Note: Descriptions are shown in the official language in which they were submitted.
HERB I DUAL 2 -HOLSTEIN LO DEW
Background of the Invention
Field of Invention
This invention pertains to the field of 2-
haloacetanilides and their use in the agronomic arts, e.g., as
herbicides.
Description of the Prior Art
The prior art relevant to this invention
includes numerous disclosures of 2 haloacetanilides which may
be unsubstituted or substituted with a wide variety of
substituents on the aniline nitrogen atom and on the aniline
ring including alkyd, alkoxy, alkoxyalkyl, halogen, etc.,
radicals.
As relevant to the invention compounds, which
are characterized by having an alkoxymethyl radical on the
aniline nitrogen, an alkoxy radical in one ortho position and a
specific alkyd radical in the other ortho position, the closest
prior art known to the inventor are US. Patent Numbers
3,442,945 and 3,547,620. The most relevant disclosures in the
'945 and '620 patents are the compounds
2'-tert-butyl-2-chloro-N-methoxymethyl-6'-methoxyaacetanilide
and its broom analog (Examples 18 and 34 of the '620 patent and
Examples 18 and 36 of the '945 patent respectively).
US. Patents 4,070,389 and 4,152,137 disclose a
generic formula which encompasses compounds of the type
disclosed in said '945 and '620 patents. However, the only
disclosed species compound having an alkyd radical in one ortho
US position and an alkoxy radical in the other ortho position has
an alko~yethyl radical on the aniline nitrogen atom; compounds
of this type are discussed in more detail below.
other less-relevant prior art are Belgian Pat.
No. 810,763 and German Application No 2,402,983; the compounds
ox these references include compounds of the type disclosed in
said ~389 and '137 patents and are characterized by an
.,
J
--2--
alkoxyalkyl radical having two or more carbon atoms between the
aniline nitrogen atom and the oxygen atom of the alkoxy moiety.
The most relevant specific disclosures in said Belgian '763
patent and German '983 application appear to be compounds
having an ethoxyethyl radical on the aniline nitrogen atom, a
methoxy or ethics radical in one ortho position and a methyl or
ethyl radical in the other ortho position; referring to the
'763 patent, see Compound Numbers 7, 13 and 18; other less-
relevant homology of these compounds are also disclosed, erg.,
Compounds 6, 9, 16 and 17, which have methoxyethyl or
methoxypropyl radicals substituted on the nitrogen atom and a
methoxy or ethics radical in one ortho position and a methyl
radical in the other ortho position.
The above '945 patent contains some herbicidal
data relative to those above-mentioned compounds having a
chemical configuration most closely related to the invention
compounds, and some data are presented in the other patents for
other homologous and analogous compounds less-closely related
in chemical structure, e.g., said Compounds Numbers 6 and 9 in
said '763 patent. More particularly, these most relevant
references, while disclosing herbicidal activity on a variety
of weeds, do not disclose any data for any compounds which are
shown to additionally and/or simultaneously control the hard-
to-kill perennial weeds, quack grass and yellow nut sedge and a
broad spectrum of annual weeds including such hard-to-kill
annual broadleaf weeds as prickly side, hemp sesbania, Jim son-
weed, etc. and annual grass weeds such as seedling
Johnson grass, shatter cane, Alexander grass (brusher),
panicums (Texas, Fall and wild pros millet), red rice and
itch grass (Raoulgrass), while also controlling other noxious
perennial and annual weeds, e.g., smarted, lambs quarter,
pugged, foxtails,- large crabgrass and barnyard grass.
I
~Z~3~5~
--3--
A highly useful and desirable property of
herbicides is the ability to maintain weed control over an
extended period of time, the longer the better during each crop
season. With many prior art herbicides, weed control is
adequate only for 2 or 3 weeks, or, in some superior cases,
perhaps up to 4-6 weeks, or, before the chemical loses its
effective phytotoxic properties. Accordingly, one disadvantage
of most prior art herbicides is their relatively short soil
longevity.
Another disadvantage of some prior art
herbicides, somewhat related to soil longevity under normal
weather conditions, is the lack of weed control persistence
under heavy rainfall which inactivates many herbicides.
A further disadvantage of many prior art
lo herbicides is limitation of their use in specified types of
soil, i.e., while some herbicides are effective in soils having
small amounts of organic matter, they are ineffective in other
soils high in organic matter or vice-versa. It is, therefore,
advantageous that a herbicide be useful in all types of soil
ranging from light organic to heavy clay and muck.
Yet another disadvantage of many prior art
herbicides is the limitation to a particular effective mode of
application, i.e., by reemergence surface application or by
soil incorporation mode of application. It is highly desirable
to be able to apply a herbicide in any mode of application,
whether by surface application or by soil incorporation.
And, finally, a disadvantage in some herbicides
is the necessity to adopt and maintain special handling
procedures due to the toxic nature thereof. Hence, a further
pa desideratum is that a herbicide be safe to handle.
It is, therefore, an object of this invention
to provide a group of herbicidal compounds which overcome
.,
37~:
--4--
the above-mentioned disadvantages of the prior art and provide
a multiplicity of advantages heretofore unachieved in a single
group of herbicides.
It is an object of this invention to provide
herbicides which control hard-to kill perennial and annual
weeds such as quack grass, yellow nut sedge, seedling
Johnson grass, prickly side, hemp sesbania, shatter cane,
Alexander grass, panicums, red rice, and itch grass, as well as,
and in addition to, a broad spectrum of other noxious weeds,
e.g., smarted, lambs quarters, pugged, jimsonweed, foxtails,
barnyard grass and crabgrass, and also provide increased
suppression of resistant weeds such as ragweed, velvet leaf,
morning glory and cocklebur, while maintaining crop safety in a
plurality of crops including soybeans, cotton, peanuts, rape
and/or bush beans.
It is a further object of this invention to
provide herbicidal effectiveness in the soil for periods
ranging up to 18 weeks.
Yet another object of this invention is to
provide herbicides which resist leaching and dilution due to
high moisture conditions, e.g., as heavy rainfall.
Still another object of this invention is the
provision of herbicides which are effective over a wide range
of soils, e.g., ranging from light-medium organic to heavy clay
and muck.
Another advantage of the herbicides of this
invention is the flexibility available in the mode of
application, i.e., by reemergence surface application and by
soil incorporation.
Finally, it is an advantage of the herbicides of
this invention that they are safe and require no special
handling procedures.
The above and other objects of the invention
will become more apparent from the detailed description
75~
below.
Summary of the Invention
The present invention relaxes to herbicidally
active compounds, herbicidal compositions containing these
compounds as active ingredients and herbicidal method of use of
said compositions in particular crops.
It has now been found that a selective group of
2-haloacetanilides characterized by specific
hydrocarbyloxymethyl radicals on the aniline nitrogen atom,
specific alkoxy radicals in one ortho position and hydrogen or
a methyl or ethyl radical in the other ortho position possess
unexpectedly superior and outstanding herbicidal properties
vis-a-vis prior art herbicides, including homologous compounds
of the most relevant prior art.
A primary feature of the herbicidal compositions
of this invention is their ability to control a wide spectrum
of weeds, including weeds controllable by current herbicides
and, additionally, a plurality of weeds which, individually
and/or collectively, have heretofore escaped control by a
single class of known herbicides, while maintaining crop safety
with respect to one or more of a plurality of crops including,
particularly, soybeans, cotton, peanuts, rape and snap beans,
and others as well. While prior art herbicides are useful for
controlling a variety of weeds, including on occasion certain
resistant weeds, the unique herbicides of this invention have
been found to be capable of controlling or greatly suppressing
a plurality of resistant perennial and annual weeds, such as
the perennials quack grass and yellow nut sedge, annual
broadleaf such as prickly side, hemp sesbania, jimsonweed,
smarted, lambs quarters, pugged and annual grasses such as
shatter cane, Alexander grass, seedling Johnson grass, Texas
panicum, wild pros millet, red rice, itch grass, and other
noxious weeds such as fall panicum,
I
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foxtails, barnyard grass and crabgrass Improved weed stand
reduction has also been achieved in resistant weeds such as
ragweed, velvet leaf, morning glory and cocklebur.
The compounds of this invention are
characterized by the formula
I OR
wherein R is ethyl, n-propyl, isopropyl, isobutyl, sec-butyl,
cyclopropylmethyl, ally or propargyl;
Al is methyl, ethyl, n-propyl or isopropyl and
R2 is hydrogen, methyl or ethyl; provided that;
When R2 is hydrogen, Al is ethyl and R is ally;
When R2 is ethyl, Al is methyl and R is
isopropyl;
When Al is methyl, R is ethyl, isopropyl,
isobutyl, sec-butyl or cyclopropylmethyl;
When Al is ethyl, R is sec-butyl, ally or
propargyl;
When Al is n-propyl, R is ethyl and
When Al is isopropyl, R is ethyl or n-propyl.
The preferred species of compound of this
invention is 2'-methoxy-6'-methyl-N-(isopropoxymethyl)-2-
chloroacetanilide.
