Benzohydrazide derivatives as herbicides and desiccant...

Details Benzohydrazide derivatives as herbicides and desiccant... Benzohydrazide derivatives as herbicides and desiccant...

2002-07-17

2004-08-03

Rao, Deepak (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S280000, C544S311000, C544S312000, C548S370100, C548S375100

Reexamination Certificate

active

06770597

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to novel benzohydrazide derivatives, their salts and compositions containing them, intermediates, a process for producing them, and their use as herbicides.
2. Description of the Related Art
EP 195346 disclosed the herbicidal utility of uracil derivatives, in which the phenyl ring of the described compounds were substituted by carboxyl moiety. JP 01139581 and WO 92/06962 disclosed benzohydrazide, in which the phenyl ring of the described compounds were substituted by tetrahydrophthalamide and pyrazole moiety respectively. WO99/52878 described benzohydrazide derivatives with pyridazinone moiety. EP0745599 described thiotrione derivatives as an intermediate. WO97/33875 and WO97/40018 disclosed benzonitrile derivatives. Phthalimide derivative was disclosed in Indian J. Chem., Sect. B (1986), 25B(3), 308-311. Despite the broad coverage of these patents and literature, the general structure of the present invention has not been described.
The specific benzohydrazides and related compounds of the formula I mentioned below are novel and can be used to effectively control a variety of broad or grassy leaf plant species.
SUMMARY OF THE INVENTION
The 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 present application describes certain herbicidal benzohydrazide derivatives of the formula (I) including all geometric, tautomeric and stereoisomers, and their salts, as well as compositions containing them and methods of preparation for these compounds.
wherein
X is hydrogen or halogen;
Y is represented by hydrogen, halogen, nitro, (C
1-4
)alkyl, (C
1-4
)alkoxy, (C
1-4
)haloalkyl or (C
1-4
)haloalkoxy;
T is represented by N or CH;
Z is one of the following groups;
A is oxygen, sulfur or NR
4
;
R
1
, R
2
, R
3
and R
4
are independent of each other and may be selected from the group consisting of hydrogen, cyano, (C
1-6
)alkyl, (C
1-6
)haloalkyl, (C
1-6
)alkoxy,(C
1-6
)haloalkoxy, (C
1-6
)alkoxyalkyl, (C
2-6
)alkynyl, (C
2-6
)alkenyl, aryl, heteroaryl, aryloxy, heteroaryloxy, (C
3-6
)cycloalkyl, (C
3-6
)cyclocarbonyl, carboxy, (C
1-6
)alkylcarbonyl, arylcarbonyl, (C
1-3
)haloalkylcarbonyl, (C
1-6
)alkylcarbonyloxy, (C
1-6
)haloalkylcarbonyloxy, (C
1-6
)alkoxycarbonyl, (C
1-6
)haloalkoxycarbonyl, (C
1-6
)alkylthiocarbonyl, (C
1-6
)haloalkylthiocarbonyl, (C
1-6
)alkoxythiocarbonyl, (C
1-6
)haloalkoxythiocarbonyl,(C
1-6
)alkylamino, arylsulfonylamino, arylamino, (C
1-6
)alkylthio, arylthio, (C
2-6
)alkenylthio, (C
2-6
)alkynylthio, (C
1-6
