RU2125994C1 - 2-chloro-n-[(4-methoxy-6-methyl-1,3,5-triazine-2-yl)-amino- -carbonyl]-benzenesulfamide potassium salt, and method of control over weed - Google Patents

Abstract

FIELD: organic chemistry, agriculture. SUBSTANCE: invention relates to 2-chloro-N-[(4-methoxy-6- -methyl-1,3,5-triazine-2-yl)-aminocarbonyl] -benzenesulfamide that is used as a herbicide in flax culturing or in combination with other herbicides, for example, targa-super and 2M-4X. The salt is used as an agent for control weed in the amount not more 5 g/ha. EFFECT: enhanced effectiveness. 4 cl, 9 tbl, 4 ex

Description

Изобретение относится также к способу борьбы с нежелательной растительностью в посевах льна путем обработки растений гербицидным препаратом на основе соли формулы I, а также ее смеси с другими гербицидно-активными соединениями, например с диметиламинной солью 2-метил-4-хлорфеноксиуксусной кислоты.The invention relates to chemicals for controlling weeds in crops of crops based on derivatives of sulfonyltriazinyl urea, in particular to salts of 2-chloro-N - / (4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl / benzenesulfamide (chlorosulfuron) and specifically to its potassium salt of the formula I:

The invention also relates to a method for controlling undesirable vegetation in flax crops by treating plants with a herbicidal preparation based on a salt of formula I, as well as its mixture with other herbicidal active compounds, for example, dimethylamine salt of 2-methyl-4-chlorophenoxyacetic acid.

где наряду с другими радикалы могут иметь следующие значения:

X,V-метил, метокси, А-азот, W-кислород, а также его натриевые, калиевые, кальциевые, 2-хлорэтилтриэтиламмониевые соли в количестве 0,005-2,0 кг/га (патент СССР N 1435141).It is known to use an N-substituted nitrogen-containing heterocyclic sulfonylurea derivative of the general formula II as a herbicide:

where, along with other radicals, they can have the following meanings:

X, V-methyl, methoxy, A-nitrogen, W-oxygen, as well as its sodium, potassium, calcium, 2-chloroethyltriethylammonium salts in an amount of 0.005-2.0 kg / ha (USSR patent N 1435141).

 Of the salts of chlorosulfuron, which is also described in this patent, sodium and calcium salts are characterized, used at a dose of 0.005 kg / ha for the active substance.

 The herbicidal effect of the described compounds, including salts, extends to weeds in crops of cereal crops, in particular wheat.

где М - аммоний, замещенный аммоний, щелочной метал (натрий) и ионы карбоциклических и неорганических кислот (патент США N 4936900).Known herbicidal compositions based on sulfonylurea salts of the general formula III:

where M is ammonium, substituted ammonium, an alkali metal (sodium) and ions of carbocyclic and inorganic acids (US patent N 4936900).

 The potassium salt of chlorosulfuron is not described or characterized in any of the sources of information known to us.

 It is known to use a clay preparation in the form of a 75% dry fluid suspension (the active substance is chlorosulfuron-2-chloro- / N- (4-methoxy-6-methyl-1,3,5-triazin-2-yl) -aminocarbonyl / benzene sulfamide) as a herbicide on flax in a dose of 13 - 20 g / ha (List of chemical and biological agents for controlling pests, plant diseases and weeds, plant growth regulators and pheromones approved for use in agriculture, including farming, forestry and communal farms for 1992 - 1996. Plant protection, N 3, 1993) or at a dose of 10 - 15 g / ha d. (NN Melnikov et al. Handbook, Pesticides and plant growth regulators. Moscow, Chemistry, 1995, p. 189).

 In order to increase the efficiency of the herbicidal action of 2-chloro-N - / (4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl / benzenesulfamide, its potassium salt of formula I was obtained in flax crops.

 Compound I can be prepared in a known manner from 2-chloro-N - / (4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl / benzenesulfamide (chlorosulfuron) and potassium hydroxide.

 Compound I was tested as a herbicide on flax in the form of an aqueous solution of 85% water-soluble granules to which a surfactant was added.

 The use of the potassium salt of chlorosulfuron in the cultivation of flax provided a higher economic effect in comparison with clay: the herbicidal activity increased by 4-19% depending on the type of weed, the yield of flax seeds and flax straw increased, and the quality of flax straw improved. In addition, the protective effect of the drug against flax diseases (anthracnose, paslio, polysporosis) was noted.