Additional species of this invention are as
hollows:
2'-methoxy-6'-methyl-N-(ethoxymethyl)-2-
chloroacetanilide,
s
137~
--7--
2'-methoxy-6'-methyl-N-(1-sec-butoxy-methyl)-
2-chloroacetanilide,
2'-ethoxy-6'-methyl-N-tallyloxymethyl)-
2-chloroacetanilide,
2'-ethoxy-6'-me-thyl-N-(propargyloxymethyl)-
2-chloroacetanilide,
2'-ethoxy-~-(allyloxymethyl)-2-chloro-
acetanilide t
2l-methoxy-6'-ethyl-N-(isopropoxy-methyl)-2-
chloroacetanilide,
2'-ethoxy-6'-methyl-N-(l-methylpropoxy-
methyl)-2-chloroacetanilide,
2'-n-propoxy-6l-methyl-N-(ethoxymethyl)-
2-chloroacetanilide,
2'-isopropoxy-6'-methyl-N-(ethoxymethyl)-
2-chloroacetanilide and
2'-isopropoxy-6'-mekhyl-N-(n-propoxy-
methyl)-2-chloroacetanilide.
The utility of the compounds of this invention
as the active ingredient in herbicidal compositions formulated
therewith and the method of use thereof will be described
below.
Detailed Description of the Invention
The compounds of this invention may be made in a
variety of ways. For example, these compounds may be prepared
by the azomethine route described in the above-mentioned US.
Patent Numbers 3,442,945 and 3,547,620. According to the
azomethine process, the appropriate primary aniline is reacted
with formaldehyde to obtain the corresponding methyleneaniline
(substituted phenylazomethine), which is then reacted with a
haloacetylating agent such as chloroacetyl chloride or
chloroacetyl android which, in turn, is reacted with the
appropriate alcohol to obtain the corresponding N-alkoxymethyl-
2-chloroacetanilide as the final product.
3~5~
-3- Aye
Another procedure described in Gore detail
below involve the transetherlfication of the appear-
private N-methylene eth~r-2-haloaceta~ilide with the
desired alcohol to obtain toe corre~porlding tran~eth~r-
S flied ~-hydrocarbylmethyl-2-haloacetanilid2O
till another process for producing compounds
accord to this invention involves an N-alkylation of
the anion of the appropriate secondary 2 haloac~tanilide
with an alXylati~g agent under basic conditions The
N-alkylation process is described in more detail yin
Examples 11-14 herein.
This example described the preparation of one
preferred species, 2'-methoxy 6'-methyl~N (isopropoxy-
methyl)-2-chloroacetanilide.
2'-methoxy-6l-methyl~N (methoxymethyl) 2-
chloroacetanilide (0.025 mole) in 100-150 ml. of is-
propanol containing about 0.02 mow of methane sulphonic
acid was relaxed under a Sexuality extxactio~ apparatus
the thimble of which contained activated PA Molecular
Sieves (25 g) to absorb the liberated methanol. The
course ox the reaction was followed by gig. When no-
action was complete, the excess alcohol was removed in
vacua and the residue taken up in ether or chloroform.
,
US The solution was washed with I sodium carbonate soul-
Shea, dried (Mg2SO4) and evaporated. The product we
` purified by Kugelrohx distillation Yield, 55%; pale
amber solid, mop. 43-415.
~2~:~L37~
g
Anal: Caulked for C14H20ClNO3(%): C, 58.84; Ho 7.05;
N, 4.90; Of, 12.41.
Found: C, 58.55j H, 7.08;
N, 4.89; Of, 12.45
The product was identified as described in the lead sentence of
this example
Examples 2-9
Following substantially the same procedures,
quantities of reactants and general conditions described in
Example 1, but substituting the appropriate alcohol to effect
the transetherification to obtain the end product, other N-
hydrocarbyloxy-methyl-2-haloacetanilides according to the above
formula were prepared; these compounds are identified in
Table I.
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Example 10
This example describes the preparation of the N-
(methoxymethyl) tertiary aniline starting materials used to
prepare the final products in Examples 1-9.
The N-methylene ether substituted 2-
chloroacetanilide starling materials used in Examples 1-9 were
prepared by alkylating the appropriate secondary 2-
haloacetanilide by the N-alkylation process referred -to above.
That process will be illustrated in this example with respect
to the preparation of the starting material in Example 1.
2l-methoxy-6'-methyl-2-chloroacetanilide Tao
mow), bromomethyl methyl ether (0.05 molt and
benzyltriethylammonium bromide (2 g) were dissolved in
ethylene chloride (70 ml). Sodium hydroxide solution (40 ml
of 50%) was then added portions with stirring and cooling
keeping -the temperature between 20 and 25C. when addition was
complete, the mixture was stirred for an additional 1.5 hours.
Water (100 ml) was then added with cooling and the layers
separated. The ethylene chloride layer was washed twice with
30 ml saturated sodium chloride solution, dried (Mg2SO4) and
evaporated. The residual product was crystallized or distilled
in vacua to obtain a yellow liquid, by 140C at 1.2 mm Ho.
Anal. Caulked or C12H16ClNO3 (%): C, 55.92; I, 6.26;
N, 5.44;
Found: C, 56.15; H, 6.33;
N, 5.36
The product was identified as 2'-methoxy-6'-methyl-N
(Mathoxymethyl)-2-chloroacetanilide.
Similarly, the starting N-methylene ether
substituted 2-chloroacetanilides ox Examples 2-9 were prepared
by alkylation of the corresponding secondary aniline with
bromomethyl methyl ether, respectively; the analogous
chloromethyl and iodomethyl methyl ethers can also be used.
I
-13-
The secondary aniline starting material used in
this example to prepare the tertiary N-methoxyme-thyl compound
was prepared by the chloroacetylation of the corresponding
primary amine as follows:
2-methoxy-6-methylaniline Tao molt in
ethylene chloride (30 ml) was stirred vigorously with a 10
sodium hydroxide solution (0.05 molt while a solution of
chloroacetyl chloride (0.033 molt in ethylene chloride (20 ml)
was added keeping the temperature between 15-25C with external
cooling. The reaction mixture was stirred for a further 30
minutes after the addition was complete, the layers separated
and the ethylene chloride layer washed with water, dried and
evaporated in vacua. The product was crystallized from a
suitable solvent to obtain white needles, my 130-131C.
Anal. Caulked for CloH12ClNO2(%): C, 56.21; H, 5.66
lo N, 6.56; Of, 16.59
Found: C, 56.16; H, 5.66
N, 6.57; Of, 16.55.
The product was identified as 2'-methoxy-6'-methyl-2-
chloroacetanilide.
The secondary anilides used as starting
materials in Examples 2-9 were prepared in a similar manner.
The primary amine used to prepare the above-
mentioned secondary anilides may be prepared by known means,
e.g., by catalytic reduction of the corresponding substituted
nitrobenzene in ethanol using platinum oxide catalyst.
As mentioned above, the products of this
invention may also be prepared directly from the secondary
aniline by use of said N-alkylation process, without first
preparing the N hydrocarbyloxymethyl intermediate (as described
in Example 10), which is then transetherified to the final
product as described in Example 1. Examples 11-14 illustrate
the preparation of species of this invention by
- " I I
-14-
said N-alkylatio~ process.
Example 11
2'-n-propoxy-6'-methyl-2-chloroacetanilide (4.3S
g), chloromethyl ethyl ether, 3.4g, benzyltriethyl-ammonium
5 chloride, (1.5 g) were mixed in 250 ml of ethylene chloride
and chilled. To the mixture was added 50 ml of 50% Noah at
15C and stirred for 2 hours, then 100 ml of water was added.
The layers were separated, washed with water, then dried over
McCoy and evaporated. The product was purified by Kugelrohr
10 distillation to obtain 4.8 g (89% yield) of clear liquid, by.
130 C at 0.07 mm Hug.
Anal. Caulked for C15H22ClNO3(~): C, 60.10; H, 7.40;
Of, 11.83
Found: C, 59.95; H, 7.39;
Of, 11.79
The product was identified as 2'-n-propoxy-6'-methyl-N-
(ethoxymethyl)-2-chloroacetanilide.
Example 12
2'-isopropoxy-6'-methyl-2-chloroacetanilide,
20 5.55 g, chloromethyl ethyl ether, 4.4g, benzyltriethylammonium
chloride, 2.5 g, in 250 ml of ethylene chloride mixed and
cooled to 0C. To the mixture was added 50 ml of 50% Noah all
at once, while maintaining the temperature below 15C. The
mixture was stirred for 2 hours, cooled, then 100 ml water
25 added. The layers were separated, washed with water, dried
over McCoy and evaporated to obtain 4.7 g (69~ yield) of the
product, a yellow oil.
Anal. Caulked for C15H22ClNO3(%): C, 60.10; H, 7n40;
N, 4.67; Of, 11.83;
Found: C, 60.10; H, 7.40;
N, 4.64; Of, 11.73~
The product was identified as 2'-isopropoxy-6'-methyl-N-
(ethoxymethyl)-2-chloroacetanilide.
Example
Following substantially the same procedure
described in Examples 11 and 12, but using chloromethyl
propel ether as the alkylating agent, 5.0 g (88% yield
of a yellow oil was obtained.
Anal. Caulked for C16H24ClN03(~): C, 61.24; H, 7.71;
N, clue, 11.30.
Found: C, 61.18; H, 7.76;
N, clue, 11.31.
The product was identified as 2'-isopropoxy-6'-methyl-N
(n-propoxymethyl)-2-chloroacetanilide.
