Potassium salt of 2-chloro-n-[(4-methoxy-6-methyl-1,3,5-triazine-2 - yl)aminocarbonyl]benzosulfimide and method of controlling undesirable vegetation

 

(57) Abstract:

Potassium salt of 2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazine-2-yl)aminocarbonyl] benzosulfimide is used as a herbicide on flax, both individually and jointly with other herbicides, for example Targ-super and 2M-4. The specified salt use in controlling undesirable vegetation in crops of flax in the amount of not more than 5 g/ha 2 c. and 2 C.p. f-crystals, 9 PL.

The invention relates to chemical means of weed control in crops based on derivatives sulfonilmocevina, in particular salts of 2-chloro-N-/(4-methoxy-6-methyl-1,3,5-triazine-2-yl) aminocarbonyl/benzosulfimide(chlorsulfuron) and specifically to its potassium salt of formula I:

< / BR>
The invention relates also to a method of controlling undesirable vegetation in crops of flax by processing plants weed-killing drug on the basis of salts of formula I, as well as its mixture with other herbicide-active compounds, for example with dimethylamine salt of 2-methyl-4-chlorophenoxyacetic acid.

It is known the use of the herbicide N-substituted nitrogen-containing heterocyclic derivative sulfonylureas total FD is from, W is oxygen, and its sodium, potassium, calcium, 2-chloroethylamine salt in the amount of 0.005-2.0 kg/ha (patent USSR N 1435141).

Of salts chlorsulfuron, which is also described in this patent is characterized by sodium and calcium salts are used at a dose of 0.005 kg/ha according to the current matter.

Herbicide action described compounds, including salts, apply to weeds in crops of cereals, in particular wheat.

Known herbicide compositions based on salts of sulfonylureas of the General formula III:

< / BR>
where M is ammonium, substituted ammonium, alkali metal (sodium) ions and carbocyclic and inorganic acids (U.S. patent N 4936900).

Potassium salt of chlorsulfuron none of the known sources of information are not described not described.

Known drug use clay in the form of a 75% dry fluid suspension (active substance - chlorsulfuron-2-chloro-N-(4-methoxy-6-methyl-1,3,5-triazine-2-yl)-aminocarbonyl /benzosulfimide) as a herbicide on flax at a dose of 13 to 20 g/ha (List of chemical and biological means of pest control, plant diseases and weeds, plant growth regulators and Fermo is, Plant protection, No. 3, 1993 ) or at a dose of 10 - 15 g/ha of nutrient content (N.N. Melnikov and others, Handbook, Pesticides and plant growth regulators. Moscow, "Chemistry", 1995, S. 189).

In order to increase the effectiveness of the herbicide 2-chloro-N-/(4-methoxy-6-methyl-1,3,5-triazine-2-yl)aminocarbonyl/benzosulfimide in flax crops received its potassium salt of formula I.

Compound I can be obtained in a known manner from 2-chloro-N-/(4-methoxy-6-methyl-1,3,5-triazine-2-yl)aminocarbonyl/benzosulfimide(chlorsulfuron) and potassium hydroxide.

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

The use of potassium salt of chlorsulfuron in the cultivation of flax ensured in comparison with glenum a higher economic effect: herbicide activity increased by 4-19% depending on the type of weed, increased harvest flax seed and flax straw, as well as improved quality of flax straw. Moreover, it is noted samitee effect of the drug against diseases of flax (Anthracnose, Palio, polvorosa).

Potassium salt of chlorsulfuron effective against a wide variety of plants, SAARC field (Spergularia campestris A. ), chamomile odorless (Matricaria inodora L. ), chamomile (ordinary, wild) (M. chamomila L.), chamomile scent (American/) (M. matricaria des (Less.)P.), Popovka field (Anthemis arveusis L.), Popovka smelly (dog Daisy) (A. cotula L), Popovka dye (A. tinetoria L.), wild radish (Raphanus raphamistrum L.), common winter cress (Barbarea Vulgaris R. Br.), shepherd's purse (Capsellabursa pastoris Med.), the field field (Tklaspiarvense L. ), starwort average) (woodlouse) (Stellaria media Vill), starwort grass (S. graminea L. ), pikulnik (medovnik) ordinary (barbed) (Galeopsis tetrahit L. ), pikulnik beautiful (a prominent, noticeable, "Zebra") (G. speciosa Mill), pikulnik lednikoviy (CABRI) (G. ladanum L. ), white dead-nettle (deaf nettle) (Lamium album L.), purple dead-nettle (L. purpureum L. ), spotted dead-nettle (L. maculatum L.), dead-nettle stereohedra (L. amplexicaule L.), white pigweed (Chenopodium album L.) and other dicotyledonous plants.

