IL43825A - Herbicidal preparations containing alpha-phenoxy alkanoic acid oxime esters - Google Patents

Herbicidal preparations containing alpha-phenoxy alkanoic acid oxime esters

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Publication number
IL43825A
IL43825A IL43825A IL4382573A IL43825A IL 43825 A IL43825 A IL 43825A IL 43825 A IL43825 A IL 43825A IL 4382573 A IL4382573 A IL 4382573A IL 43825 A IL43825 A IL 43825A
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IL
Israel
Prior art keywords
ester
methyl
add
ketoxime
acid
Prior art date
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IL43825A
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IL43825A0 (en
Original Assignee
Schering Ag
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Publication date
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Publication of IL43825A0 publication Critical patent/IL43825A0/en
Publication of IL43825A publication Critical patent/IL43825A/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)
  • Wood Science & Technology (AREA)
  • General Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Zoology (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (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)
  • Medicines Containing Plant Substances (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pyridine Compounds (AREA)

Abstract

1458825 Herbicidal application of phenoxycarboxylic acid oxime esters SCHERING AG 17 Dec 1973 [15 Dec 1972] 58373/73 Heading A5E [Also in Division C2] Herbicidal compositions comprise as active ingredient a compound of the general formula: in which R 1 and R 2 each represents an unsubstituted or a mono-, di- or poly-substituted aromatic, aliphatic, cycloaliphatic, araliphatic or heterocyclic hydrocarbon group, and R 1 may also represent a hydrogen atom, or R 1 and R 2 together with the adjacent carbon atom represent an unsubstituted or a mono-, di- or polysubstituted cycloaliphatic hydrocarbon group which may be interrupted by a nitrogen hetero atom and/or an oxygen hetero atom, R 3 represents a hydrogen atom or a 1-3 alkyl group, n represents 0, 1, 2 or 3, and each X represents a 1-3 alkyl group, a 1-3 alkoxy group, a halogeno-alkyl group or a halogen atom. There may also be added other herbicides such as maleic hydrazide. 3- amino-1, 2, 4-triazole, N-(1, 1-dimethyl-2- propyl)-3, 5-dichlorobenzamide, N, N-di-(npropyl)-2, 6-dinitro-4-trifluoro-methylaniline, 4- amino-3, 5, 6-trichloro-picolinic acid and 1, 1'- dimethyl-4, 4'-bipyridylium salts. [GB1458825A]

Description

Herbicldal preparations containing a-phenoxy al kanolc add ox1 me esters The present Invention Is concerned with herblcldal preparations / containing a-phenoxy-alkanolc add oxlme esters as active substances, and also with the use of such oxlme esters for controlling undeslred plant growth, especially In grass crops.
The combating of undeslred plant growth 1n grass crops cannot be carried out satisfactorily with the known herbicides, because they possess hardly any activity against millet species, for example Digltaria sangulnalis, Echinochloa crus galll and Setarla faberii. These species of millet constitute a group of annual Phanerogamae which are so profusely distributed 1n many areas sown with grass crops that they jeopardise the cultivation of these crops or the use of the areas.
Accordingly, the problem hitherto has been to provide a herbicide which 1s capable of combating especially these species of millet, and this problem 1s solved by the present invention.
The present Invention provides a herblcldal preparation which comprises a compound of the general formula I 1n which and R2 each represent an aromatic, aliphatic, cycloallphatic or aral1phat1c group which groups may be unsubstltuted or optionally mono-, dl- or polysubstltuted by alkyl, halogen, alkoxy, halogenoalkyl or nitro groups and R^ may also represent a hydrogen atom or R1 and R2 together with the adjacent carbon atom represent a cycloallphatic hydrocarbon group which may optionally be mono-, d1- or polysubstltuted by alkyl, Rg represents a hydrogen atom or a lower alkyl group, jn represents 0, 1, 2 or 3, and each X represents a lower alkyl group, a lower alkoxy group, a halogeno-alkyl group or a halogen atom, in admixture or conjunction with a suitable carrier. The preparation may of course contain one or more compounds of the general formula I.
The present Invention also provides a method of protectlns living plant against weeds, wherein the area 1n the vicinity of a living plant 1s treated with a compound of the general formula I.
The present Invention further provides a method of protecting a crop area against weeds, wherein a crop area 1s treated with a compound of the general formula I.
As aromatic hydrocarbon groups represented by Rj and Rg there come Into consideration, for example, phenyl and naphthyl groups, as aliphatic hydrocarbon groups, for example, those containing 1 to 12 carbon atoms, for example methyl, ethyl, propyl, Isopropyl and butyl, as cycloallphatic hydrocarbon groups those containing 5 to 8 carbon atoms, for example cyclohexyl, and as arallphatlc hydrocarbon groups, for example, benzyl and phenyl-ethyl , and these groups may be substituted, for example, 1n the same or different ways by lower alkyl groups, for example methyl or ethyl, halogen atoms, for example chlorine or bromine, lower alkoxy groups, for example methoxy or ethoxy. As lower alkyl groups represented by R3 and as the other lower alkyl and lower alkoxy groups mentioned above there come Into consideration those containing 1 to 3 carbon atoms.
Rl and Rg together with the adjacent carbon atom may also form a cycloallphatic 5- to 8-membered ring, for example cyclohexyl dene and cyclo-octylldene, which may be mono-, d1- or poly-substituted by lower alkyl groups, for example methylβ and/or by othor groups, and which may also be nterrupted by —and/or 0 hotbro atoms.
When n represents 2 or 3, the substltuents represented by X may be the same or different.
The compounds used 1n accordance with the present Invention exhibit, surprisingly, a very good herblddal action agalest the above-mentioned species of millet, and are therefore especially suitable for combating these very resistant weeds. Especially distinguished 1n this connection are those compounds n which Rj and Rg 1n the above general φ formula I each represents an alkyl group containing 1 to 4 carbon atoms or a phenyl group that may be substituted by a nltro group , a methyl group or a chlorine atom, and Rj may (also represent a hydrogen atom, or R.| and to§ether with the adjacent carbon atom represent a cyclohexyl ldene or a trlmethyl -cyclohexenylldene group, Rj represents a hydrogen atom or a methyl group, n. represents 0 or an Integer from 1 to 3 and each X represents a methyl group or a halogen atom. The groups represented by Rj and R2 may be Identical or different.
The action of these compounds also extends to many other weeds , for example Slnapsls sp. , Solanum sp. . Medlcago sp. , Stellarla media.
Seneclo vulgaris . Matricaria obfonomllla, Lamlum amplexlcaule, Centaurea cyanus . Amaranthus retroflexus , Gal ium aparine , Chrysanthemum segetum, I omea purpurea dnd Polygonum Lapathl foil urn.
A further Important advantage of the compounds used In accordance with the present Invention Is their excel lent tolerabll l ty towards cultivated grasses, barley, wheat, oats , rye, maize, rice and potatoes, which are not Impaired by the treatments.
The rates of appl ication are, depending on the region of use and the nature of the plants, approximately 0,5 to 3 kg of active substance per hectare; when two or more compounds of the general formula I are used the range of approximately 0.5 to 3 kg refers of course to the total amount appl ied of these compounds.
