NO139150B - HERBICID AGENT CONTAINING OXIMESTERS - Google Patents

HERBICID AGENT CONTAINING OXIMESTERS Download PDF

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Publication number
NO139150B
NO139150B NO4774/73A NO477473A NO139150B NO 139150 B NO139150 B NO 139150B NO 4774/73 A NO4774/73 A NO 4774/73A NO 477473 A NO477473 A NO 477473A NO 139150 B NO139150 B NO 139150B
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compounds
agents
oximesters
acid
agent containing
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NO4774/73A
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Norwegian (no)
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NO139150C (en
Inventor
Ludwig Nuesslein
Friedrich Arndt
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Schering Ag
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Publication of NO139150C publication Critical patent/NO139150C/en

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    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
    • 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
    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
    • A01N39/04—Aryloxy-acetic acids; Derivatives thereof
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
    • F16C—SHAFTS; FLEXIBLE SHAFTS; ELEMENTS OR CRANKSHAFT MECHANISMS; ROTARY BODIES OTHER THAN GEARING ELEMENTS; BEARINGS
    • F16C2208/00—Plastics; Synthetic resins, e.g. rubbers
    • F16C2208/20—Thermoplastic resins
    • F16C2208/30—Fluoropolymers
    • F16C2208/32—Polytetrafluorethylene [PTFE]

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  • 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)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pyridine Compounds (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Description

Foreliggende oppfinnelse angår herbicide midler inneholdende fenoxycarboxylsyreoximestere som virkestoff for anvend- The present invention relates to herbicidal agents containing phenoxycarboxylic acid oximesters as active ingredients for use

else til bekjempelse av uønsket plantevekst særlig i gresskulturer. etc. to combat unwanted plant growth, especially in grass crops.

Bekjempelsen av uønsket plantevekst i gresskulturer er bare mulig i utilstrekkelig grad med de kjente herbicider da disse neppe er virksomme mot hirsearter som f.eks. blodhirse, hønsehirse og Setaria faberii. Disse hirsearter danner en gruppe av ettårige frø-planter som i mange flater bevokst med gresskulturer er så sterkt ut-bredt at de gjør virkningen av disse kulturer eller utnyttelsen av flatene tvilsom. The control of unwanted plant growth in grass crops is only possible to an insufficient extent with the known herbicides as these are hardly effective against millet species such as e.g. blood millet, chick millet and Setaria faberii. These millet species form a group of annual seed plants which are so widespread in many areas covered with grass crops that they make the effect of these crops or the utilization of the areas questionable.

Oppgaven ved foreliggende oppfinnelse er derfor å fremskaffe et herbicid som spesielt muliggjør bekjempelsen av disse hirsearter. The task of the present invention is therefore to provide a herbicide which particularly enables the control of these millet species.

Denne oppgave løses ifølge oppfinnelsen ved et middel som karakteriseres ved et innhold av minst én forbindelse med den generelle formel: According to the invention, this task is solved by an agent which is characterized by a content of at least one compound with the general formula:

hvor R er hydrogen, alkyl med 1-4 carbonatomer eller fenyl, og er alkyl med 1-6 carbonatomer, fenyl, nitrofenyl, fenoxymethyl eller methoxyethyl, R^ og R2 kan dessuten sammen med det carbonatom til hvilket de er bundet, være cyclopentyliden, methylcyclopentyliden, cyclohexyliden, dimethy1-cyclohexenyliden eller trimethyl-cyclohexenyliden, R^ er hydrogen eller methyl, where R is hydrogen, alkyl with 1-4 carbon atoms or phenyl, and is alkyl with 1-6 carbon atoms, phenyl, nitrophenyl, phenoxymethyl or methoxyethyl, R^ and R2 together with the carbon atom to which they are attached can also be cyclopentylidene, methylcyclopentylidene, cyclohexylidene, dimethyl-cyclohexenylidene or trimethyl-cyclohexenylidene, R^ is hydrogen or methyl,

X er methyl og/eller halogen, og n er 1, 2 eller 3- X is methyl and/or halogen, and n is 1, 2 or 3-

Dessuten strekker virkningen av disse forbindelser seg også til mange andre ugress, f.eks. Sinapis sp., Solanum sp., lusernarter, vassarve, åkersvineblom, kamilleblom, myktvetann, kornblomst, dusk-amarant, klengemaure, gullkrave, Ipomea purpurea og rødt hønsegress. Moreover, the effect of these compounds also extends to many other weeds, e.g. Sinapis sp., Solanum sp., alfalfa species, water sedge, field pig's flower, chamomile flower, soft wheatgrass, cornflower, tassel amaranth, sedge ant, golden collar, Ipomea purpurea and red hen's grass.

