FR2479200A1 - HYDROCARBYL OR HYDROCARBYLOXYALKYL-2-HALOACETANILIDE COMPOUNDS USEFUL FOR THE DESTRUCTION OF WEEDS ASSOCIATED WITH RICE, AND HERBICIDE COMPOSITIONS COMPRISING THE SAME - Google Patents

Abstract

HYDROCARBYL- OR HYDROCARBYLOXYALKYL-2-HALOACETANILIDE COMPOUNDS HAVING THE FORMULA: (CF DRAWING IN BOPI) WHERE R IS THE ALLYL, CHLOROALLYL, PROPARGYL, 1-METHOXY-PROPARBICAL-FORMULA-2-HYDROCARBYL, CHLOROALLYL, PROPARGYL, 1-METHOXY-PROPETH-FORMULA-2-RADICAL-YLOXY-PROPARBICAL-YLX CHOR OR R IS THE ALLYL GROUP OR A RADICAL ALKYL IN C ARE ACTIVE INGREDIENTS IN HERBICIDE COMPOSITIONS USED IN VARIOUS HARVESTING PLANTS, ESPECIALLY IN REPIQUE RICE; HERBICIDES ARE PARTICULARLY EFFECTIVE AGAINST THE ANNUAL AND PERENNIAL WEEDS COMMONLY ASSOCIATED WITH RICE.

Description

1.

  The present invention relates to the field of 2-

  haloacetanilides and their use in agronomic techniques, for example as herbicides, particularly

  for use in transplanted rice.

  The compounds of the present invention are characterized in that they are 2-chloroacetanilides having

  a specific combination of n-butoxy radical in a

  ortho group, one ethyl group in the other position ortho, and, as a substituent on the anilide nitrogen atom, a group selected from the group consisting of allyl, chloroallyl, propargyl, 2-methoxypropyl, 2-yl or radical

  having the formula -CH2OR1 o R1 is a C1-15 alkyl radical.

  The prior art relating to the present

  invention, includes many descriptions of 2-haloacetals

  nilides which may be unsubstituted or substituted by a large number of substituents on the aniline nitrogen atom and / or on the anilide ring comprising alkyl radicals,

  alkenyls, alkynyls, alkoxys, polyalkoxys, alkoxyalkyls,

  terocyclic, halogen, etc. The most interesting compounds

  Prior art products in this field appear to be those described in the following references: U.S. Patent Nos. 3,268. 584, No. 3,442,945, No. 3,547,620, n

  3,773,492, No. 4,152,137 and Belgian Patent No. 810,763. How-

  2. None of these prior art references provide results for compounds of the type described here,

  showing that they are useful herbicides for rice

  and do not describe or suggest the particular species of the present invention. The 2-haloacetanilides of the prior art, which are known to have utility as herbicides for transplanted rice, differ markedly in structure from those described herein. Specifically, these prior art herbicides all contain lower alkyl radicals in both ortho positions relative to the nitrogen atom.

  of anilide and an alkoxyalkyl radical on this nitrogen atom.

  Accordingly, these prior art rice herbicides are not related to and do not suggest those described herein. However, to provide a basis for comparison, the relative herbicidal efficacy of the compounds according to the present invention is compared to the known herbicide.

  under the trademark Machete (the registered trademark of the

  Monsanto Company) whose active ingredient is 2 ', 6'-diethyl-N (n-butoxymethyl) -2-chloroacetanilide (common name "butachlor) .Butachlor and its homologue (" ethylbutachlor "here) are described as herbicides for rice in U.S. Patent No. 3,663,200. In the known prior art of 2-haloacetanilide herbicides, only the herbicide

  said Machete has obtained so far a commercial status.

  While herbicides for the prior art rice have been found useful, it is continually needed

  improved herbicides for rice that control or destroy

  resistant weeds of economic importance

  at lower rates of application, which maintain the

  control or control of these weeds for

  longer periods of time, while maintaining the security

  rice harvests and improved toxicity with respect to

  harbor to fish and mammals.

  It has been found that the herbicides of the prior art

  above mentioned shared one or more

  undesirable properties as herbicides for transplanted rice.

  3. Among certain disadvantages of herbicides of the technique

  for transplanted rice, there is their overall performance

  weakly for the control and / or removal of

  economically important long-lived perennial herbs consisting of Cyperus serotinus, Eleocharis

  kuroguwai and Sagittaria trifolia with a decrease in

  ficiency for the control or suppression of bad

  annuals consisting of Echinochloa crus-galli and, to a lesser extent, Monochoria vaginalis in a period of 2-6 weeks. These performance weaknesses appear

  particularly at lower rates of application, ie

  say lowering up to 0.19 kg / ha and even less. In fact,

  Field tests have shown that in some cases

  However, some herbicides of the prior art could selectively not control Eleocharis kuroguwai at rates below 6 kg / ha or even 3 kg / ha for

  periods as short as' 2 or 3 weeks. In a similar way

  In the field tests, it has also been found that some prior art rice herbicides do not provide significant Sagittaria suppression.

trifolia after 4 or 5 weeks.

  It is, therefore, an object of the present invention.

  to provide a class of herbicides which is particularly

useful for transplanted rice.

  Another object of the present invention is the

  vision of selected herbicides that: (1) are safe (i.e., produce no more than about 15% damage) on the transplanted rice at rates up to at least 2.24 kg /Ha; (2)

  selectively control Echinochloa crus-galli, Mono-

  choria vaginalis, Cyperus serotinus and Eleocharis kurogu-

  wai, and (3) which provide increased suppression of the Sagita-

taria trifolia.

  Finally, it's an advantage of the herbicides of the

  present invention that they are safe and do not require

  special operating procedures.

  The objects listed above and other objects of

  the present invention will become more apparent from the description

4.

detailed below.

  The present invention relates to compounds having

  herbicidal compositions, herbicidal compositions containing these compounds as active ingredients and the herbicidal method of using these compositions in various crops, including

  especially in transplanted rice.

  The Applicant has now found that a separate group

  of 2-haloacetanilides, characterized by combinations of

  specific radicals on the anilide nitrogen atom, a specific alkoxy radical in an ortho position and a

  ethyl radical in the other ortho position, possesses

  selective herbicidal herbs and

  unexpectedly as herbicides for transplanted rice, compared to herbicides of the prior art

  related, belonging to the most recent prior art

  interesting, including a commercial herbicide for rice.

  A main feature of herbal compositions

  Bicides of the present invention are their ability to control and / or control annual and perennial narrowleaf weeds in transplanted rice, particularly the predominantly economically important annual weeds such as Echinochloa crus-galli. , Monochoria vaginalis, and resistant perennials such as Cyperus serotinus, Eleocharis kuroguwai and

  Sagittaria trifolia and other noxious weeds.

  The compounds of the present invention are characterized

rised by the formula:

0

ClCH2C R N C2H5 0-n-C H

  o R is the allyl, chloroallyl, propargyl, 1-methoxy group

  5. xyprop-2-yl or a radical having the formula -CH20R1, o R1

  is the allyl group or a C1-5 alkyl group, preferably

a C3-5 alkyl radical.

