CH640513A5 - OPTICALLY ACTIVE PHENYL ALKANIC ACID M-PHENOXYBENZYL ESTER. - Google Patents

OPTICALLY ACTIVE PHENYL ALKANIC ACID M-PHENOXYBENZYL ESTER. Download PDF

Info

Publication number
CH640513A5
CH640513A5 CH257479A CH257479A CH640513A5 CH 640513 A5 CH640513 A5 CH 640513A5 CH 257479 A CH257479 A CH 257479A CH 257479 A CH257479 A CH 257479A CH 640513 A5 CH640513 A5 CH 640513A5
Authority
CH
Switzerland
Prior art keywords
isopropyl
phenoxybenzyl
cyano
mites
esters
Prior art date
Application number
CH257479A
Other languages
German (de)
Inventor
Gerald Berkelhammer
Venkataraman Kameswaran
Original Assignee
American Cyanamid Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US05/890,568 external-priority patent/US4199595A/en
Priority claimed from US05/890,721 external-priority patent/US4178460A/en
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Publication of CH640513A5 publication Critical patent/CH640513A5/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • 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
    • 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
    • A01N37/34—Nitriles
    • 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
    • C—CHEMISTRY; METALLURGY
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/08—Preparation of carboxylic acids or their salts, halides or anhydrides from nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/58—Preparation of carboxylic acid halides
    • C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/612—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/612—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
    • 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

Description

Gegenstand der Erfindung sind daher die Ester aus race-mischem a-Cyano-m-phenoxybenzylalkohol und (+)-ct-Iso-propyl-4-di- oder -tri-fluormethoxyphenylessigsäure, ein in-sektizides Mittel und ein Verfahren zur Bekämpfung von Insekten und Milben, die wie in der genannten US-PS beschrieben ausgeführt werden können. The invention therefore relates to the esters of race-mixed a-cyano-m-phenoxybenzyl alcohol and (+) - ct-iso-propyl-4-di- or tri-fluoromethoxyphenylacetic acid, an insecticidal agent and a process for combating Insects and mites that can be carried out as described in said U.S. Patent.

Die Herstellung der racemischen Säuren und ihrer Ester ist in der genannten US-PS beschrieben. Die optisch aktiven Säuren können aus den racemischen Säuren durch Racemat-spaltung erhalten werden, die in üblicher Weise ausgeführt werden kann. The preparation of the racemic acids and their esters is described in the aforementioned US patent. The optically active acids can be obtained from the racemic acids by resolution, which can be carried out in a conventional manner.

Durch die folgenden Beispiele wird die Erfindung weiter erläutert. The invention is further illustrated by the following examples.

Beispiel 1 example 1

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

Eine warme Lösung (60 °C) von 4,96 g (—)-alpha-Phenylethylamin in 20 ml wässrigem Ethanol (60% Ethanol) wird zu einer warmen Lösung (60 °C) von 20 g der racemischen Säure in 50 ml wässrigem Ethanol (60% Ethanol) gegeben, wobei mit einem Magnetrührer gerührt wird. Während des langsamen Abkühlens der Lösung auf Zimmertemperatur fallt das Salz in Form einer weissen kristallinen Substanz aus. Nach Stehenlassen der Mischung über Nacht werden die Feststoffe abfiltriert, mit 10 ml wässrigem Ethanol gewaschen und getrocknet. Man erhält so 9,5 g Substanz vom F. = 184 bis 188 °C. Der Drehwert der aus diesem Salz erhaltenen Säure beträgt [alpha]pmracrtemp- = +37,1° A warm solution (60 ° C) of 4.96 g of (-) - alpha-phenylethylamine in 20 ml of aqueous ethanol (60% ethanol) becomes a warm solution (60 ° C) of 20 g of the racemic acid in 50 ml of aqueous Ethanol (60% ethanol) was added, stirring with a magnetic stirrer. As the solution slowly cools to room temperature, the salt precipitates in the form of 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. 9.5 g of substance of mp = 184 to 188 ° C. are obtained in this way. The rotation value of the acid obtained from this salt is [alpha] pmracrtemp- = + 37.1 °

