EP0000934B1 - Indan-5-yl-N-alkyl-carbaminsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Pflanzenschutzmittel - Google Patents

Indan-5-yl-N-alkyl-carbaminsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Pflanzenschutzmittel Download PDF

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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
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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
Application number
EP78100703A
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German (de)
English (en)
French (fr)
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EP0000934A1 (de
Inventor
Detlef Dr. Grotkopp
Karlfried Dr. Wedemeyer
Wilhelm Dr. Brandes
Hans Dr. Scheinpflug
Peter Dr. Roessler
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Bayer AG
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Bayer AG
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Filing date
Publication date
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Publication of EP0000934A1 publication Critical patent/EP0000934A1/de
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Publication of EP0000934B1 publication Critical patent/EP0000934B1/de
Expired legal-status Critical Current

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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.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
EP78100703A 1977-08-31 1978-08-18 Indan-5-yl-N-alkyl-carbaminsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Pflanzenschutzmittel Expired EP0000934B1 (de)

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 (de) 1979-03-07
EP0000934B1 true EP0000934B1 (de) 1980-07-23

Family

ID=6017749

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EP78100703A Expired EP0000934B1 (de) 1977-08-31 1978-08-18 Indan-5-yl-N-alkyl-carbaminsäureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Pflanzenschutzmittel

Country Status (16)

Country Link
US (1) US4228181A (pt)
EP (1) EP0000934B1 (pt)
JP (1) JPS5446760A (pt)
AT (1) AT359334B (pt)
AU (1) AU517929B2 (pt)
BR (1) BR7805641A (pt)
CA (1) CA1102822A (pt)
CS (1) CS199220B2 (pt)
DD (1) DD138144A5 (pt)
DE (2) DE2739193A1 (pt)
DK (1) DK384478A (pt)
HU (1) HU176060B (pt)
IL (1) IL55444A (pt)
IT (1) IT7827109A0 (pt)
PL (1) PL110894B1 (pt)
ZA (1) ZA784946B (pt)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE2422T1 (de) * 1978-11-06 1983-03-15 Ciba-Geigy Ag 1h-inden-1-on-derivate, verfahren zu ihrer herstellung sowie ihre verwendung in mikrobiziden mitteln und zur bekaempfung von mikroorganismen.
JPS61207304A (ja) * 1985-03-11 1986-09-13 Toyo Soda Mfg Co Ltd 農園芸用殺菌剤
ES2203988T3 (es) * 1997-11-06 2004-04-16 Smithkline Beecham Plc Compuestos de pirimidinona y composiciones farmaceuticas que los contienen.

Family Cites Families (3)

* Cited by examiner, † Cited by third party
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

Also Published As

Publication number Publication date
DE2860075D1 (en) 1980-11-13
AU517929B2 (en) 1981-09-03
CA1102822A (en) 1981-06-09
JPS5446760A (en) 1979-04-12
BR7805641A (pt) 1979-04-10
DE2739193A1 (de) 1979-03-08
US4228181A (en) 1980-10-14
CS199220B2 (en) 1980-07-31
PL209266A1 (pl) 1979-06-04
ZA784946B (en) 1979-08-29
DK384478A (da) 1979-03-01
PL110894B1 (en) 1980-08-30
IT7827109A0 (it) 1978-08-29
EP0000934A1 (de) 1979-03-07
AT359334B (de) 1980-11-10
ATA631978A (de) 1980-03-15
DD138144A5 (de) 1979-10-17
IL55444A (en) 1982-02-28
IL55444A0 (en) 1978-10-31
HU176060B (en) 1980-12-28
AU3934678A (en) 1980-03-06

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