Note: Descriptions are shown in the official language in which they were submitted.
~784~)'7
R.J.~immons et al 2-2-2
--2--
This invention relates to m-isopropyl phenylureas,
to a process for the control of undesirable vegetation with
said compounds and to herbicidal compositions containing
said compounds.
m-alkyl phenylureas in which the alkyl group is
methyl or halosubstituted methyl are known, as is their
herbicidal activity. Specifically, the trifluoroemthyl
derivative is sold commercially as a herbicide. However, the
trifluoromethyl derivative has a broad spectrum of activity
and damages many desirable crops including established lawns.
It is, therefore, insufficiently selective to use for weed '
control of lawns. German patent 1,911,610, dated October 1,
1970, discloses a group of polyhaloethyl and -propyl derivatives
possessing herbicidal activity with greater selectivity.
However, the patent discloses only pre-emergence herbicidal
activity and neither the German patent, nor the prior art,
discloses how the propyl derivatives are prepared. Moreover,
the degree of herbicidal effectiveness of the known m-alkyl
phenylureas appears to decrease as the fully halogenated alkyl
group increases in length from methyl through propyl. The
trifluoromethyl is the most effective herbicide, the fully
fluorinated ethyl derivative is not as effective and the
isopropyl derivatives disclosed in the German patent possess
insufficient herbicidal activity to be of value for weed
~5 control.
--2--
~ "''.
. .. : . - . . , . ~
. .
.
` iO78407
.
:`:
R.J. Timmons et al 2-2-2
:'
It is, therefore, a primary object of the present
invention to provide a new class of m-isopropyl phenylureas.
It is an additional object of this invention to
provide a new class of herbicidal compounds for the post-
emergence control of weeds, and more specifically for theselective post-emergence control of monocot weeds in lawn~.
;` It has now been discovered that compounds of the
. ~
following structural formula are effective herbicides for
post-emergence weed control:
'`''` 10
>N C NH= ~_
R ~ CFnH3-n
~ FORMULA I
! CFm~3_m
in which R is from the group consisting of hydrogen, methyl,
ethyl and methoxy; m and n are integers from 0 to 3; and X is
hyarogen when the sum (m+n) exceeds 4, and otherwise X is
from the group consisting of H, F, and Cl. The compounds of
;j the invention are used by applying a growth inhibiting amount
to undesirable vegetation, including both monocotyledonous
and dicotyledonous weeds. They are particularly useful for the
selactive post-emergence control of monocotyledonous weeds
in lawns.
Control of standing dicot weeds in grass lawns can
be readily effected by application of known herbicides. However,
.
~ : .
` 1C~78407
R. J. Timmons et al 2-2-2
-4-
,;
such control is not presently avaiLable for emerged monocot
weeds in lawns. Probably the most successful instance of
salective grass control is post-emergence control of crabgrass
with derivatives of methanèarsenic acid. But the use of such
materials has come under increasing attack on ecology grounds.
Insofar as is known, no satisfactory material is available for
the selective post-emergence control of tall fescue, bentgrass,
; poa annua, nimblewill, or quackgrass in lawns.
The m-isopropyl phenylureas of the above Formula I
possess high activity against many of these noxious monocotyl-
edonous weeds whilP maintaining tolerance to desirable lawn
grasses. The present compounds therefore, offer to fulfill the
long-sought goal of post-emergence control of monoctyledonous
weeds in grass lawns.
Examples of compounds falling within Formula I which
have been found to be useful in the invention include the
following~
1. Compounds in which X is hydrogen and m and n are
each three:
\N _ C _ NH ~ O ~
" 3 2
l-Methyl-3-m-(1,1,1,3,3,3-hexafluoro-2-propyl) phenylurea
1,1-Dimethyl-3-m-tl,1,1,3,3,3-hexafluoro-2-propyl) phenylurea
l-Methoxy-l-methy1-3-m-(1,1,1,3,3,3-hexafluoro-2-propyl)-
phenylurea
--4--
. .
.
Q78~)7
'''
R. J. Timmons et al 2-2-2
-5-
l-Ethyl-l-methyl-3-_-(1,1,1,3,3,3-hexafluoro-2-propyl)-
phenylurea
~- 2. Compounds in which X is fluorine and m and n are
. each two:
CH3
C~
. CF(C~IF2)2
~ .
