N-acylsulfonamides, novel mixtures of herbicides and...

Details N-acylsulfonamides, novel mixtures of herbicides and... N-acylsulfonamides, novel mixtures of herbicides and...

1997-05-27

2001-05-22

Clardy, S. Mark (Department: 1616)

Plant protecting and regulating compositions

Antidotes

Antidote contains organic nitrogen compound wherein the...

Reexamination Certificate

active

06235680

ABSTRACT:

The invention relates to the technical field of crop protection products, preferably safeners against phytotoxic side effects of pesticides, in particular herbicides, in crop plants; in particular, it relates to combinations of active substances and antidotes which are outstandingly suitable for use against competing harmful plants in crops of useful plants.
When using crop treatment products, in particular herbicides, against harmful plants in crops, undesirable damage may occur on the crop plants. In particular when the herbicides are not fully compatible with the crop plants (selective), the possibilities of using the herbicides are only limited. In such cases, they cannot be employed, or can be employed only in such low rates of application that the desired broad herbicidal activity is not guaranteed. For example, a large number of herbicides from the series of the sulfonylureas cannot be employed selectively in maize, rice or other cereals. It is therefore desirable to avoid phytotoxicity of the herbicides to the crop plants or to reduce it as much as possible. Compounds which are suitable for reducing phytotoxic side effects of herbicides on crop plants are termed safeners or antidotes.
U.S. Pat. No. 3,498,780 discloses 1,4-substituted arylsulfonamides and their herbicidal activity when used pre-emergence. U.S. Pat. No. 4,266,078 describes the use of N-acylsulfonamides as safeners for thiocarbamate and haloacetanilide herbicides to be employed pre-emergence; a use as safeners for herbicides which are active post-emergence is not disclosed. Furthermore, U.S. Pat. No. 4,434,000 discloses N-benzenesulfonylcarbamates as safeners for urea herbicides. EP-A-365484, EP-A-597807 and EP-A600836 have already disclosed N-acylsulfamoyl-phenylureas and their use as safeners for various classes of herbicides.
Recent experimental work has shown, entirely unexpectedly, that N-(acylsulfamoylphenyl)alkanamides are outstandingly suitable for markedly reducing, or fully reversing, phytotoxic side effects of pesticides, for example of herbicides which can be employed post-emergence, for example the sulfonylureas or imidazolinones, which act as acetolactate synthase inhibitors (ALS inhibitors), or the fatty acid biosynthesis inhibitors, such as the (hetero)aryloxyphenoxycarboxylic acid derivatives, on crop plants such as, for example, maize, rice or other cereals.
Active ingredients of safeners to be employed in accordance with the invention are compounds of the formula (I) and salts thereof
where
R
1
is hydrogen, a hydrocarbon radical, a hydrocarbonoxy radical, a hydrocarbonthio radical or a heterocyclyl radical, each of the last-mentioned 4 radicals being unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, carboxyl, formyl, carboxamide, sulfonamide and radicals of the formula —Z
a
—R
a
, each hydrocarbon moiety preferably having 1 to 20 carbon atoms and a carbon-containing radical R
1
, including substituents, preferably having 1 to 30 carbon atoms,
R
2
is hydrogen or (C
1
-C
4
)-alkyl, preferably H, or
R
1
and R
2
together with the group of the formula —CO—N— are the radical of a 3- to 8-membered saturated or unsaturated ring and
R
3
, in the event that n=1, or the R
3
radicals independently of one another, in the event that n is greater than 1, is, or are, in each case halogen, cyano, nitro, amino, hydroxyl, carboxyl, formyl, CONH
2
, SO
2
NH
2
or a radical of the formula —Z
b
—R
b
,
R
4
is hydrogen or (C
1
-C
4
)-alkyl, preferably H,
R
5
, in the event that m=1, or the R
5
radicals independently of one another, in the event that m is greater than 1, is, or are, in each case halogen, cyano, nitro, amino, hydroxyl, carboxyl, CHO, CONH
2
, SO
2
