Frac Moa Poster 2007
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A: Nucleic Acid Synthesis A1: A1: RNA RNA synthesis synthesis > > RNA RNA polymerase polymerase II
## 4: 4: PA-fungicides PA-fungicides (phenylamides) (phenylamides)
## 8: 8: hydroxy hydroxy (2-amino)-pyrimidines (2-amino)-pyrimidines
HO
HO
O
O S
N
N
O
N
B: Mitosis and Cell Division
N HN
O
HO
HO
N
O
metalaxyl-M metalaxyl-M
N
O
OH HO
benalaxyl
O
bupirimate bupirimate
metalaxyl metalaxyl
N
N
O O
N
oxazolidinones
furalaxyl furalaxyl
dimethirimol dimethirimol
Cl
HO
N
O
O
O
O
O
HO
N
N
N
N H
N
NH
N N H
N
H N
N
fuberidazole fuberidazole
O
N
N H
O
oxadixyl oxadixyl
carbendazim carbendazim
ethirimol ethirimol
NH
B2: B2: > ß-tubulin > ß-tubulin assembly assembly in in mitosis* mitosis*
A4: A4: DNA DNA supercoiling supercoiling > > DNA DNA topoisomerase topoisomerase type type IIII (gyrase) (gyrase)
## 32: 32: heteroaromatics heteroaromatics
## 31: 31: carboxylic carboxylic acids acids
isoxazoles
isothiazolones O
H N
O
N
S
O
O
oxolinic oxolinic acid acid (bactericide) (bactericide)
octhilinone octhilinone
N N
N
N H
N
amisulbrom amisulbrom
## 20 20 phenylureas phenylureas
## 11 Quinone outside outside Inhibitors Inhibitors )) 11 QoI QoI fungicides fungicides (( Quinone
methoxyacrylates
O
flutolanil
O
N
## 99 Anilino-Pyrimidines Anilino-Pyrimidines (( AP AP fungicides fungicides ))
F O
F
H N
N
F
O Cl
Br
N
Cl
O
N H
O
Cl
N H
O
O
pyrazole carboxamides
oxathiin carboxamides
N H
Cl
N
O
F
N
O
O
O
S
O N H
pyridine carboxamides
N
F
zoxamide zoxamide
pencycuron pencycuron
O
N
O Cl
F
N N
O
F
O
Cl N H
boscalid boscalid
carboxin carboxin
binapacryl binapacryl
## 24 antibiotics hexopyranosyl antibiotics 24 hexopyranosyl
H2 N OH
O
NH
NH2
NH2
N H HO
NH
N
O
O
fenamidone fenamidone
F
O
benzylcarbamates
O
F
OH
N
O
blasticidin-S blasticidin-S
N
N
N H
O
O N O
N
O
N
N
## 25 25 glucopyranosyl glucopyranosyl antibiotics antibiotics
mepanipyrim mepanipyrim
E2: E2: Osmotic Osmotic signal signal transduction transduction > MAP // histidinehistidine- kinase kinase (os-2, (os-2, HOG1) HOG1) > MAP
## 41 41 tetracycline tetracycline antibiotics antibiotics
NH
HO
N
HO
OH O
O
NH
OH
OH NH2
HN
OH
OH
O
N H
H N
O
OH
O HN
pyrimethanil pyrimethanil
O
N
N
O
fenpiclonil fenpiclonil
O Cl
Cl
Cl
O
dicloran dicloran
+
N
O
O
Cl
Cl
Cl
Cl
O
O P
O
O
S
P
dimethomorph dimethomorph
O
O Cl
O
vinclozolin vinclozolin
Cl
O
S
O
S
S
benzenes
Cl
chloroneb chloroneb
Cl Cl N
Cl
S
N
N H
N
iprovalicarb iprovalicarb
OH
Cl
N
N
N
Cl
N Cl
Cl
bitertanol bitertanol
F
metconazole
O
F
F
pyrifenox pyrifenox
M: Multi Site Action anthraquinones
inorganics
F
O
triazolobenzothiazole
Si N
F
Cl
O O
O
nuarimol nuarimol
Cl
O Cl
O
OH
difenoconazole difenoconazole
triadimenol triadimenol
Cl
propiconazole
N
Cl
N
S
HO
O S N H
OH
N
propionamide
Cl
N
H H N
N
O
H N
N
S
S
Fe
O Cl
O
O
N H
diclocymet diclocymet
fenoxanil fenoxanil
cyanoacetamideoxime
N
U: Recent Molecules* thiazole carboxamides
phthalamic acid
H S S N
O O
N
O
Cl
N
O
Cl
oxpoconazole oxpoconazole
prochloraz prochloraz
O
O
N
N H
O
N H
H H33PO PO33
PH
AlH3
N H
thiocarbamates
naftifine naftifine (antimycotic) (antimycotic)
benzenesulfonamides
benzotriazines O
fenhexamid fenhexamid O
N
N
N
O
Cl
N
N
N
+
N
Cl
Cl O
+
H N
pyributicarb pyributicarb (herbicide) (herbicide)
