CN1146321C - Fungicide composite for farm and garden use - Google Patents
Fungicide composite for farm and garden use Download PDFInfo
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- CN1146321C CN1146321C CNB001280988A CN00128098A CN1146321C CN 1146321 C CN1146321 C CN 1146321C CN B001280988 A CNB001280988 A CN B001280988A CN 00128098 A CN00128098 A CN 00128098A CN 1146321 C CN1146321 C CN 1146321C
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Abstract
The present invention relates to a novel bactericide composition comprising formamide of formula (I) having bactericidal activity and a known compound having bactericidal activity. The novel bactericide composition exhibits strong bactericidal activity, wherein the compound of formula (I) is as defined in the specification.
Description
The present invention relates to the benzamide type of known Fungicidally active and the new antifungal blend compositions of known Fungicidal active compound.
The benzamide type and the optical isomer thereof of the Fungicidally active that the present invention uses are known, see Japanese Patent Application Publication 15867-1986,201855-1987 and 11550-1990 number.At " The Pesticide Manual "; the 9th edition, 1991, during Britain crop protection association publishes; but also at " Noyaku Handbook " (agricultural chemicals handbook) 1989, Nisshokuho edits the compound of having described known Fungicidally active in (Japanese plant protection association).
In rice cropping, the extensive use rice transplanter carries out machinery to be transplanted, and is starved of simultaneously and prevents and treats the rice field crop pest together, fungicide is administered on the seedling case prevents and treats crop pest, and can save the labour in applications of fungicides.
For consideration to bio-safety and Environmental security, be starved of and reduce fungicide consumption and application times greatly, this situation further requires to study extensively and profoundly reducing dosage.
Specifically, be starved of and prevent and treat very important rice blast and other disease that remains in the rice field to be prevented and treated simultaneously, in control operation, save the labour again, and be starved of the biological safety that has improved more.
Have now found that following new fungicide blend compositions has extra high Fungicidally active, said composition comprises:
(A) benzamide type of the Fungicidally active of following formula:
R wherein
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,
Condition is an asymmetric carbon atom, C
*, have (R)-configuration (definitely) and (B) at least a be selected from down the group Fungicidal active compound:
(Z)-2 '-methyl acetanilide 4,6-dimethyl pyrimidine-2-base track,
(RS)-and 1-is right-chlorphenyl-4, and 4-dimethyl-3-(1H-1,2,4-triazol-1-yl-methyl) penta-3-alcohol,
Methyl isophthalic acid-(butyl carbamoyl)-2-benzimidazole carbamate, the tetrachloro isophthalonitrile,
5-ethyl-5,8-dihydro-8-oxo [1,3] dioxole is [4,5-g] quinoline-7-carboxylic acid also,
The 5-methyl isophthalic acid, 2,4-triazol [3,4-b] benzothiazole and
1,2,5, the 6-nafoxidine is [3,2,1-i, j] quinoline-4-ketone also.
Astoundingly, the Fungicidally active blend compositions of the bond of the benzamide type of the Fungicidally active that contains formula (I) representative of the present invention and known Fungicidal active compound, because the collaborative and synergistic effect of the mixture of active component of the present invention, has significant fungicidal action, the angle of the technique effect that this synergistic effect is produced from independent each reactive compound of application is seen and be can not see in advance, so can also reduce its consumption greatly.Specifically, the mycocidal blend compositions of the present invention is especially to rice blast in the paddy field, exist fabulous and certain effect by Fusarium and the fungus-caused rice seedling damping off of rhizopus and bacterial leaf-blight.
The benzamide type of using in the blend compositions about this Fungicidally active, its preferred substituted can be as following definition:
R
1Represent methylidene, ethyl or isopropyl,
R
2Represent hydrogen or methyl,
R
3Represent hydrogen or methyl and
Z represents chlorine.
Below address the examples for compounds of general formula (I) representative:
N-(R)-[1-(4-chlorphenyl)-ethyl]-2, the mixture of the diastereoisomer of 2-two chloro-1-ethyls-3t-methyl isophthalic acid r-cyclopropane carboxamide,
N-(R)-[1-(4-chlorphenyl)-ethyl]-2, the mixture of 2-two chloro-1-isopropyl cyclopropane carboxamide diastereoisomers,
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.