En annen vesentlig fordel ved forbindelsene som anvendes ifølge oppfinnelsen, er deres utmerkede forlikelighet overfor kulturgress, bygg, hvete, havre, rug, mais, ris og poteter, som ikke påvirkes av behandlingen. Another significant advantage of the compounds used according to the invention is their excellent compatibility with cultivated grasses, barley, wheat, oats, rye, maize, rice and potatoes, which are not affected by the treatment.

Anvendelsesmengden utgjør alt efter anvendelsesområdet og plantearten ca. 0,5 - 3 kg virkestoff/ha. Depending on the area of application and the plant species, the amount of application amounts to approx. 0.5 - 3 kg active substance/ha.

Anvendelsen ifølge oppfinnelsen av forbindelsene med formel I kan skje alene eller som blanding av flere virkestoffer og dessuten også i blanding med andre plantevernmidler og Skadedyrbekjempelses-midler. Hvis det er hensikten å gjøre virkespektret bredere, kan også andre herbicider tilsettes, hvorved naturligvis selektiviteten fremdeles opprettholdes. Som herbicid virksomme blandingspartnere er f.eks. de følgende egnet: virkestoffer fra gruppene carboxyl-syrer og deres derivater, carbaminsyrederivater, fenoler og deres derivater, substituerte ureaer, substituerte triaziner, difenylether-derivater, anilider, uraciler, nitriler og andre organiske herbicider som maleinhydrazid, 3-amino-l,2,4-triazol, N-(l,l-dimethyl-2-propyl)-3,5-diklorbenzamid, N,N-di-(n-propyl)- 2,6-dinitro-4-trifluor-methylanilin , 4-amino-3,5,6-triklorpicolinsyre, 1,1'-dimethyl-4,4'-bipyridyliumsalter. The use according to the invention of the compounds of formula I can take place alone or as a mixture of several active substances and also in a mixture with other plant protection products and pest control agents. If the intention is to make the spectrum of action wider, other herbicides can also be added, whereby selectivity is of course still maintained. Mixture partners active as herbicides are e.g. the following are suitable: active substances from the groups carboxylic acids and their derivatives, carbamic acid derivatives, phenols and their derivatives, substituted ureas, substituted triazines, diphenyl ether derivatives, anilides, uracils, nitriles and other organic herbicides such as maleic hydrazide, 3-amino-1,2 ,4-triazole, N-(1,1-dimethyl-2-propyl)-3,5-dichlorobenzamide, N,N-di-(n-propyl)- 2,6-dinitro-4-trifluoro-methylaniline , 4 -amino-3,5,6-trichloropicolinic acid, 1,1'-dimethyl-4,4'-bipyridylium salts.

Alt efter anvendelsesformålet kan også andre stoffer tilsettes, f.eks. også ikke-fytotoksiske tilsetninger, som med herbicidene kan gi en synergisk virkningsøkning, som fuktemidler, emulgatorer, opp-løsningsmidler, oljeaktige tilsetninger og andre. Depending on the intended use, other substances can also be added, e.g. also non-phytotoxic additives, which with the herbicides can give a synergistic increase in effectiveness, such as wetting agents, emulsifiers, solvents, oily additives and others.

Fortrinnsvis anvendes de virkestoffer som skal anvendes ifølge oppfinnelsen eller deres blandinger i form av preparater som pulvere, strømidler, granulater, oppløsninger, emulsjoner eller suspensjoner under tilsetning av flytende og/eller faste bærere hhv. fortynnings-midler, og eventuelt fuktemidler, heftemidler, emulgeringsmidler og/eller dispergeringsmidler. Preferably, the active substances to be used according to the invention or their mixtures are used in the form of preparations such as powders, flow agents, granules, solutions, emulsions or suspensions with the addition of liquid and/or solid carriers respectively. diluents, and possibly wetting agents, binding agents, emulsifying agents and/or dispersing agents.

Egnede flytende bærere er f.eks. vann, alifatiske og aromatiske hydrocarboner som benzen, toluen, cyclohexanon, isoforon og dessuten mineraloljefraksjoner. Suitable liquid carriers are e.g. water, aliphatic and aromatic hydrocarbons such as benzene, toluene, cyclohexanone, isophorone and also mineral oil fractions.

