UA97798C2 - Use of strobilurin or salt thereof for improving tolerance of plants to low temperatures and method for improving tolerance of plants to low temperatures - Google Patents

Abstract

The present invention relates to the use of an active compound that inhibits the mitochondrial breathing chain at the level of the b/c1 complex for improving the tolerance of plants to low temperatures.

Description

The actual invention relates to the use of compounds that suppress the mitochondrial respiratory chain at the level of rB/s1 complex, especially active strobilurin compounds, to increase the resistance of plants to low temperatures and/or frosts.

Temperature is one of the main factors affecting plant growth. Low temperatures (down to 0"C) and frost (temperatures below 0"C) can slow down the germination and growth of plants and have a significant effect on their development and on the quantity and quality of their products. Agricultural plants such as corn, sugar beet, rice, soybean, potato, tomato, red pepper, melon, cucumber, bean, pea, banana and citrus species are damaged and/or significantly stunted at temperatures below 57C. Even temperatures that are slightly below 0"C lead to partial or complete death of these plant species. Late frosts close to the time of flowering, for example, repeatedly lead to significant yield losses, for example, in varieties of seed and stone fruits such as apple, pear, quince, peach, nectarine, apricot, plum, prune, almond, or cherry. Chilling or frost-damaged plants show signs of dieback, such as leaves, flowers, and buds. Frost-damaged flowers do not develop fruit at all. or develop already damaged fruit or fruit with damaged skin that are difficult to sell, if at all.Severe chilling damage and frost damage result in the death of the entire plant.

Therefore, damage from cooling and damage from frost are important loss factors for the agricultural sector. Existing options for preventing chilling damage and frost damage with are rather unsatisfactory due to their complexity or the fact that it is often not possible to obtain the same results. Possibilities that should be mentioned in this context are the breeding of cold- and frost-resistant plant species, the placement of cold-sensitive plants in a greenhouse with subsequent planting in the soil as late as possible, cultivation under plastic film, air circulation in the stand, blowing in warm air, placement of heaters in a stand, and irrigation protection from frost.

ORE 4437945 oyissus plant-strengthening products containing vitamin E, which are said to reduce the harmful effect of phytotoxic agrochemicals and other abiotic stressors on the plant. These compositions may additionally contain cryoprotectants, such as glycerin. A cryoprotectant, which is optionally present, is not described as having the effect of preventing damage from chilling or frost damage.

U. Hak and K. Oogyipd describe in Rnuzioa. Riapi 63. 287-292 (1985) that abscisic acid can increase frost resistance to low temperatures in hardened winter wheat.

The task of the valid invention is to obtain a composition that increases the resistance of plants to low temperatures and/or frosts.

This task is performed when using an active compound that suppresses the mitochondrial respiratory chain at the level of the B/si complex, to increase the resistance of plants to low temperatures. Particularly suitable for the purposes of the present invention are

Active compounds that suppress the mitochondrial respiratory chain at the level of the B/c1 complex are known as fungicides from the literature (see, for example, Oespeta-Mopodgarniep Va. 129, 27-38, MSN Mepadzdeteipzsnai

M/eipneit 1993; Mage! Rhodisi Nerohiv 1993, 565-574; Viospet. boss. Thapv 22, 635 (1993)). However, there has been no suggestion until now that such active compounds can be effectively used to increase the resistance of plants to low temperatures and/or frost, which was found only within the framework of the present invention.

A particularly important class of active compounds that suppress the mitochondrial respiratory chain at the level of the B/c1 complex are strobilurins. Strobilurins are mainly known as fungicides for a long time and, in some cases, have also been described as insecticides (EP-A 178 826; EP-A 253 213; MO 93/15046; MO 95/18789; MO 95/21153; MO 95 /21154; MO 95/24396; UMO 96/01256; UMO 97/15552; MO 97/27189). Famoxadone (5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-2,4-oxazolidinedione) is also an example of an active compound that suppresses the mitochondrial respiratory chain at the level of the rB/c1 complex.

Individual examples of suitable strobilurins are compounds of the formula kl me and ee I ! XX

In which the variables are defined below:

X means halogen, C-C4-alkyl or trifluoromethyl; t means 0 or 1;

O means С(-СН-СН3)-СООСН», С(-СН-ОСН3З)-сСОоОснН», С(-М-ОСН3)-СОМНеН»z, С(-М-ОСиН3)-СООСН with,

М(-ОсСН3)-СООСН», or group О1 и и и и и т в осн, с! where Z denotes a bond with a phenyl ring;

And means -0-В -СН2гО-В, -ОСН»e-В, -"СНg5-В, -"СНАСН-В, -С-0-В, -«СНgОо-М-С(А)-В, -Sng8-M C(8)-B -CHgO-M-C(B)-CH-CH-B, or -CHgO-M C(B)-C(B2) M-OVU, where

B means phenyl, naphthyl, 5- or b-alene heteroaryl or 5- or b-alene heterocyclyl, which contains one, two or three nitrogen atoms and/or one oxygen or sulfur atom or one or two oxygen atoms and/ or sulfur, where the cyclic system is unsubstituted or substituted by one, two or three Be groups:

And independently of each other mean cyano group, nitro group, amino group, aminocarbonyl, aminothiocarbonyl, halogen, Ci-Cv-alkyl, Ci-Cv-haloalkyl, C1i-Cv-alkylcarbonyl, C1i-Cv-alkylsulfoyl, Ci1-Cv-

alkylsulfinyl, C3-Cv-cycloalkyl, C-Cv-alkyloxy group, C-Cv-haloalkyloxy group, C1-Cv-alkyloxycarbonyl, C1-Cv- alkylthio group, C1-Cv-alkylamino group, di-C1i-Cv-alkylamino group, C1i-Cv- alkylaminocarbonyl, di-C1-Cv- alkylaminocarbonyl, C-Cv-alkylaminothiocarbonyl, di-Ci-Cv-alkylaminothiocarbonyl, Co-Cv-alkenyl, C2-Cv- alkenyloxy group, phenyl, phenoxy group, benzyl, benzyloxy group, 5- or 6-membered heterocyclyl, 5- or 6-membered heteroaryl, 5- or b-membered heteroaryloxy group, C(-MOVZ2)-B? or OS(B2)2-C(B2)-MONE, where cyclic radicals, in turn, can be unsubstituted or substituted by one, two, three, four or five Be groups:

AND? independently of each other mean cyanogroup, nitro group, halogen, amino group, aminocarbonyl, aminothiocarbonyl, Ci-Cv-alkyl, Ci-Cv-haloalkyl, Ci-Cv-alkylsulfonyl, C1i-Cv-alkylsulfinyl, C3-Cv-cycloalkyl,

