CS219855B2 - Herbicide means - Google Patents

Abstract

N-alkoxymethyl-2-haloacetanilide compounds, herbicidal compositions containing said compounds as the active ingredient and herbicidal method of use in various crops, particularly sorghum. Herbicides herein are particularly effective against hard-to-control weeds particularly seedling johnsongrass and/or shattercane, white proso millet, yellow nutsedge and redroot pigweed in addition to yellow foxtail, barnyardgrass and crabgrass.

Description

The present invention relates to a class of N-alkoxymethyl-2-haloacetanilide derivatives, herbicidal compositions containing the compounds as active ingredient and herbicidal. methods used in various crops, especially sorghum. The herbicides described herein are particularly effective against hard-to-control. weeds, especially halip sorghum and / or shattercane seedlings, millet, bilberry, buckwheat, and pig-tailed hedgehog and bloody deer.

The present invention relates to 2-haloocetonilides and their use in agricultural production as herbicides.

The prior art articles disclose numerous discoveries of 2-haloacetanilides which are unsubstituted or substituted by very diverse substituents on the anilide nitrogen atom and on the onillide ring, wherein substituents include alkyl, alkoxy, alkoxyalkyl, halogen and the like.

The compounds of the invention are characterized in that they have an alkoxymethyl or alkenyloxymethyl group on the nitrogen of the onilide, an alkoxy group or an alkenyl group in one ortho position and hydrogen or a particular alkyl group in the other ortho position. The earliest prior publications known to the author are US Patents 3,442,145'45 and 3,547,620. The most relevant substances disclosed in US Patent Nos. 3,442,945 and 3,547,620 are 2'-tert-butyl-2-chloro compounds. -N-methoxymethyl-6'-methoxyocetonilide and its bromo analogue (Examples 18 and 34 of US Patent No. 3,547,620 and Examples 18 and 36 of US Patent No. 3,442,945).

U.S. Pat. Nos. 4,079,389 and 4,152,137 disclose a general formula that includes compounds of the type set forth in U.S. Patent Nos. 3,442,945 and 3,547,620. However, only the derivatives described herein contain an alkyl group in one ortho position and an alkoxy group. in the second ortho position, they have an alkoxyethyl group on the anilide nitrogen atom. Compounds of this type are described in more detail below.

Other less important earlier publications are Belgian Patent No. 8110 763 of the Federal Republic of Germany No. 24 02 983. The compounds of these publications include compounds of the type disclosed in U.S. Patents 4,070,389 and 4,152,137, and are characterized in that alkoxyalkyl the groups have two or more carbon atoms between the anilide nitrogen atom and the oxygen atom of the alkoxy moiety. The most important individual discoveries mentioned after Belgian patent No. 8110 763 and the German publication No. 24 02 983 are apparently compounds having an ethoxyethyl group on the anilide nitrogen atom, a methoxy or ethoxy group in one ortho position and a methyl or isopropyl group in the other ortho- position. In reference to Belgian Patent No. 810 · 763, reference is made to compounds No. 7, 16 and 18. Other less important homologues of these compounds are also described, such as compounds 6, 9 and 17 having a nitrogen atom substituted with methoxyethyl or methoxypropyl, methoxy or ethoxy in one ortho position and methyl in another ortho position.

The above-mentioned U.S. Patent No. 3,442,945 discloses the compounds listed above having the chemical configuration closest to the compounds of the invention and containing certain herbicidal data. Some data are also given for other homologues and analogous compounds without a close chemical structure. Similarly, some data for compounds 6 and 9 in Belgian Patent No. 810,763 are mentioned. In particular, these most important references, when describing a herbicidal effect on various weeds, do not provide any data for some compounds which prove suitable for additional and / or at the same time controlling hard-to-control narrow-leaved weeds, seedling johnsongrass seedlings and / or shattercane belonging to the same plant genus as common sorghum and other hard-to-control weeds such as bentweed, millet (Panicum miliaceum), less resistant weeds such as yellow foxtail, hedgehog corn and bloody dew while sorghum remains intact. Said Belgian Patent No. 810,763 discloses data showing that Compound No. 6 destroys sorghum. However, there is no mention of the effect of compound 9 on sorghum. As will be illustrated below, the novel compounds of the invention have infinitely superior properties as selective herbicides to sorghum compared to homologous compounds of the previous species.

It is an object of the present invention to provide herbicides that selectively control hard-to-control weeds, such as sorghum seedlings and / or shattercane. Certain derivatives of the present invention suppress other hard-to-control weeds, such as bentweed, gooseberry and millet, in addition to less resistant weeds, such as fox-tails, hedgehogs, corn-legged blooms, especially in sorghum generally better than earlier products.

The foregoing and other features of the invention will become more apparent from the detailed description set forth below.

The present invention relates to herbicidally active compounds, to herbicidal compositions comprising the compounds as active ingredients of herbicidal methods for the use of such compositions in particularly sown areas, in particular sorghum.

It has now been discovered to be selected. a group of 2-haloacetonilides characterized in that it contains certain alkoxymethyl or olkenyloxymethyl groups on the anilide nitrogen atom, certain alkoxy groups in one ortho-position ο hydrogen or methyl group in the other ortho-position has unexpectedly superior and excellent selective herbicidal properties , as a sorghum herbicide against earlier herbicides, including homologous compounds from the most important previous publications.

A first feature of the herbicidal compositions of the present invention is their ability to selectively control narrow-leaved weeds, holep sorghum seedlings and / or shattercane, which are directed to the same plant genus as sorghum. In fact, they are common sorghum, and shattercane are both a kind of two-color sorghum. Therefore, it is extremely difficult to selectively suppress shattercan and sorghum seedlings in common sorghum without simultaneously damaging the common sorghum. In addition, some of the compounds of the invention also suppress other hard-to-control species, such as bent-tailed pigweed, broadgrass and / or millet. All of the compounds of the invention suppress other species, such as fox-tail, hedgehog, legwort and other harmful weeds.

The compounds of the invention have a general formula

where

R is isopropyl, n-butyl, isobutyl, sec-butyl, allyl or 2-methylbutyl,

R 1 represents methyl, isopropyl, n-butyl or allyl and

R 2 and R 3 are hydrogen or methyl, with the proviso that

R1, R2 and R5 are each methyl when R is n-butyl, isobutyl or sec-butyl,

R2 and R3 are each hydrogen when R is isopropyl, isobutyl or sec-butyl and

R 1 is isopropyl or n-butyl and

R2 is hydrogen;

R 3 is methyl when

R is 2-methylbutyl or allyl and R 1 is allyl.

