A method of combating fungi

 

(57) Abstract:

Usage: agriculture, chemical method of combating fungi. The inventive method of combating fungi with the use of pyrimidine derivatives f-ly I, where R1-H, halogen, C1-C3-alkyl, C1-C2-halogenated, C1-C3-alkoxy, R2hydrogen, halogen, R3-C1-C4halogenated, cyclopropyl; R4unsubstituted or substituted with halogen, stands, cyclopropyl, at a dose of 0.05 to 1.6 kg/ha connection Structure f-ly I:

The invention relates to a method of combating fungi on plants by practicing their new derivatives of 2-aniline-pyrimidine of the General formula I

NN where R1hydrogen, halogen; C1-C3-alkyl, C1-C2-halogenated,1-C3-alkoxy;

R2hydrogen, halogen;

R3WITH1-C4-alkyl, C1-C3-halogenated, cyclopropyl;

R4unsubstituted or substituted with halogen, methyl cyclopropyl.

Under halogenation depending on the number of carbon atoms should be understood substituted with halogen methyl, ethyl, propyl, butyl and their isomers such as isopropyl, isobutyl, tert-buo number of carbon atoms means, for example, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

N-Pyrimidinedione compounds known. In the published European patent application 0224 339 and patent DD 151 404 described compounds which have the structure N-2-pyrimidinyl, effective against damaging plants fungi. Known compounds could not hitherto fully meet the existing requirements. The compounds of formula I in accordance with the invention differ significantly from the known compounds by introduction of at least one cycloalkane residue and other substituents in the structure of anilinopyrimidines, resulting in the case of new compounds is achieved unexpectedly high fungicidal activity and insecticidal activity.

The compounds of formula I are at room temperature stable oils, resins or solid substances, which differ valuable microbicide properties. They can be used in the agricultural sector or related fields for the control of noxious plants by microorganisms. Biologically active substances of formula I in accordance with the invention differ at low feed concentrations are not only wonderful and the equipment is 2-phenylamino-4-methyl-6-cyclopropyl-pyrimidine.

The compounds of formula I possess biological activity against phytopathogenic fungi of the following classes: Fungi deuteromycota (insbesondere Botrytis, Jerner Pyricularia, Helminthosporium, Fusarium, Septoria, Cercospora and Alternaria); Basidiomyceten (Z. B. Rhizootonia, Hemileia, Puccinia).

In addition, they act against a class of records of Ascomycetes (for example (Z. B. Ventura und Erysiphe, Podoaphaera, Monilinia, Uncinula) and oomycetes (for example) (Z. B. Phytopthora, Pythium, Plasmopara).

The compounds of formula I can be used also as an etching means for processing seeds (fruit, tubers, grains) and cuttings of plants for protection against fungal infections as well as against existing in the land of phytopathogenic fungi. The compounds of formula I are effective also against harmful insects, for example against pests of cereal crops, in particular pests of rice.

As the target crops to be stated here use for plant protection as an example, should mention the following types of plants: cereals (wheat, barley, rye, oats, rice, corn, sorghum, and various spices); sugar beet and fodder beet, fruits, nuts and berry plants (apples, pears, plums, peaches, almonds, cherries, currants, strawberries and raspberries), leguminous plants (peas, lentils, beans, soybeans), massry (melon, cucumbers, melons), fibre plants (cotton, flax, hemp, jute), citrus plants (oranges, lemons, mandarins), vegetables (spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika), Laurel (avocado, cinnamony, camphor) or plants such as tobacco, nuts, coffee, sugar cane, tea, pepper, vines, hops, plants, bananas and natural rubber), as well as ornamental plants.

Biological active substances of formula I is applied on the processed surface or plants usually in the form of compositions independently or simultaneously, or sequentially with other biologically active substances.

The preferred method of application of biologically active substances of formula 1, is applied on the surface of leaves. The frequency of application and consumption rates are selected in dependence on the extent of involvement of the respective pathogen. Biologically active substance of the formula I can also come in the plants from the ground through their roots (systemic effect) so that the habitat of the plant is impregnated with a liquid prepared medication or substances introduced into the ground in solid form, for example in the form of a granulate (entry in the land). In the case of rice the value of the formula I can also be applied to seeds so what grain or impregnated with liquid ready preparation of biologically active substances, or their cover solid finished product.

The compounds of formula I are used in a dose of 0.05-1.6 kg/ha

In table. the above compounds used according to the invention.

Biological examples.

P R I m e R 1. Action against Venturia inaegualis on Apple shoots (residual protective action).

