Three-membered Carbocyclic Ring Containing Patents (Class 558/407)
  • Publication number: 20150094474
    Abstract: The present invention relates to derivatives of compounds which are known to be of use in the field of agriculture. These derivatives are differentiated from the parent active compound by virtue of being redox derivatives of the active compound. This means that one or more of the functional groups in the active compound has been converted to another group in one or more changes one or more of which may be considered to represent a change of oxidation state relative to the groups in the original compound. We refer to these compounds generally as redox derivatives. The compounds are of use as insecticides, herbicides and insect repellents.
    Type: Application
    Filed: March 13, 2013
    Publication date: April 2, 2015
    Inventors: William Thompson, Peter Jackson, Derek Lindsay, Thomas Screen, Benjamin Moulton, Christopher Urch
  • Patent number: 8461370
    Abstract: A process for producing comprising reacting a 3-formyl-2,2-dimethylcyclopropanecarboxylate and propionitrile in the presence of a base to obtain 3-(2-cyano-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid or its salt.
    Type: Grant
    Filed: April 5, 2010
    Date of Patent: June 11, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toru Uekawa, Jun Ohshita, Ichiro Komoto, Kouji Yoshikawa
  • Patent number: 8440853
    Abstract: An ester compound represented by formula (1): wherein R2 represents hydrogen, fluorine, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkoxymethyl, or C1-C4 alkylthiomethyl; and R2 represents C1-C4 alkyl, has an excellent pest control effect and is therefore useful as an active ingredient of a pest control agent.
    Type: Grant
    Filed: February 18, 2011
    Date of Patent: May 14, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Noritada Matsuo
  • Patent number: 8202904
    Abstract: The present invention relates to a compound of formula (I), stereoisomers thereof or the mixture of these stereoisomers, wherein: X represents a halogen atom, i.e. F, Cl, Br. The present invention also relates to a process for preparing the compound, and to a use of the compound in the preparation of an insecticide for controlling or killing vectors in the public hygiene and disease control, and to a use of the compound in the preparation of an insecticide for controlling or killing insects, nematodes, and mites in agriculture or horticulture.
    Type: Grant
    Filed: July 10, 2008
    Date of Patent: June 19, 2012
    Assignee: East China Normal University
    Inventors: Xinzhuo Zou, Shuxv Gao, Huihua Cai
  • Publication number: 20100286265
    Abstract: The present invention relates to a compound of formula (I), stereoisomers thereof or the mixture of these stereoisomers, wherein: X represents a halogen atom, i.e. F, Cl, Br. The present invention also relates to a process for preparing the compound, and to a use of the compound in the preparation of an insecticide for controlling or killing vectors in the public hygiene and disease control, and to a use of the compound in the preparation of an insecticide for controlling or killing insects, nematodes, and mites in agriculture or horticulture.
    Type: Application
    Filed: July 10, 2008
    Publication date: November 11, 2010
    Applicant: EAST CHINA NORMAL UNIVERSITY
    Inventors: Xinzhuo Zou, Shuxv Gao, Huihua Cai
  • Patent number: 7468453
    Abstract: A process for the preparation of gamma-cyahlothrin comprising a) chlorinating 1R cis-Z 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl cyclopropanecarboxylic acid to give 1R cis-Z 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl cyclopropanecarboxylic acid chloride; b) esterifying 1R cis-Z 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl cyclopropanecarboxylic acid chloride with 3-phenoxy benzaldehyde in the presence of a source of cyanide to form a diastereoisomeric mixture of cyhalothrin isomers and c) epimerising the diastereoisomeric mixture under conditions in which the least soluble diastereoisomer crystallises from solution.
    Type: Grant
    Filed: December 9, 2003
    Date of Patent: December 23, 2008
    Assignee: Syngenta Limited
    Inventors: Stephen Martin Brown, Brian David Gott
  • Patent number: 7217682
    Abstract: A 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl 2,2-dimethyl-3-(2-cyano-3-hydrocarbyloxy-3-oxo-1-propenyl) cyclopropanecarboxylate given by the formula (1): wherein G represents C1–C4 alkyl or C3–C4 alkenyl, has excellent pests controlling effect.
    Type: Grant
    Filed: November 20, 2002
    Date of Patent: May 15, 2007
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Tatsuya Mori
  • Patent number: 6908945
    Abstract: A cyclopropanecarboxylic acid ester compound of formula (1): has an excellent pesticidal efficacy, and a pesticidal composition comprising it as an active ingredient is useful for controlling pests.
    Type: Grant
    Filed: April 10, 2003
    Date of Patent: June 21, 2005
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Tatsuya Mori
  • Patent number: 6528675
    Abstract: Ethers and esters of cyanohydrins that contain optically detectable moieties are highly effective for detecting, monitoring, and measuring the activity of enzymes that cause the cleavage of certain types of substrates. The cyanohydrins function as proaldehydes and proketones, spontaneously converting to aldehydes and ketones, respectively, which provide a large increase in optical detectability relative to both the starting esters and ethers and the cyanohydrins.
    Type: Grant
    Filed: October 3, 2001
    Date of Patent: March 4, 2003
    Assignee: The Regents of the University of California
    Inventors: Bruce D. Hammock, Guomin Shan, Rong Zhang
  • Patent number: 6331564
    Abstract: The present invention provides a class of chemical compounds useful as efficacious drugs in the treatment of sickle cell disease and diseases characterized by unwanted or abnormal cell proliferation, and in particular inflammatory diseases associated with unwanted cellular proliferation. The active compounds are substituted triaryl methane compounds or analogues thereof where one or more of the aryl groups is replaced with a heteroaryl, cycloalkyl or heterocycloalkyl group and/or the tertiary carbon atom is replaced with a different atom such as Si, Ge, N or P, the compounds inhibit mammalian cell proliferation, inhibit the Gardos channel of erythrocytes, reduce sickle erythrocyte dehydration and/or delay the occurrence of erythrocyte sickling or deformation.