` l-Methyl-3-_-(1,1,2,3,3-pantafluoro-2-propyl)phenylurea,
. 1,1-Dimethyl-3-m-(1,1,2,3,3-pentafluoro-2-propyl)phenylurea, and
; 10 1-Methoxy-l-Methyl-3-_-~1,1,2,3,3-pentafluoro-2-propyl)-
phenylurea.
3. Compounds in which X is chlorine and m and n
~ are each two:
:: CH3 o
/ N C WH - ~
: CCl (CHF2)2
.
l-Methyl-3-m-(2-Chloro-1,1,3,3-tetrafluoro-2-propyl)phenylurea,
1,1-Dimethyl-3-m-(2-chloro-1,1,3,3-tetrafluoro-2-propyl)-
phenylurea,
20 . 1-Ethyl-l-methyl-3-m-(2-chloro-1,1,3,3-tetrafluoro-2-propyl)-
phenylurea, and
l-Methoxy-l-methyl-3-m-(2-chloro--1,1,3,3-tetrafluoro-2-propyl)-
phenylurea.
` ~C378407
.:
R. J. Timmons et al 2-2-2
-6-
4. Compounds in which X is fluorine, m is 0 and
n is three:
C}13 "
N C____NH < ~ O~ ~
CF'' 3
\ CH3
l-~ethyl-3-m-(l,l,l,2-tetrafluoro-2-propyl) phenylurea,
Dimethyl-3-mr(1,1,1,2-tetrafluoro-2-propyl) phenylurea, and
l-Methoxy-l-methyl-3-m~l,l,~tetrafluoro-2-propyl)phenylurea.
`:
5. Compounds in which X is hydrogen and m and n
-~ lO are 0: o
\ N - C NH - ~ O ~
C11 (C~13)2
l-Methyl-3-m-(2-propyl) phenylurea,
l-l-Dimethyl-3-m-(2-propyl) phenylurea, and
l-Methoxy-l-methyl-3-m-(2-propyl) phenylurea.
. .
: ~ .
of the foregoing compounds, the most active appear to be the
l,l-dimethylureas (in which R is methyl).
The unobvious nature of the present discovery is
:. .
demonstrated by the lack of herbicidal activity shown by a
number of closely related compounds. The compounds falling
within the scope of Formula I generally demonstrate 80~ or
; ~ ~
'
~ -6-
. . !
~ ~ . ' ' , ' ' `
-
` ` `` ~.~3784(~
, .
R. J. Timmons et al 2-2-2
- 7 ~
greater control of several indicator weeds at 5 ox 10 lbs per
acre and often control one or more weeds at 1 lb/acre. The
following closely related compounds failed to give as much as
-` 50% control of a single weed species at either 5 or 10 lbs/acre:
O
N C N ~
; CX (CF3)2-
in which R=CH3 and X=OCH3; R=CH3 and X=F; R=OCH3 and X=F;
and R=CH3 and X=Cl, and
CH3 ~
R ~ ~ C
F ICClF2)2
in which R=CH3 or OCH3.
me compounds of the invention are prepared from the
corresponding m-isopropylaniline intermedia~e, many of which
are themselves new compounds. The latter compounds and their
preparation are the subject of our co-pending Canadian ~pplication
No. 195,128 filed of even date herewith and reference should be
i 20 made to tha foregoing application for a complete description of
~he preparation of the intermediates. In general, the m-isopro-
pylanilines are pxepared by reacting benzene in the presence of
a metal halide catalyst with a ketone of the formula:
CFnH3_n
Cl-O
CFmH3_m
- 1~7~3407
.
R. J. Timmon~ et al 2-2-2
-8-
in which m and n are integers from 0 to 3 to produce a 2-phenyl
isopropanol, halogenating the 2-phenyl isopropanol to produce
a 2-halo-isopropyl benzene, nitra~ing the 2-halo-isopropyl
benzene to produce a m-(~-halo-isopropyl) nitro-benzene, and
hydrogenating the m-(2-halo-isopropyl) nitro-benzene to produce
the m-isopropylaniline intermediate. The phenylureas are
produced from the m-isopropylanilines by converting the latter
-~ with phosgene to isocyanates which readily react with aliphatic
amines to produce the ureas.
