Bicyclo Ring System Having The Hetero Ring As One Of The Cyclos Patents (Class 549/462)
  • Patent number: 4647676
    Abstract: A process for the isolation of a dihydroxybenzenemonoether from a reaction mixture containing solvent, ether and unreacted dihydroxybenzene, comprising contacting the reaction mixture with at least one hydrocarbon which is not miscible or only partially miscible with the reaction mixture, the ether selectively entering the hydrocarbon. Advantageously the reaction for the preparation of the monoether is carried out in an alcohol, a ketone, a dipolar aprotic solvent or a polyhydroxyalkyl ether, or a mixture thereof with water, the hydrocarbon used as extracting agent has a boiling point between about 80.degree. and 300.degree. C., and the extraction is carried out in the presence of water whereby there is an increase in the selectivity of the extraction.
    Type: Grant
    Filed: May 23, 1984
    Date of Patent: March 3, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Manfred Lenthe, Udo Allenbach, Gerhard Buttner, Karl-Friedrich Christmann
  • Patent number: 4647677
    Abstract: A process for preparing 2,3-dihydro-7-aminobenzofurans by reaction between 2,3-dihydro-7-halobenzofurans and ammonia in the presence of a copper catalyst, is described. The 2,3-dihydro-7-aminobenzofurans are useful as intermediates for insecticides.
    Type: Grant
    Filed: July 10, 1985
    Date of Patent: March 3, 1987
    Assignee: Mitsubishi Chemical Industries Limited
    Inventors: Mitsuhiko Tamura, Haruo Katsumata, Takemi Nakanome
  • Patent number: 4639536
    Abstract: 2,3-Dihydro-2,2-dimethyl-7-hydroxybenzofuran is prepared by reacting catechol with isobutylene oxide or with a compound having the general formula ##STR1## wherein R is halogen or hydroxyl, and X is halogen, in the presence of a base to form the intermediate 2-(2-hydroxy-2-methylpropoxy) phenol and then thermally dehydrating, rearranging and cyclizing the resulting intermediate phenol in the presence of an acid catalyst to form 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran.
    Type: Grant
    Filed: August 30, 1984
    Date of Patent: January 27, 1987
    Assignee: Union Carbide Corporation
    Inventors: Constance A. Fellows, Wallace Y. Fu
  • Patent number: 4628058
    Abstract: N-(2,3-dihydrobenzofuran-2-yl)-azolylureas of the formula ##STR1## where R is hydrogen or alkyl, X is hydrogen, halogen, nitro, cyano, trifluoromethyl, alkyl, alkoxy, alkylthio, phenyl or phenoxy, m is an integer from 1 to 4, Y is CH or N, R.sup.1 is alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, cycloalkyl or cycloalkylalkyl or an unsubstituted or substituted phenyl or benzyl radical, and R.sup.2 and R.sup.3 are each hydrogen or alkyl, and fungicides which contain these compounds.
    Type: Grant
    Filed: March 19, 1985
    Date of Patent: December 9, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Costin Rentzea, Stefan Karbach, Eberhard Ammermann, Ernst-Heinrich Pommer
  • Patent number: 4617407
    Abstract: Compounds having the formula: ##STR1## are antagonists of leukotrienes of C.sub.4, D.sub.4 and E.sub.4, the slow reacting substance of anaphylaxis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory and cytoprotective agents.
    Type: Grant
    Filed: August 30, 1984
    Date of Patent: October 14, 1986
    Assignee: Merck Frosst Canada, Inc.
    Inventors: Robert N. Young, Joshua Rokach
  • Patent number: 4617314
    Abstract: Benzofuran- and benzopyran-carboxamide derivatives of the formula: ##STR1## wherein l is 1 or 2; X is hydrogen atom, amino group or halogen atom; Y is --S(O).sub.m --R.sup.3 wherein R.sup.3 is lower alkyl group and m is 0, 1 or 2, or ##STR2## wherein R.sup.4 and R.sup.5 are the same or different and are each hydrogen atom or lower alkyl group; R.sup.1 is hydrogen atom, lower alkyl group, arylthiomethyl group, halogenomethyl group or ##STR3## wherein R.sup.6 and R.sup.7 are the same or different and are each hydrogen atom or lower alkyl group or R.sup.6 and R.sup.7 together with the adjacent nitrogen atom form a hetrocycle; R.sup.2 is hydrogen atom or lower alkyl group; and Z is ##STR4## wherein p is 2 or 3, R.sup.8 and R.sup.9 are the same or different and are each lower alkyl group or R.sup.8 and R.sup.9 together with the adjacent nitrogen atom form a heterocycle, or ##STR5## wherein q is 0 or 1, n is 1 or 2, R.sup.
