Alkylidenehydrazinophenylsulfonylureas, processes for their...

Details Alkylidenehydrazinophenylsulfonylureas, processes for their... Alkylidenehydrazinophenylsulfonylureas, processes for their...

1999-02-17

2001-07-24

Ford, John M. (Department: 1611)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S213000, C504S225000, C544S211000, C544S212000, C544S206000, C544S207000, C544S208000, C544S209000, C544S197000, C544S198000, C544S113000, C540S481000, C540S598000

Reexamination Certificate

active

06265348

ABSTRACT:

It is known that phenylsulfonylureas having hydrazine partial structures have herbicidal properties. These are chiefly hydrazones (EP-A-382 437, EP-A-562 575) or heterocyclic compounds with an incorporated hydrazine structure (EP-A-382 436, EP-A-384 602).
Surprisingly, phenylsulfonylureas with certain substituted hydrazone radicals which are particularly suitable as herbicides or plant growth regulators have now been found.
The present invention relates to 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 last two radicals mentioned, including substituents, preferably contains 1 to 20 carbon atoms,
R
2
is phenyl or heterocyclyl, where each of the last two radicals mentioned is unsubstituted or substituted, or (C
1
-C
6
)haloalkyl, (C
2
-C
6
)alkenyl, (C
2
-C
6
)alkynyl or [(C
1
-C
4
)alkoxy]-carbonyl and
R
3
is (C
1
-C
6
)alkyl, which is 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
)alkoxy]-carbonyl and unsubstituted or substituted phenyl, or is (C
2
-C
6
)alkenyl, (C
2
-C
6
)alkynyl, (C
3
-C
6
)cycloalkyl, phenyl or heterocyclyl, where each of the last 5 radicals mentioned is unsubstituted or substituted, or
R
2
is hydrogen or (C
1
-C
4
)alkyl and
R
3
is [(C
1
-C
4
)alkoxy]carbonyl-(C
1
-C
4
)alkyl, which is unsubstituted or substituted by (C
1
-C
4
)alkylthio or halogen, or phenyl-(C
1
-C
4
)alkyl, which is unsubstituted or substituted in the phenyl radical, or (C
2
-C
6
)alkenyl, which is 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
)alkoxy]-carbonyl and unsubstituted or substituted phenyl, or (C
2
-C
6
)alkynyl or (C
3
-C
6
)cycloalkyl, where each of the last two radicals mentioned is unsubstituted or substituted, or phenyl, which is substituted by one or more radicals from the group consisting of F, Br, CN, NO
2
, (C
1
-C
4
)haloalkyl, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkylthio and [(C
1
-C
4
)alkoxylcarbonyl, or (C
2
-C
6
)alkyl, which is substituted by one or more radicals from the group consisting of halogen and (C
1
-C
4
)alkoxy, or furyl, or
R
2
is (C
1
-C
4
)alkyl and
R
3
is CF
3
, or
R
2
and R
3
, together with the methylene carbon atom, are a cycrkylene or heterocyclylene radical having 4 to 8 ring atoms, which is unsubstituted or substituted, and
R
4
is H, an unsubstituted or substituted aliphatic hydrocarbon radical having 1 to 6 carbon atoms in the hydrocarbon part and one or more substituents, where the substituents are chosen from the group consisting of halogen, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkylthio, (C
3
-C
4
)alkylsulfonyl, [(C
1
-C
4
)alkyl]carbonyl, [(C
1
-C
4
)-alkoxy]carbonyl, CN, substituted and unsubstituted phenyl and (C
3
-C
6
)cycloalkyl, or (C
2
-C
6
)alkenyl or (C
2
-C
6
)alkynyl or an acyl radical having preferably 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 last four radicals mentioned is unsubstituted or substituted by one or more halogen atoms in the alkyl part,
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 and Y independently of one another are H, halogen, (C
1
-C
4
)alkyl, (C
1
-C
4
)alkoxy or (C
1
-C
4
)alkylthio, where each of the last 3 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 mono- or di-(C
1
-C
4
)alkyl]-amino, (C
3
-C
6
)cycloalkyl, (C
2
-C
5
)alkenyl, (C
2
-C
5
)alkynyl, (C
2
-C
5
)-alkenyloxy or (C
2
-C
5
)alkynyloxy and
Z is CH or N.
The compounds of the formula (I) can form salts in which the hydrogen of the —SO
2
—NH-group is replaced by a cation suitable for agriculture. These salts are, for example, metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or else ammonium salts or salts with organic amines. Salt formation can likewise occur by addition of an acid onto basic groups, such as, for example, amino and alkylamino. Suitable acids for this are strong inorganic and organic acids, for example HCl, HBr, H
2
SO
4
or HNO
3
.
In formula (I) and all the following formulae, the alkyl, alkoxy, haloalkyl, haloalkoxy, alkylamino and alkylthio radicals and the corresponding unsaturated and/or substituted radicals can in each case be straight-chain or branched in the carbon skeleton. Unless specifically stated, the lower carbon skeletons, for example having 1 to 6 carbon atoms, or in the case of unsaturated groups having 2 to 6 carbon atoms, are preferred for these radicals. Alkyl radicals, including 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, or 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; alkenyl is, for example, allyl, 1-methyl-prop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methyl-but-3-en-1-yl and 1-methyl-but-2-en-1-yl; and alkynyl is, for example, propargyl, but-2-yn-1-yl, but-3-yn-1-yl and 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 between C-1 and C-2 (C-1 is the position with “yl”).
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 or alkynyl, respectively, 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 comments 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; aryl here 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; the corresponding definition applies to a hydrocarbon radical in a hydrocarbonoxy radical.
A heterocyclic radical or ring (heterocyclyl) can be saturated, unsaturated or heteroaromatic; it preferably contains one or more hetero units in the ring, preferably from the group consisting of N, O, S, SO and SO
2
; preferably, it is an aliphatic heterocyclyl 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. The heterocyclic radical can be, for example, 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 hetero atoms, for example pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, thienyl, thiazolyl, oxazolyl, furyl, pyrrolyl, pyrazolyl and imidazolyl, or is a partly or completely hydrogenated radical, such as oxiranyl, pyrrolidyl, piperidyl, piperazinyl, dioxolanyl, morpholinyl or tetrahydrofuryl. Possible

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