Development of catalytic carbon-carbon-bond formation reactions and their application to analysis of pesticide residues

• Project/Area Number: 20550137
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Environmental chemistry
• Research Institution: Toyohashi University of Technology
• Principal Investigator: IWASA Seiji Toyohashi University of Technology, 大学院・工学研究科, 准教授 (30303712)
• Project Period (FY): 2008 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000); Fiscal Year 2010: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000); Fiscal Year 2009: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000); Fiscal Year 2008: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
• Keywords: ハプテン / 免疫化学測定法 / 抗原抗体反応 / 残留農薬触媒反応 / ELISA / イムノアッセイ / エマメクチン / アゾキシストロビン / 触媒反応 / 残留農薬 / ELISA法 / リンカー / センサー / 抗体

Research Abstract

We developed a novel catalyst for carbon-carbon bond formation and successfully applied it for analysis of insecticide residues in agricultural products by a prepared mouse monoclonal antibody using enzyme-linked immunosorbeninsectitide residuest assay (ELISA). The working range was ppm-ppb level. The assay was sufficiently sensitive for analysis of the maximum residue limits in agricultural products in Japan. Our results indicate that the system we developed was useful for analysis of insecticide residues in agricultural products because rapid operation, highly accurate, flexible mobility, cheap, environmentally friendly system so on. The kits are now commercially available.

Research Products

• [Journal Article] Ru(II)-and Ir(I) Catalyzed Hydrogen Peroxide Oxidation of Hydroxamic Acids and their Subsequent Hetero Diels-Alder Cycloadditions with Chiral N-Dienyl Lactams (2010)
  • Author(s): Ahmad Fakhruddin, Kesiny Phomkeona, Abdel-Moneim Abu-Elfotoh, Kazutaka Shibatomi, Seiji Iwasa
  • Journal Title: Letters in Organic Chemistry 7 Pages: 475-478
  • Peer Reviewed
• [Journal Article] Asymmetric Inter-and Intramolecular Cyclopropanation Reactions Catalyzed by a Reusable Macroporous-Polymer-Supported Chiral Ruthenium(II)/Phenyloxazoline Complex (2010)
  • Author(s): Abdel-Moneim Abu-Elfotoh, Kesiny Phomkeona, Kazutaka Shibatomi, Seiji Iwasa
  • Journal Title: Angew.Chem.Int.Ed. 49 Pages: 8439-8443
  • Peer Reviewed
• [Journal Article] Asymmetric Inter- and Intramolecular Cyclopropanation Reactions Catalyzed by a Reusable Macroporous-Polymer-Supported Chiral Ruthenium(II)/Phenyloxazoline Complex (2010)
  • Author(s): Abdel-Moneim, Abu-Elfotoh, Kesiny Phomkeona, Kazutaka Shibatomi, Seiji Iwasa
  • Journal Title: Angewandte.Chemie.Inernationalt.Edition Volume: 49 Pages: 8439-8443
  • Peer Reviewed
• [Journal Article] Ru(II)- and Ir(I) Catalyzed Hydrogen Peroxide Oxidation of Hydroxamic Acids and their Subsequent Hetero Diels-Alder Cycloadditions with Chiral N-Dienyl Lactams (2010)
  • Author(s): Ahmad Fakhruddin, Kesiny Phomkeona, Abdel-Moneim Abu-Elfotoh, Kazutaka Shibatomi, Seiji Iwasa
  • Journal Title: Letters in Organic Chemistry Volume: 7 Pages: 475-478
  • Peer Reviewed
• [Journal Article] Development of an Enzyme-Linked Immunosorbent Assay for Residue Analysis of the Insecticide Emamection Benzoate in Agricultural Products (2009)
  • Author(s): Kondo, M., Yamashita, H., Uchigashima, M., Kono, T., Takemoto, T., Fujita, M., Saka, M., Iwasa, S,, Ito, S., Miyake, S.