N H
O
F
N N H
## 34 34 tecloftalam tecloftalam
O O
N Cl
## 37 37 diclomezine diclomezine
N H
## 42 42 methasulfocarb methasulfocarb
F
HN N
O
F F
## U5 U5 ethaboxam ethaboxam
## U6 U6 cyflufenamid cyflufenamid
I
O
O
Br
O
N N
O
## U7 U7 proquinazid proquinazid
O
O
## U8 U8 metrafenone metrafenone
O
NHCH2CH2NHCS2-
S
Cl
Cl
S
N
N O
O
Cl
Cl
Cl
Cl
N S 3 H S
S
S
S
N
S
N O
F
captafol captafol S
H S
2+
S H
tolylfluanid tolylfluanid
Mn N S H S
x
Zn
N
H S N
mancozeb mancozeb
H S N S Zn (NH3)-
S
O N
H N
maneb maneb
S N H
O
S
propineb propineb
S N
Zn
S
Cl Cl
folpet folpet
S S
S
Cl
NH2 HN
N HN
S
The groupings can change when new results become known. Yellow zones represent accepted mode of action groups or in cases where resistance is known, cross resistance groups. In spite of this general classification, cases of incomplete or even lacking cross resistance are known within some groups with some pathogens.
O
S
O
O S
N H
S
O S
F
F
quinazolinone
thiocarbamates
O N H
Cl Cl
Cl
Cl
F F Cl
## 36 36 flusulfamide flusulfamide
Cl
Cl
pyridazinones
S
O
N
O
## 35 35 triazoxide triazoxide
Cl
## 33 33 phosphorous phosphorous acid acid
## 33 33 fosetyl-Al fosetyl-Al
O
O
OH
N
## 27 27 cymoxanil cymoxanil
terbinafine terbinafine (antimycotic) (antimycotic)
O
O
HO
N
2+
Mn SH
metiram
N
Mode of action of fungicides based on the FRAC fungicide list (published at www.frac.info/publications )
phenyl acetamides
S F
dichlofluanid dichlofluanid
O
NHCH2CH2NHCS2-
HS
O
Cl
2+
N
tiadinil tiadinil
N
S
simeconazole simeconazole
phosphorous acid
ethylphosphonates
Cl Cl
Cl
Zn SH S
N S H S
carpropamid carpropamid
S
Cl
captan captan
N
O Cl
N O
S
S
ferbam ferbam
probenazole probenazole
* Temporary status; information on mode of action and / or resistance risk is still uncertain
FRAC Mode of Action Poster January 2007
Cl
S
isotianil isotianil
Cl
OH
## 18 18
N
HO
Cl
O
O
N N
F
©
S
chlorothalonil chlorothalonil
O
N
anilazine anilazine
HS
N O
OH
Unknown Mode of Action
G4: G4: SBI SBI class class IV: IV: > squalene epoxidase > squalene epoxidase
F
Cl
pefurazoate
Cl Cl
sulphamides
N
N N
Cl
O
S
carboxamide
N H
O
polyoxin polyoxin BB
F
Si
N
N
epoxiconazole epoxiconazole
F
O
Cl
N N
O HO N H
H2 N
O
N
triflumizole triflumizole O
N
Cl
Cl
N
N
imibenconazole imibenconazole O
OH
O
O
N
O N
N
N
N
N
O
Cl S
Cl
N
phthalimides
Cl
H N
N
Cl
Cl
HO
allylamines
Cl
N
N
prothioprothioconazole conazole
Cl
N
O
imazalil imazalil
N
triticonazole triticonazole N
N H
F
N
Cl
OH
N
Cl
cyclopropane carboxamide
NH2 O
O
## 17 hydroxyanilides 17 hydroxyanilides
N
Cl
diniconazole diniconazole
Cl
N
hexaconazole
N
N
triazines
Cl
N
O
N
HO
N
dithianon dithianon
copper copper preparations preparations
## P: host defe eennccee in induc duct P: hos hosttt def hos defe def induc in ductttiioonn
O
G3: G3: SBI SBI class class III: III: hydroxyanilides hydroxyanilides >3-keto >3-keto reductase reductase in in C4-demethylation C4-demethylation
fenarimol fenarimol
O
N
N
N OH
N
Cl
Cl
Cu Cu
PP33:: uncle uncl pat ay uncleeaarr pathw uncle pathway pathw hway ay
Cl
Cl
N
Cl
PP22:: uncle uncl pat uncleear uncle ar path pathhwwaayy path
## 16.2 Inhibitors (MBI-D) Biosynthesis Inhibitors (MBI-D) 16.2 Melanin Melanin Biosynthesis
N
N
Cl
N
tricyclazole tricyclazole
sulphur sulphur ..
