Title:
COCKROACH-AGGREGATING ATTRACTING SUBSTANCE, COCKROACH-AGGREGATING ATTRACTANT, AND COCKROACH EXTERMINATING AGENT
Document Type and Number:
WIPO Patent Application WO/2015/098681
Kind Code:
A1
Abstract:
The problem of providing a cockroach-aggregating pheromone and a cockroach-aggregating attractant or a cockroach exterminating agent which includes the cockroach-aggregating pheromone is solved by a compound represented by any of general formulas (I) through (III) or a salt thereof, which is a cockroach-aggregating attracting substance.
Inventors:
NISHIMURA YUKIHIRO (JP)
SAKUMA MASAYUKI (JP)
UENO TAMIO (JP)
MATSUO NORITADA (JP)
KOUTANI YASUYUKI (JP)
SAKUMA MASAYUKI (JP)
UENO TAMIO (JP)
MATSUO NORITADA (JP)
KOUTANI YASUYUKI (JP)
Application Number:
PCT/JP2014/083519
Publication Date:
July 02, 2015
Filing Date:
December 18, 2014
Export Citation:
Assignee:
UNIV KYOTO (JP)
DAINIPPON JOCHUGIKU KK (JP)
DAINIPPON JOCHUGIKU KK (JP)
International Classes:
C07C49/747; A01N43/12; A01N43/16; A01N63/00; A01P7/04; A01P19/00; C07D307/88; C07D311/76; C07D311/78
Domestic Patent References:
| WO2011051225A1 | 2011-05-05 | |||
| WO2012166617A2 | 2012-12-06 |
Foreign References:
| JPH04504265A | 1992-07-30 | |||
| CN103408528A | 2013-11-27 | |||
| JPS6169747A | 1986-04-10 |
Other References:
BESTMANN, HANS JUERGEN ET AL.: "Pheromones. 86. 3,4-Dihydroisocoumarins: a new class of tracking pheromones in ants", ANGEWANDTE CHEMIE, vol. 104, no. 6, 1992, pages 757 - 8
LANGER, PETER ET AL.: "Efficient synthesis of biaryl lactones by domino retro-Michael-aldol- lactonization reactions", CHEMICAL COMMUNICATIONS, 2002, pages 168 - 169
MATSUI, MASANAO ET AL.: "Synthesis of isochroman-1,3-diones. A new synthesis of (+-) sclerin", AGRICULTURAL AND BIOLOGICAL CHEMISTRY, vol. 32, no. 4, 1968, pages 492 - 5
TOKOROYAMA, TAKASHI ET AL.: "Syntheses of sclerin analogs", NIPPON KAGAKU KAISHI, 1974, pages 136 - 46
LANGER, PETER ET AL.: "Efficient synthesis of benzopyrano[2,3-b]pyridines by sequential reactions of 1,3-bis-silyl enol ethers with 3- cyanobenzopyrylium triflates", TETRAHEDRON LETTERS, vol. 44, no. 27, 2003, pages 5133 - 5135
HASHMI, A. STEPHEN K. ET AL.: "Gold catalysis: five new bonds by a domino hydroarylation/ cycloisomerization", TETRAHEDRON, vol. 61, no. 26, 2005, pages 6231 - 6236
PUNDT, THOMAS ET AL.: "One-pot synthesis of aryl fluorides by [3+3] cyclization of 1,3-bis(silyl enol ethers) with 2-fluoro-3-silyloxy-2-en-1- ones", TETRAHEDRON LETTERS, vol. 48, no. 15, 2007, pages 2745 - 2747
BOULANGE, AGATHE ET AL.: "Diastereoselective IBX Oxidative Dearomatization of Phenols by Remote Induction: Towards the Epicocconone Core Framework", CHEMISTRY - A EUROPEAN JOURNAL, vol. 17, no. 37, 2011, pages 10241 - 10245
ZHOU, ZHONG-YU ET AL.: "Two new cleistanthane diterpenes and a new isocoumarine from cultures of the basidiomycete Albatrellus confluens", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 57, no. 9, 2009, pages 975 - 978
DATABASE REGISTRY 16 November 1984 (1984-11-16), accession no. 2710-10-9
SOMMART, UBONTA ET AL.: "Modiolin and phthalide derivatives from the endophytic fungus Microsphaeropsis arundinis PSU-G18", TETRAHEDRON, vol. 68, no. 48, 2012, pages 10005 - 10010
HUSSAIN, IBRAR ET AL.: "Synthesis of Dibenzo [b,d]pyran-6-ones Based on [3 + 3] Cyclizations of 1,3-Bis(silyl enol ethers) with 3-Silyloxy- 2-en-1-ones", JOURNAL OF ORGANIC CHEMISTRY, vol. 72, no. 16, 2007, pages 6255 - 6258
KURAMATA, MASATO ET AL.: "Citrinolactones A, B and C, and sclerotinin C, plant growth regulators from Penicillium citrinum, Bioscience", BIOTECHNOLOGY, AND BIOCHEMISTRY, vol. 71, no. 2, 2007, pages 499 - 503