    Type: Grant
    Filed: September 23, 1998
    Date of Patent: December 18, 2001
    Assignee: Ion Pharmaceuticals, Inc.
    Inventors: Carlo Brugnara, Jose Halperin, Emile M. Bellot, Jr., Mark Froimowitz, Richard John Lombardy, John J. Clifford, Ying-Duo Gao, Reem M. Haidar, Eugene W. Kelleher, Falguni M. Kher, Adel M. Moussa, Yesh P. Sachdeva, Minghua Sun, Heather N. Taft
  • Patent number: 6300372
    Abstract: Novel 3-cyano-3-(3,4-disubstituted)phenylcyclohexyl-1-carboxylates or derivatives thereof and their corresponding cyclohexenyl analogs are described herein. These compounds inhibit the production of Tumor Necrosis Factor and are useful in the treatment of disease states mediated or exacerbated by TNF production. These compounds are also useful mediating or inhibiting the enzymatic or catalytic activity of phosphodiesterase IV and are therefore useful in treating diseases in need of mediation or inhibition thereof.
    Type: Grant
    Filed: January 30, 1996
    Date of Patent: October 9, 2001
    Assignee: SmithKline Beecham Corporation
    Inventors: Siegfried B. Christensen, IV, Cornelia Jutta Forster
  • Patent number: 6028103
    Abstract: The present invention provides a class of chemical compounds useful as efficacious drugs in the treatment of sickle cell disease and diseases characterized by unwanted or abnormal cell proliferation. The active compounds are substituted triaryl methane compounds or analogues thereof where one or more of the aryl groups is replaced with a heteroaryl, cycloalkyl or heterocycloalkyl group and/or the tertiary carbon atom is replaced with a different atom such as Si, Ge, N or P. The compounds inhibit mammalian cell proliferation, inhibit the Gardos channel of erythrocytes, reduce sickle erythrocyte dehydration and/or delay the occurrence of erythrocyte sickling or deformation.
    Type: Grant
    Filed: March 19, 1997
    Date of Patent: February 22, 2000
    Assignees: Children's Medical Center Corporation, Ion Pharmaceuticals, Inc.
    Inventors: Carlo Brugnara, Jose Halperin, Emile M. Bellot, Jr., Mark Froimowitz, Richard John Lombardy, John J. Clifford, Ying-Duo Gao, Reem M. Haidar, Eugene W. Kelleher, Falguni M. Kher, Adel M. Moussa, Yesh P. Sachdeva, Minghua Sun, Heather N. Taft
  • Patent number: 5504112
    Abstract: A compound in all possible stereoisomeric forms and their mixtures of the formula ##STR1## wherein X is selected from the group consisting of hydrogen, --CN, alkyl, alkenyl and alkynyl of up to 4 carbon atoms and aralkynyl of up to 10 carbon atoms, Y is selected from the group consisting of halogen, --CF.sub.3, --CH.sub.2 F and --CHF.sub.2 and R.sub.1 is hydrogen and R.sub.2 is halogen or R.sub.1 and R.sub.2 are --CF.sub.3 or R.sub.1 and R.sub.2 are individually halogen.
    Type: Grant
    Filed: May 15, 1995
    Date of Patent: April 2, 1996
    Assignee: Roussel Uclaf
    Inventors: Didier Babin, Marc Benoit, Raphael Bouchet, Jean-Pierre Demoute
  • Patent number: 5420159
    Abstract: All possible stereoisomeric forms and mixtures thereof of a compound of the formula ##STR1## wherein X is selected from the group consisting of hydrogen, alkyl, alkenyl and alkynyl of up to 4 carbon atoms, --CN and aralkynyl of up to 10 carbon atoms, Y is selected from the group consisting of halogen, --CH.sub.2 F, --CHF.sub.2, and --CF.sub.3, A is selected from the group consisting of ##STR2## having pesticidal properties.
    Type: Grant
    Filed: September 26, 1994
    Date of Patent: May 30, 1995
    Assignee: Roussel-Uclaf
    Inventors: Didier Babin, Marc Benoit, Jean-Pierre Demoute
  • Patent number: 5340835
    Abstract: A compound selected from the group consisting of all stereoisomeric forms and mixtures thereof of a compound of the formula ##STR1## wherein Y and Z are individually selected from the groups consisting of hydrogen, halogen, --CF.sub.3, alkyl, alkoxy and alkylthio of 1 to 8 carbon atoms and aryl, aryloxy and arylthio of up to 14 carbon atoms optionally substituted with at least one member of the group consisting of halogen, hydroxy optionally esterified etherified, --CF.sub.3 and alkyl of 1 to 8 carbon atoms and R is alkyl of 1 to 8 carbon atoms or the remainder of a pyrethrinoid alcohol having excellent pesticidal properties and their preparation and intermediates.
    Type: Grant
    Filed: January 19, 1993
    Date of Patent: August 23, 1994
    Assignee: Roussel-UCLAF
    Inventors: Didier Babin, Marc Benoit, Jean-Pierre Demoute, Fabienne Pilorge, Nicole Reinier
  • Patent number: 5336670
    Abstract: Compounds of the formula ##STR1## wherein X is hydrogen, halogen or an optionally substituted alkyl, Y is selected from the group consisting of hydrogen, halogen optionally substituted alkyl, an optionally substituted aryl or arylalkyl, --(CH.sub.2).sub.m Si (Alk.sub.1).sub.3, --(CH.sub.2).sub.n OAlk.sub.2 or --(CH.sub.2).sub.p SAlk.sub.3, m, n and p are an integer from 0 to 6, Alk.sub.1, Alk.sub.2 and Alk.sub.3 are alkyl and R is alkyl of 1 to 18 carbon atoms or the remainder of an alcohol used in the pyrethrinoid series having pesticide properties.