  The preferred species of the present invention are those wherein R is the propargyl group, 1-methoxypropyl, and R 1 is allyl, n-propyl, sec-butyl, 2-methylbutyl or isoamyl. Other species of the present invention are those

  o R, in the formula above, is the allyl group, chloro

  allyl or -CH 2 O OR 1 groups where R 1 is methyl,

isopropyl, n-butyl or isobutyl.

  The utility of the compounds of the present invention,

  as active ingredients in herbicidal compositions.

  formulated with these compounds, and the process for their use

  will be described below.

  The compounds of the present invention can be

  done in many ways. For example, these compounds may

  can be prepared by N-alkylation of the 2-halogen anion

  suitable secondary acetanilide with an alkylating agent,

in basic conditions.

  Example 1 below illustrates the use of this N-alkylation to prepare a species of the present invention. A modified N-alkylation process is described in

  example 2 to prepare another species of the present invention.

  vention. The modified N-alkylation process described in the example

  ple 2 here involves the in situ preparation of the halogen ethers

  methyl and alkyl or alkenyl, used as

  start in the N-alkylation process.

EXAMPLE 1

  2'-n-butoxy-6'-ethyl-2-chloroacetanilide, in

  5.4 g (0.02 mole), propargyl bromide in

  2.6 g (0.022 mole) and 2.0 g of benzyltrichloride

  thylammonium were mixed in 150 ml of

  thylene and cooled. In the 15 C mixture, 45 ml of 50% NaOH was added all at once and stirred for 5 minutes, then 150 ml of cold water was added. The layers were separated, washed with water and then dried on 6.

  MgSO4 and evaporated by the so-called Kugelrohr device to obtain

  4.75 g (73% yield) of yellow oil, boiling point

118 C at 0.03 mm Hg.

  Analysis calculated for C17ClNO3 (%): C, 66.33; H, 7.20;

C1,11,52;

Found: C, 66.35; H, 7.21;

C1,11,50

  The product has been identified as N-propargyl-2'-n-

  butoxy-6'-ethyl-2-chloroacetanilide.

EXAMPLE 2

  By following substantially the same procedure as

  that described in Example 1, but substituting the bromine

  As an alkylating agent, 4.9 g (79% yield) of yellow oil boiling at 128 ° C. (device

says Kugelrohr under 0.05 mm Hg).

  Analysis calculated for C17H24ClNO2 (%): C, 65.90; H, 7.81;

C1,11,44;

  Found: C, 65.89; H, 7.81; Cl, 11.42

  The product has been identified as N-allyl-2-n-butoxy-

6'-ethyl-2-chloroacetanilide.

EXAMPLE 3

  This example describes a modification of the N-alkylation process described in Example 1. In this embodiment of the process, the alkylating agent is formed in situ,

  thus making a more efficient, more economical operation

that and simpler.

  In a cooled mixture of 6.96 g (0.12 mole) of

  allyl cool, 1.8 g (0.12 mole) of anhydrous paraformaldehyde and 150 ml of methylene chloride, 4.71 g (0.06 mole) of acetyl chloride; the mixture was

  stirred for 90 minutes until all the para-formal-

  dehyde be dissolved. In the mixture, 5.4 g (0.02 mol) of 2'-n-butoxy-6'-ethyl-2-chloroacetanilide was then added,

  2.0 g of benzyltriethylammonium chloride and 50 ml of chlorine

  methylene chloride. The mixture was cooled to 1000 ° C. and 50 ml of 50% NaOH was added all at once and

247920-0

7.

  stirred for 15 minutes. The layers have been separated,

  dried with MgSO 4 and evaporated by the so-called Kugelrohr device to obtain 6.0 g (92% yield) of clear oil, boiling at 122 ° C. at 0.04 mm Hg. for C18H26ClNO3 (%): C, 63.61; H, 7.71;

C1,10,43.

Found: C, 63.60; H, 7.74;

C1,10,42.

  The product has been identified as N- (allyloxymethyl) -

  2'-n-butoxy-6'-ethyl-2-chloroacetanilide.

EXAMPLE 4

  By following substantially the same procedure

  than that described in Example 3, but substituting 2-

  butanol as the alkylating agent, there was obtained 4.15 g (yield

  78%) of 118 C light boiling point oil

  0.02 mm Hg (Kugelrohr device).

  Calcd for C19H30ClNO3 (%): C, 64.12; H, 8.50; Cl, 9.96; Found: C, 64.05; H, 8.52; Cl, 9.90

  The product has been identified as N- (sec-butoxymethyl)

  thyl) -2'-n-butoxy-6'-ethyl-2-chloroacetanilide.

  - The starting material consisting of secondary anilide

  re, used in the above exenples, is prepared according to

  known processes, for example by haloacetylation of the amine

  corresponding primary ne with haloacetylating agents such as haloacetyl halide or haloacetic acid anhydride. Typically, the appropriate amount of the appropriate primary amine is dissolved in a solvent, such as methylene chloride, containing a base, for example 10% NaOH, and stirred vigorously, while mixing with a

  solution of the haloacetyl halide, for example chlorine

  chloroacetyl, with external cooling, for example

  at 15-25 C. The layers are separated and the soil layer is

  The organic layer is washed with water, dried and evaporated under vacuum. The primary amines used to prepare the secondary anilides can also be prepared by

  known means, for example by catalytic reduction of nitro-

  benzene corresponding to appropriate substitution, for example a 2-alkoxy-6-alkylnitrobenzene, in a solvent such as an alcohol, for example ethanol, using a catalyst

with platinum oxide.

EXAMPLE 5

  This example describes the preparation of N- (2-methoxy-

  prop-2-yl) -2'-n-butoxy-6'-ethyl-2-chloroacetanilide.

  In a cooled solution of N- (2-methoxyprop-2-

  yl) -2'-n-butoxy-6'-ethylaniline, in an amount of 4.42 g (0.016 mol) in 0.0176 mol of 10% NaOH and in 100 ml of

  CH 2 Cl 2 was added 2 g (0.0176 mol) of chlorobutylene chloride.

  acetyl drop by drop; the solution was stirred for 10 minutes

  minutes, the layers thus formed were separated and the

  get organic washed with water, dried over MgSO 4 and evapo-

  by the so-called Kugelrohr device to give 3.5 g (

  65%) of yellow oil with a boiling point of 132 ° C

under 0.07 mm Hg.

  Analysis calculated for C18H28ClNO3 (%): C, 63.24; H, 8.26;

C1,10,37;

Found: C, 63.16, 8.27

C1,10,36

  The product has been identified as in the first

phase of this example.

  The starting material consisting of secondary anilide used in Example 5, is obtained by known oyers (for example as in Belgian Patent No. 810,763 mentioned

  above). Thus, 19.3 g (0.1 mole) of 2'-n-butoxy-6'-ethyl-

  aniline were heated at 50 ° C. in 15 ml of ethanol and in 15 ml of glacial acetic acid, then 9.68 g (0.11 mol)

  of methoxyacetone and 0.1 g of PtO2 were added and the

  The mixture was hydrogenated at 50 ° C for 4 hours; the mixture was filtered, evaporated by the so-called Kugelrohr device at 100 C,

  under 0.07 mm Hg, to obtain a yellow oil.

