SU1591797A3 - Herbicidal composition - Google Patents

Description

The invention relates to chemical means of protection, plants and can be used in agriculture. The purpose of the invention is to increase the pro. The invention relates to chemical means of plant protection and may find application in agriculture.

The purpose of the invention is to increase the prolonged action.

According to the invention, the duration of action of thiol-carbamate herbicides can be extended by using compounds of the formula

Ζ

II. К ₅ '^ -Ύ (0) _η -0-Ν <

Πβ,

the values of the radicals are given in table. one.

The compounds used as prolongators according to the invention,

2

longing action. According to the invention, the duration of action of the herbicidal drug eptam is 3-ethnyl, n-di-n-propylthiol carbamate or his. mixtures with the antidote ^ - Ν, Ν-diallyl dichloroacetamide can be increased by the joint use of these drugs with a compound of the formula Κ ₄ Υ (0) „С (Х) Ы (Ку) (К *), where with η = 1 - eight; Ζ - O; - ethyl; K ^ and K - 3 chloroallyl, and with η = Ο Υ, Ζ each - 0 or 8, K - lower alkyl, alkenyl, phenyl, substituted alkyl or phenyl;

K £ - - alkyl, allyl, chlorallyl; K hydrogen, lower alkyl, alkenyl, benzyl _? chlorallil, furfuril. The most active compound is 8-3τηπ-Ν, Ν-6ηο- (3 chloroallyl) thiol carbamate. The mass ratio of herbicide and prolongator (3: 1) - (0.75: 1). The proposed prolongators are more effective than the known. 6 tabl.

in high doses, known as herbicides. They can be obtained by reacting a secondary amine and a substituted chloroformate in the presence of an acid acceptor.

Bis- (3-haloallyl) -thiolcar bamate prolongators can be obtained by reacting bis- (3-haloallyl) amine with the substituted chloroformate in the presence of a base and a solvent.

И р і мір 1. Preparation of ethylN, бис-bis- (3-chlorallyl) thiolcar bamate. '

Getting Ν, Ν-bis- (3-chlorallyl) cyanamide. Sodium hydroxide (120 g,

20% aqueous solution, 0.6 mol)

add drop by drop and mix in

811, „, 1591797

04

3

1591797

four

25.2 g (0.3 mol) of a 50% aqueous solution of cyanamide, while maintaining a temperature of 0-8 ° C.

After that, 55.5 g (0.5 mol) of 1.3 - $ dichloropropylene and 3.4 g (0.01 mol) of tetrabutylphosphonium bromide are added dropwise to the mixture.

The reaction mixture is then slowly heated to 80.degree. C., the mixture becomes a dark orange color. It is heated at 80 ° C for 40 minutes and then cooled to room temperature.

The product is extracted with ether and washed three times with water, after which traditional methods of drying over magnesium sulphate, filtration and stripping are used. The unreacted starting material is removed during rotation.

evaporator under high vacuum.

Exit 87%. The product (41.5 g) is regenerated as a dark orange oil, the ι structure of the product is confirmed as 25 K, N-bis- (3-chloroallyl) cyanamide using mass spectroscopy, nuclear magnetic resonance and infrared spectroscopy.

Getting Ν, Ν-bis- (3-chlorallyl) amine. N, Ν-bis- (Z-chlorallil) cyanamide (38.2 g, 0.2 mol) is placed in a flask and 16 ml of concentrated H ^ AO ₄ in 92 ml of water are added, the mixture is refluxed for 4 hours while stirring and then cooled to room temperature, after which 50 ml of water are added. The mixture is extracted with 50 ml of ether and the ether extract is discarded. 200 ml of water are added to the aqueous phase. In an ice bath, while stirring, a solution of 47.4 g of NaOH in 92 ml of water is slowly added dropwise. The mixture is then extracted three times with ether, the ethereal phases are combined, washed with food twice with water, dried over magnesium sulfate, filtered and stripped. The product yield is 85%. The product (28.2 g) is regenerated as a liquid of dark orange color.

Getting ethyl-Ν, Ν-di- (3-chloro al · *: "·. ·., Lil) -thiolcarbamate. Bis- (3-chloroallyl) amine (52.3 g, 0.315 mol) is added dropwise to ethyl chlorothio-formate (37.4 g, 0.300 mol) in the presence of sodium hydroxide (13.2 g, 0.330 mol), water ⁵⁵ (100 ml) and ethyl ether (200 ml) in a 500-mm flask. The reaction flask is cooled in dry ice to

5-10 ° C, the reaction is exothermic.

The mixture is divided in phases. The ether phase is washed with a dilute hydrochloric acid solution and water, dried over magnesium sulfate and concentrated in a rotary evaporator.

The weight of the residual liquid is 73.1 g. Theoretical percentage yield is 95.9%. The refractive index is ηΏ ^3β 1,5341. The product is confirmed by nuclear magnetic resonance (NMR), gas chromatographic mass spectroscopy (GHMS) and infrared spectroscopy (IR).

Example 2. Preparation of n-butyl, Ν-bis- (3-chlorall il) ^ thiol-carbamate.

Bis- (3-chloroallyl) amine (1.2 g) is combined with 0.7 g of triethylamine (TEA) and 30 ml of dichloromethane. The mixture is cooled in an ice bath. Temperature supported live below 18 ° C. Бу-Butylchlorothioformat (1.1 g) is added dropwise.

The mixture is then stirred at room temperature for 2 hours. The product is extracted using conventional techniques. Specifically, the mixture is washed once with saturated sodium bicarbonate solution, and then once with water. The next day, the mixture is dried over magnesium sulfate, filter-g is rubbed and stripped.

