CS219856B2 - Herbicide means - Google Patents

Abstract

Hydrocarbyl or hydrocarbyloxyalkyl-2- haloacetanilide compounds, herbicidal compositions containing said compounds as the active ingredient and herbicidal method of use in various crops, particularly transplant rice. The herbicides herein are particularly effective against annual and perennial weeds commonly associated with rice.

Description

The invention relates to herbicidal compositions which contain, as active ingredient, haloacetanilides and are suitable for agricultural purposes, in particular rice transplanting.

The invention thus relates to 2-chloroacetanilide having the specific combination of n ^J butoxy groups in ortho position, an ethyl radical in the other position, and as a substituent on the anilide ring-nitrogen group selected from the group consisting of · allyl, chloroallyl, propargyl, 2-methoxyprop A -2-yl group or a group of formula - CH 12 OR 1, wherein R 1 is an alkyl group having 1 to 5 carbon atoms.

Numerous 2-haloacetanilides closest to the active ingredients of the invention are unsubstituted or substituted with various substituents on the anilide nitrogen atom and / or on the anilide ring, which substituents include alkyl, alkenyl, alkynyl, alkoxy, polyalkoxy an alkoxyalkyl group, a heterocyclyl group, a halogen atom and other groups. The most related compounds of the prior art are protected in U.S. Patent Nos. 3,268,584, 3,442,945, 3,547,620, 3,773,492, 4,221,237, and Belgian Patent No. 810,763. However, in the case of none of the known compounds it does not disclose that it is suitable for transplanting rice, and none of these patents discloses compounds herbicidally active as in the present invention, and therefore, herbicidally active compounds are not now protected or recommended as herbicidal agents of a particular type as in the present invention.

The 2-haloacetanilides known from the prior art as suitable rice transplanting herbicides differ considerably in their structure from the 2-haloacetanilides of the present invention. In particular, all of the herbicidally active compounds known hitherto contain lower alkyl groups in both ortho positions to the anilide nitrogen atom and an alkoxyalkyl group on this nitrogen atom. Therefore, the herbicidal active ingredients for rice cultivation are not derived and are not objectable against the active ingredients according to the invention. However, in order to allow comparison, the relative herbicidal activity of the active compounds according to the invention is compared with that of the active compounds according to the invention

Θ the herbicidal MACHETE (trademark of Monsanto Company), the active ingredient of which is 2‘, 6‘-diethyl-N- (n-butoxymethyl) -2-chloroacetanilide (commonly referred to as butachlor). Butachlor and its hoimologists (here referred to as "ethyl butachlor") are protected as herbicidally effective rice cultivators in U.S. Patent 3,663,200. Of the 2-haloacetanilide herbicides known in the art, only the herbicidal composition MACHETE is commercially available at present.

Although the herbicidal rice cultivation agents known in the art are considered useful, there is a constant effort to improve them, aimed at resistant weed plants at low rates of use, which is economically significant, while maintaining devastating or suppressing effects to such weeds for a long time at harmless to cultivated rice and at reduced toxicity to fish and mammals.

The aforementioned herbicidal herbicides have one or more undesirable properties when used in rice transplanting. Some deficiencies of herbicidal rice transplants include their generally poor effectiveness in controlling and / or suppressing economically important resistant perennial weeds such as Cyperus serotinus, Eleocharis kuroguwai and Sagittatia trifolia along with reduced eradication efficiency or · Suppression of annual weed plants of Echinochloa crus-galli and, to a lesser extent, Monochoria vaginalis within two to six weeks. This drawback is particularly evident at lower doses used, for example at a dose less than 0 ^; , 19 kg / ha) and at lower rates. In fact, field trials have shown that in some treatments some of the prior art herbicidal compositions fail to respect the selectivity of elimination of Eleocharis kuroguwai at a dose below 6 kg / ha or even at a dose of 3 kg / ha in less than 2 or 3 weeks. Similarly, it has been found in field trials that some of the prior art herbicidal agents fail to account for significant suppression of Sagittaria trifolia after four to five weeks.

It is therefore an object of the present invention to provide a class of herbicidal compositions particularly suitable for transplanting rice that are selective and (1) safe, i.e., do not cause more than 15% damage when transplanting rice at a dose of at least 2.24 kg / ha. restraining the hedgehog corn (Echinochloa cruss-galli, Monochoriu vaginalis, the sedge (Cyperus serotinus) and Eleocharis kuroguwai and 3) would increasingly suppress the sagittaria (Sagitaria trifolia). They would be safe in use, ie they would not require any special precautions for use.

The invention therefore relates to herbicidal compositions which contain, as active ingredient, 2-haloacetanilides of the general formula I, characterized by a particular combination of groups on the anilide nitrogen atom, the ortho position alkoxy group and the second ortho position ethyl group having unexpectedly higher and excellent selectivity Herbicidal properties as herbicidal agents for transplanting rice with respect to herbicidally active formulations with active ingredients, the closest structures known in the art, including commercial herbicidal agents for rice cultivation.

The main feature of the herbicidal compositions according to the invention is their ability to control and / or suppress annual and perennial narrow-leaved weeds in rice crops, especially the predominant and economically important annual plants such as Echinochlca crus-galli, Moncchoria vaginalis and perennial plants such as flatsedge (Cyperus serotinus), Eleochoris kuroguwai, and sagltaria trifolia and similar harmful weeds.

The herbicidal compositions according to the invention contain as active ingredient compounds of the formula I

where it means

R is an allyl, chlorallyl, propargyl, 1-methoxyprop-2-yl group or a group of the formula -CH 2 OR 1 wherein R is

R 1 is C 1 -C 5 alkyl, preferably C 3 -C 5 alkyl.

Preferred are the active compounds according to the invention of formula I wherein R is a propargyl, 1-methoxyprop-2-yl group and of formula I wherein R1 is a n-propyl, sec-butyl, 2-methylbutyl or isoamyl group. Further preferred are active compounds of formula I wherein R is allyl, chlorallyl or. a group of the formula —CH2OR1, ........__________________________________________________________ where is

R 1 is methyl, isopropyl, nbulyl or -isobutyl.

