PL149105B1 - Herbicide of prolonged action - Google Patents

Abstract

A controlled release herbicidal composition comprises 0.5 to 95% by weight of one or more alpha - chloroacetanilide derivatives of the formula I <IMAGE> as active ingredients, optionally with further herbicidally active ingredients, in admixture with 1 to 80% by weight of extenders selected form the group of (1) a N,N-diallylacetamide derivative of the formula II <IMAGE> or (2) a N-allyl-N',N'-disubstituted glycinamide derivative of the formula III <IMAGE> or (3) a 2,6-dinitroaniline derivative of the formula IV <IMAGE> or (4) a dithiocarbamate derivative of the formula V <IMAGE> in admixture with usual additives, wherein the weight ratio of the herbicidal active agent(s) and the extender(s) is 200:1 to 1:10.

Description

PATENT DESCRIPTION

POLAND

REPUBLIC

FOLK

Additional patent to patent no. Pending: 86 05 09 / P. 267993 / Priority 85 05 10 Hungary

READING ROOM

P® * rOMweg>

Int. Cl. ⁴ A01N 37/22 A01N 37/18

OFFICE

PATENT

PRL

Application published: 87 04 06 Patent description published: 90 04 30

Inventor:

The holder of the patent: Śszakmaggarorszagi Vegylm & vek> Sajobabony / Węggry /

PROLONGED ACTING WEIGHT AGENT

The invention relates to herbicidal compositions of prolonged action, comprising as active eubetancję 0.5-95% by weight of alpha-chloroacetanilide derivative of general formula 1, wherein R and R are the same or different and represent a hydrogen atom, a low aluminum ^{alkyl and} O 1-3 ^h atomac atoms ^{and R} is a ^p roete altio branched ^group of alkHową having from 1 to ⁶ carbon atoms, or a alkoksyalkioową having 1-4 C atoms in each part alkioowej and as a means to prolong the action to co- 1-80% by weight / CH of N-allyl -, - * - ^d ipocl sieve wio n ^{Y hg} licynoami ^d uo formula og ^ E ^ m 2 ^inclu wherein ^R and ^R are identical ^±] .ub different and oznaćkają wcooru atom, a straight or branched an alkyl group of 1-6 carbon atoms, an alkenyl group of 2-6 carbon atoms, cyclohexyl or substituted up to twice by an alkyl group or a chloro atom, a phenyl or a benzyl group, or

and. ^R together form ^{l h} ańcuc he same ^angle so ^ncoy, kt ^yellow r ^{s t} atom azctu Worz heteoocykliczn ^{yp y} ^ e lerśc ^{and N, R} is an optionally substituted mono- suggested ^d of ^{d t} y ^y times a ^ c ^ mem lorowca c ^h a straight or branched alkioową with 1-5 C atoms alkenyl of 2-5 atomch atoms, or benzyl, in addition to 1-96% by weight of a solid carrier and / or liquid diluting agent and 0.1-25 wt% substanoji surfactants, whereby the weight ratio of herbicides to prolonging action is 200: 1 - 1: 10

⁰⁶ -chloroacetanilide derivatives are used in agriculture in large areas as an active subatanism of weed control agents. Active substances and their use are described, for example, in US Pat. No. 2 863 752, 2 864 683,

442 945 and 3 547 620 and in the publication RPN No. 2 320 340. In agriculture, the part J N-isopropylea cc tanilide (Propachlor) is used; 2-methyl-6-ethylc-N- (rtoxymethyl) - octa-chloooac6tatilide (Aoβtcohlor); 2,6-diethoo-N- / butoxymealo / - oæ-chloroacθtatilid / Butachlor /; 2,6-diethyl-N- (me to ksyme alo) - oh -chloroacetanilide (A la chlorine) and 2- (ryl-bβtyl-N- (2-IMtokθy-1im) / trio-ethylcol-c ^ ύ .oroacerynilid / MιtbBchlor /, ^ in order to increase activity and selectivity zenia derivatives are oc-chloroacetstilidu in combination with other herbicides, eg. derivatives of triazine, or karbomidowymi trrβlo ^k aΓa / mnn0owy / s, as shown in the U.S. patent No. 178 892; 178 895;

179 092; 179 093; 181 621 and 181 849.