Apple branches with young shoots length of 10-20 cm were sprayed with a broth for spraying prepared from wettable powder of biologically active substances (0,006% of active substance). After 24 hours the treated plants were infected with a spore suspension of fungi. The plants are then incubated for 5 days at 90-100% relative humidity and then stood over the next 10 days in the greenhouse at 20-24aboutC. Lesion scabs were evaluated 15 days after infection.

Compounds from tables show against Venturia good efficiency (lost less than 20% ). Thus, connection 1.1, 1.5, 1.10, 1.11, 1.19, 1.26, 1.32, 1.33, 1.34, 1.36, 1.42, 1.43, 1.46, 1.49, 1.52, 1.56, 1.61, 1.66, 1.69, 1.76, 1.84, 1.85 reduce the defeat of Venturia to 0-10% of the Untreated, but infected control plants were amazed Venturia 100% the result of damaged apples were thus treated, that damaged areas sprayed broth to spray prepared from wettable powder of biologically active compounds (0,002 active substance). Processed fruits immediately after it was infected with a spore suspension of the fungus and during the week kept at high humidity at a temperature of about 20aboutC. the evaluation calculated the decayed damaged areas and hence taken out fungicidal action of the test substance.

Connection table showed against Botrytis good efficiency (lost less than 20% ). For example, connection 1.1, 1.3, 1.5, 1.7, 1.10, 1.11, 1.18, 1.19, 1.20, 1.26, 1.29, 1.30, 1.31, 1.32, 1.33, 1.34, 1.36, 1.38, 1.41, 1.42, 1.43, 1.46, 1.49, 1.52, 1.54, 1.56, 1.61, 1.63, 1.65, 1.66, 1.68, 1.69, 1.76, 1.79, 1.84, 1.85, 1.86 reduced defeat Botryis to 0-10% Neobrabotannye infected control plants were amazed Botrytis 100%

P R I m e R 3. Action against Erysiphae graminis on barley.

a) Residual-protective action.

Barley plants with a height of about 8 cm were sprayed with a broth of spray prepared from wettable powder of biologically active substances (0,006% of active substance). After 3-4 hours the treated plants were suffused with spores of the fungus. The infected barley plants were placed in the blitz showed towards Erysiphae good efficiency (lost less than 20% ). Connection 1.1, 1.5, 1.10, 1.19, 1.20, 1.26, 1.32, 1.33, 1.34, 1.36, 1.42, 1.43, 1.46, 1.49, 1.54, 1.61, 1.76, 1.84, 1.85 reduced defeat Erysiphae to 0-10% of Untreated infected control plants showed opposite defeat 100%

P R I m e R 4. Activity against Helminthosporium gramineum. Wheat was soaked with a spore suspension of the fungus and again dried. Soaked grain protravlivanie obtained from a wettable powder suspension of the test substance (600 million-1the active substance, considering the weight of the seeds). After two days of grain was placed on the appropriate agrarian plates and four days later evaluated the development of colonies of the fungus around the grain. The number and size of colonies of the fungus were used for evaluation of the test substance. Table joins greatly hinder the defeat of the fungus (0-10% of lesions).

P R I m e R 5. Action against Colletotrichumlagenarium on cucumbers.

The cucumber plants after germination within 2 weeks sprayed with a broth for spraying prepared from wettable powder of the biologically active substance (concentration of 0.002% ). After 2 days, the plants were infected with a spore suspension (h spores/ml) of the fungus and incubated for 36 h at 23aboutC and high humidity. Incubation was then continued at normal humidity Vosloo infected control plants were affected by the fungus from 100%

Compounds from tables showed good efficacy and prevented an extensive lesion of the disease. Defeat the fungus was reduced to 20% or less.

P R I m e R 6. a) contact action against Nepgotettix cinoticeps and Nilaparvate lugens (Nymphen).

The test was carried out on the sprouted rice plants. For this were planted in pots (diameter 5.5 cm, respectively, about 4 plants 14-20 days) with a height of about 15 cm

The plants were sprayed on a rotating plate 100 ml of the prepared aqueous suspension containing 400 million-1 of the biological active substances. After drying spattered layer on each plant was planted on 40 nymphs (larvae) of the test animals at the third stage of development. To prevent the spread of cicadas, plants with larvae was surrounded by open both sides of the cylinder and covered by a metal grid. After 6 days the nymphs reached the stage of development of adults on the treated plants. Assessment of destruction in percent was carried out 6 days after planting nymphs. The experiment was carried out at approximately 27aboutC, 60% relative humidity and period lighting 16 PM

b) Systemic action against Nilaparvata lugens (water). The rice plants approximately 10-the bottom of asego testing of biologically active substances with a concentration of 100 million-1 and were closed with a plastic lid with a hole in it. The root of rice plants through a hole in the plastic cover was placed in the prepared test solution. Then on the rice plants were planted about 20 days (larvae Nelaparvata lugens under development N 2 and N 3 and covered with a plastic cylinder. The experiment was carried out at approximately 25 C and 60% relative humidity with a period of light 16 hours five days was evaluated destroyed the test animals compared to the untreated control. Thus, it was found that the biologically active substance flowing through the root, striking animals on the upper parts of plants.

