CN1062413C - Fungicidal and insecticidal composition - Google Patents
Fungicidal and insecticidal composition Download PDFInfo
- Publication number
- CN1062413C CN1062413C CN96106643A CN96106643A CN1062413C CN 1062413 C CN1062413 C CN 1062413C CN 96106643 A CN96106643 A CN 96106643A CN 96106643 A CN96106643 A CN 96106643A CN 1062413 C CN1062413 C CN 1062413C
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- Prior art keywords
- germicidal
- methyl
- compound
- insecticidal
- rice
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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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/14—Ethers
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
To obtain a complex germicidal and insecticidal agent exhibiting an especially excellent germicidal and insecticidal effect with a lower dose by using an established specific germicidal carboxamide and an established specific germicidal compound in combination and a synergistic effect owing to mixing of the both compounds. The objective complex germicidal and insecticidal agent contains (A) a compound expressed by the formula (Z is halogen; R<1> is 1-4C alkyl; R<2> is H, methyl or ethyl; R<3> is H or methyl) or its optical isomer and a compound selected from specific germicidal compounds such as S.S'-(2- dimethylaminotrimethylene) bis(thiocarbamate), N, N-dimethyl-1.2.3-trithian-5- ylamine, 2-tertbutylimino-3-isopropyl-5-phenyl-1.3.5-thiadiazinan-4-one and 2-(4- ethoxyphenyl)-2-methylpropyl-3-phenoxybenzyl ether as active ingredients. Said complex germicidal and insecticidal agent exhibits a strong germicidal and insecticidal action without chemical injury to cultured plants with only a slight toxicity to warm-blooded animals.
Description
The present invention relates to have known benzamide type or its known optical isomer and the new antifungal of knowing compound the sixth of the twelve Earthly Branches and insecticidal synergistic active compound composition of Fungicidally active with insecticidal activity.
Disclose some and had the benzamide type (openly speciallyying permit communique No.15867/1986,201855/1987 and 11550/1990) of Fungicidally active referring to Japan Patent.
In the cultivation of paddy rice, extensively adopt rice transplanter to carry out machine rice transplantation in recent years; And in control rice pest and crop pest, being starved of seedling case applying pesticide, and the labour who saves applying pesticides with while pest control and crop pest.
For bio-safety and environmental protection, not only be starved of the consumption that reduces insecticide greatly, but also require to significantly reduce their application times, this situation further requires the problem that as far as possible reduces dosage is carried out extensive studies.
Specifically, in the cultivation of paddy rice, at the important disease of important pests of needs controls (rice that for example belongs to coleoptera resembles plant hopper and the leafhopper that belongs to insect etc., belongs to Semiptera) and needs control rice blast for example, be starved of the labour that pest control and fungi, saving control simultaneously operate and also improve biological safety greatly.
Have now found that benzamide type or its optical isomer and at least a new active compound composition with known compound of insecticidal activity by formula (I) expression have extra high antifungal and insecticidal activity.
Wherein z represents halogen atom;
R
1Represent C
1-4Alkyl;
R
2Represent hydrogen atom, methyl or ethyl;
R
3Represent hydrogen atom or methyl; Described compound with insecticidal activity is selected from: s, s '-(2-dimethylamino trimethylene) two (thiocarbamates), N, N-dimethyl 1,2,3-trithiane-5-base amine, 2-tertbutylimido-3-isopropyl-5-phenyl-1,3,5-thiaziazinane-4-ketone, 2-(4-ethoxyl phenenyl)-2-methyl-propyl 3-phenoxy benzyl ether and (RS)-alpha-cyano-3-phenoxy benzyl (RS)-2,2-two chloro-1-(4-ethoxyl phenenyl) cyclopropanecarboxylcompound.
To have the benzamide type of Fungicidally active or its optical isomer by above-mentioned formula (I) expression above-mentioned opposite with above-mentioned known compound pest control and crop pest with insecticidal activity with using respectively, desinsection of the present invention and Fungicidal active substance composition be simultaneously pest control and crop pest unexpectedly, and because the mixture of two kinds of active components has collaborative and synergistic effect, so use very low dosage just can reach significant desinsection and fungicidal effect, this effect is unexpected by only using two kinds of technique effects that reactive compound produced respectively.
