CN1073802C - Fungicidally active compositions - Google Patents

Fungicidally active compositions Download PDF

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Publication number
CN1073802C
CN1073802C CN94118806A CN94118806A CN1073802C CN 1073802 C CN1073802 C CN 1073802C CN 94118806 A CN94118806 A CN 94118806A CN 94118806 A CN94118806 A CN 94118806A CN 1073802 C CN1073802 C CN 1073802C
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methyl
composition
compound
ethyl
reactive compound
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CN1111476A (en
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仓桥良雄
泽田治子
金原太郎
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Bayer CropScience KK
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Nihon Bayer Agrochem KK
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48

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  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

A germicidal composition for agriculture and horticulture is obtained by combinedly using A) and B) which contain active composition of the formula I.

Description

Fungicidally active agent
The present invention relates to new Fungicidally active agent, other also is the composition of known fungicide wherein to comprise the benzamide type of known Fungicidally active and some.
Disclosing clear 61-15 867 from Japan Patent, as can be known, is known according to the benzamide type of Fungicidally active used in the present invention in clear 62-201 855 peaceful 2-11550 numbers, and the activity of these materials is good; But when using with low dosage, also staying some problems sometimes has to be solved.
And, known that following compound can be used to prevent and treat fungi: 5-chloro-N-(1,3-dihydro-1,1,3-trimethyl-4-isobenzofuran-base)-1,3-dimethyl-1H-pyrazole-4-carboxamide, methyl-(E)-methoxyimino-[α-(o-tolyl oxygen)-o-tolyl] acetic acid esters, (E)-2-methoxyimino-N-methyl-2-(2-phenoxy phenyl) acetamide, methyl-(E)-2-{2-[6-(2-cyano-benzene oxygen)-pyrimidine-4-base oxygen] phenyl }-the 3-methoxy acrylate, 2 ＇, 6 ＇-two bromo-2-methyl-4 ＇-trifluoromethoxy-4 ＇-Trifluoromethyl-1,3-thiazole-5-formailide and 3-allyloxy-1,2-benzisothiazole-1, the 1-dioxide (discloses clear 45-38 080 with reference to Japan Patent, No. 268, peaceful 3-246, EP-OS (European patent prospectus) 0,468,684, the flat 4-15228 of Japan Patent prospectus, peaceful 2-131481 number of clear-63-23852).But when using with low dosage, the activity of these materials is not always satisfactory.
In rice cropping, use rice transplanter to carry out the transplanting operation of machinery usually to rice shoot.It also is known in the crop of rice field seedling case applications of fungicides being prevented and treated fungal disease, and applications of fungicides can be saved the labour by this way.
From biological safety and environmental protection angle, press for amount of application that reduces fungicide in large quantities and the kind that reduces the reactive compound of using.For achieving the above object, need carry out a large amount of research to reduce application dosage.
Especially, be starved of when adopting laborsaving method of operating and improving biological safety the fungi that causes disease by control, and important disease rice blast in the control rice cropping.Therefore, an object of the present invention is in rice cropping,, realize control rice blast by using fungicide with effective low dosage.
Have now found that the new compositions that contains following reactive compound has extraordinary Fungicidally active:
A) formamide of at least a following formula
Figure C9411880600051
Wherein
R 1Represent the alkyl of 1 to 4 carbon atom,
R 2Represent hydrogen atom or methyl,
R 3Represent hydrogen atom or methyl and
Z represents halogen atom,
With the carbon atom of asymmetric replacement, C is for (R)-configuration (definitely) is a condition;
With
B) at least a being selected from down organized the compound that comprises:
5-chloro-N-(1,3-dihydro-1,1,3-trimethyl-4-isobenzofuran-base)-1,3-dimethyl-1H-pyrazole-4-carboxamide, methyl-(E)-methoxyimino-[α-(o-tolyl oxygen)-o-tolyl] acetic acid esters, (E)-2-methoxyimino-N-methyl-2-(2-phenoxy phenyl) acetamide, methyl-(E)-2-{2-[6-(2-cyano-benzene oxygen)-pyrimidine-4-base oxygen] phenyl }-the 3-methoxy acrylate, 2 ＇, 6 ＇-two bromo-2-methyl-4 ＇-trifluoromethoxy-4 ＇-Trifluoromethyl-1,3-thiazole-5-formailide and 3-allyloxy-1,2-benzisothiazole-1, the 1-dioxide.