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149 105

The weed control agents should, in addition to their high activity and appropriate selectivity, have an optimal duration of action, it is known that the concentration of herbicides immediately after application is quite high and which, due to the metabolism of the active ingredient, decreases in a shorter or longer time. The metabolism of the active substance is not influenced by the substrate, as well as by other conditions. The decrease in effect results from the decrease in concentration and the measured active substance content. in the substrate. It is also known that the disintegration time of an active ingredient is reduced when it is used repeatedly at the same site. Action is getting smaller and after. a certain number of apply causes. weed outgrowth and damage to crops. To prevent this, increasing amounts of anti-killer agents are used, which is uneconomical and at the same time harmful to the environment. This problem was solved by prolonging the action of the herbicides. The research proved that the activity of thiolcarbamate derivatives can be maintained for a long time in soil with kαrbaminiaooi derivatives (Hungarian patent specification No. WJ-OST / 30317 /; 4-phenyl-1,2,3-thiadiazoles (Hungarian Patent No. HJ-OOT / 28 322); amines or amine salts / HU-OST / 26 610 / or organic phosphorus compounds / Hungarian patent description HJ-PS 185 612 /. / e the additional subtandje themselves show no or little herbicidal activity and do not additionally influence the effect of the thiodocarbamilyαn derivatives. By preventing the disintegration, the auxiliaries increase the effectiveness of the active substances.

Studies leading to the prolongation of the action of the oc-chloroacetanilide derivatives have been performed. It was also ensured that the simultaneous use of aminal derivatives can significantly increase the duration of action and in some cases also the selectivity (Hungarian patent application No. 3856 / B4 /). The auxiliary substances help to adjust the optimal duration of action and to reduce the amount of active substance used, and to double its selectivity.

It has surprisingly been found that the duration of action and the selectivity of the o? -Chloroacetanilide derivatives can be significantly increased by adding the N-allyl-N *, N'-disubstituted glioylamide derivatives of the general formula 2 (Table 1)

Table 1

Useful N-allyl-N *, N * -disubstituted glycitamide derivatives of the general formula 2

Relationship no r4 r5 ^r6 2 - 1 phenyl ethyl mtyl 2-2 fe nyl ethyl ethyl 2-3 fe nyl ethyl n-propyl 2-4 phenyl ethyl i-propyl 2-5 fe nyl ethyl allyl 2-6 phenyl ethyl n-butyl 2-7 phenyl ethyl aec-butyl 2-8 fe nyl ethyl i-butyl 2-9 phenyl ' ethyl tert-butyl 2-10! And allyl allyl mtyl 2-11 allyl allyl ethyl 2-12 allyl allyl allyl 2-13 ethyl ethyl allyl 2-14 i-butyl i-butyl ethyl 2-15 mtyl mtyl n-propyl 2-16 installments! mtyl i-propyl 2-17 mtyl mtyl allyl 2-18 mtyl mtyl ethyl

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Table 1 / continued /

Relationship no R ⁴ r5 ^r6 2-19 ethyl ethyl n-propyl 2-20 ethyl ethyl i-propyl 2-21 ethyl ethyl ethyl 2-22 cyclohekdyl ethyl ethyl 2-23 phenyl H. ethyl 2-24 allyl H. allyl 2-25 n-propyl n-propyl allyl 2-26 cyclohexyl H. allyl 2-27 fe nyl H. allyl 2-28 2,6-diiethylphenyl H. ethyl 2-29 2,6-diethylphenyl H. ethyl 2-30 hexaethylene hexaie so much noiiina ethyl 2-31 3-chloro-phenyl H. ethyl 2-32 ethyl ethyl n-butyl 2-33 ethyl ethyl i-butyl 2-34 ethyl ethyl sec-butyl 2-35 ethyl ethyl tert-butyl 2-36 fe nyl wtyl ethyl 2-37 fe nyl mtyl n-propyl 2 - 3Θ phenyl weyl allyl 2-39 phenyl i-propyl ethyl 2-40 phenyl i-propyl allyl 2-41 | | wtyl H. wtyl 2-42 | And ethyl H. ethyl 2-43 n-propyl H. n-propyl | 2-44 i-pyropyl H. i-propyl And 2-45 AND n-butyl H. n-butyl 2-46 i-butyl H. i-butyl 2 - 47 sec-butyl H. sec-butyl 2-48 benzyl H. benzyl 2-49 n-propyl n-propyl allyl 2-50 phenyl weyl mtyl 2-51 phenyl ityl i-propyl 2-52 2,6-dm tylphyl H. mtyl 2-53 2,6-dimethylphenyl H. allyl 2-54 2,6-diethylphenyl H. wtyl 2-55 2,6-diethylphanyl H. allyl 2-56 allyl H. n-butyl 2-57 allyl H. i-butyl 2-58 allyl H. i-propyl 2-59 allyl H. n-propyl 2-60 allyl H. ethyl j

The abovementioned compounds, their preparation and their use as poison are known from Hungarian patent application 2565/83 · Ioh, their suitability for use in extending the duration of action of an active ingredient of a parasiticide was previously unknown.