Ci-Cv-Alkoxy group, Ci-Cv-haloalkyl group, Ci-Cv-Alkoxycarbonyl, Ci-Cv-Alkylthiogruiu, Ci-Cv-alkyl amino group, di-C1i-Cv-alkylamino group, C1-Cv-alkylaminocarbonyl, di-Ci- C1-alkylaminocarbonyl, /-C1-Cv- alkylaminothiocarbonyl, / di-Ci-Cv-alkylaminothiocarbonyl, Co-Cv-alkenyl, Co-Cv-alkenyloxy group, /C3-Cv- cycloalkyl, C3-Cv-cycloalkenyl, phenyl, phenoxy group, phenylthio group, benzyl, benzyloxy group, 5- or 6-membered heterocyclyl, 5- or b-membered heteroaryl, 5- or b-membered heteroaryloxy or C(-MOV)-B8;

VU, VU independently of each other mean hydrogen or Ci-Cv-alkyl;

IN! means hydrogen, cyano group. C1-Cα-alkyl, C1-Cα-haloalkyl, C3-C6-cycloalkyl, C1-Cα-alkyl, or C-

C.-alkylthio group;

IN? means phenyl, phenylcarbonyl, phenylsulfonyl, 5- or b-membered heteroaryl, 5- or b-membered heteroarylcarbonyl or 5- or b-membered heteroarylsulfonyl, where the ring system may be unsubstituted or substituted with one, two, three, four or n by NU groups,

C1-Cio-alkyl, C3-C6-cycloalkyl, Co-Cio-alkenyl, C2-Cio-alkynyl, C1i1-Cio-alkylcarbonyl, Co-Cio-alkenylcarbonyl,

C3-Cio-alkynylcarbonyl, C1-Cio-alkylsulfonyl or C(-MOV2)-PE, where the carbon chains may be unsubstituted or substituted by one, two, three, four or five B- groups:

Ag independently of each other means cyano group, nitro group, amino group, aminocarbonyl, aminothiocarbonyl, halogen, C-Cv-alkyl, C-Cv-haloalkyl, C1i-Cv-alkylsulfonyl, C1-Cv-alkylsulfinyl, C1-Cv- alkoxy group, C- C1-Cv-alkoxy group, C1i-Cv-Alkoxycarbonyl, C1-Cv-alkylthio group, C-Cv-alkylamino group, di-

C1i-Cv-alkylamino group, C-Cv-alkylaminocarbonyl, di-C1-Cv-alkylaminocarbonyl, C-Cv-alkylaminothiocarbonyl, di-

Ci-Cv-alkylaminothiocarbonyl, Co-Cv-alkenyl, Co-Cv-alkenyloxy group,

C3-C8-cycloalkyl, C3-C8-cycloalkyloxy, 5- or b-membered heterocyclyl, 5- or b-membered heterocyclyloxy, benzyl, benzyloxy, phenyl, phenoxy, phenylthio, 5- or 6b-membered heteroaryl, 5- or 6 -h-len heteroaryloxy or heteroarylthio group, where the cyclic groups can be partially or completely halogenated or can be replaced by one, two or three Na groups; and

VAZ means hydrogen, Ci-Cv-alkyl, Co-Cv-alkenyl, Co-Cv-alkynyl, where the carbon chains may be partially or fully halogenated or may be substituted with one, two, three, four or five B groups; and strobilurin compounds selected from the group containing methyl-(2-chloro-5-|1-(3-methylbenzyloxyimino)-ethyl|-benzyl)-carbamate, methyl-(2-chloro-5-(1-(b -methylpyridin-2-ylmethoxyimino)-ethyl|-benzyl)-carbamate, 2-(2-(6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yloxy)-phenyl)-2-methoxyimino- M-methylacetamide and methyl ether

C-methoxy-2-(2-(M-(4-methoxyphenyl)-cyclopropylcarboximidoylsulfanylmethyl)-phenyl)-acrylic acid; and their salts.

Active compounds of the formula | belong to the class of active compounds strobilurins, which were known for a long time to be active as fungicides and. in individual cases, also as insecticides. They are described, among other things, in EP 178 826; ER 253 213; MO 93/15046; MO 95/18789; UMO 95/21153; UMO 95/21154; MO 95/24396; MO 96/01256; MO 97/15552; UMO 97/27189.

According to the present invention, the cold stress that plants may experience if the temperature drops can be prevented or the stress can be effectively reduced by the present invention.

In crop production, low temperatures mean low temperatures and frosts, i.e. temperatures from 157C, preferably in the range from 157C to -157C, especially preferably from 107C to -10"C and especially from 107C to -57C. In addition, temperature ranges from 10"C or 117C to 0"C and from 5"C to 0"C as well as temperature ranges below 0"C can be harmful to the corresponding crop. Thus, the temperature that causes plant damage may also depend on the crop in question.

The compounds used according to the invention are preferably used to increase the resistance of plants to the temperature range from -157C to 157C, especially preferably from -107C to 10"C and especially from -57C to 10"C. In addition, improving the resistance of plants to temperature ranges from 107C or 11 "C to OS, from 5"C to 0"C as well as to temperature ranges below 0"C is particularly important.

In the case of cold-sensitive plants, the compounds used according to the present invention, especially the strobilurin compound, more precisely the compound of formula I, are used especially to increase the resistance of plants to low temperatures and to reduce the cold stress of plants in case of a decrease in temperature, respectively. As a rule, this means resistance to temperatures in the range from 0"C to 15"C, especially from 07 to 1070. In the case of frost-sensitive plants - in addition to the above-mentioned cold-sensitive plants, for example, seed and drupe species during flowering period and citrus species and other plants, which, while resistant to cold, are not resistant to frost - these compounds are especially also suitable for increasing the resistance of plants to temperatures in the range from -157C to 0"C, especially preferably from -107C to 0"C, and especially from -57C to 0".

The stability of masses means especially the reduction or prevention of damage from cooling and/or frost on plants.

According to the present invention, cold stress is not limited to frost damage through the formation of ice crystals, but damage can also occur at higher temperatures than those mentioned above, especially for sensitive plants. For such plants, temperatures from, for example, 10"C to 57C or from 107C to 0"C can cause significant damage. According to the present invention, it has been found that it is also possible to prevent sensitive plants from such damage by applying a compound that inhibits the mitochondrial respiratory chain at the level of the B/si complex, especially a compound of formula I. Thus, for example, coffee, corn, rice, soy and citrus fruits can be effectively protected against cold stress.

