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CN1044072C - Insecticidal and fungicidal agents - Google Patents

Insecticidal and fungicidal agents Download PDF

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Publication number
CN1044072C
CN1044072C CN90101242A CN90101242A CN1044072C CN 1044072 C CN1044072 C CN 1044072C CN 90101242 A CN90101242 A CN 90101242A CN 90101242 A CN90101242 A CN 90101242A CN 1044072 C CN1044072 C CN 1044072C
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China
Prior art keywords
chloro
picolyl
nitroethylene
methylamino
amino
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CN90101242A
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CN1046836A (en
Inventor
坪井真一
仓桥良雄
坂和填二
本田育郎
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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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
    • A01N47/44—Guanidine; Derivatives thereof

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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

A novel active compound having great insecticidal and bactericidal effects, containing a specific nitro compound comprising the fomular (I) and at least one compound selected from diisopropyl 1,3-dithiolan-2-ylidene malonate, 5-methyl-1,2,4- triazolo[3,4-b]benzothiazole, O-ethyl S,S-diphenylphosphorodithioate, 3- allyloxy-1,2-benzothiazole 1,1dioxide and 1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-i, j]quinolin-4one. an established bactericidal .

Description

Insecticidal and fungicidal agents
The present invention's step and the new active agent combinations with desinsection antifungal humidification, wherein contain known nitro compound and at least a known compound that is selected from following compound:
1,3-dithiolane-2-subunit malonic acid diisopropyl ester,
The 5-methyl isophthalic acid, 2,4-triazol (3,4-b) benzothiazole,
O-ethyl-S, S-diphenyl phosphorodithioate,
3-allyloxy-4,5-benzothiazole-1, the 1-dioxide, and
1,2,5,6-tetrahydrochysene-4 H-pyrrolo-(3,2,1-i, j) quinoline.
Some nitro compound has insecticidal activity and is disclosed (referring to Japanese patent application 299419/1988).
In addition, it is also open that following compound has antifungal, particularly blast resisting pyriform spore (Pyricularia Oryzae) activity:
1,3-dithiolane-2-subunit malonic acid diisopropyl ester,
The 5-methyl isophthalic acid, 2,4-triazol (3,4-b) benzothiazole,
O-ethyl-S, S-diphenyl phosphorodithioate,
3-allyloxy-4,5-benzothiazole-1, the 1-dioxide, and
1,2,5,6-tetrahydrochysene-4 H-pyrrolo-(3,2,1-i, j) quinoline.(referring to pesticidal Manual, the 7th edition, 1983, publish by BritishCrop.Protection Council).
Have been found that the new active agent combinations of being made up of the nitro compound and at least a compound that is selected from following one group of compound of formula (I) has extra high desinsection Fungicidally active,
Figure C9010124200051
R in the formula 1Expression hydrogen atom or C 1-4Alkyl; R 2Expression-S-R ' or
Figure C9010124200052
, R wherein 3Expression C 1-4Alkyl, R 4And R 3Each represents hydrogen atom or C 1-4Alkyl; Y represents CH or N; Described one group of compound comprises:
1,3-dithiolane-2-subunit malonic acid diisopropyl ester,
The 5-methyl isophthalic acid, 2,4-triazol (3,4-b) benzothiazole,
O-ethyl-S, S-diphenyl phosphorodithioate,
3-allyloxy-4,5-benzothiazole-1, the 1-dioxide, and
1,2,5,6-four oxygen-4 H-pyrrolo-(3,2,1-i, j) quinoline.
Surprisingly, the activity of active agent combinations of the present invention is much higher than the summation of each active substance effect, therefore has a real enhancement effect.In addition, active agent combinations of the present invention shows good desinsection fungicidal action simultaneously to insect and corps diseases.
Therefore, desinsection Fungicidal combinations of the present invention is very effective for controlling disease and insect simultaneously and save the labour in arviculture, and very significantly technical progress is provided in commercial Application.
In the nitro compound of formula (I), that can mention has a following compounds:
1-(2-chloro-5-picolyl amino)-1-methyl mercapto-2-nitroethylene;
1-(2-chloro-5-picolyl amino)-1-methylamino-2-nitroethylene;