In addition, desinsection of the present invention and Fungicidal active substance composition also can have stable and excellent effect and effect simultaneously, not only can prevent and treat the primary pest that occurs in the rice cropping, as belong to Semiptera plant hopper and leafhopper, belong to the rice root weevil of coleoptera and belong to lepidopterous rice leaf roller (even they have resistance to known insecticide such as organic phosphorus compound and carbamates), and can prevent and treat and generally acknowledge it is the most harmful rice blast.
According to the present invention, a kind of material in the described active compound composition defines with above-mentioned formula (I) usually.
In the formula (I), preferably,
Z represents the chlorine atom,
R
1Represent methylidene, ethyl, n-pro-pyl or isopropyl,
R
2Represent hydrogen atom or methyl,
R
3Represent hydrogen atom or methyl.
As the instantiation of formula (I) compound, can enumerate:
N-(1-(4-bromophenyl) ethyl)-2,2-two chloro-1,3,3-trimethyl cyclopropane carboxamide, N-(1-(4-chlorphenyl) ethyl)-2,2-two chloro-1,3,3-trimethyl cyclopropane carboxamide, N-(1-(4-chlorphenyl) ethyl)-2,2-two chloro-1-ethyls-3-methyl cyclopropane formamide, N-(1-(4-chlorphenyl) ethyl)-2,2-two chloro-1-isopropyl cyclopropane carboxamides, N-(R)-(1-(4-chlorphenyl) ethyl)-2, the non-enantiomer mixture of 2-two chloro-1-ethyls-3t-methyl isophthalic acid r-cyclopropane carboxamide, N-(R)-(1-(4-chlorphenyl) ethyl)-2, the non-enantiomer 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, N-(R)-(1-(4-chlorphenyl) ethyl)-(1S)-2,2-two chloro-1-isopropyl cyclopropane carboxamides.
Above-claimed cpd is disclosed by document this day disclosure special permission communique 15867/1986,201855/1987 and 11550/1990 above-mentioned.
The used known compound with insecticidal activity is by " Pesticide Manual " the 8th edition (British Crop Protection Council publication) and disclosed those compounds of NoyakuBinran (insecticide handbook, version in 1988) in 1987 in desinsection of the present invention and the Fungicidal active substance composition.
According to the present invention, the weight ratio between the active component that is comprised in each blend compositions can change in the scope of broad.In general, per 1 part (weight) can use 0.05～10 part (weight) by formamide or its optical isomer of the Fungicidally active of formula (I) expression, preferably 0.1～5 part of known compound that (weight) has insecticidal activity.
Yet if desired, above-mentioned weight ratio can change according to the extent of damage that insect and fungi are caused.
Desinsection of the present invention and Fungicidal active substance composition have excellent desinsection and Fungicidally active, so they can advantageously use as desinsection and fungicide in using such as blade dispenser, applying drug underwater, soil pesticide, soil fusion dispenser, the dispenser of seedling case etc.
Desinsection of the present invention and Fungicidal active substance composition have strong desinsection and fungicidal action, and therefore, they preferably use as desinsection that mixes and fungicide.In addition; active compound composition of the present invention is very low to the phytotoxicity of cultivated plant; toxicity to warm blooded animal is also very low; so; said composition can be safely and is used to prevent and treat various fungies, insect effectively; particularly hexapeopoda pest and plant disease, with guarantee crops particularly rice class plant be protected.These reactive compounds are in the whole process in vegetative period or in a certain period, and common, insect and disease responsive and that chemoresistance is arranged are had very high activity usually.
As plant disease and hexapeopoda pest, can propose and specifically be exemplified below:
As plant disease, can enumerate following fungi: Plasmodiophoromycetes, ovum mattress guiding principle, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and deuteromycetes.
Particularly, the Magnaporthe grisea that belongs to deuteromycetes can remain the antifungal spectrum of desinsection of the present invention and Fungicidal active substance composition.
The insect of the present invention's control comprises: coleoptera such as rice root weevil, rice resemble, rice leaf beetles; Lepidoptera such as striped rice borer, cnaphalocrocis medinalls guenee, rice green caterpillar, rice plant skipper; Semiptera such as rice leafhopper, brown planthopper, small brown rice planthopper, white-backed planthopper, Bemisia spp; Orthoptera such as African mole cricket, African migratory locust.
Desinsection of the present invention and Fungicidal active substance composition can be mixed with conventional preparation.