The following examples illustrate the preparation
of the phenylurea compounds of the invention. Examples 1-5
illustrate the preparation of the isocyanate, while examples
6-22 illustrate the preparation of the final phenylurea com~
pounds from the isocyanate.
Example 1
The following procedure was used in the preparation
of each of the isocyanates of Examples 1-5 from the isopropyl-
aniline.
A phosgene cylinder was connected to a trap and in
turn to a gas addition tube entering the reaction flask. This
flask was equipped with a mechanical stirrer, thermometer, and
condenser which was replaced with a dropping funnel during the
. : . . ~ . , ~ .
~78407
R. Jo Timmons et al 2-2-2
_9_
addition of isopropylaniline. The top of the condenser (or
. dropping funnel) was equipped with an adaptor. The adaptor was
~ ~a6~ k~
~ connected via Tygon~tubing through a trap to a magnetically-
stirred solution of 30~ NaOH. Ethyl acetate was dried over
MgSO4, and a 2-liter portion was employed per mole of isopropyl-
aniline reagent. The isopropylaniline was dissolved in 5 ml.
of ethyl acetate per gram, and the remaining ethyl acetate
was placed in the reaction 1ask.
The phosgene stream was started and the ethyl acetate
in the reaction flask saturated at room temperature ~pproxi-
mately 20 minutes). The condenser was replaced with a dropping
funnel containing the solution of isopropylaniline in ethyl
acetate. The isopropylaniline was added dropwise while the
phosgene stream was continued. After the addition was complete,
the dropping funnel was replaced and heat was applied until
gentle reflux was attained. In each case, l hour of ref~ux
while phosgene addition was continued was sufficient to convey
any insoluble amine hydrochloride into the soluble isocyanate.
The phosgene stream was stopped, and dry nitrogen was passed
ao through to remove most excess phosgene while the solution was
refluxed for a second hour. After the solution had cooled,
the bulk of the solven~ was removed by distillation with
aspirator vacuum. The remainder of the solvent was removed
with a rotary evaporator to leave the crude produc~. The
1~78407
R. ~. Timmons et al 2-2-2
-10-
specific isorpopylaniline used in this example was m-(l,l,l-
3,3,3-hexafluoro-2-propyl) aniline. The reaction product was
O=C=N ~
C}~(CF3)2
m~(l~ 3~3~3-Hexafluoro-2-propyl) phenyl Isocyanate
Liquid, b.p. 114-124C. (45 mm). IR: 4.38~ (N=C-O).
The same procedure was used to prepare the follow-
ing isocyanates from the corresponding isopropylanilines.
Example 2.
O=C=N_ ~
CF(CHF2)2
m-(1,1,2,3,3-Pentafluoro-?-propyl) phenyl Isocyanate
~iquid, b.p. 115-120C. (15 mm). IR: 4.38~ (N-C-O).
Example 3.
O=C=N ( ~
CCl(CHF2)2
~-(2-Chloro-1,1,3,3-tetrafluoro-2-pro ~ ) phenyl Icocyanate
Clear, colorless liquid, b.p. 132-138C. (llmm). IR: 4.39~J
(N=C=O).
Example 4.
r
O-C=N--<~ /CF3
~ ~13
m- (1, 1 ,1, 2-tetrafluoro-2-propyl)~ nyl Isocyanate
Liquid, b.p. 115C. (30 mm.) IR: 4.40~ (N=C=O).
--10--
,
.
; 1~78407
R. J. Timmons et al 2-2-2
--11--
Example 5.
O=C=N- ~
C1~(C113)2
':....................... .
` m-Isopropylphenyl Isocyanate
,
Liquid, B.P. 55C. (0.5 mm.). IR: 4.38~ (N-C=O).
Examples 6-22.
The following procedure was used to convert the
isocyanate to the final phenylurea compound by reaction with
the appropriate aliphatic amine, CH3NRH, where R has the same
meaning as in Formula I above.
Methylamine, dimethylamine, and methylethylamine
were commercially available reagent grade chemicals. Methoxy-
methylamine was generated as ne~eded by covexing its hydro-
chloride with 5 ml. of ether per gram and slowly adding l0
lS NaOH to generate a solution of the free amine in ~ther.
