DD149601A6 - PROCEDURE FOR THE CONTROL OF INSECTS AND MILKS - Google Patents

PROCEDURE FOR THE CONTROL OF INSECTS AND MILKS Download PDF

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Publication number
DD149601A6
DD149601A6 DD79219673A DD21967379A DD149601A6 DD 149601 A6 DD149601 A6 DD 149601A6 DD 79219673 A DD79219673 A DD 79219673A DD 21967379 A DD21967379 A DD 21967379A DD 149601 A6 DD149601 A6 DD 149601A6
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German Democratic Republic
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alpha
ppm
insects
acid
mites
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DD79219673A
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German (de)
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Gerald Berkelhammer
Venkataraman Kameswaran
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American Cyanamid Co
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Priority claimed from US05/890,721 external-priority patent/US4178460A/en
Priority claimed from US05/890,568 external-priority patent/US4199595A/en
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Publication of DD149601A6 publication Critical patent/DD149601A6/en

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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • 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
    • A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • 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
    • A01N37/36—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 singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A01N37/38—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 singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
    • 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
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/38—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
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    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
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    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
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    • C07C69/614—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety of phenylacetic acid

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Abstract

Die Erfindung betrifft eine weitere Ausgestaltung des Verfahrens zur Bekaempfung von Insekten und Milben nach Patent 136 689. Nach dem Hauptpatent bringt man die Insekten und Milben ihren Aufenthaltsort, ihre Brutstaetten oder ihr Futter mit einer insektizid oder akarizid wirksamen Menge bestimmter Phenylalkansaeure-m-phenoxybenzylester in Kontakt. Die erfindungsgemaesz verwendeten Wirkstoffe sind von erhoehter Wirksamkeit. Als Wirkstoff wird erfindungsgemaesz (+-)-alpha-Cyano-m-phenoxybenzyl-(+)-alpha-isopropyl-4-di-oder trifuormethoxyphenylacetat verwendet.The invention relates to a further embodiment of the method for combating insects and mites according to patent 136 689. According to the main patent to bring the insects and mites their whereabouts, their Brutstaetten or their food with an insecticidal or acaricidally effective amount of certain phenylalkansÄure m-phenoxybenzylester in Contact. The agents used in the invention are of enhanced efficacy. The active ingredient used according to the invention is (+ -) - alpha-cyano-m-phenoxybenzyl - (+) - alpha-isopropyl-4-di- or trifluoromethoxyphenylacetate.

Description

2 19 67 2 19 67

Anwendungsgebiet der Erfindung · Areas of application of the invention

Die Erfindung betrifft eine weitere Ausbildung des Gegenstandes von Patent 136 689.The invention relates to a further embodiment of the subject matter of patent 136 689.

Charakteristik der bekannten technischen Lösungen Gegenstand des Hauptpatents ist ein Verfahren zur Bekämpfung von Insekten und Milben, indem man die Insekten und Milben, ihren Aufenthaltsort, ihre Brutstätten oder ihr Futter mit einer insektizid oder akärizid wirksamen Menge eines entsprechenden Wirkstoffs in Kontakt bringt, das dadurch gekennzeichnet ist, daß man als Wirkstoff Phenylalkansäure-m-phenoxybenzylester der allgemeinen Formel Characteristics of the known technical solution e n subject of the main patent is a process for controlling insects and mites by bringing to the insects and mites, their location, their breeding grounds or their food with an insecticidally or akärizid effective amount of a corresponding active compound in contact, characterized in that the active ingredient is phenylalkanoic acid m-phenoxybenzylester of the general formula

// RCF2X // RCF 2 X

worin der Substituent der Formel RCF2X- in m- oder p-Stellung zu dem Kohlenstoffatom steht, an das die Alkansäureestergruppe gebunden ist, undwherein the substituent of the formula RCF 2 X- is in the m- or p-position to the carbon atom to which the alkanoic acid ester group is bonded, and

X ein Schwefelatom, ein Sauerstoffatom, eine Sulfinylgruppe oder eine Sulfonylgruppe,X is a sulfur atom, an oxygen atom, a sulfinyl group or a sulfonyl group,

R ein Wasserstoffatom, ein Fluoratom, ein Chloratora, eine Difluormethylgruppe oder eine Trifluormethylgruppe,R is a hydrogen atom, a fluorine atom, a chloratora, a difluoromethyl group or a trifluoromethyl group,

