UA78555C2 - Method for immunizing plants against bacterioses and compounds used - Google Patents

Abstract

The invention relates to a method for immunizing plants against bacterioses, characterized in that the plants, the soil, or seeds are treated with an effective quantity of a compound of formula (I), wherein: X represents halogen, C1-C4 alkyl or trifluoromethyl; m is equal to 0 or 1; Q represents C (=CH-CH3) -COOCH3, C (=CH-OCH3)-COOCH3, C(=CH-OCH3) -CONHCH3, C(=N-OCH3)-COOCH3, C(=N-OCH3) -CONHCH3 or N(-OCH3)-COOCH3; A represents -O-B, -CH2O-B, -CH2S-B, -OCH2-B, -CH=CH-B, -C=C-B, -CH2O-N=C(R1)-B or -CH2O-N=C(R1)-C(R2)=N-OR3, whereby B represents optionally substituted phenyl, naphthyl, 5-membered or 6-membered hetary) or 5-membered or 6-membered heterocyclyl, containing one to three N atoms and/or one 0 atom or S atom or one or two 0 atoms and/or S atoms; R1 represents hydrogen, cyano, alkyl, alkyl halide, cycloalkyl, alkoxy; R2 represents optionally substituted phenyl, phenylcarbonyl, phenylsulfonyl, 5-membered or 6-membered hetaryl, 5-membered or 6-membered hetarylcarbonyl or 5-membered or 6-membered hetarylsulfonyl, and; R3 represents hydrogen, optionally substituted alkyl, alkenyl and alkynyl. This effective quantity of the compound is absorbed by the plants or seeds.

Description

Description of the invention

The invention relates to a method of immunizing plants against bacteriosis (bacterial diseases), which is characterized by the fact that plants, soil or seed materials are treated with an effective amount of the compound of formula I

Ha p A 70 and a f de

X denotes halogen, C.4-C alkyl or trifluoromethyl; t is equal to 0 or 1;

O denotes the groups С(-СН-СН3)-СООСН», С(-СН-ОСНаИ)-СООСНУ с(-М-ОоСНУх)-СооМНеН», С(-М-ОСНя)-СООСН» or M(-ОСНУх) - SOOSN with;

A denotes -О-В, -СНОВ-В, -СНоВ-В, -ОСНОо-В, -СН-СН-В, -С-0-В, СНоО-М-С(83-В 0 or 20. - SN.O-M-S(B7)-S(B7)-M-OVU, moreover

B represents phenyl, naphthyl, 5-ene or b-ene hetaryl or 5-ene or b-ene heterocyclyl, which contains from one to three M-atoms and/or one O- or 5-atom or one or two O- and/or 5-atoms, and the cyclic system is substituted or unsubstituted by one to three KU residues:

Kk? denotes cyano, nitro, amino, aminocarbonyl, aminothio-carbonyl, halogen, C4-Cv-alkyl, C.--Cv-haloalkyl c 29 C.-Ce-alkylcarbonyl, C.-C-alkylsulfonyl, C.-Cv-alkylsulfoxyl , Ca-Cv-cycloalkyl, C.--Cv-alkyl (U

C.-Cv-halogenalkoxy, C.i-Cv-alkyloxycarbonyl, C.-Cv-alkylthio), C.i-Cv-alkylamino, di-C.-Cv-alkylamino,

C.-Cv-alkylaminocarbonyl, di-C.-Cv-alkylaminocarbonyl, C.-Cv-alkylaminothiocarbonyl, di-

C.-Cv-alkylaminothiocarbonyl, C.v.-Cv-alkenyl, C.v.-Cv-alkenyloxy, phenyl, phenoxy, benzyl, benzyloxy, 5- or b-membered heterocyclyl, 5- or b-membered hetaryl, 5- or b -ch-lenny hetaryloxy, С(-МОКо)-OKR or

ОС(Ко)-С(Кр8)-МОКр and the cyclic residues are substituted or unsubstituted with the help of one to three О residues of KO; i am

IN? denotes cyano, nitro, halogen, amino, aminocarbonyl, aminothiocarbonyl, C.i-Cv-alkyl, C.4-Cv-gapogenalkyl, c

C.-Cv-alkylsulfonyl, C.i-Cv-alkylsulfoxyl, C.i.-Cv-cycloalkyl, C.i.-Cv-alkyl, C.i-Cv-halogenalkoxy

Zo C-C-Alkoxycarbonyl, C.4-Cv-alkylthio, C.4-Cv-alkylamino, di-C.-Cv-alkylamino, C.-Cv-alkylaminocarbonyl, di- -

C.-Cv-alkylaminocarbonyl, C.-Cv-alkylaminothiocarbonyl, di-C.i-Cv-alkylaminothiocarbonyl, Co-Cv-alkenyl,