Be because the associating and the synergistic effect of the mixture of active component, to have very significantly fungicidal effect astoundingly according to the composition of Fungicidally active of the present invention.Even owing to use this composition under low-down dosage, it also is very effective that composition is compared with independent compound, so the technique effect that obtains based on independent application of active compound can not be anticipated this synergistic effect.And, on the control rice blast, there is fabulous and definite effect especially according to Fungicidal composition of the present invention.
Provided total definition of the formamide of in thing combined according to the invention, using in the formula (I).In the formula
R 1Preferred represent methylidene, ethyl or isopropyl,
R 2Preferred hydrogen atom or the methyl represented,
R 3Preferred hydrogen atom or the methyl represented,
Z -The preferred chlorine atom of representing.
Below addressed the example of formula (I) representation compound:
N-(R)-[1-(4-chlorphenyl)-ethyl]-2, the 2-two chloro-1-ethyls-diastereomeric mixture of 3t-methyl isophthalic acid r-cyclopropane carboxamide,
N-(R)-[1-(4-chlorphenyl)-ethyl]-2, the diastereomeric mixture of 2-two chloro-1-isopropyl cyclopropane carboxamides,
N-(R)-[1-(4-chlorphenyl)-ethyl]-(1S)-2,2-two chloro-1-ethyls-3t-methyl isophthalic acid r-cyclopropane carboxamide and
N-(R)-[1-(4-chlorphenyl)-ethyl]-(1S)-2,2-two chloro-1-isopropyl cyclopropane carboxamides.
When reactive compound existed with concrete weight ratio in according to the composition of reactive compound of the present invention, synergistic effect was obvious especially.But the weight ratio of the reactive compound in composition according to the present invention can change in quite wide scope.Usually, can use about 0.02 to about 50 weight portions, preferably approximately 0.1 (B) group compound to about 10 weight portions to formula (I) formamide of per 1 weight portion.
According to the composition of Fungicidal active compound of the present invention exist fabulous Fungicidally active and, in fact, this composition can be used to prevent and treat harmful phytopathogenic fungi in practice.
Composition useful as fungicides according to the present invention is to prevent and treat various phytopathogenic fungis, as club root Gammaproteobacteria, Oomycete, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, deuteromycetes etc., this composition also can be used as bactericide to prevent and treat various plant malignant bacterias, comprise utmost point hair Bacteriaceae, Rhizobiaceae, enterobacteria section, Corynebacteriaceae, Streptomycetaceae etc.
Specifically, there is fabulous preventive and therapeutic effect in the composition according to reactive compound of the present invention to rice blast pathomycete (Pyricularia oryzae).
According to the composition of Fungicidal active compound of the present invention, under control phytopathogenic fungi desired concn, good compatibility is arranged with plant.Therefore, when using this composition, can handle the acrial part of plant effectively, and can handle seed and rhizome, and also can carry out soil treatment.
Composition according to reactive compound of the present invention only has very low-level toxicity to warm blooded animal, so this composition can be used safely.
The composition of reactive compound can be formulated into the mixture of (A) group formamide and other (B) group reactive compound according to the present invention.Selectively, can prepare preparation that contains a kind of reactive compound and the another kind of preparation that contains other reactive compound individually, then before use, in the field of employment, with so two kinds of preparations mixing of preparation.
