Acylated aminophenylsulfonylureas, processes for their...

Details Acylated aminophenylsulfonylureas, processes for their... Acylated aminophenylsulfonylureas, processes for their...

1999-02-25

2002-12-24

Raymond, Richard L. (Department: 1611)

Organic compounds -- part of the class 532-570 series

Organic compounds

Nitrogen attached directly or indirectly to the purine ring...

C544S331000, C544S332000, C544S122000, C544S123000, C544S238000, C544S295000, C544S296000, C560S013000, C564S026000, C564S049000, C564S074000, C564S079000, C564S083000, C564S085000, C564S086000, C504S214000, C504S215000

Reexamination Certificate

active

06498253

ABSTRACT:

Acylated aminophenylsulfonylureas, processes for their preparation and their use as herbicides and plant growth regulators.
The invention relates to the technical field of herbicides and plant growth regulators, in particular herbicides for selective combating of broad-leaved weeds and graminaceous weeds in crops of useful plants.
It is known that phenylsulfonylureas which are substituted by heterocyclic substituents and carry an amino or a functionalized amino group on the phenyl ring have herbicidal and plant growth regulating properties (EP-A-1515; EP-A-7687 (=U.S. Pat. No. 4,383,113); EP-A-30138 (=U.S. Pat. No. 4,394,506); U.S. Pat. No. 4,892,946; U.S. Pat. No. 4,981,509; EP-A-116518 (=U.S. Pat. No. 4,664,695, U.S. Pat. No. 4,632,695)).
Phenylsulfonylureas which contain, on the phenyl ring, a carboxyl group or a function derived from the carboxyl group in the 2-position and an N-alkyl-N-acyl-amino group in the 5-position have furthermore already been proposed in German Patent Application P 42 36 902.9 (WO-94/10154).
Surprisingly, it has now been found that certain phenylsulfonyl ureas which are substituted by heterocyclic substituents are particularly suitable as herbicides and plant growth regulators.
The present invention relates to compounds of the formula (I) and salts thereof
in which
W
1
is an oxygen or sulfur atom,
W
2
is an oxygen or sulfur atom,
n is 0, 1, 2 or 3, preferably 0 or 1, in particular 0,
R is halogen, alkyl or alkoxy, independently of other substituents R if n is greater than 1,
R
1
is hydrogen or an unsubstituted or substituted hydrocarbon or hydrocarbonoxy radical,
R
2
is hydrogen or an unsubstituted or substituted hydrocarbon radical,
or the group
NR
1
R
2
is a heterocyclic ring having 3 to 8 ring atoms, which is unsubstituted or substituted and contains the N atom of the group NR
1
R
2
as a hetero-ring atom and can also contain further hetero-ring atoms,
R
3
is an acyl radical,
R
4
is hydrogen or an aliphatic hydrocarbon radical,
X, Y independently of one another are halogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
1
-C
6
-alkylthio, where each of the last three radicals mentioned is unsubstituted or substituted by one or more radicals from the group consisting of halogen, C
1
-C
4
-alkoxy and C
1
-C
4
-alkylthio, or are C
3
-C
6
-cycloalkyl, C
2
-C
6
-alkenyl, C
2
-C
6
-alkynyl, C
3
-C
6
-alkenyloxy or C
3
-C
6
-alkynyloxy, and
Z is CH or N.
In formula (I) and in the formulae used below, the alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio radicals and the corresponding unsaturated and/or substituted radicals can be in each case straight-chain or branched in the carbon skeleton. If not stated specifically, the lower carbon skeletons, for example having 1 to 4 carbon atoms or, in the case of unsaturated groups, having 2 to 4 carbon atoms, are preferred for these radicals. Alkyl radicals, including those 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, and heptyl radicals, such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, and alkenyl is, for example, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl; and alkynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl or 1-methylbut-3-yn-1-yl.
Halogen is, for example, fluorine, chlorine, bromine or iodine. Haloalkyl, -alkenyl and -alkynyl are alkyl, alkenyl or alkynyl which are partly or completely substituted by halogen, preferably by fluorine, chlorine and/or bromine, in particular by fluorine or chlorine, for example CF
3
, CHF
2
, CH
2
F, CF
