RU1797459C - Method of selective struggle against weeds in cereals - Google Patents

Abstract

An object of the invention is the use of chloroacetanilide herbicides for the treatment of cereal crops together with the antidote of the series of 2-chloro-4-trifluoromethyl-thiazole-5-carboxylic acids of the general formula g-HC (CI) -HN-C (CF3) C-CONR2R3. where RZ is hydrogen, methyl, propargyl, benzyl, trichloroaniline, furfuryl, 1-cyanocyclohexyl or 1-cyanodimethylmethyl, Yaz is hydrogen, methyl, phenyl, chlorophenyl, benzyl, chlorobenzyl, propargyl, 1-cyanocyclopentyl, in the ratio herbicide : antide 6: 1-1: 6. These antidotes are more effective in protecting crops than the known analogue in structure. 8 tab.

Description

The invention relates to the protection of cultivated plants from the phytotoxic effect of herbicides, and may find application in agriculture.

The purpose of the invention is to reduce the phytotoxic effect of herbicides.

Herbicides are known to be from various classes of substances, such as triazines, urea derivatives, carbamates, thiol carbamates, haloacetanilides, halogen-phenoxyacetic acids, etc. when applied in an effective dose, along with the weed to be destroyed, crop plants are also damaged to a certain extent. To counter this problem, various substances have already been proposed that can specifically counteract the harmful effect of the herbicide on the crop plant, i.e. protect the crop without

at the same time, a noticeable effect on the action of the herbicide on the weeds being destroyed. It turned out that the proposed antidotes both with respect to cultivated plants and with respect to the herbicide and, if necessary, also depending on the type of application, are very specific, i.e. a certain antidote is often suitable only for one particular crop plant and for certain classes of herbicides.

It has been found that thiazole-5-carboxylic acid amides of formula I are surprisingly successfully used to protect crops, in particular crops, against the harmful effects of agricultural chemicals such as halogenacyl herbicides . Therefore, amides of thiazole-5-carbon-. howling acid is called as follows

S

ABOUT

Vj

4

ate about

with

The text also contains antidotes, antidotes or protective substances.

Amides of thiazole-5-carboxylic acid correspond to formula I

Starting from 2-chloro-4-trifluoromethylthiazole-5-carboxylic acid chloride, other active substances of the formula I can be prepared by known methods and in accordance with the following reaction scheme

Particularly effective the proposed compounds as antidotes for herbicides: M-ethoxymethyl-M-chloroacetyl-2-ethyl-6

methylaniline,

Y-chloroacetyl-M- (2-methoxyethyl) -2,6-di methylaniline,

N-chloroacetyl-Y- (2-p-propoxyethyl} -2, b-dimethylaniline,

M-Chl "Shdetyl-M- (2-methoxyethyl) -2-ethyl

-6-methylaniline,

M-chloroacetyl-M- (methoxyethyl) -2,6-diethyleniline,

Y-chloroacetyl-M- (2-methoxy-1-methylethyl) -2-methylaniline,

Y-chloroacetyl-M- (2-methoxy-1-methylethyl) -2,6-dimethylaniline |

M-chloroacetyl-M- {2-methoxy-1-methylethyl- and l) -2,6-d of ethyl n and l and n,

1M-chloroacetyl-M- (2-methoxy-1-methyl-yl) -2-ethyl-6-methylaniline,

M- (2-ethoxyethyl) -M-chloroacetyl-2, b-diethyleniline,

M-chloroacetyl-M- (2-p-propoxyethyl) -2-ethyl-6-methylaniline,

M-chloroacetyl-M- (2-p-prog10xyethyl) -2, 6-diethylaniline.

PRI me R 1. Obtaining 2-chloro-5 / -M- (1 cyano-cyclopentyl M-methyl-carbamoyl / 3-trifluoromethyl-thiazole

CF

3 gt

Nys

C1

with

-NX

CN

sn Solution of 112.5 g of 2-chloro-4-trifluoromethyltisol-5-carboxylic acid chloride (0.45 mol) is added to 200 ml of acetonitrile, at 0 °, a mixture of 55.9 g of 1-cyano-1-methylamino-cyclopentane is instilled ( 0.45 mol) and 46.0 g of triethylamine (0.45 mol). The amine hydrochloride precipitates. The suspension is stirred overnight at room temperature and then mixed in 2 liters of water.

The precipitated oil was taken up in ethyl acetate, dried over sodium sulfate and the solvent was distilled off under reduced pressure. The residue is crystallized by stirring with ether. Receive

colorless crystals. Melting point 134-136 ° C: yield 125 g (83% of theory).

Similarly, for this example receive are given in table. 1 amides of thiazole-5-carboxylic acid.