  • Journal Title: Journal of Agricultural and Food Chemistry 57 Pages: 359-364
  • Peer Reviewed
• [Journal Article] Design and Synthesis of Novel Molecular Ru(II) Catalyst and its Applications to Highly Active Carbene Insertion Reactions of Diazo Ester (2009)
  • Author(s): Phomkeona, K., Nguyen M.N., Shibatomi, K., Iwasa, S.
  • Journal Title: Journal of Science and Engineering 45,5A Pages: 37-42
  • Peer Reviewed
• [Journal Article] Synthesis of a Novel Microporous Polymer-supported Ru(II) Catalyst and its Applications to Highly Efficient N-H Insertion Reactions (2009)
  • Author(s): Abu-Elftoh, A.-M., Phomkeona, K., Lorbriayao, B., Jingbaohom, N., Shibatomi, K., Iwasa, S.
  • Journal Title: Journal of Science and Engineering 45,5A Pages: 118-123
  • Peer Reviewed
• [Journal Article] Design and Synthesis a Novel Microporous Polymer-Supported Chiral Ru(II) Catalyst and its Applications to Highly Stereoselective Catalytic Asymmetric Cyclopropanations (2009)
  • Author(s): Abdel-Moneim Mohamed Abu-Elfotoh, Kesiny Phomkeona, Bounphak Lorbriayao, Ni-on Jingbaohom, Kazutaka Shibatomi, Seiji Iwasa
  • Journal Title: Journal of Science and Technology 47 Pages: 500-506
  • Peer Reviewed
• [Journal Article] Synthesis of a Novel Microporous Polymer-Supported Ru(II) Catalyst and its Applications to Highly Efficient N-H Insertion Reactions (2009)
  • Author(s): Abu-Elfotoh, A.-M.M., Murakami, S., Phomkeona, K., Lorbriayao, B., Jingbaohom, N., Shibatomi, K., Iwasa, S
  • Journal Title: Journal of Science and Engineering 45, 4E Pages: 500-5006
  • Peer Reviewed
• [Journal Article] Design and Synthesis of Novel Molecular Ru(II) Catalyst and its Applications to Highly Active Carbene Insertion Reactions of Diazo Ester (2009)
  • Author(s): Phomkeona, P., Ngoc, M.N., Souliyaseng, P., Shibatomi, K., Iwasa, S.
  • Journal Title: Journal of Science and Engineering 45, 4E Pages: 37-42
  • Peer Reviewed
• [Journal Article] Development of an Enzyme-Linked Immunosorbent Assay for Residue Analysis of the Insecticide Emamection Benzoate in Agricultural Products (2009)
  • Author(s): Kondo, M., Yamashita, H., Uchigashima, M., Kono, T., Takemoto, T., Fujita, M., Saka, M., Iwasa, S., Ito, S., Miyake, S.
  • Journal Title: Journal of Agricultural and Food Chemistry 57 Pages: 359-364
  • Peer Reviewed
• [Journal Article] Chiral Bis(2-oxazolinyl)xanthene(xabox)/Transition Metal Complexes Catalyzed 1, 3-Dipolar Cycloaddition Reactions (2008)
  • Author(s): Phomkeona, K., Iwasa, S., Ishima, Y., Takemoto, T., Shibatomi, K., Nishiyama, H.
  • Journal Title: Tetrahedron 64 Pages: 1813-1822
  • Peer Reviewed
• [Journal Article] Chiral bis (2-oxazolinyl) xanthene (xabox)/transition metal complexes catalyzed 1, 3-Dipolar cycloaddition reactions and Diels-Alder reactions (2008)
  • Author(s): Phomkeona, K., Takemoto, T., Ishima, Y., Shibatomi, K., Iwasa, S., Nishiyama, H.
  • Journal Title: Tetrahedron 64 Pages: 1813-1822
  • Peer Reviewed
• [Journal Article] Lewis Acid-catalyzed Asymmetric Fluorination of ・ -Keto Esters : Dramatic Improvement in Enantioselectivity by Changing the Operation Sequence (2008)
  • Author(s): Shibatomi, K., Tsuzuki, Y., Iwasa, S.