1-(2-ammonia-5-picolyl)-3-nitro-2-methyl isothiourea;
3-(2-chloro-5-picolyl)-1-methyl-2-nitroguanidine;
1-(2-chloro-5-picolyl amino)-1-dimethylamino-2-nitroethylene;
1-(N-(2-chloro-5-picolyl)-N-methylamino)-1-methylamino-2-nitroethylene;
1-(N-(2-chloro-5-picolyl)-N-methylamino)-1-dimethylamino-2-nitroethylene;
3-(2-chloro-5-picolyl)-1,1-dimethyl-2-nitroguanidine;
1-(2-chloro-5-picolyl amino)-1-ethylamino-2-nitroethylene;
1-amino-1-(N-(2-chloro-5-picolyl)-N-methylamino)-2-nitroethylene;
3-(2-chloro-5-picolyl)-1,3-dimethyl-2-nitroguanidine;
3-(2-chloro-5-picolyl)-1,1,3-trimethyl-2-nitroguanidine;
1-amino-1-(N-(2-chloro-5-picolyl)-N-ethylamino)-2-nitroethylene;
1-(N-(2-chloro-5-picolyl)-N-ethylamino)-1-methylamino-2-nitroethylene;
1-(N-(2-chloro-5-picolyl)-N-n-pro-pyl amino)-1-methylamino-2-nitroethylene;
1-(N-(2-chloro-5-picolyl)-N-ethylamino)-1-ethylamino-2-nitroethylene; And
3-(2-chloro-5-picolyl)-3-ethyl-1-methyl-2-nitroguanidine.
These active substances are described by Japanese patent application 229419/1989.
In desinsection Fungicidal active substance combination of the present invention, the Fungicidal active substance that can mention has:
1,3-dithiolane-2-subunit malonic acid diisopropyl ester (for simplicity, hereinafter using term " Isoprothiolane ");
The 5-methyl isophthalic acid, 2,4-triazol (3,4-b) benzothiazole (for simplicity, hereinafter using term " triazole benzene thiophene ");
O-ethyl-S, S-diphenyl phosphorodithioate (for simplicity, hereinafter using term " Hinosan ");
3-allyloxy-4,5-benzothiazole-1,1-dioxide (for simplicity, hereinafter using term " thiophene bacterium alkene "); And
1,2,5,6-tetrahydrochysene-4H-pyrroles-(3,2,1-i, j) quinoline-4-ketone (for simplicity, hereinafter using term " 4-lilodidone ")
In addition, equally also can use (5-amino-2-methyl-6-(2,3,4,5,6-penta hydroxy group cyclohexyl oxygen base) tetrahydropyran-3-base) amino-alpha-imino acetate and hydrochloride (kasugarnycin) thereof, S-benzyl diisopropyl thiophosphate (iprobenfos) and 4,5,6, the 7-Rabcide replaces above-mentioned Fungicidal active substance to obtain same effect.
Above-mentioned Fungicidal active substance is known.
Desinsection Fungicidal active substance combination of the present invention demonstrates good desinsection Fungicidally active, therefore, they can advantageously be used for various application methods such as leafage dispenser, or deep layer dispenser, soil treatment, pesticide-clay mixture, the processing of seedling case etc. under water as insecticidal and fungicidal agents.
Desinsection Fungicidal combinations of the present invention demonstrates strong desinsection fungicidal action, and therefore, they can be preferably used as insecticidal and fungicidal agents.In addition; reactive compound of the present invention has very low phytotoxicity and warm blooded animal is had very low toxicity cultivated plant; so bond of the present invention can be used for controlling various fungies, insect safely and effectively; particularly hexapeopoda pest and plant disease are to guarantee the particularly protection of paddy crop of crops.These active bonds the whole process in each stage of plant growth or a certain period commute catch an illness and disease-resistant seed all has very high activity usually.
As plant pest, that can mention and specifically enumerate has: coleoptera such as rice root weevil, rice resemble, Oulema oryzae; Lepidoptera such as striped rice borer, cnaphalocrocis medinalls guenee, rice green caterpillar, rice hesperiidae; Semiptera such as rice leafhopper, brown planthopper, small brown rice planthopper, white-backed planthopper, various green stinkbug; And orthoptera such as African mqb mole cricket, African migratory locust.
As phytopathogenic fungi, specifiable have Archimycetes guiding principle, Phycomycetes, Ascomycetes, Basidiomycetes, Fungi Imperfecti etc. to reach other various plant diseases.
As the representative instance of above-mentioned various plant disease antifungal spectrums, have rice blast pyriform spore, the Helminthosporium of brown spot of rice that can mention are revolved the spore bacterium, and they are a kind of phytopathogenic fungis that cause spike of rice death.But the antifungal spectrum is not limited to top described.
