NL8000112A - DIURETHANES, METHOD FOR PREPARING THE SAME, AND HERBICIDES BASED ON THESE COMPOUNDS. - Google Patents
DIURETHANES, METHOD FOR PREPARING THE SAME, AND HERBICIDES BASED ON THESE COMPOUNDS. Download PDFInfo
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Nh * TO 8790Nh * TO 8790
Diurethanen, werkwijze voor het bereiden daarvan, alsmede op deze verbindingen gebaseerde herbiciden.Diurethanes, process for their preparation, as well as herbicides based on these compounds.
De uitvinding heeft betrekking op diurethanen, op een werkwijze voor het bereiden daarvan, alsmede op herbiciden op basis van deze verbindingen.The invention relates to diurethanes, to a process for their preparation, and to herbicides based on these compounds.
De herbicide-werking van diurethanen is reeds bekend. Be-5 kende actieve verbindingen van dit type bezitten een selectieve herbicidewerking, in het bijzonder met betrekking tot Beta-bieten (Duits octrooischrift 1.567*151) of sojabonen (Duits oc-trooischrift 2.658.897)*The herbicidal action of diurethanes is already known. Known active compounds of this type have a selective herbicidal action, in particular with respect to Beta beet (German patent 1,567 * 151) or soybeans (German patent 2,658,897) *
De onderhavige uitvinding heeft tot doel de ontwikkeling 10 van een herbicide, dat een zeer goede werking bezit ten opzich te van moeilijk te bestrijden onkruidsoorten en tegelijkertijd een verdraaglijkheid, in het bijzonder ten opzichte van katoen-culturen, vertoont.The object of the present invention is to develop a herbicide which has a very good effect on difficult to control weeds and at the same time exhibits tolerability, in particular with respect to cotton cultures.
Dit probleem wordt volgens de uitvinding opgelost door een 15 herbicide, dat gekenmerkt is, doordat het ten minste een ver binding met de algemene formule 1 bevat, waarin C^-C^-alkyl of fenylethyl; Rg C^C^-alkyl, halogeen-C,,-C^-alkyl, Cg-C^-alkenyl, halogeen-C^-C^-alkenyl, Cg-C^-alkynyl of halogeen-C^-C^-alkynyl} Y waterstof of fluor en X zuurstof of zwavel 20 voorstellen.This problem is solved according to the invention by a herbicide, characterized in that it contains at least one compound of the general formula 1, in which C 1 -C 2 alkyl or phenylethyl; Rg C ^ C ^ -alkyl, halogen-C, -C1 -alkyl, Cg-C ^ -alkenyl, halogen-C ^ -C ^ -alkenyl, Cg-C ^ -alkynyl or halogen-C ^ -C ^ -alkynyl} Y represent hydrogen or fluorine and X oxygen or sulfur.
De verbindingen volgens de uitvinding vertonen verrassen-derwijze een uitstekende verdraaglijkheid in katoenculturen, hetgeen bij de bekende verbindingen met analoge constitutie niet het geval is.The compounds of the invention surprisingly exhibit excellent tolerability in cotton cultures, which is not the case with the known analogous compounds.
25 De nieuwe verbindingen vertonen bovendien.een zeer goede werking ten opzichte van moeilijk te bestrijden onkruidsoorten, zoals Amaranthus, Stellaria, Matricaria, en andere, die zowel vóór als na het opkomen bestreden kunnen worden.The new compounds also show a very good effect against difficult to control weeds, such as Amaranthus, Stellaria, Matricaria, and others, which can be controlled both before and after emergence.
Toor het bestrijden van deze zaad-onkruidsoorten zijn in 800 0 1 12 - 2 - de regel toe te passen hoeveelheden van 1 tot maximaal 5 kg actieve verbinding/ha voldoende, waarbij de verbindingen volgens de uitvinding behalve bij katoen ook bij andere culturen van verbruiksplanten, zoals soja, aardnoten, aardappelen, maïs, 5 rijst, Sorghum en graan, een selectieve werking vertonen.In order to control these seed weed species, amounts of 1 to a maximum of 5 kg of active compound / ha are generally sufficient in 800 0 1 12 - 2 - the compounds according to the invention, in addition to cotton, also being used in other cultures of consumer plants. such as soy, groundnuts, potatoes, corn, rice, sorghum, and grain, exhibit a selective action.
De verbindingen volgens de uitvinding kunnen hetzij alleen, hetzij als mengsel onderling, hetzij als mengsel met andere actieve verbindingen worden toegepast. Desgewenst kunnen andere plantenbeschermingsmiddelen of middelen ter bestrijding van 10 schadelijke organismen, al naar gelang het gewenste doel, worden toegevoegd.The compounds of the invention can be used either alone or as a mixture with one another or as a mixture with other active compounds. If desired, other plant protection agents or agents for controlling harmful organisms, depending on the desired purpose, can be added.
Yoor zover een verbreding van het werkingsspeetrum beoogd wordt, kunnen ook andere herbiciden worden toegevoegd. Zo zijn b.v. als herbicide werkzame mengcomponenten geschikt: 15 actieve verbindingen uit-de groepen der triazinen, aminotriazo-len, aniliden, diazinen, uracilen, alifatische carbonzuren en halogeencarbonzuren, gesubstitueerde benzoëzuren en aryloxycar-bonzuren, hydraziden, amiden, nitrilen, 'esters van dergelijke carbonzuren,, carbamidezuuresters en thiocarbamidezuuresters, 20 ureumderivaten, 2,3,6-trichloorbenzyloxyisopropanol en thiocy-aan-bevattende middelen en andere. Onder andere toevoegsels dient b.v. ook te worden verstaan niet-fytotoxische toevoegsels, die bij herbiciden een synergistische verhoging van de werking tot stand brengen, zoals bevochtigingsmiddelen, emulgatoren, 25 oplosmiddelen en olie-achtige toevoegsels.As far as a broadening of the action spectrum is envisaged, other herbicides can also be added. For example, e.g. suitable herbicidal mixing components: active compounds from the groups of triazines, amino triazoles, anilides, diazines, uraciles, aliphatic carboxylic acids and halocarboxylic acids, substituted benzoic acids and aryloxycarboxylic acids, hydrazides, amides, nitriles, esters of such carboxylic acids, , carbamic acid esters and thiocarbamic acid esters, urea derivatives, 2,3,6-trichlorobenzyloxyisopropanol and thiocyanates and others. Among other additives, e.g. also to be understood non-phytotoxic additives which produce a synergistic increase in the effect of herbicides, such as wetting agents, emulsifiers, solvents and oily additives.
Het verdient aanbeveling de bovenomschreven nieuwe actieve verbindingen of mengsels daarvan toe te passen in de vorm van preparaten, zoals poeders, strooisels, granulaten, oplossingen, emulsies of suspensies, onder toevoeging van vloeibare en/of 30 vaste dragers of verdunningsmiddelen en desgewenst van bevoch-tigings-, hecht-, emulgeer- en/of dispergeermiddelen.It is recommended to use the above-described new active compounds or mixtures thereof in the form of preparations, such as powders, litters, granulates, solutions, emulsions or suspensions, with the addition of liquid and / or solid carriers or diluents and, optionally, of wetted toning, bonding, emulsifying and / or dispersing agents.
Geschikte vloeibare dragers zijn b.v. water, alifatische en aromatische koolwaterstoffen, zoals benzeen, tolueen, xyleen, cyclohexanon, isoforon, dimethylsulforyde, dimethylformamide en 800 0 1 12 * Λ - 3 - voorts frakties van minerale oliën.Suitable liquid carriers are e.g. water, aliphatic and aromatic hydrocarbons, such as benzene, toluene, xylene, cyclohexanone, isophorone, dimethyl sulforyde, dimethylformamide and 800 0 1 12 * Λ - 3 - further fractions of mineral oils.
Als vaste dragers zijn geschikt: minerale aarden, b.v, tonsil, silicagel, talk, kaolien, attaclay, kalksteen, kiezel-zuur en plantaardige produkten, b.v. meelsoorten.Suitable solid carriers are: mineral earths, e.g., tonsil, silica gel, talc, kaolin, attaclay, limestone, silicic acid and vegetable products, e.g. flours.
5 Als oppervlakactieve stoffen kunnen b.v. worden genoemd: calciumligninesulfonaat, polyoxyethyleen-alkylfenolethers, naftaleensulfonzuren en zouten daarvan, fenolsulfonzuren en zouten daarvan, formaldehyde-condensatieprodukten, vetalcohol-sulfaten, alsmede gesubstitueerde benzeensulfonzuren en de zou-10 ten daarvan.As surfactants, e.g. are mentioned: calcium lignin sulfonate, polyoxyethylene alkyl phenol ethers, naphthalene sulfonic acids and their salts, phenol sulfonic acids and their salts, formaldehyde condensation products, fatty alcohol sulfates, as well as substituted benzene sulfonic acids and their salts.
Het gehalte aan actieve verbinding of actieve verbindingen in de verschillende preparaten kan binnen ruime grenzen variëren. Zo bevatten de middelen b.v. ongeveer 5 tot 95 gew.$ actieve verbindingen, ongeveer 95 tot 5 gew.$ vloeibare of vaste 15 dragers, alsmede desgewenst ten hoogste 20 geir.% oppervlakac tieve verbindingen.The content of active compound or active compounds in the different preparations can vary within wide limits. For example, the agents contain e.g. about 5 to 95% by weight of active compounds, about 95 to 5% by weight of liquid or solid carriers, and optionally at most 20% by weight surfactants.
Het toepassen van de middelen kan op de gebruikelijke wijze plaatsvinden, b.v..met.water als drager in te verspuiten hoeveelheden van ongeveer 50 tot 1000 liter/ha. Toepassing van 20 de middelen bij de zogenaamde "Low-volume"- en "Ultra-Low-Volu- me"-werkwijze is even zeer mogelijk als toepassing in de vorm van zogenaamde microgranulaten.The use of the agents can take place in the usual manner, for instance with amounts of about 50 to 1000 liters / ha to be sprayed with water as a carrier. The use of the agents in the so-called "Low-volume" and "Ultra-Low-Volume" process is just as possible as use in the form of so-called micro-granulates.
