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FRAC Code List ©*2017: Fungicides sorted by mode of action (including FRAC Code numbering) INTRODUCTION The following table lists commercial fungicides according to their mode of action and resistance risk. The most important bactericides are also included. The Table headings are defined as: MOA Code Different letters (A to I, with added numbers) are used to distinguish fungicide groups according to their biochemical mode of action (MOA) in the biosynthetic pathways of plant pathogens. The grouping was made according to processes in the metabolism starting from nucleic acids synthesis (A) to secondary metabolism, e.g. melanin synthesis (I) at the end of the list, followed by host plant defence inducers (P), recent molecules with an unknown mode of action and unknown resistance risk (U, transient status, until information about mode of action and mechanism of resistance becomes available), and chemical multi-site inhibitors (M). Fungicidal compositions of biological origin are grouped according to the main mode of action within the respective pathway categories. A newly introduced category “Biologicals with multiple modes of action” (BM) is used for agents from biological origin showing multiple mechanisms of action without evidence of a dominating mode of action. Target Site and Code If available, the biochemical mode of action is given. In several cases the precise target site may not be known, however, a grouping within a given pathway / functional cluster is still possible. Grouping can also be made due to cross resistance profiles within a group or in relation to other groups. Group Name The Group Names listed are based on chemical relatedness of structures which are accepted in literature (e.g. The Pesticide Manual). They are based on different sources (chemical structure, site of action, first important representative in group). Chemical Group Grouping is based on chemical considerations. Nomenclature is according to IUPAC and Chemical Abstract name. FRAC Code List© 2017 Page 1 of 12 Common name BSI/ISO accepted (or proposed) common name for an individual active ingredient expected to appear on the product label as definition of the product. Comments on Resistance Details are given for the (molecular) mechanism of resistance and the resistance risk. If fieldresistance is known to one member of the Group, it is most likely but not exclusively valid that cross resistance to other group members will be present. There is increasing evidence that the degree of cross resistance can differ between group members and pathogen species or even within species. For the latest information on resistance and cross resistance status of a particular pathogen / fungicide combination, it is advised to contact local FRAC representatives, product manufacturer’s representatives or crop protection advisors. The intrinsic risk for resistance evolution to a given fungicide group is estimated to be low, medium or high according to the principles described in FRAC Monographs 1, 2 and 3. Resistance management is driven by intrinsic risk of fungicide, pathogen risk and agronomic risk (see FRAC pathogen risk list). Similar classification lists of fungicides have been published by T. Locke on behalf of FRAG – UK (Fungicide Resistance, August 2001), and by P. Leroux (Classification des fongicides agricoles et résistance, Phytoma, La Défense des Végétaux, No. 554, 43-51, November 2002). FRAC Code Numbers and letters are used to distinguish the fungicide groups according to their cross resistance behaviour. The numbers were assigned primarily according to the time of product introduction to the market. The letters refer to P = host plant defence inducers, M = chemical multi-site inhibitors, U = unknown mode of action and unknown resistance risk, and BM = biologicals with multiple modes of action. Reclassification of compounds based on new research may result in codes to expire. This is most likely in the U – section when the mode of actions gets clarified. These codes are not re-used for new groups; a note is added to indicate reclassification into a new code. Last update: February 2017 Next update decisions: January2018 * Disclaimer The FRAC Code List is the property of FRAC and protected by copyright laws. The FRAC Code List may be used for educational purposes without permission from FRAC. Commercial use of this material may only be made with the express, prior and written permission of FRAC. Inclusion to the FRAC Code List is based on scientific evaluation of the mode of action of the active ingredients; it does not provide any kind of testimonial for the use of a product or a judgment on efficacy. FRAC Code List© 2017 Page 2 of 12 MOA TARGET SITE AND CODE A: nucleic acids synthesis A1 RNA polymerase I A2 adenosindeaminase GROUP NAME CHEMICAL GROUP COMMON NAME acylalanines PA – fungicides (PhenylAmides) hydroxy(2-amino-) pyrimidines A3 DNA/RNA synthesis heteroaromatics (proposed) oxazolidinones oxadixyl butyrolactones ofurace hydroxy(2-amino-) pyrimidines bupirimate dimethirimol ethirimol isoxazoles hymexazole isothiazolones octhilinone A4 DNA topoisomerase type II (gyrase) carboxylic acids carboxylic acids benzimidazoles MBC fungicides (Methyl ß-tubulin assembly Benzimidazole in mitosis Carbamates) B: Cytoskeleton and motor proteins B1 B2 ß-tubulin assembly in mitosis N-phenyl carbamates benalaxyl benalaxyl-M (=kiralaxyl) furalaxyl metalaxyl metalaxyl-M (=mefenoxam) thiophanates N-phenyl carbamates COMMENTS FRAC CODE Resistance and cross resistance well known in various Oomycetes but mechanism unknown. High risk. See FRAC Phenylamide Guidelines for resistance management Medium risk. Resistance and cross resistance known in powdery mildews. Resistance management required. 8 Resistance not known. 32 Bactericide. Resistance known. Risk in fungi unknown. oxolinic acid Resistance management required. Resistance common in many benomyl fungal species. Several target carbendazim site mutations, mostly fuberidazole E198A/G/K, F200Y in β-tubulin thiabendazole gene. Positive cross resistance between the group members. Negative cross resistance to Nthiophanate Phenylcarbamates. thiophanate-methyl High risk. See FRAC Benzimidazole Guidelines for resistance management. Resistance known. Target site mutation E198K. Negative cross diethofencarb resistance to benzimidazoles. High risk. Resistance management required. B3 benzamides toluamides zoxamide ß-tubulin assembly in mitosis thiazole carboxamide ethylamino-thiazolecarboxamide phenylureas benzamides 31 1 10 ethaboxam Low to medium risk. Resistance management required. 22 phenylureas pencycuron Resistance not known. 20 pyridinylmethylbenzamides fluopicolide Resistance not known. 43 phenamacril Resistance known in Fusarium graminearum. Target site mutations in the gene coding for myosin-5 found in lab studies. Medium to high risk. Resistance management required. 47 B4 cell division (proposed) 4 B5 delocalisation of spectrin-like proteins B6 actin/myosin/fimbrin cyanoacrylates aminocyanoacrylates function FRAC Code List© 2017 Page 3 of 12 MOA TARGET SITE AND CODE GROUP NAME CHEMICAL GROUP COMMON NAME C1 pyrimidinamines Pyrimidinamines diflumetorim complex I NADH Oxido-reductase pyrazole-MET1 pyrazole-5carboxamides tolfenpyrad phenyl-benzamides benodanil flutolanil mepronil C2 C. respiration SDHI (Succinatecomplex II: succinate-dehydro- dehydrogenase inhibitors) genase phenyl-oxo-ethyl thiophene amide pyridinyl-ethylbenzamides furan- carboxamides oxathiincarboxamides thiazolecarboxamides pyrazole-4carboxamides N-methoxy-(phenylethyl)-pyrazolecarboxamides pyridinecarboxamides pyrazinecarboxamides COMMENTS FRAC CODE Resistance not known. 