ES344436A1 - Cyclopropane carboxylic acids and derivatives thereof having insecticidal properties - Google Patents

Cyclopropane carboxylic acids and derivatives thereof having insecticidal properties

Info

Publication number
ES344436A1
ES344436A1 ES344436A ES344436A ES344436A1 ES 344436 A1 ES344436 A1 ES 344436A1 ES 344436 A ES344436 A ES 344436A ES 344436 A ES344436 A ES 344436A ES 344436 A1 ES344436 A1 ES 344436A1
Authority
ES
Spain
Prior art keywords
alkyl
heterocyclic
acid
methyl
aryl
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
ES344436A
Other languages
Spanish (es)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
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
Application filed by Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of ES344436A1 publication Critical patent/ES344436A1/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C21/00—Acyclic unsaturated compounds containing halogen atoms
    • C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
    • C07C21/14—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing bromine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C22/00—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom
    • C07C22/02—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings
    • C07C22/04—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
    • C07C35/04—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a three or four-membered rings
    • C07C35/045—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a three or four-membered rings containing a four-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41—Preparation of salts of carboxylic acids
    • C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
    • 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
    • C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C61/16—Unsaturated compounds
    • C07C61/35—Unsaturated compounds having unsaturation outside the rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C61/16—Unsaturated compounds
    • C07C61/40—Unsaturated compounds containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/42—Singly bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/10—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/20—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hydrogen atoms and substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
    • C12C11/00—Fermentation processes for beer
    • C12C11/02—Pitching yeast

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Food Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Novel compounds of the formula wherein Z 1 and Z 2 are each H, alkyl, aralkyl, aryl, alkenyl or alkynyl not conjugated with the ring, cycloalkyl, cycloalkenyl or heterocyclic, or Z 1 + Z 2 is alkylene R is OH, Cl or OR1 in which R1 is C 1-6 alkyl, 5-benzyl-fur-3-ylmethyl, dicarboximidomethyl, heterocyclic or 2-methyl- 3-R11-6-keto-cyclopent-2-enyl wherein R11 is alkyl, alkenyl, alkynyl, aryl, aralkyl, cycloalkyl, cycloalkenyl or heterocyclic A is in which R 1 is H or alkyl, R 2 and R 3 are each alkyl, aralkyl, aryl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, or heterocyclic, R 3 having at least 2 carbon atoms, or R 2 and R 3 and the adjacent C atom form a C 3-7 carbon homocycle, saturated or unsaturated and optionally mono- or di-methyl or ethyl and/or methoxy or ethoxy substituted, or a polynuclear aromatic system or a similarly optionally substituted heterocycle, R 4 is methyl or ethyl, R 5 is H, methyl or ethyl or R 4 and R 5 form a saturated or unsaturated fused on homocycle or heterocycle, and Y and Y1 are aliphatic hydrocarbon chains, are prepared by reacting a sulphone of the formula H-A-SO 2 -Ar (Ar is optionally substituted aryl) in the presence of a basic agent with a compound of the formula Z 1 . Z 2 .C = CH.CO 2 R1 (R1 is C 1-6 -alkyl) to give products where R1 is C 1-6 alkyl which may be then transesterified or hydrolysed to the free acids and these re-esterified via functional derivatives such as the acid halides. The racemic acids may be resolved by means of an optically active organic base. The novel compounds wherein R 1 is H, Z 1 and Z 2 are each CH 3 and R 2 and R 3 and the intervening carbon atom form a 3 or 4 carbon homocycle are also prepared by reacting a cyclopropyl or cyclobutyl triaryl phosphonium halide with dl-trans-caronaldehydic acid. Other novel compounds comprise the l-ephedrine salts of d- and l-trans-3,3-dimethyl-2- cyclopentylidenemethyl - 1 - cyclopropane carboxylic acid, the d- and l-forms of this acid and the d- and dl-forms of the sodium salt of this acid. Reference has been directed by the Comptroller to Specification 1,168,797.
ES344436A 1966-08-26 1967-08-25 Cyclopropane carboxylic acids and derivatives thereof having insecticidal properties Expired ES344436A1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
FR74405A FR1505423A (en) 1966-08-26 1966-08-26 New derivatives of cyclopropane and method of preparation
FR74404A FR1507192A (en) 1966-08-26 1966-08-26 Novel aryl allylsulfones and method of preparation
FR96425A FR1527844A (en) 1966-08-26 1967-02-24 New acids and esters derived from cyclopropane and method of preparation
FR110719A FR93112E (en) 1966-08-26 1967-06-16 New derivatives of cyclopropane and method of preparation.
FR114833A FR94309E (en) 1966-08-26 1967-07-19 New cyclopropane derivatives and method of preparation.