Among the present invention, the weight ratio of each self-contained active component changes in quite wide scope in the various blend compositions.Usually, the benzamide type of the Fungicidally active of the general formula of per 1 part of weight ratio (I) representative can use about 0.02 to about 50 parts of weight ratios, preferably approximately 0.1 compound to the known Fungicidally active of above-mentioned (B) groups of about 10 parts of weight ratios.
There is fabulous Fungicidally active in the blend compositions of Fungicidally active of the present invention, and in fact, and said composition can be used for the phytopathogenic fungi of kill harmful in practice.
Composition of the present invention is prevented and treated various phytopathogenic fungis as fungicide usually, fungi as Plasmodiophoromycetes, Oomycete, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, deuteromycetes etc., and also can be used as bactericide and prevent and treat the various plants malignant bacteria, comprise the bacterium of pseudomonadaceae, Rhizobiaceae, enterobacteria section, Corynebacteriaceae, Streptomycetaceae etc.
Concrete, the blend compositions of activity of the present invention exists can be to the rice warm disease, and bacterial blight of rice is by the fabulous killing action of Fusarium, pythium and the fungus-caused rice seedling damping off of rhizopus.
When killing the essential concentration of phytopathogenic fungi, the blend compositions of Fungicidally active of the present invention and plant have good compatibility.Therefore, when using composition, can implement the processing that plant shoot divides, also can handle seed and rhizome, but also can carry out soil treatment.
The blend compositions of activity of the present invention is very low to the warm blooded animal toxic level, so said composition can be used safely.
The blend compositions of activity of the present invention can be mixed with the mixture of the compound of Fungicidal carboxamides class and known Fungicidally active.In addition, also can prepare a kind of preparation that contains a kind of reactive compound and the another kind of preparation that contains another kind of reactive compound separately, like this, Zhi Bei two kinds of preparations can mix before use on the spot thus.
Natural and synthetic material, microcapsule formulations, coated composition that is used for seed that the above-mentioned preparation of addressing herein can be full of for liquor, wetting powder, emulsion, suspending agent, pulvis, foaming agent, paste, granula, tablet, aerosol, with reactive compound and preparation (as fumigation tube, fumigation tank and stifling dish) and micro-cold spray agent and the thermal spray agent of using with combustion apparatus.
Can adopt conventional method to produce these preparations, for example by with reactive compound and filler, promptly liquid or liquid gas or solid diluent or carrier mix, and can choose the use surfactant wantonly, i.e. emulsifier, dispersant and/or blowing agent and prepare.When liquid used water as filler, for example organic solvent also can be used as cosolvent.
Usually, described liquid diluent or carrier can be: aromatic hydrocarbons, as dimethylbenzene, toluene and Fluhyzon class; Chloro aromatic hydrocarbons or chloro aliphatic hydrocarbon are as chlorobenzene class, dichloroethane class and carrene; Aliphatic series or cycloaliphatic hydrocarbons, as cyclohexane or paraffinic, mineral oil level part for example; Alcohols is as butanols or ethylene glycol and their ethers and ester class; Ketone such as acetone, methyl ethyl ketone, methyl iso-butyl ketone (MIBK) or cyclohexanone; Or intensive polar solvent, as dimethyl formamide and dimethyl sulfoxide (DMSO); And water.
The liquid gas diluent or carrier is meant it is the liquid of gas at normal temperatures and pressures, and for example, aerosol propellant is as halogenated hydrocarbon and butane, propane, ammonia and carbonic acid gas.
The solid diluent that uses can be the natural minerals that ground, as kaolin, clay, talcum, from chalk, quartz, Attagel, imvite or diatomite and the synthetic material that ground, as silicic acid, aluminium oxide and the silicate of high dispersive.
The solid carrier that granule adopts can be the natural rock of crushing and classification, as calcite, marble, float stone, sepiolite and dolomite, and inorganic and organic synthesis particle powder, the particle of organic product such as sawdust, cocoa husk, corn ear and tobacco stem in addition.