The above-mentioned preparation that can address is a liquor, wetting powder, emulsion, suspending agent, pulvis, foaming agent, paste, granule, tablet, aerosol is with the natural and synthetic material of reactive compound dipping, microcapsules, be used for the coated composition of seed and be used for the preparation of combustion apparatus, as smoke cartridge, smoke candle and smog circle, and cold mist agent of ultra low volume and ultra low volume thermal fog.
Can produce these preparations by known method, for example, under the situation of selectively using surfactant, by being mixed with filler, reactive compound prepares preparation, said filler is the diluent or carrier of liquid or liquid gas or solid, said surfactant is an emulsifier, dispersant, and/or foam agent.Under the situation of water, also can with an organic solvent for example, organic solvent be used as cosolvent as filler.
Liquid diluent or the carrier that can address are generally: arene, and as dimethylbenzene, toluene and Fluhyzon class, chlorinated aromatics or chlorinated aliphatic, as chlorobenzene, dichloroethane and chloromethanes, aliphatic hydrocarbon or cycloaliphatic hydrocarbons, as cyclohexane or paraffin, for example, mineral oil fractions, alcohols is as butanols or ethylene glycol and their ether and ester class, ketone, as acetone, methyl ethyl ketone, methyl iso-butyl ketone (MIBK) or cyclohexanone, or extremely give birth to solvent by force, as dimethyl formamide and dimethyl sulfoxide (DMSO), and water.
The liquid gas diluent or carrier means and be the liquid of gas under normal temperature and normal pressure, for example, aerosol propellant, as halogenated hydrocarbons and butane, propane, nitrogen and carbonic acid gas.
Spendable solid carrier is the particle of natural minerals, as kaolin, and clay, talcum, chalk, quartz, Attagel, imvite or diatomite and synthetic mineral particle, as the silicic acid of high dispersive, aluminium oxide and silicate.
The solid carrier that can be used for granule is to pulverize the also natural rock of split pole, as calcite, and marble, float stone, sepiolite and dolomite, and inorganic synthetic particle and organic dust, with the particle such as the sawdust of organic product, shuck, corncob core and potato haulm.
Spendable emulsifier and/or foam agent are nonionic and anion emulsifier, as polyoxyethylene-fatty acid ester, and polyoxyethylene-aliphatic alcohol ester, for example, alkylaryl polyglycol ether, alkylsulfonate, alkyl sulfate, arylsulfonyl salt and albumin hydrolysate.Dispersant comprises, for example, and lignin sulfite waste liquor and methylcellulose.
Sticker such as carboxymethyl cellulose and natural polymer and synthetic polymer, (as gum Arabic, polyvinyl alcohol and polyvinyl acetate) can be used on pulvis, in the preparation of granule or missible oil form.
The colouring agent that may use such as first machine pigment, for example, iron oxide, titanium oxide and Prussia orchid, and organic dyestuff, as alizarin dyes, azo dyes or metal phthalocyanine dyestuff and trace nutrients, as iron, manganese, boron, copper, cobalt, molybdenum and zinc salt.
Usually in preparation, can contain 0.1 to 95% reactive compound by weight, preferably contain 0.5 to 90% reactive compound by weight.
Reactive compound of the present invention can be present in above-mentioned preparation or other application form, selectively, they can use with other known activity material, these materials such as insecticide, miticide, nematocide, weed killer herbicide, birds repellant, growth regulator, fertilizer and/or soil structure improver.
Active compounds of the present invention, they can its dosage forms or use with its type of service, and its type of service prepares by further dilution, as stock solution, emulsion suspension, powder is stuck with paste particle and tablet.Can use these formulations in a usual manner, for example, water by sprinkling, dipping, spray cloth, spraying, atomizing, stifling, immersion liquid suspends, and dressing dusts, and broadcasts sowing, dried dressing, moist dressing, wet type dressing, the mode of oar liquid dressing or involucrum.
When on the each several part that is administered to plant, the concentration of the reactive compound of type of service can change within a large range.Usually, this concentration is by weight 0.0001 to 1%, is preferably by weight 0.001 to 0.5%.
