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

 

(57) Abstract:

Usage: agriculture, chemical means of plant protection. The inventive compounds f-ly I, where X is oxygen or sulfur, R is chlorine, bromine; R1, R2, R3independently from each other hydrogen or C1-C4-alkyl; R4hydrogen, hydroxy, C1-C4-alkyl; R3-R4together represent a carbonyl (=O), provided that R1, R2R5, R6all are C1-C4-alkyl; R5is hydrogen, C1-C4-alkyl; R6is hydrogen, C1-C4-alkyl, C1-C4-alkylthio or C1-C4-alkylsulfonyl, provided that when R6-C1-C4-alkylsulfonyl, then R3and R4together are carbonyl; R7is methyl or ethyl; R8-halogen, nitro, or RbSOnwhere n is 0 or 2, Rb-C1-C3-talkie or salt it, and also the use of compounds f-ly I in herbicide compositions in amounts of 0.5 to 95 wt. and in the method of controlling undesirable vegetation at the dose 0,056-1.14 kg/ha Structure of f-crystals I. 3 C. p. f-crystals. 5 table.

The invention relates to 1,3-cyclohexandione, as well as a means of protection of plants, particularly to g is the derivative of 1,3-cyclohexandione, for example, 2-/2,4-dibromo-/3-/2-methoxyethoxy/-benzo - yl/-4,4,6,6-tetramethyl-1,3,5-cyclohexane-trione as a herbicide. However, the known compounds exhibit insufficient herbicide activity.

The aim of the invention is to increase herbicide action.

This goal can be achieved by derivatives of 1,3-cyclohexandione formula 1:

where X represents oxygen or sulfur, R is chlorine, bromine, R1, R2,R3independently from each other hydrogen or C1-C4-alkyl, R4hydrogen, hydroxy, C1-C4-alkyl, R3and R4together represents a carbonyl (=0), provided that R1, R2, R5, R6all are WITH1-C4the alkyl, R5is hydrogen, C1-C4-alkyl, R6hydrogen, C1-C4-alkyl, C1-C4-alkylthio or1-C4-alkylsulfonyl, with the proviso that when R6WITH1-C4-alkyl or C1-C4-alkylsulfonyl, then R3and R4together are carbonyl, R7methyl or ethyl, R8halogen, nitro, or R6SOnwhere n is 0.2, is an R6C1-C3-alkyl or salt, and herbicide composition, R is riby undesirable vegetation in the processing space, where they grow compound of formula (1) in the dose 0,056-1.14 kg/ha.

P R I m e R 1. 2-(2'-Bromo-3'-(2-methoxyethoxy)-4 - ethylsulfonyl)-1,3-cyclohexandione.

2-Bromo-3-(2-methoxyethoxy)-4-ethylal - radioactive-benzoic acid (6,1 g 0,018 mol) was diluted in 50 ml of methylene chloride was added 2 drops of DMF followed by slow addition of oxalicacid (3,81 g 0,03 mole). After complete addition the solution was heated under reflux for 1 h, cooled and concentrated under vacuum. The crude acid chloride acid was diluted in 25 ml of methylene chloride and was added 2.24 g (0,02 mol) of 1,3-cyclohexandione, followed by the addition of excess triethylamine (4.0 g). After stirring overnight the organic layer was washed three times with 1 N. hydrochloric acid, dried and concentrated. The crude enol ester was dissolved in 25 ml of acetonitrile, and added ten drops of acetonecyanohydrin and 4 ml of triethylamine and the reaction mixture stirred at room temperature for 48 hours the Organic phase was washed three times 1H. hydrochloric acid and then extracted base. Extracts Foundation joined and podkolis and was extracted three times the ka - gel using a mixture of ether(methylene chloride)acetic acid, giving of 3.96 g of pure 2-/2-bromo-3/-2-methoxyethoxy/-4-ethylal - phenylbenzyl/-1,5-cyclohexandione.

In table.1 presents some compounds, which are obtained according to the procedure described above. The number of connections assigned to each connection and they are used in the rest of the description.

For compounds 1-38 confirmed R spectra, which are fully aligned with their structure.

Herbicide screening trials.

As mentioned earlier, the described compounds, obtained by the described method are phyto-toxic compounds, which are useful and valuable in dealing with various kinds of plants. Selected compounds of this invention were tested as herbicides as follows.

P R I m m e R 2. Preschedule mnogoostrovye herbicide trials.

The day before processing the seeds of the twelve different weed species were planted in loamy-sandy soil of the individual rows using one species per row across the width of the tray or plots. Used weeds spickle green (FT), annual bluegrass (ARC), barnyard grass (WC), sorghum bicolor (SHC), wild oat (WO), Vatanka broadleaf (BSG), onomea annual (AMC), sesbania (SESB), lie 20-40 seedlings on the number after germination, depending on the size of the plants.

