DK160967B - PROCEDURE AND HERBICIDE PREPARATION FOR THE FIGHT AGAINST WEEDS IN THE GROWTH OF A CORN CROP - Google Patents
PROCEDURE AND HERBICIDE PREPARATION FOR THE FIGHT AGAINST WEEDS IN THE GROWTH OF A CORN CROP Download PDFInfo
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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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/88—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with three ring hetero atoms
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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
- 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
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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
- 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
- A01N37/48—Nitro-carboxylic acids; Derivatives thereof
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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
- 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
-
- 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
- A01N43/34—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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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- 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)
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- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
iin
DK 160967 BDK 160967 B
Den foreliggende opfindelse angår en fremgangsmåde til bekæmpelse af ukrudt i kornafgrøder og herbicidpræparater til anvendelse ved en sådan fremgangsmåde.The present invention relates to a method for controlling weeds in grain crops and herbicide preparations for use in such a method.
Hidtil har de bredbladede ukrudtsarter, Matricaria spp, vist sig at 5 være særligt resistente over for konventionelle herbicider og har således forårsaget stor skade på vinter- og vårkornafgrøder, såsom hvede, byg, havre og rug. Det har nu vist sig, at disse ukrudtsarter ved anvendelse af en kombination af særlige kendte herbicider kontrolleres i overraskende høj grad, idet der iagttages synergistisk virkning i over-10 ensstemmelse med den velkendte "Colby ligning" (Weeds, 15, 20-22, 1967). Desuden har kontrol af andre problematiske ukrudtsarter vist sig at være meget tilfredsstillende, når kombinationen anvendes, idet der igen iagttages synergistisk virkning i adskillige tilfælde.So far, the broadleaf weeds, Matricaria spp, have been found to be particularly resistant to conventional herbicides and have thus caused great damage to winter and spring cereals, such as wheat, barley, oats and rye. It has now been found that, using a combination of particular known herbicides, these weed species are surprisingly controlled, observing synergistic effect in accordance with the well-known "Colby equation" (Weeds, 15, 20-22, 1967). In addition, control of other problematic weed species has proven to be very satisfactory when used in combination, with synergistic effect again being observed in several cases.
I overensstemmelse med den foreliggende opfindelse tilvejebringes 15 der således en fremgangsmåde til bekæmpelse af ukrudt på voksesteder for kornafgrøder, hvilken fremgangsmåde er ejendommelig ved, at man efter fremkomst af afgrøden tilfører voksestedet en diphenylether med formlen IThus, in accordance with the present invention, there is provided a method for controlling weeds at cereal crop growing sites, which is characterized in that after the emergence of the crop, a diphenyl ether of formula I is added.
0 20 Cl 250 20 Cl 25
og et eller flere chlorphenoxyalkansyrederivater med formlen II _/CHand one or more chlorophenoxyalkanoic acid derivatives of formula II-CH
30 Γ\_30 Γ \ _
Cl-^ y-0-X-C00HCl-y-O-X-C00H
35 hvori X er -CH(CHg)-, -CHg- eller -(CHg)^-, eller salte eller estre deraf, idet forbindelsen med formlen I tilføres i en mængde på 0,25 til 3,0 kg/ha, og forbindelsen med formlen II eller salte eller estre deraf tilføres i en mængde på 0,5 til 3,0 kg/ha, når der anvendes en forbindelse \ 2Wherein X is -CH (CHg) -, -CHg- or - (CHg) 2 -, or salts or esters thereof, the compound of formula I being supplied in an amount of 0.25 to 3.0 kg / ha, and the compound of formula II or salts or esters thereof is fed at an amount of 0.5 to 3.0 kg / ha when using a compound \ 2
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med formlen II eller salte eller estre deraf, hvori X er -CH(CH3)-, forbindelsen med formlen I tilføres i en mængde på 0,7 til 2,0 kg/ha, og forbindelsen med formlen II eller salte eller estre deraf tilføres i en mængde på 0,7 til 3,0 kg/ha, når der anvendes en forbindelse med formlen 5 II eller salte eller estre deraf, hvori X er -CHg-, og forbindelsen med formlen I tilføres i en mængde på 0,25 til 3,0 kg/ha, og forbindelsen med formlen II eller salte eller estre deraf tilføres i en mængde på 0,1 til 3,5 kg/ha, når der anvendes en forbindelse med formlen II eller salte eller estre deraf, hvori X er -(CHgJg-, idet vægtmængden af for-10 bindeiserne med formlen II er baseret på syreækvivalenten i de tilfælde, hvor et salt eller en ester af en forbindelse med formlen II anvendes, og idet afgrøden ikke er vårhvede, når der anvendes en enkelt forbindelse med formlen II eller salte eller estre deraf, hvori X er -CH(CH3)-.of formula II or salts or esters thereof, wherein X is -CH (CH 3) -, the compound of formula I is fed at an amount of 0.7 to 2.0 kg / ha and the compound of formula II or salts or esters thereof is added in an amount of 0.7 to 3.0 kg / ha when using a compound of formula 5 II or salts or esters thereof, wherein X is -CHg- and the compound of formula I is added in an amount of 0.25 to 3.0 kg / ha and the compound of formula II or salts or esters thereof is added in an amount of 0.1 to 3.5 kg / ha when using a compound of formula II or salts or esters thereof, wherein X is - (CH 2 J 2 -, the weight amount of the compounds of formula II being based on the acid equivalent in cases where a salt or ester of a compound of formula II is used and the crop is not spring wheat when a single compound of formula II or salts or esters thereof, wherein X is -CH (CH 3) -.
I almindelighed tilføres forbindelsen med formlen I i en mængde på 15 0,7 til 2,0 kg/ha og forbindelsen eller forbindelserne med formlen II i en mængde på 0,7 til 3,0 kg/ha.Generally, the compound of formula I is fed in an amount of 0.7 to 2.0 kg / ha and the compound or compounds of formula II in an amount of 0.7 to 3.0 kg / ha.
