2-[ 2,3,4-triple-substituted benzoyl]-1,3-cyclohexandione or their salts, herbicide composition and method of controlling undesirable vegetation

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

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).

Clumps of Russian centaury are treated with tank mixture comprising 1.8-2.4 l 2-ethylhexyl ether + Cynidone-ethyl, 0.012-0.015 kg Rimsulfone + thiphenesulfurone-methyl, and 57.6-147.6 L water in a rate of 60-150 L/ha in the weed budding-flowering period. Agent is prepared by consecutively adding mother liquors of herbicides to water followed by agitation for 20 min.

Sulfonylaminourea and phenoxyacetic acid derivatives-based herbicidal composition contains nonionic surfactant, anion-active surfactant sulfonol, kaolin as carrier, and carbon white. As sulfonylaminourea and phenoxyacetic acid derivatives it contains 3-(6-methyl-4-methoxy-1,3,5-triazinyl-2-)-1-(2-chlorophenylsulphonyl)urea and 2-methyl-4-chlorophenoxyacetic acid sodium salt, respectively. Additionally composition contains triethanolamine or diethanolamine, disubstituted potassium phosphate as stabilizer in the component ratio of (mass %): 2-methyl-4-chlorophenoxyacetic acid sodium salt 55-72; 3-(6-methyl-4-methoxy-1,3,5-triazinyl-2-)-1-(2-chlorophenylsulphonyl)urea 0.3-0.4; nonionnic surfactant 0.05-0.15; sulfonol 0.05-0.15; triethanolamine or diethanolamine 0.15-0.2; carbon white 0.37-1.5; disubstituted potassium phosphate 1.0-2.0; and balance: kaolin. Composition components are separately applied on carrier surface. More specifically triethanolamine or diethanolamine is separately mixed with kaolin; 3-(6-methyl-4-methoxy-1,3,5-triazinyl-2-)-1-(2-chlorophenylsulphonyl)urea, and carbon white are separately mixed with kaolin; disubstituted potassium phosphate, nonionic surfactant, and sulfonol are separately mixed with kaolin; and 2-methyl-4-chlorophenoxyacetic acid sodium salt also is separately mixed with kaolin. Mixtures are conditioned for 24 h at room temperature and then are blended to provide mentioned above component ratio in product.

Invention relates to selective herbicidal compositions, containing customary auxiliary substances, as well as: a) herbicidal effective amount of compound of formula I or agriculture acceptable salt thereof wherein R are independently C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₄-alcoxy-C₁-C₄-alkyl, or C₁-C₄-alcoxy-C₁-C₄-alcoxy-C₁-C₄-alkyl; m = 2; Q is group of formula wherein R₂₃ is hydroxyl and Y is C₁-C₄-alkylen bridge; and b) synergetically effective amount of one or more herbicides; and methods for controlling of undesired plants in tame cultures using the said composition. Also disclosed is composition containing customary auxiliary substances, as well as herbicidal and synergetically effective amount of 4-hydroxy-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]octo-3-ene-2-one of formula 2.2 and herbicidal antagonistically effective amount of antidote of formula 3.1. Compositions based on 4-hydroxy-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]octo-3-ene-2-one and herbicidal antagonistically effective amount of antidote, as well as methods for controlling of weeds and cereal grasses in tame cultures also are described.

Invention relates to herbicidal agent containing compound of general formula I wherein X represents residue X¹ or X² and Z, R¹ and R² are as defined in claim of invention, and additional active substance selected from group containing bromoxynil, dicamba, flufenacete, metolachlor, atrazine, pendimethaline, imazetapir, iodosulfuron, nicosulfuron, 2-amino-4-(1-fluoro-1-methyl)-6-(3-phenyl-1-cyclobuthyl-1-propylamino)-1,3,5-triazine and N-[(4,6-dimethoxy-pyrimidine-2-yl)-aminocarbonyl]-2-dimethylamino-carbonyl-5-formyl-benzenesulfonamide. Compound of formula I and additional active substance are taken in mass ratio of 1:20-10:1, respectively.