Example 14
Following the same procedure described in
Examples 11~13, but substituting the appropriate sea-
aniline and halo methyl ally ether, a yellow oil, by
134C/0.08 mm Hug (Kugelrohr) was obtained.
Anal. Caulked for C14H18ClN03(~: C, 59.26; H, 6.39;
N, 6.94; Of, 12.49.
Found: C, 59.20; H, 6.41;
20N, 6.95; Of, 12.52.
The product was identified as 2'-ethoxy-N-(allyloxy-
methyl)-2~chloroacetanilide.
The herbicides of this invention have been
found to possess unexpectedly superior properties as
reemergence herbicides, most particularly in the
selective control of hard-to-kill perennial and annual
weeds including such perennials as quack grass and
yellow nut sedge; annual broadleaf weeds such as prickly
side, hemp sesbania, jimsonweed, smarted,
lambs quarters, pugged and annual grasses such as
seedling Johnson grass, shatter cane, Alexander grass
(Brusher plantaginea), Texas panicum, red rice, wild
pros millet,-itchgrass, foxtails (e.g., green and
giant), barnyard grass and large crabgrass. Improved
weed stand reduction relative to prior art acetanilides
has also been achieved on other resistant species such
as ragweed, velvet leaf, morning glory and
I
16-
cocklebur.
Selective control and increased suppression of
the above-mentioned weeds with the invention herbicides has
been wound in a variety of crops including soybeans, cotton,
peanuts, rape and snap beans (bush beans). Selectivity has
been shown in some tests in sugar beets, field corn, sweet corn,
wheat, barley and sorghum; however, these crops are usually
less tolerant to the invention herbicides than are -the
foregoing crops. It will he understood by those skilled in the
art that not all of the above-named weeds are selectively
controlled by all the invention compounds under all conditions
of climate, soil type, moisture and/or herbicide application
modes.
In order to illustrate the unexpectedly superior
properties of the compounds of this invention both on an
absolute basis and on a relative basis, comparative tests were
conducted in the greenhouse and in the field with
compounds of the prior art most closely related in chemical
structure to the invention compounds, (2) other homology within
the scope of said prior art which have superior herbicidal
properties, and (3) commercial herbicidal compounds of chemical
structure generally related to that of the invention compounds.
All of the compounds in the comparative tests below are
generically defined as substituted phenyl-N-alkoxyalkyl 2-
haloacetanilides. As used in the tables of data herein the
compared prior art compounds are identified as follows:
A. 2'-methoxy-6'-tert-butyl-N-(methoxymethyl-2-
chloroacetanilide; (Example 18, US. Patents
3,442,945 and 3,547,620).
B. Matthew' tert-butyl-N-(m~thoxymethyl)-2-
bromoacetanilide; (Example 34 of said '620 patent
and Example 36 of said '945 patent).
C. 2',6'-diethyl-N-(methoxymethyl)-2-
chloroacetanilide; (Example 5 of said '620 and
'945 patents; this compound has the common
~LZ~3~
name i'alachlor" and is the active ingredient in
the commercial herbicide LASS I, a registered
trademark of Monsanto Company).
D. 2'-met'nyl-6'-ethyl-N-(ethoxymethyl)~2-
chloroacetanilide; (Example 53 in said '620
patent; common name "acetochlor").
En 2',6'-dimethyl-N-(isopropoxymethyl)-2-
chloroacetanilide; (Example 31 of said '520
patent and Example 33 of said '945 patent).
F. 2'-methoxy-6'-methyl-N-(methoxyethyl)-2-
chloroacetanilide; (Compound No. 6 in said
Belgian '763 patent).
G. 2'-methoxy-6'-methyl-N-(ethoxyethyl)-2-
chloroacetanilide; (Compound No. 7 in Belgian
Patent Mow 810,763).
H. 2'-methoxy-6'-methyl-N-(l-methoxyprop-2-yl)-2-
chloroacetanilide; (Compound No. 9 in said
Belgian '763 patent) and
I. 2'-methyl-6'-ethyl-N-(l-methoxyprop-2-yl)-2-
chloroacetanilide; Us Patent No. 3,937,730;
common name "metolachlor"; this compound is the
active ingredient in commercial herbicide
"Dual", a registered trademark of Ciba-Geigy
Corporation).
In the reemergence herbicidal tests, compounds
of this invention were compared with compounds A-I of the prior
art with respect to control of various perennial and annual
weeds, with emphasis on the hard~to-kill species which are
prevalent infestations in such important crops as soybeans,
3Q cotton, peanuts, rape and bush beans. Test results are
presented below.
In the discussion of data below, reference is
made to herbicide application rates symbolized as "GROW" and
!,`~`
-18-
"GROW"; these rates are given in pounds per acre Lisa which
are convertible into kilograms per Hector (kg/ha) by
multiplying the lb/A rate by 1.12. GROW defines the maximum
rate of herbicide required to achieve 15% or less crop injury,
and GROW defines the minimum rate required to achieve 85~
inhibition of weeds. The GROW and GROW rates are used as a
measure of potential commercial performance, it being
understood, of course that suitable commercial herbicides may
exhibit greater or lesser plant injuries within reasonable
limits.
A further guide to the effectiveness of a
chemical as a selective herbicide is the "selectivity factor"
("SF") for a herbicide in given crops and weeds. The
selectivity factor is a measure of the degree of crop safety
and is expressed in terms of the GREGORY ratio, it the
GROW rate for the crop divided by the GROW rate for the weed,
both rates in lb/A. In the tables below, where used,
selectivity factors are shown in parenthesis following the
weed; the symbol "NO" indicates "non-selective"; marginal or
undetermined selectivity is indicated by a dash (-) after the
weed and a blank space indicates that the plant species was not
in a particular test, that the data was not obtained for some
reason or was less significant than other data present, e.g.,
some shorter term observations are omitted in favor of longer
term data or longer term data omitted because shorter term data
was definitive of a particular herbicidal activity.
Since crop tolerance and weed control are inter-
related a brief discussion of this relationship in terms of
selectivity factors is meaningful. In general, it is desirable
that crop tolerance values be high, since higher concentrations
of herbicide are frequently desired for one reason or another.
Conversely, it is desirable that weed control rates be small,
i.e., have high unit activity, for economical and possibly
ecological reasons. However, small rates of application of a
35 herbicide may not be adequate to control certain weeds and a
I I
--19--
larger rate may be required. Hence the best herbicides are
those which control the greatest number ox weeds with the least
amount of herbicide and provide the greatest degree of crop
safety, i.e. crop tolerance. Accordingly, use is made of
"selectivity factors" (defined above) to quantify the
relationship between crop safety and weed control. With
reference to the selectivity factors listed in the tables, the
higher the numerical value, the greater selectivity of the
herbicide for weed control in a given crop.
The reemergence tests referred to herein
include both greenhouse and field tests. In the green-
house tests, the herbicide is applied either as a surface
application after planting the seeds or vegetative propagules
or by incorporation into a quantity of soil to be applied as a
cover layer over the test seeds in proceeded test containers.
In the field tests, the herbicide is propellant incorporated
PI into the soil, i.e., the herbicide is applied to the
surface of the soil, then incorporated therein by mixing means
followed by planting of the crop seeds.
The surface application test method used in the
greenhouse is performed as follows: containers, e.g., aluminum
pans typically 9.5" x 5~25" x 2.75" t24.13 cm x 13.34 cm x 6.99
cm) or plastic pots 3.75" x 3.75" x 3" t9.53 cm x ~.53 cm x
7.62 cm) having drain holes in the bottom, are level-filled
with Jay silt loam soil then compacted to a level 0.5 inch
(1.27 cm) from the top of the pots. The pots are then seeded
with a plant species to be tested, then covered with an 0.5
inch layer of the test soil. The herbicide is then applied to
the surface of the soil with a belt sprayer at 20 gal/A, 30 psi
~187 l/ha, 2.11 kg/cm2); other sprayer means, e.g., a DeVilbiss
sprayer, are also used on occasion. Each pot receives 0.25
inch t0.64 cm) water as overhead irrigation and the pots are
then placed on greenhouse benches for subsequent sub-irrigation
as needed. As an alternative procedure, the overhead
irrigation may be omitted. Observations of herbicidal effects
I r-3 r
-20-
are made about three weeks after treatment.
The herbicide treatment by soil incorporation
used in greenhouse tests are as follows:
A good grade of top soil is placed in aluminum
5 pans and compacted to a depth of three-eighths to one-half inch
from the top of the pan. On the top of the soil is placed a
number of seeds or vegetative propagules of various plant
species. The soil required to level fill the pans after
seeding or adding vegetative propagules is weighed into a pan.
10 The soil and a known amount of the active ingredient applied in
a solvent or as a wettable powder suspension are thoroughly
mixed, and used to cover the prepared pans. After treatment,
the pans are given an initial overhead irrigation of water,
equivalent to one-fourth inch (0.64 cm) rainfall, then watered
15 by sub-irrigation as needed to give adequate moisture for
germination and growth. As an alternative procedure, the
overhead irrigation may be omitted. Observations are made
about three weeks after seeding and treating.
In a first series of tests, reemergence
20 herbicidal activity data it presented in Table II comparing the
relative efficacy of invention compounds with relevant prior
art compounds against yellow nut sedge and quack grass in
soybeans, cotton and corn.
