkoxy and C
1
-C
4
-alkoxy; or represents furoyl, thienyl; or represents C
1
-C
4
-alkyl substituted by phenyl, halogenophenyl, C
1
-C
4
-alkylphenyl, C
1
-C
4
-alkoxyphenyl, halogeno-C
1
-C
4
-alkylphenyl, halogeno-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 represents phenylaminocarbonyl which is unsubstituted or substituted up to three times on the phenyl by identical or different substituents from

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