The compounds used in accordance with the present Invention may be appl ied singly or a sr; a mixture of two or several active substances , and also 1n admixture with other plant protecting and pest combating agents. When it Is desired to widen the spectrum of action there may also be added other herbicides , 1n which case the selectivity 1s , of course , not always maintained. As herblddal ly active co-components for mixtures there are suitable, for example, active substances belonging to the groups of carboxyHc adds andjderlvatlves thereof, cachajQic as4d *Hpr1vat1vp¾ , dlphenyl ether derivatives, anil Ides, uracils, nltrlles and other k organic herbicides, for example malelc hydraz de, 3-am1no-l ,2,4-tr1-azole, N-(l ,l-d1methyl-2-propyl)-3,5-d1chlorobenzam1de, N.N-dl-frv-propyl )-2 ,6-dl n1 tro-4-tr f 1 uoro-methylan 1 ne , 4-am1 no-3 ,5 ,6- tr1 chloro-plcol nlc add and 1 ,1 '-dimethyl -4,4* -blpyridy 11 urn salts.
Depending on the purpose of use there may be added other substances, among which there are to be understood, for example, also phytotoxlc non-pytotoxtc additives, which may produce a synergistic ncrease 1n activity with herbicides, for example wetting agents, emulsifiers, solvents and oily additives.
The active compounds of the general formula I or mixtures thereof used 1n accordance with the present nvention are advantageously applied in the form of herblddal preparations, for example powders, spraying or dusting agents, granules, solutions, emulsions or suspensions, with the addition of liquid and/or solid vehicles or diluents and, 1f desired, of surface-active agents, for example wetting, adherent, emulsifying and/or dispersing agentss Suitable liquid carriers, are, for example, water, aliphatic and aromatic hydrocarbons, for example benzene, toluene, cyclohexanone and Isophorone and, also mineral oil fractions.
As solid carriers there are suitable mineral earths, for example tonsil, silica gel, talcum, kaolin, Attaclay, limestone and silicic acid, and vegetable products, for example meals.
As surface-active agents there may be mentioned, for example, calcium Hgn1rf ulphonate, polyoxyethylene octyl-phenyl ethers, naphthalene — sulphon c adds, pheno sul phonic adds, formaldehyde condensates, fatty alcohol sulphates and alkali metal and at (call ne earth metal salts of fatty adds.
The total amount of the active compound or compounds of the general formula I in the various herblddal preparations may vary within Bide limits. For example, the preparations may contain approximately 20to of liquid or solid carrier, and, If desired, also up to 20% by weigh y ^ of surface-active agent(s) .
The preparations may be applied In the usual manner, for example, wi th water as carrier 1n quantities of spray Hquor from 100 to 1 ,000 l itres per hectare. For the total destruction of weeds there may be applied directly quantities of spray Hquor exceeding 1 ,000 l itres per hectare that are sometimes used. It 1s also possible to use the agents In the so-called "ultra-low-volume method" . They may furthermore be appl ied 1n the form of mlcrogranules.
It Is also possible, for example, to apply the preparations ready for use by spraying or scattering them on the soil still free from weeds. By Incorporating the preparations In the soil their activity is generally increased.
The compounds used In accordance with the preset^ Invention may be prepared as-descplbed below.-- by reacting The-preseRt-inveBti9R-acGoWlingly-furthe*:-pr.ovidas-a-process-for the-manufactupe-ef-a-CQmpouRdr— of-the-genepa^-fermu^a-i-j-wherein an oxime of the general formula In which R^ and R2 have the meanings given above , or an alkali metal salt thereof, for example the sodium or potassium salt, s- reacted, an a- al kanoic . „ a) with & phenoxy-earbexy44e acid hal lde of the general formula In which R3 , n and X have the meanings given above and Hal represents a halogen atom, If desired 1n the presence of an ac1d-b1nd1ng ageet, for example an organic or Inorganic base, for example trl ethyl amine, dimethyl -aniline , pyridine, sodium carbonate or sodium hydroxide solution , and of a solvent, for example a chlorinated hydrocarbon , ether, ester, nitrlle , add amide or water, preferably methylene chloride , tetrahydrofuraflj, 1 d oxan, ethyl acetate, acetonltrl le or dimethyl formamtte , or b) with an acid anhydride of the general formula 1n w§1ch R3, ji and X have the meanings given above , 1f desired 1n the presence of an acid-binding agent, for example pyridine, N,N-d1methyl- anlUne or tr1 ethyl amine, and of a sol ent, for example an al iphatic or aromatic hydrocarbon, and especial ly benzene , pyridine, tetrahydrof uran , dloxan , dimethyl sulphoxlde , acetonltrlle or d1 methyl formamlde.
Some compounds used 1n accordance with the present I vention are given 1n the fol lowing Table I .