Voorbeelden van de in de algemene formule door B1 voorgestelde groepen zijn b.v. methyl, ethyl, propyl, isopropyl, 25 butyl, isobutyl, sec-butyl of 2-fenylethyl en voorbeelden van de door E^ voorgestelde groepen zijn methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, allyl, propargyl, ehloor-ethyl, 1-chloormethylethyl, 4-cbloorbutynyl, 1-methylpropynyl en 4-cbloorbutenyl.Examples of the groups represented by B1 in the general formula are e.g. methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or 2-phenylethyl and examples of the groups represented by E 1 are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, allyl, propargyl, chloroethyl, 1-chloromethyl ethyl, 4-chlorobutynyl, 1-methylpropynyl and 4-chlorobutyl.
30 Van de verbindingen volgens de uitvinding munten door een uitstekende selectieve herbicide-werking in het bijzonder uit: IT-ethyl-3-fluorcarbanilzuur-(3-ethoxycarbonylaminofenyl)-ester, lT-ethyl-3-fluorcarbanilzuur-(3-methoiycarbonylaminofenyl)-ester, N-ethyl-3-fluorcarbanilzuur-^3-(1-methylethoxycarbonylamino)- 800 0 1 12 - 4 - fenyl__7-ester, E-ethyl-4-fluorcarbanilzuur-(3-ethoxycarbonyl-aminofeny1)-ester, 4-fluor-E-methylcarbanilzuur-(3-e thoxycar-bony laminof eny l) -ester, N-ethyl-3-fluorcarbanilzuur-/~3-0-methylethoxycarbonylamino)-fenyl_7-ester, F-ethyl-4-fluorcar-5 banilzuur-/”3-(l-methylethoxycarbonylamino)-fenyl_7-ester, 4- fluor-E-methylcarbanilzuur-/- 3-(l-oethylethoxycarbonylamino)-fenyl_7-ester, 3-fluσr-l!T-methylcarbanilzuuΓ-/,'"3-(l-niethylethoxy-carbonylamino)-fenylJ7-ester, E-ethyl-3,4-difluorcarbanilzuur-(3-ethoxycarbonylaminofenyl)-ester en ÏT-ethyl-2-fluorcarbanil- 10 zuur-(3-niethoxycarbonylaminofenyl)-ester.The compounds according to the invention excel in particular by their excellent selective herbicidal action: IT-ethyl-3-fluorobarbanilic acid (3-ethoxycarbonylaminophenyl) ester, 1T-ethyl-3-fluorobarbanilic acid (3-methylcarbonylaminophenyl) - ester, N-ethyl-3-fluorocarbanilic acid- ^ 3- (1-methylethoxycarbonylamino) - 800 0 1 12 - 4 - phenyl-7-ester, E-ethyl-4-fluorocarbanilic acid (3-ethoxycarbonylaminopheny1) -ester, 4- fluoro-E-methylcarbanilic acid (3-thoxycarbony laminofenyl) ester, N-ethyl-3-fluorobarbanilic acid / ~ 3-0-methyl-ethoxycarbonylamino) -phenyl-7-ester, F-ethyl-4-fluorcarcar-5 banilic acid - / "3- (1-methyl-ethoxycarbonylamino) -phenyl-7-ester, 4-fluoro-E-methylcarbanilic acid - / - 3- (1-ethyl-ethoxycarbonylamino) -phenyl-7-ester, 3-fluoro-1! -methylcarbanil-acid, / 3- (1-Nonhylethoxy-carbonylamino) -phenyl-7-ester, E-ethyl-3,4-difluororcarbanilic acid (3-ethoxycarbonylaminophenyl) ester and -T-ethyl-2-fluorocarbanilic acid (3-nonhoxycarbonylaminophenyl) -ester.
De tot nu toe niet bekende verbindingen kunnen worden be reid volgens een voor analoge verbindingen bekende methode.The previously unknown compounds can be prepared by a method known for analogous compounds.
Yolgens de uitvinding kunnen de nieuwe verbindingen worden bereid door: 15 a) verbindingen met de algemene formule 2 in tegenwoordig heid van een zuuracceptor, b.v. onder toevoeging van overmaat amine of van een anorganische base, zoals b.v, natronloog, na-triumcarbonaat, kaliumcarbonaat of een tertiaire organische base, zoals b.v. triëthylamine, om te zetten met een amine met de al- 20 gemene formule 3» of b) verbindingen met de algemene formule 4» in tegenwoordigheid van een tertiaire organische base, zoals b.v. triëthylamine of pyridine of in de vorm van alkalizouten, bij temperaturen van 0° tot 100°C te laten reageren met carbamoylchloriden met de 25 algemene formule 5» of c) verbindingen met de algemene formule 6 katalytisch, b.v. onder toepassing van nikkel in methanol, tot het overeenkomstige amine te hydrogeneren en vervolgens in tegenwoordigheid van een zuuracceptor, b.v. een anorganische base, zoals natronloog, 30 natriumcarbonaat of kaliumcarbonaat of van een tertiaire organische base, zoals b.v. triëthylamine, met verbindingen met de algemene formule 7, om te zetten in de gewenste eindprodukten en deze daarna op de gebruikelijke wijze te isoleren? waarbij in deze formules , Eg, Y en X de eerdergenoemde 800 0 1 12 - 5 - * «ir betekenissen bezitten.According to the invention, the new compounds can be prepared by: a) compounds of the general formula 2 in the presence of an acid acceptor, e.g. adding excess amine or an inorganic base, such as, for example, caustic soda, sodium carbonate, potassium carbonate or a tertiary organic base, such as e.g. triethylamine, reacting with an amine of the general formula 3 »or b) compounds of the general formula 4» in the presence of a tertiary organic base, such as e.g. triethylamine or pyridine or in the form of alkali salts, reacting with carbamoyl chlorides of the general formula 5 »at temperatures from 0 ° to 100 ° C, or c) compounds of the general formula 6 catalytically, e.g. using nickel in methanol to hydrogenate to the corresponding amine and then in the presence of an acid acceptor, e.g. an inorganic base, such as caustic soda, sodium carbonate or potassium carbonate, or of a tertiary organic base, such as e.g. converting triethylamine, with compounds of the general formula 7, into the desired end products and then isolating them in the usual manner? wherein in these formulas, Eg, Y and X the aforementioned 800 0 1 12 - 5 - 5 ir meanings.
De bereiding van de verbindingen volgens de uitvinding wordt door het volgende voorbeeld (i) nader toegelioht.The preparation of the compounds according to the invention is further illustrated by the following example (i).
Voorbeeld IExample I
5 N-Ethyl-3-fluorcarbanilzuur-/""3-(ethylthio-carbonylamino)- fenyl_/-ester-5 N-Ethyl-3-fluorocarbanilic acid - / "" 3- (ethylthio-carbonylamino) - phenyl / - ester-
In een oplossing van 13,9 S (.0,1 mol) N-ethyl-3-fluorani-line in 70 ml ethylacetaat werd onder roeren en koelen tot 10 tot 15°C een oplossing van 26,0 g (0,1 mol) chloormierezuur-10 /~3-(ethylthio-carbonylamino)-fenyl_i7’-ester in 70 ml ethylace taat en tegelijkertijd een oplossing van 13,8 g (0,1 mol) kali-umcarbonaat in 50 ml water gedruppeld. Bij 15°C werd 30 min nageroerd en vervolgens de organische fase afgescheiden en onder toevoeging van ijs met verdund zoutzuur en water gewassen. Na 15 drogen met magnesiumsulfaat werd onder verminderde druk inge dampt. Het indampresidu werd uit ethylacetaat/pentaan herkris-talliseerd.In a solution of 13.9 S (0.1 mol) N-ethyl-3-fluoroaniline in 70 ml ethyl acetate, a solution of 26.0 g (0.1) was added with stirring and cooling to 10 to 15 ° C. moles of chloroformic acid 10 / 3- (ethylthio-carbonylamino) -phenyl-17'-ester in 70 ml of ethyl acetate and at the same time drop a solution of 13.8 g (0.1 mole) of potassium carbonate in 50 ml of water. The mixture was stirred at 15 ° C for 30 min and then the organic phase was separated and washed with dilute hydrochloric acid and water under ice, with addition of ice. After drying with magnesium sulfate, evaporation was carried out under reduced pressure. The evaporation residue was recrystallized from ethyl acetate / pentane.
Opbrengst» 29,4 g » 81$ N-ethyl-3-fluorcarbanilzuur-/"*3-(ethylthiocarbonylamino)-fenyl__7-ester, smeltpunt 127°C.Yield »29.4 g» 81% N-ethyl-3-fluorocarbanilic acid - / * 3- (ethylthiocarbonylamino) -phenyl-7-ester, mp 127 ° C.