(CHC13, C = 1,439 g/100 ml). Zweimaliges Umkristallisieren dieses Salzes aus wässrigem Ethanol (60% Ethanol) (CHC13, C = 1.439 g / 100 ml). Recrystallize this salt twice from aqueous ethanol (60% ethanol)

führt zu weissen Nadeln vom F. = 185 bis 187 °C, und die daraus erhaltene Säure zeigt [alpha]§mmertemp- = +40,4° (CHC13,C = 1,353 g/100 ml. leads to white needles of F. = 185 to 187 ° C, and the acid obtained from it shows [alpha] §mmertemp- = + 40.4 ° (CHC13, C = 1.353 g / 100 ml.

30 Herstellung von ((+)-alpha-Cyano-m-phenoxybenzyl)-(+)-alpha-isopropyl-4-difluormethoxyphenylacetat Die oben erhaltene (+)-Säure wird nach den in den Beispielen 15 und 16 der oben erwähnten US-PS beschriebenen Arbeitsweisen in den Ester übergeführt. N23D = 1,5432; 35 NMR (CDCI3) delta 6,8 bis 7,5 (m, 13H, ArH), 6,43 (t, J = 74Hz, 1H, OCHF2), 6,30 und 6,23 (2S, IH, CH-CN), 3,27 (d, J = 10 Hz, 1H, CH-CH(CH3)2). 30 Preparation of ((+) - alpha-cyano-m-phenoxybenzyl) - (+) - alpha-isopropyl-4-difluoromethoxyphenylacetate The (+) - acid obtained above is obtained according to the methods described in Examples 15 and 16 of the above-mentioned US Pat. PS described working methods converted into the ester. N23D = 1.5432; 35 NMR (CDCI3) delta 6.8 to 7.5 (m, 13H, ArH), 6.43 (t, J = 74Hz, 1H, OCHF2), 6.30 and 6.23 (2S, IH, CH- CN), 3.27 (d, J = 10 Hz, 1H, CH-CH (CH3) 2).

40 Beispiel 2 40 Example 2

Optische Spaltung von alpha-Isopropyl-4-trifhiormethoxyphenylessigsäure Eine Mischung aus 26,2 g der racemischen Säure und 12,1 g (—)-alpha-Phenylethylamin in 21 wässrigem Ethanol 45 (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 °C. Das Salz wird zweimal aus einem Liter bzw. 600 ml wässrigem Ethanol so (60% Ethanol) umkristallisiert, und man erhält 8,0 g Substanz vom F. = 194 bis 196 ~C. Die (-t-)-Säure wird durch Neutralisieren des Salzes mit verdünnter Salzsäure, Extrahieren mit Ether und Verdampfen des Lösungsmittels erhalten. Optical resolution of alpha-isopropyl-4-trifhiormethoxyphenylacetic acid A mixture of 26.2 g of the racemic acid and 12.1 g (-) - alpha-phenylethylamine in 21 aqueous ethanol 45 (60% ethanol) is heated on a steam bath and dissolved Allow to cool slowly to room temperature. The salt is filtered off and dried. 16.9 g of substance of mp = 189 to 193 ° C. are obtained. The salt is recrystallized twice from one liter or 600 ml of aqueous ethanol in this way (60% ethanol), and 8.0 g of substance of mp = 194 to 196 ° C. are obtained. The (-t -) acid is obtained by neutralizing the salt with dilute hydrochloric acid, extracting with ether and evaporating the solvent.

55 [alpha]|jmmerteinp- = +35,5C (CHC13, C = 6,0 g/100 ml). 55 [alpha] | jmmerteinp- = + 35.5C (CHC13, C = 6.0 g / 100 ml).