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The substances of the general formula 2 can be used to extend the duration of action of the active ingredient of the herbicide containing Propachlor, Acctochlor, Alach! ^, Ritachlor or Mtholaohlor. crops, type of weeds, soil characteristics and other conditions, and can be varied over a wide range.

The formulations contain 0.5% by weight of ^< 55% by weight of active ingredient and 1-80% by weight of extender, the weight ratio of active ingredient to additive being 200: 1 - 1:10, preferably 60: 1-3: 1, especially 12 : 1 - 15: 1

The amount of extender used depends primarily on the decomposition capacity of the soil. In general, the amount used is 0.2-10 kg of adjuvant per hectare of soil surface, preferably 0.5-5 kg per hectare, in particular 1-2 kg per hectare.

According to the invention, there are also claimed concentrate formulations, as well as formulations obtained from them by dilution which are suitable for use, as well as those which are prepared in mixers (tanks) immediately prior to use.

The formulations according to the invention can be used in the form of solid or liquid preparations known in agriculture, which contain, in addition to the organic substance, the agent extending the action of the enzyme substance, 1-96% by weight of solid or liquid diluent, and optionally 0.1-25% by weight of surfactant. . Natural or synthetic, organic or inorganic substances can be mentioned as agricultural carriers. The solid carriers used are, for example, alumina, natural or synthetic silicates, cream acid, dolomite, kaoli, vegetable granules and starch. As: o liquid carriers can be used, for example, water, alcohols, esters, ketones, aromatic mineral oil fractions, alffathic or cyclic hydrocarbons, chlorinated hydrocarbons, dimethylformamide, diTtylsulfoxide and N-imtyypyrrolidone.

The following may be used as surfactants: ionic and / or ionic emulsifying, dispersing or wetting agents, e.g. salts of lignin sulfilic acid, salts of phenol sulfilic acid or naphthaenosullyl acid, ethylene oxide and ρoliklide alcohol. fatty acids, fatty acids or fatty acid amides, further arylalkyl sulfonates, substituted phenols, alkylphenols, arylfernls and polyoxyethylated phenols, further creosol-formaldehyde condem, ethanoloot lye and the like. The compositions according to the invention may be in the form of solid powders, dusts or granules, or as liquid solution preparations, suitable for emulsifying concentrates, emulsions, concentrated suspensions, wettable powders, dusting powders or pastes.

The compositions according to the invention can also be used mixed with known plant protection products. In the mixtures, herbicides, pests, fungicides, bactericides and plant growth regulators, those which are not harmful, can be used with derivatives of oC, o, o, o, o, o.

The preparations are used, if appropriate, after dilution in the usual manner, e.g. by spraying, spraying, sprinkling or dusting.

Composition 1 and the preparation of the compositions according to the invention are further defined in the following non-limiting examples.

Example I - wetted powder. 5 g of Alaohlor and 0.8 g of the N-alliOo-N, N * -disubstituted glycinamide derivative (compound No. 2-9) are dissolved in 10 g of dichloromethane. The solution is applied to the / 24.2 g / carrier / amorphous diatomaceous earth /. The solution is evaporated in a vortex-flow dryer at 30-40 ° C. 60 g of the carrier - diatomaceous earth, 3 g of a wetting agent - sodium alkali sulfonic acid, 3 g of cresol-oomaldehyde condensate and 4 g of a dispersant - sulfite lye are introduced into the powder mixture. The mixture is finely ground in an Alpina 63C / ΚοπΙγορΙθχ / mill. Thus, a wettable powder is obtained with an active ingredient content of 5.8% by weight, the ratio of Alachlor to Compound No. 2-9 being 6.25: 1.

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Example II- emulsified concentrate. 50 g of Alaohlor and 0.25% of the N-allyl-N *, N-dipositaviral glycinamide derivative (compound 2-24) dissolve 22 g of xylene and 21.75 g of dichloromethane in the meshesin. As much as 6 g of the mixture of emulsifiers consisting of the calcium salt of an alkyl acid and a pρligliPoOowPgP fatty acid ester are added to the solution. All of the hρropea O ^ is mixed by mixing and filtered. There is thus obtained an emulsified concentrate with an active ingredient content i) of 50.25 wt / wt, wherein the Alachlor-o 'ratio of compound No. 2-24 is 200: 1.