Forbindelsen med formlen I er kendt som bifenox, og dens fremstilling er beskrevet i britisk patentskrift nr. 1.232.368, og dens anvendelse som herbicid i Proc. N.E. Weed Sci. Conf. 1973, 27, 31.The compound of formula I is known as bifenox, and its preparation is described in British Patent Specification No. 1,232,368 and its use as a herbicide in Proc. N.E. Weed Sci. Conf. 1973, 27, 31.
20 Forbindelsen med formlen II, hvori X er -CH(CH3)-, er kendt som mecoprop.The compound of formula II wherein X is -CH (CH 3) - is known as mecoprop.
Forbindelsen med formlen II, hvori X er -CHg-, er kendt som M.C.P.A.The compound of formula II wherein X is -CHg- is known as M.C.P.A.
Forbindelsen med formlen II, hvori X er -(CH^Xø-» er kendt som 25 M.C.P.B.The compound of formula II wherein X is - (CH 2 X 4 - is known as M.C.P.B.
Mecoprop, M.C.P.A., M.C.P.B., deres salte og estere, deres fremstilling og deres herbicide egenskaber er vel underbygget i litteraturen.Mecoprop, M.C.P.A., M.C.P.B., their salts and esters, their preparation and their herbicidal properties are well supported in the literature.
Forbindelserne med formlen II kan anvendes i fri syreform-el1 er i en salt- eller esterform, som er ikke-phytotoxisk overfor kornsorter.The compounds of formula II can be used in free acid form or in a salt or ester form which is non-phytotoxic to cereals.
30 Som eksempler på saltformer kan angives alkalimetal-, f.eks. natrium- og kaliumsaltformerne og ammonium-, al kyl ammonium- og alkanolammoniumsaltformerne, f.eks. ethanol ammoniumsal tformen. Som eksempler på esterformer kan angives de lavere, f.eks. Cj_8, al kyl esterformer, f.eks. methyl- og octyl esterformerne. Anvendelsen af sådanne salt- og ester-35 former er omfattet af den foreliggende opfindelse.As examples of salt forms, alkali metal, e.g. the sodium and potassium salt forms and the ammonium, alkyl, the ammonium and alkanolammonium salt forms, e.g. ethanol ammonium salts. As examples of ester forms, the lower ones may be mentioned, e.g. C8-8, all cool ester forms, e.g. the methyl and octyl ester forms. The use of such salt and ester forms is encompassed by the present invention.
Ved fremgangsmåden ifølge opfindelsen anvendes forbindelsen med formlen I (bifenox) fortrinsvis i en tilført mængde på 0,7 til 1,5 kg/ha, og særligt foretrukket i en mængde på ca. 0,75 til 1,0 kg/ha.In the process of the invention, the compound of formula I (biphenox) is preferably used in an applied amount of 0.7 to 1.5 kg / ha, and especially preferably in an amount of approx. 0.75 to 1.0 kg / ha.
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Forbindelsen med formlen II, hvori X er -CH(CH3)- eller -(CHgJj-, dvs. mecoprop eller M.C.P.B., anvendes fortrinsvis i en tilført mængde på 1,0 til 2,0 kg/ha. Forbindelsen med formlen II, hvori X er -CHg-, dvs.The compound of formula II wherein X is -CH (CH 3) - or - (CH 2 J 2 -, i.e., mecoprop or MCPB) is preferably used in an applied amount of 1.0 to 2.0 kg / ha. The compound of formula II wherein X is -CHg-, i.e.
M.C.P.A., anvendes fortrinsvis i en tilført mængde på 0,7 til 1,5 5 kg/ha, og særligt foretrukket i en mængde på ca. 0,75 til 1,0 kg/ha.M.C.P.A., is preferably used in an amount of 0.7 to 1.5 5 kg / ha, and particularly preferably in an amount of approx. 0.75 to 1.0 kg / ha.
Vægtforholdet mellem forbindelsen med formlen I og forbindelsen eller forbindelserne med formlen II er sædvanligvis i intervallet fra 1:4 til 3:1. Når bifenox anvendes sammen med mecoprop eller M.C.P.B., er vægtforholdet mellem den første og den sidste fortrinsvis i intervallet 10 fra 1:3 til 1,5:1, særligt foretrukket ca. 1:2. Når bifenox anvendes sammen med M.C.P.A., er vægtforholdet mellem den første og den sidste fortrinsvis i intervallet fra 1:2 til 2:1, særligt foretrukket ca. 1:1.The weight ratio of the compound of formula I to the compound or compounds of formula II is usually in the range of 1: 4 to 3: 1. When bifenox is used in conjunction with mecoprop or M.C.P.B., the weight ratio of the first to the last is preferably in the range of 10 from 1: 3 to 1.5: 1, especially preferably about 1: 3. 1: 2. When bifenox is used in conjunction with M.C.P.A., the weight ratio of the first to the last is preferably in the range of 1: 2 to 2: 1, especially preferably about 1: 2. 1: 1.
Når det drejer sig om forbindelser med formlen II, er ovenstående vægtmængder og -forhold baseret på syreækvivalenten deraf, hvis der an-15 vendes et salt eller en ester.In the case of compounds of formula II, the above weight amounts and ratios are based on the acid equivalent thereof if a salt or ester is used.
Fremgangsmåden ifølge opfindelsen gennemføres fortrinsvis, når afgrøden er mellem étblad-stadiet og tilsynekomsten af det andet led.The process according to the invention is preferably carried out when the crop is between the one leaf stage and the appearance of the second link.
