EP0000934B1 - Esters 5-indanyliques de l'acide N-alkylcarbamique, leurs procédés de préparation ainsi que leur application comme pesticides - Google Patents
Esters 5-indanyliques de l'acide N-alkylcarbamique, leurs procédés de préparation ainsi que leur application comme pesticides Download PDFInfo
- Publication number
- EP0000934B1 EP0000934B1 EP78100703A EP78100703A EP0000934B1 EP 0000934 B1 EP0000934 B1 EP 0000934B1 EP 78100703 A EP78100703 A EP 78100703A EP 78100703 A EP78100703 A EP 78100703A EP 0000934 B1 EP0000934 B1 EP 0000934B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- spp
- carbamic acid
- hydroxy
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
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- 241000254086 Tribolium <beetle> Species 0.000 description 1
- 241001259047 Trichodectes Species 0.000 description 1
- 241000255993 Trichoplusia ni Species 0.000 description 1
- 241000267823 Trogoderma Species 0.000 description 1
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 235000013447 Xanthosoma atrovirens Nutrition 0.000 description 1
- 240000001781 Xanthosoma sagittifolium Species 0.000 description 1
- 241000353223 Xenopsylla cheopis Species 0.000 description 1
- 241001466337 Yponomeuta Species 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000012173 estrus Effects 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000004459 forage Substances 0.000 description 1
- 231100000162 fungitoxic Toxicity 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- YYSQBMZXENQLHN-UHFFFAOYSA-N methyl-(3,3,6,7-tetramethyl-1,2-dihydroinden-5-yl)carbamic acid Chemical compound CC1=C(C)C(N(C(O)=O)C)=CC2=C1CCC2(C)C YYSQBMZXENQLHN-UHFFFAOYSA-N 0.000 description 1
- UFEJKYYYVXYMMS-UHFFFAOYSA-N methylcarbamic acid Chemical compound CNC(O)=O UFEJKYYYVXYMMS-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 230000004660 morphological change Effects 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
Classifications
-
- 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
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/22—O-Aryl or S-Aryl esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
- C07C271/42—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/44—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
- C07C37/0555—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group being esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Definitions
- the present invention relates to new indan-5-yl-N-alkyl-carbamic acid esters, several processes for their preparation and their use as crop protection agents.
- N-methyl-carbamic acid ester of 5-hydroxyindane is insecticidal (cf. US Pat. Nos. 2,870,057 and 3,084,096). Furthermore, it has already become known that the N-trichloromethylthiotetrahydrophthalimide has strong fungicidal properties (cf. Science, Vol. 115, p. 84 (1952)). However, this active ingredient, which is important in practice, has only a protective effect.
- the compounds have strong fungicidal and arthropod-inhibiting properties and can therefore be used as crop protection agents.
- the indan-5-yl-N-alkyl-carbamates according to the invention have a surprisingly high fungicidal activity and are superior to the previously known N-trichloromethylthio-tetrahydropthalimide even at low application rates. Furthermore, they can be used not only as protective, but also as curative agents.
- the substances according to the invention thus represent an enrichment of the technology. For use as crop protection agents it is of interest that the active substances are able to inhibit the development of arthropods.
- reaction sequence according to process a) can be represented by the following formula:
- R2 preferably represents hydrogen and lower alkyl having 1 to 4 carbon atoms and R 3 and R 4 chlorine and lower alkyl having 1 to 4 carbon atoms.
- the compounds can be analogous to previously known processes (cf.
- the starting materials, phosgene and alkyl isocyanate required for process a), or phosgene and alkylamine for process variants b) and c), which are also required for the preparation of the compounds of formula (I) according to the invention, are generally known.
- Those alkyl isocyanates or alkyl amines which contain an alkyl radical having 1 to 4 carbon atoms are preferably used. These include: methyl isocyanate, ethyl isocyanate, butyl isocyanate, and the following amines: methylamine, ethylamine, isopropylamine, butylamine, isobutylamine.
- the radical R ' preferably denotes alkyl having 1 to 4 carbon atoms.
- the reaction according to process a) can be carried out in inert solvents.
- inert solvents e.g. Hydrocarbons, such as gasoline and benzene, chlorinated hydrocarbons, such as chlorobenzene, but also ethers, such as dioxane, or mixtures of these solvents.
