SU724074A3 - Herbicide - Google Patents

Abstract

Plant growth influencing prepns. contain >=1 cpd. of formula (I) where R1 = ethyl or isopropyl R2 = H, (m)ethyl, or isopropyl; A = -CH2-CH2- opt. mono ethyl- or mono- or dimethyl substd. R3 = 1-3C alkyl. 3-4C alkenyl or cyclopropyl (methyl); X = Cl or Br. They are prepd. by reacting a cpd. (II) with a haloacetylation agent, pre. the anhydride- of halide of chloro- or bromoacetic acid, pref. at 20-100 degrees C opt. in the presence of an acid-binding agent such as a tert. amine.

Description

The invention relates to Chemical means for controlling weeds in crops of cultivated plants, namely to herbicidal compositions containing one or more organic substances as an active substance. Herbicidal compositions containing substituted chloroacetic acid anilides as active substances, for example 2,6-dialkyl-H-alkoxymethylchloroacetanium, are known. Types tl, 2-tert-al-kil-6-alkyl-L-alkoxyalkyl chloroacetanilides 2 and 2, b -diethyl-y-butoxymethyl (or N-butoxyethyl) chloro-acetanilide 3, However, the known herbicidal compositions of this group do not satisfy all the requirements imposed on herbicides with a selective effect, for example, are not effective for resistant weeds, and in large doses damage the plants. The aim of the invention is a new herbicide composition, a more effective suppression of weeds and a deist having the most potent deist. The preferred herbicidal composition contains as an active substance the substituted anilides of loroacetic acid of the general formula where K. ethyl or isopropyl; R, methyl or ethyl; alkyl C, alkenyl Cj-Cd, cyclopropyl or cyclopropylmethyl; an unsubstituted ethylene chain or an ethylene chain substituted once with an ethyl group or once or twice with a methyl group. The form of application of the composition of the usual: solutions, emulsions, powders, pastes, etc. They are prepared by well-known methods: The content of soluble substances in these forms is 0.0109 wt.%. The method of obtaining compounds of this general formula is based on the reaction of M-alkoxyalkyl-substituted aniline

with anhydride or chloroacetic acid chloride. -.

The composition is recommended for combating various weeds in crops of cereals, vegetables and other crops both in pre-emergence, post-emergence and application. Its consumption rate (according to the active substance) is 0.110 kg / ha, preferably 0.5-5 kg /

The following are compounds complying with the indicated general formula.

1.2-Ethyl-6-methyl-L- (2-methoxyethyl) chloroacetanilide. ;

2,2-Ethyl-b-methyl-L- (2-ethoxyethyl; sh6 a1Cetanilide,

3.2-Ethyl-6-methyl-L- (2-propoxyethyl) chloroacetanilide.

4.2-Ethyl-b-methyl-L- {2-isopropoxyethyl) chloroacetanilide.

5.2-Ethyl - b-methyl-L- (2-allyloxyethyl) chloroacetanilide.

6.2-Ethyl-6-methyl-L- (1-methoxy-pro-2-yl) hlrr-acetanilide.

7.2-Ethyl-6-methyl-Y- (2-methoxypropyl) chloroacetanilide.

8.2,6-Diethyl-Y- (2-methoxyethyl) chloroacetanilide.

. 9.2,6-Diethyl-Y- (2-ethoxyC ethyl) chloacetanilide.

ten . 2,6-Diethyl-1- (2-propoxyethylchloroacetanilide.

11.2, b-Diethyl-L- (1-methoxyprop-2-yl) chloroacetanilide.

12.2-Isopropyl-6-methyl-N- (2-methoxyethyl) chloroacetanilide.

13 .2-Isopr6pyl-b-methyl-L- (2-ethoxyethyl) chloroacetanilide.

14.2-Isopropyl-b-ethyl-L- (2-methoxyethyl) chloroacetanilide.

15.2-Ethyl-6-methyl-L- (2-ethoxypropyl) hl-6-roxetanilide.

16.2, b-Diethyl-L- (2-isopropoxy ethyl chloroacetanilide.,

17.2, b-Diethyl-L- (2-ethoxypropyl 1 chloroacetanilide.

18.2-Ethyl-6-megyl-N- (2-cycloproposiethyl) chloroacetanilide.

19.2-Methyl-6-K- (3-methoxybut-2-yl) chloroacetanilide. ,

20. 2-Methyl-6-ethyl-L- (1-methoxybut-2-yl) chloroacetanilide.

