NO115321B - - Google Patents
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- Publication number
- NO115321B NO115321B NO15843765A NO15843765A NO115321B NO 115321 B NO115321 B NO 115321B NO 15843765 A NO15843765 A NO 15843765A NO 15843765 A NO15843765 A NO 15843765A NO 115321 B NO115321 B NO 115321B
- Authority
- NO
- Norway
- Prior art keywords
- benzofuranyl
- parts
- methylcarbamate
- carbon atoms
- melting point
- Prior art date
Links
- 230000000749 insecticidal effect Effects 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- SSUFJVXUMQIJAX-UHFFFAOYSA-N 1-benzofuran-2-yl carbamate Chemical compound C1=CC=C2OC(OC(=O)N)=CC2=C1 SSUFJVXUMQIJAX-UHFFFAOYSA-N 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- -1 for example soap Chemical class 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000000080 wetting agent Substances 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 241000238631 Hexapoda Species 0.000 description 5
- 241000255969 Pieris brassicae Species 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- BNZKLIMILUCWCN-UHFFFAOYSA-N 1-benzofuran-4-yl N-methylcarbamate Chemical compound CNC(OC1=CC=CC2=C1C=CO2)=O BNZKLIMILUCWCN-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 240000007124 Brassica oleracea Species 0.000 description 4
- 241000257226 Muscidae Species 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- GBUKRBYIEYYQGM-UHFFFAOYSA-N 1-benzofuran-2-ylcarbamic acid Chemical class C1=CC=C2OC(NC(=O)O)=CC2=C1 GBUKRBYIEYYQGM-UHFFFAOYSA-N 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- CFBCZETZIPZOGW-UHFFFAOYSA-N 1-benzofuran-4-ol Chemical compound OC1=CC=CC2=C1C=CO2 CFBCZETZIPZOGW-UHFFFAOYSA-N 0.000 description 2
- DKDMRNDZLXOMBJ-UHFFFAOYSA-N 1-benzofuran-7-yl N,N-dimethylcarbamate Chemical compound CN(C(OC1=CC=CC=2C=COC21)=O)C DKDMRNDZLXOMBJ-UHFFFAOYSA-N 0.000 description 2
- LVKKPBPHGILWOM-UHFFFAOYSA-N 1-benzofuran-7-yl n-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC2=C1OC=C2 LVKKPBPHGILWOM-UHFFFAOYSA-N 0.000 description 2
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 2
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 2
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 2
- 241001606077 Tatochila autodice Species 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 150000005846 sugar alcohols Chemical class 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- WXVRAHOQLYAQCR-UHFFFAOYSA-N 1-benzofuran-7-ol Chemical compound OC1=CC=CC2=C1OC=C2 WXVRAHOQLYAQCR-UHFFFAOYSA-N 0.000 description 1
- KYCZRSVIJUQOAJ-UHFFFAOYSA-N 1-butylnaphthalene;sulfuric acid Chemical class OS(O)(=O)=O.C1=CC=C2C(CCCC)=CC=CC2=C1 KYCZRSVIJUQOAJ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 235000011303 Brassica alboglabra Nutrition 0.000 description 1
- 235000011302 Brassica oleracea Nutrition 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 229920005682 EO-PO block copolymer Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 108010009736 Protein Hydrolysates Proteins 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000005667 attractant Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- OOZFJMRPUVMHEW-UHFFFAOYSA-N dioctyl sulfate Chemical compound CCCCCCCCOS(=O)(=O)OCCCCCCCC OOZFJMRPUVMHEW-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- FLGPRDQFUUFZBL-UHFFFAOYSA-N formaldehyde;naphthalen-1-ol Chemical class O=C.C1=CC=C2C(O)=CC=CC2=C1 FLGPRDQFUUFZBL-UHFFFAOYSA-N 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-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
- 239000004571 lime Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 239000003750 molluscacide Substances 0.000 description 1
- 230000002013 molluscicidal effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Insekticid preparat. Insecticide preparation.