I
-21~ AGO
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-23-
Reverence to the data in Table II will show
that, in general, the compounds of this invention as a class
are significantly more active, i.e., have a higher unit of
activity, against both yellow nut sedge and quack grass and
exhibit greater crop safety in soybeans and cotton than the
reference compounds.
More particularly, with respect to yellow
nut sedge control, it will be noted that every invention
compound tested was outstandingly more active against yellow
10 nut sedge than Compounds A and B, which are structurally the
most closely related ox the reference compounds, and Compound
H, which while less closely related than A and B may be
considered more closely related in certain aspects to the
invention compounds than are Compounds, C, D, E and It In
lo still more particular, it will be noted that the compound of
Example 1, having a GROW of 0.09 lb/A, was approximately twice
as active as the most active reference compound, Compound E
(GROW of 0.15), while having a crop safety factor three times
as great as Compound E in soybeans and equivalent safety in
20 cotton. It will also be noted that the invention compounds of
Examples 2 and 12 also had equivalent and greater,
respectively, unit activity than Compound E against yellow
nut sedge. Moreover, although reference Compounds F and G have
a fairly high unit activity, neither compound was selective
25 against yellow nut sedge in soybeans, nor was Compound F
selective in cotton. Although Compound G did selectively
control nut sedge in cotton, the degree of safety was less than
that for all invention compounds except Example 2 and markedly
less than that for Examples 5, 6 and 13. The selectivity
I factors ox the compounds of Examples 9 and 14 against nut sedge
in soybeans were particularly outstanding.
With respect to quack grass control, the compound
of Example 2 was almost three times as active as the most
active reference chemical, Compound D, while maintaining
.
V C
-24-
equivalent crop safety in soybeans. Invention compound of
Example 3 also had greater unit activity against quakers and
three times the soybean safety as Compound D. Again, it will
be noted that every invention compound tested against
quac~grass had outstandingly superior unit activity relative to
Compounds A and B, the most-closely related reference compounds
tested. Although the unit activity of Compound H against
quack grass was slightly higher than that for the compounds of
Examples 9 and 14, the selectivity factors for -the latter
compounds against quack grass in soybeans was about twice that
of Compound H, the next closest related of the reference
compounds. Moreover, reference Compounds A, B, F and G were
non-selective against quack grass in soybeans.
Further observations to note in the data of
Table II are that of all compounds tested, the compounds of
Example 5, 6, 9 and 14 had the outstandingly highest safety
factors in soybeans relative to both yellow nut sedge and
quack grass. The compounds of Examples 5, 6 and 13 had by far
the highest safety factors in cotton relative to yellow
nut sedge. It is further to be noted that the outstanding crop
safety factors of the compounds of Examples 5, 6, 9, 13 and 14
are accompanied by very low GROW rates, indicating high unit
activity against yellow nut sedge and quack grass. In these
tests, most of the invention compounds were non-selective in
corn as were all but three of the reference compounds.
However, the compound of Example 14 exhibited outstandingly
superior selectivity relative to both quack grass and yellow
nut sedge in corn.
In other comparative tests, the reemergence
herbicidal activities of reference Compounds C and D and the
compound of Example I were tested against various annual
broadleaf weeds at an application rate of 3.0 lb/A (3.36
kg/ha). Observations were made 6-7 weeks after treatment (WIT)
and the percent control of the weeds recorded; the data prom
these tests are shown in Table III.
Jo O
I
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-25-
TABLE III
Annual Broadleaf Weed Control
Preemer~ence, 6-7 WIT
Percent Control at 3.0 lb/A
cod Compound
jam C D
Prickly side 93 35 73
Hemp sesbania 100 0 69
Pugged 83 62 88
Smarted 88 64 76
Lambs quarter 75 61 81
Ragweed 72 53 43
Jimsonweed 98 68 98
From the data in table III, it is apparent that
the compound of Example I exhibited outstandingly superior
activity relative to Compound C against every annual broadleaf
weed tested. Similarly, the compound of Example 1 exhibited
markedly superior activity relative to Compound D against
prickly side, hemp sesbania, smarted and ragweed, while
exhibiting equivalent activity against jimsonweed, and slightly
less unit activity against pugged and lambs quarters.
In further comparative tests, field tests were
conducted to determine the relative reemergence herbicidal
activities and crop selectivities of the compound of Example 1
relative to reference Compounds C, D, E and I against
barnyard grass, prickly side and hemp sesbania in soybeans.
These tests were conducted in discrete plots of clay (Starkey)
soil containing 2.0% organic matter and treated with various
concentrations of each herbicide applied as an emulsifiable
concentrate at an application volume of 30 gal/A (280.5 kg/ha).
Observations were made 4 weeks and 7 weeks after treatment.
Based upon three replications, the test data show that at the 7
weeks observation, the only compound which selectively
controlled hemp sesbania was the compound of Example l; such
control (GROW) was achieved with only 1.75 lb/A (1.96 kg/ha),
whereas the GROW for each of Compounds C, E and I was 5.0 lb/A
-26-
(5.6 kiwi) and 4.5 lb/A (5.0 kg/ha) for Compound D. The GROW
in soybeans was 3.5 lo (3.9 kg/ha) resulting in a 2.0 folk
safety factor for the compound of Example l. Thus, it required
about 3 times as much of the reference compounds to achieve
GROW as required by the compound of Example l, but without
selectivity in soybeans.
Compounds C and D were non-selective against
prickly side in soybeans at 7 WATT Compound I required 3.75
lb/A ~4.2 kg/ha) and Compound E required 2.5 lb/A I kg/ha)
to achieve ~R85 and selectivity factors of lo fold and 1.5
fold, respectively. In contrast t the compound of Example 1
achieved GROW with only 0.75 lb/A (0.8 kg/ha) and a selectivity
factor of 4.7 fold in soybeans.
Compounds C, D and E were non-selective against
barnyard grass in soybeans at 7 WATT Compound I and the
compound of Example 1 had substantially equivalent safety
factors, i.e., 1.5 fold vs. 1.4 fold, respectively.
Thus, the above field tests show that, but for
comparable control of barnyard grass relative to Compound It the
compound of Example l was significantly superior to reference
Compounds C, D, E and I in the selective control of all three
annual weeds in soybeans at 7 weeks after treatment.
In further tests to determine relative
herbicidal activities and selectivities for still longer
I periods of time, the same herbicides used in the preceding test
were again tested in the field, this time in discrete plots of
soil of silty clay to silty clay loam containing 3~0 - 3.5%
organic matter. In parallel tests, emulsifiable concentrates
of the respective herbicides were surface applied and propellant
incorporated for reemergence control, again a-t 30 gal/A
containing the appropriate concentration of herbicide as active
37~
-27-
ingredient. In these tests, the herbicides were compared
against the perennial weed quack grass and the annual broadleaf
weeds ragweed, pugged and smarted in soybeans. These tests
were exposed to heavy rainfall measuring 1.75 in. (4.45 cm) on
the fifth day after treatment ("DOT") and 0.9 in. (2.29 cm),
0.6 in. (1,52 cm). OWE in. (1.27 cm) and 0.5 in. of rain on
succeeding days. The test data are shown in Table IV.
v~3~7~
-28- AGO
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-30-
Referring to -the data in table IV, it will be
noted that in the propellant incorporated tests none of the
reference compounds selectively controlled any ox the test
weeds in soybeans at rates up to 6.0 lb/A (6.7 kg/ha)l the
maximum test rate, at the 6 weeks and 9.5 weeks observations.
As indicated hereinabove, selectivity is indicated by a
selectivity factor, or GREGORY ratio, of 1.0 or greater; the
greater the value, the greater the selectivity. In contrast,
the compound of Example 1 exhibited selective control of
quack grass, pugged and smarted at 6.0 weeks and control of
quack grass and smarted at 9.5 weeks. The herbicidal activity
of the compound of Example 1 is shown to be on the order ox 3
or more times as great as the reference compounds against
quack grass and pugged (except for Compound D) and
approximately 2 or more times as active as the reference
compounds (except for Compound D at 6 and 3.5 weeks and
Compound E at 9.5 woks None of the herbicides selectively
controlled ragweed in this test, but the compound of Example 1
was more active against this weed than the reference compounds
at 6 weeks.
In the test data based on surface application of
the herbicides, again, none of the reference chemicals
selectively controlled any of the weeds in the test in soybeans
at rates of 6.0 lb/A or less at 6 weeks or 9.5 weeks
observations, except for Compound D in pugged at the 9.5 weeks
observation. In these tests, selective weed control was
observed for the compound of Example 1 in quack grass and
smarted at 6 weeks and in pugged at 9.5 weeks; the safety
factor here was slightly greater than that for Compound D,
i.e., 1.3 vs. 1.1 fold. gain, the compound of Example 1
exhibited much more herbicidal activity than the reference
compounds in these tests.
From the data in Table IV, it is apparent that
from the criteria of unit activity against weeds, soybean
-31-
tolerance to the herbicides, safety factors and modes of
herbicide application, the compound of Example 1 exhibited
substantially superior properties as a reemergence herbicide
than did the compared reference compounds.
The persistent weed control exhibited by the
compound of Example 1 under the heavy rainfall conditions noted
above demonstrated that the compound was not readily leached.