As these preparations, preparation and the micro-cold mist and the warm mist preparation that can propose solution, emulsion, suspension, pulvis, wetting powder, Pao Droplets agent, paste, granula, aerosol, natural and synthetic material section, microcapsules, the composition that is used to dress seed, use with combustion apparatus (as stifling box, fumigation tank, fumigate coil pipe) with the reactive compound dipping.
These preparations can prepare with known method, for example, are that the gas of liquid or liquefaction or solid diluent or carrier mix with reactive compound and filler, and can randomly use surfactant is emulsifier, dispersant and/or foam agent.Under the situation of water, for example also can use organic solvent as secondary solvent as filler.
As liquid diluent or carrier, can enumerate aromatic hydrocarbons such as dimethylbenzene, toluene and Fluhyzon usually; Chlorinated aromatic hydrocarbons or chlorinated aliphatic hydrocarbon such as chlorobenzene, vinyl chloride and carrene; Aliphatic hydrocarbon or alicyclic such as cyclohexane or alkane, for example mineral oil fractions; Alcohol is as butanols or ethylene glycol and their ether and ester; Ketone such as acetone, MEK, methyl iso-butyl ketone (MIBK) or cyclohexanone; Or intensive polar solvent such as dimethyl formamide and dimethyl sulfoxide (DMSO); And water.
The diluent for gases of so-called liquefaction or carrier are meant and are the liquid of gaseous state, for example aerosol propellant such as halogenated hydrocarbons and butane, propane, nitrogen and carbonic acid gas at normal temperatures and pressures.
As solid diluent, can use natural material such as the synthetic material section of kaolin, clay, talcum, chalk, quartz, Attagel, montmorillonite or diatomite and fine grinding such as silicic acid, aluminium oxide and the silicate of high dispersive of fine grinding.
As the solid carrier of using for granula, can use natural stone such as calcite, marble, float stone, sepiolite and the dolomite of crushing and classification, and the particle of the synthetic particle of inorganic and organic powder and organic material section such as sawdust, cocoa husk, corncob and tobacco stem.
As emulsifier and/or foam agent, can use nonionic and anionic emulsifier such as polyethylene glycol oxide-fatty acid ester, polyethylene glycol oxide-fatty alcohol ether (for example alkylaryl polyglycol ether), alkylsulfonate, alkyl sulfate, arylsulphonate and albumin hydrolysate.Dispersant comprises, for example, and lignin sulfite waste liquor and methylcellulose.
In the preparation of pulvis, granula or missible oil form, can use sticker such as carboxymethyl cellulose and natural and synthetic polymer (as gum Arabic, polyvinyl alcohol and polyvinyl acetate).
Can use colouring agent such as inorganic pigment, for example iron oxide, titanium dioxide and Prussian blue; Organic dyestuff such as alizarin dyes, azo dyes or metal phthalocyanine dyestuff; And trace element such as molysite, manganese salt, boron salt, mantoquita, cobalt salt, molybdenum salt and zinc salt.
Said preparation contains for example 0.1～95% (weight), the preferably reactive compound of 0.5～90% (weight).
Desinsection of the present invention and Fungicidal active substance composition can so use, or use, or randomly to use with the type of service that other activating agent such as insecticide, bactericide, mildewcide, fungicide, growth regulator or weed killer herbicide prepare by it with the preparation of its commercially practical.The example of insecticide comprises, for example by organophosphorus ester, carbamate, carboxylate, chlorohydrocarbon and the insecticide that obtains from the insect killing substance of microorganism.
In addition, desinsection of the present invention and Fungicidal active substance composition can be the confections with synergist, adopt the preparation or the type of service of commercially practical type.Term " synergist " is meant the compound that itself does not have activity but promote the reactive compound effect.
In the preparation of commercially available type, the content of desinsection of the present invention and Fungicidal composition can change in very wide scope, promptly about 0.00001～100% (weight), preferably about 0.001～5% (weight).
Desinsection of the present invention and Fungicidal active substance composition can use with the conventional method that is suitable for concrete preparation.
Desinsection of the present invention and Fungicidal active substance composition can be mixed with the mixture of above-mentioned general formula (I) reactive compound and known compound on the spot, take for example so-called bucket mix formulation form.
