# US 5,705,454 A · Turfgrass management method

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- Number: US 5,705,454 A
- Document ID: US5705454A
- Status: Granted
- Kind: A
- Application number: 08/451,334
- Filed: 1995-05-26
- Granted: 1998-01-06
- Earliest claimed: 1985-02-04
- Assignees: American Cyanamid Company
- Inventors: Prithvi Raj Bhalla; Robert Michael Herrick; Donald Wakeford Gates
- Web page: https://patentgrep.com/patent/US5705454A

## Abstract

The present invention relates to chemical compositions comprising imidazolinone compounds that are suitable for use in turfgrass management. The invention also provides methods for altering the growth and reducing mowing frequency, suppressing seed head formation and controlling undesirable vegetation in turfgrass.

## Claims

### Claim 1

A method for retarding growth and suppressing seed heading in turfgrasses, which comprises applying to the foliage or soil surrounding said turfgrasses a composition comprising a solid or liquid diluent and an imidazolinone compound, in an mount sufficient to retard growth and suppress seedheading in turfgrass, having the structure: ##STR7## wherein X is N or CR.sub.3 ; R is hydrogen; C.sub.1 -C.sub.12 alkyl optionally substituted with one of the following groups: C.sub.1 -C.sub.4 alkoxy, halogen, hydroxyl, C.sub.3 -C.sub.6 cycloalkyl, benzyloxy, furyl, phenyl, halophenyl, C.sub.1 -C.sub.4 alkylphenyl, C.sub.1 -C.sub.4 alkoxyphenyl, nitrophenyl, carboxyl, C.sub.1 -C.sub.3 alkoxycarbonyl, cyano or tri(C.sub.1 -C.sub.3) alkylammonium;
C.sub.3 -C.sub.12 alkenyl optionally substituted with one of the following groups: C.sub.1 -C.sub.3 alkoxyl, phenyl, halogen or C.sub.1 -C.sub.3 alkoxycarbonyl, or with two C.sub.1 -C.sub.4 alkoxy groups or two halogen atoms;
C.sub.3 -C.sub.6 cycloalkyl optionally substituted with one or two C.sub.1 -C.sub.3 alkyl groups;
C.sub.3 -C.sub.10 alkynyl; or
a cation;
R.sub.1 and R.sub.2 are each hydrogen, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.4 hydroxyalkyl, C.sub.1 -C.sub.6 alkoxy, C.sub.1 -C.sub.4 alkythio, phenoxy, C.sub.1 -C.sub.4 haloalkyl, OCF.sub.2 CHF.sub.2, OCF.sub.3, OCHF.sub.2, nitro, cyano, C.sub.1 -C.sub.4 alkylsulfonyl, NR.sub.4 R.sub.5, C.sub.3 -C.sub.8 straight or branched alkenyloxy optionally substituted with one to three halogens, C.sub.3 -C.sub.8 straight or branched alkynyloxy optionally substituted with one to three halogens, or phenyl optionally substituted with one C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen;
R.sub.3 is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkythio, C.sub.1 -C.sub.4 alkoxyl, CF.sub.3, NO.sub.2, OCF.sub.3, OCHF.sub.2 or OCF.sub.2 CHF.sub.2 ;
R.sub.4 is hydrogen or C.sub.1 -C.sub.4 alkyl;
R.sub.5 is C.sub.1 -C.sub.4 alkyl;
and, when taken together, R.sub.1 and R.sub.2, in the case of X.dbd.CR.sub.3, may form a ring in which R.sub.1 R.sub.2 is represented by
(1) the structure: --(CH.sub.2).sub.n --, where n is an integer of 2, 3 or 4; or
(2) by the structure: ##STR8## where L, M, R.sub.6 and R.sub.7 each represent hydrogen; halogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.3 alkoxy; and, in the case of X.dbd.N, R.sub.1 R.sub.2
(1) may form a ting in which R.sub.1 R.sub.2 is represented by the structure --(CH.sub.2).sub.n --, where n is an integer of 3 or 4; or
(2) when taken together with the carbons to which they are attached may form a 5-membered ring containing one O or S; or
(3) may form a ring represented by the structure; ##STR9## where L, M, R.sub.6 and R.sub.7 each represent hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1-C.sub.4 alkoxy, C.sub.1 -C.sub.4 alkylthio, C.sub.1 -C.sub.4 alkylsulfonyl, C.sub.1 -C.sub.4 haloalkyl, NO.sub.2, CN, phenyl, phenoxy, amino, C.sub.1 -C.sub.4 alkylamino, diloweralkylamino, chlorophenyl, methylphenyl, phenoxy substituted with one Cl, CF.sub.3, NO.sub.2 or CH.sub.3 group, OCF.sub.2 CHF.sub.2, OCF.sub.3, OCHF.sub.2, C.sub.3 -C.sub.8 straight or branched alkenyloxy optionally substituted with one to three halogens, or C.sub.3 -C.sub.8 straight or branched alkynyloxy optionally substituted with one to three halogens;
or an N-oxide thereof when X.dbd.N provided that R cannot be alkenyl or alkynyl and R.sub.1 and R.sub.2
cannot be NR.sub.4 R.sub.5 or alkylthio; an optical isomer thereof or a mixture of region isomers thereof, alone and in combination with N-›2,4-dimethyl-5››(trifluoromethyl) sulfonyl!amino!phenyl!-acetamide.