  Analysis calculated for C16H27NO2 (%): C, 72.41; H, 10.25; 9.

N, 5.28;

Found: C, 72.36; H, 10.27;

N, 5.23

  The product has been identified as N- (1-methoxyprop-2-

yl) -2'-n-butoxy-6'-ethylaniline.

EXAMPLES 6-13

  Following substantially the same procedure and conditions as described in Examples 1-4, using the same secondary anilide but substituting the appropriate alkylating agent as the starting material and the appropriate amounts, the corresponding products in Examples 7-13 corresponding to the formula in Table I were prepared. Thus, Examples 6-12 were prepared according to the N-alkylation procedure described in Examples 3 and 4 and the product of Example 13 was prepared by the method of

N-alkylation of Examples 1 and 2

TABLE I

  o ClCH2C N / CH2OR1 úCgH r 0-n-C4H9 Example Analse Analvse

R P.E. 0C

  (mm Hg) Calculated Element Found: ## STR2 ## ## STR1 ##

-CH2CHCH2 CH3

13 /

(0.04)

(0.03)

(0.02)

(0.03)

  ## STR1 ## wherein: Y, Y4, 8.72, 9.58, 64.12, 8.50, 9.96, 63.24, 8.26, 37, 64.94, 8.72, 9.58, and OJ 8.75 9.58 64.06 8.53, 06 63.31 8.27, 42.64, 86 8.72 9.62 eA, t% C. TABLE I (Continued) n-C4H9 128 C 64.2 64.05

(0.03) H 8.50 B, 49

  Cl 9.96 9.91 11 CH3 f130 C 61.24 61.31

(0.04) H 7.71 7.71

  tI CC 10.30 10.33 12.i-C H 1119 C 63.24 63.41

! 3 7 (0.02) H 8.26 8.31

j | 13 t C1I Ci I 10,37.10,46

13 C 1

I0 -CH C = CH 136.C 59.31 59.47

2i

(0,1) H! 6.73 6.78

C- - 120.60 20.52

  As noted above, the compounds of the present invention

  This invention has been shown to be effective against major Asian weeds as herbicides for transplanted rice. However, the herbicidal activity of pre-emergence and post-emergence against other weeds in

  other plants to be harvested was also shown. The

  Tables II and III summarize the results of these tests

  to determine the herbicidal activity of pre-emergence

of the present invention. -

  The pre-emergence tests were conducted as follows: A good quality of top soil is placed in

  aluminum boxes and compacted to a depth

  9.5 mm to 12.7 mm from the top of the box. Au-

  above ground, a number of seeds or

  vegetative pagules of various species of plants. The soil required

  To fill at the box level, after seeding or addition of vegetative propagules, is weighed in a box. Soil and a known amount of the active ingredient, applied

  in a solvent or in the form of a suspension of wettable powder

  lable, are totally mixed and used to cover the prepared boxes. After treatment, the boxes are sent to a greenhouse bench where they are moistened by underwater irrigation, as needed to provide adequate moisture

  for germination and growth.

  Approximately 2 weeks after seeding and

2479200-

11.

  the treatments, the plants were observed and the results

  registered states. Tables II and III below summarize these results. Herbicide evaluation was obtained using a fixed scale based on the percentage of damage to each plant species. Evaluations are defined

as following: -

% of control Rating

* 0-24 O

-49 1

50-74 2

-100 3

  Not determined 5 The plant species used in a series of tests, the results of which are presented in Table II, are identified by a letter according to the following legend: A Canada Thistle E Lamb Quarter I Johnson B Nielle Herb Fields F Beautiful Grass J Brome Fluffy

  C Yellow Carex G Carex Velvet Leaf

D Volubilis gardens walnut yard

H Grass of charla-

tan IV 12.

TABLE II

  Pre-emergence activity Composed of i Plant species Example n kg / ha -A B C D E F G H I J K

! 1 $ 11.2 3 2 1 2 3 3 3 3 3 3 3

, 6 3 2 12 32 3 30 33

2 11.2 3 2 2 3 3 3 3- 3 3 3 3

, 6 2 1 1 1 1 1 3 2 0 3- 3

3 11.2 5 O 1 1 2 2 3 3 3 3 3

5,6 5 O O O- 3 2 2 3 3 3 3

4 11.2 3 00 0 2 1 3 2- 0 3 3

, 6 3 O O 0 1 2-- 2 3 o 3 -3

11.2 5 O 1 0 3 2 3 3 5 3 3

, 6% 5 O O O 2 3 1 3 5 3 3

6 11.2 5 O O 0 O 1 O 3 O 3 3

, 6 5 O O 0 0 O 3 O O 3 3

7 11.2 2 0 3 2 3 3 3 3 1 3 3

, 6 3 1 2 3 3 3 2 3 1 3 3

8 11.2 3 0 0 O 2 1 3- '2 1 3 3

5.6 3 1 O O 2 1 3 2 O 3 3

9 11.2 5 O 0 O O 1 1 2 0 3 3

, 6 5 O O O O O O O 3 3

11.2 3 0 1 1 -1 2 2 3 3 33 3-

, 6 1 O O O 3 1 1 1 1 3 3

11 11,2 3 1 2 3 3 2 3 3 2 3 3

, 6 O 0 2 2 2 1 3 2 3 3 3

12 11.2 2 O 1 3 -3 1 3 3 2 3 3

, 6 1 0 1 1 1 1 3 2 1 3 3

13 11.2 O O 1 O 2 O 3 2 O 3 3

5,6 O O O O 1 O O 1 O 3 3

  The compounds were further tested using

  the above procedure on the following plant species

  : L Soy R Hemp Sesbania M Sugar Beet E Lamb Quarter N Wheat F Beautiful Grass C Velvet Leaf O Rice: i H

OH

OH

  ## STR5 ##

O OI'U O

king or CoH o OH a

Ia> I -

0) (1) K) EH H

you 5-1 j E-scQ

0 -H

> C C

PAm a> a> Ca'n i r-HHnoQ Oa> Car4

0- a> H $ -

  ## STR5 ## wherein: ## STR2 ## is a compound of the formula ## STR1 ## wherein: ## STR2 ## LnLnLnLnLnLnLnLnLn U7LOLnLO UM M * MH For a U) L rirrH 0 t-0000 ri NM oo rin m oe o S (N r- OO

r -'i c'0 0 0-

M M000

  C 'oooooooooooooooooooooooooooooooooooooooooooooooooooooo

0 N 0 H00

  1 40 i0 0 nmmiN OO evleiciH O M iN00 M ri 000 n O O O eH000

N H O O O

NH000

OOO1OO

Cici H DOO N r -1 0

0 7 0 0 0

  ciciei O M c ci o ci en ni o HODO MiN HO

-4 0 0 1

  ## EQU1 ## where ## STR1 ##

O 0 00 0

("4 O OO O '