Preferred compounds of the invention are:

N- (isobutoxymethyl) -2‘-methoxy-3‘, b‘-dimethyl-2-chloro-racetanilide,

N- (n-butoxymethyl) -2'-methoxy-2,4-dimethyl-acetonitrile,

N- (sec-uto xy-J-methyl-2'-methoxy "XY-3 ', ^16'-d; methyl-2-chloϊacetanilid,

N- (allyloxymethyl) -2‘-allyloxy-6‘-methyl-2-chloroacetamide,

N- (2-methylbutoxymethyl) -2'-allyloxy-6-methyl-2-chloroacetanilide,

N- (isopropoxymethyl) -2‘-isopropyloxy-2-chloroacetanilide,

N- (isobutoximethyl) -2‘-isopropoxy-2-chloroacetanilide a

N- (sec-butoxymethyl) -2‘-n-butoxy-2-chloroacetamide.

The use of the compounds of this invention as active ingredients in the hetbicidal formulations which they form as well as methods of using them are described below.

The compounds of the invention can be prepared by various methods. These compounds can be prepared according to the procedure described in the above-mentioned U.S. Pat. Nos. 3,442,145 and 3,547,612. By the azomethine process, a suitable primary aniline is reacted with formaldehyde to give the corresponding nethylenaniline (substituted with a haloacetylating agent, such as chloroacetylanhydride, which is further reacted with the appropriate alcohol. N, N-chloroacetanilide.

Another method for the preparation of the compounds of this invention consists in N-alkylating the anion of a suitable secondary 2-halogenoacetanilide with an alkylating agent under basic conditions.

The correction of said N-alkylation process is described in Example 1 for the preparation of the compounds of the invention. N-alkylation procedure described in Example 1 involves in situ generation · halogenmethylalkyletberů ^one used as starting materials in the process JSalkylačním. . :

Example 1

This example describes the use of an N-alkylation process to produce compounds of the invention. In this example, the alkylating agent is formed in situ to provide an efficient, economical and simple operation.

To a cold mixture of 9.25 g (0.125 mol) of isobutylalcohol, 1.180 g (0.062 mol) of anhydrous paraformaldehyde and 100 ml of nethylene chloride, add · 7.56 g (0.062 mol) of acetyl bromide · Stir until all paraformaldehyde is dissolved, This is about 45 minutes and then 4.55 g (0.02 mol) of 2'-methoxy-3 ', 6'-dimethyl-2-chloroacetanilide and 2.0 g of benzyltriethylenomide chloride in 100 ml are added. The mixture was cooled to 15 ° C and 50 ml of 50% sodium hydroxide was added in one portion and stirred for 5 minutes, 160 ml of cold water was added to the mixture, the layers were separated, washed with water, dried with magnesium sulfate and evaporated. 5.0 g · (79% yield) of a yellow liquid having a boiling point of 107 DEG C. at a pressure of 2.7 Pa is obtained.

Analysis for C16H24ClNO3:

found:

C 61.24%, H 7.71%, Cl 11.30-%, calculated:

С 61.24%, Η 7.72%, Cl 11.2'8%.

The product was identified as N -isobutoxymethyl) -2‘-methoxy-3‘, 6‘-dimethyl-2-chloroacetanilide.

Examples 2 to 8

Using essentially the same procedure followed

Table I under the same conditions as those described in Example 1, but substituting the appropriate secondary anilideim and alkylating agent as starting materials in their appropriate amounts produced the corresponding N- (alkoxymethyl) - and N- (alkenyloxymethyl) -2-haloacetanilides. These compounds are identified in Table I, where they are listed together with some physical properties.

Example # Compound Empirical formula Boiling point, ° C (pressure, Pa) Element Analysis,% Calculated Found 2 N- (isopropoxymethyl) - C.15H22ClNO3 11.3 C 60,110 60.38 -2‘-isopropoxy- (1,3) H 7,410 6.80 -2-chloroacetanilide Cl 11.83 11.94 3 N- (isobutoxymethyl) - СмНгаСШОз 113 C 61.24 61.2i3 -2‘-lsopropoxy-2- (4.0) H 7.71 7,7'2 -chloracelanilide Cl 11.30 11.30 4 N- (allyloxymethyl) - C18H20ClNO3 116 C 62.03 61.98 -2‘-allyloxy-6‘-methyl- (4.0) H 6.51 6.53 -2-chloroacetanild Cl 11.44 11.44 5 N-sec-butoxymethyl-2'-n-butyl- C17H26ClNO3 115 C 62.28 62.18 (2.7) H 7.99 8.03 -2-chloroacetanilide Cl 10.81 10.80 6 N- (n-butoxymethyl) -2‘-methoxy-3‘, 6‘- C16H25CINO3 108 C 61.24 61.15 (13.3) H 7.71 7.79 -dimethyl-2-chloroacetanilide Cl 11.30 11.30 7 N - ('sec-butoxy- C16H24ClNO3 116 C 61.24 61,1'3 Methyl 1) ^-2-one! thoxy- (9.3) H 7.71 7.78 -3‘, 6‘-dimethyl-2- -chlonacetanilide Cl 11.30 11.24 8 N- (2-methylbutoxy- C18H26ClNO3 118 C 63.61 613.61 methyl) -2‘-allyl- (10.7) H 7.71 7.79 -6‘-Methyl-2-chloro- Cl 10.43 10.44

асе melting people

The secondary anilides used as starting materials in the production described in the above examples are prepared according to known methods, for example by the haloacetylation of the corresponding primary amines with such haloacetylating agents, such as haloacetyl halide or anhydride. Usually, a suitable amount of the appropriate primary amine is dissolved in a solvent such as methylene chloride containing a base such as HO% sodium hydroxide and stirred vigorously while introducing a solution of a haloacetyl halide such as chloroacetyl chloride while cooling to 15-25 ° C. The layers were separated and the organic solvent layer was washed with water, dried and evaporated in vacuo.

The primary amines used for the production of secondary anilides can also be prepared by known methods, for example by catalytic reduction of the corresponding nitrobenzene which is suitably substituted, for example 2-alkoxy-6-alkylnitrobenzene, in a solvent such as an alcohol such as ethanol using a platinum oxide catalyst. to give 2-alkenyloxy- (e.g. -allyloxy) -6'-alkyl compounds. Chemical reductions using iron and acetic acid can be used.

As mentioned above, the compounds of the invention have been found to be effective as herbicides, particularly as pre-emergence herbicides, although a post-emergence effect has also been found. Tables II and III summarize the results of the tests performed to determine the pre-mergent herbicidal effect of the compounds of the invention.