TABLE I Name of the compound Physical constant 3,#-D1chlorophenoxy-acet1c add methyl (1 - 20 metfiyl -propyl ) ketox me-ester nD " 1.5360 2- ( 2 ,4-D1 chl orophenoxy ) -propl onl c ad d 20 acetone oxlme-ester nD = 1.5390 2,4-01chlorophenoxy-acet1c add acetone o Srtme-ester M.p. : 81 eC (2-Methyl -4-chl orophenoxy )-acet1 c ad d acetone oxlme-ester M.p. : 58°C 2,4-D1chlorophenoxy-acet1c add (3 ,5 ,5-trlmethyl -2-cycl ohexenone ox1me)-ester M.p. : 112eC (2-Methyl -4-chl orophenoxy}acet1 c ad d (3, 5 , 5- tH methyl -2-cycl ohexenone ox1me)ester M.p. : 96°C 2,4,5-Tr chlorophenoxy-acet c add acetone oxlme-ester M.p. : 83°C 2- ( 2 ,4-D1 chl orophenoxy ) -propl on1 c ad d (3 ,5 ,5- trlmethyl -2-cycl ohexenone ox1me )-es ter n20 e nD 1 .5495 2-(2-Methyl-4-chlorophenoxy)-prop1on1c add 20 acetone oxlme-ester 1 .5248 Name of the compound Physical constant 2- ( 2, 4-D1chlorophenoxy) -propionic add acetophenone oxlme-ester M.p. : 102eC 2-(2,4-D1chlorophenoxy)-prop1on1c acid methyl 20 Isobutyl ketoxime-ester riQ = 1.5245 2- ( 2, 4-D1chlorophenoxy) -propionic add (3- nitrobenzaldox1me)-ester M.p. : 72eC 2- (2, 4-Dichlorophenoxy) -propionic add 20 benzophenone oxlme-ester nn " 1.6005 2,4^,5-Trlchlorophenoxy-acetlc acid cycfphexanone oxlme-ester ( 2- ethyl-4-chlorophenoxy)-acet1c add cyclo hexanone oxlme-ester 2- (2 ,4 ,5-Tri chl orophenoxy ) -propl on1 c ad d acetone oxlme-ester 2-(2,4,5-Tr1chlorophenoxy)-prop1on1c acid cyclohexanone oxime-ester 4-Bromophenoxy-acetic acid acetone oxime-ester 4-Bromophenoxy-acet1c add cyclohexanone oxime- ester 2-(2,4-D1methylphenoxy)-prop1onic acid acetone ox1 ester 2,4-Dichlorophenoxy-acetic acid methyl ethyl ketoxime-ester 2,4-D1chlorophenoxy-acet1c acid diethyl ketoxime-ester 2,4-Dichlorophenoxy-acetic acid methyl propyl ketoxime-ester 2-(2,4-D1chlorophenoxy)-prop1on1c add methyl ethyl ketoxime-ester 2-(2,4-D1chlorophenoxy)-prop1onic acid diethyl ketoxlme-estdr 2-(2,4-D1chlorophenoxy)-prppion1c acid methyl propyl ketoxime-ester 3 Chlorophenoxy-acet1c acid acetone oxime-ester 2,4-Dichlorophenoxy-acetic acid methyl isobutyl ketoxime-ester 2,4-Dichlorophenoxy-acetic acid methyl isopropyl ketoxime-ester (2-Methyl-4-chl orophenoxy acet1c acid methyl ethyl ketoxime-ester 2- (2 ,4-D1chlorophenoxy)-prop1onic add, butyrophenone oxlme-ester \ nD 1.5666 (2-Methyl-4-chlorophenoxy acetic add diisobutyl ketoxlme-ester nD 1.5112 2-(2# -D1chlorphenoxy)-propion1c acid di isobutyl ketoxlme-ester nD - 1.Sv14.0 2- (2- ethyl-4-chlorophenoxy)-prop1on1c add d1 isobutyl ketoxime-ester nD a 1 .5040 2,4-D1ch1orophenoxy-acet1c acid di isobutyl ketoxlme-ester 20 nD ° 1.5210 2,4-D1chlorophenoxy-acet1c add phenoxyacetone oxlme-ester n20« 1.5720 2- ( 2, 4-Dichlorophenoxy)- propionic add phenoxy-acetone oxlme-ester n20o nD ° 1.5628 2- (2- ethyl -4-chlorophenoxy) -propionic add diethyl ketoxlme-ester nD - 1.5179 2-(2-Methyl-4-chlorophenoxy)-propion1c acid methyl ethyl ketoxlme-ester n20o 1.5223 2-(2- ethyl-4-chlorophenoxy)-propion1c acid methyl propyl ketoxlme-ester n 0= 1.5177 2- (2-Methyl-4-chlorophenoxy) -propionic add methyl Isobutyl ketoxime-ester n20« 1 .5125 2,4,5-Trlchlorophenoxy-acetlc add diethyl ketoxime-ester M.p. : ; 55°C 2,4,5-Trichlorophenoxy-acetlc add methyl ethyl ketoxime-ester 20 1.5581 2,4 ,5-Trichlorophenoxy-acetlc acid methyl propyl ketoxime-ester r,20= 1 .5450 2,4,5-Trichlorophenoxy-acetic add methyl Isobutyl ketoxim ,ee^2go ester 1 1..5261 (2-Methyl-4-chlorophenoxy)-acet1c add dlpropyl ketoxlme-ester n D20» 1 .5210 n20n nD 1 .5319 2- (2,4-D1chlorophenoxy)-proptoii1c acid dlpropyl 20 ketoxlme-ester nD - 1 .5210 2,4,5-Trichlorophenoxy-acetic acid dlpropyl ketoxlme-ester M.P. : ; 44°C 2,4,5-Trlchlorophenoxy-acetlc add dilsobutyl ketoxlme- ester 1 .5287 nD Name of the compound , Physical consent 2-(2-Methyl-4-c Torophenoxy)-propion1c adi dlpropyl 2n ketoxlme-ester njj a 1.5090 (2-Methy1-4~chlorophenoxy)-acet1c acid methyl Isopropyl 20 ketoxlme-ester n^ β 1.5282 2-(2-Methyl-4-chlorophenoxy)-prop1on1c add methyl -g Isopropyl ketoxlme-ester np * 1.5163 2-{2,4-D1chlorophenoxy)-prop1on1c acid methyl Isopropyl ?n ketoxlme-ester njj = 1.5283 2,4,5-Tr1chlorophenoxy-acet1c add methyl sopropyl N ketoxlme-ester M.p. : 72eC (2-Methyl-4-chlorophenoxy)-acet1c add methyl hexyl 2Q ketoxlme-ester nD B 1.5160 2,4-Dlchlorophenoxy-acetlc add methyl hexyl ketoxime- 9n ester nj - 1.5255 2- (2-Methyl-4-chlorophenoxy) -propionic add methyl hexyl 2n ketoxlme-ester nD * 1.5080 2-(2,4-D1chlorophenoxy)-prop1on1c add methyl hexyl 20 ketoxlme-ester njj = 1.5182 2, 95-Tr1chlorophenoxy-acet1c add methyl hexyl ketoxime- «n ester n^ «1.5328 2-(2~Methyl-4-chlorophenoxy)-prop1on1c add (3,5,5- «η trlmethyl-2-cycl ohexenone ox1me)-ester nQ β 1.5418 2-4-D1chlorophenoxy-acet1c add (3,5-d1methyl-2- cyclohexenone ox1me)-ester M.p. : 77 - 80eC 2-(2,4-D1chlorophenoxy)-prop1on1c add (3,5-d1methyl- 2-cycl ohexenone ox1me)-ester 2,4,5-Trlchlorophenoxy-acetic add (3,5,5-trlmethyl 20 2-cycl ohexenone ox1m nee))-ester nQ a 1.5678 2»4-D1chlorophenoxy-acet1c a d cyclohexanone oxlme-ester n^ B 1.5569 2-(2,4-D1chlorophenoxy)-prop1on1c acid cyclohexanone 2n oxlme-ester ηβ ■ 1.