The product (2.3 g) is registered as a light yellow oil. The refractive index is ηϋ ^{? 0} 1.5414. The structure is confirmed by NMR, GHMS and IR.

Approximately 3. Preparation of benzyl, Ν-bis-3-chloroallylthiocarbamate.

The procedures described in Example 2 are used. 1.4 g of benzyl chloro thioform ta are used. The product (2.4 g) is. a light orange viscous oil, ηϋ ²⁰ 1,5896.

Example 4. Tests, on the rise. herbicidal activity.

In tabl. 2 presents the test data for herbicidal activity for typical prolonged compounds within the scope of the invention, showing their effectiveness in prolonging the herbicidal activity of thiol carbamate herbicides. The effect is visible when comparing the degree of weed control in the experimental baskets treated with a thiol-carbamate herbicide or the proposed compound. A prolongator, with what is observed in such baskets,

five

1591797 ⁶

treated with both thiol carbamate herbicide and the proposed prolongator compound. The soil used is sandstone loam, pretreated with a thiol carbamate herbicide to mimic the usual field that has been used for the preliminary application of herbicides.

In most cases, the health tests are carried out with a thiol carbamate and an antidote formulation (in Table 2, the soil has been pretreated and then treated with a thiol carbamate herbicide only).

The effectiveness of the prolongator in minimizing the degradation of the thiol carbamate herbicide in the soil is checked by comparing the herbicidal activity of the herbicide or herbicide and antidote, when they are applied alone, with herbicidal activity 20, when these formulations are brought together with the prolongator in various dosages. One herbicide or a herbicide and an antidote without a prolongator show insignificant herbicidal 25 activity in the structured soil, which is 0-5%. The compound of the prolongator in each case significantly increases the herbicidal activity in the structured soil. zo

The last column in the table. 2 shows the absence or negligible herbicidal activity of each prolon- '. gator in the previously untreated soil at a dose of 4.48 kg / ha. In most cases, the prolongator closes up the pre-planting (ΡΡΙ), RNE - the pre-emergence superficial introduction of prolon [gator at a dose of 4.48 kg / ha.

I. Experiments on 8-ethyl Ν, Ν-di-n-propyl to thiol-carbamate (eptam) and antidote.

A. Pre-tillage.

Solution ₁ is prepared by diluting an emulsifiable liquid concentrate containing 0.72 kg / l (76.8 wt.%) 45 eptam herbicide in 200 ml water so that the resulting concentration of herbicide in the solution of 2000 mg / l. 200 ml of this solution is then added to 90.8 kg of soil, to which 50–15 fertilizer 17–17–17 (Ν-Ρ ₂ 0 ₅ -Κ ₂ 0 On a mass basis) is added before reaching a concentration of 50 ppm by weight with respect to soil.

The mixture is stirred in a rotating mixer for 10-30 minutes. 55

Then the soil is placed in round plastic containers with a diameter of 19.0 cm and a depth of 19.0 cm. The applied herbicidal dose is 3.36 kg / ha. Soil

stamped and leveled with a razmetechik rows in order to print one row across the width of each container. This row is seeded with chicken millet (Eszpozina sgiz-§a111). A sufficient amount of seeds is grown to produce several seedlings. Then the containers are placed in a greenhouse, in which the temperature is maintained at 20-30 ° C, the greenhouse is irrigated daily by a sprinkler.

6 weeks after treatment, the soil is left to dry and the foliage of the plants is removed. After that, the soil is passed through a screen with a cell size of 0.4 cm to remove roots and lumps of earth.

₍ B. Testing Herbicides.

The solution is prepared by diluting the emulsifiable liquid concentrate containing 0.72 kg / l (76.8 wt.%) Of the herbicide 5-ethyl-S, N-din-propylthiocarmat (eptam) in 675 ml of water, so that the resulting concentration of herbicide in solution .14 mg / ml.

5 ml of this solution is then added to 1.35 kg of soil, giving a dose in soil equivalent to 3.36 kg / ha of the herbicide.

Connection prolongator used in industrial form. Each sample of the prolongator is dissolved in 5 ml of acetone and 14.5 ml of water so that the resulting concentration of the prolongator in a solution of 1.54 mg / ml, 5 ml of this solution is then added to 1.35 kg of soil, giving a rate in soil equivalent to 4, 48 kg / ha prolongator.

5 ml of the prolongator solution and 5 ml of the herbicide solution are mixed in a reservoir. The resulting mixture (10 ml) is then added to 1.35 kg of soil and embedded in the soil using a rotating mixer. 10 ml of the mixture and 1.35 kg of soil are placed in a rotating mixer and embedded in the soil, obtaining the rate of herbicide and prolongator in the soil, equal to 3.36 and 4.48 kg / ha, respectively.

Some prolongators are tested at different doses. In such cases, the appropriate volume (ml) of the prolongator solution is mixed in the tank with 5 ml of the herbicide stock solution to obtain the desired dose of 0.56; 1.12 or 2.24 kg / ha.

The treated soil is then placed

in aluminum baskets (8,9x19,5x

x6.4 cm). The soil is tamped and you

1591797

eight

using a razmerchika rows for printing six rows across the width of the basket. Experienced weeds are chicken millet - IP, $ EsHhposYoa sgiz-eaPg (b), wild oat Io, Akepa £ a £ ia (b), zasdeg sape 8HS, Zog ^ bjht h1nog (b) MypsN. ·

P-10 t11o (bargain bicol) is also used as an indicator of plant growth. Sow two rows of chicken millet.

One row of Maika BepaN ΧΣ-25Α of the form 2еа haaus (b) is also sown.