<.0000

("H 00 0

0 01 0 0 0

in O O O O H0000 co7 0 0 0

<0000

  cn H O Y O N O r-4 O O i M M N i H rm r i M 1 HOOO0

<1 000

ri H O O

<10000

cimiooa (% o o o o r o

< "0000

  in ooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooooo

1H000 0

m o o o

this one N 'H- H-

<-. 0000

cvi v> c HO M C (4 H o o

C'4000

N C'4 HH O

  MOoo 00 00 h oto o o mo o o o rm e "-4 O O 'O

1 0 0 0 0

M r O O 'O

-A O H O O

nn 0 1 0 0 M N O- a O if O O O O

1 0000

  H0000 _: N 0. to, H -oci00 Go r. ## EQU1 ## where ## EQU1 ##, where ## EQU1 ## o - o o, - io4 o os OOH 0k0 NOO unt.St 5 * ,. 5.t.S.t .. t..t..t..t..t..k, t.k, t. r O un------000 000 000 000 000)) 000 000 000))))))))))))))))))))

0a) Ln-o, 3, :: i. i.-

  ## EQU1 ## TABLE III (Continued i0 i0 o * 0

1. 1 1 1 O

  Herbicides have been found to possess unexpected properties as herbicides for rice.

of this

epic, so

more specifically

  especially for the effective selective control of bad

  resistant annuals, important from the economic point of view

  of Echinochloa crus-galli and Mono-

  choria vaginalis, and perennial weeds consisting of

  by Cyperus serotinus (except for one exception

  two) and Eleocharis kuroguwai, while in some cases suppressing the perennial weed Sagittaria trifolia, in greater proportion than the commercial herbicide called

  Machete, and by controlling or deleting

  many other annual and perennial weeds less resistant.

  To illustrate the superior properties of

  Of the compounds of the present invention, both on an absolute basis and on a relative basis, comparative tests were conducted in the greenhouse. In these tests, the herbicide Machete (the only commercially available herbicide for rice, consisting of 2-haloacetanilide) was tested in 1il, 6 1.12 0.28 0.06, 6 1.12 0.28 0 , 0.6, 6 1.12 0.28, 6 1.12 0.28 0.06 0.01, 6 1.12 0.28 0.06 0.01 15.

comparative goals.

  In the discussion of the experimental results

  below, on occasion, reference is made to herbicide application rates symbolized by "GR ,," and "GR'85" these rates are given in kilograms per hectare (kg / ha). The GR15 rate defines the maximum rate of herbicide required to produce 15% or less damage to the plants to be harvested and the GR85 rate defines the minimum rate required to obtain 85% inhibition.

  GR15 and GR85 are used together

  I am measured by the potential commercial performance, obviously being of course that the suitable commercial herbicides may show more or less damage.

  to plants within limits - reasonable.

  Another guide to the effectiveness of a chemi-

  that as a selective herbicide is the "selectivity factor

  "(" FS ") for a herbicide in given crop plants and in specific weeds.The selectivity factor is a measure of the relative degree of safety for

  plants to be harvested and damaged

  besides, and is expressed in terms of the GR15 / GR85 ratio, ie

  say the GR15 rate for the crop plant divided by the rate

  GR85 for the weed, these two rates being in kg / ha.

  Since tolerance for harvesting and weed control are interrelated, a brief discussion of this relationship in terms of selectivity factors is significant. In general, it is desirable

  that the safety factors for the plants to be harvested, -

  that is, herbicide tolerance values are high, since higher herbicide concentrations are

  are often desired for one reason or another

  be. Reciprocally, it is desirable that the rates of

  weed control is low, that is,

  the herbicide has a high unit activity for reasons

  economic and possibly ecological sounds. However, low rates of herbicide application may not be adequate to control some weeds and

  more important may be required. As a result, the best

  bicides are those who control the greatest number of people,

  herbs with the least amount of herbicide and

  provide the greatest degree of safety for plants with

  colter, that is, tolerance to the plants to be harvested. Accordingly, selectivity factors (defined above) are used to quantify the relationship between crop safety and weed control;

  the higher the numerical value, the greater the selection

  herbicide activity for weed control

  10 in a given crop.

  In a comparative test in the greenhouse, results of herbicidal activity were obtained and are presented in Table IV, comparing the relative efficacy of the compounds

  Examples 1, 3-6, 8 and 9, which are representative compounds

  of the present invention, with tubachlor (ingredient

  active in the so-called Machete product, which is a commercial herbicide for rice) as selective herbicides against

  Asian weeds, important from the point of view of

  nomic, commonly associated with transplanted rice.

  The procedure used in this test in the greenhouse was as follows: an upper soil consisting of loam soils, containing about 0.05 wt.% Of Krillium, was sieved through a 0.6 cm mat and subjected to fumigation for a period of time. about 5-10 days before use. Pots are then filled by the soil formed by loam soils called Ray up to a level to allow a depth of flooding

  2.54 cm. Rice plants (Bluebelle) 2-3 weeks old

  are transplanted into the pots and bulbs or seeds of the experimental weeds also planted in the

  pots. The pots are then drowned and the chemical experi-

  mental applied to the surface of the flood water. Drenching water is reduced to allow germination of the Echinochloa crusgalli seed (backyard grass) and the pots are subsequently re-drowned and maintained in this plant.

  state. Observations of the percent inhibition using

  on a scale of 0-100% are carried out about 3 weeks

after treatment (SAT).

17.

  The experimental results presented in the table

  Table IV below represents the percentage of inhibition of plants within the limits of the experimental

  0.28 kg / ha to 2.24 kg / ha. The results are expressed as

  GR15 and GR85, respectively, for rice and weeds, as explained above; selectivity factors are shown in parentheses below each weed; "NS" means non-selective within the limits of experimental rates. The degree of control of

  Sagittaria trifolia, one of the weeds

  the most important problems on the commercial level, and the

  The most resistant 2-haloacetamide resistant herbicide to experimental weeds is presented in the last column of Table IV; the percentage of control presented is indicated for the maximum experimental rate of 2.24 kg / ha. The weed species are identified as follows: Echinochloa crus-galli (EC), Monochoria vaginalis (MV),

  Cyperus Serotinus (CS), Eleocharis kuroguwai (EK) and Sagitta-

ria trifolia (ST).

