FRAC Classification of Fungicides · 2020-01-20 · pyrimethanil mepanipyrim cyprodinil hymexazole...

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C2: inhibition of complex II: succinate-dehydrogenase # 7 SDHI (Succinate dehydrogenase inhibitors) FRAC Mode of Action Poster © This version updated March 2019 pyridines C: Respiration nzovindiflupyr Extract from the cotyledons of lupine plantlets 作物永續發展協會 台灣分會 S i n c e 2 0 0 1 財團法人植物保護科技基金會 Plant Protection Science And Technology Foundation OSBPI Oxysterol binding protein homologue inhibition (Giant Knotweed Extract) 1,2,4,-thiadiazole triazoles pyridines piperazines pyrimidines Polyoxin B flumorph dimethomorph pyriofenone metrafenone thifluzamide penflufen furametpyr isofetamid carboxin iprovalicarb phenyl acetamides pyridazinones benzene- sulfonamides valinamide carbamates diclomezine flusulfamide valifenalate benthiavalicarb pyrimorph cinnamic acid amides mandelic acid amides mandipropamid piperalin pepridyl pyrimidine nucleoside piperidines fenpropidin spiroketal- amines spiroxamine morpholines dodemorph fenpropimorph tridemorph aldimorph fenpiclonil fludioxonil oxytetracycline (bactericide) triforine pyrifenox fenarimol pyrisoxazole nuarimol triflumizole imazalil pefurazoate oxpoconazole prochloraz fenhexamid fenpyrazamine triadimenol penconazole propiconazole triticonazole mefentrifluconazole triadimefon myclobutanil tetraconazole metconazole tebuconazole fluquinconazole fenbuconazole flutriafol hexaconazole flusilazole triazolinthione prothioconazole imibenconazole epoxiconazole diniconazole difenoconazole simeconazole cyproconazole bitertanol bromuconazole azaconazole etaconazole ipconazole pyrimethanil mepanipyrim cyprodinil octhilinone hymexazole isothiazolones isoxazoles oxolinic acid (bactericide) oxazolidinones butyrolactones acylalanines oxadixyl ofurace metalaxyl-M furalaxyl benalaxyl-M dimethirimol ethirimol metalaxyl bupirimate benalaxyl quinoxyfen proquinazid fluopimomide fluopicolide phenamacril ethaboxam thiophanate thiophanate- methyl thiabendazole pyridinylmethyl -benzamide aminocyanoacrylates aryloxyquinoline quinazolinone diethofencarb * negative cross-resistance to B1 pencycuron benzophenone benzoylpyridine imidazoles streptomycin (bactericide) kasugamycin blasticidine-S zoxamide benzimidazoles thiophanates toluamide benomyl carbendazim fuberidazole ethylamino-thiazole carboxamide triazoxide tebufloquin ferimzone teclofthalam cymoxanil flutianil picarbutrazox validamycin dodine cyflufenamid #U12 #U06 # 37 #36 benzotriazines phthalamic acid #34 #35 #27 #U13 #U14 #U16 #U17 #U18 thiocarbamates terbinafine (antimycotic) pyributicarb (herbicide) naftifine (antimycotic) amino- pyrazolinones hydroxyanilides allylamines cyanoacetamide oxime cyano- methylene thiazolidine pyrimidinone-hydrazones 4-quinolyl acetate • Temporary status; information no mode of action and/or resistance risk is still uncertain dimethachlone vinclozolin iprodinoe chlozolinate procymidone dicarboximides boscalid aryl-phenyl-ketones oxycarboxin fenfuram oxathiin- carboxamides pyridine-carboxamides pydiflumetofen F2: phospholipid biosynthesis methyltransferase pyraziflumid pyrazophos iprobenfos edifenphos dicloran biphenyl tolclofos- methyl FRAC Classification of Fungicides Fungal control agents by cross resistance pattern and mode of action 2019 (www.frac.info) B: Cytoskeleton and Motor Proteins 細胞骨架與微管動力蛋白 C: Respiration 呼吸作用 A: Nucleic Acids Metabolism 核酸代謝 G: Sterol Biosynthesis in Membranes 固醇類生合成 D: Amino Acid and Protein Synthesis 胺基酸與蛋白質生合成 E: Signal Transduction 信息傳遞 Unknown Mode of Action 未知機制 BM : Biologicals with Multiple Modes of Action 多作用點生物型殺菌劑 NC : Not Classified 未分類 C7: ATP transport (proposed) # 38 silthiofam famoxadone imidazolinones fluazinam fluoxastrobin thiazole carboxamides polypeptide lectin BM 01: plant extract (BLAD) Phosphorous acid phosphorous acid P6: microbial elicitors #P06 laminarin P4: polysaccharide elicitors #P04 polysaccharide P1: salicylate related #P01 benzothiodiazole BTH A1: RNA polymerase I A2: adenosin-deaminase A4: DNA