N
imidazoles
O N
N
flutriafol
pyroquilon pyroquilon
I2: I2: > > dehydratase dehydratase in in melanin melanin biosynthesis biosynthesis
HN
N
N
fthalide fthalide
## 19 19 polyoxins polyoxins
spiroketalamines O
Cl
OH
penconazole
HO
N
N
S
Cl
OH
acibenzolaracibenzolarS-methyl S-methyl
N
OH
Cl
N
N F F
O
N
Cl
OH
N H
OH
H4: H4: chitin chitin synthesis synthesis > chitin synthase synthase > chitin
spiroxamine spiroxamine
N
triadimefon triadimefon N
N
HO
O
Cl N
N Cl
flusilazole
HO
cyproconazole cyproconazole
N
piperalin piperalin
fenpropifenpropimorph morph
N N
Cl
S O
dithiocarbamates & relatives
O
dodemorph dodemorph
F
O N
Cl
N
N
O
OH
myclobutanil
O
N
## P: host defe eennccee in induc duct P: hos hosttt def hos defe def induc in ductttiioonn
N
N
N
N
N
Cl
O
Cl
Cl
N
S
S S
Cl
N
tridemorph tridemorph
pyrimidines
O
N
chloronitriles N
O
S S
O
OH
validamycin validamycin
O
N
N
bromuconazole bromuconazole
N
Cl
HO
OH O
HO
n= 10 to 13 n=12: ~ 70%
N
tetraconazole tetraconazole
Cl
valiphenal valiphenal
N
## P: P: host host defence defence induction induction
## 16.1 Biosynthesis Inhibitors Inhibitors (MBI-R) (MBI-R) 16.1 Melanin Melanin Biosynthesis
Cl
N
O
Cl
N
N
(CH2)n
N
N
N
fluquinconazole N
N
N
aldimorph aldimorph
Cl
N
fenpropidin fenpropidin
N
Cl
Cl
F
S N H
benthiavalicarb benthiavalicarb
# 26 glucopyranosyl antibiotic
O
O
F
O Cl
N
OH
F
N N
N
Br
N
N
N O
(CH2 )n
Cl
Cl
pyridines N
N
tebuconazole tebuconazole
O
prothiocarb prothiocarb
P1: P1: salicylic salicylic pathway pathway
HO
O
n= 11
N
N
fenbuconazole
Cl
triforine triforine
HO
O N
N
H N
O
etridiazole etridiazole
P: Host Defence Inducer
pyrroloquinolione
O N H
O
O
I1: I1: > > reductase reductase in in melanin melanin biosynthesis biosynthesis
OH
O
O O
H N
O
N H
S O
I: Melanin Synthesis in Cell Wall
NH
Cl
pyridines
O
O
O
H3: trehalase and inositol biosynthesis
N
N
Cl
Cl Cl
ipconazole ipconazole
N
H N
O
tolclofostolclofosmethyl methyl
H: Glucan Synthesis
HO
N H
O
mandipropamid mandipropamid
valinamide carbamates
iodocarb iodocarb
O
thiadiazoles
piperidines
morpholines
Cl
O
O
O
N H
O I
O
biphenyl biphenyl
O
P O
isoisoprothiolane prothiolane
dithiolanes
Cl
N
N
Cl
N
azaconazole azaconazole
Cl
N
flumorph flumorph
O
Cl
isobenzofuranone
N
N
N
N
O
N
HN
HO
F O
O
Cl
Cl
Cl
piperazines
Cl
N
propamocarb propamocarb
thiophosphate
S
fludioxonil fludioxonil
## 55 amines amines
N Cl
quintozene quintozene (PCNB) (PCNB)
tecnazene tecnazene (TCNB) (TCNB) O
O
N
N H
O
mandelic acid amides
cinnamic acid amides
O
N
O
## 40 Acid Amides Amides 40 Carboxylic Carboxylic Acid (CAA (CAA fungicides) fungicides)
O
Cl S