    Type: Grant
    Filed: March 20, 1984
    Date of Patent: October 14, 1986
    Assignee: Yoshitomi Pharmaceutical Industries Ltd.
    Inventors: Tetsuya Tahara, Kiyoharu Hayano, Michihide Setoguchi, Takemi Fukuda
  • Patent number: 4616082
    Abstract: New hydroquinone ether compounds of formula I are described: ##STR1## wherein p is 1 or 2 and Q is 0 or 1, provided that p+q is 1 or 2, R is a residue of formula II ##STR2## and R.sub.o, R.sub.oo, R.sub.1, R.sub.2, R.sub.3, Q, n and k are as defined in the specification,The new compounds are useful e.g. as stabilizers in photographic material.
    Type: Grant
    Filed: June 7, 1985
    Date of Patent: October 7, 1986
    Assignee: Ciba-Geigy AG
    Inventor: Frederick H. Howell
  • Patent number: 4594438
    Abstract: A process for preparing 2,2-dimethyl-2,3-dihydro-7-hydroxybenzofuran, which comprises(a) heating a 2,2-dihalo-6-halo-6-(1-haloisobutyl)cyclohexanone in the presence of a dehydrohalogenation agent, hydroylzing the resulting 2-isobutenyl-6-halophenol in the presence of a copper compound catalyst and an alkali, and cyclizing the resulting 1,2-dihydroxy-3-isobutenylbenzene in the presence of a cyclization catalyst,(b) heating a 2,2-dihalo-6-halo-6-(1-haloisobutyl) cyclohexanone in the presence of a dehydrohalogenation agent, reacting the resulting 2,2-dimethyl-2,3-dihydro-7-halobenzofuran with at least one metal selected from the group consisting of lithium, sodium and magnesium, oxidizing the resulting metal compound, and hydrolyzing the oxidized metal compound, or(c) heating a 2,2-dihalo-6-halo-6-(1-haloisobutyl) cyclohexanone in a carboxylic acid in the presence of a salt of a carboxylic acid.
    Type: Grant
    Filed: October 22, 1984
    Date of Patent: June 10, 1986
    Assignee: Mitsubishi Chemical Industries, Ltd.
    Inventors: Naoshi Imaki, Takemi Nakanome
  • Patent number: 4590271
    Abstract: Compounds of the formula (II) ##STR1## or a salt, N-oxide or acyl derivative thereof, wherein Y is a group ##STR2## which is linked to the pyrimidinylmethyl moiety at the 1 or 7-position and is optionally substituted at the 2, 3, 4 or 6-position or at the 7-position when the linkage to the pyrimidinylmethyl moiety is at the 1-position wherein X is an oxygen or sulphur atom, a group CH.sub.2, a group S(O).sub.n where n=1 or 2, a group NR.sup.1 wherein R.sup.1 is hydrogen C.sub.1-4 alkyl or a group COR.sup.2 where R.sup.2 is hydrogen, C.sub.1-4 alkoxy or amino and the dotted line represents a single or double bond, have antimicrobial activity. Processes for making these compounds, pharmaceutical compositions containing them and the medical use of the compounds are also disclosed.
    Type: Grant
    Filed: April 29, 1983
    Date of Patent: May 20, 1986
    Assignee: Burroughs Wellcome Co.
    Inventors: Susan M. Daluge, Paul M. Skonezny, Barbara Roth, Barbara S. Rauckman
  • Patent number: 4587259
    Abstract: Certain miticidal 2-(2-alkyl-2,3-dihydro-benzofuran-7-yl)-hydrazinecarboxylic acid esters.
