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R&D Reports

vol. 2005 - II (2005.11.30 issue)

Discovery and Development of a Novel Pyrethroid Insecticide ‘Metofluthrin (SumiOne®, Eminence®)’

Metofluthrin (SumiOne®, Eminence®) is an exciting novel pyrethroid discovered by Sumitomo Chemical Co., Ltd. It was registered in Japan in January 2005 and has now been under worldwide development for environmental health use. Metofluthrin has extremely high knockdown activity against various insect pests especially mosquitoes, as well as relatively high volatility and low mammalian toxicity. This is applicable to not only existing formulations and devices such as a mosquito coil and a liquid vaporizer, but also various new type products such as a fan vaporizer, a paper emanator and a resin emanator. It is noted that knockdown activity of Metofluthrin is more than 40 times higher than that of d-allethrin against southern house mosquitoes in a mosquito coil formulation. This paper describes the discovery story, insecticidal efficacies in various formulations, synthetic methods and safety evaluations of Metofluthrin.
( 4~16 by Noritada MATSUO,Kazuya UJIHARA,Yoshinori SHONO,Tomonori IWASAKI,Masayo SUGANO,Tomonori YOSHIYAMA,Satoshi UWAGAWA )

Development of a novel anti-tumor drug ‘amrubicin’, a completely synthetic anthracycline

Amrubicin is a completely synthetic anthracycline derivative. In contrast, however, the anthracyclines used clinically thus far have been produced by fermentation or semisynthesis. Amrubicin is structurally distinguishable from other anthracyclines by the amino group at the 9-position and its unique sugar moiety. In April 2002, Amrubicin was approved in Japan for the treatment of non-small cell lung cancer and small cell lung cancer.
( 17~26 by Toshihiro NOGUCHI,Mitsuharu HANADA,Takashi YAMAOKA,Shinya MORISADA,Shinji ICHII )

Synthesis of Pharmaceutical Intermediates Aiming at Construction of Optically Active Tertiary Alcohols as a Key Technology

We are developing novel synthetic methods of pharmaceutical intermediates aiming at construction of optically active tertiary alcohols. Now, we have found that the tetrasubstituted carbon center was easily constructed by the L-proline catalyzed direct asymmetric aldol reaction between cyclohexanone and ethyl phenylglyoxylate, which gave the corresponding aldol adduct in good yield with excellent diastereo- and enatioselectivity. Herein, we also report a practical synthetic route of (S)-CHPGA as a key intermediate for the preparation of (S)-Oxybutynin.
( 27~32 by Tetsuya IKEMOTO,Osamu TOKUDA,Wei-Guo GAO )

Development of High Performance Elastomer ‘Tafthren®’

High performance elastomer "Tafthren®", which exhibit distinguished miscibility with polypropylene, has been developed by precise stereochemical and sequencial control of polyolefins with new homogeneous catalyst developed in Sumitomo chemical Co., Ltd. Many important properties of polypropylene, like flexibility, heat resistance, scratch resistance, transparency, adhesion properties and so on, could be improved remarkably by the addition of Tafthren®, that could not be improved by the utillization of conventional olefinic elastomers or plastomers as modifiers. In addition, Tafthren® is expected as an environmentally friendly material, because Tafthren® is comprising from substantially same component as polypropylene, so recycle becomes easier than conventional modifier used systems. In this article, some of the practical features and practical application examples of Tafthren® will be introduced.
( 33~40 by Hirofumi JOHOJI,Hidetake HOZUMI,Tadaaki NISHIYAMA,Harunori FUJITA,Akio IMAI )

Technology of Controller Performance Monitoring and Diagnosis in Chemical Plants

The controller performance monitoring technique, which is based on the principle of minimum variance control, can evaluate the performance of many PID controllers in a plant at a time and is applicable in online. It is important that the origins of failure are analyzed for lower performance controllers. One of them is valve failure and is identified by the proposed methods. In this article, the technology of controller performance monitoring and diagnosis is mentioned and its applications in practical chemical plants are shown.
( 41~49 by Hidekazu KUGEMOTO )

Alternative methods for the safety evaluation of chemicals

To evaluate the toxicity of chemicals, sometimes the alternative methods instead of prescribed methods are very useful. As the alternative methods have their own sensitivity to distinguish chemical toxicity, we have to consider the detection principle and the sensitivity of the methods before use. Many alternative methods are developing now. It is desirable that the detection sensitivity and the results consistency between the alternative and the prescribed methods will be increased by the improvement of the methods and/or the ingenious way of using. In this review, we describe the public situation, trend, and our examination of the alternative methods to detect genotoxic, skin irritating or skin sensitizing potential of chemicals.
( 50~58 by Mika OTA,Yosuke NAKAMURA,Sachiko KITAMOTO,Takashi MORIMOTO )

Development of PSA Gas Separation Technology to Reduce Greenhouse Effect

"Pressure Swing Adsorption" is playing a role of one of the Gas Separation Technologies to save energy consumption instead of Absorption or Distillation in the field of chemical industry. Especially this technology should be focused on "Saving Energy" which will contribute to the reduction of CO2 emission to cause Greenhouse Effect. Sumitomo Seika has improved this technology to expand its application field to promote "Saving Energy": In this paper, "Simultaneous N2/O2 Production Process" to save energy consumption is described and "Methanol Steam Reforming Hydrogen Generator" to produce lower cost hydrogen is introduced.
( 59~66 by Kazuo HARUNA,Masanori MIYAKE,Hiroaki SASANO )

Palladium Charcoal-Catalyzed Suzuki-Miyaura Coupling and Iridium-Catalyzed Aromatic C-H Borylation

We report here on the "Palladium Charcoal-Catalyzed Suzuki-Miyaura Coupling and Iridium-Catalyzed Aromatic C-H Borylation." In the Pd/C-catalyzed Suzuki-Miyaura coupling, we found that the combination of non-prereduced Pd/C and a phosphine ligand, such as PPh3, was essential for the reaction of halopyridines and haloquinolines. In the catalytic C-H borylation of arenes, we found that 2,6-diisopropyl-N-(2-pyridylmethylene) aniline acted as a good ligand. The bulkiness around the imine moiety was important for obtaining the products in high yields.
( 67~75 by Mayumi NISHIDA,Tsuyoshi TAGATA )

Concernig Sumitomo Chemical Systems Service’s Initiative on the Personal Information Protection Act

The Personal Information Protection Act, which implements the 8 Principles of the Privacy Guidelines of the Organization for Economic Co-operation and Development (OECD), went into full effect in April 2005. The background and requirements of the Act are outlined. Then will be explained the direction with respect to the Act for this company, which is in the business of handling personal information, each process for dealing with the "Safety Management Measures" enacted by this company referring to the Ministry of Economy, Trade and Industry's guidelines, and the "Compliance Program".
( 76~87 by Hiroshi NISHIKAWA,Toshinori GOTO,Toshiko SATOMURA )

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