N-heteroaryl-substituted pyridine derivatives and their use...

Details N-heteroaryl-substituted pyridine derivatives and their use... N-heteroaryl-substituted pyridine derivatives and their use...

2000-10-30

2002-04-09

Dentz, Bernard (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S243000, C504S240000, C544S236000, C544S237000, C544S238000, C544S282000, C544S285000, C544S300000, C544S310000

Reexamination Certificate

active

06369002

ABSTRACT:

The present invention relates to new, herbicidally active, substituted n-pyridyl-nitrogen heterocycles, methods for the preparation thereof, compositions comprising these compounds, and the use thereof for weed control, especially in crops of cultivated plants, such as grain, cereals, maize, rice, cotton, soybeans, rape, sorghum, sugar cane, sugar beet, sunflowers, vegetables, plantations, and forage crops or for the inhibition of plant growth and for non-selective control of weeds.
N-Phenyl and N-pyridylpyrazole compounds and N-pyridyltetramethylenetriazolidinediones with a herbicidal action 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. Nos. 5,306,694 and 4,406,689.
Also known as herbicides are N-pyridylimides, N-(2-pyridyl)pyridazinones and 3-phenyluracils, as described for example in WO 92/00976, JP-A-58-213 776 and EP-A-0 438 209.
N-(Phenyl)tetrahydroimidazoles with a herbicidal action are described for example in U.S. Pat. No. 5,112,383.
New substituted n-pyridylnitrogen heterocycles have now been found with herbicidal and growth-inhibiting properties.
Accordingly, the invention relates to compounds of formula I
wherein
R
1
is hydrogen, fluorine, chlorine, bromine or methyl;
R
2
is C
1
-C
4
alkyl, C
1
-C
4
halogenalkyl, halogen, hydroxy, C
1
-C
4
alkoxy, C
1
-C
4
halogenalkoxy, nitro, amino or cyano;
R
3
is cyano or R
4
C(O)—;
R
4
is hydrogen, fluorine, chlorine, C
1
-C
8
alkyl, C
2
-C
8
alkenyl, C
2
-C
8
alkinyl, C
3
-C
6
cycloalkyl, C
1
-C
8
halogenalkyl, cyano-C
1
-C
4
alkyl, C
2
-C
8
halogenalkenyl, 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 substituted once to three times by halogen, C
1
-C
4
alkyl or C
1
-C
4
halogenalkyl, benzyl, benzyl substituted once to three times on the phenyl ring by halogen, C
1
-C
4
alkyl or C
1
-C
4
halogenalkyl; or
R
3
is R
5
X
1
C(O)—;
X
1
is oxygen, sulfur,
R
5
is hydrogen, C
1
-C
8
alkyl, C
3
-C
8
alkenyl, C
3
-C
8
alkinyl, C
3
-C
6
cycloalkyl, C
3
-C
6
cycloalkyl-C
1
-C
6
alkyl, C
1
-C
8
halogenalkyl, C
3
-C
8
halogenalkenyl, cyano-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, (oxiranyl)-CH
2
—, oxetanyl, C
1
-C
4
alkylthio-C
1
-C
4
alkyl, phenyl, phenyl substituted once to three times by halogen, C
1
-C
4
alkyl or C
1
-C
4
halogenalkyl, benzyl, benzyl substituted once to three times on the phenyl ring by halogen, C
1
-C
4
alkyl or C
1
-C
4
-halogenalkyl, phenyl-C
2
-C
6
alkyl, C
1
-C
6
alkyl-CO—C
1
-C
4
alkyl,
 R
8
X
2
C(O)—C