Oppfinnelsen vedrører insekticide preparater som festar av eller inneholder visse karbamater som er blitt funnet å ha insekticid aktivitet. The invention relates to insecticidal preparations which bind off or contain certain carbamates which have been found to have insecticidal activity.
Det er blitt funnet at benzofuranylkarbamater som beskrevet i det følgende er aktive som insekticider, og visse av disse er særlig aktive mot kålormer og husfiuer med høy grad a<y>varighet. It has been found that benzofuranylcarbamates as described below are active as insecticides, and certain of these are particularly active against cabbage worms and houseflies with a high degree of persistence.
Oppfinnelsen vedrører altså et insekticid preparat som er kjennetegnet ved at det består av eller som aktiv bestanddel inneholder et ben-zofuranylkarbamat med formelen: The invention therefore relates to an insecticidal preparation which is characterized by the fact that it consists of or contains as an active ingredient a benzofuranylcarbamate with the formula:
hvor en av gruppene R<1>og R<4>er -O.CO.N.R<7>R<8>, hvor R<7>er en alkylgruppe med 1—5 karbonatomer<p>g R<8>er hydrogen eller en alkylgruppe med 1-7-5 karbonatomer, idet resten av gruppene R^,R<2>, R? pg R<4>er hydrogen, halogen eller alkyir grupper med 1-tt5 karbonatomer, Ru og R<1>4 er hydrogen eller aJkylgrupper med l-^-rES karbonatomer. where one of the groups R<1>and R<4>is -O.CO.N.R<7>R<8>, where R<7>is an alkyl group with 1-5 carbon atoms<p>g R<8> hydrogen or an alkyl group with 1-7-5 carbon atoms, the rest of the groups R^, R<2>, R? pg R<4> is hydrogen, halogen or alkyl groups with 1-tt5 carbon atoms, Ru and R<1>4 are hydrogen or alkyl groups with 1-4 carbon atoms.
Et insekticid preparat ifølge oppfinnelsen som inneholder benzofuranylkarbamater som angitt i det foregående, inneholder også minst ett av de stoffer som omfatter fuktemidler, faste fortynningsmidler, oppløsningsmidler (særlig høytkokende oppløsningsmidler) og spiselige stoffer som tiltrekker skadelige insekter. An insecticidal preparation according to the invention which contains benzofuranyl carbamates as stated above also contains at least one of the substances comprising wetting agents, solid diluents, solvents (especially high-boiling solvents) and edible substances which attract harmful insects.
Preparatet ifølge oppfinnelsen benyttes til The preparation according to the invention is used for
behandling av planter, områder (f. eks. jord) og stoffer som kan angripes av skadelige insekter, hvor det påføres eller innkorporeres en insekticid blanding som angitt i det foregående. Materialer som kan angripes av skadelige insekter omfatter slike stoffer som tre, papir, tekstil og tekstil-stoffer. treatment of plants, areas (e.g. soil) and substances that can be attacked by harmful insects, where an insecticidal mixture is applied or incorporated as indicated above. Materials that can be attacked by harmful insects include such substances as wood, paper, textiles and textile materials.
I insekticide preparater kan benzofuranyl-karbamatene innkorporeres f. eks. med faste inerte medier omfattende pulveriserte eller opp-delte faste stoffer, f. eks. lere, slik som kinalere, sand, kalk, glimmer, gjødningsmidler og lignende, idet slike produkter enten omfatter støv eller større partikler. In insecticidal preparations, the benzofuranyl carbamates can be incorporated, e.g. with solid inert media comprising powdered or divided solids, e.g. clay, such as china clay, sand, lime, mica, fertilizers and the like, as such products either include dust or larger particles.
