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United States Patent |
5,705,454
|
Bhalla
,   et al.
|
January 6, 1998
|
Turfgrass management method
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.
Inventors:
|
Bhalla; Prithvi Raj (East Windsor, NJ);
Herrick; Robert Michael (Mercerville, NJ);
Gates; Donald Wakeford (Yardley, PA)
|
Assignee:
|
American Cyanamid Company (Madison, NJ)
|
Appl. No.:
|
451334 |
Filed:
|
May 26, 1995 |
Intern'l Class: |
A01N 043/40; A01N 043/42; A01N 043/50 |
Field of Search: |
504/253,130,245,139
|
References Cited
U.S. Patent Documents
4608079 | Aug., 1986 | Los | 504/245.
|
4957536 | Sep., 1990 | Orwick et al. | 504/253.
|
Primary Examiner: Clardy; S. Mark
Attorney, Agent or Firm: Costello, Jr.; Charles F.
Parent Case Text
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is a division of Ser. No. 235,937, filed May 2, 1994, U.S.
Pat. No. 5,591,693, which is a division of Ser. No. 833,221, filed Feb.
10, 1992, U.S. Pat. No. 5,340,791, which is a division of Ser. No.
411,444, filed Sep. 22, 1989, U.S. Pat. No. 5,116,403, which is a
continuation of Ser. No. 818,591, filed Jan. 15, 1986, abandoned, which is
a continuation-in-part of Ser. No. 698,191, filed Feb. 4, 1985, abandoned,
Claims
What is claimed is:
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.
2. 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.
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.
4. 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.
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.
6. The method of claim 2, comprising applying to turfgrasses
2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl) 3-quinolinecatboxylic
acid.
7. The method of claim 2, comprising applying to turfgrasses
5-ethyl-2-(4-isopropyl-4-methy-5-oxo-2-imidazolin-2-yl )nitclinic acid.
8. 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.
9. The method of claim 2, comprising applying to turfgrasses methyl
2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-6-methoxy nicotinate.
10. 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.
11. 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.
Description
BACKGROUND OF THE INVENTION
Maintenance of lawns, sport fields, playgrounds, parks, golf courses,
roadsides and cemeteries represents a growing area of interest. The annual
investment in time, labor, chemical treatments, fertilization and
equipment for the maintenance of turfgrasses was shown in 1965 to be over
4.2 billion dollars. Additionally, it was shown in 1965 that about 50% of
total annual lawn care expenditures was almost equally divided between
labor (23.5%) and equipment (26.5%).
Since a significant portion of the investment in turfgrass management is
devoted to labor costs, and the cost associated with purchasing,
maintaining and operating maintenance equipment, it would be highly
desirable to be able to supplement turfgrass management practices with
chemical treatments which reduce the maintenance requirements of the
grass. The development and use of chemical treatments which retard the
growth of grass, and hence the frequency of mowing, reduce and inhibit
heading, control undesirable weeds and are not injurious to the grass and
do not alter its appearance could significantly reduce the overall
maintenance costs for turfgrass management.
Advances in the development of chemical herbicide treatments for the
control of weeds have resulted in a wide variety of chemicals which are
suitable for weed control in turf. Advances in the field of plant growth
regulators have resulted in the discovery that certain of these chemicals
are suitable for use on turfgrasses. For example, mefluidide,
(Embark.RTM.)N-›2,4-dimethyl-5-››(trifluoromethyl)sulfonyl!amino!phenyl!ac
etamide, a plant growth regulator produced by 3M Company, is registered for
use as a growth and development retardant on turf and ornamental species.
More recently, work in the area of turfgrass treatment has resulted in the
evaluation of mixtures of chemicals in an attempt to enhance effects,
improve safety margins, obtain several effects at the same time, reduce
rates of application or alter the effect obtained on one specific species.
Certain chemical combinations useful as turfgrass treatments were reported
by K. J. Tautvydas in the Proceedings of Tenth Annual Meeting of the Plant
Growth Regulator Society, 1983. This article discloses synergistic growth
retardation of Kentucky bluegrass and johnsongrass with certain mixtures
of mefluidide and chlorsulfuron,
2-chloro-N-›(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl!benzenesu
lfonamide, and a similar effect on bluegrass, johnsongrass and bermudagrass
with certain mixtures of mefluidide and methyl
2-››››(4,6-dimethyl-2-pyrimidinyl)amino!carbonyl!amino!sulfonyl!benzoate.
