Method for controlling of cultural plant phytopathogenic diseases and fungicide composition

FIELD: agriculture, fungicides.

SUBSTANCE: claimed method includes treatment of contaminated cultural plants or cultivation area thereof with effective amount of composition, containing A) N-sulfonylvaline amide of formula I 1, wherein R1 represents hydrogen or haloprenyl; and R1 represents C1-C4-alkyl, in combination with B) methalaxyl, or fluozinam, or mancoceb, or chlorithalonyl, or strobyluzine, or pyraclostrobine, or acibenzolar-S-methyl, or dimethoform, or fludioxonyl, or cimoxanyl, or imazalyl in synergistically effective amounts. Fungicide composition containing effective combination of A and B in synergistically effective amounts in combination with agriculturally acceptable carrier and optionally with surfactant.

EFFECT: composition of increased fungicidal action due to synergic effect.

8 cl, 12 ex

 

The present invention relates to new fungicidal compositions intended for the treatment of phytopathogenic diseases of cultivated plants, especially diseases caused by phytopathogenic fungi, and to a method of combating phytopathogenic diseases of cultivated plants.

It is known that certain sulfonylamide derivatives have biological activity against phytopathogenic fungi (see, for example, WO 95/30651 and WO 99/07647, where their properties are described and methods of production). At the same time as used on plants fungicides designed to handle a variety of crops of agricultural plants, well-known various fungicides from other chemical classes of compounds. However, the resistance of cultivated plants and their activity against phytopathogenic parasitic fungi on plants in many cases, and in various aspects not always meet the needs of agricultural practice.

When creating the present invention, it was found that the application of (a) N-sulfonylamide formula I

where R1denotes hydrogen, C1-C4alkyl, C3-C6cycloalkyl or halophenol and

R2stands With1-C4alkyl,

in combination

B) or metalaxyl formula II, including meta is axil-M formula IIa

or fluazinam formula III

or MANCOZEB formula IV

or chlorthalonil formula V

or strobilurins formula VI

where Z denotes CH or N, and R stands for

first of all with strobilurins formula VIa, VIb or VIc

(VIc) picoxystrobin

or pyraclostrobin (BAS 500F) formula VII

either acibenzolar-S-stands formula VIII

or dimethomorph formula IX

or fludioxonil formula X

or cymoxanil formula XI

or imazalil formula XII, including S-imazalil formula XIIa

is especially effective for combating or preventing fungal diseases of cultivated plants. Such compositions have enhanced as a result of synergistic fungicidal activity.

In the context of the present description, the term composition refers to the different compositions of components a)and B), for example, in the form of separate "ready to use" form, in the form of a combined mixture for spraying containing separate formulations of the individual active substances, for example, in the form of a mixture, prepared in the tank, i.e. the "tank mixtures"and to the joint application of the individual active substances that contribute sequentially, i.e. one after another in a short period of time, comprising, for example, several hours or days. The procedure for making components a) and B) is not essential for implementing the present invention.

The composition of the invention may also comprise more than one of the active substances constituting the component (B), if you want to expand the range of controlled diseases. For example, agricultural practices may be appropriate to combine two or three compounds constituting component (B), with any of the compounds of formula I, or any preferred group of compounds of formula I.

In WO 95/30651 and WO 99/07647 describes the following specific compounds of formula I.

Table 1
Conn. No.R1R2
I.01NWith2H5
I.02NCH3
I.03CH3CH3
I.04CH3With2H5
I.05With2H5With2H5
I.06With2H5CH3
I.07With3H5cycleCH3
I.08With3H5cycleWith2H5
I.09With5H9cycleCH3
I.10With5H9cycleCH3
I.113-Cl-C6H5With2H5
I.123-Cl-C6H5CH3
I.134-Cl-C6H5With2H5
I.144-Cl-C6H5CH3
I.153-Br-C6H5With2H5
I.163-Br-C6H5CH3
I.C74-Br-C6H5With2H5
I.18 4-Br-C6H5CH3
I.194-Cl-C6H5With3H7-n
I.204-Cl-CBH5WithCH7-out
I.214-Cl-CBH5With4H9-n
I.224-Cl-C6C5With4H9-Deut

The preferred embodiment of the present invention are those compositions which comprise as component A) a compound of formula I, where R1denotes hydrogen, methyl, ethyl, chlorophenyl or bromophenyl, or where R1denotes hydrogen, ethyl, 4-chlorophenyl or 4-bromophenyl, or where R1represents 4-chlorophenyl, or where R2denotes methyl or ethyl, or R2denotes methyl. A preferred subgroup of compounds characterized in that R1denotes hydrogen, ethyl, 4-chlorophenyl or 4-bromophenyl and R2denotes methyl or ethyl. In another preferred subgroup of compounds R1represents 4-chlorophenyl, and R2denotes methyl or ethyl.

Among the compounds of the present invention, the most preferred are mixtures of compounds I.01, I.11, I.12, I.13, I.14, I.15, I.17, I.19, I.20, I.21 I.22 and with compounds representing a component of the), primarily marketed products that fall within the specified range of compounds, i.e. with marketed products, which are specified in this document. Most preferred are the combination of compounds I.13 with any connection representing a component B), the combination of compounds I.14 with any connection representing a component B), the combination of compounds I.15 with any connection representing a component B), the combination of compounds I.17 with any connection representing a component B), the combination of compounds I.19 with any connection representing a component B), the combination of compounds I.20 with any connection representing a component B), the combination of compounds I.21 with any connection representing a component B), and the combination of compounds I.22 with any compound constituting the component (B).

Salts of the active substances derived amine and research, produced by reaction with acids, for example with halogen acids such as hydrofluoric acid, hydrochloric acid, Hydrobromic acid and itestosterone acid, or sulfuric acid, phosphoric acid or nitric acid, or with organic acids such as acetic acid, triperoxonane acid, trichloroacetic Ki the lot, propionic acid, glycolic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, formic acid, benzolsulfonat acid, para-toluensulfonate acid, methanesulfonate acid, salicylic acid, para-aminosalicylic acid and 1,2-naphthalenedisulfonic acid.