)alkylsulfinyl, (C
2-6
)alkenylsulfinyl, (C
2-6
)alkynylsulfinyl, (C
1-6
)alkylsulfonyl, (C
2-6
)alkenylsulfonyl, (C
2-6
)alkynylsulfonyl, arylsulfonyl, where any of these groups may be optionally substituted with one or one more of the following group consisting of halogen, hydroxy, mercapto, cyano, nitro, amino, caboxy, (C
1-6
)alkyl, (C
1-6
)haloalkyl, (C
1-6
)alkylcarbonyl, (C
1-6
)alkylcarbonyloxy, (C
1-6
)haloalkylcarbonyl, (C
1-6
)haloalkylcarbonyloxy, (C
1-6
)alkoxy, (C
1-6
)alkoxycarbonyl, aminocarbonyl, (C
1-6
)alkylaminocarbonyl, (C
1-6
)haloalkoxy, (C
1-6
)haloalkoxycarbonyl, (C
1-6
)alkylsulfonyl, (C
1-6
)haloalkylsulfonyl, aryl, haloaryl, alkoxyaryl, aryoxy, arylthio, haloaryloxy, heteroaryl, heteroaryloxy and (C
3-7
)cycloalkyl;
When R
2
and R
3
are taken together with the atoms to which they are attached, they represent a three to seven membered substituted or unsubstituted ring optionally containing oxygen, carbonyl, S(O)
n**
or nitrogen with following optional substitutions, one to three halogen, cyano, nitro, hydroxy, amino, carbonyl, (C
1-6
)alkyl, (C
1-6
)haloalkyl, (C
1-6
)alkylcarbonyl, (C
1-6
)alkylcarbonyloxy, (C
1-6
)haloalkylcarbonyl, (C
1-6
)haloalkylcarbonyloxy, (C
1-6
)alkoxy, (C
1-6
)alkoxycarbonyl, aminocarbonyl, (C
1-6
)alkylaminocarbonyl, (C
1-6
)haloalkoxy, (C
1-6
)haloalkoxycarbonyl, (C
1-6
)alkylsulfonyl, (C
1-6
)haloalkylsulfonyl, aryl, heteroaryl or (C
3-7
)cycloalkyl;
R
5
and R
6
are independent of each other and may be selected from the group consisting of hydrogen, (C
1-6
)alkyl, (C
2-6
)alkenyl, (C
2-6
)alkynyl, (C
1-6
)alkoxycarbonyl and heteroarylcarbonyl;
where any of these groups may be optionally substituted with one or more of the following groups consisting of halogen, hydroxy, cyano, nitro, amino, caboxyl, (C
1-6
)alkyl, (C
1-6
)haloalkyl, (C
1-6
)alkylcarbonyl, (C
1-6
)alkylcarbonyloxy, (C
1-6
)haloalkylcarbonyl, (C
1-6
)haloalkylcarbonyloxy, (C
1-6
)alkoxy, (C
1-6
)alkoxycarbonyl, aminocarbonyl, (C
1-6
)alkylaminocarbonyl, (C
1-6
)haloalkoxy, (C
1-6
)haloalkoxycarbonyl, (C
1-6
)alkylsulfonyl, (C
1-6
)haloalkylsulfonyl, aryl, heteroaryl and (C
3-7
)cycloalkyl;
When R
5
and R
6
are taken together with the atoms to which they are attached, they represent a three to seven membered substituted or unsubstituted ring optionally containing oxygen, carbonyl, S(O)
n**
or nitrogen with following optional substitutions, one to three halogen, cyano, nitro, hydroxy, amino, carbonyl, (C
1-6
)alkyl, (C
1-6
)haloalkyl, (C
1-6
)alkylcarbonyl, (C
1-6
)alkylcarbonyloxy, (C
1-6
)haloalkylcarbonyl, (C
1-6
)haloalkylcarbonyloxy, (C
1-6
)alkoxy, (C
1-6
)alkoxycarbonyl, aminocarbonyl, (C
1-6
)alkylaminocarbonyl, (C
1-6
)haloalkoxy, (C
1-6
)haloalkoxycarbonyl, (C
1-6
)alkylsulfonyl, (C
1-6
)haloalkylsulfonyl, aryl, heteroaryl or (C
3-7
)cycloalkyl;
R
7
may be selected from the group consisting of hydrogen, (C
1-6
)alkyl, (C
