NO149173B - Substituerte n-fenyl-n`-benzoyl-urinstoffer for anvendelse som insekticider og insekticid middel inneholdende slike forbindelser - Google Patents
Substituerte n-fenyl-n`-benzoyl-urinstoffer for anvendelse som insekticider og insekticid middel inneholdende slike forbindelser Download PDFInfo
- Publication number
- NO149173B NO149173B NO770042A NO770042A NO149173B NO 149173 B NO149173 B NO 149173B NO 770042 A NO770042 A NO 770042A NO 770042 A NO770042 A NO 770042A NO 149173 B NO149173 B NO 149173B
- Authority
- NO
- Norway
- Prior art keywords
- spp
- phenyl
- benzoyl
- substituted
- insecticides
- Prior art date
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- 241000254109 Tenebrio molitor Species 0.000 description 1
- 241000131345 Tipula <genus> Species 0.000 description 1
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- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical class ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
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- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 241001414985 Zygentoma Species 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 244000000054 animal parasite Species 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000002969 artificial stone Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 150000008047 benzoylureas Chemical class 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
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- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 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
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
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- 244000078703 ectoparasite Species 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
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- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
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- 238000000227 grinding Methods 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 239000010903 husk Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
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- 239000001023 inorganic pigment Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- 239000004579 marble Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N methyl iso-propyl ketone Natural products CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
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- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229940068984 polyvinyl alcohol Drugs 0.000 description 1
- 239000004540 pour-on Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
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- 239000011701 zinc Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/43—Y being a hetero atom
- C07C323/44—X or Y being nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
- C07C275/48—Y being a hydrogen or a carbon atom
- C07C275/54—Y being a carbon atom of a six-membered aromatic ring, e.g. benzoylureas
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Oppfinnelsen vedrører nye N-fenyl-N'-benzoy1-urin-
stoffer for> anvendelse som insekticider.
Det er allerede kjent at bestemte benzoylurinstoffer,
som f.eks. N-(2,6-diklorbenzoyl)-N'-(4-klor- resp. 3,^-diklor-fenyl)-urinstoff har insekticide egenskaper (sammenlign DOS:
2.123-236). Det er blitt funnet at de nye N-fenyl-N'-benzoylurinstoffer med formel I
hvori
R betyr halogenalkyl med 1 til H karbonatomer,
R-<*-> betyr hydrogen eller halogen, ;R 2 betyr halogen, nitro, alkyl eller alkoks-y med 1 til 3 karbonatomer pr.'alkyl- resp. alkoksyrest og ;X betyr et oksygen- eller svovelatom, mens ;n betyr et helt tall fra 0 til 5, ;har sterke insekticide egenskaper. ;De nye N-fenyl-N'-benzoylurinstoffer med formel I fåes når ;a) substituerte aniliher- med formel ;omsettes eventuelt i nærvær av et oppløsningsmiddel med benzoyl-isocyanater med formel ;hvori ;R, R 1 , R 2, X og n har overnevnte betydning, eller ;b) substituerte fenylisocyanater med formel ;;omsettes eventuelt i nærvær av et oppløsningsmiddel med ;benzamider med formel ;;hvori ;R, R 1 , R 2, X og n har overnevnte betydning. Overraskende har de nye N-fenyl-N'-benzoyl-urin-stoffer ifølge oppfinnelsen en vesentlig bedre' insekticid virkning enn de nærmestliggende fra teknikkens stand tidligere kjente forbindelser av analog konstitusjon og samme virknings-retning. Stoffene ifølge oppfinnelsen er således en ekte berik-ning av teknikken. ;Anvender man ifølge fremgangsmåte a) 3-klor-4-trifluormetoksyanilin og 2-klorbenzoylisocyanat og ifølge fremgangsmåte b) 3-klor-4-trifluormetoksy-fenylisocyanat og 2,6-dif luorbenzamid som utgangsstof f er, så kan re*aksjonsf or løpet gjengis med følgende formelskjema:
Utgangsstoffene som skal anvendes er generelt defi-nert med formlene II til V. Fortrinnsvis betyr imidlertid her: R rettlinjet eller forgrenet halogenalkyl med 1 til
3, spesielt 1 eller 2 karbonatomer,
R"'" hydrogen eller klor,
R 2 nitrOj fluor, klor, brom, jod, metyl, etyl,
metoksy eller etoksy og
n er 0 til 3.