Chlorosulfuron potassium salt is effective against a wide range of plants that clog flax crops:
field torus (Spergula arvensis L.), linseed torica (S.linicola L.), large torica (S. maxima Weihe), field torica (Spergularia campestris A.), odorless chamomile (Matricaria inodora L.), medicinal chamomile (ordinary , wild) (M. chamomila L.), odorous chamomile (American /) (M. matricaria des (Less.) P.), field umbilicus (Anthemis arveusis L.), smelly umbilicus (dog chamomile) (A.cotula L ), umbilical crayfish (A.tinetoria L.), wild radish (Raphanus raphamistrum L.), common colza (Barbarea Vulgaris R.Br.), shepherd’s bag (Capsellabursa pastoris Med.), field yarrow (Tklaspiarvense L.), star medium) (wood louse) (Stellaria media Vill), cereal starlet (S. graminea L.), Pikulnik (mellifer) ordinary (prickly) (Galeopsis tetrahit L.), Pikulnik beautiful (prominent, noticeable, "chaffinch") (G.speciosa Mill), Cistus pikulnik ("cabra") (G.ladanum L.), white cod (deaf nettle) (Lamium album L.), purple nettle (L. purpureum L.), speckled green nettle (L.maculatum L.), creeping nettle (L. amplexicaule L.), white gauze (Chenopodium album L.) and other dicotyledonous plants.

 The possibility of using the drug in a mixture with other herbicides: 2M-4X, Targa Super, Nabu, Lontrel, fungicides: Ronilan, Folicurum, Tilt, Benlat and others, fertilizers: boric acid, zinc sulfate, urea was revealed.

 French patent application No. 7834783, publication number 2440158, describes, among many others, a herbicidal composition based on chlorosulfuron and 2-methyl-4-chlorophenoxyacetic acid (2M-4X, MCPA). The recommended doses for chlorosulfuron are 20 to 240 g / ha, preferably 30 to 125 g / ha, for 2M-4X, respectively 300 to 2000 and 300 to 1000 g / ha ai.

 The tests showed that when processing flax crops with a mixture of potassium salt of the formula I 2M-4X, good results can be obtained if the potassium salt of chlorosulfuron is used in doses of 1 - 5 g / ha a.a., and 2M-4X - in doses of 300 - 500 g / ha a.v.

 The use of 2M-4X on flax at a consumption rate of 0.45 - 1.0 kg / ha is known (N. N. Melnikov et al. Reference: Pesticides and plant growth regulators, M., "Chemistry", 1995, p. 112).

 Example 1. Potassium salt of 2-chloro-N / (4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl / benzenesulfamide (Option I).

3.9 g (0.028 mol) are added dropwise to 10 g (0.028 mol) of 2-chloro-N - / (4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl / benzenesulfamide. ) 40% potassium hydroxide. Then the mixture is stirred for another 5 minutes and the resulting pasty mass is dried at a temperature of 50 ^o C. Receive 11.1 g (98%) of potassium salt of 2-chloro-N - / (4-methoxy-6-methyl-1,3, 5-triazin-2-yl) aminocarbonyl / benzenesulfamide.

 Option 2

To 10 g (0.028 mol) of 2-chloro-N - / (4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl / benzenesulfamide, 100 g of ethanol are added, the suspension is stirred and then 1, 7 g (0.028 mol) of 90% potassium hydroxide. The resulting mixture is heated with stirring to 55-60 ^o C and maintained at this temperature for 20 minutes. Then the reaction mass is cooled to 0 ^o C, the precipitate is filtered off and dried at a temperature of 50 ^o C. Get 8 g (80%) of potassium salt of 2-chloro-N - / (4-methoxy-6-methyl-1,3,5- triazin-2-yl) aminocarbonyl / benzenesulfamide.

Physico-chemical properties of the substance:
Molecular Weight: 395.5
Melting point: 176 ^o C (decomposed)
Solubility,% at 20 ^o C: in water: 7 - 9, in ethanol: 1.6,
in benzene: 1.3; in acetone: 0.3.

