Comprehensive Analysis of the New Pyrazole Amide Fungicide - Furametpyr
Product Overview and Development History
Furametpyr, as a representative compound of pyrazole amide fungicides, was first developed and marketed by Sumitomo Chemical Co., Ltd. in Japan in 1996. The birth of this innovative compound is based on the structural foundations of two important fungicides—Sumitomo's metalaxyl and Japan Pesticides' fluazinam. Researchers cleverly introduced a benzofuran group onto the nitrogen atom of the amide group through molecular design, ultimately obtaining this structurally novel and highly active fungicidal molecule.
From the perspective of fungicide development history, furametpyr holds milestone significance as it is the first pyrazole amide compound among succinate dehydrogenase inhibitor (SDHI) class fungicides. This breakthrough discovery has opened new directions for subsequent SDHI-class fungicide research and development, with international agrochemical giants such as Syngenta and BASF developing various performance-enhanced pyrazole amide products based on furametpyr's molecular structure.
Chemical Properties and Physicochemical Characteristics
The systematic chemical name for furametpyr is rac-5-chloro-1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-3H-benzofuran-4-yl]pyrazole-4-carboxamide; its molecular formula is C17H20ClN3O2 with a relative molecular mass of 333.813; CAS registration number: 123572-88-3. This compound appears as colorless or light brown crystalline solid at normal temperature and pressure with distinct melting point characteristics.
Analyzing from physicochemical properties perspective shows that furametpyr has a melting point of 150.2°C; under conditions at 25°C its vapor pressure is 4.7×10^-6 Pa indicating low volatility. Solubility tests reveal that this compound has a solubility in water at 225 mg/L (25°C), while showing significant differences in organic solvents: solubility in n-hexane is 1 g/L; toluene shows solubility at 30 g/L; methanol at134 g/L; isopropanol at36 g/L; acetone reaches109 g/L; cyclohexane achieves204 g/L; ethyl acetate stands64 g/L while chloroform peaks467g/Land acetonitrile hits58g/L.Its octanol/water partition coefficient (logP) standsat2 .36(25 °C),indicating certain lipophilicity.
Thermal stability studies indicate that around150 °C,f uram et pyr exhibits crystallization melting endothermic peak,and decomposition occurs within220–300 °C range accompanied by exothermic phenomena.Thermogravimetric analysis reveals mass loss begins around190 °C ,withsignificant acceleration once temperatures exceed250 °C.These thermodynamic data provide crucial reference points for determining formulation processingand storage conditions.
Mechanism Of Action And Biological Activity
Fur amet pyr actsas atypicalsuccinate dehydrogenaseinhibitor(SD HI ) targetingcomplex II(the succinate-coenzyme Q oxidoreductase)within mitochondrial electron transport chain.In-depth mechanism studies showthiscompound can strongly inhibit electron transfer systems using succinate assubstratebyinterferingwithkeymetabolite generationin tricarboxylic acid cycle(TCA cycle),resulting energy metabolism disruptionin pathogens leadingto bacteriostatic effects . Fromdisease control perspectives ,furam et pyr demonstrates unique dual action modes.On one hand,it effectively inhibits germination process from sclerotia to mycelial growth ;on other hand ,for already formed lesions pathogens,this agentcan blockfurther expansionof mycelium promoting pathogen inactivity thus controlling secondary infections.It’s particularly noteworthythatfuram et pyr also displays significant inhibitory activity againstsclerotial formationprocesses which adds special value during comprehensive disease management efforts . n### Control Spectrum And Application Techniques f uram et pyr showcases broad-spectrum antifungal activity especially exhibiting excellent control efficacyagainst basidiomycete pathogens.This agent proves outstandingly effective againstvariousplant diseases causedbyRhizoctoniaand Corticiumincludingimportantrice sheath blight,rice sclerotinia disease,and white root rot etc.Additionally,itshows goodcontrol effectsonwheat leaf spot diseasescausedbySeptoria fungi too . nIn practical applications common formulations include1 .5%granules ,0 .5%powdered form,and15 %wettable powderetc.Field trialdata indicatesapplicationwithin7 daysbefore inoculation(preventive treatment )up until three days post-inoculation(treatment application )achieves stablecontrol outcomes.Specifically,treatingwater surfaceusingeach10 mu withabout34 kgsof1 .5% granules yieldsideal results both preventivelyor therapeutically regardlessofthe approach taken.Lettersfromresearchers confirmthat environmental factors have limited impactontheeffectiveness offuram et p yr including soil types infiltration levels temperatureconditionswhich significantlyenhancesitsapplicabilityandreliabilityacrosscomplexfieldenvironments.# Synthesis Route And Process Features Fura met p y r synthesis follows typicalpreparation routesfor4-formamidopyrazoled compounds.Thecore synthetic strategy involves constructing keyamide bondsvia condensation reactions betweenbenzofuran structuredcompoundsandspecific acyl chlorides.This synthesis pathway shares similaritieswiththose usedfor similarfungicideslike thiamethoxamfluazinamfluopyram chlorfenapir revealingcommoncharacteristics inherentto pyrazo lamidetypecompoundssynthesis.Fromprocess standpoint,synthesizingfurame tp yr entailsmultiplecriticalstepsincludingchiral center constructionchlorination reactionsofthepy razoleringfinal amidation processes.Control overreactionconditions,catalyst selectionpurification methods greatly influenceyieldqualityofthe final product.Withadvancements insynthetic technologies,reports now existshowcasingoptimizedreactionconditions employingnew catalysts markedly improve yieldoptical purityofkey intermediates.# Market Status And Development ProspectsDespite beingoneoftheearliestdevelopedSDHIclassfungicides,f urame tp yr maintains clear market positioning focusedoncontrollingrice sheath blight.Theagent possessesexcellent systemic translocationactivity demonstrating moderateresidual effectivenessagainstsheathblight contributingtowards long-termstableapplicationsintheJapanese market.Howeversinceprolongeduse resistanceissueshave emergedleadingto decliningeffectivenessduration.Comparatively speaking,inChina f urame tp yr hasn’t securedofficialregistrationyet presentingpotential opportunities domestically consideringeconomic aspects.As matureSDHIclassfungicide variety,f urame t p y r boastsobviouscost-performance advantages regardingproduction costs promotion expensesespeciallyundercurrenthighoverallusage costs associatedwithSD HI classproducts.Outlook suggestsfuturedevelopment may face two pathways:on one sidethroughformulation improvementscombining techniques delayingresistance emergence expandingcontrol spectrum ;while on another corestructure remains viableleadcompound paving way towardsnext-generation SD HIfungicides.Additionally,given increasingdemandsforagriculturalproduct quality safety lower mammalian toxicityenvironmental friendlinesscould become competitive edges intothemarketplace.