β489 2-(2-Methyl-4-chlorophenoxy)-prop1on1c add cyclohexanone 2Q oxlme-ester np » 1.5372 2,4-D1chlorophenoxy-acet1c add methyl (2-methoxy-ethyl ) «η ketoxlme-ester nD B 1.5412 2-(2,4-D1chlorophenoxy)-prop1on1c add methyl (2-methoxy- 20 ethyl ) ketoxlme-ester p β 1.5311 (2-Methyl-4-chlorophenoxy)-acet1c acid ethyl butyl ketoxime- 2n ester n^ = 1.5200 2,4-D1chlorophenoxy-acet1c acid ethyl butyl ketoxime- 20 Name of the compound Physical constant 2- (2-Methyl-4-chlorophenoxy) -propionic add ethyl «η butyl ketoxlme-ester nQ β 1.5122 2- (2, 4-Dbhlorophenoxy) -propionic acid ethyl butyl «n ketoxlme-ester nD β 1.5218 2 »4,5-Tr1chlorophenoxy-acet1c add ethyl butyl 2n ketoxlme-ester 1.5375 (2-Methyl-4-chlorophenoxy)-acet1c add cycl opentanone oxlme-ester .p. : 70-72°C 2 ,4-D1chlorophenoxy-acet1c add cycl opentanone oxlme-ester 011 2,4 ,5-Trichlorophenoxy-acetic acid cycl opentanone oxlme-ester M.p. : 100-J02°C (2-Methyl-4-chlorophenoxy>-acd*1c add (3-methyl-cycl opentanone ox1me)-ester M.p. : 71 - 72eC 2,4-01chlorophenoxy-acet1c add (3-methyl -cyclo- 20 pentanone oxime) -ester nD = 1 .5485 2,4-D1chlorophenoxy-acet1c add ethyl pentyl ketoxlme-ester i D20- 2-(4- Chloro-2-methylphenoxy)-prop1on1c acid ethyl 20. pentyl ketoxime-ester 2- ( 2 , 4-Dichlorophenoxy) -propionic acid ethyl pentyl ketoxlme-ester 2,4,5-Trichlorophenoxy-acetic acid ethyl pentyl ketoxlme-ester (4-Chloro-2-methylphenoxy>acetic acid ethyl pentyl ketoxlme-ester 2,4-D1chlorophenoxy-acet1c acid ethyl Isopropyl ketoxlme-ester 2,4,5-Trichlorophenoxy-acetic add ethyl isopropyl ketoxlme-ester 2-(2-Methyl -4-chlorophenoxy)-prop1onic acid ethyl Isopropyl ketoxime-ester 2- (2 , 4-D1chlorophenoxy) -propionic acid ethyl isopropyl ketoxlme-ester (2-Methyl-4-chlorophenox^-acetic acid ethyl Isopropyl (4-Chloro-2-methylphenoxy) acet1c add isopropyl pentyl ketoxlme-ester 2,4-D1chlorophenoxy-acet1c acid Isopropyl pentyl ketoart ester Name of the compound · Physical cons ant^ 2-(4-Chloro-2-methylphenoxy)-pro$1on1c add Isopropyl pentyl ketoxlme-ester (4-Ch1oro-2-methylphenoxy-)acet1c acid ethyl propyl ketoxlme-ester 2,4-D1chlorophenoxy-acet1c add methyl tert.-butyl ketoxime-ester 2-(4-Chloro-2-methylpBenoxy)-prop1on1c add methyl tert.-butyl ketoxlme-ester 2-(2,4-D1chlorophenoxy)-prop1onic acid Isopropyl pentyl ketoxlme-ester 2,4-D1chlorophenoxy-acet1c acid Isopentyl methyl ketoxlme- ester 2-(4-Chloro-2-methyl henoxy)-propionic add Isopentyl methyl ketoxlme-ester (4-Chloro-2-methylphenoxy)-acetic add Isopentyl methyl tetoxlme-ester 2,4,5-Trichlorophenoxy-acatic add Isopentyl methyl .20. ketoxime-ester nQ a 1.5354 2-(4-Chloro-2-methylphenoxy)-propion1c add butyl methyl 2n ketoxlme-ester nQ = 1.5119 20 2,4-D1chlorophenoxy-acet1c add butyl methyl ketoxlme-ester nR = 1.5338 2-(2,4-D1chlorophene,xy)-propion1c acid Isopentyl methyl 2n ketoxlme-ester nD * 1,5215 2-(2,4-Dichlorophenoxy)-propionic add butyl methyl 2n ketoxlme-ester np = 1.5246 2,4,5-Trichlorophenoxy-acetic add butyl methyl ketoxime- .20. ester n^= 1.5351 4-Chloro-2-methylphenoxy-acet1c add butyl methyl 20 ketoxlme-ester nQ * 1.5208 2,4»5-Tr1chlorophenoxy-acet1c add methyl tert. -butyl ketoxlme-ester .p.: 106eC 2-(2,4 D1chlorophenoxy)-prop1onic acid ,hiethyl tert.-butyl 20 ketoxlme-ester ' nQ β 1.5246 (4-Chloro-2-methyl henoxy>acet1c acidiethyl tert.-butyl «o ketoxlme-ester nQ β 1.5209 2-(2-Methyl-4-chlorophenoxy)-propionic acid (3-methyl- 20. cyclopentanone oxlme^-ester n^a 1.5272 2-(2,4-D1chlorophenoxy)-prop1onic add (3-methyl- 2o cyclopentanone ox1me)-ester Q B 1.5418 Name of the compound t Physical constant 2,4-Dichlorophenoxy-acetic add ethyl propyl ketoxlme- 9n ester n^ - 1 .5282 2-(2,4-D1chlorophenoxy)-prop1onic add dthyl propyl 2n ketoxime-ester Q B 1 .5240 2-(2-Methyl -4-chlorophenoxy)-propion1c acid ethyl propyl ketoxime-ester0 1 .5133 2,4,5-Trlchlorophenoxy-acetic acid ethyl propyl ketoxime-ester 1 .5440 2,4,5-TrichIorophenoxy-acetic acid (3-methyl -cyclopentanone oxime)-ester .p. r, 119-120°C \ (2- ethyl -4-chlorophenoxy)-acetic acid di lsopropyl 20 ketoxime-ester n. I .9 1 J 2,4-Dichlorophenoxy-acetic acid dl isopropyl ketoxime- ester n^°= ί .5271 \ 2-(2-Methyl-4-chlorophenoxy)-prop1onic acid dlisopropyl ketoxime-ester 2-(2,4-D1chlorophenoxy)-prop1on1c acid dlisopropyl ketoxime-ester np - 1.5190 \ 2,4-D1chlorophenoxy-acet1c acid 3-pentanone oxime-ester n*°« 1 ,5411 2,4-Dichlorophenoxy-acetic acid 4-heptanone oxime-ester 20 hp = 1 ,5319 The compounds of the general formula I are colourless and odourless , oily or crystal line substances which are , for example, insoluble in water Herblcldal preparations ready for use of the compounds of the general formula I and mixtures thereof can be made i n a known manner, for example, by mixing or grinding methods . If desired, the Individual components may be mixed together only shortly before being used, for example, by the so-called tank mix method carried out in practice.
The fol lowing Examples Illustrate the Invention. Example 1 Il lustrates the manufacture of a compound of the general formula I and Examples 2 to 6 Il lustrate the herblcldal activity of the compounds of the general formula I .
Example 1 >_C 2.4-D1chlorophenoxy-acet1c add methyl (l-methyl-propyl )ketoxlme-ester 29.4 grams of 2,4-d1chlorophenoxy-acet1c add chloride were added dropwlse, while stirring, to a solution of 14.1 grams of methyl (1-methyl-propyl ) tetoxlme and 12.4 grams of trl ethyl amine 1n 200 ml of aceton trlle, during which the temperature rose to 45°C. The reaction mixture was stirred for a further 3 hours , then poured Into 2 litres of water, and the oil that separated was extracted with ether. The ethereal phase was agitated with a dilute solution of sodium hydroxide and then with water, and dr½d over magnesium sulphate. The solvent was distil led off and the remainder thereof was removed In a high vacuum. The oil that remained behind weight 20 36.0 grams (92¾ of the theoretical yield) ; nj ■ 1 .5360.