### Claim 2 (depends on 1)

The method of claim 1 wherein X is N; R is H or a cation; and R.sub.1 and R.sub.2 are either separately or the same, H or C.sub.1 -C.sub.4 alkyl.

### Claim 3

A method for retarding growth and suppressing seed heading in a turfgrass, the method comprising: applying to the foliage or soil surrounding the turfgrass, a sufficient quantity of a composition having an mount of 2-(4'-isopropyl-4-methyl-5-oxo -2-imidazolin-2-yl)-5-methyl-nicotinic acid or salt thereof.

### Claim 4 (depends on 3)

The method of claim 3 wherein the composition has an active ingredient consisting essentially of 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-5-methyl-nicotinic acid or salt thereof and is applied at a rate of from about 25 to 200 grams per hectare.

### Claim 5

A method for retarding growth and suppressing seedheading in turfgrasses, which comprises applying to the foliage or soft surrounding the turfgrasses, a sufficient quantity of a composition having a synergistic effective amount of at least one compound comprising the structure: ##STR10## wherein X is N or CH; R is H, C.sub.1 -C.sub.4 alkyl, or a cation; R.sub.1 and R.sub.2 are each H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkyloxy, C.sub.3 -C.sub.6 alkenyloxy, or R.sub.1 and R.sub.2 taken together with the carbons to which they are attached may form a 6 membered ring; and the optical isomer thereof.

### Claim 6 (depends on 2)

The method of claim 2, comprising applying to turfgrasses 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl) 3-quinolinecatboxylic acid.

### Claim 7 (depends on 2)

The method of claim 2, comprising applying to turfgrasses 5-ethyl-2-(4-isopropyl-4-methy-5-oxo-2-imidazolin-2-yl )nitclinic acid.

### Claim 8 (depends on 2)

The method of claim 2, comprising applying to turfgrasses either or both methyl 6-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) m-toluate and methyl 2-(5-isopropyl-5-methyl-4-oxo-2-imidazolin-2-yl) p-toluate.

### Claim 9 (depends on 2)

The method of claim 2, comprising applying to turfgrasses methyl 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-6-methoxy nicotinate.

### Claim 10 (depends on 2)

The method of claim 2, comprising applying to turfgrasses 5-(allyl-oxy)-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinic acid.

### Claim 11 (depends on 2)

The method of claim 2, comprising applying to turfgrasses 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl )nitclinic acid or salt thereof.