Example - III - emulsified ends of nnrat. 30 g of Butachlor and 20 g of the compound 2-24 are dissolved in a mixture of 16 g of xylene, 16 g of dichloromethane and 8 g of dimethylformamide. The solution is mixed with 10 g of an emulsifier mixture consisting of the calcium salt of tlkioayy0sulfopic acid and pρligliPlPowθgρ fatty acid ester. The whole is homogenized by mixing for 15-20 minutes and filtered. There is thus obtained an emulsifiable concentrate with an active ingredient content of 50% by weight, with a ratio of Butachlor to compound No. 2-24 of 3: 2.

Example IV- Emulsifiable coorthrate. 5 g of the active ingredient Alachlor is combined with 32 g of the compound 2-46 and dissolved in a mechanine consisting of 25 g of xylene, 20 g of dichloromethane and 15 g of dimethylformamide. To this, 6.5 g Emulspgene * 1 IP / alkyl polyethylene glycol ether / and 1.5 g Eml * (EL ene'3 / ethoxylated castor oil /, hpmogene and filtered) are added while stirring. % of the active ingredient is 37% by weight, with a ratio of A-achlor to compound No. 2-46 being 1: 6.4.

Example V - emulsifiable concertrat. 65 g of Alachlor and 6 g of compound No. 2-57 are dissolved in a mixture consisting of 12 g of xylene and 11 g of dimylformamide.

A mixture of emulsifiers consisting of 4 g Emu ^ ogen EL, homopennEUjβ is introduced into the solution for 15 minutes and 1 day. This gives an emulsified concentrate with an active ingredient content of 70% by weight, the ratio of A.a chloro to compound 2-57 being 13.:1

Example V - emulgpoaloy rat concert. 5 g of Aceto-3n are combined with 32 g of the compound No. 2-33 and are dissolved in a mixture consisting of 20 g of xylene, 15 g of dichloromethane and 10 g of dim3-omiamldium. The emulsifier mixture is added to the solution with stirring, which consists of 6 g Emulgen IP and 2 g Emulgen EL. The whole is homogenized and filtered. Thus, an emulsifiable concentrate is obtained with an active substance content of 37% by weight, with a ratio of AGatoch ^ !! to the compound 2-33 in the ^ axis 1: 6.4.

Example 7 - wettable powder. In a ball mill, 45 g of Propalone and 15 g of Compound No. 2-24, 2 g of an aliphatic sulfonic acid sodium salt wetting agent, 3 g of a dispersant - krecliformaldehyde conderaets, 5 g of sulfite lye, 15 g of a synthetic carrier are homogenized. of silicate and 15 g of diatomaceous earth. Thus, a wettable powder with an active ingredient content of 60% is obtained, the ratio of Propachlor to compound 2-24 being 3: 1.

Example VIII - eralgable konocnnrat. 65 g of the compound 2-24 are dissolved in a mixture of 5 g xylene, 5 g of diohloronethane and 4 g of dimethylformamide. 1 g of a mixture of emulsifiers / calcium salt of alkiPaayyPolulfopic acid and iPliglkPoOowgp fatty acid ester / and hpmopenOzuje are introduced into the solution. This gives an emulsified concentration of rat with a content of 85% by weight of the active ingredient prolonging action.

Example U - emulsified concertrat. 60 g of Aco tadkor and 2 g of the compound 2-24 are dissolved in a mixture of 12 g of xylene, 10 g of dichloronethane and 8 g of dimethylformamide. 8 g of the mixture of emulsifiers / calcium salt of kwaeu alkiPoaryPslUlphonic 1 of polyglylPoPo fatty acid ester / 1 are introduced into the solution with stirring / 1, filtered after 15-20 minutes of stirring. The resulting concentrate has an active substance content of 62% by weight, the ratio of Acetone to compound 2-24 being 30: 1.

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Example X - emulsifiable concentrate. 60 g of Aootohlor and 10 g of the compound 2-25 are dissolved in a mixture of 15 g of xylene and 8 g of dimtylformamide. 4 g of Emulsogen IP 1 and 3 g of Emlsogen EL are introduced into the solution. The mixture is homogenized with stirring for 15 minutes and then filtered. This gives an emulsified concentrate with an active ingredient content of 70% by weight, the ratio of Acetochlor to compound 2-25 being 6: 1.

