Disubstituted methylidene hydrazinophenyl sulfonylureas,...

Details Disubstituted methylidene hydrazinophenyl sulfonylureas,... Disubstituted methylidene hydrazinophenyl sulfonylureas,...

1998-09-16

2001-12-18

Ford, John M. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S215000, C540S601000, C544S295000, C544S296000, C544S122000, C544S123000, C544S321000, C544S323000, C544S324000, C544S331000, C544S332000

Reexamination Certificate

active

06331506

ABSTRACT:

This is a 371 of PCT/EP97/01244, filed Mar. 12, 1997.
It is known that phenylsulfonylureas having hydrazine partial structures have herbicidal properties. These are primarily hydrazones (EP-A-382 437, EP-A-562 575) or heterocycles having an incorporated hydrazine structure (EP-A-382 436, EP-A-384 602).
In the German Patent Applications No. P 44 42 229.6 an No. 19 521 668.7, phenylsulfonylureas have already been preposed which have carboxy(derivative) groups or sulfur substituents in position 2 and which are substituted with hydrazone radicals in position 5.
Surprisingly, there have now been found phenylsulfonylureas having certain hydrazone radicals carrying electron-withdrawing substituents which are particularly suitable as herbicides or plant grog regulators.
The present invention accordingly provides compounds of the formula (I) or salts thereof
in which
R
1
is H or a hydrocarbon radical which is unsubstituted or substituted, or a heterocyclyl radical which is unsubstituted or substituted, where each of the two last-mentioned radicals including substituents has preferably 1 to 20 carbon atoms,
a) R
2
is CN, NO
2
or acyl preferably having 1 to 20 carbon atoms and
R
3
is CN, NO
2
, acyl preferably having 1 to 20 carbon atoms, CF
3
, aryl or a heterocyclic radical, where each of the two last-mentioned radicals is unsubstituted or substituted, or
b) R
2
R
3
C together form a carbocyclic or heterocyclic ring Which has at least one carbon atom substituted by an oxo group in a position adjacent to the carbon atom in position 1 of the group CR
2
R
3
, or
c) R
2
is NO
2
or [(C
1
-C
4
)alkyl]carbonyl and R
3
is H or (C
1
-C
4
)alkyl,
R
4
is H, an unsubstituted or substituted aliphatic hydrocarbon radical having 1 to 6 carbon atoms in the hydrocarbon moiety and one or more substituents, where the substituents are selected from the group consisting of halogen, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkylthio, (C
1
-C
4
)alkylsulfonyl, [(C
1
-C
4
)alkyl]carbonyl, [(C
1
4
)alkoxy]carbonyl, CN, substituted and unsubstituted phenyl and (C
3
-C
6
)cycloalkyl, or is (C
3
-C
6
)alkenyl or (C
3
-C
6
)alkynyl or an acyl radical preferably having 1 to 20 carbon atoms,
R
5
is H, halogen, NO
2
, CN, (C
1
-C
4
alkyl, (C
1
-C
4
)alkoxy, [(C
1
C
4
)alkyl]carbonyl or [(C
1
-C
4
)alkoxy]carbonyl, where each of the four last-mentioned radicals is unsubstituted or substituted in the alkyl moiety by one or more halogen atoms,
R
6
is H or (C
1
-C
4
)alkyl, preferably H or CH
3
,
W is an oxygen or sulfur atom, preferably an oxygen atom,
X, Y independently of one another are H, halogen, (C
1
-C
4
)alkyl, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkylthio, where each of the 3 last-mentioned radicals is unsubstituted or substituted by one or more radicals selected from the group consisting of halogen, (C
1
-C
4
)alkoxy and (C
1
-C
4
)alkylthio, or is mono- or di[(C
1
-C
4
)alkyl]amino, (C
3
-C
6
)cycloalkyl, (C
2
-C
5
)alkenyl, (C
3
-C
5
)alkynyl, (C
3
-C
5
)alkenyloxy or (C
2
-C
5
)alkynyloxy and
Z is CH or N.
The compounds of the formula (I) can form salts where the hydrogen of the —SO
2
—NH— group is replaced by an agriculturally suitable cation. These salts are, for example, metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium s or else ammonium salts and salts with organic amines. Likewise salt formation. may occur by addition of an acid to basic groups, such as, for example, amino and alkylamino. Acids which are suitable for this purposes are strong inorganic and organic acids, for example HCl, HBr, H
2
SO
4
or HNO
3
.
In the formula (I) and all subsequent formulae, the radicals alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio and the corresponding unsaturated and/or substituted radicals can in each case be straight-chain or branched in the carbon skeleton. Unless specifically indicated, the lower carbon skeletons, for example those having 1 to 6 carbon atoms or, in the case of unsaturated groups, 2 to 6 carbon atoms, a for these radicals. Alkyl radicals, also in the composite meaning such as alkoxy, haloalkyl, etc., 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-heptyl, 1-methylhexyl and 1,4-dimethylpentyl; alkenyl and alkynyl radicals have the meaning 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; alkynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methyl-but-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 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 correspondingly to (C
3
-C
4
)alkynyl etc.
Cycloalkyl is a carbocyclic, saturated ring system having 3-8 carbon atoms, for example cyclopropyl, cyclopentyl or cyclohexyl.
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; 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; the same applies correspondingly 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; aryl is a mono-, bi- or polycyclic aromatic system, for example phenyl, naphthyl, tetrahydronaphthyl, indenyl, indanyl, pentalenyl, fluorenyl and the like, preferably phenyl;
a hydrocarbon radical is preferably alkyl, alkenyl or alkynyl having up to 12 carbon atoms or cycloalkyl having 3, 4, 5, 6 or 7 ring atoms or phenyl; this applies correspondingly to a hydrocarbon radical in a hydrocarbonoxy radical.
A heterocyclic radical or ring (heterocycyl) may be saturated, unsaturated or heteroaromatic; it preferably contains one or more hetero units in the ring, preferably selected from the group consisting of N, O, S, SO, SO
2
; it is preferably an aliphatic heterocyclic radical having 3 to 7 ring atoms or a heteroaromatic radical having 5 or 6 ring atoms and contains 1, 2 or 3 hetero units. For example, the heterocyclic radical may be a heteroaromatic radical or ring (heteroaryl), such as, for example, 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, or it is a partially or fully 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 heterocycyl or heteroaryl 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, carboxyl, cyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and dialkylaminocarbonyl,

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