-2-2 1-9*73-2-2 1-9 * 73

R- eine Ethylgruppe, eine- n-Propylgruppe, eine Isopropylgruppe, eine tert.-Butylgruppe oder eine Isopropenylgruppe undR is an ethyl group, a n-propyl group, an isopropyl group, a tert-butyl group or an isopropenyl group, and

R_ ein Wasserstoffatom oder eine CyanogruppeR_ is a hydrogen atom or a cyano group

bedeuten, oder ein optisches Isomeres einer solchen Verbindung verwendet.mean, or uses an optical isomer of such a compound.

Die Herstellung dieser Phenylalkansäure-m-pheno'xybenzylester erfolgt dadurch, daß man eine Verbindung der allgemeinen FormelThe preparation of these phenylalkanoic acid m-pheno'xybenzylester takes place in that a compound of the general formula

CH-COACH-COA

in der A ein Halogenatom bedeutet und R und R„ die oben ange gebenen Bedeutungen besitzen, mit einem m-Phenoxybenzylalkohol der allgemeinen Formelin which A is a halogen atom and R and R "have the meanings given above, with an m-phenoxybenzyl alcohol of the general formula

CH-OHCH-OH

in der R3 die oben angegebenen Bedeutungen besitzt, in Gegenwart eines tertiären organischen Amins als Säureakzeptor und eines inerten organischen Lösungsmittels bei einer Temperatur von 10 bis 30 CC umsetzt.in which R 3 has the meanings given above, in the presence of a tertiary organic amine as the acid acceptor and an inert organic solvent at a temperature of 10 to 30 C C is reacted.

Bei der weiteren Bearbeitung dieses Gebiets hat sich gezeigt, daß einige der im Hauptpatent beschriebenen Ester besonders insektizid und akarizid wirksam sind, wenn sie von optisch aktiven Säuren abgeleitet werden.In further processing of this field, it has been found that some of the esters described in the main patent are particularly insecticidal and acaricidal when derived from optically active acids.

g des Wesens, der Erfindung g of the essence, the invention

Gegenstand der Erfindung ist daher ein Verfahren zur Bekämpfung von Insekten und Milben, das dadurch gekennzeichnet ist, daß man als Wirkstoff .(+_) -alpha-Cyano-m-phenoxybenzyl-(+)-alpha-isopropyl-4-di- oder -trifluormethoxyphenylacetat verwendet.The invention therefore relates to a method for controlling insects and mites, which is characterized in that the active ingredient. (+ _) -Alpha-cyano-m-phenoxybenzyl - (+) - alpha-isopropyl-4-di- or Trifluoromethoxyphenylacetat used.

219 673219 673

Die hierzu benötigten optisch aktiven Wirkstoffe werden durch übliche optische Spaltung erhalten.The optically active agents required for this purpose are obtained by conventional optical cleavage.

Ausführunpisb ei spieleExecution games

Durch die folgenden Beispiele wird die Erfindung weiterThe following examples further illustrate the invention

erläutert.explained.

Beispiel ΊExample Ί

Optische Spaltung von alpha-Isopropy1-4-difluormethoxyphenylessigsäure Optical cleavage of alpha-isopropyl-4-difluoromethoxyphenylacetic acid

