Acylsulfamoylbenzamides, crop protection compositions...

Details Acylsulfamoylbenzamides, crop protection compositions... Acylsulfamoylbenzamides, crop protection compositions...

1998-09-25

2001-06-26

Clardy, S. Mark (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

Plural active ingredients

C504S141000, C504S144000, C546S250000, C546S251000, C546S252000, C546S268100, C546S276100, C546S279100, C546S314000, C546S315000, C546S316000, C546S317000, C564S080000, C564S086000, C564S087000

Reexamination Certificate

active

06251827

ABSTRACT:

The present invention relates to crop protection compositions which comprise acylsulfamoylbenzamides and, if appropriate, pesticides, and also to certain acylsulfamoylbenzamides and to processes for their preparation.
When controlling undesirable organisms in crops of plants which are useful for agriculture or forestry by using pesticides, the useful plants are frequently also damaged to a greater or lesser extent, in a manner which is undesirable per se, by the pesticides employed. This effect is encountered in particular with the use of a considerable number of herbicides in crops of useful plants such as maize, rice, or cereals, and there primarily in the post-emergence application. In some instances, the useful plants can be protected against the phytotoxic properties of the pesticides by employing safeners or antidotes, without adversely affecting the pesticidal activity against the harmful organisms.
Compounds which have hitherto been disclosed as safeners have various chemical structures. Thus, U.S. Pat. No. 4,902,340 discloses derivatives of quinolin-8-oxy-alkanoic acids as safeners for herbicides from the group of the diphenyl ethers and the pyridyloxyphenoxypropionic acids, and EP-A 0 520 371 discloses isoxazolines and isothiazolines as safeners for various kinds of herbicides, aryloxyphenoxycarboxylic acids, sulfonylureas and imidazolinones being mentioned as preferred herbicides in the latter publication.
In
Nippon Kagaku Kaishi,
1975, 123-126, (
Chem. Abstr.,
(1976), 84: 17204), Imai et al. describe three acylsulfamoylbenzamides, in particular the compounds
2-(benzoylsulfamoyl)-N-phenylbenzamide
2-(benzoylsulfamoyl)-N-benzylbenzamide
4-(2-benzoylsulfamoylbenzoylamino)benzoic acid
A particular biological activity or other properties of these compounds are not mentioned.
EP-A 0 562 512 discloses acylsulfamoylbenzamides which carry an aminocarbonyl group in position 2 or in position 6 of the pyridine ring. EP-A 0 590 520 discloses acylsulfamoylbenzamides which are optionally substituted in position 2 or in position 6 of the pyridine ring by an ester group. EP-A 0 673 932 mentions acylsulfamoylbenzamides which in each case carry an aminocarbonyl group in position 2 and position 4 of the pyridine ring. In these three publications, the acylsulfamoylbenzamides mentioned are described as medicaments for fibrotic diseases. A safener action of acylsulfamoylbenzamides has hitherto not been known.
When using safeners for protecting useful plants against damage by pesticides, it has been found that in many instances known safeners still have certain disadvantages. These include:
the safener reduces the activity of the pesticides, in particular those of herbicides, against the harmful plants
the crop-protecting properties are insufficient
in combination with a given herbicide, the spectrum of the useful plants in which the safener/herbicide is to be employed is not sufficiently wide
a given safener cannot be combined with a sufficiently large number of herbicides.
It is an object of the present invention to provide crop protection compositions comprising compounds having improved safener action and, optionally, pesticides.
This object is achieved by crop protection compositions comprising, optionally, one or more pesticides, which comprise at least one acylsulfamoylbenzamide of the formula I, if appropriate also in the form of its salt,
in which
x is CH or N;
R
1
is hydrogen, heterocyclyl or a hydrocarbon radical, where the two last-mentioned radicals are optionally substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, carboxyl, CHO, CONH
2
, SO
2
NH
2
and Z
a
—R
a
;
R
2
is hydrogen, hydroxyl, (C
