Fungicidal agent and a method of combating fungi


 

(57) Abstract:

Describes a new antifungal agent, which contains one derived valinamide General formula I, where R1is isopropyl or sec.butyl and R2- chlorine, methyl, ethyl or methoxy. It differs in that it additionally contains a compound of formula II-XXI specified in paragraph 1 of the claims, or oxychloride of copper in a weight ratio of compound I and compound II or compound III, or oxychloride of copper equal to 1:(1-100). The tool, which may also contain additives target, can be used for combating fungi by treating the useful plants, the one specified derivative of the formula I and optionally a compound of formula II-XXI or oxychloride of copper, and the derived valinamide formula I and the compound of the above formula or oxychloride of copper used in the weight ratio of (1:1-100), and in an effective amount. Describes also a method of combating fungi. The technical result - increased fungicidal activity at low expenditures. 3 S. and 42 C.p. f-crystals, 3 PL.

The invention relates to the field of pest control, in particular fungicidal tool and method of combating fungi.

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where R1- ISO-propyl or sec.butyl and

R2- chlorine, methyl, ethyl or methoxy (see application N ER 472996, MKI: C 07 C 271/22, A 01 N 47/12, 1992).

A disadvantage of the known means is that in some cases its activity at low flow is not fully satisfactory.

It is also known that numerous aliphatic, aromatic or heterocyclic compounds containing nitrogen, sulfur, halogen and/or phosphorus, can be used for combating fungi (see K. H. büchel. "Pflanzenschutz und Schadlingsbekampfung" p. 122, 132, 136 - 138, 140, 141, 145, 146 and 153, ed. Georg Thieme Verlag, Stuttgart 1977, application EP 219756, EP 31257, EP 40345, DE 1567169, DE 2201063, DE 2324010, DE 2732257, FR 2254276, GB 1448810, GB 1500581, GB 2058059, US 3260588 and Brighton Corp Protection Conference(1992) 5 - 6, 435 - 437 and 5-2, 403 - 405).

The activity of the respective substances with a low consumption, however, is not always satisfactory.

The objective of the invention is to develop a fungicidal agent-based derivative valinamide General formula (I), the activity of which at low flow always satisfactory.

This task is solved proposed fungicidal agent containing one derived valinamide General formula (I)

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where R1is isopropyl or vtie formula (II)

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or the compound of formula (III)

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or the compound of formula (IV)

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or the compound of formula (V)

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or the compound of formula (VI)

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or the compound (VII)

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or the compound of formula (VIII)

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or the compound of formula (IX)

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or the compound of formula (X)

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or the compound of formula (XI)

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or the compound of formula (XII)

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or the compound of formula (XIII)

< / BR>
or the compound of formula (XIV)

< / BR>
or aluminum adduct compounds of the formula (XV)

< / BR>
or the compound of formula (XVI)

< / BR>
or methyl ester (E)-2-{-[6-(2-cianfrocca)pyridine-4 - yloxy] phenyl}-3-ethoxyacrylate acid of the formula (XVII)

< / BR>
or methyl ester (E)-methoxyimino[-(o-trioxi)-o-tolyl]acetic acid of formula (XVIII)

< / BR>
or the compound of formula (XIX)

< / BR>
where X=Cl, Y=CO or-CH(OH)-

or

Y = -CH(OH)-

or the compound of formula (XX)

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or the compound of formula (XXI)

< / BR>
where R1means of chlorbenzyl and R2- cyclopentyl, or oxychloride of copper in a weight ratio of compounds (I) to the compound (II) or the compound (III) to (XXI) or oxychloride of copper equal to 1:(1 to 100).

The structural formula of the active n shall be in the form of a mixture of different isomers or in the form of an individual isomer.

Preferred compounds of formula (I) are compounds in which the amino acid level formed from ISO-propylenecarbonate-L-valine or Deut. -butoxycarbonyl-L-valine and phenethylamine link or racemic form, or has S(-)-configuration, in particular, however, R(+)- configuration.

Particularly preferred compounds of formula (I) in which R1means isopropyl, in particular, include the following compounds: complex 1-metaliteracy ether [2-methyl-1-[[[-1-(4-chlorophenyl)ethyl]amino] carbonyl]-propyl] -carbamino acid of the formula (Ia)

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complex 1-metaliteracy ether [2-methyl-1-[[[-1-(4- were)ethyl]amino] -carbonyl]-propyl]-carbamino acid of the formula (IB)

< / BR>
complex 1-metaliteracy ether [2-methyl-1-[[[-1-(4- ethylphenyl)ethyl]amino] carbonyl]-propyl]-carbamino acid of the formula (IB)

< / BR>
and complex 1-metaliteracy ether [2-methyl-1-[[[-1-(4- methoxyphenyl)ethyl] amino]carbonyl]-propyl]-carbamino acid of the formula (Iك)

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and their isomers (according to the above data).

