N-pyridyl herbicide compounds

Details N-pyridyl herbicide compounds N-pyridyl herbicide compounds

2000-10-10

2002-04-30

Davis, Zinna Northington (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S243000, C504S244000, C504S253000, C504S260000, C544S238000, C544S333000, C546S272400, C546S274400, C546S305000, C546S306000, C546S309000

Reexamination Certificate

active

06380134

ABSTRACT:

The present invention relates to novel herbicidally active substituted N-pyridyl-nitrogen heterocycles, processes for their preparation, compositions comprising these compounds, and their use for controlling weeds, especially in crops of useful plants such as, for example, cereals, maize, rice, cotton, soya, oil seed rape, sorghum, sugar cane, sugar beet, sunflowers, vegetables, plantation crops and forage plants, or for inhibiting the growth of plants, and for nonselective weed control.
N-phenyl- and n-pyridyl-pyrazole compounds and N-pyridyltetramethylene triazolidine diones which are herbicidally active are described, for example, in EP-A-0 370 332, DE-A-3 917 469, DE-A-19 518 054, DE-A-19 530 606, U.S. Pat. No. 5,306,694 and U.S. Pat. No. 4,406,689. Also known as herbicides are N-pyridylimides, N-(2-pyridyl)pyridazinones and N-phenyluracils, as described, for example, in WO 92/00976, JP-A-58-213 776 and EP-A-0 438 209. N-(phenyl)tetrahydroimidazoles having herbicidal activity are described, for example, in U.S. Pat. No. 5,112,383.
There have now been found novel substituted N-pyridyl-nitrogen heterocycles which have herbicidal and growth-inhibitory properties.
The present invention thus relates to compounds of the formula I
 in which
A ═N— or
R
1
is hydrogen, fluorine, chlorine, bromine or methyl;
R
2
is C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, halogen, R
6
O—, nitro, amino or cyano;
R
3
is halogen, nitro, amino, R
4
NH—, R
4
R
5
N—, azido or CIS(O)
2
—;
R
4
and R
5
independently of one another are C
1
-C
8
alkyl, C
3
-C
8
alkenyl, C
3
-C
8
alkynyl, C
3
-C
6
cycloalkyl, C
1
-C
8
haloalkyl, C
3
-C
8
haloalkenyl, HCO—, C
1
-C
4
alkylcarbonyl, C
1
-C
4
haloalkylcarbonyl, C
1
-C
4
alkylsulfonyl, C
1
-C
4
haloalkylsulfonyl, benzyl or benzyl which is mono- to trisubstituted on the phenyl ring by halogen, C
1
-C
4
alkyl or C
1
-C
4
haloalkyl; or
R
4
and R
5
together with the N atom to which they are bonded form a saturated or unsaturated heterocyclic ring which contains O, N or S as further hetero atoms and which can be substituted by halogen, C
1
-C
3
alkyl, C
1
-C
3
haloalkyl, C
1
-C
3
alkoxy, C
1
-C
4
alkoxycarbonyl, C
1
-C
3
alkylS(O)
n1
—, nitro or cyano; or
R
3
is R
6
O—;
R
6
is hydrogen, C
1
-C
8
alkyl, C
3
-C
8
alkenyl, C
3
-C
8
alkynyl, C
3
-C
6
cycloalkyl, C
1
-C
8
haloalkyl, cyano-C
1
-C
8
alkyl, C
3
-C
8
haloalkenyl, hydroxy-C
1
-C
4
alkyl, C
1
-C
4
alkoxy-C
1
-C
4
alkyl, C