Co-Cv-alkenyloxy, C3-C6-cycloalkyl, C3-C.-cycloalkenyl, phenyl, phenoxy, phenylthio, benzyl, benzyloxy, 5- or b-membered heterocyclyl, 5- or b-- hetaryl, 5- or b --linen hetaryloxy or С(-МОКо)-Окр; « du Co, Kr denote hydrogen or C.-Cv-alkyl; with c B" denotes hydrogen, cyano, Ci-Su-alkyl, Ci-Ci-haloalkyl, C3-Ci-cycloalkyl, Ci-Calkoxy;

IN? denotes phenyl, phenylcarbonyl, phenylsulfonyl, 5- or b-membered hetaryl, 5- or b-membered;" hetarylcarbonyl or 5- or b-lene hetarylsulfonyl, and the ring systems are substituted or unsubstituted by one to three Co residues,

C.4-Cio-alkyl, C3-Ce-cycloalkyl, C-Cio-alkenyl, C-C-o-alkynyl, C4-C4o-alkylcarbonyl, C-Cio-alkenylcarbonyl, and C.-C.o-alkynylcarbonyl, C. -Cio-alkylsulfonyl, or C(K2)-MOB?, and the hydrocarbon residues of these groups are substituted or unsubstituted by one to three K- residues:

IN? denotes cyano, nitro, amino, aminocarbonyl, aminothio-carbonyl, halogen, C4-Cv-alkyl, C.4-Cv-haloalkyl o C.-Ce-alkylsulfonyl, C.-Cv-alkylsulfoxyl, C.-Cv-alkoxy, C.-Sev-halogenalkoxy, C.-Sev-alkoxycarbonyl, c 20 C.1-Sev-alkylthio, S.-Svalkylamino, di- C.-Sv-alkylamino, C.-Sev-alkylaminocarbonyl, di-

C.-Cv-alkylaminocarbonyl, C.-Cv-alkylaminothiocarbonyl, di-C.i-Cv-alkylaminothiocarbonyl, Co-Cv-alkenyl, sl Co-Cv-alkenyloxy

C3-Ce-cycloalkyl, C3-Ce-cycloalkyloxy, 5- or b-ene heterocyclyl, 5- or b-ene heterocyclyloxy, benzyl, benzyloxy, phenyl, phenoxy, phenylthio, 5- or b-membered hetaryl, 5- or b-membered hetaryloxy and 29 Hetarylthio, wherein the cyclic groups in turn may be partially or fully halogenated or may

HF) have from one to three Co residues, and KZ denotes hydrogen, C1-C8-alkyl, Co-C8-alkenyl, Co-C8-alkynyl,

And the hydrocarbon residues of these groups are unsubstituted or substituted with one to three K- residues; which are assimilated by plants or seed material. Along with this, the invention relates in general to the use of compounds of formula I for the immunization of plants against bacterial diseases.

Bacteria are found in temperate and humid-warm climate regions as pathogens (bacterial diseases) on numerous plants. As a result of these diseases, among other things, large economic losses occur.

In general, it is known, for example, the death of all fruit and berry plantations caused by various species of Egmipia ("bacterial burn" on pears and apple trees), as well as wet rot on potatoes and many other plants, in5 different plant tumors caused by agrobacteria and necrosis caused by Hapipotopadep on various types of vegetable crops, rice, wheat and citrus fruits. Bacterial diseases caused by Rzepdotopadep are especially dangerous,

in particular, on vegetable, tree and shrub fruit crops and on tobacco plants.

Conventional fungicides, which interfere with the metabolic processes specific to fungi, do not act against bacteria, which is not unexpected. Until now, the fight against them was possible only through the use of antibiotics (for example, streptomycin, blasticidin Z or kazugamycin), which, however, was rarely practiced.

The large-scale use of antibiotics in agriculture is controversial, since these antibiotics use basically the same mechanisms of action as against bacterial pathogens in medicine and veterinary medicine. At the same time, they can contribute to the development of resistance. In addition, due to their mostly complex molecular structure, antibiotics are expensive and can only be obtained by biotechnological means. 70 Therefore, the beneficial principle is the use, accordingly, the stimulation of protective mechanisms characteristic of plants.

The European application (EP-A 420 803) describes the immunizing action of benzo-1,2,3-thiazole derivatives against various phytopathogenic microorganisms. From international application MU0O-A 96/37493| a similar effect of pyridylthiazoles is known.

However, the action of these substances in many cases is unsatisfactory.

The task of this invention is to develop a method of wide application that does not interfere with the mechanisms of fighting bacteria in humans or animals, is ecologically and toxicologically harmless, does not harm plants, and provides effective immunization against phytobacteria.