- the reaction is carried out by adding a tertiary amine, e.g. Triethylamine or diazabicyclooctane, catalyzed.
- the reaction temperatures can be varied within a wide range. In general, however, you will work between 0 and 150 ° C, preferably between 20 and 110 ° C.
- the 5-hydroxy-indane of the formula (II) is advantageously in the presence of inert solvents, such as aromatic, optionally chlorinated, hydrocarbons, e.g. Benzene, toluene, xylene or chlorobenzene, with an excess of phosgene in the chlorocarbonic acid ester.
- inert solvents such as aromatic, optionally chlorinated, hydrocarbons, e.g. Benzene, toluene, xylene or chlorobenzene, with an excess of phosgene in the chlorocarbonic acid ester.
- the hydrochloric acid formed is bound by dropwise addition of a base, advantageously sodium hydroxide, and the pH of the reaction solution is thus kept below 7.
- a base advantageously sodium hydroxide
- the chlorocarbonic acid ester is reacted with the equivalent amount of alkylamine either after isolation or directly in the reaction solution obtained. It is also convenient to work in the presence of inert solvents such as aromatic and aliphatic, optionally chlorinated hydrocarbons, such as benzene, toluene, chlorobenzene, gasoline, carbon tetrachloride, or ethers, such as dioxane.
- inert solvents such as aromatic and aliphatic
- optionally chlorinated hydrocarbons such as benzene, toluene, chlorobenzene, gasoline, carbon tetrachloride, or ethers, such as dioxane.
- the reaction temperatures can in turn be varied within a certain range; one generally works between -20 and + 20 ° C, preferably between -10 and + 10 ° C.
- the 5-hydroxy in the formula (11) with the equivalent amount of phosgene to the bis (indanyl) carbonic acid ester is expediently carried out in inert solvents, such as aromatic hydrocarbons, for example benzene and toluene, the hydrochloric acid formed being bound by adding a base, preferably alkali metal hydroxide.
- the pH of the reaction solution should be around 8.
- the reaction temperature can vary within a substantial range, it is generally between 0 and 100 ° C, preferably between +20 and 60 ° C.
- the carbonate formed in the first stage is then broken down with alkylamine. It is convenient to work without solvents. However, the reaction can also be carried out in solvents.
- the reaction temperatures are between -30 and + 40 ° C, preferably between -10 and + 20 ° C.
- the active substances according to the invention have a strong fungitoxic effect. They do not damage crops in the concentrations necessary to control fungi. For these reasons, they are suitable for use as crop protection agents for combating fungi. Fungitoxic agents in crop protection are used to control Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes.
- the active compounds according to the invention have a broad spectrum of activity and can be used against parasitic fungi which attack above-ground parts of plants or attack the plants from the ground, and against seed-borne pathogens. They are particularly effective against parasitic fungi on above-ground parts of plants.
- the active compounds according to the invention can be used with particularly good success as crop protection agents for controlling Venturia species, for example for controlling apple scab (Fusicladium dendriticum). It should be noted that the active ingredients are not only protective, but also curative.
- Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci.
- Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Rhoralosobusumumisis, pad.
- Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Rhoralosobusumumisis,
- Nephotettix cincticeps Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.
- Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
- Acarina e.g. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp.,. Chori ., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.
- Acarina e.g. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp.
- the active compounds according to the invention can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, pastes and granules. These are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents.
- aromatics such as xylene, toluene, benzene or alkylnaphthalenes
- chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylene or methylene chloride
- aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
- Petroleum fractions oil fractions, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methytisobutyiketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water; liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and pressure, e.g.
- Aerosol propellants such as dichlorodifluoromethane or trichlorofluoromethane; as solid carriers: natural rock flour, such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powder, such as highly disperse silica, aluminum oxide and silicates; as an emulsifier; nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g.
- the active compounds according to the invention can be present in the formulations in a mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, herbicides, bird repellants, growth agents, plant nutrients and agents which improve soil structure.
- active compounds such as fungicides, insecticides, acaricides, nematicides, herbicides, bird repellants, growth agents, plant nutrients and agents which improve soil structure.
- the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
- the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, emulsions, suspensions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, dusting, scattering, dry pickling, wet pickling, wet pickling, slurry pickling or incrusting.
- the active compound concentrations in the use forms can be varied within a substantial range. They are generally between 0.1 and 0.00001 percent by weight, preferably between 0.05 and 0.0001%.