Combinations of active substances are effective against phytopathogenic fungi belonging to the following classes: Ascomycetes (for example Venturia, Podosphaera, Erysiphe, Monilinia, Mycosphaerella, Uncinula); Basidiomycetes (for example, R. Hemileia, Rhizoctonia, Puccinia); imperfect fungi (also known as Deuteromycetes; for example Botrytis, Helminthosporium, Rhynchosporium, Fusarium, Septoria, Cercospora, Alternaria, Pyricularia and Pseudocercosporella herpotrichoides); Oomycetes (e.g., Phytophthora, Peronospora., Pseudoperonospora, Albugo, Bremia, Pythium, Pseudosclerospora, Plasmopara).

Subject to the protection of cultural plants falling under the scope of the present invention include, for example, the following plant species: beet (sugar beet and fodder beet); stone fruit, pome fruit, berry crops (apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries and blackberries); leguminous plants (beans, lentils, peas, soybeans); oil crops (rape, mustard, poppy, olive, sunflower, coconut, castor, cocoa beans, groundnuts); cucumber plants (pumpkins, cucumbers, melons); fibre plants (cotton, flax, hemp, jute); citrus crops (oranges, lemons, grapefruit, mandarins); vegetables (spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, peppers); Laurel crops (avocado, cinnamon tree, camphor tree), or plants such as maize, tobacco, nuts, coffee, sugar cane, tea, vines, hops, durian, bananas and natural rubber plants, as well as turf grass and ornamental plants (flowers, shrubs, deciduous trees and evergreen trees such as conifers). This list does not limit the scope of the invention. In the context of the present invention are of special interest such crops as potatoes, tomatoes, grapes, tobacco, and other vegetable crops such as pumpkin and salad.

The compositions of the present invention can also be applied in the field of protection of technical material from damage by fungi. These technical materials and systems include wood, paper, leather, construction, cooling and heating systems, ventilation and air conditioning, etc. of the Composition of the present invention can be applied to prevent undesirable effects such as decay, discoloration or plasteline.

The compositions of the present invention is particularly effective against causative agents of downy mildew and late blight, first always is against pathogens, stir the grapes, potatoes, tomatoes, pumpkins and tobacco. In addition, they are particularly effective against pathogens of leaf spot and brown spot Solanaceae; primarily against pathogens R. Alternaria in potatoes, tomatoes, pumpkins and black rot, rubella grape leaves, powdery mildew, green plesnevelae rot and necrosis of shoots of grapes.

The number of combinations according to the invention, which should be applied should depend on various factors, such as the use of connection object processing (plant, soil, seed), the type of processing (for example, spraying, dusting, seed treatment), the aim of treatment (prophylactic or therapeutic), the type of fungi to be processed, and the processing time.

Compounds of formulas II and IIa are known under the common names of metalaxyl and metalaxyl-M, see The Pesticide Manual, 11th ed., 1997, the number of connections 470 and 471.

The compound of the formula III are known under the common name fluazinam, see The Pesticide Manual, 11th ed., 1997, room 329 connection.

The compound of the formula IV are known under the common name of MANCOZEB, see The Pesticide Manual, 11th ed., 1997, the connection number 452.

The compound of the formula V are known under the common name of CHLOROTHALONIL, see The Pesticide Manual, 11th ed., 1997, number of connections 133.

Preferred compounds of formula VI are known which are under common names, AZOXYSTROBIN VIa, Trifloxystrobin VIb and VIe, see The Pesticide Manual, 11th ed., 1997, number of connections 43, European patent EP-B-460575 and the application for the European patent EP-A-278595 or AGROW, No. 324, pp. 27, March 12, 1999.

The compound of the formula VII are known under the common name pyraclostrobin (BAS 500F), see WO 96/01256.

The compound of the formula VIII are known under the common name of acibenzolar-S-methyl, see The Pesticide Manual, 11th ed., 1997, number of connections 114.

The compound of the formula IX are known under the common name of dimethomorph, see The Pesticide Manual, 11th ed., 1997, the number of connection 244.

The compound of the formula X are known under the common name of fludioxonil, see The Pesticide Manual, 11th ed., 1997, the number of connection 334.

The compound of formula XI are known under the common name of having cymoxanil, see The Pesticide Manual, 11th ed., 1997, the number of connection 182.

The compound of the formula XII are known under the common name of imazalil, see The Pesticide Manual, 11th ed., 1997, number of connections 410, and his pure optical S-isomer of formula XIIa known under the common name of the S-imazalil, see PCT WO 00/38521.

Specific compounds constituting component (B)mentioned in the previous sections, go on sale. Other compounds constituting component (B)which fall within the scope of formula VI can be obtained by methods analogous to those known for getting marketed compounds.

P and the creation of the invention it has been unexpectedly discovered, what is the use of compounds of formula II-XII in combination with the compound of the formula I in substantially increases the effectiveness of the latter compounds against fungi, and Vice versa. Furthermore, the method according to the invention are effective against a wider spectrum of these mushrooms, which you can destroy with the help of active substances used in this way, in the case of individual application.

It should be understood that the specific preferred mixture according to the present invention can be represented by combinations of active substances of formula I or any subgroup of formula I, or specifically referred to representatives of the subgroups, with the second fungicide selected from the group comprising acibenzolar-S-methyl, AZOXYSTROBIN, CHLOROTHALONIL, having cymoxanil, dimethomorph, fluazinam, fludyoksonil imazalil, S-imazalil, MANCOZEB, metalaxyl, metalaxyl-M, picoxystrobin, pyraclostrobin (BAS 500 F) and Trifloxystrobin.