topoisomerase type II (gyrase) # 31 carboxylic acids # 32 heteroaromatics # 4 # 8 PA-fungicides (PhenylAmides) hydroxy(2-amino)-pyrimidines benodanil mepronil flutolanil phenyl- benzamides fluopyram furan- carboxamides pyridinyl-ethyl-benzamides phenyl-oxo-ethyl- thiophene amide pyraoxystrobin enoxastrobin coumoxystrobin azoxystrobin mandestrobin inpyrfluxam sedaxane flufenoxystrobin picoxystrobin orysastrobin dimoxystrobin oximino- acetamides methoxy- acetamides methoxy- acrylates metominostrobin fenaminstrobin pyribencarb triclopyricarb benzyl- carbamates pyrametostrobin pyraclostrobin kresoxim-methyl trifloxystrobin fenamidone dihydro- dioxazines oximino- acetates fenpicoxamid amisulbrom ametoctradin picolinamide fentin chloride fentin hydroxide fentin acetate # 23 # 24 fluxapyroxad penthiopyrad bixafen benzovindiflupyr isopyrazam isoflucpyram fluindapyr diflumetorim tolfenpyrad fenazaquin cyazofamid prothiocarb iodocarb propamocarb oxathiapiprolin # 44 chloroneb etridiazole # 14 F3: cell peroxidation (prop.) aromatic hydrocarbons & heteroaromatics phosphorothiolates & dithiolanes phosphorothiolates aromatic hydrocarbons tecnazene (TCNB) dithiolanes isoprothiolane # 6 thiazole- carboxamides N-methoxy-(phenyl- ethyl)-pyrazole- carboxamides pyrazole- carboxamides- # 7 C2: complex II: succinate-dehydrogenase SDHI (Succinate DeHydrogenase Inhibitors) phenylureas B4: cell division (unknown site) # 20 B1: β-tubulin assembly in mitosis # 1 # 43 B5: delocalisation of spectrin-like proteins benzamides E1: signal transduction (mechanism unknown) #13 D3: protein synthesis (ribosome, initiation step) hexopyranosyl antibiotics D1: methionine biosynthesis (cgs gene) (proposed) # 9 Anilino-Pyrimidines (AP fungcides) #M12 tolylfluanid captafol chinomethionat folpet thiocarbamates (electrophiles) methasulfocarb fluoroimide iminoctadine mixture of iminoctadine and other polyamines guazatine #M07 bis-guanidines (membrane disruptors, detergents) #M10 #M06 #M04 phthalimides (electrophiles) sulphamides (electrophiles) chlorothalonil dithianon dichlofluanid captan anilazine sulphur #M08 S #M02 #M09 #M01 inorganic triazines (unspecified mechanism) (electrophiles) dithiocarbamates & relatives (electrophiles) copper preparations Cu inorganic (electrophiles) #M03 febram zinc thiazole maneb zineb propineb ziram thiram mancozeb metiram A3: DNA / RNA synthesis (prop.) D2: protein synthesis (ribosome, termination step) enopyranuronic acid D4: protein synthesis (ribosome, initiation step) # 25 glucopyranosyl antibiotics D5: protein synthesis (ribosome, elongation step) # 41 tetracycline antibiotics G1: C14-demethulase in sterol biosynthesis (erg11/cyp51) (SBI : Class I) # 3 sulfamoyl-triazole DMI-fungicides (DeMethylation Inhibitors) H:Cell Wall Biosynthesis 細胞壁生合成 H4: chitin synthase C: Respiration 呼吸作用 F: Lipid Synthesis or Transport / Membrane Integrity or Function 脂質生合成與膜完整性 P: Host Plant Defence Induction 防衛反應誘發 Mineral oils, organic oils, inorganic salts material of biological orign glucopyranosyl antibiotic guanidines tetrazolyloxime # 19 Polyoxins E3: osmotic signal transduction MAP / histidine kinase (os-1, Daf1) # 2 C1: complex I NADH Oxido-reductase quinazoline pyrimidinamine pyrazole-5-carboxamide # 39 cyano-imidazole C4: complex III cytochrome bc1(ubiquinone reductase) at Qi site # 21 Qil fungicides (Quinone inside Inhibitors) triazolo- pyrimidylamine # 45 QoSI-fungicide (stigmatellin binding) C8: inhibition of complex III cytochrome bc1(ubiquinone reductase) at Qo site stigmatellin binding sub site) thiophene-carboxamides 2,6-dinitro-aniline MBC fungicides (=Methyl Benzimidazole Carbamates) B6: actin/myosin/fimbrin function H5: cellulose synthase # 40 Carboxylic Acid Amides (CAA fungicides) quintozene (PCNB) oxazolidine-diones methoxy-carbamates C3: complex III cytochrome bc1 (ubiquinol oxidase) at Qo site (cyt b gene) # 11 QoI fungicides (Quinone outside Inhibitors) acibenzolar- S-methyl thiadiazole carboxamide P3: salicylate related #P03 #P02 isotianil probenazole tiadinil P2: salicylate related benzothiazole Trichoderma atroviride (strain SC1) Trichoderma atroviride Trichoderma atroviride Trichoderma asperellum (strain I-1237) (strain T34) (strain LU132) Fungal Tritroderma spp. (strain K61) (strain J1446) Streptomyces griseovirides Gliocladium catenulatum Fungal Gliocladium spp. Bacterial Streptomyces spp. fosetyl-al ethyl-phosphonates P7: phosphonates #P07 phosphonates Bacterial Bacillus spp. Bacillus mycoides (Isolate J) Fungal Saccharomyces spp. Reynoutria sachalinensis P5: anthraquinone elicitors #P05 plant extract # 47 cyanoacrylates # 50 B3: β-tubulin assembly in mitosis # 22 benzamides and thiazole carboxamides azanaphthalenes E2: osmotic signal transduction MAP / histidine-kinase (os-2, HOG1) # 12 phenylpyrroles (PP-fungicides) G4: squalene epoxidase in sterol biosynthesis (erg1) # 18 (SBI : Class IV) G3:3-keto reductase in C4-demethylation (erg27) # 17 (KRI fungicides KetoReductase Inhibitors) (SBI : Class III) G2: 14 -reductase and ∆8→∆7-isomerase in sterol biosynthesis (erg2, erg24) Amines(“Morpholines”) (SBI : Class II) # 5 B2: β-tubulin assembly in mitosis * # 10 N-phenyl carbamates C6: inhibitors of oxidative phosphorylation, ATP synthase # 30 organo tins C5: uncouplers of oxidative phosphorylation # 29 dinitrophenyl crotonates meptyl dinocap binapacryl Microbial (Bacillus sp.) Bacillus sp. and the fungicidal lipopeptides produced Bacillus amyloliquefaciens (synonym B. subtilis) strains: QST 713 FZB24 MBI600 D747 F9: lipid homeostasis and transfer/storage # 49 F8: ergosterol binding # 48 polyene natamycin (pimaricin) F7: cell membrane disruption # 46 plant extract Plant oils (mixtures) eugenol, geraniol thymol Melaleuca alternifolia (Tea Tree Extract) anthraquinones (electrophiles) maleimides (electrophiles) #M11 chloronitriles (unspecified mechanism) #M05 I2: dehydratase in melanin biosynthesis I1: dehydratase in melanin biosynthesis #16.2 #16.1 Melanin Biosynthesis Inhibitors: Dehydratase (MBI-D) carboxamide cyclopropane carboxamide diclocymet fthalide tolprocarb Melanin Biosynthesis Inhibitors: Reductase (MBI-R) isobenzo-furanone pyrrolo-quinolione pyroquilon F4: cell membrane permeability, fatty acids (prop.) # 28 carbamates F6: microbial disrupters of pathogen cell membranes piperidinyl- thiazole- isoxazoline tricyclazole triazolobenzo-thiazole fenoxanil carpropamid I3: polyketide synthase in melanin biosynthesis #16.3 trifluoroethyl-carbamate Cell walls of Saccharomyces cerevisiae Strain LAS117 propionamide M: Chemicals with Multi-Site Activity 多點作用機制 quinoxalines (electrophiles) pyrimidinamines,pyrazole-MET1, quinazoline pyrazine- carboxamides N-cyclopropyl-N- Benzyl-pyrazole- carboxamides BM 02: microbial (living microbes or extract, metabolites) I: Melanin Synthesis in Cell Wall 黑色素生合成 醯基丙胺類 免賴得 貝芬替 腐絕 甲基多保淨 多保淨 賓克隆 氟比來 苯醯胺類 座賽胺 歐索林酸 依瑞莫 布瑞莫 右滅達樂 滅達樂 本達樂 右本達樂 殺紋寧 賽普洛 派美尼 滅派林 嘉賜黴素 土黴素 保米黴素 鏈黴素 三唑類 比多農 芬克座 得克利 四克利 滅特座 溴克座 環克座 護矽得 護汰芬 邁克尼 三泰芬 三泰隆 普克利 平克座 菲克利 易胺座 待克利 達克利 依普座 依滅列 撲克拉 披扶座 賽福座 尼瑞莫 芬瑞莫 嘧啶類 吡啶類 比芬諾 賽福寧 蕈狀芽孢桿菌 芬普福 三得芬 嗎啉類 哌啶類 克絕 克枯爛 護汰寧 快諾芬 普快淨 二氟林 脫芬瑞 賽座滅 安美速 亞托敏 平氟芬 氟克殺 福拉比 亞派占 白克列 賽氟滅 氟派瑞 嘉保信 滅普寧 福多寧 克收欣 百克敏 三氟敏 凡殺同 滅脫定 扶吉胺 白粉克 百蟎克 三苯醋錫 三苯羥錫 氟硫滅 達滅淨 賽芬胺 多寧 滅芬農 富米綜 滅速克 維利黴素 礦物油、有機油 生物性來源 無機鹽類 保粒黴素甲 達滅芬 曼普胺 倍利芬 撲殺熱 三賽唑 熱必斯 百快隆 芬諾尼 加普胺 四氯異苯腈 腈硫醌 硫磺 蓋普丹 四氯丹 福爾培 蟎離丹 益發靈 甲基益發靈 克熱淨 銅劑 富爾邦 免得爛 甲基鋅乃浦 得恩地 鋅錳乃浦 錳乃浦 益穗成分 鋅乃浦 虎杖萃取 福賽得 亞磷酸 海帶多糖 亞汰尼 二甲醯亞胺類 依普同 克氯得 撲滅寧 免克寧 硫代磷酸酯類 丙基喜樂松 護粒松 白粉松 亞賜圃 二硫戊環類 芳香烴類與 芳香雜環類 五氯硝苯 大克爛 二氯甲氧苯 脫克松 依得利 普拔克 納他黴素 茶樹精油 枯草桿菌 液化澱粉芽孢桿菌 毆殺斯 芬殺蟎 哌嗪類 咪唑類 三苯基氯化錫 喹唑啉酮類 苯吡咯類 芳香烴類 氨基甲酸鹽類 微生物 (桿菌屬) 植物萃取物 硫代磷酸脂類 & 二硫戊環類 琥珀酸脫氫酶抑制劑 醯基苯胺類殺菌劑 丁内酯類 噁唑烷酮類 唑類 異噻唑啉酮類 芳香雜環類 羧酸類 吡喃葡醣類抗生素 苯胺嘧啶類 多烯類 影響細胞膜通透性,脂肪酸 微生物對病原菌細胞膜之破壞 結合麥角固醇 粒線體電子傳遞複合物III 細胞色素bc1 Qo位置 粒線體電子傳遞複合物III 細胞色素bc1 Qi位置 氧化磷酸化作用解偶聯劑 電子傳遞過程複合物I-NADH氧化還原酶 幾丁質生合成酶 纖維素生合成酶 水楊酸途徑 水楊酸途徑 水楊酸 途徑 固醇類生合成作用過程C14-去甲基化作用 固醇類生合成作用過程� 14 -還原酶與� 8 →� 7 異構酶 os-2, HOG1滲調作用有關MAP/histidine-kinase 所啟動之訊息傳遞過程 訊息傳遞 (機制未知) 蛋白質生合成(轉譯起始) 蛋白質生合成(延長步驟) 蛋白質生合成(終止步驟) 甲硫胺酸生合成 蛋白質生合成(轉譯起始) DNA/RNA生合成 第二型DNA拓樸異構酶 RNA生合成酶 I 腺苷脫氫酶 苯并咪唑類 os-1, Daf1滲調作用有關MAP/histidine -kinase所啟動之訊息傳遞過程 有絲分裂過程微管蛋白組合 與B1無交互抗性 有絲分裂過程 微管蛋白組合 細胞分裂 類血影蛋白之去定域化 有絲分裂過程微管蛋白組合 胺基苯酚類 固醇類生合成之角鯊烯環氧化酶 硫代胺基甲酸鹽類 