Contained in the proposed tool, the active principle of formula (II) - (XXI) are known from the above sources, with compounds of the formulas (II) - (VIII) and compounds of formula (IX), (XI) and (Hvca ER N 219756, the compound of formula (XIII) in the application DE N 1567169, the compound of formula (XIV) in the patent GB N 1500581, the compound of formula (XV) in the patent GB 2058059, the compounds of formulas (XVI) and (XVII) the source of the Brighton Crop Protection Conference(1992) 5 - 6, 435 - 37 and 5-2, 403-05, the compound of formula (XVIII) in the patent GB N 1448810, the compound of formula (XIX) in applications EP N 0040345, DE N 2324010 and DE N 2201063 and the compound of formula (XXI) in the application DE N 2732257.

The proposed tool can also contain additives target, which is an additional object of the invention.

Derived valinamide formula (I) and compounds of the formulas (II) - (XXI) taken in a preferred weight ratio equal to 1:(5-10), 1:(5-10), 1: 5, 1: (1-20), 1:(1-10), 1:(5-10), 1:100, 1:(10-50), 1:1, 1:10, 1:(5-10), 1: (1-10), 1:(5-10), 1:5, 1:5, 1:(1-5), 1:(1-5), 1:5, 1:5 and 1:5 respectively, and the preferred weight ratio derived valinamide formula (I) and oxychloride copper is 1:(5-50).

The tool according to the invention have very good fungicidal properties and can be used, in particular, in combating phytopathogenic fungi, such as, for example, plasmodiophoromycota, oomycetes, chytrids, zygomycetes, records of Ascomycetes, basidiomycetes, deuteromycetes etc.

The proposed tool is suitable in particular for the preventive fight against grime tool can be translated in the usual pest control preparations, such as, for example, solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, microcapsules made of polymeric materials, as well as in the preparations for the extremely fine distribution.

These preparations are prepared by known methods, for example by mixing the active principles or combinations of active principles with the target additives, such as fillers, such as liquid solvents, pressurized liquefied gases and/or solid carriers, if necessary with additional special additives, such as surfactants, i.e. emulsifiers and/or dispersants and/or foam-forming means. If the solvent used water, it is also possible to use organic solvents as auxiliary solvents. As liquid solvents are mainly used: fragrances, such as xylene, toluene or alkylnaphthalenes, chlorinated fragrances or chlorinated aliphatic hydrocarbons, such as, for example, chlorobenzene, chloroethylene or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, such as, for example petroleum fractions, alcohols, such as, for example, butane builtto or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethylsulfoxide, and water; liquefied gaseous diluents or carriers are such solvents and carriers, which at room temperature and atmospheric pressure are gaseous, such as, for example, aerosol precursor gases, such as butane, propane, nitrogen and carbon dioxide; as solid carriers used, for example, natural rock flours, such as, for example, kaolin, alumina, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and synthetic rock flours, such as, for example, highly dispersed silicic acid, alumina and silicates; as solid carriers for preparation of pellets used, for example, crushed and fractionated natural rocks such as calcite, marble, pumice, thick, dolomite, and also synthetic granules of inorganic and organic flours, and also granules of organic material such as, for example, wood flour, coconut shell, corn cobs and stalks of tobacco leaf; as emulsifiers and/or foam-forming means include, for example, neionogene oxyethylene ether of fatty alcohol series, for example a simple alkylarylsulphonates ether, alkyl sulphonates, alkyl sulphates, arylsulfonate, and also protein hydrolysates; as dispersing agents include, for example, exhaust Liminality liquor and methylcellulose.

Drugs may also enhance the adhesion of a substance, such as, for example, carboxymethylcellulose, natural and synthetic powdered, granular or Latecoere polymers, such as, for example, gum-Arabicas, polyvinyl alcohol, polyvinyl acetate, and also natural phospholipids, such as, for example, Catalina and lecithins, and synthetic phospholipids. As further additives can be called mineral and vegetable oils.

In addition, they can contain colorants such as inorganic pigments, such as, for example, iron oxide, titanium oxide, ferrocyanide, and organic dyestuffs, such as alizarin dyes, azo dyes and metallophthalocyanine dyes and micronutrients, such as, for example, salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

Preparations usually contain 0.1 to 95 wt.% active principles, preferably 0.5 to 90 wt.%.