De foretrukne afgrøder for behandling ved fremgangsmåden ifølge opfindelsen er vinterhvede, vårbyg og vinterbyg.The preferred crops for treatment by the process of the invention are winter wheat, spring barley and winter barley.
20 Forbindelsen med formlen I og forbindelsen eller forbindelserne med formlen II kan tilføres sammen eller hver for sig. I sidstnævnte tilfælde er tidsrummet mellem tilførslerne fortrinsvis kort, f.eks. en dag eller mindre. Det er imidlertid langt at foretrække at tilføre forbindelserne samtidigt som et enkelt præparat. For at forenkle fremstilling, 25 lagring og transport vil herbicidpræparater normalt blive fremstillet i koncentratform beregnet til fortynding i vand til den grad, der er nødvendig for at gøre det muligt at opnå ovennævnte tilførelsesmængder. Sådanne koncentratpræparater kan indeholde fra 1 til 90 vægtprocent, fortrinsvis 15 til 85 vægtprocent aktive ingredienser i forbindelse med en 30 eller flere inerte, ikke-phytotoxiske bærere derfor. Sådanne præparater vil sædvanligvis være i form af et befugteligt pulver, et emulgerbart koncentrat eller en vandig suspension eller opløsning.The compound of formula I and the compound or compounds of formula II may be added together or separately. In the latter case, the time interval between the feeds is preferably short, e.g. a day or less. However, it is far preferable to administer the compounds simultaneously as a single preparation. In order to simplify preparation, storage and transport, herbicide preparations will normally be prepared in concentrate form intended for dilution in water to the degree necessary to enable the above-mentioned application rates to be obtained. Such concentrate compositions may contain from 1 to 90% by weight, preferably 15 to 85% by weight of active ingredients, in association with a 30 or more inert, non-phytotoxic carriers therefor. Such preparations will usually be in the form of a wettable powder, an emulsifiable concentrate or an aqueous suspension or solution.
Opfindelsen tilvejebringer endvidere et herbicidpræparat til anvendelse ved fremgangsmåden ifølge opfindelsen, eventuelt efter passende 35 fortynding, hvilket præparat indeholder en forbindelse med formlen I og en eller flere forbindelser med formlen II eller salte eller estre deraf til anvendelse i de mængder og til de afgrøder, der er anført i krav 1, idet vægtforholdet mellem forbindelsen med formlen I og forbindelsen med \ 4The invention further provides a herbicide composition for use in the process of the invention, optionally after appropriate dilution, which contains a compound of formula I and one or more compounds of formula II or salts or esters thereof for use in the amounts and crops which is claimed in claim 1, the weight ratio of the compound of formula I to the compound of \ 4
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formlen II eller salte eller estre deraf er i intervallet, fra 1:4 til 3:1 (baseret på syreækvivalenten i de tilfælde, hvor et salt eller en ester af forbindelsen med formlen II anvendes. Præparatet ifølge opfindelsen kan desuden indeholde et/en ikke-phytotoxisk fortyndingsmiddel 5 eller bærer. De foretrukne vægtforholdintervaller er som angivet ovenfor.the formula II or salts or esters thereof are in the range of 1: 4 to 3: 1 (based on the acid equivalent in the case where a salt or ester of the compound of formula II is used. The composition of the invention may further contain -phytotoxic diluent 5 or carrier The preferred weight ratio ranges are as indicated above.
Herbicidpræparaterne ifølge den foreliggende opfindelse er ikke blot de såkaldte koncentratpræparatformer, men også de brugsklare fortyndede præparater, såsom tankblandinger og brugsklare sprøjtevæsker.The herbicide compositions of the present invention are not only the so-called concentrate formulations, but also the ready-to-use diluted compositions such as tank mixtures and ready-to-use spray liquids.
10 Sådanne fortyndede præparater fremstilles sædvanligvis ved fortynding af koncentratpræparater ned til den passende grad, men kan om ønsket fremstilles ved adskilt tilsætning af passende mængder af de enkelte komponenter til et/en passende fortyndingsmiddel eller bærer.Such diluted compositions are usually prepared by diluting concentrate compositions down to the appropriate degree, but may, if desired, be prepared by separately adding appropriate amounts of the individual components to a suitable diluent or carrier.
Hvad koncentratpræparaterne angår, indeholder befugtelige pulvere 15 en intim blanding af de aktive ingredienser, en eller flere inerte bærere og et eller flere passende overfladeaktive midler. Den inerte bærer kan være udvalgt blandt forskellige typer attapulgitler, montmorillonit-ler, diatoméjord, kaolin, glimmer, talkum og rensede silicater. Effektive overfladeaktive midler kan findes blandt de sulfonerede ligniner, 20 naphtha!ensulfonaterne og de kondenserede naphthalensulfonater, af kyl -succinaterne, al kyl benzensulfonaterne, al kyl sul faterne og non-ioniske overfladeaktive midler, såsom ethylenoxidadditionsforbindelser af phenol. De befugtelige pulvere kan illustreres ved de befugtelige pulvere med følgende sammensætning: 25In the case of the concentrate compositions, wettable powders 15 contain an intimate mixture of the active ingredients, one or more inert carriers and one or more suitable surfactants. The inert carrier can be selected from various types of attapulgitles, montmorillonites, diatomaceous earth, kaolin, mica, talc and purified silicates. Effective surfactants can be found among the sulfonated lignins, the 20 naphthalene sulfonates and the condensed naphthalene sulfonates, of the coolant succinates, all the cooler benzenesulfonates, all coolers and nonionic surfactants such as ethylene oxide additives of phenol. The wettable powders can be illustrated by the wettable powders of the following composition: 25
Befugtelige pulvere VægtprocentWettable powders Weight percent
Forbindelse med formlen I 1-73Compound of Formula I 1-73
Forbindelse med formlen II* 1-79 30 Et eller flere overfladeaktive midler 1-10Compound of Formula II * 1-79 One or more surfactants 1-10
Dispergeringsmiddel 0-10Dispersant 0-10
Antisammenbagningsmiddel 0-10Anti-caking agent 0-10
En eller flere inerte bærere op til 100 * Baseret på syreækvivalent.One or more inert carriers up to 100 * Based on acid equivalent.