De som utgangsstoffer anvendhare substituerte ani-liner II er kjent og fremstillbare etter litteraturkjente fremgangsmåter (sammenlign f.eks. J.Org.Chem. 25, (1960), 965 og 25,
(1964), 1; Am.Soc. 73, (1951), 5831i Bull.Soc.Chim.France 4,
(1957), 531; Z.obsc.Chim. 35, (1965), 1377 engelsk oversettelse: Am.Soc. 83 (1961), 4360 og US-patent nr. 3-387.037). Amino-gruppen kan etter vanlige fremgangsmåter omdannes i isocyanat-gruppen, f.eks. ved omsetning med fosgen, hvorved det fåes de tilsvarende fenylisocyanater (IV). Som eksempler skal det i detalj nevnes: 4-trifluormetoksy-, 4-trifluormetyltio-, 3-trifluormetoksy-, 3-trifluormetyltio-, 2-trifluormetoksy-, 2-trifluormetyltio-, 3~klor-4-trifluormetoksy-,.3-klor-4-trifluormetyltio-, 4-difluormonoklormetyltio-, 3-klor-4-difluormonoklormetyltio-, 2-klor-4-difluormonoklormetyltio-, 4-(2-klor-1,1,2-trifluor-etoksy)-, 3-klor-4-(2-klor-l,l,2-trifluoretoksy)-anilin resp.
-fenylisocyanat.
De videre som utgangsstoffer anvendbare benzoyl-isocyanater III er kjent (sammenlign J.Org.Chem. 30 (12), side 4306-4307 (1965)), likeledes som benzamidene (V) (sammenlign Beilstein "Handbuch der organischen Chemie", bind 9, side 336).
Som eksempler skal det i detalj nevnes:
2-metyl-, 2-etyl-, 3-metyl-, 3~etyl-, 4-metyl-, 4-et-yl-, 2-klor-, 4-klor-, 2,4-diklor-, 2,4-difluor-, 2,6-diklor-, 2,6-difluor-, 2-fluor-, 2-brom-, 2-jod^, ■ 2-nitro-, 3-nitro-, 4-nitro-, 2-metoksy-, 2-etoksy- og 2,3,6-triklor-benzoyl-isocya-nat resp. -benzamid.
Fremgangsmåtene til fremstilling av N-fenyl-N'-benzoylurinstoffene ifølge oppfinnelsen gjennomføres fortrinnsvis under medanvendelse av egnede oppløsnings- eller fortynnings-midler. Som slike kommer det i praksis på tale alle inerte organiske oppløsningsmidler. Hertil hører spesielt alifatiske og aromatiske, eventuelt klorerte hydrokarboner, som benzen, toluen, xylen, bensin, metylenklorid, kloroform, karbontetraklorid, klorbenzen eller etere, f.eks. dietyl- og dibutyleter, dioksan, videre ketoner, eksempelvis aceton, metyletyl-, metylisopropy1-og metylisobutylketon, dessuten nitriler, som aceto- og propionitril.
Reaksjonstemperaturen kan varieres innen et stort område. Vanligvis arbeider man mellom 0 og 120°C, fortrinnsvis ved 70 - 85°C.
Omsetningen lar man vanligvis forløpe ved normal-trykk.
Por gjennomføring av fremgangsmåten anvender man utgangskomponentene, fortrinnsvis i ekvimolare forhold. Et overskudd av den ene eller annen reaksjonskomponent medfører ingen vesentlige fordeler.
Vanligvis har man reaksjonsdeltagerne sammen i
et av de angitte oppløsningsmidler. De substituerte fenylisocyanater IV som skal anvendes ved fremgangsmåtevariant b) kan anvendes som sådanne eller uten mellomisolasjon i form av deres reaksjonsblanding som fåes etter omsetning av aminofosgen. Denne reaksjonsblanding blandes fortrinnsvis i et av de overnevnte oppløsningsmidler med benzamidet V.
Reaksjonen gjennomføres under de ovenfor angitte betingelser og produktene som utskiller seg isoleres på vanlig måte ved filtrering, vasking og eventuell omkrystallisering.
Forbindelsene fremkommer i krystallinsk form med skarpt smeltepunkt.
Som allerede flere ganger nevnt utmerker de N-fenyl-N'-benzoyl-urinstoffer ifølge oppfinnelsen seg ved en frem-ragende insekticid virkning. De virker ikke bare overfor plante-skadedyr, men også på den veterinærmedisinske sektor mot dyriske parasitter (ektoparasitter), som parasitterende fluelarver. Av denne grunn kan forbindelsen ifølge oppfinnelsen med resultat anvendes i plantebeskyttelse og på veterinærsektoren som skade-dy r s bekjempe Ise .
De virksomme stoffer egner seg ved god planteforenlig-het og gunstig varmblodstoksisitet til bekjempelse av dyriske skadedyr, spesielt insekter, som forekommer i landbruket, i skogs-bruk, i forråds- og materialbeskyttelse samt på hygienesektoren. De er virksomme mot normalt sensible og resistente typer som mot alle eller enkelte utviklingsstadier. Til de overnevnte skadedyr hører: Fra orden Isopoda f.eks. Oniscus asellus, Armadillidium vulgare,
Porcellio scaber.