丙烯胺類 磷酸酯 ATP運輸 粒線體電子傳遞複合物III 細胞色素bc1 Qo位置 有機錫 氧化磷酸化作用 ATP生合成酶抑制 三唑嘧啶類 二硝基苯胺類 二硝基酚丁烯酯類 噻吩醯胺類 酚氧基喹啉類 肽醯嘧啶核苷 細胞膜破壞 黑色素生合成過程還原酶 黑色素生合成過程還原酶抑制劑 黑色素生合成過程脫水酶 黑色素生合成過程脫水酶抑制劑 Melanin Biosynthesis Inhibitors: Polyketide synthase (MBI-P) 黑色素生合成過程 聚酮合成酶 黑色素生合成過程 聚酮合成酶抑制劑 纈胺醯胺胺基甲酸類 肉桂醯胺類 苦杏醯胺類 胺基吡唑 啉酮類 固醇類生合成C4-去甲基化 作用之3-酮還原酶 C4-去甲基化作用之 3-酮還原酶抑制劑 氰基亞甲基噻唑類 嘧啶酮腙類 氰肟乙醯胺類 鄰胺甲醯苯甲酸類 苯併三嗪類 苯磺醯胺類 噠嗪酮類 四唑基肟類 吡喃葡醣類抗生素 苯乙醯胺類 胍類 喹啉基醋酸鹽類 植物 萃取物 多醣 噻唑 醯胺類 苯併異 噻唑類 苯併噻 二唑類 噻二唑類 吡唑醯胺類 吡啶醯胺類 苯基苯醯胺類 氧硫環醯胺類 硫氮環胺類 二苯甲酮類 苯甲酰吡啶 螺縮銅胺類 硫脲甲酸類 乙胺基噻唑羧酰胺類 羥基-2-胺基嘧啶類 吡喃醣 醛酸類 吡喃 六碳醣類 抗生素 四環素類抗生素 甲氧基丙烯酯類 甲氧基乙酰胺類 肟乙酸酯類 二氫二惡嗪類 噁唑烷二酮類 甲氧基胺基甲酸酯類 苯甲基 胺基甲酸鹽類 三氟乙基胺基甲酸鹽類 無機銅類 無機硫磺類 三嗪類 氯腈類 二硫代胺基甲酸鹽類 鄰苯二甲醯亞胺類 硫醯胺類 蒽醌類 喹噁啉類 順丁烯二酰抱亞胺類 硫代胺基甲酸鹽類 胍類 苯基脲類 肌動蛋白/肌球蛋白/絲束蛋白等功能 吡啶甲基苯醯胺類 電子傳遞過程複合物II-琥珀酸脫氫酶 磷脂質生合成作用-甲基轉移酶 脂質過氧化作用 暫時之作用機制或抗性風險與未確認 本殺菌劑作用機制分群是參考 FRAC fungicide list (出自 www.frac.info/publications) 本作用機制分群會根據藥劑最新研究成果而調整。 黃色區間表示目前藥劑普遍被接受之作用機制標靶, 或此藥劑已知具抗性及交互抗性藥劑分群。 儘管如此,同類群藥劑於部分病原可能不具交互抗性 、或有不完全交互抗性之情形發生。 本表提供的內容為在出版時研究所知之資料,FRAC 及其成員公司皆不對本表內容的完整性及正確性做任何承諾。 作用機制分群 次分群 作用標靶(已知) 或可能作用標靶 FRAC 編碼 (#) 化學結構分群 作用機制 次分群名稱 棘孢木黴菌 鏈黴菌屬 木黴菌屬 黏帚黴菌 苯醯胺類 FRAC及其成員公司對本表涉及其應用也不負任何法律責任。 N-苯基胺基甲酸鹽類 圖例: O O P S O S O O O P N O N N O O S S O P O S S O O O O S N H O N H O O O S O O N H O O N H N F F F Cl F F F S N O N H Br Br O F F F F F F N N O N H F F F S N N O N H F F F Cl Cl N N O N H Cl O N N O N H F N N O N H F F N O N H Cl N S N H O N H S N O O O N O O H Cl Cl N H O O Cl N O H N N O N N N NH S O O N O H N NH N H N N H O O N O N N H N H O O N H N O N H NH N H S N H O O O O S Cl N O O O O N O O O N O O O O N O O O O N O O O N O S O O N H O O NH O O NH N H OH O H OH OH O H O H N H NH 2 N H NH 2 O O H NH N N NH N N O N O O O N N O O O O OH OH N OH O OH O OH NH 2 OH Chiral NH N N N H NH O N H 2 O O H O H OH OH OH O OH N O N H 2 N N H NH 2 O O N NH 2 NH O HO N Cl N N N O O N N N Cl Cl O O N N N Cl Cl N N N O H Cl N N N O H Cl NH N N H N Cl Cl Cl O O Cl Cl Cl OH Cl N N F O H N N N H S Cl Cl N Cl N O Cl O N Cl Cl Cl O N N N Br O O N N N Cl O Cl Cl Cl N N O OH Cl N N Cl O H N F N F N N N N F O H Si N N N O F Cl Cl OH N Cl N N OH N Cl N N Cl O H N Cl N N Cl N O N N O H O H N N N Cl N Cl N N Cl F N Si N N F Cl N Cl N N N S Cl Cl N O N N O Cl N Cl N N O F F F F N Cl N N N F N N Cl Cl N N N O O O N N N Cl Cl Cl Cl N O N N Cl N N O F F F O O O N N N O O N Cl N N O N O O N N S O N H O H Cl Cl N O O N O N O N Cl Cl N H N O O F F N H N N H N N S N H NH S N H N H S O O O O O O N H O O N F F F Cl N H O Cl Cl O O O O O Br I N N O O Cl Cl N O F Cl O O N O Cl O O O H N N N Cl N O O Cl Cl N N O OH N H NH 2 OH N H OH O O H N H 2 OH O O O O O O H O N H I N N Cl N H O F F N N Cl N S O O N N N S O O N F Br S O O N N N O N H O O O O N H F F F N O O O N N Cl O N H O Cl N Cl O N H O O O O Cl N O Cl O N N Cl O O NH Cl O N O Cl O NH 2 Cl Cl N + O O Cl Cl Cl Cl Cl N + O O Cl Cl Cl Cl N + O O O N N O O O O N N O N H O O N H N O N O N O N O O N O O O N N O O N O N O O N N O Cl F N O N Cl N H O O N O O O O N F F F N N S O NH O N O O O O O N O O NH S Si O N H Cl N N H Cl N + O O F F F F F F N + O O Sn OH Sn Cl Sn O O N N N N NH 2 N + O O N + O O O O N + O O N + O O O O Cl Cl N H O N Cl Cl N O Cl Cl Cl O O N H N Cl Cl Cl Cl N N S O S O N N N N Cl S F Cl S O O N N Cl S F Cl S O O N H NH 2 N H N H N H NH 2 NH O S N H S O O O O N S O O S N N O S N H O S Cl N N Cl O S N N Cl Cl Cl N H O Cl S N N Cl O O N H O O O N H N H O O N H O N H O O N S F Cl Cl N H S O O N + O O F F F Cl Cl Cl Cl Cl N H Cl O O O H O O N N H O N H N N N N H N N N Cl N N N + O Cl O N N H Cl O O H OH OH O N H OH O H O H O H OH OH OH O H N H N H 2 NH 2 + O O O O N Cl Cl N O (CH 2 ) C H 3 11 N O (CH 2 ) C H 3 n = 10 to 13 n = 12: ~ 70% n OH N O N N N S S 2 Zn 2+ OH O O HO HO OH OH O OH O HO OH O OH O HO O OH O HO OH H n N H Cl N N N Cl Cl S N O O Cl Cl Cl S N O O Cl Cl Cl Cl O S N O Cl Cl Cl N H N H S S S S Zn 2+ N H N H S S S S Mn 2+ Cl S O P O O Cl N N H O S N N H O O P O - O O H Al +++ 3 O Cl Cl O N H S S N H S S Zn (NH 3 )- 3 N H S S N H S S x S N S S N S N H N H S S S S Zn 2+ Cl O Cl Cl Cl O N O N S N N N H O O I O O N H O N H O O Cl N S S 3 Fe 3+