1
-C
6
)-alkyl, (C
2
-C
6
)-alkenyl, (C
2
-C
6
)-alkynyl, (C
1
-C
6
)-alkoxy, (C
2
-C
6
)-alkenyloxy, where the five last-mentioned radicals are optionally substituted by one or more identical or different radicals selected from the group consisting of halogen, hydroxyl, (C
1
-C
4
)-alkyl, (C
1
-C
4
)-alkoxy and (C
1
-C
4
)-alkylthio, or
R
1
and R
2
together with the linking nitrogen atom form a 3- to 8-membered saturated or unsaturated ring;
R
3
is halogen, cyano, nitro, amino, hydroxyl, carboxyl, CHO, CONH
2
, SO
2
NH
2
or Z
b
—R
b
;
R
4
is hydrogen, (C
1
-C
4
)-alkyl, (C
2
-C
4
)-alkenyl or (C
2
-C
4
)-alkynyl;
R
5
is halogen, cyano, nitro, amino, hydroxyl, carboxyl, phosphoryl, CHO, CONH
2
, SO
2
NH
2
or Z
c
—R
c
;
R
a
is a (C
2
-C
20
)-alkyl radical whose hydrocarbon chain is interrupted once or more than once by oxygen atoms, is heterocyclyl or a hydrocarbon radical, where the two last-mentioned radicals are optionally 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;
R
b
, R
c
independently of one another are a (C
2
-C
20
)-alkyl radical whose hydrocarbon chain is interrupted once or more than once by oxygen atoms, are heterocyclyl or a hydrocarbon radical, where the two last-mentioned radicals are optionally substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, amino, hydroxyl, phosphoryl, (C
1
-C
4
)-haloalkoxy, mono- and di-[(C
1
-C
4
)-alkyl]amino;
Z
a
is a divalent unit selected from the group consisting of O, S, CO, CS, C(O)O, C(O)S, SO, SO
2
, NR
d
, C(O)NR
d
or SO
2
NR
d
;
Z
b
, Z
c
independently of one another are a direct bond or a divalent unit selected from the group consisting of O, S, CO, CS, C(O)O, C(O)S, SO,
SO
2
, NR
d
, SO
2
NR
d
or C(O)NR
d
;
R
d
is hydrogen, (C
1
-C
4
)-alkyl or (C
1
-C
4
)-haloalkyl;
n is an integer from 0 to 4 and
m, in the case that X is CH, is an integer from 0 to 5, and, in the case that X is N, is an integer from 0 to 4.
The terms mentioned hereinabove and hereinbelow have the meanings outlined below:
The term “halogen” includes fluorine, chlorine, bromine and iodine.
The term “(C
1
-C
4
)-alkyl” is to be understood as a straight-chain or branched hydrocarbon radical having 1, 2, 3 or 4 carbon atoms, for example the methyl, ethyl, propyl, isopropyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl radical. Correspondingly, alkyl radicals having a greater range of carbon atoms are to be understood as straight-chain or branched saturated hydrocarbon radicals which contain a number of carbon atoms which corresponds to this range. The term “(C
1
-C
6
)-alkyl” thus includes the abovementioned alkyl radicals, and also, for example, the pentyl, 2-methylbutyl, 1, 1-dimethylpropyl and hexyl radical.
If the carbon chain of an alkyl radical is interrupted by more than one oxygen atoms, this means that two oxygen atoms are at no time directly adjacent.
“(C
1
-C
4
)-haloalkyl” is to be understood as an alkyl group mentioned under the term “(C
1
-C
4
)-alkyl” in which one or more hydrogen atoms are replaced by the corresponding number of identical or different halogen atoms, preferably chlorine or fluorine, such as the trifluoromethyl, the 1-fluoroethyl, the 2,2,2-trifluoroethyl, the chloromethyl, fluoromethyl, the difluoromethyl and the 1,1,2,2-tetrafluoroethyl group.
“(C
1
-C
4
)-alkoxy” is to be understood as an alkoxy group whose hydrocarbon radical has the meaning given under the term “(C
1
-C
4
)-alkyl”. Alkoxy groups embracing a larger range of carbon atoms are to be understood likewise.
The terms “alkenyl” and “alkynyl” having a prefix stating a range of carbon atoms denote a straight-chain or branched hydrocarbon radical having a number of carbon atoms corresponding to this range, this hydrocarbon radical having at least one multiple bond which can be in any position of the unsaturated radical in question. “(C
2
-C
6
)-alkenyl” thus denotes, for example, the vinyl, allyl, 2-methyl-2-propenyl, 2-butenyl, pentenyl, 2-methylpentenyl or the hexenyl group. “(C
2
-C
6
)-alkynyl” denotes, for example, the ethinyl, propargyl, 2-methyl-2-propinyl, 2-butinyl, 2-pentinyl and the 2-hexinyl group.
“(C
3
-C
8
)-cycloalkyl” denotes monocyclic alky

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