Emulgerbare koncentrater indeholder de aktive ingredienser opløst i et eller flere egnede opløsningsmidler sammen med et overfladeaktivt middel. Som eksempler på opløsningsmidler kan angives al kyl substituerede 35 5Emulsifiable concentrates contain the active ingredients dissolved in one or more suitable solvents together with a surfactant. Examples of solvents may be all alkyl substituted 35 5
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benzener, o-chlortoluen, tunge aromatiske naphthalener, glycolethere og cykliske ketoner. Til illustration af emulgerbare koncentrater kan nævnes de emulgerbare koncentrater med følgende sammensætning: 5 Emulgerbare koncentrater Væat/volumenprocentbenzenes, o-chlorotoluene, heavy aromatic naphthalene, glycol ethers and cyclic ketones. For illustration of emulsifiable concentrates, mention may be made of the emulsifiable concentrates having the following composition: 5 Emulsifiable concentrates Wett / volume percent
Forbindelse med formlen I 1-55Compound of Formula I 1-55
Forbindelse med formlen II* 1-60Compound of Formula II * 1-60
Et eller flere overfladeaktive midler 2-10 10 Co-opløsningsmiddel 0-40One or more surfactants 2-10 10 Co-solvent 0-40
Opløsningsmiddel op til 100 * Baseret på syreækvivalentSolvent up to 100 * Based on acid equivalent
Vandige suspensioner og opløsninger indeholder de aktive ingredi-15 enser suspenderet eller opløst i vand sammen med eventuelle ønskede overfladeaktive midler, fortykningsmidler, antifrysningsmidler eller præserveringsmidler. Passende overfladeaktive midler kan udvælges blandt dem, der er nævnt ovenfor i forbindelse med befugtelige pulvere. Eventuelle fortykningsmidler udvælges normalt blandt passende cellulose-20 materialer og naturgummier, medens der sædvanligvis anvendes glycoler, når et anti frysningsmiddel er nødvendigt. Præserveringsmidler kan udvælges blandt mange forskellige materialer, såsom de forskellige para-benantibakterielle midler, phenol, o-chlorcresol, phenylmercurinitrat og formaldehyd. De vandige suspensioner kan illustreres ved suspensionerne 25 med følgende sammensætning:Aqueous suspensions and solutions contain the active ingredients suspended or dissolved in water together with any desired surfactants, thickeners, antifreeze or preservatives. Suitable surfactants may be selected from those mentioned above for wettable powders. Any thickening agents are usually selected from suitable cellulose materials and natural gums, while glycols are usually used when an anti-freezing agent is needed. Preservatives can be selected from many different materials, such as the various paraben antibacterial agents, phenol, o-chlorocresol, phenylmercurine nitrate and formaldehyde. The aqueous suspensions can be illustrated by the suspensions 25 having the following composition:
Vandige suspensioner Væat/volumenprocentAqueous suspensions W / v%
Forbindelse med formlen I 4-59 30 Forbindelse med formlen II* 5-65Compound of Formula I 4-59 Compound of Formula II * 5-65
Befugtningsmiddel 0-10Wetting agent 0-10
Dispergeringsmiddel 0-6Dispersant 0-6
Fortyknings-/suspenderingsmiddel 0-5Thickener / suspending agent 0-5
Anti frysningsmiddel 0-15 35 Præserveringsmiddel 0-2Anti-freezing agent 0-15 35 Preservative 0-2
Vand op til 100 * Baseret på syreækvivalent.Water up to 100 * Based on acid equivalent.
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Præparater i form af vandige suspensioner og befugtelige pulvere foretrækkes til anvendelse ved fremgangsmåden ifølge opfindelsen, idet de giver betydeligt lavere phytotoxicitet over for kornafgrøden end præparaterne i form af emulgerbare koncentrater.Compositions in the form of aqueous suspensions and wettable powders are preferred for use in the process of the invention, as they provide significantly lower phytotoxicity to the cereal crop than the compositions in the form of emulsifiable concentrates.
5 Opfindelsen illustreres nærmere ved eksempler i det efterfølgende.The invention is further illustrated by the following examples.
I alle eksempler er mængden af mecoprop, M.C.P.A. og M.C.P.B. baseret på syreækvival enten.In all examples, the amount of mecoprop, M.C.P.A. and M.C.P.B. based on acid equivalent either.