While it is clear that a great deal of research and progress is being made
in developing chemical compositions to aid in total turf management
programs, it is also becoming clear that, due to variations in climatic
conditions and differences in preferred grass varieties within these
different growing regions, different treatments will probably be required
on a region-to-region and species-to-species basis.
SUMMARY OF THE INVENTION
It is an object of this invention to provide chemical compositions
containing certain imidazolinone compounds of the formula (I)
##STR1##
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, hydroxy, 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 alkoxy, 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
alkylthio, 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
alkylthio, C.sub.1 -C.sub.4 alkoxy, 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:
##STR2##
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 and R.sub.2
(1) may form a ring 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:
##STR3##
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; and the
N-oxides 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,
and the optical isomers thereof and mixtures of region isomers thereof,
alone and in combination with
2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinic acid or salts
thereof, maleic hydrazide,
N-›2,4-dimethyl-5-››(trifluoromethyl)sulfonyl!amino!phenyl!acetamide,
2-chloro-N-›(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl!benzenesu
lfonamide or methyl
2-››››(4,6-dimethyl-2-pyrimidinyl)amino!carbonyl!amino!sulfonyl!benzoate
and mixtures thereof, which provide compositions that reduce growth in a
variety of grass species, without being injurious, inhibit seed heading,
and control certain weeds, and further that the desired effect or group of
effects for a given variety of grass under specific growing conditions may
be obtained by altering the combination and rate of each component.
The imidazolinone compounds suitable for use in turf described in U.S. Pat.
No. 4,188,487, pending applications for U.S. Letters patent Ser. Nos.
382,041, 616,747, 631,283, 611,191 and pending application for U.S.
Letters patent, Ser. No. 635,787 as herbicides and plant growth regulators
for increasing crop yields. Surprisingly, it has been found that compounds
represented by Formula (I) are efficacious for retarding the growth of
turf and suppressing seed heads. Additionally, it has been found that the
longevity of the effect and the extent of the effect may be increased
significantly by applying formula (I) compounds in combination with one or
more of 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinic acid or
salts thereof, maleic hydrazide,
N-›2,4-dimethyl-5-››(trifluoromethyl)sulfonyl!amino!-phenyl!acetamide,
2-chloro-N-›(4-methoxy-6-methyl-1,3,5-triazin-2-yl
)aminocarbonyl!benzenesulfonamide and methyl
2-››››(4,6-dimethyl-2-pyrimidinyl)amino!carbonyl!amino!sulfonyl!benzoate.
Further, it has been found that by altering the rates of each of the
components, the desirable effects of growth retardation, head inhibition
and control of certain weeds may be obtained in a variety of grass species
without being injurious to the grass. Preferred compounds suitable for use
in turfgrass management compositions of the invention are illustrated in
Table I below.
TABLE I
______________________________________
Component
______________________________________
##STR4##
(a) X R R.sub.1 R.sub.2
N H H OCH.sub.3
(b) N H CHCHCHCH
CH CH.sub.3
CH.sub.3 H
(c) +
CH CH.sub.3
H CH.sub.3
(d) N H OCH.sub.2 CHCH.sub.2
H
(e) N H CH.sub.2CH.sub.2O
(f) N C.sub.2 H.sub.5
OCH.sub.3 H
(g) N H
##STR5##
(h) N H C.sub.2 H.sub.5
H
(i) N H
phenyl H
(j) N H
##STR6##
(k) N CH.sub.3
H OCH.sub.3
2 2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-
2-yl)nicotinic acid
3 maleic hydrazide
4 N-›'2,4-dimethyl-5-››(trifluoromethyl)-
sulfonyl!amino!phenyl!acetamide
5 chlorsulfuron, 2-chloro-N-›(4-methoxy-6-
methyl-1,3,5-triazin-2-yl)aminocarbonyl!-
benzenesulfonamide
6 methyl 2-››››(4,6-dimethyl-2-pyrimidinyl)-
amino!carbonyl!amino!sulfonyl!benzoate
______________________________________
As indicated above, the composition of the invention may be altered to
obtain different effects or the same set of effects on a different grass
species without injuring the grass. The preferred ranges of rates for each
of the components are illustrated in Table II below,
TABLE II
______________________________________
Preferred rate ranges for turf management
compositions of the invention
Composition Rate grams/hectare
______________________________________
1 5 to 500
2 0.1 to 200
1 + 2 5 to 250 + 0.25 to 2
1 + 3 5 to 250 + 20 to 5000
1 + 4 5 to 250 + 20 to 500
1 + 5 5 to 250 + 0.25 to 20
1 + 6 5 to 250 + 0.25 to 20
1 + 2 + 4 1 to 250 + 0.25 to 25 + 20 to 500
1 + 2 + 5 1 to 250 + 0.25 to 25 + 0.25 to 20
1 + 2 + 6 1 to 250 + 0.25 to 25 + 0.25 to 20
______________________________________
As discussed above, by adjusting the rates of each component the
compositions may be used on a variety of species as indicated in Table III
below.