    Type: Grant
    Filed: December 17, 1992
    Date of Patent: August 9, 1994
    Assignee: Roussel-Uclaf
    Inventors: Marc Benoit, Jean-Pierre Demoute, Jean-Marc Girodeau
  • Patent number: 5334744
    Abstract: A process for obtaining an isomer of a compound of general formulaR--CH(CN)--R' (I)wherein each of R and R' may be any organic radical linked directly or through a heteroatom to the carbon atom bearing the cyano group provided that at least one of R and R' comprises at least one resolved chiral center which is stable under the conditions of the process, or a racemic modification comprising the isomer and its enantiomer, which comprises the step of treating the epimer of the isomer, or the racemate comprising the epimer and the enantiomer of the epimer, in solution in a polar organic solvent, or in slurry in a polar organic liquid diluent in which the epimer or the racemate is partially soluble, with a source of cyanide ions, in the absence of a base, the isomer, or the racemic modification comprising the isomer and its enantiomer, being less soluble in the solvent or diluent than the epimer of the isomer, or the racemate comprising the epimer of the isomer and the enantiomer of the epimer, respectively.
    Type: Grant
    Filed: December 23, 1992
    Date of Patent: August 2, 1994
    Assignee: Zeneca Ltd.
    Inventors: Ernest S. Cleugh, David J. Milner
  • Patent number: 5247119
    Abstract: A class of substituted phenylacetonitrilehydroxyalkylaminoalkyl-ortho-substituted aryl compounds having immunosuppressive properties is described. Compounds of this class would be useful in reducing recipient rejection of transplanted organs and for treatment of autoimmune or inflammatory diseases. Compounds of particular interest are of the formula ##STR1## wherein each of m and n is a number independently selected from one to five, inclusive; wherein R.sup.1 is selected from hydrido, alkyl, hydroxyalkyl, cycloalkyl, cycloalkylalkyl, alkoxyalkyl, alkenyl and alkynyl; wherein R.sup.6 is selected from loweralkyl; wherein each of R.sup.8, R.sup.9, R.sup.10 and R.sup.12 through R.sup.16 is independently selected from hydrido, hydroxy, alkyl, hydroxyalkyl, alkoxy, alkenyl, alkynyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonylalkenyl, alkylaminocarbonyl and alkoxyalkyl; or a tautomer thereof or a pharmaceutically-acceptable salt thereof.
    Type: Grant
    Filed: May 28, 1992
    Date of Patent: September 21, 1993
    Assignee: G. D. Searle & Co.
    Inventors: Kerry W. Fowler, John M. Farah, Jr., John P. McKearn, Richard A. Mueller, Susan A. Gregory
  • Patent number: 5245073
    Abstract: Novel 2,2-dimethyl-cyclopropane carboxylic acid derivatives of the formula ##STR1## wherein X.sub.1 and X.sub.2 are individually halogen, R.sub.1 is selected from the group consisting of halogen, alkyl of 1 to 8 carbon atoms, optionally substituted aryl of 6 to 14 carbon atoms, perfluoroalkyl of 1 to 8 carbon atoms, --CN and ##STR2## R' is alkyl of 1 to 8 carbon atoms, Y is selected from the group consisting of --SO.sub.2 Alk.sub.1, --SO.sub.2 Ar, ##STR3## Alk.sub.1 is optionally unsaturated alkyl of 1 to 8 carbon atoms optionally substituted with at least one halogen, Ar is aryl of 6 to 14 carbon atoms optionally substituted with at least one halogen Alk.sub.2 and Alk.sub.3 and Alk.sub.2 ' and Alk.sub.
    Type: Grant
    Filed: August 20, 1991
    Date of Patent: September 14, 1993
    Assignee: Roussel Uclaf
    Inventors: Joseph Cadiergue, Jean-Pierre Demoute, Jean Tessier
  • Patent number: 5223536
    Abstract: The 1,4-diaryl-1-cyclopropyl-4-substituted butane pesticides of the following formula are effective as insecticides and acaricides: ##STR1## in which X and Y are independently hydrogen, halogen, alkyl, alkoxy, cycloalkylalkoxy, alkylcarbonyl, alkoxycarbonyl, haloalkyl, haloalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, trialkylamino, nitro, or cyano; or X and Y together are --OCH.sub.2 O-- or --OCF.sub.2 O-- bridging the 2-3 or 3-4 positions of the phenyl ring; Ar is 3-phenoxyphenyl, 4-fluoro-3-phenoxyphenyl, 6-phenoxypyridin-2-yl, or 2-methyl(1,1'-biphenyl)-3-yl;R is cyano, methyl, trifluoromethyl, alkenyl, alkynyl, or halogen.
