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A: Nucleic Acid Synthesis C: Respiration

A1: RNA polymerase I


# 4: PA-fungicides (PhenylAmides)
A2: adenosin-deaminase
# 8: hydroxy (2-amino)-pyrimidines
Mode of Action of Fungicides C1: inhibition of complex I
NADH Oxido-reductase
# 39 pyrimidinamines pyrazole-MET1
C4: inhibition of complex III
> cytochrome bc1(ubiquinone reductase) at Qi site
># 21 QiI fungicides (Quinone inside Inhibitors)
>
C8: inhibition of complex III
cytochrome bc1(ubiquinone reductase)
at Qo site stigmatellin binding sub site)
# 45 QoSI-fungicide (stigmatellin binding type)
triazolo-pyrimidylamine
C6: inhibitors
of oxidative
phosphorylation,
ATP synthase

FRAC classification on mode of action 2016 (www.frac.info)


pyrimidinamine pyrazole -5-carboxamide cyano-imidazole sulfamoyl-triazole
acylalanines # 30 organo tins
O O O O O Cl F
N
O F N O O NH2
O N O N Cl
N S
H F N N N N
O N
O S O
S O N N
N N N N
O O N N Br O Sn

C: Respiration
O O N N O S
benalaxyl O
N
metalaxyl
NH B: Cytoskeleton and motor proteins diflumetorim
tolfenpyrad
cyazofamid amisulbrom
N
ametoctradin O
O

bupirimate fentin acetate


O O O
O O
B1: > ß-tubulin assembly in mitosis B2: C3: inhibition of complex III C7: ATP production
C2: inhibition of complex II: succinate-dehydrogenase
O N
furalaxyl O N
# 1: MBC fungicides > ß-tubulin
tubulin assembly cytochrome bc1 (ubiquinol oxidase) at Qo site (cyt b gene) (prop.)
HO benzimidazoles (= Methyl Benzimidazole Carbamates) oxazolidine-
in mitosis* # 7 SDHI (Succinate DeHydrogenase Inhibitors) # 11 QoI fungicides ( Quinone outside Inhibitors ) # 38 thiophene-
N O methoxy- oximino- diones Sn
N N
# 10 N-phenyl carboxamides
benalaxyl-M metalaxyl-M pyrazole -4- acrylates acetamides methoxy- Cl
N
N S
H
N O
carbamates O carboxamides F
F
O
F
carbamates
H thiophanates fentin chloride
dimethirimol O fluxapyroxad methoxy-
butyrolactones oxazolidinones N O NH O
N
N N
N
H
NH
O
S O H acetamides N
N N N O O

O
N
H
fuberidazole N O N N oximino- O
Cl N H O Cl F N
O
O O S
N
H
N
H
O
S N O O O F
F O Cl
O O O
N N
O acetates O
H
O N N S F O O H N O
HO H H N O N Cl S
O
thiophanate O N O N furametpyr Cl F O sedaxane N O N
N
Si
O N N NH O H N H N
N
H bixafen O O
N O

O N S O O Sn
N N benomyl N N N N O
famoxadone
H thiabendazole F N H OH
N N N O azoxystrobin orysastrobin silthiofam
NH H H diethofencarb N
N O pyraclostrobin fentin hydroxide
H thiophanate- O imidazolinones
ofurace oxadixyl ethirimol O methyl penflufen penthiopyrad isopyrazam
pyridinyl-ethyl O
N
O
carbendazim * negative cross-resistance to B1 phenyl-oxo-ethyl benzamides mandestrobin
thiazole thiophene amide N-methoxy-(penyl- O
O
NH
C5: uncouplers of oxidative phosphorylation
kresoxim-methyl
carboxamides ethyl)-pyrazole- O
H
N
O N # 29
F
benzovindiflupyr N
S O
carboxamides N N O
N O
N dinitrophenyl crotonates
B6:
F F Cl O 2,6-dinitro-aniline
A3: DNA / RNA synthesis (prop.) A4: DNA topoisomerase B3: B4: B5: F O
F
F
dimoxystrobin
O
F
N N picoxystrobin pyrametostrobin
F
# 32: heteroaromatics type II (gyrase) >ß-tubulin assembly in mitosis cell division delocalisation actin/myosin/ F
F
F O
Br O

F
F H F
F
O
fenamidone Cl
F
F F N
# 31: carboxylic acids # 22 benzamides and (prop.) of spectrin-like fimbrin function N
N
H fluopyram
O
O O
O HN
N
O
O