TABLE III
__________________________________________________________________________
Adjusting Composition for different grass species.
Composition
Bermudagrass
Bluegrass
Fescue Rye
__________________________________________________________________________
1 5.0 to 500.0*
5.0 to 500.0
5.0 to 250.0
5.0 to 250.0
2 5.0 to 200.0
0.1 to 20.0
0.1 to 10.0
0.1 to 10.0
1 + 2 5.0 to 250.0 +
5.0 to 250.0 +
5.0 to 150.0 +
5.0 to 150.0 +
0.25 to 25.0
0.25 to 25.0
0.5 to 10.0
0.5 to 10.0
1 + 3 5.0 to 250.0 +
5.0 to 250.0 +
5.0 to 150.0 +
5.0 to 150.0 to
20.0 to 5000.0
20.0 to 5000.0
20.0 to 2500.0
20.0 to 2500.0
1 + 4 50.0 to 250.0 +
5.0 to 250.0 +
5.0 to 150.0 +
5.0 to 150.0 +
0.25 to 10.0*
6.25 to 10.0
0.25 to 5.0
0.25 to 5.0
1 + 5 5.0 to 250.0 +
5.0 to 250.0 +
5.0 to 150.0 +
5.0 to 150.0 +
0.25 to 10.0 *
0.25 to 10.0
0.25 to 5.0
0.25 to 5.0
1 + 6 5.0 to 250.0 +
5.0 to 250.0 +
5.0 to 150.0 +
5.0 to 150.0 +
0.25 to 10.0
0.25 to 10.0
0.25 to 5.0
0.25 to 5.0
1 + 2 + 4
1 to 250 +
1 to 250 +
1 to 250 +
1 to 250 +
0.25 to 25 +
0.25 to 25 +
0.25 to 10 +
0.25 to 10 +
20 to 500
20 to 500
20 to 500
20 to 250
1 + 2 + 5
1 to 250 +
1 to 250 +
1 to 250 +
1 to 250 +
0.25 to 25 +
0.25 to 25 +
025 to 25 +
0.25 to 25 +
0.25 to 10
0.25 to 10
0.25 to 5
0.25 to 5
1 + 2 + 6
1 to 250 +
1 to 250 +
1 to 250 +
1 to 250 +
0.25 to 25 +
0.25 to 25 +
0.25 to 25 +
0.25 to 25 +
0.25 to 10
0.25 to 10
25 + 0.25 to 5
0.25 to 5
__________________________________________________________________________
*Rate in grams/hectare
The compositions of the invention may conveniently be applied by
post-emergence treatment of the grass. They may be applied as a mixture of
all the ingredients or as sequential treatments. Since the formula (I)
compounds wherein R is hydrogen are acids, as is
2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinic acid and these
compounds may be applied as salts of the acid wherein R is a salt-forming
cation, the compositions may be applied as aqueous solutions and
suspensions containing non-ionic surfactants, and wetting agents which may
be prepared by introducing the components directly to water or by adding
formulations such as concentrates, suspensions, emulsions, wettable
powders, dispersible granules and the like to water prior to application.
Additionally granular compositions containing some of the compositions of
the invention may be applied to the turf followed by additional
post-emergence treatments as required. The invention is further
illustrated by the following non-limiting examples.
EXAMPLE 1
Evaluation of Compositions of the Invention for Retarding Growth
Seeds of the grass variety to be evaluated are tumbled for three minutes
with soil at a rate of 7 ounces of seed per 100 lbs of greenhouse soil
comprising a mixture by weight of sand (32%), silt (48%), and clay (20%).