20 Op analoge wijze konden de volgende verbindingen volgens de uitvinding worden bereid»The following compounds according to the invention could be prepared in an analogous manner »
Naam van de verbinding Fysische constante 3- Fluor-N-methylcarbanilzuur-(3-methoxy- Smeltpunt» 105-107°C carbonylaminofenyl)-esterName of compound Physical constant 3- Fluoro-N-methylcarbanilic acid (3-methoxy- Melting point »105-107 ° C carbonylaminophenyl) ester
25 N-Ethyl-3-flnorcarbanilzuur-(3-methoxy- Smeltpunt» 108-109°C25 N-Ethyl-3-flororcarbanilic acid (3-methoxy- Melting point »108-109 ° C
carbonylaminofenyl)-ester N-Ethyl-3-flnorcarbanilzuur-/'-5-(methyl- Smeltpunt» 125-127°C thio-carbonylamino)-fenylJ7-estercarbonylaminophenyl) ester N-Ethyl-3-flororcarbanilic acid - / - - 5- (methyl Melting point »125-127 ° C thio-carbonylamino) -phenylJ7 ester
4- Fluor-N-methylcarbanilzuur-(3-methoxy- Smeltpunt» 96-, 97°C4- Fluoro-N-methylcarbanilic acid- (3-methoxy- Melting point »96-, 97 ° C
50 carbonylaminofenyl)-ester 4-Fluor-N-methylcarbanilzuur-/~3“(methyl- Smeltpunt» 106-108°C thio-carbonylamino)-fenyl7-ester N-Ethyl-4-fluorcarbanilzuur-/”3-(®ethyl- Smeltpunt» 143-144°C thio-carbonylamino)-fenyl_i7-e8ter 80 0 0 1 12 - 6 -50 carbonylaminophenyl) ester 4-Fluoro-N-methylcarbanilic acid- / ~ 3 "(methyl Melting point» 106-108 ° C thio-carbonylamino) -phenyl7-ester N-Ethyl-4-fluorocarbanilic acid - / "3- (®ethyl - Melting point »143-144 ° C thio-carbonylamino) -phenyl_i7-e8ter 80 0 0 1 12 - 6 -
Naam van de verbinding Fysische constante lT-Ethyl-4-fluorcarbanilzuur-(3-methoxy- Smeltpunt: 117—118°C carbonylaminofenyl)-esterName of the compound Physical constant 1T-Ethyl-4-fluorocarbanilic acid (3-methoxy- Melting point: 117—118 ° C carbonylaminophenyl) ester
H-Ethyl-4-fluorcarbanilzuur-(3-ethoxy- Smeltpunt: 76- 77°CH-Ethyl-4-fluorobarbanilic acid (3-ethoxy) Melting point: 76-77 ° C
5 carbonylaminofenyl)-esterCarbonylaminophenyl) ester
!T-Ethyl-3-fluorcarbanilzuur-(3-ethoxy- Smeltpunt: 122°CT-Ethyl-3-fluorocarbanilic acid (3-ethoxy) Melting point: 122 ° C
carbonylaminofenyl)-es tercarbonylaminophenyl) -ter
3-Fluor-H-methylcarbanilzuur-(3-ethoxy- Smeltpunt: 91- 92°C3-Fluoro-H-methylcarbanilic acid- (3-ethoxy- Melting point: 91-92 ° C
carbonylaminofenyl)-estercarbonylaminophenyl) ester
10 3-Fluor-li-methylcarbanilzuur-/~3-(niethyl- Smeltpunt: 116°C10 3-Fluoro-li-methylcarbanilic acid- / ~ 3- (nonhyl- Melting point: 116 ° C
thio-carbonylamino)-fenyl(_7-esterthio-carbonylamino) -phenyl (7-ester
3- Fluor-N-methylcarbanilzuur-/_3-(ethyl- Smeltpunt: 124-125°C3- Fluoro-N-methylcarbanilic acid - / _ 3- (ethyl- Melting point: 124-125 ° C
thio-carbonylamino)-fenyl_7-e ster 4- Fluor-ïT-methylcarbanilzuur-(3-ethoxy- η^20: 1 *5472 15 carbonylaminofenyl)-esterthio-carbonylamino) -phenyl-7-e star 4-Fluorotmethylcarbanilic acid (3-ethoxy-η ^ 20: 1 * 5472 15-carbonylaminophenyl) -ester
4-Fluor-H-(2-fenylethyl)-carbanilzuur- Smeltpunt: 137°C4-Fluoro-H- (2-phenylethyl) -carbanilic acid- Melting point: 137 ° C
(3-methoxycarbonylaminofenyl)-ester(3-methoxycarbonylaminophenyl) ester
4-Fluor-U-(2-fenylethyl)-carbanilzuür- - "Smeltpunt: 103-104°C (3-e thoxy carb onylaminof eny1)-e s t e r 20 N-Ethyl-3~fluorcarbanilzuur-/”3-(l- Smeltpunt: 9S°C4-Fluoro-U- (2-phenylethyl) -carbanilic acid- - "Melting point: 103-104 ° C (3-thoxy carbonyl aminophenyl) ester 20 N-ethyl-3-fluorocarbanilic acid - /" 3- (l- Melting point: 9S ° C
methylethoxycarbonylamino)-fenyl_7-ester N'-Ethyl-4-fluorcarbanilzuur-^""3-,(l“ Smeltpunt: 84- 86°Cmethylethoxycarbonylamino) -phenyl-7-ester N'-Ethyl-4-fluorocarbanilic acid - ^ "" 3 -, (l "Melting point: 84- 86 ° C
methylethoxycarbonylamino)-fenyl_7-estermethyl ethoxycarbonylamino) -phenyl-7-ester
4-Fluor-N-methylcarbanilzuur-/”3-0- Smeltpunt: 88°C4-Fluoro-N-methylcarbanilic acid - / ”3-0- Melting point: 88 ° C
25 methylethoxycarbonylamino)-fenylJ7-esterMethyl ethoxycarbonylamino) phenyl J7 ester
!I-Ethyl-4-fluorcarbanilzuur-/”3-(ethyl- Smeltpunt: 79°C1-Ethyl-4-fluorobarbanilic acid - / - 3- (ethyl Melting point: 79 ° C
thiocarbonylaminoj-fenyl^-esterthiocarbonylamino-phenyl-1-ester
4-Fluor-li-methylcarbanilzuur-/”3-(ethyl- Smeltpunt: 97- 99°C4-Fluoro-li-methylcarbanilic acid - / ”3- (ethyl- Melting point: 97-99 ° C
thiocarbonylamino)-fenyl_7-esterthiocarbonylamino) -phenyl-7-ester
30 3-Fluor-F-methylcarbanilzuur-/”3-(2- Smeltpunt: 142-144°C30 3-Fluoro-F-methylcarbanilic acid - / ”3- (2- Melting point: 142-144 ° C
propynyloxycarbonylamino)-fenyl_J7-esterpropynyloxycarbonylamino) phenyl J7 ester
IT-Ethyl-3-fluorcarbanilzuur-/”3-( 2- Smeltpunt: 148-150°CIT-Ethyl-3-fluorobarbanilic acid - / ”3- (2- Melting point: 148-150 ° C
propynyloxycarbonylamino)-fenyl_/-e ster 80 0 0 1 12 • + - 7 -propynyloxycarbonylamino) -phenyl _ / - e star 80 0 0 1 12 • + - 7 -
Naam van de verbinding Fysische constanteName of the connection Physical constant
4-Fluor-N-(2-fenylethyl)-carbanilzuur- Smeltpunt! 117°C4-Fluoro-N- (2-phenylethyl) -carbanilic acid- Melting point! 117 ° C
£" 3-( ethylthio-carbonylamino) -feny1J-ester3- (ethylthio-carbonylamino) -phenyl-1-ester
5 4-Fluor-N-(2-fenylethyl)-carbanilzuur- Smeltpunt: 81- 83°C5 4-Fluoro-N- (2-phenylethyl) -carbanilic acid- Melting point: 81-83 ° C
/"*3-( 1 -methyle thoxy carbonylamino) -fenyl_J -ester/ "* 3- (1-methyl-thoxycarbonylamino) -phenyl-J -ester
N-Ethyl-4-fluorcarbanilzuur-(3-allyloay- Smeltpunt: 73- 74°CN-Ethyl-4-fluorocarbanilic acid- (3-allyloay- Melting point: 73- 74 ° C
carbonylaminofenyl)-estercarbonylaminophenyl) ester
10 N-Ethyl-4-fluorcarbanilzuur-(3-propynyl- Smeltpunt: 79- 80°C10 N-Ethyl-4-fluorocarbanilic acid- (3-propynyl- Melting point: 79-80 ° C
oxycarbonylaminofenyl)-esteroxycarbonylaminophenyl) ester
4-Fluor-N-(2-fenylethyl)-carbanilzuur-(3- Smeltpunt: 81°C4-Fluoro-N- (2-phenylethyl) -carbanilic acid- (3- Melting point: 81 ° C
allyloxycarbonylaminofenyl)-ester 3-Fluor-N-(2-fenylethyl)-carbanilzuur-(3- Smeltpunt: 112-113°C 15 methoxycarbonylaminofenyl)-esterallyloxycarbonylaminophenyl) ester 3-Fluoro-N- (2-phenylethyl) -carbanilic acid- (3- Melting point: 112-113 ° C 15-methoxycarbonylaminophenyl) ester