The tool poluchat other active principle as for example, fungicides, bactericides, insecticides, acaricides, nematicides and herbicides, and fertilizers or plant growth regulators.

The proposed tool can be applied as such, in the form of drugs or get them drugs, such as, for example, ready-to-use solutions, emulsifiable concentrates, emulsions, suspensions, powders for spraying, soluble powders and granules. Application carried out in the usual manner, for example by watering, spraying, dusting, dispersion, spread, dry dressing, moist dressing, wet dressing, slurry dressing or decorating.

When processing parts of plants the concentration of the active agent in the preparations can vary within wide limits. They are usually 1 - 0.0001 wt.%, preferably from 0.5 to 0.001%.

Thus, another object of the invention is a method of combating fungi by treating the useful plants, the one derived valinamide the above General formula (I), namely, that the treatment is carried out additionally, the compound of the above formulas (II) - (XXI) or copper oxychloride, and the derived valinamide formula (I)in an effective amount.

In General, the consumption of these active substances is 0.001 to 4 kg/ha.

The synergistic mixture of two active principles may be determined by the following equation (see Colby C. P. "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations", Weeds 15, pages 20 - 22, 1967):

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where X is the activity in % of the untreated control when applying the active agent in A concentration of m h/mill,

Y - activity in % of the untreated control, when using active principle B in a concentration of m h/mill,

E - expected activity in % of the untreated control, when using active principles a and B in a concentration of type h/mill.

If the actual fungicidal activity higher than calculated, the combination has vergadain activity, i.e., there is synergism. In this case, in fact, a certain activity should be higher than the value calculated on the basis of the above formula for the expected activity (E).

The technical result of the invention is illustrated by the following examples.

Example 1

Experience with Phytophthora (tomatoes); protective action

1 weight.h. specified in table 1 of the active substance is mixed with 4.7 weight.h acetone as solvent and 0.3 weight.h. alkylarylsulphonates ether as itogo action spray young plants obtained by means until until it starts to drip off the leaves.

After drying caused as specified in table 1, the amount of plants inoculant with an aqueous suspension of Phytophthora infestans and then plants installed in an incubation chamber with a temperature of about 20oC and 100% relative humidity.

3 days after inoculation assess the damage. 0% means that the degree corresponds to the degree of action of the control experiment, and 100% degree of validity means that the lesions are not observed.

The active substance in the media, the rate of consumption and the results of the experiment are summarized in table 1.

Example 2

Experience with Phytophthora (tomatoes); protective action

1 weight.h. specified in table 2 of the active substance is mixed with 4.7 weight.h acetone as solvent and 0.3 weight.h. alkylarylsulphonates ether as an emulsifier, and the resulting concentrate is diluted with water to the specified in table 2 concentration.

To test the protective effects of spray young plants obtained by means of up until it starts to drip off the leaves.

After drying caused as specified in table 1, the amount of other plants around 20oC and 100% relative humidity.

3 days after inoculation assess the damage. 0% means that the degree corresponds to the degree of action of the control experiment, and 100% degree of validity means that the lesions are not observed.

The active substance in the media, the rate of consumption and the results of the experiment are summarized in table 2.

Example 3

Experience with Phytophthora (tomatoes); protective action

1 weight.h. specified in table 3 of the active substance is mixed with 4.7 weight.h acetone as solvent and 0.3 weight.h. alkylarylsulphonates ether as an emulsifier, and the resulting concentrate is diluted with water to the specified in table 3 concentration.

To test the protective effects of spray young plants obtained by means of up until it starts to drip off the leaves.

After drying caused as specified in table 1, the amount of plants inoculant with an aqueous suspension of Phytophthora infestans and then plants installed in an incubation chamber with a temperature of about 20oC and 100% relative humidity.

3 days after inoculation assess the damage. 0% means what lesions are not observed.

The active substance in the media, the rate of consumption and the results of the experiment are summarized in table 3.