Det foretrekkes imidlertid å blande benzo-furanylkarbamatene med et fuktningsmiddel med eller uten innkorporering av pulverisert eller oppdelt fast stoff som angitt ovenfor således at det fåes et fuktbart produkt som er i stand til å anvendes som sådant eller som en suspensjon eller dispersjon i vann. However, it is preferred to mix the benzo-furanyl carbamates with a wetting agent with or without the incorporation of powdered or divided solids as indicated above so that a wettable product is obtained which is capable of being used as such or as a suspension or dispersion in water.
Om ønskes kan benzofuranylkarbamatet innkorporeres i et organisk oppløsningsmiddel, som f. eks. kan være en høyt kokende hydrokarbon, sammen med et fuktnings- eller dispergerings-middel således at det dannes et emulgerbart, flytende konsentrat som kan dispergeres i vann for utsprøytning. If desired, the benzofuranyl carbamate can be incorporated into an organic solvent, such as e.g. can be a high-boiling hydrocarbon, together with a wetting or dispersing agent so that an emulsifiable, liquid concentrate is formed which can be dispersed in water for spraying.
Fuktningsmidlene som anvendes kan omfatte anjoniske forbindelser slik som f. eks. såpe, fettsulfatestere slik som dodecylnatriumsulfat, fettaromatiske sulfonater slik som alkylbenzen-sulfonater eller butylnaftalensulfater, mere komplekse fettsulfonater, slik som amidkonden-sasjonsprodukt av oljesyre, og N-metyltaurin eller natriumsaltet av dioktylsulforavsyre. Fuktningsmidlene kan også omfatte ikke-joniske fuktningsmidler slik som f. eks. kondensasjons-produkter av fettsyrer, fettalkoholer eller alkyl-substituerte fenoler med etylenoksyd eller fett-syreestere og estere av sukker eller flerverdige alkoholer eller produkter som fåes av de siste ved kondensasjon med etylenoksyd eller produkter kjent som blokk copolymere av etylenoksyd og propylenoksyd. Fuktningsmidlene kan også omfatte katjoniske midler slik som f.eks. cetyl-tri-metylammoniumbromid og lignende. The wetting agents used can include anionic compounds such as, for example soap, fatty sulfate esters such as dodecyl sodium sulfate, fatty aromatic sulfonates such as alkylbenzene sulfonates or butylnaphthalene sulfates, more complex fatty sulfonates, such as the amide condensation product of oleic acid, and N-methyltaurine or the sodium salt of dioctylsulfuric acid. The wetting agents can also include non-ionic wetting agents such as e.g. condensation products of fatty acids, fatty alcohols or alkyl-substituted phenols with ethylene oxide or fatty acid esters and esters of sugar or polyhydric alcohols or products obtained from the latter by condensation with ethylene oxide or products known as block copolymers of ethylene oxide and propylene oxide. The wetting agents can also include cationic agents such as e.g. cetyl trimethylammonium bromide and the like.
De insekticide preparater ifølge foreliggende oppfinnelse kan inneholde spisbåre stoffer som tiltrekker insekter, slik som sukker, melasse, pro-teinhydrolysater. Slike blandinger inneholder hensiktsmessig også spesifikke tiltrekningsmidler for insekter. The insecticidal preparations according to the present invention may contain edible substances that attract insects, such as sugar, molasses, protein hydrolysates. Such mixtures suitably also contain specific attractants for insects.
De insekticide preparater ifølge foreliggende oppfinnelse kan i tillegg til benzofuranylkarbamatet inneholde andre pesticider slik som herbi-cider, insekticider (f. eks. DDT, BHC eller alfa-naftyl-N-metylkarbamat), fungicider, molluski-cider og baktericider. ■ " ' In addition to the benzofuranylcarbamate, the insecticidal preparations according to the present invention may contain other pesticides such as herbicides, insecticides (e.g. DDT, BHC or alpha-naphthyl-N-methylcarbamate), fungicides, molluscicides and bactericides. ■ " '
I de følgende eksempler er deler og prosen-ter angitt i vekt' hvis"' ihtét annet er angitt. In the following examples, parts and percentages are given by weight if otherwise stated.