    Type: Grant
    Filed: June 29, 1984
    Date of Patent: May 6, 1986
    Assignee: Shell Oil Company
    Inventors: Kurt H. Pilgram, Richard D. Skiles
  • Patent number: 4570008
    Abstract: Described are 1-hydroxymethyl-2-acyl cyclopropane derivatives defined according to the structure: ##STR1## wherein Z represents hydrogen, acyl having the structure: ##STR2## and substituted oxyacyl having the structure: ##STR3## and cyclic condensation products thereof having the structure: ##STR4## wherein R.sub.1, R.sub.2 and R.sub.3 represent C.sub.1 --C.sub.10 alkyl; wherein R.sub.1 ' represents C.sub.1 --C.sub.10 alkylidene and wherein R.sub.4, R.sub.5, R.sub.6 and R.sub.7 represent hydrogen or C.sub.1 --C.sub.3 lower alkyl; processes for preparing same by means of a reaction of a halomethyloxirane or substituted halomethyloxirane with a substituted 1,3-propanedione derivative; and organoleptic uses of such 1-hydroxymethyl-2-acyl cyclopropane derivatives in augmenting or enhancing the aroma or taste of perfume compositions, perfumed articles (e.g.
    Type: Grant
    Filed: October 19, 1984
    Date of Patent: February 11, 1986
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Marie R. Hanna, Theodore J. Tyszkiewicz
  • Patent number: 4565820
    Abstract: Hypoglycemic 5-chromanyl, 2,3-dihydro-5-benzo[b]-furanyl, 5-pyridyl, 5-quinolyl, 5-pyrrolyl, 5-indolyl, 5-thiazolyl, 5-oxazolyl, 5-isothiazolyl and 5-isoxazolyl oxazolidine-2,4-diones and the pharmaceutically-acceptable salts thereof; certain 3-acylated derivatives thereof; a method of treating hyperglycemic animals therewith; and intermediates useful in the preparation of said compounds.
    Type: Grant
    Filed: January 26, 1984
    Date of Patent: January 21, 1986
    Assignee: Pfizer Inc.
    Inventor: Rodney C. Schnur
  • Patent number: 4564691
    Abstract: A process is provided for preparing a substituted 2,3-dihydrobenzofuran of the general formula ##STR1## in which R.sub.a is hydrogen, halogen, alkyl, straight or branched having from 1 to 4 carbon atoms, aryl, alkaryl, --OH, --OR.sub.3, --N(R.sub.d).sub.2, where R.sub.3 and R.sub.d are alkyl, straight or branched having from 1 to 4 carbon atoms; R.sub.b is alkyl, straight or branched, having from 1 to 6 carbon atoms, aryl, alkaryl; and R.sub.c is hydrogen or the same as R.sub.b, by the rearrangement of a 1,1-bis(2-hydroxybenzene) alkyl and/or aryl-ethane, in the presence of catalytic amounts of a mineral acid or organic acid such as phosphoric, sulfuric or p-toluenesulfonic, at elevated temperatures from 180.degree. to 250.degree. C., and withdrawing the resulting products from the reaction mixture as they are formed. The starting 1,1-bis(2-hydroxybenzene) alkyl and/or aryl-ethane compounds may be obtained by the catalyzed reaction of a substituted biphenol with an aldehyde.
    Type: Grant
    Filed: April 19, 1984
    Date of Patent: January 14, 1986
    Assignee: Enichimica Secondaria S.p.A.
    Inventors: Carlo Neri, Villiam Giroldini, Antonio Rinaldi, Mario Traversoni, Mario Clerici
  • Patent number: 4563476
    Abstract: Substituted 5-hydroxy-2,3-dihydrobenzofuran and analogs such as the substituted 6-hydroxy-2,3-dihydrobenzopyrans were prepared from an appropriately substituted (5-hydroxy-2,3-dihydrobenzofuran-6-yl) formaldehyde or analog thereof with an aryl amine followed by reduction. These compounds were found to be potent topical anti-inflammatory agents.
    Type: Grant
    Filed: November 21, 1983
    Date of Patent: January 7, 1986
    Assignee: Merck & Co., Inc.
    Inventors: Michael N. Chang, Milton L. Hammond, Norman P. Jensen, Robert A. Zambias
  • Patent number: 4562266
    Abstract: Process for the preparation of 2,3-dihydro-2,2-dimethyl-7-benzofuranol, comprising the reaction between catechol or 4-tert.butyl catechol and isobutyraldehyde in the presence of catalytic amounts of at least one compound selected from the group consisting of the oxides, hydroxides, alcoholates and carboxylates of metals belonging to the Groups IA, IIA, IIB and VIIB of the Periodic System of the Elements and the subsequent reaction of rearrangement of the products which have been obtained, optionally previously removing one or more low-boiling components, in the presence of a compound having acidic properties, of an organic or a mineral nature. The product is useful in the synthesis of pesticides.
