NO138528B - Alkyl-n-(3-(n`-fenylcarbamoyloksy)-fenyl)-carbamater til anvendelse i herbicider - Google Patents
Alkyl-n-(3-(n`-fenylcarbamoyloksy)-fenyl)-carbamater til anvendelse i herbicider Download PDFInfo
- Publication number
- NO138528B NO138528B NO1458/72A NO145872A NO138528B NO 138528 B NO138528 B NO 138528B NO 1458/72 A NO1458/72 A NO 1458/72A NO 145872 A NO145872 A NO 145872A NO 138528 B NO138528 B NO 138528B
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- carbamoyloxy
- methylphenyl
- methyl
- herbicides
- Prior art date
Links
- 239000004009 herbicide Substances 0.000 title claims description 6
- -1 3- (N`-PHENYL CARBAMOYLOXY) -PHENYL Chemical class 0.000 title description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 25
- 239000013543 active substance Substances 0.000 description 10
- 241000196324 Embryophyta Species 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000002363 herbicidal effect Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 244000300264 Spinacia oleracea Species 0.000 description 2
- 235000009337 Spinacia oleracea Nutrition 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000003977 halocarboxylic acids Chemical class 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 150000007530 organic bases Chemical group 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- NJYFRQQXXXRJHK-UHFFFAOYSA-N (4-aminophenyl) thiocyanate Chemical compound NC1=CC=C(SC#N)C=C1 NJYFRQQXXXRJHK-UHFFFAOYSA-N 0.000 description 1
- ZRRCPKLWTBJUHI-UHFFFAOYSA-N 1-[(2,3,6-trichlorophenyl)methoxy]propan-1-ol Chemical compound CCC(O)OCC1=C(Cl)C=CC(Cl)=C1Cl ZRRCPKLWTBJUHI-UHFFFAOYSA-N 0.000 description 1
- HHIRBXHEYVDUAM-UHFFFAOYSA-N 1-chloro-3-isocyanatobenzene Chemical compound ClC1=CC=CC(N=C=O)=C1 HHIRBXHEYVDUAM-UHFFFAOYSA-N 0.000 description 1
- NDUPDOJHUQKPAG-UHFFFAOYSA-M 2,2-Dichloropropanoate Chemical compound CC(Cl)(Cl)C([O-])=O NDUPDOJHUQKPAG-UHFFFAOYSA-M 0.000 description 1
- JSIAIROWMJGMQZ-UHFFFAOYSA-N 2h-triazol-4-amine Chemical class NC1=CNN=N1 JSIAIROWMJGMQZ-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 244000237956 Amaranthus retroflexus Species 0.000 description 1
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 235000008427 Brassica arvensis Nutrition 0.000 description 1
- 244000024671 Brassica kaber Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- PXRROZVNOOEPPZ-UHFFFAOYSA-N Flupropanate Chemical compound OC(=O)C(F)(F)C(F)F PXRROZVNOOEPPZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000520028 Lamium Species 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 240000003705 Senecio vulgaris Species 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000207763 Solanum Species 0.000 description 1
- 235000002634 Solanum Nutrition 0.000 description 1
- 240000006694 Stellaria media Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- FBYUNLMTXMFAQK-UHFFFAOYSA-N butyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCCC.CCCCCCCCCCCC(=O)OCCCC FBYUNLMTXMFAQK-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbamic acid group Chemical group C(N)(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 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
- 229920005610 lignin Polymers 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- CXLDVCHKDQNLKM-UHFFFAOYSA-N methyl n-(3-hydroxy-4-methylphenyl)carbamate Chemical compound COC(=O)NC1=CC=C(C)C(O)=C1 CXLDVCHKDQNLKM-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical class ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
- C07C271/58—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Foreliggende oppfinnelse angår de nya forbindelser methyl-N- (3- (N '- (3 '-methylf enyl)-carbamoyloxy)-14— methylf enyl)-carbamat og methyl-N- (3- (N '- (3 "-klorf.en.yl)-carbamoyloxy)- h-methylfenyl)-carbamat, som er virksomme herbicider.