Elemental analysis data:
Calculated,%: C 36.4 H 2.8 Cl 9.0 N 17.7 S 8.1 O 16.2 K 9.8
Found%: C 35.8 H 2.9 Cl 9.2 N 17.3 S 8.0 O 16.3 K 10.3
PMR data: The AMP spectrum of the chlorosulfuron potassium salt (DMCO-d ₆ solution) is a spectrum of an individual compound and consists of a singlet of CH ₃ group (2.20 ppm) and a singlet of OCH ₃ group (3.75 ppm .), four-proton multiplet of aromatic protons (7.2 - 8.0 ppm) and a singlet of NH proton (8.9 ppm). There is no second NH proton in the spectrum, which indicates the formation of the potassium salt of chlorosulfuron.

 Example 2. Determination of the herbicidal activity of the potassium salt of chlorosulfuron.

 The substance was tested in the form of 85% water-soluble granules in a dose of 1 - 5 g / ha for the active substance, the working fluid flow rate of 200 l / ha.

Spraying of a plot of 25 m ^{2 was} carried out, the experiment was repeated 4 times. Flax cultivar - flax flax-Torzhok-4, sowing date - May. The seeding rate is 20 million germinating seeds per 1 hectare.

 Crop processing was carried out after germination in the flax herringbone phase, with weeds 2-5 cm high.

 Accounting for weediness: the first term - before treatment with the herbicide (June), the second term - 20 days after the treatment with the herbicide (July), the third term - before harvesting the flax (August) was carried out in accordance with the "Field Guidelines" the test of herbicides in crop production, "M., 1981, p. 46.

 Method of harvesting: flax harvesting from the entire accounting area, plow threshing, cleaning, weighing in terms of standard conditions for flax production was carried out in accordance with the “Methodological guidelines for conducting field experiments with flax”. VNIIILna, 1979, p. 72.

 Comparative tests of the well-known clay preparation in the form of a 75% dry fluid suspension, as well as a mixture of the potassium salt of chlorosulfuron with the well-known herbicide for controlling cereal weeds (porcini, wheatgrass) targa super in the form of a 5% emulsion concentrate (e. century - (R) -2- / 4- (6-chloroquinoxalin-2-yloxy) phenoxy / propionic acid ethyl ether) (NN Melnikov et al. Handbook, Pesticides and plant growth regulators. M., "Chemistry ", 1995, p. 179).

 The control option is sowing flax without weeding.

 The test results are presented in tables 1-5.

 Example 3. The fungicidal activity of the potassium salt of chlorosulfuron.

 The fungicidal activity of the potassium salt of chlorosulfuron and its clay counterpart is shown by the example of a common flax anracnose disease.

 Accounting for flax damage was carried out during the budding period of flowering and before harvesting flax.

 Plants are pulled out of the soil and their infection with diseases is analyzed and the percentage of infection is calculated (see Methodological instructions for phytopathological work with flax flax. M., Kolos, 1969, pp. 13-21).

 Example 4. Determination of the herbicidal activity of a mixture of potassium salt of chlorosulfuron and 2M-4X.

 To enhance the herbicidal activity of the potassium salt of chlorosulfuron against dicotyledonous weeds, its mixture with the known herbicide 2M-4X was used.

 Immediately before the use of the herbicide, the potassium salt of chlorosulfuron was mixed with water in the form of water-soluble granules (dose of 1-5 g / ha ai) and 2M-4X in the form of a 59% aqueous concentrate of its dimethylamine salt (dose of 300-500 g / ha AE).

 The method of processing the herbicide and the calculation of the results was carried out analogously to example 2.

 The test results are presented in tables 8, 9.

Claims (3)

1. The potassium salt of 2-chloro-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] benzenesulfamide of the formula

2. A method of controlling undesirable vegetation in flax crops by treating plants with a sulfonylurea derivative, characterized in that the potassium salt of 2-chloro-N - [(4-methoxy-6-methyl-1,3,5-triazine) is used as a sulfonylurea derivative -2-yl) aminocarbonyl] benzenesulfamide of the formula

in an amount of not more than 5 g / ha.  3. The method according to claim 2, characterized in that the potassium salt of 2-chloro-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] benzenesulfamide is used together with ethyl ether (R) -2- [4- (6-chloroquinoxalin-2-yloxy) -phenoxy] propionic acid in a ratio of 1: 25.  4. The method according to claim 2, characterized in that the potassium salt of 2-chloro-N - [(4-methoxy-6-methyl-1,3,5-triazin-2-yl) aminocarbonyl] benzenesulfamide is used together with a dimethylamine salt 2-methyl-4-chloro-phenoxyacetic acid with a component ratio of 1 to 5: 300 to 500.

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