S Br N
thiazole carboxamides N O + + O O
# 20 phenylureas proteins e.g. in vesicle isofetamid H
O flufenoxystrobin O
O
O
N N
O N
+

O
isoxazoles isothiazolones pydiflumetofen N H
ethylamino-thiazole # 43 benzamides trafficking thifluzamide
Cl
O O O
N
N trifloxystrobin
Cl
F F N
+

toluamide oxathiin O F F O dihydro- O O


O O carboxamide pyridinylmethyl-benzamide # 47 cyanoacrylates pyridine carboxamides F O
O
fluazinam
F
meptyl dinocap
mepronil dioxazines
H O carboxamides O N
N
H
O O metominostrobin
N
HO aminocyanoacrylates H enoxastrobin triclopyricarb benzyl-carbamates
O O O
O O
N
S O
O N
N
O O O O O
O Cl O O I O O O
S Cl O Cl O
Cl
N Cl N
N N N
O O flutolanil N
+
H
H H
N N N oxycarboxin N N N O
oxolinic acid O S S
H H H N Cl
Cl
N F N phenyl- coumoxystrobin O O
hymexazole octhilinone (bactericide) N
H Cl O N O N O
Cl F
F
H H benzamides O Cl F O
N
N
+

ethaboxam S HN O N O O
zoxamide pencycuron benodanil O
binapacryl
O
fluopicolide Cl carboxin fenfuram furan fluoxastrobin
boscalid fenaminstrobin
phenamacril carboxamides pyraoxystrobin pyribencarb

D: Amino Acid and Protein Synthesis E: Signal Transduction F: Lipid Synthesis and Membrane Integrity I: Melanin Synthesis in Cell Wall
D1: methionine biosynthesis D2: D3: E1: Signal transduction (mechanism unknown) F2: phospholipid biosynthesis F3: lipid peroxidation (prop.) F4: cell membrane F6: microbial disrupters of I1: reductase in I2: dehydratase in I3: polyketide
E3: Osmotic signal transduction synthase in melanin
(cgs gene) (prop.) protein synthesis protein synthesis #13 azanaphthalenes > methyltransferase # 14 aromatic hydrocarbons & heteroaromatics permeability, pathogen cell membranes melanin biosynthesis melanin biosynthesis
> MAP / histidine kinase (os-1, Daf1) # 16.1 Melanin Biosynthesis # 16.2 Melanin Biosynthesis biosynthesis
# 9 Anilino-Pyrimidines # 23 enopyranuronic acid # 24 hexopyranosyl antibiotics # 6 phosphorothiolates & dithiolanes fatty acids (prop.) # 44 Microbial (Bacillus sp.) Inhibitors:
aryloxyquinoline quinazolinone # 2 dicarboximides O
N
+ O Inhibitors: # 16.3 Melanin Biosynthesis
( AP fungicides ) aromatic hydrocarbons Reductase (MBI-R) Dehydratase (MBI-D)
OH # 28 carbamates Inhibitors: Polyketide
HN Bacillus sp. and isobenzo-furanone carboxamide synthase (MBI-P)
O
F
H 2N N O
H2 N NH Cl Cl O + O the fungicidal lipopeptides produced
O N
NH N
NH
N O O NH2 Cl trifluoroethyl-carbamate
O NH 2 NH2
O O Cl O I O
O
S
phosphorothiolates N
+
Cl Cl O
O
N N NH N N P
O dicloran Bacillus Cl N
N N H HO OH N O Cl Cl O Cl
N O
HO O
O
N
O O amyloliquefaciens O H
HO OH
N O Cl Cl O N N (synonym B. subtilis) N
O O H
OH Cl N O Cl Cl Cl strains: Cl
O Cl
cyprodinil O Cl Cl pyrazophos S
P
O
tecnazene quintozene QST 713
blasticidin-S kasugamycin iprodione Cl
quinoxyfen proquinazid O
N
O
O (TCNB) (PCNB) FZB24 fthalide diclocymet
propamocarb MBI600
pyrrolo-quinolione
NH Cl Cl
O Cl D747 cyclopropane carboxamide tolprocarb
iprobenfos O
N N D4: protein synthesis D5: protein synthesis E2: Osmotic signal transduction chlozolinate O
N
O S
P S
Cl
S biphenyl O
O O O
# 25 glucopyranosyl # 41 tetracycline antibiotics > MAP / histidine- kinase (os-2, HOG1) O P
O N F7: cell membrane N O Cl
antibiotics dithiolanes O O H
# 12 phenylpyrroles (PP- fungicides) Cl
mepanipyrim O
N O
Cl Cl edifenphos tolclofos- Cl
I
disruption (prop.) N