In accordance with this, the above method was developed. The active substances that are used are known as fungicides and, nowadays, also as insecticides | see documents ER-A 178 826; ER-A 253 213; M/0-A 93/15046;

MO-A 95/18789; MUO-A 95/21153; M/O-A 95/21154; MUO-A 95/24396; MMO-A 96/01256; UMO-A 97/15552). There have been no results on the stimulation of the "immune system" of plants, which leads to resistance against bacteriosis.

Good plant tolerance of the active substances of the formula! in the concentrations necessary for combating plant diseases, they allow both the treatment of above-ground parts of plants, and the treatment of planting and sowing material and soil. high school

In the method according to the invention, the active substance is perceived by plants either through the surface of the leaves or through the roots of the plants and is distributed in the plant sap throughout the plant. and)

In this way, the protective effect occurs after applying the method according to the invention not only on the parts of the plants that are directly sprayed, but also the resistance against bacteriosis of the entire plant increases.

In the preferred form of implementation of the method according to the invention, aerial parts of plants are treated with preparative forms of the active substance of formula I.

The preparation of the active substance, which is used in the method according to the invention, is known from the above publications. yu

For the method according to the invention, active substances with the following values of substituents, both individually and in combination, are particularly preferred. co

Particularly preferred for the method according to the invention are the active substances of the formula I!, in which C) denotes и-с(-Ссн-ОосСНУ)-сСооСснН», С(-М-ОСНУИ)-СООСН with or M(-ОСНУ»)-СООСН with.

Preferred values for residue B in formula I are phenyl, pyridyl, pyrimidinyl, triazolyl and pyrazolyl.

For the method according to the invention, the active substances of the formulas from II to II are especially preferred, in which

M stands for OSN" and MNSN", especially OSN", "

ХУ СН and УЧ, and M and with T and 7 denote independently of each other СН and M. . Preferable active ingredients of formula I, in which ОО denotes М(-ОСН 3)-СООСН»)| are the compounds described in and? publications (M/O-A 93/15046 and UMO-A 96/012561.

Preferred active substances of formula I, in which 0 denotes C(-CH-OSH 53)-СООСН", are compounds described in publications (EP-A 178 826 and EP-A 278 595). -I The preferred active ingredients of formula I in which 0 denotes С(-М-ОСН 53)-СООСН» are the compounds described in the documents (ЕР-А 253 213 and ER-А 254 426). The preferred active substances of formula I, in which 0 denotes C(-M-OSH 53)-SOMNOCH", are the compounds described in the documents (EP-A 398 692, EP-A 477 631 and EP-A 628 540).

The preferred active substances of formula I, in which 0 denotes C(-CH-CH 53)-СООСН", are the compounds described in the documents (ЕР-А 280 185 and EP-АЗ5БО 6911. сл. The preferred active substances of formula I, in which A denotes -CH20O-M-C(B 7)-B, there are compounds described in the documents (EP-A 460 575 and EP-A 463 488).

Preferable active substances of formula I, in which A stands for -O-B, are compounds described in documents EP-A 382 375 and EP-A 398 6921.

The preferred active substances of formula I, in which A stands for -"СНХО-М-С(В 7)-С(82)-М-OKU, are the compounds described in the documents (ММО-А 95/18789, M/О-А 95/21153, MUO-A 95/21154, MUO-A 97/05103 and UUO-A 97/061331). Namely) Particularly preferred active substances of formula I, in which O denotes M(-ОСН»3)-СООСН», A denotes СНо-О- and 60 B denotes 3-pyrazolyl or 1,2,4-triazolyl, and B may have one or two substituents selected from the group consisting of halogen, methyl and trifluoromethyl, and phenyl and pyridyl, in particular, 2-pyridyl, and these residues are substituted from 1 to 3 by residues ve.

These active substances are expressed by the formula ИЙ b5 y- o | M. U

M t y o. . sen

PIT in which VC?" denotes chlorine, methyl or trifluoromethyl, KE? has the value given for formula I and x is equal to 70 1 or 2, and y is equal to 0 or 1.

Especially preferred are the active substances of the formula I" (B,

Further, the active substances of the PI formula are preferred: ! - o. Oh, and the UN,

In THAT case where M stands for OSN" or INN" and U stands for M and K? denotes halogen, C.-C.-alkyl, C.-4-C.-haloalkyl or C.-C.-haloalkyl.