NH
2
or a radical of the formula —Z
c
—R
c
,
R
a
is a hydrocarbon radical or a heterocyclyl radical, each of the two last-mentioned radicals being unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, mono- and di-[(C
1
-C
4
)-alkyl]amino, or is an alkyl radical in which more than one, preferably 2 or 3, non-adjacent CH
2
groups are in each case replaced by an oxygen atom,
R
b
,R
c
independently of one another are a hydrocarbon radical or a heterocyclyl radical, each of the two last-mentioned radicals being unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, phosphoryl, halo-(C
1
-C
4
)-alkoxy, mono- and di-[(C
1
-C
4
)-alkyl]amino, or are an alkyl radical in which more than one, preferably 2 or 3, non-adjacent CH
2
groups are in each case replaced by an oxygen atom,
z
a
is a divalent group of the formua —O—, —S—, —CO—, —CS—, —CO—O—, —CO—S—, —O—CO—, —S—CO—, —SO—, —SO
2
—, —NR*—, —CO—NR*—, —NR*CO—, —SO
2
—NR*— or —NR*—SO
2
—, the bond shown on the right of the divalent group in question being the bond to the radical R
a
and the R* radicals in the last-mentioned 5 radicals independently of one another being in each case H, (C
1
-C
4
)-alkyl or halo-(C
1
-C
4
)-alkyl,
Z
b
,Z
c
independently of one another are a direct bond or divalent group of the formula —O—, —S—, —CO—, —CS—, —CO—O—, —CO—S—, —O—CO—, —S—CO—, —SO—, —SO
2
—, —NR*—, —SO
2
—NR*—, —NR*—SO
2
—, —CO—NR*— or —NR*—CO—, the bonds given on the right of the divalent group in question being the bond to the radical R
b
or R
c
, and the R* radicals in the last-mentioned 5 radicals independently of one another in each case being H, (C
1
-C
4
)-alkyl or halo-(C
1
-C
4
)-alkyl,
n is an integer from 0 to 4, preferably 0, 1 or 2, in particular 0 or 1, and
m is an integer from 0 to 5, preferably 0, 1, 2 or 3, in particular 0, 1 or 2.
In formula (I) and in the formulae used hereinbelow, the radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio and the correspnding unsaturated and/or substituted radicals can in each case be straight-chain or branched in the carbon skeleton. Unless specifically mentioned, the lower carbon skeletons, for example those having 1 to 4 carbon atoms or, in the case of unsaturated groups, 2 to 4 carbon atoms, are preferred for these radicals, Alkyl radicals, also in the composite meanings such as alkoxy, haloalkyl and the like, are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyl radicals, hexyl radicals such as n-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyl radicals such as n-heptyl radicals, 1-methylhexyl and 1,4-dimethylpentyl; cycloalkyl is a carbocyclic saturated ring system, for example having 3 to 8 ring atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like; alkenyl, alkynyl and cycloalkenyl radicals have the meanings of the unsaturated radicals which are possible and which correspond to the alkyl or cycloalkyl radicals, respectively; alkenyl is, for example, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2en-1-yl, but-2-en-1-yl, but-3-en-1-yl, methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl; cycloalkenyl is, for example, cyclopentenyl or cyclohexenyl; alkynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl or 1-methylbut-3-yn-1-yl. Alkenyl in the form “(C
3
-C
4
)-alkenyl” or “(C
3
-C
6
)-alkenyl” is preferably an alkenyl radical having 3 to 4, or 3 to 6, carbon atoms, respectively, where the double bond is not located on the carbon atom linked to the remaining moiety of the compound (I) (“yl” position). The same applies analogously to (C
3
-C
4
)-alkynyl and the like.
Halogen is, for example, fluorine, chlorine, bromine or iodine. Haloalkyl, haloalkenyl and haloalkynyl are alkyl, alkenyl and alkynyl, respectively, which are fully or partially substituted by halogen, preferably by fluorine, chlorine and/or bromine, in particular by fluorine or chlorine, such as CF
3
, CHF
2
, CH
2
F, CF
3
CF
2
, CH
2
FCHCl
2
, CCl
3
, CHCl
2
, CH
2
CH
2
Cl; haloalkyl is, for example, OCF
3
, OCHF
2
, OCH
2
F, CF
3
CF
2
O, OCH
2
CF
3
and OCH
2
CH
2
Cl; the same applies anal

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