Eksempel 1.Example 1.
Til en oppløsning av 7,0 deler 4-hydroksy-benzofuran i 100 deler dietyleter ble det tilsatt 3,5 deler metylisocyanat og 0,3 deler trietylamin. Oppløsningen stod i 1 time og ble deretter for-dampet til lite volum, (ca. 10 deler) og fortynnet med 30 deler lett benzin (kokepunkt 40—60°C), slik at man fikk 8 deler av det rå produkt med smeltepunkt 130—135°C. Dette råprodukt ble omkrystallisert fra samme oppløsningsmidler slik at det ga 5 deler 4-benzofuranyl-N-metylkarbamat med smeltepunkt 131—136°C. To a solution of 7.0 parts of 4-hydroxybenzofuran in 100 parts of diethyl ether, 3.5 parts of methyl isocyanate and 0.3 parts of triethylamine were added. The solution stood for 1 hour and was then evaporated to a small volume, (approx. 10 parts) and diluted with 30 parts of light benzine (boiling point 40-60°C), so that 8 parts of the crude product with a melting point of 130 -135°C. This crude product was recrystallized from the same solvents so that it gave 5 parts of 4-benzofuranyl-N-methylcarbamate with a melting point of 131-136°C.
Analyse:Analysis:
Funnet: C 62,70; H4,75; O 24,95%<C>10H9NO3krever: C 62,82; H4.75; 025,11% Found: C 62.70; H4.75; O 24.95%<C>10H9NO3 requires: C 62.82; H4.75; 025.11%
Eksempel 2.Example 2.
Til en oppløsning av 10 deler 7-hydroksy-benzofuran i 20 deler dietyleter ble det tilsatt 5 deler metylisocyanat og 0,3 deler trietylamin. Oppløsningen stod i 1 time og ble deretter fortynnet med 5 deler lettbensin (kokepunkt 40— 60°C), og det ble dannet et bunnfall. Dette ble frafiltrert og omkrystallisert fra de samme opp-løsningsmidler slik at det ga 7-benzofuranyl-N-metylkarbamat med smeltepunkt 139°C. To a solution of 10 parts of 7-hydroxybenzofuran in 20 parts of diethyl ether, 5 parts of methyl isocyanate and 0.3 parts of triethylamine were added. The solution stood for 1 hour and was then diluted with 5 parts light petrol (boiling point 40-60°C), and a precipitate formed. This was filtered off and recrystallized from the same solvents so that it gave 7-benzofuranyl-N-methylcarbamate with a melting point of 139°C.
Analyse:Analysis:
Funnet: C 62,55; H4,75; N7,20% C,nHftN03 krever C 62,82; H4,75; N 7,33% Found: C 62.55; H4.75; N7.20% C,nHftN03 requires C 62.82; H4.75; N 7.33%
Eksemplene 3— 6.Examples 3— 6.
På analog måte som de foregående eksempler ble følgende forbindelser fremstilt: 5-klor-7-benzofuranyl-N-metylkarbamat med In an analogous manner to the previous examples, the following compounds were prepared: 5-chloro-7-benzofuranyl-N-methylcarbamate with
smeltepunkt 127—130°C. melting point 127-130°C.
5-metyl-7-benzofuranyl-N-metylkarbamat med 5-methyl-7-benzofuranyl-N-methylcarbamate with
smeltepunkt 131—132°C. melting point 131-132°C.
2- metyl-4-benzofuranyl-N-metylkarbamat med 2- methyl-4-benzofuranyl-N-methylcarbamate with
smeltepunkt 148—150°C. melting point 148-150°C.
3- metyl-4-benzofuranyl-N-metylkarbamat med smeltepunkt 116—117°C. 3-methyl-4-benzofuranyl-N-methylcarbamate with melting point 116-117°C.
Eksempel 7.Example 7.