2-6
)alkenyl or (C
2-6
)alkynyl where any of these groups may be optionally substituted with one or more of the following groups consisting of halogen, hydroxy, cyano, nitro, amino, caboxyl, (C
1-6
)alkyl, (C
1-6
)haloalkyl, (C
1-6
)alkylcarbonyl, (C
1-6
)alkylcarbonyloxy, (C
1-6
)haloalkylcarbonyl, (C
1-6
)haloalkylcarbonyloxy, (C
1-6
)alkoxy, (C
1-6
)alkoxycarbonyl, aminocarbonyl, (C
1-6
)alkylaminocarbonyl, (C
1-6
)haloalkoxy, (C
1-6
)haloalkoxycarbonyl, (C
1-6
)alkylsulfonyl, (C
1-6
)haloalkylsulfonyl, aryl, heteroaryl and (C
3-7
)cycloalkyl;
M is halogen, dichloroiodate, tetrachloroiodate, sulfate, nitrate, formate, acetate, propionate or butylate.
Q is selected from;
wherein
A
1
and A
2
are independently oxygen or sulfur;
R
8
is hydrogen, halogen, cyano, nitro, formyl (C
1-4
)alkyl, (C
1-4
)haloalkyl, amino, (C
1-4
)alkylamino, (C
1-4
)haloalkylamino, (C
1-4
)alyloxyamino, (C
1-4
)haloalkoxyamino, (C
1-4
)alkylcarbonyl, (C
1-4
)haloalkylcarbonyl, (C
1-4
)haloalkoxycarbonyl, (C
1-4
)alkylcabonylamino, (C
1-4
)haloalkylcarbonylamino, (C
1-4
)alkoxycarbonylamino, (C
1-4
)haloalkoxycarbonylamino, (C
1-6
)alkoxyalkyl, (C
1-6
)haloalkoxyalkyl, (C
1-6
)alkylthio, (C
1-6
)haloalkylthio, (C
2-6
)alkenyl, (C
2-6
)haloalkenyl, (C
2-6
)alkynyl or (C
2-6
)haloalkynyl;
R
9
and R
10
are independent of each other and may be selected from the group consisting of hydrogen, halogen, cyano, (C
1-4
)alkyl, (C
1-4
)haloalkyl, (C
1-4
)alkoxy, (C
1-4
)haloalkoxy, (C
2-6
)alkenyl, (C
2-6
)haloalkenyl.
R
11
and R
12
are independent of each other and may be selected from the group consisting of hydrogen, halogen, (C
1-3
)alkyl, (C
1-3
)haloalkyl, hydroxy, (C
1-3
)alkoxy, (C
1-3
)haloalkoxy, cyano, nitro, amino or (C
1-6
)alkylamino;
When R
11
and R
12
are taken together with the atoms to which they are attached, they represent a three to seven membered substituted or unsubstituted ring optionally containing oxygen, S(O)
n**
or nitrogen with following optional substitutions, one to three halogen, cyano, nitro, hydroxy, amino, carbonyl, (C
1-6
)alkyl, (C
1-6
)haloalkyl, (C
1-6
)alkylcarbonyl, (C
1-6
)alkylcarbonyloxy, (C
1-6
)haloalkylcarbonyl, (C
1-6
)haloalkylcarbonyloxy, (C
1-6
)alkoxy, (C
1-6
)alkoxycarbonyl, aminocarbonyl, (C
1-6
)alkylaminocarbonyl, (C
1-6
)haloalkoxy, (C
1-6
)haloalkoxycarbonyl, (C
1-6
)alkylsulfonyl, (C
1-6
)haloalkylsulfonyl, aryl, heteroaryl or (C
3-7
)cycloalkyl;
R
13
may be selected from the group consisting of hydrogen, halogen, cyano, (C
1-4
)alkyl, (C
1-4
)alk

Affiliated with

Also associated with

Rating

Benzohydrazide derivatives as herbicides and desiccant... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Benzohydrazide derivatives as herbicides and desiccant..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Benzohydrazide derivatives as herbicides and desiccant... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3360327