    Type: Grant
    Filed: July 23, 1991
    Date of Patent: June 29, 1993
    Assignee: FMC Corporation
    Inventors: Thomas G. Cullen, Scott McN. Sieburth, Gary A. Meier, John F. Engel
  • Patent number: 5192801
    Abstract: All stereoisomeric forms and mixtures thereof of a compound of the formula ##STR1## wherein the cyclopropane copula has (1R, cis) or (1R, trans) structure, the geometry of the double bond carried by the 3-carbon atom is (E) or (Z), X is halogen, Z is selected from the group consisting of hydrogen, methyl, --CN and --C.tbd.CH, n is an integer from 1 to 5, m represents the number 5-n, Y is selected from the group consisting of hydrogen, halogen, --CH.sub.2 --CN, --OH, optionally unsaturated alkyl of 1 to 8 carbon atoms unsubstituted or substituted with at least one halogen, --CN, --COOAlk, --COAlk, --(CH.sub.2).sub.m , OAlk, --(CH.sub.2).sub.m, --S--Alk, --(CH.sub.2).sub.m, --N(Alk).sub.2, --Si(Alk).sub.3, --OAr and (CH.sub.2).sub.m, --Ar, m' is 0, 1, 2, 3 or 4, Alk is optionally unsaturated alkyl of 1 to 8 carbon atom unsubstituted or substituted with at least one halogen and Ar is aryl of 6 to 14 carbon atoms and the Ys identical or different may be on any position of the phenyl having pesticidal properties.
    Type: Grant
    Filed: February 20, 1992
    Date of Patent: March 9, 1993
    Assignee: Roussel Uclaf
    Inventors: Didier Babin, Marc Benoit, Jean-Pierre Demoute, Jean Tessier
  • Patent number: 5164411
    Abstract: The four isomer compound derived from racemic cis/trans-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid and (S)(cyano)(3-phenoxyphenyl) methanol is twice as effective as cypermethrin against certain insect species, but quite unexpectedly is significantly less toxic to mammals and certain species of fish at rates giving commercial control of target crop insects.
    Type: Grant
    Filed: October 30, 1991
    Date of Patent: November 17, 1992
    Assignee: FMC Corporation
    Inventors: Jonathan S. Baum, Michael S. Glenn
  • Patent number: 5153349
    Abstract: The invention relates to a process for the preparation of such isomer mixtures of cypermethrine of the Formula (I) ##STR1## wherein carbon atoms indicated by 1, 3 and .alpha. stand for a chiral carbon atom and the wavy line indicates cis or trans configuration related to the cyclopropane ring--which contains out of the theoretically possible 8-isomers of cypermethrine at least 95% of 1RtransS and 1StransR (Ib) isomer pair or only a mixture of 1RcisC and 1ScisR (Ia) and the isomer pair (Ib) of the ratio (Ia):(Ib)=55:45-25:75 by asymmetric transformation of second order performed in the presence of an amine base and solvent from a starting cypermethrine isomer mixture which contains next to the isomer pair (Ib) cis and other trans isomers or the isomer pair Ia+Ib at an undesired ratio.
    Type: Grant
    Filed: October 19, 1990
    Date of Patent: October 6, 1992
    Assignee: Chinoin Gyogyszer- es Vegyeszeti Termekek Gyara Rt.
    Inventors: Sandor Zoltan, Gyorgy Hidasi, Bela Bertok, Istavan Szekely, Janis Hajimichael, Sandor Botar, Lajos Nagy, Eva Somfai, Istvan Lak, Andras Rapi, Antal Gajary, Agnes Hegedus, Maria Tary
  • Patent number: 5135951
    Abstract: All stereoisomeric forms and mixtures thereof of a compound of the formula ##STR1## wherein the cyclopropane copula has (1R, cis) or (1R, trans) structure, the geometry of the double bond carried by the 3-carbon atom is (E) or (Z), X is halogen, Z is selected from the group consisting of hydrogen, methyl, --CN and --C.tbd.CH, n is an integer from 1 to 5, m represents the number 5-n, Y is selected from the group consisting of hydrogen, halogen, --CH.sub.2 --CN, --OH, optionally unsaturated alkyl of 1 to 8 carbon atoms unsubstituted or substituted with at least one halogen, --CN, --COOAlk, --COAlk, --(CH.sub.2).sub.m' OAlk, --(CH.sub.2).sub.m' --S--Alk, --(CH.sub.2).sub.m' --N(Alk).sub.2, --Si(Alk).sub.3, --OAr and (CH.sub.2).sub.m' --Ar, m' is 0, 1,2,3 or 4, Alk is optionally unsaturated alkyl of 1 to 8 carbon atom unsubstituted or substituted with at least one halogen and Ar is aryl of 6 to 14 carbon atoms and the Ys identical or different may be on any position of the phenyl having pesticidal properties.
    Type: Grant
    Filed: February 26, 1991
    Date of Patent: August 4, 1992
    Assignee: Roussel Uclaf
    Inventors: Didier Babin, Marc Benoit, Jean-Pierre Demoute, Jean Tessier
  • Patent number: 5128497
    Abstract: Crystalline pyrethroid isomers or enantiomer pairs are converted to more pesticidally active isomers by contacting a hydrocarbon slurry of the starting isomers with an epimerization agent selected from the group consisting of 1,1,3,3-tetramethylguanidine and 1,8-diazabicyclo[5.4.0]undec-7-ene, agitating the slurry while maintaining a temperature effective for conversion, and recovering the resulting isomers. The process typically is effective for enriching cypermethrin, and cyfluthrin.
    Type: Grant
    Filed: January 3, 1990
    Date of Patent: July 7, 1992
    Assignee: FMC Corporation
    Inventor: John W. Ager
  • Patent number: 5110976
    Abstract: A process is disclosed for preparing a synergistic, crystalline product consisting of solely enantiomer pair 1RCisS and 1SCisR and enantiomer pair 1RTransS and 1STransR of cypermethrin in a 3:7 to 5:5 crystalline mixture, which comprises the steps of: (a) epimerizing an oily melt or a saturated solution of enantiomer pair 1RCisS and 1SCisR and enantiomer pair 1RTransS and 1STransR in a ratio other than 3:7 to 5:5, or a mixture of enantiomer pair 1RCisS and 1SCisR, enantiomer pair 1RTransS and 1STransR together with enantiomer pair 1RCisR and 1SCisS and enantiomer pair 1RTransR and 1STransS, said saturated solution including a protic or apolar, aprotic inert organic solvent by treating said oily melt or saturated solution with an organic or inorganic base at a temperature of -15.degree. C. to 30.degree. C.