In the urea preparations, an excess of amine was
employed~ This was to account for loss due to vola~ility of
methyl-, dimethyl-, and methylethyl-amine and for lack of
complete conversi.on of the methoxy-methylamine hydrochloride
to the free amine! in ether.
A solution of the appropriate amine in dry ether
was cooled in an ice bath, and a solution of the aryl iso-
cyanate in 5 ml. of ether per gram was added dropwise below
10C. After the addition was complete, the reaction mixture
was stirred 2 hours at ambient temperature. The condenser
was removed, and the ether allowed to evaporate as the reaction
--11--
~71~0~
` R. J. Timmons et al 2-2-2
-12-
mixture stirred overnight in a hood. The crude pxoduct
which remained was purified by appropriate means. Properties
of the specific ureas prepared are given in tlle following
~xamples.
; 5 m-(1,1,1,3,3,3-Hexafluoro-2-propyl) phenyl Ureas
CH3
\ N _ C - NH - ~ ~
H(CF3)2
Analysis
Exampla R mp ~C) C=O(cm 1) C H F N
6 H 115-123 1650
7 CH3 122-123 1630 Calcd. 45.87 3.85 36.28 8.91
Found 45.90 4.78 35.94 9.00
8OCH3 67-72 1660 Calcd. 43.65 3.66 34.52 8.48
Found 43.55 3.48 34.34 8.56
9C2H5 86-88 1640
; 15 m-(1,1,2,3,3-pentafluoro-2-propyl) phenyl Ureas
CH3 O
\ N - C - NH - ~
CF(CHF2)2
Analysis
Example R mp (C) C-O (cm~l) C H F N
H113-115 1650 Calcd. 46.82 3.90 33.66 9.93
Found 46.98 3.63 33.37 10.22
` 11 CH395-96 1640 Calcd. 48.66 4.42 32.07 9.46
Found 48.37 4.22 32.62 9.68
12 CH30 oil 1680 Calcd. 46.16 4.19 30.42 8.97
Found 46.20 4.19 29.43 8.76
-12-
- - lQ789~7
.
.
,~ R. J. Timmons et al 2-2-2
; - 13 -
m-(2-chloro-1,1,3,3-tetrafluoro-2-~propyl) phenyl ureas
CH3 \ "
R ~ { ~
Cl(CHF2)2
` Anal~sis
Example R mp (C) C-0(cm~l) C _ Cl F N
13 H 137-39 1650 Calcd. 44.23 3.71 11.87 25.45 9.38
Found 43.82 4.04 12.33 24.91 9.54
14 CH3 87-88 1640 Calcd. 46.09 4.19 11.34 24.30 8.96
. Found 45.45 4.48 11.14 24.60 9.24
C2Hs 81-83 1640
16 OCH3 Oil 1670 Calcd. 43.85 3.99 10.79 23.12 8.52
Found 43.75 4.44 10.56 22.53 9.04
~,
mr(l,l,l,2-tetrafluoro-2-propyl) phenyl ureas
.~: O
~3
~N- C NH ~ ~ CF3
F
\ GH3
Example R mp (C) C=0(cm~l) C Analysis N
17 H 119-123 1650 Calcd. 50.01 4.57 28.76 10.60
Found 50.20 4.78 28.46 10.80
18 CH3 108-109 1640 Calcd. 51.80 5.07 27.31 10.07
Found 51.50 5.18 27.14 10.17
; 19OCH3 Oil 1680 Calcd. 48.98 4.79 25.83 9.52
` Founa 49.10 4.89 26.10 9.32
m-Isopropylphenyl ureas
C33 ~ C _ N~3 ~
CH(cH3)2
- 13 -
378407
;
R. J. Timmons et al 2-2-2
-14-
Analysis
Example R mp (C~? C=O(cm 1) C H N
- 20H 108-9 1660
21CH3 98-99 1650 Calcd. 69.87 8.80 13.58
E'ound 69.92 8.85 13039
22oc~3 77-78 1670
Depending on the particular compound, the type
of formulation in which it is incorporated, the character-
-~ istics of the particular area to which the formulation is
applied, etc., the compounds of the present invention may
be applied at single application rates ranging from 1 to
16 or more pounds per acre for the purposes discussed above.