When carrying out seed treatment, the per kilogram seed is used 0.001 usually to 50g, the reactive compound of preferred 0.01 to 10g/1kg seed.
When carrying out soil treatment, the reactive compound that is administered to target usually is the reactive compound of 0.00001 to 0.1% concentration by weight, preferably by weight 0.0001 to 0.02%.
Embodiment subsequently will more specifically explain the present invention, but they do not constitute any type of restriction to scope of the present invention.
Embodiment
Give birth to and survey embodiment
Test compound:
The A group:
(I)-a:N-(R)-[1-(4-chlorphenyl)-ethyl]-2, the 2-two chloro-1-ethyls-diastereomeric mixture of 3t-methyl isophthalic acid r-cyclopropane carboxamide,
(I)-b:N-(R)-[1-(4-chlorphenyl)-ethyl]-2, the diastereomeric mixture of 2-two chloro-1-isopropyl cyclopropane carboxamides,
(I)-c:N-(R)-[1-(4-chlorphenyl)-ethyl]-(1S)-2,2-two chloro-1-ethyls-3t-methyl isophthalic acid r-cyclopropane carboxamide and
The B group:
B-1:5-chloro-N-(1,3-dihydro-1,1,3-trimethyl-4-isobenzofuran-base)-1,3-dimethyl-1H-pyrazole-4-carboxamide,
B-2: methyl-(E)-methoxyimino-[α-(o-tolyl oxygen)-o-tolyl] acetic acid esters,
B-3:(E)-2-methoxyimino-N-methyl-2-(2-phenoxy phenyl) acetamide,
B-4: methyl-(E)-and 2-{2-[6-(2-cyano-benzene oxygen)-pyrimidine-4-base oxygen] phenyl }-the 3-methoxy acrylate,
B-5:2 ＇, 6 ＇-two bromo-2-methyl-4 ＇-trifluoromethoxy-4 ＇-Trifluoromethyl-1,3-thiazole-5-formailide and
B-6:3-allyloxy-1,2-benzisothiazole-1,1-dioxide.
Embodiment 1
In seedling box to the bactericidal assay of rice blast
The preparation of reactive compound:
Each reactive compound: 25 to 50 parts by weight
Carrier: diatomite/kaolin mixture of 45 to 70 parts (1: 5 mixture) by weight
Emulsifier: 5 parts polyoxyethylene alkyl phenyl ether by weight
In order to prepare various suitable preparations, with every kind of described amount single reactive compound, the emulsifier of the carrier of described amount and the carrier of described amount and described amount grinds and also to mix forming wetting powder, and the wetting powder of dilute with water scheduled volume subsequently.
Test method
With many 100cm 2The Wagner plastic casing, each fills up and forms heavy water condition with fluvisol.After soil surface is smooth, removes top water and make basin leave standstill a whole day, then at diameter 2cm of soil surface centre drill, the hole of dark 3cm is added dropwise to the water dilution preparation as the scheduled volume of above-mentioned preparation in the bottom in hole.
Three strains are inserted in the hole and cover transplanted seedling fully with the soil of drying at the rice seedling (kind Kusabue) of two leaf stage.Then all basins are placed in the greenhouse, and remained in 20 to 33 ℃ of temperature ranges 30 days, so that seedling growth, then spray inoculation rice blast fungi (rice blast) spore according to conventional methods and on the rice shoot.
Inoculate back seven days, measure the infection rate and the record of rice plant in every basin, to obtain the corresponding protection value according to following evaluation criterion.
The area (by %) of scab appears in infection rate
0 0
0.5 2 or still less
13 to 5
26 to 10
3 11 to 20
4 21 to 40
5 41 or more
Use following formula to calculate the percentage of protection value:
Wherein
The infection rate of A representative in contrast (being untreated) sub-district; With
The infection rate of B representative in handling the sub-district.
In this experiment, each experimental plot is made up of three basins.
The results are shown in table 1.