Example X! - suspension concentrate. 3 g of Aooeochlor and 2 g of compound 2-4B are dissolved in 25 g of dichloromethane, and the solution is stirred, g of diatomaceous earth as a carrier, 6 g of cresolformaldehyde condensate and 4 g of a sulfite lye powder dispersant. The mixture is finely ground in an Alpina 630 type mill. A suspension concentrate with an active ingredient content of 5% by weight is thus obtained, whereby the ratio of Acet chlorine to compound 2-48 is 3: 2.

Example XII - suspension concentrate. 12 g of Acetochlor and 16 g of compound 2-53 are dissolved in 16 g of xylene and 50 g of diatomaceous earth as a carrier, 3 g of cresol-ndite condensate and 3 g of sulfite lye powder dispersant are added to the solution with stirring. The mixture is finely ground on an Alplna 630 type mill. This gives a suspension concentrate with an active ingredient content of 28% by weight, the ratio of Aoethochlon to compound 2-53 being 3: 4.

In an analogous manner to examples ΙΧ-, herbicides according to long-acting maturation can be prepared from Acetochlor and compounds of the general formula II.

Example XIII - suspension concentrate. 25 g of Acetochlor or Butachlor and 0.5 g of the extender 2-11 are dissolved in 15.5 g of xylene and mixed with 50 g of diatomaceous earth as a carrier substance, 3 g of cresol-oommaldehyde condensate and 2 g of lye powder dispersant post-sulfin. The mixture is finely ground in an Alpina 630-type mill. A suspension concentrate is thus obtained with a content of 25.5% by weight aynonzo active ingredient, the ratio of the extender active ingredient being 50: 1.

Example XIV - suspension concentrate. 10 g of Alachlor or Butachlor and 1 g of an extender (compound 2-25) are dissolved in a mixture of 10 g xylene, 9 g of dichloromethane and 8 g of dimethylformamide. 2 g of the mixture of emulsifiers / calcium salt of rarinol-1-phinic acid and polyglycol ester of t3 acetic acid and 60 g of diatomaceous earth as carrier are introduced into the solution. The mixture is finely ground in a mill of the Alpina 63C type. The result is a suspension concentrate with an active ingredient content of 11% by weight, the ratio of active ingredient to extender being 10: 1.

Example XV - Emulsifiable Concentration !. 25 g of Alachlor or Butachlor and 10 g of an extender (compound 2-27) are dissolved in a mixture of 25 g xylene, 20 g of dichloromethane and 10 g of dimethyl sulphoxide. The solution is mixed with the emulsifying agents 7 g of ElWlsngei IP and 3 g Emulsngen EL. The mixture is homogenized and filtered. Thus, an emulsifiable concentrate is obtained with an active ingredient content of 35% by weight, the ratio of active ingredient to extender being 2.5: 1.

Example d XVI - Emulsifiable ^ ηοοη ^ θΐ. 50 g of Alachlor or Butachlor and 40 g of an extender (compound 2-24) are dissolved in 9 g of xylene and 1 g of a mixture of emulsifiers / calcium salt, alkyne sulfinic acid and 1 poly fatty acid ester are added. This gives an emulsified concentrate with an active ingredient content of 90% by weight, the ratio of active ingredient to extender being 5: 4.

Example XVII - emulsifiable ends of rtrat. 5 g of Alachlor or Butachlor and 50 g of an extender (compound 2-55) are dissolved in a mixture of 23 g of xylene and 20 g of dichloromethane. 2 g of the mixture of emulsifiers / calcium salt of rlkylaryl sulphonyl acid and polyglycoacid ester of fatty acid / are introduced into the solution. Thus, after homogenization, an emulsified concentrate is obtained with a solids content of 55% by weight, the ratio of active substance to extender being ^ ^ηοθ 1 1: 10

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The long-acting herbicides according to the invention are prepared from Alachlor or Butachlor and the prolonging agent of the general formula 2 analogously to Examples 13 to 17

Example XIII - test of an agent extending the action of a substance or not. The conducted studies showed that the effect of Propachlor, which was applied in the amount of 6 kg / ha, when sprinkling the soil in pots, was significantly prolonged by the prolongation of its action.