39 isofetamid fluopyram fenfuram carboxin oxycarboxin thifluzamide benzovindiflupyr bixafen fluxapyroxad furametpyr isopyrazam penflufen penthiopyrad sedaxane Resistance known for several fungal species in field populations and lab mutants. Target site mutations in sdh gene, e.g. H/Y (or H/L) at 257, 267, 272 or P225L, dependent on fungal species. Resistance management required. Medium to high risk. See FRAC SDHI Guidelines for resistance management. pydiflumetofen boscalid pyraziflumid azoxystrobin coumoxystrobin enoxastrobin methoxy-acrylates flufenoxystrobin Resistance known in various picoxystrobin fungal species. Target site pyraoxystrobin mutations in cyt b gene (G143A, methoxy-acetamide mandestrobin F129L) and additional C3 pyraclostrobin mechanisms. complex III: methoxy-carbamates pyrametostrobin cytochrome bc1 QoI-fungicides triclopyricarb Cross resistance shown (ubiquinol oxidase) (Quinone outside kresoxim-methyl between all members of the QoI oximino-acetates at Qo site (cyt b trifloxystrobin Inhibitors) group. gene) dimoxystrobin fenaminstrobin High risk. oximino-acetamides metominostrobin orysastrobin See FRAC QoI Guidelines for resistance management. oxazolidine-diones famoxadone dihydro-dioxazines fluoxastrobin Imidazolinones fenamidone benzyl-carbamates pyribencarb Resistance risk unknown but C4 cyano-imidazole cyazofamid assumed to be medium to high QiI - fungicides complex III: (mutations at target site known (Quinone inside cytochrome in model organisms). Inhibitors) bc1(ubiquinone Resistance management sulfamoyl-triazole amisulbrom reductase) at Qi site required. FRAC Code List© 2017 7 Page 4 of 12 11 21 C: respiration (continued) MOA TARGET SITE AND CODE GROUP NAME CHEMICAL GROUP COMMON NAME COMMENTS C5 dinitrophenyl crotonates Resistance not known. Also acaricidal activity. uncouplers of oxidative phosphorylation binapacryl meptyldinocap dinocap 2,6-dinitroanilines fluazinam Low risk. However, resistance claimed in Botrytis in Japan. (pyr.-hydrazones) (ferimzone) Reclassified to U 14 in 2012. organo tin compounds tri-phenyl tin compounds fentin acetate fentin chloride fentin hydroxide Some resistance cases known. Low to medium risk. 30 thiophenecarboxamides thiophenecarboxamides silthiofam Resistance reported. Risk low. 38 ametoctradin Not cross resistant to QoI fungicides. Resistance risk assumed to be medium to high (single site inhibitor). Resistance management required. 45 C6 inhibitors of oxidative phosphorylation, ATP synthase C7 ATP production (proposed) C8 QoSI fungicides complex III: (Quinone outside cytochrome bc1 Inhibitor, triazolo-pyrimidylamine (ubiquinone stigmatellin reductase) at Qo site, stigmatellin binding type) binding sub-site D: amino acids and protein synthesis D1 methionine biosynthesis (proposed) (cgs gene) D2 protein synthesis D3 protein synthesis D4 protein synthesis D5 protein synthesis FRAC Code List© 2017 AP - fungicides (AnilinoPyrimidines) anilino-pyrimidines cyprodinil mepanipyrim pyrimethanil enopyranuronic enopyranuronic acid acid antibiotic antibiotic blasticidin-S hexopyranosyl antibiotic hexopyranosyl antibiotic kasugamycin glucopyranosyl antibiotic glucopyranosyl antibiotic streptomycin tetracycline antibiotic tetracycline antibiotic oxytetracycline FRAC CODE 29 Resistance known in Botrytis and Venturia, sporadically in Oculimacula. Medium risk. See FRAC Anilinopyrimidine Guidelines for resistance management. Low to medium risk. Resistance management required. Resistance known in fungal and bacterial (P. glumae) pathogens. Medium risk. Resistance management required. Bactericide. Resistance known. High risk. Resistance management required. Bactericide. Resistance known. High risk. Resistance management required. Page 5 of 12 9 23 24 25 41 MOA TARGET SITE AND CODE E1 E: signal