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Publication number
NO119992B
NO119992B NO63668A NO63668A NO119992B NO 119992 B NO119992 B NO 119992B NO 63668 A NO63668 A NO 63668A NO 63668 A NO63668 A NO 63668A NO 119992 B NO119992 B NO 119992B
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Norway
Prior art keywords
benzodioxol
methylcarbamate
dimethyl
substituted
compounds
Prior art date
Application number
NO63668A
Other languages
Norwegian (no)
Inventor
P Gates
J Gillon
Original Assignee
Fisons Pest Control Ltd
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Publication date
Application filed by Fisons Pest Control Ltd filed Critical Fisons Pest Control Ltd
Publication of NO119992B publication Critical patent/NO119992B/no

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/64—Oxygen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

En spesielt foretrukken forbindelse er 2,2-dimetyl-l,3-benzodioksol-4-yl-N-metylkarbamat på grunn av dens hoye aktivitet. A particularly preferred compound is 2,2-dimethyl-1,3-benzodioxol-4-yl-N-methylcarbamate because of its high activity.

De ovenfor definerte benzodioksoler kan fremstilles ved at The benzodioxoles defined above can be prepared by

et 4-hydroksyl-l,3-benzodioksol omsettes med et isocyanat med formel- a 4-hydroxyl-1,3-benzodioxole is reacted with an isocyanate of the formula

en R^NCO eller et substituert karbamylklorid med formelen HR^NCOCl. a R^NCO or a substituted carbamyl chloride of the formula HR^NCOCl.

De substituerte benzodioksoler kan også fremstilles ved å omsette et 1,3-benzodioksolyl-4-klorformiat med et amin med formelen The substituted benzodioxoles can also be prepared by reacting a 1,3-benzodioxolyl-4-chloroformate with an amine of the formula

'r<3>nH2» Gruppen R^ har her samme betydning som angitt ovenfor. 'r<3>nH2» The group R^ here has the same meaning as stated above.

De substituerte benzodioksoler er funnet å være The substituted benzodioxoles are found to be

nyttige som insekticider, særlig mot husfluer, larver og bladlus. Dis- useful as insecticides, especially against houseflies, caterpillars and aphids. Haze-

se forbindelser virker som direkte insekticider og har også systemisk aktivitet. De substituerte benzodioksolene er også verdifulle for utryddelse av skadelige insekter, f.eks. klegg på husdyr. se compounds act as direct insecticides and also have systemic activity. The substituted benzodioxoles are also valuable for the eradication of harmful insects, e.g. lay on livestock.

De substituerte benzodioksolene er generelt uoppløselige i The substituted benzodioxoles are generally insoluble in

vann og kan prepareres ved hjelp av hvilken som helst av de metoder som brukes for uopploselige forbindelser. De substituerte benzodioksoler kan om onsket opploses i et opplosningsmiddel som ikke er blandbart med vann, f.eks. et hoytkokende hydrokarbon, hensiktsmessig inneholdende opploste emulgeringsmidler for således å virke som en selv-emulgerbar olje ved tilsetning til vann. water and may be prepared by any of the methods used for insoluble compounds. The substituted benzodioxoles can, if desired, be dissolved in a solvent which is not miscible with water, e.g. a high-boiling hydrocarbon, suitably containing dissolved emulsifiers to thus act as a self-emulsifiable oil when added to water.

De substituerte benzodioksolene kan også blandes med et fuktemiddel med eller uten et inert fortynningsmiddel for å danne et fuktbart pulver som er opploselig eller dispergerbart i vann, eller de kan blandes med det inerte fortynningsmiddel for å danne et fast eller pulverformet produkt. The substituted benzodioxoles can also be mixed with a wetting agent with or without an inert diluent to form a wettable powder that is soluble or dispersible in water, or they can be mixed with the inert diluent to form a solid or powdery product.

Inerte fortynningsmidler med hvilke de substituerte benzodioksoler kan blandes, omfatter faste inerte media bestående av pulver-formede eller findelte faste materialer, f.eks. leire, sand, kalk, glimmer, gjodningsstoffer o.l., idet slike produkter enten består av pulver eller storre partikler. Inert diluents with which the substituted benzodioxoles can be mixed include solid inert media consisting of powdered or finely divided solid materials, e.g. clay, sand, lime, mica, fertilizers etc., since such products either consist of powder or larger particles.