A layer of this seed mixture one-half inch thick is placed in a four inch
diameter pot containing greenhouse soil and the plants are allowed to
germinate and grow for six to eight weeks prior to treatment. The plants
are clipped to a height of one-half inch and are sprayed with 100 mL of an
aqueous solution containing 0.25% by volume of a nonionic surfactant
mixture alkylarylpolyoxyethyleneglycols, free fatty acids and 2-propanol,
and the formula I (a)-(k) compounds and compounds 2, 3, 4, and 5 both
alone and in combinations at various spray rates. Each treatment is
applied to three pots and the pot randomly placed in a greenhouse where
the plants are cared for employing standard greenhouse procedures. Three
weeks after treatment the plants are clipped to a height of one-half inch
and the clippings are dried in an oven for 48 hours at 90.degree. C. and
the dry weight of clippings for each treatment is recorded. Examination of
Tables IV and V below which is a summary of results obtained on tall
fescue and bermudagrass, respectively, clearly demonstrates the
effectiveness of the formula I (a)-(k) compounds alone and additionally
demonstrates the improved effectiveness of these formula I (a)-(k)
compounds in combination with compounds 2, 3, 4 and 5 for retarding the
growth of turfgrasses as measured by dry clipping weight.
TABLE IV
______________________________________
Greenhouse evaluation of compositions of
the invention on tall fescue (Festuca arundinaceae)
Rate(s) % Decrease in
Treatments g or lb/A dry wt of clipping
______________________________________
1(h) 20.0 g 37
1(h) 40.0 g 51
2 1.0 g 2
2 2.0 g 3
1(j) 20.0 g 29
1(j) 40.0 g 32
1(j) 60.0 g 25
1(h) + 2 20.0 g + 1.0 g
52
1(h) + 2 20.0 g + 2.0 g
52
1(h) + 2 40.0 g + 1.0 g
37
1(h) + 2 40.0 g + 2.0 g
76
4 0.125 lb 6
4 0.375 lb 59
1(h) + 4 20.0 g + 0.125 lb
80
1(j) + 4 40.0 g + 0.125 lb
82
1(j) + 4 20.0 g + 0.125 lb
60
1(j) + 4 40.0 g + 0.125 lb
46
1(j) + 4 60.0 g + 0.125 lb
64
3 1.5 lb 2
3 3.0 lb 7
1(h) + 3 20.0 g + 1.5 lb
45
1(h) + 3 40.0 g + 1.5 lb
66
1(j) + 3 20.0 g + 1.5 lb
70
1(j) + 3 20.0 g + 1.5 lb
70
1(j) + 3 40.0 g + 1.5 lb
49
1(j) + 3 60.0 g + 1.5 lb
46
______________________________________
TABLE V
______________________________________
Greenhouse evaluation of compositions of the invention
on burmudagrass (Cynodon sp)
Rates % Decrease in
Treatments (grams/Acre)
dry wt of clippings
______________________________________
1(h) 5.0 15.3
1(h) 10.0 14.7
1(h) 15.0 12.7
1(h) 20.0 12.7
1(h) 40.0 57.3
1(h) 100.0 71.3
2 2.00 24.7 Increase
2 4.00 8.0 Increase
2 6.00 59.3
2 8.00 82.0
1(h) + 2 5.0 + 2.0 19.3
1(h) + 2 5.0 + 4.0 44.7
1(h) + 2 5.0 + 8.0 82.0
1(h) + 2 10.0 + 0.5
34.0
1(h) + 2 10.0 + 1.0
5.3
1(h) + 2 10.0 + 2.0
38.7
1(h) + 2 10.0 + 4.0
52.0
1(h) + 2 10.0 + 6.0
86.0
1(h) + 2 10.0 + 8.0
86.7
1(h) + 2 15.0 + 0.25
38.7
1(h) + 2 15.0 + 0.5
18.7
1(h) + 2 15.0 + 1.0
2.0 Increase
1(h) + 2 15.0 + 2.0
8.0 Increase
1(h) + 2 15.0 + 4.0
10.7
1(h) + 2 15.0 + 6.0
83.3