N-Ethyl-2-fluoroarbanilzuur-(3-methojcy- Smeltpunt 106-107°CN-Ethyl-2-fluoroarbanilic acid- (3-methojcy- Melting point 106-107 ° C
carbonylaminofenyl)-estercarbonylaminophenyl) ester
N-Ethyl-3»4-difluorcarbanilzuur-(3- Smeltpunt: 121-122°CN-Ethyl-3 »4-difluorocarbanilic acid (3- Melting point: 121-122 ° C
metho3cycarbonylaminofenyl)-estermetho3cycarbonylaminophenyl) ester
20 3-Plnor-N-(2-fenylethyl)-qarbanilzuur-(3- Smeltpunt: 115°C20 3-Plnor-N- (2-phenylethyl) -carbanilic acid- (3- Melting point: 115 ° C
ethorycarbanylaminofenyl)-esterethorycarbanylaminophenyl) ester
3-Fluor-N-(2-fenylethyl)-earbanilzuur- Smeltpunt: 91- 93°C3-Fluoro-N- (2-phenylethyl) -earbanilic acid- Melting point: 91-93 ° C
C 3-( ethylthio-carbonylaaino)-fenyl_7-C 3- (ethylthio-carbonylaaino) -phenyl_7-
3-Fluor-N-methylcarbanilzuur-/-3-(1- Smeltpunt: 74- 76°C3-Fluoro-N-methylcarbanilic acid - / - 3- (1- Melting point: 74-76 ° C
25 methylethoxycarbonylamino)-fenylJ7-esterMethyl ethoxycarbonylamino) phenyl J7 ester
3-Fluor-N-methylcarbanilzuur-(3-allyloxy- Smeltpunt: 78- 80°C3-Fluoro-N-methylcarbanilic acid- (3-allyloxy- Melting point: 78-80 ° C
carbonylaminofenyl)-ester 3-Fluor-N'-ethylcarbanilzuur-(3-allyloxy- Smeltpunt: 101-103°C carbonylaminofenyl)-ester 30 4-Fluor-N-methylcarbanilzuur-(3-allyloxy- n^20: 1.5536 carbonylaminofenyl)«estercarbonylaminophenyl) ester 3-Fluoro-N'-ethylcarbanilic acid- (3-allyloxy- Melting point: 101-103 ° C carbonylaminophenyl) -ester 30 4-Fluoro-N-methylcarbanilic acid- (3-allyloxy-n ^ 20: 1.5536 carbonylaminophenyl) Ester
N-Ethyl-3-fluorcarbanilzuur-/”3-(l-chloor- Smeltpunt: 68- 70°CN-Ethyl-3-fluorobarbanilic acid - / ”3- (1-chlorine- Melting point: 68-70 ° C
methylethoxycarbonylamimO-fenyl^-ester 800 0 1 12 - 8 -methylethoxycarbonylamimO-phenyl-ester 800 0 1 12 - 8 -
Haam van de verbinding Fysische constante H-Ethyl-3t4-<iifluorcarbanilzuur-(3-ethoxy- Smeltpunt: 69- 70°0 carbonylaminofenyl)-esterName of the compound Physical constant H-Ethyl-3t4- <iifluorocarbanilic acid (3-ethoxy) Melting point: 69- 70 ° 0 carbonylaminophenyl) ester
H-Ethyl-3,4-4ifluorcarbanilzuur-/"”3- Smeltpunt: 130-132°CH-Ethyl-3,4-4ifluorocarbanilic acid - / "” 3- Melting point: 130-132 ° C
5 (methylthiocarbonylamino)-fenyl_7-ester5 (methylthiocarbonylamino) -phenyl-7-ester
2-Fluor-H-(2-fenylethyl)-carbanilzuur- Smeltpunt: 125-126°C2-Fluoro-H- (2-phenylethyl) -carbanilic acid- Melting point: 125-126 ° C
(3-methoxycarbonylaminofenyl)-ester(3-methoxycarbonylaminophenyl) ester
2-Fluor-H-(2-fenylethyl)-carbanilzuur- Smeltpunt: 128-130°C2-Fluoro-H- (2-phenylethyl) -carbanilic acid- Melting point: 128-130 ° C
(3-ethoxycarbonylamiaofenyl)-ester(3-ethoxycarbonylamiaophenyl) ester
10 2-Fluor-U-(2-fenylethyl)-carbanilzuur- Smeltpunt: 148-149°C10 2-Fluoro-U- (2-phenylethyl) -carbanilic acid- Melting point: 148-149 ° C
Z*5-C methylthiocarbonylamino)-fenylJ-esterZ * 5-C methylthiocarbonylamino) -phenyl J ester
2- Fluor-ïir-(2-fenylethyl)-carbanilzuur-/,’3- Smeltpunt: 124°C2- Fluorine (2-phenylethyl) -carbanilic acid - /, 3- Melting point: 124 ° C
(ethylthiocarbonylamino)-fenyl_7-ester -l;.(ethylthiocarbonylamino) -phenyl-7-ester -1;
15 2-Fluor-H-(2-fenylethyl)-carbanilzuur-/~3” Smeltpunt: 109-110°C15 2-Fluoro-H- (2-phenylethyl) -carbanilic acid / ~ 3 ”Melting point: 109-110 ° C
(1 -methylethoxycarbonylamino) -feny 1J- . ester(1-methylethoxycarbonylamino) -pheny 1J-. ester
3- Fluor-N-propylcarbanilzuur-(5-methoxy- Smeltpunt: -90- 92°C3- Fluoro-N-propylcarbanilic acid- (5-methoxy- Melting point: -90- 92 ° C
carbonylamino)-fenylestercarbonylamino) -phenyl ester
20 3-Fluor-H-propylcarbanilzuur-/”3-(jnethyl- Smeltpunt: 103-105°C20 3-Fluoro-H-propylcarbanilic acid - / ”3- (methyl- Melting point: 103-105 ° C
thiocarbonylamino)-fenyl__7-esterthiocarbonylamino) -phenyl-7-ester
3-Fluor-N-propylcarbanilzuur-(3-ethoxy- Smeltpunt: 103-105°C3-Fluoro-N-propylcarbanilic acid- (3-ethoxy- Melting point: 103-105 ° C
carbonylamino)-fenylestercarbonylamino) -phenyl ester
H-Ethyl-3-fluorcarbanilzuur-/—3-(1-methyl- Smeltpunt: 100-101°CH-Ethyl-3-fluorocarbanilic acid - / - 3- (1-methyl- Melting point: 100-101 ° C
25 2-propenyloxycarbonylamino)-fenylJT-ester2-propenyloxycarbonylamino) phenyl JT ester
H-Ethyl-2-fluorcarbanilzuur-/~3-(l-methyl- Smeltpunt: 109-110°CH-Ethyl-2-fluorobarbanilic acid- / ~ 3- (1-methyl- Melting point: 109-110 ° C
2-propenyloxycarbonylamino)-fenyl_7-ester H-Ethyl-4-fluorcarbanilzuur-/_3-(‘I-methyl- Smeltpunt: 73- 74°C2-propenyloxycarbonylamino) -phenyl-7-ester H-Ethyl-4-fluorobarbanilic acid - / - 3 - ("I-methyl- Melting point: 73- 74 ° C
2- propenyloxycarbonylamino)-fenyl_7~ester2-propenyloxycarbonylamino) -phenyl-7-ester
30 H-Butyl-3-fluorcarbanilzuur-(3-methoxy- Smeltpunt: 79- 80°C30 H-Butyl-3-fluorocarbanilic acid- (3-methoxy- Melting point: 79-80 ° C
carbonylamino)-fenylestercarbonylamino) -phenyl ester
3- Fluor-H-methylcarbanilzuur-/”3-(2- Smeltpunt: 94- 95°C3- Fluoro-H-methylcarbanilic acid - / ”3- (2- Melting point: 94-95 ° C
methylpropoxycarbonylamino)-fenyl_7-ester 80 0 0 1 12 _ 0 * - 9 -methylpropoxycarbonylamino) -phenyl-7-ester 80 0 0 1 12 _ 0 * - 9 -
Naam van de verbinding Fysische constante 4-Fluor-N-(2-feuylethyl)-carbaailzuur-/~3- 0^20: 1.5578 (1-methyl-2-propeayloxycarboaylamiao)-fenyl_7-ester 5 3-Fluor-ïï-(2-feaylethyl)-carbaailzuur-/""3- a^20: 1.5632 (1 -methyl-2-propeayloxycarboaylamiao) -fenyl_7-ester 3- Fluor-N-methylearbaailzuur-/"’3-(1-methyl a^20: 1.55Ö9 -2-propenyloxyearboaylamiao)-feayl_7-ester 10 4-Fluor-F-methylcarbaailzuur-/~3-(1-methyl a^20: 1.5465 -2-propenylo3cycarbonylamino)-fenyl_i7-ester lf-Butyl-4“fluorcarbaailzuur-^"3-( 1 -methyl- ^20: 1.5298 2-propenyloxycarboaylamiao)-fenyl_7-ester 4- Fluor-N-methylcarbaailzuur-^"3-(2-methyl*a^20s 1.5313 15 propoxycarboaylamiao)-feayl_7-esterName of the compound Physical constant 4-Fluoro-N- (2-feuyl ethyl) -carboxylic acid- ~ 3- 0 ^ 20: 1.5578 (1-methyl-2-propeayloxycarboaylamiao) -phenyl-7-ester 5 3-Fluoro-1-( 2-pheaylethyl) -carbic acid - / "" 3- a ^ 20: 1.5632 (1-methyl-2-propeayloxycarboaylamiao) -phenyl-7-ester 3- Fluoro-N-methyl-carboxylic acid - / "" 3- (1-methyl a ^ 20 : 1.55O9 -2-propenyloxyearboaylamiao) -pheayl-7-ester 10 4-Fluoro-F-methylcarboxylic acid- / ~ 3- (1-methyl a ^ 20: 1.5465 -2-propenylo3cycarbonylamino) -phenyl-7-ester 1-Butyl-4 "fluorocarboxylic acid - ^ "3- (1-methyl- ^ 20: 1.5298 2-propenyloxycarboaylamiao) -phenyl-7-ester 4- Fluoro-N-methylcarboxylic acid - ^" 3- (2-methyl * a ^ 20s 1.5313-propylcarboaylamiao) -pheayl_7-ester