Fra orden Diplopoda f.eks. Blaniulus guttulatus.
Fra orden Chilopoda f.eks. Geophilus carpophagus, Scutigera spee.
Fra orden Symphyla f.eks. Scutigerella immaculata.
Fra orden Thysanura f.eks. Lepisma saccharina.
Fra orden Collembola f.eks. Onychiurus armatus.
Fra orden Orthoptera f.eks. Blatta orientalis, Periplaneta ameri-cana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllo-talpa spp., Locusta migratoria migra-torioides, Melanoplus differentialis,
Schistocerca gregaria.
Fra orden Dermaptera f.eks. Forficula auricularia.
Fra orden Isoptera f.eks. Reticulitermes spp.
Fra orden Anoplura f.eks. Phylloxera vastatrix, Pemphigus spp.,
Pediculus humanus corporis, Haematopinus
spp., Linognathus spp.
Fra orden Mallophaga f.eks. Trichodectes spp., Damulinea spp.' Fra orden Thysanoptera f.eks. Hercinothrips feraoralis, Thrips
tabaci.
Fra orden Hetereoptera f.eks. Eurygaster spp., Dysdercus intermedius,
Piesma quadrata, Cimex lectularius,
Rhodnius prolixus, Triatoma spp. Fra orden Homoptera f.eks. Aleurodes brassicae, Bemisia tabaci,
Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis- bi-lobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nila-parvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp.,
Psylla spp.
Fra orden Lepidoptera f.eks. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardel-la, Hypono-meuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrys-orrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Laphygma e-xigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Cacoecia podana, Capua reticulana, Choris-toneura fumiferana, Glysia ambi-guella, Homona magnanima, Tortrix viridana.
Fra orden Coleoptera f.eks. Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylo-trupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epi-lachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Antho-•nomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopo-lites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Der-mestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.
Fra orden Hymenoptera f. eks.- Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp..
Fra orden Diptera f.eks i Åedes spp., Anopheles spp., Culex spp.,
Drosophila melanogaster, Musea spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula
paludosa.
Fra orden Siphonaptera f.eks. Xenopsylla cheopis, Ceratophyllus spp..
De virksomme stoffer kan overføres i de vanlige formuleringer som oppløsninger, emulsjoner, sprøytepulvere, suspensjoner, pulvere, forstøvningsmidler, skum, pastaer, opp-løselige pulvere, granulater, aerosoler, suspensjons-emulsjons-konsentrater, frøgodspudder, virksomme stoff-impregnerte natur-
og syntetiske stoffer, finforkapslinger i polymere stoffer og i hylsemasser for frøgods, videre i formuleringer med brennsatser, som røkepatroner, -esker, -spiraler og lignende samt ULV-kald-
og varmfortåkningsformuleringer.
Disse formuleringer fremstilles på kjent måte, f.eks. ved sammenblanding av det virksomme stoff med drøyemidler, altså flytende oppløsningsmidler, under trykk stående flytendegjorte gasser og/eller faste bærestoffer, eventuelt under anvendelse av overflateaktive midler, altså emulgeringsmidler og/eller disper-geringsmidler og/eller skumfrembringende midler. I tilfelle anvendelse av vann som drøyemiddel kan det f.eks. anvendes også organisk oppløsningsmiddel som hjelpeoppløsningsmiddel. Som flytende oppløsningsmiddel kommer det i det vesentlige i betrakt-ning: Aromater som xylen, toluen eller alkylnaftaliner, klorerte aromater eller klorerte, alifatiske hydrokarboner som klorbenzener, kloretylener eller metylenklorid, alifatiske hydrokarboner som cykloheksan eller parafiner, f.eks. jordoljefraksjoner, alkoholer som butanol eller glykol samt deres etere og estere,' ketoner som aceton, metyletylketon, metylisobutylketon eller cykloheksanon, sterkt polare oppløsningsmidler, som dimetylformamid og dimetyl-sulfoksyd samt vann; med flytendegjorte gassformede drøyemidler eller bærestoffer er det ment slike væsker som ved normal tempe-ratur og under normalt trykk er gassf ormet-,- f; eks;, aerosol-driv-gasser, som halogenhydrokarboner som butan, propan, nitrogen og karbondioksyd; som faste bærestoffer: naturlig, stenmel, som kaoliner, leirjord, talkum, kritt, kvarts, attapulgitt, mont-morillonit, diatomenjord og syntetisk stenmel, som høydispers kiselsyre, aluminiumoksyd og silikater; som faste bærestoffer for granulater: brutt eller fraksjonert naturlig sten som calcit, marmor, pimpsten, sepiolit, dolomit samt syntetiske granulater av uorganisk eller organisk mel samt granulater av organisk material som sagmel, kokosnøttskall og maiskolber og tobakksstengler; som emulgerings- .og/eller skumfrembringende middel: Ikke-ionogene og anioniske' emulgatorer som polyoksy-etylen-fettsyreestere, polyoksyi-etylen-fettalkoholetere, f.eks. alkylarylpolyglykoleter, alkylsulfonater, alkylsulfater, aryl-sulfonater samt eggehvitehydrolysatersom dispergeringsmiddel:
f.eks. lignin, sulfittavlut og metylcellylose.