Particularly preferred are the active substances of formula I, in which M denotes OSH 3 and KU denotes halogen, methyl, dimethyl or trifluoromethyl, especially methyl. yu

Considering their application, the compounds shown in the tables below are especially preferred. oh

Taeipatsya iv) sot bhn TV, so pom to" -

Osn, 7 x "vd

Osn, And t | t A U The welfare of the group Pi M LIch. Jane"

Fronil Ve zo retro ueokeniae org 1 i ro VatevE -I av Gen) -7 aa, iy eztiove avt. 17007 | I kitov so poly oh po shk po Me thatttiavk

I-th | se - 1 VsNE | osA vat eve 1 with | Jan Ge and E Z-svu tora oatiyav sya 70 sereten, 5 de, And agznia sliye sya bn, - zho ik VIGYINIg le sia | 1 c - womb avgaZV a

Tabilatsia

F) Fr

Hn) ! base, first name) In . m g 60 b5

-i m ИЙ in | t.

And axes Ш 2:сН, 7 ER-AFEZ 215 and growth of spring: | ER-ALI 215 lab nnep i sn | prAyat Em sa | MIST m with GRAT

T-5 0 Ministry of Internal Affairs; Sh t KEN, shi dosto pika Y pl | nnen: yasni Oose EG-A BIV I /0 p | nneng Hn pera 0700000 | EV veya no

H 1 - the first day of the dream.

Ts b omaSya:T VI 2-snua osniennsssyaenOoS' TER AT IZ BOV goi-ya | nnenu| No! d Osnisnu ram; | Eva t sia mon chNnena nm | 2-snia-osnisvunsisnale nos | EGeshchi? 18 TU etorkneny m 1-Staobnisnya. siv lemy, y 18 tsk - В8-62Й227 eiblitsa I

AND

! b,

And talk about her." Those,

And 1

M. ma t- U t GO sweat. Jerop

A thousand? Osn GI pasNIya-sv Uk A VES? with dv same GT osn sr ono eoyupny sg | And BVNBOgI ate 1 person сн сай 00003000Св ERA TV ВН ше | chnSVI M o| sya magy DY KRAN V: gotv | chnsn; in the dream of the ERA, her name is Shcheo,

She fr onnenIi Mo on ZE SI BELA ZIVENE yu boshno|yanenu ono sas ER-A ZUBI - -- I. e - 5 -- E-- 15 . IS

Taitatsn (ee) in! and - mo in her - Wasps, m mi « and the SAME IN Pit. Jerop

And here we are - s pa-1 sZHIN, sn | en, SS v-va ts pa | esn; sn osti pasa ERA ZOBOV "» pz |vNSKU| A SN) 0 sobs; to Aa zE ' 1

Internship |vmsz|Yi oi sn! 00 (.Obeess. I dk zamlavyay set shen -1 osn Mo s, (ost: Eva BIV pev | OsSNI Mo SN; TYA-SezyuN: ERA IOV bo t osn. Mo sn (ZAS: yu Z EBA МЙ BIV ' «sl Osn Mo SNI PBS ZhiNya ERA ZB ZE 1 Table with sl -

AND:

S-sh I a | h usn, i:

U sm ko bo b5 ti U E shi k pit. Dzherag Ombre Oso St. 007on ОЙ sn, | linguistic h- so sn.| 770005 bedrooms Huh skwtaa. pa then osv, | St | 73 sneyun,: Ton; to property, powerful, | I slept, I woke up! zvo 7 mnona | the sleep of the boulders 07 | sna pkzvsnnt m S ochvsn. | sya, a sina SN: Hn oh vteya h-7 ME 2 dis Sh Sn: God eh still m Neon | with 4 sohoni soo| s A kava chish onpepz | Sat en ebchi s triyau yod vam m-2 7 mnon, | Shnezhona's dream | sleep | gave ear macho onnsny| sia; snezervit | snu |Hekbh lov sv) h-14 chn, shcha shiSNISn Sn; Chiv, you" p ne mi mile

Tavlatsia m -ry o sn, sch

M o

In sli: roti ra olitjerstla S chi 1 MNN Ii ER-A tavra zv naya ER-A CHE BIZ y par knet ne ERA ZavVai yuyu ane ERI,

Mnenu gm EKAEVY yu sho" mnen.| m U EIz.d ZUB etsЯ 1 so

From Table y. - n | I ba « shi - s M SA) h Not ch t in Tit. the sources of her foundation, ha dod svsni 7 defects zhN or | both epi and 00 bissc 0 BRA zda zi Gb | sleep! 00 схКсоны с и ER-Vаци ЗР и лаков! "Tk (Y yaachks-sev 000 bivea de tayaya so cha |chChnstiI "77 asnrasiuyuvu 0 sla gg zam s "rerovysyutny vvkhantnyu sl 50 zi | ns no t ars siva si sna sty? we. mnon! IK Zhasue SNI St.d yava va sl saga tnnsni MIN Ka Kit Asya | respect tyu t vnena mik gave sni shogunye E ucha avtva nya o vnen,| mo mu yaeozevizlzhevvnihk | ana fled

Compounds of the formula | increase plant resistance to bacterial diseases. They have (F) special importance in the fight against bacteria on various cultivated plants, such as vegetable crops, tree or shrub fruit species and tobacco plants, as well as on the seeds of these plants.