Sufficient seeds are grown to produce approximately 20-25 seedlings per row. The basket is then placed in a greenhouse at 21-30 ° C and irrigated daily by sprinkler. by the apparatus. 20

Approximately three weeks after pickling, the degree of weed control is estimated and recorded as a percentage compared to the growth of the same species in the control cr-25 zine, having the same age, grown in structured soil, but not treated with either a herbicide or a prolongator. Scale assessment var. It ranges from 0 to 100%, where 0 is 30 and there is no effect with the growth of plants, equated to the untreated control plot, and 100% - complete destruction.

2. Experiments with 5-ethyl-S, N-di-n-propyl thiol carbamate and antidote,-diallyl dichloroacetamide.

These methods are essentially the same as 1A and 1B, except that the antidote Ν, Ν-diallyl-do dichloroacetamide is applied with a herbicide.

Prepare the basic solutions described in 1B, and additionally get a basic solution containing thiolcar bamate herbicide and antidote. 45

Emulsifiable liquid concentrate

5-ethyl-11,] I-di-n-propylthiocarbamate (82.8%) and Ν,-diallyl-dichloroacetamide (6.9%) are diluted in water so that the resulting thiol-carbamate-rich herbicide 1.14 mg / ml The weight ratio of the thiol-carbamate herbicide to the antidote is 12: 1.

An appropriate amount of the basic solution of each typical prolongator is applied to obtain the desired dose of application. Then the rest of the methodology 1B follows, including the evaluation criteria.

Tab. 2 shows where the asterisks are not marked, the test results in which the thiol carbamate herbicide and antidote are applied at a dose of 3.36 and 0.28 kg / ha, respectively, by preplant, and the prolongator are introduced at doses of 4.48; 2.24; 1.12 and 0.056 kg / ha by preplant placement.

3. Herbicidal sieve analysis dpya prolongator.

The last column of table 2 shows the screening data for herbicides for typical prolongator compounds, tested individually at a dose of 4.48 kg / ha. In most cases, prolongators close up preplant.

A, Pre-planting Termination Test.

The soil used is sandy loam, in which fertilizer 17-17-17 (Ν-Ρ ₂ 05-Κ ₂ 0 on a mass basis) is added to a concentration of 500 ppm by weight in relation to the soil.

The prolongator compounds are used in industrial form. These substances are added to 5 ml of acetone and 14.5 ml of water so that the resulting concentration of the prolongator in the solution is 1.54 mg / ml. 5 or 10 ml of this solution is added to 1.35 kg of soil in a rotating body mixture and thoroughly mixed, obtaining the amount of prolongator in the soil, equivalent to 4.48 kg / ha.

Treat the soil then placed in aluminum baskets (6.4 x 8. _# 9x x 19.0 cm). The soil is tamped and evened with a razmerchik of rows <to imprint six rows across the width of the basket. The following test weeds are used: chicken millet, wild oats, Nephilidae.

Next, K-10 ιηίΐο (hog – nishish) is also planted as an indicator of plant growth, maize X — 10 (Fig. 4) as an indicator of sensitivity. Sow two rows of chicken millet. One row of each of the remaining weeds, a plant growth indicator and maize, are planted.

Sufficient seeds are sown to produce several seedlings in each row. The baskets are then placed in a greenhouse at 21-30 ° C, irrigated daily by a sprinkler. 2 weeks after dressing

1591797

ΙΟ

seeds measure the degree of damage or control by comparing with plants from untreated plots of the same 'and the same age. The degree of damage varies from 0 to 100%, registered for each species.

B. Pre-emergence testing of herbicides.

On the day before the compounds are introduced, the seeds of eight different types of weeds are sown in the sandy loamy soil in individual rows, using one view of the row across the width of the basket. The weeds used are bristle green (GT), chicken millet (UC), wild oat (MO), one-year ipomoea (ΑΪ10), Teofrasta boree (νатι), sarepta mustard (MD), spike-leaved (RM) (or curly sorrel) as well as yellow syt (ΥΝΟ). Plant plenty of seeds in order to obtain from 20 to 40 seedlings per row after emergence, depending on the size of the plants.

Using analytical scales,

600 mg compounds prolongator, intended for testing, weighed on a piece of glassine. Paper and coupler10

15

20

25

The tion is placed in a 60-millimeter wide-weed control for the established

coiled transparent bottle and dissolved in 45 ml of acetone. 18 ml of this solution are transferred to a wide-mouth transparent bottle (60 ml) and diluted with 22 ml of a mixture of water and acetone (19: 1) containing a sufficient amount of polyoxyethylene sorbitan monolaurate emulsifier to obtain the final solution with a volume ratio of 0.5%. Then the solution is sprayed on the sown soil on a linear spray table, graded for a supply of 748 l / ha.

The dose of 4.48 kg / ha.

. After processing, the baskets are placed in a greenhouse at 21-29 ° C and irrigated using a sprinkler. 2 weeks after treatment, the degree of damage or weed control is determined by comparison with untreated control plants of the same age. Damage assessment from 0 to 100% is recorded for each species. '

The results given in table. 2, po35

40

45

50

It is said that each compound of the prolongator significantly increases the herbicidal activity of both a single herbicide and a herbicide and antidote in structured soil. These results are unexpected, since none of the prolongators have any significant herbicidal activity per se.

Example 5. It is very rare in a structured soil when herbicidal or herbicidal plus antidote compositions are tested separately, i.e. without prolongator, their herbicidal activity is more than 0-5%. Using the described methods get the test results given in table. 3 (in the table the nominal values are entered. For the eptam or eradikan separately on structured soil).