Using analytical scales were weighed 37.5 mg of the test compound on a piece of waxed paper. Paper connection were placed in 60-ml clean bottle with a wide mouth, and was dissolved in 45 ml of acetone or other solvent. 18 ml of this solution was transferred into a 60 ml wide-mouthed clean bottle and diluted 22 ml of water and acetone mixture (19: 1) containing a sufficient amount of the polyoxyethylene-sorbitan-monolaurate emulsifier to obtain a final solution of 0.5% (volume/volume). The solution is then sprayed on a cropped mailbox on a linear table for spraying, calibrated to give 40 gallons per acre (748 l-ha). The degree of application or consumable dose is 14 lb./acre (0.28 kg/ha).

After processing, the drawers or trays are placed in a greenhouse at 70-80aboutC (21-27aboutC) and watered by the spray. Two weeks after treatment is determined by the degree of damage or suppression by comparison with untreated check plants of the same age. Registers the degree of damage from 0 to 100% for each species as a percentage of suppression, where 0% means no powrie R I m e R 3. Post-harvest Novosaratovka herbicide test:

This test was conducted in the same way according to the procedure preschoolage Novosaratovka herbicide trials, except that the seeds of these twelve different weed species were sown for 10-12 days before processing. In addition, irrigation of the treated trays restricted to the soil surface and did not extend to the foliage of flowering plants.

Post-harvest Novosaratovka herbicide test.

This test is performed in an identical manner in accordance with the procedure post-harvest herbicide trials except that the seeds of the twelve weed species used in predrasudom herbicide trial was sown for 10-12 days before processing. In addition, irrigation of the treated trays is limited to the soil surface and does not apply to foliage developed plants.

The results of post-harvest Novosaratovka herbicide tests are given in table.3.

The compounds of formula 1 can be used in different formulation containing 0.5 to 95% of active substance, for example, preparative form emulgirovannie 3-90 Herbicide compound 80 Wetting agent 0.5 to 2 Dialkyl-naphthalenesulfonate

sodium 0,5 Dispersing agent 1-8 sodium Lignosulphonate 7 diluent(s) attapulgite clay

Extrusion of granular formulations of Herbicide compound 1-20 Herbicide compound 10 Binder 0-10 Ligninsulfonate 5 diluent(s) calcium Carbonate

Flowable formulations of Herbicide connection 20-70 Herbicide compound 45 Surface-active agent(s) Polyoxyethylene ether 5 Suspendisse agent(s) of 0.05-1 Artagel 0,05 Antifreeze agent 1-10 Propylene glycol 10 Antimicrobial agent 1-10 WT 0.03 Antifoam 0.1 To 1 Silicone antifoam 0.02 Solvent Water

P R I m e R 4 (comparative experiences). Below is the data that reflect the comparative analysis of compounds (U.S. patent 4797150) and compound 1 of the present application. These compounds have the following structure

O/O/< / BR>
Using the technique of pre-emergence and post-harvest Novosaratovka herbicide trials, both compounds were used in their action against the following weeds: (dose of consumption of the active substance 223 g/ha) the results of the analysis of green (FT), annual bluegrass (ARG), barnyard grass (WG), sorghum bicolor (SHC), wild oat (WO), Vatanka broadleaf (BSG), sesbania (SESB), limnocharis (VL), Cassia (SP) and changes (consumable dose), the applicant may change within 0,056-1.14 kg/ha In case of use of the compounds at a dose of 56 g/ha obtained the following results, shown in table.5.

1. 2-[2,3,4-triple-substituted benzoyl]-1,3-cyclohexandione General formula

2-[2,3,4

where X is oxygen or sulfur;

R is chlorine, bromine;

R, R1, R2independently from each other hydrogen or C3WITH1-alkyl;

R4hydrogen, hydroxy, C4WITH1-alkyl;

R4and R3together represent a carbonyl(=0), provided that R4, R1, R2and R5all WITH6WITH1-alkyl;

R4hydrogen or C5WITH1-alkyl;

R4hydrogen, C6WITH1-alkyl, C4WITH1-alkylthio,4- C1-alkylsulfonyl, with the proviso that when R4WITH6WITH1alkylthio or4WITH1-alkylsulfonyl, R4and R3together are carbonyl;

R4methyl, ethyl;

R7halogen, nitro, or R8SObwhere n is 0 or 2, RnWITHb- C1-alkyl,

or their salts.

