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Download Report Discovery and Development of a Sumitomo Chemical Co., Ltd. Agricultural Chemicals Research Laboratory New Insecticide ‘amidoflumet Tatsuya MORI (Panduck®)’ with High Miticidal Noritada MATSUO Makoto HATAKOSHI Activity against House Dust Environmental Health Division Mites Yasuyori TANAKA Environmental Health Science Laboratory Keiko OSE Amidoflumet is a new trifluoromethanesulfonanilide compound with high house dust miticidal activity which was discovered by Sumitomo Chemical, and was registered in Japan in 2004. House dust mites and their prod- ucts are known to be major household allergens to children and the elderly, and they cause asthma and atopic dermatitis. Amidoflumet shows high lethal activity against common house dust mites. In particular amidoflumet has excellent activity against predatory cheyletid mites, which often cause biting injuries to humans. These effi- cacies and its excellent safety to mammals can provide us with an important tool for controlling various house dust mites. This paper describes the discovery story, miticidal efficacies in various formulations, a method of synthesis and safety evaluations of amidoflumet. This paper is translated from R&D Report, “SUMITOMO KAGAKU”, vol. 2007-II. Introduction tional miticides for indoor use, and we have discovered and developed amidoflumet (Panduck®), which is a Various types of mites inhabit the typical home envi- new compound that exhibits activity not seen in exist- ronment, but among these, house dust mites that feed ing miticides. Amidoflumet has a higher lethal efficacy on human dandruff and food residues are found in the for the house dust mites that inhabit households in largest numbers. Their corpses and feces cause aller- general than conventional agents and is faster acting, gies.1) Therefore, control of house dust mites is an and a salient feature is its high lethal efficacy against important problem in terms of measures for allergic cheyletid mites, which have been difficult to control disorders, which have been increasing in children and with the agents used up to now. Amidoflumet has supe- elderly people in recent years, particularly, asthma and rior stability and can be adapted to various types of for- atopic dermatitis. Other known mites include mold mulations. In addition, the products that contain amid- mites (Tyrophagus putrescentiae), which occur in large oflumet for mite control have a level of safety that is the numbers in stored food products and tatami mats same or more than the products actually used up to (Japanese straw floor covering), as well as cheyletid now. mites, which are predatory mites. Pyrethroid insecti- In this paper, we will report on the history of the dis- cides have been used for the most typical house dust covery of amidoflumet, the efficacy of various prepara- mite control agents, but their effect has not always tions on house dust mites, physical and chemical prop- been satisfactory on the various types of mites that erties, manufacturing methods and safety evaluations. inhabit households. In particular, there have been no History of the Discovery. known compound that exhibit a high level of effect on the cheyletid mites that attack humans. 1. Research Background At Sumitomo Chemical Co., Ltd., we have been The corpses and excretions of house dust mites such searching for a new house dust mite control agent that as the American house dust mite (Dermatophagoides is highly effective over a wider spectrum than conven- farinae) and the European house dust mite (D. SUMITOMO KAGAKU (English 2007-II Edition) 2007-II, Report 1 Copyright © 2007 Sumitomo Chemical Co., Ltd. 1 Discovery and Development of a New Insecticide ‘amidoflumet (Panduck®)’ with High Miticidal Activity against House Dust Mites pteronyssinus), which are the main household dust romethanesulfonanilide compounds (4 – 15) containing mites, are thought of as being the main allergens caus- alkoxycarbonyl groups at the 2-position of a trifluo- ing asthma and dermatitis in children and elderly peo- romethanesulfonanilide shown in Fig. 3 from structural ple. Furthermore, there is a strong desire to eliminate similarities with phenyl salicylate (1) and benzyl ben- allergens from households to avoid the onset of these. zoate (2). Pyrethroid agents such as phenothrin, and ester com- pounds such as phenyl salicylate (1) and benzyl ben- CO2R2 zoate (2), which are shown in Fig. 1, are used as agents for preventing household dust mites. R1 NHSO2CF3 4 : R1=Cl, R2=Me 10 : R1=I, R2=Me 5 : R1=Cl, R2=Et 11 : R1=Me, R2=Me O O 6 : R1=Cl, R2=iPr 12 : R1=NO2, R2=Me 7 : R1=Cl, R2=tBu 13 : R1=OMe, R2=Me O O 8 : R1=Cl, R2=Ph 14 : R1=CF3, R2=Me OH 9 : R1=Br, R2=Me 15 : R1=H, R2=Me 1 2 Fig. 3 Synthetic method of 2-alkoxycarbonyltri- fluoromethanesulfonanilides Fig. 1 Typical active ingredients for house dust mites The test results are shown in Table 1 and 2. However, there are problems in that the efficacy of As a