Som faste bærere er mineraljord, f.eks. tonsil, silicagel, talkum, kaolin, attaclay, kalksten, kiselsyre og planteprodukter, f.eks. mel, egnet. As solid carriers are mineral soil, e.g. tonsil, silica gel, talc, kaolin, attaclay, limestone, silicic acid and plant products, e.g. flour, suitable.

Av overflateaktive stoffer kan nevnes: f.eks. calciumlignin-sulfonat, polyoxyethylen-octylfenolether, nafthalinsulfonsyrer, fenolsulfonsyrer, formaldehydkondensater, fettalkoholsulfater og fettsure alkali- og jordalkalisalter. Surface-active substances can be mentioned: e.g. calcium lignin sulfonate, polyoxyethylene octylphenol ether, naphthalene sulfonic acids, phenol sulfonic acids, formaldehyde condensates, fatty alcohol sulfates and fatty acid alkali and alkaline earth salts.

Andelen av virkestoffet eller virkestoffene i de forskjellige preparater kan variere innen vide grenser. Eksempelvis inneholder midlene ca. 20 - 80 vekt% virkestoff, ca. 80 - 20 vekt% flytende eller faste bærere såvel som eventuelt inntil 20 vekt% overflateaktive stoffer. The proportion of the active substance or active substances in the different preparations can vary within wide limits. For example, the funds contain approx. 20 - 80% by weight active ingredient, approx. 80 - 20% by weight liquid or solid carriers as well as possibly up to 20% by weight surfactants.

Påføringen av midlene kan skje på vanlig måte, f.eks. med vann som bærer i sprøytevæskemengder på 100/1000 l/ha. For den totale ugressbekjempelse kan også uten videre de delvis vanlige sprøyte-væskemengder på mere enn 1000 l/ha anvendes. Også anvendelsen av midlene i den såkalte "ultra-lavvolums"-fremgangsmåte er mulig. Likeledes er anvendelsesmåten i mikrogranulatform mulig. The agents can be applied in the usual way, e.g. with water carrying in spray liquid quantities of 100/1000 l/ha. For total weed control, the partly normal spray liquid quantities of more than 1000 l/ha can also be used without further ado. Also, the use of the agents in the so-called "ultra-low-volume" method is possible. Likewise, the method of application in microgranule form is possible.

Anvendelsen utføres f.eks. ved utsprøytning eller utstrøing av det anvendelsesferdige middel på den ennå ugressfrie jord. Ved en innarbeidelse av midlet i jorden økes som regel dets virksomhet. The application is carried out e.g. by spraying or spreading the ready-to-use agent on the still weed-free soil. When the agent is incorporated into the soil, its activity is usually increased.

Forbindelsene med formel I kan f.eks. fremstilles ved omsetning av oximer med den generelle formel: The compounds of formula I can e.g. is produced by reacting oximes with the general formula:

eller deres alkalisalter, som f.eks. natrium- eller kaliumsaltet, or their alkali salts, such as e.g. the sodium or potassium salt,

a) med fenoxycarboxylsyreklorider med formelen: a) with phenoxycarboxylic acid chlorides of the formula:

eventuelt i nærvær av en syreakseptor, som f.eks. en organisk eller uorganisk base, f.eks. triethylamin, dimethylanilin, pyridin, natriumcarbonat eller natronlut, og et oppløsningsmiddel som f.eks. klorerte hydrocarboner, ethere, estere, nitriler, syreamider eller vann, fortrinnsvis methylenklorid, tetrahydrofuran, dioxan, eddik-syreester, acetonitril eller dimethylformamid, eller b) med et syreanhydrid med den generelle formel: optionally in the presence of an acid acceptor, such as e.g. an organic or inorganic base, e.g. triethylamine, dimethylaniline, pyridine, sodium carbonate or caustic soda, and a solvent such as e.g. chlorinated hydrocarbons, ethers, esters, nitriles, acid amides or water, preferably methylene chloride, tetrahydrofuran, dioxane, acetic acid ester, acetonitrile or dimethylformamide, or b) with an acid anhydride of the general formula:

eventuelt i nærvær av en syreakseptor, f.eks. pyridin, N,N-dimethylanilin eller triethylamin, og et oppløsningsmiddel, f.eks. alifatiske eller aromatiske hydrocarboner, særlig benzen, pyridin, tetrahydrofuran, dioxan, dimethylsulfoxyd, acetonitril eller dimethylformamid, optionally in the presence of an acid acceptor, e.g. pyridine, N,N-dimethylaniline or triethylamine, and a solvent, e.g. aliphatic or aromatic hydrocarbons, in particular benzene, pyridine, tetrahydrofuran, dioxane, dimethylsulfoxide, acetonitrile or dimethylformamide,

idet R^ , , R» og X har den ovenfor angitte betydning, og Hal be-tegner et halogenatom. where R , , R , and X have the meaning indicated above, and Hal denotes a halogen atom.