Example 6. Tests with delayed planting in pre-treated soil.

This example offers additional data on herbicidal active .-; for a characteristic prolonged compound within the scope of the invention, showing its effectiveness in prolonging the herbicidal activity of three different thiol-carbamate herbicidal compounds, each of which contains an antidote. As in example 4, the effect is visible when comparing

period of time after introduction into the experimental baskets, treated with the antidote thiol-carbamate herbicidal composition, with what is observed in such baskets, treated with the same herbicidal composition, in addition, containing the characteristic compound of the prolongator.

The following thiol carbamate herbicides are used: 8-ethyl-K, N-di-n-propylthiol carbamate - eptam, 8-ethyl-P, N-di-nisobutylthiocarbamate - sutan, 8-n-propyl-P, N-di-n-propylthiocarbamate - right.

The antidote used is Ν, алdiallyl dichloroacetamide in a mass ratio with epTam 12: 1 herbicide / / antidote; 24: 1 (by the sutan); 12: 1 (with verna).

A typical compound of the prolongator in this example is ethyl N,-di-3-chloro-allyl thiol carbam t (with compound 1).

A. Pretreatment of the poch55 you (first processing).

Aluminum baskets Oh 6x15,24x

x20.32 cm) filled with sand

loamy soil. 10 ml of an aqueous basic solution containing 11.1 mg of P epta1591797

12

Ma and 0.925 mg of antidote are mixed in each of the two baskets with soil, using a 5 gallon cement mortar mixer. The main solution is obtained by suspension

134.1 mg of emulsifiable concentrate, containing 6.7 pounds of eptam and 0.56 pounds of Ν,-diallyl dichloroacetamide per gallon, in 100 ml of water. Dose out-, θ

3.36 kg / ha of eptam and 0.28 kg / ha of antidote.

Other baskets of soil are pretreated with 100 ml of a solution containing 11.1 mg of Vernama and 0.925 mg of the antidote. The main solution is obtained by suspending 132.1 mg of an emulsifiable concentrate containing

7.5 kg / ha Vernama and 0.57 pounds of antidote per gallon in 100 ml of water. A dose of 20 is the introduction of 3.36 kg / ha of Vernama and 0.28 kg / ha of antidote.

Two additional baskets of soil are pretreated with 10 ml of ra-. a site containing 14.8 mg of sutan and 25 0.615 mg of antidote. This basic solution is obtained by suspending

173.7 mg of emulsifiable concentrate, containing 0.8 kg of cassock and 0.336 kg of antidote per liter, in 100 ml of water. Dose of the administration of 4.48 kg / ha of sutan and 0.18 kg / ha of antidote.

Baskets with the soil treated with the indicated tiolkarbamatnymi gerbitsida- ¹ E in combination with antidotes, are placed in a greenhouse at 21-22 ° C for six weeks, ^ where they are supported by means of wet lung irrigation by sprinkling. No seeds are planted in the treatment baskets.

B. Herbicidal treatment (second treatment).

Six weeks after the first treatment, one basket of soil from each pair of baskets pretreated with the same herbicidal compositions is re-treated with the same (herbicide plus antidote) composition, mixing 10 ml of stock solution prepared in the same manner as described in part A, with soil, using a mixer for cement mortar with a volume of 22.68 l (ΡΡΙ application).

Another basket of each pair is treated with a reservoir mixture containing ³ 10 ml of the basic solution, a herbicide plus an antidote obtained in combination with 10 ml of the basic solution containing 3.7 mg of the prolongator, ethyl-Ν, Ν bis- (3-chlorallyl) thiol-carbamate. The core solution of the prolongator is obtained by dissolving 37 mg of technical 3τηπ-Ν, Ν-6ηο- (3-chloroallyl) thiol carbamate in 5 ml of acetone containing 2 drops of a mixture of polyoxyethylene esters of sorbitan monolaurate, followed by the addition of 95 ml of water, 20 ml of a tank mixture containing three-sided The combination of herbicide + antidote + prolongator, pre-planting, is embedded in the soil using a cement mixer with a volume of 22.68 l. Then the soil is placed again in the aluminum basket.

In each basket of soil, one row of about 50 chicken millet seeds is planted immediately to a depth of 1.4 cm (delay 0 days).

The baskets with soil are slightly irrigated and placed in a greenhouse at 21-32 ° C, the second row of chicken millet is planted in each basket 2 days after the second treatment, the other rows are planted after 5.8, 12 and 21 days after the second treatment, respectively.

Weed control results for rows sown at the same time are recorded four weeks after seeding .; Thus, estimates are made at 28-49 days after the second treatment.

In tab. 4 shows the results showing that the herbicidal activity of all three thiol carbamate herbicides is prolonged when a prolongator is included in the herbicidal composition. A prolonator tested at a dose of 1.12 and 4.48 kg / ha, respectively, in a previously untreated soil, did not show herbicidal activity against chicken millet.

Example 7. Tests with a delayed planting in untreated soil are carried out analogously to example 5, However, sandy loamy soil is not previously treated in accordance with the methods of example 6A.

The methods of Example 6B are carried out, except that the sowing occurs 0, 7, 14, 21 and 28 days, respectively, after the first and only tillage.

The data table. 5 show that

prolongator prolongs life in the soil

all three thiol carbamate herbicides

in composition with antidote. The prolonator (compound Ί) showed no

13

1591797

5 4

herbicidal activity against chicken millet when tested with a dose of 1.12 and 4 ₍ 48 kg / ha, respectively, in untreated soil.