Be described more specifically the present invention below with reference to embodiment, but these embodiment should think never and limit the scope of the present invention by mistake.Biologic test embodiment: test compound: I 1:N-(1-(4-chlorphenyl) ethyl)-2,2-two chloro-1,3,3-trimethyl cyclopropane carboxamide, I 2:N-(1-(4-chlorphenyl) ethyl)-2,2-two chloro-1-ethyls-3-methyl cyclopropane formamide, I 3:N-(1-(4-chlorphenyl) ethyl)-2,2-two chloro-1-isopropyl cyclopropane carboxamides, I 4:N-(R)-(1-(4-chlorphenyl) ethyl)-2, the non-enantiomer mixture of 2-two chloro-1-ethyls-3t-methyl isophthalic acid r-cyclopropane carboxamide, I 5:N-(R)-(1-(4-chlorphenyl) ethyl)-(1S)-2,2-two chloro-1-ethyls-3t-methyl isophthalic acid r-cyclopropane carboxamide, I 6:N-(1-(4-bromophenyl) ethyl)-2,2-two chloro-1,3,3-trimethyl cyclopropane carboxamide, I 7:N-(R)-(1-(4-chlorphenyl) ethyl]-2, the non-enantiomer mixture of 2-two chloro-1-isopropyl cyclopropane carboxamides.A:S, S '-(2-dimethylamino trimethylene) two (thiocarbamates), B:N, N-dimethyl-1,2,3-trithiane-5-base amine, C:2-tertbutylimido-3-isopropyl-5-phenyl-1,3,5-thiaziazinane-4-ketone, D:2-(4-ethoxyl phenenyl)-2-methyl-propyl 3-phenoxy benzyl ether, and E:(RS)-alpha-cyano-3-phenoxy benzyl (RS)-2,2-two chloro-1-(4-ethoxyl phenenyl)-cyclopropanecarboxylcompound.
The preparation of embodiment 1 reactive compound
Every kind of reactive compound: 5-25 part (weight)
Carrier: 70～90 parts of (weight) diatomite/kaolin mixture (1: 5 mixtures
Emulsifier: 5 parts of (weight) polyethylene glycol oxide alkyl phenyl ethers
In order to prepare the appropriate formulation of every kind of reactive compound, every kind of reactive compound of specified amount, the carrier of specified amount and the emulsifier of specified amount are mixed the wetting powder that forms every kind of reactive compound under grinding, gained wetting powder water mixed diluting with scheduled volume arrives desired concentration then, thereby forms desired preparation.Test method
Be plantation rice strain (Asahi kind) under the irrigation state in the ceramic whiteware flowerpot of 12cm at some diameters, each flowerpot is planted three strains.In the early tillering stage, water in the flowerpot by the water surface in the flowerpot with every kind of active compounds solution of a suction pipe predetermined concentration, until the dosage that reaches appointment, to prevent that simultaneously the plant corpus on soil top from contacting with this solution.
After three days, each flowerpot covers with a basket, wherein puts into the rice leafhopper nymph in ten four ages and infects, and infects and measures insect mortality in back two days.
Handled the back 20 days, and according to the method for routine the suspension of rice blast spore (Magnaporthe grisea) was sprayed onto in each flowerpot and inoculates, 25～26 ℃ of temperature and of flowerpot was placed 24 hours in transfer room under the relative moisture of 100%.Then, 20～28 ℃ of each flowerpot is moved in the glass greenhouse that remains under, inoculate back seven days, the zone (%) 00 0.5 that disease point appears in measure the infection rate of each flowerpot semilate rice strain and, also evaluate control rate (%) and phytotoxicity degree simultaneously according to following evaluation criteria record. gradient of infection is lower than 21 2～be lower than 52 5～be lower than 10 3 10～be lower than 20 4 20～be lower than 40 5 40 or highlyer calculate the control percentage with following formula:
Wherein the A representative contrasts the gradient of infection in (not being subject to processing) zone;
The B representative is subject to processing the gradient of infection in zone.
In this test, each pilot region is made up of three flowerpots.
The results are shown in the table 1 of this test.