De benyttede fuktemidler kan være anioniske forbindelser slik som f.eks. såper, fettsulfatestere slik som dodecylnatriumsulfat, oktadecylnatriumsulfat og cetylnatriumsulfat, fettaromatiske sulfo- The wetting agents used can be anionic compounds such as e.g. soaps, fatty sulfate esters such as dodecyl sodium sulfate, octadecyl sodium sulfate and cetyl sodium sulfate, fatty aromatic sulfo-

nater slik som alkylbenzensulfonater eller butylnaftalensulfonat, mer komplekse fettsulfonater slik som amidkondenseringsproduktene av olje-syre og N-metyltaurin eller natriumsulfonatet av dioktylsuccinat. nates such as alkylbenzene sulphonates or butyl naphthalene sulphonate, more complex fatty sulphonates such as the amide condensation products of oleic acid and N-methyltaurine or the sodium sulphonate of dioctyl succinate.

Fuktemidlene kan også være ikke-ioniske fuktemidler slik som kondenseringsproduktene av fettsyrer, fettalkoholer eller fettsubsti-tuerte fenoler med etylenoksyd, eller fettestere og etere av sukkere eller flerverdige alkoholer, eller de produkter som oppnåes fra de sistnevnte forbindelser ved kondensering med etylenoksyd, eller de produkter som er kjent som blokk-sampolymerisater av etylenoksyd og propylenoksyd. Fuktemidlene kan også omfatte kationiske midler slik som cetyltrimetylammoniumbromid og lignende. The humectants can also be non-ionic humectants such as the condensation products of fatty acids, fatty alcohols or fat-substituted phenols with ethylene oxide, or fatty esters and ethers of sugars or polyhydric alcohols, or the products obtained from the latter compounds by condensation with ethylene oxide, or the products which are known as block copolymers of ethylene oxide and propylene oxide. The humectants can also include cationic agents such as cetyltrimethylammonium bromide and the like.

Et insekticid preparat kan også være i form av en aerosol, hensiktsmessig ved bruk av et opplosningsmiddel og et fuktemiddel i tillegg til drivmidlet, som fortrinnsvis er et polyhalogenert alkan slik som diklordifluormetan. An insecticidal preparation can also be in the form of an aerosol, suitably using a solvent and a wetting agent in addition to the propellant, which is preferably a polyhalogenated alkane such as dichlorodifluoromethane.

Et insekticid preparat kan i tillegg til de substituerte benzodioksoler inneholde andre aktive insekticider, baktericider og fungicider, riet er funnet at det oppnås spesielle fordeler med bland-inger med andre insekticider. An insecticidal preparation can, in addition to the substituted benzodioxoles, contain other active insecticides, bactericides and fungicides, and it has been found that special advantages are achieved with mixtures with other insecticides.

I deres forskjellige anvendelsesområder kan forbindelsene ifolge oppfinnelsen brukes i forskjellige mengder; f.eks. for behandling av planter for kontroll av skadedyr på plantene anvendes forbindelsene i mengder på 17-1120 g per hektar, fortrinnsvis 35-280 g per hektar; for behandling av dyr for utryddelse av skadelige insekter, kan nevnte dyr på egnet måte dyppes i eller sproytes med en opplosning inneholdende 30-300 deler per million av den aktive forbindelse. In their different fields of application, the compounds according to the invention can be used in different amounts; e.g. for the treatment of plants for the control of pests on the plants, the compounds are used in amounts of 17-1120 g per hectare, preferably 35-280 g per hectare; for the treatment of animals for the eradication of harmful insects, said animals may be suitably dipped in or sprayed with a solution containing 30-300 parts per million of the active compound.

Folgende eksempler illustrerer fremstillingen og den insekti-cide virkning av forbindelsene ifolge oppfinnelsen, og del- og prosent-angivelsene er gitt som vektdeler og vektprosent hvis ikke annet er angitt. The following examples illustrate the preparation and the insecticidal effect of the compounds according to the invention, and the parts and percentages are given as parts by weight and percentage by weight unless otherwise stated.

