FRAC Code List*: 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, mostly not longer than 8 years, until information about mode of action and mechanism of resistance becomes available), and multi-site inhibitors (M). Target Site and Code If available, the biochemical mode of action is given. In many cases the precise target site is not known. However, a grouping can 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. 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.
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Comments on Resistance Details are given for the (molecular) mechanism of resistance and the resistance risk. If field resistance 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 manufacturers 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 rsistance, Phytoma, La Dfense des Vgtaux, 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 = multi-site inhibitors, and U = unknown mode of action and unknown resistance risk. 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 2011 Next update: December 2011

* Copyright 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.
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MOA

TARGET SITE AND CODE

GROUP NAME CHEMICAL GROUP COMMON NAME benalaxyl benalaxyl-M (=kiralaxyl) furalaxyl metalaxyl metalaxyl-M (=mefenoxam) oxadixyl ofurace bupirimate dimethirimol ethirimol hymexazole

COMMENTS

FRAC CODE

acylalanines

A1: A: nucleic acids synthesis

RNA polymerase I

PA fungicides (PhenylAmides) oxazolidinones butyrolactones

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. Resistance not known.

A2:
adenosindeaminase

hydroxy(2-amino-) pyrimidines

hydroxy(2-amino-) pyrimidines

A3:
DNA/RNA synthesis (proposed) heteroaromatics

isoxazoles isothiazolones

32

octhilinone Bactericide. Resistance known. Risk in fungi unknown. Resistance management required. Resistance common in many fungal species. Several target site mutations, mostly E198A/G/K, F200Y in -tubulin gene. Positive cross resistance between the group members. Negative cross resistance to NPhenylcarbamates. High risk. See FRAC Benzimidazole Guidelines for resistance management. Resistance known. Target site mutation E198K. Negative cross resistance to benzimidazoles. High risk. Resistance management required. Low to medium risk. Resistance management required.

A4:
DNA topoisomerase type II (gyrase) carboxylic acids carboxylic acids oxolinic acid

31

benzimidazoles MBC fungicides (Methyl -tubuline Benzimidazole assembly in mitosis Carbamates)

B1:

benomyl carbendazim fuberidazole thiabendazole

B: mitosis and cell division

thiophanates

thiophanate thiophanate-methyl

B2:
-tubulin assembly in mitosis

N-phenyl carbamates

N-phenyl carbamates

diethofencarb

10

B3:
-tubulin assembly in mitosis benzamides toluamides zoxamide

22

B4:
cell division (proposed) phenylureas phenylureas pencycuron Resistance not known

20

B5:
delocalisation of spectrin-like proteins benzamides pyridinylmethylbenzamides fluopicolide Resistance not known

43

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MOA

TARGET SITE AND CODE

GROUP NAME CHEMICAL GROUP COMMON NAME

COMMENTS

FRAC CODE

complex I NADH pyrimidinamines Oxido-reductase

C1:

pyrimidinamines

diflumetorim benodanil flutolanil mepronil fluopyram fenfuram carboxin oxycarboxin thifluzamide bixafen fluxapyroxad furametpyr isopyrazam penflufen penthiopyrad sedaxane boscalid

Resistance not known.

39

phenyl-benzamides pyridinyl-ethylbenzamides furan- carboxamides oxathiincarboxamides C2: SDHI (Succinate thiazoledehydrogenase complex II: carboxamides inhibitors) succinate-dehydrogenase pyrazolecarboxamides

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.

pyridinecarboxamides

azoxystrobin coumoxystrobin enoxastrobin methoxy-acrylates Resistance known in various flufenoxystrobin fungal species. Target site picoxystrobin pyraoxystrobin mutations in cyt b gene (G143A, F129L) and additional pyraclostrobin C3: mechanisms. methoxy-carbamates pyrametostrobin complex III: triclopyricarb cytochrome bc1 QoI-fungicides Cross resistance shown kresoxim-methyl (ubiquinol oxidase) (Quinone outside oximino acetates between all members of the QoI trifloxystrobin at Qo site (cyt b Inhibitors) group. dimoxystrobin gene) fenaminostrobin oximino-acetamides High risk. metominostrobin orysastrobin See FRAC QoI Guidelines oxazolidine-diones famoxadone for resistance management. 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. binapacryl dinitrophenyl Resistance not known. meptyldinocap C5: crotonates Also acaricidal activity. dinocap uncouplers of 2,6-dinitroLow risk. However, resistance fluazinam oxidative phosAnilines claimed in Botrytis in Japan. phorylation pyrimidinoneferimzone Resistance not known. hydrazones

C. respiration

11

21

29

C6:
inhibitors of oxidative phosphorylation, ATP synthase organo tin compounds tri phenyl tin compounds

fentin acetate fentin chloride fentin hydroxide

Some resistance cases known. Low to medium risk.