Applications in this range will in most cases provide
excellent weed control with minimal or no turfgrass injury.
It is within the province of our invention to use repeat
applications of the compounds, normally at rates below
the single application rates. Repeat applications at low
rates will typically provide control of weeds with a minimum
of turf injury in even the most difficult circumstances.
Further, mixtures of the compounds of the present
invention may be employed for the purposes described herein,
if desired.
The compounds of the present invention can be employed
in sprays, in granular formulations, as drenches or combined
with a diluent and,/or other adjuvants to make a dust and
-14-
.
iO7~
:
R. J. Timmons et al 2-2-2
- 15 -
applied with conventional dusting equipment. Depending
; upon factors such as those discussed above in conjunction
with application rates, the proportions of the ingredients
in the formulation may vary over a wide range. Generally
5 speaking, however, the proportions will fall within the
following limits:
Ingredient Parts by Weight
Carrier 8100
Solvent-sticking agent 0-3200
Phenyl urea 300-4500
Surfactant 0-1000
Appropriate carriers include organic solvents,
water, vermiculite, perlite, diatomaceous earth, clay, corn
cobs, and other materials such as those described in the
- 15 Handbook of Dust Diluents and Carriers (2d Ed.), 1955. For
granular formulations, exfoliated vermiculite is preferred.
` One suitable surfactant for use in the formulations
descri~ed herein is Triton X-100, a trademark for an octylphenoxy-
polyethoxy ethanol manufactured by Rohm & Haas Company.
Other suitable surfactants are those listed in Deter~ents and
Emulsifiers, Up-to-Date, 1968, John W. McCutcheon, Inc.
The "solvent" may include or be a sticking agent. Suitable
"solvents" include Polyvis OSH (a trademark for a polybutene having
a molecular weight of approximately 400 manufactured by the
-- 15 --
,.
. ~078407
R. J. Timmons et al 2-2-2
-16-
Cosden Oil and Chemical Company) and hexylene glycol. Other
suitable solvents-sticking agents are described in U. S. Patents
Nos. 3,076,699 and 3,083,089.
The foregoing patents also disclose methods for making
granular formulations which may be used with the compounds
of tne present invention. That is, those compounds which
are solids at room temperature may be dissolved in an
appropriate solvent and adhered to a carrier in the m~nner
disclosed in Patent No. 3,083,089. Or particles of the
compound may be adhered to a carrier with a suitable s~ick-
ing agent as described in Patent No. 3,076,699. Those
compounds which are liquids can be similarly absorbed
on exfoliated vermiculite as described in the foregoing
patents.
Diluents, stabilizers, fertilizers and other
plant nutrients, other herbicides, flow enhancing agents,
adhesives, dyes, and other adjuvants may also be employed
in formulations in which the compounds of the present
invention are incorporated. The above mentioned and other
adjuvants which may be employed are described in Weed Control
~2d Ed.), Robbins et al, McGraw-Hill Book Company, Inc.,
New York, New York, 1952, and in U. S. Patents No. 3,231,363,
issued January 25, 1966, to Victor A. Renner for PROCESS
FOR MAXING FOAMED UREA-FORMALDEHYDE FERTILIZER, and U. S.
Patent 3,705,794, issued December 12, 1972 for FOAMED
FERTILIZERS AND COMBINATION PRODUCTS which disclose various
-16-
107840~
R. J. Timmons et al 2-2-2
-17-
com'oination prod~cts in which the compounds disclosed
herein may be incorporated and methods of preparing such
formulations. tSee also Patents Nos. 3,076,699 and
3,083,089.)
A series of tests were conducted to evaluate
the herbicidal effectiveness of the compounds of the
invention as well as their degree of selectivity on
established lawns.
Initial greenhouse tests were conducted to
determine the activity of the compounds of the invention
for the post-emergence control of lawn weeds. The results
are summarized in Table I.
-17-
7~3~(17
- ' ~
,
-- 18 --
.
,' ~ ~
8 ~ u~ OD o o o o o In c~ o o o u~ OD o o o
" ~ ~ o~ u~ o o o a~ o o o o t~ ~ o o o
~ .~
,.