In tab. 6 shows the comparative data on the herbicidal activity of the known and proposed compositions.

ten

Claims (3)

Herbicidal composition comprising 3-ethyl-M, P-di-n-propylthiolcarbamate or its mixture, with Ν, Ν-diallyl dichloroacetamide in a ratio of 12: 1 and prolongator, characterized in that It contains as a prolongator a compound of the general formula 20: q, -y (o) pnc <"5 25" b 'where Υ-5ηΖ-Οηβ = 0 P ^ - C, -C4-alkyl, phenyl, 2- or 4-chlorophenyl, benzyl, allyl, 2-30 methylallyl, 2-chloroallyl, 3-chloroallyl, 3-phenylpropenyl, one ιζξζϊ 3 M. ± - .1 Μ- M. 50 0 3, Z-Dichlorallil 3, Z-Dichlorallil 3 0 51 with _r and ₅ 0 Allyl Z-Chlorallyl eight 0 52 0 Zinnamil Zinnamil eight 0 53 .Allil 0 .3-Chloralally Z-Chlorallyl eight 0 54 Ethyl 0 2-Chloralup 2-Chlorallyl eight 0 55 1-Methylallyl 0 Z-Chlorallyl Z-Chlorallyl eight 0 56 2-Chloralll 0 - ⁿ - eight 0 57 Z-Chlorallyl 0 - eight 0 58 ^ Parpyl 0 - ^and - eight 0 59 - ⁿ - 0 —’M 3 3 60 CH ₃ 5CH _and - 0 eight 0 61 Sn ₃ ssn ₂ - 0 - eight eight 62 Z-Cyanopropyl 0 eight 0 63 0 '- eight eight 64 Ethyl 0 Allyl Allyl eight 3 65 Allyl 0 * —And— eight eight 66 (3-Phenyl) -2-propynyl 0 Z-Chlorallyl Z-Chlorallyl 3 3 67 (Z-Phenyl) -2-propip 0 - ⁿ - eight 0 68 Phenyl 0 - ^and - - 0 0 69 Allyl 0 - ⁿ - 0 0 70 (2,2,2-three- 0 - 0 0 chlorallil) 0 - 0 0 71 Vinyl 0 - ^and - 0 0 72 (4-Nitro) phenyl 0 - ⁿ - 0 0 73 Z-chloropropyl 0 - 0 0 74 ί2-Chlorethyl 0 0 0 75 'Metocioethoxy · methyl 0 - eight eight 76 Methoxyethoxymethyl 0 3-hporallil Z-Chlorallyl 3 0 77 (4-methoxy) phenyl 0 0 0 78 (4-Chlorine) phenyl 0 - eight 0 79 p-tolyl 0 · 0 0 80 (4-Chlorine) phenyl about - ⁿ - 0 0 81 (Z-Trifluorometip) fenil 0 - 0 0 83 Phenyl 0 -. ⁿ - 3 0 84 (2-Chlorine) phenyl 0 eight 0 85 Ethyl 0 - Furfuril 3 0 86 0 Methoxyethyl eight , 0 87 (2-Chlorine) ethyl 0 - 0 0 88 - ⁿ - 0- - ⁿ - FURFURIL 0 0 19 1591797 - Continued table. one 2 five ...... four 6 ? 89 Allyl 0 Z-Chloromethyl Methoxy- eight 0 ethyl 90 - ⁿ - 0 Allyl - ⁿ - 0 0 91 2-Methoxy 0 - 2-methyl- eight 0 lil allyl 92 Ethyl 0 Z-Chlorallil 3-Chlorallil 8 0 (tall' (tall cis) (trance) 93 Allyl 0 Z-Chloralally Furfuril. eight 0 94 0 Methoxyethyl 8 0 95 - ^and - 0 -eleven- Furfuril eight eight 9ό Ethyl 0 (2-Methyl) - 0 allyl 97 (2-Chlorine) - 0 0 0 ethyl 98 Ethyl 0 - ⁿ - eight eight 99 Crotyl 0 - ⁿ - Z-Chlorallyl 8 eight 100 Ethyl one Z-Chlorallil Z-Chlorallil 8 0 101 2 - -eleven - eight 0 102 0 Hydrogen, eight 0 103 Allyl 0 0 0 104 0 - ⁿ - (2-Methyl) - 0 0 allyl 105 (2,3-dihyd 0 Z-Chlorallyl 8 eight roxy) propyl 106 · Ethyl 0 (2-Chlorine) ethyl (2-Chlorine) ethyl eight 0 107 _ eleven_ 0 Z-Chlorallyl Cyclopropylmethyl eight 0 108 Allyl 0 - II— 0 0 109 Ethyl 0 - ⁿ - Benzyl eight 0 110 Allyl 0 - ⁿ - _P_ 0 0 111 - Ιί— 0 2-Chlorethyl Hydrogen 0 0 112 (2,4-dinitro) phenyl 0 Z-Chlorallyl Z-Hsgorallil 3 eight 113 2- (1,3-dioxolanyl) ethyl 0 - ⁿ - - ⁿ - eight eight 114 Ethyl about. - ⁿ - - ⁿ - 0 . 