4-Fluor-N-propylcarbaailzuur-^”3-(l-methyl Smeltpuat: 75- 76°C4-Fluoro-N-propyl carboxylic acid - ^ ”3- (1-methyl Melting point: 75-76 ° C
-2-propenyloxycarboaylamiao)-£eayl_7-ester-2-propenyloxycarboaylamiao) - eayl_7-ester
N-Ethyl-2-fluorcarbaailzuur-(3-ethoxy- Smeltpuat: 151 —153°CN-Ethyl-2-fluorocarboxylic acid (3-ethoxy- Melting point: 151 - 153 ° C
carbonylamiaofeayl)-estercarbonylamiaopheayl) ester
20 iï-Ethyl-2-fluorcarbaailzuur-(3-(methyl- Smeltpuat: 160-162°C20 i-Ethyl-2-fluorocarboxylic acid (3- (methyl- Melting point: 160-162 ° C
thiocarboaylamiao)-feayl)-esterthiocarboaylamiao (pheayl) ester
N-Ethyl-2-fluorcarbaailzuur-(3-ethylthio- Smeltpuat: 146-147°CN-Ethyl-2-fluorocarboxylic acid (3-ethylthio- Melting point: 146-147 ° C
carboaylamiao)-feayl)-estercarboaylamiaO-pheayl) ester
ÏT-Ethyl-2-fluorcarbaailzuur- (3-(1 -methyl- Smeltpuat: 126-127°CIT-Ethyl-2-fluorocarboxylic acid (3- (1-methyl- Melting point): 126-127 ° C
25 ethoxycarboaylamiao)-feayl)-esterEthoxycarboaylamiaO-pheayl) ester
N-Ethyl-2-fluorcarbaailzuur-(3-(2-propy- Smeltpuat: 150°CN-Ethyl-2-fluorocarboxylic acid- (3- (2-propy- Melting point: 150 ° C)
ayloxycarboaylamiao)-feay1)-esterayloxycarboaylamiao) -feay1) -ester
2-Fluor-N-(2-feaylethyl)-carbaailzuur-(3- Smeltpuat: 72- 73°C2-Fluoro-N- (2-feaylethyl) -carboxylic acid- (3-Melting point: 72-73 ° C
allyloxycarboaylamiao)-feayl)-esterallyloxycarboaylamiao) -feayl) -ester
30 2-Fluor-Ii-(2-feaylethyl)-carbaailzuur-(3- Smeltpuat: 57- 58°C30 2-Fluoro-II- (2-feaylethyl) -carboxylic acid- (3-Melting point: 57- 58 ° C
(2-me thylpropoxycarboay lamiao.) -f eayl) -ester 4-Fluor-N-propylcarbaailzuur-3-(methoxy- β^20: 1.5345 carboaylamiaofeayl)-ester 80 0 0 1 12 - 10 -(2-methylpropoxycarboay lamiao.) -F eayl) ester 4-Fluoro-N-propylcarboxylic acid 3- (methoxy- β ^ 20: 1.5345 carboaylamiaopheayl) ester 80 0 0 1 12 - 10 -
Faam van de verbinding Fysische constanteFame of the connection Physical constant
4-Fluor-N-propylcarbanilzuur-3-(ethoxy- Smeltpunt: 64- 66°C4-Fluoro-N-propylcarbanilic acid-3- (ethoxy- Melting point: 64- 66 ° C
carhonylaminofenyl)-ester F-Butyl-4-fluorcarbanilzuur-3-(methoxy- n^20: 1.5322 5 carbonylaminofenyl)-ester F-Butyl-4-fluorcarbanilzuur-3-(ethoxy- n.^20 ï 1.5305 carbonylaminofenyl)-e stercarhonylaminophenyl) ester F-Butyl-4-fluorobarbanilic acid-3- (methoxy-n-20: 1.5322 5-carbonylaminophenyl) -ester F-Butyl-4-fluorobarbanilic acid-3- (ethoxy-n. ^ 20 ï 1.5305 carbonylaminophenyl) -e star
4-Fluor-F-butylcarbanilzuur-(3-(l-methyl- Smeltpunt: 81- 83°C4-Fluoro-F-butylcarbanilic acid- (3- (1-methyl- Melting point: 81-83 ° C)
ethoxycarbonylamino)-fenyl)-esterethoxycarbonylamino) -phenyl) ester
10 4-Fluor-F-butylcarbanilzuur-(3-ethylthio- Smeltpunt: 73- 75°C10 4-Fluoro-F-butylcarbanilic acid- (3-ethylthio- Melting point: 73-75 ° C
carbonylamino)-f eny1)-e ster F-Butyl-4-fluorcarbanilzuur-(3-(2- n^20: 1.5439 propynyloxycarbonylamino)-fenyl)-estercarbonylamino) -f eny1) -e star F-Butyl-4-fluorobarbanilic acid- (3- (2- n ^ 20: 1.5439 propynyloxycarbonylamino) -phenyl) -ester
4-Fluor-F-propylcarbanilzuur-(3-(ethyl- Smeltpunt: 53- 55°C4-Fluoro-F-propylcarbanilic acid- (3- (ethyl- Melting point: 53- 55 ° C
15 thiocarbonylamino)-fenyl)-ester 4-Fluor-3S’-propylcarbanilzuur-(3-(2- n^20: 1 · 54^1 propynyloxycarbonylamino)-fenyl)-ester15 thiocarbonylamino) -phenyl) ester 4-Fluoro-3S-propylcarbanilic acid- (3- (2- n ^ 20: 1 54 ^ 1 propynyloxycarbonylamino) -phenyl) ester
N-Butyl-4-fluorcarbanilzuur-(3-(methyl- Smeltpunt: 85- 89°CN-Butyl-4-fluorocarbanilic acid- (3- (methyl- Melting point: 85-89 ° C
thiocarbonylamino)-fenyl)-e sterthiocarbonylamino) -phenyl) -e star
20 2-Fluor-F-(2-fenylethyl)-carbanilzuur- Smeltpunt: 93- 94°C20 2-Fluoro-F- (2-phenylethyl) -carbanilic acid- Melting point: 93-94 ° C
5-(2-propynyloxycarbonylamino)-feny1_7-ester5- (2-propynyloxycarbonylamino) -phenyl-7-ester
De verbindingen volgens de uitvinding zijn oplosbaar in aceton, cyclohexanon, isoforon, tetrahydrofuran, dimethylform-25 amide, dimethylsulfoxyde en ethylacetaat.The compounds of the invention are soluble in acetone, cyclohexanone, isophorone, tetrahydrofuran, dimethylformamide, dimethyl sulfoxide and ethyl acetate.
De nu volgende voorbeelden dienen ter toelichting van de toepassingsmogelijkheden, alsmede ter vergelijking met bekende verbindingen.The following examples serve to illustrate the applications, as well as for comparison with known compounds.
Voorbeeld IIExample II
30 In een broeikas werden de in de hierna volgende tabel ver melde verbindingen volgens de uitvinding in een toe te passen hoeveelheid van 5 kg actieve verbinding/ha, geëmulgeerd in 500 liter water/ha, op Brassica en Solanum als te toetsen planten na het opkomen gespoten. Drie weken na de behandeling werd het 80 0 0 1 12 • * - 11 - behandelingsresultaat gewaardeerd, waarbij O = geen werking en 4 * vernietiging van de planten betekent.In a greenhouse, the compounds of the invention listed in the table below were emulsified in 500 liters of water / ha to be used as test plants after emergence in an amount of 5 kg of active compound / ha to be used. sprayed. Three weeks after the treatment, the 80 0 0 1 12 • * - 11 - treatment result was valued, where O = no effect and 4 * means destruction of the plants.
5 Zoals uit de tabel blijkt werd een vernietiging van de proefplanten bereikt.As shown in the table, destruction of the test plants was achieved.