The pre-allergen test is performed as follows:

The topsoil is placed in aluminum pots and compressed to a depth of 9.5 to 12.7 mm from the top of the pot. A predetermined number of seeds or vegetative shoots of different plant species are placed on the soil surface. The soil needed to reach the required height in the pot after sowing or planting the vegetative shoots is weighed. The soil and the known amount of active ingredient are incorporated into a solvent or mixed positively as a wettable powder suspension and used to coat the prepared pots. After treatment, the pots are transferred to a greenhouse workbench, where they receive an initial upper irrigation equivalent to a waterfall of 0.64 cm. The lower irrigation is then carried out as required to achieve a germinating agent for germination and growth.

Approximately two weeks after sowing and treatment, the plants are observed and the results recorded. Tables II and III below summarize the results. The fungicidal evaluation is determined on a fixed scale based on the percentage of damage to each plant species. The values are defined as follows:

The plant species used in one set of tests, the results of which are given in Table II, are identified by the letters as follows:

A poháč

B beet

C ábutílon

D povíjnice

E goosefoot white

F ferns pepper

G šáchor

H creeping grass

Halpean sorghum seedlings

J Brome (Downy Brome)

K hedgehog corns suppression%

Evaluation

0—240 —491

50—742

75—1003

Table II

Preemergent teist

Example compound no. kg / ha AND (B) C D E F Plant type G Η I J TO 1 11.2 3 3 0 ’ 3 3 3 3 3 0 3 3 5 6 1 1 0 3 2 3 3 3 0 3 3 2 11.2 0 1 1 3 1 1 0 3 0 3 3 5.6 0 0 1 2 0 1 0 0 0 3 3 3 11.2 3 O 1 1 0 2 3 2 0 3 3 5.6 0 ' 0 1 1 0 1 3 0 0 3 3 4 11.2 3 1 2 2 2 2 3 0 0 3 3 5 6 3 1 1 1 3 2 3 3 3 3 3 5 11.2 - - - - 2 2 3 2 1 3 3 5.6 0 0 0 0 · 0 ' 1 3 1 0 3 3 6 11.2 3 2 1 2 3 3 3 3 3 3 3 5.6 3 2 1 2 3 3 3 2 0 3 3 7 11.2 3 2 1 2 3 3 3 3 3 3 3 5.6 3 1 1 2 2 3 3 3 1 3 3 8 11.2 3 0 0 0 2 3 1 2 1 3 3 5.6 0 O 0 0 0 0 1 2 2 3 3 Compounds are further tested for] use sho- r: cannabis of the above  procedure on these plants: E mer white lily

F ferns pepper

L soya leguminous C abutilon M diabetes J sveřep N wheat S millet About rice The hedgehog corns the leg P sorghum T bloody bloody

B beet

Q Buckwheat The results are summarized in Table III.

D povíjnice

N ^ QOOCÚO00mOOO ^ OHHONHHQN? J Ч LJ O CO CM Ч 00 СО СО О

COOOOOOHHNNHQOMHHHHWOHONNHOOCCMHOOCOO

CO OJ О О I ΝΟΟΗΗΗ00 [ηΗΓΗΗθΓ) ΗΗΗΟΊ ^ ΗΜτ ~ ΟΊΝΜΗθΗθΟ

4Э

honors Η

Q σ

PQ

CGOQCJQNOlHHtNHQOHOOOCHOOQCWHHHMHQrHQQQPJ

NOOHONM0HO0OHMH0OOHOOOMMHHOmHHr-OOOÏ

СМг-Чфг-ЧфОффООФОФФффФфФОфФСМг-ЧФОФт-ЧФСЗфФфОО

ΙΧι

МС0иОнООННг | О0СОННООНОООГ) М0ООМН0Н0ООО

СОООСМгНфООт-ЧФфООООСМгЧООСО

NHOOO

MO00Q'MOOOCOMWúCONOQ © NOC) QCN ^ HHOmHHNH

qoo

СОгЧООФтЧффОфФффСМгЧг-ЧОфФфФФСМгЧОфгЧСМтЧОффФФО honors

Č0

CM 00 СО гЧ CO CO CO CO CO CO CO 00 00 CO rH CO CO CO 00 00 CO rH

CD H CM О CD CO r-Ч OJ ~ CD CD rH CM Ф ~ СО rH ~ CM _A О CD Т-Ч CM o CO tH см <ф Ф co in T-Γ о СЭ CD 10 г-Г CJ CD ю г-Г θ 'θ' ir r — T cT θ 'сГ юГ τ — Γ Φ θ' ΙτΓ Τ-Γ θ 'θ' ο * 'ΙΟ

OJ 00 Η CM со τ — Γ θ '10

0.28

0.06

СМ о ¹ ю со

Гх 00

It has been found that the herbicides of the invention have unexpectedly superior properties to selected pre-emergent herbicides for use in sorghum, in particular to selectively control hard-to-control weeds including at least one of weeds selected from the group consisting of sorghum sorghum seedlings, shattercane bent, flatwood and millet, among other weed-causing weeds, such as sarcophagus, which roots corn and the dew bleeds. The selective control of the above mentioned as well as other weeds with herbicides according to the invention has been found in various other useful plants including leguminous soybeans, wheat, rice and sugar beet, as mentioned in Table III above. However, the distinctly remarkable herbicidal properties of the compounds of the invention are mainly exemplified by their selective weed control in sorghum.

Comparative greenhouse tests were performed to illustrate the unexpectedly superior properties of the compounds of this invention on both absolute and relative basis.

With homologous compounds known from previous publications having a close chemical structure to the compounds of the invention; and

2] is with two other non-homologous compounds which fall within the scope of the earlier publications and wherein one of them has better properties than the sorghum herbicide and both are commercially available.

All of the compounds in the comparative tests below are generically defined as substituted phenyl-N - (hydrocarbon radical) alkyl-2-haloacetanilides. The former compounds used in the data of the tables to be compared are as follows:

A. N-methoxymethyl-2‘-methoxy-6‘-tert-butyl-2-chloroaceamide (Example 18, US Patents 3,442,945 and 3,457,620)

8. N- (methoxymethylthio) -2-methoxy-6‘-tert-butyl-2-bromoacetamide (Example 34 of US Patent No. 3,547,620 and Example 3'6 of US Patent 3,442,945);

no. N- (methoxyeihyl) -2'-methyl ^{<-methoxy-6-methyl-t} -chloracetanilid (compound no. 6 of belgického- Pat. No. 810 · 763, also shown in German Offenlegungsschrift no. 2,402,983)

D. N- (ethoxyethyl) -2 ^<methoxy-6 <-methyl-2-chloroacetanilide (compound no. 7 · from Belgian patent no. 810763 ·)

E. N- (1- ^ 1 ^^^ - 2 ^ (^ 1) -2‘-methoxy-6‘-methylchlorocetane (compound 9 of Belgian Patent No. 810763)),

F. N- (néthoxyethyl) ^-2'-et) -methoxy-6'-methyl - ^^ i ^ ^ hloraceíl anilide (compound no. 16 of Belgian Patent No. 81Č763 ·)

J. N- (isopropoxyethyl) -4-methoxymethoxy-6-m-ethyl-2-chlorocetanilide,

G. N- (ethoxyethyl) -2‘-ethoxy-b-methyl-2-chloroacetanilide (Compound No. 18 of Belgian Patent No. 810,763),

Η. N- (isopropyl) -2-chloroacetanilide (propachlor),

I. N- (methoxymethyl) -2 ^<6 -'- diethyl-2-chloroacetanilide, (Example 5 · from U.S. Patent Nos. 3,547,620 and 3,442 · 945), commonly known as "alachlor", active ingredient a commercially available herbicide LASSOR, a trademark of Monsanto Company.