Herstellung von ((±)-alpha-Cyano-m-phenoxybenzyl)-(+)-alpha-isopropyl-4-trifluormethoxyphenylacetat Unter Verwendung der (+)-alpha-Isopropyl-4-trifluor-60 methoxyphenylessigsäure wird nach den in den Beispielen 15 und 16 der obigen US-PS beschriebenen Arbeitsweisen das Produkt als blassgelbes Öl erhalten. Preparation of ((±) -alpha-cyano-m-phenoxybenzyl) - (+) - alpha-isopropyl-4-trifluoromethoxyphenylacetate using the (+) - alpha-isopropyl-4-trifluoro-60 methoxyphenylacetic acid according to the procedures in the examples 15 and 16 of the above-described procedures described the product as a pale yellow oil.

[alpha]§mmertemp- = 6,1= (CHCI3) C = 5 g/100 ml). Bei der Bewertung der insektiziden Wirkung der vor-65 stehend beschriebenen Ester nach den in der genannten US-PS beschriebenen Arbeitsweisen werden die aus den folgenden Ergänzungen zu den Tabellen I bis III der genannten US-PS ersichtlichen Ergebnisse erhalten. [alpha] §mmertemp- = 6.1 = (CHCI3) C = 5 g / 100 ml). When evaluating the insecticidal activity of the esters described above in accordance with the procedures described in the US patent mentioned, the results evident from the following additions to Tables I to III of the US patent mentioned are obtained.

25 25th

Claims (3)

640 513 640 513 PATENTANSPRÜCHE PATENT CLAIMS 1 • (( ± )-a-Cyano-m-phenoxybenzyl)-( + )-a-isopropyl-4-di- und -tri-fluormethoxyphenylacetat. 1 • ((±) -a-cyano-m-phenoxybenzyl) - (+) -a-isopropyl-4-di- and tri-fluoromethoxyphenylacetate. 2. Verfahren zur Bekämpfung von Insekten und Milben, dadurch gekennzeichnet, dass man ((+)-a-Cyano-m-phenoxybenzyl)-(+)-a-isopropyl-4-di- oder -tri-fluor- 2. A method for controlling insects and mites, characterized in that ((+) - a-cyano-m-phenoxybenzyl) - (+) - a-isopropyl-4-di- or tri-fluorine methoxyphenylacetat auf die Insekten bzw. Milben, ihren Lebensraum, ihre Brutstätten oder ihr Futter aufbringt. applies methoxyphenylacetate to the insects or mites, their habitat, their breeding grounds or their feed. 3. Insektizides Mittel, dadurch gekennzeichnet, dass es ((+)-cc-Cyano-m-phenoxybenzyl)-(+)-a-isopropyl-4-di-oder -tri-fluormethoxyphenylacetat enthält. 3. Insecticidal agent, characterized in that it contains ((+) - cc-cyano-m-phenoxybenzyl) - (+) - a-isopropyl-4-di-or -tri-fluoromethoxyphenylacetate. In der ZA-Patentanmeldung Nr. 73/4462 sind Zehntausende von Phenylessigsäureestern, u.a. 3'-Phenoxybenzyl-a-isopropyl-4-methoxyphenylacetat, -a-isopropyl-3-methoxy-phenylacetat, -a-isopropyl-4-chlorphenylacetat, -a-iso-propyl-4-methylphenylacetat, -a-isopropyl-3-chlorphenyl-acetat und -a-isopropyl-4-fluorphenylacetat, beschrieben. Es wird angegeben, dass viele dieser Verbindungen wirksame ZA Patent Application No. 73/4462 describes tens of thousands of phenylacetic acid esters, including 