Benzoic acid compounds and their use as herbicides

Details Benzoic acid compounds and their use as herbicides Benzoic acid compounds and their use as herbicides

1999-05-10

2001-07-24

Higel, Floyd D. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acids and salts thereof

C558S416000, C562S429000, C562S430000, C504S310000, C504S315000, C504S318000

Reexamination Certificate

active

06265606

ABSTRACT:

BACKGROUND OF THE INVENTION
This invention relates to novel 1-alkyl-4-benzoyl-5-hydroxypyrazole compounds and to the use of these compounds as herbicides.
A number of 1-alkyl-4-benzoyl-5-hydroxypyrazole compounds and their herbicidal utility have been disclosed in the art, for example, in U.S. Pat. Nos. 4,230,481, 4,063,925, 4,643,757, 4,744,815, 4,885,022, 4,948,887, RE34,779, RE34,408, RE34,423, and PCT Application WO 96/26206, published Aug. 29, 1996. The compounds disclosed in these documents possess a variety of substituents on the benzoyl moiety. While herbicidal activity is present in these prior art compounds, it would be highly desirable to discover related compounds that are more active as herbicides, control a broader spectrum of undesirable vegetation, are more selective to major crops, have a more desirable environmental profile, or have a more desirable toxicological profile.
SUMMARY OF THE INVENTION
It has now been found that 1-(aliphatic)hydro-carbyl-4-benzoyl-5-hydroxypyrazole compounds possessing an unsubstituted or substituted phenyl substituent in the 3-position, an alkylsulfonyl substituent in the 4-position, and one of a few selected substituents in the 2-position of the benzoyl moiety are highly active as herbicides, control a broad spectrum of undesirable vegetation, are selective to major crops, have desirable environmental profiles, and have desirable toxicological profiles.
The invention includes benzoylpyrazole compounds of Formula I:
wherein
X represents F, Cl, Br, CH
3
, C
2
H
5
, or OCH
3
;
Y represents CH
3
, C
2
H
5
, CH(CH
3
)
2
, or cyclo-C
3
H
5
;
Z represents H or benzyl (optionally possessing up to three ring substituents selected from F, Cl, Br, CN, CF
3
, NO
2
, CH
3
, C
2
H
5
, OCH
3
, and OC
2
H
5
);
W represents F, Cl, Br, CN, NO
2
, OH, R″, OR″, OCOR″, OCONHR″, OSO
2
R″, SR″, SOR″, SO
2
R″, SO
2
OR″, SO
2
NHR″, SO
2
NR″
2
, NHR″, NR″
2
, CO
2
R″, CONHR″, or CONR″
2
; or any two adjacent W together represent the fragment —O(CH
2
)m
O
— optionally mono to completely substituted with fluorine or methyl;
n represents 0, 1, 2, or 3;
m represents 1, 2, or 3;
R represents C
1
-C
4
alkyl, C
3
-C
4
alkenyl, or C
3
-C
4
alkynyl;
R′ represents H, CH
2
OCH
3
, or C
1
-C
3
alkyl;
R″ represents C
1
-C
4
alkyl, C
2
-C
4
alkenyl, or C
2
-C
4
alkynyl each optionally mono to completely substituted with fluorine or mono substituted with Cl, Br, O(C
1
-C
2
alkyl), or S(C
1
-C
2
alkyl); and when Z represents H, the agriculturally acceptable salts and esters thereof.
The invention includes herbicidal compositions containing the benzoylpyrazole compounds of Formula I in combination with an agriculturally acceptable adjuvant or carrier as well as a method of use of the compounds to kill or control undesirable vegetation by application of an herbicidal amount of the compound to the vegetation or to the locus of the vegetation. The use of the compounds to kill or control weeds in rice, wheat, barley, and turf is a preferred utility and postemergence application of the compounds to the undesirable vegetation is a preferred method of application.
The invention further includes substituted benzoic acid and other intermediates that are useful in preparing the herbicidal benzoylpyrazole compounds of Formula I.
DETAILED DESCRIPTION OF THE INVENTION
The herbicidal compounds of the present invention are benzoylpyrazole compounds of Formula I:
These compounds are characterized by possessing a
pyrazole heterocycle moiety substituted in the 1-position with an aliphatic hydrocarbyl group and in the 5-position with an hydroxy or benzyloxy group as well as in the 4-position with a benzoyl moiety. Substitution in the 3-position of the pyrazole ring with a lower alkyl moiety is optional. The benzoyl moiety is characterized by being substituted in the 3-position with a phenyl or substituted phenyl group, in the 4-position with a lower alkylsulfonyl group, and in the 2-position with a halo, lower alkyl or lower alkoxy group. The compounds of Formula I, further, include the salt and ester compounds obtained by derivatization of the 5-position hydroxy substituent of the pyrazole moiety.