30

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MOA

TARGET SITE AND CODE

GROUP NAME CHEMICAL GROUP COMMON NAME

COMMENTS

FRAC CODE

C7: C: respiration
(continued) ATP production (proposed)

thiophenecarboxamides

thiophenecarboxamides

silthiofam

Resistance reported. Risk low.

38

C8:
complex III: QxI fungicide cytochrome bc1 triazolo-pyrimidylamine (ubiquinone (Quinone x reductase) at Inhibitor) Q x (unknown) site ametoctradin Resistance risk assumed to be medium to high (single site inhibitor). Resistance management required.

45

D1: D: amino acids and protein synthesis

methionine biosynthesis (proposed) (cgs gene) AP - fungicides (AnilinoPyrimidines) anilino-pyrimidines cyprodinil mepanipyrim pyrimethanil

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.

D2:
protein synthesis

enopyranuronic enopyranuronic acid acid antibiotic antibiotic

blasticidin-S

23

D3:
protein synthesis

hexopyranosyl antibiotic

hexopyranosyl antibiotic

D4:
protein synthesis

glucopyranosyl antibiotic tetracycline antibiotic

glucopyranosyl antibiotic

D5:
protein synthesis

tetracycline antibiotic aryloxyquinoline

E1:
Signal transduction (mechanism unknown)

azanaphthalenes quinazolinone

Resistance known in fungal and bacterial (P. glumae) pathogens. kasugamycin Medium risk. Resistance management required. Bactericide. Resistance known. High risk. streptomycin Resistance management required. Bactericide. Resistance known. High risk. oxytetracycline Resistance management required. Resistance to quinoxyfen quinoxyfen known. Medium risk. Resistance management required. Cross resistance found in Erysiphe (Uncinula) necator proquinazid 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.

24

25

41

13

E: signal transduction

E2:
PP-fungicides MAP/HistidineKinase in osmotic (PhenylPyrroles) signal transduction (os-2, HOG1) phenylpyrroles fenpiclonil fludioxonil

12

E3:
MAP/Histidine- dicarboximides Kinase in osmotic signal transduction (os-1, Daf1) dicarboximides

chlozolinate iprodione procymidone vinclozolin

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MOA

TARGET SITE AND CODE

GROUP NAME CHEMICAL GROUP COMMON NAME formerly dicarboximides phosphorothiolates dithiolanes phosphoro-thiolates dithiolanes edifenphos iprobenfos (IBP) pyrazophos isoprothiolane

COMMENTS

FRAC CODE

F1: F2:
phospholipid biosynthesis, methyltrans-ferase

F: lipids and membrane synthesis

Resistance known in specific fungi. Low to medium risk. Resistance management required if used for risky pathogens.

biphenyl AH-fungicides chloroneb (Aromatic dicloran Resistance known in some aromatic hydrocarbons Hydrocarbons) quintozene fungi. F3: (chlorophenyls, (PCNB) Low to medium risk. nitroanilines) tecnazene (TCNB) Cross resistance patterns lipid peroxidation tolclofos-methyl complex due to different activity (proposed) spectra. heteroaromatics 1,2,4-thiadiazoles etridiazole

14

F4:
cell membrane permeability, fatty acids (proposed) carbamates carbamates

iodocarb propamocarb prothiocarb

Low to medium risk. Resistance management required.

28

F5: F6:
microbial disrupters of pathogen cell membranes

formerly CAAfungicides Microbial (Bacillus sp.) Bacillus subtilis and the fungicidal lipopeptides they produce Bacillus subtilis strain QST 713 No resistance reported. Assumed to be low risk based on mode of action of nonspecific membrane disruption

44

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MOA

TARGET SITE AND CODE

GROUP NAME CHEMICAL GROUP COMMON NAME piperazines pyridines pyrimidines

COMMENTS

FRAC CODE

imidazoles

G: sterol biosynthesis in membranes

DMI-fungicides (DeMethylation C14- demethylase Inhibitors) in sterol biosynthesis (SBI: Class I) (erg11/cyp51) triazoles

G1:

G2:
14-reductase and 87isomerase in sterol biosynthesis (erg24, erg2) Amines (Morpholines) (SBI: Class II)

morpholines

piperidines spiroketal-amines

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 prothioconazole See FRAC SBI Guidelines simeconazole for resistance management. tebuconazole tetraconazole triadimefon triadimenol triticonazole aldimorph Decreased sensitivity for dodemorph powdery mildews. fenpropimorph Cross resistance within the tridemorph group generally found but not to other fenpropidin SBI classes. piperalin spiroxamine Low to medium risk. See FRAC SBI Guidelines for resistance management. Low to medium risk. Resistance management required. Resistance not known, fungicidal and herbicidal activity Medical fungicides only