In further comparative field tests, the
compounds of Example 1 and reference Compounds D and E were
tested for selective control of prickly side and crabgrass in
cotton under both surface application and propellant
incorporation modes of herbicide application; yellow nut sedge
was included in the propylene incorporated tests. The soil in
these tests was silt loam having 1.7% organic matter.
Observations were taken at I, 6 and 9 weeks after treatment.
Based upon three replications, data from the surface-applied
tests showed that the compound of Example 1 had over twice the
unit activity against prickly side as Compounds D and E at 6
weeks and 1.5 times their activities at 9 weeks. Compound D
was non-selective against prickly side in cotton at 6 and 9
weeks. The selectivity factors for Compound E at 6 and 9
weeks, respectively, were 1.1 and 1.2 compared with OWE and 1.8
for the compound of Example 1. Although the unit activities of
each tested compound were comparable against crabgrass at 6
weeks, the compound of Example 1 was more active than Compound
E at 9 weeks and more selective (i.e., SO of >4.0) than
Compound D having an SO of 2.8.
In the propellant incorporated tests, after 9
weeks the unit activity of the compound of Example 1 was more
than twice that of the reference chemicals against yellow
nutse~ge, slightly less than twice the unit activity of the
reference chemicals against crabgrass and greater than one
and one-third times the unit activity of the reference
chemicals against prickly side. In this field test, the
,
3'7~
-32-
compound of Example 1 selectively controlled yellow nut sedge in
cotton up to 6 weeks after treatment, but the reference
chemicals showed no selectivity even at the 2 weeks
observation. Although none of the test chemicals selectively
controlled prickly side in -this PI test, the margin of
selectivity was much closer for the compound of Example 1 than
for the other compounds. The compound of Example 1 and
Compound E narrowly con-trolled crabgrass at 2 weeks, but were
non-selective thereafter; Compound D was not selective against
crabgrass at any of the observation dates.
Therefore, the salient conclusions derived from
the above-mentioned field tests in cotton are that the compound
of Example 1 was markedly more active than the reference
compounds against the weeds yellow nut sedge and prickly side,
while maintaining that activity for a longer period of time,
and that the compound of Example 1 had superior selectivity
factors with respect to these weeds. Moreover t the compound of
Example 1 had superior unit activity relative to Compound E and
superior selectivity relative to Compound D against crabgrass
in cotton at 9 weeks.
Further comparative tests between the compound
of Example 1 and Compounds D and E were conducted to determine
their relative herbicidal activities and soil life against the
perennial weeds yellow nut sedge and quack grass. Compounds D
and E are among the most active selective herbicides of the 2-
haloacetanilides of the prior art and have been considered as
standards for the class in tests for other herbicides against
nut sedge and quack grass and other weeds. In the tests
discussed here, two replicates of each treatment were planted
with 25 yellow nut sedge tubers and 25 quack grass rhizome
fragments. The herbicides were incorporated in the
I A i Jo 2 0
3~3P
cover layer of soil a rates surf iciest to determine
the GROW wrap i.e. the minimum rate (lb/A) required
to achieve SO c:orltrol of the weeds; if) LbJA (ho 2
kg/ha was the maximum and I 25 lbJA I 4 kg/ha ) the
5 minimum rates actually apply teal O ~bservatiorls were mace
at 3, 6" 12 and 18 sleeks. After Mach observation, ache
cover layer of soil was removed, the ova twitters and
rho zone ragmen removed and replanted and placed in
tune greenhouse for the succeeding yokel. Test results
10 are shown in Table V; WHITE meals "weeks a per
treatment" .
S AXLE V
toil Life
GROW
Yellow
I WIT
Example 1 I 25 ( <10 4 - Jo I 4 ) 3
<1.~5 I <1.25 I 6
ZOO I 25 if 4 ) I 25 ( I it ) 12
7~5 10~0 (11~2
D . ~1.25 1.4) it I 3
lo ( 1012) <1.~5 (<1.4) 6
5.25 ( 5.9) 5.0 ( 5.6) 12
Lowe (~1102) >iù.O (>11.~
E ~1.25 tC1.4) <1.25 ~<1.4) 3
1. 25 ( 1. 5 ( 1. / ) 6
7.0 ( I 10.0 ( 11.2~ 1
>10 . O ( ~11. 2 ) >10. O ( >11.
30 Reference to the data for yellow nu~se~ige control in
ruble V indicates that at 3 weeks a per treatlilent one
GROW rate of each compound was less than 1. 25 IBM
with some definite differences appearing after weeps.
By 12 weeks major difference in the control of yellow
nutseage were manifest. Thus, where it wrier only
1.25 IBM of the compound of Example 1 Jo control 50'~
ox the weed, it ruler 5.25 Lowe of Compound D gnu
7. 0 lea of Compound E to achieve tune same agree of
aye I Aglow 2 2 0
control of yellow nudge Also, a 18 IT, it
required only 7. 5 lb/A of the compound of Example 1 to
control 503 of the nut sedge as against some
indeterminate amount above 10 lb/A the maximum rate
5 used ) of Compounds D an E.
Similarly, the ~Euackgr~ss data in Tale V
show that at 6 WATT the compourld of Example 1 and
Compared D had slightly superior activity relative to
Compound E. However, at 12 WATT the outstanding
10 supremacy of the compound of Example 1 it shown in
requiring only l. 25 lb/A to achieve the same control of
quack grass as required by 5. 0 lb/A of Compound I Inca
lo. O lbtA of Compound E. The superior herbicidal
activity of the compound of Example 1 was also apparent
15 at lo WATT
A distinct aiding of a herbicide is its
ability to function in a wide variety of soil types.
Accoràlngly, data is presented in Table VI showing the
herbicidal ef~ec1 of the compound of Example 1 on
20 yule nutsecige in cotton and soybeans in a wide
variety of toil types of varying organic matter an
clay content. The herbal ire treatments were soil
incorporated with seeds planted 07 375 ion ( 0. 95 cm)
jeep, with 0,25 in (Orate cm) overhead irritation.
25 Observations were made l days a ton treatment .
Lo
- 35 - AGO 0
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The data on Table VI show that toe compound of Example
1 appears to be quite insensitive to soil type and
organic matter content exhlb1ting selective control of
yellow nu~sedge in by cot and soybeans in soils
ranging from 1.~-6.8~ organic maser and 1.~-9.6~ clay.
-Selectivity factors were greatest in Sappy clay loam.
Additional test were conducted to determine
the horsehide performance of compound of Example 1 in
soils containing a large amount of organic matter In
three replica e yield tests, the activity of the
compound ox Example 1 was tested against pug and
lambs quarters in soybeans planted in muck soil.
Compounds C, D, E and I were also tested for
comparative purposes. These tests were conducted in
both preplan incorporated and surface applied moves ox
application in muck soil containing twenty-three
percent (23~) organic matter. In these tests, in both
the PI and surface application moves, the compound
ox Example 1 exhibited the nighest unit activity
against lambs~uarte~s at WIT anal in the PI mode,
the highest selectivity factor in soybeans, i.e.,
> 2.7 vs. 1.1 for each of compounds C and D; Compounds E
an I were non-selective it IT. All compounds were
non-selective against lambs quarters at 7 WIT in either
US mode of herbicide application; Compound E was slightly
more active than the compound of Example 1 it 7 WIT in
both modes 0c herbicide application. Against pugged,
Compound D had the highest unit activity and
selectivity factor (1.9) 7 WIT in bock e PI Edna
surface application modes; in the latter move the
selectivity factor of compound D was almost twice aye
of the compound of Example 1 and Compound E; no other
compounds selectively controller pow 7 WIT in
PI or surface application modes. The compound of
I Example 1 (S.F;2.0) and Compounds an E SO I
for each selectively controlled pod 4 WIT in the
PI move.
37~
_37_ ~G-1~2
Therefore, tune above tests indicate that
relative to the reference compounds in muck toil the
best selective control of lambs quarters in soybeans is
provided by the compound of Example l applied PI
this compound had the highest unit activity and
selectivity factor at WIT ox all compounds in the
test. Moreover, the compound of Example 1 selectively
controlled pugged up to about 7 WIT in the surface
application mode and up Jo 4 WIT in the P. P. I. mode.
Compound D provided the best control ox pugged at 7
WIT in both odes ox application. The relative
performance of the compound of Example 1 and Compound D
in muck soil should be further compared witch the
relative performance of these two compounds in soils
having lesser organic matter ego, 3.0-3.5~, wherein
the compound of example l exits superior unit
activity and soil longevity coupled with seiectivi~y in
swoons in both the sur~ace-applied and PI modes
of application as shown in Table IVY
The foregoing description has emphasized the
outstanding herbicidal efficacy of the compounds of
thwack invention to control perennial weeds and annual
broadleaf weeds in soybean and cotton Further, it
has also been indicated above and occasionally
demonstrated, eye., in the tests involving
barnyard grass and crabgrass, that the compounds of this
invention also have outstanding herbicide aocivity
against annual narrowieaf weeds, i.e., grasses. In
tact, as will be demonstrated eye with respect Jo
certain annual grasses, compounds of this invention
exhibit marked superiority vis-a-vis the most
herbicidally efficacious and/or commercially available
newsstands of the prior art. As will
evident from test data herein, there are instances
35 wherein a relevant prior art 2-haloacetanilide exhibits
superior herbicidal efficacy vis-a-vis the invention
compounds with respect to specific annual wends under
3'7~
_ 3 2 I)
comparable conditions However, it will also be
eviderlt from the coDnparative test data herein that
compounds according to this invention, overall, are at
least comparable Jo and frequently are superior,
5 sometimes out. ~arldingiy Jo, to the best
2~haloacetanilid~s as selective herbicides to control
annual an perennial n~rrowleaf weeds in soybeans,
coy ton, peanuts and other crops .