The emulsifier and/or the blowing agent that adopt can be nonionic and anion emulsifier, as polyoxyethylene-fatty acid ester, polyoxyethylene-aliphatic alcohol ester, for example, the alkaryl polyglycol ether, alkylsulfonate, alkyl sulfate, arylsulphonate and albumin hydrolysate.Dispersant comprises, for example lignin sulfite waste liquor and methylcellulose.
Sticker such as carboxymethyl cellulose and natural and synthetic polymer (as gum Arabic, polyvinyl alcohol and polyvinyl acetate) can be used in the preparation of pulvis, granule or missible oil form.
Can use colouring agent such as inorganic pigment, for example, iron oxide, titanium oxide and Prussia orchid, and organic dyestuff, as alizarin dyes, diimide dyestuff or metal phthalocyanine dyestuff, and trace element, as the salt of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
Usually, can contain the reactive compound of 0.1 to 95% weight ratio in the preparation, be preferably 0.5 to 90% weight ratio.
Reactive compound of the present invention can exist with above-mentioned preparation or other type of service, randomly can exist with other known active substance, these active substances are just like insecticide, miticide, nematocide, weed killer herbicide, birds repellant, growth regulator, fertilizer and/or soil structure improver.
When using reactive compound of the present invention, they can be with itself, with its dosage form or the type of service use of preparation with its further dilution, as the forms such as solution, emulsion, suspending agent, pulvis, paste and granule that can use, can use above-mentioned preparation with conventional method, for example, water by sprinkling, soak, spraying, spraying, atomizing, steam, saturating wet, suspension, dressing, dust, distribution, drying, damp clothing, methods such as wet clothing, slurries clothing or involucrum use.
When the different piece of plant is used, the concentration of type of service reactive compound can change in wide range.It typically is 0.0001 to 1% weight ratio, be preferably 0.001 to 0.5% weight ratio.
In the processing of seed, the amount of reactive compound can be 0.001 to 50g, is preferably 0.01 to 10g/1Kg seed.
In the processing of soil, usually reactive compound is administered to target spot, concentration is the reactive compound of 0.00001 to 0.1% weight ratio, preferred 0.0001 to 0.02% weight ratio.
This paper is following can be described more specifically the present invention by embodiment, but these embodiment do not constitute limitation of the scope of the invention.
Bioexperiment embodiment
The compound of test usefulness
(I)-and a:N-(R)-[1-(4-chlorphenyl)-ethyl]-2, the mixture of the diastereoisomer of 2-two chloro-1-ethyls-3t-methyl isophthalic acid r-cyclopropane carboxamide.
(I)-and b:N-(R)-[1-(4-chlorphenyl)-ethyl]-2, the mixture of the diastereoisomer of 2-two chloro-1-isopropyl cyclopropane carboxamides,
(I)-and c:N-(R)-[1-(4-chlorphenyl)-ethyl]-1 (S)-2,2-two chloro-1-ethyls-3t-methyl isophthalic acid r-cyclopropane carboxamide,
The A:5-methyl isophthalic acid, 2,4-triazol [3,4-b] benzene isothiazole,
B:1,2,5, the 6-nafoxidine is [3,2,1-ij] quinoline-4-ketone also,
C:(RS)-and 1-is right-chlorphenyl-4, and 4-dimethyl-3-[1H-1,2,4-triazol-1-yl methyl] penta-3-alcohol,
D:(Z)-2 '-methyl acetanilide 4,6-dimethyl pyrimidine-2-base hydrazone,
E:5-ethyl-5,8-dihydro-8-oxo [1,3] benzodioxoles is [4,5-g] quinoline-7-carboxylic acid also.
F: the mixture (2: 5 mixing ratios) of methyl isophthalic acid-(butyl carbamoyl)-2-benzimidazole carbamate and tetrachloro isophthalonitrile.