They are especially suitable for combating the following plant diseases: species of Rzeyidotopa on tobacco plants, potatoes, tomatoes and leguminous crops and, in particular, species of Egmipia on fruit, vegetable crops and potatoes.

Compounds of formula II, in particular, compound 11-1, are particularly suitable for the control of Egmipia species.

Compounds of the formula | are used in such a way that plants to be protected from bacterial damage, seed material or soil are treated with an effective amount of active substances. Application 65 is carried out before infection of plants or seed material with bacteria. As a result, a significant reduction in the susceptibility of plants to bacteriosis is achieved.

Consumption rates when used for plant protection, depending on the type of pathogen and the type of plant, are in the range from 0.01 to 2.0 kg of the active substance per hectare.

When processing seed material, in general, the amount of active substance from 0.001 to 0.1 g, preferably from 0.01 to 0.05 g per kg of seed material is required.

Compounds of the formula | can be translated into the usual preparation forms for fungicides, for example, solutions, emulsions, suspensions, powders, powders, pastes and granules. The application form is oriented to the purpose of application, it should in any case ensure a thin and uniform distribution of the compounds according to the invention. 70 Preparative forms are obtained in a known manner, for example, by diluting the active substance with solvents and/or fillers, optionally using emulsifiers and dispersants, and in the case of water as a diluent, other organic solvents can be used as auxiliary agents. As auxiliary agents, the products usual for fungicides are suitable.

Preparative forms generally contain between 0.01 and 95% by weight, preferably between 0.1 and 9% by weight of the active substance.

The active substances have a purity from 9095 to 10095, preferably from 9595 to 10095 (according to the NMR spectrum).

Examples of preparative forms:

Y. bBvag. parts of the compound according to the invention are thoroughly mixed with U95wag. parts of thin kaolin.

In this way, a tool for dusting is obtained, which contains 5 wt.9 o of the active substance.

P. ЗОваг. parts of the compound according to the invention are thoroughly mixed with 92 wt. parts of powdered silica gel and 8 wt. parts of paraffin oil, which is sprayed onto the surface of this silica gel. In this way, a preparative form of the active substance with good adhesive ability is obtained (the content of the active substance is 2Zmas.9o).

Sh. 7 Ovag. parts of the compound according to the invention are dissolved in a mixture consisting of Z9Owag. parts of the science of XYLOL, bvag. parts of the addition product from 8 to 1 mole of ethylene oxide to one mole of M-monoethanolamide of oleic acid, 2 wt. parts of the calcium salt of dodecylbenzene sulfonic acid and 2 wt. parts of the product i) addition of 4O0 moles of ethylene oxide to one mole of castor oil (content of the active substance Umas.9b).

IM. 20 weights parts of the compound according to the invention are dissolved in a mixture consisting of 60 wt. parts of cyclohexanone, weight parts of isobutanol, 5 kg. parts of the product of the addition of 7 moles of ethylene oxide to thymol with isooctylphenol and 5 wt. parts of the product of the addition of 40 moles of ethylene oxide to one mole of castor oil (the content of the active substance is 16 mab.9b). i am

M. 8Ovag. parts of the compound according to the invention are well mixed with Weight. parts of the sodium salt of diisobutylnaphthalene-alpha-sulfonic acid, 10 wt. parts of the sodium salt of lignin sulfonic acid from spent sulfite alkali and 7 wt. parts of powdered silica gel and ground in a hammer mill (active substance content 8Omas.9b). M

E. Mix U9Ovag. parts of the compound according to the invention from 1Ovag. parts of M-methyl-a-pyrrolidone and obtain a solution that is suitable for use in the form of the smallest drops (the content of the active substance

ZOmas.Ob).

E. 20 kg parts of the compound according to the invention are dissolved in a mixture consisting of 40 wt. parts of "Cycpohexanone, ЗОваг. parts of isobutanol, 20 kg. parts of the product of the addition of 7 moles of ethylene oxide to the mole -ptv) of isooctylphenol and 1 Ovag. parts of the product of joining 40 moles of ethylene oxide to 1 mole of castor oil. By concentration and fine distribution of the solution in 100 OOw. parts of water to obtain an aqueous dispersion containing 0.02 wt.% of the active substance.

MICE. 20 Ovag. parts of the compound according to the invention are well mixed with Weight. parts of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 kg. parts of the sodium salt of lignin sulfonic acid from sulfite-I spent alkali and bOvag. parts of powdered silica gel and ground in a hammer mill.