Eksempel 1-5 10 Følgende befugtelige pulvere fremstilledes under anvendelse af følgende ingredienser: Vægtprocent (1) Bifenox 20 15 Mecoprop (kaliumsalt) 40Examples 1-5 10 The following wettable powders were prepared using the following ingredients: Weight percent (1) Bifenox 20 15 Mecoprop (potassium salt) 40
Natriumlaurylsul fat 3Sodium lauryl sulphate 3
Natrium!igninsul fonat 3Sodium! Igninsul phonate 3
Præcipiteret siliciumoxid 8Precipitated silica 8
Kaolin ti"l 100 20 Vægtprocent (2) Bifenox 20Kaolin to 100% Weight Percent (2) Bifenox 20
Mecoprop (natriumsalt) 27Mecoprop (sodium salt) 27
Ethoxyleret al kylphenol 4 25 Lignosulfonat 3Ethoxylated all kylphenol 4 25 Lignosulfonate 3
Sublimeret siliciumoxid 6Sublimated silica 6
Attapulgit til 100 Vægtprocent 30 (3) Bifenox 10Attapulgit for 100% by weight 30 (3) Bifenox 10
Mecoprop (diethanol aminsalt) 25Mecoprop (diethanol amine salt) 25
Natriumsalt af kondenserede naphtha!ensulfonsyrer 6Sodium salt of condensed naphthalene sulfonic acids 6
Præcipiteret siliciumoxid 10 35 Natriumaluminiumsil icat til 100 7Precipitated silica 10 35 Aluminum silicate for 100 7
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Vægtprocent (4) Bifenox 30 M.C.P.B. (natriumsalt) 45Weight Percent (4) Bifenox 30 M.C.P.B. (sodium salt) 45
Natriumlaurylsul fat 2 5 Natriumligninsulfonat 3Sodium lauryl sulphate 2 5 Sodium lignin sulfonate 3
Præcipiteret siliciumoxid 5Precipitated silica 5
Montmorillonit til 100 Vægtprocent 10 (5) Bifenox 30 M.C.P.A. (natriumsalt) 30Montmorillonite to 100% by weight 10 (5) Bifenox 30 M.C.P.A. (sodium salt) 30
Natri umi auryl sul fat 2Natri umi auryl sul fat 2
Natriumligninsulfonat 3Sodium lignin sulfonate 3
Præcipiteret siliciumoxid 5 15 Montmorillonit til 100 I hvert eksempel blev de aktive ingredienser blandet omhyggeligt med de angivne exipienser i konventionelt blandingsudstyr. Blandingerne blev så formalet yderligere i en fluidumenergimølle til en partikel-20 størrelse i intervallet fra 1 til 10 /an.Precipitated Silica 5 15 Montmorillonite to 100 In each example, the active ingredients were carefully mixed with the indicated excipients in conventional mixing equipment. The mixtures were then further milled in a fluid energy mill to a particle size ranging from 1 to 10 µm.
Eksempel 6-10 Følgende emulgerbare koncentrater fremstilledes ud fra de nedenfor viste komponenter: 25 Vægt/volumenprocent (6) Bifenox 15Examples 6-10 The following emulsifiable concentrates were prepared from the components shown below: 25% w / v (6) Bifenox 15
Mecoprop 30Mecoprop 30
Calciumdodecylbenzensul fonat 3 30 Alkylphenoxypolyoxyethylenethanoler 3Calcium dodecylbenzenesulfonate 3 Alkylphenoxypolyoxyethyleneethanols 3
Isophoron 20Isophoron 20
Xylen til 100 35 8Xylene to 100 35 8
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Vægt/volumenprocent (7) Bifenox 15Weight / Volume Percent (7) Bifenox 15
Mecopropester 20Mecopropester 20
Al kyl aryl sul fon at 4 5 Polyoxyethylentriglycerid 4Alkyl aryl sulphonate 4 5 Polyoxyethylene triglyceride 4
Cyclohexanon 20Cyclohexanone 20
Orthochlortoluen til 100 Væat/νοΐumenprocent 10 (8) Bifenox 10Orthochlorotoluene to 100 Watt / Vol% Percent 10 (8) Bifenox 10
Mecoprop 25Mecoprop 25
Ami nsalt af dodecylbenzensul fonsyre 3Amine salt of dodecylbenzene sulphonic acid 3
Polyoxyethylensorbi tal fedtsyreestere 4Polyoxyethylene sorbi number of fatty acid esters 4
Isophoron 15 15 Tung aromatisk naphtha til 100 Vægt/volumenprocent (9) Bifenox 20 M.C.P.B. (blandede butylestere) 30 20 Caleiumdodecylbenzensul fonat 3Isophorone 15 15 Heavy aromatic naphtha to 100% w / v (9) Bifenox 20 M.C.P.B. (mixed butyl esters) 30 20 Caleium dodecylbenzene sulfonate 3
Al kylphenoxypolyoxyethylenethanoler 4All kylphenoxypolyoxyethyleneethanols 4
Isophoron 30Isophoron 30
Orthochlortoluen til 100 25 Vægt/volumenprocent (10) Bifenox 20 M.C.P.A. 20Orthochlorotoluene to 100 25% w / v (10) Bifenox 20 M.C.P.A. 20
Caleiumdodecylbenzensul fonat 3Calcium dodecylbenzene sulphate 3
Al kylphenoxypolyoxyethylenethanoler 4 30 Isophoron 30Al kylphenoxypolyoxyethyleneethanols 4 30 Isophorone 30
Orthochlortoluen til 100Orthochlorotoluene to 100
De aktive ingredienser blev sat til det eller de passende opløsningsmidler under omrøring og eventuelt opvarmning for at lette op- 35 løsning af de aktive materialer. Så tilsattes de overfladeaktive midler.The active ingredients were added to the appropriate solvent (s) with stirring and optionally heating to facilitate dissolution of the active materials. Then the surfactants were added.
Opløsningerne blev så filtreret for at fjerne uopløselige urenheder.The solutions were then filtered to remove insoluble impurities.
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Eksempel 11-13 Følgende vandige suspensioner fremstilledes med de nedenfor viste komponenter: 5 Vægtprocent (11) Bifenox 30 M.C.P.A. (aminsalt) 30 (Ethyl)hydroxyethylcellul ose 0,2Examples 11-13 The following aqueous suspensions were prepared with the components shown below: 5% by weight (11) Bifenox 30 M.C.P.A. (amine salt) (Ethyl) hydroxyethyl cellulose 0.2
Ligninsul fonat 3 10 Propylenglycol 2Ligninsul phonate 3 10 Propylene glycol 2
Vand til 100 Vægtprocent (12) Bifenox 20 15 M.C.P.B. (aminsalt) 35Water to 100% by weight (12) Bifenox 20 15 M.C.P.B. (amine salt) 35
Hydroxyethylcellulose 0,2Hydroxyethyl cellulose 0.2
Aminethoxylat 3Amin ethoxylate 3
Vand til 100 20 Vægtprocent (13) Bifenox 25Water to 100 20% by weight (13) Bifenox 25
Mecoprop (aminsalt) 50Mecoprop (amine salt) 50
Hydroxyethylcellul ose 0,5Hydroxyethyl cellulose 0.5
Phosphatester 3 25 Ethylenglycol 2Phosphate ester 3 25 Ethylene glycol 2
Vand til 100Water to 100
De efterfølgende eksempler tjener til illustration af den synergistiske virkning, der påvises ved fremgangsmåden ifølge opfindelsen.The following examples serve to illustrate the synergistic effect demonstrated by the method of the invention.