Compounds that suppress the mitochondrial respiratory chain at the level of Br/s| complex, especially strobilurins, more specifically, compounds of formula I are particularly preferably used to reduce or prevent chilling damage to cold-sensitive agricultural plants, such as corn, fig. soybean, sugar beet, sugar cane, eggplant, tomato, red pepper, potato, melon, cucumber, cultivated grapes (grapes), beans, peas, banana, citrus species and coffee. In addition, the present invention can be successfully applied against cold stress in wheat, barley, sunflower and rapeseed.

In addition, according to the invention, compounds that suppress the mitochondrial respiratory chain at the level of the B/c1 complex, especially compounds of formula I, are especially preferably used to reduce or prevent frost damage in the above-mentioned cold-sensitive agricultural plants, in addition to seed and stone fruits, all citrus fruits and coffee. In the case of seed and stone fruits, these compounds are especially preferably used to prevent frost damage to the buds, flowers, leaves and young fruits of these plants. Seed and stone fruits are, for example, apple, pear, quince, peach, apricot, nectarine, cherry, plum, prune or almond, preferably apple.

Citrus species are, for example, lemon, orange, grapefruit, clementine or tangerine.

In particular, the compounds used in accordance with the present invention, especially the compounds of formula |, are used to reduce or prevent frost damage to stone fruits (eg almonds) and pome fruits, especially apples.

One embodiment of the invention relates to the use of an active compound of formula I, as defined at the beginning, or a strobilurin compound selected from methyl-(2-chloro-5-|1-(3-methylbenzyloxyimino)-ethyl|-benzyl)-carbamate and methyl- (2-chloro-5-|11-(b-methylpyridin-2-ylmethoxyimino)-ethyl|-benzyl)-carbamate.

In another embodiment of the invention, the compounds of formula I are used as defined at the beginning.

In addition, the following compounds can be used according to the invention, as listed in the tables below.

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Preferred for use according to the invention are commercially available active strobilurin compounds.

Particular preference is given to the following active compounds: compound 1-5 (pyraclostrobin), 1I-1 (cresoxim-methyl),

I-3 (dimoxystrobin), 11-11 (27 0712), TSI-3 (picoxystrobin), IM-6 (trifloxystrobin), IM-9 (enestroburin), M-16 (orysastrobin), MI-1 (methominostrobin), MII-1 (azoxystrobin) and MII-11 (fluoxastrobin). An additional compound of formula I which is suitable is fluacripyrim (methyl (E)-2-(a-(2-isopropoxy-6-(trifluoromethyl)-pyrimidin-4-yloxy)-o-tolyl-3-methoxyacrylate).

In the context of a valid invention, the term "compounds of formula I!" refers both to neutral compounds of formula I, and to other strobilurin-active compounds mentioned at the beginning, and, in addition, to their salts.

The compounds used according to the present invention, especially the compounds of formula I, are preferably used in applied doses of from 25 to 1000 g/ha, particularly preferably from 50 to 500 g/ha and especially from up to 250 g/ha.

The compositions according to the invention may, in addition, be present together with other active compounds, for example with herbicides, insecticides, growth regulators, fungicides or with fertilizers. When the compounds used according to the present invention, especially compounds (I), or compositions containing them, are combined with one or more additional active compounds, especially fungicides, it is often possible, for example, to broaden the spectrum of activity or prevent the development of resistance. A synergistic effect is often found.

The following list of fungicides, insecticides, growth retardants, and primers that may be used in conjunction with an active compound that inhibits the mitochondrial respiratory chain at the level of the B/c1 complex, particularly with an active strobilurin compound, is intended to illustrate, not limit, the possible combinations:

Strobilurins azoxystrobin, dimoxystrobin, enestroburin, fluoxastrobin, kresoxim-methyl, methominostrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, orysastrobin, methyl-(2-chloro-5-(1-(3-methylbenzyloxyimino)-

ethyl|-benzyl)-carbamate, methyl-(2-chloro-5-|1-(b-methylpyridin-2-ylmethoxyimino)-ethyl|-benzyl)-carbamate, methyl 2-(ortho-(2,5-dimethylphenyloxymethylene) )-phenyl)-3-methoxyacrylate, 2-(2-(6-(33-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yloxy)-phenyl)-2-methoxyimino-M-methylacetamide; methyl ester of 3-methoxy-2-(2-(1N-(4-methoxyphenyl)-cyclopropanecarboximidoylsulfanylmethyl)-phenyl)-acrylic acid;

Carboxamides - carboxanilides: benalaxyl, benalaxyl-M, benodanil, bixafen, boskalid, carboxin, mepronil, fenfuram, phengexamide, flutolanil, furametpir, metalaxyl, ofuraz, oxadinil, oxycarboxin, pentiopirad, thifluzamide, thiadinil, anilide 2-amino-4-methylthiazole -5-carboxylic acid, 2-chloro-M-(1,1,3-trimethylindan-4-yl)-nicotinamide, M-(4-bromobiphenyl-2-yl)-4-difluoromethyl-2-methylthiazol-5- carboxamide, M-(4-trifluoromethylbiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamide, M-(42-chloro-3'-fluorobiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole- 5-carboxamide, M-(34-dichloro-4-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methylpyrazole-4-carboxamide, M'-(3'.4-dichloro-5-fluorobiphenyl-2-yl) )-3-difluoromethyl-1-methylpyrazole-4-carboxamide, M-(2-cyanophenyl)-3,4-dichloroisothiazole-5-carboxamide, amide M-(2-(1,3-dimethylbutyl)-phenyl)-1 ,3,3-trimethyl-5-fluoro-1H-pyrazole-4-carboxylic acid, amide M-(4-chloro-35-difluorobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4 -carboxylic acid, amide //M-(2-chloro-35-difluoro biphenyl-2-yl)-3-trifluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide /M-(34-dichloro-5-fluorobiphenyl-2-yl)-3-trifluoromethyl-1-methyl- 1H-pyrazole-4-carboxylic acid amide /M-(35-difluoro-4-methylbiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid amide //M-( 35-difluoro-4'-methylbiphenyl-2-yl)-3-trifluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid, amide M-(cis-2-bicyclopropyl-2-ylphenyl)-3-difluoromethyl- 1-methyl-1H-pyrazole-4-carboxylic acid, M-(trans-2-bicyclopropyl-2-ylphenyl)-3-difluoro-stil-1-methyl-1H-pyrazole-4-carboxylic acid amide; - morpholides of carboxylic acids: dimethomorph, flumorph; - benzamides: flumetover, fluopicolide (picobenzamide), fluopyram, zoxamide, M-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formylamino-2-hydroxybenzamide; - other carboxamides: carpropamide, diclomet, mandipronamide, oxytetracycline, silthiofam, M-(6-methoxypyridin-3-yl) cyclopropanecarboxylic acid amide, M-(2-(4-I3-(4-chlorophenyl)-prop-2-ynyloxy) |-3- methoxyphenyl)-ethyl)-2-methanesulfonylamino-3-methylbutyramide, /- M-(2-(4-(3-(4-chlorophenyl)-prop-2-ynyloxy|-3- methoxyphenyl)-ethyl )-2-stansulfonylamino-3-methylbutyramide;