Eksempel 1 Example 1

2,2-dimetyl-4-hydroksy-l,3-benzodioksol (14 deler) i benzen (25 deler), ble behandlet med metylisocyanat (6 deler) og noen dråper trietylamin under avkjoling. Ftter å ha stått i 30 minutter ble de dannede krystaller av 2,2-dimetyl-l,3-benzodioksol-4-yl-N-metylkarba-mat frafiltrert og vasket med benzen, deretter med petroleum (koke-punkt under 40°C) og ga den rene forbindelse i form av et hvitt, fast stoff med smeltepunkt 129°-130°C (16 deler, 85% utbytte). 2,2-Dimethyl-4-hydroxy-1,3-benzodioxole (14 parts) in benzene (25 parts) was treated with methyl isocyanate (6 parts) and a few drops of triethylamine under cooling. After standing for 30 minutes, the formed crystals of 2,2-dimethyl-1,3-benzodioxol-4-yl-N-methylcarbamate were filtered off and washed with benzene, then with petroleum (boiling point below 40°C ) and gave the pure compound as a white solid, mp 129°-130°C (16 parts, 85% yield).

Analyse: Funnet: C 59.35; H 5.90; N 6.35 Analysis: Found: C 59.35; H 5.90; N 6.35

C11H13N04 tilsvarer: c 59.18; H 5.87; N 6.28$ C11H13N04 corresponds to: c 59.18; H 5.87; N 6.28$

Eksempel 2- 3 Example 2-3

Fremgangsmåten i eksempel 1 ble gjentatt ved å erstatte 2,2-dimetyl-4-hydroksy-l,3-benzodioksol med den behorig substituerte hydroksy-1,3-benzodioksol for å danne fSigende forbindelser: 2-etyl-2-metyl-l,3-benzodioksol-4-yl-N-metylkarbamat, smeltepunkt 86-87°C 2-tert-butyl-2-metyl-l,3-benzodioksol-4-yl-N-metylkarbamat, smeltepunkt 89°-<q>o°c. The procedure of Example 1 was repeated by replacing 2,2-dimethyl-4-hydroxy-1,3-benzodioxole with the appropriately substituted hydroxy-1,3-benzodioxole to form the following compounds: 2-ethyl-2-methyl-1 ,3-benzodioxol-4-yl-N-methylcarbamate, melting point 86-87°C 2-tert-butyl-2-methyl-1,3-benzodioxol-4-yl-N-methylcarbamate, melting point 89°-<q> o°c.

Eksempel 4 Example 4

Filterpapir med diameter på 9 cm behandlet med en vandig acetonopplosning av 2,2-dimetyl-l,3-benzodioksol-4-yl-N-metylkarbamat i en mengde tilsvarende 1,1 kg/m aktiv bestanddel, ble plasert i petriskåler med diameter på 9 cm. Voksne hunnlig.e husfluer (Musea domestica) lett bedovet med karbondioksyd ble deretter innfort i skålene og et glasslokk plasert over hver av disse. Etter 24 timer ble fluene undersokt og alle var dode. Filter paper with a diameter of 9 cm treated with an aqueous acetone solution of 2,2-dimethyl-1,3-benzodioxol-4-yl-N-methylcarbamate in an amount corresponding to 1.1 kg/m of active ingredient was placed in Petri dishes with a diameter of 9 cm. Adult female houseflies (Musea domestica) lightly anesthetized with carbon dioxide were then placed in the dishes and a glass lid placed over each of these. After 24 hours the flies were examined and all were dead.

Eksempel 5 Example 5

Kålbladprover med diameter på 7 cm ble hver påstroket med 1 ml vandig acetonopplfisning av hver av forbindelsene Cabbage leaf samples with a diameter of 7 cm were each smeared with 1 ml of aqueous acetone solution of each of the compounds

2,2-dimetyl-l,3-benzodioksol-4-yl-N-metylkarbamat, og 2,2-dimethyl-1,3-benzodioxol-4-yl-N-methylcarbamate, and