Eine warme Lösung (60 0C) von 4,96 g (-)-alpha-Phenethylamin in 20 ml wäßrigem Ethanol (60 % Ethanol) wird zu einer warmen Lösung (60 0C) von 20 g der racemischen Säure in 50 ml wäßrigem Ethanol (60 % Ethanol) gegeben, wobei mit einem Magnetrührer gerührt wird. V7ährend des langsamen Abkühlens der Lösung auf Zimmertemperatur fällt das Salz in Form einer weißen kristallinen Substanz aus. Nach Stehenlassen der Mischung über Nacht werden die Feststoffe abfiltriert, mit 1O ml wäßrigem Ethanol gewaschen und getrocknet. Man erhält so 9,5 g Substanz vom F. = 184 bis 188 0C. Der Drehwert der aus diesem Salz erhaltenen Säure beträgt /alpha/^immertemp· = + 37,1° (CHCl3, C = 1,439 g/100 ml). Zweimaliges Umkristallisieren dieses Salzes aus wäßrigem Ethanol (60 % Ethanol) führt zu weißen Nadeln vom F. = 185 bis 187 0C, und die daraus erhaltene Säure zeigt /alpha/^immertemPeratur = +40,4° (CHCl3, C = 1,353 g/100 ml.A warm solution (60 ° C.) of 4.96 g of (-) - alpha-phenethylamine in 20 ml of aqueous ethanol (60% ethanol) is added to a warm solution (60 ° C.) of 20 g of the racemic acid in 50 ml of aq Ethanol (60% ethanol), being stirred with a magnetic stirrer. During the slow cooling of the solution to room temperature, the salt precipitates as a white crystalline substance. After allowing the mixture to stand overnight, the solids are filtered off, washed with 10 ml of aqueous ethanol and dried. This gives 9.5 g of substance from mp = 184-188 0 C. The rotation of the acid obtained from this salt is / alpha / ^ · immertemp = + 37.1 ° (CHCl 3, C = 1.439 g / 100 ml ). Two recrystallizations of this salt from aqueous ethanol (60% ethanol) yields white needles, mp = 185 to 187 0 C, and the acid obtained therefrom shows / alpha / ^ immertem perature = + 40.4 ° (CHCl 3, C = 1.353 g / 100 ml.

Beispiel 2Example 2

Herstellung von (+)-älpha-Cyan-m-phenoxybenzyl-(+)-alphaisopropyl-4-difluormethoxyphenylacetat Preparation of (+) - alpha-cyan-m-phenoxybenzyl - (+) - alpha isopropyl-4-difluoromethoxyphenylacetate

Die nach Beispiel 1 erhaltene (+)-Säure wird nach den in den Beispielen 15 und 16 des Hauptpatents beschriebenen Arbeitsweisen in den Ester übergeführt. N^3 = 1,5432; NMR (CDCl3) delta 6,8 bis 7,5 (m, 13H, ArH), 6,43 (t, J- 74Hz, 1H, OCHF2), 6,30 und 6,23 (2S, 1H, CH-CN), 3,27 (d,.J=IOHz, 1H, CH-CH(CH3)2)The (+) - acid obtained according to Example 1 is converted into the ester according to the procedures described in Examples 15 and 16 of the main patent. N ^ 3 = 1.5432; NMR (CDCl3) delta 6.8 to 7.5 (m, 13H, ArH), 6.43 (t, J- 7 4 Hz, 1 H, OCHF 2), 6.30 and 6.23 (2s, 1H , CH-CN), 3.27 (d, J = IOHz, 1H, CH-CH (CH 3 ) 2 )

-.* - 2t-. * - 2t

Beispielexample

Optische Spaltung von alpha-Isopropyl-4-trifluormethöxyphenylessigsäure Optical cleavage of alpha-isopropyl-4-trifluoromethoxyphenylacetic acid

Eine Mischung aus 26,2 g der raceraischen Säure und 12,1 g (-)-alpha-Phenethylamin in 2 1 wäßrigem Ethanol (60 % Ethanol) wird zum Lösen auf einem Dampfbad erwärmt und langsam auf Zimmertemperatur abkühlen gelassen. Das Salz wird abfiltriert und getrocknet. Man erhält 16,9 g Substanz vom F. = 189 bis 193 0C. Das Salz wird zweimal aus einem Liter bzw. 600 ml wäßrigem Ethanol (60 % Ethanol) umkrisallisiert, und man erhält 8,0 g Substanz vom F. = 194 bis 196 0C. Die (+)-Säure wird durch Neutralisieren des Salzes mit verdünnter Salssäure, Extrahieren mit Ether und Verdampfen des Lösungsmittels erhalten.A mixture of 26.2 g of racemic acid and 12.1 g of (-) - alpha-phenethylamine in 2 L of aqueous ethanol (60% ethanol) is warmed to dissolve on a steam bath and allowed to cool slowly to room temperature. The salt is filtered off and dried. This gives 16.9 g of substance of mp = 189-193 0 C. The salt is recrystallized twice from one liter or 600 ml of aqueous ethanol (60% ethanol), and there are obtained 8.0 g of substance of mp = 194 to 196 0 C. the (+) - acid is obtained by neutralizing the salt with dilute Salssäure, extraction with ether and evaporation of the solvent.