Det kan i'formuleringene anvendes klebemidler som karboksymetylcellulose, naturlige og syntetiske pulverformede,
kornede eller lateksformede polymere, som gummi-arabicum, "poly-vinylalkohol, polyvinylaceta.t..
Det kan anvendes f arvestoff er. som. uorganiske, pig-menter, f.eks. jernoksyd, titanoksyd, ferrocyanblå og organiske farvestoffer som alizarin-, azo-metallftalocyaninfarvestoffer og sporenæringsstoffer som salter av jern, mangan, bor, kobber, kobolt, molybden og sink.
Formuleringene inneholder vanligvis mellom 0,1
og 95 vekti? virksomt stoff, fortrinnsvis mellom 0,5 og 90$.
Anvendelsen av de virksomme stoffer ifølge oppfinnelsen foregår i form av deres handelsvanlige formuleringer og/eller de av disse formuleringer tilberedte anvendelsesformer.
Det virksomme stoffinnhold av de fra de handelsvanlige formuleringer tilberedte anvendelsesformer kan variere innen vide områder. Den virksomme, stoffkonsentrasjon av an-vendelsesf ormene kan ligge fra 0,000000.1 til 100 vekt% virksomt stoff, fortrinnsvis mellom 0,01 og 10 vekt%.
Anvendelsen foregår i en til anvendelsesformene til-
passet vanlig måte.
Anvendelsen av de virksomme stoffer ifølge oppfinnelsen foregår i veterinærsektoren på kjent måte, som ved oral anvendelse i form av eksempelvis tabletter, kapsler, drikker, granulater, ved dermal anvendelse i form av eksempelvis dypping (Dippen), sprøytning (Sprayen), påhelling (pour-on and spot-on) og innpudring samt ved parenteral anvendelse i form av eksempelvis injeksjoner.
Eksempel A.
Phaedon-larve-prøve.
Oppløsningsmiddel: 15 vektdeler dimetylformamid.
Emulgator ■■ : 1 vektdel alkylarylpolyglykoleter.
Por fremstilling av en hensiktsmessig virksom stofftilberedning sammenblander man 1 vektdel virksomt stoff med den angitte oppløsningsmiddelmengde og den angitte emulgatormengde og fortynner konsentratet med vann til den ønskede konsentrasjon.
Med den virksomme stofftilberedning sprøyter man kålblader (Brassica oleracea) dråpefuktige og befenger dem med sij"$reddikblad-billelarver (Phaedpn cochleariae) .
Etter de angitte tider bestemmes utryddelsen i %. Her betyr 100% at alle billelarver ble utryddet; 0% betyr at ingen billelarver ble utryddet.
Virksomme stoffer, virksomme stoffkonsentrasjoner, vurderingstider og resultater fremgår av følgende tabell.
Eksempel B.
Plutella-prøve.
Oppløsningsmiddel: 15 vektdeler dimetylformamid.
Emulgator : 1 vektdel alkylarylpolyglykoleter.
Por fremstilling av en egnet virksom stofftilberedning sammenblander man 1 vektdel virksomt stoff med den angitte oppløsningsmiddelmengde og den angitte emulgatormengde og fortynner konsentratet med vann til den ønskede konsentrasjon.
Med den virksomme stofftilbered-n-i-ng -sprøyter man kålblader (Brassica oleracea) duggfuktige og befenger dem med larver av kålmark (Plutella maculipennis).
Etter de angitte tider bestemmes utryddelsen i %. Herved betyr 100$ at alle larver ble utryddet, 0% betyr at ingen larver ble utryddet.
Virksomme stoffer, virksomme stoffkonsentrasjoner, vurderingstider og resultater fremgår av følgende tabell:
Eksempel C
Laphygma-prøve.
Oppløsningsmiddel: 15 vektdeler dimetylformamid.
Emulgator : 1 vektdel alkylarylpolyglykoleter.
For fremstilling av en egnet virksom stofftilberedning sammenblander man 1 vektdel virksomt stoff med den angitte oppløsningsmiddelmengde og den angitte emulgatorme,ngde og fortynner konsentratet med vann til den ønskede konsentrasjon .
Med den virksomme stofftilberedning sprøyter man bomullsblad (Gossypium hirsutum) duggfuktige og befenger dem med larver av gressfly (Laphygma exigua).