    Type: Grant
    Filed: April 19, 1984
    Date of Patent: December 31, 1985
    Assignee: Enichimica Secondaria, S.p.A.
    Inventors: Carlo Neri, Villiam Giroldini, Mario Traversoni, Guido Guizzi, Emilio Perrotti, Antonio Rinaldi
  • Patent number: 4562267
    Abstract: Variously substituted alkyl 2-(furyl or thienyl)-2-hydroxyacetates and 2-(furyl or thienyl)-2-hydroxyacetamides are useful as intermediates for hypoglycemic oxazolidine-2,4-diones.
    Type: Grant
    Filed: October 14, 1983
    Date of Patent: December 31, 1985
    Assignee: Pfizer Inc.
    Inventor: Rodney C. Schnur
  • Patent number: 4560682
    Abstract: The present invention provides a novel organophosphoric acid ester represented by the following formula, a process for its production and a pesticidal composition containing this ester as an active ingredient: ##STR1## where R.sup.1 is an alkyl group, R.sup.2 is an alkyl group or a thioalkyl group, each of R.sup.3, R.sup.4 and R.sup.5 is a hydrogen atom, a halogen atom, an alkylthio group, a nitro group, a cyano group, an alkyl group, an alkylsulfinyl group, an alkylsulfonyl group or a trifluoromethyl group, and X is an oxygen atom or a sulfur atom.
    Type: Grant
    Filed: December 7, 1984
    Date of Patent: December 24, 1985
    Assignee: Mitsubishi Chemical Industries Ltd.
    Inventors: Ohta Hiroki, Oda Masatsugu, Kato Jun
  • Patent number: 4554283
    Abstract: Certain aphicidal 3-(2-alkyl-2,3-dihydrobenzofuran-7-yl)-5-(R,R.sup.1 -amino)-1,3,4-oxadiazol-2(3H)-ones.
    Type: Grant
    Filed: August 22, 1984
    Date of Patent: November 19, 1985
    Assignee: Shell Oil Company
    Inventors: Kurt H. Pilgram, Richard D. Skiles
  • Patent number: 4550121
    Abstract: Certain miticidal (2-substituted-2,3-dihydro-benzofuran-7-yl)diazenecarboxylic acid esters.
    Type: Grant
    Filed: August 22, 1984
    Date of Patent: October 29, 1985
    Assignee: Shell Oil Company
    Inventors: Kurt H. Pilgram, Richard D. Skiles
  • Patent number: 4549015
    Abstract: New hydroquinone ether compounds of formula I are described: ##STR1## wherein p is 1 or 2 and q is 0 or 1, provided that p+q is 1 or 2, R is a residue of formula II ##STR2## and R.sub.o, R.sub.oo, R.sub.1, R.sub.2, R.sub.3, Q, n and k are as defined in the specification.The new compounds are useful e.g. as stabilizers in photographic material.
    Type: Grant
    Filed: June 14, 1983
    Date of Patent: October 22, 1985
    Assignee: Ciba-Geigy AG
    Inventor: Frederick H. Howell
  • Patent number: 4548948
    Abstract: Compounds of formula (I): ##STR1## wherein: Ar is phenyl optionally substituted in the o-, m- or p-position by C.sub.1-4 alkyl, C.sub.1-4 alkoxy, trifluoromethyl, bromo, chloro or fluoro,pyrryl optionally N-substituted by C.sub.1-4 alkyl,2-furyl or 2-thienyl either optionally substituted in the 3-, 4- or 5-position by methyl, chloro or bromo, or3-furyl or 3-thienyl;X is oxygen, sulphur, sulphoxide or sulphone, Y is methylene, R.sub.1 and R.sub.3 are hydrogen or C.sub.1-4 alkyl, and R.sub.2 is hydrogen, C.sub.1-4 alkyl, fluoro, chloro or bromo, or X is methylene, Y is oxygen, R.sub.1 and R.sub.3 are both hydrogen, and R.sub.2 is hydrogen, fluoro, chloro or bromo; andR.sub.4 is hydrogen or C.sub.1-4 alkyl, or a salt thereof, have analgesic and/or anti-inflammatory activity.
