SU713526A3 - Fungicidic composition - Google Patents

Abstract

Fungicide compsns. contain >=1 cpd. of formula (where Y, Y", Z' and Z' are H or opt. halogenated 1-5C alkyl; M = H, a metal cation, ammonium, alkyl-ammonium or mono-, di- or tri(hydroxy)-alkyl ammonium, and n = valence of M).

Description

H- ° - ™ -:: :: ° -4

Isolation of hydrochloric acid is favored by the maintenance of temperature close to room temperature and reduced pressure.

It is also possible to obtain the same compound by using the tether phosphate of dipethyl phosphite in the presence of α-glycol.

However, the products obtained by these two methods contain not only cyclic production, but also more viscous derivatives.

The method for the preparation of the cyclic product is hydrolpsing the chemical chlorophenol and the derivative in the presence of a hydrochloric acid acceptor by exposure to a stapometer with water.

PRPMER I. Poluchenpe 2-hydrokei-4meptl-1, 3,2 - diokeaphospholapa (compounds CH1 AO 1).

A. The synthesis of 4-methyl-2-oxo-2H-1, 3, 2-dioxaphospholium is carried out by means of the 4-methyl-2-chloro-1,3,2-dpoxaphosphol 1pa gadrolysis in the presence of a hydrochloric acid acceptor such as iridide, coiviaeno reactions

CH - about.

SNZ - CH-0

. P -C -t-HOHI / Rn

CHj-O LNG

28.1 g (0.2 l) chlo) phosphite rat | py in 250 ml of anhydrous toluene n is cooled with stirring to temperature) below 10 ° C. Then you take 3.6 g (0.2 mol) of water in as a solution in 15.8 g (0.2 mol) of waterless pyridine.

At the end of the pouring, the temperature of the reactants is allowed to rise to 20 ° C. The hydrochloride is filtered off and the toluene is removed under vacuum.

Liquid oil remains, which is protected under vacuum.

Yield 57%. T. Kip. 64 ° C / 0.1 mmHg v .;

"1 1.472.

This mobile fluid, with the smell of geran1I, is soluble in all organic 1) solvent.

The NMR spectrum indicates that the product (compound I) is a mixture of two cyclic isomers.

SzNgOZR.

Calculated,%: C 29.50; H 5.74; R 25.40.

Found,%: C 29.33; H 6.13; R 25.48.

B. Impact 1 mole of anhydrous 1,2-propylene glycol per 1 mole of anhydrous phosphorus trichloride in the form of a solution in dibromometh-i. Poluacrye quantitative chlorophosphite and iipleiglycolic with (reaction)

CHj-CHOH Cl.

SNS-CH-0

I +; P-C1

P-C1

CHjOH CI

CHj-O

The reaction is exothermic, the reaction mixture is cooled. After 1 hour and 30 minutes, the solvent is removed by distillation, to obtain the first product, a pressure pump is dispensed (pi. Then 2 equivalents of water are added and the equivalent of chlorophosphite in I1de solution in aceto-nitro.

with; Use the method with diethphosphite p about p1lepgplekol according to the scheme

20CHj-CH-OHC HjO

CHj-OHC HsO I

0 0 .Р-l-2CjH50H

about

n

HarpeiiaroT mixture of one I pray each PZ reagents at 120-130 ° C under pressure, 1 120 mm Hg. Art. until termination 1 of the hl1p ol, npn, .viepHO for 3 /.

Г1е) its product obtained with a sweep of 71 °), c; 1 is viscous, colorless

oil e show: hem reframs;

“0-4,469 pt. CAT. 106-107 C / 10 mm

Hg Art.

This oil is soluble in water, alcohol, acetone, and is insoluble in aromatic solvents. SzPuOZR.

Calculated. %: C 29.50; H 5.74; R 25.40. Found,%: C 30.69; H 6.24; R 22.46. . One method is to produce a dia, alkylphoofite, which consists of introducing it in rms and at a temperature below -5 ° C}) ext) of phosphorus and a mixture of progplenglex 1 and methanol. After isolation of hydrochloric acid and methylene chloride under vacuum, compound I1 is obtained, the structure of which is confirmed by the NK spectrum.

Similarly, the following combinations were obtained:

A1) 2 - 2-hydroxy-4-chloromethyl-1,3,2-dioxaphos (| yulap, L1 3 - 2-hydrox-1,3-2-dioxaphospholane.

Forms of use of drugs are common.

Example 2. Test in vitro growth of mycelium.