Etter de angitte tider bestemmes utryddelsen i %. Herved betyr 100$ at alle larver ble utryddet., 0% betyr at ingen larver ble utryddet.
Virksomme stoffer, virksomme stoffkonsentrasjoner, vurderingstider og resultater fremgår av følgende tabell:
Eksempel D.
Prøve med parasitterende fluelarver.
Oppløsningsmiddel: 35 vektdeler etylenpolyglykolmonometyleter.
35 vektdeler nonylfenolpolyglykoleter.
For fremstilling av en egnet virksom stofftilberedning sammenblander man 30 vektdeler av det angjeldende aktive stoff med den angitte oppløsningsmiddelmengde, som inneholder overnevnte emulgatormengde og fortynner det således dannede kon-sentrat med vann til den ønskede konsentrasjon. 30 - 50 fluelarver (Lucilia cuprina) bringes i et lite prøverør som inneholder ca. 1 cm^ hestemuskulatur. På dette hestekjøtt bringes 0,5 ml av den virksomme stofftilberedning. Etter 24 timer bestemmes utryddelsesgraden i %. Derved betyr 100$ at alle, og 0% at ingen larver er blitt utryddet.
Virksomme stoffer, virksomme stoffkonsentrasjoner og resultater fremgår av følgende tabell:
FremstiIlingseksempler.
Eksempel 1.
Til 5,4 g (0,03 mol) 4-trifluormetoksy-anilin oppløst i 80 cm^ toluen har man ved 60°C en oppløsning av 6,5 g (0,03 mol) 2,6-diklor-benzoylisocyanat i 20 cm^ toluen. Blandingen omrøres 2 timer ved 80°C, en del av oppløsnings-midlet avdestilleres i vakuum og det utfelte produkt frasuges. Etter tørkning får man 10 g (84,5$ av det teoretiske) av analyse-rent N-(4-trifluormetoksy-fenyl)-N'-(2,6-diklorbenzoyl)-urin-stoff med smeltepunkt på 202°C.
På analog måte som omtalt under eksempel 1 får
man de følgende forbindelser, idet det er mulig med en optimer-
Claims (3)
1. N-fenyl-N'-benzoy1-urinstoffer for anvendelse som insekticider, karakterisert ved formel (I)
hvori
R betyr halogenalkyl med 1-4 karbonatomer, R"<*>" betyr hydrogen eller halogen,
R 2 betyr halogen, nitro, alkyl eller alkoksy med 1-3 karbonatomer pr. alkyl- resp. alkoksyrest og
X betyr et oksygen- eller svovelatom, mens n betyr et tall fra 0-5.-
2. Insekticid middel, karakterisert ved et innhold av minst et N-fenyl-N'-benzoyl-urinstoff med formel (I) ifølge krav 1.
3. Insekticid middel, karakterisert ved et innhold av en forbindelse med formel
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2601780A DE2601780B2 (de) | 1976-01-20 | 1976-01-20 | N-Phenyl-N'-benzoylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO770042L NO770042L (no) | 1977-07-21 |
| NO149173B true NO149173B (no) | 1983-11-21 |
| NO149173C NO149173C (no) | 1984-02-29 |
Family
ID=5967721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO770042A NO149173C (no) | 1976-01-20 | 1977-01-06 | Substituerte n-fenyl-n`-benzoyl-urinstoffer for anvendelse som insekticider og insekticid middel inneholdende slike forbindelser |
Country Status (38)
| Country | Link |
|---|---|
| US (1) | US4139636A (no) |
| JP (1) | JPS6031820B2 (no) |
| AR (1) | AR219487A1 (no) |
| AT (1) | AT351864B (no) |
| AU (1) | AU504246B2 (no) |
| BE (1) | BE850524A (no) |
| BG (1) | BG25060A3 (no) |
| BR (1) | BR7700289A (no) |
| CA (1) | CA1124747A (no) |
| CH (1) | CH629759A5 (no) |
| CS (1) | CS194790B2 (no) |
| DD (1) | DD129394A5 (no) |
| DE (1) | DE2601780B2 (no) |
| DK (1) | DK150594C (no) |
| EG (1) | EG12374A (no) |
| ES (1) | ES455149A1 (no) |
| FI (1) | FI63019C (no) |
| FR (1) | FR2338928A1 (no) |
| GB (1) | GB1501607A (no) |
| GR (1) | GR62096B (no) |
| HU (1) | HU176471B (no) |
| IL (1) | IL51279A (no) |
| IT (1) | IT1085852B (no) |
| KE (1) | KE2871A (no) |
| MY (1) | MY7800373A (no) |
| NL (1) | NL7700578A (no) |
| NO (1) | NO149173C (no) |
| NZ (1) | NZ183094A (no) |
| OA (1) | OA05531A (no) |
| PH (1) | PH13080A (no) |