Embodiment 1
Fungicidal test to rice blast
The preparation of reactive compound
Each reactive compound: 25 to 50 parts of weight ratios
Carrier: the diatomite/kaolin mixture of 45 to 70 parts of weight ratios be (1: 5
Mixing ratio)
Emulsifier: the polyoxyethylene alkane phenyl ether of 5 parts of weight ratios
In order to prepare appropriate formulation, with the emulsifier ground and mixed of the carrier of each reactive compound of described amount, described amount and described amount to form wetting powder, the wetting powder of dilute with water scheduled volume then.
Experimental technique
With a plurality of 100cm
2Each personal fluviogenic soil filling of Wagner plastic basin and making overflow water state.After harrowing soil surface, remove the water on it and make basin leave standstill a whole day, in the middle of the soil table, control the hole of a dark 3cm of diameter 2cm then, the bottom adds as the water-reducible preparation of the scheduled volume of above-mentioned preparation toward wherein being deep to.
In hole, implant three stalk two leaf stage rice seedling (kinds: Kusabue) and with dry soil cover to finish transplanting.After this all basins are placed in the greenhouse, keep 20 to 33 ℃ temperature range to keep 30 days, make seedling growth, spray the rice blast fungal spore that inoculation obtains according to conventional methods to it then.
Inoculate after seven days, measure the infection rate of every basin rice strain, and according to following evaluation criterion record, to obtain the corresponding protection value.
Infection rate
The area (%) of scab has taken place
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
Calculate the protection percentage by following formula:
Wherein the A representative is at the infection rate in contrast (being untreated) zone; And B represents the infection rate of processing region.
In this experiment, each pilot region is made up of three basins.
The results are shown in table 1
Table 1
| The compound of experiment usefulness | Active component dosage (g/ dish) | Protection value (%) |
| (I)-a+A (I)-a+B (I)-b+A (I)-b+B (I)-c+A (I)-c+B | 0.25+0.25 0.5+0.5 0.25+0.25 0.5+0.5 0.25+0.25 0.5+0.5 0.25+0.25 0.5+0.5 0.25+0.25 0.5+0.5 0.25+0.25 0.5+0.5 | 97 100 98 100 97 100 97 100 100 100 100 100 |
| (I)-a (I)-b (I)-c A B is untreated | 0.25 0.5 0.25 0.5 0.25 0.5 0.25 0.5 0.25 0.5 - | 40 77 37 68 60 83 38 55 47 60 0 |
Embodiment 2
(A) to the prevention effect (potted plant experiment) of rice blast
Make paddy rice (kind: Kusabue) grow in the basin of diameter 12cm.In tillering stage rice plant is sprayed the mixture of reactive compound of the present invention on the one hand, spray the independent composition of reactive compound of the present invention simultaneously on the other hand to it.Each preparation is diluted with water to predetermined concentration and makes spray liquid with as the preparation of the same procedure of embodiment 1, and above-mentioned basin is placed on around the turntable, sprays above-mentioned spray liquid to the turntable table top by nozzle, and nozzle exit pressure is 1.5Kg/cm
2, per three basin paddy rice make the leaf of rice plant moistening fully with each wetting powder of 50ml.
After two days, will remain on 25 ℃ of relative moisture with the rice plant that preparation is so handled and be in 100% the moist chamber, simultaneously the rice blast fungal spore suspension of twice spray inoculation artificial culture (50000 to 100000 spores/ml) on plant.
Inoculate after seven days, measure the infection rate of every basin rice strain, and according to following evaluation criterion record, to obtain the corresponding protection value.
Infection rate
The area (%) of scab has taken place
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
Calculate the protection percentage by following formula:
Wherein the A representative is at the infection rate in contrast (being untreated) zone; And
B represents the infection rate of processing region.
In this experiment, each test region is made up of three basins.