The compounds of formula (I) effective according to the invention can be prepared by a number of methods. For example, compounds of Formula I may be prepared by N-alkylating an anion of a suitable secondary. 2-haloacetethanilide - an alkylating agent in a basic medium.

Example 1 below illustrates the use of this N-alkylation process for the preparation of one type of compounds of Formula I. A modified N-alkylation process is described in Example 2 for the preparation of another type of compounds of Formula I. Modified N-alkylation process described in Example 2 includes the preparation in situ of the halomethyl alkyl ether or halomethyl alkenyl ether used as starting materials in the N-alkylation process.

Example 1

2'-n-Butoxy-6'-ethyl-2-chloroacetanilide, S, 4 g (0.02 mol), propargyl bromide, 2.6 g (о, О2 mol) and 2.0 g of benzyltrieithylammonium chloride are mixed with each other in 150 ml of methylene chloride and cooled rapidly. 45 ml of 4550% sodium hydroxide is added at 15 + to the mixture at once and stirred for 5 minutes, then 150 ml of cold water is added. The layers were separated, washed with water, dried (MgSO4) and evaporated in a collar flask to give 4.45 g (73-1% yield) of a yellow oil, b.p.

Analysis for C17CINO3 0 /) ·:

calculated:

C 06.33, H 7.20, Cl 11.52, found:

C 66.35, H 7.21, Cl 11.50.

The product identified as N-propargyl-4-n-butoxy-4-ethyl-2-chloroacetanilide.

Example 2

Following essentially the same procedure as described in Example 1, however, allyl bromide was used as the alkylating agent to give 4.9 g (79% yield) of yellow oil, b.p. 66 Pa, using a collar flask.

Analysis for C 17 H 24 ClNO 2 calculated (%):

C -65.90, H 7.01, Cl 11.44 found:

C 65.89, H 7.81, Cl 11.42.

The product was identified as N-allyl-2-n-butoxy-6'-ethyl-2-chloroacetanilide. ........

Example - 3

This example describes a modification of the method described in Example 1. In this embodiment, the alkylating agent is formed into a sieve, the operation is therefore more efficient, more economical and simpler.

To a rapidly cooled mixture of 6.96 g (0.12 mol) of allyl alcohol, 1.8 g (0.12 mol) of anhydrous paraformaldehyde and 1-0 ml of imethylene chloride was added 4.71 g (0.06 mol) of acetyl chloride; The mixture was stirred for 90 minutes until all paraformaldehyde had dissolved. 5.4 g (0.02 mole of 2'-n-butoxy-6'-ethyl-2-chloroacetanilide, 2.0 g of benzyltriethylammonium chloride and 50 ml of methylene chloride) are then added to the mixture and the mixture is cooled to 10 ° C. 50 ml of 50% sodium hydroxide is added in one portion and stirred for 15 minutes, the layers are separated, washed with water, dried over magnesium sulphate and evaporated using a collar flask to give 6.0 g (92% yield). of a clear oil, m.p. 122 DEG C. at 5 mm Hg.

Analysis calculated for (C16H20CINO3) (%) ^:

C 63.61, H 7.71, Cl 10.43, found:

C 63.60, H 7.74, Cl 10.42,

The product identified as N- (allyloxymethyl) -2‘-n-butoxy-6‘-ethyl-2-chloroacetanilide.

Example 4

In essentially the same manner as described in Example 3, but using 2-butanol as the alkylating agent, 4.15 g (78% yield) of a clear oil was obtained with a boiling point of 118 * 43 at 2.66 Pa using Collar flasks.

Analysis for C 19 H 30 ClNO 3 calculated (%):

C 64.12, H 8.50, Cl 9.96, found:

C 04.05, H 8.52, Cl 9.90.

Product Identified as N- (sec-butoxymethyl) -2‘-n-butoxy-6‘-ethyl-2-chloroacetanilide.

The secondary anilide as a starting material used in the methods described above is prepared by methods known per se, such as, for example, the haloacetylation of the corresponding primary amine with haloacetylating agents such as haloacetyl halide or haloacetyl anhydride. Typically suitable amount of the appropriate primary amine is dissolved in a solvent such as methylene chloride containing a base, such as 10% sodium hydroxide and stirred vigorously while mixing with a solution of a haloacetylhalide such as chloroacetyl chloride under external cooling, for example at 15 to 25 ^Q 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 preparation of secondary anilides can also be prepared by methods known per se, for example by catalytic reduction of the corresponding suitably substituted nitrobenzene, such as 2-alkoxy-6-alkylnitrobenzene, in a solvent such as an alcohol such as ethanol using platinum oxide catalyst.

Example 5

This example describes a process for the preparation of N- (2-methoccypnop-2-yl) -2'-n-butoxy-6'-ethyl-2-chloroacetanilide.

To a rapidly cooled solution of N- (2-methoxyprop-2-yl) -2'-in-butoxy-6'-ethylanilide, 4.42 g (0.016 mol) in 0.0176 mol of 10% sodium hydroxide and 100 ml of dichloromethane was added. add 2 g (0.0176 mol) of chloroacetyl chloride dropwise; the solution was stirred for 10 minutes, the layers were separated and the organic layer was washed with water, dried over magnesium sulfate and evaporated using a collar flask to give 3.5 g (05% yield) of a yellow oil, b.p. 43 at a pressure of 9.33 Pa.

Analysis for СвНгвСШОз calculated (%):

C 63.24, H 8.26, Cl 10.37, found:

C 63.16, H 8.27, Cl 10.36.

The product identified as N- (2-methoxyprop-2-yl) -2‘-n-butoxy-6‘-ethyl 1-2-chloroacetanilide.

The secondary anilide as the starting material used in the process of Example 5 is obtained in a manner known per se (for example, as described in Belgian Patent No. 810,763, cited above). 19.3 g (0.1 mol) of 2'-n-butoxy-6'-ethylainiline are heated at 50 ° C in 15 ml of ethanol and in 15 ml of glacial acetic acid, then 9.08 g (0.11) are added. mol) methoxyacetone and 0.1 g platinum oxide and the mixture is hydrogenated at 50 ° C for 4 hours; mixture was filtered and evaporated using a Kugelrohr at 10i0 ^Q C and a pressure of 9.33 mm Hg to give a yellow oil.