Active agent combinations of the present invention can change into conventional preparation such as solution, emulsion, wetting powder, suspending agent, pulvis, foaming agent, paste, granula, aerosol, with the natural or synthetic of reactive compound dipping, in polymer microcapsule microcapsules, be used for seed stir kind of composition and with the preparation of combustion apparatus as stifling pipe, fumigation tank and stifling circle use, and micro-cold and hot spray.
These preparations can prepare with known method, for example are that liquid or liquid gas or solid diluent or carrier mix with active substance and filler, and optionally also can use surfactant is emulsifier and/or dispersant and/or foaming agent.When using water as filler, also available organic solvent is as secondary solvent.
Suitable liquid flux diluent or carrier has aromatic hydrocarbons such as dimethylbenzene, toluene or Fluhyzon substantially, chlorinated aromatic hydrocarbons or chloro fat hydro carbons such as chlorobenzene, chloroethanes or carrene, fat hydrocarbon such as cyclohexane or paraffin such as mineral oil fractions, alcohols such as butanols or 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 methyl-sulfoxide, and water.
The diluent for gases or the carrier of liquefaction refer to be at normal temperatures and pressures the liquid of gaseous state, for example, and aerosol propellant such as halogenated hydrocarbon and butane, propane, nitrogen and carbonic acid gas.
As solid carrier, can use the natural mineral matter such as kaolin, clay, talcum, chalk, quartz, Attagel, imvite or diatomite and the synthetic mineral matter of pulverizing such as high dispersive silicic acid, aluminium oxide and the silicate that pulverize.As the granula solid carrier, can use natural rock such as calcite, marble, float stone, sepiolite and the dolomite of crushing and classification, and synthetic inorganic or organic powder particles and organic particle such as sawdust, cocoa husk, corncob and tobacco stems.
As emulsifier and/or foaming agent, can use nonionic or cationic emulsifier, for example, polyoxyethylene fatty acid ester, polyoxyethylene aliphatic alcohol ether are as alkaryl polyglycol ether, alkyl sulfonate, alkyl sulfate, aromatic sulfonic acid salt and albumin hydrolysate.Dispersant comprises for example wooden sulfite waste liquor and methylcellulose.
In preparation, can use the natural and synthetic polymer of adhesive such as carboxymethyl cellulose and powdery, granular or emulsus, as gum Arabic, polyvinyl alcohol and polyvinyl acetate.
Can use colouring agent, for example inorganic pigment such as iron oxide, titanium oxide and Prussia orchid, and organic dyestuff such as rubican dyestuff, azo dyes or metal phthalocyanine dyestuff.Also can use micronutrient such as molysite, manganese bronze salt, mantoquita, cobalt salt, molybdenum salt and zinc salt.
Usually, contain the active substance of 0.1～95% (weight) in the preparation, best 0.5～90% (weight).
Active agent combinations of the present invention can its commercial preparation form or type of service exist, type of service is mixed and prepares with other reactive compound such as insecticide, bactericidal agent, miticide, fungicide, growth regulator or weed killer herbicide by the commercial preparation.Insecticide comprises as phosphate, mephenesin Carbamate, carboxylate, chlorinated hydrocarbon, phenylurea, by the material of microorganisms.
In addition, active agent combinations of the present invention can its commercial preparation form and type of service exist, type of service is mixed and prepares with synergist by the commercial preparation.Synergist be can enhanced activity compound effect but itself might not activated compound.
Activity substance content from the type of service of commercial preparation preparation can change in wide range.The concentration of the active substance in the type of service can be 0.00001～100% (weight), is preferably 0.001～5% (weight).
Bond uses by the usual manner that is suitable for type of service.
Following example illustrates in greater detail the present invention.Yet, should be appreciated that the present invention never only limits to these examples.Biologic test example: substances:
Material shown in the general formula (I):
