Carbamoylphenylsulfonylureas, processes for their...

Details Carbamoylphenylsulfonylureas, processes for their... Carbamoylphenylsulfonylureas, processes for their...

1998-10-30

2001-05-08

Raymond, Richard L. (Department: 1611)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S242000, C504S243000, C544S319000, C544S321000

Reexamination Certificate

active

06228808

ABSTRACT:

It is known that phenylsulfonylureas substituted by carbamoyl groups have herbicidal properties. These are symmetric derivatives of isophthalic acid (formula A; U.S. Pat. No. 4,302,241).
Surprisingly, we have now found terephthalic acid ester amides or diamides which are particularly suitable for use as herbicides or plant growth regulators.
The present invention provides compounds of the formula (I) or salts thereof
in which
R
1
is a hydrogen atom, a hydrocarbon radical or a heterocyclyl radical, where each of the two last mentioned radicals is unsubstituted or substituted and has, including substituents, 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms,
R
2
is a group of the formula R
0
—Q
0
—, in which
R
0
is a hydrogen atom, a hydrocarbon radical or a heterocyclyl radical, where each of the two last mentioned radicals is unsubstituted or substituted and has, including substituents, 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms, and
Q
0
is a direct bond or a divalent group of the formula —O—, —SO
2
—, —NH—, —N[(C
1
-C
6
)alkyl]-, —CO—, —CO—NH— or —O—CO—NH—,
R
3
is a hydrogen atom, a hydrocarbon radical or a heterocyclyl radical, where each of the two last mentioned radicals is unsubstituted or substituted and has, including substituents, 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms,
R
4
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
5
is H or (C
1
-C
4
)alkyl, preferably H or CH
3
,
Q is O or NR*,
R* is H, (C
1
-C
4
)alkyl, (C
3
-C
4
)alkenyl or (C
3
-C
4
)alkynyl, where each of the three 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,
W is an oxygen or sulfur 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 three 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 are mono- or di[(C
1
-C
4
)alkyl]amino, (C
3
-C
4
)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 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 salts and potassium salts, or else ammonium salts or salts with organic amines. Likewise, salt formation can be carried out by adding an acid to basic groups, such as, for example, amino and alkylamino. Suitable acids for this purpose are strong inorganic and organic acids, for example HCl, HBr, H
2
SO
4
or HNO
3
.
In the formula (I) and all formulae below, the carbon-containing radicals, such as 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 stated otherwise, 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, also in the composed meanings 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 denotes, 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-methyl-but-3-en-1-yl and 1-methyl-but-2-en-1-yl; alkynyl is, for example, propargyl, but-2-in-1-yl, but-3-in-1-yl, 1-methyl-but-3-in-1-yl.
Alkenyl in the form “(C
3
-C
4
)alkenyl” and “(C
3
-C
6
)alkenyl” preferably denotes an alkenyl radical having 3 to 4 and 3 to 6 carbon atoms, respectively, where the double bond is not at the carbon atom which is linked to the remainder of the molecule of the compound (I) (“yl” position). This applies correspondingly to (C
3
-C
4
)alkynyl, etc.
Cycloalkyl is a carbocyclic saturated ring system having 3-8 carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
Halogen is, for example, fluorine, chlorine, bromine or iodine. Haloalkyl, -alkenyl and -alkynyl are alkyl, alkenyl or alkynyl 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; this applies correspondingly to haloalkenyl and other halogen-substituted radicals.
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 in this context 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.
A heterocyclic radical or ring (heterocyclyl) can be saturated, unsaturated or heteroaromatic; preferably, it contains one or more heteroatoms in the ring, preferably selected from the group consisting of N, O and S; it is preferably 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 heteroatoms. 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 one ring contains one or more heteroatoms, for example pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, thienyl, thiazolyl, oxazolyl, furyl, pyrrolyl, pyrazolyl and imidazolyl, or it is a partially or fully hydrogenated radical such as oxiranyl, oxetanyl, pyrrolidyl, piperidyl, piperazinyl, dioxolanyl, morpholinyl, tetrahydrofuryl. Substituents which are suitable for a substituted heterocyclic radical are the substituents mentioned further below, and additionally also oxo. The oxo group can also be present on the hetero ring atoms which may exist at various oxidation levels, for example on N and S.
Substituted radicals, such as substituted hydrocarbon radicals, for example substituted alkyl, alkenyl, alkynyl, aryl, phenyl and benzyl, or substituted heterocyclyl 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, 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 also unsaturated aliphatic radicals which correspond to the abovementioned saturated hydrocarbon-containing radicals, such as alkenyl, alkynyl, alkenyloxy, alkynyloxy etc. Preferred among radicals having carbon atoms are those having 1 to 4 carbon atoms, in particular 1 or 2 carbon atoms. Preferred are, in general, substituents selected from the group consisting of halogen, for example fluorine and chlori

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