Although Compound H above is less similar in structure to the homologous herbicides mentioned in U.S. Patent Nos. 3-442,945 and 3,547, in that it does not contain an alkoxyalkyl or alkenyloxyalkyl substituent on the nitrogen atom and an alkoxy substituent at the ortho position, the compound is included in the tests performed here as it is disclosed in U.S. Patent Nos. 4,073 (3,383,119 and 4,151,237) and has better properties than a commercially available sorghum herbicide compared to other compounds of said patents. it is included in the tests performed herein as it falls within the scope of US Patent Nos. 3,442,945 and 3: 5,447,620 and is available as an industrially produced herbicide.

In overmergent herbicidal tests, the compounds of the invention are compared with compounds A to I from previous citations with respect to the control of various weeds, with emphasis on the hard-to-control narrow-leaved species that predominate in sorghum. The test results are shown below.

In the analysis of the data below, reference is made to the use of a herbicide dose designated as "GRis" and "GRss". · These doses are given in kilograms per hectare (kg ^/! Ha). GRis is defined as the maximum herbicide dose required for 15% or less damage to crops. GR85 is defined as the maximum dose required to achieve 85% weed control. The GRis and GRss doses are used as a measure of the strength of the industrial product and it will be understood that suitable commercially available herbicides may cause greater or lesser damage to the plants within a reasonable limit.

Another measure of the effectiveness of a chemical as a selective herbicide is the 'selectivity factor' (abbreviated as 'SF') for the herbicide in the given crops and weeds. The selectivity factor is a measure of the relative degree of crop safety and weed damage and is expressed by the ratio GRis / GR85, i.e. the dose of GRis for the crop divided by the dose of GRas for the weeds, both of which are reported in kg / ha. In the tables below, the selectivity factor - if used - is expressed in parenthesis after the weed. The symbol NS means "selective". Marginal or questionable selectivity is indicated by the i (-) sign after the crop.

• Because the resistance of the crop and the weed control are correlated with each other, the verbal snub of this relationship with respect to the selectivity factor is important. In general, it is desirable that the safety factor for the crop plants, i.e. the herbicide resistance value, is high, because a higher concentration of herbicide is often needed for some reason. On the contrary, it is desirable that the weed control dose be small, that is to say, that the herbicide has a high unit effect for economic and possibly also ecological reasons. However, small amounts of herbicide applied. it may not be sufficient to control certain weed species, and larger doses may be needed. Therefore, the best herbicides are those which control the largest number of weeds with the least amount of herbicide and have the highest degree of safety for the crop plant, i.e. crop plants are resistant to them. Therefore, the term "selectivity factor" (as defined above) is used to quantify the relationship between crop safety and weed control. In connection with the selectivity factors shown in the table, it is noted that the higher the numerical value, the greater the selectivity of the herbicide for the suppressed weed in said crop.

Preemergence tests herein include both greenhouse and field theist tests. In greenhouse tests, the herbicide is either used for topical application after sowing alone or planting vegetative benefits, or is introduced into a specified amount of soil where it is applied as a surface layer over the test seeds in containers intended for this purpose. In field tests, the herbicide is incorporated ("P.P.I.") into the soil, i.e. the herbicide is applied to the soil surface and then introduced into it by stirring, which is carried out after planting the seeds of the useful plants.

The surface test method used in the greenhouse is carried out as follows:

Containers, such as aluminum pots, usually 24.13X1.3.34 X 6.99 cm ^l, or 9.53 X X9.53X7 7.12 cm plastic pots, equipped with drain holes in the bottom, are filled Ray-like (Ray slit loam salt) soaked to level 1.27 cm from the top of the pot. The seimens of the species to be tested are then sown in the pot and then covered with a layer of test soil 1.27 cm high. The herbicide is then applied to the soil surface with a portable sprayer at a rate of 187 liters per hectare at a pressure of 211 kPa, or with another sprayer, for example a DeVilbris sprayer, also used for this purpose. 0.64 cm of water in the form of overhead irrigation are introduced into each pot and the pots are then placed on greenhouse workbenches where irrigation from below is carried out as needed. In an alternative procedure, the top irrigation may be omitted. Observation of the herbicidal effects is made about three weeks after treatment.

O ^ (^ 1: The soil to which the herbicide is incorporated used in the greenhouse tests is as follows:

The topsoil is poured into the aluminum pots and compressed to a depth of 0.9 to 1.27 cm from the top of the pot. A specified number of seeds or vegetative shoots of different plant species are placed on the soil surface. The soil needed to fill to the rim of the pot after sowing or planting the vegetative shoots is weighed into the pot. The soil and the known amount of active ingredient used in the solvent or wettable powder suspension are thoroughly mixed and used to cover the prepared container. After treatment, the pots are first wetted with water in an amount equal to 0.64 cm of rainfall and then irrigated from the bottom as needed to obtain suitable moisture for germination and growth.

In an alternative approach, irrigation from above may be omitted. Observations are made three weeks after sowing and treatment.

In the tables below, the data for the compounds tested in several experiments is averaged from the rates applied in the range of 0.07 to 2.24 kg / ha.