Azoles - triazoles: azaconazole, biternatol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, enilconazole, epoxyconazole, fenbuconazole, flusilazole, fluhinconazole, flutriazole, hexaconazole, imibnconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazol, penconazole, propiconazole, prothioconazole, semiconazole, tebuconazole, tetraconazole, triadimenol, triadimefon, triticonazole, iniconazole, 1-(4-chlorophenyl)-2-(1,2,4|griazol-1-yl)-cycloheptanol; - imidazoles: cyazofamide, imazalil, imazalil sulfate, pefurazoate, prochloraz, triflumizole; - benzimidazole: benomyl, carbendazim, fuberidazole, thiabendazole; - others: etaboxam, etridiazole, himexazole;

Nitrogen-containing heterocyclic compounds - pyridines: fluazinem, pyrifenox, 3-I5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl|-pyridine, 2,3,5,6-tetrachloro-4-methanesulfonylpyridine, 3,4 ,5-trichloropyridine-2,6-dicarbonitrile, M-(-(5-bromo-3-chloropyridin-2-yl)-ethyl)-2,4-dichloronicotinamide, M-(5-bromo-3-chloropyridine-2 -yl)-methyl)-2,4-dichloronicotinamide; - pyrimidines: bupirimate, cyprodinil, diflumethorim, ferimzop, fenarimol, mepanipyrim, nitrapyrin, naurimol, pyrimethanil; - piperazines: triforin; - pyrroles: fludioxonil, fenpiclonil; - morpholines: aldimorph, dodemorph, dodemorph-acetate, fenpropimorph, tridemorph; - dicarboximides: iprodione, fluorimid, procymidone, vinclozolin; - others: acibenzolar-5-methyl, anilazine, blasticidin-5, captan, cypomethionate, captafol, dazomet, debacarb, diclomesin, difenzoquat, difenzoquat-methylsulfate, fenoxanil, folpet, oxolinic acid, piperaline, fenpropidine, famoxadone, phenamidon, ooctilinon, probenazole, proquinazid, pyroquilone, quinoxifene, tricyclazole, 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-(1,2,4|griazolo|1,5 - α|pyrimidine, 2-butoxy-6-iodo-33-propylchromen-4-one, M,M-dimethyl-3-(3-bromo-6-fluoro-2-methylindol-1-sulfonyl)-(1, 2, Agriazole-1-sulfonamide;

Carbamates and dithiocarbamates - dithiocarbamates: ferbam, mancozeb, maneb, metiram, metam, metasulfocarb, propineb, thiramem, zineb, ziram; - carbamates: dietofencarb, benthiavalicarb, flubenthiavalicarb, iprovalicarb, propamocarb, propamocarb hydrochloride, methyl 3-(4-chlorophsnyl)-3-(2-isopropoxycarbonylamino-3-methylbutyrylamino)-propionate, 4-fluorophenyl-M-(1-(1 -(4-cyanophenyl)-ethanesulfonyl)-but-2-yl)-carbamate;

Other fungicides - guanidines: dodin, dodin free base, guazatin, guazatin-acetate, iminoctadine, iminoctadine-triacetate, iminoctadine-tris(albesylate); - antibiotics: kasugamycin, kasugamycin-hydrochloride-hydrate, polyoxins, streptomycin, validamycin A; - organometallic compounds: fentin salts (e.g. fentin acetate, fentin chloride, fentin hydroxide); sulfur-containing heterocyclic compounds: isoprothiolane, dithianone; - organophosphorus compounds: edifenfos, fosetyl, fosetyl-aluminum, iprobenfos, pyrazofos, tolclofos-methyl, phosphoric acid and its salts; - chloroorganic compounds: thiophanate methyl, chlorothalonil, dichlofluanid, dichlofen, flusulfamide, phthalide, hexachlorobenzene, pencicuron, pentachlorophenol and their salts, quintosene, tolylfluanid, M-(4-chloro-2-nitrophenyl)-

M-ethyl-4-methylbenzenesulfonamide; - nitrophenyl derivatives: binapacryl, dichloran, dinocan, dinobuton, nitrothal-isopropyl, technazen; - inorganic active compounds: Bordeaux mixture, copper salts (e.g. copper acetate, copper hydroxide, copper oxychloride, basic copper sulfate), sulfur; - others: biphenyl, bronopol, cirlufenamide, cymoxanil, diphenylamine, metrafenone, mildiomycin, oxy-copper, prohexadione-calcium, spiroxamine, tolylfluanid, M-(cyclopropylmethoxyimino-(b-difluoromethoxy-2,3-difluorophenyl)-methyl)-2 -phenylacetamide, M'-(4-(4-chloro-3-trifluoromethylphenoxy)-2,5-dimethylphenyl)-M-ethyl-

M-methylformamidine, M'-(4--4-fluoro-3-trifluoromethylphenoxy)-2,5-dimethylphenyl)-M-ethyl-M-methylformamidine, M'««2-methyl-5-trifluoromethyl-4-( 3-trimethylsilanyl-propoxy)-phenyl)-M-ethyl-M-methylformamidine, M'-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanylpropoxy)-phenyl)-M-ethyl-M-methylformamidine;

Plant growth regulators (PNRs): auxins (eg, p-indoleacetic acid (IA), 4-indole-3-ylbutyric acid (IBA), 2-(1-naphthyl)-acetamide (MAA)), cytokinins, gibberellins, ethylene , abscisic acid.

Growth inhibitors: prohexadione and its salts, trinexapak-ethyl, chlormequat, mepiquat-chloride, diflufenzopir.

Primers: benzothiadiazole (BTN), salicylic acid and its derivatives B-aminobutyric acid (BABA), 1-methylcyclopropene (1-MCP), lipopolysaccharides (GR), neonicotinoids (e.g. acetamiprid, clothianidin, dinetofuran, fipronil, imidacloprid, thiacloprid, thiamethoxam).