Analysis for C 16 H 27 NO 2 calculated (%):

C 72.41, H 10.25, N 5.28, found:

C 72.36, H 10.27, N 5.23.

The product identified as N-J-methoxyprop-2-yl) -2)-n-butoxy-6‘-ethylaniline.

Examples 6 to 13

In essentially the same manner and under the same conditions as described in Examples 1 to 4 using the same secondary or 228856 people but suitable alkylating agents as starting materials and appropriate amounts thereof, the corresponding products of Examples 6 to 13 corresponding to the general formula are obtained. In Examples 6 to 12, the preparation was carried out in the same manner as described in the N-alkylation process in Examples 3 and 4, and the product of Example 13 was prepared by the Na-alkylation method described in Examples 1 and 2.

Table 1

CÍCW C _{£ X} ^ CH-OR. N

Example number Ri Boiling point ° C Bye 6 i-CsHii 137 (5,33) 7 i-ClHg 120 (4.0) 8 n-C3H7 117 (2,66) TT ^CHs 9 —CH3CHCH2CH5 134 (4.0) 10 n-CiHa 128 (4.0) 11 CH3 130 (5,33) 12 I-C4H7 119 (2,66) Cl AND 13 1 - CH2C = CH2 136 (1,33)

Analysis

Element Calculated Found O 64.94 64.96 H 8.72 8.75 Cl 9.53 9.58 C 64.12 64.06 H 8.50 8.53 Cl 9.96 10,06 C 63.24 63.31 H 8.36 8.27 Cl 10.37 10.42 C 64.94 64.86 H 8.72 8.72 Cl 9.58 9.62 C 64.12 64.05 H 8.50 8.49 Cl 9.96 9.91 •C 61.24 61.31 H 7.71 7.71 Cl 10.30 10.33 C 63.24 63.41 H 8.26 8.31 Cl 10.37 10.46 C 59.31 59.47 H 6.73 6.78 Cl 20 · 60 20.52

As mentioned above, the compounds of formula (I) prepared according to the invention are active against most Asian weed plants as herbicidal agents in rice transplanting. However, they also exhibited pre-emergence or post-emergence herbicidal activity in the case of other weeds in other crops. Tables II and III summarize the results of the tests performed to determine the herbicidal activity in the pre-emergence compounds of formula I.

Pre-emergence performance tests shall be carried out as follows:

Good quality potted soil is placed in aluminum bowls and pressed to a height of 9.526 millimeters to 12.7 mm from the top of the bowl. Numerous seeds or vegetative offshoots of different plant species are introduced onto the soil surface. The dishes are then weighed with the soil needed to replenish the soil to cover seeds or vegetative offshoots. The soil and the known amount of active ingredient used in the solvent or as a suspectable powder are thoroughly mixed and used to coat the prepared mixes. After treatment, the bowls are placed in a greenhouse, where they are moistened by bottom irrigation to provide the necessary moisture for emergence and growth.

About two weeks after sowing and treatment, plants were observed and the results recorded. These results are summarized in Tables II and III. Herbicidal action is assessed by a fixed scale based on the percentage damage of each plant species. This scale is as follows:

% damage Evaluation 0 to 24 0 25 to 49 1 50 to 74 2 75 to 100 ' 3 not specified 5

In one series of tests, the results of which are given in Table II, the following plant species, indicated by the following letters in the table, were used:

A thistle (Cirsicum vulgare)

B beet

C parasite, abutilone

D povíjnice

E white imerlik

F ferns pepper

G chylory (ylellow nutsedge)

H creeping grass

And Halep sorghum

J brome (downy brome)

The hedgehog corns the leg

Table II

Before emerging

Compound according to example no kg / ha AND (B) C Plant species H AND J TO D E F G 1 11.2 3 2 1 2 3 3 3 3 3 3 3 5.6 3 2 1 2 3 2 3 3 0 3 3 2; r 11.2 3 2 2 3 3 3 3 3 3 3 3 5.6 2 1 1 1 1 1 3 2 0 3 3 3. : 11.2 5 · ' 0 1 1 2 2 3 3 3 3 3 5.6 5 0 0 0 3 2 2 3 3 3 3 4 11.2 3 0 0 0 2 1 3 2 0 3 3 5.6 3 0 0 0 1 2 2 3 0 3 3 5 11.2 5 0 1 0 3 2 3 3 5 3 3 5.6 5 0 0 0 2 3 1 3 5 3 3 6  11.2 5 0 0 0 0 1 o ... 3 0 3 3 :: 5.6 5 0 0 0 0 0 3 0 0 3 3 7 11.2 2 0 3 2 3 3 3 3 1 3 3 5.6 3. 1 2 3 3 3 2 3 1 3 3 8 11.2 3 0 0 0 2 1 3 2 1 3 3 5.6 3 1 0 0 ' 2 1 3 2 0 3 3 9 11.2 5 0 0 0 0 1 1 2 0 3 3 5.6 5 0 0 0 0 0 0 0 0 3 3 10 11.2 3 0 1 1 1 2 2 3 3 3 3 5.6 1 0 0 0 3 1 1 1 1 3 3 11 11.2 3 1 2 3 3 2 3 3 2 3 3 5.6 0 0 2 2 2 1 3 2 3 3 3 12 11.2 2 0 1 3 3 1 3 3 2 3 3 5.6 1 0 » 1 1 1 1 3 2 1 3 3 13 11.2 0 0 1 0 2 0 3 2 0 3 3 5.6 0 0 0 0 1 0 0 1 0 3 3

The following plants, indicated in Table III, summarizing the test results, are tested as follows:

L soya

M sugar beet

N wheat

About rice

R hemp (hemp sesoamaj

E goosefoot white

F rays · pepper

C parasite, abutilone

P čirók

B beet

Q buckwheat

D povíjnice

J Brome (downy brome)

S millet

The hedgehog corns the leg

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It has been found that the herbicidal compositions of the present invention have unexpectedly superior properties as rice transplanting herbicides, particularly with respect to their selective action on economically important resistant annual weed plants such as the hedgehog of corn and Monochoria vaginalis and perennial weed plants such as (But with one or two exceptions) and Eleocharis kuroguwai, where in some cases they suppress the perennial weed plant Sagittaria trifolia to a greater extent than the commercially known herbicide MACHINE, and also destroy or suppress numerous other less resistant perennial and annual weeds.