(B) (potted plant experiment) tested in the therapeutic action of paddy rice rice warm disease
Carry out this experiment to measure the result of treatment of reactive compound to invading and therefore having infected the rice blast fungi of rice plant body.Promptly, similar rice plant of using in the above-mentioned prevention effect experiment (A) in being 100% thermostatic chamber, 25 ℃, relative moisture was placed two days, simultaneously, the rice blast spore suspension of same procedure spray inoculation artificial culture on plant of using with above-mentioned experiment A.Second day, use the identical method of above-mentioned prevention effect experiment, the rice plant of inoculating the rice blast fungi and cultivating in basin is sprayed the mixture of reactive compound of the present invention on the one hand, spray its independent active component on the other hand.Spray and handle after six days, adopt the method that is similar in the aforesaid prevention effect experiment, measure the infection rate of every basin rice plant, and calculate to obtain the corresponding protection value according to evaluation criterion.
The results are shown in table 2.
Table 2
| The composition of experiment usefulness | The concentration of active component (ppm) | Protection value (%) | |
| Protective effect | Therapeutic action | ||
| (I)-a+C (I)-a+D (I)-b+C (I)-b+D (I)-c+C (I)-c+D (I)-a (I)-b (I)-c C D is untreated | 10+25 20+50 10+50 20+100 10+25 20+50 10+50 20+100 10+25 20+50 10+50 20+100 10 20 10 20 10 20 25 50 50 100 - | 95 100 93 100 93 100 90 100 100 100 97 100 83 90 80 90 90 95 23 30 10 27 0 | 85 93 80 83 83 90 80 83 90 93 85 90 0 0 0 0 0 0 33 57 20 47 0 |
Embodiment 3
Antifungal experiment to seedling blight of rice and rice blast (Pyricularia oryzae)
Experimental technique 1
The seedling soil that will be suitable for the rice-cultivating strain is filled the seedling case, and (30cm * 60cm * 2cm), this seedling soil is in advance with being seeded in rhizopus fungi (2%) preparation of cultivating on the rice chaff medium.On the other hand, the seedling soil of rhizopus fungi is not inoculated in preparation respectively, but handle the back seedling soil is carried out similar rhizopus fungi inoculation, and this preparation method is suitable for making rice shoot can not be transplanted to the situation in rice field owing to infected serious seedling blight of rice.
Belt leather paddy (kind: Kusabue) after planting just at seedling soil upper seeding wheel scheduled volume, pesticidal preparations as the preparation of embodiment 1 same procedure, with predetermined concentration (500ml/ case), evenly soak into to use and water the seed that basin was handled, then cover and carry out conventional seedling cultivation with soil.
After five days, a situation arises on rice shoot by the microbial seedling blight of rice of rhizopus according to following evaluation criterion inspection, simultaneously, makes the rice shoot further growth.After 20 days, with planter (Kubota K.K. make four lines type planter) the seedling transplantation of cultivation like this to paddy field.In this experiment, use the zone and the district of being untreated of the agricultural chemical compound of above-mentioned each independent being selected from (I)-a, (I)-b, (I)-c and F, observed serious atrophy by the fungus-caused seedling blight of rice of rhizopus, respectively preparation not with the rhizopus fungi to the rice shoot of its inoculation and be used for the rice field transplanting.After transplanting 40 days, observe rice blast on rice shoot infection and be developed to the order of severity gradually.Transplanted back 65 days, the evaluation of infecting to be obtaining the protection value of this agricultural chemicals blend compositions, and carries out the evaluation of phyto toxicity.
In this experiment, be 100% with the total surface area of seedling case, by calculating the percentage of the rice shoot surface area that has infected the fungus-caused rice seedling damping off of rhizopus, estimate the infection rate of rice shoot.Under the situation of untreated plant, infecting area is about 80%.
Utilize following formula to calculate protection value (%):
Wherein the A representative contrasts the infection rate in (being untreated) zone; And
B represents the infection rate of processing region.
Experimental technique 2:
By the fungus-caused rice shoot pythium rot of Fusarium (Fusarium Sp., Phthium)
Use the similar approach of above-mentioned rhizopus fungi, use the Fusarium fungi and experimentize.
Infection area in the district of being untreated is approximately 24% of the seedling case gross area.
In each experiment, do not observe phyto toxicity.
Experimental results reduction is in following table 3.