In one reemergence test in the greenhouse /
10 the compounds of Example en 1 and 11 were compared with
Compounds C and I (both commercial 2-haloacetanilides)
for their relative herbicidal efficacy against annual
narrowl~af weeps , i I, e ., grasses in soybeans In this
test, the horsehide were incorporated into the soil
lo prior to planting seeds and observations maze and
recorded 17 jays aster treatment; the test data are
show in Table VII and represent the averages of
- d~pl irate trials .
37~
- 39 - AGO 12 2 0
I _
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so It
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C
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Pi
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H
I
40_ AGO
Referring to the data in Table VII, salient
features to be noted en that: (lo compound I exhibited
the least unit activity an selectivity of all
compounds again every weed an the test and exhibited
no selectivity lo soybeans with respect Jo wild pros
isle, red rice or itch grass; (2) Compound C way a
active as the more active of the compounds of Examples
l and if against shat~erc no and wild pros millet; (3)
the compounds of En 8 pies l and if were born superior
lo to the prior art compounds in seedling johnson~rass end
itch~rass and (4) the compound of Example if was more
active against alexanderyrass and the compound of
Example 1 was move active against red rice than the
prior art compounds.
Thus, to summarize the comparative test data
in Table VII, one or the other or both invention
compounds were as herbicidally efficacious as the best
prior art reference compound against two annual
na-crowleaf weeds (shatter cane a d w id Russ Malta.
and markedly superior against four narrow leaf weeds
(seedling Johnson grass, alexan~ergrass, red rice an
itch grass). Particularly noteworthy is the outstanding
unit activity or the compound of Example l against
seedling ~ohnsongrass (GROW 0.125 lb/A do kg/ha),
providing an outstanding selectivity factor of Jo Us
fold in soybeans compared with a selectivity factor of
.0 fold for Compound C, the better of the testes prior
art compounds. similarly, the compound of Example if
exhibiter outstanding unit activity against
Alexander grass and itch grass, providing selectivity
factors of I fold and ~4.0 fold, respectively, in
soybeans, compared with corresponding selectivity
factors of I fold and ~1.0 fold respectively, for
Compound C.
till another test was conducted in soybeans,
this tome the Texas and Fall panicum seeds were
included together with the other annual grasses
I
-41~ 12~0
mentioned in the preceding test. in tins test, the
compounds of Examples 1 and 12 were compared for
reemergence herbicidal efficacy against Error art
Compounds C, D and I. The herbicides were soil
5 incorporated and subrogated as required. The maximum
amount of he icier used ill the jest was a the rate of
1. 0 lbJA, hence the exact GROW an GROW rates above 1. ()
lea would be somewhat indeterminate. Observations
were made 2 weeJcs after treatment. The data from ifs
10 test are spawn in Table VIII.
42 1 2 0
okay
P; O I- A
Us
02 to
I
So Us o o
h
O
I
n
us
a) I o us
.. . .
V
us
I
I O
En Pi V V V I Y
H O
h o us o
L s I o o
,-- . I. _ . _ .. . .
Jo Us
I
X
I Jo Us
I O O O I
ED us us
Us
fax I or
,~: U I O O I O
Ill In lo If')
I: I
on
O O O O
I . ._ . ... _ ..
TV V
in
Us
Us
X O N Us I Cal
Pi r-i O O I
A
X X C' '
U do
I u
AnQ1ysis ox the data in Table VOW shows that the
invention compounds of Examples l and 12 exhibited the
highest unit activities an selectlvities of all
compounds in the text against seedling Johnson grass an
shatter cane; the compound of Example 12 had the highest
activity and selectivity against i~chgrass and the
compound of Examples 1 and 12 snared the highest
activities against wild pros millet with Compound D
and against Fall panicum with each of the prior art
compounds. However, the invention compound were more
selective in soybeans Han Compound It with respect to
wild pros millet. Moreover, the compound of Example
12 was the second most active compound against Texas
panicum and red rice and the compound of Example 1
lo shared the second highest activity with Compound D
against itch grass Compound D was the most active of
the jest compounds against Texas panicum,
ale~anderg~ass and Ted rice.
_ . . . . . Therefore, it will be appreciate from the
preceding comparative test data relative to herbicidal
activity involving annual grasses, that compounds ox
this invention have herbicide efficacy superior to
that of tune leading relevant prior art compounds
against certain annual grasses, ego, barnyaragrass,
crabgrass (SKI.), shatter cane Noah i~chgrass, an
equivalent or generally comparable herbicidal efficacy
against other, e.g., crabgrass (surface applies), ye
panicums, Alexander grass and red rice.
I` Otter tests in the greenhouse and/or in tune
field have shown selective control by compounds of this
invention of additional weed species in soybeans,
cotton Andre other crops. Fur example, thy compound
of Example 1 has been shown to selectively control
purple nut sedge and giant foxtail in cotton an giant
foxtail and velvet leaf in soybeans. Further, as
compared with relevant acetanilide herbicides of the
prior art, the compound of Example 1 has shown improve
_44,~ AGO
weed suppression against such resistant weeds as
ragweed, morning glory and cocklebur. Additional Leeds
against which the compounds ox this invention have
proven to be herbi~idally active include Canada
S thistle, field~bindweed, downy broke, wily buckwheat,
etch
As ligated above, compounds ox this
invention have been found to be efficacious herbicide
in a plu~allty of crops The preceding discussion and
test data were directed primarily to weed control in
soybeans and cotton, crops ox primary interest Noah
utility herein Additional tests have demonstrated the
utility ox compounds of this invention in other crops
as illustrated below
In one greenhouse test, the preemergenoe
herbicidal efficacy of the compounds of Examples if and
12 were tested soil incorporated, against quackyrQss
in rape, snap beans, sargnum and wheat. Both tested
compounds selectively controlled quack grass in rape and
snap beans, the selectivity factor of the compound of
Example 11 being 3.5 folk in both crops and that of tune
compound ox Example 12 being 3.0 fold in both crops
In this test, both compounds were nonselective against
quack grass in sorghum and wheat.
In separate greenhouse tests, the ~ompoun ox
Example 1 was also teared for its herbicidal efficacy
against yellow nut sedge and quack grass, respectively,
in rape, peanuts, sugar beets, sorghum Walt and
barley; one herbicide was applies in the soil
incorporated mode. In these tests, Compound D was
included as a reverence compound against quakers an
Compound E was included as a reference company against
yellow nutse~ge. Observations in the quakers test
were made 19 DOT and in the yellow nut sedge test id
DATE the test data are shown in Table IX; selectivity
factors for the herbicides are shown in parenthesis
aster the ~R15 razes for toe respective crops.
I
hug 1220
Jo
o o I
I
_ _ _ _
Jo Us
h O
pa . O
ago o o o
COCK O
. . pa
,4 Z
o_ _
Jig Us ill
a) o o Jo o
O C30
Jo
us in Us
I!: Z Z
O I 0
o
I V
Q us us
so
C7
O Jo
H a, . Us Us
Rho I z 2:
13 h. _ _
I Us
Jo o o
En us o o I
owe I o
. . ..
CO
I
. .
s: o en o
ô o ox
on
_ _ _ _.
n a
. id Nil t`
a) , .
PRO I O O
I
us x
a R o o I _
a so .
3 I I z o
a
.
o x x
I
I
~46- GLUE
Referring to tune data in Table IX, it is seen
that the compound of Example 1 and Compound D both
selectively controlled quack grass in peanuts, rape,
sugar beets, wheat and aureole, but the selectivity
5 factor of the compound of Example 1 Was significantly
greater than that for Compound D in peanuts, rape an
sugar beets; equivalent in wheat and Less in barley.
The compound of Example 1 selectively controlled yellow
nut sedge in each crop in tune test, except sugar beets,
whereas Compound E aid no selectively control yule
nut sedge in sugar beets, sorghum or wheat.
The high unit activity of Compounds D and E
shown in Table IX is y~nerally cnaracteristlc of the
short-term greenhouse performance (i.e., I weeks) for
these compounds against quackgrdss Edna yellow nutse~ge.
However, as shown herein, all relevant test data, both
in the greenhouse and in the field have establ Shea the
uni~onmly superior unit activity against quackg~ass and
yellow nut sedge and crop selectivity ox tune compound ox
Example 1 vis-a-vis Compound D and E for outstandingly
longer periods of time. In this connection, reference
should be made again: (l) to Table IV which contains
comparative field test data for up to 9.5 weeks for the
performance of these co~pGUnds against quakers and
other weeds in soybeans; (neither Co~npoun~ nor E
selectively controlled quack grass in soybeans even a
the 3 'NAT observation); 12i to the adore Alsatian of
the comparative field test data for the performance of
these compounds against yellow nutsecige arc: owner weeps
30 in cotton or up to nine weeks (neither Compound D nor
E selectively controlled yellow nu~sedge in cotton even
at the 2 WIT observation); and I to Table V which
sets forth comparative soil live data lo. the coinpoun~
of Example 1 and Compounds D and E against yellow
nut sedge and quack grass for 3, &, 12 and 18 weeks,
wherein thy compound of Example 1 had units of activity
higher than those of Compounds D and E at 3 IT (Do
37~
-47-
orders of magnitude at the 12 WIT observation) and by an
indeterminate amount at 18 WIT observations. It should also be
mentioned here that the combined superior unit activity, soil
life and crop selectivity of the compound of Example l vista-
vise Compounds D and E relative to yellow nut sedge andquackgrass is also applicable -to the relative performance of
these compounds in many other weeds, notably, seedling
Johnson grass, hemp sesbania, prickly side, smarted,
lambs quarters, etc.
