6-methyl-3,4-dioxo-1-(4-methoxybenzylidene)-furo[3,4-c] pyridine, manifesting stimulating germination of seeds of agricultural crops

 

(57) Abstract:

The invention relates to new biologically active chemical compound exhibiting the properties of activator germination of seeds of agricultural crops. The purpose of the invention is creating a promising growth of plants, particularly rice and sunflower. The essence of the invention. Product: 6-methyl-3,4-dioxo-1-(4-methoxybenzylidene)-furo[3,4-c] pyridine, BF C16H13NO4, yield 80%, so different. 318-320oC. Reagent 1: 6-methyl-3,4-dioxo-1(H)-furo[3,4-c] pyridine; reagent 2: anisic aldehyde. Reaction conditions: in the presence of piperidine in the medium boiling C2H5OH for 5 hours the resulting product is filtered off. The filtrate is evaporated. The residue is triturated in hot water and identified as a product. table 2.

The invention relates to new biologically active chemical compounds and can be used in agriculture.

Known application of gibberellins as activator of seed germination is similar in properties. (Melnikov N. N., Baskakov, Y. A. Chemistry of herbicides and plant growth regulators. M: Goskomizdat, 1962. S. 201). However, similar properties ineffective. Gibberellin is expensive honeycomb plants. Kiev: publishing house of the USSR Academy of Sciences. 1965, S. 407).

From known compounds proposed for use as a stimulator of plant growth, the closest in structure to the claimed technical solution is pericolace: 6-methyl-3,4-dioxo-1H-furo[3,4-c] pyridine (II) (prototype)

< / BR>
(A. S. N 1565453, 1990. Means for pre-processing stratified Apple seeds), which does not rotoscoliosis actions on agricultural crops.

The present invention solves the problem of expanding the range of cost-effective plant growth regulators, in particular agricultural crops, and ensuring environmental cleanliness.

The technical result is achieved by the synthesis of 6-methyl-3,4-dioxo-1-(4-methoxybenzylidene)-furo[3,4-c] pyridine (I), which is obtained by condensation of compound II (peritonectomy) with anise aldehyde in the presence of piperidine.

The claimed connection is a new derivative of peritonectomy (I registered at the research Institute for BISH N 9080889 from 17.02.89 year).

< / BR>
Comparative analysis of the proposed technical solutions to the prototype allows us to conclude that the claimed plant growth regulator differs so the proposed solution meets the patentability criteria of "novelty."

Our research identified the biological activity of new chemical compounds that stimulate the germination of seeds of agricultural crops, in particular rice, sunflower. This allows to make a conclusion on the conformity of the proposed technical solution to the patentability criterion of "inventive step".

Compliance with the proposed technical solution to the patentability criterion of "industrial applicability" there is no doubt, as it can be used in agriculture as a stimulator of plant growth.

The invention is illustrated in the following examples.

Example 1. Getting 6-methyl-3,4-dioxo-1-(4-methoxybenzylidene) furo[3,4-C]pyridine - compound (I).

To 0.33 g (0.002 mol) of the compound (II) in 15 ml of ethanol while heating to 60oC was added 1-2 drops of piperidine, 3.5 ml (of 0.003 mol) anisic aldehyde in 5 ml of ethanol and boiled water for 5 h under stirring. The reaction mixture was cooled, filtered, the yellow crystals were washed with a small amount of alcohol. The filtrate was evaporated. The residue is triturated in hot lodevico product 0.45 g (80%).

Compound I is crystalline substance yellow, resistant to air during storage. When the temperature 318-320oC decomposes without melting.

max(lg): 247 (4,44); 3,79 (4,43).

PMR (60 MHz), CF3COOH, , M. D.: 7.45 (2H, d, H'2); 6.63 (2H, d, H'2); 6.50 (1H, s, Ho1); 6.45 (1H, s, =CH); 3.53 (3H, s, OCH3); 2.18 (3H, s, CH3). IR spectrum , cm-1: 1800 (C=O lactone), 1675 (C=O amide), 1650, 1620, 1600, 1575 (C=C, C=N), 1280 (=COC=O); 1200, 1180, 1135, 1060, 1040 (COC).

Found, %: C 67,52; H 4,22; N 4,56. C16H13NO4< / BR>
Calculated, %: C 67,84; H 4,59; N 4,95.

The method of obtaining the compound I is simple to perform and requires no special equipment.