    Type: Grant
    Filed: February 17, 1984
    Date of Patent: October 22, 1985
    Assignee: Beecham Group p.l.c.
    Inventors: Robert W. Ward, Stephen A. Smith, Roger E. Markwell
  • Patent number: 4542229
    Abstract: A process is described for preparing 2,3-dihydro-2,2-dimethylbenzofuran-7-ol (I), which is a useful intermediary in the preparation of Carbofuran, a known multi-functional insecticide.The process consists essentially of reacting the pyrocatechol and a methallylhalide in an inert organic solvent in the presence of a solid inorganic base and a suitable catalyst, to obtain o.methallyloxyphenol with high conversion and high selectivity; this product is thermally transposed to o.methallylpyrocatechol, which is finally cyclized to the product (I) by heterogeneous catalysis in the presence of solid acid catalysts.All stages of the process can be carried out in a single reaction medium, without separating intermediate products.
    Type: Grant
    Filed: April 11, 1983
    Date of Patent: September 17, 1985
    Assignee: Brichima S.p.A.
    Inventors: Paolo Maggioni, Francesco Minisci, Mariano Correale
  • Patent number: 4540800
    Abstract: A process for the preparation of a 2,3-dihydro-2-methyl-2,3-dialkyl-7-oxybenzofuran having the formula (I): ##STR1## in which R and R' are the same or different and each represents a lower alkyl group or hydrogen atom, which comprises reacting catechol with an aldehyde having the formula (II):(RCH.sub.2)(R')CHCHO (II)or an alcohol having the formula (III):RCH.dbd.C(R')--CH.sub.2 OH (III)in a gaseous phase in the presence of a solid acid catalyst. The products are useful as intermediates in the preparation of insecticides.
    Type: Grant
    Filed: April 12, 1983
    Date of Patent: September 10, 1985
    Assignee: Ube Industries, Ltd.
    Inventors: Yukio Inaba, Taisei Igarashi, Susumu Tahara, Takashi Miyatake
  • Patent number: 4537903
    Abstract: Substituted cinnamyl-2,3-dihydrobenzofurans and analogs were prepared from the nucleophilic substitution of a cinnamylhalide with a 2,3-dihydrobenzofuran anion or an analog thereof. These compounds were found to be potent topical anti-inflammatory agents.
    Type: Grant
    Filed: October 12, 1983
    Date of Patent: August 27, 1985
    Assignee: Merck & Co., Inc.
    Inventors: Michael N. Chang, Milton L. Hammond, Norman P. Jensen, John McDonald, Robert A. Zambias
  • Patent number: 4536330
    Abstract: Described are 1-hydroxymethyl-2-acyl cyclopropane derivatives defined according to the structure: ##STR1## wherein Z represents hydrogen, acyl having the structure: ##STR2## and substituted oxyacyl having the structure: ##STR3## and cyclic condensation products thereof having the structure: ##STR4## wherein R.sub.1, R.sub.2 and R.sub.3 represent C.sub.1 -C.sub.10 alkyl; wherein R.sub.1 ' represents C.sub.1 -C.sub.10 alkylidene and wherein R.sub.4, R.sub.5, R.sub.6 and R.sub.7 represent hydrogen or C.sub.1 -C.sub.3 lower alkyl; processes for preparing same by means of a reaction of a halomethyloxirane or substituted halomethyloxirane with a substituted 1,3-propanedione derivative; and organoleptic uses of such 1-hydroxymethyl-2-acyl cyclopropane derivatives in augmenting or enhancing the aroma or taste of perfume compositions, perfumed articles (e.g.
    Type: Grant
    Filed: March 14, 1984
    Date of Patent: August 20, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Marie R. Hanna, Theodore J. Tyszkiewicz
  • Patent number: 4521539
    Abstract: Tetrahydrofuranyl substituted ethers are provided having the structural formula ##STR1## wherein A is (CH.sub.2).sub.2, CH.dbd.CH or a single bond, m is 1 to 5, B is a single bond or CH.dbd.CH, n is 1 to 4, X is O or ##STR2## wherein n' is 0, 1 or 2, R is H, lower alkyl or alkali metal and R.sup.1 is lower alkyl, arylalkyl, aryl, cycloalkyl, cycloalkylalkyl or lower alkenyl and including all stereoisomers thereof.The compounds are cardiovascular agents useful, for example, in the treatment of thrombolytic disease and as antiinflammatory agents and analgesics.