    Type: Grant
    Filed: May 7, 1991
    Date of Patent: May 5, 1992
    Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Rt.
    Inventors: Gyorgy Hidasi, Istvan Szekely, Bela Bertok, Sandor Zoltan, Lajos Nagy, Antal Gajari, Eva Somfai, Agnes Hegedus, Laszlo Pap, Rudolf Soos, Erzsebet Radvany, Sandor Botar, Tamas Szabolcsi
  • Patent number: 5089511
    Abstract: A process for the preparation of trifluoromethylvinyl compounds in all their possible steroisomeric forms and mixtures thereof comprising reacting a salt of trifluoroacetic acid with a halovinyl compound in the presence of a cuprous salt to obtain the same stero-specific compound and all possible stero-isomeric forms and mixtures thereof of 1R, trans compounds of the formula ##STR1## wherein R is an alcohol residue used in pyrethrinoid series, or an alcohol residue capable of blocking the acid function, and Z is aryl or haloaryl and the double bond has Z geometry having pesticide activity.
    Type: Grant
    Filed: January 18, 1990
    Date of Patent: February 18, 1992
    Assignee: Roussel Uclaf
    Inventors: Werner Bonin, Jean-Pierre Demoute, Jean Tessier
  • Patent number: 5082832
    Abstract: Novel 2,2-dimethyl-cyclopropane carboxylic acid derivatives of the formula ##STR1## wherein X.sub.1 and X.sub.2 are individually halogen, R.sub.1 is selected from the group consisting of halogen, alkyl of 1 to 8 carbon atoms, optionally substituted aryl of 6 to 14 carbon atoms, perfluoroalkyl of 1 to 8 carbon atoms, --CN and ##STR2## R' is alkyl of 1 to 8 carbon atoms, Y is selected from the group consisting of ##STR3## Alk.sub.1 is optionally unsaturated alkyl of 1 to 8 carbon atoms no substituted or substituted with at least one functional group, Ar is aryl of 6 to 14 carbon atoms no substituted or substituted with at least one functional group, Alk.sub.2 and Alk.sub.3 and Alk.sub.2 ' and Alk.sub.
    Type: Grant
    Filed: October 18, 1989
    Date of Patent: January 21, 1992
    Assignee: Roussel Uclaf
    Inventors: Joseph Cadiergue, Jean-Pierre Demoute, Jean Tessier
  • Patent number: 5066673
    Abstract: Substituted benzyl 2-phenylalk(en)-1-ylcyclopropanecarboxylates of the general formula I ##STR1## where R.sup.1 is halogen or in each case low molecular weight, alkyl, alkoxy, haloalkyl or haloalkoxy (n=1 to 5),R.sup.2 is halogen or, in each case low molecular weight, alkyl or haloalkyl,R.sup.3, R.sup.4 are halogen or each is an electron in a double bond formed by them together,R.sup.5 is hydrogen or, in each case low molecular weight, alkyl, alkenyl, alkynyl or cyano,R.sup.6 is halogen or alkyl (n=1 to 4),R.sup.7 is halogen (p=0 to 25),and their use for combating pests.
    Type: Grant
    Filed: February 22, 1990
    Date of Patent: November 19, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Winfried Zombik, Hans Theobald, Bernd Wolf, Ludwig Schuster, Peter Hofmeister, Christoph Kuenast
  • Patent number: 5030655
    Abstract: A compound selected from the group consisting of all possible isomeric forms and mixtures thereof of a compound of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms and cycloalkyl and cycloalkylalkyl of 3 to 8 carbon atoms, R.sub.2 is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms, cycloalkyl of 3 to 8 carbon atoms and acyl of 1 to 9 carbon atoms, X.sub.1 and X.sub.2 are individually selected from the group consisting of fluorine, chlorine, bromine, iodine, --CF.sub.3, --CN, --COOR and ##STR2## R is alkyl of 1 to 8 carbon atoms, Hal is chlorine, bromine or fluorine and R.sub.3 is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms and residue of an alcohol used in pyrethrinoid synthesis having excellent pesticidal properties.
    Type: Grant
    Filed: September 25, 1989
    Date of Patent: July 9, 1991
    Assignee: Roussel Uclaf
    Inventors: Jean Tessier, Jacques Demassey, Jean-Pierre Demoute
  • Patent number: 5028731
    Abstract: A mixture of isomers of cypermethrin or cyfluthrin enriched in the more insecticidally active c.sub.2 or t.sub.2 isomer, or both, is prepared by adding .alpha.-hydroxy-3-phenoxyphenylacetonitrile or its 4-fluoro analog to a refluxing solution of 3-(2,2-dichloroethenyl)-2-2-dimethylcyclopropanecarbonyl chloride in a hydrocarbon solvent boiling in the range of about 75.degree. to 115.degree. C. in an inert atmosphers, without an acid acceptor being present in the reaction mixture. The product is recovered by washing the reaction mixture with aqueous base.