Table 3
| The compound of experiment usefulness | The dosage of active component (g/ case) | Protection value % | ||
| The fungus-caused seedling blight of rice of rhizopus | The fungus-caused seedling blight of rice of Fusarium | The fungus-caused rice blast of rice blast | ||
| (I)-a+F (I)-b+F (I)-c+F | 0.5+0.35 1+0.7 0.5+0.35 1+0.7 0.5+0.35 1+0.7 | 90 98 88 95 93 97 | 83 88 79 85 80 93 | 90 93 88 90 93 99 |
| (I)-a, (I)-b, (I)-c F is untreated | 0.5 1 0.5 1 0.5 1 0.35 0.7 - | 0 0 0 0 0 0 78 90 0 | 0 0 0 0 0 0 60 75 0 | 65 83 60 77 83 90 0 0 0 |
Embodiment 4
Antifungal experiment to rice blast
(A) to the prevention effect (potted plant experiment) of rice blast
Make paddy rice (kind: Kusabue) grow in the basin of diameter 12cm.In tillering stage rice plant is sprayed the mixture of reactive compound of the present invention on the one hand, spray the independent composition of reactive compound of the present invention simultaneously on the other hand to it.Each preparation is diluted with water to predetermined concentration and makes spray liquid with as the preparation of the same procedure of embodiment 1, and above-mentioned basin is placed on around the turntable, sprays above-mentioned spray liquid to the turntable table top by nozzle, and nozzle exit pressure is 1.5Kg/cm
2, per three basin paddy rice make the leaf of rice plant moistening fully with each wetting powder of 50ml.
After two days, will remain on 25 ℃ of relative moisture with the rice plant that preparation is so handled and be in 100% the moist chamber, simultaneously the rice blast fungal spore suspension of twice spray inoculation artificial culture (50000 to 100000 spores/ml) on plant.
Inoculate after seven days, measure the infection rate of every basin rice strain, and according to following evaluation criterion record, to obtain the corresponding protection value.
Infection rate
The area (%) of scab has taken place
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
Calculate the protection percentage by following formula:
Wherein the A representative is at the infection rate in contrast (being untreated) zone; And
B represents the infection rate of processing region.
In this experiment, each test region is made up of three basins.
The results are shown in table 4.
Table 4
| The composition of experiment usefulness | The concentration of active component (ppm) | Leaf portion rice blast protection value (%) |
| (I)-a+E (I)-b+E (I)-c+E | 25+100 50+200 25+100 50+200 25+100 50+200 | 93 96 92 95 96 98 |
| (I)-a (I)-b (I)-c E is untreated | 25 50 25 50 25 50 100 200 - | 57 68 58 65 70 83 6 27 0 |
Embodiment 5
Bacterial leaf-blight (Pseudomonas glumae) is tested
Experimental technique:
Adopt conventional method, with the rice seedling (kind: Nihonbare) be transplanted in the paddy field of cultivating in the seedling case, then respectively in the paddy rice heading before seven days and two days (after transplanting 80 days, observe about 50% heading rate), at night, spray the dispersion liquid (10 of bacterial leaf spot bacterium with the 100 liters/dosage of 10 acres (a)
9Fragment/ml) (above-mentioned bacterium is cultivated on the PPG medium), after the inoculation, artificial water spray is to promote the breeding of leaf spot bacteria.In the end inoculate two days respectively and the Ninth Heaven after, the processing of spraying, treatment fluid adopts the predetermined concentration water diluent by each preparation of the same procedure preparation of previous embodiment 1, and treatment dosage is 150 liters/10 acres (a), and spraying is handled to adopt and born the type full automatic sprayer.
The results are shown in table 5.