TAKAHASHI, KOSAKU ET AL.: "Novel antifungal compounds produced by sterile dark, an unidentified wheat rhizosphere fungus, Bioscience", BIOTECHNOLOGY, AND BIOCHEMISTRY, vol. 69, no. 5, 2005, pages 1018 - 1020
SHAN, R. ET AL.: "Naphthalenone and phthalide metabolites from Lachnum papyraceum", JOURNAL OF NATURAL PRODUCTS, vol. 60, no. 8, 1997, pages 804 - 805
HOLLER, ULRICH ET AL.: "Fungi from marine sponges: Diversity, biological activity and secondary metabolites", MYCOLOGICAL RESEARCH, vol. 104, no. 11, 2000, pages 1354 - 1365
FEIGE, G. B. ET AL.: "Identification of lichen substances by a standardized high-performance liquid chromatographic method", JOURNAL OF CHROMATOGRAPHY, vol. 646, no. 2, 1993, pages 417 - 27
KUBOTA, TAKASHI ET AL.: "Structures of sclerin and sclerolide, metabolites of Sclerotinia libertiana", TETRAHEDRON LETTERS, 1966, pages 5205 - 10
ACHENBACH, HANS ET AL.: "Metabolites from microorganisms. XXX.", PHTHALIDES AND CHROMANOLS FROM ASPERGILLUS DURICAULIS, LIEBIGS ANNALEN DER CHEMIE, 1985, pages 1596 - 628
MUEHLENFELD, ANDREAS ET AL.: "Metabolites of microorganisms. XXXV. Asperdurin, a novel antimycotic phthalide from Aspergillus duricaulis", ARCHIV DER PHARMAZIE, vol. 321, no. 11, 1988, pages 803 - 5
ULLAH, IHSAN ET AL.
JUETTEN, PETER ET AL.: "Thiosemicarbazones of Formyl Benzoic Acids as Novel Potent Inhibitors of Estrone Sulfatase", JOURNAL OF MEDICINAL CHEMISTRY, vol. 50, no. 15, 2007, pages 3661 - 3666
NAGAOKA, HIROTO ET AL.: "A synthesis of the aromatic segment of rifamycin S", TETRAHEDRON LETTERS, vol. 22, no. 10, 1981, pages 899 - 902
TAKATORI, MASAYUKI ET AL.: "Trimorphism of 7- hydroxy-3-(p-methoxyphenyl)-4,6-dimethyl-1- indanone", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, vol. 48, no. 11, 1975, pages 3411 - 12
NAITO, SHINSUKE ET AL.: "Two new phenolic reductones from Aspergillus terreus", TETRAHEDRON LETTERS, 1969, pages 4675 - 8
MOMOSE, TSUTOMU ET AL.: "Tetralin derivatives. I. Bacteriostatic activity in vitro", PHARMACEUTICAL BULLETIN, vol. 2, 1954, pages 11 9 - 22
BARBER, JILL ET AL.: "The total synthesis of some deuterium labeled pentaketide derivatives of orsellinic acid", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1: ORGANIC AND BIO-ORGANIC CHEMISTRY, 1981, pages 1685 - 9
BRUCE, J. MALCOLM ET AL.: "Benzoquinones and related compounds. Part 2. Preferred conformations of some acyl-1,4-benzoquinones in solution", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 2: PHYSICAL ORGANIC CHEMISTRY, 1980, pages 860 - 6
SAEED, AAMER ET AL.: "Synthesis of 3,4-dihydro- 8-hydroxy-6-methoxy-7-methylisocoumarin and (±)-6,8-dimethoxy-1,7-dimethylisochroman", JOURNAL OF THE CHEMICAL SOCIETY OF PAKISTAN, vol. 15, no. 3, 1993, pages 212 - 15
GAINSFORD, GRAEME J. ET AL.: "Antifungal compounds isolated from New Zealand flax: 7-hydroxy-5- methoxy-6-methylphthalide and 4- methoxycarbonyl-beta-orcinol", ACTA CRYSTALLOGRAPHICA, SECTION C: CRYSTAL STRUCTURE COMMUNICATIONS, vol. C51, no. 4, 1995, pages 709 - 12
DUNCANSON, L. A. ET AL.: "Gladiolic acid. III. Structure of norisogladiolic acid, dihydrogladiolic acid, and cyclopolic acid", JOURNAL OF THE CHEMICAL SOCIETY, 1953, pages 3637 - 45
ISAEV, I. S. ET AL.: "Transformations of pentamethylbenzoic acid and its derivatives during nitration", ZHURNAL ORGANICHESKOI KHIMII, vol. 7, no. 11, 1971, pages 2321 - 6
MALI, RAGHAO S. ET AL.: "Novel AlCl3 catalyzed syntheses of naturally occurring (±) 8-hydroxy- 3-methyl-3,4-dihydroisocoumarins", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS, 1992, pages 883 - 4