| PL (1) | PL101199B1 (no) |
| PT (1) | PT66078B (no) |
| RO (1) | RO72521A (no) |
| SE (1) | SE424858B (no) |
| SU (1) | SU655278A3 (no) |
| TR (1) | TR19015A (no) |
| YU (1) | YU39788B (no) |
| ZA (1) | ZA77303B (no) |
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| US5245071A (en) * | 1970-05-15 | 1993-09-14 | Duphar International Research B.V. | Organic compounds derived from urea or thiourea |
| USRE32418E (en) * | 1977-05-13 | 1987-05-12 | The Dow Chemical Company | Substituted(((phenyl)amino)carbonyl)-benzamides |
| US4170657A (en) * | 1977-05-13 | 1979-10-09 | The Dow Chemical Company | Substituted(((phenyl)amino)carbonyl)-benzamides |
| DE2860137D1 (en) * | 1977-07-28 | 1980-12-11 | Ciba Geigy Ag | N-phenyl-n'-benzoyl ureas, process for their preparation, substances containing them, and their use as pesticides |
| DE2801316A1 (de) * | 1978-01-13 | 1979-07-19 | Bayer Ag | Substituierte n-phenyl-n'-(2-chlor- 6-fluor-benzoyl)-harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als insektizide |
| DE2961629D1 (en) * | 1978-03-13 | 1982-02-18 | Ciba Geigy Ag | Substituted n-phenyl-n'-fluorbenzoyl ureas, methods for their preparation and their use in combating pests |
| ZA793186B (en) * | 1978-07-06 | 1981-02-25 | Duphar Int Res | New urea and thiourea compounds, method of preparing the new compounds, as well as insecticidal compositions on the basis of these compounds |
| DE2839462A1 (de) * | 1978-09-11 | 1980-03-27 | Basf Ag | Aroylharnstoffe |
| GR73690B (no) * | 1979-01-15 | 1984-04-02 | Celamerck Gmbh & Co Kg | |
| US4339460A (en) | 1979-02-01 | 1982-07-13 | Ciba-Geigy Corporation | Pesticidal N-[4-(3'-bromoallyloxy)-phenyl]-N'-benzoyl ureas |
| US4310548A (en) | 1979-02-01 | 1982-01-12 | Ciba-Geigy Corporation | Pesticidal N-tetrafluorophenyl-N'-benzoyl ureas |
| US4505931A (en) * | 1979-02-01 | 1985-03-19 | Ciba-Geigy Corporation | Pesticidal N-(4-alkenylthio)-phenyl-N'-benzoylureas |
| US4243680A (en) * | 1979-02-07 | 1981-01-06 | Thompson-Hayward Chemical Company | Method of reducing infestation of citrus rust mites on citrus trees |
| US4348412A (en) * | 1979-07-11 | 1982-09-07 | Ciba-Geigy Corporation | Insecticidal phenylureas and methods of use thereof |
| ZA804164B (en) * | 1979-07-11 | 1981-08-26 | Ciba Geigy | Phenylureas |
| DE2928410A1 (de) * | 1979-07-11 | 1981-01-29 | Schering Ag | Acylharnstoffe, insektizide mittel enthaltend diese verbindungen sowie verfahren zu ihrer herstellung |
| US4399152A (en) * | 1980-04-03 | 1983-08-16 | Duphar International B.V. | Substituted benzoyl ureas as insecticides |
| DE3023328A1 (de) * | 1980-06-21 | 1982-01-14 | Bayer Ag, 5090 Leverkusen | Substituierte benzol-(thio)harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| US4431671A (en) * | 1980-12-12 | 1984-02-14 | Ciba-Geigy Corporation | Phenylureas |
| AR242020A1 (es) * | 1981-07-30 | 1993-02-26 | Dow Chemical Co | N-aroil n'-fenil urea sustituidos, composiciones insecticidas que los incluyen y derivados 4-halo alcoxi o 4-alquiltio benzamidas. |
| US5416102A (en) * | 1981-11-10 | 1995-05-16 | Ciba-Geigy Corporation | Method of preventing the reinfestation of dogs and cats by fleas |
| CA1190246A (en) * | 1982-04-23 | 1985-07-09 | Martin Anderson | Benzoylphenylurea derivatives, their preparation and use as pesticides |
| US4438110A (en) | 1982-04-28 | 1984-03-20 | Union Carbide Corporation | Chewing insect toxicant compositions |