I tysk offentliggjorelsesskrift nr. 1' 920 775 be-
skrives methyl-N- (3- (N'- (3 ' , h '-diklorf enyl)-carbamoyloxy)-L(— methylfenyl)-carbamat med herbicid virkning, som skal være det i praksis kjente methyl-N-(3-(N'-(3'-methylfenyl)-carbamoyloxy)-fenyl)-carbatnat overlegent.
Det har nu vist seg at forbindelsene, av den generelle formel:
hvor X sr klor eller methyl, oppviser -en god herbicid virkning og overtreffer det kjente <!>+-methylfenyl-biscarbamat heri.
Gjenstanden for foreliggende oppfinnelse er derfor nye forbindelser av den angitte generelle formel (I) med herbicid vi rkning.
Forbindelsene ifolge oppfinnelsen har.overraskende nok ikke bare en i sammenligning med det konstitusjonsanaloge virkestoff av samme virkeretning oket herbicid, virksomhet, men har dessuten også fordelen av en god forlikelighet med nytteplanter. Som nytteplanter kan her spesielt nevnes slike som ved direkte kontakt med sprøytemidlet ved en behandling i post-emergens-metoden som regel er særlig omfintlig overfor herbicider, som f.eks. beta-roer og spinat.
Forbindelsene ifolge oppfinnelsen er særlig egnet til bekjempelse av åkerugress som f.eks. Stellaria media,
Sinapis arvensis, Solanum, Senecio vulgaris, Lamium-arter, Amaranthus retroflexus, Setaria-arter og andre.
Bruks mengdene for en tilstrekkelig ag r a o 3 bek j onip als a, særlig i kulturer av beta-iroer og spinat, utgjor ca. 0,3 til 3 kg virkestoff/ha. Overraskende nok kan disse anvendelse sme/igder okes til 5 kg virkestoff/ha og mere,.uten at nytteplantekulturene derved skades, slik at der er et betraktelig sikkerhetsområde ved anvendelse av disse forbindelser.
Forbindelsene ifolge oppfinnelsen kan enten anvendes alene eller i blanding med andre virkestoffer. Eventuelt kan andre plantevern- eller pestbekjempelsesmidler, f.eks. fungicider, -Nema-todicider eller andre midler, tilsettes alt efter det onskede for-mål. En tilsetning av gjodningsstoffer er f.eks. likeledes mulig.
Såfremt der onskes å gjore virkningsspektret bredere, kan
også herbicider tilsettes, hvorved imidlertid selektiviteten natur-ligvis ikke alltid opprettholdes. Som herbicid virksomme blandings-partnere eguer seg f.eks. virkestoffer fra gruppen carbamidsyre-
og thiocnrbamidsyreestere, de substituerte aniliner og anilider, triaziner, amino-triazoler, diaziaer, som uraciler, f.eks. 3-cyclo-hexyl-5,6-trimethyluracil, 1-fenyl-lf-amiio-5-klorpyridazon(6) , alifatiske carboxylsyrer og halogencarboxyisyrer, halogenerte benzoe-syrer og fenyleddiksyrer, aryloxycarboxylsyrer, hydrazider, amider, nitriler, halogencarboxyisyrer, f.eks. 2,2-diklorpropionsyre eller dens salter, tetrafluorpropionsyre eller dens salter, estere av slike carboxylsyrer, ureaer, 2,3,6-triklorbenzyloxypropanol, rhodan-holdige midler og andre.
Alt efter anvendelsesformålet kan også andre stoffer tilsettes, blant disse f.eks. også ikke-fytotoksiske tilsetninger, som med herbicidene kan gi en synergistisk virkningsokning, som fuktemidler, emulgatorer, opplosningsmidler, oljeaktige tilsetninger og andre.•
Hensiktsmessig anvendes virkestoffene ifolge oppfinnelsen i form av preparater som pulvere, stromidler, granulater, opplosninger, emulsjoner eller suspensjoner, under tilsetning av flytende og/eller faste bærerstoffer, henholdsvis fortynningsmidler, og eventuelt fukte-, hefte-, emulgerings- og/eller dispergeringshjelpemidler.