transduction signal transduction (mechanism unknown) GROUP NAME CHEMICAL GROUP aryloxyquinoline COMMON NAME quinoxyfen azanaphthalenes quinazolinone proquinazid phenylpyrroles fenpiclonil fludioxonil dicarboximides chlozolinate dimethachlone iprodione procymidone vinclozolin E2 MAP/HistidinePP-fungicides Kinase in osmotic (PhenylPyrroles) signal transduction (os-2, HOG1) E3 MAP/Histidinedicarboximides Kinase in osmotic signal transduction (os-1, Daf1) FRAC Code List© 2017 COMMENTS Resistance to quinoxyfen known. Medium risk. Resistance management required. Cross resistance found in Erysiphe (Uncinula) necator but not in Blumeria graminis. Resistance found sporadically, mechanism speculative. Low to medium risk. Resistance management required. Resistance common in Botrytis and some other pathogens. Several mutations in OS-1, mostly I365S. Cross resistance common between the group members. Medium to high risk. See FRAC Dicarboximide Guidelines for resistance management. Page 6 of 12 FRAC CODE 13 12 2 MOA TARGET SITE AND CODE GROUP NAME CHEMICAL GROUP F1 formerly dicarboximides F2 F: lipid synthesis or transport / membrane integrity or function phospholipid biosynthesis, methyltransferase F3 lipid peroxidation (proposed) phosphorothiolates phosphoro-thiolates dithiolanes Dithiolanes F5 edifenphos iprobenfos (IBP) pyrazophos isoprothiolane biphenyl AH-fungicides chloroneb (Aromatic aromatic hydrocarbons dicloran Hydrocarbons) quintozene (PCNB) (chlorophenyls, tecnazene (TCNB) nitroanilines) tolclofos-methyl heteroaromatics 1,2,4-thiadiazoles etridiazole carbamates carbamates iodocarb propamocarb prothiocarb F4 cell membrane permeability, fatty acids (proposed) COMMON NAME COMMENTS Resistance known in specific fungi. Low to medium risk. Resistance management required if used for risky pathogens. 6 Resistance known in some fungi. Low to medium risk. Cross resistance patterns complex due to different activity spectra. 14 Low to medium risk. Resistance management required. 28 formerly CAA-fungicides Bacillus subtilis syn. B.amyloliquefaciens* *synonyms for Bacillus strain QST 713 amyloliquefaciens are Bacillus Bacillus subtilis and B. subtilis var. F6 amyloliquefaciens amyloliquefaciens (previous Bacillus sp. and the strain FZB24 microbial taxonomic classification). fungicidal lipopeptides microbial disrupters (Bacillus sp.) Bacillus produced Resistance not known. of pathogen cell amyloliquefaciens membranes strain MBI600 Induction of host plant defence Bacillus described as additional mode amyloliquefaciens of action for strain FZB24. strain D747 extract from Melaleuca alternifolia F7 terpene hydrocarbons, (tea tree) cell membrane plant extract terpene alcohols and Resistance not known. Plant oils (mixtures): disruption terpene phenols eugenol, geraniol, (proposed) thymol amphoteric macrolide antifungal antibiotic Resistance not known natamycin F8 polyene from Streptomyces agricultural, food and topical (pimaricin) ergosterol binding natalensis or medical uses. S. chattanoogensis OSBPI Resistance risk assumed to be oxysterol binding medium to high (single site F9 piperidinyl-thiazoleprotein oxathiapiprolin inhibitor). Resistance lipid homeostasis isoxazolines management required. and transfer/storage homologue inhibition (Previously U15). FRAC Code List© 2017 FRAC CODE Page 7 of 12 44 46 48 49 MOA TARGET SITE AND CODE GROUP NAME CHEMICAL GROUP COMMON NAME piperazines pyridines pyrimidines imidazoles G: sterol biosynthesis in membranes G1 DMI-fungicides (DeMethylation C14- demethylase Inhibitors) in sterol biosynthesis (SBI: Class I) (erg11/cyp51) triazoles triazolinthiones G2 14-reductase and 87isomerase in sterol biosynthesis (erg24, erg2) amines (“morpholines”) G3 3-keto reduc-tase, (SBI: Class III) C4- de-methylation (erg27) G4 squalene-epoxidase (SBI class IV) in sterol biosynthesis (erg1) FRAC Code List© 2017 triforine pyrifenox pyrisoxazole fenarimol nuarimol There are big differences in the imazalil activity spectra of DMI oxpoconazole fungicides. pefurazoate prochloraz Resistance is known in various triflumizole fungal species. Several azaconazole resistance mechanisms are bitertanol known incl. target site mutations bromuconazole in cyp51 (erg 11) gene, e.g. cyproconazole V136A, Y137F, A379G, I381V; difenoconazole cyp51 promotor; ABC diniconazole transporters and others. epoxiconazole etaconazole Generally wise to accept that fenbuconazole cross resistance is present fluquinconazole between DMI fungicides active flusilazole against the same fungus. flutriafol hexaconazole DMI fungicides are Sterol imibenconazole Biosynthesis Inhibitors (SBIs), ipconazole but show no cross resistance to metconazole other SBI classes. myclobutanil penconazole Medium risk. propiconazole simeconazole See FRAC SBI Guidelines tebuconazole for resistance management. tetraconazole triadimefon triadimenol triticonazole prothioconazole morpholines aldimorph dodemorph fenpropimorph tridemorph piperidines fenpropidin piperalin (SBI: Class II) COMMENTS spiroketal-amines spiroxamine hydroxyanilides fenhexamid amino-pyrazolinone fenpyrazamine thiocarbamates pyributicarb allylamines naftifine terbinafine Decreased sensitivity for powdery mildews. Cross resistance within the group generally found but not to other SBI classes. FRAC CODE 3 5 Low to medium risk. See FRAC SBI Guidelines for resistance management. Low to medium risk. Resistance management required. 17 Resistance not known, fungicidal and herbicidal activity. 18 Medical fungicides only. Page 8 of 12 MOA TARGET SITE AND CODE H: cell wall biosynthesis H3 GROUP NAME CHEMICAL GROUP COMMON NAME Formerly glucopyranosyl antibiotic (validamycin) H4 polyoxins chitin synthase H5 CAA-fungicides (Carboxylic Acid Amides) cellulose synthase peptidyl pyrimidine nucleoside polyoxin cinnamic acid amides dimethomorph flumorph pyrimorph valinamide carbamates mandelic acid amides I: melanin synthesis in cell wall I1 reductase in melanin biosynthesis I2 dehydratase in melanin biosynthesis I3 polyketide synthase in melanin biosynthesis P: host plant defence induction P1 salicylic acid pathway MBI-R (Melanin Biosynthesis Inhibitors – Reductase) MBI-D (Melanin Biosynthesis Inhibitors – Dehydratase) MBI-P (Melanin Biosynthesis Inhibitors – Polyketide synthase) benzothiadiazole (BTH) FRAC CODE reclassified to U18 26 Resistance known. Medium risk. Resistance management required. 19 Resistance known in Plasmopara viticola but not in Phytophthora infestans. benthiavalicarb Cross resistance between all iprovalicarb members of the CAA group. valifenalate Low to medium risk. See FRAC CAA Guidelines for resistance management. mandipropamid isobenzo-furanone fthalide pyrrolo-quinolinone pyroquilon triazolobenzothiazole cyclopropanecarboxamide COMMENTS Resistance not known. 40 16.1 tricyclazole carpropamid Resistance known. Medium risk. Resistance management required. 16.2 carboxamide diclocymet propionamide fenoxanil trifluoroethylcarbamate tolprocarb Resistance not known. 16.3 benzo-thiadiazole (BTH) acibenzolar-Smethyl Resistance not known. P 01 Resistance not known. P 02 P2 benzisothiazole benzisothiazole probenazole (also antibacterial and antifungal activity) P3 thiadiazolecarboxamide thiadiazolecarboxamide tiadinil isotianil Resistance not known. P 03 P4 natural compound polysaccharides laminarin Resistance not known. P 04 P5 plant extract complex mixture, ethanol extract extract from Reynoutria sachalinensis (giant knotweed) Resistance not known. P 05 P6 microbial Bacillus cereus group Bacillus mycoides isolate J Resistance not known. P 06 FRAC Code List© 2017 Page 9 of 12 MOA TARGET SITE AND CODE unknown GROUP NAME CHEMICAL GROUP COMMON NAME cyanoacetamideoxime cyanoacetamideoxime U: Unknown mode of action (U numbers not appearing in the list derive from reclassified fungicides) ethyl phosphonates COMMENTS FRAC CODE Resistance claims described. Low to medium risk. Resistance management required. 