3 115 (2,2-diethoxy) ethyl 0 eight 3 116 Allyl 0 (2-Methyl) allyl 0 0 118 - ⁿ - 0 Allyl (Methoxy) ethyl 0 0 119 (2-dioxole • nyl) methyl 0 Z-Chlorallyl Z-Chlorallyl eight eight 120 2-butenyl 0 - ⁿ - - ⁿ - 0 0 124 Crotyl 0 - ⁿ - - ⁿ - 3 0 125 (3,4,4-Trifluoro) -2-butenyl 0 - ^{1 |} - 3 0 126 2-butenyl 0 Z-Chlorallyl 3-Chlorallyl 0 0 127 Parargil 0 - ⁿ - - ⁿ - 0 0 128 2-butenyl 0 - ⁿ - - ⁿ - -.V · 0 0 ? one ~ ΐ 3 1-1 - ~ - _g ⁶ 1 ⁷ ten 0 Allyl -II 8 0 eleven Pc ₃ H ₇ ~ 0 - ⁿ - -and 8 0 12 n — C ₊ H ₉ - 0 -and 8 0 13 ps ₃ H ₇ - 0 from-With ₄ N $ -n 8 0 14 Phenyl 0 with _a p-n ₇ - η-C h) 1 7 8 0 15 P ₊ C ₉ - 0 Z-Chlorallyl • Allyl 8 0 sixteen 2-Chlorallyl 0 Allyl -. ⁿ - 8 0 17 Allyl 0 Z-Chlorallyl 8 0 18 0 _and_ · P-Szn ^ 8 0 nineteen - 0 n-C _a H ₇ -n 8 0 20 2-Methylallyl 0 Allyl Allyl •thirty 21 CH ₃ 5CH, - 0 - PС ₃ 1Ц 50 22 CH ₃ 5CH _g - 0 from-With ₄ N <) IZO-S ₄ N d 8 0 23 2-butenyl 0 Allyl Allyl 8 0 24 - 0 2-Methylallyl thirty 25 Parargil 0 Allyl 8 0 26 2-Cyanostil 0 n-C ₇ H _E n-C ₃ H _g thirty 27 · C ₂ H ^ 8CH ₂ - 0 'C and _{5 g} -With ₂ ND. 8 0 28 C ^ CHF, - 0 Allyl Allyl 8 0 29 CH ₃ 8C ₂ H ₄ - 0 - 8 0 thirty with _{2N y} 0 Z-Chlorallyl Z-Chlorallyl 0 0 31 n-C _a H ₇ 0 0. 0 32 П-С4Н3- 0 • 3 Chloralally Z-Chlorallyl 0 0 33 from-With ₄ N ₉ - 0 „_M_ 0 0 34 from SzNι / 0 0 0 35 ® -sn _g ' 0 - ⁿ - - 35 '| ⁰ θ 36 ^sn s ~ 0 ~ - ^and - 0 0 37 Z-Chlorallyl 0 Allyl Allyl 8 3 38 0 Z-Chlorallyl Z-Chlorallyl 8 '3 39 Allyl 0 - ^and - - ⁿ - 8 3 40 CH _E - 0 _1T_ - 8 8 41 3, 3-Dichlorallzl (og ^SN 2- " 0 8 3 42 0 8 8 ^: 43 ^C 1 ^H 5 " 0 8 8 44 Cyanomethyl 0 - ¹ * - 8 8 45 from _{2 to 5} - • 0 Z-Chlorallyl (high cis) ;: Z-Chlorallyl (high cis) ^; . '. 8 0 46 ^{with 1N} 5- 0 Z-Chlorallyl (tall trance) 3 — Chloralgil (tall trance) 8 0 47 ^C 1 ^H -5 0 2-Butenip 2-butenyl 8 0 48 ? S. ^ Yiwu 0 Parargil ' Parargil 8 0 49 s * n $ 0 0 0 1591797 18 Continued table. one 2! 1591797 , · 22 - - Continuation table 1 one 2 3 four . ⁵ I ί to 129 (3,4,4-Trifluoro) -3- 0 3-Chloralum.p 3-Chlorallyl 3 3 butenyl 0 130 Phenyl 0 Allyl Allyl 3 131 - 0 Isopropyl Isopropyl 3 0 132 -AND- 0 Isobutyl Isobutyl 3 0 T a b l i c a 2 Compound Activity on the general population weed Ζ Eradikan + (* -eptam + • prolongator prolongator) kg / ha And with a key prolongator 3.36 + 0.056 ' 3.36 + 1.12] 3, 36 + 2.24 | W, 36 + 4.48 one - - one . 100* 7e 70 81 * 87 * 96 * - 58 82 96 96 - 61 75 95 97 - 68 86 95 98 · - 62 86 92 98 - 80 91 94 96 - 66 74 82 89 - 2 21 58 74 98 0 3 28 47 65 96 0 four 25 50 85 97 0 five 40 82 92 96 0 6 26 38 65 85 0 7 12 24 44 63 0 eight - - - 34 * 0 9 - - - 62 * .0 6 * 15* 29 * 50* - ten. 69 * 0 four* 12* 18* 27 * - eleven 85 * 0 2 * eleven* 21 * 40 * - 12 73 * * 0 four* 7 * sixteen* 29 *  - 13 -  - - 51 * 0 14 - - - 38 * 0 15 - - - 78 * 34 four* 18* 33 * 59 * - sixteen . - - - 92 * 57 17 - - - 100* 46 18 - ' - - 100* 69 nineteen - - - 81 * 0 6 * 14* 38 * 47 * - 20 - . - - 89 * 63 21 - - 100* 46> 22 - - 94 * 21 6 * 23 * 38 * 71 * · - 23 - - - 61 * 29 23 159179 / 24 Continued table. 2 "Nm · * - Compound • Activity on the total weed population,% Eradikan + prolongator, kg / ha (# - eptam + prolongator) Exclusively ProLugator 3.36 + 0.056 3.36 + 1.1g | 3.36 + 2.24 3.36 + 4.48 24 - - - 63 * 14 25 -  - - 92 * 50 26 -  - - 35 * 0 27 - - - 47 * 15 28 - - - 48 * eight 29 - - 66 * 23 · thirty . 43. 51 76 96 0 31 12 36 65 84 0 32 6 nineteen 42 55 0 33 0 five 20 36 0 34 0 2 20 52 0 35 0 eight 13 27 0 36 - - 78 0 - - - 47 0 29 35 46 74 - 38 - - - 87 '0 68 90 92 96  - 39 - - 89 0 77 . 95 95 - 95 - · 40 - - - 87 0 70 82 92 97 0 41 - - - 34 0 RNE 42 - - - 67 2 47 55 17 82 - 43 - - 88 0 64 77 89 95 0 44 -  - 92 0 65 86 88 95 - 45 sixteen 32 61 81 five 46 85 96 97 97 7 60 83 85 •. 