In the first comparative example, the data on the pre-emergence herbicidal activity are given in Table IV. The relative efficacy of the compounds of Examples 1 and 5, representative of the present invention, is confronted with the close compounds of previous publications, with Compounds A, B, D, F and G as selective herbicides against individual weeds generally associated with sorghum. The weeds used in the tests are indicated in the tables with the following abbreviations:

LO amaranth bent

CH Halpean Sorghum seedlings · SC shattercane

PM millet

JN hedgehog corns foot RK bloody PS psárka ŠA šáohor

219853

1β

Table IV

Compound sorghum GRis Dose (kg / ha) LO GRss Dose (kg / ha) CH RK AND 0.28 2.24 (NS) <0.14 (> 2.0) <0.14- (2.0) (B) <0.14 0.28 (NS) <0.14 (-) <0.14 (-) D <0.14 0.28 (NS) <0.14 (-) <0.14 (-) G <0.14 0.28 (NS) <0.14 - (-) <0.14 F <0.14 0.34. (NS) <0.14 (-) <0.14 (-) Example 1 1.12 2.24 (NS) 0., 1.4 (8.0) <0,1.4- (> 8.0) Example 5 <2.24 > 2.24 (-) 0.14 (> 1i6, O) <0.14 (> 16.0) ΞΙο ^ ι ^^ QP O GR85 Dose (kg / ha). JN SA PM PS AND 0.56 (NS) <0.14 (> 2.0) 1.57 (NS) 1.12 (NS) <0.14 (> 2, O) (B) 0.28 (NS) <0.14 (-) 1.12 (NS) C.56 (NS) <0.14 D <0.14 (NS) <0.14 (-) <0.14 (NS) <0.14 (NS) <0.14 (-) G 0.2.6 (NS) <0.14 (-) <0.14 (-1,56 (NS) <0.14 (-) F 0.14 (NS) <0.14 (-) 0.34 (NS) 0.56 (NS) <0.14 (-) Example 1 207 (NS) <0.14 f> 8.0) 2.07 (NS) 1.67 (NS) <0.14 (> 8.0) Example 5 2 24 (> 1.0) 0.14 (> 16.0) 1.46 (> 1.5)> 2.24 (-) 0 - 56 (> 4.0)

In view of the data in Table IV, it appears that, in view of the safety of the crop (as indicated by the GRis dose for sorghum), the compounds of the invention are extremely good compared to the compounds known to date. Especially with respect to the known compounds of the closest related structure, for example Compounds A and B with the configuration corresponding to N-alkoxy-ethyl-2'-alkoxy-6'-alkyl-2-haloacetanilide, the compounds of the invention are safer in the test performed for sorghum from at least 8.0 to greater than 16, more than Compound B, and from at least 4.0 to greater than 8.0 times, compared to Compound A. Similarly, the compounds of the invention are safer for sorghum. from 8.0 to more than 16, 10, of the thyte, compared to the previously described homologues, compounds D, F and G, each of which causes more than 1.5% sorghum damage at a very low dose, less than 0.14 kg / ha.

Table V

With respect to weed control given by the doses of GRss used for each weed, it should be noted that all previously known compounds used in the tests, except for compound A, are either completely non-selective or their selectivity is problematic or marginal against all weeds in the tests in sorghum. Compared to Compound A, the compounds according to the invention are 4.0 to δ, δ-kaat are more effective against the seedlings of the t-eye, the bloody chicken leg, and the 4, 0-rabbit. more effective against the palate - The compound of the example - tk ^ - ηη ^ - null-selectively-suppressed-and-chorus and has a selective selectivity with respect to the variegated and millet, while the compound has no effect.

In another comparative test compound is compared - Example - to SUJ - ргеете еп ^ n - η & ΓΜιΜη - V- effec- relation к sO ^ i ^ i ^ ⁱ ^ er Inami C, D and. - The Ooiocrto Suffered Aoou listed in Table V.

Compound GRis Dose GRss Batch (kg / ha) (kg / hk) sorghum CH JN RK PS

D <0.14 0.14 (NS) <0.14 (-) <0.14 (-) <0.14 (-) C <0.14 0.28 (NS) <0.14 (-] <0.14 (-) <0.14 (-) J <0.14 0.14 (NS) <0.14 (-)) <0.14 (-) <0.14 (-) Example 1 1.12 0.84 (1.3) <0.14 (> 8.0) <0.14 (> 8.0.) <0.14 (> 8.0)

1B

In connection with the data in Table V, it should be noted that the compound of the invention of Example 1 has a significantly higher safety factor for sorghum than the compounds known hitherto, that is to say at least 8.0 times safer. However, the compound of the invention, in addition to having a higher safety factor for the useful plant, also exhibits a uniform and extremely good selectivity factor, compared to the prior art compounds, against each of the weeds tested. It should be noted that the compounds C, D and J previously known do not have a positive selectivity in utility plants against the sorghum seedlings. Selectivity of these compounds against remaining weeds

Table VI is at best problematic or marginal, and in any case, the low safety factor of these compounds renders the herbicides unsuitable for sorghum.

Further pre-emergence herbicidal data from other tests for compounds 1-8 are shown in Table VI.

Table VI lists the doses of GRis and GR85 for each compound of the invention in sorghum and weeds. The value of the -selectivity factor is in parentheses. Multiple test values represent the average of the indicated number of -tests. White area under individual weeds! indicates that weeds were not present in the test for the compound in question.

Compound GRis dose (kg / ha) sorghum LO Example 1a 1.14 > 0.41 (> 2.8) Example 2 > 1.12 Example 3 > 1.12 Example 4b 0.57 0.43 (1.3) Example 5 ^C > 2.24 > 2.24 (-) Example -6 ^C 0.7 0.14 (5.0) Example 7 ^d > 0.7 0.35 (> 2.0) Example 8 > 1.12 Table VI - continuation Compound JN ŠA Example l ^and 0.0195 (12.0) 1.0 (1.14) Example 2 -0.22 (-5.0) Example 3 0.28 - (> 4.0) Example 4.b <0.09 (> 6.4) 0.35 (1.6) Example 5c 0.116 - (> 14.0) > 1.9 (~ 1.2) Example -6C <0.11 (> 6.4) 0.413. (1,6) Example 7 ^d <0.09 (> 7.8) 0.84 (NS) Example- 8 0.28 (> 4.0)

Dose GRas (kg / ha) SC CH RK 0.43 (2.7 <0.09 (> 12.7) 0.97 (1,18) 0.56 (> 2.0) <0.14 (> 8.0) 0.56 (> 2.0'j) 0.28 (> 4.0) <0.16 (> 3.6) 0.09 (> 6.4) <0.15 (> 3.8) 0.28 (> 8.0) <0.12. (> 18.7) 1,3 ( > 1,7) 0.14 (5., 0) <0.14 (> 5.0) 0.14 (> 5.0) - <0.09 (> 7.8) > 0.11 (—6.4) <0.07 (> • 10.0) 0.21 (> 5.3) 0.28 (> 4.0) Dose GR85 kg / ha) PM PS 0.75 (1.52) 0.12 (9.5). 0.16 (> 7O) 0.46 (> 2.4) 0.64 (NS) 0.09 (6.4) > 1.4 (-1.6) 0.3.6 (> 6.2) 0.21 (3.3) <0.11 (> 6.4) 0.21 (> 3.3) <0.09 (> 7.8) 0, -28 (> 4.0)

a. The figure represents the average of seven times the experiment.

b. The figure represents the average of five times the experiment.

c. The figure represents the average of the duplicate experiment.

d. The figure represents the average of three replicate experiments.