Egnede flytende bærerstoffer er f.eks. vann, alifatiske og aromatiske hydrocarboner som benzen, toluen, xylen, cyclohexanon, isoforon, dessuten mineraloljefraksjoner.
Som faste bærerstoffer egner seg mineraljord, f.eks. tonsil, silicagel, talkum, kaolin, attaclay, kalksten, kiselsyre og plante-produkter, f.eks. mel.
Av overflateaktive stoffer kan nevnes f.eks. calciumlignin-sulfonat, polyoxyethylen-octylfenolether, nafthalensulfonsyrer, fenolsulfonsyrer, formaldehydkondensater, fettalkoholsulfåter og alkali- og jordalkalisalter av fettsyrer.
Mengden av virkestoffet eller virkestoffene i de forskjellige preparater kan variere innen vide grenser. Eksempelvis inneholder midlene ca. 20 - 80 vekt# virkestoffer, ca. 80 - 20 vekt# flytende eller faste bærerstoffer såvel som eventuelt inntil 20 vekt# over-
flateaktive midler.
Påføringen av midlene kan skje på vanlig måte, f.eks. med vann som bærer 1 sproytevæsker, på 100 - 1000 l/ha. For total ugressbekjempelse kan under visse omstendigheter påfores nodvendige sproytevæskemengder på mer enn 1000 l/ha. En anvendelse av midlene i såkalt "ultralavvolum-metoder" er likeledes mulig og også deres anvendelse i form av såkalte mikrogranulater.
De nye forbindelser av formel (I) fremstilles f.eks. fra klormaursyre-3-alkoxycarbonylamino-6-methylfenylesteren ved omsetning med kloraniliner eller toluidiner,- eller fra 3-alkoxycarbonylamino-6-methylfenol og de tilsvarende isocyanater, fortrinnsvis under tilsetning av katalytiske mengder av en tertiær organisk base som f.eks. triethylamin, eller en organisk tinnforbindelse som f.eks. dibutyl-dilaurat. De kan også fremstilles fra de tilsvarende 3-nitrofenyl-6-methyl-N-arylcarbamater ved hydrering av nitrogruppen til amino-gruppen, f.eks. under anvendelse av Raney-nikkel/hydrogen i methanol og påfblgende omsetning med klormaursyre-alkylester, fortrinnsvis under tilsetning av en uorganisk eller en organisk tertiær base.
Fremstillingen av forbindelsene av den generelle formel (I)
kan derfor skje:
a) ved omsetning av en forbindelse av den generelle formel:
med isocyanater av den generelle formel: hvor X er som ovenfor angitt, i nærvær av en katalysator, fortrinnsvis en tertiær organisk base eller en organisk tinnforbindelse, eller b) ved omsetning av en forbindelse,av den generelle formel:
med aminer av den generelle formel:
hvor X er som ovenfor angitt, i nærvær av en syreakseptor, eller c) ved katalytisk reduksjon av en forbindelse av den generelle formel:
hvor X er som ovenfor angitt, til det tilsvarende amin med påfolg-ende omsetning med en forbindelse av den generelle formel:
De folgende eksempler belyser fremstilling av forbindelsene ifolge oppfinnelsen.
Methyl- N-( N'-( 3'- klorfenyl)- carbamoyloxy)-^- methylfenyl)- carbamat
En opplesning av 9?06 g (0,05 mol) 3-methoxycarbonylamino-6-methylfenol i 50 ml tetrahydrofuran tilsettes 0,5 ml triethylamin og 8,<!>+ g 3-klorfenylisocyanat. Efter 3 timer ved værelsetemperatur felles reaksjonsproduktet ved tilsetning av pentan. •
Utbytte: lk, 8 g = 88,5$ av det teoretiske.