In addition, as the second fungicide, representing the component (B), preferred are metalaxyl and metalaxyl-M.

The mass ratio of the components a) and B) are chosen in such a way as to obtain a synergistic fungiidae action. Typically, the mass ratio of the components a) and B) is from 2000:1 to 1:1000.

A synergistic effect of the composition can be seen from the fact that NGF is iceee action of the composition, contains the components A)+B) is higher than the sum of the fungicidal action of each of components a) and B) separately.

If component B) is a metalaxyl formula II, the mass ratio (a) and (B) is, for example, from 40:1 to 1:400, preferably from 20:1 to 1:100 and most preferably from 10:1 to 1:20.

If component B) is a metalaxyl-M of the formula IIa, the mass ratio (a) and (B) is, for example, from 80:1 to 1:200, preferably from 40:1 to 1:50 and more preferably from 20:1 to 1:20.

If component B) is fluazinam formula III, the mass ratio (a) and (B) is, for example, from 40:1 to 1:100, preferably from 20:1 to 1:50 and most preferably from 20:1 to 1:10.

If component B) is MANCOZEB formula IV, the mass ratio (a) and (B) is, for example, from 4:1 to 1:600, preferably from 1:1 to 1:100 and most preferably from 1:4 to 1:20.

If component B) is CHLOROTHALONIL formula V, the mass ratio (a) and (B) is, for example, from 4:1 to 1:400, preferably from 1:1 to 1:100 and most preferably from 1:4 to 1:20.

If component B) is AZOXYSTROBIN formula VIa, the mass ratio (a) and (B) is, for example, from 40:1 to 1:200, preferably from 20:1 to 1:100 and most preferably from 10:1 to 1:20.

If component B) is trifl xystrobin formula VIb, the mass ratio (a) and (B) is, for example, from 40:1 to 1:200, preferably from 20:1 to 1:100 and most preferably from 10:1 to 1:20.

If component B) is picoxystrobin formula VIc, the mass ratio (a) and (B) is, for example, from 80:1 to 1:200, preferably from 40:1 to 1:100 and most preferably from 20:1 to 1:20.

If component B) is pyraclostrobin (BAS 500F) of the formula VII, the mass ratio (a) and (B) is, for example, from 80:1 to 1:200, preferably from 40:1 to 1:100 and most preferably from 20:1 to 1:20.

If component B) is acibenzolar-S-methyl of the formula VIII, the mass ratio (a) and (B) is, for example, from 2000:1 to 1:8, preferably from 1000:1 to 1:1 and most preferably from 500:1 to 10:1.

If component B) is dimethomorph formula IX, the mass ratio (a) and (B) is, for example, from 40:1 to 1:200, preferably from 20:1 to 1:100 and most preferably from 10:1 to 1:20.

If component B) is a fludyoksonil formula X, the mass ratio (a) and (B) is, for example, from 80:1 to 1:100, preferably from 40:1 to 1:50 and most preferably from 10:1 to 1:20.

If component B) is the result of having cymoxanil formula XI, the mass ratio (a) and (B) is, for example, from 40:1 to 1:100, preferably from 20:1 to 1:50 and most preferably from 20:1 to 1:1.

If component B) is imazalil formula XII or its isomer S-imazalil formula XIIa, the mass ratio (a) and (B) is, for example, from 1:400 to 400:1, preferably from 1:200 to 200:1 and most preferably from 1:20 to 20:1; respectively from 1:200 to 200:1, preferably from 1:100 to 100:1 and most preferably from 1:10 to 10:1.

The method according to the invention provides for the application to be processed plants or their habitat an effective fungicide quantity, in a mixture or separately, the compounds of formula I and the compounds constituting component (B).

The concept of "habitat" in the context of this description refers to the fields, which are subject to processing plants or who sowed seeds of cultivated plants or to a place where the soil is sown seed. In the context of the present description, the term "seed" refers to a material for propagation, such as cuttings, seedlings, seeds, sprouted or soaked seeds.

New compositions are highly effective against a broad spectrum of phytopathogenic fungi, in particular from the classes Ascomycetes, Basidiomycetes and Oomycetes. Some of them have a systemic effect and can be used as a fungicide for treatment of leaves and soil fungicides.

The fungicide is s compositions are of special interest to fight a large number of species of fungi in various crops or their seeds, especially on such field crops as potato, tobacco, and sugar beets, and wheat, rye, barley, oats, rice, maize, lawns, cotton, soybeans, coffee, sugarcane, fruit and ornamental crops in the horticulture and viticulture, and in vegetables such as cucumbers, beans and pumpkin.

The composition is applied by treating the fungi or the seeds, plants or materials that are in danger of defeat mushrooms, or soil effective as a fungicide number of active substances.

Agents can be made before or after infection by fungi of the materials, plants or seeds.

New compositions are especially useful for combating plant diseases caused by the following pathogens:

Alternaria spp. on fruits and vegetables,

Botrytis cinerea (grey mould) on strawberries, tomatoes and grapes,

Bremia lactucae on lettuce,

Cercospora arachidicola on peanuts,

Colletotrichum musae on banana,

Erysiphe cichoracearum and Sphaerotheca fuliginea on the pumpkins

Fusarium spp. and Verticillium spp. on various plants, etc,

Fusarium moniliforme on bananas,

Fusarium pallidoroseum bananas,

Monilinia fructigena on Apple trees,

Penicillium digitatum on citrus fruit,

Penicillium expansum on Apple trees,

Penicillium italicum on citrus fruits,

Peronospora. tabacina on tobacco,

Phyctaena vagabunda on Apple trees,

Phytophthora infestans on potatoes and tomatoes,

Plasmopara viticola on grapes,

Pseudoperonospora cucbensi on what aquah,

Pyricularia oryzae on rice,

Pythium spp. lawn grasses, ornamental plants and cotton,

Rhizoctonia spp. on cotton, rice and lawn grass,

Uncinula necator, Guignardia bidwellii and Phomopsis viticola on grapes,

Verticillium theobromae on the bananas.