En avkjølt omrørt oppløstning av vannfri dimetylamin (9,5 deler) i isopropyleter (40'delef^ tilsattes en oppløsning av 4-benzofuranylklor-format (13 deler) i benzen (50 deler) over' et tidsrom av 15 minutter idet temperaturen ble holdt under 25°C. Blandingen ble deretter vasket med fortynnet saltsyre og deretter med vann inntil vaskevannet var nøytralt. Det organiske lag ble tørket med natriumsulfat, og oppløs-ningsmidlet fjernet ved destillasjon. Fraksjone-ring av den resterende olje ga 4-benzofuranyl-N, N-dimetylkarbamat som en fargeløs olje med kokepunkt 102—104°C/0,2 mm hvilken størknet til en gulaktig fast masse med smeltepunkt 48— 50°C. To a cooled stirred solution of anhydrous dimethylamine (9.5 parts) in isopropyl ether (40 parts) was added a solution of 4-benzofuranyl chloroformate (13 parts) in benzene (50 parts) over a period of 15 minutes while maintaining the temperature below 25° C. The mixture was then washed with dilute hydrochloric acid and then with water until the wash water was neutral. The organic layer was dried with sodium sulfate, and the solvent removed by distillation. Fractionation of the remaining oil gave 4-benzofuranyl-N , N-dimethylcarbamate as a colorless oil with a boiling point of 102—104°C/0.2 mm which solidified to a yellowish solid with a melting point of 48—50°C.
Analyse:Analysis:
Funnet: C 64,25; H5,50; N6,65% CnHnNO., krever: C 64,38; H5,40; N 6,83% Found: C 64.25; H5.50; N6.65% CnHnNO., requires: C 64.38; H5.40; N 6.83%
Eksemplene 8— 9.Examples 8-9.
Følgende forbindelser ble fremstilt ved hjelp av analoge fremgangsmåter som i eksempel 7: 7-benzofuranyl-N,N-dimetylkarbamat med The following compounds were prepared using analogous procedures as in Example 7: 7-benzofuranyl-N,N-dimethylcarbamate with
smeltepunkt 69—71 °C. 3-metyl-4-benzofuranyl-N,N-dimetylkarbamat, melting point 69-71 °C. 3-methyl-4-benzofuranyl-N,N-dimethylcarbamate,
oljeaktig væske.oily liquid.
Eksempel 10.Example 10.
Glassplater med en diameter på 9 cm ble be-handlet med en acetonoppløsning av hver av forbindelsene 4-benzofuranyl-N-metylkarbamat og 7-benzofuranyl-N-metylkarbamat slik at man fikk et jevnt belegg som var lik 3,3 milligram per dm<2>og 9 milligram per dm<2>. Ved 10 dagers mellomrom ble voksne husfluer (Musea domestica) innesluttet med disse overflater i 24 ti-mers tidsrom, hvoretter dødeligheten ble talt. Det ble funnet at med begge forbindelser ga begge påføringsforhold 100 pst. drepning av husfluer, 10, 20, 30, 40, 50 og 60 dager etter behandling. Glass plates with a diameter of 9 cm were treated with an acetone solution of each of the compounds 4-benzofuranyl-N-methylcarbamate and 7-benzofuranyl-N-methylcarbamate so that a uniform coating was obtained which was equal to 3.3 milligrams per dm< 2>and 9 milligrams per dm<2>. At 10-day intervals, adult houseflies (Musea domestica) were enclosed with these surfaces for a 24-hour period, after which mortality was counted. It was found that with both compounds, both application rates produced 100 percent kill of houseflies, 10, 20, 30, 40, 50 and 60 days after treatment.
Eksempel 11.Example 11.