Sm.p.: 165 - 1S6°C.
Analogt kan methyl-N-(3-(N'-(3' -methylfenyl) -carbamoyloxy)-1!--methylfenyl)-carbarnat fremstilles.
Sm.p.: 175 - 176°C.
Forbindelsene ifolge oppfinnelsen er uoppløselige i vann og bensin, og opploselige i aceton, tetrahydrofuran, dimethylformamid og dimethylsulfoxyd.
Av de folgende eksempler fremgår den herbicide virkning av forbindelsene ifolge oppfinnelsen.
Eksempel
I drivhus ble de nedenfor anforte planter i post-ernergens-tilstand behandlet med forbindelsene ifolge oppfinnlsen: Methyl-N-(3-(N'-(3'-methylfenyl)-carbamoyloxy)-^-methylfenyl)-carbamat og methyl-N-(3-(N1-(3'-klorfenyl)-carbamoyloxy)-4-methylfenyl)-carbarnat, såvel som med sammenligningsforbindelsen methyl-N-(3-(N1 -(3' -diklorfenyl) -carbamoyloxy) -4-methylfenyl) -carbamat ved påforingsmengder av 1 kg virkestoff/ha. Midlene ble påfort som emulsjoner i 500 1 vann pr. hektar. Bedommelsen skjedde 1'4 dager efter behandlingen.
Videre ble forbindelsene ifolge oppfinnelsen: methyl-N-(3- (N'-(3'-methylfenyl)-carbamoyloxy)-^-methylfenyl)-carbamat (I) og
methyl-N- (3- (N '- (3 '-klorf enyl)-carbamoyloxy)-1+-methylf enyl)-carbamat (II)
sammenlignet med forbindelsen
methyl-N-(3-(N'~(3'-klorfenyl)-carbamoyloxy)-fenyl)-carbamat (V) ifolge norsk patent 12<+ 109 ved post-emergensbehandling av de i tabell 2 angitte plantearter i drivhus. Forbindelsene ble an-vendt i en mengde på 3 kg virkestoff pr. hektar, emulgert i 500 1 vann pr. hektar. Bedommelsen skjedde lh dager efter behandling..
Som det sees av tabell 2, hadde forbindelsene ifolge oppfinnelsen en bedre forlikelighet med kulturplantene enn sammenligningsforbindelsen.
Claims (1)
- Alkyl-N-(3-(N'-fenylcarbamoyloksy)-fenyl)-carbamater til anvendelse i herbicider.karakterisert ved at de har den generelle formel:hvor X er klor eller methyl.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2121957A DE2121957C3 (de) | 1971-04-27 | 1971-04-27 | Diurethane sowie diese enthaltende herbizide Mittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO138528B true NO138528B (no) | 1978-06-12 |
| NO138528C NO138528C (no) | 1978-09-20 |
Family
ID=5806810
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1458/72A NO138528C (no) | 1971-04-27 | 1972-04-26 | Alkyl-n-(3-(n`-fenylcarbamoyloksy)-fenyl)-carbamater til anvendelse i herbicider |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US3869504A (no) |
| JP (1) | JPS5142172B1 (no) |
| AT (1) | AT315573B (no) |
| AU (1) | AU468474B2 (no) |
| BE (1) | BE782741A (no) |
| CA (1) | CA961501A (no) |
| CH (1) | CH563111A5 (no) |
| CS (1) | CS168457B2 (no) |
| DD (1) | DD100140A5 (no) |
| DE (1) | DE2121957C3 (no) |
| DK (1) | DK131853C (no) |
| ES (1) | ES401034A1 (no) |
| FI (1) | FI56526C (no) |
| FR (1) | FR2136704A5 (no) |
| GB (1) | GB1393964A (no) |
| HU (1) | HU164984B (no) |
| IE (1) | IE36324B1 (no) |
| IL (2) | IL39231D0 (no) |
