Herbicidal substituted pyridines, their preparation, and...

Details Herbicidal substituted pyridines, their preparation, and... Herbicidal substituted pyridines, their preparation, and...

2002-06-21

2004-09-21

Huang, Evelyn Mei (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S225000, C504S251000, C504S252000, C504S253000, C504S257000, C504S244000, C504S230000, C504S235000, C504S238000, C504S242000, C504S247000, C504S248000, C546S276100, C546S300000, C546S280400, C546S284400, C546S261000, C546S279100, C546S153000, C546S175000, C546S176000, C544S124000, C544S180000, C544S238000, C544S298000, C544S405000

Reexamination Certificate

active

06794336

ABSTRACT:

It is known that substituted pyridines may possess herbicidal and plant growth regulating properties (cf., e.g., EP-A-0955300, WO 98/04550, EP-A-0955292, WO 00/75112, WO 01/00580, and WO 99/28301). In some cases, however, in the course of their use, these compounds have disadvantages, such as high persistency or inadequate selectivity in important crops, for example. Furthermore, EP-A-0196184 describes substituted pyridines.
Special 2,6-substituted pyridines have now been found which can be used with advantages as herbicides and plant growth regulators.
The present invention accordingly provides compounds of the formula (I) and/or salts thereof
in which
R
1
is identical or different at each occurrence and is H, halogen, CN, nitro, SF
5
, (C
1
-C
8
)alkyl which is unsubstituted or substituted, for example, by one or more radicals from the group consisting of halogen, (C
1
-C
8
)alkoxy, (C
1
-C
8
)alkylthio, (C
1
-C
8
)alkylsulfinyl, (C
1
-C
8
)alkylsulfonyl, [(C
1
-C
8
)alkoxy]-carbonyl, and CN, or is (C
2
-C
8
)alkenyl or (C
2
-C
8
)alkynyl which are unsubstituted or substituted, for example, by one or more radicals from the group consisting of halogen, CN, (C
1
-C
8
)alkoxy, and (C
1
-C
8
)alkylthio,
 or is (C
1
-C
8
)alkoxy, [(C
1
-C
8
)alkyl]-carbonyl or (C
1
-C
8
)alkylsulfonyl, each of the radicals being unsubstituted or substituted, for example, by one or more radicals from the group consisting of halogen, CN, (C
1
-C
8
)alkoxy, and (C
1
-C
8
)alkylthio,
 or is S(O)
p
—R
7
, where
p=0, 1 or 2 and
R
7
is (C
1
-C
8
)alkyl, (C
1
-C
8
)haloalkyl or NR
8
R
9
, where
 R
8
and R
9
independently of one another are identical or different and are H, (C
1
-C
8
)alkyl, (C
2
-C
8
)alkenyl, (C
7
-C
10
)arylalkyl, (C
7
-C
10
)alkylaryl or (C
6
-C
10
)aryl, each of the last-mentioned five radicals being unsubstituted or substituted, for example, by one or more radicals from the group consisting of halogen, CN, (C
1
-C
8
)alkoxy, and (C
1
-C
8
)alkylthio,
 or is a group of the formula
where R
10
is (C
1
-C
8
)alkyl which is unsubstituted or substituted, for example, by one or more radicals from the group consisting of halogen, CN, (C
1
-C
8
)alkoxy, and (C
1
-C
8
)alkylthio, and
 W=O or S,
A is optionally substituted aryl, e.g., an optionally substituted phenyl radical, or is an optionally substituted heterocyclic radical, e.g., an optionally substituted heteroaromatic radical, such as optionally substituted pyridyl, pyrazolyl or thienyl,
X is O or S,
R
2
,R
3
,R
4
, and R
5
are identical or different and are H, halogen, CN, (C
1
-C
8
)alkoxy or (C
1
-C
8
)alkyl, each of the two last-mentioned radicals being unsubstituted or substituted, for example, by one or more radicals from the group consisting of halogen, CN, (C
1
-C
8
)alkoxy, and (C
1
-C
8
)alkylthio,
m is 0 or 1,
R
6
is H, (C
1
-C
8
)alkyl or (C
1
-C
8
)alkoxy, each of the two last-mentioned radicals being unsubstituted or substituted, for example, by one or more radicals from the group consisting of halogen, (C
1
-C
8
)alkoxy, (C
1
-C
8
)alkylthio, (C
1
-C
8
)alkylsulfinyl, (C
1
-C
8
)alkylsulfonyl, [(C
1
-C
8
)alkoxy]-carbonyl, and CN, or is (C
2
-C
8
)alkenyl or (C
2
-C
8
)alkynyl, which are unsubstituted or substituted, for example, by one or more radicals from the group consisting of halogen, CN, (C
1
-C
8
)alkoxy, and (C
1
-C
8
)alkylthio,
 or is hydroxyl or an acyl radical such as formyl, [(C
1
-C
8
)alkyl]-carbonyl, [(C
2
-C
8
)alkenyl]-carbonyl, [(C
2
-C
8
)alkynyl]-carbonyl, (C
1
-C
8
)alkylsulfonyl, (C
2
-C
8
)alkenylsulfonyl or (C
2
-C
8