3030
Eksempel AExample A
Nogle feltforsøg blev gennemført på vinterhvede og et på vårbyg på sand- og lermuldjord. Tilførsel blev foretaget som tankblandinger med et rygbåret sprøjteanlæg i et volumen på 300-800 liter/ha. Afgrødestadiet 35 ved tilførslen varierede fra tidspunktet, hvor der begyndte at komme skud, til det stadium, hvor det andet knæ var synligt. Der blev foretaget visuelle vurderinger af den herbicide aktivitet fra 2 til 15 uger efter tilførslen under anvendelse af Barratt og Horsfall (1945) 10Some field trials were conducted on winter wheat and one on spring barley on sandy and clay soil. Supply was made as tank mixtures with a back-mounted spray system at a volume of 300-800 liters / ha. The crop stage 35 at inflow varied from the time when shots started to the stage at which the second knee was visible. Visual assessments of the herbicidal activity were made from 2 to 15 weeks after application using Barratt and Horsfall (1945) 10
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vurderi ngssystemet.assessment system.
I den efterfølgende tabel er anført gennemsnittet af de opnåede resultater i form af procent kontrol af ukrudtsarterne Matricaria spp for de enkelte herbicider bifenox, mecoprop og M.C.P.A. og for tank-5 blandingskombinationer af bifenox + mecoprop og bifenox + M.C.P.A., idet der også er anført kontrolværdien beregnet ved hjælp af Colby-formlen for additiv virkning. Koncentraterne, ud fra hvilke de vandige sprøjtevæsker dannedes, var bifenox 80% befugteligt pulver, mecoprop 55% vandig opløsning og M.C.P.A. 40% vandig opløsning.The following table shows the average of the results obtained in terms of percent control of the weed species Matricaria spp for the individual herbicides bifenox, mecoprop and M.C.P.A. and for tank-5 blend combinations of bifenox + mecoprop and bifenox + M.C.P.A., also indicating the control value calculated by the Colby formula for additive action. The concentrates from which the aqueous sprays were formed were bifenox 80% wettable powder, mecoprop 55% aqueous solution and M.C.P.A. 40% aqueous solution.
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TabelTable
Doseringsværdi % Kontrol kg/ha Iagttaget Colby-formel 15 _Dosage value% Control kg / ha Observed Colby formula 15
Bifenox 1,0 16,1Bifenox 1.0 16.1
Bifenox 1,5 25,5Bifenox 1.5 25.5
Bifenox 2,0 40,3 20 M.C.P.A. (aminsalt) 0,8 38,5 M.C.P.A. (aminsalt) 1,6 64,8Bifenox 2.0 40.3 20 M.C.P.A. (amine salt) 0.8 38.5 M.C.P.A. (amine salt) 1.6 64.8
Mecoprop (aminsalt) 2,0 54,8Mecoprop (amine salt) 2.0 54.8
Bifenox + M.C.P.A.Bifenox + M.C.P.A.
(aminsalt) 1,0 + 0,8 85,1 48,4 25 (aminsalt) 1,5 + 0,8 93,4 54,2 (aminsalt) 2,0 + 1,6 95,3 79,0(amine salt) 1.0 + 0.8 85.1 48.4 (amine salt) 1.5 + 0.8 93.4 54.2 (amine salt) 2.0 + 1.6 95.3 79.0
Bifenox + mecoprop (aminsalt) 1,0 + 2,0 86,0 62,1 (aminsalt) 1,5 + 2,0 89,0 66,3 30 _Bifenox + mecoprop (amine salt) 1.0 + 2.0 86.0 62.1 (amine salt) 1.5 + 2.0 89.0 66.3
Det fremgår således af ovenstående, at der iagttages en virkelig synergi sti sk virkning ved anvendelse af fremgangsmåden ifølge opfindelsen. Der bemærkedes en svag svidning af afgrøden, som voksede op der-35 efter.Thus, it is apparent from the above that a truly synergistic effect is observed using the method of the invention. A slight stinging of the crop was noticed, which grew up thereafter.
Ud over fortræffelig kontrol af Matricaria spp kontrolleredes følgende ukrudstsarter godt (mere end 80%) ved anvendelse i separate forsøg af ovenstående kombinerede tankblandinger: Anethum graveolens,In addition to excellent control of Matricaria spp, the following weed species were well controlled (more than 80%) when used in separate experiments of the above combined tank mixtures: Anethum graveolens,
DK 160967 BDK 160967 B
ππ
Capsella bursa-pastoris, Centaurea cyanus, Fumaria officinalis, Lamium amplexicaule, Papaver rhoeas, Sil ene spp og Stellaria media.Capsella bursa-pastoris, Centaurea cyanus, Fumaria officinalis, Lamium amplexicaule, Papaver rhoeas, Sil ene spp and Stellaria media.