Publications (1)

Publication Number Publication Date
ES344436A1 true ES344436A1 (en) 1968-10-16

Family

ID=38863090

Family Applications (3)

Application Number Title Priority Date Filing Date
ES344435A Expired ES344435A1 (en) 1966-08-26 1967-08-25 Cyclopropane carboxylic acids and derivatives thereof having insecticidal properties
ES344436A Expired ES344436A1 (en) 1966-08-26 1967-08-25 Cyclopropane carboxylic acids and derivatives thereof having insecticidal properties
ES350839A Expired ES350839A1 (en) 1966-08-26 1968-02-23 Cyclopropane carboxylic acids and derivatives thereof having insecticidal properties

Family Applications Before (1)

Application Number Title Priority Date Filing Date
ES344435A Expired ES344435A1 (en) 1966-08-26 1967-08-25 Cyclopropane carboxylic acids and derivatives thereof having insecticidal properties

Family Applications After (1)

Application Number Title Priority Date Filing Date
ES350839A Expired ES350839A1 (en) 1966-08-26 1968-02-23 Cyclopropane carboxylic acids and derivatives thereof having insecticidal properties

Country Status (14)

Country Link
AT (2) AT289754B (en)
BE (1) BE702662A (en)
CH (3) CH509961A (en)
CS (3) CS180551B2 (en)
DE (1) DE1668603B2 (en)
DK (3) DK140720B (en)
ES (3) ES344435A1 (en)
FR (5) FR1505423A (en)
GB (2) GB1207371A (en)
IL (2) IL38182A (en)
NL (2) NL162060C (en)
SE (2) SE391330B (en)
SU (1) SU691076A3 (en)
YU (5) YU33952B (en)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3714153A (en) * 1970-06-22 1973-01-30 Roussel Uclaf Novel cyclopropanecarboxylic acids
US4045469A (en) 1971-06-25 1977-08-30 The Procter & Gamble Company Insecticidal esters of spiro carboxylic acids
BE791304A (en) * 1971-11-12 1973-05-14 Procter & Gamble 1-ACENAPHTENOL ESTERS
DE2326077C2 (en) * 1972-05-25 1985-12-12 National Research Development Corp., London Unsaturated cyclopropanecarboxylic acids and their derivatives, their preparation and insecticides containing them
HU168432B (en) * 1973-08-15 1976-04-28
DE2857020A1 (en) * 1977-07-04 1981-01-08 Astra Laekemedel Ab A NOVEL INTERMEDIATE FOR PREPARATION OF THERAPEUTICALLY ACTIVE PYRIDINE COMPOUNDS
DE2730515A1 (en) * 1977-07-06 1979-01-18 Bayer Ag SUBSTITUTED PHENOXYBENZYLOXYCARBONYL DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDES AND ACARICIDES
FR2426673A1 (en) * 1978-05-25 1979-12-21 Nat Res Dev PYRETHRINE TYPE PESTICIDES
FR2428029A1 (en) * 1978-06-06 1980-01-04 Roussel Uclaf ESTERS OF CYCLOPROPANE CARBOXYLIC ACIDS SUBSTITUTED BY A-CYANE ALCOHOL, PROCESS FOR THEIR PREPARATION AND INSECTICIDE OR NEMATICIDE COMPOSITIONS CONTAINING THEM
FR2443452A1 (en) * 1978-12-08 1980-07-04 Roussel Uclaf NEW PROCESS FOR THE SPLITTING OF DL CIS ACID AND DL CHRYSANTHEMIC TRANS
FR2455024A1 (en) * 1979-04-03 1980-11-21 Roussel Uclaf NEW PROCESS FOR THE SPLITTING OF ACIDS D, L-CIS 2,2-DIMETHYL 3- (2 ', 2'-DIHALOVINYL) CYCLOPROPANE-1-CARBOXYLIC
FR2455018A1 (en) * 1979-04-26 1980-11-21 Roussel Uclaf ALLETHROLONE DERIVATIVES AND THEIR PREPARATION PROCESS
DE2926671A1 (en) * 1979-07-02 1981-01-15 Bayer Ag METHOD FOR THE PRODUCTION OF CYCLOPROPANE-CARBONIC ACID DERIVATIVES AND NEW INTERMEDIATE PRODUCTS THEREFOR AND METHOD FOR THE PRODUCTION THEREOF
FR2479192A1 (en) * 1980-03-28 1981-10-02 Roussel Uclaf PROCESS FOR THE PREPARATION OF TETRA-SUBSTITUTED CYCLOPROPANIC DERIVATIVES
FR2490633A1 (en) 1980-09-24 1982-03-26 Roussel Uclaf PROCESS FOR THE PREPARATION OF CYCLOPROPANE CARBOXYLIC ACID DERIVATIVES WITH ALDEHYDE FUNCTION
US5504245A (en) * 1994-09-30 1996-04-02 Eastman Chemical Company Processes for the preparation of cyclopropanecarboxylic acid and derivatives thereof