In particular, with reference to the data in Table VI, it is noted that each compound of the invention. tested against both Halep sorghum seedlings and shattercane selectively suppresses these weeds in sorghum at a dosage range of 0.57 to 2.24 kg / ha. The result cannot be compared to any compound known to date, including the commercially available Hal herbicidal compounds. In addition, compound H is considered to be the most important commercially available herbicide for sorghum.

With three exceptions, except that all of the compounds of the invention cause positive selective control of all weeds tested, except that the positive selectivity is devoid of the compound of Example 4 against millet and the compound of Example 7 against the broadleaf and the border selectivity has the compound of Example 5. against a kind bent.

Since the pre-emergence herbicidal data given in Tables IV to VI are obtained by the same procedures, the comparison of the herbicidal activity of the compounds of the invention in Table VI can also be made with respect to the herbicidal activity of the previously known compounds listed in Tables IV and V. Here again, it is clearly demonstrated that each of the compounds of the invention is substantially superior to all very related prior compounds both in terms of crop safety without exception and the overall selectivity of weed control apparent from the selectivity factor, except in isolated cases. . Especially of all the test compounds known so far, only Compound A (Table IV) causes positive selective control of Halep sorghum seedlings, Common Rosebud, Hedgehog Feet and Fifth Common in Sorghum Compound A is non-selective against the remaining weeds tested. which does not selectively suppress Compound A, the compounds of the invention exhibit particularly high selectivity, with the exception of the compounds of Examples 2 and 3, which act against Compound A against halopean sorghum seedlings and again low safety factor for sorghum and / or nonselectivity; the problematic selectivity of the respective previously known compounds against all weeds in the above tests renders these compounds completely unsuitable as herbicides for sorghum.

As previously described, compounds H and I mentioned in the earlier patents mentioned above are active ingredients of commercially produced herbicides. Compound H is widely used as a sorghum herbicide. Although none of these compounds is a homologue, isomer or analog of the compounds of the invention, they were telstated in the same manner and again using the same weeds as in the tests for the compounds of the invention as shown in Tables IV to VI for the purpose of , determining their pre-emergence herbicidal activity compared to the compounds of the invention. (Based on the average of five-fold test for Compound I and nine-fold telst for Compound H), it is determined that none of the compounds selectively suppresses shattercane in sorghum and that Compound H does not selectively suppress the sorghum seedlings, whereas Compound I has only selectivity has a selectivity factor of about 1.2 against sorghum seedlings. In addition, both H and I do not selectively suppress the remaining weeds listed in Tables IV and VI. Therefore, it is clear that the compounds of the invention have significant advantages even with respect to industrially produced herbicides for selective weed control in sorghum.

The compounds of the invention have a selective herbicidal effect in a variety of useful plants other than sorghum, as shown in Table III above. In other tests, the compound of Example 5 also appears to be suitable in an amount in excess of 1.12 kg / ha for peanut, corn, cotton, cucumber, god, pea, tomato and soybean.

From the foregoing detailed description, it can therefore be concluded that the compounds of the present invention have unexpected and extremely good herbicidal properties, both absolute and relative to most structurally related compounds or otherwise related homologs and analogs, including the industrially produced prior art 2- haloacetanilides. The compounds of the invention show excellent crop safety, sorghum and selectivity, especially with respect to hard-to-control species, such as halep sorghum seedlings and shattercane, and other difficult weeds such as bent-grass, broadgrass, millet, foxtail, hedgehog corns, bloody dew and the like, as shown in Tables II to VI.

The herbicidal compositions of the present invention include concentrates that require dilution prior to administration, comprising at least one active ingredient and an adjuvant in liquid or solid form.

The compositions are prepared by mixing the active ingredient with an excipient, including diluents, fillers, carriers and processing aids, to provide the composition in the form of finely divided solid particles, granules, pellets, solutions, dispersions or emulsions. Thus, the active ingredient can be used with an excipient such as a particulate solid, an organic liquid, water, a wetting, dispersing or emulsifying agent or any suitable combination thereof.

The compositions according to the invention, in particular liquids and wettable powders, preferably contain, as adjuvant, at least one surfactant in an amount sufficient to obtain said composition readily dispersible in water or oil. The incorporation of a surfactant into the composition greatly increases its effectiveness. The term "surfactant" includes wetting, dispersing, suspending and emulsifying agents. Anionic, cationic and nonionic agents can be used as well.

Preferred wetting agents are alkylbenzene sulphonates and, alkylnaphthalene sulphonates, sulphonated higher aliphatic alcohols, amines or acid amides, long-chain esters derived from sodium isothionate, sodium sulphosuccinate esters, sulphated or sulphonated fatty acid esters, petroleum sulphonates, sulphonates of vegetable oils, sulphonates of vegetable oils alkylphenol derivatives (especially isooctylphenol and nonylphenol); and polyoxyethylene derivatives of higher monoesters derived from fatty acids and hexitoanhydrides (e.g. sorbitan). Preferred dispersants are methylcellulose, polyvinyl alcohol, sodium lignin sulfonates, polymeric alkyl naphthalenesulfonates, sodium naphthalenesulfonate and polymethylene bisnaphthalenesulfonate.

Wettable powders are water dispersible compositions comprising at least one active ingredient, an inert solid carrier and at least one wetting and dispersing agent. Inert solid fillers are usually of mineral origin, such as natural clays, diatomaceous earth, synthetic minerals from 1918 to 555 incorporated in silica and the like. Examples of such fillers include kaolinity, attapregite clays, and synthetic magnesium silicate. Wettable powder compositions of the present invention typically comprise from about 0.5. up to 60 parts (preferably from 5 to 20 parts) of the active ingredient, from about 0.25 to 25 parts (preferably from 1 to 15 parts) of the wetting agent, from about 0.25 to 25 parts (e.g. preferably from 1.0 to 15 parts) of a dispersant and from 5 to about 95 parts (preferably from 55 to 50 parts) of an inert solid filler, wherein all parts represent the weight of the total composition. If desired, 0.1 to 2.0 parts of the solid inert filler may be replaced by a corrosion inhibitor, a foam-preventing agent, or both.

Other formulations include dust concentrates containing from 0.1 to 60% by weight of the active ingredient in a suitable filler. These dusts can be diluted for use to a concentration in the range of about 0.1 to 10% by weight.

Aqueous suspensions or emulsions may be prepared by mixing an aqueous mixture of the water-insoluble active ingredient and the emulsifying agent until uniform distribution and then homogenizing to obtain a stable emulsion of very fine discrete particles. The resulting concentrated suspension is characterized by an extremely small particle size, so that when diluted and sprayed, the coverage is very uniform. Suitable concentrations of these formulations contain from about 0.1 · 60% · preferably 5 to ^50:% by weight of active ingredient, the upper limit being determined by the solubility limit of active ingredient in the solvent.