    Type: Grant
    Filed: November 17, 1989
    Date of Patent: July 2, 1991
    Assignee: FMC Corporation
    Inventor: Michael S. Glenn
  • Patent number: 5024828
    Abstract: Novel isomers or mixtures of isomers of radioactive pyrethrinoids marked with iodine of the formula ##STR1## wherein X.sub.1 is selected from the group consisting of halogen and --CF.sub.3, X.sub.2 is a halogen, R is the residue of an amino acid of the formula R--NH.sub.2 or a derivative thereof containing an iodine acceptor group and marked with iodine.sup.125 or iodine.sup.131, process for their preparation and intermediates and their use in radioimmunological determination.
    Type: Grant
    Filed: January 28, 1987
    Date of Patent: June 18, 1991
    Assignee: Roussel Uclaf
    Inventors: Jean-Pierre Demoute, Gaetan Touyer, Michel Mouren
  • Patent number: 5013754
    Abstract: According to the present invention there is provided a synergistic insecticidal composition containing more than one active ingredients and being harmless to environment characterized by comprising in an amount of from 0.001 to 99% by weight a synthetic pyrethroid of the Formula /I/ ##STR1## namely substantially only the 1RtransS and 1StransR entantiomer-pair /Ib/ out from the possible eight isomers--optionally in admixture with an amount of up to 100% by weight of one or more activator/s/ and auxiliary agent/s/, particularly antioxidants, stabilizing agents, wetting agents, emulsifying agents, dispersing agents, antifoam agents, diluents and/or fillers.The enantiomer-pair Ib consisting of the 1RtransS and 1StransR isomers is new and the invention also relates to the said new enantiomer-pair and a process for the preparation thereof.
    Type: Grant
    Filed: June 16, 1989
    Date of Patent: May 7, 1991
    Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Rt.
    Inventors: Gyorgy Hidasi, Istvan Szekely, Bela Bertok, Sandor Zoltan, Lajos Nagy, Antal Gajari, Eva Somfai, Agnes Hegedus, Laszlo Pap, Rudolf Soos, Erzsebet Radvany, Sandor Botar, Tamas Szabolcsi
  • Patent number: 4997970
    Abstract: Crystallizable pyrethroid isomers or enantiomer pairs are converted to more pesticidally active isomers by contacting a hydrocarbon slurry of the starting isomers with a base and a catalyst, the catalyst being substantially soluble in the slurry and selected from a quaternary ammonium compound, a quaternary phosphonium compound and a crown ether, agitating the slurry while maintaining a temperature effective for conversion, and recovering the resulting isomers. The tendency to form benzoin ester by-product is reduced by including in the slurry a weak base, an aldehyde scavenger such as a metabisulfite, and/or a tetraalkyl (C.sub.1 -C.sub.5) ammonium halide catalyst dissolved in an aprotic solvent such as an organic nitrile. The process typically is effective for enriching cypermethrin, cyfluthrin and (cyano (3-phenoxyphenyl)methyl 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylate in the more active species.
    Type: Grant
    Filed: May 23, 1988
    Date of Patent: March 5, 1991
    Assignee: FMC Corporation
    Inventor: John W. Ager, Jr.
  • Patent number: 4983630
    Abstract: There are provided new 2,2-difluorocyclopropylethane derivatives of general formula I ##STR1## in which A, B and R.sup.1-5 have the meanings given in the description and processes for their preparation. The compounds of the invention can be used as pesticides, especially against insects and mites.
    Type: Grant
    Filed: November 28, 1988
    Date of Patent: January 8, 1991
    Assignee: Schering Aktiengesellschaft
    Inventors: Peter Wegner, Hartmut Joppien, Gunter Homberger, Arnim Kohn
  • Patent number: 4970330
    Abstract: A compound of the formula ##STR1## wherein one of Y and Z is a perhaloalkyl group having 1 to 2 carbon atoms and the other is halogen or methyl; and R is OR.sup.1 in which R.sup.1 represents a phenoxybenzyl group optionally substituted in the alpha position by a cyano or ethynyl group.
    Type: Grant
    Filed: December 30, 1982
    Date of Patent: November 13, 1990
    Assignee: Imperial Chemical Industries PLC
    Inventor: Roger K. Huff
  • Patent number: 4925874
    Abstract: Novel 2,2-dimethyl-cyclopropane carboxylic acid derivatives of the formula ##STR1## wherein X.sub.1 and X.sub.2 are individually halogen, R.sub.1 is selected from the group consisting of halogen, alkyl of 1 to 8 carbon atoms, optionally substituted aryl of 6 to 14 carbon atoms, perfluoroalkyl of 1 to 8 carbon atoms, --CN and ##STR2## R' is alkyl of 1 to 8 carbon atoms, Y is selected from the group consisting of --SO.sub.2 Alk.sub.1, --SO.sub.2 Ar, ##STR3## Alk.sub.1 is optionally unsaturated alkyl of 1 to 8 carbon atoms no substituted or substituted with at least one functional group, Ar is aryl of 6 to 14 carbon atoms no substituted or substituted with at least one functional group, Alk.sub.2 and Alk.sub.3 and Alk.sub.2 ' and Alk.sub.
    Type: Grant
    Filed: November 20, 1987
    Date of Patent: May 15, 1990
    Assignee: Roussel Uclaf
    Inventors: Joseph Cadiergue, Jean-Pierre Demoute, Jean Tessier
  • Patent number: 4920231
    Abstract: A process for the preparation of trifluoromethylvinyl compounds in all their possible streoisomeric forms and mixtures thereof comprising reacting a salt of trifluoroacetic acid with a halovinyl compound in the presence of a cuprous salt to obtain the same stereo-specific compound and all possible stereo-isomeric forms and mixtures thereof of 1R, trans compounds of the formula ##STR1## wherein R is an alcohol residue used in pyrethrinoid series, or an alcohol residue capable of blocking the acid function, and Z is aryl or haloaryl and the double bond has Z geometry having pesticide activity.