iprobenfos iprobenfos
procymidone procymidone
G2: G2: SBI SBI class class II: II: Amines Amines 14-reductase > -reductase (erg24) -isomerase (erg2) → ∆∆77-isomerase > ∆∆14 (erg24) and (erg2) and ∆∆88→
## 33 DeMethylation Inhibitors (=DMI (=DMI fungicides) fungicides) DeMethylation Inhibitors
+
N
Cl
edifenphos edifenphos
O
N
Cl
G: Sterol Biosynthesis Inhibitors (SBI fungicides) G1: G1: SBI SBI class class I: I: DMI DMI fungicides fungicides > >C14 C14 demethylase demethylase (erg11/cyp51) (erg11/cyp51)
O
silthiofam silthiofam
F5: F5: phospholipid phospholipid biosynthesis biosynthesis and and cell cell wall wall deposition deposition (prop.) (prop.)
Cl NH2
O
N
F
Cl
oxytetracycline oxytetracycline (bactericide) (bactericide)
triazoles
Si
O
O
F
O
O
O
N Cl
OH OH OH
streptomycin streptomycin (bactericide) (bactericide)
F4: F4: cell cell membrane membrane permeability, permeability, fatty fatty acides acides (prop.) (prop.)
O
+
O
Cl
H N
NH2 NH2 NH
O
Cl
O
Cl
O
Chiral
O O
S
N N
## 28 carbamates 28 carbamates
Cl
chlozolinate chlozolinate
## 12 12 phenylpyrroles phenylpyrroles (PP(PP- fungicides) fungicides)
HO
N
F3: F3: lipid lipid peroxidation peroxidation (prop.) (prop.)
O
iprodione iprodione
O
N
Cl
HO
P O
N
pyrazophos pyrazophos
O
Cl
O O
D5: D5: protein protein synthesis synthesis
O
N
quinoxyfen quinoxyfen
kasugamycin kasugamycin
D4: D4: protein protein synthesis synthesis
N H
H N
ferimzone ferimzone
## 14 14 aromatic aromatic hydrocarbons hydrocarbons & & heteroaromatics heteroaromatics
N
O
O
NH
F
N
phosphorothiolates
S
O NH
O
Cl
OH
cyprodinil cyprodinil
O
F
pyribencarb pyribencarb
nitrobenzenes
Cl
OH
HO
## 38 38 thiophenethiophenecarboxamides carboxamides
+
N
fluazinam fluazinam
Cl
O
dihydrodioxazines
metominometominostrobin strobin
N O
N Cl
O
fluoxastrobin fluoxastrobin
O
+
O
O
N
HN
O
O
C7: C7: ATP ATP production production (prop.) (prop.)
F
O
## 66 phosphorothiolates phosphorothiolates & & dithiolanes dithiolanes
## 22 dicarboximides dicarboximides
F
O
HO
F
F
O NH
O
NH2
OH
fentin fentin hydroxide hydroxide
F: Lipid and Membrane Synthesis, Cell Wall Deposition F2: F2: phospholipid phospholipid biosynthesis biosynthesis > > methyltransferase methyltransferase
E3: E3: Osmotic Osmotic signal signal transduction transduction > > MAP MAP // histidine histidine kinase kinase (os-1, (os-1, Daf1) Daf1)
OH OH N
HN
#13 #13 quinolines quinolines
O
O
dinocap dinocap
N
Cl
N
N
OH
+
N
N
N
N
O
Sn
O O
O
NH S
furametpyr furametpyr
E: Signal Transduction E1: E1: G-proteins G-proteins in in early early cell cell signalling signalling (prop.) (prop.)