By thin distribution of the mixture in 2000Owag. parts of water, a solution for spraying is obtained, which contains about 0.9% by weight of the active substance. Aqueous preparative forms can usually be prepared from emulsion concentrates, pastes or powders that are wetted (powders for spraying, oil dispersions) by adding water. For the production of emulsions, pastes or oil dispersions, substances as such or dissolved in oil can be homogenized in water with the help of wetting agents, adhesion activators, dispersants or emulsifiers. Concentrates may also be prepared which consist of the active substance, a wetting agent, an adhesion promoter, a dispersant or an emulsifier and possibly a solvent and an oil which can be diluted with water. 5B The concentration of the active substance in ready-to-use preparations can vary widely.

In general, it is from 0.0001 to 1095, preferably from 0.01 to 195. (F, Active substances can be used with success at particularly low consumption rates, and there is an opportunity to use preparations with more than 95% by weight of the active substance or even apply the active substance without additives. In the active substances can be added oils of various types, herbicides, other fungicides, other means of pest control, bactericides, if necessary, also immediately before use (mixtures in the tank). These means can be mixed with means according to the invention in a weight ratio from 1:1O0 to 10:1.

Indication of the effect of induced stability of the active substance of formula I! to bacteria can be carried out as indicated on the package or in the product information sheet. The indication can be carried out on drugs that 65 Can be used in combination with active substances of formula I.

Induction (stimulation) of resistance can also be an indication that can be the subject of official approval for the use of the active substance of formula I.

Action of compounds of the formula | can be shown by the following tests. Examples of applications to stimulate resistance to bacteria. Plant material

For the tests, tobacco plants (Misoiipia jarasit su. Hapipi-ps) are grown at 252C, 5995 air humidity and a daily light period of 16 hours (150-200μM quantum/s/m'7) for a period of time from b to 8 weeks in diving soil - mixtures (typical mixture of type EO 73). Some of the plants are fertilized once a week by adding commercially available flower fertilizer (1095 total nitrogen, 995 phosphate, 7905 potassium) to the irrigation water in the recommended dosage. 70 Application of the active substance

The active substance as a 0.immol aqueous solution (diluted with 195 vol/vol dimethylsulfoxide) is sprayed onto the plants or infiltrated directly into the tissue of the leaves using a very fine injection cannula.

Control plants are similarly treated with solutions that do not contain the active substance. To reduce the effect of biological dispersion in some tests, half of the leaves (to the left and right of the middle rib) are treated with a 75% solution of the active substance, and the other half of the same leaf is treated with a control solution.

After application and subsequent inoculation with Rzepdotopaz zugipdae, the plants are left in the breeding chamber.

Inoculation / infection and determination of resistance

Treated as described above with the active substance, tobacco plants, respectively, leaves, infect Rzeiidotopaz zuypdaee ru. Utah strain YuSZ3000; supplier: Vgiap biazKam/is:, Opimegeiu oi Saijogpia, Wegkeiu, SA) or

IRzedotopaz zugipdae ru. yarasi (German Collection of Microorganisms and Cell Cultures, Braunschweig,

Germany). To do this, the bacteria are grown for 1 day at 30 °C in Kipudz B medium, centrifuged, washed and in a solution of 10 mmol of MoSi" set to a density of 109 si ml". About 200 ml (2 x 107.7 ml") of this inoculum is infiltrated through small wounds in leaves applied by cannula directly into the tissue of 29 leaves. at

Next week, the development of leaf necrosis as a result of infection is determined. The absence of necrotic symptoms is characteristic of the induced stability of leaf tissue.

Determination of bacterial growth

To quantify the population of bacteria, cut out two pieces (0 1 cm) from the infected zone of the leaf and homogenize them in 500 ml of sterilized water. A number of diluted preparations are placed on Kipuz B agar and after 2 days of incubation at 3092C, the density of the initial population (one hundred) per one puck of a leaf is calculated from the number of colonies that have formed. at

An example of application of p

Increased resistance to Rzendotopaz zugipdae ru. ota О0СЗ000 (incompatible interaction) and the slow formation of symptoms of the disease caused by Rzepdotopaz zugipdae ru. (arasi (combined interaction), on tobacco leaves after treatment with the active substance 1-5.

Example.1. Immunization against Rzeidotopaz zugipdae ru. yabashi (compatible interaction)

Thanks to treatment (from 24 to 48 hours before inoculation) with the help of "-0.0195-th composition of active" substances 1-5 in the case of a compatible host-pathogen combination, the growth of bacteria is inhibited and the formation of C7C70 symptoms of the disease is reduced. c Kinetics of growth of Rzeidotopaz zugipdae ru. (arasi after infection of Kipd B-environment with a colony in the presence, "with, respectively, in the absence of the active substance I-5 shows that the active substance itself has no effect on the growth of ip mio bacteria.