To demonstrate the unexpectedly superior properties of the compounds of formula I, both absolute and relative, greenhouse tests are carried out. In these tests, MACHETE, the only commercial herbicide currently available containing 2-haloacetanilide as active ingredient in rice-9 cultures, is used for comparison.

In discussing the results below, occasional references to the doses of herbicidal composition used are referred to as "GRis" and "GRes"; they are the doses in kilograms per hectare (kg / ha) that are convertible into pounds per acre (lbs / A) by dividing the dose in kg / ha by 1.12. "GRis" means the maximum herbicide dose required to 151% or less damage to a crop plant, and "GRes" means the minimum dose required to achieve 85% inhibition of weed plants. Gris and benefits Gres is used as a measure of possible operating properties, which means that vhcdné commercial herbicides may be _greater, or less destructive efficiency of the plants within reasonable limits.

Another guide for assessing the effectiveness of a chemical as well as a selective herbicidal composition is the &quot; selective factor &quot; (&quot; SF &quot;) for the herbicidal composition in a given crop plant and for a given weed plant. The selective factor is a measure of the relative degree of safety for a crop plant and the detrimental effect on a weed plant and is expressed by the ratio GRis / GRss, that is, by dividing the GRis / ss value for a crop plant by GR35 for a weed. / ha (optionally in 1b / A).

Since the tolerance for crop plants and the weed destruction are interrelated, a brief discussion of this relationship is relevant with regard to the selectivity factor. In general, it is desirable that the safety factor for crop plants, i.e. the herbicidal tolerance value for crop plants, is high, because for one reason or another it is often desirable to use higher concentrations of herbicide. On the contrary, it is desirable that the weed control dose should be small, i.e., that the herbicidal composition has a high unit efficacy, for economic and possibly also environmental reasons. However, small doses of herbicide use may not be sufficient to control certain weed plants, and higher doses of the herbicidal composition may be desirable. Thus, the best herbicidal compositions that kill a greater number of weed plants using a small amount of herbicidal composition while at the same time the highest degree of tolerance for crop plants. Therefore, a selectivity factor, as defined above, is used to quantify the relationship between inertia to crop plants and the weed control; the higher the numerical value of the selectivity factor, the higher the selectivity of the herbicidal composition with respect to weed control in a given crop plant.

In one comparative test in a greenhouse, the herbicidal activity values are obtained and are given in Table IV, showing the relative activity of the compounds of Example 1. 3 to 6, 8 and 9, representative compounds of the invention, with butachlor (the active substance). a commercial herbicidal composition for rice called MA.CHETE as a selective herbicide against economically important Asian weed plants commonly found in rice cultivation.

The following procedure is used in this greenhouse test: Ray potted soil containing approximately 50% by weight of krill and sieved through a 0.6 cm sieve is sieved for 5 to ¹⁰ days prior to use. The mugs were filled with this soil until they were filled to a height of 2.54 cm. Plants of rice (Bluebelle) 2 to 3 weeks old are replanted in pots and weed seedlings are also sewn into pots. The pots are then flooded and test chemicals are applied to the floodwater surface. The flood water is reduced to be able to germinate barnyardgrass (Echinochloa crus-galli] and then again flooded and maintained in těchto- conditions. After -se-experience an percent inhibition using a scale of 0 to ^1ϋ0!% Within three weeks after treatment (WAT).

The values shown in Table IV show the percent inhibition of plants within the test dose of 0.28 kg / ha to 2.24 kg / ha (0.25 to 2.0 lb / Å). Values are expressed as doses of GRis and GRes for rice and weed plants, as explained above: selectivity factors are shown in brackets for each weed; the term "NS" means "non-selective" within the test dose. The degree of pest control (Sagittaria trifolia), one of the most economically important weeds, and the weeds most severely affected for several years, is shown in the last column of Table IV; the percent destructive effect at the maximum dose tested is 2.24 kg / ha. Tested weed plants are indicated in the table as follows:

E'C Hedgehog Corns Echinochloa crus-galii

MV Monochoria vaginalis,

CS (Cyperus serotinus)

EK Eleocharis kuroguwai

ST pinch · (Ságilttaria trifolia)

Table IV

Compound GR15 according to kg / ha) of rice example EC number

MV

GR85 (kg / ha)

CS EK ST

Herbicidal effect at 2.24 kg / ha (%)

Butachlor 2.24 <0.28 (> 8.0) <0.25 (> 8.0) <0.25 (> 8.0) 0.4 (5.0) > 2.24 (NS) 15 Dec 1 2.24 <0.28 <0.28 <0.28 <0 28 > 2.24 65 (> 8.0) (> 8.0) (> 8.0) (> 8.0) (NS) 3 > 2.24 <0.28 <0.28 <0.28 <0.28 > 2.24 30 (> 8.0) (> 8.0) (> 8.0j (> 8.0) (NS) 4 > 2.24 <0.28 <0.28 <0.28 <028 > 2.24 20 May (> 8.0) (> 8.0) (> 8.0) (> 8.0J (NS) 5 > 2.24 <0.28 <0.28 <0.28 <0 · 28 > 2.24 10 (> 8.0) (> 8.0) (> 8.0) (> 8.0) (NS) 6 > 2.0 <0.28 <0.28 <0.28 043 > 2.24 10 (> 8.0) (> 8.0) (> 8.0) í> 4,7) (NS) 8 1.96 <0.28 <0.28 <0.28 <0 28 > 2.24 70 (> 7) (> 7.0) (> 7.0) (> 7.0) (NS) 9 1.87 <0.28 <0.28 0.211 0.88 > 2,2.4 25 (> 6.7) (> 6.7) (5.4) (1.9) (NS)

The values in Table IV illustrate some important advantages of the compounds of formula I with respect to butachlor.