For processing plants compound of formula I is applied at the rate of from 5 to 2000 g A.I/ha, preferably from 10 to 1000 g A.I/ha, for example 50, 75, 100, or 200 g A.I/ha, in combination with the compound constituting the component (B), which apply at the rate of from 1 to 5000 g A.I/ha, in particular from 2 to 2000 g A.I/ha, for example 100, 250, 500, 800, 1000, 1500 g A.I/ha, depending on the class of chemical the substances used as component B).

If component B) is a metalaxyl formula II, it is used in combination with the compound of the formula I with a consumption rate of, for example, from 50 to 2000 g A.I/ha

If component B) is a metalaxyl-M of the formula IIa, then it is used in combination with the compound of the formula I with a consumption rate of, for example, from 25 to 1000 g A.I/ha

If component B) is fluazinam formula III, it is used in combination with the compound of the formula I with a consumption rate of, for example, from 50 to 500 g A.I/ha

If component B) is MANCOZEB formula IV, it is used in combination with the compound of the formula I with a consumption rate of, for example, from 500 to 3000 g A.I/ha

If to the ponent B) is CHLOROTHALONIL formula V, it is used in combination with the compound of the formula I with a consumption rate of, for example, from 500 to 2000 g A.I/ha

If component B) is AZOXYSTROBIN formula VIa, it is used in combination with the compound of the formula I with a consumption rate of, for example, from 50 to 1000 g A.I/ha

If component B) is Trifloxystrobin formula VIb, then it is used in combination with the compound of the formula I with a consumption rate of, for example, from 50 to 1000 g A.I/ha

If component B) is picoxystrobin formula VIc, then it is used in combination with the compound of the formula I with a consumption rate of, for example, from 25 to 1000 g A.I/ha

If component B) is pyraclostrobin (BAS 500F) of the formula VII, it is used in combination with the compound of the formula I with a consumption rate of, for example, from 25 to 1000 g A.I/ha

If component B) is acibenzolar-S-methyl of the formula VIII, it is used in combination with the compound of the formula I with a consumption rate of, for example, from 1 to 40 g A.I/ha

If component B) is dimethomorph formula IX it is used in combination with the compound of the formula I with a consumption rate of, for example, from 50 to 1000 g A.I/ha

If component B) is a fludyoksonil formula X, then it is used in combination with the compound of the formula I with a consumption rate of, for example, from 25 to 500 g A.I/ha

If component B) is from the battle of having cymoxanil formula XI, it is used in combination with the compound of the formula I with a consumption rate of, for example, from 25 to 500 g A.I/ha

If component B) is imazalil formula XII or its isomer S-imazalil formula XIIa, it is used in combination with the compound of the formula I with a consumption rate of, for example, from 5 to 2000 g A.I/ha, respectively, from 3 to 1000 g A.I/ha

In agricultural practice the norms of consumption of the composition depend on the type of exposure and range from 0.02 to 4 kg of active substance per hectare.

If the active substances used for the treatment of seeds, it is usually sufficient to use the consumption rate of from 0.001 to 50 g A.I/kg and preferably from 0.01 to 10 g/kg seed.

The invention also relates to fungicidal compositions comprising a compound of formula I and the compound constituting the component (B).

The composition according to the invention can be applied in any conventional form, for example in the form of double packaging, quickly soluble granules, liquid formulation, mulgirigala concentrate or wettable powder, in combination with acceptable agricultural auxiliaries. Such compositions can be obtained in the usual way, for example by mixing the active ingredients with appropriate excipients (diluents or solvents, and optionally the other members of the preparative form ingredients, such as surfactants). In that case, if you want to maintain effectiveness over a long period of time, you can also use the usual formulations of slow release. Specific compositions intended for use as forms for spraying, such as dispersible in water concentrates or wettable powders, may contain surfactants such as wetting and dispersing agents, for example condensation products of formaldehyde and naphthalenesulfonate, alkylarylsulfonate, ligninsulfonate, aliphatic alkylsulfate and ethoxylated alkylphenol and an ethoxylated aliphatic alcohol.

Preparative form intended for seed, causing the seeds are well known manner, using a combination according to the invention and a diluent acceptable for seed preparative form, for example in the form of aqueous suspensions or in the form of a dry powder having good adhesive properties in relation to seeds. Such compositions intended for seed, known in this area. Compositions intended for seed, may contain a single active ingredient or combination of active substances in encapsulated form, for example in the form of capsules with IU the slow release of active substances or in the form of microcapsules.

In General, the compositions include from 0.01 to 90 wt.% active ingredient, from 0 to 20% is acceptable for agriculture surfactant and 10 to 99.99% solid(s) or liquid(s) assisted(s) of the substance, the active substance is at least a compound of formula I in combination with the compound constituting the component (B), and optionally other active substances, in particular bactericides or preservatives or other Concentrated forms of the compositions generally contain from about 2 to 80 wt.%, preferably about 5 to 70 wt.% the active substance. Used for processing the preparative forms of compositions may contain, for example, from 0.01 to 20 wt.%, preferably from 0.01 to 5 wt.% the active substance. Despite the fact that as provided in the sale of the compositions is generally preferable concentrated compositions, the end user typically uses dilute compositions.

The following examples are given to illustrate the concept of "active ingredient" refers to a mixture of compound I and the compounds constituting component (B)in a certain ratio.

Examples preparative forms

Wettable powders

in)
Componentsa)6)
the active ingredient25%50%75%
[I:compb)=1:3(a), 1:2(b)1:1(V)]
sodium lignosulphonate5%5%-
sodium lauryl sulfate3%-5%
diisobutyldimethoxysilane sodium-6%10%
polietilenglikolya ether of phenol (7-8 moles of ethylenoxide)-2%-
highly dispersed silicon dioxide5%10%10%
kaolin62%27%-

The active ingredient is thoroughly mixed with excipients and the mixture is thoroughly ground in an appropriate mill, receiving wettable powders which can be diluted with water to obtain suspensions of any desired concentration.