Example 2 The compouhds l isted 1n the following Table were sprayed in a greenhouse on millet plants of the species mentioned at the rate of 3 kg of the active compound being tested per hectare. The plants were 1n the 2- to 3-1 eaf stage at the time of the treatment. An aqueous emulsion of the compounds was used 1n each case and was applied at the rate of 500 litres per hectare.
The results were evaluated 2 weeks after the treatment according to a scale of values extending from 0 to 10, the value 0 representing "totally destroyed" and the value 10 representing "not damaged" .
The results ishow the excellent herblddal action against mil let plants.
- - Active compound n preparation of the present nvention , 2, 4-D1chlorophenoxy-acet1c acid acetone oxime-ester 0 2-Methyl -4-chl orophenoxy-acetl c ad d acetone oxime-ester 0 2- (2j4-D1chlorophenoxy)-prop1on1c add acetone oxime-ester 1 1 2- (2-Meth 1 -4-chl orophenoxy )-propi oni c add acetone oxime-ester 1 1 2- (2 ,4 , 5-Tri chl orophenox ) -prop on1 c add acetone oxime-ester 2 3 2-(2,4,5-Tr1chlorophenoxy)-prop1onic add cyclohexanone oxime-ester 3 3 2,4-D1chlorophenoxy-acet1c add methyl ethyl ketox1me-ester 5 3 2,4-D1chlorophenoxy-acet1c acid methyl propyl ketoxlmet- estdr 5 4 2 ,4-Di chl orophenoxy-acetl c add methyl isobutyl ketoxlme-ester 1 1 2,4-D1chlorophenoxy-acetic add methyl Isopropyl ketoxlme-ester 4 3 IH-Methyl -4-chl orophenoxy )-acet1c add methyl ethyl ketoxlme-ester 5 2 fc- ethyl -4-chl orophenoxy acet 1c add diethyl ketoxlme-ester 5 5 (2-Methyl -4-chbrophenoxy)-acet1c add methyl propyl ketoxlme-ester 5 5 ( 2-Methyl -4-chl orophenoxy)-acet1c add d1 isobutyl ketoxlme-ester 2 2 2-(2 ,4-D1chlorophenoxy)-prop1on1c add dilsobutyl ketoxlme-ester 1 2-(2-Mathyl-4-chlorophen¾Ay)-brop1on1c add dilsobutyl ketoxlme-ester 1 3 2, 4-D1 chl orophenoxy-acetl c add dilsobutyl ketoxlme-ester 5 1 2,4-Dlchlorophenoxy-acetic acid phenoxy- ace tone oxime-ester 4 4 2- (2-Methyl -4-chl orophenoxy ) -propl oni c acid diethyl ketoxlme-ester 4 2- (2-Methyl -4-chl orophenoxy ) -propl on1 c add methyl Isobutyl ketoxlme-ester 4 4 2,4,5-Tr1chlorophenoxy-acet1c add diethyl ketoxlme-ester 4 4 Active compound 1n preparation of the present nvention 2 ,4 , 5-TY1 chl orophenoxy-acetl c ad d methyl ethyl ketoxlme-ester 3 4 - 5 2,4,5-Trlchlorophenoxy-acetic acid methyl propyl ketoxlme-ester 4 5 1 0 2 ,4 ,5-Trlchl orophenoxy-acet c ad d methyl Isobutyl ketoxlme-ester — 3 0 _ 2-Methyl -4-chl orophenoxy-acetl c ad d d1 propyl ketoxlme-ester _ 0 0 1 2,4-D1chlorophenoxy-acet1c add dlpropyl ketoxlme-ester 5 0 0 1 Untreated 10 10 10 10 0 tt totally destroyed 10 = not damaged Example 3 The crop plants and weeds l isted tn the fol lowing Table were sprayed tn a greenhouse by the post-emergence method with the compounds l isted at the rate of 1 kg of active compound being tested per hectare, the active compounds tn each case being applied 1n the form of an aqueous emulsion using 500 l itres per hectare.
The results were evaluated 2 weeks after the treatment tn the manner described in Example 2.
It was found that the weeds suffered considerable damage while the crop plants were completely protected.. 10 s- Active compound 1n preparation of the present g « >> /invention 2- (2,4-D1chlorophenox )-prop1on1c acid acetone oxirae-ester 2,4-Dlch orophenoxy-acetlc acid acetone oxlme- ester (2-Methyl-4-chlorophenoxy)-acet1c acid acetone oxlme-ester (2-Methyl-4-chlorophenoxy)-acet1c add (3,5.5- tri meth l -2-cy cl ohexenone ox1 me ) -ester 2- (2 ,4-Di chl orophenoxy )-prop1on1 c aci d (3,5,5- tr1 me th 1 -2-cyc 1 ohexenone oxl me ) -es ter - 10 10 2,4-D1chlorophenoxy-acet1c acid (3,5,5 tr1methyl-2-cyclohexenone oxime)-ester 2-(2,4-D1chlorophenoxy)-prop1on1c add acetophenone oxime-ester 10 10 10 2- (2,4-D1chlorophenoxy)-propionic acid (3- n1 trobenzal doxlme )-ester 10 10 10 2- (2, 4-D1ehl orophenoxy )-propionie acid benzophenone oxlme-ester 10 10 10 2- ( 2-Methyl -4-chl orophenoxy )-prop1 oni c ad d acetone oxlme-este 10 10 _ 2,4,5-Tr1chlorophenoxy-acet1c acid cyclohexa- none oxime-ester 10 10 10 (2-Methyl-4-chlorophenoxy)-acet1c acid cyclohexanone oxlme-ester 10 10 10 10 10 4 2,4-Dlchlorophenoxy-acetlc acid diethyl ketoxime-ester 10 10 10 10 _ 4 2-(2,4-D1chlorophenoxy)-prop1on1c acid methyl ethyl ketoxime-ester 10 10 10 10 10 1 2-(2,4-Dlchlorophenoxy)-prop1on1c acid diethyl ketoxime-ester 10 10 10 10 10 3 2-(2,4-D1chlorophenoxy)-prop1onic acid methyl propyl ketoxime-ester 10 10 10 10 10 1 2-(2»4-D1ch*orophenoxy)-prop1onic acid butyrophenone oxlme-ester 10 10 10 10 10 2 2-(2,4-Dichlorophenoxy)-prop1on1c acid phenoxy-acetone oxlme-ester 10 10 10 10 10 0 2-(2-Methyl-4-chlorophenoxy)-prop1on1c add methyl ethyl ketoxime-ester 10 10 10 10 10 0 2-(2- ethyl-4-chlorophenoxy)-;prop1on1c acid methyl propyl ketoxime-ester 10 10 10 10 10 0 2-(2,4-D1chlorophenoxy)-prop1onic acid dlpropyl ketoxime-ester 10 10 10 10 10 0 2t4,5-Trichlorophenoxy-acet1c acid dlpropyl ketoxime-ester 10 10 10 10 10 2 Untreated 10 10 10 10 10 10 0 = totally destroyed 10 = not damaged Example 4 The weeds listed 1n the following Table were sprayed In a greenhouse by the post-emergence method with the compounds l isted at the rate of 0.3 kg of active compound being tested per hectare , the active compounds in each case being appl ied 1n the form of an aqueous emulsion using 500 li tres per hectare.