    Type: Grant
    Filed: May 10, 1984
    Date of Patent: June 4, 1985
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Jagabandhu Das
  • Patent number: 4511391
    Abstract: The invention concerns novel compounds of the formula I ##STR1## wherein: X is selected from halogen, nitro, cyano, alkyl, substituted alkyl, alkenyl, alkynyl, hydroxy, alkoxy, substituted alkoxy, alkenyloxy, alkynyloxy, alkanoyloxy, alkoxycarbonyl, alkylthio, alkylsulfinyl, alkylsulfonyl, sulfamoyl, substituted sulfamoyl, benzyloxy, substituted benzyloxy, amino, substituted amino, and the groups formyl and alkanoyl and the oxime, imine and Schiff base derivatives thereof;Y and Z are independently selected from methylene, oxygen and sulfur provided that at least one of Y and Z is selected from oxygen and sulfur;R.sup.1 is selected from hydrogen, alkyl, alkenyl alkynyl, substituted alkyl, acyl, alkylsulfonyl, benzenesulfonyl, substituted benzenesulfonyl, and an inorganic or organic cation;R.sup.2 is selected from alkyl, alkenyl, alkynyl, substituted alkyl, haloalkenyl and haloalkynyl;R.sup.3 is selected from alkyl, fluoroalkyl, alkenyl, alkynyl and phenyl;R.sup.4 is selected from hydrogen, halogen, cyano, C.
    Type: Grant
    Filed: May 24, 1983
    Date of Patent: April 16, 1985
    Assignee: ICI Australia Limited
    Inventors: Alexander Serban, Keith G. Watson, Graham J. Bird, Graeme J. Farquharson
  • Patent number: 4496748
    Abstract: The invention relates to 13-oxabicyclo[10.3.0]pentadecanes alkylated in the 14-position and, optionally, in the 15-position and to 13-oxabicyclo[10.4.0]hexadecanes alkylated in the 14-position and, optionally, in the 16-position. The compounds according to the invention may be used as odorizers.
    Type: Grant
    Filed: August 4, 1982
    Date of Patent: January 29, 1985
    Assignee: Consortium Fur Elektrochemische Industrie GMBH
    Inventor: Helmut Gebauer
  • Patent number: 4495353
    Abstract: The invention relates to a process for substituting for a halogen atom attached to the nuclear carbon atom of an aromatic ring, a substituent of the formula -O-R wherein R represents alkyl, alkenyl, alkynyl or benzyl, which process comprises reacting the halogen-substituted aromatic compound with an alcoholate of the formula M.sup.n+ [O--R].sub.n.sup..crclbar. wherein M is an alkali metal atom or alkaline earth metal atom, n is the valency of M, and R is as defined above, in the presence of an active catalyst mixture comprising (i) a formic acid ester of an organic alcohol having the formula R.sup.2 --O--CO--H wherein R.sup.2 is as defined for R above; and (ii) a cuprous salt; in a liquid medium which is a solvent for the catalyst mixture and in which the halogen-substituted aromatic compound is at least partially soluble, under substantially anhydrous conditions and a non-oxidizing atmosphere. The invention further relates to a catalyst used in the above process.
    Type: Grant
    Filed: June 13, 1983
    Date of Patent: January 22, 1985
    Assignee: Sterling Drug Inc.
    Inventor: Robert J. Bryant
  • Patent number: 4480118
    Abstract: This invention relates to a novel carboxylic acid ester represented by the following general formula (I) and an insecticidal and/or acaricidal composition containing the same as an active ingredient: ##STR1## wherein X is represented by the formula, ##STR2## and further also relates to a carboxylic acid or a reactive derivative thereof represented by the general formula, ##STR3## wherein R.sub.16 is hydroxy group, chlorine or bromine atom, or a C.sub.1-2 alkoxy group, W is oxygen atom or --CH.sub.2 -- group, k is an integer of 0 or 1, E is hydrogen, chlorine, fluorine or bromine atom, and n is an integer of 1 to 4.