2-etyl-2-metyl-l,3-benzodioksol-4-yl-N-metylkarbamat, 2-ethyl-2-methyl-1,3-benzodioxol-4-yl-N-methylcarbamate,

i hvert tilfelle ved konsentrasjoner tilsvarende bladpåstrykninger av 11.2, 5.6, 1.12, O.56 og 0.28 kg/hektar aktiv bestanddel. Når det påforte materialet var torket på bladene, ble hver bladprove plasert i en petriskål med diameter 9 cm hvor det var anbragt ti annetstadium-larver av den hvite kålsommerfugl (Pieris brassicae), og skålen ble dekket med et glasslokk. Det ble foretatt tre like forsok med hver forbindelse ved hvert konsentrasjonsnivå. Etter 48 timer ble larvene undersokt, og alle var dode. in each case at concentrations corresponding to leaf applications of 11.2, 5.6, 1.12, 0.56 and 0.28 kg/hectare of active ingredient. When the applied material had dried on the leaves, each leaf sample was placed in a petri dish with a diameter of 9 cm where ten second-stage larvae of the white cabbage butterfly (Pieris brassicae) were placed, and the dish was covered with a glass lid. Three identical experiments were performed with each compound at each concentration level. After 48 hours the larvae were examined and all were dead.

Eksempel 6 Example 6

En vandig suspensjon inneholdende 100 deler per million av 2,2-dimetyl-l,3-benzodioksol-4-yl-N-metylkarbamat ble sproytet i mengder tilsvarende 585 1 Per hektar på bonner (Vicia faba) hvor det befant seg voksende, vingelose bladlus (Megoura viviae). Etter denne behandling ble plantene plasert i glassbur som var dekket med gas for å gi ventilasjon. Hver behandling ga fullstendig utryddelse av blad-lusene i lopet av 24 timer sammenlignet med ingen utryddelse på kon-trollplanter. An aqueous suspension containing 100 parts per million of 2,2-dimethyl-1,3-benzodioxol-4-yl-N-methylcarbamate was sprayed in amounts equivalent to 585 1 per hectare on beans (Vicia faba) where there were growing, wingless aphid (Megoura viviae). After this treatment, the plants were placed in glass cages that were covered with gas to provide ventilation. Each treatment produced complete eradication of the aphids within 24 hours compared to no eradication on control plants.

Fksempel 7 Example 7

Et fuktbart pulverformet preparat ble laget ved å findele folgende: A wettable powdered preparation was made by comminuting the following:

Dette var egnet for dispersjon i vann og sproyting av planter. I This was suitable for dispersion in water and spraying plants. IN

Eksempel 8 Example 8

Et "5$ granulært preparat ble laget som folger: Granulær kalksten og Z% "Carbowax" ble tromlet sammen i 30 minutter. 5% fin-delt 2,2-dimetyl-l,3-benzodioksol-4-yl-N-metylkarbamat ble deretter' tilsatt og det hele tromlet i 15 minutter." 1.25% "Calflo E" (et kal-siumsilikat) ble deretter tilsatt og tromlet i ytterligere 75 minutter for å hindre sammenklebing av granulatene. Granulatene ble deretter til slutt siktet gjennom en 12-mesh sikt. A "5$ granular preparation was made as follows: Granular limestone and Z% "Carbowax" were tumbled together for 30 minutes. 5% finely divided 2,2-dimethyl-1,3-benzodioxol-4-yl-N-methylcarbamate was then' added and the whole drummed for 15 minutes." 1.25% "Calflo E" (a calcium silicate) was then added and tumbled for an additional 75 minutes to prevent sticking of the granules. The granules were then finally sieved through a 12-mesh sieve.

Eksempel 9 Example 9

Sylindriske puter av bomull med en diameter på ca. 1 cm og lengde på 2 cm, ble behandlet med 1/2 ml acetonopplosninger av folgende karbamater: 2,2-dimetyl-l,3-benzodioksol-4-yl-N-metylkarbamat, 2-etyl-2-metyl-l,3-benzodioksol-4-yl-N-metylkarbamat, 2,2-dietyl-l,3-benzodioksol-4-yl-N-metylkarbamat, 2-tert-butyl-2-metyl-l,3-benzodioksol-4-yl-N-metylkarbamat. Cylindrical cushions made of cotton with a diameter of approx. 1 cm and length of 2 cm, were treated with 1/2 ml acetone solutions of the following carbamates: 2,2-dimethyl-1,3-benzodioxol-4-yl-N-methylcarbamate, 2-ethyl-2-methyl-1, 3-benzodioxol-4-yl-N-methylcarbamate, 2,2-diethyl-1,3-benzodioxol-4-yl-N-methylcarbamate, 2-tert-butyl-2-methyl-1,3-benzodioxol-4- yl-N-methylcarbamate.