1) R1=isopropyl, R2=Cl

2) R1=isopropyl, R2=OCH3< / BR>
3) R1=isopropyl, R2=C2H5< / BR>
4) see table.1

5) R1=Deut.butyl, R2=Cl

6) R1=Deut.butyl, R2=OCH3< / BR>
7) R1=Deut.butyl, R2=C2H5m

1. Fungicidal agent containing one derived valinamide General formula I

< / BR>
where R1is isopropyl or sec.butyl;

R2- chlorine, methyl, ethyl or methoxy,

characterized in that it additionally contains a compound of the formula II

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or the compound of formula III

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or the compound of formula IV

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or the compound of formula V

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or the compound of formula VI

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or the compound of formula VII

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or the compound of formula VIII

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or the compound of formula IX

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or a compound of the formula X

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or the compound of formula XI

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or the compound of formula XII

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or the compound of formula XIII

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or the compound of formula XIV

< / BR>
or aluminum adduct,

connection Frieda-4-yloxy] phenyl}-3-ethoxyacrylate acid of formula XVII

< / BR>
or methyl ester (E)-methoxyimino[-(o-trioxi)-o-tolyl]acetic acid of formula XVIII

< / BR>
or the compound of formula XIX

< / BR>
where X=Cl, Y=CO or-CH(OH)- or Y=-CH(OH)-

or the compound of formula XX

< / BR>
or the compound of formula XXI

< / BR>
where R1means of chlorbenzyl;

R2- cyclopentyl,

or oxychloride of copper in a weight ratio of compound I to the compound II or compound III - XXI, or oxychloride of copper equal to 1 : (1 to 100).

2. Fungicidal agent under item 1, characterized in that the derived valinamide formula I and the compound of formula II is taken in a weight ratio of 1 : (5 - 10).

3. Fungicidal agent under item 1, characterized in that the derived valinamide formula I and the compound of formula III is taken in a weight ratio of 1 : (5 - 10).

4. Fungicidal agent under item 1, characterized in that the derived valinamide formula I and the compound of formula IV is taken in a weight ratio of 1 : 5.

5. Fungicidal agent under item 1, characterized in that the derived valinamide formula I and compound of formula V is taken in a weight ratio of 1 : (1 to 20).

6. Fungicidal agent under item 1, characterized in that the derived valinamide formula I and the compound of formula VI ve valinamide formula I and the compound of formula VII is taken in a weight ratio of 1 : (5 - 10).

8. Fungicidal agent under item 1, characterized in that the derived valinamide formula I and the compound of formula VIII is taken in a weight ratio of 1 : (1 to 100).

9. Fungicidal agent under item 1, characterized in that the derived valinamide formula I and the compound of formula IX is taken in a weight ratio of 1 : (10 - 50).

10. Fungicidal agent under item 1, characterized in that the derived valinamide formula I and the compound of formula X is taken in a weight ratio of 1 : 1.

11. Fungicidal agent under item 1, characterized in that the derived valinamide formula I and the compound of formula XI is taken in a weight ratio of 1 : (1 to 10).

12. Fungicidal agent under item 1, characterized in that the derived valinamide formula I and the compound of formula XII is taken in a weight ratio of 1 : (5 - 10).

13. Fungicidal agent under item 1, characterized in that the derived valinamide formula I and the compound of formula XIII is taken in a weight ratio of 1 : (1 to 10).

14. Fungicidal agent under item 1, characterized in that the derived valinamide formula I and the compound of formula XIV is taken in a weight ratio of 1 : (5 - 10).

15. Fungicidal agent under item 1, characterized in that the derived valinamide formula I and compounds derived valinamide formula I and the compound of formula XVI is taken in a weight ratio of 1 : 5.

17. Fungicidal agent under item 1, characterized in that the derived valinamide formula I and the compound of formula XVII is taken in a weight ratio of 1 : (1 to 5).

18. Fungicidal agent under item 1, characterized in that the derived valinamide formula I and the compound of formula XVIII is taken in a weight ratio of 1 : (1 to 5).

19. Fungicidal agent under item 1, characterized in that the derived valinamide formula I and the compound of formula XIX is taken in a weight ratio of 1 : 5.

20. Fungicidal agent under item 1, characterized in that the derived valinamide formula I and the compound of formula XX is taken in a weight ratio of 1 : 5.

21. Fungicidal agent under item 1, characterized in that the derived valinamide formula I and the compound of formula XXI is taken in a weight ratio of 1 : 5.

22. Fungicidal agent under item 1, characterized in that the derived valinamide formula I and oxychloride of copper taken in a weight ratio of 1 : (5 - 50).