3
-C
6
alkenyloxy-C
1
-C
4
alkyl, C
3
-C
6
alkynyloxy-C
1
-C
4
alkyl, C
1
-C
4
alkoxy-C
1
-C
4
alkoxy-C
1
-C
4
alkyl, C
1
-C
4
alkylthio-C
1
-C
4
alkyl, C
1
-C
8
alkylcarbonyl, C
1
-C
8
alkoxycarbonyl, C
3
-C
8
alkenyloxycarbonyl, benzyloxy-C
1
- or —C
2
alkyl, benzylcarbonyl, benzyloxycarbonyl, phenyl,phenyl-C
2
-C
8
alkyl, benzyl, pyridyl, pyrimidinyl, pyrazinyl or pyridazinyl, it being possible for these aromatic and heteroaromatic rings to be optionally mono- to trisubstituted by halogen, C
1
-C
4
alkyl or C
1
-C
4
haloalkyl; or
R
6
is R
7
X
1
C(O)—C
1
-C
8
alkyl- or
X
1
is oxygen, sulfur or
R
7
is hydrogen, C
1
-C
8
alkyl, C
3
-C
8
alkenyl, C
3
-C
8
alkynyl, C
3
-C
6
cycloalkyl, C
1
-C
8
haloalkyl, C
3
-C
8
haloalkenyl, C
1
-C
4
alkoxy-C
1
-C
4
alkyl, C
3
-C
6
alkenyloxy-C
1
-C
4
alkyl, C
1
-C
4
alkylthio-C
1
-C
4
alkyl, phenyl, phenyl which is mono- to trisubstituted by halogen, C
1
-C
4
alkyl or C
1
-C
4
haloalkyl, or benzyl or benzyl which is mono- to trisubstituted on the phenyl ring by halogen, C
1
-C
4
alkyl or C
1
-C
4
haloalkyl;
R
8
is hydrogen, C
1
-C
8
alkyl, C
3
-C
8
alkenyl, C
3
-C
8
alkynyl, C
3
-C
6
cycloalkyl, C
1
-C
8
haloalkyl or benzyl; or
R
3
is R
9
S(O)
n1
—;
n
1
is 0, 1 or 2;
R
9
is C
1
-C
8
alkyl, C
3
-C
8
alkenyl, C
3
-C
8
alkynyl, C
3
-C
6
cycloalkyl, C
1
-C
8
haloalkyl, carboxy-C
1
-C
4
alkyl, C
1
-C
4
alkoxycarbonyl-C
1
-C
4
alkyl, benzyloxycarbonyl-C
1
-C
4
alkyl, C
1
-C
4
alkylthio-C(O)—C
1
-C
4
alkyl, C
3
-C
5
alkenyloxycarbonyl-C
1
-C
4
alkyl, C
1
-C
4
alkylaminocarbonyl-C
1
-C
4
alkyl, di-C
1
-C
4
alkylaminocarbonyl-C
1
-C
4
alkyl, C
3
-C
5
alkenylaminocarbonyl-C
1
-C
4
alkyl, C
3
-C
8
haloalkenyl, C
1
-C
4
alkoxy-C
1
-C
4
alkyl, C
3
-C
6
alkenyloxy-C
1
-C
4
alkyl, C
1
-C
4
alkylthio-C
1
-C
4
alkyl, phenyl, phenyl which is mono- to trisubstituted by halogen, C
1
-C
4
alkyl or C
1
-C
4
haloalkyl, or benzyl or benzyl which is mono- to trisubstituted on the phenyl ring by halogen, C
1
-C
4
alkyl or C
1
-C
4
haloalkyl, and, if n
1
is 0,
R
9
is additionally hydrogen, C
1
-C
8
alkylcarbonyl, R
10
X
2
C(O)— or R
10
X
2
C(O)—C
1
— or —C
2
alkyl;
X
2
is oxygen, sulfur or
R
10
is hydrogen, C
1
-C
8
alkyl, C
3
-C
8
alkenyl, C
3
-C
8
alkynyl, C
3
-C
6
cycloalkyl, C
1
-C
8
haloalkyl, C
3
-C
8
haloalkenyl, C
1
-C
4
alkoxy-C
1
-C
4
alkyl, C
3
-C
6
alkenyloxy-C
1
-C
4
alkyl, C
1
-C
4
alkylthio-C
1
-C
4
alkyl, phenyl, phenyl which is mono- to trisubstituted by halogen, C
1
-C
4
alkyl or C
1
-C
4
haloalkyl, or benzyl or benzyl which is mono- to trisubstituted on the phenyl ring by halogen, C
1
-C
4
alkyl or C
1
-C
4
haloalkyl;
R
11
is hydrogen, C
1
-C
8
alkyl or C
3
-C
8
alkenyl; or
R
3
is R
12
R
13
NS(O)
2
—;
R
12
is hydrogen, C
1
-C
8
alkyl, C
2
-C
8
alkenyl, C
3
-C
8
alkynyl or C
3
-C
6
cycloalkyl;
R
13
is hydrogen, C
1
-C
8
alkyl, C
3
-C
8
alkenyl, C
3
-C
8
alkynyl, C