| IT (1) | IT953689B (no) |
| LU (1) | LU65013A1 (no) |
| NL (1) | NL7205757A (no) |
| NO (1) | NO138528C (no) |
| PL (1) | PL83665B1 (no) |
| SE (1) | SE379760B (no) |
| SU (1) | SU528850A3 (no) |
| YU (1) | YU39162B (no) |
| ZA (1) | ZA722840B (no) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2703838A1 (de) * | 1977-01-31 | 1978-08-10 | Basf Ag | Diurethane |
| JPS5434571U (no) * | 1977-08-09 | 1979-03-07 | ||
| JPS54147570U (no) * | 1978-04-04 | 1979-10-13 | ||
| JPS5897448U (ja) * | 1981-12-22 | 1983-07-02 | タイガー魔法瓶株式会社 | ガス器具の点火装置 |
| JPS59113653U (ja) * | 1983-01-14 | 1984-08-01 | 松下電器産業株式会社 | ガス点火装置 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3535101A (en) * | 1966-09-07 | 1970-10-20 | Schering Ag | Herbicide and algicide means |
-
1971
- 1971-04-27 DE DE2121957A patent/DE2121957C3/de not_active Expired
-
1972
- 1972-03-02 DD DD161259A patent/DD100140A5/xx unknown
- 1972-03-03 DK DK101672A patent/DK131853C/da not_active IP Right Cessation
- 1972-03-06 YU YU00566/72A patent/YU39162B/xx unknown
- 1972-03-16 SU SU1759869A patent/SU528850A3/ru active
- 1972-03-17 CS CS1811A patent/CS168457B2/cs unknown
- 1972-03-21 ES ES401034A patent/ES401034A1/es not_active Expired
- 1972-03-21 LU LU65013D patent/LU65013A1/xx unknown
- 1972-03-28 FI FI864/72A patent/FI56526C/fi active
- 1972-04-06 US US241801A patent/US3869504A/en not_active Expired - Lifetime
- 1972-04-16 IL IL7239231Q patent/IL39231D0/xx unknown
- 1972-04-18 CH CH571272A patent/CH563111A5/xx not_active IP Right Cessation
- 1972-04-18 IL IL39231A patent/IL39231A/xx unknown
- 1972-04-19 IT IT23348/72A patent/IT953689B/it active
- 1972-04-24 GB GB1893372A patent/GB1393964A/en not_active Expired
- 1972-04-25 IE IE544/72A patent/IE36324B1/xx unknown
- 1972-04-25 SE SE7205443A patent/SE379760B/xx unknown
- 1972-04-25 PL PL1972154971A patent/PL83665B1/pl unknown
- 1972-04-26 AU AU41580/72A patent/AU468474B2/en not_active Expired
- 1972-04-26 HU HUSCHE389*1A patent/HU164984B/hu unknown
- 1972-04-26 JP JP47042549A patent/JPS5142172B1/ja active Pending
- 1972-04-26 NO NO1458/72A patent/NO138528C/no unknown
- 1972-04-26 FR FR7214827A patent/FR2136704A5/fr not_active Expired
- 1972-04-26 AT AT367072A patent/AT315573B/de active
- 1972-04-27 ZA ZA722840A patent/ZA722840B/xx unknown
- 1972-04-27 NL NL7205757A patent/NL7205757A/xx not_active Application Discontinuation
- 1972-04-27 BE BE782741A patent/BE782741A/xx not_active IP Right Cessation
- 1972-04-27 CA CA140,756A patent/CA961501A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2121957C3 (de) | 1979-11-29 |
| SE379760B (no) | 1975-10-20 |
| IL39231D0 (en) | 1972-06-28 |
| AT315573B (de) | 1974-05-27 |
| NL7205757A (no) | 1972-10-31 |
| YU39162B (en) | 1984-08-31 |
| BE782741A (fr) | 1972-10-27 |
| YU56672A (en) | 1982-05-31 |
| FI56526B (fi) | 1979-10-31 |
| ZA722840B (en) | 1973-02-28 |