The results were evaluated 2 weeks after the treatment by the method described in Example 2.
The preparation used 1n accordance with the present invention damaged the weeds more strongly than the preparation used for comparison.
Example 5 The species of plants listed In the following Table were sprayed 1n a greenhouse by the post-emergence method with the compounds listed at a limiting concentration of 0.3 kg of active compound being tested per hectare. The compounds were 1n each case applied In the form of an aqueous emulsion.
The agent used for comparison exhibited a very low herblcldal action. On the other hand, the compounds used 1n accordance with the present nvention caused considerable damage to the weeds whi le completely sparing the crop plants .
The results are expressed by a scale extending from 0 to 10, the value 0 representing "total ly destroyed" and the value 10 representing "not damaged" . if.
Active compound In preparation of the present Invention 2-(2,4-D1chlorophenoxy)-prop1on1c add methyl propyl ketoxime-ester 10 10 10 1 2-(2,4-Dichlorophenoxy)-prop1on1c add methyl isopropyl ketoxime- ester 10 10 10 1 2-(2,4-Dichlorophenoxy)-prop1on1c add methyl Isobutyl ketoxime- ester 10 10 10 1 2-(2,4-D1chlorophenoxy)-prop1onic acid methyl hexyl ketoxime-ester 10 10 10 1 2-(2,4-D1chlorophenoxy)- ropionic add dipropyl ketoxime-ester 10 10 10 1 2-(2,4-D1chlorophenoxy)-prop1onic acid diisobutyl ketoxime-ester 10 10 10 1 2-(2,4-Dichlorophenoxy)-prop1onic acid cycl ohexanone oxime-ester 10 10 10 1 ' (2-Methyl-4-chlorophenoxy)-acet1c acid ethyl butyl ketoxime-ester 10 10 10 1 ~* 2,4-D1chlorophenoxy-acetic acid ethyl butyl ketoxime-ester 10 10 10 1 2-(2-Methyl-4-chlorophenoxy)-propionic add ethyl butyl ketoxime- ester 10 10 10 1 Active compound in preparation for comparison 2-(2,4-Dichlorophenoxy)-propion1c acid 10 10 10 1 totally destroyed not damaged i Maze h Wtae l Byera Example 6 In a greenhouse Setaria 1ta11ca was sprayed by the post-emergen¾e φ method with the compounds listed 1n the following Table at the rate of 5 kg of active compound being tested per hectare, and 1n each case n the form of an aqueous emulsion using 500 litres per hectare.
The results were evaluated 3 months after the treatment, the symbols meaning: 0 a not damaged 1 a sl ightly damaged 2 ° medium damage 3 β heavy damage and 4 « total ly destroyed.
The results show the excellent action of the preparations used in accordance with the present invention.
Active compound 1n preparation of the present nvention Sfetarla Itallca 2- ( 2, 4-D1chlorophenoxy) -propionic acid acetone oxime-ester 4 2,4-D1chlorophenoxy-acet1c acid acetone oxime-ester 4 £-Methyl-4-chlorophenoxy)-acet1c add acetone oxime-ester 4 2,4-D1chlorophenoxy-acet1c add ( 3,5,5- tr me thy 1-2-cyclo- hexenone ox1me)-ester 4 (2-Methyl-4-chlorophenoxy acet1c add (3,5,5-tr1methyl-2- cyclohexenone ox1me)-ester 4 2,4,5-Tr1chlorophenoxy-acet1c add acetone oxime-ester 4 2-(2,4-D1cblorophenoxy)-prop1on1c acid (3,5,5-tr1methyl-2- cyclohexenone ox1me)-ester 3 2,4,5-Trlchlorophenoxy-acetlc add ethyl pentyl ketoxlme-ester 4 2- (4-Chloro-2-methylphenoxy) -propionic add ethyl pentyl ketoxlme- ester 4 2-(2,4-D1chlorophenoxy)-prop1on1c add ethyl pentyl ketoxlme- ester 4 (4-Chloro-2-methylphenoxy)-acet1c add ethyl pentyl ketoxlme-ester 4 2,4-D1chlorophenoxy-acet1c add ethyl pentyl ketoxlme-ester 4 2,4-D1chlorophenoxy-acet1c add ethyl Isopropyl ketoxlme-ester 4 2,4,5-Tr1chlorophenoxy-acet1c add ethyl Isopropyl ketoxlme- ester 4 2-(2-Methyl-4-chlorophenoxy)-prop1on1c add ethyl Isopropyl ketoxlme-ester 4 2-(2,4-D1chlorophenoxy)-prop1on1c add ethyl Isopropyl ketoxlme-ester 4 2-Meth l-4-chloro henox )-acet1c add eth l iso ropyl ketoxlme- Active compound 1n preparation of the present invention Setarla (4-Chloro-2-methyTphenoxy^acet1c add Isopropyl pentyl ketoxime-ester 4 2,4-Dichlorophenoxy-acetic add Isopropyl pentyl ketoxime-ester 4 2-(4-Chloro-2-methyl phenoxy)-prop1onic add Isopropyl pentyl ketoxime-ester 4 2-(2,4-D1chlorophenoxy)-prop1on1c add Isopropyl pentyl ketoxime- ester 4 2,4-Dichlorophenoxy-acetic add Isopentyl methyl ketoxime-ester 4 (4-Chloro-2-methylpbenoxy)acet1c add ethyl propyl ketoxime-ester 4 2- (4-Chloro-2-methy\>henoxy) -propionic add Isopentyl methyl ketoxime-ester 4 (4-Chloro-2-methylphenoxy)-acet1c add isopentyl methyl ketoxime- ester 4 2,4,5-Trlchlorophenoxy-acetic add Isopentyl methyl ketoxime- ester 4 2-(4-Chloro-2-methylphenoxy)-prop1on1c add butyl methyl ketoxime- ester 4 2,4-Dichlorophenoxy-acetic add butyl methyl ketoxime-ester 4 2- (2 ,4-D1chlorophenoxy)-prop1on1c acid Isopentyl methyl ketoxime- ester 4 2- (2,4-D1chlorophenoxy)~prop1on1c acid butyl methyl ketoxime- ester 4 2,4,5-THchlorophenoxy-acetlc acid butyl methyl ketoxime-ester 4 (4-Chloro-2-methylphenoxy)-acet1c add butyl methyl ketoxime-ester 4 2,4-Dichlorophenoxy-acetic add methyl tert. >butyl ketoxime-ester 4 2-(4-Chloro-2-methyl phenoxy)-prop1on1c acid methyl tert. -butyl ketoxime-ester 4 2 ,4,5-Trichlorophenoxy-acetlc add mejhyl tert. -butyl ketoxime- ester 4 2-(2,4-D1chlorophenoxy)-propionic acid methyl tert. -butyl ketoxime-ester 4 (2-Methyl-4-chlorophenoxy)acet1c add methyl tert.