The possibility of using the drug in a mixture with other herbicides: 2M-4X, Targa super, Naboo, lontrel, fungicides: ronilan, folicur, tilt, Benet and others, fertilizers: boric acid, zinc sulfate, urea.

In the application for French patent N 7834783, publication number 2440158 described among many other herbicide composition based chlorsulfuron and 2-methyl-4-chlorophenoxyacetic sour the public 300 - 2000 and 300 to 1000 g/ha of nutrient content

The tests have shown that when processing flax mixture of potassium salt of formula I, 2M-4 good result can be obtained if the potassium salt of chlorsulfuron be applied in doses of 1 to 5 g/ha of nutrient content, and 2M-4 at doses of 300 - 500 g/ha of nutrient content

The use of 2M-4 on the flax at the rate of 0.45 to 1.0 kg/ha is known (N. N. Melnikov and other Reference: the Pesticides and plant growth regulators, M., "Chemistry", 1995, S. 112).

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

To 10 g (0,028 mol) of 2-chloro-N-/(4-methoxy-6-methyl-1,3,5-triazine-2-yl)aminocarbonyl/benzosulfimide under stirring is added dropwise to 3.9 g (0,028 mol) of 40% potassium hydroxide. The mixture is then stirred for 5 minutes and the resulting pasty mass is dried at a temperature of 50oC. Obtain 11.1 g (98%) of the potassium salt of 2-chloro-N-/(4-methoxy-6-methyl-1,3,5-triazine-2-yl)aminocarbonyl/benzosulfimide.

Option 2.

To 10 g (0,028 mol) of 2-chloro-N-/(4-methoxy-6-methyl-1,3,5-triazine-2-yl)aminocarbonyl/benzosulfimide add 100 g of ethanol and the suspension is stirred and then added 1.7 g (0,028 mol) of 90% potassium hydroxide. The resulting mixture is heated under SUP>oC, the precipitate is filtered off and dried at a temperature of 50oC. Receive 8 g (80%) of the potassium salt of 2-chloro-N-/(4-methoxy-6-methyl-1,3,5-triazine-2-yl)aminocarbonyl/benzosulfimide.

Physico-chemical properties of the substance:

Molecular weight: 395,5

Melting point: 176oC (decomposition)

Solubility, % at 20oC: in water: 7 - 9, in ethanol: 1,6,

in benzene: 1,3, acetone: 0,3.

Elemental analysis data:

Calculated,%: C 36,4 Cl H 2,8 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

Data PMR: Range AMP potassium salt of chlorsulfuron (solution DMCO-d6) represents a range of individual compounds and consists of a singlet CH3group (2,20 M. D.), singlet OCH3group (3.75 M. D.), cameratoting multiplet, aromatic protons (7,2 - 8,0 m D.) and singlet NH-proton (8,9 M. D. ). In the spectrum there is no second NH-proton, which indicates the formation of the potassium salt of chlorsulfuron.

Example 2. The definition of a weed-killing activity of the potassium salt of chlorsulfuron.

The substance was tested in the form of 85% of the energy of water-soluble granules at a dose of 1 to 5 g/ha according to the current matter, the rate of fluid flow 200 l/ha

Were obrycki is - may. The seeding rate is 20 million viable seeds per 1 hectare.

The processing of crops was carried out after germination phase herringbone linen, at the height of weeds 2 to 5, see

Accounting contamination: 1st period - before treatment with the herbicide (June), 2nd period - 20 days after herbicide treatment (July), 3rd term - before the harvest flax (August) was conducted in accordance with the "guidelines for field testing of herbicides in crop production", M, 1981, S. 46.

Method of harvest: harvesting flax from across an area, polaneczky threshing, cleaning, weighing with the terms of the standard condition the flax was conducted in accordance with the "guidelines for conducting field experiments with flax". UniLine, 1979, S. 72.