91 - 52 13 35 40 , 49: 0 PKE 53 77 99 99 99 0 100 99 100 100 - ' 54 33 40 · 51 79 0 PKE 55 - - - 91 0 54 70 86 97 - 56 - - - 100 0 34 57 64 94 - 57 - - 80 0 41 • 50 64 93 - 58 - - - 89 five 70 79 97 97 - 59 - - - 97 0 '29 42 501 63 - - - - 70 60 - - - - 82 0 25 44 61 94 - 61 - - - 94 · 0 25 26 1591797 Continued table. 2 . I · Y Compound Activity on the total Eradikan + prolongator, (* -Eptam + prolongator) weed population, Ζ kg / ha Exceptionally prolongator 3.36 + 0.056 36 + 1.12 ^ 3, 36 + 2.24 3.36 + 4.48 39 70 89 96 62 - - - 90 0 - - - 92 0 20 39 75 96 - 63 - -. - 47 ‘ 0 - - -. 53 0 64 - - - 64 thirty - - · - 75 38 65 - - - 94. 28 - - - 98 - 68 56 68 100 - 66 - - 27 ^e 0 ^С 25 thirty 60 96 67 - - - 41 ^C 0 ^e 68 - - - 49 ^e 0 ^e -  - - 100 0 - - - 98 0 100 100 100 100 - 70 - - - 27 ^e 0 ^e - - - 100 0 - - 97 0 , 99 99 100 Y0 - 72 - - - 38 ^C 0 ^e 73 - - - 54С about ^with 74 - - - ' 97 - - - - 96 0 ^e 94 82 99 100 75 - - - 49 0 76 - - - 31 0 ‘77 - - 31 0 78 - -  - 22 0 79 - - • - 46 0 80 - - 35 0 81 - - - 22 0 83 -  - - 88 0 52 71 ' 61 94 - 84 - - - 100 0 84 75 98 99 - 85 . - - - 97 6 32 33 62 99 - 86 - - - 100 62 74 54 93 99 - 87 - . - - 94 0 12 00 sixteen 67 - 88 - - - 78 0 y 37 76 70 74  - 89 - - - 98 0 22 27 82 99 - 27 Connect · performance 90 91 92 93 94 95 96 97 98 99 Ϊ00 101 102 103 104 105 106 107 108 109 110 111 112 113 ¹¹⁴ 115 116 118 119 134 125 126 1591797 28 Continued table. 2 Activity on the total weed population, X Eradikan + prolongator, (# -apparat + prolongator) kg / ha Exceptional but prolongator 3.36 + 0.05b) ) 36 + 1.12 | W, 36 + 2.24 ¹ 3.36 + 4.48  - - - 32 0 - - - 89 73 94 98 100 100 thirty - - -. 100 0 . 53. 28 64 97 . - - - - 100 35 57 66 97 100 - - - - 81 0 46 29 53 47 - - - - 96 79 - - - 96 0 81 74 92 94, - g · - - ’$ 3 eight 72 61 90 93 - - - - 82 0 72 68 75 89 - - - - 94 0 43 52 68 - 89 - · - - - - 34 0 32 26 22 50 - - - - 91 sixteen - - - 18 0 - ' - - 94 0 - - - 21 0 -G - - 22 0 - - 100 89 - - - 99 · 0 93 99 100 100 - 75 96 99 99 - - - - 82 47 - - - 98 0 80 86 97 100 - - - - 7.1 0 - - - 67 0  - - 89 0 89 87 91 ’ 99 - - - 98 0 64 93 98 98 - - - 13 0 -. - ' - 94 0 71 89 99 98 - - - - 32 0 - - - 24 0.. - - - 90 .0 - - - 95 0 - - - 99 0 65 62 76 • 77 - 29 1591797 thirty Continuation of table 2 Compound Activity on the general population weed 7 Eradikan + (* -eptam + prolongator prolongator) kg / ha Exceptionally prolongator 3.36 + 0.056 I.3.36 + 1.12 | 3, 36 + 2.24 | W , 36 + 4.48 127 - ,, 100 0 94 98 100 99 - 128 - - - 100 0 92 99 99 95 - 129 57 64 69 91 - - - 100 0 130 - - - 21 0 131 - - 14 0 132. - - - 24 ' 0 Π p names the с - average of 2 tests; e - medium her from 3 tests. Table 3 Compound prolongator Activity on the total weed population Go Eradikan + prolongator, kg / ha (* - eptam + prolongator) 2-butenyl, crotyl, 3,4,4-trifluorobutenyl, propargyl, C ^ -C ^ alkylthiomethyl, 2-cyano-35 ethyl, 3-cyanopropyl, methoxyethoxyethyl; - C ₂ -C ₄ -alkyl, 2-chloroethyl; allyl, 2-chlorallil, 3-chlorallyl, zinnamyl; K £ is hydrogen, C 2 ^- C ₊ -alkyl, 2-chloroethyl, benzyl, allyl, 2-methylallyl, 2-chloroallyl, 3-chloroallyl, cinnamyl, methoxyethyl, cyclopropylmethyl ^ furfuryl; when η = 1 K ^ -ethyl, K ^ -and Κγ- 