Invention describes a synergetic composition with the effective content of components (A) and (B) wherein (A) means herbicide chosen from the group of compounds of the formula (I): wherein R¹, R², R, X, Y and Z have values given in the invention claim or their salts; (B) means one or some herbicides among the following groups: (B1) selective herbicides with activity in some dicotyledonous cultures against monocotyledonous and dicotyledonous weeds; (B2) selective herbicides with activity in some dicotyledonous cultures against dicotyledonous weeds; (B3) selective herbicides with activity in some dicotyledonous cultures with preferable effect against monocotyledonous weeds. Also, invention describes a method for control against weeds using the proposed composition. Using the combination of proposed herbicides results to the synergetic effect.

Invention relates to herbicidal composition containing (A) mesotrion and (B) the second herbicide selected from amicarbazone, metribuzine, flumetsulfam, trifloxysulfuron, pyriphthalide, prosulfocarb or herbicidically active salts thereof in (A):(B) ratio from 32:1 to 1:3. Disclosed is method for controlling of undesired plants which includes application of herbicidically effective amount of said composition into locus with such plants.

Seeds are treated by spraying in leaf clamping step with titanium tetrachloride diluted in dimethylsulfoxide (DMSO). Concentration of DMSO is 0.1-2 %; titanium tetrachloride consumption is up to 50 g per 1 hectare of seeds. Ratio of titanium tetrachloride:dimethylsulfoxide is 100-200 l per 1 hectare. Treatment is carried out twice in vegetation period, namely the first treatment is carried out in leaf clamping step and the second one in 15-20 days before harvesting of root crops.

Method involves introducing into said weed locus combination of mesotrione and triazine, selected from the group consisting of atrazine, cyanazine, propazine, terbutilazine, trietazine, simazine and metribuzine. Mesotrione is introduced in an amount of from 20 to 210 g/hectare, triazine in an amount of from 0.1 to 2 kg/hectare.

Invention concerns new photoinitiators, method of their obtainment, compositions hardening with irradiation, and application of those compositions in coating preparation. Invention claims photoinitiators of formulae I , where R₁, R₂, R₃ and R₄ are independently C₁-C₈alkyl or benzyl; or R₁ and R₂ together and/or R₃ andR₄ together are cyclohexyl; R₅ is hydrogen; A is OH, Br, -O-C₁-C₁₂alkyl, -O-R₇, where R₇ is linear or forked C₂-C₂₁hydroxyalkyl carbon chain interrupted by 1 to 9 oxygen atoms; or -NR₈R₉, where R₈ and R₉ are independently C₁-C₂₁alkyl or C₂-C₄alkyl substituted by one or more OH groups; A' is -O-; X and Y are independently -OH or -N(CH₃)₂; n is 2; R₆ is linear or forked divalent -CO-NH-(C₂-C₁₆alkylene)-(NH-CO)- radical or linear or forked -CO-NH-(C₀-C₉alkylene)-(NH-CO)- which can be interrupted by phenylene, or linear or forked divalent -C₂-C₅₀alkylene radical with carbon chain interrupted by 1 to 15 oxygen atoms.

Invention refers to production method of 1-(4-chlorophenyl)-2-cyclopropylpropane-1-one being a by-product for making biologically active substances, as well as to production method for 1-(4-chlorophenyl)-2-methyl-3-butene-1-one being a by-product for making 1-(4-chlorophenyl)-2-cyclopropylpropane-1-one. Production method for 1-(4-chlorophenyl)-2-cyclopropylpropane-1-one consists that 4-chlorobenzonitrile reacts with crotyl chloride or bromide and zinc in organic solvent and optionally with aluminium chloride. Hydrolysis of reaction mixture 2M with hydrochloric acid results in separation 1-(4-chlorophenyl)-2-methyl-3-butene-1-one thereafter purified. It reacts dibromomethane, zinc and copper monochloride in organic solvent with catalyst added or in ultrasonic bath. It is followed with separation of end product by common method.

M-chlorobenzophenone is used as an intermediate product in synthesis of original anticonvulsant "halodif" (m-chlorobenzhydrylurea). The method involves diazotisation of 2-amino-5-chlorobenzophenone at room temperature using p-toluenesulfonic acid and polymer diazotising agent, with subsequent treatment of the obtained diazonium tosylate with an aqueous solution of sodium hypophosphite.

