Method for improving the selectivity of 1,3-cyclohexanedione...

Details Method for improving the selectivity of 1,3-cyclohexanedione... Method for improving the selectivity of 1,3-cyclohexanedione...

1999-05-28

2003-04-01

Qazi, Sabiha (Department: 1616)

Plant protecting and regulating compositions

Plant growth regulating compositions

C504S191000, C504S190000, C504S348000, C504S349000, C504S350000, C544S064000, C544S225000, C562S430000, C564S085000, C564S086000, C564S092000, C564S097000, C568S329000, C558S412000, C558S396000, C558S397000, C560S012000, C560S021000

Reexamination Certificate

active

06541422

ABSTRACT:

FIELD OF THE INVENTION
The present invention is directed to the use of metal chelates as a delivery system to improve the selectivity of 2-(substituted benzoyl)-1,3-cyclohexanedione compounds as post-emergence herbicides in crops.
BACKGROUND OF THE INVENTION
The protection of crops from weeds and other undesirable vegetation which inhibit crop growth is a constantly recurring problem in agriculture. To help combat this problem researchers in the field of synthetic chemistry have produced an extensive variety of chemicals and chemical formulations effective in the control of such unwanted growth. Chemical herbicides of many types have been disclosed in the literature and a large number are in commercial use.
Unfortunately, many of such herbicides exhibit phytotoxicity to the desired crop as well as to the weeds sought to be controlled. Thus, there is a long-standing need for selective herbicides which will control frequently occurring weeds but which will not adversely affect the crop plants when applied at herbicidally effective levels.
U.S. Pat. Nos. 4,780,127, 4,938,796, 5,006,158 and 5,089,046 disclose 2-(substituted benzoyl)-1,3-cyclohexanedione compounds having the general structure:
wherein X, Q and Z have the meanings set forth hereinafter. These dione compounds have proved to be effective pre-emergent and postemergent herbicides against a wide variety of grasses, broadleaf weeds and sedges. Moreover, PCT Application No. 97/27748 discloses that metal chelates of 2-(substituted benzoyl)-1,3-cyclohexanedione compounds have proved to be chemically stable for long periods of time under normal as well as extreme temperature conditions.
The parent cyclohexanedione exhibits a substantial phytotoxic effect. In contrast, it has now been discovered that metal chelates of 2-(substituted benzoyl)-1,3-cyclohexanedione compounds will effectively control a broad range of weeds without exhibiting any substantial phytotoxic effect on the crop itself.
SUMMARY OF THE INVENTION
The present invention is directed to methods of selectively controlling weeds and other undesirable vegetation in a given crop such as wheat. In one embodiment of this invention, the method comprises the postemergent application of an herbicidally effective amount of a metal chelate of a 2-(substituted benzoyl)-1,3-cyclohexanedione to the locus of such weeds and other vegetation. In another embodiment of this invention, the method comprises the postemergent application of an herbicidally effective amount of a metal chelate of a 2-(substituted benzoyl)-1,3-cyclohexanedione to the locus of such weeds and other vegetation, said metal chelate having been formulated as a microcapsule.
As is employed herein, the term “herbicide” is used to denote a compound which controls or modifies the growth of plants. The term “herbicidally effective amount” is used to indicate the quantity of such compound which is capable of producing a controlling or modifying effect. Controlling or modifying effects include all deviations from natural development, for example: killing, retardation, leaf burn, albinism, dwarfing, and the like. The term “plants” refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits.
DETAILED DESCRIPTION OF THE INVENTION
The present invention relates to the use of metal chelates of herbicidal dione compounds to selectively control weeds and other undesirable vegetation in a given crop such as wheat. These herbicidal dione compounds have the general formula (I):
wherein X represents a halogen atom; a straight- or branched-chain alkyl or alkoxy group containing up to six carbon atoms which is optionally substituted by one or more groups —OR
1
or one or more halogen atoms; or a group selected from nitro, cyano, —CO