Table 1
Test compound Active component dosage (g/ seedling box) Protection value (%) Calculated value E (Colby)
According to the present invention
(Ⅰ)-a+ (B-4) 0.25+0.25 0.5+0.5 98 100 58 84
(Ⅰ)-a+ (B-6) 0.25+0.5 0.5+1.0 96 100 53 79
(Ⅰ)-b+ (B-4) 0.25+0.25 0.5+0.5 95 99 55 83
(Ⅰ)-b+ (B-6) 0.25+0.5 0.5+1.0 93 97 50 77
(Ⅰ)-c+ (B-4) 0.25+0.25 0.5+0.5 100 100 75 91
(Ⅰ)-c+ (B-6) 0.25+0.5 0.5+1.0 100 100 73 89
Known
(Ⅰ)-a 0.25 0.5 37 63 - -
(Ⅰ)-b 0.25 0.5 33 60 - -
(Ⅰ)-c 0.25 0.5 63 80 - -
(B-4) 0.25 0.5 33 57 - -
(B-6) 0.5 1.0 26 43 - -
M: a kind of effect of active component wherein
N: the effect of another kind of composition
E: the Expected Results of using the composition of representing with the percentage of untreated control.The dosage of active component (g/ seedling case) is expressed and is changed into every Wagner plastic basin (100m 2) in dosage numerical value or be expressed as every plastics seedling case (dose value of 30 * 60 * 3cm).
Embodiment 2
Foliage application experiment to rice blast
Test method
Rice plant (kind Kusabue) is planted in the porcelain basin of diameter 12cm.In the paddy rice 3-4 leaf phase,, paddy rice is sprayed the solution of reactive compound preparation and that have predetermined concentration as described in example 1 above with the dosage of per 3 basin 50ml.Second day, spray twice with the spore suspension of rice blast pathomycete Pyricularia orgzae (prior artificial culture) to plant, for reaching the purpose of infection, plant is remained in the greenhouse of 25 ℃ of temperature and relative moisture 100%.
Inoculate after seven days, the infection rate of rice blast in every basin is measured and record according to following evaluation criterion.The area (by %) of scab appears in infection rate
0 0
0.5 be not higher than 2
1 3-5
2 6-10
3 11-20
4 21-40
5 41 or bigger
Use following formula to calculate the percentage of protection value:
Figure C9411880600151
Wherein
The infection rate of A representative in contrast (being untreated) sub-district; And
The infection rate of B representative in handling the sub-district.
In this test, each experiment sub-district is made up of three basins.
The results are shown in table 2.
Table 2
Test compound Active component dosage (ppm) Protection value (%) Calculated value E (Colby)
According to the present invention
(Ⅰ)-a+ (B-2) 25+25 50+50 93 100 76 91
(Ⅰ)-a+ (B-3) 25+50 50+100 93 97 73 90
(Ⅰ)-b+ (B-2) 25+25 50+50 90 90 74 89
(Ⅰ)-b+ (B-3) 25+50 50+100 87 95 70 88
(Ⅰ)-c+ (B-2) 25+25 50+50 98 100 82 93
(Ⅰ)-c+ (B-3) 25+50 50+100 93 100 79 93
Known
(Ⅰ)-a 25 50 57 73 - -
(Ⅰ)-b 25 50 53 67 - -
(Ⅰ)-c 25 50 67 80 - -
(B-2) 25 50 45 67 - -
(B-3) 50 100 37 63 - -
Embodiment 3
Heavy water dispenser experiment to rice blast
By the amount of every basin three strain clumps, rice plant (kind Kusabue) is planted in the ceramic whiteware basin of diameter 12cm, and under heavy water condition, cultivate.In the early tillering stage, with solution preparation and reactive compound with predetermined concentration as described in example 1 above, with pipette by shown in dosage pour on the water surface of every basin, simultaneously in experiment, should avoid the plant corpus of rice plant acrial part directly to contact with medicament.