Ethylene regulators: inhibitors of ethylene biosynthesis, which inhibit the transformation of 5-adenosyl-ii-methionine into 1-aminocyclopropane-1-carboxylic acid (ACC), such as derivatives of vinylglycine, hydroxylamines, derivatives of oxime esters; inhibitors of ethylene biosynthesis, which block the conversion of ACC to ethylene. selected from the group containing: ions of boh or Min- in a form accessible to plants; phenol radical acceptors such as n-propyl gallate; polyamines such as putrescine, spermine or spermidine; structural analogues of ACC, such as α-aminoisobutyric acid or 11-aminocyclopropene-1-carboxylic acid; salicylic acid or acibenzolar-5-methyl; structural analogues of ascorbic acid, which act as ACC oxidase inhibitors, such as prohexadione-Ca or trinexapak-ethyl; and triazolyl compounds, such as paclobutrazol or iniconazole, as inhibitors of cytochrome P-450-dependent monooxygenases, the main task of which is to block the biosynthesis of gibberellins; inhibitors of ethylene action selected from the group containing: structural analogs of ethylene, such as 1-methylcyclopropene or 2,5-norbornadiene and 3-amino-1,2,4-triazole or Ad--- ions.

The active compounds mentioned above are well known and commercially available.

In a preferred embodiment of the invention, compounds that suppress the mitochondrial respiratory chain at the level of the p/c1 complex, especially strobilurin compounds, especially compounds of the formula |, are used according to the invention in combination with bioregulators, especially with primers.

In a preferred embodiment of the invention, compounds that inhibit the mitochondrial respiratory chain at the level of B/c1 complex, especially strobilurin compounds, especially compounds of formula II, are used according to the invention in combination with prohexadione-Ca, and/or with trinexapak-ethyl and/or with a generally accepted cryoprotectant as an auxiliary substance.

In an additional preferred embodiment of the invention, compounds that inhibit the mitochondrial respiratory chain at the level of the B/c1 complex, especially strobilurin compounds, especially compounds of formula I, are used according to the invention in combination with vitamin E or its derivative and/or with abscisic acid and/or with a generally accepted cryoprotectant as an auxiliary substance.

The weight ratio of compounds that suppress the mitochondrial respiratory chain at the level of Br/c1 complex, especially strobilurin compounds, especially compounds of formula I, to vitamin E or its derivatives is preferably from 1:1 to 1:20, especially preferably from 1:5 to 1 :20 and especially from 1:5 to 1:15. The weight ratio of the compounds used according to the invention, especially the compounds of formula I, to abscisic acid is preferably from 1:0.05 to 1:1, especially preferably from 1:0.05 to 1:0.5 and especially from 1:0.1 to 1:0.3. The weight ratio of the compounds used according to the invention, especially the compounds of formula I, to the cryoprotectant is preferably from 1:10 to 1:1000, especially preferably from 1:10 to 1:500 and especially from 1:10 to 1:100.

In the context of the present invention, vitamin E refers to all compounds of the vitamin E group, such as α- to C-tocopherols and tocotrienols and their isomers, salts and esters, regardless of whether these compounds are of natural or synthetic origin. A-tocopherol is the most commonly used substance. which occurs in nature (ABV-a-tocopherol) or its ester with a C-C-carboxylic acid, such as formic acid, acetic acid, propionic acid or butyric acid. Atocopherol acetate is especially used.

Abscisic acid is (5)(--)-5-(1-hydroxy,b,b-trimethyl-4-oxo-2-cyclohexenyl)-3-methyl-cis/trans-2,4-pentadienoic acid.

Cryoprotectants suitable for plant treatment include, for example, alcohols such as propanol and butanol, polyols such as ethylene glycol or glycerol, (poly)zephyropolyols such as diethylene glycol, triethylene glycol and polyethylene glycols of molecular weight up to 500, and formic acid salts, such as, especially, sodium, potassium, ammonium, calcium and magnesium salts of formic acid. The most widely used cryoprotectant is glycerin. The use of one or more salts of formic acid is also preferred.

In plant physiology, primers are compounds known for host activity. Priming is known as a process that results in an increase in the ability of plants to overcome both biotic (e.g. fungal pathogens) and abiotic (e.g. drought) stresses. Since primers interact in a complex way with the transmission of signals in the plant, in general they can be classified as a subgroup of bioregulators (review in Sopgaia and a). (2006) Riitipd: Sseycipu geadu Gog bashe. MoiIestsag Riapi-Misgobe Ipiegasiopv 19: 1062-1071).

Ethylene regulators mean substances that block the natural formation of the plant hormone ethylene or its action. (See, for example, reviews by M. Pereptap (1979), Viozupipeviv apa asiip oi eiiNuIepe, Appiai

Journal of Scientific Research 30: 533-591; 5.E. Mapud apa M.E. Neutap (1984), Euiepe BiozupiNneziv apa yiv gedshayop ip podpeg riapi5, Appia! Vemiem oi Riapi Rpuzioiyudu 35: 155-189; H.5. 5ivieg her a!. (2003).

MO2005044002).

The compounds used according to the invention, especially the compounds of formula !, or their combinations with the above excipients, are generally used as compositions, as they are commonly used in the field of plant protection.

For example, they can be diluted with water in the form of concentrated solutions, suspensions or emulsions and applied by spraying. The forms used depend on the type of plant or part of the plant to which they will be applied; in each case, the vials should ensure as good as possible the distribution of active compounds and excipients.

In addition to the compounds used according to the invention, especially the compounds of formula I, optionally with vitamin E and/or abscisic acid and/or a cryoprotectant, the compositions may contain excipients used for the preparation of dosage forms, such as are commonly used to formulate products for plant protection, for example, inert auxiliary substances and/or surface-active substances, such as emulsifiers, dispersants, wetting agents, etc.

Suitable surfactants are alkaline, alkaline earth, and ammonium salts of aromatic sulfonic acids, such as lignosulfonic acid, phenolsulfonic acid, naphthalene sulfonic acid, and dibutylnaphthalene sulfonic acid, and fatty acids, alkyl and alkylaryl sulfonates, alkyl, lauryl ether, and sulfates of fatty alcohols, and salts of sulfated hexa- , hepta- and octadecanols and glycol ethers of fatty alcohols, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene or naphthalene sulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl-, or nonylphenol, alkylphenyl polyglycol ethers, tributylphenyl polyglycol ether , alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol ethers, spent lignosulfite solutions, methyl cellulose or siloxanes. Examples of suitable siloxanes are polyester/polymethylsiloxane copolymers, also called spreaders or penetrants.

Inert excipients used for the preparation of preparations are mainly: petroleum fractions with medium to high boiling points, such as kerosene and diesel fuel, in addition, coal tar and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons such as paraffins, tetrahydronaphthalene, alkylated naphthalene and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, highly polar solvents such as amines such as M- methylpyrrolidone, and water.