400 g of medium-bonded soil (Arana bound: 60), pH ^^ «5.68, humus content: 1.87%, NO ^ + NO ^« 9.2 ppm, were poured into pots with a capacity of 1000 g of soil,

P ₂ ° 5 = ⁸ ppm * 1 ^ 2 ° = 200 ppm. 4 grains of maize type ΝΚΧ-20 were sown in this soil,

MVCS 484 and II 97 SC and 0.5 g Panicum miiaceurn and covered with 100 g of soil. For the treatment, 6 kg / ha of Propachlor and the active ingredient prolonging agent were used separately or in combination in an amount of 0.1-0.5-2.0-4.0 kg / ha.

The active ingredient Propachlor was used as a commercial herbicide under the name SATBCID 65 WP after dilution with water. As an agent prolonging the action of the active ingredient, the emulsifiable concentrates according to Example 3I were used, after dilution, they were poured onto the soil. For treatment in combination with an agent extending the action of the active ingredient, either the above two altered agents were used one after the other or the agents according to Examples 1-2 were used. The biological effect is not influenced by the type and type of treatment. Thereafter, 60% of its water absorption capacity was poured over the soil and the water loss was replenished daily. After sowing, sowing was assessed after 13 days by a fire of green mass. The second seeding was carried out after the 15th day and its evaluation after 23 days. ^ ynni ^ :! are given in Table 2.

Table 2

Weed weight measurement results for the second sowing

Herbicide An agent that extends the action of the active substance Herbicide + agent extending the action of the active ingredient / p + q kg / ha / Name J Dose / kg / ha / Weight of weeds / * / X Relationship no Dose / kg / ha / Weed weight / W / y P. weed weight% Propachlor 6 70 IIII 0.1 108 75 0.5 105 15 2.0 102 36 1 1 4.0 90 42

Γ

When evaluating the results, it was found that when using Propachlor alone, the weeds were completely controlled at the first sowing (0% of the weight of the weeds), however, the effect on the weeds of this substance was negligible (70% of the weight of the hooks) on the second sowing. The maize was not damaged and its green mass was the same as in the control sample.

The action of Propachlor was clearly prolonged by the use of the agent according to the invention. This shows that excellent weed control (last row) is achieved on the second sowing.

Example XIX - trial of an agent extending the action of an active ingredient of a herbicide. The biological tests were carried out according to Example 13 using the weed Pca pratengis. The weed weight measurements for the second sowing are given in Table 3. When evaluating the results, it was found that when Propachlor was used, the first spraying weeds fell obliviously / 0% of the weed weight / the active substance hardly affected the weeds of the second sowing / 93% of the weeds / . The pericidal activity of the active substance can be improved by combination with the extender and the active substance because the weeds of the second sowing are completely controlled / last row of table 3 / δ

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Table 3

Herbicide An agent that extends the action of the active substance Herbicide + agent prolonging the action of the active substance / p + q kg / ha / Name Dose / kg / ha / P. Weight weeds /% / X Relationship no Dose / kg / ha / Weight weeds / «/ c weed weight% Propachlor 6 93 HII 0.1 96 51 0.5 78 0 2.0 74 19 4.0 69 7

Example XX - Herbicide Extender Test The biological tests were carried out according to Example 13 using Acoeochlor as active ingredient and compounds 2-10, 2-17, 2-24, 2-25, 2-27 as the extender. 2-33, 2-48 and 2-53. · The extenders are sprayed onto the soil after suitable dilution of the emulsified concentrates. · Formulations containing Acetochlor as active ingredient and as extenders of formula 2 are prepared according to Examples 2 and II-. The most important data and the results of weed weight measurement for the second sowing are presented in Table 4. The N-allyl-N, * I-disubstituted glycinamide derivatives of the formula II do not exhibit a herbicidal effect on their own. the second seeding is significantly higher than expected The first seeding is completely deposited and the maize cultivation has not been damaged.

Table 4

j ^W rode ^k herbicide / dose - p / Compound prolonging action Examples preparations Ratio The weight of the weeds - /% / Center weed- deadly / XI / Extend- wife / Y / Connection / X + Y / Relationship no Dawta = q / kg / ha / Acetochlor 2-10 at 1 IX 30: 1 55 102 48 / 3 kg / ha / 0.5 X 6: 1 100 40 2.0 ΧΙ 3: 1 97 32 4.0 ΧΙΙ 3: 4 86 10 Acetochlor 2-17 0.1 IX 30: 1 55 109 53 / 3 kg / ha / 0.5 X 6: 1 104 40 2.0 ΧΙ 3: 2 98 thirty 4.0 . ΧΙΙ 3: 4 90 22 Acetochlor 2-24 0.1 IX 30: 1 55 108 50 / 3 kg / ha / 0.5 X 6: 1 105 48 2.0 XI 3: 2 102 42 4.0 XII 3: 4 90 39 Acetochlor 2-25 0.1 IX 30: 1 55 97 41 / 3 kg / ha / 0.5 X 6: 1 95 37 2.0 XI 3: 2 95 31 4.0 XII 3: 4 93 28 Acetochlor 2-27 at 1 IX 30: 1 55 99 44 / 3 kg / ha / 0.5 X 6: 1 98 41 2.0 XI 3: 2 93 39 AND 4.0 XII 3: 4 1 91 AND 35