. ,,~
u~ o o o ~ ~ 1~ ~ o ~ o u~ In
o o o
'~ h ~ ~D o u~ co o ~ ~
o o o
,:'
.~ ~
,- ~ ~ o u~ o co oo o ~n OD 0~ 0 0 0 0 1`~ o o O
3 ~ N C~ I` O 1` 1~ CO O al ~ O t` O O O
~1 O
O ~ P
O
H ~
C o o In o o o o u~ o oo ~ o o o o o
P~ ~ o o u~ o a~ o o ~ o oo o~ o o o o o
`; ~ m ,~
. ~
~ ~ O O U~ CO O O O O CO Lr~ O O O
h CD r~ o o~ ~ co r~ o o~ i o o o
::
.
., _
. ~
~ o In In o oo o o o o o o o o o o o
-
O !3 ID r~ CO ~ O_I N ~) ~ U~ ~D r~ ~ ~ O _I N
~ X ~1 ~ I ~1 ~ N N
., ,
U7 0 U~
--I
-- 18 --
~C17840'7
.~
R. J. Timmons et al 2-2-2
--19--
; It is clear from Table I that the compounds
'~ of the present invention possess a high order of activity
, against both monocots and dicots at 5 to 10 pound per
acre.
Additional tests were run at a lower application
rate to determine whether the compounds give celective control
of undesirable grass and weeds in the presence of Rentucky
bluegrass. Table II records the results from several of the
examples on bentgrass, pigweed, and bluegrass when applied
by the same test method, but at one pound per acre.
--19--
10'78407
.' I
o-
;,i
~ I o o ~ o o o o In o
'dP'~ ~ I
: ~m
l ~ol ~ O ~
~q .~ ~ o
al I ~ ~ ~
; ~ ~ ~ o ~ o o o o ~ o u~
I ~1 al ~ O In
` . _
f ~
O 1` ~ O -I N 1` co o~ o
w l ~1 ~I r~l N N N
1~ 0
. . ,
~ ~7840~
R. J. Timmons et al 2-2-2
-21-
Table II demonstra~es the selectivity of the
: herbicidal compounds of the invention. Compounds of
examples 6, 8, 13, 14, 15 and 16 gave no post-emergence
kill of either weeds or bluegrass at one pound per acre
and thus are not included in Table II. The compounds
of these examples require higher application rates.
Further tests were conducted to test the herbicidal
effectiveness of m-heptafluoroisopropyl and m-chlorohexa-
fluoroisopropyl, i.e., compounds outside the scope of
Formula I. The three compounds tested were:
(1) 1,1-dimethyl-3-m-(1,1,1,2,3,3,3-heptafluoro-
2-propyl) phenylurea,
(2) 1-methoxy-1-methyl-3-m-(1,1,1,2,3,3-hepta-
fluoro-2-propyl) phenylurea and
(3) 1,1-dimethyl-3-m-(2-chloro-1,1,1,3,3,3-
hexafluoro-2-propyl) phenylurea
; The results from the same initial greenhouse test of post-
emergence weed control as reported in Table I for the examples
of the present in~ention are shown in Table III for the hepta-
fluoroisopropyl compounds (1) and (2) and the chloro-hexa-
fluoroisopropyl case (3).
-21-
378~1~7
-22-
~Q
~n
~C
_I U
~; m
Iol;~~
~ o O O
`.` ~ ..
J ; : ;
l~ol O O
.
Q)~,
P ~ U~
o .
~ ,,
C~ ,
. . . . . . .. ~ ~. . . . . . . .
~L(378~07
.
R. J. Timmons et al 2-2-2
23-
Comparison of the results in Table III with those
of the active compounds in Tables I and II illustrate the
striking loss of activity observed in compounds which are
structurally similar to, but outside the scope of, Formula I
5 of the invantion.
Similarly, the pre-emergence herbicide activity
of the compounds in Table III were examined. The results
.. for annual bluegrass lPoa annua), barnyard grass (Echinochloa
crus-galli), redroot pigweed (Amaranthus retroflexus), wheat-
grass and Bermudagrass are shown in Table IV.
.~. .
~. .