23. Fungicidal agent containing one derived valinamide General formula I

< / BR>
where R1is isopropyl or sec.butyl;

R2- chlorine, methyl, ethyl or methoxy,

and the target additives, characterized in that it additionally contains a compound of the formula II
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< / BR>
or the compound of formula VI

< / BR>
or the compound of formula VII

< / BR>
or the compound of formula VIII

< / BR>
or the compound of formula IX

< / BR>
or a compound of the formula X

< / BR>
or the compound of formula XI

< / BR>
or the compound of formula XII

< / BR>
or the compound of formula XIII

< / BR>
or the compound of formula XIV

< / BR>
or aluminum adduct,

or the compound of formula XV

< / BR>
or the compound of formula XVI

< / BR>
or methyl ester (E)-2-{2-[6-(2-cianfrocca)pyridine-4-yloxy-4-yloxy]phenyl}-3-ethoxyacrylate acid of formula XVII

< / BR>
or methyl ester (E)-methoxyimino[-(o-trioxi)-o-tolyl]acetic acid of formula XVIII

< / BR>
or the compound of formula XIX

< / BR>
where X=Cl, Y=CO or-CH(OH)- or Y=-CH(OH)-

or the compound of formula XX

< / BR>
or the compound of formula XXI

< / BR>
where R1means of chlorbenzyl;

R2- cyclopentyl,

or oxychloride of copper in a weight ratio of compound I to the compound II or compound III - XXI, or oxychloride of copper equal to 1 : (1 to 100).

24. Fungicidal agent for p. 23, characterized in that the derived valinamide formula I and the compound of formula II is taken in a weight ratio of 1 : (5 - 10).<�e formula III are taken in a weight ratio of 1 : (5 - 10).

26. Fungicidal agent for p. 23, characterized in that the derived valinamide formula I and the compound of formula IV is taken in a weight ratio of 1 : 5.

27. Fungicidal agent for p. 23, characterized in that the derived valinamide formula I and compound of formula V is taken in a weight ratio of 1 : (1 to 20).

28. Fungicidal agent for p. 23, characterized in that the derived valinamide formula I and the compound of formula VI is taken in a weight ratio of 1 : (1 to 10).

29. Fungicidal agent for p. 23, characterized in that the derived valinamide formula I and the compound of formula VII is taken in a weight ratio of 1 : (5 - 10).

30. Fungicidal agent for p. 23, characterized in that the derived valinamide formula I and the compound of formula VIII is taken in a weight ratio of 1 : (10 - 50).

31. Fungicidal agent for p. 23, characterized in that the derived valinamide formula I and the compound of formula IX is taken in a weight ratio of 1 : (10 - 50).

32. Fungicidal agent for p. 23, characterized in that the derived valinamide formula I and the compound of formula X is taken in a weight ratio of 1 : 1.

33. Fungicidal agent for p. 23, characterized in that the derived valinamide formula I and SoE fact, that the derived valinamide formula I and the compound of formula XII is taken in a weight ratio of 1 : (5 - 10).

35. Fungicidal agent for p. 23, characterized in that the derived valinamide formula I and the compound of formula XIII is taken in a weight ratio of 1 : (1 to 10)

36. Fungicidal agent for p. 23, characterized in that the derived valinamide formula I and the compound of formula XIV is taken in a weight ratio of 1 : (5 - 10).

37. Fungicidal agent for p. 23, characterized in that the derived valinamide formula I and the compound of formula XV is taken in a weight ratio of 1 : 5.

38. Fungicidal agent for p. 23, characterized in that the derived valinamide formula I and the compound of formula XVI is taken in a weight ratio of 1 : 5.

39. Fungicidal agent for p. 23, characterized in that the derived valinamide formula I and the compound of formula XVII is taken in a weight ratio of 1 : (1 to 5),

40. Fungicidal agent for p. 23, characterized in that the derived valinamide formula I and the compound of formula XVIII is taken in a weight ratio of 1 : (1 to 5).

41. Fungicidal agent for p. 23, characterized in that the derived valinamide formula I and the compound of formula XIX is taken in a weight ratio of 1 : 5.

42. Fungicidal ratio of 1 : 5.

43. Fungicidal agent for p. 23, characterized in that the derived valinamide formula I and the compound of formula XXI is taken in a weight ratio of 1 : 5.

44. Fungicidal agent for p. 23, characterized in that the derived valinamide formula I and oxychloride of copper taken in a weight ratio of 1 : (5 - 50).

45. A method of combating fungi by treating the useful plants, the one derived valinamide General formula I

< / BR>
where R1is isopropyl or sec.butyl;

R2- chlorine, methyl, ethyl or methoxy,

characterized in that the treatment is carried out additionally, the compound of formula II - XXI under item 1 or oxychloride of copper, and the derived valinamide formula I and the compound of the above formula or oxychloride of copper used in a weight ratio of 1 : (1 to 100), and in an effective amount.

 

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