Verbindingen volgens de uitvinding Solanum Brassica 3- Fluor-N-methylcarbanilzuur-(3-methoxy- carbonylaminofenyl)-ester 4 4 10 N-Ethyl-3-fluorcarbanilzuur-(3-methoxy- carbonylaminofenyl)-ester 4 4 N-Ethyl-3-fluorcarbanilzuur-/"" 3-(®ethyl-thio-carbonylamino)-fenyl__7-ester 4 4 4- Fluor-ft-methylcarbanilzuur-(3-methoxy- 15 carbonylaminofenyl)-ester 4 4 4-Fluor-ÏT-methylcarbanilzuur-/'” 3-(®ethyl-thio-carbonylamino)-fenyl_7-ester 4 4 N-Ethyl-4-fluorcarbanilzuur-/_ 3“(®ethyl-thio-carbonylamino)-fenyl_7-ester 4 4 20 ïï-Ethyl-4-fluorcarbanilzuur-(3-methoxy- carbonylaminofenyl)-ester 4 4 N-Ethyl-4-fluorcarbanilzuur-(3~ethoxy- carbonylaminofenyl)-ester 4 4 !T-Ethyl-3-fluoroarbanilzuur-(3-ethoxy-25 carbonylaminofenyl)-ester 4 4 3-Fluor-N-methylcarbanilzuur-(3-ethoxy- carbonylaminofenyl)-ester 4 4 3- Fluor-rr-methylcarbanilzuur-/"" 3-(methyl- thio-carbonylamino)-fenyl_7-ester 4 4 30 3-FlTior''ft*,®e‘fchylcarbanilzuur-/"" 3-(ethyl- thio-carbonylamino)-fenyl_7-ester 4 4 4- Fluor-ÏI-methylcarbanilzuur-( 3-ethoxy- carbonylaminofenyl)-ester 4 4 800 0 1 12 - 12 -Compounds according to the invention Solanum Brassica 3-Fluoro-N-methylcarbanilic acid (3-methoxy-carbonylaminophenyl) ester 4 4 10 N-Ethyl-3-fluorocarbanilic acid (3-methoxy-carbonylaminophenyl) -ester 4 4 N-Ethyl-3 -Fluorocarbanilic acid- / "" 3- (ethylethyl-thio-carbonylamino) -phenyl-7-ester 4 4 4-Fluoro-ft-methylcarbanilic acid (3-methoxy-carbonylaminophenyl) -ester 4 4 4-Fluoro-IT-methylcarbanilic acid- / '”3- (ethylethyl-thio-carbonylamino) -phenyl-7-ester 4 4 N-Ethyl-4-fluorobarbanilic acid - / 3 3“ (®-ethyl-thio-carbonylamino) -phenyl-7-ester 4 4 20 ï-Ethyl- 4-Fluorecarbanilic acid (3-methoxy-carbonylaminophenyl) ester 4 4 N-Ethyl-4-fluorocarbanilic acid (3-ethoxy-carbonylaminophenyl) -ester 4 4-T-Ethyl-3-fluoroarbanilic acid (3-ethoxy-25-carbonylaminophenyl) ) -ester 4 4 3-Fluoro-N-methylcarbanilic acid- (3-ethoxy-carbonylaminophenyl) -ester 4 4 3-Fluoro-rr-methylcarbanilic acid- / "" 3- (methylthio-carbonylamino) -phenyl-7-ester 4 4 30 3-FlTior'ft *, ®e'fchylcarbanilic acid- / "" 3- (ethylthio-carbonylamino) -phenyl-7-ester 4 4 4-Fluoro-II-methylcarbanil acid (3-ethoxy-carbonylaminophenyl) ester 4 4 800 0 1 12 - 12 -
Verbindingen volgens de uitvinding Solanum Brassica 4-Fluor-H-(2-fenylethy1)-carbanilzuur- (3-methoxycarbonylaminofenyl)-ester 4 4 4-Fluor-ïf-( 2-fenylethyl) -carbanilzuur-5 (3-ethoxycarbonylaminofenyl)-ester 4 4 N-Ethyl-3-fluorcarbanilzuur-/” 3-0-methyl-ethoxycarbonylamino)-fenyl_7-ester 4 4 ÏT-Ethyl-4-fluorcarbanilzuur-/""3-( 1-methyl-ethoxycarbonylamino)-fenyl_7-ester 4 4 10 4-Fluor-ïï-methylcarbanilzuur-/- 3-(l-methyl- ethoxycarbonylamino)-fenylJ7-ester 4 4 ïf-Ethyl-4-fluorcarbanilzuur-/"" 3-(ethylthio-carbonylamino)-fenyl_7-ester 4 4 4-Fluor-H-methylcarbanilzuur-/"’ 3-(ethyl- 15 thiocarbonylamino)-fenyl_7-ester 4 4 3- Fluor-N-methylcarbanilzuur-/"" 3-(2- propynyloxycarbonylamino)-fenyl_J7-ester 4 4 U--Ethyl-3-fluorcarbanilzuur-/"’3-(2- propynyloxycarbonylamino)-fenyl_7-ester 4 4 20 4-Fluor-ïï-(2-fenylethyl )-carbanilzuur-/~* 3- ethylthiocarbonylamino)-fenyl_7-ester 4 4 4- Fluor-IT-( 2-f enylethyl)-carbanilzuur-/~ 3- (l-methylethoxycar'bonylamino)-fenyl_i7-ester 4 4 N-Ethyl-4-fluorcarbanilzuur-(3-allyloxy- 25 carbonylaminofenyl)-ester 4 4 U-Ethyl-4-fluorcarbanilzuur-(5-propynyl-oxycarbonylaminofenyl)-ester 4 4 4-Fluor-N-(2-fenylethyl)-carbanilzuur-(3-allyloxycarbonylaminofenyl)-ester 4 4 30 3-Fluor-ïï-(2-fenylethyl)-carbanilzuur-(3- methoxycarbonylaminofenyl)-ester 4 4 3-Fluor-N-methylcarbanilzuur-/~ 3-(1-methyl-ethoxycarbonylamino)-fenyl_7-ester 4 4 80 0 0 1 12 - 13 -Compounds according to the invention Solanum Brassica 4-Fluoro-H- (2-phenylethy1) -carbanilic acid- (3-methoxycarbonylaminophenyl) ester 4 4 4-Fluorofly- (2-phenylethyl) -carbanilic acid-5 (3-ethoxycarbonylaminophenyl) - ester 4 4 N-Ethyl-3-fluoro-carbanilic acid- / 3-0-methyl-ethoxycarbonylamino) -phenyl-7-ester 4 4-Ethyl-4-fluoro-carbanilic acid - / "" 3- (1-methyl-ethoxycarbonylamino) -phenyl_7- ester 4 4 10 4-Fluoro-1-methylcarbanilic acid - / - 3- (1-methyl-ethoxycarbonylamino) -phenyl-7-ester 4 4-Ethyl-4-fluorocarbanilic- / "" 3- (ethylthio-carbonylamino) -phenyl-7- ester 4 4 4-Fluoro-H-methylcarbanilic acid- / "3- (ethyl-thiocarbonylamino) -phenyl-7-ester 4 4 3-Fluoro-N-methylcarbanilic-acid /" "3- (2-propynyloxycarbonylamino) -phenyl_J7-ester 4 4 U - Ethyl-3-fluorocarbanilic acid - / "3- (2-propynyloxycarbonylamino) -phenyl-7-ester 4 4 20 4-Fluoro-2- (2-phenylethyl) -carbanilic- / ~ * 3-ethylthiocarbonylamino) - phenyl-7-ester 4 4 4-Fluoro-IT- (2-phenylethyl) -carbanilic acid- ~ 3- (1-methyl-ethoxycarbonylamino) -phenyl-7-ester 4 4 N-Ethyl-4-fluoro carbanilic acid (3-allyloxy-25-carbonylaminophenyl) -ester 4 4 U-Ethyl-4-fluorobarbanilic acid (5-propynyl-oxycarbonylaminophenyl) -ester 4 4 4-Fluoro-N- (2-phenylethyl) -carbanilic acid- (3- allyloxycarbonylaminophenyl) ester 4 4 30 3-Fluoro-2- (2-phenylethyl) -carbanilic acid- (3-methoxycarbonylaminophenyl) ester 4 4 3-Fluoro-N-methylcarbanilic acid / ~ 3- (1-methyl-ethoxycarbonylamino) - phenyl_7-ester 4 4 80 0 0 1 12 - 13 -
Verbindingen volgens de uitvinding Solanmn Brassica 3-Fluor-IT-methylcarbanilzuur-(3-allyl- oxycarbonylaminofenyl)-ester 4 4 3- Fluor-!i-etliylcarbanilzuur-(3-allyl- 5 oxycarbonylaminofenyl)-ester 4 4 4- Fluor-N-methylcarbanilzuur-(3-allyl- oxycarbonylaminofenyl)-ester 4 4 IT-Ethyl-3-i“luorcarbanilzuur-/"” 3-(1-chloormethylethoxycarbonylamino)-fenyl_7-10 ester 4 4 ïï-Ethyl-2-fluorcarbanilzuur-(3-methoxy- carbonylaminofenyl)-ester 4 4 N-Etliyl-3,4“difluorcarbanilzuur-(3- methoxycarbonylaminofenyl)-ester 4 4 15 3-Fluor-!i-( 2-fenylethyl)-carbanilzuur- (3-ethoxycarbonylaminofenyl)-ester 4 4 5- Fluor-N-(2-fenylethyl)-earbanilzuur-/” 3- (ethylthiocarbonylamino)-fenyl_7-ester 4 4 3-Fluor-ïï-(2-fenylethyl)-carbanilzuur-/”3- 20 (ethylthiocarbonylamino)-fenyl_7-ester 4 4 N-Ethyl-3,4-difluorcarbanilzuur-(3-ethory-carbonylaainofenyl)-ester 4 4 ïï-Ethyl-3,4-difluorcarbanilzuur-/-3- (methylthiocarbonylamino)-fenyl_7-ester 4 4 25 2-Fluor-N-(2-fenylethyl)-carbanilzuur-(3- methoxycarbonylaminofenyl)-ester 4 4 2-Fluor-]T-(2-fenyletiiyl)-carbanilzuur-(3-ethoxycarbonylaminofenyl)-ester 4 4 2-Flnor-ïï-(2-fenylethyl)-carbanilzuur-/” 3-30 (methylthiocarbonylamino)-fenyl_7-ester 4 4 2-Fluor-N-(2-fenylethyl)-carbanilzuur-/~3-(ethyltbiocarbonylamino)-fenyl^-ester 4 4 2-Fluor-N-(2-fenylethyl)-carbanilzuur-/” 3-(1-methylethorycarbonylamino)-fenyl-7'-ester 4 4 80 0 0 1 12 - 14 -Compounds according to the invention Solanmn Brassica 3-Fluoro-IT-methylcarbanilic acid (3-allyl-oxycarbonylaminophenyl) ester 4 4 3-Fluoro-1-etliylcarbanilic acid (3-allyl-oxycarbonylaminophenyl) ester 4 4 4-Fluor- N-methylcarbanilic acid (3-allyl-oxycarbonylaminophenyl) ester 4 4 IT-Ethyl-3-i-luorcarbanilic acid- / "3- (1-chloromethyl-ethoxycarbonylamino) -phenyl-7-10 ester 4 4-Ethyl-2-fluorocarbanilic acid- (3-methoxy-carbonylaminophenyl) ester 4 4 N-Etliyl-3,4 "difluorocarbanilic acid- (3-methoxycarbonylaminophenyl) ester 4 4 15 3-Fluoro-! I- (2-phenylethyl) -carbanilic acid- (3-ethoxycarbonylaminophenyl) ) -ester 4 4 5- Fluoro-N- (2-phenylethyl) -earbanilic acid- / "3- (ethylthiocarbonylamino) -phenyl-7-ester 4 4 3-Fluoro-1- (2-phenylethyl) -carbanilic acid - /" 3- 20 (ethylthiocarbonylamino) -phenyl-7-ester 4 4 N-Ethyl-3,4-difluorocarbanilic acid- (3-ethory-carbonylaainophenyl) -ester 4 4-Ethyl-3,4-difluorocarbanilic acid - / - 3- (methylthiocarbonylamino) -phenyl_7 ester 4 4 25 2-Fluoro-N- (2-phenylethyl) -carbanilic acid- (3-methoxycarbonylaminophenyl) -e star 4 4 2-Fluoro-] T- (2-phenyletiiyl) -carbanilic acid- (3-ethoxycarbonylaminophenyl) ester 4 4 2-Flnor-1- (2-phenylethyl) -carbanilic acid- / ”3-30 (methylthiocarbonylamino) - phenyl-7-ester 4 4 2-Fluoro-N- (2-phenylethyl) -carbanilic acid- / ~ 3- (ethyl-biocarbonylamino) -phenyl-ester 4 4 2-Fluoro-N- (2-phenylethyl) -carbanilic- / 3 - (1-methylethorycarbonylamino) -phenyl-7'-ester 4 4 80 0 0 1 12 - 14 -