Etter å ha stått og torket i 12 timer ble putene behandlet med 1 ml blodserum fra sauer og infisert med 20 forstestadium-larver av sauespyfluen (Lucilia sericata). Etter 24 timer ble spyfluene undersokt og alle var dode; insekter som befant seg på ubehandlede puter var upåvirket. After standing and drying for 12 hours, the pads were treated with 1 ml of sheep blood serum and infected with 20 first-stage larvae of the sheep blowfly (Lucilia sericata). After 24 hours the blowflies were examined and all were dead; insects on untreated pads were unaffected.

For å demonstrere aktiviteten og toksisiteten til forbindelsene ifolge foreliggende oppfinnelse i forhold til disse egenskaper hos tidligere kjente forbindelser ble det foretatt en sammenligning mellom den tidligere kjente forbindelse 2,3-dihydro-2,2-dimetyl-7-benzofuranyl-N-metylkarbamat, som er kjent fra norsk patent nr. 109812, og 2,2-dimetyl-l,3-benzodioksol-4-yl-N-metylkarbamat ifolge foreliggende oppfinnelse. Aktiviteten for den nevnte kjente forbindelse ble bestemt under forsok med melbiller (Tribolium confusum), og det ble funnet at i en mengde på 1000 deler forbindelse per million del be-handlingsopplosning ble ingen av billene drept. I motsetning til dette ga den nevnte forbindelse ifolge foreliggende oppfinnelse en fullstendig utryddelse av Tribolium confusum i en mengde på 100 deler per million. In order to demonstrate the activity and toxicity of the compounds according to the present invention in relation to these properties of previously known compounds, a comparison was made between the previously known compound 2,3-dihydro-2,2-dimethyl-7-benzofuranyl-N-methylcarbamate, which is known from Norwegian patent no. 109812, and 2,2-dimethyl-1,3-benzodioxol-4-yl-N-methylcarbamate according to the present invention. The activity of the said known compound was determined during experiments with flour beetles (Tribolium confusum), and it was found that in an amount of 1000 parts of compound per million parts of treatment solution none of the beetles were killed. In contrast, the said compound according to the present invention gave a complete eradication of Tribolium confusum in an amount of 100 parts per million.

Toksisiteten overfor pattedyr for benzodioksolene ifolge foreliggende oppfinnelse er meget lavere enn den samme virkning for de kjente benzofuranylkarbamater, hvilket gjor at forbindelsene ifolge oppfinnelsen er meget tryggere å benytte. Toksisitetsverdiene er gitt i tabellen nedenfor: The toxicity to mammals of the benzodioxoles according to the present invention is much lower than the same effect for the known benzofuranyl carbamates, which means that the compounds according to the invention are much safer to use. The toxicity values are given in the table below:

Forbindelse """ m^^er ^6 legemsvekt Rotte Rotte Mus (oralt forsok) (dermalt forsok) Compound """ m^^er ^6 body weight Rat Rat Mouse (oral test) (dermal test)

Hydroksybenzodioksolene med formelen: The hydroxybenzodioxoles with the formula:

hvor R 1 og R 2 har samme betydning som angitt ovenfor, som er mellom-produkter, med unntagelse av de tilfelle hvor R 1 og R 2 er metyl, er where R 1 and R 2 have the same meaning as stated above, which are intermediate products, with the exception of the cases where R 1 and R 2 are methyl, are

nye forbindelser. Disse forbindelser fremstilles hensiktsmessig fra 1,2,3-trihydroksybenzen (pyrogallol) ved omsetning med det egnede keton i nærvær av fosforpentaklorid ved bruk av keton som opplosningsmiddel. new connections. These compounds are conveniently prepared from 1,2,3-trihydroxybenzene (pyrogallol) by reaction with the appropriate ketone in the presence of phosphorus pentachloride using ketone as solvent.