Compounds of the Invention

.RI

CF3 T-T-CO-N. C1

and H in

(I)

Table 1

.RI

-N. R

and H in

Biological examples.

The ability of the compounds of formula I to protect cultivated plants from the phytotoxic effect of potent herbicides can be seen from the following example. In the description of the experiments, the compounds of formula I are called antidotes or antidotes.

PRI me R 2. Experience with the herbicide and antidote in corn.

The herbicide and antidote are applied together as a mixture from the tank in a pre-emergence process.

Plastic containers (25 cm long x 17 cm wide and 12 cm high) are filled with sandy loam and seeds of LG 5 maize are sown. After coating the seeds, the substance tested as an antidote along with the herbicide is sprayed as a mixture from the reservoir onto the soil surface. 21 days after application, the protective effect of the antidote is evaluated as a percentage. In this case, plants treated with one herbicide (without protective action) and completely untreated control plants (100% protective effect) serve as a reference.

The tested compounds reduce the harmful effects of the herbicide to such an extent that no longer affects the crop,

PRI me RZ. Experience planted in water

Rice-Protective Action a

Continuation of table 1

The antidote and herbicide are applied as a mixture from the reservoir before germination;

Rice seeds are pre-soaked in water for 44 hours at 30 ° C.

Then, 500 ml plastic pots are filled up to two cm below the edge with sandy loam. The herbicide N-chlorocetyl-G2-propoxyethyl) -2,6-diethylaniline at a concentration of 250 g of active substance per hectare together with the substance tested as an antidote at a concentration of 1500 g of active substance is sprayed onto the soil surface.

Then pre-soaked seeds are planted on the marshy surface of the soil.

The earth is kept moist and the water level is gradually increased according to rice growth. 18 days after application of the drug, the protective effect of the antidote in percent is evaluated. In this case, the plants treated with one herbicide and completely untreated control plants are used as the basis. The protective effect is the difference between the damage that the plants treated with one herbicide suffer and the damage that the treated plants herbicide and antidote of the plant. The results are summarized in table 2.

Table 2

about

38

38

fifty

38

PRI me R 4. Experience with corn.

The herbicide and antidote are applied as a mixture from the reservoir before germination. To verify the antidote effect, corn seeds (varieties LG-9) are planted in pots of 9 cm diameter in the ground. Plants are cultivated in a greenhouse under suitable temperature and light conditions. Watering and fertilizing plants is carried out as needed.

The antidote is applied as a mixture from the reservoir together with the herbicide at a rate of water consumption of 550 l / ha in a pre-emergence process. The herbicide used was

The protective effect of the antidotes according to the invention in relation to corn

P rimerb. Experience millet and corn. The herbicide and antidote are applied as a mixture from the reservoir in a pre-emergence process.

To check the antidote effect, the seeds of sorghum (millet cultivar Funk G-623) and corn (varieties Blitzard) are grown in pots with a diameter of 11 cm in the ground. Cultivation of plants takes place in a greenhouse under suitable conditions of temperature and light. Watering or fertilizing plants is done as needed. The cultivation of Echlnochloa (weed) is carried out in the same way. The application of the antidote is carried out as a mixture from the tank together with the herbicide at a rate of water consumption of 550 l / ha in a pre-emergence process. The herbicide used is Y- (2-methoxy-10

M- (2-methoxy-1-methylzyl) -Y-chloroacetyl-2-ethyl-6-methylaniline (1) at a rate of 8 kg / ha. The antidote of the invention was mixed at a rate of 1.5 kg / ha. To determine the effect, after 21 days the total damage (phytotoxicity) of the plants was evaluated (% phyto, 0% phyto no damage, as untreated control plants., 100% phyto total damage). From the difference in damage when treated with one herbicide and a combination of herbicide + antidote, the following is obtained. 3 protective effect in%,

Table 3

methylethyl) -M-chloroacetyl-2-ethyl-6-methyl-aniline, metolachlor (1) or M- (isopropyl) -M-chloroacetyl-3,3,5-trimethyl-cyclohex-1-enamide. Trimexachlor (2) at the indicated flow rates as 1/4.

To determine the protective effect after 21 days (Table 5), we evaluate the total damage (phytotox) on the plants (0% phyto-no damage, like untreated control plants, 100% phyto-complete damage). From the phyto difference when treated with a single herbicide and a combination of herbicide + antidote, the protective effect shown in Table 4 is obtained in%.

Table 4

PRI me R 6. Experience with millet.

The herbicide and antidote are applied as a mixture from the reservoir in a pre-emergence process.

To test the antidote effect, sorghum seeds (Funka G-623) are planted in pots 9 cm in diameter in the ground.

