N-heteroaryl-N′-(pyrid-2-yl-sulfonyl) ureas, processes...

Details N-heteroaryl-N′-(pyrid-2-yl-sulfonyl) ureas, processes... N-heteroaryl-N′-(pyrid-2-yl-sulfonyl) ureas, processes...

1994-11-03

2001-11-13

Seaman, D. Margaret (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S210000, C544S253000, C544S278000, C544S319000, C544S320000

Reexamination Certificate

active

06316388

ABSTRACT:

The invention relates to the technical field of herbicides and plant growth regulators, in particular herbicides for the selective control of dicotyledon weeds and grass weeds in crops of useful plants.
It is known that some 2-pyridylsulfonylureas have herbicidal and plant-growth-regulating properties; compare EP-A-13,480, EP-A-272,855, EP-A-84,224, U.S. Pat. No. 4,421,550, EP-A-103,543 (U.S. Pat. No. 4,579,583) U.S. Pat. No. 4,487,626, EP-A-125,864, WO 88/04,297 and WO 91/10,660 (ZA 91/0,173).
More 2-pyridylsulfonylureas which have specific radicals in the 3-position of the pyridyl radical and which are suitable as herbicides and 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, (C
1
-C
6
)alkyl which is unsubstituted or substituted by one or more radicals selected from the group comprising halogen, nitro, (C
1
-C
4
)alkoxy, (C
3
-C
6
)cycloalkyl, aryl and substituted aryl, or aryl in which the aryl radical is unsubstituted or substituted by one or more radicals selected from the group comprising halogen, nitro, (C
1
-C
4
)alkyl, (C
1
-C
4
)haloalkyl and (C
1
-C
4
)alkoxy,
R
2
is H, (C
1
-C
6
)alkyl, (C
2
-C
6
)alkenyl or (C
2
-C
6
)alkynyl, each of the three last-mentioned radicals being unsubstituted or substituted by one or more radicals selected from the group comprising halogen, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkylthio, (C
1
-C
4
)alkylsulfynyl, (C
1
-C
4
)alkylsulfonyl, nitro, cyano and thiocyanato, or (C
1
-C
6
)alkoxy or (C
1
-C
6
)alkylthio, the last-mentioned 2 radicals being unsubstituted or substituted by one or more radicals selected from the group comprising halogen, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkylthio, aryl and substituted aryl, (C
3
-C
7
)cycloalkyl or (C
3
-C
7
)cycloalkoxy, the last-mentioned 2 radicals being unsubstituted or substituted by one or more radicals selected from the group comprising (C
1
-C
4
)alkyl, (C
1
-C
4
)alkoxy, (C
1
-C
4
)alkylthio, (C
1
-C
4
)haloalkyl and halogen, or aryl, substituted aryl or a radical of the formula NR
a
R
b
,
R
3
is (C
1
-C
4
)alkyl, (C
1
-C
3
)haloalkyl, halogen, NO
2
, CN, (C
1
-C
3
) or (C
1
-C
4
)-alkoxy, (C
1
-C
3
) haloalkoxy, (C
1
-C
3
)alkylthio, (C
1
-C
3
)alkoxy-(C
1
-C
3
)alkyl, [(C
1
-C
3
)alkoxy]-carbonyl, (C
1
-C
3
)alkylamino, di[(C
1
-C
3
)alkyl]-amino, (C
1
-C
6
)-alkylsulfynyl, (C
1
-C
3
)alkylsulfonyl, SO
2
NR
c
R
d
or C(O)NR
e
R
f
,
R
a
, R
b
, R
c
, R
d
, R
e
and R
f
independently of one another are H, (C
1
-C
4
)alkyl, (C
3
-C
6
)alkenyl, (C
3
-C
6
)alkynyl, [(C
1
-C
4
)alkyl]-carbonyl, arylcarbonyl, which is unsubstituted or substituted in the aryl radical, or the pairs R
a
and R
b
, R
c
and R
d
or R
e
and R
f
together with the N atom linking them are a heterocyclic saturated or unsaturated ring which is unsubstituted or substituted and which has 3 to 7 ring atoms and 0, 1 or 2 further hetero atoms selected from the group comprising N, O and S,
R
4
is H or (C
1
-C
4
)alkyl, preferably H or CH
3
, in particular H,
m is 0 or 1, preferably 0,
n is 0, 1 or 2, preferably 0 or 1,
A is a radical of the formula
X and Y independently of one another are H, halogen, (C
1
-C
3
)alkyl, (C
1
-C
3
)alkoxy or (C
1
-C
3
)alkylthio, the abovementioned alkyl-containing radicals being unsubstituted or mono- or polysubstituted by halogen or mono- or disubstituted by (C
1
-C
3
)alkoxy or (C
1
-C
3
)alkylthio, or a radical of the formula NR
5
R
6
, (C
3
-C
6
)cycloalkyl, (C
2
-C
4
)alkenyl, (C
2
-C
4
)alkynyl, (C
3
-C
4
)alkenyloxy or (C
3
-C
4
)alkynyloxy,
R
5
and R
6
independently of one another are H, (C
1
-C
3
)alkyl or (C
3
-C
4
)alkenyl,
W is O or S, preferably O,
Z is CH or N, preferably CH,
X
1
is CH
3
, OCH
3
, OC
2
H
5
or OCF
2
H,
Y
1
is —O— or —CH
2
—,
X
2
is CH
3
, C
2
H
5
or CH
2
CF
3
,
Y
2
is OCH
3
, OC
2
H
5
, SCH
3
, SC
2
H
5
, CH
3
or C