  • Journal Title: Chemistry Letters 37 Pages: 2-3
  • Peer Reviewed
• [Presentation] Asymmetric Inter-and Intramolecular Cyclopropanation Reactions Catalyzed by Reusable Macroporous Polymer-Supported Chiral Ru(II)-pheox Complex (2010)
  • Author(s): Abdel-Moneim Abu-Elfotoh, Kesiny Phomkeona, Kazutaka Shibatomi, Seiji Iwasa
  • Organizer: The 11^<th> International Chemistry Conference and Exhibition in Africa (11 ICCA), The Role of Chemistry in Development of Africa
  • Place of Presentation: Luxor, EGYPT.(Poster Presentation)
• [Presentation] Catalytic Asymmetric Carbene Transfer Reactions to Functionalized Alkenes : Highly Efficient Synthesis of Optically Active Cyclopropyl Amine and Ether Anologues (2010)
  • Author(s): Kesiny Phomkeona, Abdel-Moneim Abu-Elfotoh, Kazutaka Shibatomi, Seiji Iwasa
  • Organizer: The 11^<th> International Chemistry Conference and Exhibition in Africa (11 ICCA), The Role of Chemistry in Development of Africa
  • Place of Presentation: Luxor, EGYPT.(Oral Presentation)(依頼講演)
• [Presentation] Hydrogen Peroxide Oxidation of Phenol Derivatives Catalyzed by Microporous Polymer-Supported Ru(II)-dm-pheox (2010)
  • Author(s): Abdel-Moneim Mohamed Abu-Elfotoh, Nguyen Minh Ngoc, Kesiny Phomkeona, Kazutaka Shibatomi, Seiji Iwasa
  • Organizer: The 2^<nd> Regional Conference on Global Environmental Issues for Sustainable Development in the ASEN Region
  • Place of Presentation: Ho Chi Minh City,VIETNAM.(Oral Presentation)
• [Presentation] Catalytic Asymmetric Carbene Transfer Reactions to Functionalized Alkenes : Highly Efficient Synthesis of Optically Active Cyclopropyl Amine and Ether Analogues (2010)
  • Author(s): Seiji Iwasa
  • Organizer: The 11^<th> International Chemistry Conference and Exhibition in Africa (11 ICCA)
  • Place of Presentation: Luxor, EGYPT
• [Presentation] Creation, and breakthrough, Microporous Polymer-Supported Chiral Ru(II)-pheox Complex as an Efficient Catalyst for Enantioselective Cyclopropanation Reactions (2009)
  • Author(s): Abdel-Moneim Abu-Elfotoh, Kesiny Phomkeona, Kazutaka Shibatomi, Seiji Iwasa
  • Organizer: Global COE in chemistry (Material Science Frontier Seminar), The most advanced science based on manufacturing technology : Molecular design
  • Place of Presentation: Nagoya University, JAPAN.(Poster Presentation No.P-30)
• [Presentation] Design and Synthesis of a Novel Microporous Polymer-Supported Chiral Ru(II)-pheox Catalyst With High Reactivity, Enantioselectivity, Reusability and Storage Ability in Cyclopropanation Reactions (2009)
  • Author(s): A.M.Abu-Elfotoh, K.Phomkeona, K.Shibatomi, S.Iwasa
  • Organizer: The Eleventh International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-11)
  • Place of Presentation: Rihga Royal Hotel Kyoto, JAPAN.(Poster Presentation No.PC-053)
• [Presentation] Design and Synthesis a Novel Microporous Polymer-Supported Chiral Ru(II) Catalyst and its Applications to Highly Stereoselective Catalytic Asymmetric Cyclopropanations (2009)