3'-phenoxybenzyl-a-isopropyl-4-methoxyphenylacetate, -a-isopropyl-3-methoxy-phenylacetate, -a-isopropyl-4-chlorophenylacetate, -a-iso-propyl-4-methylphenylacetate, -a-isopropyl-3 -chlorophenyl acetate and -a-isopropyl-4-fluorophenylacetate. Many of these compounds are said to be effective Schädlingsbekämpfungsmittel sind und sich für die Bekämp-io fung der verschiedensten Insekten und Milben eignen. Es werden jedoch weder die erfindungsgemässen Ester noch Verfahren zur Synthese derselben beschrieben. They are pesticides and are suitable for controlling a wide variety of insects and mites. However, neither the esters according to the invention nor processes for the synthesis thereof are described. Gegenstand der US-PS Nr. 4 199 595 sind Phenylalkan-säure-m-phenoxybenzylester der Formel: US Pat. No. 4,199,595 relates to phenylalkanoic acid m-phenoxybenzyl esters of the formula: 15 15 rcf2x ch-c0-0-ch-! rcf2x ch-c0-0-ch-! r- r- worin der Substituent der Formel RCF2X- in m- oder p-Stellung zu dem Kohlenstoffatom steht, an das die Alkan-säureestergruppe gebunden ist, X Schwefel, Sauerstoff, Sul-finyl oder Sulfonyl bedeutet, R Wasserstoff, Fluor, Chlor, Difluormethyl oder Trifluormethyl darstellt, R2 Ethyl, n-Propyl, Isopropyl, tert.-Butyl oder Isopropenyl bedeutet und R3 Wasserstoff oder Cyano darstellt, sowie die optischen Isomeren dieser Verbindungen. wherein the substituent of the formula RCF2X is in the m- or p-position to the carbon atom to which the alkanoic acid ester group is attached, X is sulfur, oxygen, sulfinyl or sulfonyl, R is hydrogen, fluorine, chlorine, difluoromethyl or trifluoromethyl represents R2 represents ethyl, n-propyl, isopropyl, tert-butyl or isopropenyl and R3 represents hydrogen or cyano, and the optical isomers of these compounds. Die genannte US-PS offenbart auch Verfahren zur Herstellung der oben definierten Verbindungen und Verfahren zur Bekämpfung von Insekten und Milben. The aforementioned US patent also discloses methods for producing the compounds defined above and methods for controlling insects and mites. Bei der weiteren Bearbeitung dieses Gebiets hat sich gezeigt, dass einigen der in der genannten US-PS beschriebenen Ester besonders grosse Bedeutung zukommt, wenn sie von optisch aktiven Säuren abgeleitet sind. Further processing of this area has shown that some of the esters described in the above-mentioned US Pat. Are particularly important if they are derived from optically active acids.
CH257479A 1978-03-20 1979-03-19 OPTICALLY ACTIVE PHENYL ALKANIC ACID M-PHENOXYBENZYL ESTER. CH640513A5 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
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
US05/890,721 US4178460A (en) 1976-10-01 1978-03-20 2-Haloalkyl(oxy-, thio-, sulfinyl-, or sulfonyl)-phenylalkanoic acids