The claimed connection refers to low toxicity to warm-blooded animals, LD50> 2000 mg/kg

Example 2. The study astragulus properties of 6-methyl-3,4-dioxo-1- (4-methoxybenzylidene)-furo[3,4-C]pyridine rice.

Step 6-methyl-3,4-dioxo-1-(4-methoxybenzylidene)-furo[3,4-C]pyridine on the germination of rice varieties "Spalicek" studied under laboratory conditions in accordance with GOST N 12038-84. The drug I similar properties - gibberellins and prototype (II) was used by pre-sowing seed soaking with water 0,1; 0,05; 0,01; of 0.005 and 0.001% solutions C is in the form of water of 0.001% solution. Seeds were germinated in Petri dishes on moist filter paper at a temperature of 28oC. For each repetition was used for 50 PCs of seeds. Experiment was repeated 4 speed.

During germination was determined vigor on the 3rd day of germination on day 7, the length of the root and the height of the sprout 7-day, their wet weight.

The results of the study are given in table. 1.

Analysis of the data given in table. 1, showed that optimally trigger the increase in the dose of 6-methyl-3,4-dioxo-1-(4 - methoxybenzylidene)-furo[3,4-c]pyridine of formula I is 0.001%. At this dose germination is increased by 10% relative to control and gibberellins, germination by 11% relative to control and 9% relative to gibberellins. Under the action of the drug is observed activation of the growth and development of seedlings; thus, the length of the stem relative to the control is increased by 31.8%, root - 18%, relative to the gibberellin respectively 16% and 15%. Wet weight of shoot and root increased by 21% and 9% compared with the control. The prototype does not influence the germination, growth and development of seedlings and germination increases by 6%.

Activation of the growth and development of the root allows the seedlings better scriplet the new processes of rice and seed treatment the claimed connection will allow you to get quality seed.

Example 3. Step 6-methyl-3,4-dioxo-1-(4-methoxy-benzylidene)- furo[3,4-C]pyridine on the germination of sunflower seeds.

The effect of the drug was studied under laboratory conditions in accordance with GOST N 12038-86. The product I and the prototype II was applied by treating the seeds with the use of aqueous solutions of concentrations 0,05; 0,01; 0,005; 0,001; 0,0005%, gibberellin - similar properties - with a mass fraction of 0.001%. Inlaying conducted at a rate of 10 l of solution per 1 ton of seeds. The seeds were laid in rolls of moist filter paper. During germination was determined vigor on the 3rd day of germination on day 5, the length of root and stalk, raw weight of 5-day-old seedlings. The research results are summarized in table. 2.

The connection I in the optimal stimulating dose of 0.001% increases the germination of seeds of sunflower varieties of "Firstborn" is 9%, the length of the stem and main radicle, respectively, at 10 and 18%, of the weight of the stem and root of 14 and 21% vs. control. Gibberellins and prototype a significant effect on the germination of seeds do not have, the prototype has a small effect on the length and weight of roots, increasing respectively by 7 and 13%. However, the similar and the prototype is almost 2 times lower on all counts C is a dose of 0.001% more efficient than its counterpart and prototype and significantly improves seed quality of sunflower seeds. This may allow to reduce the seeding rate seeds per hectare, which determines the economic feasibility of its application.

Summarizing the data of tables 1 and 2 by the action of the claimed compounds I in optimal concentration of 0.001% on the growth and development of crops, particularly rice and sunflower, it should be noted the increase in energy of germination and germination of rice seeds and sunflower seeds relative to control, respectively, at 10 and 11, 7 and 9%. The claimed connection increases the seedlings and wet weight, respectively. The length of the stalk of rice and sunflower increased by 10% and 31.8%, respectively, and the root of 18% relative to control. Compared with gibberellin noted any difference of 16% and 6%, 15% and 12%. The analogues of the properties and structure a significant impact on energy and germination of rice and sunflower do not have.

The fact that the claimed compound is a derivative of peritonectomy obtained in the processing of waste production of vitamin B6enables recycling of waste and makes the production of ecologically clean. This makes economic is Skye toxicity and the dose (0.1 g/t seed) ensure the ecological safety of the claimed compounds.

6-Methyl-3,4-dioxo-1-(4-methoxybenzylidene)-furo[3,4-c]-pyridine of the formula

< / BR>
manifesting stimulating germination of seeds of agricultural crops.

