Fused tricyclic compounds, process for their preparation,...

Details Fused tricyclic compounds, process for their preparation,... Fused tricyclic compounds, process for their preparation,...

2002-03-18

2004-08-03

Shah, Mukuno (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S225000, C544S101000, C544S058600, C544S058700

Reexamination Certificate

active

06770596

ABSTRACT:

BACKGROUND OF THE INVENTION
It is known that some benzoxazine type compounds show herbicidal activity. They are described in U.S. Pat. No. 4,734,124, 4,761,174, 5,084,084 or 5,281,571, European Patent publication No. 0170191 or German Patent publication No. 3927438. Certain fused tricyclic compounds with herbicidal activity were described in European Patent publication No. 406993.
However, it is not known that benzoxazine type compounds with a functional group introduced at position 5 followed by cyclization afford fused tricyclic compounds which exhibit herbicidal activity.
SUMMARY OF THE INVENTION
This invention delineates a method for the control of undesired vegetation in a plantation crop by the application to the locus of the crop an effective amount of a compound described herein. The herbicidal compounds of the present invention are described by the following formula (I) or its salt:
wherein Q is a heterocycle selected from the group consisting of Q1 to Q24:
wherein R
1
is hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, amino, alkoxyalkyl, acetyl, alkoxycarbonylamino, alkylcarbonylamino or alkoxycarbonyl;
R
2
is alkyl, haloalkyl, alkoxy, haloalkoxy or unsubstituted or substituted phenyl;
R
3
is hydrogen, halogen, nitro, amino, alkylamino, haloalkylamino, cyano or amide;
R4 and R
5
are independently oxygen, sulfur or imino;
Q6, Q7, Q10, Q16 or Q17 may be unsaturated containing one or two double bonds in the 6-membered ring;
Y is hydrogen or halogen;
—L—X— is —O—, —S—, —S(O)—, —S(O)
2
— —CR
6
R
7
—, —CR
6
R
7
—O—, —O—CR
6
R
7
—, —CR
6
R
7
—S—, S—CR
6
R
7
—, —CR
6
R
7
—S(O)—, —S(O)—CR
6
R
7
, —CR
6
R
7
—S(O)
2
—, —S(O)
2
—CR
6
R
7
—, —CR
6
R
7
—CR
6
R
7
—, —CR
6
═CR—, —NR
6
—, —CR
6
═N—, —N═CR
6
—, —N═N—, —CR
6
R
7
—NR
6
— or —NR
6
—CR
6
R
7
—;
A is —O—, —S—, —S(O)—, S(O)
2
, —NH—, —C(O)—, —C(S)—, —C(NH)— or —CR
6
R
7
—;
A′ is —O—, —S—, —S(O)—, S(O)
2
, —NH—, —C(O)—, —C(S)—, —C(NH)— or —CR
10
R
11
—;
n is an integer of 0 to 2;
m is an integer of 0 to 2;
B is N, CH, C, or N
+
E is a bond, —O—, —S—, —S(O)—, —S(O)
2
—, —NH—, —C(O)—, —C(S)—, —C(NH)—, —CR
12
R
13
—, —CR
12
R
13
—CR
12
R
13
—, —CR
12
═CR
13
—, ═CR
12
— or —NR
12
—;
D is —NR—, —N═CR
14
—, —O—, —S—, —S(O)—, —S(O)
2
—, —CR
14
R
15
— or —CR
14
═CR
15
—;
R
6
, R
7
, R
8
, R
9
, R
10
, R
11
, R
12
, R
13
, R
14
and R
15
are independently hydrogen, halogen, hydroxy, cyano, nitro, amino, alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, benzyl, aryl, heteroaryl, alkoxy, haloalkoxy, aryloxy, heteroaryloxy, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, amninocarbonylamino, alkylaminocarbonylamino, arylaminocarbonylamino, alkoxyalkyl, alkylthioalkyl, alkoxycarbonylalkyl, cycloalkoxycarbonylalkyl, alkylcarbonyloxyalkyl, alkylcarbonylaminoalkyl, alkoxyalkylcarbonylalkyl, heterocycloalkyl, alkylsulfonyl, arylsulfonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, heteroarylcarbonyl, alkylthiocarbonyl, cycloalkyloxycarbonyl, arylthio-carbonyl, aryl-thiocarbonyl, heteroaryloxycarbonyl, aminocarbonyl, alkylaminocarbonyl, arylaminocarbonyl, heteroarylaminocarbonyl, alkoxycarbonylcarbonyl or arylcarbonylcarbonyl where any of these groups may be substituted with at least one substituent selected from the group consisting of halogen, cyano, nitro, amino, dialkylamino, hydroxyl, carboxyl, alkyl, alkenyl, alkynyl, cycloalkyl, alkylcarbonyl, alkylcarbonyloxy, alkoxy, alkoxycarbonyl, alkylthio, alkylthiocarbonyl, alkoxythiocarbonyl alkylaminocarbonyl, arylaminocarbonyl, alkylsulfonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, aryl, arylcarbonyl, aryloxy, aryloxycarbonyl, arylthio, heteroaryl, heteroaryloxycarbonyl and methylenedioxy, wherein the alkyl moiety or aryl moiety may be substituted with at least one substituent selected from the group consisting of halogen, cyano, nitro, alkyl, alkoxy, haloalkyl, haloalkoxy, alkoxycarbonyl, cycloalkyl, aryl and heterocycloalkyl;
R is hydrogen, alkyl alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkoxyalkoxyalkyl, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aryloxycarbonyl, alkoxycarbonylalkyl, alkoxyalkoxycarbonylalkyl, cycloalkoxycarbonylalkyl, aralkyl, heteroaralkyl, aryloxyalkyl or heteroaryloxyalkyl where any of these groups may be substituted with at least one substituent selected from the group consisting of halogen, cyano, nitro, amino, carboxyl, alkylthioalkyl, hydroxyalkyl, CON(R
16
)R
17
and COON(R
16
)R
17
;
R
16
and R
17
are independently hydrogen, halogen, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxyalkyl, alkylthioalkyl, alkoxycarbonylalkyl, cycloalkoxycarbonylalkyl, alkylcarbonyloxyalkyl, alkylcarbonylaminoalkyl, alkoxyalkylcarbonylalkyl, phenyl or benzyl where any of these groups may be substituted with at least one substituent selected from the group consisting of halogen, cyano, carboxyl, hydroxy, nitro and amino.


REFERENCES:
patent: 4734124 (1988-03-01), Chang et al.
patent: 4761174 (1988-08-01), Chang et al.
patent: 5084084 (1992-01-01), Satow et al.
patent: 5281571 (1994-01-01), Woodard et al.
patent: 5364856 (1994-11-01), Booher et al.
patent: 3927438 (1991-02-01), None
patent: 0 170191 (1986-02-01), None
patent: 0406993 (1991-01-01), None
Kost, L.G., et al. (M.V. Lomonosov State Univ., Moscow). Khim. Geterotsikl. Soedin., Akad Naut Latv. SSR 1996 (1), 39-45 (Russ).

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