| DE3217619A1 (de) * | 1982-05-11 | 1983-11-17 | Bayer Ag, 5090 Leverkusen | 2,4-dihalogenbenzoyl-(thio)harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| DE3217620A1 (de) * | 1982-05-11 | 1983-11-17 | Bayer Ag, 5090 Leverkusen | 2,5-dihalogenbenzoyl-(thio)harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| DE3223505A1 (de) * | 1982-06-24 | 1983-12-29 | Bayer Ag, 5090 Leverkusen | Substituierte benzoyl-(thio)harnstoffe, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| US5001266A (en) * | 1982-07-26 | 1991-03-19 | The Dow Chemical Company | Substituted aniline compounds |
| US4868215A (en) * | 1982-07-26 | 1989-09-19 | The Dow Chemical Company | Substituted N-aroyl N'-phenyl urea compounds |
| US4529819A (en) * | 1982-08-02 | 1985-07-16 | The Dow Chemical Company | Method for making benzoylphenylureas |
| ZA835661B (en) * | 1982-09-16 | 1984-04-25 | Shell Res Ltd | Pesticidal benzoylurea compounds |
| US4560770A (en) * | 1983-02-09 | 1985-12-24 | Ciba-Geigy Corporation | Pesticidal compositions based on N-pyrrolylphenyl-N'-benzoylurea compounds |
| JPS6092260A (ja) * | 1983-10-27 | 1985-05-23 | Nippon Tokushu Noyaku Seizo Kk | 新規アニリン誘導体 |
| DE3431219A1 (de) * | 1984-08-24 | 1986-03-06 | Bayer Ag, 5090 Leverkusen | Benzoylharnstoffe |
| JPS6197255A (ja) * | 1984-10-18 | 1986-05-15 | チバ‐ガイギー アクチエンゲゼルシヤフト | 置換ｎ―ベンゾイル―ｎ’―２．５―ジクロロ―４―ヘキサフルオロプロピルオキシフェニル尿素、その製造方法及び該化合物を含有する組成物 |
| US5135953A (en) * | 1984-12-28 | 1992-08-04 | Ciba-Geigy | Use of acyl urea compounds for controlling endoparasites and ectoparasites of warm-blooded animals |
| US5288756A (en) * | 1985-10-14 | 1994-02-22 | Ciba-Geigy Corporation | Benzoylphenylureas |
| JPS62207250A (ja) * | 1986-02-28 | 1987-09-11 | チバ−ガイギ− アクチエンゲゼルシヤフト | ベンゾイルフェニル尿素、その製造方法および該化合物を含有する殺虫、殺ダニ剤 |
| US5157155A (en) * | 1987-02-04 | 1992-10-20 | Sumitomo Chemical Company, Limited | Benzoylurea derivative and its production and use |
| AU595417B2 (en) * | 1987-02-04 | 1990-03-29 | Sumitomo Chemical Company, Limited | A benzoylurea derivative and its production and use |
| US4925875A (en) * | 1987-07-21 | 1990-05-15 | Ciba-Geigy Corporation | N-benzoyl-N'-2,5-dihalo-4-perfluoroalkoxyphenylureas, pesticidal compositions containing them and their use in the control of pests |
| JP2661709B2 (ja) * | 1988-07-08 | 1997-10-08 | ダウ・ケミカル日本株式会社 | 高活性な農薬水和剤の製法 |
| DE19953775A1 (de) | 1999-11-09 | 2001-05-10 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| DE10018370A1 (de) * | 2000-04-14 | 2001-10-18 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| DE10043610A1 (de) * | 2000-09-05 | 2002-03-14 | Bayer Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| DE10248257A1 (de) * | 2002-10-16 | 2004-04-29 | Bayer Cropscience Ag | Wirkstoffkombinationen im insektiziden und akariziden Eigenschaften |
| DE102004001271A1 (de) | 2004-01-08 | 2005-08-04 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden Eigenschaften |
| DE102006031978A1 (de) * | 2006-07-11 | 2008-01-17 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| EP2039248A1 (de) * | 2007-09-21 | 2009-03-25 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| DE102007045957A1 (de) | 2007-09-26 | 2009-04-09 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akarziden Eigenschaften |
| EP2127522A1 (de) | 2008-05-29 | 2009-12-02 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| EP2410849A1 (de) | 2009-03-25 | 2012-02-01 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden eigenschaften |
| EP2382865A1 (de) | 2010-04-28 | 2011-11-02 | Bayer CropScience AG | Synergistische Wirkstoffkombinationen |
| CN102090409A (zh) * | 2011-03-25 | 2011-06-15 | 通化农药化工股份有限公司 | 1-(4-三氟甲氧基苯基)-3-(2，6-二氟苯甲酰基)脲与抗生素类杀虫剂农药复配制剂 |
| CN102177905B (zh) * | 2011-03-25 | 2013-07-17 | 通化农药化工股份有限公司 | 1-(4-三氟甲氧基苯基)-3-(2，6-二氟苯甲酰基)脲制剂 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL160809C (nl) * | 1970-05-15 | 1979-12-17 | Duphar Int Res | Werkwijze ter bereiding van benzoylureumverbindingen, alsmede werkwijze ter bereiding van insekticide prepara- ten op basis van benzoylureumverbindingen. |