1) The compounds of Examples 3-6 have a higher safety factor for rice than butachlor.

2) The compounds of Examples 1, 3, 5 and 8 have a higher selectivity factor against Eleocharis-curoguwa than butachlor.

3) The compounds of Example 1, 3, 4, 8 and 9 have a higher percentage of Saglt-taria trifolia than butachlor.

The overall improved properties of the compounds of the formula (I) active according to the invention are particularly pronounced for the compounds of Examples 1, 3 to 6, in view of the herbicidal action, as is clear from the values given in Table IV.

In another greenhouse comparative test, other compounds of the formula I are also compared with butachlor as standard herbicidal agents for rice transplanting. The compounds of Examples 2, 7 and 10 to 13 and butachlor were tested as described above; the test results are given in Table V.

Table V

Compound according to example no GRis (kg / ha) rice EC MV GR85 (kg / ha) EN EK ST Herbicidal effect at 2.24 kg / ha (%) Butachlor 1.68 0.99 1.3 > 2.24 0.71 > 2.24 25 (IN) (1,3) (NS) (2.4) (NS) 2 .1,8 <0 28 <0 25 0.78 <0.28 > 2.24 10 (> 7.2) (> 7.2) (2 6) (> 7.21 (NS) 7 > 2.24 <0.28 <0.43 > 0.52 0 47 > 2.24 0 (> 8.0) (> 5.3) (4.3) (4 8) (NS) 10 > 2.24 <0.28 <0.28 > 2.24 <0.28 > 2.24 0 (> 8.0) (> 8, C] (NS) (> 8.0) (NS) 11 1.12 <0.38 <0.28 0.95 <0.23 > 2.34 10 (4.01 (> 4.0) (1,2) (> 4.0) (NS) 12 0., 75 <028 «0.28 l.íi <0.28 > 2.24 15 Dec (> 2.7) í> 2,7) (NS) (> 2.7) (NS) 13 L12 <0 28 <0 28 1.0 <0.28 > 2.24 20 May (> 4.0) f> 4.0) (i>) (> 4 Ό) (NS)

Referring again to the values given in Table V, it is again clear that the compounds of formula I are preferable to butachlor:

1) The compounds of Examples 2, 7 and 10 show a higher safety factor in rice crops than butachlor.

2) All compounds of the invention have a higher selectivity factor with respect to Echinochloa crus-galli, Monochoria vagilis, Cyperu * s serotinus except for the compound of Example 10) and against Eleooharis kuroguwai than Butachlor. .

Although butachlor has higher safety factors than the compounds of Examples 11-13 and a greater percentage of Sagitaria trifolia destruction than the compounds of Formula I, this advantage is undermined by the significantly lower selectivity with respect to the other weeds tested. It is noted that although the test results in the greenhouse and field vary from test to test (more in greenhouse tests than in the field), the comparative values reported in the tables were found under the same conditions with respect to all herbicidal compositions tested. .

In other comparative tests in the greenhouse, a maximum test rate of 1.12 kg / ha and another maximum test rate of 2.24 kg / ha of the compound of Example 3 and butachlor were tested on plateau rice. It was found that, as the center of the two tests, the compound of Example 3 selectively kills Echinoichloa crus-galli at a dose of 0.31 kg / ha (0.277 lb / Α) while not damaging rice at a dose greater than 1.43. kg / ha (1.23 lb / Α), so that its selectivity factor is at least 4.6. In contrast, butachlor (a commercially available herbicide for rice crops) must be used at a rate of 0.7 kg / ha [0.6 (25 lb / Α) to selectively control the same weed while not damaging the rice at a dose greater than 1 / 68 kg / ha and greater than 1.5 lb / a), so that its selectivity factor is at least 2.4, ie approximately half that of the compounds of Example 3.

In further greenhouse tests, the compound of Example 3 was tested for efficacy against annual weed plants in diabetes at the tested doses of 0.0-7.12 kg / ha (0.0325-1.0 Ib / A). GR15 and GRss values for diabetes and various weeds are given in Table VI, the selectivity factors for the herbicidal agent against weeds in diabetes are indicated in brackets below the weed plant; 'NS' means 'non-selective' within the test range. The following abbreviations are used in the table:

BYG = hedgehog corns leg, W0 = oat deaf,

DB = Bone,

RRP = bent-grass, BG = field fox, LCG = tree frog and YFT = fox

Table VI

GR15 kg / ha BYG WO sugar beet

DB

GR85 kg / ha

RRP BG LCG YFT

over 1.12 less than 0.07 0.28 0.21 (larger (larger [larger than 16) than 4) than 5.3 Values in Table VI show that

Example 3 selectively kills all tested weed plants with the exception of amaranth bent at a rate below 1.12 kg / ha, thus demonstrating the utility of this compound as an active herbicide in an important crop plant.

The compound of formula (I) can be safely used without any precautions to be taken when handling herbicidal compounds; therefore no special measures are required.

It follows from the above that the compounds of the formula I have unexpectedly and significantly improved herbicidal properties both absolutely and with respect to the structurally similar compounds known from the prior art, one of which is butachlor as an active ingredient of commercial herbicidal compositions. In particular, the compounds according to the invention have shown excellent selective herbicidal action, in particular for controlling economically important Asian weeds and several-year-old weeds in rice transplanting. The compounds of the formula I have an excellent destructive action against annual grasses of Echinochloa crus-galli and Monochoria vaginalis and against several-year-old weeds such as Cyperus serotinus, Eleocharis kuroguwai and some of the compounds of formula I are particularly effective against Sagitaría trifolia, wherein the compounds of formula I destroy and / or suppress other less resistant annual grasses and perennial weeds, as shown in Tables II, III and IV.

The herbicidal compositions of the invention include concentrates which must be diluted before use containing at least one active ingredient and excipients; in liquid or solid form. The herbicidal compositions of the invention are prepared by mixing the active ingredient with excipients including diluents, extenders, carriers and conditioning agents to form the finely divided solid particles, granules, pellets, solutions, suspensions or dispersions. Thus, the active ingredients may be used with an adjuvant such as a finely divided solid, liquid of organic origin, water, a wetting agent, a dispersing agent, an emulsifying agent or any suitable mixture thereof.