Transcript of FRAC Classification of Fungicides · 2020-01-20 · pyrimethanil mepanipyrim cyprodinil hymexazole...

Page 1: FRAC Classification of Fungicides · 2020-01-20 · pyrimethanil mepanipyrim cyprodinil hymexazole octhilinone isoxazoles isothiazolones oxolinic acid (bactericide) butyrolactones

ferbam

mancozeb

propineb

#M6 sulphamides

C2: inhibition of complex II: succinate-dehydrogenase

# 7 SDHI (Succinate dehydrogenaseinhibitors)

FRAC Mode of Action Poster ©This version updated March 2019

pyridines

Unknown Mode of Action

C: Respiration

nzovindiflupyr

Extract from the cotyledons of

lupine plantlets

作物永續發展協會 台灣分會

Since 2001

財團法人植物保護科技基金會Plant Protection Science And Technology Foundation

OSBPI Oxysterol bindingprotein homologue inhibition

(Giant KnotweedExtract)

1,2,4,-thiadiazole

triazoles

pyridines

piperazines

pyrimidines

Polyoxin B

flumorph

dimethomorph

pyriofenonemetrafenone

thifluzamide

penflufen

furametpyr

isofetamid

carboxin

iprovalicarb

phenylacetamides

pyridazinones

benzene-sulfonamides

valinamide carbamates

diclomezine

flusulfamide

valifenalate

benthiavalicarb

pyrimorph

cinnamic acidamides

mandelic acid amides

mandipropamidpiperalin

pepridyl pyrimidine nucleoside

piperidines

fenpropidin

spiroketal-amines

spiroxamine

morpholines

dodemorph

fenpropimorph

tridemorph

aldimorph

fenpiclonil fludioxoniloxytetracycline(bactericide)

triforine

pyrifenox

fenarimol

pyrisoxazole

nuarimol

triflumizole

imazalil

pefurazoate

oxpoconazole

prochloraz

fenhexamid

fenpyrazamine

triadimenol

penconazole

propiconazole

triticonazole

mefentrifluconazole

triadimefon

myclobutanil

tetraconazole

metconazole

tebuconazole

fluquinconazole

fenbuconazole

flutriafol

hexaconazole

flusilazole

triazolinthioneprothioconazole

imibenconazole

epoxiconazole

diniconazole

difenoconazole

simeconazole

cyproconazole

bitertanol

bromuconazole

azaconazole

etaconazole

ipconazole

pyrimethanil

mepanipyrim

cyprodinil

octhilinonehymexazole

isothiazolonesisoxazoles

oxolinic acid(bactericide)

oxazolidinonesbutyrolactones

acylalanines

oxadixylofurace

metalaxyl-M

furalaxyl

benalaxyl-M

dimethirimol

ethirimol

metalaxyl

bupirimate

benalaxyl

quinoxyfen proquinazid

fluopimomide

fluopicolide

phenamacrilethaboxam

thiophanate

thiophanate-methyl

thiabendazole

pyridinylmethyl-benzamide

aminocyanoacrylates

aryloxyquinoline quinazolinone

diethofencarb

* negative cross-resistance to B1

pencycuron

benzophenone benzoylpyridine

imidazoles

streptomycin(bactericide)

kasugamycinblasticidine-S

zoxamide

benzimidazoles

thiophanates

toluamide

benomyl

carbendazim

fuberidazole

ethylamino-thiazolecarboxamide

triazoxide

tebufloquinferimzone

teclofthalam

cymoxanil

flutianil

picarbutrazoxvalidamycin

dodine

cyflufenamid

#U12

#U06 # 37

#36 benzotriazines

phthalamic acid#34 #35 #27

#U13 #U14

#U16 #U17

#U18

thiocarbamates

terbinafine(antimycotic)

pyributicarb(herbicide)

naftifine(antimycotic)

amino-pyrazolinones

hydroxyanilides allylamines

cyanoacetamide oxime

cyano-methylene thiazolidine

pyrimidinone-hydrazones

4-quinolyl acetate

• Temporary status; information no mode of action and/or resistance risk is still uncertain

dimethachlone

vinclozolin

iprodinoe

chlozolinate

procymidone

dicarboximides

boscalid

aryl-phenyl-ketones

oxycarboxin

fenfuram

oxathiin-carboxamidespyridine-carboxamides

pydiflumetofen

F2: phospholipid biosynthesis methyltransferase

pyraziflumid

pyrazophos

iprobenfos

edifenphos

dicloran

biphenyl

tolclofos-methyl

FRAC Classification of FungicidesFungal control agents by cross resistance pattern and mode of action 2019 (www.frac.info)

B: Cytoskeleton and Motor Proteins 細胞骨架與微管動力蛋白 C: Respiration 呼吸作用

A: Nucleic Acids Metabolism 核酸代謝

G: Sterol Biosynthesis in Membranes 固醇類生合成

D: Amino Acid and Protein Synthesis 胺基酸與蛋白質生合成 E: Signal Transduction 信息傳遞

Unknown Mode of Action 未知機制 BM : Biologicals with Multiple Modes of Action多作用點生物型殺菌劑

NC : Not Classified 未分類

C7: ATP transport(proposed)

# 38

silthiofamfamoxadone

imidazolinones

fluazinam

fluoxastrobin

thiazole carboxamides

polypeptide lectinBM 01: plant extract

(BLAD)

Phosphorous acid

phosphorousacid

P6: microbial elicitors#P06

laminarin

P4: polysaccharideelicitors

#P04 polysaccharide

P1: salicylate related

#P01 benzothiodiazole BTH

A1: RNA polymerase I A2: adenosin-deaminase

A4: DNA topoisomerasetype II (gyrase)

# 31 carboxylic acids# 32 heteroaromatics

# 4 # 8 PA-fungicides (PhenylAmides) hydroxy(2-amino)-pyrimidines

benodanil

mepronil

flutolanil

phenyl-benzamides

fluopyram

furan-carboxamides

pyridinyl-ethyl-benzamides

phenyl-oxo-ethyl-thiophene amide

pyraoxystrobin

enoxastrobin

coumoxystrobin

azoxystrobin

mandestrobin

inpyrfluxam

sedaxane

flufenoxystrobin

picoxystrobin

orysastrobin

dimoxystrobin

oximino-acetamides

methoxy-acetamides

methoxy-acrylates

metominostrobin

fenaminstrobinpyribencarb

triclopyricarb

benzyl-carbamates

pyrametostrobin

pyraclostrobin

kresoxim-methyl

trifloxystrobin

fenamidone

dihydro-dioxazines

oximino-acetates

fenpicoxamidamisulbrom ametoctradin

picolinamide

fentin chloride

fentin hydroxide

fentin acetate

# 23 # 24

fluxapyroxad

penthiopyrad

bixafen

benzovindiflupyr

isopyrazam

isoflucpyram

fluindapyr

diflumetorim tolfenpyrad fenazaquin cyazofamid

prothiocarb

iodocarb

propamocarb

oxathiapiprolin

# 44

chloroneb

etridiazole

# 14

F3: cell peroxidation (prop.)aromatic hydrocarbons & heteroaromatics

phosphorothiolates & dithiolanes

phosphorothiolates

aromatichydrocarbons

tecnazene(TCNB)

dithiolanes

isoprothiolane

# 6

thiazole-carboxamides N-methoxy-(phenyl-

ethyl)-pyrazole-carboxamides

pyrazole-carboxamides-

# 7

C2: complex II: succinate-dehydrogenase

SDHI (Succinate DeHydrogenase Inhibitors)phenylureas

B4: cell division(unknown site)

# 20

B1: β-tubulin assembly in mitosis

# 1

# 43

B5: delocalisation ofspectrin-like proteins

benzamides

E1: signal transduction (mechanism unknown)

#13

D3: protein synthesis(ribosome, initiation step)

hexopyranosyl antibiotics

D1: methionine biosynthesis(cgs gene) (proposed)

# 9 Anilino-Pyrimidines (AP fungcides)

#M12

tolylfluanidcaptafol

chinomethionat

folpetthiocarbamates (electrophiles)

methasulfocarb

fluoroimide

iminoctadine

mixture ofiminoctadine

and otherpolyamines

guazatine

#M07 bis-guanidines

(membrane disruptors, detergents)

#M10 #M06 #M04 phthalimides

(electrophiles)sulphamides

(electrophiles)

chlorothalonildithianon

dichlofluanidcaptan

anilazine

sulphur

#M08

S

#M02 #M09

#M01

inorganic

triazines(unspecified mechanism)

(electrophiles)

dithiocarbamates& relatives

(electrophiles)

copperpreparations

Cu

inorganic(electrophiles)

#M03

febram zinc thiazole

maneb

zineb

propineb

ziramthiram

mancozeb

metiram

A3: DNA / RNA synthesis (prop.)