Was also conducted comparative tests of known drug clays in the form of a 75% dry fluid suspension, and the mixture of the potassium salt of chlorsulfuron with known herbicide against grass weeds (cynodon, wheat grass) Targ-super in the form of a 5% emulsion concentrate (D. C. - (R)-2-/4-(6-chlorination-2-yloxy)phenoxy/propionic acid ethyl ester) (N.N. Melnikov and others, Handbook, Pesticides and plant growth regulators. M., "Chemistry", 1995, S. 179).

The Checkpoints For Important Locations The Example 3. The fungicidal activity of the potassium salt of chlorsulfuron.

The fungicidal activity of the potassium salt of chlorsulfuron and similar clay is shown on the example of common disease of flax antracnose.

Accounting defeat flax conducted during budding flowering and before the harvest of flax.

Plants pulled from the soil and analyzed their infection diseases and calculated the percentage of infection (see guidance on phytopathological works with flax-fiber. M., "Kolos", 1969, S. 13-21).

Example 4. The definition of a weed-killing activity of the mixture of the potassium salt of chlorsulfuron and 2M-4.

To enhance herbicide activity of the potassium salt of chlorsulfuron against dicotyledonous weeds used a mixture thereof with a known herbicide 2M-4.

Just before applying the herbicide was mixed with water potassium salt of chlorsulfuron in the form of water-soluble granules (dose 1 - 5 g/ha of nutrient content) and 2M-4X as 59% aqueous concentrate his dimethylamine salt (dose 300 - 500 g/ha of nutrient content).

Methods of herbicide treatment and consideration of the results was carried out analogously to example 2.

The results of the tests are presented in tables 8, 9.

1. Potassium is iby undesirable vegetation in crops of flax by processing plants sulfonylurea derivatives, characterized in that as a function of sulfonylurea use potassium salt of 2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazine-2-yl)aminocarbonyl] benzosulfimide formula

< / BR>
not more than 5 g/ha

3. The method according to p. 2, characterized in that the potassium salt of 2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazine-2-yl)aminocarbonyl] benzosulfimide share with ethyl ether (R)-2-[4-(6-chlorination-2-yloxy)-phenoxy] propionic acid at the ratio of 1 : 25.

4. The method according to p. 2, characterized in that the potassium salt of 2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazine-2-yl)aminocarbonyl] benzosulfimide share with dimethylamine salt of 2-methyl-4-chloro-phenoxyalkanoic acid in a ratio of components 1 to 5 : 300 - 500.

 

Same patents:

The invention relates to a new derived arylsulfonyl-triethynylbenzene formula I

which can find application in agriculture as a herbicide for weed control in cereal crops and flax, as well as herbicide composition based on it

The invention relates to a new cyclopropylamino-1,3,5-triazines and their salts of General formula

< / BR>
in which R1- alkyl, cycloalkyl, alkylsilanes; R2bis (2-hydroxyethyl)amino, 3-hydroxy-1-azetidine, 3-methoxy-1-azetidine, 3-oxo-1-azetidine, morpholine-, 4-hydroxypiperidine, thiomorpholine-, S-oxide-thiomorpholine-, S, S-dioxide-thiomorpholine-, 3-thiazolidine, S-oxide-3-thiazolidine, S, S-dioxide-3-thiazolidine or 8-oxa-3-azabicyclo/3,2,1/ Oct-3-yl

The invention relates to chemical means of plant protection, in particular by preparative form known herbicide

The invention relates to new pyridinesulfonamide General formula I or their acceptable for agriculture salts, have a weed-killing activity, as well as to a method for their production and compositions for combating the growth of unwanted vegetation

The invention relates to new derivatives of arylsulfonamides, namely, potassium salt of N-(4,6-dimethylpyrimidin-2-yl)-N'-/2- (methoxycarbonyl)phenylsulfonyl/urea (potassium salt of sulfometuron-methyl), which may find application in forestry planting cedar (Siberian pine, Korean) and non-agricultural land use as a herbicide

The invention relates to chemical means of weed control in cereal crops, namely, compositions containing the derivatives of the sulfonylureas, have a weed-killing activity, or their salts in the mixture with the herbicide action derived organic acids or their salts, namely, the herbicide composition based on a mixture of ammonium salt of 2-chloro-N-/(4-methoxy-6-methyl-1,3,5-triazine-2-yl) aminocarbonyl/-benzosulfimide (chlorsulfuron) formula