    Type: Grant
    Filed: March 30, 1989
    Date of Patent: April 24, 1990
    Assignee: Roussel Uclaf
    Inventors: Werner Bonin, Jean-Pierre Demoute, Jean Tessier
  • Patent number: 4902697
    Abstract: Derivatives of 2,2-dimethylcyclopropanecarboxylic acid endowed with insecticidal and acaricidal activity, and having the formula ##STR1## wherein: R is an alkyl, cycloalkyl, alkenyl or alkynyl radical having from 1 to 8 carbon atoms, optionally substituted with halogen atoms, or R is an aryl radical optionally substituted with halogen atoms, alkyl or alkoxyl radicals;Y is O or S;X is H, F, Cl, Br, --CH.sub.3, or --CF.sub.3 ;R.sub.1 represents a group having the formula: ##STR2## wherein: X.sub.1 =H or F; X.sub.2 =H, --CN, or --C.tbd.CH; Q=O or CH.sub.2 ; A=CH or N when X1=H, X2=CN and Q=O.
    Type: Grant
    Filed: August 25, 1987
    Date of Patent: February 20, 1990
    Assignee: Montedison S.p.A.
    Inventors: Luigi Capuzzi, Franco Bettarini, Paolo Castoro, Pietro Massardo, Vincenzo Caprioli
  • Patent number: 4879302
    Abstract: All possible stereoisomeric forms and mixtures thereof of a compound of the formula ##STR1## wherein A is selected from the group consisting of hydrogen, optionally unsaturated alkyl and haloalkyl of 1 to 18 carbon atoms, optionally substituted with aryl or a heterocyclic and optionally interrupted by --O-- or --S--, optionally unsaturated cycloalkyl of 3 to 18 carbon atoms, aryl of 6 to 14 carbon atoms and heterocyclic, B is selected from the group consisting of hydrogen, alkyl of 1 to 18 carbon atoms optionally interrupted by --S-- or --O-- and optionally substituted with at least one member of the group consisting of halogen, --OH, alkoxy of 1 to 8 carbon atoms, --SH, thioalkoxy of 1 to 8 carbon atoms, --NO.sub.2 and --CN and R is selected from the group consisting of optionally unsaturated alkyl of 1 to 18 carbon atoms and residue of an alcohol used in the synthesis of pyrethrinoid esters having pesticidal activity.
    Type: Grant
    Filed: October 29, 1987
    Date of Patent: November 7, 1989
    Assignee: Roussel Vclaf
    Inventors: Jean Tessier, Jean-Pierre Demoute, Joseph Cadiergue
  • Patent number: 4874887
    Abstract: The present invention relates to a novel process for the preparation of insecticidally active esters of the general formula (I) ##STR1## wherein R.sub.1 and R.sub.2 are the same or diferent from each other and represent a hydrogen or a halogen atom; R.sub.3 represents ##STR2## (wherein R.sub.4 and R.sub.5 represent a chlorine or bromine atom or a methyl group when R.sub.4 is identical to R.sub.5, but R.sub.4 represents a chlorine or bromine atom or a methyl group and R.sub.5 represents a trifluoromethyl group when R.sub.4 is different from R.sub.5, and R.sub.6 represents a halogen atom or a difluoromethoxy group); and R.sub.8 represents a hydrogen or a cyano group.The characteristic of the present invention is a one-step procedure comprising directly condensing an organic acid, an aldehyde (and a water-soluble cyanide) in the presence of a phase transfer catalyst and a water-soluble inorganic base by the use of a sulphonyl compound as a condensing reagent.
    Type: Grant
    Filed: October 7, 1988
    Date of Patent: October 17, 1989
    Assignee: Lucky, Ltd.
    Inventors: Sang H. Jung, Seung K. Kim
  • Patent number: 4864052
    Abstract: A 2,2-dimethylcyclopropanecarboxylic acid derivative having the formula: ##STR1## wherein R.sup.1 is an alkyl group or an aryl group, R.sup.2 is a hydrogen atom, an acyl group, a sulfonyl group or an alkyl group, and each of X.sup.1 and X.sup.2 is a halogen atom.
    Type: Grant
    Filed: April 14, 1988
    Date of Patent: September 5, 1989
    Assignee: Sagami Chemical Research Center
    Inventors: Tamejiro Hiyama, Makoto Fujita
  • Patent number: 4849536
    Abstract: A process for the preparation of .alpha.-cyanobenzyl esters of cyclopropane carboxylic acids and substituted alkanoic acids by treating a carboxylic acid and a benzaldehyde with a metal cyanide, followed by treatment with a sulfonyl halide.
    Type: Grant
    Filed: February 1, 1988
    Date of Patent: July 18, 1989
    Assignee: Sandoz Ltd.
    Inventor: John M. Gruber
  • Patent number: 4849449
    Abstract: Novel stereoisomers or mixtures of stereoisomers of compounds of the formula ##STR1## wherein R is the residue of an alcohol used in the pyrethrinoid field having remarkable pesticidal properties and being surprisingly stable.