D2: protein synthesis(ribosome, termination step)

enopyranuronic acid

D4: protein synthesis(ribosome, initiation step)

# 25 glucopyranosyl antibiotics

D5: protein synthesis(ribosome, elongation step)

# 41 tetracycline antibiotics

G1: C14-demethulase in sterol biosynthesis (erg11/cyp51)

(SBI : Class I)# 3

sulfamoyl-triazole

DMI-fungicides (DeMethylation Inhibitors)

H:Cell Wall Biosynthesis 細胞壁生合成H4: chitin synthase

C: Respiration 呼吸作用

F: Lipid Synthesis or Transport / Membrane Integrity or Function 脂質生合成與膜完整性

P: Host Plant Defence Induction 防衛反應誘發

Mineral oils, organic oils,

inorganic salts material of biological orign

glucopyranosylantibiotic guanidinestetrazolyloxime

# 19 Polyoxins

E3: osmotic signal transduction MAP / histidine kinase (os-1, Daf1)

# 2

C1: complex I NADH Oxido-reductase

quinazolinepyrimidinamine pyrazole-5-carboxamide# 39

cyano-imidazole

C4: complex III cytochrome bc1(ubiquinone reductase) at Qi site

# 21 Qil fungicides (Quinone inside Inhibitors)

triazolo-pyrimidylamine

# 45 QoSI-fungicide (stigmatellin binding)

C8: inhibition of complex IIIcytochrome bc1(ubiquinone reductase)at Qo site stigmatellin binding sub site)

thiophene-carboxamides

2,6-dinitro-aniline

MBC fungicides (=Methyl Benzimidazole Carbamates)

B6: actin/myosin/fimbrin function

H5: cellulose synthase

# 40 Carboxylic Acid Amides(CAA fungicides)

quintozene(PCNB)

oxazolidine-diones

methoxy-carbamates

C3: complex III cytochrome bc1 (ubiquinol oxidase) at Qo site (cyt b gene)

# 11 QoI fungicides (Quinone outside Inhibitors)

acibenzolar-S-methyl

thiadiazole carboxamide

P3: salicylate related

#P03

#P02

isotianil

probenazoletiadinil

P2: salicylate relatedbenzothiazole

Trichodermaatroviride

(strain SC1)

Trichodermaatroviride

Trichodermaatroviride

Trichodermaasperellum

(strain I-1237)

(strain T34)

(strain LU132)

FungalTritroderma spp.

(strain K61)

(strain J1446)Streptomycesgriseovirides

Gliocladiumcatenulatum

FungalGliocladium spp.Bacterial

Streptomyces spp.

fosetyl-alethyl-phosphonates

P7: phosphonates#P07 phosphonates

BacterialBacillus spp.

Bacillusmycoides

(Isolate J)

FungalSaccharomyces spp.

Reynoutriasachalinensis

P5: anthraquinoneelicitors

#P05 plant extract

# 47 cyanoacrylates # 50

B3: β-tubulin assembly in mitosis

# 22 benzamides and thiazole carboxamides

azanaphthalenes

E2: osmotic signal transduction MAP / histidine-kinase (os-2, HOG1)

# 12 phenylpyrroles (PP-fungicides)

G4: squalene epoxidase insterol biosynthesis (erg1)

# 18 (SBI : Class IV)

G3:3-keto reductase inC4-demethylation (erg27)

# 17 (KRI fungicides KetoReductase Inhibitors)

(SBI : Class III)

G2: ∆14-reductase and ∆8→∆7-isomerase in sterolbiosynthesis (erg2, erg24)

Amines(“Morpholines”) (SBI : Class II) # 5

B2: β-tubulin assembly

in mitosis*

# 10 N-phenyl carbamates

C6: inhibitors of oxidative

phosphorylation, ATP synthase

# 30 organo tins

C5: uncouplers of oxidative phosphorylation

# 29

dinitrophenyl crotonates

meptyl dinocap

binapacryl

Microbial (Bacillus sp.)

Bacillus sp. andthe fungicidal lipopeptides produced

Bacillusamyloliquefaciens

(synonym B. subtilis) strains:

QST 713 FZB24MBI600 D747

F9: lipid homeostasisand transfer/storage

# 49

F8: ergosterolbinding

# 48 polyene

natamycin(pimaricin)

F7: cell membranedisruption

# 46 plant extract

Plant oils (mixtures)eugenol, geraniol

thymol

Melaleucaalternifolia

(Tea Tree Extract)

anthraquinones(electrophiles)

maleimides (electrophiles)#M11

chloronitriles(unspecified mechanism)

#M05

I2: dehydratase inmelanin biosynthesis

I1: dehydratase inmelanin biosynthesis

#16.2 #16.1 Melanin Biosynthesis Inhibitors: Dehydratase (MBI-D)

carboxamide

cyclopropane carboxamide

diclocymetfthalide

tolprocarb

Melanin Biosynthesis Inhibitors: Reductase (MBI-R)

isobenzo-furanone

pyrrolo-quinolione

pyroquilon

F4: cell membrane permeability,fatty acids (prop.)

# 28 carbamates

F6: microbial disrupters ofpathogen cell membranes

piperidinyl-thiazole-

isoxazoline tricyclazole

triazolobenzo-thiazole

fenoxanil

carpropamid

I3: polyketidesynthase in melanin

biosynthesis

#16.3

trifluoroethyl-carbamate

Cell walls ofSaccharomyces

cerevisiaeStrain LAS117

propionamide

M: Chemicals with Multi-Site Activity 多點作用機制

quinoxalines(electrophiles)

pyrimidinamines,pyrazole-MET1, quinazoline

pyrazine-carboxamides

N-cyclopropyl-N-Benzyl-pyrazole-

carboxamides

BM 02: microbial (living microbes or extract,metabolites)