,

and ammonium salts of 2-methoxy-3,6-dichlorobenzoyl acid(dicamba) formula

,

where

R1- CH3or C2H5;

R2- H or CH2CH2OH

Herbicide tool // 2106089
The invention relates to the field of plant protection, in particular to the herbicide agent, consisting of two active substances

The invention relates to the compound N-pyridylsulfonyl-N'-pyrimidinylidene formula 1

< / BR>
where R1denotes methyl or methoxy and R2denotes hydrogen or methyl; compounds and salts of these compounds with amines, bases, alkali or alkaline earth metal or Quaternary ammonium bases have good herbicide and regulating plant growth properties during selective use before and after germination

FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention describes a synergistic composition of herbicides comprising components (A) and (B) wherein (A) represents herbicide taken among the group of the formula (I):

wherein R1 means (C1-C4)-alkyl; R2 means (C1-C4)-alkyl; R3 means hydrogen atom; X and Y mean (C1-C4)-alkoxy-group; (B) represents one or two herbicides taken among the group of compounds or their acceptable forms: alachlor, metolachlor, acetochlor, dimetenamide, atrazine, cyanasin, metribusin, fluthiamide, nicosulfuron, rimsulfuron, primisulfuron, pendimetalin, sulcotrion, dicamba, mesotrion, isoxachlortol, metosulam, anilofos, fenoxaprop-ethyl, setoxydim, diclofop-methyl, MCPA, bromoxynil, pyridat, clopyralid, iodosulfuron-methyl, ethoxysulfuron, amidosulfuron, gluphosinat-amminium, isopropylammonium-glyphosate, imasetapir wherein components (A) and (B) are taken in the effective doses. Also, invention describes a method for control of weeds by using above indicated herbicide composition. Invention provides the development of the synergistic herbicide composition eliciting high activity.

EFFECT: improved method for control, valuable properties of composition.

6 cl, 26 tbl, 3 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: claimed mixture from herbicides and antidotes contains (A) herbicidically active substance based on phenylsulfonylureas of formula I and salts thereof (in formula R1 is hydrogen or C1-C6-alkyl; R2 is C1-C3-alkyl; R3 is C1-C3-alkoxy; R4 is hydrogen or C1-C4-alkyl; Hal is fluorine, chlorine, bromine, or iodine); and (B) antidote of formulae II or III , wherein X is hydrogen, halogen, C1-C4-alkyl; C1-C4-alkoxy, nitro or C1-C4-haloalkyl; Z is hydroxyl, C1-C8-alkoxy, C3-C6-cycloalkoxy, C2-C8-alkenyloxy, C2-C8-alkynyloxy; R5 is C1-C2-alkandiyl chain optionally substituted with one or two C1-C4 alkyl residues or (C1-C3-alcoxy)carbonyl; W is bivalent heterocyclic residue; n = 1-5; in weight ratio herbicide/antidote of 100:1-1:100. Also disclosed is method for protection of cultural plants against phytotoxic side effect of herbicidically active substance of formula I. Claimed method includes antidote application of formulae II or III on plant, plant parts, plant seeds or seeding areas before or together with herbicidically active substance in amount of 0.005-0.5 kg/hectare in weight ratio of 100:1-1:100.

EFFECT: mixture for effective selective weed controlling in cultural plant, particularly in maize and grain cultures.

8 cl, 2 ex, 7 tbl

FIELD: agriculture, in particular herbicide compositions.

SUBSTANCE: invention relates to weed controlling method for tolerant grain crops using (A) road spectrum herbicides selected from group (A1) glufosinate (salt) and related compounds; (A2) glyphosate (salt) and related compounds; and (B) one or more herbicides selected from group containing (B1) herbicides selectively effecting in grain crops especially against monocotyledonous weeds effecting on folia and/or soil (residual benefit); or (B2) herbicides selectively effecting in grain crops against monocotyledonous or dicot weeds effecting especially on folia; or (B3) herbicides selectively effecting in grain crops against monocotyledonous or dicot weeds effecting on folia or soil; or (B4) herbicides selectively effecting in grain crops against monocotyledonous or dicot weeds effecting on folia; wherein components (A) and (B) are used in synergic ration. Also are described herbicide compositions containing (A1) ) glufosinate (salt) and related compounds and herbicide from group (B); as well as herbicide compositions containing(A2) glyphosate (salt) and related compounds and herbicide from group (B); wherein components (A) and (B) are used in synergically effective ration.