2
H
5
,
X
3
is CH
3
or OCH
3
,
Y
3
is H or CH
3
,
X
4
is CH
3
, OCH
3
, OC
2
H
5
, CH
2
OCH
3
or Cl,
Y
4
is CH
31
OCH
3
, OC
2
H
5
or Cl,
Y
5
is CH
3
, C
2
H
5
, OCH
3
or Cl.
In formula (I) and hereinafter, hydrocarbon-containing radicals such as, for example, alkyl, alkoxy, haloalkyl and alkylthio radicals as well as the corresponding unsaturated and/or substituted radicals can in each case be straight-chain or branched in the hydrocarbon moiety. Alkyl radicals, also in composite meanings such as alkoxy, haloalkyl and the like, are methyl, ethyl, n- or i-propyl or n-, i-, t- or 2-butyl; alkenyl and alkynyl radicals have the meanings of the unsaturated radicals which are possible and which correspond to the alkyl radicals, such as 2-propenyl, 2- or 3-butenyl, 2-propynyl or 2- or 3-butynyl. Halogen is fluorine, chlorine, bromine or iodine. Haloalkyl is alkyl which is substituted by one or more atoms selected from the group comprising halogen; haloalkyl is, for example, CF
3
, CHF
2
, CH
2
CF
3
. Aryl is, for example, phenyl, naphthyl, tetrahydronaphthyl, indanyl, fluorenyl and the like, preferably phenyl. Substituted aryl or substituted phenyl is preferably aryl or phenyl each of which is substituted by one or more, preferably 1 to 3, radicals selected from the group comprising halogen, alkyl, haloalkyl, haloalkoxy, nitro, cyano, alkoxycarbonyl, alkanoyl, carbamoyl, mono- and dialkylaminocarbonyl, mono- and dialkylamino, alkylsulfynyl or alkylsulfonyl, preferred alkyl-containing radicals being those which have 1 to 4 carbon atoms, in particular 1 to 2 carbon atoms; particularly preferred are methyl, methoxy and chlorine. Examples of heterocyclic radicals R
2
═NR
a
R
b
are pyrrole, imidazole, pyrazole, triazole, pyrazolone, oxazoles, oxazolones, propane sultams, butane sultams, pyrrolidone, piperidine and morpholine.
The invention also relates to all stereoisomers which are embraced by formula (I) and mixtures thereof. Such compounds of the formula (I) contain one or more asymmetric carbon atoms or else double bonds which are not mentioned separately in the formulae (I). The possible stereoisomers which are defined by their specific spatial arrangement such as enantiomers, diastereomers, Z and E isomers, however, are all embraced by formulae I and can be obtained from mixtures of the stereoisomers by customary methods or else by stereoselective reactions in combination with the use of stereochemically pure starting materials.
The compounds of the formula (I) can form salts in which the hydrogen of the —SO
2
—NH—group is replaced by an agriculturally suitable cation. Examples of these salts are metal salts, in particular alkali metal or alkaline earth metal salts, or else ammonium salts or salts with organic amines. Salt formation can equally be effected by addition reaction with a strong acid with the pyridine moiety of the compound of the formula (I). Acids which are suitable for this purpose are strong inorganic and organic acids, for example HCl, HBr, H
2
SO
4
or HNO
3
.
Preferred compounds of the formula I according to the invention or salts thereof are those in which
R
1
is H, (C
1
-C
4
)alkyl which is unsubstituted or substituted by 1 to 3 radicals selected from the group comprising halogen or by (C
1
-C
2
)alkoxy or (C
3
-C
5
)cycloalkyl.
Other preferred compounds of the formula (I) according to the invention or salts thereof are those in which
R
2
is H, (C
1
-C
4
)alkyl which is unsubstituted or substituted by one or more halogen atoms or by (C
1
-C
2
)alkoxy, or (C
2
-C
4
)alkenyl, (C
2
-C
3
)alkynyl, (C
3
-C
5
)cycloalkyl, (C
1
-C
4
)alkoxy which is unsubstituted or substituted by one or more halogen atoms or by phenyl, or a radical of the formula NR
a
R
b
in which R
a
and R
b
independently of one another are H or (C
1
-C
4
)alkyl.
Other preferred compounds of the formula (I) according to the invention or salts thereof are those in which
R
3
is (C
1
-C
4
)alkyl, (C
1
-C
3
)haloalkyl, halogen, (C
1
-C
3
)alkoxy or nitro and
n is 0, 1 or 2, preferably 0 or 1.
Other preferred compounds of the formula (I) or salts thereof are those in which
R
1
is H, (C
1
-C
4
)alkyl, (C
1
-C
4
)haloalkyl or &

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