CA1221379A - Herbicidal 2-haloacetanilides - Google Patents

Abstract

HERBICIDAL 2-HALOACETANILIDES Abstract of the Disclosure The disclosure herein relates to a group of N-hydrocarbyloxymethyl-2-haloacetanilide compounds, herbicidal compositions containing said compounds as the active ingredient and herbicidal method of use in various crops, particularly, soybeans, cotton, peanuts, rape and bush beans. The herbicides herein are particularly effective against hard-to-kill perennial weeds such as quackgrass and yellow nutsedge and against annual weeds, including prickly sida, hemp sesbania, seedling johnsongrass, shattercane, etc.

Description

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

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.

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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~:

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

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~

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.

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-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.

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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.

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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

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

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 !,`~`

"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

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 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.

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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 .

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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.

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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

(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~

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.

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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 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~

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 .

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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 .

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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.

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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.

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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~

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

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

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

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 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 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.

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.

Claims (45)

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:

1. Compounds of the formula wherein R is ethyl, n-propyl, isopropyl, isobutyl, sec-butyl, cyclopropylmethyl, allyl or propargyl;
R1 is methyl, ethyl, n-propyl or isopropyl and R2 is hydrogen, methyl or ethyl; provided that;
when R2 is hydrogen, R1 is ethyl and R is allyl;
when R1 is ethyl, R1 is methyl and R is isopropyl;
when R1 is methyl, R is ethyl, isopropyl, isobutyl; sec-butyl or cyclopropylmethyl;
when R1 is ethyl, R is sec-butyl, allyl or propargyl ;
when R1 is n-propyl, R is ethyl and when R1 is isopropyl, R is ethyl or n-propyl.

2. Compound according to Claim 1 which is 2'-methoxy-6'-methyl-N-(isopropoxymethyl)-2-chloro-acetanilide.

3. Compound according to Claim 1 which is 2'-methoxy-6'-methyl-N-(ethoxymethyl)-2-chloroacet-anilide.

4. Compound according to Claim 1 which is 2'-methoxy-6'-methyl-N-(1-methylpropoxymethyl)-2-chloroacetanilide.

5. Compound according to Claim 1 which is 2'-ethoxy-6'-methyl-N-(allyloxymethyl)-2-chloro-acetanilide.

6. Compound according to Claim 1 which is 2'-ethoxy-6'-methyl-N-(propargyloxymethyl)-2-chloro-acetanilide.

7. Compound according to Claim 1 which is 2'-ethoxy-6'-methyl-N-(1-methylpropoxymethyl)-2-chloro-acetanilide.

8. Compound according to Claim 1 which is 2'-n-propoxy-6'-methyl-N-(ethoxymethyl)-2-chloro-acetanilide.

9. Compound according to Claim 1 which is 2'-isopropoxy-6'-methyl-N-(ethoxymethyl)-2-chloro-acetanilide.

10. Compound according to Claim 1 which is 2'-isopropoxy-6'-methyl-N-(n-propoxymethyl)-2-chloro-acetanilide.

11. Compound according to Claim 1 which is 2'-ethoxy-N-(allyloxymethyl)-2-chloroacetanilide.

12. Compound according to Claim 1 which is 2'-methoxy-6'-ethyl-N-(isopropoxymethyl)-2-chloro-acetanilide.

13. Method for combatting undesirable plants associated with crop plants which comprises applying to the locus of said plants a herbicidally effective amount of a compound having the formula wherein R is ethyl, n-propyl, isopropyl, isobutyl, sec-butyl, cyclopropylmethyl, allyl or propargyl;
R1 is methyl, ethyl, n-propyl or isopropyl and R2 is hydrogen, methyl or ethyl; provided that;

when R2 is hydrogen, R1 is ethyl and R is allyl;
when R2 is ethyl, R1 is methyl and R is isopropyl;
when R1 is methyl, R is ethyl, isopropyl, isobutyl, sec-butyl or cyclopropylmethyl;
when R1 is ethyl, R is sec-butyl, allyl or propargyl;
when R1 is n-propyl, R is ethyl and when R1 is isopropyl, R is ethyl or n-propyl.

14. Method according to Claim 13 wherein said compound is 2'-methoxy-6'-methyl-N-(isopropoxy-methyl)-2-chloroacetanilide.

15. Method according to Claim 13 wherein said compound is 2'-methoxy-6'-methyl-N-(ethoxymethyl)-2-chloroacetanilide.

16. Method according to Claim 13 wherein said compound is 2'-methoxy-6'-methyl-N-(1-methyl-propoxymethyl)-2-chloroacetanilide.

17. Method according to Claim 13 wherein said compound is 2'-ethoxy-6'-methyl-N-(allyloxymethyl)-2-chloroacetanilide.

18. Method according to Claim 13 wherein said compound is 2'-ethoxy-6'-methyl-N-(propargyloxy-methyl)-2-chloroacetanilide.