1
-C
6
-alkyl,
 or R
8
X
2
C(O)—C
3
-C
6
cycloalkyl;
X
2
is oxygen, sulfur,
R
8
is hydrogen, C
1
-C
8
alkyl, C
3
-C
8
alkenyl, C
3
-C
8
alkinyl, C
3
-C
6
cycloalkyl, C
1
-C
8
halogenalkyl C
3
-C
8
halogenalkenyl, cyano-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, (oxiranyl)-CH
2
—, oxetanyl, C
1
-C
4
alkylthio-C
1
-C
4
alkyl, phenyl, phenyl substituted once to three times by halogen, C
1
-C
4
alkyl or C
1
-C
4
halogenalkyl, benzyl, benzyl substituted once to three times on the phenyl ring by halogen, C
1
-C
4
alkyl or C
1
-C
4
halogenalkyl, or phenyl-C
2
-C
6
alkyl; R
6
, R
7
, R
9
and R
10
are independently of one another hydrogen, C
1
-C
8
alkyl, C
3
-C
8
alkenyl, C
3
-C
8
alkinyl, C
1
-C
8
halogenalkyl or benzyl; or
R
3
is B
1
—C
1
-C
8
alkyl, B
1
—C
2
-C
8
alkenyl, B
1
—C
2
-C
8
alkinyl, B
1
—C
1
-C
8
halogenalkyl, B
1
—C
2
-C
8
halogenalkenyl, B
1
—C
1
-C
4
alkoxy-C
1
-C
4
alkyl, B
1
—C
1
-C
4
alkylthio-C
1
-C
4
alkyl or B
1
—C
3
-C
6
cycloalkyl;
B
1
is hydrogen, cyano, hydroxy, C
1
-C
8
alkoxy, C
3
-C
8
alkenyloxy, R
11
X
3
C(O)—, C
1
-C
4
alkylcarbonyl or C
1
-C
4
halogenalkylcarbonyl;
X
3
has the same meaning as X
2
;
R
11
has the same meaning as R
8
; or
R
3
is B
2
—C(R
12
)═CH—;
B
2
is nitro, cyano or R
13
X
4
C(O)—;
R
12
is cyano or R
14
X
5
C(O)—;
X
4
and X
5
have the same meaning as X
2
; and
R
13
and R
14
have the same meaning as R
8
;
R
15
is C
1
-C
3
alkyl, C
1
-C
3
halogenalkyl or amino;
R
16
is C
1
-C
3
halogenalkyl, C
1
-C
3
alkyl-S(O)
n1
, C
1
-C
3
halogenalkyl-S(O)
n1
or cyano; or
R
16
and R
15
together form a C
3
- or C
4
alkylene or C
3
- or C
4
alkenylene bridge which may be substituted by halogen, C
1
-C
3
halogenalkyl or cyano;
n
1
is 0, 1 or 2;
R
17
is hydrogen, C
1
-C
3
alkyl, halogen, C
1
-C
3
halogenalkyl or cyano; or
R
17
and R
16
together form a C
3
- or C
4
alkylene or C
3
- or C
4
alkenylene bridge which may be substituted by halogen, C
1
-C
3
halogenalkyl or cyano;
R
18
is hydrogen, C
1
-C
3
alkyl, halogen or cyano;
R
19
is C
1
-C
3
halogenalkyl; or
R
19
and R
18
together form a C
3
- or C
4
alkylene or C
3
- or C
4
alkenylene bridge which may be substituted by halogen, C
1
-C
3
halogenalkyl or cyano;
R
20
is hydrogen or C
1
-C
3
alkyl or halogen; or
R
20
and R
19
together form a C
3
- or C
4
alkylene or C
3
- or C
4
alkenylene bridge which may be substituted by halogen, C
1
-C
3
halogenalkyl or cyano;
R
21
is hydrogen, C
1
-C
3
alkyl, halogen, C
1
-C
3
halogenalkyl, R
40
O—, R
41
S(O)
n
2
, R
42
(R
43
)N,
R
45
(R
46
)N—C(R
44
)═N—, hydroxy, nitro or N≡C—S—;
R
40
is C
1
-C
3
alkyl, C
1
-C
3
halogenalkyl, C
2
-C
4
alkenyl, C
3
- or C
4
alkinyl or C
1
-C
5
alkoxycarbonyl-C
1
-C
4
alkyl;
R
41
is C
1
-C
4
alkyl or C
1
-C
4
halogenalkyl;
n
2
is 0, 1 or 2;
R
42
is hydrogen, C
1
-C
4
alkyl, C
1
-C
4
halogenalkyl, C
3
-C
6
cycloalkyl, OHC— or C
1
-C
4
alkylcarbonyl;
R
43
, R
44
, and R
46
