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

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

1998-12-03

2001-09-25

Raymond, Richard L. (Department: 1621)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C544S105000

Reexamination Certificate

active

06294503

ABSTRACT:

The present invention relates to fused heterocycle compounds, process for their preparation, and herbicidal compositions containing them.
BACKGROUND OF THE INVENTION
It is known that some benzoxazine compounds as herbicides. They are described in U.S. Pat. Nos. 4,734,124,4,761,174,5,084,084 or 5,281,571, European Patent publication No. 0170191 or German Patent publication No. 3927438.
However, it is not known that benzoxazine compounds introduced functional groups at position 5 of the benzoxazine ring.
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;
R
4
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;
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
6
)R
7
and COON(R
6
)R
7
;
R
6
and R
7
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;
W is O, S or imino;
n is an integer of 0 or 1;
—L—X— is —O—, —S—, —CR
8
R
9
—, —CR
8
R
9
—O—, —CR
8
R
9
—S—, —CR
8
R
9
—CR
8
R
9
—, —CR
8
═CR
9
—, —CR
8
═N—, —N═CR
9
— or —N═N—;
R
8
and R
9
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;
Y is hydrogen or halogen;
Z is nitro, isocyanate, amino, hydroxyl, thiol, formyl, carboxyl, cyano, halogen, unsubstituted or substituted alkyl, alkenyl, alkylcarbonyl, arylcarbonyl, azido or one of the following:
wherein R
10
is alkyl, alkenyl, alkynyl, amino, cycloalkyl, heterocycloalkyl, alkylsulfonyl, arylsulfonyl, benzyl, aryl, heteroaryl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, alkoxycarbonyl, alkylthiocarbonyl, cycloalkyloxycarbonyl, aryloxycarbonyl, arylthio-carbonyl, arylthiocarbonyl, 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
11
is hydrogen or any one of the groups represented by R
10
;
R
10
and R
11
may combine to form a 4-8 membered heterocyclic ring;
wherein R
12
is alkyl, haloalkyl, dialkylamino, unsubstituted or substituted aryl or heteroaryl;
R
13
is hydrogen, halogen or any of the groups represented by R
12
;
—OR
10
, —SR
10
, —CH
2
R
14
, —CH(R
14
)
2
, —C(R
14
)
3
or —CH═CHR
14
wherein R
14
is carboxyl, alkyl, alkenyl, alkynyl, amino, cycloalkyl, heterocycloalkyl, alkylsulfonyl, arylsulfonyl, benzyl, aryl, heteroaryl, alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heterocrylcarbonyl, alkoxycarbonyl, alkylthiocarbonyl, cycloalkyloxycarbonyl, aryloxycarbonyl, arylthio-carbonyl, arylthiocarbonyl, 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, alkythiocarbonyl, 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;
provided that
(1) Z is not nitro or amino when Q is Q3 and R
2
is haloalkyl; and
(2) Z is not amino or
wherein R
10
is alkyl, alkenyl or alkynyl, and R
11
is hydrogen, alkyl, alkenyl or alkynyl, when Q is Q20.
DETAILED DESCRIPTION OF THE INVENTION
In the above definitions, the term alkyl used either alone or in compound words such as haloalkyl or alkoxy indicates either straight chain or branched alkyls containing 1-8 carbon atoms. Alkenyl and alkynyl include straight chain or branched alkenes and alkynes respectively containing 2-8 carbon atoms. The term halogen either alone or in the compound words such as haloalkyl indicates fluorine, chlorine, bromine, or iodine. Further a haloalkyl is represented by an alkyl partially or fully substituted with halogen atoms that may be same or different. A cycloalkyl group implies a saturated or unsaturated carbocycle containing 3-8 carbon atoms. A heterocycloalkyl group is a cycloalkyl group carrying 1-4 heteroatoms which are representd by oxygen, nitrogen, or sulfur atoms. An aryl group signifies an aromatic carbocycle containing 4-10 carbon atoms. A heteroaryl group is an aromatic ring containing 1-4 heteroatoms which are represented by oxygen, nitrogen, or sulfur atoms, and may for example be furanyl, pyridyl, thienyl, pyrimidinyl, benzofuranyl, quinolyl, benzothienyl or quinoxalyl.
The compound of the formula (I) may form a salt with an acidic substance or a basic substance. The salt with an acidic substance may be an inorganic acid salt such as a hydrochloride, a hydrobromide, a phosphate, a sulfate or a nitrate. The salt with a basic substance may be a salt of an inorganic or organic base such as a sodium salt, a potassium salt, a calcium salt, a quarternary ammonium salt such as ammonium salt or a dimethylamine salt.
The compound of the formula (I) may exist as geometrical or optical isomers and the present invention includes all of these isomeric forms.
Preferred compounds for the reasons of ease of synthesis or greater herbicidal efficacy are represented by the formu

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