1(h) + 2 15.0 + 8.0
78.0
1(h) + 2 20.0 + 0.25
48.7
1(h) + 2 20.0 + 0.5
16.7
1(h) + 2 20.0 + 1.0
18.0
1(h) + 2 20.0 + 2.0
54.0
1(h) + 2 20.0 + 4.0
45.3
1(h) + 2 20.0 + 6.0
66.7
1(h) + 2 25.0 + 0.25
7.3
1(h) + 2 25.0 + 0.50
27.3
1(h) + 2 25.0 + 1.0
36.7
1(h) + 2 25.0 + 2.0
75.3
1(h) + 2 25.0 + 4.0
76.0
1(h) + 2 30.0 + 6.0
88.0
1(h) + 2 30.0 + 0.25
36.7
1(h) + 2 30.0 + 0.50
20.0
1(h) + 2 30.0 + 1.0
42.7
1(h) + 2 30.0 + 2.0
78.0
1(h) + 2 30.0 + 4.0
64.7
1(h) + 2 30.0 + 0.25
16.0
1(h) + 2 35.0 + 0.50
44.0
1(h) + 2 35.0 + 1.0
31.3
1(h) + 2 35.0 + 2.0
58.7
1(h) + 2 40.0 + 0.25
48.0
1(h) + 2 40.0 + 0.50
32.7
1(h) + 2 40.0 + 1.0
42.0
1(h) + 2 40.0 + 2.0
68.0
4 50.0 5.3
4 100.0 5.3 Increase
4 500.0 48.0
1(h) + 4 10.0 + 50.0
35.3
1(h) + 4 10.0 + 100.0
27.3
1(h) + 4 10.0 + 500.0
47.3
1(h) + 4 15.0 + 50.0
12.0
1(h) + 4 15.0 + 100.0
4.0
1(h) + 4 15.0 + 500.0
17.3
1(h) + 4 20.0 + 50.0
29.3
1(h) + 4 20.0 + 100.0
34.0
1(h) + 4 20.0 + 500.0
50.0
1(h) + 4 25.0 + 50.0
54.0
1(h) + 4 25.0 + 100.0
63.3
1(h) + 4 25.0 + 500.0
12.0
2 + 4 0.5 + 50.0
9.3 Increase
2 + 4 0.5 + 100.0
18.0 Increase
2 + 4 0.5 + 500.0
36.7
2 + 4 1.0 + 50.0
33.3
2 + 4 1.0 + 100.0
42.0
2 + 4 1.0 + 500.0
48.0
2 + 4 2.0 + 50.0
26.7
2 + 4 2.0 + 100.0
48.0
2 + 4 2.0 + 500.0
75.3
2 + 4 4.0 + 50.0
37.3
2 + 4 4.0 + 100.0
20.7
2 + 4 4.0 + 500.0
33.3
______________________________________
EXAMPLE 2
Evaluation of Compositions of the Invention on a Mix Stand of Grasses Which
Include Tall Fescue (Festuca arundinaecae); Kentucky bluegrass (Poa
pratensis), Annual Ryegrass (Lolium multiforum) and Perennial Ryegrass
(Lolium petrenne)
A six foot by twenty foot plot containing a mixed stand of grasses which
include tall rescue (Festuca arundinaecae); Kentucky bluegrass (Poa
pratensis), annual ryegrass (Lolium mulciforum) and perennial ryegrass
(Lolium perenne) is mowed at a height of one and one-half inches.
Twenty-four hours after mowing the plot is sprayed with an aqueous
solution containing 0.25% by volume of a nonionic surfactant mixture of
alkylarylpolyoxyechyleneglycols, free fatty acids, and 2-propanol and
formula I (a)-(k) compounds and compounds 2, 3, 4 and 5 alone and in
combinations at a variety of concentrations. Sufficient aqueous solution
is applied to provide the equivalent of 25 gal/acre of spray. Each
treatment is applied co three plots which are situated randomly within the
test area and the results for each treatment are obtained by averaging the
three replicates. The height of each treatment plot is measured at three
weeks and five weeks after treatment to determine the effectiveness of the
treatment in retarding growth. Examination of Table VI below which is a
summary of the results obtained on the mixed stand of grasses demonstrates
the effectiveness of the formula I (a)-(k) compounds alone and
additionally demonstrates the improved effectiveness of these formula I
(a)-(k) Compounds in combination with compounds 2, 3, 4 and 5 for
retarding the growth of turfgrasses.