Cultivation of plants takes place in a greenhouse under suitable conditions of temperature and light. Watering or fertilizing plants is done as needed.

The application of the antidote is carried out as a mixture from the reservoir together with the herbicide at a rate of water consumption of 550 l / ha in a pre-emergence process. M- (2-methoxy-1-methi) is used as the herbicide. Continuation of Table 4

5

ethyl) -M-chloroacetyl-2-ethyl-6-methyl-aniline (metolachlor) at a consumption rate of 1.5 kg / ha. The antidote of the invention is also added at a rate of 1.5 kg / ha.

To determine the protective effect, after 21 days, the total damage (phytotox) on the plants is evaluated (0% phyto-no damage, like untreated control plant, 100% phyto-complete damage). From the phyto difference when treated with a single herbicide and a combination of herbicide + antidote, the following is obtained. 5 protective action.

The protective effect of the antidotes according to the invention in relation to millet

Note er 7. Experience with rice.

The antidote and herbicide are applied in a pre-emergence process as a mixture from a reservoir.

To test the antidote effect, rice seeds are planted in pots of 9 cm diameter in the ground. Cultivation of plants takes place in a greenhouse under suitable conditions of temperature and light. Watering and fertilizing is carried out in plants as needed.

The application of the antidote is carried out as a mixture from the tank together with the herbicide at a rate of water consumption of 550 l / ha c. pre-emergence method (rge). As the herbicide, either M - (2-label) is used. The protective effect of the antidotes according to the invention in relation to rice

An example. Experience with different varieties of rice and weeds.

The antidote and herbicide are applied as a mixture from the reservoir in a post-emergence method.

To test the antidote effect, the seeds of 8 rice varieties are planted in pots with a diameter of 11 cm in the ground. Cultivation of plants is carried out in a greenhouse under suitable conditions of temperature and light. Horticulture or fertilizer is produced in plants as needed. Sorn Ki Echinochloa,

Table 5

si-1-methylethyl) -M-chloroacetyl-2-ethyl-6-methyl-anilide, Metolachlor (1), or M- (2-methoxy-ethyl-phenylsulfonylE-M - b-dimethoxy-1, 3,5-triazin-2-yl) -urea (4) at

specified rate of consumption. The antidote of the invention is admixed at a rate of 1.5 kg / ha for herbicide 1 or 30-60 g / ha for herbicide 4. To determine the protective effect, the total is evaluated after 21 days

damage (phytotox) on plants (0% phyto no damage, like untreated control plants, 100% phyto full damage). From the phyto difference when treating with a herbicide alone and with a combination of herbicide + antidote, the protective effect given in Table 6 is obtained.

Table 6

Rottbocllia, Dlgitavla grow in the same way.

The application of the antidote is carried out as a mixture from the reservoir together with the herbicide at a rate of water consumption of 550 l / ha in the post-emergence method (post). As a herbicide, K2-methoxyethylphene. Sulfonite} - N - (4,6-dimethoxy-1,3,5-triazin-2-yl) -urea.Nu (4) or 2P $ -enantiomer of complex propynyl is used to spray plants - 2- / 4- (5-chloro-3-fluoro-pyridin-2-yloxy) -phenoxy / -propionic acid ester (5)

at the indicated rate of consumption. Antidote No. 1.040 is added at the indicated rate of application. To determine the protective effect, 21 days after the application of the herbicide, the total damage (phytotox) on the plants is evaluated (0% phyto no damage,

Table Protection of rice plants from the harmful effects of herbicides

as untreated control plants, 100% phyto complete damage). From the phyto difference when treated with a single herbicide and a combination of herbicide + antidote, the following is obtained. 7 protective action

moist marshy soil (clay with sand) in plastic containers (area 4 x 9 cm; volume 500 ml). The herbicide M-chloracetyl-M- (2-propoxyethyl) -2,6-diethylaniline at a concentration of 500 and 1000 g of active substance per hectare, and the tested antidote at concentrations of 125, 250 and 500, respectively, 250, 500 and 1000 g the active substance per hectare is sprayed together as a tank mixture onto the surface of the soil.

The soil is kept wet and the water level rises with the growth of rice plants. Plant damage scores Table 8

The protective effect of antidotes according to the invention

0

applied 21 days after application of test substances and is recorded as a percentage. Plants that were only treated with the herbicide and plants that were not treated or damaged were used as controls for evaluating the protective effect. A protective effect is the difference between damage to plants that have only been treated with a herbicide and damage to plants that have been treated with a herbicide and an antidote. The results are summarized in the table below. 8.

nineteen

Continuation of the table, 8

21

Continuation of the table. 8

Continuation of the table. 8