TABLE IV

  GR1 GR85 1 Control (kg / ha) _ _ (_kg / ha), of ST for Compound EC MV CS EK ST 2.24 kg / ha of _ _ i (%) __ Butanol chlorine 2, 24 <0.28 <0.25 <0.25 0.4> 2.24

(> 8.0) (> 8.0) (> 8.0) (5.0) (NS)

  Ex.1.24 <0.28 <0.28 <0.28 <0.28> 2.24

(> 8.0) (> 8.0) (> 8.0) (> 8.0) (NS)

  Ex.3> 2.24 <0.28 <0.28 <0.28 <0.28> 2.24

(> 8.0) (> 8.0) (> 8.0) (> 8.0) (NS)

  Ex.4> 2.24 <0.28 <0.28 <0.28 <0.28> 2.24

(> 8.0) (> 8.0) (> 8.0) (> 8.0) (NS)

  Ex.5> 2.24 <0.28 <0.28 <0.28 <0.28> 2.24

(> 8.0) (> 8.0) (> 8.0) (> 8.0) (NS)

  Ex.6> 2.0 <0.28 <0.28 <0.28 0.43> 2.24

(> 8.0) (> 8.0) (> 8.0) (> 4.7) (NS)

  Ex.8 1.96 <0.28 <0.28 <0.28 <0.28 <2.24 70

(> 7) (> 7.0> (> 7.0) (> 7.0) (NS)

  Ex.9 1.87 <0.28 <0.28 0.31 0.86> 2.24

___ (> 6.7) (> 6.7) (5.4) (1.9.) (NS)

  18. Referring to the results in Table IV,

  will see several important advantages of the compounds of the pre-

  This invention compared to butachlor as follows: (1) Examples 3-6 had higher safety factors for rice; (2) Examples 1, 3-5 and 8 had higher selectivity factors against EK and (3) Examples 1, 3, 4, 8 and 9 all exhibited ST control with a percentage

  superior to butachlor. The overall superiority of the compounds

  the present invention, particularly those of the examples

  -10 1 and 3-6, compared with the commercial herbicide, is clearly

  presented in the results in Table IV.

  In another comparative test in the greenhouse, others

  compounds according to the present invention have also been compared with

  butachlor res as a standard herbicide for rice

  transplanted. The compounds of Examples 2, 7 and 10-13 and the butadiene

  chlor were tested according to the procedure described above; the experimental results are shown in Table V.

TABLE V

GRs Rate GR85 Control

  (kq / ha) _ (kg / ha) 5% of Si Compo- Riz EC MV CS EK ST for 2.24 kg / ha (%) Butane 1.68 0.99 1.3> 2.24 0 , 71> 2.24 chlor I (1,7) (1,3) (NS) (2,4) (NS) Ex. 2 1.8 <0.28 <0.25 0.78 <0, 28> 2.24 10

(> 7.2) (> 7.2) (2.6) (> 7.2) (NS)

  Ex. 7> 2.24 <0.28 <0.43 <0.52 0.47> 2.24 0

(> 8.0) (> 5.3) (4.3) (4.8) (NS)

  Ex.10> 2.24 <0.28 <0.28> 2.24 <0.28> 2.24 0

(> 8.0) (> 8.0) (NS) (> 8, O) (NS)

  Ex.ll 1.12 <0.28 <0.28 0.95 <0.28> 2.24

(4.0) (> 4.0) (1.2) (> 4.0) (NS)

  Ex.12 0.75 <0.28 <0.28 1.8 <0.28> 2.24

(> 2.7) (> 2.7) - (NS) (> 2.7) (NS)

  Ex.13 1.12 <0.28 <0.28 1.0 <0.28> 2.24

(> 4.0) (> 4.0) (1.1) (> 4.0) (NS)

  Table V, the present invention provides a further explanation that each of the compounds of the present invention has one or more advantages over butachlor as follows: (1) Examples 2, 7 and 10 19. had superior safety factors in rice and (2) each compound of the invention exhibited selectivity factors against EC, MV, CS (except Example 10) and EK superior to butachlor. Although the butachlor has safety factors higher than Examples 11-13 and a control percentage of the ST higher than the compounds of the

  In the present invention, these advantages are compensated by means of

  significantly lower selectivity factors in most weeds in the test. It should be mentioned that, although field and greenhouse tests vary from one test to another (more in the greenhouse than in the field usually), the comparative results presented in

  the tables here have been provided under identi-

  compared to all herbicides in the test.

  In other comparative tests in the greenhouse, one at a maximum experimental rate of 1.12 kg / ha and one at a maximum

  maximum experimental level of 2.24 kg / ha, the compound of the

  ple 3 and butachlor were tested in rice seeded in mountainous terrain. We found that as average

  of two tests, the compound of Example 3 was selectively

  Echinochloa crus-galli (backyard grass) at 0.31 kg / ha while maintaining a safety for rice at a rate> 1.43kg / ha, providing a selectivity factor of at least 4, 6. In contrast, butachlor (commercial herbicide for

  rice) required 0.7 kg / ha to selectively control.

  same weed, with rice safety maintained at> 1.68 kg / ha, providing a selectivity factor of at least 2.4, ie about half that of the compound

of Example 3.

  In other tests in the greenhouse, the compound of Example 3 was tested for activity against annual weeds in sugar beets, at experimental levels in the range of 0.07 to 1.12 kg / ha. GR15 and GR85 for sugar beets and various weeds are shown in Table VI; selectivity factors for weed herbicide in sugar beets are shown in parentheses under weeds; "NS" means 20. non-selective within the experimental limits. The following abbreviations are used in the table: barnyard grass (BYG), wild oat (WO), downy brome (DB), red-rooted parrot (RRP), black grass (BG), large wild grass (LCG) ) and yellow fox tail (YFT).

TABLE VI

I GR Rate GR85 Rate

(kg / ha) (kg / ha) -

Bettera BYG WO DB RRP BG LCG YFT

yes to su

cre

  > 1.12 <0.07 0.28 O, 21> 1.12 0.14 0.14 0.14

  (> 16) (> 4) (> 5.3) (NS) (> 8) (> 8) (> 8)

  The results in Table VI show that the compound of Example 3 selectively controlled each weed in the test, except red-rooted hawthorn, at well rates.

  less than 1.12 kg / ha, proving the general character of

  ral of this compound as an effective herbicide in

harvest important.

  The compounds of the present invention can be used safely with the normal degree of care required

  to handle herbicidal compounds; no special precaution

this is required.

  Accordingly, it will be appreciated from the description of

  As previously described, the compounds of this invention have shown unexpectedly superior herbicidal properties, both absolutely and relative to structurally relevant compounds in the prior art, one of which ( the

  butachlor) -is the active ingredient in a commercial herbicide.

  this. More particularly, the compounds of the present invention

  have been shown to be remarkable selective herbicides, especially

  especially for the control of Asian, annual and perennial weeds, important from an economic point of view,

in the rice transplanted.

  More particularly, compounds according to the present invention

  the invention has a remarkable control of annual grasses consisting of Echinochloa crus-galli, and 21. Monochoria vaginalis and perennial weeds such as

  Cyperus serotinus, Eleocharis kuroguwai, and some

* Some members are particularly effective against Sagita-

  taria trifolia, while controlling and / or removing from

  annual grasses and other perennial weeds

  less resistant, including those mentioned in the

  II, III and VI above, and others.

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

  are prepared by mixing the active ingredient with an adjuvant

  including diluents, extension products (char-

  ges), carriers and packaging agents for

  compositions in the form of finely divided particulate solids, granules, pellets, solutions, dispersions or emulsions. Thus, the active ingredient can

  be used with an adjuvant such as a finely divided solid

  a liquid of organic origin, water, a wetting agent, a dispersing agent, an emulsifying agent or

  any suitable combination of these products.

  The compositions of the present invention, particularly

  liquids and wettable powders, contains

  preferably as conditioning agents one or more

  It is also possible to use enough surfactants to make a given composition readily dispersible in water or in oil. The incorporation of a surfactant into the compositions greatly enhances their effectiveness. By the term "surfactant", it is understood that wetting agents, dispersing agents,

  suspending and emulsifying agents are included.