Mulgirigala concentrates

active substance (I:compb)=1:6)10%
polietilenglikolya ether op (4-5 moles
ethylenoxide)3%
modellen onsultant calcium 3%
polietilenglikolya ether of castor oil (35
moles of ethylenoxide)4%
cyclohexanone30%
Kiselyova mixture50%

Emulsions of any required concentration for use in the field of plant protection products can be prepared by dilution of such concentrates with water.

Dusty

Componentsa)b)in)
active substance (I:compb)=1:6)5%6%4%
(a); 1:2 (b); 1:10 ()]
talc95%--
kaolin-94%-
mineral fillers--96%

Ready-to-use dusty obtained by mixing the active ingredient with the carrier and grinding in an appropriate mill. Such powders can also be used in the form of powders for seed treatment.

Extruded granules

active substance (I:compb)=2:1)15%
sodium lignosulphonate2%
carboxymethylcellulose1%
kaolin82%

The active substance is mixed and milled with auxiliary substances and moisten with water. The mixture ekstragiruyut and then dried in the air stream.

Granules coated

active substance (I:compb)=1:10)8%
polyethylene glycol (molecular weight:
200 atomic mass)3%
kaolin89%

Finely ground active ingredient is uniformly fed into the mixer, to the kaolin moistened with polyethylene glycol. In this way receive a dust free granules coated.

Suspension concentrate

active substance (I:compb)=1:8)40%
propylene glycol10%
simple ether nonylphenolethoxylates (15
moles of ethylenoxide)6%
sodium lignosulphonate10%
carboxymethylcellulose1%
silicone oil in the form of a 75%water
emulsion1%
water32%

Finely ground active ingredient is thoroughly mixed with auxiliary substances, receiving a suspension concentrate from which suspensions of any desired concentration can be prepared by dilution with water. Such diluted formulation can be applied for processing by spraying, watering or dipping living plants, as well as material for reproduction of plants and to protect them from infection by microorganisms.

Suspension capsules slow release

28 parts of a combination of compounds of formula I and the compounds constituting component (B), or each of these compounds separately mixed with 2 parts of an aromatic solvent and 7 parts of a mixture (8:1) colorvision/polymethylenepolyphenylisocyanate. This mixture emuleret in a mixture, containing 1.2 parts of polyvinyl alcohol, 0.05 part of non and 51.6 parts of water, to obtain particles of the desired size. To this emulsion is added a mixture containing 2.8 parts of 1,6-diaminohexane 5.3 parts of water. The mixture is stirred until completion of the polymerization reaction.

The resulting suspension capsules stabilized by adding a 0.25 parts of a thickening agent, and 3 parts of dispersing agent. Preparative form of suspense the capsules contains 28% of active substances. The average diameter of the capsules is 8-15 microns.

The resulting composition is applied to seeds in the form of a water suspension using a device suitable for this purpose.

Biological examples

It is believed that the combination of active substances has a synergistic effect, if the activity of the combination of active substances is higher than the sum of the activities of the individual components.

The value of E, i.e. the activity expected for this composition of active substances, are estimated using the so-called Colby formula as follows (Colby S.R. "Calculating synergistic and antagonistic responses of herbicide combination". Weeds, t.15, p.20-22; 1967):

part./million means the number of milligrams of active ingredient (A.I.) per liter of mixture for spraying;

X means the activity (in %) of the active substance I using p ppm million active substance;

Y means the activity (in %) of the active substance II when using q frequent./million active substance.

The expected (additive) activity of active substances (A)+B) when using p+q ppm million active substance in accordance with the formula

If you have received actually active (On) higher than expected activity (E), the activity of the composition is vergadain, i.e. a synergistic effect. In mathematical terms, the coefficient is ecient synergy SF corresponds to the O/E. In agricultural practice, is that the value of SF≥1,2 indicates a significant increase in activity compared to a net sum of activities (expected activity), whereas the value of SF≤0,9 indicates the loss of activity compared with the expected activity.

In another embodiment, a synergistic effect can be determined from graphs of dependence of activity on the dose according to the so-called method of Wadley. In accordance with this method the efficiency of the A.I is determined by comparison of the extent of damage by the fungus treated plants and untreated, similarly infected and grown in the same conditions, the control plants. Each A.I. test in 4-5 concentrations. Graphs of dependence of activity on the dose used to determine the values of the EU90(i.e. the concentration of A.I, providing 90%eradication of the disease) of individual compounds and combinations of compounds EUMoloch.). These experiments allow to determine the values for mixtures when this mass ratio compared with the values that would be obtained if there were only an additive effect of the components of the EU90(A+B)home screen.). Is EU90(A+B)home screen.) compute method Wadley (Levi and others, EPPO-Bulletin 16, 1986, 651-657):

where a and b represent the mass ratio of the compounds a and B in the mixture and indexes (A), (B) and (A+B) are obtained in reality the values of the EU90compounds a, B or this composition A+b Ratio EU90(A+B)projection/EU90(A+B)reciprepresents the coefficient of the interaction, i.e. the ratio of synergism (SF). In the case of synergism SF>1.

Example-1: effectiveness against Plasmopara viticola on grapes

5-week-old seedlings of grapes Gutedel treated with the test compound in the form of a corresponding formulation in the chamber for spraying. After 1 day after application of active substances and mixtures of active substances of plant grapes inoculant by spraying the underside of leaves of the test plants with a suspension of sporangia (4×104the sporangia/ml) of Plasmopara viticola. After an incubation period of 6 days in the greenhouse at +21°C and relative humidity of 95% of the evaluated cases. Interaction of fungicides in mixtures calculated by the method of Colby.