- active ingredient 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, are generally required.
- the compounds according to the invention inhibit the development of arthropods.
- the experiments described below demonstrate the arthropod development-inhibiting activity of the compounds according to the invention.
- the morphological changes such as half pupated animals, incompletely hatched larvae or caterpillars, defective wings, pupal cuticles in adults, etc., are assessed as malformations.
- the compounds according to the invention also have an insecticidal activity.
- Emulsifier 0.3 part by weight of alkyl aryl polyglycol ether
- the amount of active ingredient required for the desired active ingredient concentration in the spray liquid is mixed with the stated amount of solvent and the concentrate is diluted with the stated amount of water which contains the additives mentioned.
- the spray liquid is used to spray young apple seedlings, which are in the 4- to 6-leaf stage, until they drip wet.
- the plants remain in the greenhouse for 24 hours at 20 ° C. and a relative humidity of 70%. They are then inoculated with an aqueous conidia suspension of the apple scab pathogen (Fusicladium dendriticum) and incubated for 18 hours in a humid chamber at 18 to 20 ° C. and 10096 relative atmospheric humidity.
- the infestation of the seedlings is determined 15 days after the inoculation.
- the rating values received are converted into percent infestation. 0% means no infection, 100% means that the plants are completely infected.
- Emulsifier 0.3 part by weight of alkyl aryl polyglycol ether
- the amount of active ingredient required for the desired active ingredient concentration in the spray liquid is mixed with the stated amount of solvent and the concentrate is diluted with the stated amount of water which contains the additives mentioned.
- Young apple seedlings which are in the 4 to 6 leaf stage, are inoculated with an aqueous conidia suspension of the apple scab pathogen (Fusicladium dentriticum) and incubated for 18 hours in a humid chamber at 18 to 20 ° C. and 100% relative atmospheric humidity. The plants then come into the greenhouse. They dry up.
- apple scab pathogen Feusicladium dentriticum
- the plants are sprayed with the spray liquid, which is produced in the manner described above, to the point of dripping wet. Then the plants come back into the greenhouse.
- the infestation of the apple seedlings is determined 15 days after the inoculation.
- the rating values received are converted into percent infestation. 0% means no infection, 100% means that the plants are completely infected.
- the compound according to the invention corresponding to preparation example 1 shows a good effect which is superior to the comparative preparation given in the prior art.
- Test animals Plutella maculipennis (caterpillars in the 4th stage of development) 20 pieces
- active compound 2 parts by weight of active compound are mixed with the stated amount of solvent, emulsifier and enough water to form a 1% mixture which is diluted with water to the desired concentration.
- test animals are fed leaves of the fodder plants, which are provided with a uniform spray coating of the active compound mixture of the selected concentration, so that the stated amounts of active compound in ppm (parts per million) are obtained on the leaves until the development of the Imago.
- the compound according to the invention according to Preparation Example 1 shows good effectiveness. It outperforms the known comparative 2,2-dimethyl-6-methoxy-benzopyran.
- Lining synthetic lining (carrot powder with yeast powder)
- Emulsifier 5 parts by weight of alkylaryl polyglycol ether
- active compound 4 parts by weight of active compound are mixed with the stated amount of solvent, emulsifier and enough water to produce a 1% mixture which is diluted with water to the desired concentration.
- the eggs of the test animals are placed on a bowl of artificial feed into which the selected concentration of the active ingredient mixture is incorporated, so that the specified amount of active ingredient in ppm (parts per million) is reached.
- the development up to the hatching of the flies is observed.