After five days, according to conventional methods to the spore suspension spray inoculation of plant with the rice blast fungi, and in 23 to 25 ℃ temperature range and under the condition of relative moisture 100%, kept 24 hours, then plant to be transferred in the glass greenhouse, the temperature in the greenhouse remains between 20 to 28 ℃.Inoculate after seven days, the method among the embodiment 1 of pressing measure infection rate and according to above-mentioned evaluation criterion record to obtain protection value (%), the results are shown in table 3.
Table 3
Test compound Active component dosage (kg/ha) Protection value (%) Calculated value E (Colby)
According to the present invention
(Ⅰ)-a+ (B-3) 0.25+0.25 0.5+0.5 87 99 75 93
(Ⅰ)-a+ (B-4) 0.25+0.25 0.5+0.5 90 95 73 90
(Ⅰ)-a+ (B-6) 0.25+0.5 0.5+1.0 83 97 64 85
(Ⅰ)-b+ (B-3) 0.25+0.25 0.5+0.5 87 95 73 92
(Ⅰ)-b+ (B-4) 0.25+0.25 0.5+1.0 83 95 70 87
(Ⅰ)-b+ (B-6) 0.25+0.25 0.5+1.0 33 87 61 81
(Ⅰ)-c+ (B-3) 0.25+0.25 0.5+0.5 90 100 79 97
(Ⅰ)-c+ (B-4) 0.25+0.25 0.5+0.5 90 100 77 95
(Ⅰ)-c+ (B-6) 0.25+0.5 0.5+1.0 83 97 69 92
Known (I)-a 0.25 0.5 57 80 - -
(Ⅰ)-b 0.25 0.5 53 75 - -
(Ⅰ)-c 0.25 0.5 63 90 - -
(B-3) 0.25 0.5 43 67 - -
(B-4) 0.25 0.5 37 50 - -
(B-6) 0.5 1.0 17 23 - -
Embodiment 4
Heavy water test to rice sheath blight disease
By the amount of every basin one strain clump, rice plant (kind Kusabue) is planted in the ceramic whiteware basin of diameter 12cm, and under heavy water condition, cultivate.At the booting stage of plant, the solution of reactive compound that will prepare as described in example 1 above and that have predetermined concentration, with pipette by shown in dosage pour on the water surface of every basin, simultaneously in experiment, should avoid the plant corpus of rice plant acrial part directly to contact with medicament.
After ten days,, with the inoculation of banded sclerotial blight fungi,, plant is remained on 25 to 30 ℃ of temperature, in the inoculating hood of relative moisture about 90% ten days in order to promote to infect in plant bottom according to conventional application process.
According to the scab of expansion, press accurate mensuration of commentary price card and infect grade.
Figure C9411880600191
N: for trying the water the rice plants sum
n 1: bottom blade infects the strain number of banded sclerotial blight
n 2: bottom second layer blade infects the strain number of banded sclerotial blight
n 3: the 3rd layer of blade in bottom infects the strain number of banded sclerotial blight
By infecting grade, calculate the protection value according to following formula:
The results are shown in the table 4:
Table 4
Test compound Active component dosage (kg/ha) Protection value (%)
According to the present invention: (I)-a+ (B-1) 2.0+0.1 2.0+0.3 75 90
(Ⅰ)-a+ (B-4) 2.0+1.8 2.0+1.6 73 93
(Ⅰ)-a+ (B-5) 2.0+0.3 2.0+0.6 63 93
(Ⅰ)-b+ (B-1) 2.0+0.1 2.0+0.3 70 87
(Ⅰ)-b+ (B-4) 2.0+0.8 2.0+1.6 67 87
(Ⅰ)-b+ (B-5) 2.0+0.3 2.0+0.6 57 90
(Ⅰ)-c+ (B-1) 2.0+0.1 2.0+0.3 80 93
(Ⅰ)-c+ (B-4) 2.0+0.8 2.0+1.6 80 93
(Ⅰ)-c+ (B-5) 2.0+0.3 2.0+0.6 65 97
Known: (I)-a 2.0 0
(Ⅰ)-b 2.0 0
(Ⅰ)-c 2.0 0
(B-1) 0.1 0.3 47 45
(B-4) 0.8 1.6 60 78
(B-5) 0.3 0.6 50 87
As shown in embodiment, there is fabulous Fungicidally active in phytopathogenic fungi according to the composition of reactive compound of the present invention.And because synergistic effect, under the low working concentration of the various active composition that comprises in the composition than independent application, there is gratifying control efficiency in the present composition.