Unge kålplanter (Brassica oleracea) med 3—4 virkelige blader ble sprøytet med vandig acetonoppløsning av 4-benzofuranyl-N-metylkarbamat inneholdende 0,1 pst. og 0,03 pst. av forbindelsen. Ved mellomrom etter sprøytning ble annet trinn av larver av hvite kålsommerfugler (Pieris brassicae) innelukket med planten idet det ble anvendt elektriske grenser i et tidsrom av 48 timer, hvoretter dødeligheten ble be-stemt. Resultatene er angitt i følgende tabell: Young cabbage plants (Brassica oleracea) with 3-4 true leaves were sprayed with aqueous acetone solution of 4-benzofuranyl-N-methylcarbamate containing 0.1% and 0.03% of the compound. At intervals after spraying, second instar larvae of white cabbage butterflies (Pieris brassicae) were enclosed with the plant using electrical barriers for a period of 48 hours, after which mortality was determined. The results are shown in the following table:
Eksempel 12. Example 12.
Filterpapir med en diameter på 9 cm be-handlet med en vandig acetonoppløsning av hver av forbindelsene 7-benzofuranyl-N-metylkarbamat, 7-benzofuranyl-N,N-dimetylkarbamat, 4-benzofuranyl-N,N-dimetylkarbamat og 4-benzofuranyl-N-metylkarbamat med mengder ekva-lent med 111 og 11 milligram per kvadratdesi-meter ble anbragt i bunnen av Petriskåler med en diameter på 9 cm. Porsjoner av voksne husfluer av hunkjønn (Musea domestica) som var svakt anestisert med karbondioksyd, ble deretter innført i skålene, og det ble anbragt et glasslokk på hver. Etter 24 timer ble fluene undersøkt, og det ble funnet at 100 pst. av disse som var be-handlet med hver forbindelse var blitt drept med begge påføringsmengder. Filter paper with a diameter of 9 cm treated with an aqueous acetone solution of each of the compounds 7-benzofuranyl-N-methylcarbamate, 7-benzofuranyl-N,N-dimethylcarbamate, 4-benzofuranyl-N,N-dimethylcarbamate and 4-benzofuranyl- N-methylcarbamate in amounts equivalent to 111 and 11 milligrams per square decimeter were placed in the bottom of Petri dishes with a diameter of 9 cm. Portions of adult female houseflies (Musea domestica) lightly anesthetized with carbon dioxide were then introduced into the dishes, and a glass lid was placed on each. After 24 hours the flies were examined and it was found that 100% of those treated with each compound had been killed by both application rates.
Eksempel 13.Example 13.
7 cm skiver av kålblader ble malt med 1 mil-liliter vandig acetonoppløsning av hver av forbindelsene som er angitt i det. følgende ved kon-sentrasjoner som var lik bladpåføringer på 1130, 565, 113, 56 og 28 g per aktiv bestanddel per mål. Etter tørking ble hver bladskive anbragt i en 9 cm Petriskål, infisert med ti larver av annet stadium av hvite kålsommerfugler (Pieris brassicae) og dekket med et glasslokk.; Det ble gjort tre forsøk med hver konsentrasjon. Etter 48 timer ble larvene undersøkt, og antall døde ble notert. Prosent dødelighet er angitt i det føl-gende. 7 cm slices of cabbage leaves were ground with 1 ml aqueous acetone solution of each of the compounds indicated therein. following at concentrations which were equal to foliar applications of 1130, 565, 113, 56 and 28 g per active ingredient per measure. After drying, each leaf disc was placed in a 9 cm Petri dish, infested with ten second instar larvae of cabbage white butterflies (Pieris brassicae) and covered with a glass lid.; Three experiments were performed with each concentration. After 48 hours, the larvae were examined and the number of dead was noted. Percentage mortality is indicated in the following.