are independently of one another hydrogen or C
1
-C
4
alkyl;
R
45
is C
1
-C
4
alkyl;
R
22
is hydrogen, C
1
-C
4
alkyl, halogen, C
1
-C
4
halogenalkyl, C
2
-C
4
alkenyl, C
3
-C
5
halogenalkenyl, C
3
- or C
4
alkinyl, C
1
-C
4
alkoxy, C
1
-C
4
alkylcarbonyl, C
1
-C
4
halogenalkylcarbonyl, C
2
-C
4
alkenylcarbonyl, C
2
-C
4
halogenalkenylcarbonyl, C
2
-C
4
alkinylcarbonyl, C
2
-C
4
halogenalkinylcarbonyl, C
1
-C
4
alkylcarbamoyl, C
1
-C
4
alkylS(O)
n3
, C
3
- or C
4
alkinylS(O),
n3
, OHC—, nitro, amino, cyano or N≡C—S—;
n
3
is 0, 1 or 2;
R
23
and R
24
independently of one another are hydrogen, C
1
-C
4
alkyl, halogen, C
1
-C
4
halogenalkyl or cyano
R
25
and R
26
are independently of one another hydrogen, methyl, halogen, hydroxy or ═O;
R
27
and R
28
are independently of one another hydrogen, C
1
-C
4
alkyl or C
1
-C
4
halogenalkyl;
R
29
and R
30
are independently of one another hydrogen, C
1
-C
3
alkyl or halogen;
R
31
and R
32
independently of one another are hydrogen or C
1
-C
4
alkyl; or
R
31
and R
32
together form the group
R
47
and R
48
are independently of one another C
1
-C
4
alkyl; or
R
47
and R
48
together form a C
4
or C
5
alkylene bridge;
R
33
is hydrogen or C
1
-C
3
alkyl; or
R
33
together with R
32
forms a C
3
-C
5
alkylene bridge which may be broken by oxygen and/or substituted by halogen, C
1
-C
4
alkyl, C
2
-C
4
alkenyl, C
1
-C
3
alkylcarbonyloxy, C
1
-C
3
alkylsulfonyloxy, hydroxy or ═O;
R
34
, R
35
, R
36
and R
37
are independently of one another hydrogen, C
1
-C
3
alkyl, C
3
- or C
4
alkenyl or C
3
-C
5
alkinyl; or
R
34
and R
35
on the one hand and R
36
and R
37
on the other each form a C
2
-C
5
alkylene or C
3
-C
5
alkenylene bridge, which may be broken by oxygen, —C(O)—, sulfur, or —S(O)
2
—;
R
38
is hydrogen, C
1
-C
4
alkyl, C
1
-C
4
halogenalkyl, C
3
- or C
4
alkenyl or C
3
- or C
4
alkinyl;
R
39
is hydrogen, C
1
-C
4
alkyl, C
1
-C
3
alkoxy-C
1
- or —C
2
alkyl, C
1
-C
4
halogenalkyl, C
3
- or C
4
alkenyl, C
3
- or C
4
halogenalkenyl or C
3
- or C
4
alkinyl; or
R
39
and R
38
together form a C
3
-C
5
alkylene bridge; and
X
6
, X
7
, X
8
, X
9
, X
10
, X
11
, X
12
, X
13
, X
14
, X
15
, X
16
, X
17
, X
18
and X
19
are independently of one another oxygen or sulfur,
and the agrochemically acceptable salts and stereoisomers of these compounds of formula I.
In the definitions listed hereinbefore, halogen is taken to mean iodine, preferably fluorine, chlorine and bromine.
The alkyl, alkenyl and alkinyl groups mentioned in the substituent definitions may

Affiliated with

Also associated with

Rating

N-heteroaryl-substituted pyridine derivatives and their use... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with N-heteroaryl-substituted pyridine derivatives and their use..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and N-heteroaryl-substituted pyridine derivatives and their use... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2881602