    Type: Grant
    Filed: December 30, 1981
    Date of Patent: October 30, 1984
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazunori Tsushima, Noritada Matsuo, Makoto Hatakoshi, Toshihiko Yano, Nobushige Itaya
  • Patent number: 4469879
    Abstract: Trichloropolyfluoro-bicyclo ethers are novel compounds, useful as a solvent or thermal medium for various pharmaceutical chemicals. They are produced by the reaction of perfluoro-bicyclo ether with anhydrous aluminum chloride.
    Type: Grant
    Filed: January 14, 1983
    Date of Patent: September 4, 1984
    Assignees: Agency of Industrial Science and Technology, Ministry of International Trade & Industry
    Inventors: Takashi Abe, Hajime Baba, Eiji Hayashi, Shunji Nagase
  • Patent number: 4467104
    Abstract: Esters of 2-(2-chlorocarbonyl)-2-(2,3-dihydro-2-alkylbenzofuran-7-yl)hydrazinecarbox ylic acid, useful as pesticides and/or as percursors to pesticides.
    Type: Grant
    Filed: August 2, 1982
    Date of Patent: August 21, 1984
    Assignee: Shell Oil Company
    Inventors: Kurt H. Pilgram, Richard D. Skiles
  • Patent number: 4463184
    Abstract: A novel process is provided for the preparation of carbofuran and certain intermediate products. 1,2-Cyclohexanedione is alkylated with a beta-methallyl compound and the resulting product subjected to a Claisen rearrangement/aromatization to provide the carbofuran phenol. Reaction of the phenol with methyl isocyanate converts the phenol to the desired carbofuran.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: July 31, 1984
    Assignee: Union Carbide Corporation
    Inventor: David A. Hunt
  • Patent number: 4451662
    Abstract: A process for preparing 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran which comprises subjecting o-methallyloxyphenol to a rearrangement and cyclization reactions in the presence of, as a catalyst, aluminum halide and N-substituted aniline derivative, or a complex of both these compounds.
    Type: Grant
    Filed: June 11, 1982
    Date of Patent: May 29, 1984
    Assignee: Otsuka Kagaku Yakuhin Kabushiki Kaisha
    Inventors: Tsukasa Maekawa, Takeshi Gondo
  • Patent number: 4435422
    Abstract: Described are compounds of the formula ##STR1## wherein R.sub.1 and R.sub.2 independently of one another denote hydrogen or loweralkyl; A is CO, CH.sub.2, O, S, SO or CHOH; X is hydrogen, halo, loweralkyl, or --CH.sub.2 NR.sub.1 R.sub.2 wherein R.sub.1 and R.sub.2 are as defined above; W is COOR wherein R is hydrogen or alkyl of 1-10 carbon atoms, CH.sub.2 OH, CONR.sub.1 R.sub.2 or CH.sub.2 NR.sub.1 R.sub.2 wherein R.sub.1 and R.sub.2 are as defined above; Z.sub.1 and Z.sub.2 independently of one another denote hydrogen, halo or loweralkyl; and pharmaceutically acceptable salts thereof.The compounds are effective as diuretic agents.
    Type: Grant
    Filed: September 15, 1982
    Date of Patent: March 6, 1984
    Assignee: Abbott Laboratories
    Inventors: Cheuk M. Lee, James A. Parks
  • Patent number: 4431668
    Abstract: Cyclopropane carboxylic acid ester derivatives and optical and geometrical isomers thereof expressed by the general formula: ##STR1## wherein R.sub.1 represents hydrogen atom or methyl group, R.sub.2 represents alkyl group, alkenyl group, haloalkyl group, haloalkenyl group having 1-6 carbon atoms and a group selected from the groups of the general formulae (II), (III) and (IV): ##STR2## in which n is an integer of 2-5, R.sub.4 represents methyl group, chlorine atom or methoxy group, and R.sub.3 represents a group selected from the groups of the general formulae (V), (VI), (VII), (VIII), (IX) and (X): ##STR3## in which X represents oxygen atom or vinylene group, R.sub.5 represents allyl group, propargyl group, benzyl group, phenoxy group or 2,2-dichlorovinyloxy group, R.sub.6 represents hydrogen atom, methyl group or halogen atom, R.sub.7 represents hydrogen atom, cyano group, ethynyl group or trifluoromethyl group and m is an integer of 1-2, R.sub.