In another form of aqueous suspension, the water-immiscible herbicide is encapsulated to form a microencapsulated phase dispersed in the aqueous phase. In one embodiment, small capsules are prepared by bringing together an aqueous phase comprising a ligninisulphonate emulsifier, a water-insoluble chemical and p-olymethylene polyphenylisocyanate, dispersing a water-immiscible phase in the aqueous phase, and then adding the multifunctional amine. The isocyanate and amine derivative react to form a solid urea coating around the particles of water-insoluble chemical, thereby forming microcapsules. Typically, the concentration of the microencapsulated material is in the range of 480 to 700 g per liter, preferably 480 to 600 g per liter, based on the total composition.

Concentrates are usually solutions of the active ingredient in water-immiscible or water-miscible solvents to a limited extent, together with a surfactant. Suitable solvents for the active ingredient of the invention include dimethylformamide, dimethylsulfoxide, N-methylpyrrolidone, hydrocarbons and water-immiscible esters or ketones. Other very strong liquid concentrates may be prepared by dissolving the active ingredient in a solvent and then diluting it, for example, with kerosene, at a spray concentration.

The concentrate compositions generally contain about 0.1 to 95 parts (preferably 5 to 60 parts) of the active ingredient about 0.25 to 50 parts (preferably 1 to 215 parts) of the surfactant, and 4 to 94 parts of the solvent are needed, wherein all parts are by weight and based on the total weight of the emulsifiable oil.

Granules are formulations of physically stable particles which contain the active ingredient adhered or deposited on the matrix of inert finely divided filler particles. To facilitate leaching of the active ingredient from the particles, a surfactant may be present in the composition, for example some of those listed above. Natural clays, porophyllite, Ulit and vermiculite are examples of possible groups of special mineral fillers. Preferred fillers are porous, preformed particles having absorbent properties, such as preformed and sieved attapulgite particles or thermally expanded vermiculite particles and finely divided clays such as kaolin, hydrated attapulgite or bentonic clays. These fillers are sprayed with or mixed with the active agents to form herbicide granules.

The granular compositions of the present invention may contain from about 0.1 to about 30 parts, preferably from about 3 to 20 parts, by weight, per 100 parts by weight of clay and from 0 to about 5 parts. by weight of surfactant per 10 parts by weight of clay particles.

The compositions of the present invention may also contain other ingredients, for example, fertilizers, other herbicide, other pesticides, preservatives and the like used as adjuvants or combinations with any of the adjuvants described above. Chemicals suitably in combination with the active ingredients of the invention include, for example, triazines, ureas, carbamates, acetamides, acetanilides, uracils, acetic acid or phenol derivatives, thiocarbamates, triazoles, benzoic acids, nitriles, biphenyl ethers and the like, as set forth below. substances.

Heterocyclic nitrogen / sulfur derivatives

2-Chloro-4-ethylamino-6-isopropylbutylamino-triazine

2-Chloro-4,6-bis (isopropylamino) -sym triazine

2-Chloro-4,6-bis (ethylamino) -isyl-

-triazine.

3-Isopropyl-1H-2,1,3-benzothiadiazin-4- (3: H-one-2,2-dioxide)

3-Amino-1,2,4-triazole

6,7-Dihydrodipyrido (1,2-a: 2 ‘, Г-е) pyrazidinium salts

5-Bromo-3-isopropyl-6-methyluracil-1,1'-dimethyl-4,4‘-bipyridinium compound i

213855

Ureas

4N ^t -i ( '4jChlorf phenoxy) phenyl-N, N-dimethylurea

N, N-Dimethyl-N- (3-chloro-4-methylphenyl) urea

3- (3,4-Dichloro-phenyl) -1,1-di (4- (ethyl) -urea)

1,3-Dimethyl-3- (2-benzothiazolyl) urea

3- (p-Chlorophenyl) -1,1-dimethylurea

1-Butyl-3- (3,4-dichlorophenyl) -1-methylurea

Caramates / thiodocarbamates

2- Chlo: rallyl (diethyldithiocarbamate)

S- (4-Chlorobenzyl) -N, N-diethyldithiocarbamate

Isopropyl N- (3-chlorophenyl) carbamate

S-2,3-Dichlorallyl (N, N, N-diisopropylthiolcarbamate)

Ethyl (N, N-dipropylthiolcarbamate)

S-Propyl (dipropylthirlcarbamate)

Acetamides / acetanilides / anilines / amides

2-Chloro-N, N-diadlylacetamide. N, N-Dichloromethyl-2,2-diCenylacetamide

N- (2,4-Dimethyl-4-yl-55 - {[(trifluorometbyl) sulfonyl] amino) phenyl Jacetamide

N-Isopropyl-2-chloroacetanilide

N -Diethyl-N-methoxymethyl-4-chloroacetanilide

2‘-Methyl-6‘-ethyl-N- (2-methoxy-2-propyl) -2-chloroacetanilide α, α, f Trifluoro-2,6-dimethyl-N, N-dipropyl-β-toduidine

N- (1,1-Dimethylpropinyl) -3,5-dichlorobenzamide

Acids / esters / alcohols

Lactic acid 2,2-dichloropropene

2-Methyl-4-chlorophenoxyacetic acid

2,4-Dichlorophenoxyacetic acid

Methyl 2- [4- [2,4-dichloro-enoxy] -phenoxy] -propionate

3-Amino-2,5-dichlorobenzoic acid

2-Methoxy-3,6-dichlorobenzoic acid

ZAi-trichlorophenyl · acetic acid

N-1-Naphthylphthalic acid

Sodium 5- [2-chloro-4- (trifluoromethylphenoxy) -2-nitrobenzoate

4, α-Dinitho-o-seik, t-butylphenoi

N- (phosphonomethyl) glycine, its ¹

C 1-6 monoalkylamine and alkali metal salts and combinations thereof

Ethers

2,4-Dichlorophenyl-4-nitrophenyl ether

2-Chloro-α, α, β-trifluoro-p-tolyl-3-ethoxy-4-mirodiphenyl ether

Various substances

2,6-ШсЬ1огЬbnzo-nitTil

Methanesonic acid monosodium salt

Methanesonic acid disodium salt

Fertilizers suitable in combination with the active ingredient include, for example, ammonium nitrate, urea, potash and superphosphate. Other suitable ingredients include materials in which the plant organism roots and grows, such as compost, manure, humuls, sand, and the like.

Herbicidal compositions of the types described above are exemplified in several; of the illustrative embodiments below.

Emulsifiable concentrates

AND.

Percentage of weight

Example compound 150.0

A mixture of calcium dodecylbenzenesulfonic acid and polyoxyethylene ethers _with (for example

At-lox R 3437F and A-tox 3438F) 5.0

Mo night h lorbenzene45,0 '

100.00

В.