The effects of the products according to the invention on the growth of mycelium of fungi are heard:

Rhizoctonia solani, responsible for necrosis of the root zone;

Fusarium oxysporum, responsible for tracheomycosis;

Fusarium nivale, responsible for the atrophy of shoots ZLEKOV;

Fusarium roseum, responsible for fusariose cereals;

Sclerotinia minor, responsible for sclerocyne;

Sclerotinia sclerotiorum, responsible for sclerocinosis;

Pythium de Baryanum, responsible for seedling atrophy;

Phonopsis viticoia, responsible for excrement;

Septoria nodorum, responsible for saptorioz (septoriose) cereals;

Helminthosporium, responsible for helminitis psoriasis (helminthosporiose);

Verticillium, responsible for vcrticilliose (verticilliosis);

Cercospora beticola, responsible for cercoliosis (cercosporiose);

Gleosporium perennaus, responsible for rotting the block during storage.

For each experiment, method I "planes with a solution of agar (Agar Plate dilution) are used. A mixture of agar and acegonic is poured into a Petri dish at a temperature of about 50 ° C. solution or wetted by the fungus

Rhizoctonia

Fusarium o.xysport.rn

Fusarium nivale

Fusarium roseum

Sclerotinia minor

Sclerotinia sclerotiori: m

Pvthium

Phonopsis

Septoria

Helminthosporiuni

Verticillium

Cercospora

Gleosporium

Example 3. In vivo test on terrestrial fungi (champignon dusol).

The effects of the products according to the invention on Pythium de Vaguapit are produced on cucumbers.

For each experiment, proceed as follows. Mix the medium containing the fungus culture with sterilized earth and supply the vessels with the mixture. After 8 days, the earth is infected. It is then treated by pouring a suspension of the test substance in various concentrations. It is (suspension) formed smaroshka. containing the test substance at a concentration of 0.25 g1l.

Wetted powder is obtained by mixing for 1 min in the incisor crusher (un broyeur aconteaux) of the following components,%:

Active test substance 20

Anti-blocking agent (calcium lignosulfonate) 5

Wetting agent .. (sodium alkylaryl sulfonate) 1

Filler (aluminum silicate) 74.

This wettable powder is then mixed with a proportion of water for use at the desired dose.

The agar mixture is allowed to solidify and the mycete mycelium culture rings are placed.

As a control, take a Petri dish, similar to the previous one, but agarova, the medium of which does not contain active substance.

After 4 days at 20 ° C, the surface of the observed inhibition zone is estimated and expressed as a percentage relative to the seed grain.

The results of the Ire.details in Table. one.

Table 1% inhibited

product 2 1

50 60 (i5 70

100 50

100 50 70 70

100 90

powdered powder, obtained as in at least 2.

Then the treated soil is sown with cucumber seeds.

Records of production, t, t after 15 days and after sowing, after counting the destroyed or sick plants in relation to the untreated control sample or the same-colored sample.

Under these conditions, 95% entrapment is observed for products 1 and 2 at a dose of 0.5 g / l.