    Type: Grant
    Filed: November 14, 1978
    Date of Patent: February 14, 1984
    Assignee: Dainippon Jochugiku Kabushiki Kaisha
    Inventors: Yoshio Katsuda, Yoshihiro Minamite
  • Patent number: 4430341
    Abstract: Water soluble quaternary ammonium salt compounds exhibit outstanding insecticidal and miticidal activity coupled with reduced mammalian toxicity and acceptable phytotoxicity.
    Type: Grant
    Filed: August 24, 1977
    Date of Patent: February 7, 1984
    Assignee: Union Carbide Corporation
    Inventor: Barbara W. Kaplan
  • Patent number: 4426385
    Abstract: Novel bicyclooxyphenyl ureas, such as 1-(bicyclooxyphenyl)-benzoyl ureas, are provided which exhibit pesticidal activity. The compositions are conveniently prepared by reacting an isocyanate with either an amide or a bicyclooxyaniline.
    Type: Grant
    Filed: September 28, 1981
    Date of Patent: January 17, 1984
    Assignee: Union Carbide Corporation
    Inventor: Paul A. Cain
  • Patent number: 4380654
    Abstract: A process for preparing 2,3-dihydro-2,2-dimethyl-7-hydroxybenzofuran in which 2-methallyloxyphenol is heated to a temperature in the range of 150.degree. C. to 250.degree. C. in the presence of a solvent and a Lewis acid catalyst under an autogenous pressure of 20 to 60 psig is disclosed and exemplified.
    Type: Grant
    Filed: February 18, 1982
    Date of Patent: April 19, 1983
    Assignee: FMC Corporation
    Inventors: Borivoj R. Franko-Filipasic, Philip B. Hobson
  • Patent number: 4360468
    Abstract: This invention relates to the preparation of 13-oxabicyclo[10.3.0]pentadecane. More specifically, this invention relates to a process for preparing 13-oxabicyclo[10.3.0]pentadecane which comprises the steps of:(a) reacting cyclododecanone with elemental bromine in an organic solvent to form .alpha.-bromocyclododecanone;(b) reacting .alpha.
    Type: Grant
    Filed: September 29, 1981
    Date of Patent: November 23, 1982
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Horst Upadek, Klaus Bruns
  • Patent number: 4347192
    Abstract: Derivatives of .alpha.,.beta.-unsaturated ketones having anticonvulsant activity and methods of their preparation from heterocyclic phosphonium salts and acyclic phosphoranes are disclosed.
    Type: Grant
    Filed: July 24, 1980
    Date of Patent: August 31, 1982
    Assignee: G. D. Searle & Co.
    Inventor: Richard A. Mueller
  • Patent number: 4341792
    Abstract: Heterobicyclic glyoxylic acids, L- and DL-heterobicyclic glycines and their derivatives of the formulae ##STR1## and pharmaceutically acceptable cationic and acid addition salts thereof, wherein R is OR.sup.2 or NHR.sup.3 ;R.sup.2 is hydrogen or alkyl having from one to four carbon atoms;R.sup.3 is hydrogen, alkyl having from one to four carbon atoms, alkoxyalkyl having from one to four carbon atoms in each of the alkyl groups or R.sup.4 R.sup.5 C.sub.6 H.sub.3 CH.sub.2 -- where R.sup.4 and R.sup.5 are H, OH, F, Cl, Br, I, or alkyl or alkoxy having from one to four carbon atomsR.sup.1 is hydrogen, alkyl having from one to four carbon atoms or R.sup.4 R.sup.5 C.sub.6 H.sub.3 --; X is oxygen or sulfur; n is 0 or 1 and the broken line represents an optionally present double bond; useful in treatment of diseases and conditions which are characterized by reduced blood flow, reduced oxygen availability or reduced carbohydrate metabolism in the cardiovascular system.
    Type: Grant
    Filed: July 6, 1981
    Date of Patent: July 27, 1982
    Assignee: Pfizer Inc.
    Inventors: Ian T. Barnish, Peter E. Cross
  • Patent number: 4336195
    Abstract: Cyclic ethers such as tetrahydrofuran, dioxane, and tetrahydropyran are produced by reacting dimethyl carbonate with an appropriate primary dihalide in the presence of a quaternary ammonium or phosphonium salt.
    Type: Grant
    Filed: February 2, 1981
    Date of Patent: June 22, 1982
    Assignee: The Dow Chemical Company
    Inventor: James M. Renga