The herbicidal compositions according to the invention,

over 1.12 · [NS] 0Д4 (greater than 8) 0.14 (greater than 8) 0.14 (greater than 8) particularly liquid and wettable pills,

preferably, they contain a conditioning agent, one or more surfactants in sufficient quantity to disperse the composition readily in water or oil. The incorporation of a surfactant into the herbicidal composition of the present invention greatly enhances its effectiveness. The term "surfactant" refers to wetting agents, dispersing agents, suspending agents, and emulsifying agents. Anionic, cationic or nonionic agents can be used as easily.

Preferred wetting agents include alkylbenzenesulfonates and alkylnaphthalenesulfonates, sulfated matt alcohols, amines or acid amides, long chain sodium isothionate esters, sodium sulfosuccinate esters, sulfated or sulfonated fatty acids in the form of esters, petrolsulfonates, sulfonated vegetable oils glycols, polyoxyethylene derivatives of alkylphenols (particularly isooctylphenol · and nonylphenol) and polyoxyethylated derivatives of mono-higher fatty acid esters of hexitolanhydride (such as sorbitan).

Wettable powders are water dispersible mixtures containing one or more active ingredients, an inert solid extender and one or more simulants and dispersing agents. Inert fixed extenders are generally mineral substances; of origin, such as natural clays, diatomaceous earth and synthetic minerals derived from silica and the like. Examples of such extenders are kaolinity, attapulgif earth, and synthetic magnesium silicate. The wettable powder compositions of the invention generally contain from 0.5 to 60 parts (preferably 5 to 20 parts) of the active ingredient, about 0.25 to 25 parts (preferably 1 to 15 parts) of the surfactant, about 0.25 to 25 parts. 25 parts (preferably 1.0 to 15 parts) of a dispersant and about 5 to 95 parts (preferably 5 to 50 parts) of an inert solid extender, all parts being by weight and refer to the weight of the herbicidal composition as of the whole. Optionally, about 0.1 to 2.0 parts of the solid inert extender may be replaced by a corrosion inhibitor, or an anti-foaming agent, or both.

Other types of compositions include powder concentrates containing 0.1 to 60% by weight of the active ingredient on a suitable extender; these powders may be diluted for use in concentrations of about 0.1 to 10% by weight.

Aqueous suspensions or emulsions can be prepared by mixing an aqueous mixture of a water-insoluble active ingredient and an emulsifying agent until uniformly dispersed and then homogenizing to form an emulsion of finely divided particles. The resulting aqueous suspension is characterized by an extremely small particle size, so that after dilution and spraying it provides a very uniform coating. Suitable concentrations are about 0.1 to 60% by weight, preferably 5- to 50% by weight of the active ingredient, the upper limit being determined by the solubility limit of the active ingredient in the solvent.

In another form of the aqueous suspension, the water-insoluble -herbicide is encapsulated to form a microcapsule phase-dispersed in the aqueous phase. In one embodiment, tiny capsules are formed by contacting an aqueous phase comprising a lignin sulphonate emulsifier - and a water-insoluble agent and - polymethylene polyphenylisocyanate, by dispersing the water-insoluble phase into the aqueous phase and then adding a polyfunctional amine. The isocyanate and amine -compounds and interest-react to form a solid urea-coating wall around the water-immiscible chemical particles to form microcapsules from the chemical. Generally, the concentration of the microencapsulated material is about 480 to 700 g / liter of the composition as a whole, preferably 480 to 600 g / liter.

Concentrates are generally solutions of the active ingredient in a water-insoluble or partially water-miscible solvent containing a surfactant. Suitable solvents for the active compound according to the invention are dimethylformamide, dimethylsulfoxide, N-methylpyrrolidone, hydrocarbons and water-immiscible ethers, esters and ketones. However, other highly concentrated liquid concentrates may be prepared by dissolving the active ingredient in a solvent and then diluting, for example, with kerosene to a concentration suitable for spraying.

The concentrate compositions generally contain. 0.1 to 95 parts, preferably 5 to 60 'parts of active ingredient, about 0.25 to 50' parts, preferably 1 to 25 parts of surfactant and optionally 4 to 94 parts of solvent, all parts being are by weight and refer to the total weight of the emulsifiable oil.

Granules are understood to mean physically stable particulate formulations containing the active ingredient adhered or dispersed in the matrix of an inert, finely divided, particulate carrier. As a rule, to aid in the leaching of the active ingredient from the particles, such compositions comprise a surfactant of the above type. Examples of suitable classes of particulate mineral extenders include natural clays, pyrophyllites, illite and vermiculite. Preferred extender are porous, adsorptive, preformed particles such as preformed and screened attapulgite particles, or heat expanded vermiculite particles and finely divided clays such as kaolin clays, hydrated attapulgrate or bentonite clays. These extenders are sprayed with the active ingredient or mixed with the active ingredient to form a herbicidal granulate.

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

The herbicidal compositions of the invention may also contain other ingredients such as fertilizers, other herbicidal compositions, other pesticidal compositions, safety ingredients and the like as excipients or in admixture with the aforementioned excipients. J.ak ^^ c ^ · ATO other herbicidal active substances, usable in combination with the active ingredients of the present invention include especially a rice e.g., methyl 5- (2,4-dichlorophenoxy] ^{-2-nitro-benzoyl} (current - designation 'bifenox', active ingredient of the herbicidal composition M0D0WN ^R ), 1,3-dimethyl-4- (2,4-dichlorobenzoyl) - ^; 5-pyrazolyl paratoluenesulfonate (code number '5W-751'), alpha- ( beta-naphthoxy oxypropionanilide (codename "MT-101"), 2i, 4-dichloro-3'-m'ethoKy-4'-nitrodiphenyl ether (codename "X-512"), 3,4-dichloropropionanilide - (common to " When used for crops other than rice, other herbicidally active compounds may also be used in admixture with the active ingredients of the invention. Such other compounds include, for example, triazines, ureas, carbamates, acetamides, acetanilides, uracids, acetic acid in the form of derivatives not phenol derivatives, thiolcarbamates, triazoles, benzoic acids, nitriles, biphenyletheres and the like, which are exemplified below:

Heterocyclic nitrogen / sulfur containing derivatives:

2-chloro-d-ethylamino-b-isopropylanyno-sym-triazine,

2-chloro-4,6-bis (isopropylamino) -symtriazine,

2-chloro-4,6-bis (ethylamino-sym-triazine),

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

3-amino-1,2,4-triazole,

6,7-dihydrodipyrido (1,2-a: 2 \ 1‘-с) pyrazidium salt,

5-bromo-3-isopropyl-6-methyluracil

N-dimethyl-N-bipyridinlum,

5-tert-butyl-3- (2,4-dichloro-5-isopropoxyphenyl) -1,3,4-oxadiazo-2-one;

Ureas:

N‘-i (4-chlorophenoxy) phenyl-N, N-dimethylurea,

N, N-dimethyl-N‘-C3-chloro-4-methylphenyl) urea,

3- (3,4-Dichloro-phenyl) -1,1-dimethyl-urea,

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

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

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

Carbamates / thiolcarbamates:

2-chloroallyl diethyldithiocarbamate

S- (4-chlorobenzyl) -N, N-diethylthiolcarbamate, isopropyl N- (3-chlorophenyl) carbamate,

S-2,3-dichlorallyl-N, N-diisopropylthiolcarbamate, ethyl N, N-dipropylthiolcarbamate,

S-propyldipropylthiolcarbamate.

Acetamides / acetanilides / anilides / amides:

2-chloro-N, N-diallylacetamide,

N, N-dimethyl-2,2-diphenylacetamide,

N- {2,4-dimethyl-5- [[(trifluoromethylsulfonyl) amino] phenyl} acetaimide,

N-isopropyl-2-chloroacetamide, 2 ', 6'-diethyl-N-methoxymethyl-2-chloroacetanilide,

2'-methyl-6'-ethyl-N- (2-methoxyprop-2-yl) -2-chloroacetanilide, alpha, alpha, alpha-trifluoro-2,6-dinitro-N _; N-dipropyl-p-toluidine, n- (1,1-dimethylpropynyl) -3,5-dichlorobenzamide.

Acids / esters / alcohols

2,2-dichloropropionic acid,

2-Methyl-4-chlorophenoxyacetic acid

2,4-dichlorophenoxyacetic acid, methyl 2- [4- (2,4-dichlorophenoxy) propionate,

3-amino-2,5-dichlorobenzoic acid,

2-imethoxy-3,6-dichlorobenzoic acid,

2.3.6- trichlorophenylacetic acid,

N-1-naphthylphthalamic acid,

Sodium 5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitroibenzoate,

4,6-dinitro-o-sec-butylphenol,

N- (phosphonomethyl) glycine and its C 1 -C 6 monoalkylamine and alkali metal salts and mixtures thereof.

Ethers:

2,4-dichlorophenyl-4-nitrophenyl ether,

2-chloro-alpha, alpha, alpha-trifluoro-p-tolyl-3-ethoxy-4-nitrodiphenyl ether,

Different:

2,6-dichlorobenzonitrile, monosodium hydrogen methane arsonate, disodium methanarsonate.

The herbicidal compositions of the invention may be used singly, as a mixture with other herbicidal compositions, or may be used sequentially using other herbicidal compositions. For example, treatment of transplanted rice with the herbicidal composition of the invention may be followed by treatment with other herbicides or mixtures of such herbicides such as S-4-chlorobenzyldiethylthiocarbamate (common name "benthiocarb") plus 2-chloro-4,6-di (ethylammo) -1,3 , 5-triazine (common name 'simazine') or 3-isopropyl- (1H) -benzo-2,1,3-thiadiazin-4-one 2,2-dioxide (common name 'bentazone') or such as 444 -chloro-2-methylphenoxybutyric acid (common name "MOPB").

The herbicidal compositions according to the invention are intended primarily for transplanted rice. However, as shown in Table V for the compound of Example 3, at least some of the active ingredient members of Formula I may also be used directly in rice sowing. However, because of the high unit activity of the compounds of the invention, directly sown rice is resistant to some members of the compounds of formula I. Therefore, it is within the scope of the invention to combine the herbicidal compositions of the invention with safety agents and antibodies to promote compatibility of both transplanted rice and sown rice. Such safety enhancers are disclosed in connection with the herbicidal compositions of the present invention the phenylglyoxylonitrile-2-oximocyanomethyl ether disclosed in U.S. Pat. No. 4,152,137, 2,4-disubstituted 5-thiazolylcarboxylic acid and derivatives thereof, described in U.S. Pat. No. 4199 506 and other similar rice-protecting agents for 2-haloacetanilides.

Fertilizers which can be used in admixture with the herbicidal compositions of the present invention are those mentioned

26

such as ammonium nitrate, urea, C. potash -or · superphosphate. Other useful ingredients These include materials in which -the plant- Example 7 compound 50.0 - organisms grow and grow, N-Methylpyrrolidone-n 50,0: such as compost, fertilizer, humus, sand and 100.010 similar materials. The herbicidal compositions of the above-mentioned ty- D. pu are further described by way of example: Example compound -8 5.0 Ethoxylated castor oil 20.0 I. Emulsifiable concentrates Rhodamin B 0.5 Dimethylformamide 74.5 % by weight 100.00 AND. III. Emulsion Example 1 60.0 % by weight Ethoxylated phosphate ester

alcohol _and 4.1215.