G3:
hydroxyanilides 3-keto reduc-tase, (SBI: Class III) C4- de-methylation (erg27) hydroxyanilides fenhexamid

17

G4:
squalene-epoxidase (SBI class IV) in sterol biosynthesis (erg1)

thiocarbamates

pyributicarb naftifine terbinafine

18

allylamines

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MOA

TARGET SITE AND CODE

GROUP NAME CHEMICAL GROUP COMMON NAME

COMMENTS

FRAC CODE

H3:
trehalase and inositol-biosynthesis glucopyranosyl antibiotic glucopyranosyl antibiotic validamycin Resistance not known

26

H: cell wall biosynthesis

H4:
polyoxins chitin synthase

peptidyl pyrimidine nucleoside

polyoxin

Resistance known. Medium risk. Resistance management required.

19

cinnamic acid amides CAA-fungicides (Carboxylic Acid Amides) cellulose synthase

H5:

valinamide carbamates mandelic acid amides

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 fthalide pyroquilon tricyclazole carpropamid diclocymet fenoxanil acibenzolar-Smethyl probenazole (also antibacterial and antifungal activity) tiadinil isotianil laminarin Resistance known. Medium risk. Resistance management required. Resistance not known

dimethomorph flumorph

40

I: melanin synthesis in cell wall

I1:
reductase in melanin biosynthesis

MBI-R (Melanin Biosynthesis Inhibitors Reductase) MBI-D (Melanin Biosynthesis Inhibitors Dehydratase) benzothiadiazole BTH

isobenzo-furanone pyrrolo-quinolinone triazolobenzothiazole cyclopropanecarboxamide carboxamide propionamide benzo-thiadiazole BTH

16.1

I2:
dehydratase in melanin biosynthesis

16.2

P1: P: host plant defence induction

salicylic acid pathway

Resistance not known

P2 P3 P4 (proposed)

benzisothiazole

benzisothiazole

Resistance not known

thiadiazolecarboxamide natural compound

thiadiazolecarboxamide

Resistance not known

Resistance not known

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MOA

TARGET SITE AND CODE unknown

GROUP NAME CHEMICAL GROUP COMMON NAME

COMMENTS Resistance claims described. Low to medium risk. Resistance management required.

FRAC CODE

cyanoacetamideoxime

cyanoacetamideoxime ethyl phosphonates

cymoxanil

27

unknown (U numbers not appearing in the list derive from reclassified fungicides)

phosphonates

Few resistance cases reported in few pathogens. Low risk phophorous acid and salts fosetyl-Al teclofthalam (Bactericide) triazoxide flusulfamide diclomezine Resistance not known Resistance not known Resistance not known Resistance not known

33

unknown unknown unknown unknown

phthalamic acids benzotriazines benzenesulfonamides pyridazinones

phthalamic acids benzotriazines benzenesulfonamides pyridazinones

34 35 36 37 42 U5 U6

Unknown mode of action

unknown microtubule disruption (proposed) unknown

thiocarbamate

thiocarbamate

methasulfocarb

Resistance not known

thiazole carboxamide phenylacetamide

ethylamino-thiazole carboxamide

ethaboxam

Resistance not known Resistance in Sphaerotheca. Resistance management required Less sensitive isolates detected in wheat powdery mildew. Medium risk. Resistance management required. Resistance known in Venturia inaequalis. Low to medium risk. Resistance management recommended. Resistance not known

phenyl-acetamide

cyflufenamid

actin disruption (proposed)

aryl-phenylketone

benzophenone benzoylpyridine

metrafenone pyriofenone

U8

Cell membrane disruption (proposed)

guanidines

guanidines

dodine

U12

unknown

thiazolidine

cyano-methylenethiazolidine

flutianil mineral oils, organic oils, potassium bicarbonate, material of biological origin

U13

not classified

unknown

diverse

diverse

Resistance not known

NC

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MOA

TARGET SITE AND CODE

GROUP NAME CHEMICAL GROUP COMMON NAME inorganic inorganic inorganic inorganic copper (different salts) sulphur ferbam mancozeb maneb metiram propineb thiram zineb ziram captan captafol folpet chlorothalonil dichlofluanid tolylfluanid guazatine iminoctadine anilazine dithianon

COMMENTS

FRAC CODE

M1 M2

Multi-site contact activity

dithiocarbamates and relatives

dithio-carbamates and relatives

M3
Generally considered as a low risk group without any signs of resistance developing to the fungicides No cross resistance between group members M1 to M9

multi-site contact activity

phthalimides chloronitriles (phthalonitriles) sulfamides

phthalimides chloronitriles (phthalonitriles) sulfamides

M4 M5 M6 M7 M8 M9

guanidines triazines quinones (anthraquinones)

guanidines triazines quinones (anthra-quinones)

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