2. Herbicide composition comprising a derivative of 1,3-cyclohexandione and target additives, characterized in that as a derivative of 1,3-cyclohexandione 1, R2independently from each other hydrogen or C3WITH1-alkyl;

R4hydrogen, hydroxy, C4WITH1-alkyl;

R4and R3together represent a carbonyl(=o), provided that R4, R1, R2, R5all WITH6WITH1-alkyl;

R4hydrogen or C5WITH1-alkyl;

R4hydrogen, C6WITH1-alkyl, C4WITH1- alkylthio,4- C1-alkylsulfonyl, with the proviso that when R4WITH6WITH1-alkylthio or4WITH1-alkylsulfonyl, R4and R3together are carbonyl;

R4methyl, ethyl;

R7halogen, nitro, or R8SObwhere n is 0 or 2, and RnWITHb- C1-alkyl,

or its salt it in the amount of 0.5 to 95 wt. targeted supplements - the rest.

3. The method of controlling undesirable vegetation by processing the square, on which grow unwanted plants derived 1,3-cyclohexandione, characterized in that 1,3-cyclohexandione used as a compound of General formula

3< / BR>
where X is oxygen or sulfur;

R is chlorine or bromine;

R, R1and R2independently from each other hydrogen or C3WITH1-Ala the battle carbonyl(=0) if what R4, R1, R2and R5all WITH6WITH1-alkyl;

R4hydrogen, C5WITH1-alkyl;

R4hydrogen, C6WITH1-alkyl, C4WITH1-alkylthio or4- C1-alkylsulfonyl, provided that when R4WITH6WITH1-alkylthio or4WITH1-alkylsulfonyl, R4and R3together are carbonyl;

R4methyl or ethyl;

R7halogen, nitro, or R8SObwhere n is 0 or 2, and RnWITHb- C1-alkyl,

or its salt at a dose 0,056 1.14 kg/ha

 

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Herbicidal agent // 2271659

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1 tbl, 1 ex

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4 cl, 2 dwg, 9 ex

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6 ex

FIELD: chemistry.

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5 cl, 1 ex

FIELD: chemistry.

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EFFECT: method enables to obtain desired products with high output in a single step.

1 tbl, 3 ex

FIELD: chemistry.

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EFFECT: method enables to obtain a product with high output.

20 cl, 15 tbl, 8 ex

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EFFECT: method makes it possible to realise process at room temperature, reduce its duration and obtain meta-chlorobenzophenone with high output.

2 ex

FIELD: chemistry.

SUBSTANCE: 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 Qb; Qb 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.

EFFECT: novel enones of formula, applied as initial materials for obtaining 5-halogenalkyl-4,5-dihydroisoxazoles.

15 cl, 14 tbl, 8 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing 1,3-dicarbonyl compounds containing a dibenzosuberenyl fragment, which are of interest as a starting compounds for synthesis of biologically active substances, as well as ligands capable of coordinating metals. The method includes reacting dibenzosuberenol and 1,3-dicarbonyl compounds at 40°C for 30-180 min in a medium of 1,2-dichloroethane or nitromethane with catalysis of 5 mol % scandium triflate.

EFFECT: method enables to obtain the desired compounds with output of 63-86%.

11 ex

FIELD: chemistry.

SUBSTANCE: invention relates to processes of preparing aromatic or fatty-aromatic ketones by reaction of aromatic chlorides or bromides or iodides with an aliphatic or aromatic nitriles, including intramolecular reactions containing nitrile group of aromatic chlorides, bromides or iodides, initially resulting compound with bond C=N undergoes subsequent hydrolysis to form the desired product. In particular, a process of preparing aromatic or aliphatic-aromatic ketones of the general formula R1C(O)R2, where R1 - aryl or hetaryl, and R2 - aryl or hetaryl or alkyl comprises reacting aromatic halide R1X, wherein R1 - aryl or hetaryl, and X=Cl, Br, I with nitriles R2CN, where R2 - aryl or hetaryl, or alkyl, which is carried out in the presence of a catalyst comprising nickel atom coordinated with a chelate ligand containing 1,4-diazabutadiene fragment (N=C-C=N), and a reducing agent in an ether solvent at molar ratios: R1X:R2CN, located within the range of from 2:1 to 1:20, Ni:(chelating ligand) is located within the range of from 1:1 to 1:2, Ni:R1X, is located in the range of from 1:200 to 1:2, the reducing agent: R1X, is located in the range of from 1:2 to 10:1, and the volume of the solvent with respect to the amount of the halide R1X is in the range of 0.5 to 20 ml/mmol, at a reaction temperature of 0-120°C, and the subsequent hydrolysis of the initially formed compound with the connection of C=N.

EFFECT: expansion of the arsenal of tools, the use of compounds as starting aryl bromides and aryl chlorides, cheaper and more readily available; use of at least twice lower catalyst loads; possibility of carrying out the reaction at a lower temperature; the possibility of carrying out the reaction in a shorter time.

18 cl, 40 ex

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