Bifenox + M.C.P.A. kombinationen gav desuden god kontrol (højere end 80%) af følgende ukrudtsarter. Anagallis arvensis, Chenopodium 5 album, Polygonum aviculare, Ranunculus arvensis, Ranunculus repens,Bifenox + M.C.P.A. the combination also gave good control (higher than 80%) of the following weed species. Anagallis arvensis, Chenopodium 5 album, Polygonum aviculare, Ranunculus arvensis, Ranunculus repens,
Raphanus raphanistrum, Rumex crispus, Sinapis arvensis, Sonchus arvensis og Veronica hederi folia.Raphanus raphanistrum, Rumex crispus, Sinapis arvensis, Sonchus arvensis and Veronica hederi folia.
Bifenox + mecoprop kombinationen gav desuden god kontrol (højere end 80%) af Gallium aparine.The Bifenox + mecoprop combination also gave good control (higher than 80%) of Gallium aparine.
1010
Eksempel BExample B
Følgende væksthusforsøg blev gennemført for at påvise effektiviteten af bifenox kombineret med M.C.P.B.The following greenhouse experiments were conducted to demonstrate the efficacy of bifenox combined with M.C.P.B.
15 FremgangsmådeMethod
Frø; Gallium aparine Matricaria recutita Veronica persica 20 Plantning: 0,5 cm dybde. (Matricaria sp let dækning)Frog; Gallium aparine Matricaria recutita Veronica persica 20 Planting: 0.5 cm depth. (Matricaria sp light coverage)
Temperatur/belvsning: Væksthus (kold)Temperature / exposure: Greenhouse (cold)
Vanding: Efter behov Gødning; IngenIrrigation: As needed Fertilizer; None
Forsøgsplan: randomiseret blok (4 gentagelser) 25 Størrelse af behandlet parti: 10 x 10 cm potterTrial plan: randomized block (4 repetitions) 25 Size of treated lot: 10 x 10 cm pots
Jordtextur: LermuldSoil texture: Clay earth
Tilførselsudstvr: Mikrosprøjteanlæg med enkelt dyse, 50 cm bånd- 2 bredde, volumen i forhold til areal 50 ml pr. m .Supply equipment: Single nozzle micro spray system, 50 cm bandwidth 2, volume in relation to area 50 ml per unit. m.
Ukrudtsstadium ved tilførsel: 3-5 virkelige blade.Weed stage at application: 3-5 real leaves.
30 I den efterfølgende tabel er anført gennemsnittet af de opnåede resultater i form af procent kontrol af ukrudtsarterne sammen med kontrolværdien bestemt ved Colby-formi en. For Veronica persicas vedkommende blev der foretaget en visuel kontrol vurdering. For de to andre arter be- 35 stemtes frisk vægt af skud.30 The following table shows the average of the results obtained in terms of percent control of the weed species together with the control value determined by the Colby Form. For Veronica persica, a visual control assessment was performed. For the other two species, fresh weight of shoots was determined.
Bifenoxen, ud fra hvilken sprøjtevæsken dannedes, var et 80% be-fugteligt pulver, M.C.P.B.én var en 48% vandig opløsning, og kombinationen en tankblanding.The biphenoxene from which the spray liquid was formed was an 80% wettable powder, the M.C.P.B.en a 48% aqueous solution and the combination a tank mixture.
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1212
Ukrudtsarter. % Kontrol Mængde Matricaria Sp Galium aparine Veronica persica kg/ha 5 Iagttaget Colby Iagttaget Colby Iagttaget ColbyWeed species. % Control Quantity Matricaria Sp Galium aparine Veronica persica kg / ha 5 Observed Colby Observed Colby Observed Colby
Bifenox 0,75 56,5 62,5 77,0 10 M.C.P.B. 1,0 7,5 0,0 73,0 M.C.P.B. 1,5 2,4 0,0 78,0Bifenox 0.75 56.5 62.5 77.0 10 M.C.P.B. 1.0 7.5 0.0 73.0 M.C.P.B. 1.5 2.4 0.0 78.0
Bifenox 15 + MCPB 0,75+1,0 73,0 60,0 72,1 62,5 100,0 94,0 " 0,75+1,5 82,0 57,5 78,3 62,5 100,0 96,0 20 Det fremgår således af det ovenstående, at der iagttages en virke lig synergistisk virkning ved anvendelse af fremgangsmåden ifølge op-f i ndel sen.Bifenox 15 + MCPB 0.75 + 1.0 73.0 60.0 72.1 62.5 100.0 94.0 "0.75 + 1.5 82.0 57.5 78.3 62.5 100 Thus, from the foregoing, it is apparent that an effective synergistic effect is observed using the method of the invention.
Eksempel CExample C
25 Dette eksempel illustrerer yderligere den synergistiske virkning, der påvises ved kombinationen af bifenox + mecoprop, når den anvendes til kontrol af det bredbladede ukrudt Matricaria spp.This example further illustrates the synergistic effect demonstrated by the combination of bifenox + mecoprop when used to control the broadleaf weed Matricaria spp.
Vinterhvede såedes i Frankrig i oktober i en dybde på 3 cm og en mængde på 150 kg/ha. Afgrøden fik lov til at gro uden behandling indtil 30 den efterfølgende marts, på hvilket tidspunkt afgrøden var på vækststadium 4-5 (se Plant Pathol., 3, 128-9, (1954)).Winter wheat was sown in France in October at a depth of 3 cm and an amount of 150 kg / ha. The crop was allowed to grow without treatment until 30 the following March, at which time the crop was at growth stage 4-5 (see Plant Pathol., 3, 128-9, (1954)).
Bifenox og mecoprop blev så tilført separat og kombineret med hinanden som en tankblanding og sprøjtet på arealet, hvor afgrøden dyrkedes, under anvendelse af et rygbåret sprøjteanlæg i en mængde på 300 35 liter pr. hektar. Vurderinger, som ukrudtskontrolvurderinger, blev foretaget mellem 2 og 5 uger efter tilførsel.Bifenox and mecoprop were then fed separately and combined with each other as a tank mixture and sprayed onto the area where the crop was grown, using a back-mounted spraying system at a rate of 300 35 liters per liter. acres. Assessments, such as weed control assessments, were made between 2 and 5 weeks after application.