    Type: Grant
    Filed: December 9, 1986
    Date of Patent: July 18, 1989
    Assignee: Roussel Uclaf
    Inventors: Jean Tessier, Jean-Pierre DeMoute, Joseph Cadiergue
  • Patent number: 4732903
    Abstract: Novel isomers and mixtures thereof of cyclopropane carboxylic acid derivatives with a 3-unsaturated side chain of the formula ##STR1## wherein A' is selected from the group consisting of wherein B is selected from the group consisting of --CH.sub.2 --, ##STR2## --O-- and --S--, R.sub.4 is selected from the group consisting of hydrogen, --CH.sub.3,--C.tbd.N--CONH.sub.2, --CSNH.sub.2 and --C.tbd.CH, n is an integer from 0, 1 or 2 and R.sub.5 is selected from the group consisting of halogen and --CH.sub.3 ##STR3## wherein R.sub.13 is selected from the group consisting of hydrogen and ##STR4## wherein R.sub.13 has the above definition and the benzoyl is in the 3- or 4-position, ##STR5## wherein R.sub.14 is selected from the group consisting of hydrogen, methyl, ethynyl and --CN and R.sub.15 and R.sub.16 are individually selected from the group consisting of hydrogen, bromine and fluorine and ##STR6## wherein R.sub.14 has the above definition, p is 0, 1 or 2, each R.sub.
    Type: Grant
    Filed: July 17, 1985
    Date of Patent: March 22, 1988
    Assignee: Roussel Uclaf
    Inventors: Jacques Martel, Jean Tessier, Andre Teche
  • Patent number: 4723027
    Abstract: Preparation of certain optically-active alpha-hydroxynitriles or a mixture enriched therein comprises treating an aldehyde with hydrogen cyanide in a substantially water-immiscible, aprotic solvent in the presence of a cyclo(D-phenylalanyl-D-histidine) as a catalyst.
    Type: Grant
    Filed: January 27, 1986
    Date of Patent: February 2, 1988
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Donald W. Stoutamire, Walter Dong
  • Patent number: 4689342
    Abstract: Novel esters in all possible isomeric forms or a mixture thereof having the formula ##STR1## wherein Y is selected from the group consisting of hydrogen, halogen, --OAlK and ##STR2## AlK is alkyl of 1 to 6 carbon atoms, n is 0, 1 or 2, Z is selected from the group consisting of --O-- and --S--, R.sub.1 is selected from the group consisting of (a) optionally unsaturated alkyl of 1 to 8 carbon atoms and optionally unsaturated cycloalkyl or cycloalkylalkyl of 3 to 8 carbon atoms optionally substituted with at least one member of the group consisting of halogen, --OH, --SH, --OR', --SR', ##STR3## --SO.sub.2 AlK.sub.2, --SO.sub.3 AlK.sub.3, aryl optionally substtuted with at least one member of the group consisting of --OH, alkoxy of 1 to 8 carbon atoms, alkyl of 1 to 8 carbon atoms, halogen, --CF.sub.3, --OCF.sub.3, --SCF.sub.3 and ##STR4## R' is alkyl of 1 to 8 carbon atoms, R" and R'" are individually selected from the group consisting of hydrogen and alkyl of 1 to 8 carbon atoms, AlK.sub.1, AlK.sub.2 and AlK.
    Type: Grant
    Filed: November 21, 1983
    Date of Patent: August 25, 1987
    Assignee: Roussel Uclaf
    Inventors: Jean Tessier, Jean-Pierre Demoute
  • Patent number: 4681969
    Abstract: A process is described by which the pair of isomers represented by (R)-.alpha.-cyano-4-fluoro-3-phenoxybenzyl (1R,cis)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylate and its enantiomer is converted by base catalyzed epimerization in solution into the insecticidally more useful isomer pair represented by (S)-.alpha.-cyano-4-fluoro-3-phenoxybenzyl (1R,cis)-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane carboxylate and its enantiomer, which may then be caused to crystallize out from the solution.
    Type: Grant
    Filed: August 26, 1985
    Date of Patent: July 21, 1987
    Assignee: Imperial Chemical Industries PLC
    Inventors: John Williams, Michael J. Robson
  • Patent number: 4670464
    Abstract: A process for the relative enrichment of a solution of .alpha.-cyano-4-fluoro-3-phenoxybenzyl 3-(Z-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropane carboxylate with respect to the enantiomeric pair of isomers represented by (S)-.alpha.-cyano-4-fluoro-3-phenoxybenzyl (1R,cis)-3-(Z-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopro pane carboxylate and (R)-.alpha.-cyano-4-fluoro-3-phenoxybenzyl (1S,cis)-3-(Z-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopro pane carboxylate which comprises subjecting a solution comprising the enantiomeric pair of isomers (R)-.alpha.-cyano-4-fluoro-3-phenoxybenzyl (1R,cis)-3-(Z-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopro pane carboxylate and (S)-.alpha.-cyano-4-fluoro-3-phenoxybenzyl (1S,cis)-3-(Z-2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopro pane carboxylate in an organic solvent to the action of a base to effect epimerization.
    Type: Grant
    Filed: June 27, 1985
    Date of Patent: June 2, 1987
    Assignee: Imperial Chemical Industries PLC
    Inventors: Peter Doyle, Alan J. Whittle
  • Patent number: 4668701
    Abstract: A compound of formula I: ##STR1## in which formula: D represents hydrogen or a cyano group;X represents halogen;A represents an alkyl group (typically a C.sub.1 -C.sub.6 alkyl group);n is 0 to 4;RCOO. represents a residue of an acid RCO.sub.2 H, which acid, or an ester-forming derivative of which acid, on reaction with .alpha.-cyano-3-phenoxybenzyl alcohol or an ester-forming derivative thereof, gives rise to an .alpha.-cyano-3-phenoxybenzyl ester having pesticidal properties.
    Type: Grant
    Filed: January 30, 1986
    Date of Patent: May 26, 1987
    Assignee: National Research Development Corporation
    Inventors: Michael Elliott, Norman F. Janes, Richard L. Elliott