Also Published As

Publication number Publication date
CS180598B2 (en) 1978-01-31
SE369517B (en) 1974-09-02
NL162060B (en) 1979-11-15
NL172853B (en) 1983-06-01
FR93112E (en) 1969-02-14
DK140720C (en) 1980-04-21
FR1527844A (en) 1968-06-07
DK131538B (en) 1975-08-04
NL6711770A (en) 1968-02-27
GB1207372A (en) 1970-09-30
DE1793721B2 (en) 1976-12-23
YU33952B (en) 1978-09-08
ES350839A1 (en) 1969-05-16
FR1507192A (en) 1967-12-29
DK140720B (en) 1979-11-05
SE391330B (en) 1977-02-14
DE1668603C3 (en) 1974-08-22
YU290379A (en) 1983-10-31
NL172853C (en) 1983-11-01
YU35568B (en) 1981-04-30
GB1207371A (en) 1970-09-30
CH491071A (en) 1970-05-31
DE1668603B2 (en) 1974-01-17
DE1668603A1 (en) 1971-07-01
SU691076A3 (en) 1979-10-05
FR94309E (en) 1969-08-01
ES344435A1 (en) 1968-10-16
AT287671B (en) 1971-02-10
NL162060C (en) 1980-04-15
CH491851A (en) 1970-06-15
NL7906529A (en) 1980-01-31
BE702662A (en) 1968-02-14
YU168567A (en) 1980-10-31
DK131538C (en) 1976-01-05
CS180551B2 (en) 1978-01-31
DK133579C (en) 1976-11-01
DK133579B (en) 1976-06-14
YU33942B (en) 1978-09-08
DE1793721A1 (en) 1972-10-19
AT289754B (en) 1971-03-15
CS180599B2 (en) 1978-01-31
IL38182A (en) 1975-11-25
CH509961A (en) 1971-07-15
IL28541A (en) 1975-11-25
YU168467A (en) 1978-02-28
YU42168A (en) 1978-02-28
FR1505423A (en) 1967-12-15

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