Verbindingen volgens de uitvinding _ Solanum Brassica 2-Fluor-N-(2-fenylethylJ-carbanilzuur-/"" 3“ (2-propynyloxycarbonylamino)-fenyl_7-ester 4 4 Iï-Ethyl-2-fliiorcarbanilzuur-(3-etkoxy-* 3 carbonylaminofenyl)-ester 4 4 ET-Ethyl-2-fluorcarbanilzuur-(3-iaethyl-thiocarbonylamino)-fenyl)-ester 4 4 N-Ethyl-2-fluorcarbanilzuur-(3-(ethyl- thiocarbonylamino)-fenyl)-ester 4 4 10 N-Ethyl-2-fluorcarbanilzuur-(3-(1 -methyl- ethoxycarbonylamino)-fenyl)-ester 4 4 U-Ethyl-2-fluorcarbanilztrar-(3-(2-propy-nyloxycarbonylamino)-fenyl)-ester 4 4 2-Fluor-ïf-( 2-f enylethyl)-carbanilzuur-( 3-15 allyloxycarbonylamino)-fenyl)-ester 4 4 2-Fluor-IT-( 2-fenylethyl)-carbanilzuur-( 3-(2-methylpropoxycarbonylamino)-fenyl)-ester 4 4 4-Fluor-H-propylcarbanilzuur-3-(methoxy-carbonylaminofenyl)-ester 4 4 20 4-ï’luor-H-propylcarbanilzuur-3-(ethoxy- carbonylaminofenyl)-ester 4 4 N-Butyl-4-flnorcarbanilzuur-3-(methoxy- carbonylaminofenyl)-ester 4 4 ïï-Butyl-4-fluoroarbanilzuur-3-(ethoxy-25 carbonylaminofenyl)-ester 4 4 4-Fluor-IT-butylcarbanilzuur-( 3-( 1 -methyl-ethoxycarbonylamino)-fenyl)-ester 4 4 4-Fluor-N-butylcarbanilzuur-(3-ethylthio-carbonylamino)-fenyl)-ester 4 4 30 ïï-Butyl-4-fluorcarbanilzuur-(3-(2- propynyloxycarbonylamino)-fenyl)-ester 4 4 4-Fluor-U-propylcarbanilzuur-(3-(ethy1- thiocarbonylamino)-fenyl)-ester 4 4 80 0 0 1 12 «Γ - 15 -Compounds according to the invention - Solanum Brassica 2-Fluoro-N- (2-phenylethyl-J-carbanilic acid- / "" 3 "(2-propynyloxycarbonylamino) -phenyl-7-ester 4 4-Ethyl-2-flioriorcarbanilic acid- (3-etkoxy- * 3-carbonylaminophenyl) ester 4 4 ET-Ethyl-2-fluorocarbanilic acid (3-iaethyl-thiocarbonylamino) -phenyl) -ester 4 4 N-Ethyl-2-fluorocarbanilic acid (3- (ethyl-thiocarbonylamino) -phenyl) -ester 4 4 10 N-Ethyl-2-fluorocarbanilic acid- (3- (1-methyl-ethoxycarbonylamino) -phenyl) -ester 4 4 U-Ethyl-2-fluorocarbanilztrar- (3- (2-propy-nyloxycarbonylamino) -phenyl) - ester 4 4 2-Fluoro-2- (2-phenyl-ethyl) -carbanilic acid- (3-15 allyloxycarbonylamino) -phenyl) -ester 4 4 2-Fluoro-IT- (2-phenylethyl) -carbanilic acid- (3- (2 -methylpropoxycarbonylamino) -phenyl) ester 4 4 4-Fluoro-H-propylcarbanilic acid-3- (methoxy-carbonylaminophenyl) ester 4 4 20 4-Fluoro-H-propylcarbanilic acid 3- (ethoxy-carbonylaminophenyl) -ester 4 4 N-Butyl-4-flororcarbanilic acid-3- (methoxy-carbonylaminophenyl) ester 4 4-Butyl-4-fluoroarbanilic acid-3- (ethoxy-25-carbonylaminophenyl) ester 4 4 4-Fluoro-IT-butylcarbanilic acid (3- (1-methyl-ethoxycarbonylamino) -phenyl) -ester 4 4 4-Fluoro-N-butylcarbanilic acid (3-ethylthio-carbonylamino) -phenyl) -ester 4 4 30 Butyl 4-fluorocarbanilic acid (3- (2-propynyloxycarbonylamino) phenyl) ester 4 4 4-Fluoro-U-propylcarbanilic acid (3- (ethyl-1-thiocarbonylamino) phenyl) ester 4 4 80 0 0 1 12 « Γ - 15 -
Verbindingen volgens de uitvinding Solanum Brassica 4-Fluor-N-propylcarbanilzuur-(3-( 2- propynyloxycarbonylamino)-fenyl)-ester 4 4 N-Butyl-4-fluorcarbanilzuur-(3-(inethyl-5 thiocarbonylamino)-fenyl)-ester 4 4 ÏT-Ethyl-3-f’luorcarbanilzuur-( 3-( 1 -methyl- 2-propenyloxycarbonylamino)-fenyl)-ester 4 4 N-Ethyl-2-fluorcarbanilzuur-(3-(1-methyl- 2-propenylorycarbonylamino)-fenyl)-ester 4 4 10 U-Ethyl-4-fluorcarbanilzuur-(3-(1-methyl- 2- propenyloxycarbonylainino)-fenyl)-ester 4 4 N-Butyl-3-fluorcarbanilzuur-(3-methoxy-carbonylamino)-fenylester 4 4 3- Fluor-ÏT-methylcarbanilzuur-(3-( 2-methyl- 15 propoxycarbonylamino)-fenyl)-ester 4 4 4- Fluor-IT-( 2-fenylethyl)-oarbanilzuur-(3-(1-methyl-2-propenyloxycarbonylamino)- fenyl)-ester 4 4 3 -Fluor-ïf- (2-f eny le thy 1) - carbanil zuur- (3 -20 (1 -methyl-2-propenyloxycarbonylainino)- fenyl)-ester 4 4 3- Fluor-N-iaethylcarban.ilzuur-( 3-( 1 -methyl- 2-propenyloxyearbonylamino)-fenyl)-ester 4 4 4- Fluor-N-methylcarbaailzuur-(3-(l-methyl- 25 2-propenyloxycarbonylamino)-fenyl)-ester 4 4 H'-Butyl-4-fluorcarbanilzuur-(3-(l -methyl- 2- propenyloxycarbonylamino)-fenyl)-ester 4 4 4-Fluor-N-methylcarbanilzuur-(3-C 2-methyl-propoxycarbonylamino)-fenyl)-ester 4 4 30 3-Fluor-N-propylcarbanilzuur-(3-methoxy- carbonylamino)-fenylester 4 4 3- Fluor-N-propylcarbanilzuur-(3-(methyl- thiocarbonylamino)-fenyl)-ester 4 4 80 0 0 1 12 - 16 -Compounds according to the invention Solanum Brassica 4-Fluoro-N-propylcarbanilic acid- (3- (2-propynyloxycarbonylamino) -phenyl) -ester 4 4 N-Butyl-4-fluorocarbanilic acid- (3- (inethyl-5-thiocarbonylamino) -phenyl) - ester 4 4--Ethyl-3-fluorocarbanilic acid- (3- (1-methyl-2-propenyloxycarbonylamino) -phenyl) -ester 4 4 N-Ethyl-2-fluorocarbanilic acid- (3- (1-methyl-2- propenylorycarbonylamino) -phenyl) ester 4 4 10 U-Ethyl-4-fluorobarbanilic acid- (3- (1-methyl-2-propenyloxycarbonylainino) -phenyl) -ester 4 4 N-Butyl-3-fluorobarbanilic acid (3-methoxy-) carbonylamino) -phenyl ester 4 4 3-Fluoro-IT-methylcarbanilic acid- (3- (2-methyl-propoxycarbonylamino) -phenyl) -ester 4 4 4-Fluorine-IT- (2-phenylethyl) -oarbanilic acid- (3- ( 1-methyl-2-propenyloxycarbonylamino) -phenyl) -ester 4 4 3 -Fluoro-1- (2-phenyle thy 1) -carbanil acid- (3 -20 (1-methyl-2-propenyloxycarbonylainino) -phenyl) ester 4 4 3- Fluoro-N-iaethylcarbanililic acid- (3- (1-methyl-2-propenyloxyearbonylamino) -phenyl) -ester 4 4 4- Fluoro-N-methylcarboxylic acid- (3- (1-methyl- 25 2-prope nyloxycarbonylamino) -phenyl) -ester 4 4 H'-Butyl-4-fluorobarbanilic acid- (3- (1-methyl-2-propenyloxycarbonylamino) -phenyl) -ester 4 4 4-Fluoro-N-methylcarbanilic acid- (3-C 2 -methyl-propoxycarbonylamino) -phenyl) -ester 4 4 30 3-Fluoro-N-propylcarbanilic acid (3-methoxy-carbonylamino) -phenyl ester 4 4 3-Fluoro-N-propylcarbanilic acid (3- (methylthiocarbonylamino) -phenyl ) -ester 4 4 80 0 0 1 12 - 16 -
Verbindingen volgens de uitvinding Solanum Brassica 3- Fluor-N-propylcarbanilzuur-(3-etho:cy- carbonylamino)-fenylester 4 4Compounds of the invention Solanum Brassica 3-Fluoro-N-propylcarbanilic acid (3-etho: cyccarbonylamino) phenyl ester 4 4
Voorbeeld IIIExample III
5 In een broeikas werden de in de hierna volgende tabel ver melde verbindingen volgens de uitvinding in een toe te passen hoeveelheid van 5 kg actieve verbinding/ha, geëmulgeerd in 600 liter water/ha, op Brassica en Solanum als proefplanten vóór het opkomen gespoten. Drie weken na de behandeling werd het be-10 handelingsresultaat gewaardeerd, waarbij 0 = geen werking en 4 * vernietiging van de planten betekent.In a greenhouse, the compounds of the invention listed in the table below were sprayed onto Brassica and Solanum as pre-emergence test plants in an amount of 5 kg of active compound / ha to be used, emulsified in 600 liters of water / ha. The treatment result was evaluated three weeks after the treatment, where 0 = no effect and 4 * means destruction of the plants.