LUO, SHI-LIN ET AL.: "Isocoumarins from American cockroach (Periplaneta american a) and their cytotoxic activities", FITOTERAPIA, vol. 95, 13 March 2014 (2014-03-13), pages 115 - 120
LANGER, PETER ET AL.: "Efficient synthesis of biaryl lactones by domino retro-Michael-aldol- lactonization reactions", CHEMICAL COMMUNICATIONS, 2002, pages 168 - 169
MATSUI, MASANAO ET AL.: "Synthesis of isochroman-1,3-diones. A new synthesis of (+-) sclerin", AGRICULTURAL AND BIOLOGICAL CHEMISTRY, vol. 32, no. 4, 1968, pages 492 - 5
TOKOROYAMA, TAKASHI ET AL.: "Syntheses of sclerin analogs", NIPPON KAGAKU KAISHI, 1974, pages 136 - 46
LANGER, PETER ET AL.: "Efficient synthesis of benzopyrano[2,3-b]pyridines by sequential reactions of 1,3-bis-silyl enol ethers with 3- cyanobenzopyrylium triflates", TETRAHEDRON LETTERS, vol. 44, no. 27, 2003, pages 5133 - 5135
HASHMI, A. STEPHEN K. ET AL.: "Gold catalysis: five new bonds by a domino hydroarylation/ cycloisomerization", TETRAHEDRON, vol. 61, no. 26, 2005, pages 6231 - 6236
PUNDT, THOMAS ET AL.: "One-pot synthesis of aryl fluorides by [3+3] cyclization of 1,3-bis(silyl enol ethers) with 2-fluoro-3-silyloxy-2-en-1- ones", TETRAHEDRON LETTERS, vol. 48, no. 15, 2007, pages 2745 - 2747
BOULANGE, AGATHE ET AL.: "Diastereoselective IBX Oxidative Dearomatization of Phenols by Remote Induction: Towards the Epicocconone Core Framework", CHEMISTRY - A EUROPEAN JOURNAL, vol. 17, no. 37, 2011, pages 10241 - 10245
ZHOU, ZHONG-YU ET AL.: "Two new cleistanthane diterpenes and a new isocoumarine from cultures of the basidiomycete Albatrellus confluens", CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 57, no. 9, 2009, pages 975 - 978
DATABASE REGISTRY 16 November 1984 (1984-11-16), accession no. 2710-10-9
SOMMART, UBONTA ET AL.: "Modiolin and phthalide derivatives from the endophytic fungus Microsphaeropsis arundinis PSU-G18", TETRAHEDRON, vol. 68, no. 48, 2012, pages 10005 - 10010
HUSSAIN, IBRAR ET AL.: "Synthesis of Dibenzo [b,d]pyran-6-ones Based on [3 + 3] Cyclizations of 1,3-Bis(silyl enol ethers) with 3-Silyloxy- 2-en-1-ones", JOURNAL OF ORGANIC CHEMISTRY, vol. 72, no. 16, 2007, pages 6255 - 6258
KURAMATA, MASATO ET AL.: "Citrinolactones A, B and C, and sclerotinin C, plant growth regulators from Penicillium citrinum, Bioscience", BIOTECHNOLOGY, AND BIOCHEMISTRY, vol. 71, no. 2, 2007, pages 499 - 503
TAKAHASHI, KOSAKU ET AL.: "Novel antifungal compounds produced by sterile dark, an unidentified wheat rhizosphere fungus, Bioscience", BIOTECHNOLOGY, AND BIOCHEMISTRY, vol. 69, no. 5, 2005, pages 1018 - 1020
SHAN, R. ET AL.: "Naphthalenone and phthalide metabolites from Lachnum papyraceum", JOURNAL OF NATURAL PRODUCTS, vol. 60, no. 8, 1997, pages 804 - 805
HOLLER, ULRICH ET AL.: "Fungi from marine sponges: Diversity, biological activity and secondary metabolites", MYCOLOGICAL RESEARCH, vol. 104, no. 11, 2000, pages 1354 - 1365
FEIGE, G. B. ET AL.: "Identification of lichen substances by a standardized high-performance liquid chromatographic method", JOURNAL OF CHROMATOGRAPHY, vol. 646, no. 2, 1993, pages 417 - 27
KUBOTA, TAKASHI ET AL.: "Structures of sclerin and sclerolide, metabolites of Sclerotinia libertiana", TETRAHEDRON LETTERS, 1966, pages 5205 - 10
ACHENBACH, HANS ET AL.: "Metabolites from microorganisms. XXX.", PHTHALIDES AND CHROMANOLS FROM ASPERGILLUS DURICAULIS, LIEBIGS ANNALEN DER CHEMIE, 1985, pages 1596 - 628
MUEHLENFELD, ANDREAS ET AL.: "Metabolites of microorganisms. XXXV. Asperdurin, a novel antimycotic phthalide from Aspergillus duricaulis", ARCHIV DER PHARMAZIE, vol. 321, no. 11, 1988, pages 803 - 5
ULLAH, IHSAN ET AL.