EFFECT: effective controlling of weeds in grain crops.

6 cl, 70 tbl, 3 ex

FIELD: organic chemistry, agriculture, herbicide composition.

SUBSTANCE: invention relates to herbicide composition, containing conventional inert additives and mixture of a) herbicidically effective amount of substance satisfying the formula I [in formula R1 and R3 are the same or different C1-C4-alkyl; R4 and R5 together form groups of formulae: -C-R6(R7)-O-C-R8(R9)-C-R10(R11)-C-R12(R13)-(Z1), -C-R14(R15)-C-R16(R17)-O-C-R18(R19)-C-R20(R21)-(Z2), or -C-R22(R23)-C-R24(R25)-C-R26(R27)-O-C-R28(R29)-(Z3), wherein each R6-R29 is hydrogen; G is hydrogen or -C(X2)-X3-R31; X2 and X3 independently are oxygen; R31 is C1-C10-alkyl]; b) herbicidic synergic amount of at least one herbicide selected from group containing sulfonylureas, phenoxyacetic acids, as well as florsulam, tralcoxidim, klodinafol-propargil, phenoxaprop-P-ethyl, trifluramine, pendimethaline, picolinafen, etc. Composition also may contain safety effective amount of protective agent, such as chloquintocet-mexyl and additive (e.g., mineral oil or C8-C22-fat acid alkyl esters) in amount of 0-2 mass %. Also disclosed is method for selective controlling of weeds and grassy plants in cultural plants by treatment of cultural plants, seeds or seedlings thereof, or vegetation area thereof with claimed composition.

EFFECT: effective composition and method for weed controlling.

5 cl, 11 tbl, 7 ex

FIELD: agriculture, in particular method for controlling of weeds.

SUBSTANCE: claimed method for controlling of weeds in tolerant maize cultures includes application of composition comprising (A) road spectrum herbicide from group (A1) glufosinate (salt) and analogs, (A2) glyfosate (salt) and analogs; (B) one or more herbicides from group (B1) cyanazin, alachlor, nicosulfurone, rimsulfurone, sulkotrion, mesotrion, and penthoxamid; (B2) pendimethalyne, methosulam, isoxaflutol, metribuzin, chloransulam, flumetsulam, linuron, florasulam, and isoxachlorotol; and (B3) bromoxinyl, chlorpyralid, tifensulfuron, MCPA (2-methyl-4-chlorophenoxyacetic acid), halosulfuron, and sulfosulfuron, wherein (A) and (B) components are in synergic effective ration. Also disclosed are herbicidal compositions including compound from group (A1) or )F2) and herbicide from group (B).

EFFECT: effective controlling of weeds in tolerant maize cultures.

6 cl, 55 tbl, 3 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to new substituted thienyl(amino)sulfonylureas of formula I ,

wherein A represents nitrogen or methane; Q represents direct bond or imino; R1 represents fluorine, chlorine, bromine, unsubstituted C1-C4-alkyl, C1-C4-alkoxyl optionally substituted with halogen, unsubstituted C1-C4-alkylthio, or di(C1-C4-alkyl)amino; R2 represents hydrogen or C1-C4-alkyl. Compounds of present invention are useful as herbicide agents.

EFFECT: new compounds with herbicide activity.

5 cl, 11 tbl, 5 ex

FIELD: agriculture, in particular herbicide compositions.

SUBSTANCE: invention relates to weed controlling method for tolerant cotton crops using (A) road spectrum herbicides selected from group (A1) glufosinate (salt) and related compounds; (A2) glyphosate (salt) and related compounds; and (B) herbicides selected from group containing diurone, trifluraeline, linuron, and pendimethalin; lactofen, oxyfluoren, bispiribac and salts thereof, pyrithiobac and salts thereof; setoxydim, cyclosidim, and cletodim; wherein components (A) and (B) are used in synergistically effective ratio. Also are described herbicide compositions containing compound from group (A1) or (A2) and herbicide from group (B).

EFFECT: effective controlling of weeds in cotton crops.

9 cl, 12 tbl, 3 ex

Up!