Claims (11)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7829989A GB2027344A (en) | 1978-07-15 | 1978-07-15 | Herbicidal formulation |
| GB7829989 | 1978-07-15 | ||
| GB7849440 | 1978-12-21 | ||
| GB7849440 | 1978-12-21 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK291679A DK291679A (en) | 1980-01-16 |
| DK160967B true DK160967B (en) | 1991-05-13 |
| DK160967C DK160967C (en) | 1991-11-18 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK291679A DK160967C (en) | 1978-07-15 | 1979-07-11 | PROCEDURE AND HERBICIDE PREPARATION FOR THE FIGHT AGAINST WEEDS IN THE GROWTH OF A CORN CROP |
Country Status (31)
| Country | Link |
|---|---|
| KR (1) | KR830002045B1 (en) |
| AR (1) | AR225418A1 (en) |
| AT (1) | AT364572B (en) |
| AU (1) | AU527751B2 (en) |
| BG (1) | BG30615A3 (en) |
| BR (1) | BR7904487A (en) |
| CH (1) | CH641011A5 (en) |
| DD (1) | DD144858A5 (en) |
| DE (1) | DE2927908A1 (en) |
| DK (1) | DK160967C (en) |
| EG (1) | EG13945A (en) |
| ES (1) | ES482463A1 (en) |
| FI (1) | FI62204C (en) |
| FR (1) | FR2430723B1 (en) |
| GR (1) | GR69817B (en) |
| HK (1) | HK73885A (en) |
| HU (1) | HU180832B (en) |
| IE (1) | IE48774B1 (en) |
| IL (1) | IL57767A (en) |
| IT (1) | IT1117178B (en) |
| LU (1) | LU81499A1 (en) |
| MA (1) | MA18523A1 (en) |
| MX (1) | MX5912E (en) |
| NL (1) | NL7905400A (en) |
| NZ (1) | NZ190989A (en) |
| PL (1) | PL116679B1 (en) |
| PT (1) | PT69919A (en) |
| RO (1) | RO78004A (en) |
| SE (1) | SE7906014L (en) |
| SU (1) | SU860674A3 (en) |
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| GB8403342D0 (en) * | 1984-02-08 | 1984-03-14 | Velsicol Chemical Ltd | Herbicidal compositions |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US3652645A (en) * | 1969-04-25 | 1972-03-28 | Mobil Oil Corp | Halophenoxy benzoic acid herbicides |
| NL175780C (en) * | 1972-11-17 | 1985-01-02 | Rhone Poulenc Inc | PROCESS FOR PREPARING A HERBICIDE PREPARATION CONTAINING AT LEAST A PHENOXYNITROBENZOATE |
| JPS5924122B2 (en) * | 1973-08-20 | 1984-06-07 | 北興化学工業 （株） | herbicide composition |
| JPS50125030A (en) * | 1974-03-23 | 1975-10-01 | ||
| EP0001328A1 (en) * | 1977-09-23 | 1979-04-04 | FISONS plc | Method and composition for combating weeds |
-
1979
- 1979-07-10 AR AR277235A patent/AR225418A1/en active
- 1979-07-10 SE SE7906014A patent/SE7906014L/en not_active Application Discontinuation
- 1979-07-10 IL IL57767A patent/IL57767A/en unknown
- 1979-07-11 FR FR7917994A patent/FR2430723B1/en not_active Expired
- 1979-07-11 DK DK291679A patent/DK160967C/en not_active IP Right Cessation
- 1979-07-11 DE DE19792927908 patent/DE2927908A1/en not_active Ceased
- 1979-07-11 AT AT0483979A patent/AT364572B/en not_active IP Right Cessation
- 1979-07-11 NL NL7905400A patent/NL7905400A/en not_active Application Discontinuation
- 1979-07-12 RO RO7998138A patent/RO78004A/en unknown
- 1979-07-12 GR GR59590A patent/GR69817B/el unknown
- 1979-07-12 NZ NZ190989A patent/NZ190989A/en unknown
- 1979-07-12 TR TR20527A patent/TR20527A/en unknown
- 1979-07-12 FI FI792193A patent/FI62204C/en not_active IP Right Cessation
- 1979-07-12 AU AU48889/79A patent/AU527751B2/en not_active Ceased
- 1979-07-13 LU LU81499A patent/LU81499A1/en unknown
- 1979-07-13 HU HU79LI346A patent/HU180832B/en unknown
- 1979-07-13 SU SU792790363A patent/SU860674A3/en active
- 1979-07-13 MA MA18720A patent/MA18523A1/en unknown
- 1979-07-13 DD DD79214330A patent/DD144858A5/en unknown
- 1979-07-13 ES ES482463A patent/ES482463A1/en not_active Expired
- 1979-07-13 MX MX798191U patent/MX5912E/en unknown
- 1979-07-13 BG BG044331A patent/BG30615A3/en unknown
- 1979-07-13 PT PT69919A patent/PT69919A/en active IP Right Revival
- 1979-07-13 BR BR7904487A patent/BR7904487A/en not_active IP Right Cessation
- 1979-07-13 IT IT49754/79A patent/IT1117178B/en active
- 1979-07-13 CH CH655079A patent/CH641011A5/en not_active IP Right Cessation
- 1979-07-14 EG EG424/79A patent/EG13945A/en active
- 1979-07-14 PL PL1979217116A patent/PL116679B1/en unknown
- 1979-07-16 KR KR7902370A patent/KR830002045B1/en active
- 1979-08-08 IE IE1325/79A patent/IE48774B1/en not_active IP Right Cessation
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1985
- 1985-09-26 HK HK738/85A patent/HK73885A/en not_active IP Right Cessation
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