Compound 1.1-(2-chloro-5-picolyl amino)-1-methylamino-2-nitroethylene,
Compound 2.1-(2-chloro-5-picolyl amino)-1-dimethylamino-2-nitroethylene,
Compound 3.1-(N-(2-chloro-5-picolyl)-N-methylamino)-1-dimethylamino-2-nitroethylene,
Compound 4.3-(2-chloro-5-picolyl)-1,1-dimethyl-2-nitroguanidine,
Compound 5.3-(2-chloro-5-picolyl)-1,3-dimethyl-2-nitroguanidine.
Known Fungicidal active substance:
(A) Hinosan, (B) Isoprothiolane,
(C) triazole benzene thiophene, (D) 4-lylodidone,
(E) thiophene bacterium alkene, (F) Rabcide.
Example 1
Water surface is used potency test: the preparation of substances:
Every kind of active substance: 5～25 parts (weight)
Carrier: 70～90 parts of (weight) diatomite and mixing in kaolinic 1: 5
Compound
Emulsifier: 5 parts of (weight) polyoxyethylene alkyl phenyl ethers
Active substance, carrier and emulsifier pulverizing and the mixing of above-mentioned specified amount are respectively formed a kind of wetting powder.Described wetting powder dilute with water and mixing with scheduled volume.Test method:
(kind: Asahi) being planted in diameter with the plantation amount of three strains is in 12 centimetres the ceramic whiteware basin, and it is grown under heavy water state with the paddy crop.Early stage at minute dish, every kind of active substance of previously prepared predetermined concentration is poured on the surface of water with the amount of appointment, note directly not being poured on the acrial part of paddy plant.After three days, cover the ceramic whiteware basin, brown planthopper (Nilaparvata lugens) four-age larva is put into basin by the quantity of 10 in every basin with cage.Put into two days later,, and calculate lethality the dead insects counting.
Then, use conventional method, the spore suspension of rice blast pyriform spore is sprayed onto on the plant, and be that 23～25 ℃, relative moisture are to place 24 hours in 100% the incubator in temperature, transfer to temperature then and be in 20～28 ℃ the glass greenhouse the ceramic whiteware basin.Inoculate after seven days, connect following standard evaluation and calculate the degree that each basin is subjected to disease, and calculate control rate (%), check phytotoxicity simultaneously.
The percentage in degree of disease infringement zone
0 0
0.5 below 2 or 2
1 3-5
2 6-10
3 11-20
4 21-40
More than 51 or 41
×100
In this test, a pilot region comprises three basin crops.
Result of the test is summarised in the table 1.
Table 1
Subject composition The concentration of active substance (kg/ha) The result
The lethality of brown planthopper (%) Rice blast control rate (%)
Compound 1+ (D) compound 1+ (E) compound 2+ (D) compound 2+ (E) compound 3+ (D) compound 3+ (E) compound 4+ (D) compound 4+ (E) compound 5+ (D) compound 5+ (E) compound 1 compound 2 compounds 3 compounds 4 compounds 5 (D) (E) are untreated 0.25+2 0.25+3 0.25+2 0.25+3 0.25+2 0.25+3 0.25+2 0.25+3 0.25+2 0.25+3 0.25 0.25 0.25 0.25 0.25 2 3 100 100 100 100 100 100 100 100 100 100 95 75 70 90 60 0 0 0 100 97 100 93 100 97 100 100 100 100 0 0 0 0 0 100 93 0
Annotate: in the example 1 used all mixtures and unification compound all not discovery can cause phytotoxicity.
Example 2
Be applied to the potency test in the seedling growing box:
The preparation of substances:
Water (25 parts) is added in the mixture of being made up of 5 (or 4) part active substance, 30 parts of bentonites (imvite), 63 (or 64) part talcum and 2 parts of ligninsulfonates, and they are fully kneaded.With the squash type granulator this mixture being made granularity is 10～40 purpose particles, then at 40～50 ℃ of dry down particles that form.
Make rice seedlings growth in seedling growing box (30 cm x are come * 2 centimetres for 60 lis), and emerging back 21 days, active material particle (0.25%) and the 50 gram triazole benzene thiophene particles (4%) of using 50 gram general formulas (I) equably for every case.After the dispenser, from every case, take out the rice seedlings of three strain band soil, be transplanted in the flowerpot (1/10000 acre) in the greenhouse.Transplanted back three days, and gave plastics cage on each basin cover, then 10 brown planthoppers (Nilaparavatalugens) four-age larva is put in the cage.Two days later, to the insect counts of death, and calculate lethality.