/alpha/£iKlinertemp· = +35,5° (CHCl3, C=6,0 g/100 ml)./ alpha / lKlinertemp * = + 35.5 ° (CHCl 3 , C = 6.0 g / 100 ml).

Beispiel 4Example 4

Herstellung von ( + )-alpha-Cyan-m-phenoxybenzyl-( + )-alpha-• isopropyl-4-trifluormethoxyphenylacetatPreparation of (+) -alpha-cyano-m-phenoxybenzyl (+) -alpha- • iso propyl-4-acetate trifluormethoxyphe

Unter Verwendung der (+)-alpha-Isopropyl-4-trifluormethoxyphenylessigsäure wird nach den in den Beispielen 15 und 16 äes Hauptpatents beschriebenen.Arbeitsweisen das Produkt als blaßgelbes öl erhalten.Using (+) - alpha-isopropyl-4-trifluoromethoxyphenylacetic acid, the product is obtained as a pale yellow oil according to the procedures described in Examples 15 and 16 of the main patent.

/alpha/^inunerternp· =6,1° (CHCl37 C = 5 g/100 ml)./ alpha / inunerternp = 6.1 ° (CHCl 37 C = 5 g / 100 ml).

Bei der Verwertung der Insektiziden Wirkung der vorstehend beschriebenen Ester nach den im Hauptpatent beschriebenen Arbeitsweisen werden die aus den folgenden Ergänzungen zu den Tabellen I bis III des Hauptpatents ersichtlichen Ergebnisse erhalten. · ;·'In the utilization of the insecticidal activity of the above-described esters according to the operations described in the main patent, the results shown in the following additions to Tables I to III of the main patent are obtained. · ; · '

Tabelle..!·Table..!·

Bewertung derReview of Verbindung * . .. 'Connection * . .. ' insektiziden Wirkunginsecticidal activity Tabakraupeniarve . '· 1.EntwicklungsstadiumTobacco caterpillar. '· 1st development stage 100 ppm100 ppm TQ ppm TQ ppm Blatthüpferleafhopper 10 ppm10 ppm 1 ppm1 ppm Blattlaus aphid 10 ppm10 ppm ii ppmppm 300 ppm300 ppm 100 .100. 100100 100 ppm100 ppm 9090 00 100 PPm100 PPm 100100 100100 00 ( + )-Säurc · . _^__ CN (+j-Alkohol F-CHO -V x>- CH-CO-O-CH -f^ >0 -f^ Π \—/ ι LJlJ(+) Acid ·. _ ^ __ CN (+ j-Alcohol F-CHO -V x > - CH-CO-O-CH-f ^> 0 -f ^ Π \ - / ι LJlJ 100100 100100 100100 %- Mortalität β % - mortality β

Tabelle- II .. . · Bewertung -der Insektiziden Wirkung Table II ... · Evaluation of the insecticidal effect

Moskitolarvenmosquito larvae 0,4 ppm0.4 ppm ü,0 4 ppm 'ü, 0 4 ppm ' •• O7OÜ4 ppmO 7 O 4 ppm , .%· Mortalität·% · Mortality 10Ü ppm10μppm 10 ppm10 ppm . , 100 PP^.100 pp ^. 10 ppm10 ppm •• Verbindungconnection 1,2 ppm1.2 ppm 100100 100100 100100 Baumwollraupecotton caterpillar 100100 100100 tAexikanifsehQ .. Marienk"a"f ertAexikanifsehQ .. Marienk "a" f he 100100 100100 1 PP1 pp (+)-Säure' . CN; ' (+)-Alkohol. . P2CHO-^ \\-CH-CO-O-CH-γ^^Οη^^ ^^ CK(CH3J2 ^J ^J) (+) - acid '. CN; '(+) - alcohol. , P 2 CHO- ^ \\ - CH-CO-O-CH-γ ^^ Οη ^^ ^^ CK (CH 3 J 2 ^ J ^ J) 100100 lööö ppmLööö ppm 300 ppm300 ppm SS 100100 100100