Claims (6)

1. agricultural is used and garden antifungal composition, it is characterized in that it contains active components A) and mixture B):
A) formamide of at least a following formula
Figure C9411880600021
Wherein
R 1Represent ethyl or isopropyl,
R 2Represent hydrogen atom or methyl,
R 3Represent hydrogen atom and
Z represents the chlorine atom,
With the carbon atom of asymmetric replacement, C *, for (R)-configuration (definitely) is a condition;
With
B) at least a being selected from down organized the compound that comprises:
Methyl-(E)-methoxyimino-[α-(o-tolyl oxygen)-o-tolyl] acetic acid esters, (E)-and 2-methoxyimino-N-methyl-2-(2-phenoxy phenyl) acetamide and methyl-(E)-2-{2-[6-(2-cyano-benzene oxygen)-pyrimidine-4-base oxygen] phenyl }-the 3-methoxy acrylate, wherein (A) group reactive compound is 1 with (B) weight ratio of group reactive compound: 0.1-1: 10.
2. according to the composition of claim 1, formamide wherein is the compound of formula (I), in the formula (I)
R 1Represent methylidene, ethyl or isopropyl,
R 2Represent hydrogen atom or methyl,
R 3Represent hydrogen atom or methyl and
Z represents the chlorine atom.
3. according to the composition of claim 1, formamide wherein is selected from one group of compound being made up of following compound:
N-(R)-[1-(4-chlorphenyl)-ethyl]-2, the 2-two chloro-1-ethyls-diastereomeric mixture of 3t-methyl isophthalic acid r-cyclopropane carboxamide,
N-(R)-[1-(4-chlorphenyl)-ethyl]-2, the diastereomeric mixture of 2-two chloro-1-isopropyl cyclopropane carboxamides,
N-(R)-[1-(4-chlorphenyl)-ethyl]-(1S)-2,2-two chloro-1-ethyls-3t-methyl isophthalic acid r-cyclopropane carboxamide and
N-(R)-[1-(4-chlorphenyl)-ethyl]-(1S)-2,2-two chloro-1-isopropyl cyclopropane carboxamides.
4. the method for control fungi is characterized in that the mixture according to the reactive compound of claim 1 is administered to fungi and/or its spot.
5. according to the purposes of the composition for preventing and controlling fungi of the reactive compound of claim 1.
6. the preparation method of fungicide composite is characterized in that mixing with filler and/or surfactant according to the composition of the reactive compound of claim 1.
CN94118806A 1993-11-25 1994-11-25 Fungicidally active compositions Expired - Fee Related CN1073802C (en)

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CN104642314B (en) * 2015-02-04 2017-05-17 宁波工程学院 Application of N-furan phenol methyl ether-5-yl) chromene-4-amide as sterilizing agent
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Citations (1)

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Publication number Priority date Publication date Assignee Title
US4988734A (en) * 1988-05-07 1991-01-29 Bayer Aktiengesellschaft Fungicidal stereoisomers of N-(R)-(1-aryl-ethyl)-1-alkyl-2,2,-dichloro-cyclopropanecarboxamides

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4988734A (en) * 1988-05-07 1991-01-29 Bayer Aktiengesellschaft Fungicidal stereoisomers of N-(R)-(1-aryl-ethyl)-1-alkyl-2,2,-dichloro-cyclopropanecarboxamides

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