The established effect is based on the stimulation of the plant's inherent protective ability, respectively, resistance 75 to the pathogen. -AND

Ge | Table A (9) Growth of Rveidotopav zugipday ru. garasi in an inoculated leaf of a tobacco plant about Agreement) (leaf washers") sny a i PO t o ka Example 2: Immunization against Rzepdotopazg zugipdae ru. Utah OSZ3000 incompatible interaction)

Also in the case of incompatible interaction (that is, the plant itself quickly reacts to the introduced pathogen with the formation of "Protective"-) necrosis, in which the infected areas of the leaves die and the formation of symptoms is greatly reduced.

Table B

The development of damage to tobacco leaves after inoculation of the intercostal zone with Rzetsdotopaz 5ugipdae ru. ota ЮСЗО000 b5 leaves (95 surfaces of the intercostal zone) left

Active ingredient 1-5 16611611 jan nn nn i o i Po ny I ny z PO I PO I PO kp v 680 di la 15600001 levv 0 |777111161117111111ю111111111111111lo

After applying the composition of the active substance 1-5, small necrotic zones are limited directly to the inoculation sites on the wounds of the leaves. The leaves of the control plants wilt after 24 hours and die completely after 48 hours.

Claims (9)

The formula of the invention 1. A method of immunizing plants against bacteriosis, which differs in that plants, soil or sowing material are treated with an effective amount of the compound of the formula I ХХО) Kk se A o o o where X means halogen, C.4-C,-alkyl or trifluoromethyl; t is equal to 0 or 1; Іо) (in means groups Ф(-СН-СНУЗ)-СООСН,, Ф(-СнН-ОоСНУ)-СООСН», Ф(-М-ОСНУ)-СОМНеН with, ою С(-М-ОСНай)-СООСН with or M(-OSNU)-СООСН"; A means -О-В, -"СНХО-В, -ОСНо-В, -СНАСН-В, -С 2 С-В, СНоО-М-АС(В )-В or -"СНХО-М-С(Б 7)-С(22)-М-ОКУ, which) and с Б means phenyl, naphthyl, 5--len or b--len hetaryl or 5--len or b- -lene heterocyclyl, which Z0 contains from one to three M-atoms and/or one O- or 5-atom or one or two O- and/or 5-atoms, wherein the O ring system is substituted or unsubstituted by one to three of the remains of KU: K? means cyano, nitro, amino, aminocarbonyl, aminothiocarbonyl, halogen, C-Cv-alkyl, C-Cv-haloalkyl, C.Ci-alkylcarbonyl, C.i-Ce-alkylsulfonyl, C.-Ci-alkylsulfoxyl, C.-Ci-cycloalkyl, C.-Ci-alkyl, « 20 C.i-Ci-halo-alkoxy, C.-Ci-alkyloxycarbonyl , C.-Cv-alkylthio, C.-Cv-alkylamino, di-C--Cv-alkylamino, -in C.1-Cv-alkylaminocarbonyl, di-Ci-Cv-alkylaminocarbonyl, C.i-Cv-alkylaminothiocarbonyl, di-C--Cv-alkylaminothiocarbonyl, Co-Cv-alkenyl, Co-Cv-alkenyloxy, phenyl, phenoxy, benzyl, benzyloxy, 5- or b-membered heterocyclyl, 5- or b-membered hetaryl, 5- or b-membered hetaryloxy, C(-MOBL)ОВ g or ОоС(87)5-С(В c)-МОВ c, and the cyclic residues are substituted or unsubstituted by one to three -1 residues B; VE? means cyano, nitro, halogen, amino, aminocarbonyl, aminothiocarbonyl, C-Cv-alkyl, C.i-Cv-haloalkyl, because C.-Cv-alkylsulfonyl, C.i-Cv-alkylsulfoxyl, C3-Ce-cycloalkyl, C .-Cv-Alkoxy, C.-Cv-Halo-Alkoxy, 1 C.-Cv-Alkoxycarbonyl, C.-Cv-alkylthio), C.-Cv-alkylamino, di-Ci-Cv-alkylamino, C.-Cv-alkylaminocarbonyl, sl 50 di-Ci-Cv-alkylaminocarbonyl, C. -Cv-alkylaminothiocarbonyl, di-Ci-Cv-alkylaminothiocarbonyl, Co-Cv-alkenyl, Co-Cv-alkenyloxy, Cz-Ce-cycloalkyl, Cz-C.-cycloalkenyl, phenyl, phenoxy, phenylthio, benzyl, benzyloxy, 5- or sl b-membered heterocyclyl, 5- or b-membered hetaryl, 5- or b--membered hetaryloxy or C(I-MOCLZOV c; K i, K g mean hydrogen or C 1-6-alkyl; B" means hydrogen, cyano, C4-C4-alkyl, C4-C4-haloalkyl, C3-C6-cycloalkyl, C4-C4-alkoxy; o B? means phenyl, phenylcarbonyl, phenylsulfonyl, 5- or b-membered hetaryl, 5- or β-membered hetarylcarbonyl or 5- or β-membered hetarylsulfonyl, and the cyclic systems are substituted or unsubstituted by means of one to three K 5 residues, in C.4-Cio-alkyl, C3-Ce-cycloalkyl, Co- C0-alkenyl, C0-C0-alkynyl, C4-C-o-alkylcarbonyl, C0-C0-alkenylcarbonyl, C3-C0-alkynylcarbonyl, C.