vinclozolin methyl chloroneb Cl


HO
O
# 46 plant extract. Cl O

HO O Chiral iodocarb
HO O S Cl pyroquilon
O
OH O OH O O carpropamid
HO OH
NH O
O H H Cl Cl Cl Cl
NH OH
NH2 N N O S triazolobenzo-thiazole propionamide
O OH procymidone
N N NH2 O N N
OH N N O
HN
OH
N
H
NH OH OH N
Cl
iso- S Melaleuca alternifolia
F O O N
HN NH2
oxytetracycline prothiolane S N N
H N O Cl
pyrimethanil streptomycin (bactericide) Cl
F O (Tea Tree Extract) N
dimethachlone etridiazole N N
O
(bactericide) H
fenpiclonil fludioxonil prothiocarb
S Cl
1,2,4-thiadiazole
tricyclazole fenoxanil

G: Sterol Biosynthesis in membranes H:Cell Wall Biosynthesis P: Host Plant Defence Induction M:
#M6Multi Site Action
sulphamides
P1: salicylic pathway P2:
G1: C14-demethylase in sterol biosynthesis (erg11/cyp51) G2:∆14-Reductase and ∆8→ ∆7-isomerase in sterol H4: chitin synthase H5: cellulose synthase benzothiodiazole BTH benzothiazole
#M9 anthraquinones #M5 chloronitriles

# 3 DMI-fungicides (DeMethylation Inhibitors) biosynthesis (erg2, erg 24) # 19 Polyoxins # 40 Carboxylic Acid Amides
N
(SBI: Class I) # 5 Amines(“Morpholines”) (SBI: Class II) (CAA fungicides) O S O
O
O #M1/2 inorganics N
S
Cl S Cl Cl
N
S
triazoles O piperazines
cinnamic acid N
S
O S
O O NH 2
amides N N Cl
Cl Cl O O N
N
N
HN
Cl O
OH
O HO mandelic acid #M8 triazines Cl
Cl
piperidines
O acibenzolar- sulphur dithianon chlorothalonil
N Cl morpholines HO
N OH amides probenazole
O etaconazole HO N N H2 N H S-methyl .
O N
N
O
O

N
OH
Cu
N Cl
Cl N Cl H
N
P4: #M4 phthalimides
P3:
HN
N Cl N N #M6 sulphamides
NH
dimethomorph copper
N Cl O OH
polysaccharide Blad
Cl
Cl Cl
O
O preparations N N
azaconazole N ipconazole
HO pyridines triforine
O
(CH 2) 11 N O Polyoxin B thiadiazole carboxamide
O N
N fenpropidin
N
H
O
Cl
Polypeptide (lectin)
Cl N H 3C Cl O O
OH N N
O OH
O
N
Extract from cotyledons
N Cl
anilazine S S of lupine plantlets
N Cl Cl Cl flumorph HO
HO
O
OH
N S N
O HO Cl
pyridines aldimorph mandipropamid O OH
O
OH
#M3 dithiocarbamates & relatives Cl Cl O
N
peptidyl pyrimidine nucleoside OHO
O
OH F
N fenbuconazole N
tebuconazole N O S HO
O
OHO
O
OH
O
OH Cl
H
N N N O piperalin N N OH n
O Cl
N H
F
Cl Cl H2 N
S S- captan dichlofluanid #M12 polypeptide
Cl Cl F Cl Cl fenpropimorph pyrimorph N
O Cl O N (CH2) n N O Zn2+ from plant extract
bitertanol F metconazole F
pyrifenox H3 C
valinamide isotianil laminarin N S 3+ N N
N F spiroketal- Fe S
Cl
carbamates H2 N S- O O
N
Br N N
n = 10 to 13 amines S
3
Cl
S S
N N n = 12: ~ 70% N
N Cl N N N S O
N
N
pyrimidines tridemorph O
H
O
H
N
P5: ferbam
febram zinc thiazole
Cl Cl
F #M10 quinoxalines
fluquinconazole tetraconazole pyrisoxazole O N
N O N
H
plant extract O
Cl
Cl
O Cl N H O O
N O
Cl
O
O O O
N O N
N Cl F
N
N
Cl
S Reynoutria captafol tolylfluanid
N
N dodemorph O iprovalicarb F
valifenalate Cl N
H
N
sachalinensis H S
N S
H S
S mancozeb S
OH O N N H
N O H N S 2+
bromuconazole myclobutanil N N N Mn
Si F O N S Zn (NH 3)-
S N
N N S N S H
F
H H S 3 H S O
spiroxamine
O
(Giant Knotweed x
S
N tiadinil
N
Cl
N Extract)
Cl
N
N Cl
benthiavalicarb N S chinomethionat
Cl metiram S maneb Cl
OH H
flusilazole triadimefon nuarimol N S 2+
HO Cl Zn Cl
S N
H O Cl #M7 guanidines
N S
N Cl
HO N #M11 maleimides
N
N
S folpet
N F N
N
G3:3-Keto reductase G4: Squalene epoxidase in propineb
cyproconazole F penconazole N
N O
imidazoles fenarimol
Unknown Mode of Action NC : Not Classified N S
S N N S
Zn
2+ NH 2