Example 4. In vivo organ survival test: Test for M | Ildew (mold) tomato Phytophora infestans. Fla fresh seed and tomato leaf are placed a drop of spas pz spore suspension of 80000 pellucid / hl, and suspension, disassembled by a junction of wetted powder of the same composition as such, oipsappy in pr); leter 2, in s.tuchas nepacTiiopiiMoro product or acetone solution. Under these conditions, 95% -11% protection is observed for products 1 and 2 at a dose of 0.5 g / l, product 1 exhibits a 75-95% shear at a dose of 0.125 g / l. G1 p and measure 5. In ivo test on Plasmopara viticola plants. A. Safety processing. Treated with chickens puffedroot} pz pistol grape plants, cultivated in the soil, on the lower surface of the leaves with an aqueous suspension of a wettable powder, having c-following; eecoBoii composition,%: Active test ventilator20 Anti-blocking medium (calcium calcium sulphonate) 5 Cm and h and tel (alklpl sodium sulfonate sodium) 1 Pannolptel (aluminum silicate) 74 rasba1; .) g; test specimen active semecTBO in a dose-taking manner; each test is repeated two times. After 48 h, osus1st1 l from 3nr); izheniem and nanomenpenii on the lower i; o the supernumerary leaves of the aqueous suspension of about 80,000 units / sign spore of the selected fungus. The soils are then placed 48 hours later in a domestic chamber with a relative temperature of 100% at a temperature of 20 ° C. The plants are monitored 9 dpi after infection. Under these conditions, it is observed that at a dose of 0.5 g of Compound 1, 2, and 3, 95% iivio is protected. In addition to T01H), it is stated that each of the tested probes does not show amenable |) and toxicity. 15. System test (c1 sy systcnue) by corpulent abeorbcin in the case of 1 p 01rad; 1. Several roots of water are harvested (variety Camay), each is found in a thicket containing a worm (1a vermiciilite) and a nutrient solution of a 40 solution with 0.1 g / l of an intact extract. After two days, the fences are contaminated with an aqueous suspension containing 100,000 spores / s - “Plasmopara viticola. RT incubate for 48 / in a chamber at 20 ° C and 100% relative humidity. An observation of the degree of infection takes place after about 7 days (but relates to an infected control sample, which is watered by a 40 cm diet). Under these conditions, it is observed that the cell, L1 1, absorbs |) 0 cobalt 1 mi. ikazy) ast 95% - the first place of the litter vshug) hell against the mildew, which in turn proves well the systemic nature of the regional economy. B. System test by lstovoy abso)) on a milda of grapes. Treated on staggy 7. clean, several roots of grapes (variety Camay), nrnchem each is located in h-aHJKy, containing a mixture of pure earth and sand. The treatment is carried out by pulverizing (spraying) the s.machpvaemuyu containing g / l of active nsngugeemy veHiecTBa, on the bottom surface of the lowest 4 litas. For 48 hours in a chamber at 20 ° C and 100: -the relative humidity. The control of the degree of infection has been observed after the expiration of an eye. It is 7 dpi on the 5-7th leaves from the bottom, and it relates the LPO to the control sample, WHO IS) Obabotan distilled water. Under these conditions, it is observed that soy ;; The jVg 1 exhibits a 95% protection of liejixHiix grape litas nrotnv mildew. The sysgemia ascertained by the passer-by example, is confirmed, Kior.ta actinopoo is used (npii leaf vol); trick. P) and measure G. The sample (test) is fresh; h; 1, ear grapes on the mildew. jiyiiHbi Grapevine (Camay) infection at the end of the month of August as a result of obi, rain and tea leaves. These vines are then treated with expired liHii 8, 14, and 23. Tiieji is congruent with the pulp quality of 50% of .with the wetted pores; OH1:; s of the connected no. Pabludenden, expressed in H1) centered but related to the zagzazhennom, but not necessarily a different control sample, p. ala1; 1L C (; answer3 epile after 2, 8, 20, 35 p 45 dpi after the last treatment (dose 2 g / l)., 1i: employment 2100 870 2015 2510 45O C; equant; e ispany. were wasps C: Stv; genes on grape plapattsp x (Camay ginograd) with its use from oneG of compounds 1 according to the invention i 2.5 g / l, and from .Tpyroft sides 1.1 from yeno.nog a) chesky (;: and; drv vs milG) Dew, as l i: -i; (gtilenbislokp.karbamate Margapts) and folpel). C. Chzhloe pz of these soD1 || 1e1 1 n sprinkle; / :( iu, i;: i; r i4 (cK (je isss: and 1o ;;;: ipe. Oc: ich: tv: 1I from aia.K)) gich1o, as (P: e: m: o n Mr P. Nn. with the same difference as; p ::;; h; 10 would not be done by the processor, but with the help of a syringe

lei spore suspensions in various points of Eupygrads leaves.

Research on the therapeutic effect.

The viruses are analogous to the above mentioned example, but first they infect with dots and then the active compound is sprayed.

Nin only when oil spots characteristic of mildew appear on the leaves of the grapes.

In tab. 2 shows active compounds, doses and results expressed in the number of infection points, with an average of 7 results.

Lktivnos compound

Claims (2)

Control Compound “And Compound 1 .1eeb The preventive effect of Kaitan and Folpel at the dose recommended by the supplier, respectively 180 and 150 grams, is as good as the preventive effect of Compound 1. The therapeutic effect of these compounds (Captai and Folpel) is almost none. is. At a dose of 300 g / hl, the results remain the same and, in addition, the strong phytotoxicity of these two fungicides is noted. These results can be supplemented with data obtained from studies on the root system, on the one hand, using compounds 11 1 and on the other hand, using maneb, captafol and polnel in the amount of 0.1 g,. Under these conditions, 95% protection was observed with compound L 1. Thus, the proposed fungicide composition has an enhanced fungicide and Y | M action. Claims of the Invention: A fungicidal composition comprising lecheonos action 179 3 154 is an active substance and additive,; and | brine is a carrier, diluent and filler, characterized in that. that, in order to enhance the fungicidal ... it contains as an active substance a compound obHieii of the formula Z with -O where Y, Y is hydrogen. Z is hydrogen, Z is hydrogen, methyl, chloromethyl, in the amount of 20-85 weight. % Sources of information taken into account in the case of eksnertse: 1.Patent of Fra1schii Le 2063651, cl. From 07 d 105/00. helib. 1971. 2..Melnikov P.P. “Chemistry of pesticides. .M., “Chemistry, 1968, p. 241 (irototnp).