The connection from the table showed as in test a) and test (b) strong devastating effect against pests of rice. The degree of destruction is 80% or more. Using compounds 1.1, 1.5, 1.11, 1.32, 1.34, 1.43, 1.46, 1.149, 1.76 was achieved almost complete destruction (98-100%).

P R I m e R 7. Comparison of the activity of biologically active substances of this application with the compounds of the prior art

1. Connection (PS(5-167,1(1+2)+C)

X1NH Verb. N 1.1

X2NH Verb. N 1.11

X3NH Verb. N 1.32

X4FNHOnce.N1.19< / BR>
X5NH Verb. N 1.33

Y1NH

Y2FNH

Y3NH

YaboutC. When evaluating calculate rotten lesions and from this conclude fungicidal action of the test substance.

Comparative way, untreated, but infected control plants show defeat Botrytis 100%

2. Action against Venturia inaegualis on Apple shoots.

Apple cuttings with fresh shoots length of 10-20 cm are sprayed prepared from wettable powder of biologically active substances broth for spraying (0,006% of active substance). After 24 hours the treated plants infect suspension of conidia of the fungus. The plants are then incubated for 5 days at a relative humidity of 90-100% and over the next 10 days is kept in a greenhouse at 20-24aboutC. Defeat partnoy evaluated 15 days after infection.

Comparative way, untreated, but infected control plants show perepicivat prepared from wettable powder of biologically active substances broth for spraying (0,006% of active substance). After 3-4 hours the treated plants opilivayut conidia of the fungus. The infected barley plants kept in a greenhouse at about 22aboutAnd 10 days later evaluate the defeat of the mushroom.

Comparative way, untreated, but infected control plants show defeat Erysiphae 100%

Evaluation

1. A METHOD of COMBATING FUNGI by treating the plants pyrimidine derivative of General formula

< / BR>
where R1hydrogen, halogen, C1-C3-alkyl, C1-C2-halogenated,1-C3-alkoxy;

R2hydrogen, halogen;

R3WITH1-C4-alkyl, C1-C3-halogenated, cyclopropyl;

R4unsubstituted or substituted with halogen, stands cyclopropyl,

at the dose of 0.05-1.6 kg/ha

2. The method according to p. 1, characterized in that the processing plants are 2 to phenylamino-4-methyl-6-cyclopropylamino at a dose of 0.05-1.6 kg/ha

 

Same patents:

The invention relates to methods of producing derivatives of 2-anilinopyrimidines or acid additive salts of novel biologically active compounds, which can find application in agriculture

Herbicide tool // 2041626

The invention relates to new derivatives of pyrimidine or triazine and their salts, in particular derivatives of pyrimidine or triazine represented by the General formula I, and also relates to a herbicide composition containing these derivatives, pyrimidine or triazine or their salts as active substances, which can be used on rysownika, soils upland conditions or space not occupied for agricultural crops

The invention relates to a new derivative of uracil with herbicide action

The invention relates to new derivatives of arylsulfonamides, which can be used in agriculture as a herbicide for weed control in soybean crops, in particular in a mixture with other compounds

The invention relates to a new derived hexahydropirimidine series, namely TRANS-4-azido-3,6-dimethylhexylamine - midin-2-tion of formula I, manifesting nematocidal activity and which may find application in agriculture

The invention relates to a derivative of acrylic acid, useful in agriculture (especially as fungicides but also as plant growth regulators, insecticides and nematicides), to the processes of their production, agricultural (especially fungi) compositions containing them and to methods of using them to combat fungi, especially fungal infections of plants, for regulating the growth of plants and to destroy or suppress insect and nematode pests

The invention relates to new derivatives of acrylic acid, having fungicidal activity, which can find application in agriculture

The invention relates to the derivatives of uracil and their use in agriculture, namely use as herbicides

The invention relates to the derivatives of pyrimidine, herbicide compositions and chemical method of weed control with their use

FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention describes substituted benzoylcyclohexanediones of the general formula (I):

wherein m = 0 or 1; n = 0 or 1; A means a single bond or alkanediyl (alkylene) with 1-4 carbon atoms; R1 means hydrogen atom or unsubstituted alkyl with from 1 to 6 carbon atoms; R2 means methyl; R3 means hydrogen atom, nitro-, cyano-group, halogen atom, alkyl with from 1 to 4 carbon atoms substituted with halogen atom, alkoxy-group with from 1 to 4 carbon atoms or alkyl sulfonyl with from 1 to 4 carbon atoms; R4 means nitro-group, halogen atom, unsubstituted alkyl with from 1 to 4 carbon atoms of that substituted with halogen atom; Z means heterocycle, and herbicide agent based on thereof. Also, invention describes substituted derivatives of benzoic acid of the general formula (III):

wherein values n, A, R3, R4 and Z are given above. These compounds represent the parent substances used for preparing compound of the formula (I). Compounds of the formula (I) elicit high and selective herbicide activity.

EFFECT: valuable properties of compounds.

7 cl, 8 tbl, 7 ex

FIELD: agriculture, in particular herbicide compositions.

SUBSTANCE: invention relates to weed controlling method for tolerant cotton crops using (A) road spectrum herbicides selected from group (A1) glufosinate (salt) and related compounds; (A2) glyphosate (salt) and related compounds; and (B) herbicides selected from group containing diurone, trifluraeline, linuron, and pendimethalin; lactofen, oxyfluoren, bispiribac and salts thereof, pyrithiobac and salts thereof; setoxydim, cyclosidim, and cletodim; wherein components (A) and (B) are used in synergistically effective ratio. Also are described herbicide compositions containing compound from group (A1) or (A2) and herbicide from group (B).

EFFECT: effective controlling of weeds in cotton crops.

9 cl, 12 tbl, 3 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: method involves carrying out a seasonal single treatment of plant leaves with asymmetrical derivative of 4,6-bis-(aryloxy)pyrimidine of the formula: wherein X means chlorine atom (Cl), nitro- or cyano-group. Invention provides enhancing the long-term time of plants protection.

EFFECT: enhanced effectiveness and valuable properties of compounds.

6 cl, 6 tbl

FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention relates to new derivatives of uracil of the formula [I] eliciting the herbicide effect, herbicide composition based on thereof and a method for suppression of weed growth. In the formula [I] W means oxygen (O), sulfur (S) atom or imino-group; Y means oxygen atom (O) or sulfur atom (S); R1 means (C1-C3)-alkyl or (C1-C3)-halogenalkyl; R2 means (C1-C3)-alkyl; R4 means hydrogen atom (H) or methyl; R5 means (C1-C6)-alkyl, (C1-C6)-halogenalkyl, (C3-C6)-alkenyl, (C3-C6)-halogenalkenyl, (C3-C6)-alkynyl or (C3-C6)-halogenalkynyl; X1 means halogen atom, cyano- or nitro-group; X2 means hydrogen atom (H) or halogen atom; each among X3 and X4 means independently hydrogen atom (H), halogen atom, (C1-C6)-alkyl, (C1-C6)-halogenalkyl, (C3-C6)-alkenyl, (C3-C6)-halogenalkenyl, (C3-C6)-alkynyl, (C3-C6)-halogenalkynyl, (C1-C6)-alkoxy-(C1-C6)-alkyl, (C1-C6)-alkoxy-, (C1-C6)-halogenalkoxy-, (C1-C6)-alkoxycarbonyl-(C1-C6)-alkoxy- or cyano-group. Also, invention relates to new intermediate substances used for preparing compounds of the formula [I] corresponding to formulae [VII] , [XXXIV] and [XXXIII] wherein in compound of the formula [VII] W means oxygen (O), sulfur (S) atom or imino-group; Y means oxygen (O) or sulfur atom (S); in compounds of formulae [XXXIV] and [XXXIII] W means oxygen atom (O); R17 means oxygen atom (O); R4 means hydrogen atom (H) or methyl. Also, invention relates to methyl- or ethyl-[2-(5-amino-2-chloro-4-fluorophenoxy)phenoxy]acetate not early described in the literature.

EFFECT: valuable herbicide properties of compounds.