Example b-2: activity against Plasmopara viticola on the leaf disks grapes (variety Gutedel)

The effectiveness of the compounds against Plasmopara viticola can be estimated in laboratory experiments on leaf disks in 24-hole plates (using 4 disks to assess variations).

Connection is by means of formula I and compounds representing the component (B), individually and mixtures thereof is applied against the lower side of the leaf disk, lying 0.2%water agar, one day before inoculation.

Inoculation is carried out by spraying the underside of leaves with a suspension of sporangia (70,000 sporangia/ml). After incubation for 7-8 days (under standard conditions in a climatic chamber at 18°With a light cycle of 12 h light/12 h darkness) measure the affected area (the area in which sporulation occurs) of each leaf disc and expressed as % of the total area of leaf disk. Activity is expressed as % relative to the level of development of the disease in the fully infected untreated leaf disks of grapes. The expected interaction of components in the mixture (E-values) calculated according to Colby.

Results

Table 2
Component a (part./million) connection I.14Component B (part./million) compound IIaMix ratio (A:B)The resulting activity (in %)Expected activity (in %)The coefficient of synergy (SF)
0,136
0,05 /td> 18
0,19
0,055
0,0253
0,10,11:169421,7
0,050,051:136221,6
0,10,51:584481,7
0,050,251:541241,7
0,050,51:1071342,1
Component a (part./million) connection I.14Component B (part./million) compound IVMix ratio (A:B)The resulting activity (O %)Expected activity (in %)The coefficient of synergy (SF)
0,0518
0,515
0,253
0,050,251:527211,3
0,050,51:1053301,7
Component a (part./million) connection I.14Component B (part./million) connection VIaMix ratio (A:B)The resulting activity (in %)Expected activity (in %)The coefficient of synergy (SF)
0,136
0,0518
0,0110
0,010
0,050,015:124181,3
0,010,011:122102,1
0,011:1047361,3

Component a (part./million) connection I.14Component B (part./million) connection IXMix ratio (A:B)The resulting activity (in %)Expected activity (in %)The coefficient of synergy (SF)
0,136
0,0518
0,0110
162
0,0514
0,010
0,050,015:122181,2
0,050,051:150291,7
0,010,011:1 22102,2
0,111:1091761,2
Component a (part./million) connection I.14Component B (part./million) compound XIMix ratio (A:B)The resulting activity (O %)Expected activity (in %)The coefficient of synergy (SF)
0,2536
0,0518
0,0258
0,010
0,250,02510:181641,3
0,050,015:12436181,3

Similar results were obtained using other compounds constituting component B). Similar results were obtained also when using other compounds of the formula I, for example I.01, I.11, I.12, I.13, I.15, I.17, I.19, I.20, I.21 I.22 and in combination is the be connections, representing the component (B).

Example b-3: activity against Uncinula necator on grapes

Plant grapes "Gutedel" at the 4-6 leaf stage inoculant conidia Uncinula necator by dusting the tested plants conidia. After keeping for 2 days under conditions of high humidity and low light intensity plants incubated in growth chamber for 10-14 days at a relative humidity of 70% and a temperature of 22°C. 3 days after inoculation applied active substances and mixtures by spraying aqueous suspensions obtained by suspendirovanie active substances in demineralized water and proper breeding. For each treatment using 5 plants. 12 days after inoculation the results of the experiment are estimated by determining the percentage of the fungus affected leaves compared with the level of disease control plants. Interaction of fungicides in mixtures are calculated according to the method of Colby.

Example b-4: activity against Phytophtora infestans on tomatoes

(a) Medical action

Plants of tomato varieties "Roter Gnom" grow for three weeks and then sprayed with a suspension of zoospores of the fungus and incubated in a chamber at +18-+20°and saturated atmospheric humidity. Hydration stopped after 24 hours After drying of the plants they are sprayed with a mixture (to ncentrate 200 ppm million), obtained from the preparative form of active substances in the form of a wettable powder. After drying of the applied spray coating the plants return for 4 days in a hydrating chamber. The number and size of the typical damage of leaves that emerged during this time, used as a criterion for evaluating the effectiveness of the tested substances.

b) Preventive system action

The active substance formulations in the form of wettable powder, is applied at a concentration of 60 ppm million (in relation to the volume of soil) to the soil surface flower pots, which are 3-week-old plants of tomato varieties "Roter Gnom". After three days the underside of leaves are sprayed with a suspension of zoospores Phytophtora infestans. Then the plants are incubated for 5 days in the chamber for spraying at +18 -+20°and saturated atmospheric humidity. The number and size of the typical damage of leaves that emerged during this time, used as a criterion for evaluating the effectiveness of the tested substances.

Example B-5: activity against Phytophtora on potato plants

a) Residual protective action

2-3-week-old potato plants (cultivar Bintje) grown for 3 weeks and then sprayed with a mixture for spraying (0.02% of active substance)prepared from smachiwausa the Xia powder active ingredients. After 24 hours the treated plants are infected by a suspension of sporangia of the fungus. Defeat the fungus evaluated after incubation of the infected plants for 5 days at a relative atmospheric humidity of 90-100% and a temperature of +20°C.

b) System action

Mixture for spraying (0,002% of active substances in terms of the volume of soil)prepared from wettable powder of the active substances, watering the soil around 2-3-week-old potato plants (cultivar Bintje), which were grown for 3 weeks. Take precautions to ensure that the mixture for spraying did not get on above-ground parts of plants. After 48 hours the treated plants are infected by a suspension of sporangia of the fungus. Defeat the fungus evaluated after incubation of the infected plants for 5 days at a relative atmospheric humidity of 90-100% and a temperature of +20°C.

Example B-6: activity against Phytophtora infestans on the leaf discs of potato (cultivar Bintje)

The effectiveness of the compounds against Phytophtora infestans can be estimated in laboratory experiments on leaf disks in 24-hole plates (using 4 disks to assess variations).