19. Method according to Claim 13 wherein said compound is 2'-ethoxy-6'-methyl-N-(1-methyl-propoxymethyl)-2-chloroacetanilide.

20. Method according to Claim 13 wherein said compound is 2'-n propoxy-6'-methyl-N(ethoxymethyl)-2-chloroacetanilide.

21. Method according to Claim 13 wherein said compound is 2'-isopropoxy-6'-methyl-N-(ethoxy-methyl)-2-chloroacetanilide.

22. Method according to Claim 13 wherein said compound is 2'-ethoxy-N-(allyloxymethyl)-2-chloro-acetanilide.

23. Method according to Claim 13 wherein said compound is 2'-methoxy-6'-ethyl-N-(isopropoxy-methyl)-2-chloroacetanilide.

24. Method according to Claim 13 wherein said crops are soybeans, cotton, peanuts, rape, bush beans, sugarbeets, sorghum, wheat or barley.

25. Method according to Claim 24 wherein said undesirable plants are perennial grass and sedge weeds and annual weeds.

26. Method according to Claim 25 wherein said perennial weeds are quackgrass and yellow nutsedge.

27. Method according to Claim 25 wherein said annual weeds are broadleaf weeds.

28. Method according to Claim 27 wherein said broadleaf weeds are prickly sida, hemp sesbania, pigweed, smartweed, lambsquarters and jimsonweed.

29. Method according to Claim 25 wherein said annual weeds are grasses.

30. Method according to Claim 29 wherein said grasses are foxtails, barnyardgrass, crabgrass, panicums, shattercane, alexandergrass, red rice and itchgrass.

31. Method according to any of Claims 24, 25 or 26 wherein said compound is 2'-methoxy-6'-methyl-N-(isopropoxymethyl)-2-chloroacetanilide.

32. Method for selectively controlling the growth of weeds in soybeans, cotton, peanuts, rape, snap beans, sugarbeets, sorghum, wheat or barley which comprises applying to the locus of said weeds a herbicidally-effective amount of 2'-methoxy-6'-methyl-N-(isopropoxymethyl)-2-chloroacetanilide.

33. Method for suppressing weed stands of ragweed, morningglory, cocklebur and velvetleaf which comprises applying to the locus thereof a herbicidally-effective amount of 2'-methoxy-6'-methyl-N-(isopropoxy-methyl)-2-chloroacetanilide.

34. Herbicidal compositions comprising an adjuvant and a herbicidally effective amount of a compound having the formula wherein R is ethyl, n-propyl, isopropyl, isobutyl, sec-butyl, cyclopropylmethyl, allyl or propargyl;
R1 is methyl, ethyl, n-propyl or isopropyl and R2 is hydrogen, methyl or ethyl; provided that;
when R2 is hydrogen, R1 is ethyl and R is allyl;
when R2 is ethyl, R1 is methyl and R is isopropyl;
when R1 is methyl, R is ethyl, isopropyl, isobutyl, sec-butyl or cyclopropylmethyl;
when R1 is ethyl, R is sec-butyl, allyl or propargyl;
when R1 is n-propyl, R is ethyl and when R1 is isopropyl, R is ethyl or n-propyl.

35. Composition according to Claim 34 wherein said compound is 2'-methoxy-6'-methyl-N-(isopropoxymethyl)-2-chloroacetanilide.

36. Composition according to Claim 34 wherein said compound is 2'-methoxy-6'-methyl-N-(ethoxymethyl)-2-chloroacetanilide.

37. Composition according to Claim 34 wherein said compound is 2'-methoxy-6'-methyl-N-(1-methylpropoxymethyl)-2-chloroacetanilide.

38. Composition according to Claim 34 wherein said compound is 2'-ethoxy-6'-methyl-N-(allyloxymethyl)-2-chloroacetanilide.

39. Composition according to Claim 34 wherein said compound is 2'-ethoxy-6'-methyl-N-(propargyloxymethyl)-2-chloroacetanilide.

40. Composition according to Claim 34 wherein said compound is 2'-ethoxy-6'-methyl-N-(1-methylpropoxymethyl)-2-chloroacetanilide.

41. Composition according to Claim 34 wherein said compound is 2'-n-propoxy-6'-methyl-N-(ethoxymethyl)-2-chloroacetanilide.

42. Composition according to Claim 34 wherein said compound is 2'-isopropoxy-6'-methyl-N-(ethoxymethyl)-2-chloroacetanilide.

43. Composition according to Claim 34 wherein said compound is 2'-isopropoxy-6'-methyl-N-(n-propoxymethyl)-2-chloroacetanilide.

44. Composition according to Claim 34 wherein said compound is 2'-ethoxy-N-(allyloxy-methyl)-2-chloroacetanilide.

45. Composition according to Claim 34 wherein said compound is 2'-methoxy-6'-ethyl-N-(isopropoxymethyl)-2-chloroacetanilide.