Transplanted the back 20 days, when rice seedlings take root and well-grown after, be sprayed onto on the plant with the spore suspension of conventional method, and be that 23～25 ℃, relative moisture are to keep 24 hours in 100% the incubator in temperature, transfer to then in 20～28 ℃ the glass greenhouse flowerpot with rice blast pyriform spore.Inoculate back seven days, calculate the degree that each basin is subjected to disease by following standard evaluation and estimation, and calculate control rate (%), check phytotoxicity simultaneously.
The percentage in the degree infringement zone of disease
0 0
0.5 below 2 or 2
1 3-5
2 6-10
3 11-20
4 1-40
More than 5 41 or 41
×100
In this test, a pilot region is made up of three basin crops.
Result of the test is summarised in the table 2.
Table 2
Subject composition The concentration of active substance (gram/case) The result
The lethality of brown planthopper (%) Rice blast control rate (%)
Compound 1+ (c) compound 2+ (c) compound 3+ (c) compound 4+ (c) compound 5+ (c) compound 1 compound 2 compounds 3 compounds 4 compounds 5 (c) are untreated 0.125+2 0.125+2 0.125+2 0.125+2 0.125+2 0.125 0.125 0.125 0.125 0.125 2 100 100 100 100 100 90 75 70 95 60 0 0 97 97 93 100 100 0 0 0 0 0 93 0
Annotate: in the example 2 used all mixtures and unification compound all not discovery can cause phytotoxicity.
Example 3 (1) brown planthoppers (Nilaparvata lugens) test: the preparation of substances:
Every kind of active substance: 30～40 parts (weight)
Carrier: 55～65 parts of (weight) diatomite and kaolinic 1: 5
Mixture
Emulsifier: 5 parts of (weight) polyoxyethylene alkyl phenyl ethers
Active substance, carrier and the emulsifier of above-mentioned specified amount are pulverized and mixing, and each forms a kind of wetting powder.Described wetting powder dilute with water and mixing with scheduled volume.Test method:
Three high 15 centimetres strain rice seedlings are planted respectively in the about 13 lis of flowerpots that come of diameter.Planted back ten days, and the rate of application of the water diluent of the active substance of previously prepared predetermined concentration with every basin 20ml was sprayed onto on the plant with spray gun.After spray liquid is air-dry, gives cage on each pot cover, and in every basin, put into ten brown planthopper four-age larvas, after three days,, and calculate lethality the insect counts of death.(2) the leafage dispenser is to the potency test test method of rice blast:
Make paddy rice (kind: Asahi) in diameter is 12 centimetres bique basin, grow, and the active substance dilution with previously prepared predetermined concentration is sprayed onto on the plant with per three basin 50ml rate of application in 3～4 leaf stages.Second day, be inoculated on the crop by the spore suspension of twice spraying with the rice blast pyriform spore of artificial culture.Then each basin is remained on temperature and be 25 ℃, relative moisture and be in 100% the culturing room to cause infection.Inoculate back seven days, with following standard evaluation and calculate the degree that each basin is subjected to disease, and calculate control rate (%), check phytotoxicity simultaneously crop.The percentage in degree of disease infringement zone
0 0
0.5 below 2 or 2
1 3-5
2 6-10
3 11-20
4 21-40
More than 5 41 or 41 * 100
In this test, a pilot region is made up of three basin crops.
The result of the test of test (1) and (2) is summarised in the table 3.
Table 3
Subject composition The concentration of active substance (ppm) The result
Brown planthopper Rice blast
Lethality (%) Control rate (%)
Compound 1+, (A) compound 1+, (A)+, (F) compound 1+, (B) compound z+, (A) compound 2+, (B) compound 3+, (A) compound 3+, (B) compound 4+, (A) compound 4+, (A)+, (F) compound 4+, (B) compound 5+, (A) compound 5+, (A)+, (F) compound 5+, (B) compound 1 compound 2 compounds 3 compounds 4 compounds 5, (A), (B), (F) be untreated 8+40 8+20+20 8+50 8+40 8+50 8+40 8+50 8+40 8+20+20 8+50 8+40 8+20+20 8+50 8 8 8 8 8 40 50 40 100 100 100 100 100 100 100 100 100 100 100 100 100 45 20 15 40 20 0 0 0 0 95 100 90 93 90 98 90 100 100 90 95 100 90 0 0 0 0 0 60 67 90 0
Annotate: in the example 3 used all mixtures and unification compound all not appearance can cause phytotoxicity.