Connections separately and mixtures thereof is applied against the lower side of the leaf disk, lying 0.2%water agar, one day before inoculation. Inoculation is carried out by applying to each drive one to the lip (30 ml) suspension of sporangia (50,000 sporangia/ml). After incubation for 6 days (under standard conditions in a climatic chamber at 18°With a light cycle of 12 h light/12 h darkness) measure the affected area (the area in which sporulation occurs) of each leaf disc and expressed as % of the total area of leaf disk. Activity is expressed as % relative to the level of development of the disease on completely amazed untreated leaf disks of grapes. The expected interaction fungicidal components in mixtures (E-values) calculated according to Colby.

Results

Table 3
Component a (part./million) connection I.14Component B (part./million) compound IIIMix ratio (A:B)The resulting activity (O %)Expected activity (in %)The coefficient of synergy (SF)
0,0511
0,0250
0,011
0,529
0,050
0,0250
0,050,51:126112,3

Component a (part./million) connection I.14Component B (part./million) compound IIIMix ratio (A:B)The resulting activity (O %)Expected activity (in %)The coefficient of synergy (SF)
0,0250,0251:160the 5.7
0,050,251:566341,9
0,010,051:5919,0
0,050,51:1066371,8
Component a (part./million) connection I.14Component B (part./million) connection VMix ratio (A:B)The resulting activity (O %)Expected activity (in %)The coefficient synergis is a (SF)
0,0511
0,50
0,050,51:1014111,3
Component a (part./million) connection I.14Component B (part./million) compound VIIIMix ratio (A:B)The resulting activity (O %)Expected activity (in %)The coefficient of synergy (SF)
0,0250
0,250
0,0250,251:10302,9

Similar results were obtained using other compounds constituting component B). Similar results were obtained also when using other compounds of the formula I, for example I.01, I.11, I.12, I.13, I.15, I.17, I.19, I.20, I.21 I.22 and, in combination with the compounds constituting component (B).

Example B-7: activity against Monilinia fructigena on apples

Mature fruit are susceptible the CSOs varieties of apples treated preparative form of the test mixture in the chamber for spraying. After one day after application of active substances and mixtures of active substances apples inoculant by spraying directly tested apples spore suspension Monilinia fructigena (4×104spores/ml). After incubation for 7-14 days at a temperature of +21°C and relative humidity of 95% in growth chamber estimate the number of cases of the disease and its severity. Interaction of fungicides in mixtures are calculated according to the method of Colby.

Example B-8: activity against Penicillium expansum on apples

The Mature fruit of susceptible varieties of apples treated preparative form of the test mixture in the chamber for spraying. After one day after application of active substances and mixtures of active substances apples inoculant conidia of Penicillium expansum by spraying the test apples suspension of conidia of Penicillium expansum. After incubation for 7-14 days at a temperature of +22°C and relative humidity 70% in growth chamber estimate the number of cases of the disease and its severity. Interaction of fungicides in mixtures are calculated according to the method of Colby.

Example B-9: activity against Phlyctaena vagabunda on apples

The Mature fruit of susceptible varieties of apples treated preparative form of the test mixture in the chamber for spraying. After one day after application of active substances and mixtures acting is x substances apples inoculant conidia Phlyctaena vagabunda by spraying the test apples suspension of conidia. After incubation for 7-14 days at a temperature of +22°C and relative humidity 70% in growth chamber estimate the number of cases of the disease and its severity. Interaction of fungicides in mixtures are calculated according to the method of Colby.

Example 10: activity against Colletotrichum musae on banana

Ripe bananas process preparative form of the test mixture in the chamber for spraying. After one day after application of active substances and mixtures of active substances bananas inoculant conidia of Colletotrichum musae by spraying the test of bananas suspension of conidia. After incubation for 7-14 days at a temperature of +22°C and relative humidity 70% in growth chamber estimate the number of cases of the disease and its severity. Interaction of fungicides in mixtures are calculated according to the method of Colby.

Example B-11: activity against Fusarium moniliforme on bananas

Ripe bananas process preparative form of the test mixture in the chamber for spraying. After one day after application of active substances and mixtures of active substances bananas inoculant conidia of Fusarium moniliforme by spraying the test of bananas suspension of conidia. After incubation for 7-14 days at a temperature of +22°C and relative humidity 70% in growth chamber estimate the number of cases of the disease and its series is asnosti. Interaction of fungicides in mixtures are calculated according to the method of Colby.

Example b-12: activity against Penicillium digitatum on citrus

The Mature fruit of susceptible cultivars of orange handle preparative form of the test mixture in the chamber for spraying. After one day after application of active substances and mixtures of active substances oranges inoculant conidia of Penicillium digitatum by spraying the test of oranges suspension of conidia. After incubation for 7-14 days at a temperature of +22°C and relative humidity 70% in growth chamber estimate the number of cases of the disease and its severity. The mutual influence of fungicides in mixtures are calculated according to the method of Colby.

The mixture according to the invention exhibit high activity when tested according to the methods described in all the above examples are not presented specific data.

1. A method of combating phytopathogenic diseases of cultivated plants capable of handling cultivated plants or places of their growth, infected with this phytopathogenic disease, an effective amount of a composition containing

A) N-sulfonylamine formula I

where

R1denotes hydrogen or halophenol, and R2stands With1-C4alkyl;

in combination

B) or metalaxyl formula II, including metalaxyl-M of the formula IIa

or fluazinam formula III

or MANCOZEB formula IV

or chlorthalonil formula V

or strobilurins formula VI

where Z denotes CH or N, and R stands for

first of all with strobilurins formula VIa, VIb or VIc

(VIc) picoxystrobin

or pyraclostrobin (BAS 500F) formula VII

either acibenzolar-S-stands formula VIII

or dimethomorph formula IX

or fludioxonil formula X

or cymoxanil formula XI

or imazalil formula XII, including S-imazalil formula XIIa.

in synergistic effective amounts.