| DE2232730A1 (de) * | 1972-07-04 | 1974-01-24 | Bayer Ag | Substituierte cyclohexan-2,6-dion-1carbonsaeureanilide und -thioanilide, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und fungizide |
| DE2405733C2 (de) * | 1974-02-07 | 1984-12-13 | Bayer Ag, 5090 Leverkusen | Amidocarbonylthiobarbitursäurederivate und deren Salze, Verfahren zu ihrer Herstellung sowie ihre Verwendung zur Bekämpfung von Insekten, Milben und Pilzen |
| DE2405732A1 (de) * | 1974-02-07 | 1975-08-21 | Bayer Ag | Ekto- und endoparasitenmittel |
| DE2438747C2 (de) * | 1974-08-13 | 1982-10-14 | Bayer Ag, 5090 Leverkusen | Benzoylureido-diphenyläther, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide |
| GB1460419A (en) * | 1975-02-06 | 1977-01-06 | Bayer Ag | Benzoylureido-diphenyl ethers and their use as insecticides |
| DE2504983C2 (de) * | 1975-02-06 | 1982-10-21 | Bayer Ag, 5090 Leverkusen | Benzoylureido-nitro-diphenyläther, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide |
| DE2531279C2 (de) * | 1975-07-12 | 1983-07-14 | Bayer Ag, 5090 Leverkusen | N-(3-Trifluormethyl-4-halogen-phenyl)- N'-benzoyl-harnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide |
-
1976
- 1976-01-20 DE DE2601780A patent/DE2601780B2/de active Granted
- 1976-12-30 OA OA56033A patent/OA05531A/xx unknown
-
1977
- 1977-01-06 NO NO770042A patent/NO149173C/no unknown
- 1977-01-07 YU YU37/77A patent/YU39788B/xx unknown
- 1977-01-13 RO RO7789040A patent/RO72521A/ro unknown
- 1977-01-14 PT PT66078A patent/PT66078B/pt unknown
- 1977-01-17 NZ NZ183094A patent/NZ183094A/xx unknown
- 1977-01-17 CH CH55077A patent/CH629759A5/de not_active IP Right Cessation
- 1977-01-17 BR BR7700289A patent/BR7700289A/pt unknown
- 1977-01-17 BG BG035178A patent/BG25060A3/xx unknown
- 1977-01-17 TR TR19015A patent/TR19015A/xx unknown
- 1977-01-17 GB GB1687/77A patent/GB1501607A/en not_active Expired
- 1977-01-18 PH PH19359A patent/PH13080A/en unknown
- 1977-01-18 DD DD7700196993A patent/DD129394A5/xx unknown
- 1977-01-18 IL IL51279A patent/IL51279A/xx unknown
- 1977-01-18 PL PL1977195379A patent/PL101199B1/pl unknown
- 1977-01-18 FI FI770137A patent/FI63019C/fi not_active IP Right Cessation
- 1977-01-18 IT IT19412/77A patent/IT1085852B/it active
- 1977-01-19 BE BE174196A patent/BE850524A/xx not_active IP Right Cessation
- 1977-01-19 ZA ZA77303A patent/ZA77303B/xx unknown
- 1977-01-19 CA CA270,015A patent/CA1124747A/en not_active Expired
- 1977-01-19 CS CS77367A patent/CS194790B2/cs unknown
- 1977-01-19 ES ES455149A patent/ES455149A1/es not_active Expired
- 1977-01-19 SU SU772439799A patent/SU655278A3/ru active
- 1977-01-19 DK DK019877A patent/DK150594C/da not_active IP Right Cessation
- 1977-01-19 SE SE7700531A patent/SE424858B/xx not_active IP Right Cessation
- 1977-01-19 EG EG37/77A patent/EG12374A/xx active
- 1977-01-19 GR GR52607A patent/GR62096B/el unknown
- 1977-01-19 AU AU21449/77A patent/AU504246B2/en not_active Expired
- 1977-01-19 HU HU77BA3498A patent/HU176471B/hu unknown
- 1977-01-20 AT AT33777A patent/AT351864B/de not_active IP Right Cessation
- 1977-01-20 FR FR7701568A patent/FR2338928A1/fr active Granted
- 1977-01-20 JP JP52004478A patent/JPS6031820B2/ja not_active Expired
- 1977-01-20 NL NL7700578A patent/NL7700578A/xx not_active Application Discontinuation
- 1977-01-20 AR AR266261A patent/AR219487A1/es active
-
1978
- 1978-02-27 US US05/882,295 patent/US4139636A/en not_active Expired - Lifetime
- 1978-08-10 KE KE2871A patent/KE2871A/xx unknown
- 1978-12-30 MY MY373/78A patent/MY7800373A/xx unknown
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