23 cl, 17 sch, 9 tbl, 11 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to selective herbicidal compositions, containing customary auxiliary substances, as well as: a) herbicidal effective amount of compound of formula I or agriculture acceptable salt thereof wherein R are independently C1-C6-alkyl, C1-C6-haloalkyl, C1-C4-alcoxy-C1-C4-alkyl, or C1-C4-alcoxy-C1-C4-alcoxy-C1-C4-alkyl; m = 2; Q is group of formula wherein R23 is hydroxyl and Y is C1-C4-alkylen bridge; and b) synergetically effective amount of one or more herbicides; and methods for controlling of undesired plants in tame cultures using the said composition. Also disclosed is composition containing customary auxiliary substances, as well as herbicidal and synergetically effective amount of 4-hydroxy-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]octo-3-ene-2-one of formula 2.2 and herbicidal antagonistically effective amount of antidote of formula 3.1. Compositions based on 4-hydroxy-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]octo-3-ene-2-one and herbicidal antagonistically effective amount of antidote, as well as methods for controlling of weeds and cereal grasses in tame cultures also are described.

EFFECT: compositions useful in effective controlling of many weeds both in pre-spring and post-spring phases.

5 cl, 63 tbl, 12 ex

FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention elates to novel derivatives of uracil of the formula [I] possessing herbicide activity, a herbicide composition based on thereof and to a method for control of weeds. In derivatives of uracil of the formula [I] the group Q-R3 represents a substituted group taken among:

wherein a heterocyclic ring can be substituted with at least a substitute of a single species taken among the group involving halogen atom, (C1-C6)-alkyl-(C1-C6)-alkoxy; Y represents oxygen, sulfur atom, imino-group or (C1-C3)-alkylimino-group; R1 represents (C1-C3)-halogenalkyl; R2 represents (C1-C3)-alkyl; R3 represents OR7, SR8 or N(R9)R10; X1 represents halogen atom, cyano-group, thiocarbamoyl or nitro-group; X2 represents hydrogen or halogen atom wherein each among R7, R8 and R10 represents independently carboxy-(C1-C6)-alkyl and other substitutes given in the invention claim; R9 represents hydrogen atom or (C1-C6)-alkyl. Also, invention relates to intermediate compounds used in preparing uracil derivatives.

EFFECT: improved preparing method, valuable properties of compounds.

40 cl, 16 sch, 12 tbl, 65 ex

FIELD: organic chemistry, chemical technology, herbicides, agriculture.

SUBSTANCE: invention relates to new sulfonamides of the formula (I):

and their salt wherein A represents substituted or unsubstituted benzene ring or 5-membered, or 6-membered substituted or unsubstituted heteroaromatic ring taken among the group comprising thienyl, pyrazolyl, imidazolyl, pyridyl wherein optional substitutes are taken among the group consisting of halogen atom, substituted or unsubstituted (C1-C4)-alkyl, unsubstituted or substituted (C1-C4)-alkoxy-group, nitro-group, phenyl, phenoxy-group, benzoyl and (C1-C4)-alkylcarboxylate when any alkyl fragment in the latter indicated substituted is substituted with one or some halogen atoms, (C1-C4)-alkoxy-groups, cyano-group and phenyl; Q represents -O-, -S- or group of the formula: -CXX' wherein X and X' can be similar or different and each represents hydrogen atom, halogen atom, cyano-group, alkyl comprising 1-8 carbon atoms, or the group -ORa, -SRa; or one of X and X' represents hydroxy-group and another has values determine above; Ra means (C1-C8)-alkyl, phenyl; Rb means (C1-C8)-alkyl, phenyl; Y means nitrogen atom or the group CR9; R1 means unsubstituted (C1-C8)-alkyl or that substituted with halogen atom, cyano-group, phenyl or (C1-C4)-alkoxycarbonylamino-group, or it represents phenyl; R2 means hydrogen atom (H), (C1-C4)-alkyl; R3 and R4 can be similar or different and each represents (C1-C4)-alkyl, (C1-C4)-alkoxy-group, halogen atom; R9 means hydrogen atom (H) under condition that when Q represents oxygen atom (O) or -S- then ring A represents 5-membered substituted or unsubstituted heteroaromatic ring and determined above. Compounds of the formula (I) possess the herbicide activity that allows their using for eradication of weeds. Also, invention describes a method for preparing compounds of the formula (I).

EFFECT: improved preparing method, valuable properties of compounds.

9 cl, 5 tbl, 18 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to pest controlling agents containing compound of formula I in mixture with active fungicidal material selected from azoxystrobin, tebuconazol, prothioconazol etc., in mass ratio of formula I/active fungicidal material providing marked synergic action.

EFFECT: enhanced assortment of pest controlling agents based on nitromethylene derivatives.

2 cl, 15 tbl, 9 ex

Up!