 

Same patents:

The invention relates to polycyclic aminecontaining compounds, to their optically pure enantiomers, the way they are received, to Farmaceutici on their basis, as well as to new intermediate compounds for the synthesis of polycyclic compounds

The invention relates to androidiani carboxanilides, compositions based on them and the way to deal with arteriotomy and can be used in agriculture

The invention relates to a series of new derivatives of compounds known as "milbemycin", which are characterized by the presence of heterocyclic substituted mercaptoacetate group at the 13-position

The invention relates to certain 13-alkyl-23-imino - 13-halogen-23-imino-LL-F28249-compounds and to their use for combating endo - and ectoparasitic infections and infestations in warm-blooded animals

FIELD: agriculture.

SUBSTANCE: invention describes a method for feeding potato and tomato with 6-benzylaminopurine an aqueous solution taken in the concentration 10-4 M and growing pants up to preparing harvest according to technology accepted for the culture crop. Invention proposes 3-fold treatment of plants for vegetation: at the lateral branching phase, at onset of forming economically value organs and immediately after the growth termination. Method provides the effective enhancing the productivity of the most important vegetable crops - tomato and potato.

EFFECT: improved enhancing method.

6 tbl, 4 ex

FIELD: organic chemistry, chemical technology, herbicides.

SUBSTANCE: invention describes a method for preparing compounds of the formula (I):

wherein each R1, R2, R3 means independently of one another (C-C6)-alkyl; R can represent also pyridyl; R4 and R5 in common with nitrogen atoms to which they are joined form unsaturated 5-8-membered heterocyclic ring that can be broken by oxygen atom; G means hydrogen atom. Method involves interaction of compound of the formula (II):

wherein R1, R2 and R3 have above given values; R6 is a group RR9N-; R7 is a group R10R11N-; each among R8, R, R10 and R11 means independently of one another hydrogen atom or (C1-C6)-alkyl in inert organic solvent being optionally with the presence of a base with compound of the formula (IV) ,

(IVa)

or (IVb) ,

wherein R4 and R have above given values; H x Hal means hydrogen halide. The prepared compound of the formula (I) wherein G represents ammonium cation is converted to the corresponding compound of the formula (I) by treatment with Brensted's acid wherein G represents hydrogen atom. Also, invention describes compound of the formula (II) wherein R1, R2, R3, R6 and R7 have above indicated values.

EFFECT: improved preparing method.

9 cl, 12 ex

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: agriculture, plant science, plant protection.

SUBSTANCE: the suggested herbicidal composition of selective action contains, except generally accepted additional substances for the composition, a mixture as an active substance including a) herbicidally efficient quantity of compound of formula (I) , where R1 and R3 each independently means ethyl, ethynyl, C1- or C2alkoxy; R4 and R5 forms together the group Z2-CR14(R15)-CR16(R17)-O-CR18(R19)-CR20(R21)-(Z2); R14, R15, R16, R17, R18, R19, R20 and R21 means hydrogen; G means hydrogen, -C(X1)-R30, -C(X2)-X3-R31; X1, X2, X3 means oxygen; R30, R31 each independently means C1-C10alkyl, or salts or diastereoisomer of compound of formula (I), and b) efficient quantity of antidote of formula IIa to prevent harmful action of herbicide, where R22 means hydrogen, alkaline-earth metal or ethyl, or of formula IIb , where R23 means hydrogen, alkaline-earth metal or ethyl, and method for selective control for weed plants and grasses in cultivated plants. Thus, the antidote decreases the damage of cultivated plants induced by herbicide of formula (I).

EFFECT: higher efficiency of plant protection.

3 cl, 4 ex, 4 tbl

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: organic chemistry, veterinary science.

SUBSTANCE: invention relates to a method for control over exto- and endoparasites taken among group including acariform mites, parasitoformous mites and nematodes parasitizing in animals, productive cattle and domestic animals. Method involves applying veterinary preparation comprising 1-[4-chloro-3-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl]-3-(2,6-difluoro)urea and compound of the formula (i):

wherein R1 means one of radicals:

or ; R2 means -CH(CH3)-CH3, -CH(CH3)-C2H5, -C(CH3)=CH-CH(CH3)2 or cyclohexyl; R3 means hydrogen atom or hydroxy-group if a bond between atoms 22 and 23 represents a double bond, or it means hydrogen atom or group =N-O-CH3 if an ordinary bond presents between atoms 22 and 23; R4 means HO-, and the preparation can be in free form or in physiologically acceptable form. Invention provides preparing preparations with good tolerance and rapid effect and persistence with respect to different helminth-associated diseases, parasitiformous and acariformous mites being without adverse effect on normal behavior of animals.