I: Melanin Synthesis in Cell Wall 黑色素生合成

醯基丙胺類

免賴得

貝芬替

腐絕

甲基多保淨

多保淨

賓克隆

氟比來

苯醯胺類

座賽胺

歐索林酸

依瑞莫

布瑞莫

右滅達樂

滅達樂本達樂

右本達樂

殺紋寧

賽普洛

派美尼

滅派林

嘉賜黴素

土黴素

保米黴素

鏈黴素

三唑類

比多農

芬克座 得克利

四克利

滅特座

溴克座

環克座

護矽得

護汰芬

邁克尼

三泰芬

三泰隆

普克利

平克座

菲克利

易胺座

待克利

達克利

依普座

依滅列

撲克拉

披扶座

賽福座

尼瑞莫

芬瑞莫

嘧啶類

吡啶類

比芬諾

賽福寧

蕈狀芽孢桿菌

芬普福

三得芬

嗎啉類

哌啶類

克絕克枯爛

護汰寧

快諾芬 普快淨

二氟林 脫芬瑞 賽座滅 安美速

亞托敏

平氟芬

氟克殺

福拉比

亞派占

白克列

賽氟滅

氟派瑞

嘉保信 滅普寧

福多寧

克收欣

百克敏

三氟敏

凡殺同

滅脫定

扶吉胺白粉克

百蟎克

三苯醋錫

三苯羥錫

氟硫滅達滅淨

賽芬胺

多寧

滅芬農

富米綜

滅速克

維利黴素

礦物油、有機油生物性來源無機鹽類

保粒黴素甲 達滅芬

曼普胺

倍利芬

撲殺熱

三賽唑

熱必斯

百快隆

芬諾尼

加普胺

四氯異苯腈腈硫醌硫磺

蓋普丹

四氯丹

福爾培

蟎離丹益發靈

甲基益發靈

克熱淨

銅劑

富爾邦

免得爛

甲基鋅乃浦

得恩地

鋅錳乃浦

錳乃浦

益穗成分

鋅乃浦

虎杖萃取

福賽得

亞磷酸

海帶多糖亞汰尼

二甲醯亞胺類

依普同

克氯得

撲滅寧

免克寧

硫代磷酸酯類

丙基喜樂松

護粒松

白粉松

亞賜圃

二硫戊環類

芳香烴類與芳香雜環類

五氯硝苯

大克爛

二氯甲氧苯脫克松

依得利

普拔克

納他黴素茶樹精油

枯草桿菌 液化澱粉芽孢桿菌

毆殺斯

芬殺蟎

哌嗪類

咪唑類

三苯基氯化錫

喹唑啉酮類

苯吡咯類

芳香烴類氨基甲酸鹽類 微生物 (桿菌屬)

植物萃取物

硫代磷酸脂類 & 二硫戊環類

琥珀酸脫氫酶抑制劑

醯基苯胺類殺菌劑

丁内酯類 噁唑烷酮類

異口咢唑類 異噻唑啉酮類

芳香雜環類 羧酸類

吡喃葡醣類抗生素

苯胺嘧啶類

多烯類

影響細胞膜通透性,脂肪酸 微生物對病原菌細胞膜之破壞

結合麥角固醇

粒線體電子傳遞複合物III 細胞色素bc1 Qo位置

粒線體電子傳遞複合物III 細胞色素bc1 Qi位置

氧化磷酸化作用解偶聯劑

電子傳遞過程複合物I-NADH氧化還原酶

幾丁質生合成酶 纖維素生合成酶 水楊酸途徑 水楊酸途徑

水楊酸途徑

固醇類生合成作用過程C14-去甲基化作用

固醇類生合成作用過程�14-還原酶與�8→�7異構酶

os-2, HOG1滲調作用有關MAP/histidine-kinase所啟動之訊息傳遞過程

訊息傳遞 (機制未知)蛋白質生合成(轉譯起始)

蛋白質生合成(延長步驟)

蛋白質生合成(終止步驟)甲硫胺酸生合成

蛋白質生合成(轉譯起始)

DNA/RNA生合成第二型DNA拓樸異構酶

RNA生合成酶 I 腺苷脫氫酶

苯并咪唑類

os-1, Daf1滲調作用有關MAP/histidine-kinase所啟動之訊息傳遞過程

有絲分裂過程微管蛋白組合

與B1無交互抗性

有絲分裂過程微管蛋白組合

細胞分裂

類血影蛋白之去定域化有絲分裂過程微管蛋白組合

胺基苯酚類

固醇類生合成之角鯊烯環氧化酶

硫代胺基甲酸鹽類

丙烯胺類

磷酸酯

ATP運輸

粒線體電子傳遞複合物III 細胞色素bc1 Qo位置

有機錫

氧化磷酸化作用ATP生合成酶抑制

三唑嘧啶類

二硝基苯胺類

二硝基酚丁烯酯類

噻吩醯胺類

酚氧基喹啉類

肽醯嘧啶核苷

細胞膜破壞

黑色素生合成過程還原酶

黑色素生合成過程還原酶抑制劑

黑色素生合成過程脫水酶

黑色素生合成過程脫水酶抑制劑Melanin Biosynthesis Inhibitors:

Polyketide synthase (MBI-P)

黑色素生合成過程聚酮合成酶

黑色素生合成過程聚酮合成酶抑制劑

纈胺醯胺胺基甲酸類

肉桂醯胺類

苦杏醯胺類

胺基吡唑啉酮類

固醇類生合成C4-去甲基化作用之3-酮還原酶

C4-去甲基化作用之3-酮還原酶抑制劑

氰基亞甲基噻唑類 嘧啶酮腙類

氰肟乙醯胺類鄰胺甲醯苯甲酸類

苯併三嗪類

苯磺醯胺類

噠嗪酮類

四唑基肟類 吡喃葡醣類抗生素

苯乙醯胺類

胍類喹啉基醋酸鹽類

植物萃取物

多醣噻唑

醯胺類

苯併異噻唑類

苯併噻二唑類

噻二唑類

吡唑醯胺類

吡啶醯胺類

苯基苯醯胺類

氧硫環醯胺類

硫氮環胺類

二苯甲酮類 苯甲酰吡啶

螺縮銅胺類

硫脲甲酸類

乙胺基噻唑羧酰胺類

羥基-2-胺基嘧啶類

吡喃醣醛酸類 吡喃

六碳醣類抗生素

四環素類抗生素

甲氧基丙烯酯類

甲氧基乙酰胺類

肟乙酸酯類

二氫二惡嗪類

噁唑烷二酮類

甲氧基胺基甲酸酯類

苯甲基胺基甲酸鹽類

三氟乙基胺基甲酸鹽類

無機銅類

無機硫磺類

三嗪類

氯腈類

二硫代胺基甲酸鹽類

鄰苯二甲醯亞胺類 硫醯胺類

蒽醌類

喹噁啉類

順丁烯二酰抱亞胺類

硫代胺基甲酸鹽類

胍類

苯基脲類

肌動蛋白/肌球蛋白/絲束蛋白等功能

吡啶甲基苯醯胺類

電子傳遞過程複合物II-琥珀酸脫氫酶

磷脂質生合成作用-甲基轉移酶脂質過氧化作用

暫時之作用機制或抗性風險與未確認

本殺菌劑作用機制分群是參考 FRAC fungicide list(出自 www.frac.info/publications) 本作用機制分群會根據藥劑最新研究成果而調整。黃色區間表示目前藥劑普遍被接受之作用機制標靶,或此藥劑已知具抗性及交互抗性藥劑分群。儘管如此,同類群藥劑於部分病原可能不具交互抗性、或有不完全交互抗性之情形發生。