Present invention relates to a method for synthesis of 4,4'-difluorobenzophenone, the main raw product for synthesis of aromatic polyester-ketones. The method involves a first step where fluorobenzene reacts with formaldehyde under conditions for catalysis with organic sulphonic acids to form difluorodiphenylmethane. The product is extracted and oxidised with nitric acid at the second step to 4,4'-difluorobenzophenone.

Present invention relates to a method of producing fluorine-containing tetraketones of general formula: , where I) R₁=CHCH(CH₃)₂; R₂=CH₃; II)R₁=CH₂; R₂=Ph III) R₁=CHCH₂CH₃; R₂=Ph, which can be used as synthons for producing their fluorine-containing aza- and thio-analogues, β-hydroxyketones, pyrazoles, isoxazoles, as well as biologically active substances. The method involves reacting a diester of perfluoro-dicarboxylic acid with an alkylketone in the presence of sodium hydride in the medium of an organic solvent. The diester of perfluoro-dicarboxylic acid used is dimethyl ester of perfluoro-dodecane dicarboxylic acid and the alkylketone used is: acetophenone, methyl isobutyl ketone or propyl phenyl ketone, and the process is carried out in the presence of a catalyst - dibenzo-24-crown-8 ester, in molar ratio diester of perfluoro-dicarboxylic acid: alkylketone: sodium hydride: catalyst equal to 1 : (2-3.5) : 1 : (0.00025-0.0005).

Invention relates to an improved method of producing a compound of formula , where Z is optionally substituted phenyl and Q is phenyl or 1-naphthalenyl, each optionally substituted. The method involves distillation of water from a mixture containing a compound of formula , a compound of formula , a base containing at least one compound selected from a group comprising alkali-earth metal hydroxides of formula 4 M(OH)₂, where M is Ca, Sr or Ba, alkali metal carbonates of formula 4a (M¹)₂CO₃ , where M¹ is Li, Na or K, 1,5-diazabicyclo[4,3.0]non-5-ene and 1,8-diazabicyclo[5.4.0]undec-7-ene, and an aprotic solvent capable of forming a low-boiling azeotrope with water. The invention also relates to a method of producing a compound of formula 2, a method of producing a compound of formula from a compound of formula 1 and a compound of formula 2.

Meta-chlorobenzophenone is obtained by diazotization of 2-amino-5-chlorobenzophenone at room temperature. Diazotization is carried out in mixture of icy acetic and hydrochloric acids with application of water solution of sodium nitrate with the following processing of obtained salt of diazonium with water solution of sodium hypophosphite or copper protoxide in ethyl alcohol for 0.5-1 h.

Invention relates to a method of obtaining a compound of formula , where R¹ represents CHX₂, CX₃, CX₂CHX₂ or CX₂CX₃; each X independently represents Cl or F; Z represents phenyl, optionally substituted with one or more substituents, independently selected from R²; and each R² independently represents halogen, C₁-C₆ alkyl or C₁-C₆ halogenalkyl; Q represents Q^b; Q^b represents 1-naphthalenyl, optionally substituted with R³; each R³ independently represents halogen, C₁-C₆ alkyl, C₁-C₆ halogenalkyl, -C(=W)N(R⁴)R⁵ or-C(=W)OR⁵; each R⁴ represents H; each R⁵ represents H or C₁-C₆ alkyl, optionally substituted with R⁶; each R⁶ represents C₂-C₇ alkylaminocarbonyl or C₂-C₇ halogenalkylaminocarbonyl; and each W independently represents O; including the stage, at which a compound of formula , where R¹, Q and Z are determined before for the formula 1 compound, contacts with hydroxylamine in the presence of a base. Hydroxylamine is obtained from the hydroxylamine salt. The base includes one or more compounds, selected from amine bases, hydroxide bases of alkali metals, alkoxide bases of alkali metals and carbonate bases of alkali metals. The invention also relates to the formula 2 compound, N-oxides and their salts, and such a particular compound as 4-acetyl-1-naphthalenecarbonyl chloride.