^butyl ketoxime- ester 2-(2-Methyl-4-chlorophenoxy)-propionic acid acetone oxime-ester 2-(2,4-D1chlorophenoxy)-propionic acid acetophenone oxime-ester 2-(2,4-Dichlorophenoxy)-prop1onic acid methyl isobutyl ketoxime- ester 2,4,5-Trichlorophenoxy-acetic acid cyclohexanone oxime-este (2- ethyl-4-chlorophenoxy)-acet1c add cyclohexanone oxime-ester 2- (2,4,5-Tr1chlorophenoxy)-prop1on1c add acetone oxime-ester 2-(2,4,5-Trichlorophenoxy)-prop1on1c add cycl ohexanone oxlme- ester 4-Bromophenoxy-acetic add acetone oxime-ester 4-Bromophenoxy-acetic acid cyclohexanone oxime-ester Active compound In preparation of the present Invention Setarla Itallca 2,4-D1chlorophenoxy-acet1c acid diethyl letoxlme-ester 4 2,4-D1chlorophenoxy-acet1c acid methyl propyl tetoxlme-este . 3 2,4-D1chlorophenoxy-acet1c add methyl (1-methyl propyl) ketoxime-ester 4 2,4-D1chlorophenoxy-acet1c acid methyl Isobutyl ketoxime-ester 4 2,4-D1chlorophenoxy-acet1c add methyl Isopropyl ketoxime-ester $ (2-Methyl-4-chlorophenoxy)acet1c add methyl ethyl ketoxime-ester , 3 (2-Methyl-4-chlorophenoxy-)acet1c add diethyl ketoxime-ester \3 (2-Methyl-4-chlorophenoxy}acet1c acid methyl propyl ketoxime-ester 3 (2-Methyl-4-chlorophenoxy-)acet1c add dllsobutyl ketoxime-ester 4 2-(2,4-D1chlorophenoxy)-prop1on1c add dllsobutyl ketoxime-ester 4 2-(2- ethyl-4-chlorophenoxy)-propionic add dllsobutyl ketoxime- ester 4 2,4-D1chlorophenoxy-acet1c add dllsobutyl ketoxime-ester 4 2,4-D1chlorophenoxy-acet1c add phenoxy-acetone oxime-ester 4 2- (2,4-D1chlorophenoxy)-propionic add phenoxy-acetone oxime-ester4 2- (2- ethyl-4-chlorophenoxy)-propionic add diethyl ketoxime-ester 3 2-(2- ethyl-4-chlorophenoxy)-propionic add methyl Isobutyl kej xlme-ester 3 2,4,5-Tr chlorophenoxy-acet1c acid diethyl ketoxime-ester 3 2,4,5-Trlchlorophenoxy-acetlc add methyl ethyl ketoxime-ester 4 (2-Methyl-4-chlcrophenoxy)acet1c add dlpropyl ketoxime-ester 4 2,4-D1chlorophenoxy-acet1c add dlpropyl ketoxime-ester 4 2-(2,4-D1chlorophenoxy)-prop1on1c acid dlpropyl ketoxime-ester 4 2,4,5-Trlchlorophenoxy-acetlc acid dlpropyl ketoxime-ester 3 2,4,5-Trlchlorophenoxy-acetlc add dllsobutyl ketoxime-ester 4 2-(2-Methyl-4-chlorophenoxy)-propionic acid dlpropyl ketoxime- ester 3 (2-Methyl-4-chlorophenoxy)-acetic acid methyl Isopropyl ketoxime- ester 4 2-(2-Methyl-4-chlorophenoxy)-prop16n1c add methyl Isopropyl ketoxime-ester 4 2,4,5-Trlchlorophenoxy-acetlc add mtthyl Isopropyl ketoxime- ester 4 (2-Methyl-4-chlorophenox¾-acetic acid methyl hexyl ketoxime-ester 4 2,4-Dichlorophenoxy-acetic acid methyl hexyl ketoxime-ester 4 2-(2-Methyl-4-chlorophenoxy)-propion1c acid methyl hexyl ketoxime-ester 4 2-(2,4-D1chlorophenoxy)-prop1on1c add methyl hexyl ketoxime- ester 4 2,4,5-Trlchlorophenoxy-acetlc add methyl hexyl ketoxime-ester 4 2-(2- ethyl-4-chlorophenoxy)-propionic acid (3,5,5-trlmethyl- 2-cyclohexenone oxime)-ester 4 Active compound 1n preparation of the present Invention Setarla taHca 2,4-Dlchlorophenoxy-acetic add (3 ,5-d1methyl-2-cyclohexenone Λ ox1me)-ester 4 2-(2 ,4-D1chlorophenoxy)-prop1on1c add (3 ,5-dimethyl-2- cyclohexenone ox1me)j - ester 4 2,4,5-Trichlorophenoxy-acetlc acid (3,5,5-tr1methyl -2- cyclohexenone oxime) -ester 4 2,4-D1chlorophenoxy-acet1c add cyclohexanone oxime-ester 4 2-(2s4-D1chlorophenoxy)-propionic acid cyclohexanone oxime-ester 4 2-(2-Methyl-4-chlorophenoxy)-prop1on1c acid cyclohexanone oxime- ester 3 2,4-Dichiorophenoxy-acetic acid methyl (2-methoxy-ethyl )- ketoxime-ester 4 1 - (2 ,4-Dichlorophenoxy)-propionic acid methyl (2-methoxy-ethyl ) ketoxime-ester 4 2,4-Dichlorophenoxy-acetic add ethyl butyl ketoxime ester 4 2- (2,4-D1chlorophenoxy)*sprop1onic add ethyl butyl ketoxime- ester 3 2,4,5-Trlchlorophenoxy-acetic acid ethyl butyl ketoxime-ester 4 (2-Methyl -4-chlorophenoxy)-acet1c acid cyclopentanone oxime-ester 4 2,4-D1chl orophenoxy-acet1c acid cyclopentanone oxime-ester 4 2 ,4,5-Trichlorophenoxy-acetlc acid cyclopentanone oxime-ester 3 (2-Methyl -4-chlorophenoxy)-acet1c add (3-methyl -cyclopentanone oxime) -ester 4 2,4-D1chlorophenoxy-acet1c acid (3-methyl -cyclopentanone oxime)- ester 4 2-(2- ethyl -4-chlorophenoxy) 'propionic acid (3-methyl -cyclopentanone oxime) -ester 3 2- (2fl-D1chlorophenoxy)-prop1onic acid (3-methyl -cyclopentanone oxime) -ester 3 2,4-D1chlorophenoxy-acet1c add ethyl propyl teoxlme-ester 4 2-(2,4-Dichlorophenoxy)-propionic acid ethyl propyl ketoxime- ester 4 2-(2- (Methyl-4-chlorophenoxy)-prop1on1c acid ethyl propyl ketoxime-ester 4 2,4,5-Trichlorophenoxy-acetlc add dthyl propyl ketoxime-ester 4 2,4,5-Trichlorophenoxy-acetlc acid (3-methyl -cyclopentanone oxlme)- ester 4 (2-Methyl-4-chlorophenoxy-)acetic add dilsopropyl ketoxime-ester 4 2,4-Dichlorophenoxy-acet1c acid dilsopropyl ketoxime-ester 4 2-(2-Methyl-4-chlorophe oxy) r-prop1on1c acid dilsopropyl ketoxime-ester 4 2-(2,4-D1chlorophenoxy)-prop1on1c add dilsopropyl ketoxime- ester 4 - -

Claims (25)

1. WHAT WE CLAIM IS:- 1. A herblddal preparation which comprises a compound of the general formula I 1n which and Rg each represent an aromatic, aliphatic, cycloaliphatlc or arallphatlc group, which groups may be unsubstituted or optionally mono-, d1- or polysubstltuted by alkyl, halogen, alkoxy, halogenoalkyl or nltro groups and may also represent a hydrogen atom or R^ and Rg together with the adjacent carbon atom represent a cycloaliphatlc hydrocarbon group which may optionally be mono-, d1- or polysubstltuted by alkyl, Rg represents a hydrogen atom or a lower alkyl group, n, represents 0, 1, 2 or 3, and each X represents a lower alkyl group, a lower alkoxy group, a halogeno-alHyl group or a halogen atom, 1n admixture or conjunction with a suitable carrier.