Claims (2)

1. Substituerte benzodioksoler med insekticid virkning, karakterisert ved at de har formelen: 12 S hvor R og R er alkyl med 1-6 karbonatomer, og RJ er alkyl med 1-4 karbonatomer.1. Substituted benzodioxoles with insecticidal action, characterized in that they have the formula: 12 S where R and R are alkyl with 1-6 carbon atoms, and RJ is alkyl with 1-4 carbon atoms. 2. Substituert benzodioksol ifolge krav 1, karakterisert ved at det er 2,2-dimetyl-l,3-benzodioksol-4-yl-N-metyl-karbamat.2. Substituted benzodioxol according to claim 1, characterized in that it is 2,2-dimethyl-1,3-benzodioxol-4-yl-N-methyl-carbamate.
NO63668A 1967-02-21 1968-02-20 NO119992B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB817467A GB1220056A (en) 1967-02-21 1967-02-21 Substituted benzodioxoles

Publications (1)

Publication Number Publication Date
NO119992B true NO119992B (en) 1970-08-10

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AT (3) AT296983B (en)
BE (1) BE710916A (en)
CH (1) CH482401A (en)
CS (1) CS166704B2 (en)
CY (1) CY636A (en)
DE (1) DE1667979C3 (en)
DK (1) DK133282C (en)
FI (1) FI51262C (en)
FR (1) FR1602292A (en)
GB (1) GB1220056A (en)
IE (1) IE31956B1 (en)
IL (1) IL29413A (en)
MY (1) MY7200116A (en)
NL (1) NL154216B (en)
NO (1) NO119992B (en)
SE (1) SE372765B (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1386095A (en) * 1971-05-04 1975-03-05 Fisons Ltd Preparation of 4-hydroxybenzodioxoles
DE2436721C3 (en) * 1973-08-09 1978-09-21 Istituto Luso Farmaco D'italia S.R.L., Mailand (Italien) 13-Benzodioxole derivatives, process for their preparation and pharmaceuticals containing these compounds
AU1069976A (en) * 1975-03-18 1977-08-04 Hoffmann La Roche Alkylene dioxy phenyl carbamates
GB1555474A (en) 1975-08-14 1979-11-14 Fisons Ltd Pesticidal composition and method of compatingpests
GB1579422A (en) * 1976-05-08 1980-11-19 Fisons Ltd 2,2 - dimethyl-1,3 - benzodioxol - 4 - yl - n - methylcarbamate
FR2360305A1 (en) * 1976-08-04 1978-03-03 Ile De France NEW 2,3-ALKYLENE BIS (OXY) BENZAMIDE SUBSTITUTES, THEIR DERIVATIVES AND THEIR PREPARATION METHODS
US4378367A (en) * 1978-05-16 1983-03-29 Fbc Limited Compositions containing 2,2-dimethyl-1,3-benzodioxol-4-yl N-methylcarbamate for treating seeds
AT375654B (en) * 1982-05-13 1984-08-27 Gerot Pharmazeutika METHOD FOR PRODUCING NEW PYROGALLOL [THERS AND THEIR SALTS
AT375360B (en) * 1982-12-23 1984-07-25 Gerot Pharmazeutika METHOD FOR PRODUCING NEW 1,3-BENZODIOXOL DERIVATIVES AND THEIR SALTS
JPS59155357A (en) * 1983-02-14 1984-09-04 ユ−エスヴイ−・フア−マシユ−テイカル・コ−ポレ−シヨン Benzoheterocyclic carbamate

Also Published As

Publication number Publication date
BE710916A (en) 1968-08-16
IE31956B1 (en) 1973-02-21
SE372765B (en) 1975-01-13
AT296983B (en) 1972-03-10
FR1602292A (en) 1970-11-02
GB1220056A (en) 1971-01-20
FI51262C (en) 1976-12-10
DE1667979A1 (en) 1971-07-15
AT283812B (en) 1970-08-25
DK133282C (en) 1976-09-20
NL6802492A (en) 1968-08-22
IE31956L (en) 1968-08-21
DK133282B (en) 1976-04-20
MY7200116A (en) 1972-12-31
FI51262B (en) 1976-08-31
IL29413A (en) 1972-04-27
CS166704B2 (en) 1976-03-29
DE1667979C3 (en) 1978-06-01
DE1667979B2 (en) 1977-10-06
CY636A (en) 1972-03-27
NL154216B (en) 1977-08-15
CH482401A (en) 1969-12-15
AT295530B (en) 1972-01-10

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