Example compound 285.0

A mixture of calcium dodecylsulfonic acid and alkylaryl polyol tert-alcohol 4,5

Aromatic hydrocarbon solvent with 9 carbon atoms11.0 “” ”100.00

IV. Wettable powders

Compound of Example 3 A mixture of calcium salt of dodecylbenzenesulfonic acid and polyoxyethylene ethers [e.g. 5.0 Percentage of weight AND. Atlox 343I7F) 1.0 Example 3 compound 25.0 Xylene 94.0 Sodium lignosulfonate 3.0 100.00 Sodium N-methyl-N-oleyltaurate 1.0 II. Liquid concentrates Amorphous silica (synthetic silica) 71.0 AND. B. 100.00

Percentage of weight Compounds of Example 5 Sodium dioctylsulfokcinate 80.00 1,25 Example 4 compound 10.0 Calcium lignosulfonate 2.75 Xylene 90.0 Amorphous silica (synthetic 100.00 silicon dioxide) 16.00

100.00

В.

Percentage of weight

Example 5 compound 85.0 C. Dimethylsulfoxide 15.0 100.00 Example 6 compound 10.0 Sodium lignosulfonate 3.0 C. Sodium N-methyl-N-oleyltaurate 1.0 Kaolinite clay 86.0 · Example 6 compound '50, 0 100.00 N-methylpyrrolidone 50.0 100.00 V. Popraš D. Percentage of weight Example 7 compound 5.0 AND. Ethoxylated castor oil 20.0 Example 3 compound 2,0 Rhodamin В 0.5 Dimethylformamide 74.5 Attapulgit 98.0 100.00 100.00 III. Emulsion B. Percentage of weight Example 4 compound 60.0 Montrnorillonit 40.0 AND. 100.00 Compound of Example 8 Polyoxyethylene / polyoxypropylene block copolymer 40.0 C. Example 5 compound 30,00 with butanol (eg Tergitol ^R XH) 4.0 Bentonite 70,00 100.00 Water 56.0 100.00 D. B. Example 6 compound 1.0 Diatomaceous earth 99.0 Example 1 compound 5 /) 100.00

Polyoxyethylene / polyoxypropylene block copolymer with butanol 3.5

Water 91.5

100.00

VI. Granule

Percentage-weight

AND.

Example compound 715.0 ’

Granular attapulgite (0.36-0.7 mm) 85.0-100.00

B.

Example compound -830.0

Diatomaceous earth (0.36 to 0.7 mm) 70.0

100.00

C..

Example 10.5

Bentonite (0.36 to 0.7 mm) 99.5

~ .......... 100.00

D.

Example compound 25.0

Pyrophyllite (0.36 to 0.7 mm) 9-5.0

100.00

VII. Microcapsules

Percentage of weight

AND.

The compound of Example 4 encapsulated in -purea-packaging49.2

Sodium lignosulfonate (for example

Reax 88RB) 0.9

Water49.9

100.00

Percentage of weight

B.

Example 5 encapsulated in a polyurea coating of 10.0

Potassium lignosulfonate (for example

Reax (C-21) 0.5

Water89.5

I - 100 100.00

C.

The compound of Example 6 encapsulated in a polyurea coating 80.0

Magnesium lignosulfonate (for example

Treax® LTM] 2.0

Water18.0

..... 100,00

When working in accordance with the present invention, an effective amount of the acetanilides of the invention is applied to soil-containing plants or introduced into the aqueous environment by any conventional means. The application of the liquid and the particulate solid composition to the soil can be carried out by conventional methods, for example by means of a duster, a quick sprayer, a manual sprayer and a sprayer. The compositions can also be used from aircraft as a dust or spray, due to their efficacy in small doses. The application of the herbicidal compositions to aquatic plants is usually accomplished by adding the compositions to the aquatic environment in an area in which the suppression of aquatic plants is desired.

The use of an effective amount of the compounds of this invention at the site of occurrence of undesirable plants is essential and is critical to the practice of this invention. The exact amount of active ingredient to be used depends on various factors, including plant species, degree of development, type of soil and its condition, amount of rainfall and the individual acetanilide used. For selective pre-emergence application to plants or soil, doses of from about 0.02 to about 11.2 kg / ha, preferably from about 0.04 to about -5.6%, are generally used. »Kg / ha or suitably from 1.12 to 5.6 kg / ha of acetanilides. In some cases, lower or higher doses may be required and those skilled in the art can readily determine from the above description and examples above the optimum amount of the composition which must be used in any particular case.

The term "soil" is used in its broadest sense to include all common "soils" as defined in WeBster's New International Dictionary, Second Edition, not abbreviated (196i). in which vegetation can take root - and grow - and include not only clay but also compost, manure, mud, humus, sand and the like, which are adapted to promote plant growth.

Although the invention is described with respect to specific modifications, the details are not intended to limit the scope included in the following subject matter of the invention.

Claims (5)

What is claimed is: 1. A herbicidal composition comprising an adjuvant and a herbicidally effective amount of a compound of the general formula: EMI10.1 wherein: R is isopropyl, n-butyl, isobutyl, sec-butyl, allyl or 2-methylbutyl, R 1 represents methyl, isopropyl, n-butyl or allyl and R 2 and R 5 are hydrogen or methyl, with the proviso that R 1, R 2 and R 3 are each methyl when R is n-butyl, isobutyl or sec-butyl; and R 3 is each hydrogen when R is isopropyl, isobutyl or sec-butyl; R 1 is isopropyl or n-butyl and R 2 is hydrogen, and R 3 is methyl when R is 2-methylbutyl or allyl and R 1 is allyl. 2. A compound according to claim 1, wherein the active ingredient is N- (isobutoxymethyl) -2‘-methoxy- '3. A composition according to claim 1, characterized in that the active substance contains · N- (allyloxymethyl] -2 ^¢ allyloxy-β'-2-rnelhyl chlbracetanilid. 3 ‘, 6‘-dimethyl-2-chloroacetanilide. 4. A composition according to claim 1, wherein the active ingredient is N- (sec-butoxymethyl) -2‘-n-butoxy-2-chloroacetanilide. '5. 2. A composition according to claim 1, wherein the compound is selected from the group consisting of: N- (n-butoxymethyl) -2'-methoxy-3 ', 6'-dimethyl-2-chloroacetanediol. N- · (sec-butoxymethyl) -2‘-methoxy-3‘, - 6‘-dimethyl-2-chloroacetanilide, N- (2-methylbutoxymethyl) -2'-allyloxy-6'-methyl-2-chloroacetanilide, N- (isopropoxymethyl) -2‘-isopropoxy-2-chloroacetanilide, N- (isobutoxymethyl) -2'-isopropoxy-2-chloroacetanilide.