Publications (1)

Publication Number Publication Date
CH640513A5 true CH640513A5 (en) 1984-01-13

Family

ID=27128953

Family Applications (2)

Application Number Title Priority Date Filing Date
CH257479A CH640513A5 (en) 1978-03-20 1979-03-19 OPTICALLY ACTIVE PHENYL ALKANIC ACID M-PHENOXYBENZYL ESTER.
CH257379A CH641638A5 (en) 1978-03-20 1979-03-19 PHENYL ALKANIC ACID-M-PHENOXYBENZYL ESTER.

Family Applications After (1)

Application Number Title Priority Date Filing Date
CH257379A CH641638A5 (en) 1978-03-20 1979-03-19 PHENYL ALKANIC ACID-M-PHENOXYBENZYL ESTER.

Country Status (17)

Country Link
JP (1) JPS54135742A (en)
AR (1) AR228014A1 (en)
AT (1) AT367965B (en)
AU (2) AU525146B2 (en)
BR (1) BR7901697A (en)
CH (2) CH640513A5 (en)
DD (5) DD152539A5 (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

Publication number Publication date
DD150455A6 (en) 1981-09-02
ATA204979A (en) 1982-01-15
DD152539A5 (en) 1981-12-02
CH641638A5 (en) 1984-03-15
SE444313B (en) 1986-04-07
PL123011B1 (en) 1982-09-30
AU525146B2 (en) 1982-10-21
DD154535A5 (en) 1982-03-31
GB2017688B (en) 1982-08-18
NZ189915A (en) 1981-04-24
AU528525B2 (en) 1983-05-05
DD143601A5 (en) 1980-09-03
DD149601A6 (en) 1981-07-22
ES8105253A1 (en) 1981-05-16
GB2017688A (en) 1979-10-10
GR74446B (en) 1984-06-28
DK112679A (en) 1979-09-21
NL7902153A (en) 1979-09-24
ES478785A0 (en) 1983-02-01
JPS6362507B2 (en) 1988-12-02
JPS54135742A (en) 1979-10-22
HU182016B (en) 1983-12-28
SE7902467L (en) 1979-11-19
AU4525179A (en) 1979-09-27
BR7901697A (en) 1979-10-16
ES8303283A2 (en) 1983-02-01
AR228014A1 (en) 1983-01-14
AU4524279A (en) 1979-09-27
AT367965B (en) 1982-08-25
RO79551A (en) 1982-08-17
PL214234A3 (en) 1980-08-25
ES478787A0 (en) 1981-05-16

Similar Documents

Publication Publication Date Title
DE2653189C2 (en) Cyclopropane compounds, processes for their preparation and insecticides containing these compounds
CH650493A5 (en) D-(+)-alpha-phenoxypropionic acid derivatives
DE3941966A1 (en) HALOGENED OLEFINS, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS A PEST CONTROL
DE2433680A1 (en) 2,3-DIHYDRO-2,2-DIMETHYL-7-BENZOFURANYLMETHYLCARBAMATE-N-AMINOSULFENYL DERIVATIVES, PROCESS FOR THEIR PRODUCTION AND INSECTICIDAL COMPOSITIONS CONTAINING THESE COMPOUNDS
DE2905650C2 (en)
DE2509416A1 (en) DINITROBENZOTRIFLUORIDE
CH640513A5 (en) OPTICALLY ACTIVE PHENYL ALKANIC ACID M-PHENOXYBENZYL ESTER.
EP0007089B1 (en) Acylanilides with herbicidal and fungicidal activity, process for their preparation and their use
DD147610A5 (en) FUNGICIDAL AGENT
DE1542777A1 (en) Selective herbicidal agents
DD158239A5 (en) PROCESS FOR PREPARING CYCLOPROPANCARBOXY ACID ESTERS DERIVATIVES
US2384306A (en) Esters of halonitrophenols
EP0046950B1 (en) Optically active isomers of trans-3(2-(4-chlorophenyl)-vinyl)-2,2-dimethyl-cyclopropion-1-ic acid-(alpha-cyano-4-fluoro-3-phenoxy-benzyl)-esters, process for their preparation and their use as ectoparasiticides
DE2415437A1 (en) HETEROCYCLIC COMPOUNDS AND PROCESS FOR THE PRODUCTION OF THE SAME AND COMPOSITIONS OF SUBSTANCE WHICH CONTAIN THEM
DE2440381A1 (en) 2-(4-Phenylthio-phenyl)-alkanoic acids - prepd. e.g. by reacting 4-phenylthio-phenols with ketones and trihalo-methanes
DE2061133A1 (en) Pesticidal compound, process for its preparation and use
DE2727326A1 (en) METHOD FOR MANUFACTURING CYANOESTERS
DE2909827A1 (en) PHENYLALCANIC ACID-M-PHENOXYBENZYLESTER, METHOD FOR THEIR PREPARATION AND THE USE
DE2628188A1 (en) PHENOXY ALKYLAMIDES AND THEIR USE AS ACARICIDES
DE3108203C2 (en)
DD154799A1 (en) AKARICIDAL AGENTS
DE3246847C2 (en)
AT257268B (en) Pest control mixtures
DE2608506A1 (en) NEW PHOSPHORUS COMPOUNDS, THEIR PRODUCTION AND COMPOSITIONS WITH THESE COMPOUNDS
DE1795077C3 (en) Thionophosphonic acid esters, process for their preparation and compositions containing them

Legal Events

Date Code Title Description
PL Patent ceased