Det følgende eksempel belyser fremstillingen av forbindelsene som anvendes ifølge oppfinnelsen. The following example illustrates the preparation of the compounds used according to the invention.

2, 4- diklorfenoxyeddiksyremethyl-( 1- methylpropyl)- ketoximester 2, 4-Dichlorophenoxyacetic acid methyl-(1-methylpropyl)-ketoxy ester

.29,4 g2,4-diklorfenoxyeddiksyreklorid dryppes under omrøring til en oppløsning av 14,1 g methyl-(1-methylpropyl)-ketoxim og 12,4 g triethylamin i 200 ml acetonitril, hvorved temperaturen stiger til 45°C. Reaksjonsblåndingen omrøres i ytterligere 3 timer, helles i 2 1 vann, og den utskilte olje ekstraheres med ether. Etherfasen ut-rystes med fortynnet natronlut og derpå med vann og tørres over natriumsulfat. Oppløsningsmidlet avdestilleres, og rester av det fjernes i høyvakuum. Den tilbakeblivende olje veier 36,0 g (92% av det teoretiske), n^<u> = 1,5360. .29.4 g of 2,4-dichlorophenoxyacetic acid chloride is added dropwise with stirring to a solution of 14.1 g of methyl-(1-methylpropyl)-ketoxime and 12.4 g of triethylamine in 200 ml of acetonitrile, whereby the temperature rises to 45°C. The reaction mixture is stirred for a further 3 hours, poured into 2 1 of water, and the separated oil is extracted with ether. The ether phase is shaken out with dilute caustic soda and then with water and dried over sodium sulphate. The solvent is distilled off, and its residues are removed under high vacuum. The remaining oil weighs 36.0 g (92% of the theoretical), n^<u> = 1.5360.

Andre forbindelser som anvendes ifølge oppfinnelsen, er oppført i de følgende tabeller. Other compounds used according to the invention are listed in the following tables.

Forbindelsene er farve- og smakløse, oljeaktige eller krystall-inske stoffer som f.eks. er uoppløselige i vann og bensin, og er oppløselige i aceton, methylenklorid, tetrahydrofuran, dimethylformamid, cyclohexanon og isoforon. The compounds are colourless, tasteless, oily or crystalline substances such as e.g. are insoluble in water and petrol, and are soluble in acetone, methylene chloride, tetrahydrofuran, dimethylformamide, cyclohexanone and isophorone.

Utgangsmaterialene for fremstilling av forbindelsene ifølge oppfinnelsen er i og for seg kjente og kan fremstilles ved kjente fremgangsmåt er. The starting materials for producing the compounds according to the invention are known per se and can be produced by known methods.

Fremstillingen av de anvendelsesferdige preparater av forbindelsene ifølge oppfinnelsen og blandinger av dem, kan utføres på i og for seg kjent vis, f.eks. ved blandings- eller malingsmetoder. Om ønskes kan enkeltkomponentene også tilblandes først kort før deres anvendelse, som det f.eks. gjøres i praksis i den såkalte tankblande-metode. The preparation of the ready-to-use preparations of the compounds according to the invention and their mixtures can be carried out in a manner known per se, e.g. by mixing or painting methods. If desired, the individual components can also be mixed only shortly before their use, as e.g. is done in practice in the so-called tank mixing method.

De følgende eksempler belyser den herbicide virkning av forbindelsene som anvendes ifølge oppfinnelsen. The following examples illustrate the herbicidal effect of the compounds used according to the invention.

Eksempel 1 Example 1

De i tabellen oppførte forbindelser ble i drivhus sprøytet på The compounds listed in the table were sprayed on in greenhouses

hirseplanter av de angitte arter i en dosering på 3 kg virkestoff/ha. Plantene befant seg på behandlingstidspunktet i 2- til 3-bladstadiet. Der ble anvendt vandige emulsjoner av forbindelsene som ble påført i en mengde på 500 l/ha. millet plants of the indicated species in a dosage of 3 kg of active substance/ha. At the time of treatment, the plants were in the 2- to 3-leaf stage. Aqueous emulsions of the compounds were used, which were applied in a quantity of 500 l/ha.