Tabelletable

IIIIII

Verbindung  connection •• . "Insek-fc-izida Wirkung ', "Insek-fc-izida effect" 300300 lüü ppmlüü ppm TO ppmTO ppm ·' ' ·· '' · ppmppm •• ppmppm 11 ppi11 ppi 100100 00 -- 100100 100100 1010 -Ä · ?: V>-CH-CO-O-CH - -/ ' -* CH(CH^)2 -Ä · : V> -CH-CO-O-CH - - / ' - * CH (CH ^) 2 % Mortalität _ .. · .% Mortality _ .. ·. Tabakraupe im 3. 1 Entv.'icklunasstadiumTobacco caterpillar in the third one Entv.'icklunasstadium Kohlraube i.3.Ent wicklungsstadium Coal. I.3. Development stage ·.·(+)-Alkohol. · (+) - alcohol 1000 ppm1000 ppm 1000 ppm1000 ppm (-f.)--Säure ' F2CHO -(-f.) - Acid 'F 2 CHO - 100100 100100 •• Phosphatresistcnte. ·"·-·- -Milben -·- --"-Phosphatresistcnte. · "- · · - - Milking - · - -" - loo σ ppmloo σ ppm 100100

Claims (1)

ErfindungsanpsruchErfindungsanpsruch Weitere Ausbildung des Verfahrens zur Bekämpfung von Insekten und Milben nach Patent 136 689, dadurch gekennzeichnet , daß man als Wirkstoff (+)-alpha-Cyano-m-phenoxybenzyl-(+)-alpha-isopropyl-4-dioder -trifluormethoxyphenylacetat verwendet.Further development of the method for controlling insects and mites according to patent 136 689, characterized in that one uses as active ingredient (+) - alpha-cyano-m-phenoxybenzyl - (+) - alpha-isopropyl-4-di or trifluoromethoxyphenylacetate.
DD79219673A 1978-03-20 1979-03-20 PROCEDURE FOR THE CONTROL OF INSECTS AND MILKS DD149601A6 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US05/890,721 US4178460A (en) 1976-10-01 1978-03-20 2-Haloalkyl(oxy-, thio-, sulfinyl-, or sulfonyl)-phenylalkanoic acids
US05/890,568 US4199595A (en) 1976-10-01 1978-03-20 M-phenoxybenzyl and α-cyano-M-phenoxybenzyl esters of 2-haloalkyl (oxy-, thio-, sulfinyl-, or sulfonyl)phenylalkanoic acids

Publications (1)

Publication Number Publication Date
DD149601A6 true DD149601A6 (en) 1981-07-22

Family

ID=27128953

Family Applications (5)

Application Number Title Priority Date Filing Date
DD79211693A DD143601A5 (en) 1978-03-20 1979-03-20 PROCESS FOR THE PREPARATION OF PHENYL ALKANSAEURE M-PHENOXYBENZYL ESTERS
DD79220007A DD152539A5 (en) 1978-03-20 1979-03-20 PROCESS FOR THE PRODUCTION OF PHENYL ALKANSAURES
DD79220465A DD154535A5 (en) 1978-03-20 1979-03-20 PROCESS FOR PREPARING (+) - ALPHA-ISOPROPYL-4-DI-OR-TRIFLUOROMETHOXYPHENYL ACIDIC ACID
DD79211694A DD150455A6 (en) 1978-03-20 1979-03-20 PROCESS FOR THE PREPARATION OF PHENYL ALKANSANIC M-PHENOXY BENZYL ESTERS
DD79219673A DD149601A6 (en) 1978-03-20 1979-03-20 PROCEDURE FOR THE CONTROL OF INSECTS AND MILKS

Family Applications Before (4)

Application Number Title Priority Date Filing Date
DD79211693A DD143601A5 (en) 1978-03-20 1979-03-20 PROCESS FOR THE PREPARATION OF PHENYL ALKANSAEURE M-PHENOXYBENZYL ESTERS
DD79220007A DD152539A5 (en) 1978-03-20 1979-03-20 PROCESS FOR THE PRODUCTION OF PHENYL ALKANSAURES
DD79220465A DD154535A5 (en) 1978-03-20 1979-03-20 PROCESS FOR PREPARING (+) - ALPHA-ISOPROPYL-4-DI-OR-TRIFLUOROMETHOXYPHENYL ACIDIC ACID
DD79211694A DD150455A6 (en) 1978-03-20 1979-03-20 PROCESS FOR THE PREPARATION OF PHENYL ALKANSANIC M-PHENOXY BENZYL ESTERS

Country Status (17)