)alkynylsulfonyl, each of the last-mentioned six radicals being unsubstituted or substituted, for example, by one or more radicals from the group consisting of halogen, CN, (C
1
-C
8
)alkoxy, and (C
1
-C
8
)alkylthio, or is phenylcarbonyl or phenylsulfonyl, the phenyl radical in each of the two last-mentioned radicals being unsubstituted or substituted, for example, by one or more radicals from the group consisting of halogen, CN, NO
2
, (C
1
-C
8
)alkyl, (C
1
-C
8
)haloalkyl, and (C
1
-C
8
)alkoxy, R
6
preferably being other than hydroxyl, and
B is an acyl radical, e.g., [(C
1
-C
8
)alkyl]-carbonyl such as linear or branched [(C
1
-C
8
)-alkyl]-carbonyl or [(C
3
-C
6
)cycloalkyl]-carbonyl, each of the radicals being unsubstituted or substituted, for example, by one or more radicals from the group consisting of halogen, (C
1
-C
8
)alkoxy, (C
1
-C
8
)alkylthio, (C
1
-C
8
)alkylsulfinyl, (C
1
-C
8
)alkylsulfonyl, [(C
1
-C
8
)alkyl]-carbonyl, [(C
1
-C
8
)alkoxy]-carbonyl, and CN, or
 is [(C
2
-C
8
)alkenyl]-carbonyl or [(C
2
-C
8
)alkynyl]-carbonyl, each of the last-mentioned two radicals being unsubstituted or substituted, for example, by one or more radicals from the group consisting of halogen, CN, (C
1
-C
8
)alkoxy, and (C
1
-C
8
)alkylthio,
 or is (C
1
-C
8
)alkylsulfonyl, such as linear or branched C
1
-C
8
-alkylsulfonyl or (C
3
-C
8
)cycloalkylsulfonyl, or is (C
2
-C
8
)alkenylsulfonyl or (C
2
-C
8
)alkynylsulfonyl, each of the radicals being unsubstituted or substituted, for example, by one or more radicals from the group consisting of halogen, CN, (C
1
-C
8
)alkoxy, and (C
1
-C
8
)alkylthio,
 or is phenylcarbonyl or phenylsulfonyl, the phenyl radical in each of the two last-mentioned radicals being unsubstituted or substituted, for example, by one or more radicals from the group consisting of halogen, CN, NO
2
, (C
1
-C
8
)alkyl, (C
1
-C
8
)haloalkyl, and (C
1
-C
8
)alkoxy,
 or is mono- or di-[(C
1
-C
8
)alkyl]-aminosulfonyl, formyl or a group of the formula —CO—CO—R′ in which R′=H, OH, (C
1
-C
8
)-alkoxy or (C
1
-C
8
)alkyl, each of the last-mentioned two radicals being unsubstituted or substituted, for example, by one or more radicals from the group consisting of halogen, CN, (C
1
-C
8
)alkoxy, and (C
1
-C
8
)alkylthio, or
 is a group of the formula
 in which
W is an oxygen or sulfur atom (i.e., O or S),
T is O or S,
R
11
is (C
1
-C
8
)alkyl, (C
2
-C
8
)alkenyl or (C
2
-C
8
)alkynyl, each of the three last-mentioned radicals being unsubstituted or substituted, for example, by one or more radicals from the group consisting of halogen, CN, (C
1
-C
8
)alkoxy, (C
1
-C
8
)alkylthio, [(C
1
-C
8
)alkyl]-carbonyl, and [(C
1
-C
8
)alkoxy]-carbonyl,
R
12
and R
13
are identical or different and are H, (C
1
-C
8
)alkyl, (C
2
-C
8
)alkenyl or (C
2
-C
8
)alkynyl, each of the three last-mentioned radicals being unsubstituted or substituted, for example, by one or more radicals from the group consisting of halogen, CN, (C
1
-C
8
)alkoxy, (C
1
-C
8
)alkylthio, [(C
1
-C
8
)alkyl]-carbonyl, and [(C
1
-C
8
)alkoxy]-carbonyl, and
 the radicals R
12
and R
13
may together with the nitrogen atom form a heterocyclic radical which has 5 or 6 ring members, may contain further heteratoms from the group consisting of N, O and S, and is unsubstituted or substituted, for example, by (C
1
-C
8
)alkyl or an oxo group,
or
B and R
6
together form a 4- or 5-membered chain, e.g. of the formula
(—CH
2
)
m
—D— or —D
1
—(CH
2
)
m1
—D—, the chain being unsubstituted or substituted, for example, by one or more, preferably from one to four, (C
1
-C
4
)alkyl radicals, D and D
1
independently of one another being SO
2
or CO, and m=3 or 4 and m
1
=2 or 3,
with the exception of N-hydroxy-N-[(6-phenoxy-2-pyridyl)methyl]-acetamide and its salts.
In the formula (I) and below, the carbon-containing radicals such as alkyl, alkoxy, haloalkyl, alkylamino and alkylthio radicals and also the corresponding unsaturated and/or substituted radical may in each case be straight-chain or branched in the carbon framework or, for carbon numbers of 3 or more, may also be cyclic. Unless indicated specifically, for these radicals the lower carbon frameworks, e.g., those having from 1 to 6 carbon atoms or, in the case of unsat

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