TABLE VI
______________________________________
Evaluation of compositions of the invention on a
mix stand of grasses which include Tall Fescue
(Festuca arundinaecae), Kentucky Bluegrass
(Poa pratensis), Annual Ryegrass (Lolium multiforum)
and Perennial Ryegrass (Lolium perenne)
% Decrease
in height
Rate(s) 22-25 36-38
Treatments g or lb/A DAT* DAT*
______________________________________
1(h) 25.0 g 16 --
1(h) 50.0 g 24 --
1(h) 75.0 g 10 --
1(b) 1.0 g 14 --
1(b) 2.0 g 30 19
1(b) 2.5 g -- --
1(b) 5.0 g -- --
1(d) 25.0 g 10 --
1(d) 50.0 g 14 --
1(d) 75.0 g 23 --
1(a) 20.0 g 38 37
1(a) 40.0 g 42 40
1(a) 60.0 g 37 34
3 5.0 lb 14 --
5 3.5 g 8 --
5 7.0 g 4 --
4 0.5 lb 23 8
1(h) + 1(b) 25.0 g + 2.5 g
-- --
1(h) + 1(b) 25.0 g + 5.0 g
15 --
1(h) + 2 25.0 g + 1.0 g
28 --
1(h) + 2 25.0 g + 2.0 g
29 --
1(h) + 2 50.0 g + 1.0 g
-- 10
1(h) + 2 50.0 g + 2.0 g
26 12
1(d) + 2 25.0 g + 1.0 g
23 --
1(d) + 2 25.0 g + 2.0 g
11 --
1(h) + 3 25.0 g + 1.5 lb
16 13
1(h) + 3 50.0 g + 1.5 lb
29 12
1(h) + 4 25.0 g + 0.125 lb
42 16
1(h) + 4 50.0 g + 0.125 lb
38 27
1(h) + 5 20.0 g + 3.5 g
16 --
1(d) + 4 25.0 g + 0.125 lb
37 13
1(d) + 5 25.0 g + 3.5 g
19 13
1(d) + 3 25.0 g + 1.5 lb
31 14
1(d) + 3 50.0 g + 1.5 lb
29 14
1(k) 20.0 g 27 --
1(k) 40.0 g 29 11
1(k) 60.0 g 24 31
1(k) 80.0 g 37 41
1(d) 20.0 g 22 --
1(d) 40.0 g 24 --
1(d) 60.0 g 19 --
1(d) 80.0 g 35 23
2 1.0 g -- --
2 2.0 g -- 7.2
1(k) + 2 20.0 g + 1.0 g
21 16
1(k) + 2 20.0 g + 2.0 g
28 25
1(k) + 2 40.0 g + 1.0 g
22 34
1(k) + 2 40.0 g + 2.0 g
32 30
1(d) + 2 20.0 g + 1.0 g
16 --
1(d) + 2 20.0 g + 2.0 g
19 13
1(d) + 2 40.0 g + 1.0 g
19 --
1(d) + 2 40.0 g + 2.0 g
26 29
4 0.125 lb 26 29
4 0.375 lb 15 19
4 + 2 0.125 lb + 1 g
34 29
4 + 2 0.125 lb + 2 g
38 25
4 + 1(k) 0.125 lb + 20 g
31 23
4 + 1(d) 0.125 lb + 20 g
29 13.5
5 2.0 g -- --
5 7.0 g 15 --
5 + 2 2.0 g + 1.0 g
21 4
5 + 4 + 2 2.0 g + 0.125 g +
28 5.8
1.0 g
5 + 4 + 1(d)
2.0 g + 0.125 g +
27 --
20.0 g
5 + 4 + 1(k)
2.0 g + 0.125 g +
44 10
20.0 g
______________________________________
*DAT = Days after treatment
EXAMPLE 3
Evaluation of
2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)-5-methyl-nicotinic Acid
for Retarding Growth of Turfgrasses
An evaluation of another composition of the invention is conducted using
the procedure of Example 1 above and Bermudagrass (Cynodon doctylon) as
the turfgrass species.
The test composition,
2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-yl)-5-methyl-nicotinic acid, is
applied to said turfgrass at rates of from 25 to 200 grams per hectare.
Test compound is applied in the form of an aqueous solution as described
in Example 1 and treated plants were held in the greenhouse for 60 days
after treatment and then harvested.
Data obtained are reported in Table VII below.
TABLE VII
______________________________________
Rate Phytotoxicity
Clipping* Clipping*
(g/ha)
Rating** Fresh Weight (g)
Dry Weight (g)
______________________________________
0 0 369 97
25 0 231 (37.4%) 59 (39.1%)
50 0 209 (43.3%) 54 (44.3%)
100 1 163 (55.8%) 41 (57.7%)
150 3 114 (69.1%) 30 (69.0%)
200 5 68 (81.5%) 23 (76.2%)
______________________________________
*% Reduction over checks is shown in parenthesis.
**Phytotoxicity Rating ranges from 0 meaning no injury to 10 meaning
complete kill.
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