In one multi-crop/weed test, the reemergence
activity of the compound of Example l was further tested in the
field against certain annual weeds in several crops. on
parallel tests the herbicides were surface applied and pro-
plant incorporated. Observations were made and recorded 33
days after treatment for the propellant incorporated test and 34
DOT for the surface-applied tests. In both tests, the compound
of Example l selectively controlled barnyard grass and green
foxtail in field corn soybeans, cotton, bush beans and
peanuts; lambs quarters were also controlled in soybeans.
Additionally in the PI test, barnyard grass and foxtail
were also selectively controlled in sorghum and sweet corn.
Therefore, it will be appreciated from the
foregoing detailed description that compounds according to this
invention have demonstrated unexpected and outstandingly
superior herbicidal properties both absolutely and relative to
the most structurally relevant compounds, other related
homology and analogs and commercial 2-haloacetanilides of the
prior art. More particularly, compounds of this invention have
demonstrated outstanding unit activity, soil longevity and crop
safety with respect to perennials and annual broadleaf
and narrow leaf weeds in soybeans, cotton, peanuts,
rape, and snap beans and other crops. Still more
particularly, compounds of this invention have
Jo
US- guy
demonstrated superior herbiciaal activity against the
perennials yellow nut sedge and ~uackgrass; annual
broadleaf such as hemp sesbania, prickly side,
lambs quarters and smarted and annual narrow leaf weeps
such as barnyard grass, crabgrass PI shatter cane
and itchgra~s. Moorer t compounds of this invention
have been shown Jo be generally comparable to the best
of the relevant prior art compounds in the control of
other annual grass weeps such as seedling Johnson grass,
crabgrass (surface applied), the foxtails Texas
panicum, Allah panicum, wild pros millet,
Alexander grass and red rice and annual broadleaf weeds
such as pugged an jimsonwee~. Finally, compounds of
this invent ion have also demonstrated increased
activity and suppression of resistant annual broadleaf
weeds such a morning glory, cocklebur, ragweed and
veivetleaf.
Toxicology studies on the compound of Example
l have indicated the compound Jo by quite safe It was
slightly toxic by ingestion (single dose OLD - 2,6~0
mg~kg), slightly toxic through single dermal
applications (DLD50 Lowe mgjkg), a slight eye an
skin irritant No special handling procedures ennui
normal precautions are deemed necessary.
~49~ AGO
The herbicidal compositions of tins invention
including concentrates which require ablution prior Jo
application contain at least one active ingredient and
an adjutant in Lowe or solid form. The compositions
are prepare by a~mlxing the active ingredient with an
ad junta including delineates, extenders, carriers and
conditioning agents to provide compositions in the form
of finely-di~ided particulate solids, granules,
pullets, sullenness dispersions or emulsions 9 Thus the
active ingredient can be used with an adjutant such as
a finely-dividea solid, a liquid of organic origin,
water, a wetting agent, a dispersing agent, an
emulsifying agent or any suitable combination of these.
The compositions of this invention,
lo particularly locoweeds and wettable powders, preferably
contain as a conditioning agent one or more
surface-actlve agents in mounts sufficient to fencer a
given composition readily dispersible in water or in
oil. The incorporation of a surface-active agent into
the compositions greatly enhances their efficacy. By
tune term "surace-active agent" it is understood that
wetting agents, dispersing agents, suspending agents
and emulsifying agents are inkwell therein. anionic,
~50- A 1220
cat ionic and n~n-lorlls~ agents can be use win equal
facility O
Preferred wetting events are alicyl Bunsen
and alkyd naphthalene sulfonates/ sulfated fatty
5 alcohols, amaryllis or acid asides, long chain acid esters
of sodium isothionate, esters of sodium sulfosuccinate,
sulfated or sulfonated Patty aria esters petroleum
sulfonates, sul~onated vegetable oils, deterrer
acetylenic glycols, poiyoxyethylene derivatives of
alkylphenol~ (particularly isooct~lphenol and
nonylphen~l) and polyoxyethylene derivatives of the
Monroe fatty acid esters of hexitol androids
(e.g., sorbitan). Preferred dispersants are methyl
cellulose polyvinyl alcohol sodium lignin sulfonates,
polymeric alkyd, naphthalene sealants, sodium
naphthalene sulfonate, and the polyethylene
bisnaphthalene silent.
Wettable powders are water-aispersible
compositions containing one or more active ingredients,
an inert solid extender and one or more wetting an
dispersing agents. The inert solid extenders are
usually ox mineral origin SEIKO as tune natural cloys,
diatomaceous earth and synthetic minerals derived from
silica dud the like. examples of such extenders
include coolants, attapulgite clay and synthetic
magnesium silicate. The wettable powders colnpositions
of this invention usually contain from about 0.5 to 60
parts (preferably from 5~20 parts) of active
ingredient, from about 0.25 to 25 parts (preferably
1-15 parts) of wetting agent, from about U.25 to 25
part (preferably 1.0-15 parts) of dis~ersant and iron
5 to about 95 parts preferably 5-50 parts) of inert
solid extender, all parts being by weight ox the total
composition. Where required, fragile about 0.1 to 2.0
parts of the solid inert extender can be replaced by a
corrosion inhibitor of anci-foaming dent OLD born.
Other formulations include dust concentrates
comprising from 0.1 to 60% by weight of the active ingredient
on a suitable extender; these dusts may be diluted for
application at concentrations within the range of from about
0.1-10% by weight.
Aqueous suspensions or emulsions may be prepared
by stirring an aqueous mixture of a water-insoluble active
ingredient and an emulsification agent until uniform and then
homogenized to give a stable emulsion of very finely-di~ided
particles. The resulting concentrated aqueous suspension is
characterized by its extremely small particle size, so that
when diluted and sprayed, coverage is very uniform. Suitable
concentrations of these formulations contain from about 0.1-60%
preferably 5-50~ by weight of active ingredient, the upper
limit being determined by the volubility limit of active
ingredient in the solvent.
In another form of aqueous suspensions, a water-
immiscible herbicide is encapsulated to form micro encapsulated
phase dispersed in an aqueous phase. In one embodiment, minute
capsules are formed by bringing together an aqueous phase
containing a lignin sulfonate emulsifier and a water-immiscible
chemical and polyethylene polyphenylisocyanate, dispersing the
water-immiscible phase in the aqueous phase followed by
addition of a polyfunctional amine. The isocyanate and amine
compounds react to form a solid urea shell wall around
particles of the water-immiscible chemical, thus forming
micro capsules thereof. Generally, the concentration of the
micro encapsulated material will range from about 480 to 700 g/l
of total composition, preferably 480 to 600 glue
Concentrates are usually solutions of active
ingredient in water-immiscible or partially water-
,;
I
-52- A 1220
immiscible sonnets together with a surface active
agent. Suitable solvents for the avow ingredient ox
this invention include dimethylEormide,
dimethylsulfGxide, N-methylpyrro1idone, hydrocarbons
and water-immiscible ethers, esters or cauterizes
How Yen, other high strength liquid concentrates may be
formulated by dissolving the active ingredient in a
solvent then diluting, e.g., with kerosene, to spray
concentration.
pa Thy concentrate compositions herein generally
contain from about 0.1 to 95 parts (preferably 5-60
parts) active ingredient, about 0.25 to 50 parts
(preferably lo parts) surface active agent and where
require about 4 to 94 parts solvent, elf parts being
lo by weight based on the total weight of emulsifiable
oil 7
Granules are physically stable partlcul~te
compositions comprising active ingredient adhering to
or distributed through a basic. matrix of an inert,
finely-divided particulate extender. In order to air
leaching ox the active ingrealent from toe particulate,
a surface active agent such as those listed
herein before can be present in thy composition.
Natural clays, ~yrophyllites, islet an vermiculite
are examples of operable classes of particulate Ininera
extenders. Thy preferred extenders are the porous,
absorptive, preformed particles such as prerormec; an
screened particulate attapulgite or neat expanded,
particulate vermiculite and the finely divide Lowe
such as kaolin clays, hydrated autopilot or
bentonitic cloys. These extenders are sprayed or
blended with the active ingredient to form the
herbicide granules.