Bedømmelsen skjedde 2 uker efter behandling, idet der ble bedømt efter en bedømmelsesskala 0 - IO hvor 0 betyr "totalt tilintetgjort", og 10 betyr "ikke skadet". The assessment took place 2 weeks after treatment, as it was assessed according to an assessment scale 0 - IO where 0 means "totally destroyed", and 10 means "not damaged".

Resultatene viser den utmerkede herbicide virkning mot hirse-plant er. The results show the excellent herbicidal effect against the millet plant.

Eksempel 2 Example 2

De i det efterfølgende oppførte kulturplanter og ugress ble i drivhus besprøytet- ved post-emergensmetoden med forbindelsene i en dosering på 1 kg virkestoff/ha, idet disse ble anvendt i form av vandige emulsjoner i en mengde på 5O0 l/ha. The subsequently listed cultivated plants and weeds were sprayed in greenhouses by the post-emergence method with the compounds in a dosage of 1 kg of active substance/ha, as these were used in the form of aqueous emulsions in a quantity of 5O0 l/ha.

Bedømmelsen skjedde 2 uker efter behandling ved den samme metode som beskrevet i eksempel 1. The assessment took place 2 weeks after treatment using the same method as described in example 1.

Der ble fastlagt betraktelig beskadigelse av ugressene ved fullstendig skåning av kulturplantene. Considerable damage to the weeds was determined when the cultivated plants were completely spared.

Eksempel 3 Example 3

De i tabellen oppførte kulturplanter og ugress ble i drivhus ved post-ernergensmetoden besprøytet med de oppførte forbindelser i en dosering på 0,3 kg virkestoff/ha, idet disse ble anvendt i form av vandige emulsjoner med 500 l/ha. The cultivated plants and weeds listed in the table were sprayed in greenhouses using the post-energetic method with the compounds listed in a dosage of 0.3 kg of active substance/ha, as these were used in the form of aqueous emulsions with 500 l/ha.

Bedømmelsen skjedde 2 uker efter behandling ved samme metode som beskrevet i eksempel 1. The assessment took place 2 weeks after treatment using the same method as described in example 1.

Midlene anvendt ifølge oppfinnelsen skadet ugressene under skåning av kulturplantene sterkere enn sammenligningsmidlet. The agents used according to the invention damaged the weeds while sparing the cultivated plants more strongly than the comparison agent.

Eksempel 4 Example 4

I drivhus ble de nedenfor anførte plantearter ved post-emergensmetoden besprøytet med forbindelsene i en grensekonsentrasjon på 0,3 kg virkestoff/ha. Forbindelsene ble herved anvendt i form av vandige emulsjoner. In greenhouses, the plant species listed below were sprayed using the post-emergence method with the compounds in a limit concentration of 0.3 kg of active substance/ha. The compounds were used in the form of aqueous emulsions.

Sammenligningsmidlet viste en meget liten herbicid virkning. The comparator showed a very small herbicidal effect.

I motsetning til dette ble der med forbindelsene som anvendes ifølge oppfinnelsen, oppnådd en betraktelig beskadigelse av ugressene ved fullstendig skåning av kulturplantene. In contrast to this, with the compounds used according to the invention, considerable damage to the weeds was achieved by completely sparing the cultivated plants.

E ksempel 5 Example 5

I drivhus ble stor busthirse ved post-emergensmetoden besprøytet med forbindelsene i en"dosering på 5 kg virkestoff/ha, idet disse ble anvendt i form av vandige emulsjoner med 500 l/ha. In greenhouses, big bush millet was sprayed by the post-emergence method with the compounds in a dosage of 5 kg of active substance/ha, as these were used in the form of aqueous emulsions with 500 l/ha.

Bedømmelsen skjedde 3 måneder efter behandling, idet der ble anvendt følgende bedømmelsesskala: The assessment took place 3 months after treatment, using the following assessment scale:

0 = ikke skadet 0 = not damaged

1 = svakt skadet 1 = slightly damaged

2 = midlere beskadigelse 2 = moderate damage

3 = sterk beskadigelse 3 = severe damage

og 4 r= totalt tilintetgjort. and 4 r= totally destroyed.

Resultatene viser den utmerkede virkning av de ifølge oppfinnelsen anvendte midler. The results show the excellent effect of the agents used according to the invention.