JUETTEN, PETER ET AL.: "Thiosemicarbazones of Formyl Benzoic Acids as Novel Potent Inhibitors of Estrone Sulfatase", JOURNAL OF MEDICINAL CHEMISTRY, vol. 50, no. 15, 2007, pages 3661 - 3666
NAGAOKA, HIROTO ET AL.: "A synthesis of the aromatic segment of rifamycin S", TETRAHEDRON LETTERS, vol. 22, no. 10, 1981, pages 899 - 902
TAKATORI, MASAYUKI ET AL.: "Trimorphism of 7- hydroxy-3-(p-methoxyphenyl)-4,6-dimethyl-1- indanone", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, vol. 48, no. 11, 1975, pages 3411 - 12
NAITO, SHINSUKE ET AL.: "Two new phenolic reductones from Aspergillus terreus", TETRAHEDRON LETTERS, 1969, pages 4675 - 8
MOMOSE, TSUTOMU ET AL.: "Tetralin derivatives. I. Bacteriostatic activity in vitro", PHARMACEUTICAL BULLETIN, vol. 2, 1954, pages 11 9 - 22
BARBER, JILL ET AL.: "The total synthesis of some deuterium labeled pentaketide derivatives of orsellinic acid", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1: ORGANIC AND BIO-ORGANIC CHEMISTRY, 1981, pages 1685 - 9
BRUCE, J. MALCOLM ET AL.: "Benzoquinones and related compounds. Part 2. Preferred conformations of some acyl-1,4-benzoquinones in solution", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 2: PHYSICAL ORGANIC CHEMISTRY, 1980, pages 860 - 6
SAEED, AAMER ET AL.: "Synthesis of 3,4-dihydro- 8-hydroxy-6-methoxy-7-methylisocoumarin and (±)-6,8-dimethoxy-1,7-dimethylisochroman", JOURNAL OF THE CHEMICAL SOCIETY OF PAKISTAN, vol. 15, no. 3, 1993, pages 212 - 15
GAINSFORD, GRAEME J. ET AL.: "Antifungal compounds isolated from New Zealand flax: 7-hydroxy-5- methoxy-6-methylphthalide and 4- methoxycarbonyl-beta-orcinol", ACTA CRYSTALLOGRAPHICA, SECTION C: CRYSTAL STRUCTURE COMMUNICATIONS, vol. C51, no. 4, 1995, pages 709 - 12
DUNCANSON, L. A. ET AL.: "Gladiolic acid. III. Structure of norisogladiolic acid, dihydrogladiolic acid, and cyclopolic acid", JOURNAL OF THE CHEMICAL SOCIETY, 1953, pages 3637 - 45
ISAEV, I. S. ET AL.: "Transformations of pentamethylbenzoic acid and its derivatives during nitration", ZHURNAL ORGANICHESKOI KHIMII, vol. 7, no. 11, 1971, pages 2321 - 6
MALI, RAGHAO S. ET AL.: "Novel AlCl3 catalyzed syntheses of naturally occurring (±) 8-hydroxy- 3-methyl-3,4-dihydroisocoumarins", JOURNAL OF THE CHEMICAL SOCIETY, CHEMICAL COMMUNICATIONS, 1992, pages 883 - 4
LUO, SHI-LIN ET AL.: "Isocoumarins from American cockroach (Periplaneta american a) and their cytotoxic activities", FITOTERAPIA, vol. 95, 13 March 2014 (2014-03-13), pages 115 - 120
Attorney, Agent or Firm:
IWATANI, Ryo (JP)
Tatsu Iwatani (JP)
Tatsu Iwatani (JP)
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