- the active compounds according to the preparation examples according to the invention show good activity.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (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)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (4)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2739193 | 1977-08-31 | ||
DE19772739193 DE2739193A1 (de) | 1977-08-31 | 1977-08-31 | Indan-5-yl-n-alkyl-carbaminsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als pflanzenschutzmittel |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0000934A1 EP0000934A1 (fr) | 1979-03-07 |
EP0000934B1 true EP0000934B1 (fr) | 1980-07-23 |
Family
ID=6017749
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP78100703A Expired EP0000934B1 (fr) | 1977-08-31 | 1978-08-18 | Esters 5-indanyliques de l'acide N-alkylcarbamique, leurs procédés de préparation ainsi que leur application comme pesticides |
Country Status (16)
Country | Link |
---|---|
US (1) | US4228181A (fr) |
EP (1) | EP0000934B1 (fr) |
JP (1) | JPS5446760A (fr) |
AT (1) | AT359334B (fr) |
AU (1) | AU517929B2 (fr) |
BR (1) | BR7805641A (fr) |
CA (1) | CA1102822A (fr) |
CS (1) | CS199220B2 (fr) |
DD (1) | DD138144A5 (fr) |
DE (2) | DE2739193A1 (fr) |
DK (1) | DK384478A (fr) |
HU (1) | HU176060B (fr) |
IL (1) | IL55444A (fr) |
IT (1) | IT7827109A0 (fr) |
PL (1) | PL110894B1 (fr) |
ZA (1) | ZA784946B (fr) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0011601B1 (fr) * | 1978-11-06 | 1983-02-09 | Ciba-Geigy Ag | Dérivés de 1H-indène-1-one, procédé pour leur préparation et leur utilisation dans des agents microbicides et pour la lutte contre les microorganismes |
JPS61207304A (ja) * | 1985-03-11 | 1986-09-13 | Toyo Soda Mfg Co Ltd | 農園芸用殺菌剤 |
CA2309177A1 (fr) * | 1997-11-06 | 1999-05-20 | Stephen Allan Smith | Composes de pyrimidinone et compositions pharmaceutiques les renfermant |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3084096A (en) * | 1955-08-29 | 1963-04-02 | Union Carbide Corp | Indanyl n-methyl carbamate |
US2870057A (en) * | 1957-11-26 | 1959-01-20 | Gulf Research Development Co | 4- or 5-indanyl n-methyl carbamate |
DE2603835A1 (de) * | 1976-02-02 | 1977-08-04 | Bayer Ag | Indan-5-yl-n-methylcarbaminsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide |
-
1977
- 1977-08-31 DE DE19772739193 patent/DE2739193A1/de not_active Withdrawn
-
1978
- 1978-08-08 US US05/932,055 patent/US4228181A/en not_active Expired - Lifetime
- 1978-08-18 DE DE7878100703T patent/DE2860075D1/de not_active Expired
- 1978-08-18 EP EP78100703A patent/EP0000934B1/fr not_active Expired
- 1978-08-29 IL IL55444A patent/IL55444A/xx unknown
- 1978-08-29 JP JP10449978A patent/JPS5446760A/ja active Pending
- 1978-08-29 DD DD78207528A patent/DD138144A5/xx unknown
- 1978-08-29 IT IT7827109A patent/IT7827109A0/it unknown
- 1978-08-29 PL PL1978209266A patent/PL110894B1/pl unknown
- 1978-08-29 AU AU39346/78A patent/AU517929B2/en not_active Expired
- 1978-08-30 BR BR7805641A patent/BR7805641A/pt unknown
- 1978-08-30 CA CA310,331A patent/CA1102822A/fr not_active Expired
- 1978-08-30 DK DK384478A patent/DK384478A/da unknown
- 1978-08-30 CS CS785628A patent/CS199220B2/cs unknown
- 1978-08-30 ZA ZA00784946A patent/ZA784946B/xx unknown
- 1978-08-31 HU HU78BA3699A patent/HU176060B/hu unknown
- 1978-08-31 AT AT631978A patent/AT359334B/de not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
JPS5446760A (en) | 1979-04-12 |
ZA784946B (en) | 1979-08-29 |
EP0000934A1 (fr) | 1979-03-07 |
IL55444A0 (en) | 1978-10-31 |
PL110894B1 (en) | 1980-08-30 |
US4228181A (en) | 1980-10-14 |
DE2739193A1 (de) | 1979-03-08 |
HU176060B (en) | 1980-12-28 |
IL55444A (en) | 1982-02-28 |
DK384478A (da) | 1979-03-01 |
PL209266A1 (pl) | 1979-06-04 |
CA1102822A (fr) | 1981-06-09 |
IT7827109A0 (it) | 1978-08-29 |
AT359334B (de) | 1980-11-10 |
CS199220B2 (en) | 1980-07-31 |
AU3934678A (en) | 1980-03-06 |
ATA631978A (de) | 1980-03-15 |
DD138144A5 (de) | 1979-10-17 |
BR7805641A (pt) | 1979-04-10 |
DE2860075D1 (en) | 1980-11-13 |
AU517929B2 (en) | 1981-09-03 |
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