Claims (1)

Herbicid middel, karakterisert ved at det inneholder minst én forbindelse med den generelle formel:Herbicide, characterized in that it contains at least one compound with the general formula: hvor R^ er hydrogen, alkyl med 1-4 carbonatomer eller fenyl,where R^ is hydrogen, alkyl with 1-4 carbon atoms or phenyl, og R2 er alkyl med 1-6 carbonatomer, fenyl, nitrofenyl, fenoxymethyl eller methoxyethyl, R^ og R2 kan dessuten sammen med det carbonatom til hvilket de er bundet, være cyclopentyliden, methylcyclopentyliden, cyclohexyliden, dimethy1-cyclohexenyliden eller trimethyl-cyclohexenyliden, R^ er hydrogen eller methyl,and R2 is alkyl with 1-6 carbon atoms, phenyl, nitrophenyl, phenoxymethyl or methoxyethyl, R^ and R2, together with the carbon atom to which they are attached, can also be cyclopentylidene, methylcyclopentylidene, cyclohexylidene, dimethyl-cyclohexenylidene or trimethyl-cyclohexenylidene, R ^ is hydrogen or methyl, X er methyl og/eller halogen, og n er 1, 2 eller 3.X is methyl and/or halogen, and n is 1, 2 or 3.
NO4774/73A 1972-12-15 1973-12-14 HERBICID AGENT CONTAINING OXIMESTERS NO139150C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2262402A DE2262402A1 (en) 1972-12-15 1972-12-15 HERBICIDAL PHENOXYCARBONIC ACID OXIMESTER

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NO139150B true NO139150B (en) 1978-10-09
NO139150C NO139150C (en) 1979-01-31

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JP (1) JPS5319657B2 (en)
AR (1) AR213382A1 (en)
AT (1) AT328217B (en)
BE (1) BE808636A (en)
BG (1) BG20754A3 (en)
BR (1) BR7309821D0 (en)
CA (1) CA1013587A (en)
CH (1) CH584510A5 (en)
CS (1) CS170111B2 (en)
DD (1) DD108031A5 (en)
DE (1) DE2262402A1 (en)
ES (1) ES420904A1 (en)
FI (1) FI55927C (en)
FR (1) FR2327234A1 (en)
GB (1) GB1458825A (en)
HU (1) HU168995B (en)
IE (1) IE38640B1 (en)
IL (1) IL43825A (en)
IT (1) IT1048161B (en)
LU (1) LU68996A1 (en)
NL (1) NL7317222A (en)
NO (1) NO139150C (en)
PL (1) PL91626B1 (en)
RO (1) RO68556A (en)
SU (2) SU525417A3 (en)
ZA (1) ZA739503B (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1509034A (en) * 1975-06-30 1978-04-26 Shell Int Research Herbicides
US4200587A (en) * 1977-11-28 1980-04-29 Hoffmann-La Roche Inc. 2-[P-(p-Substituted phenoxy)phenoxy]propionyl oximes
EP0052798B1 (en) * 1980-11-26 1985-05-08 F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft Oxime esters, processes for their preparation, their use and compositions containing these esters

Also Published As

Publication number Publication date
FI55927C (en) 1979-11-12
BR7309821D0 (en) 1974-09-24
RO68556A (en) 1981-08-30
JPS4986539A (en) 1974-08-19
GB1458825A (en) 1976-12-15
JPS5319657B2 (en) 1978-06-22
NL7317222A (en) 1974-06-18
PL91626B1 (en) 1977-03-31
CS170111B2 (en) 1976-08-27
NO139150C (en) 1979-01-31
AT328217B (en) 1976-03-10
ZA739503B (en) 1974-11-27
BG20754A3 (en) 1975-12-20
BE808636A (en) 1974-06-14
IT1048161B (en) 1980-11-20
FR2327234B1 (en) 1978-03-24
SU525417A3 (en) 1976-08-15
HU168995B (en) 1976-08-28
DE2262402A1 (en) 1974-08-01
FR2327234A1 (en) 1977-05-06
IE38640B1 (en) 1978-04-26
ES420904A1 (en) 1976-05-01
AU6365273A (en) 1975-06-19
DD108031A5 (en) 1974-09-05
FI55927B (en) 1979-07-31
CA1013587A (en) 1977-07-12
AR213382A1 (en) 1979-01-31
ATA1048373A (en) 1975-05-15
IE38640L (en) 1974-06-15
IL43825A0 (en) 1974-03-14
IL43825A (en) 1977-03-31
LU68996A1 (en) 1974-02-22
SU511853A3 (en) 1976-04-25
CH584510A5 (en) 1977-02-15

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