21.2,6-Diethyl-Y- (1-methoxy-2-yl) chloroacetanilide.

Example. Pre-emergence application.

After 1 day after sowing the tested plants in the growing vessels, diluted aqueous suspensions of the active substances are sprayed onto the soil surface in such concentrations as to ensure consumption rates of 2, 1 and 0.5 kg / ha. Vegetative vessels can be kept at 22-25 0 and approximately 70% relative humidity. The results are estimated. 28 days later according to the following scale:

9 - no effect (as experience

for comparison) 1 - full effect

8-2 - various intermediate

degree of effect

- means that the tests were not performed.

As compounds for comparison, halogenoacetanilides known from U.S. Pat. No. 3,54762 are used:

2-methyl-b-ethyl-L- (ethoxymethyl) chloroacetanilide (A), 2, b-diethyl-L- (methoxymethyl) chloroacetanilide (B, tractive product). The results are shown in Table 1.

Table 1

sixteen

7,

eight

9

9

9

9

Continuing Tile.1

. . PRI mme R 2. Pre-emergence application.

Immediately after sowing the tested plants into growing vessels, the active ingredients are applied in the form of an aqueous suspension obtained from a 25% wettable powder, spreading it in such a way as to ensure consumption rates of 4, 2, 1 and 0.5 kg / ha.

Continuation

Then the vegetation vessels are maintained at 22-25 ° C and 50-70% relative humidity. After 28 days, the evaluation of the experiment was carried out according to the scale given in Example 1,

The halogenoacetanilides A and B mentioned in Example 1 are used as compounds for comparison.

The results of the experiment are presented in Table 2, - I toopoI 1o l || ooosoN t oso O4invo.

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, H-H (N f-1-CHSMGCH gNgTSgCh -

rg,) ГЧ ГЧ Г4 F-i r 1-4 rsl m TJ

-I I G4 I

GN CM 1-4 .4 iH 1-t

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p 3. Pre-emergence primaprime some. Plastic baths 30 cm deep and with edges 30x50 cm long are filled with medium-sized field soil. Appropriate seeds are sown on the soil surface and then covered with approximately 2 cm of soil and moistened. During the day, a dilute suspension of the active substance is used, the concentrations correspond to consumption rates of 1,0,5,0,0; 25 and 0,125 kr / ra. The vessels are kept at 22–25 s and approximately 70% normal air humidity.

Compounds B are used as compounds for comparison, as well as compound G - 2, b-diethyl-S - (butoxyethyl) chloroacetanilide, mentioned in U.S. Pat. No. 3,547,620, as a control compound.

After 20 days, an assessment is made. The results are shown in Table 3 as damage in percent of test plants. In this case, the area of more severe weed damage is illustrated more extensively than the areas of moderate and minor damage. Conversely, the area of minor damage to beneficial plants is more strongly differentiated.

Table 3

PRI me R 4, Herbicidal action against natural weeds.

For field trials in western France, t) plowed and harrowed fields sowed maize at a distance of 60 cm between rows; The field was then divided into sections of 4 m in size, each of which expected approximately 60-75 cucumber plants. Continuation

Ruza. After 1 day of sowing, the plots were treated with active ingredients in a concentration determined for them (in the form of emulsions). For comparison, apply A and B,

The score after 35 days was related to the condition of the crop and naturally-sprouting herbs. Damage to plants (in percent) is given in Table 4.

Table 4

15

72407416

Continued table. four

Claims (1)

SUMMARY OF THE INVENTION A herbicidal composition containing an active ingredient, a chloroacetanilide derivative, a solvent and an emulsifier, / or a filler, and / or a dispersant, characterized in that, in order to increase the efficiency of the composition, it is taken chloroacetanilide derivative compound of the general formula R; A - 0y ₃ C sn _g C1 II about - ethyl or isopropyl; methyl or ethyl; - alkyl C ^ - Cj, alkenyl where R ₃ ^r 2 45 R ₃ Cj-Cd, cyclopropyl or cyclopropylmethyl; A - unsubstituted ethylene Tables a5 Consumption rate, kg / ha Wipe Bristles Bramble Rice 2 1 1 1 6 1 1 1 1 8 0.5 1 1 ' 1 9 chain or ethylene chain, 50 substituted once. but or twice with a methyl group, in an amount of 0.1-90 wt.%.