27 Few resistance cases reported in few pathogens. Low risk. phosphorous acid and salts 33 cymoxanil fosetyl-Al unknown phosphonates unknown phthalamic acids phthalamic acids teclofthalam (Bactericide) Resistance not known. 34 unknown benzotriazines benzotriazines triazoxide Resistance not known. 35 unknown benzenesulfonamides benzenesulphonamides flusulfamide Resistance not known. 36 unknown pyridazinones pyridazinones diclomezine Resistance not known. 37 unknown thiocarbamate thiocarbamate methasulfocarb Resistance not known. 42 unknown phenylacetamide phenyl-acetamide cyflufenamid Resistance in Sphaerotheca. Resistance management required U 06 benzophenone metrafenone Less sensitive isolates detected in wheat powdery mildew. Medium risk. Resistance management required. U 08 U 12 actin disruption (proposed) aryl-phenylketone benzoylpyridine pyriofenone cell membrane disruption (proposed) guanidines guanidines dodine Resistance known in Venturia inaequalis. Low to medium risk. Resistance management recommended. unknown thiazolidine cyano-methylenethiazolidines flutianil Resistance not known. U 13 unknown pyrimidinonehydrazones pyrimidinonehydrazones ferimzone Resistance not known (previously C5). U 14 U 16 complex III: cytochrome bc1, unknown binding site (proposed) 4-quinolylacetate 4-quinolyl-acetates tebufloquin Not cross resistant to QoI. Resistance risk unknown but assumed to be medium. Resistance management required. Unknown tetrazolyloxime tetrazolyloximes picarbutrazox Resistance not known. Not cross resistant to PA, QoI, CAA. U 17 Unknown (Inhibition of trehalase) glucopyranosyl antibiotic glucopyranosyl antibiotics validamycin Resistance not known. Induction of host plant defense by trehalose proposed (previously H3). U 18 FRAC Code List© 2017 Page 10 of 12 MOA M: Chemicals with multi-site activity NC: not classified TARGET SITE AND CODE unknown multi-site contact activity GROUP NAME CHEMICAL GROUP COMMON NAME FRAC CODE Resistance not known. NC diverse diverse mineral oils, organic oils, potassium bicarbonate, material of biological origin inorganic inorganic copper (different salts) M 01 inorganic inorganic sulphur M 02 dithiocarbamates and relatives dithio-carbamates and relatives ferbam mancozeb maneb metiram propineb thiram zinc thiazole zineb ziram M 03 phthalimides phthalimides captan captafol folpet M 04 Generally considered as a low risk group without any signs of resistance developing to the fungicides. chloronitriles (phthalonitriles) chloronitriles (phthalonitriles) chlorothalonil sulfamides sulfamides dichlofluanid tolylfluanid M 06 bis-guanidines bis-guanidines guazatine iminoctadine M 07 triazines triazines anilazine M 08 quinones (anthraquinones) quinones (anthra-quinones) dithianon M 09 quinoxalines quinoxalines chinomethionat / quinomethionate M 10 maleimide maleimide fluoroimide M 11 Formerly polypeptides from plant extracts (“BLAD”) FRAC Code List© 2017 COMMENTS reclassified to BM1 Page 11 of 12 M 05 M12 MOA TARGET SITE BM: Biologicals with multiple modes of action multiple effects on cell wall, ion membrane transporters; chelating effects polypeptide (from plant extract) competition, mycoparasitism, antibiosis, lytic enzymes and induced resistance microbial (Trichoderma spp.) FRAC Code List© 2017 GROUP NAME CHEMICAL GROUP COMMON NAME COMMENTS FRAC CODE polypeptide (lectin) extract from the cotyledons of lupine plantlets (“BLAD”) Resistance not known (previously M12). BM 01 Trichoderma spp. and the fungicidal metabolites produced Trichoderma atroviride strain SC1 Resistance not known BM 02 Page 12 of 12