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continued Table 4

Center herbicidal / dose - p / Compound prolonging action Examples preparations Ratio Weed weight /% / Center weed- deadly / XI / Extend- wife / Y / Calling / X + y / Relationship no Dose = q / kg / ha / Acetochlor ' / 3 kg / ha / Acetochlor / 3 kg / ha / Acetochlor / 3 kg / ha / 2-33 2-48 2-53 0.1 0.5 2.0 4.0 19.2 0.1 0.5 2.0 4.0 0.1 0.5 2.0 4.0 IX X XI XII VI IX X XI XII IX X XI XII 30: 1 6: 1 3: 2 3: 4 1: 6.4 30: 1 6: 1 3: 2 3: 4 30: 1 6: 1 3: 2 3: 4 55 55 55 110 107 100 95 62 100 98 94 89 99 97 92 90 49 45 40 36 10 48 46 40 36 40 32 twenty 12

Example XXI - Herbicide Extender Test The biological tests were carried out according to Example XX, using Alachlor as active ingredient, and compounds 2-9, 2-11, 2-24, 2-25 as extenders.

2-26, 2-27, 2-46, 2-55, and 2-57. Formulations containing Alachlor and compounds extending the action of the active ingredient were prepared according to Examples I, II, IV, V and XIII-XVII.

The most important data and the results of the weed weight measurement for the second sowing are presented in Table 5.

When evaluating the results, it was found that the application of Alachlor completely controlled the weeds of the first sowing. The active substance has hardly any effect on the weeds of the second sowing (67% of the weight of weeds). The herbicidal activity of the active ingredient can be significantly improved by combining chlorine with an active ingredient extender of the N - 11000 - N, 'N'-disubstituted glycinamide derivative of the general formula II in the formulations indicated.

Table 5

Center herbicidal / dose - p / Compound prolonging action Examples preparations Ratio The weight of the weeds /% / Wednesday weed Extend- wife / Y / I will combine not / X + Y / Relationship no Dose = q / kg / ha? Alachlor 2-9 0.38 V 13: 1 67 104 62 / 5 kg / ha / 0.8 AND 6.25: 1 100 48 32.0 IV 1: 6.4 98 37 50.0 XVII 1:10 96 twenty Alachlor 2-11 0.1 XIII 50: 1 67 101 59 / 5 kg / ha / 0.5 XIV 10: 1 99 50 2.0 XV 2.5: 1 95 46 4.0 XVI 5: 4 83 thirty Alachlor 2-4 0.025 II 200: 1 67 110 60 / 5 kg / ha / 0.1 MII 50: 1 108 51 0.5 XIV 10: 1 105 47 2.0 XV 2.5: 1 102 41 4.0 XV 5: 4 90 38 Alachlor 2-25 0.1 XIII 50: 1 67 97 41 / 5 kg / ha / 0.5 XIV 10: 1 95 40 2.0 XV 2.5: 1 95 43 4.0 XVI. 5: 4 93 21

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continued Table 5

Center herbicidal / dose - p / Compound prolonging action Examples preparations Ratio Weed weight /% / Center weed- deadly / X / Extend- wife / Y / Combining Benie / X + YY Relationship no Dose »o / kg / ha / Alachlor 2-26 0.38 AND 13: 1 67 98 44 / 5 kg / ha / 0.8 AND 6.25: 1 97 39 32.0 II 1: 6.4 92 thirty 50.0 XIII 1:10 90 19 Alachlor 2-27 0.1 XIII 50: 1 67 99 43 / 5kg / ha / 0.5 III 10: 1 98 37 2.0 XI 2.5: 1 93 31 4.0 XVI 5: 4 91 28 Alachlor 2-46 0.38 AND 13: 1 67 112 60 / 5 kg / ha / 0.8 AND 6.25: 1 110 57 32.0 II 1: 6.4 105 50 50.0 XIII 1:10 100 45 Alachlor 2-55 0.38 AND 13: 1 67 98 52 / 5 kg / ha / 0.8 AND 6.25: 1 96 47 32.0 II 1: 6.4 91 40 50.0 XIII 1:10 87 33 Alachlor 2-57 0.38 AND 13: 1 67 109 53 / 5 kg / ha / 0.8 AND 6, -25: 1 100 48 32.0 rv 1: 6.4 99 40 and_ 50.0 XIII 1:10 97 35