  Anionic, cationic and nonionic agents may

  to be used with equal ease.

  Preferred wetting agents are alkylbenzenes

  zen- and alkylnaphthalenesulfonates, sulfated fatty alcohols, amines or acid amides, esters of long chain acids of sodium isethionate, esters of sodium sulfosuccinate, esters of fatty acids. sulphated or sulphonated, petroleum sulphonates,

  sulphonated vegetable oils, acetylenic glycols referred to

  polyoxyethylene derivatives of alkylphenols (for example,

  especially isooctylphenol and nonylphenol) and

  polyoxyethylenic esters of higher fatty acid esters

  monocarboxylic anhydrides of hexitol (for example,

  Bitan). Preferred dispersion products are methyl-

  cellulose, polyvinyl alcohol, lignin sulphonates

  sodium, polymeric alkylnaphthalenesulfonates, naphthalene

  sodium sulphonate and polymeric bisnaphthalene sulphonates

thylène.

  Wettable powders are dispersive compositions

  sands in water containing one or more ingredients

  a solid inert extender (filler) and one or more wetting and dispersing agents. Products

  inert solids are usually of mineral origin.

  such as natural clays, diatomaceous earth

  and synthetic minerals from silica and

  guages. Examples of these extension products include-

  kaolinites, so-called attapulgite clay and synthetic magnesium silicate. The wettable powder compositions of the present invention ordinarily contain about 0.5 to 60 parts (preferably 5-20 parts) of active ingredient, about 0.25 to 25 parts (preferably 1-15 parts) of wetting agent. about 0.25 to 25 parts (preferably 1.0-15 parts) of dispersion product and about 5 parts to about 95 parts (preferably 5-50 parts) of inert solid extension product, all parts being by weight relative to the total composition. When required, about 0.1 to 2.0 parts of the solid inert extender product can be

  replaced by a corrosion inhibitor or an anti-

foam or both.

  Other formulations include concentrates of

  dust comprising 0.1 to 60% by weight of the active ingredient

  tif on a suitable extension product; these dusts can be diluted for application in concentrations

  in the range of about 0.1-10% by weight.

  23. Suspensions or aqueous emulsions may

  prepared by stirring an aqueous mixture of an ingredient

  water-insoluble active ingredient and an emulsifying agent

  until they are uniform and then homogenize

  to give a very finely divided emulsion of particles

  Sees. The resulting concentrated aqueous suspension is

  tered by its extremely small particle size,

  so that, when diluted and pulverized, the

  is very uniform. Suitable concentrations of these

  formulations contain about 0.1-60%, preferably 5-

  %, by weight of active ingredient, the upper limit being determined by the solubility limit of the active ingredient

in the solvent.

  In another form of aqueous suspension, a herbal

  Water-immiscible bicide is encapsulated to form a microencapsulated phase dispersed in a water-soluble phase. In an exemplary embodiment, tiny capsules are formed

  by bringing together an aqueous phase containing an emulsion

  lignin sulphonate, a non-miscellaneous chemical

  water and polymethylene polyphenyl isocyanate, in

  dispersing the immiscible phase with water in the aqueous phase

  followed by the addition of a polyfunctional amine. The components

  Isocyanate and amine salts react to form a solid wall of urea casing around the particles of the product

  water-immiscible chemical, thus forming microcap-

  sules. Generally, the concentration of microenvironmental matter

  capsulated will range from approximately 480 to 700 g / l of total composition,

preferably 480 to 600 g / l.

  Concentrates are usually-solutions -

  of active ingredient in water immiscible solvents or

  partially immiscible with water, with a surfactant

  active. Suitable solvents for the active ingredient of the

  The present invention includes dimethylformamide, dimethylformamide,

  thylsulfoxide, N-methylpyrrolidone, hydrocarbons and

  ethers, esters or ketones immiscible with water.

  However, other high concentration liquid concentrates can be formulated by dissolving the active ingredient in a solvent and then diluting, for example with kerosene, to

the spray concentration.

  The concentrate compositions here contain genera

  typically about 0.1 to 95 parts (preferably 5-60 parts) of active ingredient, about 0.25 to -50 parts (preferably

  1-25 parts) of surfactant and, where this is

  ge, about 4 to 94 parts of solvent, all parts being

  by weight based on the total weight of the emulsion oil

nable.

  The granules are physical particulate compositions

  sically stable comprising the active ingredient adhering to or

  distributed through a basic matrix of a product of exten-

  Inert particulate fraction, finely divided. To help the

  If the active ingredient is isolated from the particulate product, a surfactant, such as those mentioned above, may be present in the composition. Natural clays,

  pyrophyllites, illite and vermiculite are examples

  Many well-functioning classes of mineral extension products

  particulate matter. The preferred extension products are porous, absorbent, preformed particles, such as

  preformed and sieved particulate attapulgite or vermicul-

  particulate expanded thermally and fine clays

  such as kaolin clay, the attap-

  - hydrated cottage or bentonite clays. These products of ex-

  Voltage are sprayed or mixed with the active ingredient

  to form the herbicidal granules.

  The granular compositions of the present invention

  may contain from about 0.1 to about 30 parts, preferably

  preferably about 3 to 20 parts by weight of active ingredient per 100 parts by weight of clay and 0 to about 5 parts

  by weight of surfactant per 100 parts by weight of

particle size.

  The compositions of the present invention may

  also contain other additives, for example

  grapes, other herbicides, other pesticides, products

  and the like, used as adjuvants or in combination with

  with any of the adjuvants described above.

  25. Other herbicidal compounds useful in combination with the active ingredients of the present invention, particularly

  for use in transplanted rice include, for example,

  Methyl 5- (2,4-dichlorophenoxy) -2-nitrobenzoate, (common name "bifenox", active ingredient in the herbicide known as Modown), paratoluenesulfonate

  1,3-dimethyl-4- (2,4-dichlorobenzoyl) -5-pyrazolyl

  code code "SW 751"), α- (3-naphthoxy) propionanilide (de

  code code "MT-101"), the 2,4-dichloro-3'-methylene ether

  xy-4'-nitrodiphenyl (code designation "W-52"), 3,4-

  dichloropropionanilide (common name "propanil"), etc. For use in other unincorporated crop plants

  rice, other herbicide compounds may also be

  combined with the compounds according to the present invention.