本表提供的內容為在出版時研究所知之資料,FRAC及其成員公司皆不對本表內容的完整性及正確性做任何承諾。

作用機制分群

次分群

作用標靶(已知)或可能作用標靶

FRAC 編碼 (#)

化學結構分群

作用機制次分群名稱

棘孢木黴菌

鏈黴菌屬

木黴菌屬

黏帚黴菌

苯醯胺類

FRAC及其成員公司對本表涉及其應用也不負任何法律責任。

N-苯基胺基甲酸鹽類

圖例:

OO

PS

O

S

OO

O

P

NON

NO

O

SS

O

P

OS

S

O

OO

O

S

NH

O

NHO

O

O

S O

O

NH

O

O

NH

N

F

F

FClFF

F

SN

O

NH

Br

Br

OFF FF

F

F

NN

O

NH

FF FS

NN

O

NH

FF F

Cl

Cl

NN

O

NH

ClO

NN

O

NH

F

NN

O

NH

FFN

O

NH

Cl

NS

NH

O

NH

S

N

O

O

ON

O

OH

Cl

Cl

NH

O

O

Cl

N

OH

N

N

O

NNN

NH

SO

O

N

OH

N

NH

NH

NNH

OO

N

O

NNH

NH

OO

NH

N O

NH

NH

NH

S

NH

O

O

O

O

S

Cl

N

OO

O

O

N

O

O

O

N

O

OO

O

N

O O

O

O

N

O O

O

N OS

O ONH

O O

NH

O

O

NH

NH

OH

OH

OH

OH

OH

OH

NH

NH2NH

NH2

OOH

NH

NN

NH

NN

O

N

O

O

O

NN

OO

O

OOH

OH

NOH

O

OH

OOH

NH2

OH

Chiral

NH

NN

NH

NH

O

NH2

O

OH

OH OH

OH

OH

O

OH

N

O

NH2N

NH

NH2O

O

N

NH2

NH

OHO

N

ClNN

N

O

O

NN

NCl

Cl

O

O

NN

NCl

Cl

NN

N

OH

Cl

NN

N

OH

Cl

NH

N

NH

NCl

ClCl

O

O

Cl

Cl Cl

OHCl

NN

F

OH

N

NNH

S

ClCl

N

Cl

N

O

ClO

N

Cl

Cl

Cl

O

N

NN

Br

O

O

NN

NCl

O

Cl

Cl Cl

N

N

O

OHCl

NN

Cl

OH

N

F

N

F

N

N

NN

FOH

Si

NN

N

OF

Cl

ClOH

N ClN

N

OH

N

Cl

NN

Cl

OHN

Cl

NN

Cl

N O

NN

OH

OH

NNN

Cl

N

Cl

N

N

Cl

F

N

Si

N

N

F

Cl

N

Cl

N

N

N

S

Cl

Cl

N O

NN

O

Cl

N

Cl

NN

OF

F

F

F

N

Cl

NN

N

FN

N

ClCl

N

NN

O

O

O

NN

NCl

Cl Cl Cl

N

O

N

N

Cl

NN

O

F F

FOO

O

N

N N O

O

NCl

NN O

N

O ONN

S

O

NH

OH

Cl

Cl

NO

O

N

O

N

O

N

Cl

Cl

NH

N

O

OF

F

NH

N

NH

N N

S

NH

NHS

NH

NH

S

O

O

OO

O

O

NH

O

O

N

F

F

F

Cl

NH

OCl

Cl

OO

O

OO

Br

I

N

N

O

O

Cl

Cl N

O

F

Cl

O

O

N

O

Cl

O

O

OH

N

NN

Cl

N

O

O

Cl

Cl

N

N

O OH

NH

NH2

OHNH

OH

O

OHNH2

OH

O

O

OO

OOH

O

NH

I

NN

ClNH

O

F

FN

N

Cl

NSO

O

N

N

NSO

O

N

F

Br

S

OO

N

N

NO N

H

O

O

O

O

NH

FFF

NO

O

ON

NCl O

NH

O

Cl

N

Cl

O

NH

O

O O

OCl

NO

Cl

ON

N

Cl

O

O

NH

Cl

O N

O

Cl

O

NH2

ClCl

N+O O

Cl Cl

Cl

ClCl

N+O O

Cl Cl

ClCl

N+O O

O

N N

OO

O

ON

NO N

H

O

O

NH

N

ON

O

NO

NO

O

NO

O

ONN

O

O

NO

NO

O

NN

OCl FN

ON

Cl

NH

O

O

NO O

O

ON

F

F

F

N

NS O

NH

O

NO

O

O

OO

NO O

NH

SSi

O

NH

Cl

NNH

Cl

N+

O

O

F

F F

F FF

N+

O

O

Sn

OH

Sn

Cl

Sn

OO

N

NN

N

NH2

N+

O O

N+O

O

O

O

N+O

O

N+

O O

O

O

Cl

Cl

NH

O

N

ClCl

N

O

Cl

Cl

Cl

O

O

NH

N

Cl Cl

ClCl

N

N

SO

SO

N

N

N

N

Cl

S

F

Cl SO

O

N

N

Cl

S

F

Cl SO

O

NH

NH2

NH

NH

NH

NH2

NH

O

SNH

SO

O

O

O

NS

O O

SN

N

O S

NH

OS

Cl

N

N Cl

OS

N N

Cl Cl

Cl

NH

O

ClS

N

N

Cl

O

O

NH

O

O

O

NH

NH

O

O

NH

O

NH

O

O N

S

F

Cl

Cl

NH

SO

ON+

O

OF

F F

Cl

ClCl

Cl

Cl

NH

Cl

OOOH

O

ON

NH

O

NH

N

NN

NH

N

N

NCl

NN

N+

O Cl

ONN

H Cl

O

OH

OH

OH

ONH

OH

OH

OH

OH OH

OH

OH

OH

NH

NH2

NH2+

O

O

O ON

ClCl

N O(CH2)CH3

11

N O(CH2)CH3

n = 10 to 13n = 12: ~ 70%

n

OH

NO

NN

N

S

S

2

Zn2+

OHO

OHO

HO

OH

OHO

OHOHO

OH

O

OHOHOO

OHOHO

OH

H n

NH

ClN

NN

Cl

Cl

SN

O

O ClCl

Cl

SN

O

O ClCl

ClCl

O

SN

O

ClCl

ClNH

NH

S

S

S

S Zn2+

NH

NH

S

SS

S Mn2+

ClS

OP

O

OCl

NNH

O

S NNH

O

O

P O-O

O

HAl+++

3

O

Cl

Cl

O

NH

SS

NH

SS

Zn (NH3)-

3

NH

SS

NH S

S

x

S

N SS N

S

NH

NH

S

SS

S Zn2+

Cl

O

Cl

Cl

ClO

N O

N

S

N

N

NH

O

O

I

O

O

NH

O

NH

O

O

Cl

N

S

S

3

Fe3+