EFFECT: valuable properties of compounds.

7 cl, 3 tbl, 8 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: 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.

EFFECT: compositions useful in effective controlling of many weeds both in pre-spring and post-spring phases.

5 cl, 63 tbl, 12 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to herbicidal composition containing synergetically effective amounts of (A) and (B) components, wherein (A) has formula II (R1 is C1-C6-alkyl, substituted with halogen; R2, R3 and R4 are hydrogen; R5 is rest of formula -B1-Y1, wherein B1 is direct bond and Y1 is acyclic C1-C6-hydrocarbon or cyclic C3-C6-hydrocarbon; F is -CH2-CH2-, -CH2-CH2-CH2- and CH2-O-; X are independently halogen or C1-C4-alkoxy; n = 0-2; and (B) represents one or more herbicides, selected from group containing isoprothuron, flufenacet, anylophos, ethoxysulphuron, mecoprop-(P), ioxinyl, florazulam, pendimethalin, MV 100, etc. Also disclosed is method for weed controlling using abovementioned composition.

EFFECT: composition with improved herbicidal action.

12 cl, 23 ex, 23 tbl

FIELD: agriculture, in particular method for controlling of specific insect pests.

SUBSTANCE: invention relates to method for controlling of lepidopterous, homopterous, hemipterans, coleopterous, and physopods by contacting of said pests or environment thereof with effective amount of compound of formula I SSS1, N-oxide or agriculturally acceptable salt thereof being effective against abovementioned insects, wherein A and B are independently O or S; R1, R2 represent H, C1-C6-alkyl; R3 represents H, optionally substituted C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkinyl, or C3-C6-cycloalkyl; R4 represents H, C1-C6-alkyl, C2-C6-alkinyl, C1-C6-haloalkyl, CN, halogen, C1-C4-alkoxy, C1-C4-haloalkoxy, NO2;. R5 represents H, C1-C6-alkyl, C1-C6-haloalkyl, C1-C4-hydroxyalkyl, CO2R11R12, halogen or C1-C4-alkoxy; R6 represents H, C1-C6-alkyl, C1-C6-haloalkyl; R7 represents H, C1-C6-alkyl, C2-C6-alkenyl, C1-C6-haloalkyl, phenyl ring, benzyl ring, or 5-6-membered heteroaromatic rind, naphthyl ring system, or 8-10-membered condensed heterodicyclic system. Also claimed are compound of formula I and benzoxazine derivative of formula 10 .

EFFECT: compounds effective against agriculture spineless depredators.

22 cl, 13 tbl, 1 dwg, 24 ex

FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention describes a composition showing the selective effect and comprising as conventional inert adjuvants and the following mixture as an active component: a) effective amount of compound of the formula (I): as a herbicide wherein each R1 and R3 means independently of one another (C1-C4)-alkyl; R4 and R5 mean the group: -C-R14(R15)-C-R16(R17)-O-R18(R19)-C-R20(R21)-(Z2) wherein R14, R15, R16, R17, R18, R19, R20 and R21 mean hydrogen atom; G means hydrogen atom, -C(X1)-R30, alkaline metal cation, earth-alkaline metal cation, sulfonium or ammonium cation; X1 means oxygen atom; R30 means hydrogen atom, (C1-C10)-alkyl, and salts and diastereomers of compounds of the formula (I) under condition that R1 and R3 don't methyl group simultaneously; b) effective amount of protective agent (antidote) for prevention of hazard effect of herbicide wherein antidote is taken among the group comprising clochintocet, clochintocet with alkaline metal cation, earth-alkaline metal cation, sulfonium or ammonium cation, clochintocet-mexil, mefenpir, mefenpir with alkaline metal cation, earth-alkaline metal cation, sulfonium or ammonium cation and mefenpir-diethyl, and c) additive comprising (C8-C22)-saturated acids alkyl ester or emulsified vegetable oil, or mineral oil taken in the amount 0.01-2% as measured to the spraying mixture mass. Also, invention describes a method for selective control of weed and grassy plants in cultural plant plantings that involves using the abovementioned composition for treatment. Invention provides the selective effect in control of weed and grassy plants, in particular, in cereals crops plantings.

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

3 cl, 8 tbl, 2 ex

Up!