  • Author(s): Abdel-Moneim Mohamed Abu-Elfotoh, Kesiny Phomkeona, Bounphak Lorbriayao, Ni-on Jingbaohom, Kazutaka Shibatomi, Seiji Iwasa
  • Organizer: The 2^<nd> Regional Conference on Chemical Engineering : Chemical Engineering for Sustainable Development and Collaboration in the ASEAN Region
  • Place of Presentation: Rex Hotel, Ho Chi Minh City, VIETNAM.(Oral Presentation O-1B)
• [Presentation] Synthesis a Novel Microporous Polymer-Supported Ru(II) Catalyst and its Applications to Highly Efficient N-H Insertion Reactions (2009)
  • Author(s): Abdel-Moneim Mohamed Abu-Elfotoh, Safumi Murakami, Kesiny Phomkeona, Bounphak Lorbriayao, Ni-on Jingbaohom, Kazutaka Shibatomi, Seiji Iwasa
  • Organizer: The 2^<nd> Regional Conference on Chemical Engineering : Chemical Engineering for Sustainable Development and Collaboration in the ASEAN Region
  • Place of Presentation: Rex Hotel, Ho Chi Minh City, VIETNAM.(Poster Presentation P-17)
• [Presentation] Microporous Polymer-supported Chiral Ru(II)pheox Catalysts and their Successful Application to Catalytic Asymmetric Cyclopropanation Reactions with High Reactivity, Enantioselectivity and Re-usability (2009)
  • Author(s): A.Abu-Elfotoh, K.Phomkeona, K.Shibatomi, S.Iwasa
  • Organizer: The 1^<st> AUN/SEED-Net, Regional Conference on Materials 2009
  • Place of Presentation: Equatorial Hotel Penang, MALAYSIA.(Oral Presentation)
• [Presentation] Novel Transition Metal Complexes for Catalytic Hydrogen Peroxide Oxidation of Phenol Derivatives (2009)
  • Author(s): Tsuzuki, K., Fakhruddin, A., Shibatomi, K., Iwasa, S.
  • Organizer: International Conference on Green & Sustainable Chemistry
  • Place of Presentation: Singapore
• [Presentation] Catalytic Asymmetric Cyclopropanation of Alkenes with Diazoesters Catalyzed By Chiral Phenyloxazolinyl (Pheox) Ruthenium (II) Complexes (2008)
  • Author(s): Phomkeona. K., Takemoto, T., Iwasa, S.
  • Organizer: 9th Tetraheclron Symposium : Challenges in Organic Synthesis
  • Place of Presentation: Berkeley. CA USA .
  • Year and Date: 2008-07-22
• [Book] Mew Acid Catalysis in Modern Organic Synthesis : Transition-metal Lewis Acids : From Vanadium to Platinum (2008)
  • Author(s): Iwasa, S., Nishiyama, H.
  • Total Pages: 45
  • Publisher: Wiley-VCH Verlag GmbH & Co. KGaA
• [Remarks] ホームページ等
• [Patent(Industrial Property Rights)] アゾキシストロビン誘導体、アゾキシストロビンに対する抗体、またはそのフラグメントならびにそれらの抗体またはフラグメントを用いた測定キットおよび測定方法 (2010)
  • Inventor(s): 岩佐、三宅, その他
  • Industrial Property Rights Holder: 堀場製作所
  • Industrial Property Number: 2010-149812
  • Filing Date: 2010
• [Patent(Industrial Property Rights)] アゾキシストロビン誘導体、アゾキシストロビンに対する抗体、またはそのフラグメントならびにそれらの抗体またはフラグメントを用いた測定キットおよび測定方法 (2010)
  • Inventor(s): 岩佐、三宅, その他
  • Industrial Property Rights Holder: 堀場製作所
  • Industrial Property Number: 2010-149812
  • Acquisition Date: 2010
• [Patent(Industrial Property Rights)] 特許権 (2009)
  • Inventor(s): 岩佐精二, ほか6名
  • Industrial Property Rights Holder: 岩佐精二, ほか6名
  • Industrial Property Number: 2009-156192
  • Filing Date: 2009-06-30