1
-C
8
haloalkyl, C
1
-C
4
alkoxy-C
1
-C
4
alkyl, C
1
-C
4
alkylcarbonyl, C
1
-C
4
haloalkylcarbonyl, benzyl, benzoyl, or benzyl or benzoyl which are mono- to trisubstituted on the phenyl ring by halogen, C
1
-C
4
alkyl or C
1
-C
4
haloalkyl;
W is a group
 or
R
14
is C
1
-C
3
alkyl, C
1
-C
3
haloalkyl or amino;
R
15
is C
1
-C
3
haloalkyl, C
1
-C
3
alkyl-S(O)
n2
—, C
1
-C
3
haloalkyl-S(O)
n2
— or cyano; or
R
15
and R
14
together form a C
3
or C
4
alkylene bridge which can be substituted by halogen, C
1
-C
3
haloalkyl or cyano;
n
2
is 0, 1 or 2;
R
16
is hydrogen, C
1
-C
3
alkyl, halogen, C
1
-C
3
haloalkyl or cyano; or
R
16
and R
15
together form a C
3
or C
4
alkylene bridge which can be substituted by halogen, C
1
-C
3
haloalkyl or cyano;
R
17
is hydrogen, C
1
-C
3
alkyl, halogen or cyano; R
18
is C
1
-C
3
haloalkyl; or
R
18
and R
17
together form a C
3
or C
4
alkylene or C
3
or C
4
alkenylene bridge, both of which can be substituted by halogen, C
1
-C
3
alkyl or C
1
-C
3
haloalkyl;
R
19
is hydrogen, C
1
-C
3
alkyl or halogen; or
R
19
and R
18
together form a C
3
or C
4
alkylene or C
3
or C
4
alkenylene bridge, both of which can be substituted by halogen, C
1
-C
3
alkyl or C
1
-C
3
haloalkyl;
R
20
and R
21
independently of one another are hydrogen or C
1
-C
4
alkyl; or
R
20
and R
21
together are a group of
R
25
and R
26
independently of one another are C
1
-C
4
alkyl; or
R
25
and R
26
together form a C
4
or C
5
alkylene bridge;
R
22
is hydrogen or C
1
-C
3
alkyl; or
R
22
and R
21
together form a C
3
-C
5
alkylene bridge which can be interrupted by oxygen and substituted by halogen, C
1
-C
4
alkyl, C
1
-C
3
haloalkyl, C
2
-C
4
alkenyl, C
1
-C
3
alkylcarbonyloxy, C
1
-C
3
alkoxycarbonyl, C
1
-C
3
alkylsulfonyloxy, hydroxyl or ═O;
R
23
and R
24
independently of one another are hydrogen or C
1
-C
3
alkyl; or
R
23
and R
24
together form a C
2
-C
5
alkylene bridge which can be interrupted by oxygen, sulfur, —C(O)— or —S(O)
2
—; and
X
3
, X
4
, X
5
, X
6
, X
7
, X
8
and X
9
independently of one another are oxygen or sulfur, and the agrochemically tolerated salts and stereoisomers of these compounds of the formula I.
In the abovementioned definitions, halogen is to be understood as meaning iodine, preferably fluorine, chlorine and bromine.
The alkyl, alkenyl and alkynyl groups in the definitions of substituents can be straight-chain or branched, and this also applies to the alkyl, alkenyl and alkynyl moiety of the alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkenyloxycarbonyl, alkenyloxyalkyl, alkynyloxyalkyl-, alkylS(O)
n2
—, alkylsulfonyloxy, alkylthioalkyl, alkoxyalkyl, alkoxyalkoxyalkyl, alkylamino, dialkylamino, phenylalkyl and R
7
X
1
C(O)—C
1
-C
8
alkyl groups. Alkyl groups, are, for example, methyl, ethyl, n-propyl, iso-pro

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