The compounds of Formula I are sometimes named as (2,3,4-trisubstituted phenyl)(1-alkyl-5-hydroxy-1H-pyrazol-4-yl)methanone compounds, but are more often referred to in the art as 1-alkyl-4-(2,3,4-trisubstituted benzoyl)-5-hydroxypyrazole compounds. The latter terminology is used herein. The compounds of Formula I wherein Z represents hydrogen are sometimes referred to as 1-alkyl-4-(2,3,4-trisubstituted benzoyl)-2-pyrazolin-5-one compounds; that is, as the keto tautomers of the formula illustrated.
The bond between the optionally substituted 3-phenyl substituent and the benzoyl moiety of the compounds of Formula I is restricted in its rotation due to steric factors and, as a result, in cases wherein the phenyl ring is asymmetrically substituted, the compounds often exist in two optical isomer forms. The definition of the compounds of the invention includes each of these isomers singly and when combined in any proportion.
The most distinguishing feature of the compounds of Formula I is the presence of the phenyl or substituted phenyl substituent in the 3-position of the benzoyl moiety. The presence of such a substituent has been found to impart unexpectedly beneficial herbicidal, environmental, and toxicological properties to benzoyl-pyrazole compounds.
Suitable substituents on the phenyl ring (W) include halo; cyano; nitro; hydroxy; optionally substituted lower alkyl, alkenyl, and alkynyl; optionally substituted lower alkoxy, alkenyloxy, and alkynyloxy; optionally substituted lower alkylcarbonyloxy, alkenylcarbonyloxy, and alkynylcarbonyloxy; optionally substituted lower alkylaminocarbonyloxy, alkenylaminocarbonyloxy, and alkynylaminocarbonyloxy; optionally substituted lower alkylsulfonyloxy, alkenylsulfonyloxy, and alkynylsulfonyloxy; optionally substituted lower alkylthio, alkenylthio, and alkynylthio; optionally substituted lower alkylsulfinyl, alkenylsulfinyl, and alkynylsulfinyl; optionally substituted lower alkylsulfonyl, alkenylsulfonyl, and alkynylsulfonyl; optionally substituted lower alkoxysulfonyl, alkenyloxysulfonyl, and alkynyloxysulfonyl; optionally substituted lower alkylaminosulfonyl, alkenylaminosulfonyl, and alkynylaminosulfonyl; optionally substituted di(lower alkyl)aminosulfonyl, alkenylaminosulfonyl, and alkynylaminosulfonyl; optionally substituted lower alkylamino, alkenylamino, and alkynylamino; optionally substituted di(lower alkyl)amino, alkenylamino, and alkynylamino; optionally substituted lower alkoxycarbonyl, alkenyloxycarbonyl, and alkynyloxycarbonyl; optionally substituted lower alkylaminocarbonyl, alkenylaminocarbonyl, and alkynylaminocarbonyl; and optionally substituted di(lower alkyl)aminocarbonyl, alkenylaminocarbonyl, and alkynylaminocarbonyl. There can be zero, one, or multiple such substituents present. In addition, any two adjacent W together can represent an optionally substituted ((poly) -methylene)dioxy fragment. The following W substituents are explicitly included in the compounds of Formula I: F, Cl, Br, CN, NO
2
, OH, R″, OR″, OCOR″, OCONHR″, OSO
2
R″, SR″, SOR″, SO
2
R″, SO
2
OR″, SO
2
NHR″, SO
2
NR″
2
, NHR″, NR″
2
, CO
2
R″, CONHR″, and CONR″
2
(wherein R″ represents C
1
-C
4
alkyl, C
2
-C
4
alkenyl, or C
2
-C
4
alkynyl each optionally mono to completely substituted with fluorine or mono substituted with Cl, Br, O(C
1
-C
2
alkyl), or S(C
1
-C
2
alkyl)) and, for any two adjacent W taken together, the fragment —O(CH
2
)
m
O— (wherein m represents 1, 2, or 3) optionally mono to completely substituted with fluorine or methyl. Compounds wherein W represents fluoro, chloro, methyl, ethyl, hydroxy, methoxy, ethoxy, 1-methylethoxy, 2-propenyloxy (allyloxy), or methoxy-methoxy are sometimes preferred and compounds wherein W represents

Affiliated with

Also associated with

Rating

Benzoic acid compounds and their use as herbicides does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Benzoic acid compounds and their use as herbicides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Benzoic acid compounds and their use as herbicides will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2492683