The used aqueous forms of the compounds used according to the invention, especially compounds I, or their combinations with vitamin E and/or abscisic acid and/or cryoprotectant, can be prepared from preparative forms stored, such as emulsions, concentrates, suspensions, pastes, powders, wettable, or water-dispersible granules by adding water. To obtain emulsions, pastes or oil dispersions, the compounds used according to the present invention, especially the compounds of formula I, or their above-mentioned combination with vitamin E and/or abscisic acid and/or cryoprotectant, can be homogenized as such or dissolved in oil or solvent in water using a wetting agent, tackifier, dispersant or emulsifier. Naturally, the forms used should include excipients applicable in preparative forms that are stored.

In a preferred embodiment of the invention, the compounds used according to the invention, especially the compounds of formula I, or the aforementioned combination thereof, are used in the form of an aqueous spray mixture. The aqueous spray mixture contains, respectively, the compound in an amount preferably from 50 to 200 ppt. When the above combination is used as a spray mixture, it should include vitamin E preferably from 50 to 4000 ppm, more preferably from 500 to 3500 ppm and especially from 1000 to 3000 ppm; abscisic acid in an amount preferably from 0 to 200 ppm, especially preferably from 2.5 to 100 ppm and especially from 5 to 15 ppm, and a cryoprotectant in an amount preferably from 0 to 50,000 ppm, especially preferably from 500 to 20,000 ppm, and especially from 500 to 10,000 rrt.

The components used according to the invention, especially the active strobilurin compound, also the active compound and/or cryoprotectant can be applied to plants or plant parts as a mixture or separately; in the latter case, the individual components should be applied within as short an interval as possible.

The active compounds, especially the strobilurins used according to the invention, can be used for application to all the above-mentioned plants, in addition to plant species that differ from them. Depending on the parts of the plant to which they will be applied, they can be applied by means of apparatus that are essentially known and commonly used in agricultural practice, preferably in the form of an aqueous spray solution or spray mixture.

The method of the invention is suitable for foliar application to growing agricultural plants, for application to the soil before sowing or growth, including complete soil treatment and application to the furrow, which provide protection of the early stages of corn, wheat, soybeans, cotton and other useful plants against the cooling effect.

The application is carried out by spraying, so that there are points of contact, or by etching the seeds.

Treat either the entire aerial part of the plant or only certain parts of the plant, such as flowers, leaves or fruits. The choice of individual plant parts to be processed depends on the plant species and their developmental stages. Late stages can be protected mainly by foliar treatments. In one embodiment, the application is carried out on seeds. It is preferable to process embryos, seedlings, buds and flowers at various stages of development, and young fruits.

The application is preferably carried out before the period of lowering the temperature or frost.

Preferably, it is carried out at least 12 hours, especially preferably at least 24 hours and especially 36 hours - 20 days before the expected onset of temperature drop or frost.

For seed treatment, mainly the active compound is used in amounts from 1 to 1000 g/100 kg, preferably from 5 to 100 g/100 kg of seed.

The present invention also relates to a method of increasing the resistance of plants to low temperatures, preferably to reduce or prevent chilling damage and frost damage of plants, which includes the application of an aqueous composition comprising a compound used according to the invention, especially a compound of formula I, to seeds, plants or parts of plants.

What has been said above relates to the compounds used in accordance with the invention, especially the compounds of the formula

It, other components, water composition and application, is used here similarly.

The resistance of plants to low temperatures and frosts is clearly increased when active strobilurin compounds are used according to the invention. In particular, chilling damage and frost damage to plants is prevented or at least reduced when used in accordance with the invention. An additional advantage of the use according to the invention of a compound that suppresses the mitochondrial respiratory chain at the level of the B/c1 complex, especially active strobilurin compounds, such as kresoxime-methyl, pyraclostrobin and orysastrobin, especially pyraclostrobin and orysastrobin, preferably kresoxime-methyl and orysastrobin, especially orysastrobin, consists in their activity against bacterial burn of fruit trees. Thus, treated plants according to the invention are not only more resistant to low temperatures, but also additionally protected from this flower infection.

The protective effect of treatments against chilling was not only measured quantitatively in a controlled environment (e.g. pear, maize, Agaridorvzis, wheat), but also observed for other crops, both under practical field conditions (e.g. sugar beet, oranges). indicating the broad applicability of the principle.

The examples that follow are intended to illustrate the invention, but without imposing any limitations.

Example 1 111 Experiment

Agaridorziz Shaiyapa plants were grown in pots (diameter 8 cm) in controlled environmental conditions at 21 °C during the day and at 197 °C during the night, with a light regime of 9 hours of light and 15 hours of darkness per day.

Chemical treatment was carried out 18 days after sowing. Each pot was treated with 500 ml of spray solution according to the treatment list below using a commercial sprayer. 1) Untreated, 2) Orysastrobin (250 ppm), 3) Orysastrobin (500 ppm), 4) Pyraclostrobin (500 ppm).

After chemical treatment, the pots were placed in the same growth conditions for three days. The pots were then exposed to three different environmental conditions to induce cold stress:

Control plants (A) were maintained under the same conditions as described above.

Stressed plants (B) were moved for 2 days to 6"C with a 9-15 hour day-night cycle. This cold treatment allows Agaridorziz plants to acclimatize to a certain volume of the next freezing stress (-4"C, 24 h. in the dark) (Mappeg eyii ai., 1999, Soid-ipdisei iyeegipd YuiIegapse ip Agabidorziv, Riapi

RPuvzioiodu 120, 391-399).

Stressed plants (C) were not cold-hardened and kept for an additional 2 days in the control environment before being transferred to -4°C without light for one day.

After these treatments, all pots were returned to standard growth conditions (controlled environmental conditions) as described above. - with. 21"stes 6's -4-S

A (control plants) | 18 days after sowing, if there are | days.///////Ї- 77777771

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From the day and 9 days after the chemical treatment (through 3 days after recovery from the freezing treatment) the tests were evaluated by visual assessment, noting the symptoms in 95 leaf damage.

Three days after the chemical treatment, no leaf damage was observed there. After the stress treatment, the following damage to the leaf was assessed:

Stressed state of processing (1) 250 ppt (2) 500 ppt (3) 500 ppt (4) sutures and PT; I Po I POLON THUYA PON U

The selected environmental conditions were sufficient to cause severe damage to the leaf. As expected, the 2-day period of cold hardening from stressful conditions "B" contributed to the reduction of stress symptoms. However, as can be seen from the results, the most effective reduction of stress symptoms was achieved by the chemical treatments of the invention. Chemical treatments with both orysastrobin and pyraclostrobin were very effective in reducing chilling symptoms in Agaridorvy plants under various stress conditions.