2. JV the property according to claim 1, where component A) is a compound of formula I, where R1denotes hydrogen, chlorophenyl or bromophenyl, or where R1denotes hydrogen, 4-chlorophenyl or 4-bromophenyl, or where R1represents 4-chlorophenyl, or where R2denotes methyl or ethyl, or R2denotes methyl, or R1denotes hydrogen, 4-chlorophenyl or 4-bromophenyl and R2denotes methyl or ethyl, or R1represents 4-chlorophenyl, and R2denotes methyl or ethyl.

3. The method according to claim 1 or 2, where component B) selected from the group including acibenzolar-S-methyl, AZOXYSTROBIN, CHLOROTHALONIL, having cymoxanil, dimethomorph, fluazinam, fludyoksonil imazalil, S-imazalil, MANCOZEB, metalaxyl, metalaxyl-M, picoxystrobin, pyraclostrobin (BAS 500F) and Trifloxystrobin.

4. The method according to claim 1 or 2, where component B) is a metalaxyl or metalaxyl-M

5. The method according to any one of claims 1 to 4, where component A) is chosen from the group comprising compounds:

I.01:N-[2-{3-methoxy-4-(2-propyne-1-yloxy)-phenyl}-ethyl]-amide 2-ethyl-sulfonylamino-3-methylmalonic acid,

I.11:N-[2-{3-methoxy-4-(3-(3-chlorophenyl)-2-propyne-1-yloxy)-phenyl}-ethyl]-amide

2 ethylsulfonyl-3-methylmalonic acid,

I.12:N-[2-{3-methoxy-4-(3-(3-chlorophenyl)-2-propyne-1-yloxy)-phenyl}-ethyl]-amide

2 methylsulfonylamino-3-methylmalonic acid,

I.13:N-[2-{3-methoxy-4-(3-(4-chlorophenyl)-2-propyne-1-yloxy)-phenyl}-ethyl]-amide

2 ethylsulfonyl-3-methylmalonic acid,

I.14:N-[2-{3-methoxy-4-(3-(4-chlorophenyl)-2-propyne-1-yloxy)-phenyl}-ethyl]-amide

2 methylsulfonylamino-3-methylmalonic acid,

I.15:N-[2-{3-methoxy-4-(3-(3-bromophenyl)-2-propyne-1-yloxy)-phenyl}-ethyl]-amide

2 ethylsulfonyl-3-methylmalonic acid,

I.17:N-[2-{3-methoxy-4-(3-(4-bromophenyl)-2-propyne-1-yloxy)-phenyl}-ethyl]-

amide 2-ethylsulfonyl-3-methylmalonic acid,

I.19:N-[2-{3-methoxy-4-(3-(4-chlorophenyl)-2-propyne-1-yloxy)-phenyl}-ethyl]-amide

2 propylsulfonyl-3-methylmalonic acid,

I.20:N-[2-{3-methoxy-4-(3-(4-chlorophenyl)-2-propyne-1-yloxy)-phenyl}-ethyl]-amide

2-(1-methylethylenediamine)-3-methylmalonic acid,

I.21:N-[2-{3-methoxy-4-(3-(4-chlorophenyl)-2-propyne-1-yloxy)-phenyl}-ethyl]-amide

2 butylsulfonyl-3-methylmalonic acid, and

I.22:N-[2-{3-methoxy-4-(3-(4-chlorophenyl)-2-propyne-1-yloxy)-phenyl}-ethyl]-amide

2-Deut-butylsulfonyl-3-methylmalonic acid.

6. The method according to claim 5, where component A) is a connection:

I.13:N-[2-{3-methoxy-4-(3-(4-chlorophenyl)-2-propyne-1-yloxy)-phenyl}-ethyl]-amide 2-ethylsulfonyl-3-methylmalonic acid, or

I.14:N-[2-{3-methoxy-4-(3-(4-chlorophenyl)-2-propyne-1-yloxy)-phenyl}-ethyl]-the foreign Ministry

2 methylsulfonylamino-3-methylmalonic acid, or

I.15:N-[2-{3-methoxy-4-(3-(3-bromophenyl)-2-propyne-1-yloxy)-phenyl}-ethyl]-

amide 2-ethylsulfonyl-3-methylmalonic acid, or

I.17:N-[2-{3-methoxy-4-(3-(4-bromophenyl)-2-propyne-1-yloxy)-phenyl}-ethyl]-

amide 2-ethylsulfonyl-3-methylmalonic acid, or

I.19:N-[2-{3-methoxy-4-(3-(4-chlorophenyl)-2-propyne-1-yloxy)-phenyl}-ethyl]-amide

2 propylsulfonyl-3-methylmalonic acid, or

I.20:N-[2-{3-methoxy-4-(3-(4-chlorophenyl)-2-propyne-1-yloxy)-phenyl}-ethyl]-amide

2-(1-methylethylenediamine)-3-methylmalonic acid, or

I.21:N-[2-{3-methoxy-4-(3-(4-chlorophenyl)-2-propyne-1-yloxy)-phenyl}-ethyl]-amide

2 butylsulfonyl-3-methylmalonic acid.

7. Fungicidal composition comprising effective as a fungicide combination of components a) and B) according to claim 1 in synergistic effective amounts in combination with an acceptable agricultural carrier and optionally a surface-active substance.

8. The composition according to claim 7, where the mass ratio of A) to B) is from 2000:1 to 1:1000.



 

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or its salt wherein Y represents halogenalkyl group comprising from 1 to 2 carbon atoms and halogen atoms from 1 to 5; m = 0; Q represents compound of the formula:

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or its salt wherein Y represents halogenalkyl group comprising from 1 to 2 carbon atoms and halogen atoms from 1 to 5; m = 0; Q represents compound of the formula:

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