3-chloroallyl; when Υ is O and ’Ζ is 0 η = 0 P ₄ ~ C ^ -C ^ alkyl, chloroethyl, phenyl, allyl, butenyl, 3,4,4-trifluorobutenyl, 2-butenyl, phenyl, substituted in the para-methyl, trifluoromethyl, chlorine, methoxy group; P ^ - allyl, 3-chloroallyl; P ^ is hydrogen, benzyl, cyclopropylmethyl, methoxyethyl, 2-methylallyl, 3-chlorallyl, furfuryl; when Υ - 3, Ζ-8, η = 0, P ₄ ~ ethyl, allyl, 3-chloroallyl, dichloralli, crotyl, 3,4,4-trifluoro butenyl, propargyl, 3-phenyl-2-butynyl, methylthiomethyl / methoxyethoxymethyl, cyanomethyl, 2,2-diethoxyethyl, 2,3 dihydroxypropyl, 3-cyanopropyl, 2-chlorobenzyl, G, 3-dioxolanylethyl, 2-dioxolanylmethyl; P ^ -allyl, 3-chloroallyl; P - allyl, 2-methylallyl, 3-chloroallyl, methoxyethyl, furfuryl in a mass ratio of herbicide: prolongator, equal to 3: 1 - 0.75: 1. Table! Compound η P ₅ Υ Ζ one 2 3 four five 6 7 one from _{2 to 5} - 0 Z-Chlorallyl 3 — Chlorallil 5 0 2 p-SZN ^ - 0 eight 0 3 ps ₄ N d - 0 3 0 four from-With ₊ N _E ' 0 - ⁿ - - ⁿ - five 0 five CH- 0 . - ⁿ - 3 0 6 five iso-SzN ^ 0 Z-Chlorallyl 3 — Chlorallil 3 ' 0 7 Benzyl 0 3 0 eight η-0 ₅ Η _Ί - 0 - from ₂ n _£ -and 3 0 9 pc. ^ H -, - 0 P “SzN7 -n 3 0 1591797 (θ Continuation of table 1 3.36 + 0.00 3.36 + 0.05b ’ 3.36 + 1.12 3.36 + 2 one 6C 80 88 98 10 ^th 77 78 92 47 21 ^e * - - - 10 ^th 2 sixteen 32 48 21 ^e * - 10 ^th eleven 27 45 49 21 ^e * - - - 50 21 ^e * - - - 10 ^th five eleven 25 51 21 ^e * - - - 10 ^th 53 83 89 120 12  - - - 121 12 - - - 122 12 -  - - 123 12 - - ---------- _Ί Exceptionally prolongator 3.36 + 4.48 94 7 94 '- 83 * 7 72 - 78 * 21 63 · - ' 43 * - 70 * 0 50 '0 96 * 59 91 -  99 - 100 - 100 - Ϊ00 - T a 8 l to c a 4 The first treatment, kg / g * The second treatment after 6 weeks, kg / ha Destruction of chicken millet, X, 28-49 days after the second treatment Herbicide | Antidote Herbicide ANT1 "DOT Prolongator Ding delayed landing one 0 13 | 3 I 3 | 12 ‘2 | 0 0 0 0 . 0 0 0 0 · 0 0 0 Eptam 3,36 0.28 Eptam 3,36 0,28 0 20 0 0 0 0 0 Eptam 3,36 0.28 Eptam 3,36 0,28 1.12 100 96 95 50 15 ' 0 Vernam 3.36 0.28 Vernam 3.36 0.28 0 0 0 0 0 0 0 Leerkam 3.36 0.28 Vernam 3.36 0.26 1.12 98 100 100 100 100 100 Soutache 4,48 0.18 Sutan 4.48 0.16 0 60 20 thirty ten . thirty 0 Sutan 4.48 0.18 Sutan 4.48 0.18 1.12 99 99 99 100 100 97 . 32 Table 5 31 1591797 "herbicide kg / ha The first tillage, kg / ha The destruction of chicken millet, 7 °, after 28-49 days Antidote Prolongator Days of delay in landing 0 · ’I 14 I 21 | 28 0 0 0 0 0 0 0 0 EP.tam 3.36 0.28 0 100 60 0 0 0 Eptam 3.36 0.28 1.12 100 100 99 97 60 Vernam 3.36 0.28 0 100 99 60 20 0 Vernam | 3.36 0.28 1.12 100 100 96 ’96 96 Sutan 4.48 0.18 0 100 : 100 96 65 thirty Sutan 4.48 0.18 1.2 100 100 100 100 100 T a b l and C a 6 Activity on a common weed population, 7. Known compound (patent of the USSR No. 1106442, tab. 2), kg / ha The proposed connection, kg / ha number 3.36 + 2.24 ^ 3.36 + 4.48 number | 3.36 + 2.24 | 3.36 + 4.48 one 29 47 one 87 96 2 18 12 sixteen '- 92 ' 3 • 26. 21 17 - 100 four 0 \ five 18 - 100 . five ten eleven 21 100 6 13 17 22 94 7 15 13 25 92 Note. The amount of herbicide 5-ethyl-SchP-di-npropylthiocarbamate (ERTS) is 3.36 kg / ha, and the prolongator 2.24 or 4.48 kg / ha, depending on the specified. Assessment carried out 3 weeks after treatment.