Example 2 2.1 Experiment

A single branch on a mature Vovs pear tree in full flower development was pollinated to runoff with a Rgtiziipe? ZVU/s at a ratio of 1.03 grams per two liters, equivalent to 14.5 ounces per acre at 200 gallons per acre (Riizipe 38 commercial preparation of pyraclostrobin and boscalid manufactured by VABE

Akiispdeseiivspamt). biidaga? 309 (a commercially available adjuvant) was added to R'iviipe and applied at a rate of 0.297 ml per two liters, equivalent to 2.0 ounces per 100 gallons or 4.0 ounces per acre.

Aerosol Rgiziipe plus 5idaga was applied, where a separate control branch on the nearest tree was left unsawed.

After one day, a temperature-controlled branch cage covering a 2-meter section of the cut branch was applied to reduce the temperature from the ambient temperature of 3.97C to -3.7°C. The time required to reach this temperature was approximately 10 minutes. was slightly increased and kept between -3.37C and -2.8"C for 5 minutes.

Blooms were assessed for frost damage five days later. Whole flowers on each daw that were in the cage were counted. A flower was considered injured if there was visible discoloration at the base of the pistils in the calyx. 2.2 Results

Control branch: a total of 283 flowers, 202 (7190) healthy and 81 (2995) damaged

A branch treated according to the present invention: a total of 163 flowers 147 (9095) healthy and 16 (10905) damaged

Thus, Riiziipe" applied before low-temperature processing gave a significant degree of frost protection to pear blossoms.

Example C 3.1 Experiment

Corn seeds (7ea tauv; cultivar Riopeeg herbicide-resistant ZZ3R71) were treated using:

T1: Water (untreated)

T2: Pyraclostrobin (5 g of active component/ 100 kg of seeds) tT3: Azoxystrobin (1 g of active component/ 100 kg of seeds).

Subsequently, the treated seeds were planted in plastic pots (6 cm x b cm x 7 cm) filled with sand (metro mix). The seeds were grown in a growth chamber (Sopmigop) at 25°C and 60 95 humidity under a 16/8 h dark/light cycle for 5 days (seedlings were at code 10). At this point, the seedlings were placed at -57°C at After cold stress, viable seedlings were maintained, grown until they reached code 13. At this stage, they were subjected to an additional 2 hours of cold stress at -570.

Finally, the number of damaged seedlings (90) for each seed treatment was recorded. 3.2 Results 11111111 (Water) | T2 (Pyraclostrobin) | TZ (Azoxystrobin)

The selected environmental conditions were sufficient to cause severe damage to the leaf. As can be seen from the results, seed treatment with chemical products of the formula | of the invention leads to an effective reduction of cold stress symptoms, while control plants treated only with water are severely damaged.

Example 4

Adult citrus trees (Siygi5 vzipepziz) were treated with three foliar applications of 1600 g/ha of pyraclostrobin at intervals of 14 - 18 days. Application was started shortly before the initial freezing in winter seasons. Temperatures fell as low as -6°C in three separate cold weather events. Damage is not expected to decrease with extremely low temperatures. However, even under these extreme conditions, plants growing in the pyraclostrobin-treated plot showed fewer signs of leaf burn and fruit drop than untreated plants control The results of this experiment show a strong chilling protection of pyraclostrobin in citrus.

Claims (25)