Eksempel 14 Example 14
Et fuktbart pulver ble fremstilt som følger: 4-benzofuranyl-N-metylkarbamat 20 % A wettable powder was prepared as follows: 4-benzofuranyl-N-methylcarbamate 20%
Sulfatert dodecylalkohol-ethylenoksyd kon-densasjonsprodukt kommersielt tilgjengelig for fuktningsmiddel som «HOE Sulfated dodecyl alcohol-ethylene oxide condensation product commercially available for wetting agent as "HOE
S2/154» 1 % S2/154" 1%
Sulfonert naftol-formaldehyd kondensa- • Sulfonated naphthol-formaldehyde condensa- •
sjonsprodukt, kommersielt tilgjengelig tion product, commercially available
fuktningsmiddel som «DIAPOL PT» 5 % wetting agent such as "DIAPOL PT" 5%
Kinalere 74 % Chinalar 74%
Dette produkt kunne lett dispergeres i vann This product was easily dispersed in water
for sprøytningsformål. for spraying purposes.
Eksempel 15.Example 15.
7 cm plater av kålblader ble bestrøket med 1 ml vandig acetonoppløstning av den nedenfor angitte forbindelse i konsentrasjonen som er ekvivalent til bladpåføringer på 10, 5, 1, 0,5 og 0,25 kg av aktivt stoff per hektar. Etter tørking ble hver bladplate plassert i 9 cm diameter petriskål, infisert med 10 annet stadium larver av hvit kålsommerfugl (Pieris brassicae) og dekket med en glassplate. Tre paralleller ble gjort ved hver konsentrasjon. Etter 48 timer ble larvene undersøkt og antall døde ble oppført. Mortali-tetsprosenten er angitt nedenfor. 7 cm plates of cabbage leaves were coated with 1 ml aqueous acetone solution of the compound indicated below in the concentration equivalent to foliar applications of 10, 5, 1, 0.5 and 0.25 kg of active substance per hectare. After drying, each leaf plate was placed in a 9 cm diameter Petri dish, infested with 10 second-stage larvae of white cabbage butterfly (Pieris brassicae) and covered with a glass plate. Three parallels were made at each concentration. After 48 hours, the larvae were examined and the number of dead was recorded. The mortality rate is given below.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB2421164A GB1101415A (en) | 1964-06-11 | 1964-06-11 | Benzofuranyl carbamates and pesticidal compositions containing them |
GB4304364 | 1964-10-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
NO115321B true NO115321B (en) | 1968-09-16 |
Family
ID=26256986
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO15843765A NO115321B (en) | 1964-06-11 | 1965-06-10 |
Country Status (8)
Country | Link |
---|---|
BE (1) | BE665313A (en) |
CH (1) | CH434867A (en) |
FI (1) | FI42255B (en) |
FR (1) | FR1458960A (en) |
GB (1) | GB1101415A (en) |
IL (1) | IL23650A (en) |
NL (1) | NL6507520A (en) |
NO (1) | NO115321B (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0116938A1 (en) * | 1983-02-14 | 1984-08-29 | Usv Pharmaceutical Corporation | Benzoheterocyclic carbamates |
-
1964
- 1964-06-11 GB GB2421164A patent/GB1101415A/en not_active Expired
-
1965
- 1965-06-01 IL IL2365065A patent/IL23650A/en unknown
- 1965-06-03 CH CH776865A patent/CH434867A/en unknown
- 1965-06-04 FI FI134365A patent/FI42255B/fi active
- 1965-06-10 NO NO15843765A patent/NO115321B/no unknown
- 1965-06-10 FR FR20195A patent/FR1458960A/en not_active Expired
- 1965-06-11 NL NL6507520A patent/NL6507520A/xx unknown
- 1965-06-11 BE BE665313A patent/BE665313A/xx unknown
Also Published As
Publication number | Publication date |
---|---|
GB1101415A (en) | 1968-01-31 |
NL6507520A (en) | 1965-12-13 |
FR1458960A (en) | 1966-11-18 |
IL23650A (en) | 1969-03-27 |
CH434867A (en) | 1967-04-30 |
FI42255B (en) | 1970-03-02 |
BE665313A (en) | 1965-12-13 |
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