  For example, these other compounds include triazines, ureas, carbamates, acetamides, acetanilides, uracils, acetic acid or phenol derivatives, thiolcarbamates, triazines, benzoic acids, nitriles, ethers, and the like. biphenyl and the like, such as: Heterocyclic nitrogen / sulfur derivatives 2-chloro-4-ethylamino-6-isopropylamino-s-triazine 2-chloro-4,6-bis (isopropylamino) -s-triazine 2-chloro-4, 6-bis (ethylamino) -s-triazine

  3-Isopropyl-1H-2,1,3-benzothiadia 2,2-dioxide

  zin-4- (3H) -one 3-amino-1,2,4-triazole

  the salt of 6,7-dihydrodipyrido (1,2-a: 2 ', 1'-c) -pyrazi-

  dinium 5-bromo-3-isopropyl-6-methyluracil 1,1'-dimethyl-4,4'-bipyridinium 5-t-butyl-3- (2,4-dichloro-5-isopropoxyphenyl) -1,3 , 4oxadiazol-2-one Ureas N '- (4-chlorophenoxy) phenyl-N, N-dimethylurea N, N-dimethyl-N' - (3-chloro-4-methylphenyl) urea 3- (3,4) 1,3-dimethyl-3- (2-benzothiazolyl) urea-3- (pchlorophenyl) -1,1-dimethylurea 1-butyl-3- (3,4-dimethylurea) -1,4-dimethylurea dichlorophenyl) -1methylurea Carbamates / thiolcarbamates 2-chloroallyl diethyldithiocarbamate S- (4-chlorobenzyl) N, N-diethylthiolcarbamate N- (3chlorophenyl) isopropyl carbamate

  S-2,3-dichloro N, N-diisopropylthiolcarbamate

  allyl ethyl N, N-dipropylthiolcarbamate S-propyl dipropylthiolcarbamate Acetamides / acetanediols / anilines / amides 2-chloro-N, Ndiallylacetamide N, N-dimethyl-2,2-diphenylacetamide N- (2) N-Isopropyl-2chloroacetanilide, 2 ', 6'-diethyl-N-methoxymethyl-2-chloroacetanilide, 4-dimethyl-5- [[(trifluoromethyl) sulfonyl] amino] phenyl) acetamide

  2'-methyl-6'-ethyl-N- (2-methoxyprop-2-yl) -2-

chloroacetanilide

  Α, α, α-trifluoro-2,6-dinitro-N, N-dipropyl-p-toluene

  N- (1,1-dimethylpropynyl) -3,5-dichlorobenzamide Acids / esters / alcohols 2-dichloropropionic acid 2-methyl-4-chlorophenoxyacetic acid 2,4-dichlorophenoxyacetic acid 2- Methyl 4- (2,4-dichlorophenoxy) phenoxy] propionate 3-amino-2,5-dichlorobenzoic acid 1-methoxy-3,6-dichlorobenzoic acid 2,3,6-trichlorophenylacetic acid N-naphthylphthalamic acid

  5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-

  sodium nitrobenzoate 4,6-dinitro-o-sec-butylphenol N (phosphonomethyl) glycine, its monoalkyl (C 1-6) amine salts, its alkali metal salts and their

27. -

  combinations. Ethers 2,4-dichlorophenyl-4-nitrophenyl ether

  2-chloro-α, α, α-trifluoro-p-tolyl-3-ethoxy ether

  4-nitrodiphenyl Various products 2,6-dichlorobenzonitrile methanearsonate monosodium acid disodium methanearsonate Herbicides of the present invention may be

  used individually or in mixtures with other

  herbicides and they can be used according to a

  sequential use with other herbicides. For example,

  treatments of a plant to be harvested consisting of rice

  with the herbicides of the present invention may be followed by treatments with other herbicides or with

  mixtures such as S-4-chlorobenzyl diethylthiocarbamate

  the (common name "benthiocarb") plus 2-chloro-4,6-di (ethyl-

  mino) -l, 3,5-triazine (common name "simazine") or the 2,2-diol

  3-isopropyl- (1H) -benzo-2,1,3-thiadiazin-4-one (commonly referred to as

  "bentazone") or 4- (4-chloro-2-methylphenoxy) buty-

(common name "MCPB").

  The compounds of the present invention have their use

  main in the transplanted rice. However, as indicated by the experimental results for the compound of Example 3 in Table V, at least some members of this class

  may also be used in rice seeded directly

  ment. However; as a result of the high unitary activity of

  compounds according to the present invention, the rice seeded directly

  This may be less tolerant to certain members of the compounds of the present invention. Accordingly, it is within the scope of the present invention to combine these herbicides with safety products or

  antidotes to reinforce the tolerance of both rice

  qué and rice sown directly. Security products

  examples, which are intended to be useful with herbicides

  of the present invention, include cyanomeric ether,

  28. Phytylglyoxylonitrile 2-oxime described in

  U.S. Patent No. 4,152,137, 5-thiazolecarboxylic acids

  2,4-disubstituted compounds and their derivatives as described in

  US Patent No. 4,199,506, and other security products.

  known for 2-haloacetanilides in rice.

  Useful fertilizers in combination with ingre-

  Active ingredients include, for example, ammonium nitrate,

  urea, potassium carbonate and superphosphate. On au

  useful additives include materials in which

  plant organisms take root and grow, such as

  compost, fertilizer, humus, sand and the like.

  Herbicidal formulations of the types described above

  above are given as examples in several examples.

  illustrative examples below.

  I. Emulsifiable Concentrates A. Compound of Example 1 Ester consisting of phosphate of alcohols

  ethoxylates (for example, a product known as

  as filed by GAFAC RE-610) Tertiary ethoxylated amine from fatty oils such as palm oil (e.g. product known under the trademark Ethomeen C / 12) Monochlorobenzene C9 (T-400) aromatic solvent B. Compound of Example 3 Product called GAFAC RE-610 Product known under the registered trademark Ethomeen C / 12

- MCB

  C. Compound of Example No. 4 Dodecylbenzenesulfonate Blend

  calcium / polyoxyethylene ethers (eg

  duit said Atlox 3437F)% by weight, 0 4.125 0.875 13.5 31.5, 00 46.45 4.125

- 0.875

  48.55, 00, 0 1.0 29. Xylene II. Liquid concentrates A. Compound of Example No. 5 Xylene B. Compound of Example No. 6 Dimethyl sulfoxide C. Compound of Example No. 7 N-methylpyrrolidone D. Compound of Example No. 8 Ethoxylated castor oil Product called Rhodamine Dimethylformamide 94.0.0.0% by weight, 0.000.0.0.0.0.0.0.0.0 0.5 74.5,00 III. Emulsions A. Composed of Example No. 9

  Polyoxyethyl block copolymer

  lene / polyoxypropylene with butanol (e.g. product known under the tradename Tergitol XH) Water B. Compound of Example No. 10

  Polyoxyethyl block copolymer

  lene / polyoxypropylene with butanol Water% by weight, 4.0 56.0, 00, 0 3, 91.5, 00 IV. Wettable powders A. Compound of Example No. 1 Sodium lignosulfonate N-methyl-N-sodium oleyl-taurate% by weight, 0 3.0 1.0 30. Amorphous silica (synthetic) B. Compound of Example 3 Sodium dioctyl sulfosuccinate Calcium lignosulfonate Amorphous silica (synthetic) C. Compound of Example No. 4 Sodium lignosulfonate N-methyl-N-oleyl-sodium taurate Clay kaolinite V. Dust A. Compound of Example No. 10 Attapulgite B. Compound of Example No. 11 Montmorillonite C. Compound of Example No. 12 Bentonite D. Compound of Example No. 13 Diatomaceous earth% by weight 2.0 98.0, 00, 0.0, 00, 0, 0, 00 1.0 99.0, 00 VI. Granules A. Compound of Example No. 1 Granular Attapulgite (Passing

  mesh sieve included

  0.841 mm and 0.420 mm, ie 20-40 mesh) B. Compound of Example No. 3 Diatomaceous earth (passing through a sieve with mesh size between% by weight, 0.000