result, it was clear that compounds with halogen these agents is insufficient for house dust mite and atom substitutions at the 4-position on the benzene ring mold mite control, and they exhibit almost no effect on exhibited a high lethal activity for both American house cheyletid mites which cause a great deal of damage by dust mites (Df ) and mold mites (Tp). On the other hand, biting humans. In addition, these cheyletid mites are compounds 12 and 14 with nitro group and trifluo- pests that are difficult to remove, and it is known that romethyl group substitutions, which are both electron other miticides cannot remove them sufficiently.2) The withdrawing groups, showed insufficient activity. authors started on investigative research to discover a In addition, compounds 11 and 13 with a methyl household dust mite controlling agent that had a high group and a methoxy group substitutions, which are level of efficacy for these cheyletid mites. Moreover, sterically about the same size as a chlorine atom, only we focused on not only house dust mites, but also mold mites and cheyletid mites. Table 1 Miticidal activity of 2-alkoxycarbonyltri- fluoromethanesulfonanilides against D. 2. Discovery of Insecticidal Trifluoromethanesul- farinae (Df) and T. putrescentiae (Tp) fonanilide Compounds 2 Previously, the authors had discovered that the Compound Dose (mg/m ) – Activity (%) Df Tp series of trifluoromethanesulfonanilide compounds (3) No. R1 R2 8 (mg/m2) 80 (mg/m2) shown in Fig. 2 exhibited a high level of lethal activity 4 Cl Me + + + + + + 3) for houseflies and cockroaches. 5 Cl Et + + + + + + 6 Cl iPr + + + + + + 7 Cl tBu + + + + + + NHSO2CF3 8 Cl Ph + + +* – 9 Br Me + + + + + + Xn 10 I Me + + + + + + 11 Me Me + + +* – 3 12 NO2 Me – + + + Fig. 2 Insecticidal trifluoromethanesulfonanilides 13 OMe Me +* – 14 CF3 Me – + + + 15 H Me + + +* – 3. Discovery of Amidoflumet (Panduck®) + + + : 100% mortality, + + : > 90% mortality, + : 70 – 90% mortality, Therefore, we focused on the miticidal activity of this – : Almost the same as untreated sample group of compounds and synthesized a series of trifluo- * : 80 (mg/m2) SUMITOMO KAGAKU (English 2007-II Edition) 2007-II, Report 1 Copyright © 2007 Sumitomo Chemical Co., Ltd. 2 Discovery and Development of a New Insecticide ‘amidoflumet (Panduck®)’ with High Miticidal Activity against House Dust Mites Table 2 Miticidal activity of 2-alkoxycarbonyltri- Table 3 Physical and chemical property of amidoflumet fluoromethanesulfonanilides against C. moorei (Cm) Molecular formula C9H7ClF3NO4S Molecular weight 317.67 Compound Dose (mg/m2) – Activity (%) Appearance Slightly yellow or colorless crystalline solid Cm Melting point 81 ~ 85°C No. R1 R2 –1 80 (mg/m2) Vapor pressure ca. 1.51 × 10 Pa(Gas saturation method) 4 Cl Me + + + Acid dissociation constant pKa = ca.3.8 5 Cl Et + + + Distribution coefficient logP = 2.13(pH5, 24°C)(Ambient shake flask method) 6 Cl iPr + + + logP = 4.13(pH1, 24°C)(do.) 7 Cl tBu + + + logP = –0.28(pH9, 24°C)(do.) 9 Br Me + + + Solubility Soluble in following solvents : 10 I Me + + + Acetonitrile, N,N-Dimethylformamide, Acetone, Methanol, Ethanol + + + : 100% mortality, + + : > 90% mortality, + : 70 – 90% mortality, Thermal analysis Endothermy observed at ca.82°C – : Almost the same as untreated sample Weight loss by vaporization began at around 80°C exhibited a low level of activity. white crystalline powder. It is easily dissolved in polar Next, when we focused on alkoxycarbonyl groups at solvents such as N,N-dimethylformamide, acetonitrile the 2-position on the benzene ring, and compounds and methanol, but it dissolves poorly in water. The where R2 was a lower alkyl group with one to three car- melting point is around 82°C, and it does not decom- bon atoms exhibited a high level of lethal activity pose when melted. The dissociation constant pKa is against both American house dust mites and mold approximately 3.8, and as the pH becomes lower the mites. On the other hand, there was a significant proportion of the nonionic form increases, so the solu- decrease in the activity with the phenyl ester (8), which bility in water becomes lower. For solutions at various is sterically larger than a lower alkyl group. pH (1, 5 and 9), the 1-octanol layer partition increased Furthermore, the compounds 4 – 7, 9 and 10, which as the pH became lower. In differential thermal analy- exhibited a high level of activity for American house sis, endothermy and weight loss because of melting dust mites and mold mites, also showed the same high around 80°C were observed. level of activity for Chelacaropsis moorei (Cm). From these results, it was clear that a number of one to three 2. Stability carbon atoms was suitable for R2. Amidoflumet was stable even when stored for 36 From the activity on some species of house dust months at 25°C and humidity of 60% and for six months mites above and from the activity in various formula- at 40°C and humidity of 75%.
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