Table 1
Embodiment 2 (ⅰ) is to the preparation of the blade dispenser test reactive compound of brown planthopper and light red leafhopper
| Subject composition | The concentration of active component (kg/ hectare) | Effect | |
| The lethality of rice leafhopper (%) | The control value (%) of rice blast | ||
| D+I.1+I.2+I.3+I.4+I.5+I.6+I.7 E+I.1+I.2+I.3+I.4+I.5+I.6+I.7 I.7 I.6 I.5 I.4 I.3 I.2 I.1 D E be not subject to processing | 1+1 1+1 1+1 1+0.5 1+0.5 1+1 1+0.5 2+1 2+1 2+1 2+0.5 2+0.5 2+1 2+0.5 1 2 1 1 1 0.5 0.5 1 0.5 - | 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 0 0 0 0 0 0 0 0 | 83 83 77 91 93 80 91 87 83 73 91 91 83 91 0 0 73 67 70 87 87 67 85 0 |
Every kind of reactive compound: 30～40 parts (weight)
Carrier: 55～65 parts of (weight) diatomite/kaolin mixture (1: 5 mixture)
Emulsifier: 5 parts of (weight) polyethylene glycol oxide alkyl phenyl ethers
In order to prepare the appropriate formulation of every kind of reactive compound, every kind of reactive compound of specified amount, the carrier of specified amount and the emulsifier of specified amount are mixed the wetting powder that forms every kind of reactive compound under grinding, then, with the gained wetting powder water mixed diluting of scheduled volume to desired concentration, thereby form desired preparation.Test method
Be about the rice strain that plantation three plant height degree in the flowerpot of 13cm are about 15cm at each diameter, took root back ten days at it, with the dosage of 20ml/ basin each flowerpot is sprayed the aqueous solution of above-mentioned every kind of active agent preparations of predetermined concentration with spray gun, after the preparation that so sprays becomes dry, each flowerpot covers a basket, simultaneously put into brown planthopper nymph and the light red leafhopper larva that is respectively three ages and four ages therein with the ratio of ten/basin, after five days, measure the brown planthopper death toll then, after three days, measure light red leafhopper death toll, to obtain every kind of insect mortality.(ⅱ) the blade dispenser of rice blast is tested
Be plantation rice strain (Asahi kind) in the porcelain flowerpot of 12cm at some diameters.In 3～4 leaf phases, this rice strain is sprayed the preparation of every kind of reactive compound of above-mentioned preparation with the amount of 50ml/3 basin.Second day, with the suspension of rice blast fungal spore (Magnaporthe grisea, artificial culture) this plant is sprayed twice, placing temperature then is that 25 ℃, relative moisture are that 100% greenhouse infects.
Inoculate back seven days, measure the infection rate of rice blast and according to following evaluation criteria record; Also evaluate control value (%) and phytotoxicity simultaneously.The zone (%) 00 0.5 that disease point appears in gradient of infection is lower than 21 2～and be lower than 52 5～be lower than 10 3 10～be lower than 20 4 20～be lower than 40 5 40 or higher
Calculate the control percentage with following formula:
Wherein the A representative contrasts the gradient of infection in (not being subject to processing) zone;
The B representative is subject to processing the gradient of infection in zone.
In this test, each test region is made up of three flowerpots.
Above (ⅰ) and (ⅱ) described in the test the results are shown in the table 2.
Table 2
| Subject composition | The concentration of active component (ppm) | Effect | ||
| The lethality of light red leafhopper (%) | The lethality of brown planthopper (%) | The control value (%) of rice blast | ||
| A+I.1+I.2+I.4+I.6 B+I.2+I.3+I.5+I.7 C+I.2+I.3+I.4+I.5+I.7 I.7 I.6 I.5 I.4 I.3 I.2 I.1 A B C be not subject to processing | 40+40 40+40 40+20 40+40 40+40 40+40 40+20 40+20 8+40 8+40 8+20 8+20 8+20 40 40 8 40 40 40 20 20 40 20 - | 100 100 100 100 100 100 100 100 0 0 0 0 0 100 100 0 0 0 0 0 0 0 0 0 | 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 0 0 0 0 0 0 0 0 | 95 100 100 95 100 97 100 100 100 97 100 100 100 0 0 0 87 93 91 93 97 85 93 0 |
Claims (4)
1. kill true mattress composition, it is characterized in that it contains benzamide type or its optical isomer by (1) formula (I) expression
Wherein Z represents chlorine or bromine,
R
1Represent methylidene, ethyl or isopropyl,
R
2Represent hydrogen atom or methyl and
R
3Represent hydrogen atom or methyl,
(2) N, N-dimethyl 1,2, the active compound composition that the 3-trithiane-5-base amine is formed, wherein, (1) is 1: 0.1 to 1: 5 with the weight ratio of (2).