, 0 - 71.0, 00, 0 1.25 2.75 16.00, 00, 0 3.0 1.0 86.0, 00 31. 0.841 mm and 0.420

mm) C. Compound of example-n 4

  Bentonite (passing through the sieve to open

  mesh size between 0.841 mm and 0.420 mm) D. Composed of Example 5

  Pyrophyllite (passing through the sieve to open

  mesh size between 0,841 mm and 0,420 mm) VII. Microcapsules A. Compound of Example No. 1 encapsulated in a polyurea shell wall Sodium lignosulfonate (eg, product known under the tradename Reax 88 B) bound to Water B. Compound of ExEaple embedded image in a polyurea envelope wall Potassium lignosulfonate (for example a product known under the trade name Reax C-21) Water J in a product of the invention C. Compound of Example No. 4 encapsulated wall polyurea shell Magnesium salt of lig nosulfate

known under the trademark -

  , 0, 00 0.5, 0, 00, 0, 0, 00 49.2 0.9 49.9, 00, 0 0.5

89.5 -

  , 00, 0 Treax LTM) 2.0 Water 18.0 .00 When operating according to the present invention, effective amounts of the acetanilides of the present invention

  are applied to the soil containing the plants, or are incorporated

32.

  in aquatic environments, in any manner whatsoever

  re ok. The application of liquid compositions and particulate solid compositions to the soil can be carried out by conventional methods, for example with mechanical dust-forming devices, pulverizing devices,

  telescopic and hand-held actuators and

  dust by spraying. The compositions can also be applied from aircraft in the form of

  dust or spray, as a result of their effectiveness.

  at low doses. The application of herbicidal compositions

  aquatic plants is usually carried out in addition to

  both the compositions with aquatic environments in the zone o

  control of aquatic plants is desired.

  The application of an effective amount of the compounds of

  the present invention at the place where the bad herbs are found.

  unwanted person is essential and critical for the

  of the present invention. The exact amount of ingredient

  to be used depends on a variety of factors, including the use of

  in aqueous media or soil media, the species

  this plant and its stage of development, the type and condition of the soil, the amount of rainfall and the specific anilide used. In a selective pre-emergence application to plants or soil, a dose of 0.02 to about 11.2 kg / ha, preferably about 0.04 to about 5.60 kg / ha, or suitably

  1.12 to 5.6 kg / ha of acetanilide is usually employed.

  Higher or lower rates may be sufficient or

  in some cases. For example, in some tests on rice seeded in mountainous terrain, compounds according to

  The present invention has shown a measurable value of endom-

  mowing to backyard grass at extremely low rates.

  Thus, the compound of Example 3 had a control of 5% of backyard grass at a rate of 0.035 kg / ha and the compound of

  Example 5 showed 10% control of

  yard at the rate of 0.0175 kg / ha. A person experienced in

  the technique can easily determine from this description.

  tion, including the example above, the optimum rate to be applied

  in any particular case.

  The term "soil" is used in its broadest sense to include all classical soils, as defined in the New Webster International Dictionary, 2nd edition, unabridged (1961). Thus, the term refers to any substance or medium in which vegetation can take root and grow and includes not only the earth,

  but also compost, fertilizer, manure (garbage), human

  mus, sand and the like adapted to maintain the growth

plant life.

  The present invention is not limited to the examples

  which has just been described, it is necessary to

  which may be subject to variations and modifications

will be known to the man of the art.

34.

Claims (11)

  1 - Compounds, characterized in that they have the mule: 0 ClCH2C X R \ N / C2H5 o-n-C4H9   o R is allyl, chloroallyl, propargyl, l-methoxy-   prop-2-yl, or a hydrocarbyloxymethyl radical having the   mule -CH20R1 o R1 is the allyl group or an alkyl radical in C1_5.   2 - Compound according to claim 1, characterized in   it is formed by N-propargyl-2'-n-butoxy-6'-ethyl-2-   chloroacetanilide. 3 - Compound according to claim 1, characterized in   what it is formed by N- (1-methoxyprop-2-yl) -2'-n-butoxy- 6'-ethyl-2-chloroacetanilide.   4-compound according to claim 1, characterized in   it is formed by N- (allyloxymethyl) -2'-n-butoxy-6 '-   ethyl-2-chloroacetanilide. 5 - Compounds according to claim 1, characterized   in that R1 is a C35 alkyl radical.   6 - Compound according to claim 5, characterized in   it is formed by N- (n-propoxymethyl) -2'-n-butoxy-6'- ethyl -2-chloroacetanilide.   7 - Compound according to claim 5, characterized in   it is formed by N- (sec-butoxymethyl) -2'-n-butoxy-6'- ethyl-2-chloroacetanilide.   8 - Compound according to claim 5, characterized in   what it is formed by N- (2-methylbutyl) -2'-n-butoxy-6'- ethyl-2-chloroacetanilide.   9 - Compound according to claim 5, characterized in   it is formed by N- (isoamyloxymethyl) -2'-n-butoxy-6'-   ethyl-2-chloroacetanilide. 35. - Compound according to claim 5, characterized   in that it is formed by N- (isobutoxymethyl) -2'-n-butoxy-   6'-ethyl-2-chloroacetanilide. 11 - Compound according to claim 5, characterized in that it is formed by N- (n-butoxymethyl) -2'-n-butoxy-6'-ethyl-2-chloroacetanilide. 12 - Herbicidal compositions, characterized in that they comprise an adjuvant and a herbicidally effective amount of a compound having the formula: ClCH2C 2 N / R C2H5O-n-C4H9   o R is allyl, chloroallyl, propargyl, l-methoxy-   prop-2-yl or a hydrocarbyloxymethyl radical having the formula   -CH2OR1, where R1 is the allyl group or an alkyl radical in C1_5.   13 - Composition according to claim 12, characterized   in the application of the provisions of any Claims 2 to 11.   14 - Method for combating undesirable plants   in plants to be harvested, characterized in that   apply to the place where these unwanted plants are found a herbicidally effective amount of a compound having the formula: ClCH2C R \ N / C2H5OO-n-C4H9   o R is allyl, chloroallyl, propargyl, l-methoxy-   prop-2-yl or a hydrocarbyloxymethyl radical having the formula   36. -CH2OR1, where R1 is an allyl group or an alkyl radical in C1-5.   - Process according to claim 14, characterized   in that the plant to be harvested is transplanted rice.   16 - Process according to claim 15, characterized in that the provisions of any one of Claims 2 to 11.   17 - A method for controlling weeds in transplanted rice, characterized in that it consists in applying to the place where these weeds are found a   effective herbicidal amount of N- (allyloxy)   methyl) -2'-n-butoxy-6'-ethyl-2-chloroacetanilide or N-   propargyl-2'-n-butoxy-6'-ethyl-2-chloroacetanilide or N-   (1-Methoxyprop-2-yl) -2'-n-butoxy-6'-ethyl-2-chloroacetaniline of.