Ethoxylated-tertiary amine app.

derived from fatty oil as from 0.875 The compound of Example 9 40.0 of palm oil Polyoxy ethylene block icopolymer / Monnohlorobenzene 13.5 / polyoxypropylene poles with butanol 4.0 Aromatic solvent with 9 atoms Water 56.0 carbon 31.5 1 (0100 100.00 B. Compound of Example 10 B. 5.0 Example 3 compound 46.46 Polyoxyethylene / polyoxypropylene block copolymer Ethoxylated phosphate ester with butanol 3.5 91.5 alcohol Ethoxylated tertiary amine 4,125 Water 0.875 48.55 IV. Wettable powders 100.00 derived from fatty oil as a fuel oil Monoc hlorobenzene 100.00 % weight % weight AND. C. Example 4 compound 5.0 The compound of Example 1 Sodium lignin sulfonate ^N-Me: N-methyl-sodium oleyllaurát 25-, O ^! 3.0 1 <0i Calciumdodecylbenzene- Amorphous silica [synthetic 1 71,0- sulfonate and polyoxyethylene ether 1.0 100.00 Xylene 94.0 B. 100.00 II. Liquid concentrates Compound of Example 3 Sodium dioctyteulfosuccinate 80.01 1,25 % weight Calcium lignosulfonate Amorphous silica 2.75 AND. (synthetic j 16.00 100.00 Example 5 compound 10.0 % hm otnostní Xylene 90.0 100.00 C. B. Example 6 compound 8S », 0 Compound of Example 4 Sodium Lignosulfonate 10.01 3.0 К-МеШуЬМ-оГеуИаига! sodium 1.0 Dimethylsulfoxide 15.0 Kaolinite clay 86.0 110.00 100.00

V. Pills AND. % by weight Compound of Example 10 2,0- Attapulgit 98.0 100.00 B. The compound of Example 11 60.0 M-OTitmorillonite 40.0 100.00 C. Example 112 30.0 Bentonite 7001 100.00 D. Example 13 compound ϋ, ο Kieselguhr 9 £) Д> 100.00 VI. Granule % by weight AND. Compound of Example 1 15.0 Granular attapulgite (0.36 to 0.7 mm) 85.0 ΙΟΟ, ΟΟ % by weight B. Example 3 compound 30,0 · Diatomaceous earth (0.316 - 0.7 mm) 70,0 ' 100.00 C. The compound of Example 4 30.0 Bentonite), 36 to 07 mm) 7001 100.00 D. The compound of Example 5 5.0 Pyrophyllite - (0.36 to -0.7 mm) 95.0 100.0 VII. Microcapsules % by weight

A. ' Example 1 encapsulated in polyurea • new-packaging-walls Lig.nosulfonate sodium 49.2 0.9 Water 49.9 100.00 B. The compound of Example 3 not encapsulated in the polyurea envelope wall 10.0 Potassium ligosulfonate 0.5 Water 89.5 000,00 % by weight C. The compound of Example 4 encapsulated in a polyurea shell wall 80.0 Magnesium salt of lignosulfonate Water 2,0 111,0 '

100.00

When using the herbicidal compositions according to the invention, an effective amount of acetanilides is introduced into the soil containing the plants or is introduced into the aqueous medium by any conventional means. The treatment of the soil with liquid or solid particulate formulations is possible in any conventional manner, for example, with a powder sprayer, an arm and hand syringe, and a spray sprayer. The herbicidal compositions can also be applied from the aircraft in the form of a powder or spray, as they are effective even in small doses. The treatment of aquatic plants with the herbicidal compositions of the invention is generally accomplished by adding the compositions to an aqueous environment in an area where the control of aquatic plants is desired.

The use of an effective amount of an active compound of the formula I according to the invention in a place where undesirable plants are undesirable is important and of decisive importance. The exact amount of active substance to be used depends on various factors, including use in an aquatic or soil environment, the plant species and state of development, the type and conditions of the soil, the amount of rainfall and the specific anilide used. . In selective use, before application to plants or to the soil, it is generally used at rates of from 1.02 to 11.2 kg / ha, preferably from 0.04 to 6.6 kg / ha, or suitably from 1.12 to - 5.6 kg / ha of acetanilides. Lower or higher doses may be sufficient or desirable in certain cases. For example, in some trials of rice-sown rice, the herbicidal compositions of the invention showed a measurable

219056 mfru damage hedgehogs corn feet at extremely small doses. Thus, the compound of Example 3 shows 5% damage to hedgehog corns at an active dose of 0.035 kg / ha (0.03113 lb / A) and the compound of Example 5 shows 10% damage to hedgehog corns at a dose of 0.175 kg / ha (0.01563 lb / A). Based on the above, those skilled in the art will readily determine the optimal dosage for each particular case.

The term "soil" is used herein in the broadest sense, and the term includes all common "soils" as defined in Webster New International Dictionary, II. edition, Unabridged (1961). Thus, the term “soil” refers to any substance or environment in which plants can take root and grow and include not only clay but also commum, mud, sludge, humus, sand and similar substrates on which plants grow.

While the invention is described with respect to specific modifications, the details are not intended to be limiting.

Claims (6)

pRedmet vynalezu A herbicidal composition comprising, in addition to the adjuvants, a herbicidally effective amount of a compound of formula I R is an allyl, chlorallyl, propargyl, 1-methoxyprop-2-yl or a hydroxycarbonyloxymethyl group of the formula -CH 2 OR 1, where R 1 is C 1 -C 5 alkyl. 2. A herbicidal composition as claimed in claim 1, characterized in that it contains N-propargyl-Z-n-butoxy-4-ethyl-Z-chloroacetanilide as the active compound of the formula I. 3. A composition according to claim 1 wherein said compound of formula I which is N- ^{(l-methoxyprop-2'-yl)} -2'-n-butoxy-6'-ethyl-2-chloroacetanilide. 4. A herbicidal composition as claimed in claim 1, wherein the active ingredient is N- (sec-butoxymethyl) -2 n-n-butoxy-6‘-ethyl-2-chloroacetamide. 5. A herbicidal composition as claimed in claim 1, characterized in that it contains N- (2-methylbutyl) -2‘-n-butoxy-6‘-ethyl-2-chloroacetanilide as the active compound of the formula I. 6. A herbicidal composition as claimed in claim 1, wherein the active ingredient is a compound of formula (I) wherein R1 is C3 -C5 alkyl or N- (isoamyloxymethyl) -2'-n-. butoxy-4'-ethyl-2-chloroacetanilide, N- (is-obutoxymethyl) -4'-n-butoxy-1'-ethyl-2-chloroacetanilide and N- (n-butoxymethyl) -2'-n-butoxy-6 ' -ethyl-2-chloroacetanilide.