| CA961501A (en) | 1975-01-21 |
| DK131853C (da) | 1976-03-08 |
| IT953689B (it) | 1973-08-10 |
| IL39231A (en) | 1975-03-13 |
| IE36324B1 (en) | 1976-10-13 |
| SU528850A3 (ru) | 1976-09-15 |
| IE36324L (en) | 1972-10-27 |
| CH563111A5 (no) | 1975-06-30 |
| FR2136704A5 (no) | 1972-12-22 |
| DE2121957A1 (de) | 1972-11-16 |
| DK131853B (da) | 1975-09-15 |
| JPS5142172B1 (no) | 1976-11-13 |
| US3869504A (en) | 1975-03-04 |
| DE2121957B2 (de) | 1979-03-29 |
| DD100140A5 (no) | 1973-09-12 |
| GB1393964A (en) | 1975-05-14 |
| PL83665B1 (no) | 1975-12-31 |
| CS168457B2 (no) | 1976-06-29 |
| ES401034A1 (es) | 1975-01-16 |
| FI56526C (fi) | 1980-02-11 |
| LU65013A1 (no) | 1972-07-11 |
| AU468474B2 (en) | 1976-01-15 |
| AU4158072A (en) | 1973-11-01 |
| HU164984B (no) | 1974-05-28 |
| NO138528C (no) | 1978-09-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HU213362B (en) | Herbicidal copositions containing n-/(1,3,5-triazine-2-yl)-carbamoyl/-benzol-sulfonamide derivatives and method for producing the active agents and for weed control | |
| US4129436A (en) | N'-[4-(substituted phenethyloxy)phenyl]-N-methyl-N-methoxyurea | |
| US4123256A (en) | N-(4-substituted benzyloxy)phenyl)-N-methyl-N-methoxyurea | |
| US5071470A (en) | Herbicidal 1,3,5-triazin-2-ylaminocarbonylamino-sulfonylbenzoic esters | |
| NO138528B (no) | Alkyl-n-(3-(n`-fenylcarbamoyloksy)-fenyl)-carbamater til anvendelse i herbicider | |
| EP0000324B1 (en) | Substituted cyclopropylmethoxy anilides, their preparation and their use as herbicides | |
| NO135471B (no) | ||
| AU613008B2 (en) | Novel cyclohexanediones | |
| CA1056394A (en) | M-diurethanes | |
| GB1596224A (en) | Substituted benzene-1,3-diurethanes and their use as herbicides and fungicides | |
| JPS6256864B2 (no) | ||
| US3872157A (en) | Substituted anilide carbamates | |
| NO135472B (no) | ||
| US4153447A (en) | Herbicidal methylphenyl carbamates | |
| US3969102A (en) | Herbicides | |
| US3242209A (en) | Iminomethyleneureas | |
| US4843177A (en) | Substituted acetamide derivatives with an antidote action, antidote compositions containing such compounds, selective herbicide compositions containing these antidotes and a process for the preparation of substituted acetamide derivatives | |
| JPH0453863B2 (no) | ||
| US4257805A (en) | Herbicidal (4-substituted-phenylamino)-3-(trifluoromethyl)phenyl)ureas | |
| EP0269141B1 (en) | 1-carbamoyl-2-pyrazoline derivatives having herbicidal activity | |
| US4239524A (en) | Thiadiazolyl ureas with herbicidal effect | |
| US4039315A (en) | N-(Difluorochloromethylmercaptophenyl)ureas as herbicides | |
| US3931312A (en) | Novel N(-difluoromethylmercaptophenyl) urea compounds and herbicidal compositions | |
| CA1221379A (en) | Herbicidal 2-haloacetanilides | |
| IL44275A (en) | Carbamoyloxyphenyl-carbamic acid esters and herbicidal compositions containing the same |