Table 5
| The composition of experiment usefulness | The concentration of active component (ppm) | Bacterial leaf-blight | |
| Spike of rice shrinkage factor (%) | Protection value (%) | ||
| (I)-a+E (I)-b+E (I)-c+E | 25+100 50+200 25+100 50+200 25+100 50+200 | 45.6 32.5 43.7 32.6 33.5 20.5 | 51 65 53 65 64 78 |
| (I)-a (I)-b (I)-c E is untreated | 25 50 25 50 25 50 100 200 - | 79.1 69.8 80.9 67.9 75.3 71.6 52.1 40.0 93.0 | 15 25 13 27 19 23 44 57 0 |
Claims (4)
1. agricultural and garden antifungal blend compositions is characterized in that it contains the composition of the active substance of being made up of following compound:
(A) benzamide type of the Fungicidally active of following formula:
R wherein
1Represent ethyl or isopropyl,
R
2Represent hydrogen atom or methyl,
R
3Represent hydrogen atom or methyl and
Z represents the chlorine atom,
Condition is asymmetric carbon atom C
*Has (R)-configuration (definitely); (B) Fungicidal active compound (Z)-2 '-methyl acetanilide 4,6-dimethyl pyrimidine-2-base hydrazone, wherein (A) group compound and (B) weight ratio of compound be between 1: 0.1 to 1: 10.
2. kill the method for fungi, it is characterized in that making the antifungal blend compositions of claim 1 to act on fungi and/or their habitat.
3. the blend compositions of application rights requirement 1 is killed the purposes of fungi.
4. the preparation method of Fungicidal composition is characterized in that making the blend compositions of claim 1 to mix with filler and/or surfactant.
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59396/1993 | 1993-02-25 | ||
| JP05939693A JP3195109B2 (en) | 1993-02-25 | 1993-02-25 | Agricultural and horticultural fungicide composition |
| JP69148/1993 | 1993-03-05 | ||
| JP69150/1993 | 1993-03-05 | ||
| JP06914993A JP3560620B2 (en) | 1993-03-05 | 1993-03-05 | Agricultural and horticultural fungicide composition |
| JP69149/1993 | 1993-03-05 | ||
| JP5069150A JPH06256119A (en) | 1993-03-05 | 1993-03-05 | Bactericide composition for agricultural and horticultural use |
| JP5069148A JPH06256120A (en) | 1993-03-05 | 1993-03-05 | Bactericide composition for agricultural and horticultural use |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN94101945A Division CN1071542C (en) | 1993-02-25 | 1994-02-25 | Agricultural and horticultural fungicidal compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1307805A CN1307805A (en) | 2001-08-15 |
| CN1146321C true CN1146321C (en) | 2004-04-21 |
Family
ID=27463759
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN94101945A Expired - Fee Related CN1071542C (en) | 1993-02-25 | 1994-02-25 | Agricultural and horticultural fungicidal compositions |
| CNB001280988A Expired - Fee Related CN1146321C (en) | 1993-02-25 | 2000-12-01 | Fungicide composite for farm and garden use |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN94101945A Expired - Fee Related CN1071542C (en) | 1993-02-25 | 1994-02-25 | Agricultural and horticultural fungicidal compositions |
Country Status (3)
| Country | Link |
|---|---|
| KR (1) | KR100314196B1 (en) |
| CN (2) | CN1071542C (en) |
| BR (1) | BR9400668A (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11723362B2 (en) * | 2019-09-19 | 2023-08-15 | -The United States of America, as represented by The Secretary of Agriculture | Broad-spectrum synergistic antimicrobial compositions |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3815728A1 (en) * | 1988-05-07 | 1989-11-16 | Bayer Ag | STEREOISOMERS OF N- (R) - (1-ARYL-ETHYL) -1-ALKYL-2,2-DICHLORO-CYCLOPROPANCARBONIC ACID AMIDES |
-
1994
- 1994-02-21 KR KR1019940003057A patent/KR100314196B1/en not_active IP Right Cessation
- 1994-02-24 BR BR9400668A patent/BR9400668A/en not_active IP Right Cessation
- 1994-02-25 CN CN94101945A patent/CN1071542C/en not_active Expired - Fee Related
-
2000
- 2000-12-01 CN CNB001280988A patent/CN1146321C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CN1307805A (en) | 2001-08-15 |
| KR100314196B1 (en) | 2002-11-23 |
| CN1093521A (en) | 1994-10-19 |
| CN1071542C (en) | 2001-09-26 |
| BR9400668A (en) | 1994-09-27 |
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