3
CF
2
, CH
2
FCHCl, CCl
3
, CHCl
2
and CH
2
CH
2
Cl; haloalkoxy 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; corresponding statements apply to haloalkenyl and other radicals substituted by halogen.
A hydrocarbon radical is a straight-chain, branched or cyclic and saturated or unsaturated aliphatic or aromatic hydrocarbon radical, for example alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or aryl, preferably alkyl, alkenyl or alkynyl having up to 12 carbon atoms or cycloalkyl having 5 or 6 ring atoms or phenyl; corresponding statements apply to a hydrocarbonoxy radical.
Aryl is a mono-, bi- or polycyclic aromatic system, for example phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl and the like, preferably phenyl; aryloxy is preferably an oxy radical corresponding to the aryl radical mentioned, in particular phenoxy.
Heteroaryl or a heteroaromatic radical is a mono-, bi- or polycyclic aromatic system in which at least 1 ring contains one or more heteroatoms, for example pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, thienyl, thiazolyl, oxazolyl, furyl, pyrrolyl, pyrazolyl and imidazolyl, and also bicyclic or polycyclic aromatic or araliphatic compounds, for example quinolinyl, benzoxazolyl and the like. Heteroaryl also includes a heteroaromatic ring, which is preferably 5- or 6-membered and contains 1, 2 or 3 hetero-ring atoms, in particular from the group consisting of N, O and S. In the substituted case, the heteroaromatic ring can also be benzo-fused.
A heterocyclic radical or ring can be saturated, unsaturated or heteroaromatic; it contains one or more hetero-ring atoms, preferably from the group consisting of N, O and S; it is preferably 5- or 6-membered and contains 1, 2 or 3 hetero-ring atoms. The radical can be, for example, a heteroaromatic radical or ring as defined above, or is a partly hydrogenated radical, such as oxiranyl, pyrrolidyl, piperidyl, piperazinyl, dioxolanyl, morpholinyl or tetrahydrofuryl. Possible substituents for a substituted heterocyclic radical are the substituents mentioned below, and in addition also oxo. The oxo group can also occur on the hetero-ring atoms which can exist at various oxidation levels, for example in the case of N and S.
Substituted radicals, such as substituted hydrocarbon radicals, for example substituted alkyl, alkenyl, alkynyl, aryl, phenyl and benzyl, or substituted heteroaryl, a substituted bicyclic radical or ring or a substituted bicyclic radical, if appropriate with aromatic moieties, are, for example, a substituted radical which is derived from the unsubstituted parent substance, in which the substituents are, for example, one or more, preferably 1, 2 or 3, radicals from the group consisting of halogen, alkoxy, haloalkoxy, alkylthio, hydroxy, amino, nitro, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino, such as acylamino, mono- and dialkylamino, and alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl and, in the case of cyclic radicals, also alkyl and haloalkyl, and the unsaturated aliphatic radicals corresponding to the saturated hydrocarbon-containing radicals mentioned, such as alkenyl, alkynyl, alkenyloxy, alkynyloxy and the like. In the case of radicals with carbon atoms, those having 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms, are preferred. Substituents from the group consisting of halogen, for example fluorine and chlorine, C
1
-C
4
-alkyl, preferably methyl or ethyl, C
1
-C
4
-haloalkyl, preferably trifluoromethyl, C
1
-C
4
-alkoxy, preferably methoxy or ethoxy, C
1
-C
4
-haloalkoxy, nitro and cyano are as a rule preferred. The substituents methyl, methoxy and chlorine are particularly preferred here.
Mono- or disubstituted amino is, for example, alkylamino, dialkylamino, acylamino, arylamino or N-aryl-N-alkylamino.
Optionally substituted phenyl is preferably phenyl which is unsubstituted or substituted once or several times, preferably up to three times by identical or different radicals from the group consisting of halogen, C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-haloalkyl, C
1
-C
4
-haloalkoxy and nitro,

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