.
t
-23-
78407
.:
. -24 -
':
0
~ ~ o o o
n~ ~
m
In
O~
i~
.. ~ C~ o o
. ~ ~
.' ~
~` ~
. ~ CO O o
3 :~ ~
~Uo ~ o~ o o o
,1 ~q
:~
o
.. ~o ~
. o o o o
~'
~ '~
2~,
.. ._
~ ,, ~ ~
.. . . .
. . . . ...
.. . . . ..
-
7846~7
R. J. Timmons et al 2-2-2
-25-
It is evident from the above that compounds containing
the fully-halogenated isopropyl group also posses no signif-
icant pre-emergence herbicide activity.
Activity of the m-isopropylphenylureas of the
S in~ention in the greenhouse was confirmed in a variety of
~ield t~sts conducted with selected compounds. Post-emergence
monocot control activity was determined by applying the chemicals
as sprays to 1 foot by 2 foot plots of established grassy
weeds. Tolerance to desirable grasses was measured by spray-
ing the compounds on 1 foot by 2 foot plots of Windsor
~entucky bluograss. The resu ts are shown in Table V.
.
7~3407
~ ~n
O ~n
~ h
.~ ~ U
~ ~ o o o o o o o o o o o r~
m
~o
~'~`. O U~ O O C~ O O U~ O
o ~ ~ 1 o
,. ~ ,.,
~ O O O O ~O OU~ ~ CO ~ 00 -
:~ O ~ o ,~
,. ~ ~: ~
'~ g u~ ~ In o o ~
c ~ N ~ ~I~ N cn
m
:~
. ~
:'
o
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: R. J. Timmons et al 2-2-2
-27-
: Table V de~onstrates the ability o~ the compounds
of this invention to selectively des~trQy undesirable grasses
. such as bentgrass, Poa annua, and, i.n some cases, crabgrass
; in the presenca of desirable lawn species such as ~entucky
Bluegrass.
Additional testing was conducted on larger, 2'
~. .
X 3' plots. The chemicals were formulated both on granular
carricrs and ao sprays. Thc results are recordcd iA Table VI.
-27-
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-29-
Similarly, two of the m-isopropyl phenylureas of
the invention were tested for selective post-emergence
~icot control in the field. The chemicals were formulated
both on granular carriers and as sprays. These formulations
were applied to 2' X 3' plots of various dicot weed~ and
also to bluegra~s sod to determine the turf tolerance of
the formulations. The resul~s are shown in Table VII.
.
-29-
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R. J. Timmons et al 2-2-2
-31-
In the above field tests, the chemicals were applied
to the plant foliage. That is, sprays were directed at and
allowed to dry on the foliage. Granular materials were
applied to previously moistened foliage to promote adherance.
S The following Tabel VIII shows the activity of
the herbicides when applied to the soil rather than the foliage.
` In this case, the chemicals were applied as sprays or granular
formulations and immediately "watered in", i.e. washe~ off
the foliage onto the soil. In an initial test for soil
activity, several of the m-isopropyl phenylureas were applied
as sprays and then watered in to 1' X 2' plots of actively
growing grassy and broadleaf weeds. A 1' X 2' strip of blue-
grass sod was employed to measure turf tolerance. Table
VIII lists the results.
-31-
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R. J. Timmons et al 2-2-2
;: -33-
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One of the more preferred compounds, l-methyl-
3-m-(2-propyl) phenylurea (compound of example 20) was
placed in an advanced test for activity against dicotyledonous
weeds through the soil. It was applied as a granular ~ormula-
tion and immediately watered in to 2' X 3' plots.
:
-33-
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~. J. Timmons et al 2-2-2
-35-
The data in Tables I through IX illustrate the
versatility of the compounds of the present invention for
weed control in lawns. Both greenhouse and field data
illustrate the ability of these materials to control grassy
and broadleaf weeds without harming desirable lawn grasses.
In addition, the compounds are active both as granular and
spray formulations and may be applied either to the foliage
or the soil. The latter properties are important when the
compounds are applied commercially under a variety o field
conditions. Moreover, Table III and IV demonstrate the
herbicidal ln~ffectiveness of compounds outside the scope of
~ormula ~.
.
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-35-
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