Example a'd XXII - herbicide extender test. The biological tests were carried out according to Example XTIII, using Butachlor as active ingredient, and compounds 2-24, 2-25, 2-27 as extenders of the active ingredient. The prolonging action compounds were used in the form of preparations prepared according to Examples III, XIII-XII.

The most important data and the results of the weed weight measurement for the second sowing are given in Table 6.

Table 6

Center The relationship extends Examples πλ Iz Weed weight /% / herbicidal ing action preparations u UUoUIlu tL / dose - p / Center Extend- I will connect no Relationship Dose = q weed wife / X + Y / no / kg / ha / deadly / X / / Y / Butachlor 2-24 0.1 XIII 50: 1 75 108 74 / 5 kg / ha / 0.5 XII 10: 1 105 65 2.0 XI 2.5: 1 102 54 3.3 III 3: 2 92 51 Butachlor 2-25 0.1 XIII 50: 1 75 97 71 / 5 kg / ha / 0.5 XII 10: 1 95 62 2.0 XI 2.5: 1 95 56 4.0 XVI 5: 4 93 51 Butachlor 2-27 0.1 XIII 50: 1 75 99 63 / 5 kg // ha / 0.5 XII 10: 1 98 55 2.0 XI 2.5: 1 93 51 4.0 XI 5: 4 91 44

Example XXIII. The biological tests were carried out according to example CTIII using Propachlor as active ingredient and active ingredient extenders of general formula 2 / 2-30 and 2-31 /.

149 105

The results of the measurement of weed weight at the second sowing are presented in Table 7.

When evaluating the results, it was found that when using Propachlor, its herbicidal action is significantly prolonged by combining it with an extending agent.

Tables 7

Center herbicidal Compound prolonging action Stoaunok Weight weeds /% / center / dose - p / Extend- Connection Relationship Dawta = q herbicidal wife no / kg / ha? n / / Y / / X + Y / Propachlor 2-30 0.5 12: 1 70 101 58 / 6 kg / ha / 2.0 3: 1 99 37 4.0 3: 2 96 25 Pupa chlorine 2-31 0.5 12: 1 70 100 42 / 6 kg / ha / 2.0 3: 1 98 thirty 4.0 3: 2 95 10

Claims (1)

Patent claim The herbicide of the przedłżżonym action, characterized in that the active substanoję contains 0,8-95% by weight of derivatives of ^ jo -chloroacetanilidu of formula 1 wherein R 'and R are the same or different and represent a hydrogen atom, an alkyl group ^j for 1-3 ^h atomac atoms and ^R is a straight or ^{PG ± ±} ałęzion ^{g PE} ru a] .kilową having from 1 to ⁶ carbon atoms or a alkoksyalkioową having 1-4 carbon atoms in each alkyl moiety as well as a means extenders 1- 80% by weight of N-allUo-N / N * ^{- s} dipod ion ⁱⁿ the ^y c ^h glicynoami ^d uo general formula 2 ^{wherein R} and R are identical ^± i.ub different and represent a hydrogen atom, straight or branched an alkyl group of 1-6 carbon atoms, an alkenyl group of 2-6 carbon atoms, cyclohexyl or substituted up to twice by an alkyl group of 1-3 carbon atoms or halogen, phenyl or -be ^eskers yl ^{group, and LB} R i. ^{R t} together with the ^^ ^y chain. ^h eksaratylenową wherein ^Y atom nitric t ^wo WHO heteroc ^yk large ring, R ^b is optionally pods ^t awiln ^{JE d} to m i; y ^y times with a halogen atom a straight or branched alkioową with 1-5 carbon atoms, alkenyl of 2 -5 carbon or benzyl atoms, in addition to 1-96% by weight of solid carrier and / or liquid diluent and 0.1-25% by weight of surfactants, the weight ratio of herbicides to extenders being 2 (03: 1- 1:10. WZ0R 1 DESIGN 2