(Het) arylsulfonylureas having an amino function, their...

Details (Het) arylsulfonylureas having an amino function, their... (Het) arylsulfonylureas having an amino function, their...

1997-05-13

2002-06-25

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S215000, C544S320000, C544S321000, C544S323000, C544S324000, C544S331000, C544S332000, C544S058500, C544S054000, C544S063000, C544S066000, C544S096000, C544S122000, C544S123000, C544S296000, C540S601000

Reexamination Certificate

active

06410482

ABSTRACT:

DESCRIPTION
The invention relates to the technical field of herbicides and plant growth regulators, in particular of herbicides for controlling broad-leaved weeds and grass weeds in crop plants.
N-Pyrimidinyl- or N-triazinyl(het)arylsulfonylureas carrying one or more certain substituents in the aromatic or heteroaromatic moiety are known to have herbicidal properties.
For example, phenylsulfonylureas having a nitrogen function with a certain substitution pattern (such as acylamino- or N-acyl-N-alkylamino) are potent herbicides; cf. for example DE-A4230933, EP-A-116 518, U.S. Pat. No. 4,885,337, U.S. Pat. No. 4,892,946, U.S. Pat. No. 4,53,971, U.S. Pat. No. 4,369,058.
Surprisingly, it has now been found that sulfonylureas having specific nitrogen radicals are particularly suitable for use as herbicides and plant growth regulators.
The present invention provides compounds of the formula (I) or salts thereof,
in which
A is an aromatic or heterocyclic divalent bridge, for example a carbocyclic aromatic or a saturated or unsaturated heterocyclic or heteroaromatic bridge, which is unsubstituted or substituted and linked to the SO
2
group in the respective compound of the formula (I) by a direct bond or via a group of the formula O, S, NH or CH
2
, where NH or CH
2
are optionally substituted by C
1
-C
6
-alkyl radicals,
B is a group which contains an imino-containing 3 atom fragment from the group of the fragments of the formulae N═C—N, N═C—S, N═C—O and N═C—C and which is attached to the radical A via a nitrogen atom of the fragment,
R is H or an aliphatic radical,
W is an oxygen or sulfur atom,
X and Y are each independently of the other hydrogen, halogen, C
1
-C
6
-alkyl, C
1
-C
6
-alkoxy, C
3
-C
6
-alkylthio, C
3
-C
6
-cycloalkyl, C
3
-C
6
-cycloalkoxy, C
3
-C
6
-cycloalkylthio, C
2
-C
6
-alkenyl, C
5
-C
6
-cycloalkenyl, C
2
-C
6
-alkynyl, C
3
-C
6
-alkenyloxy, C
5
-C
6
-cycloalkenyloxy or C
3
-C
6
-alkynyloxy, each of the last eleven radicals being unsubstituted or substituted by one or more radicals from the group consisting of halogen, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-haloalkoxy and, in the case of cyclic radicals, also C
1
-C
4
-alkyl and C
1
-C
4
-haloalkyl, or are mono- or di-(C
1
-C
4
-alkyl)amino and
Z is CH or N.
In formula (I) and all subsequent formulae, the radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio and the corresponding unsaturated and/or substituted radicals can be in each case straight-chain or branched in the carbon skeleton. Unless specifically indicated, 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, pentyls, hexyls, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyls, such as n-heptyls, 1-methylhexyl and 1,4-dimethylpentyl. Cycloalkyl is a cycloaliphatic hydrocarbon radical, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl and the like; alkenyl, cycloalkenyl and alkynyl radicals have the meanings of the unsaturated radicals which are possible and which correspond to the alkyl radicals; 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; cycloalkenyl is, for example, cyclopentenyl and cyclohexenyl; alkynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl,
Alkenyl in the form of “(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 in which the double bond is not positioned at the carbon atom attached to the remainder of the molecule of the compound (I) (“yl” position). The same applies analogously to (C
3
-C
4
)-alkynyl, etc.
Halogen is, for example, fluorine, chlorine, bromine or iodine. Haloalkyl, -alkenyl and -alkynyl are alkyl, alkenyl and alkynyl, respectively, which are partially or fully 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
, 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 analogously to haloalkenyl and other halogen-substituted radicals.
A hydrocarbon radical is a straight-chain, branched or cyclic, 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 3 to 8 ring atoms, preferably 5 or 6 ring atoms, or phenyl; the same applies analogously to a hydrocarbonoxy radical.
An organic radical is a carbon-containing radical having one or more optionally substituted aliphatic and/or (hetero)aromatic radicals. An aliphatic radical is a non-aromatic organic radical which may, in addition to carbon atoms and hydrogen atoms, also contain hetero atoms, preferably a non-aromatic hydrocarbon radical which 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.
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.
Hetaryl or a heteroaromatic radical is a mono-, bi- or polycyclic aromatic system in which at least 1 ring contains one or more hetero atoms, for example pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, thienyl, thiazolyl, oxazoyl, furyl, pyrrolyl, pyrazolyl and imidazolyl. If substituted, this in particular also includes bicyclic or polycyclic aromatic compounds or compounds fused with cycloaliphatic rings, for example quinolinyl, benzoxazolyl, etc. Hetaryl 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. If substituted, the heteroaromatic ring may also be benzo-fused.
A heterocyclic radical (heterocyclyl) or ring (heterocycle) may be saturated, unsaturated or heteroaromatic; it preferably contains one or more hetero ring atoms, preferably selected from the group consisting of N, O and S; it is preferably a non-aromatic ring having 3 to 8 ring atoms and 1 to 3 hetero ring atoms from the group consisting of N, O and S, or it is a heteroaromatic ring having 5 or 6 ring atoms and contains 1, 2 or 3 hetero ring atoms from the group consisting of N, O and S. For example, the radical may be a heteroaromatic radical or ring as defined above, or it is a partially hydrogenated radical such as oxiranyl, pyrrolidyl, piperidyl, piperazinyl, dioxolanyl, morpholinyl, tetrahydrofuryl. Suitable substituents for a substituted heterocyclic radical are the substituents mentioned further below, and additionally also oxo. The oxo group may also be located 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 hetaryl 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 skeleton, the substituents being, for example, one or more, preferably 1, 2 or 3, radicals selected from the group consisting of halogen, alkoxy, haloalkoxy, alkylthio, hydroxyl, amino, nitro, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl, substituted amino, such as acylamino, mono- or dialkylamino, and alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl a

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