-C.o-alkylsulfonyl, or C(B.)-MOV8, including the hydrocarbon residues of these groups are substituted or unsubstituted by one to three KU residues; KK stands for cyano, nitro, amino, aminocarbonyl, aminothiocarbonyl, halogen, C1-C6-alkyl, C4-C6-haloalkyl C.-Cv-alkylsulfonyl, C.i-Cv-alkylsulfoxyl, C.i-Cv-alkoxy, C.-Cv-halogenalkoxy, C.-Cv-alkoxycarbonyl, because C.-Cv-alkylthio, C.i-Cv -alkylamino, di-Ci-Cv-alkylamino, C.-Cv-alkylaminocarbonyl, di-C-i-Cv-alkylaminocarbonyl, C.-Cv-alkylaminothiocarbonyl, di-C--Cv-alkylaminothiocarbonyl, Co-Cv-alkenyl, Co-Cv-alkenyloxy, C3-Ce-cycloalkyl, C3-Ce-cycloalkyloxy, 5- or b-ene heterocyclyl, 5- or b-ene heterocyclyloxy, benzyl, benzyloxy, phenyl, phenoxy, phenylthio, 5- or b-membered hetaryl, 5- or b-membered hetaryloxy and hetarylthio, and the cyclic groups in turn may be partially or fully halogenated or may have from one to three KU residues; and BZ means hydrogen, Ci-Cv-alkyl, Co-Cv-alkenyl, Co-Cv-alkynyl, and the hydrocarbon residues of these groups are unsubstituted or substituted by one to three VC residues; which is assimilated by plants or seed material. 2. The method according to claim 1, which differs in that the active substance of the formula I is used, while O means 70 c(СнН-ОоСНУ)-сСоОоСснН», С(-М-ОСНУИ)-СООСН» or MЩ-ОСНУ)-СООСН ". C. The method according to any of claims 1 or 2, which differs in that t is zero and the substitutes in the formula have the following meanings: A means -О-В, -"СНЯО-В, -"СНЙО-М-С( В 7)-В or СНо-О-М-С(В. )-С(82)-М-OK; B means phenyl, pyridyl, pyrimidinyl, pyrazolyl, triazolyl, and these cyclic systems are substituted by one 19 or two KU residues; IN? means C1-C8-alkyl, Co-C8-alkenyl, C3-C8-cycloalkyl, and these groups are unsubstituted or substituted by one or two B residues; B means C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkyl, C1-C6-halogenoxy, benzyl, phenyl or phenoxy; or phenyl, substituted or unsubstituted by one or two KU residues; and BZ means C 1 -C 1 -alkyl, C 1 -C 6 -alkenyl or C 1 -C 6 -alkynyl. 4. The method according to any of claims 1-3, which is characterized by the fact that an effective amount of the compound of formula I is used for processing; (1) с и я о и М T-- - т осн, (89, ю осн, ю where T denotes a carbon or nitrogen atom, KU denotes chlorine, methyl or trifluoromethyl, KO has the values given for IS o) compounds of formula I , x is equal to 1 or 2 and y is equal to zero or 1. so 5. The method according to any of claims 1-3, which is characterized by the fact that an effective amount of the compound of the formula is used for processing: with . And" U where M means OSN", U means M and K? means methyl, dimethyl or halogen. 6. The method according to any one of claims 1-5 for immunization against Egmipia species. -and 7. The method according to any of claims 1-6, and plants are treated. co 8. The method according to any of claims 1-6, and seed materials are processed. 9. Application of compounds of formula I according to any of claims 1-5 for immunization of plants against bacteriosis. 1 Official Bulletin "Industrial Property". Book 1 "Inventions, useful models, topographies of integrated microcircuits", 2007, M 4, 15.04.2007. State Department of Intellectual Property of the Ministry of Education and Science of Ukraine. F) name) 60 b5