The granular compositions ox this invention
35 may contain from about 0.1 to about 30 parts preferably
from about to 20 parts by weight of active in~redlerlt
per lo parts by weight of clay an O to about 5 parts
-53~ 1220
by weight of surface active Kent per ~00 parts by
weight of particulate clay
The compositions OX this invention can also
contain other adamants, for example, fertilizers
5 other herbicides, other pesticides, safeness an tile
Like used as adjuvan s or in combination with any of
the above-described adjuv~nts~ Czechs useful in
combination with the active ingredient of this
invention include, for example treasons, ureas,
carbamates, acetamides~ acetanilides, uracils, acetic
acid or phenol derivatives, t~liolcarb~m~tes, rissoles,
benzoic acids, nitrites t biphenyl ethers and the like
such as:
2-Chloro-4-ethylamino-6-isopropylamino-s-triazine
2-Chloro~,6-bis(isopropylamino)-s-triazine
- 20Chloro;4,6-bis(ethylamino)-s-triazine
3-Isopropyl-lH-2/i,3~benzothiadiazin-4 (one
2,2 dioxide
3-Amino-1,2,4-triazoie
6,7-Dihydrodipyriao~1,2-~:2',1'-c)-pyrazidilnlum
salt
S-Bromo-3-isopropyl~6-me~hylura
1,1'-Dimethyl-4,4'-bipyridinium
Ureas
N'-(4-chlorophenoxy) phenyL-N,N-dimethylurea
N,N-dimethyl-N'-(3-chloro-~-metnylphenyl) urea
3-(3,4-dichlorophenyl~-1,1 dimethylurea
1,3-Dimethyl-3-(2-~enzothiazolyl) urea
3-(p-Chloropheny~ -dimethylurea
l-Butyl~-(3,4-iahlorophenyl)-1-methylured
I
`- -54- A: 12:20
C~rbamates~Thloicar~amates
Jo .
2-Chloroallyl diethyldithiocarb~ate
So chlorobenæyl)N,N~diethy1thioicarbamate
Isopropyl N-(3-~h10ropheny1) carbamate
S S-2,3-dichloroallyl N,N-diisopropy1tnioicar~ama~e
Ethyl N,Ndipropy1~hio1ca-rbamate
propel dipropyl~hio1c~rbamate
~=~~
2-Chioro-N,N-diallylacetamide
N,NdLmethyl-2,2-diphenylacet~mide
N-(2,4-dimethyl-5-LL(trifluoromethy1~sulfonyl]
amino]phenyl)acetamide
N~Isopropyl-~-chloroacetanil ire
2 ', 6 ' -l;)iethyl-N em thoxymethyl-2-chloroacetanilide
2 ' -Methyl-6 ' ethyl ( 2-methoxyprop-2 ye -2-
chloroacetanilide
do I -Trif1uoro-2,6-ainitro-N,L~-
dipropyl-~-toluidine
N-(l,1-dimethylpropynyl)-3,5-alch10robenz~luia~
Aciàs/Esters/Aicohols
2, ~-Dici~loropropionic Shea
2-Me~hyL-4-chlorophenoxyacetic acid
2,~-Di~nlorophenoxyacetic aria
methyl 2-~4-t2,4-aichlorophenoxy)phenoxyi
preappoint
3-Amino-2,5-dichlorobenzolc Sue
2-Methoxy-3,~-dichlorobenz3ic aria
~,3,6-Trich10ropheny1acetic acid
N-l-naphthylphthalamic acid
I sodium 5-i2-ch10ro-~-(trifluoroMe~hy1)~heno~y~
nitrobenzoate
US 20
4,6~Dinitro~o-se~-buty1pnenol
N-(phosphonometnyl~ Lawson an its C1 -
mono~lkyl amine an alkaline m~tai swept no
combinations thereof
Ethers
2,4-Dich1Orophenyi-~-nitropheny1 ether
sheller- ox, GC,c~ -trifluoro-~-~olyl-3-ethoxy-
4-nitrodiphenyl ether
~isceIlaneous
2,6-~ichlorobenxonitrile
Mainsail aria meth~ne~rson~te
sodium methanears~nate
Fertilizers useful in corllbination with the active
ingredient include, for example, ammonium nitrate,
urea, potash and superphospnate. tuner useful
additaments include materials in which plant organisms
take root and grow Such as compost manure, humus, sane
and the icky
Herbicidal formulations of the types dozier
above are exemplified in several illustrative
embodiments below.
I. _ulsifiabie Concentrates
Pun
A. Compound Of Example No. 150.u
Calcium doàe~y1benzene sulk
fonate~polyoxyethy1ene ethers blend
(ego At lox 3437F and Attics 343~F)5.0
Monoch1Orobenzene 45~0
iuOo (JO
I
-56- A 1220
a. Compound of Example No. 12 OWE
Calcium duds su~fonate/al
kylaryl polyether alcohol blend I.
Cog aromatic hydrocarbons solvent 0
S 1~)0 o US
I Compound of Example No. 13 5.0
Calcium doaecylbenzene sulfonate/
polyoxyethylenP others blend (erg., At lox
3437F) lo
I Zillion 94~0
lug.
IT
Weight Percent
A. Compound of Example No. l Lowe
Zillion OWE
loo 00
B. Compound of Example No. 2 ~5.0
Dimetnyl sulfoxide lid
100. 00
I Compound ox sample No. 3 50.0
N-methylpyrrolldone 50.U
100. 00
D. Compound ox Example No. 4 5.0
Ethoxyla~ed cds~or oil 20.0
Radiomen B Ox
Dim ethyl formamide 74.5
100. 00
AYE 1220
Isle Emulsion
___
I con
. Compound OX example No. 1~0,0
Polyoxyethylene/polyoxy-
propylene block copol~mer with Bunnell
ego., Tergitol~ I I
Waxer 56 0
isle. 00
B. Compound of Example No. 55.0
Polyoxyethylene~poiyoxy-
propylene block copolymer with buttonhole 3~5
Tory lo
10~.0
IV. Welt bye Powder
:~35L'~
A Compound of Example No 125.0
Sodium lignosulfonate mu
Sodium N-methyl-N;-oleyl-taurate lug
Amorphous silica (synthetic 71.0
100.00
B. Compound of Example No. 68~.0
Sodium ductile suifosuccinate 1.25
Calcium lignosulfonate 2-75
Amorphous silica synthetic) owe
Lowe
C. Compound of Example No. Lowe
~OaiUTn lignosulfon~te 3~0
sodium N-methyl-N-oleyl-taurate 1.0
Coolant clay I
100. (I
~58- A 1220
V. Dusts
W 14h C icy eke
. Compound of Example No. 1 2. 0
Attapulglte 9Sd. O
lo. 00
By Compound of Example No.. 600 0
~lo~norillonite 40 . O
100.0
CO Compound ox ~xa~aple No. 9 I 0
Bentonite 70 . 0
10~. 00
D. Compound of Example No. I 1. 0
Diatomaceous jar h 99 . 0
100. I
VIM Granules
Lowe
A. Communed of Example No. 1 15., 0
Granular attapulgite (20~40 mesh) ~5.0
100, I)
I B. Compound or Example No . 23 0 . 0
Diatomaceous earth ( 20/40 I lo
lout I
C. Compound of Example No. 13 0. 5
Bentonite 20/40 ) . 5
lo 00
D. Compound of Example No. 14 S. 0
Powerful 1 i lo ( I Us 0 Jo 5 . O
10~. Us
I A aye
VIM En
A Compound ox example No 1
encapsulated in puller Hell wall ~9.2
Sodium lignosul~ona~e (eye
5 Relax 88~B) Or
Water 4g.~
LOWE. 00
B. Compound of Example No. 12
encapsulated in puller shell well 10.0
potassium lignosulfonate ego,
Rex C 21) .5
Water 89.5
0
C. Compound of Expel No 13- en-
15 capsulated in puller shell wall ~0.0
Magnesium salt ox 1ig~osu~fate
(Trucks LIT 200
Water I a
lljO. I
I When operating in accordance with the present
invention, effective amounts of the acetaniiices of
this invention are applied to the soil containing the
plants, or are incorporated into aquatic media in any
convenient fashion. The application of liquid an
particulate solid compositions to the soil eon be
carried out by conventional methods, e.g., power
dusters, boom and hand sprayers and spray austere. The
compositions can also be applied from airplanes as a
dust or a spray because of their effectiveness at Low
dosages. The application of herbicidal compositions
to aquatic plants is usually carried out by ceding tune
compositions to the aquatic media in the are where
control of the aquatic plants is desired.
60- A 12Z0
The application of an effective amount of the
compounds of this invention to the locus of undesired
weeds is essential an critical for the practice of the
present invention. The exact amount of active
ingredient to be employed is dependent upon various
factors, including the plant species end tare ox
development thereof, the type and Canaan of soil,
the amount ox rainfall and the specific aceEanilide
employed. In selective reemergence application to the
plants or Jo the soil a dosage of prom 0, a to about
Ll.2 kg~ha, preferably from about I to about 5.60
kg/ha, or suitably from 1.12
to 5.6 kiwi of acetanilide is usually employed. Lower
or higher rates may be required in some instances. One
skilled in the art can readily determine from this
specification, including the above example, the optimum
rate to be applied in any particular case.
The term "isle" is employed in its broadest sense
to be inclusive of all conventional "soils" as define
in Webster's New International Dictionary, Second
Edition, Unabridged (1961). Thus the term refers to
any substance or media in which vegetation may take
root and grow, and includes not only earth but also
compost, manure, muck, humus, sand an the like,
await to support plant growth.
Although the invention is described with respect
to specific modifications, the details errs are not
to be construed as limitations except to the extent
indicated in the hollowing claims.