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JP (1) JPS54135742A (en)
AR (1) AR228014A1 (en)
AT (1) AT367965B (en)
AU (2) AU528525B2 (en)
BR (1) BR7901697A (en)
CH (2) CH640513A5 (en)
DD (5) DD143601A5 (en)
DK (1) DK112679A (en)
ES (2) ES8303283A2 (en)
GB (1) GB2017688B (en)
GR (1) GR74446B (en)
HU (1) HU182016B (en)
NL (1) NL7902153A (en)
NZ (1) NZ189915A (en)
PL (1) PL123011B1 (en)
RO (1) RO79551A (en)
SE (1) SE444313B (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2837524A1 (en) * 1978-08-28 1980-03-20 Bayer Ag Phenylacetic acid ester derivs. from pyrethroid alcohol(s) - useful as insecticides and acaricides, and new intermediates
IL61348A (en) * 1979-11-28 1984-05-31 American Cyanamid Co (-)-alpha-cyano-m-phenoxybenzyl(+)alpha-isopropyl-4-difluoromethoxy-phenylacetate,its preparation and its use as an insecticide
JPS56133253A (en) * 1980-03-24 1981-10-19 Sumitomo Chem Co Ltd Optical isomer of cyanohydrin ester, its production and insecticide and acaricide containing the same as effective ingredient
JPS56139445A (en) * 1980-04-02 1981-10-30 Sumitomo Chem Co Ltd Stereoisomer of cyanohydrin ester, its production and insecticide, acaricide containing the same as active principle
JPS5793948A (en) * 1980-12-02 1982-06-11 Sumitomo Chem Co Ltd Preparation of stereoisomer mixture of higher active phenylacetic ester derivative
DE3103325A1 (en) * 1981-01-31 1982-08-26 Bayer Ag, 5090 Leverkusen 4-FLUOR-3-HALOPHENOXY-BENZYL ESTER, METHOD FOR THE PRODUCTION AND USE THEREOF IN PEST CONTROL, AND NEW INTERMEDIATE PRODUCTS AND METHOD FOR THE PRODUCTION THEREOF
FR2512815B1 (en) * 1981-04-16 1989-04-14 Roussel Uclaf NOVEL DERIVATIVES OF CYCLOPROPANE CARBOXYLIC ACID, THEIR PREPARATION METHOD, THEIR APPLICATION TO THE CONTROL OF PESTS
IL69304A0 (en) * 1982-08-23 1983-11-30 American Cyanamid Co Method for the preparation of difluoromethoxyaromatic compounds

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5133612B2 (en) * 1973-04-19 1976-09-21 Sumitomo Chemical Co
IL52973A (en) * 1976-10-01 1983-10-31 American Cyanamid Co Alpha-(haloalkoxy and haloalkyl-thiophenyl)alkanoic acid ester derivatives,their preparation and insecticidal and acaricidal compositions containing them

Also Published As

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GB2017688A (en) 1979-10-10
CH641638A5 (en) 1984-03-15
PL123011B1 (en) 1982-09-30
AT367965B (en) 1982-08-25
NL7902153A (en) 1979-09-24
ES478787A0 (en) 1981-05-16
ES478785A0 (en) 1983-02-01
NZ189915A (en) 1981-04-24
AU525146B2 (en) 1982-10-21
JPS6362507B2 (en) 1988-12-02
SE444313B (en) 1986-04-07
DK112679A (en) 1979-09-21
ES8303283A2 (en) 1983-02-01
PL214234A3 (en) 1980-08-25
ATA204979A (en) 1982-01-15
BR7901697A (en) 1979-10-16
AR228014A1 (en) 1983-01-14
ES8105253A1 (en) 1981-05-16
DD154535A5 (en) 1982-03-31
SE7902467L (en) 1979-11-19
HU182016B (en) 1983-12-28
JPS54135742A (en) 1979-10-22
AU4524279A (en) 1979-09-27
DD152539A5 (en) 1981-12-02
CH640513A5 (en) 1984-01-13
DD143601A5 (en) 1980-09-03
GB2017688B (en) 1982-08-18
AU528525B2 (en) 1983-05-05
AU4525179A (en) 1979-09-27
GR74446B (en) 1984-06-28
DD150455A6 (en) 1981-09-02
RO79551A (en) 1982-08-17

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