2
R
2
—S(O)
m
R
1
, —O(CH
2
)
m
OR
1
, —COR
2
, —OSO
2
R
4
, —NR
2
R
3
, —SO
2
NR
2
R
3
, —CONR
2
R
3
and —CSNR
2
R
3
;
R
1
represents a straight- or branched-chain alkyl group containing up to six carbon atoms which is optionally substituted by one or more halogen atoms;
R
2
and R
3
each independently represents a hydrogen atom; or a straight- or branched-chain alkyl group containing up to six carbon atoms which is optionally substituted by one or more halogen atoms;
R
4
represents a straight- or branched-chain alkyl, alkenyl or alkynyl group containing up to six carbon atoms optionally substituted by one or more halogen atoms; or a cycloalkyl group containing from three to six carbon atoms;
each Z independently represents halo, nitro, cyano, S(O)
m
R
5
, OS(O)
m
R
5
, (C
1
-C
6
)alkyl, (C
1
-C
6
)alkoxy, (C
1
-C
6
)haloalkyl, (C
1
-C
6
)haloalkoxy, carboxy, (C
1
-C
6
)alkylcarbonyloxy, (C
1
-C
6
)alkoxycarbonyl, (C
1
-C
6
)alkylcarbonyl, amino, (C
1
-C
6
)alkylamino, (C
1
-C
6
)dialkylamino having independently the stated number of carbon atoms in each alkyl group, (C
1
-C
6
)alkylcarbonylamino, (C
1
-C
6
)alkoxycarbonylamino, (C
1
-C
6
)alkylaminocarbonylamino, (C
1
-C
6
)dialkylaminocarbonylamino having independently the stated number of carbon atoms in each alkyl group, (C
1
-C
6
)alkoxycarbonyloxy, (C
1
-C
6
)alkylaminocarbonyloxy, (C
1
-C
6
)dialkylaminocarbonyloxy, phenylcarbonyl, substituted phenylcarbonyl, phenylcarbonyloxy, substituted phenylcarbonyloxy, phenylcarbonylamino, substituted phenylcarbonylamino, phenoxy or substituted phenoxy;
R
5
represents cyano; —COR
6
; —CO
2
R
6
; or —S(O)
m
R
7
;
R
6
represents hydrogen or straight- or branched-chain alkyl group containing up to six carbon atoms;
R
7
represents (C
1
-C
6
)alkyl, (C
1
-C
6
)haloalkyl, (C
1
-C
6
)cyanoalkyl (C
3
-C
8
)cycloalkyl optionally substituted with halogen, cyano or (C
1
-C
4
)alkyl; or phenyl optionally substituted with one to three of the same or different halogen, nitro, cyano, (C
1
-C
4
)haloalkyl, (C
1
-C
4
alkyl, (C
1
-C
4
)alkoxy or —S(O)
m
R
8
;
R
8
represents (C
1
-C
4
)alkyl, (C
1
-C
4
)alkyl substituted with halogen or cyano, phenyl or benzyl;
each Q independently represents C
1
-C
4
alkyl or —CO
2
R
9
wherein R
9
is C
1
-C
4
alkyl;
m is zero, one or two;
n is zero or an integer from one to four;
r is one, two or three; and
z is 0 or an integer from 1 to 6.
As used herein, the terms “halogen” and “halo” include fluorine, chlorine, bromine and iodine atoms. In polyhalogenated groups, the halogens may be the same or different. The term “substituted” in terms of “substituted phenylcarbonyl,” “substituted phenylcarbonyloxy,” “substituted phenylcarbonylamino” and “substituted phenoxy” means having one to five substituents, which may be the same or different, selected from the following: halo, nitro, cyano, S(O)
m
R
2
, (C
1
-C
6
)alkyl, (C
1
-C
6
)alkoxy, (C
1
-C
6
)haloalkyl, (C
1
-C
6
)haloalkoxy, carboxy, (C
1
-C
6
)alkylcarbonyloxy, (C
1
-C
6
)alkylcarbonyl, (C
1
-C
6
)alkoxycarbonyl, (C
1
-C
6
)alkylcarbonylamino, amino, (C
1
-C
6
)alkylamino and (C
1
-C
6
)dialkylamino having independently the stated number of carbon atoms in each group.
The 2-(substituted benzoyl)-1,3-cyclohexanedione compounds of formula I are described, inter alia, in U.S. Pat. Nos. 4,780,127, 4,938,796, 5,006,158 and 5,089,046, the disclosures of which are incorporated herein by reference. Herbicidal 2-(substituted benzoyl)-1,3-cyclohexanedione compounds for use in this invention may be prepared by the methods described in the aforementioned patent publications, or by the application and adaptation of known methods used or described in the chemical literature.
2-(substituted benzoyl)-1,3-cyclohexanedione compounds especially useful in the present invention include those in which z is zero; X is chloro, bromo, nitro, cyano, C
1
-C
4
alkyl, —CF
3
, —S(O)
m
R
1
or —OR
1
; n is one or two; and each Z is independently chloro, bromo, nitro, cyano, C
1
-C
4
alkyl, —CF
3
, —OR
1
, —OS(O)
m
R
5
or —S(O)
m
R
5
. Examples of preferred cyclohexanedione compounds are 2-(2′-nitro-4′-methylsulfonylbenzoyl)-1,3-cyclohexanedione, 2-(2′-nitro-4′-methylsulfonyloxybenzoyl)-1,3-cyclohexanedione and 2-(2′-chloro-4′-methylsulfonylben

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