Zoals uit de tabel blijkt, werd een vernietiging van de 15 proefplanten bereikt.As shown in the table, destruction of the 15 test plants was achieved.
Verbindingen volgens de uitvinding Solanum Brassica 4- Fluor-N-methylcarbanilzuur-(3-methoxy- carbonylaminofenyl)-ester '4 - — 4 U-Ethyl-4-fluorcarbanilzuur-(3-methoxy- 20 carbonylaminofeny1)-ester 4 4 IT-Ethyl-4-fluorcarbanilzuur-(3-ethoxy- carbonylaminofenyl)-ester 4 4 4-Fluor-lf-methylcarbanilzuur-(3-ethoxy- carbonylaminofenyl)-ester 4 4 25 N-Ethyl-4-fluorcarbanilzuur-/”~3-( 1 -methyl- ethoxycarbonylamino)-fenyl_7-ester 4 4Compounds according to the invention Solanum Brassica 4- Fluoro-N-methylcarbanilic acid (3-methoxy-carbonylaminophenyl) -ester 4 - 4 U-Ethyl-4-fluorobarbanilic acid (3-methoxy-carbonylaminophenyl) -ester 4 4 IT- 4-Fluoro-1-methylcarbanilic acid (3-ethoxy-carbonylaminophenyl) ester 4 4 25 N-Ethyl-4-fluorocarbanilic acid - / ~ 3- (1-methyl-ethoxycarbonylamino) -phenyl-7-ester 4 4
Onbehandeld O 0Untreated O 0
Voorbeeld IVExample IV
In een broeikas werden de in de navolgende tabel genoemde 30 planten na het opkomen met de vermelde middelen in een hoeveel heid van 1 kg actieve verbinding/ha behandeld. De middelen werden voor dit doel gelijkmatig over de planten versproeid. Hier vertoonden de middelen volgens de uitvinding drie weken na de behandeling een grote selectiviteit naast een uitstekende wer- 800 0 1 12 - Π - king ten opzichte ran het onkruid. Het rergelijkingsmiddel vertoonde de selectiviteit niet.In a greenhouse, the plants listed in the following table were treated with the stated agents in the amount of 1 kg of active compound / ha after emergence. The agents were sprayed evenly over the plants for this purpose. Here, the agents of the invention three weeks after treatment showed great selectivity in addition to excellent action against weeds. The comparator did not show selectivity.
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Claims (27)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2901658 | 1979-01-15 | ||
| DE19792901658 DE2901658A1 (en) | 1979-01-15 | 1979-01-15 | DIURETHANE, METHOD FOR PRODUCING THESE COMPOUNDS AND HERBICIDES CONTAINING THEM |
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| Publication Number | Publication Date |
|---|---|
| NL8000112A true NL8000112A (en) | 1980-07-17 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8000112A NL8000112A (en) | 1979-01-15 | 1980-01-08 | DIURETHANES, METHOD FOR PREPARING THE SAME, AND HERBICIDES BASED ON THESE COMPOUNDS. |
Country Status (35)
| Country | Link |
|---|---|
| JP (1) | JPS5823865B2 (en) |
| AR (1) | AR224143A1 (en) |
| AT (1) | AT365411B (en) |
| AU (1) | AU532736B2 (en) |
| BE (1) | BE881152A (en) |
| BG (2) | BG31465A3 (en) |
| BR (1) | BR8000161A (en) |
| CA (1) | CA1128061A (en) |
| CH (1) | CH645343A5 (en) |
| CS (1) | CS212336B2 (en) |
| DD (1) | DD148709A5 (en) |
| DE (1) | DE2901658A1 (en) |
| DK (1) | DK16380A (en) |
| EG (1) | EG14116A (en) |
| ES (1) | ES487720A1 (en) |
| FI (1) | FI794081A (en) |
| FR (1) | FR2446275A1 (en) |
| GB (1) | GB2040939B (en) |
| GR (1) | GR71679B (en) |
| HU (1) | HU181682B (en) |
| IL (1) | IL59126A (en) |
| IN (1) | IN153545B (en) |
| IT (1) | IT1130864B (en) |
| MA (1) | MA18702A1 (en) |
| MX (1) | MX5743E (en) |
| NL (1) | NL8000112A (en) |
| PH (1) | PH15195A (en) |
| PL (1) | PL125248B1 (en) |
| PT (1) | PT70692A (en) |
| RO (1) | RO79454A (en) |
| SE (1) | SE8000278L (en) |
| SU (1) | SU942587A3 (en) |
| TR (1) | TR20529A (en) |
| YU (1) | YU1180A (en) |
| ZA (1) | ZA80244B (en) |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1567151C3 (en) * | 1965-04-09 | 1974-02-21 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Diurethanes, processes for the preparation of these compounds and herbicidal compositions containing them |
| US3535101A (en) * | 1966-09-07 | 1970-10-20 | Schering Ag | Herbicide and algicide means |
| US3901936A (en) * | 1966-10-15 | 1975-08-26 | Schering Ag | Process for the preparation of n-carbamoyloxyphenyl carbamates |
| DE2413933A1 (en) * | 1974-03-20 | 1975-09-25 | Schering Ag | DIURETHANE WITH SELECTIVE HERBICIDAL EFFECT |
| JPS5140073A (en) * | 1974-06-28 | 1976-04-03 | Siemens Ag | SHIRIKONNODOOPINGUHOHO |
| DE2557552C2 (en) * | 1975-12-18 | 1984-12-20 | Schering AG, 1000 Berlin und 4709 Bergkamen | Diurethanes and herbicidal agents containing these compounds as active ingredients |
| DE2638897C2 (en) | 1976-08-28 | 1978-10-26 | Basf Ag, 6700 Ludwigshafen | Diurethanes and herbicides containing them |
| DE2650796A1 (en) * | 1976-11-03 | 1978-05-11 | Schering Ag | DIURETHANE, METHOD FOR PRODUCING THESE COMPOUNDS AND THE SELECTIVE HERBICIDAL PRODUCT CONTAINING THEM |
-
1979
- 1979-01-15 DE DE19792901658 patent/DE2901658A1/en not_active Withdrawn
- 1979-12-24 IN IN940/DEL/79A patent/IN153545B/en unknown
- 1979-12-28 FI FI794081A patent/FI794081A/en not_active Application Discontinuation
-
1980
- 1980-01-03 YU YU00011/80A patent/YU1180A/en unknown
- 1980-01-08 NL NL8000112A patent/NL8000112A/en not_active Application Discontinuation
- 1980-01-10 TR TR20529A patent/TR20529A/en unknown
- 1980-01-11 DD DD80218424A patent/DD148709A5/en unknown
- 1980-01-11 AT AT0013980A patent/AT365411B/en not_active IP Right Cessation
- 1980-01-11 MX MX808584U patent/MX5743E/en unknown
- 1980-01-11 SU SU802867755A patent/SU942587A3/en active
- 1980-01-11 PH PH23505A patent/PH15195A/en unknown
- 1980-01-12 EG EG21/80A patent/EG14116A/en active
- 1980-01-14 SE SE8000278A patent/SE8000278L/en not_active Application Discontinuation
- 1980-01-14 IT IT19194/80A patent/IT1130864B/en active
- 1980-01-14 GR GR60957A patent/GR71679B/el unknown
- 1980-01-14 HU HU8063A patent/HU181682B/en unknown
- 1980-01-14 MA MA18899A patent/MA18702A1/en unknown
- 1980-01-14 BG BG8046235A patent/BG31465A3/en unknown
- 1980-01-14 IL IL59126A patent/IL59126A/en unknown
- 1980-01-14 BG BG8046234A patent/BG31495A3/en unknown
- 1980-01-14 RO RO8099869A patent/RO79454A/en unknown
- 1980-01-14 PL PL1980221361A patent/PL125248B1/en unknown
- 1980-01-14 PT PT70692A patent/PT70692A/en unknown
- 1980-01-14 CA CA343,600A patent/CA1128061A/en not_active Expired
- 1980-01-15 CS CS80312A patent/CS212336B2/en unknown
- 1980-01-15 GB GB8001303A patent/GB2040939B/en not_active Expired
- 1980-01-15 ZA ZA00800244A patent/ZA80244B/en unknown
- 1980-01-15 AU AU54604/80A patent/AU532736B2/en not_active Ceased
- 1980-01-15 DK DK16380A patent/DK16380A/en not_active Application Discontinuation
- 1980-01-15 AR AR279638A patent/AR224143A1/en active
- 1980-01-15 CH CH32280A patent/CH645343A5/en not_active IP Right Cessation
- 1980-01-15 BE BE0/198971A patent/BE881152A/en not_active IP Right Cessation
- 1980-01-15 ES ES487720A patent/ES487720A1/en not_active Expired
- 1980-01-15 FR FR8000793A patent/FR2446275A1/en active Granted
- 1980-01-16 JP JP55002672A patent/JPS5823865B2/en not_active Expired
- 1980-09-10 BR BR8000161A patent/BR8000161A/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BV | The patent application has lapsed |