1. Application of strobilurin or its salt to increase resistance of plants to low temperatures, and the plant is selected from the group including corn, rice, wheat, barley, sunflower, rapeseed, soybean, sugar beet, sugar cane, potato, tomato, red pepper, eggplant, melon, cucumber, beans, peas, banana, grapes, seed and stone fruits, citrus fruits and coffee, where strobilurin or its salt is applied to the seeds. 2. Application according to claim 1, in which strobilurin is a compound of the formula Xa A and in which X means halogen, C-C-alkyl or trifluoromethyl; t means 0 or 1; O stands for С(СН-СН3)-СООСН», С(СН-ОСН3)-сСОоОССН», С(-М-ОСН3)-СОМНеН3, С(-М-ОСН3)-СООСсН», M(-ОСН3)- СООСН ;", or group 01 and A (C | M-OSH, 07 also where Ж means a connection with a phenyl ring; A means -ОО-В, -СН2гО-В, -ОСНо-В, -СНг5-В, - "СНеСН-В, -С-6-В, -СНгОо-М-С(В)-В, -СНg5-М-С(В)-В, -СНго- M-С(В)-СН- CH-B or -CHgO-M-C(B")-C(82)-M-OVZ, where B means phenyl, naphthyl, 5- or 6-membered heteroaryl or 5- or 6-membered heterocyclyl, which contains one, two or three nitrogen atoms and/or one oxygen or sulfur atom or one or two oxygen and/or sulfur atoms, where the ring systems are unsubstituted or substituted by one, two or three KU groups: Ve independently of each other means a cyano group, nitro group, amino group, aminocarbonyl, aminothiocarbonyl, halogen, C1i-Cv-alkyl, C1i-Cv-haloalkyl, C1i-Cv-alkylcarbonyl, C1i-Cv-alkylsulfonyl, C1-Cv-alkylsulfinyl, C3-Cv- cycloalkyl, C-Cv- alkoxy group, C1i-Cv-haloalkyl group, C1-Cv-alkyloxycarbonyl, C-Cv-alkylthio group, C1-Cv- alkylamino group, di-Ci-Cv-alkylamino group, C1-Cv-alkylaminocarbonyl, di-Ci-Cv-alkylaminocarbonyl, /C1-Cv- alkylaminothiocarbonyl, di-C1i1-Cv-alkylaminothiocarbonyl, C2-Cv-alkenyl, Co-Cv-alkenyloxy group, phenyl, phenoxy group, benzyl, benzyloxy group , 5- or b-membered heterocyclyl, 5- or b6-membered heteroaryl, 5- or 6-membered heteroaryloxy group, С(-МОВ2)-В? or OS(K2)2-C(B2)-MORE, where cyclic radicals, in turn, can be unsubstituted or substituted by one, two, three, four or five groups Re: A? independently of each other mean cyano group, nitro group, halogen, amino group, aminocarbonyl, aminothiocarbonyl, C1i-Cv-alkyl, Ci-Cv-haloalkyl, Ci-Cv-alkylsulfonyl, Ci-Cv-alkylsulfinyl, C3-Cv-cycloalkyl, C1-Cv -alkoxy group, C1i-Cv-haloalkyl group, C1i-Cv-alkoxycarbonyl, C1-Cv-alkylthio group, C1i-Cv-alkylamino group, di-C1i-Cv-alkylamino group, Ci-Cv-alkylaminocarbonyl, di-C1-Cv-alkylaminocarbonyl, Si -C1-alkylaminothiocarbonyl, di-C1-C1-alkylaminothiocarbonyl, Co-Cv-alkenyl, Co-Cv-alkenyloxy group, C3-Cv-cycloalkyl, C3-C6-cycloalkenyl, phenyl, phenoxy group, phenylthio group, benzyl, benzyloxy group, 5- or 6b-membered heterocyclyl, 5- or b-membered heteroaryl, 5- or b-membered heteroaryloxy or C(-MOP)-B8; VU, BB independently of each other mean hydrogen or Ci-Cv-alkyl; IN! means hydrogen, cyano group, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C1-C4-alkylthio group; IN? means phenyl, phenylcarbonyl, phenylsulfonyl, 5- or b-membered heteroaryl, 5- or b-membered heteroarylcarbonyl or 5- or b-membered heteroarylsulfonyl, where the ring system may be unsubstituted or substituted with one, two, three, four or five groups Ka, C-C0-alkyl, C3-C6-cycloalkyl, C2-Sio-alkenyl, C2-Cio-alkynyl, C1-Cio-alkylcarbonyl, C2-Cio-alkenylcarbonyl, C3-Cio-alkynylcarbonyl, C-Cio-alkylsulfonyl or С(-МОВ2)-ВР, where the carbon chains can be unsubstituted or substituted by one, two, three, four or five K- groups: Бе independently of each other mean a cyano group, a nitro group, an amino group, an aminocarbonyl, an aminothiocarbonyl, a halogen, C1-Cv-alkyl, C1-Cv-haloalkyl, C1i-Cv-alkylsulfonyl, C1i-Cv-alkylsulfinyl, C1-Cv-alkoxy group, C1-Cv- haloalkoxy group, C1-Cv-alkoxycarbonyl, C1i-Cv-alkylthio group, C1- Cn-alkylamino group, di-C1i-Cn-alkylamino group, C1-Cn-alkylaminocarbonyl, di-Ci-Cn-alkylaminocarbonyl, C1i-Cn-alkylaminothiocarbonyl, di-C1-Cn-alkylaminothiocarbonyl yl, C2-Cv-alkenyl, Ce-Cv-alkenyloxy group, C3-Cv-cycloalkyl, C3-Cv-cycloalkyloxy group, 5- or b-membered heterocyclyl, 5- or b6-membered heterocyclyloxy group, benzyl, benzyloxy group, phenyl, phenoxy group, a phenylthio group, a 5- or b-membered heteroaryl, a 5- or b-membered heteroaryloxy or a heteroarylthio group, where the cyclic groups may be partially or fully halogenated or may be substituted by one, two or three KU groups; and VAZ means hydrogen, C1i-Cv-alkyl, Co-Cv-alkenyl, Co-Cv-alkynyl, where carbon chains can be replaced by one, two, three, four or five K- groups; or a strobilurin compound selected from the group containing methyl-(2-chloro-5-|1-(3-methylbenzyloxyimine)-ethyl|-benzyl)- carbamate, methyl-(2-chloro-5-(1-(b- methylpyridin-2-ylmethoxyimine)-ethyl|-benzyl)-carbamate, 2-(2-(6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yloxy)-phenyl)-2-methoxyimine-h -methylacetamide and methyl ester of 3-methoxy-2-(2-(4-(4-methoxyphenyl)-cyclopropanecarboximidoylsulfanylmethyl)-phenyl)-acrylic acid. 3. Application according to claim 2, in which strobilurin is a compound of the formula |. 4. Use according to claim 2 or 3, in which the compound of formula I is selected from the group containing pyraclostrobin, kresoxymethyl, dimoxystrobin, 290712, picoxystrobin, trifloxystrobin, enestroburin, orysastrobin, methominostrobin, azoxystrobin and fluoxastrobin. 5. Use according to any one of claims 2-4, in which the compound of formula I is selected from the group containing pyraclostrobin, kresoxim-methyl, dimoxystrobin and orysastrobin. 6. Use according to any one of claims 2-5, in which the compound of formula I is selected from the group containing azoxystrobin, pyraclostrobin and orysastrobin. 7. Use according to any one of claims 2-6, in which the compound of formula I is orysastrobin. 8. Application according to any of claims 1-7 for increasing the resistance of plants to low temperatures in such plants as corn, rice, soybeans, seed and stone fruits, citrus fruits and coffee. 9. Application according to claim 8 for increasing the resistance of plants to low temperatures in such plants as almonds, corn, soybeans, citrus fruits and coffee. 10. Application according to any of claims 1-7 for increasing the resistance of plants to frost damage. 11. Application according to claim 10 for increasing the resistance of plants to frost damage, in such plants as corn, rice, soybeans, seed and stone fruits, citrus fruits and coffee. 12. Application according to claim 11 for increasing plant resistance to frost damage in such plants as corn, soybeans, citrus fruits and coffee. 13. Application according to any of claims 1-7 for increasing the resistance of plants to frost damage of flowers, young fruits and seedlings. 14. Use according to any of claims 1-7, in which strobilurin or its salt is used together with an additional active compound from the group of fungicides and growth retardants. 15. Use according to any of claims 1-7, in which strobilurin or its salt is used together with an additional active compound selected from the group of compounds with deterrent activity - primers and 1-methylcyclopropene (1-MOP). 16. Application according to any of claims 1-13 in combination with prohexadione-Ca and/or trinexapak-ethyl, and/or commonly accepted cryoprotectants. 17. Use according to any of claims 1-13 in combination with vitamin E and/or abscisic acid and/or conventional cryoprotectants. 18. Application according to claim 16 or 17, in which the cryoprotectant is selected from glycerol and a salt of formic acid. 19. Application according to claim 17, in which strobilurin or its salt and vitamin E are taken in a mass ratio of 1:11 to 1:20. 20. Use according to any one of claims 17-19, in which strobilurin or its salt and abscisic acid are taken in a mass ratio of 1:0.05 to 1:1. 21. Application according to any one of claims 16-20, in which strobilurin or its salt and generally accepted cryoprotectants are taken in a mass ratio of 1:10 to 1:500. 22. Application according to any one of claims 1-7, in which strobilurin or its salt is in the form of an aqueous spray solution containing the mentioned compound in an amount from 5 to 1000 ppm. 23. Use according to any one of claims 1-7, in which the rate of use of strobilurin or its salt is in the range of up to 1000 g/ha. 24. The method of increasing resistance of plants to low temperatures, in which the composition containing at least one strobilurin or its salt according to any of claims 1-7 is applied to plant seeds. 25. The method according to claim 24, in which the composition is an aqueous composition.