HO N
in C4-de-methylation sterol biosynthesis (erg1) S S
HN N
H
NH
2
N N
Cl (erg27) # 18 (SBI class IV) piperidinyl- thiazole HN
H
N
O N Cl cyanoacetamide- ethyl- F
thiram S ziram
O Cl Cl
# 17 (SBI :Class III) oxime phosphonates isoxazoline H
2+ mixture of
NH2
flutriafol O triadimenol O S
N
N S
Zn
O Cl HO O S S H iminoctadine iminoctadine
N
Cl O
O
phenyl CN CF3 pyrimidinone- S
and other
N Cl
N N
Cl
N
N hydroxyanilides O O N Cl
acetamides N
hydrazones Mineral oils, organic oils, polyamines fluoroimide
Cl N
H - phosphorous H
Cl
N HO N O O Al+++ Cl Cl O potassium bicarbonate, zineb .
difenoconazole OH propiconazole imazalil
O Cl
allylamines O N
H
N
H
P acid
N O
Cl
# U15 material of biological
N HO N # 34 # U13 origin guazatine
Cl N N
N N O N
3
teclofthalam flutianil H oxathiapiprolin
N N
N
N Si F F # 27 # 33 N
O O Cl N H3PO3
Cl N Cl F H cymoxanil fosetyl-al phthalamic cyano-methylene N
OH
hexaconazole HO
F triticonazole triflumizole Cl
N terbinafine acid thiazolidine Legend:
N # U16
N Cl
# U6
N O (antimycotic) # 33 tetrazolyloxime tebufloquin
N
triazolinthione fenhexamid # U14 mode of action group
C: Respiration
N O cyflufenamid
N
Cl N N phosphorous ferimzone Mode of action of fungicides based on the FRAC fungicide list
N
Cl O benzene- acid 4-quinolyl acetate (published at www.frac.info/publications )
diniconazole simeconazole Cl thiocarbamates benzotriazines sub-group
N S
Cl Cl pefurazoate N amino-pyrazolinones naftifine sulfonamides thiocarbamates
(antimycotic) The groupings can change when new results become known. C2: inhibition of complex II: > target site of action
N HO N O
N
N
S
Cl
N O
+ pyridazinones guanidines
O
O Yellow zones represent accepted mode of action groups or in > succinate-dehydrogenase (where known) or putative
N Cl Cl Br O cases where resistance is known, cross resistance groups. In spite target site (=prop.)
F O
imibenconazole
Cl
HN
N
N
O
oxpoconazole
O N N O N H
N
S
O F
F O
O
of this general classification, cases of incomplete or even lacking # 7 SDHI (Succinate dehydrogenase
S
N S O F O O O # U17 cross resistance are known within some groups with some inhibitors)
N N O O FRAC code no. (#)
N O Cl Cl N +
N Cl H picarbutrazox
N
Cl prothioconazole N Cl
N S H2N N # U8 OH
OH HO pathogens. and group name
O
N H
N # 35 O
# 42 + metrafenone HO O OH

pyributicarb # 36 N N
NH2 Although details presented herein are accurate to our knowledge at chemical (sub-) group
epoxiconazole prochloraz triazoxide flusulfamide H methasulfocarb O HO
O
HO N OH
fenpyrazamine (herbicide) Cl OH
H
OH
the time of publication, neither FRAC nor its member companies
# 37 O arylphenyl HO
make any representation or warranty with regard to the content of thiazole carboxamides
# U12 # U8 glucopyranosyl # U18
•Temporary status; information on mode of action and diclomezine ketones this presentation, in particular with regard to its correctness and
dodine pyriofenone validamycin
/ or resistance risk is still uncertain antibiotic completeness. Neither FRAC nor its member companies assume
any liability for the content of this presentation or its use.
FRAC Mode of Action Poster ©
Updated February 2016