Claims (5)

1. desinsection Fungicidal composition, it comprises
(A) nitro compound of (1) insecticidal effective dose, it is selected from
1-(2-chloro-5-picolyl amino)-1-methyl mercapto-2-nitroethylene;
1-(2-chloro-5-picolyl amino)-1-methylamino-2-nitroethylene;
1-(2-chloro-5-picolyl)-3-nitro-2-methyl isothiourea;
3-(2-chloro-5-picolyl)-1-methyl-2-nitroguanidine;
1-(2-chloro-5-picolyl amino)-1-dimethylamino-2-nitroethylene;
1-[N-(2-chloro-5-is than pyridine methyl)-N-methylamino]-1-methylamino-2-nitroethylene;
1-[N-(2-chloro-5-picolyl)-N-methylamino]-1-dimethylamino-2-nitroethylene;
3-(2-chloro-5-picolyl)-1,1-dimethyl-2-nitroguanidine;
1-(2-chloro-5-picolyl amino)-1-ethylamino-2-nitroethylene;
1-amino-1-[N-(2-chloro-5-picolyl)-N-methylamino]-the 2-nitroethylene;
3-(2-chloro-5-picolyl)-1,3-dimethyl-2-nitroguanidine;
3-(2-chloro-5-picolyl)-1,1,3-trimethyl-2-nitroguanidine;
1-amino-1-[N-(2-chloro-5-picolyl)-N-ethylamino]-the 2-nitroethylene;
1-[N-(2-chloro-5-picolyl)-N-ethylamino]-1-methylamino-2-nitroethylene;
1-[N-(2-chloro-5-picolyl)-N-n-pro-pyl amino]-1-methylamino-2-nitroethylene;
1-[N-(2-chloro-5-picolyl)-N-ethylamino]-1-ethylamino-2-nitroethylene; And
3-(2-chloro-5-picolyl)-3-ethyl-1-methyl-2-nitroguanidine; (B) at least a fungicide of antifungal effective dose, it is selected from:
(2) 1,3-dithiolane-2-subunit malonic acid diisopropyl ester,
(3) 5-methyl isophthalic acid, 2,4-triazol [3,4-b] benzothiazole,
(4) O-ethyl-S, S-diphenyl phosphorodithioate,
(5) 3-allyloxy-4,5-benzothiazole-1, the 1-dioxide, and
(6) 1,2,5,6-tetrahydrochysene-4H-pyrrolo-[3,2,1-i, j] quinoline.
2. according to the desinsection Fungicidal composition of claim 1, wherein nitro compound is selected from: 1-(2-chloro-5-picolyl amino)-1-methylamino-2-nitroethylene; 1-(2-chloro-5-picolyl amino)-1-dimethylamino-2-nitroethylene; 1-[N-(2-chloro-5-picolyl)-N-methylamino]-1-dimethylamino-2-nitroethylene;
3-(2-chloro-5-picolyl)-1,1-dimethyl-2-nitroguanidine;
3-(2-chloro-5-picolyl)-1,3-dimethyl-2-nitroguanidine.
3. according to the desinsection Fungicidal composition of claim 1, it is characterized in that (A) in the active agent combinations and (B) weight ratio are 1: 5～1: 16.
4. the method for control insect and fungi is characterized in that, makes the active agent combinations according to claim 1 or 2 act on insect and fungi and/or its habitat.
5. the method for preparing the desinsection Fungicidal composition is characterized in that the active agent combinations of claim 1 or 2 is mixed with filler and/or surfactant.
CN90101242A 1989-03-10 1990-03-10 Insecticidal and fungicidal agents Expired - Fee Related CN1044072C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP56124/89 1989-03-10
JP5612489 1989-03-10

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CN1046836A CN1046836A (en) 1990-11-14
CN1044072C true CN1044072C (en) 1999-07-14

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CN90101242A Expired - Fee Related CN1044072C (en) 1989-03-10 1990-03-10 Insecticidal and fungicidal agents

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CN (1) CN1044072C (en)

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CN1046836A (en) 1990-11-14
KR900013852A (en) 1990-10-22
KR0160766B1 (en) 1998-11-16

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