2. A preparation as claimed in claim 1, wherein ^ and each represents an alkyl group containing 1 to 4 carbon atoms, an unsubstituted phenyl group or a phenyl group substituted by a nltro group, a methyl group or a chlorine atom, and R-j may also represent a hydrogen atom, or R-j and Rg together with the adjacent carbon atom represent a eye lohexyll dene or a trlmethyl-cyclohexenyHdene group, R^ represents a hydrogen atom or a methyl group, n represents 0, 1, 2 or 3, and each X represents a methyl group or a halogen atom.
3. A preparation as claimed 1n claim 1 or 2, containing one or more compounds selected from the compounds listed in Table I herein.
4. A preparation as claimed in any one of claims 1 to 3, which 1s In the form of a powder, a spraying or dusting agent, granules, a solution, an emulsion or a suspension.
5. A preparation as claimed In any one of claims 1 to 4, containing a single compound of the general formula I 1n an amount of approximately 20 to 80% by weight.
6. A preparation as claimed 1n any one of claims 1 to 4, containing two or more compounds of the general formula I 1n a total amount of approximately 20 to 80% by weight.
7. A preparation as claimed 1n any one of claims 1 to 6 , containing a single surface-active agent 1n an amount of up to 20% by weight.
8. A preparation as claimed in any one of claims 1 to 6, containing two or more surface-active agents In a total amount of up to 20% by weight.
9. Any one of the herblcidal preparations as claimed 1n claim 1 and substantially as described In Examples 2 to 4 herein.
10. Any one of the herblcidal preparations as claimed 1n claim 1 and substantial ly as described 1n Example 6 herein. v
11. l l . A method of protecting a living plant against weeds , wherein the area 1n the vicinity of a l iving plant 1s treated with a compound of the general formula I given In claim 1 , 1n which R-j , R2 , jjn and X have the meanings given 1n claim 1 .
12. A method as claimed 1n claim 11 , wherein R-j , R2 » 3 n and X have the meanings given in claim 2.
13. A method as claimed 1n claim 11 or 12 , wherein the area 1s treated with one or more compounds selected from the compounds l isted in Table I herein.
14. A method as claimed 1n claim 11 , wherein the area 1s treated with a herblcidal preparation as claimed 1n any one of claims 1 , 2 and 9.
15. A method as claimed 1n claim 11 , wherein the area 1s treated with a herblcidal preparation as claimed 1n any one of claims 3 to 8 and 10.
16. A method as claimed In any one of claims 11 to 15, wherein a single compound of the general formula I Is used for the treatment 1n an amount of approximately 0.5 to 3 kg per hectare. 43825/2
17. A method as claimed 1n any one of claims 11 to 15, wherein two * or more compounds of the general formula I are used for the treatment in a total amount of approximately 0.5 to 3 kg per hectare. o ,
18. A method as claimed 1n claim 11, conducted substantially as described 1n Example 3 or 5 herein.
19. A method of protecting a crop area against weeds, wherein a crop area 1s treated with a compound of the general formula I given 1n claim 1, 1n which R-j, R2» R3, n and X have the meanings given 1n claim 1.
20. A method as claimed 1n claim 19, wherein Rj, R2» R3. n. and X have the meanings given 1n claim 2.
21. A method as claimed 1n claim 19 or 20, wherein the area 1s treated with one or more compounds selected from the compounds listed in Table 1 herein.
22. A method as claimed 1n claim 19, wherein the area Is treated with a herblddal preparation as claimed 1n any one of claims 1, 2 and 9.
23. A method as claimed in claim 19, wherein the area 1s treated with a herblddal preparation as claimed 1n any one of claims 3 to 8 and 10.
24. A method as claimed In any one of claims 19 to 23, wherein a single compound of the general formula I 1s used for the treatment In an amount of approximately Θ.5 to 3 kg per hectare.
25. A method as claimed 1n any one of claims 19 to 23, wherein two or more compounds of the general formula I are used for the treatment In a total amount of approximately 0.5 to 3 kg per hectare. For the Applicants Wolff, Bregman and Goller By: _¾.Λ-Α¾Λ
IL43825A 1972-12-15 1973-12-14 Herbicidal preparations containing alpha-phenoxy alkanoic acid oxime esters IL43825A (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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IL43825A0 IL43825A0 (en) 1974-03-14
IL43825A true IL43825A (en) 1977-03-31

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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
DE3170423D1 (en) * 1980-11-26 1985-06-13 Hoffmann La Roche Oxime esters, processes for their preparation, their use and compositions containing these esters

Also Published As

Publication number Publication date
NL7317222A (en) 1974-06-18
NO139150C (en) 1979-01-31
BR7309821D0 (en) 1974-09-24
JPS4986539A (en) 1974-08-19
FR2327234A1 (en) 1977-05-06
DD108031A5 (en) 1974-09-05
SU525417A3 (en) 1976-08-15
HU168995B (en) 1976-08-28
IE38640B1 (en) 1978-04-26
CS170111B2 (en) 1976-08-27
CA1013587A (en) 1977-07-12
ATA1048373A (en) 1975-05-15
NO139150B (en) 1978-10-09
IE38640L (en) 1974-06-15
ES420904A1 (en) 1976-05-01
BG20754A3 (en) 1975-12-20
AT328217B (en) 1976-03-10
JPS5319657B2 (en) 1978-06-22
FR2327234B1 (en) 1978-03-24
BE808636A (en) 1974-06-14
PL91626B1 (en) 1977-03-31
RO68556A (en) 1981-08-30
DE2262402A1 (en) 1974-08-01
IL43825A0 (en) 1974-03-14
FI55927C (en) 1979-11-12
LU68996A1 (en) 1974-02-22
FI55927B (en) 1979-07-31
ZA739503B (en) 1974-11-27
SU511853A3 (en) 1976-04-25
AU6365273A (en) 1975-06-19
CH584510A5 (en) 1977-02-15
IT1048161B (en) 1980-11-20
GB1458825A (en) 1976-12-15
AR213382A1 (en) 1979-01-31

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