2. the method for control fungi and harmful insect is characterized in that making the active compound composition of claim 1 to act on fungi and harmful insect and/or their habitat.
3. the active compound composition of claim 1 is prevented and treated the application of true mattress and harmful insect.
4. prepare the method for antifungal and Pesticidal combination, it is characterized in that, the active compound composition of claim 1 is mixed with filler and/or surfactant.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP273277/1990 | 1990-10-15 | ||
| JP2273277A JP2973370B2 (en) | 1990-10-15 | 1990-10-15 | Combined fungicide |
| JP273277/90 | 1990-10-15 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN91109562A Division CN1034982C (en) | 1990-10-15 | 1991-10-15 | Fungicidal and insecticidal composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1137859A CN1137859A (en) | 1996-12-18 |
| CN1062413C true CN1062413C (en) | 2001-02-28 |
Family
ID=17525604
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN91109562A Expired - Fee Related CN1034982C (en) | 1990-10-15 | 1991-10-15 | Fungicidal and insecticidal composition |
| CN96106645A Expired - Fee Related CN1060914C (en) | 1990-10-15 | 1996-05-20 | Fungicidal and insecticidal composition |
| CN96106643A Expired - Fee Related CN1062413C (en) | 1990-10-15 | 1996-05-20 | Fungicidal and insecticidal composition |
| CN96106644A Expired - Fee Related CN1062414C (en) | 1990-10-15 | 1996-05-20 | Fugicial and insecticidal composition |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN91109562A Expired - Fee Related CN1034982C (en) | 1990-10-15 | 1991-10-15 | Fungicidal and insecticidal composition |
| CN96106645A Expired - Fee Related CN1060914C (en) | 1990-10-15 | 1996-05-20 | Fungicidal and insecticidal composition |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN96106644A Expired - Fee Related CN1062414C (en) | 1990-10-15 | 1996-05-20 | Fugicial and insecticidal composition |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JP2973370B2 (en) |
| KR (1) | KR0168853B1 (en) |
| CN (4) | CN1034982C (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3810480B2 (en) * | 1996-05-30 | 2006-08-16 | バイエルクロップサイエンス株式会社 | Bactericidal insecticidal composition |
| CN1060359C (en) * | 1996-09-25 | 2001-01-10 | 河南省宛西制药厂 | Complete Chinese medical preparation for chronic fatigue syndrome and process thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6115867A (en) * | 1984-07-02 | 1986-01-23 | Nippon Tokushu Noyaku Seizo Kk | N-benzyl-cyclopropanecarboxamide derivative, its preparation and agricultural and horticultural fungicide |
| JPH021150A (en) * | 1989-02-07 | 1990-01-05 | Mitsubishi Metal Corp | Substrate for semiconductor device with excellent heat-radiating property |
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 |
-
1990
- 1990-10-15 JP JP2273277A patent/JP2973370B2/en not_active Expired - Fee Related
-
1991
- 1991-10-14 KR KR1019910018014A patent/KR0168853B1/en not_active IP Right Cessation
- 1991-10-15 CN CN91109562A patent/CN1034982C/en not_active Expired - Fee Related
-
1996
- 1996-05-20 CN CN96106645A patent/CN1060914C/en not_active Expired - Fee Related
- 1996-05-20 CN CN96106643A patent/CN1062413C/en not_active Expired - Fee Related
- 1996-05-20 CN CN96106644A patent/CN1062414C/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6115867A (en) * | 1984-07-02 | 1986-01-23 | Nippon Tokushu Noyaku Seizo Kk | N-benzyl-cyclopropanecarboxamide derivative, its preparation and agricultural and horticultural fungicide |
| JPH021150A (en) * | 1989-02-07 | 1990-01-05 | Mitsubishi Metal Corp | Substrate for semiconductor device with excellent heat-radiating property |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1137859A (en) | 1996-12-18 |
| CN1137860A (en) | 1996-12-18 |
| CN1034982C (en) | 1997-05-28 |
| KR920007535A (en) | 1992-05-27 |
| CN1147336A (en) | 1997-04-16 |
| KR0168853B1 (en) | 1999-01-15 |
| CN1060914C (en) | 2001-01-24 |
| JP2973370B2 (en) | 1999-11-08 |
| CN1060576A (en) | 1992-04-29 |
| CN1062414C (en) | 2001-02-28 |
| JPH04149105A (en) | 1992-05-22 |
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