O
O
+
Cl
fluopicolide fluopicolide
+
+
O
N
O H N
enestrobin enestrobin N H
N
Cl
O
trifloxystrobin trifloxystrobin
N O
O
O S
N
O
O
O
O
N
penthiopyrad penthiopyrad
N
dimoxystrobin dimoxystrobin
O
F F
oxycarboxin oxycarboxin
N H
F
N
NH F
O O
O
O
imidazolinones
O
N
pyraclostrobin pyraclostrobin O
F
N H
N
Cl
N
Cl
O
O
picoxystrobin picoxystrobin
S
N
O
O
famoxadone famoxadone
O
O
O O
O
F
HN
Cl
N
orysastrobin orysastrobin
kresoximkresoximmethyl methyl
F
F
Br
thifluzamide thifluzamide
Cl
OH
Cl
N
H N O
O
Sn Cl
fentin fentin chloride chloride
O
O
N
O
O
O
O N H
N O
azoxystrobin azoxystrobin
mepronil mepronil
F
diflumetorim diflumetorim
O O
fenfuram
F
F
## 29 29
N
methoxycarbamates O
O
O
diethofencarb diethofencarb
HN
H N
H2N
O
fentin fentin acetate acetate
NH O
O
N
F
O
N H
S
N
N
## 43 43 acylpicolides acylpicolides
Cl
D3: D3: protein protein synthesis synthesis
## 23 acid 23 enopyranuronic enopyranuronic acid
Sn
oxazolidinediones
oximinoacetates
N
O
N H
O
N H
thiazole carboxamides
oximinoacetamides
O
O
benodanil benodanil
O
B5: B5: delocalisation delocalisation of of spectrin-like spectrin-like proteins proteins
B4: B4: cell cell division division (prop.) (prop.)
N H
I
O
N H
thiophanatethiophanatemethyl methyl
## 22 22 benzamides benzamides
D: Amino Acid and Protein Synthesis D2: D2: protein protein synthesis synthesis
O
S
** negative negative cross-resistance cross-resistance to to B1 B1
D1: D1: methionine methionine biosynthesis biosynthesis (cgs (cgs gene) gene) (prop.) (prop.)
## 30 30 organo organo tins tins
O
N
C5: C5: uncouplers uncouplers of of oxidative oxidative phosphorylation phosphorylation
F O
O N
O
O
hymexazol hymexazol
B3: B3: >ß-tubulin >ß-tubulin assembly assembly in in mitosis mitosis
## 10 10 N-phenyl N-phenyl carbamates carbamates
O
HO
O
cyazofamid cyazofamid
furan carboxamides
F F
F
A3: A3: DNA DNA // RNA RNA synthesis synthesis (prop.) (prop.)
F
C3: C3: inhibition inhibition of of complex complex III III > > cytochrome cytochrome bc1 bc1 (ubiquinol (ubiquinol oxidase) oxidase) at at Qo Qo site site
## 77 carboxamides carboxamides
benzamides
O
O O
S
N H
thiabendazole thiabendazole
benzimidazoles
H N
S
NH
ofurace ofurace
O O S
Cl
O
Br
C2: C2: inhibition inhibition of of complex complex II: II: > > succinate-dehydrogenase succinate-dehydrogenase
## 39 39 pyrimidinpyrimidinamines amines
O
thiophanate thiophanate
S
N H
O
thiophanates
O O
S
N H
benomyl benomyl N
H N
S
O
N H
N H
O
HO
N N
S
O
C1: C1: inhibition inhibition of of complex complex II (prop.) (prop.)
## 1: 1: MBC MBC fungicides fungicides (= (= Methyl Methyl Benzimidazole Benzimidazole Carbamates) Carbamates) N
butyrolactones
N O N
C: Respiration
B1: B1: > > ß-tubulin ß-tubulin assembly assembly in in mitosis mitosis
HO
O
N
C6: C6: inhibitors inhibitors of of oxydative oxydative phosporylation, phosporylation, ATP ATP synthase synthase
># inside Inhibitors) Inhibitors) ># 21 21 QiI QiI fungicides fungicides (Quinone (Quinone inside
O
chiral HO HO
C4: C4: inhibition inhibition of of complex complex III III > > cytochrome cytochrome bc1 bc1 at at Qi Qi site site
FRAC classification on mode of action 2007 (www.frac.info)
acylalanines O
C: Respiration
Mode of Action of Fungicides
A2: A2: purine purine metabolism metabolism > > adenosin-deaminase adenosin-deaminase
Although details presented herein are accurate to our knowledge at the time of publication, neither FRAC nor its member companies make any representation or warranty with regard to the content of this presentation, in particular with regard to its correctness and completeness. Neither FRAC nor its member companies assume any liability for the content of this presentation or its use.
thiram
H S N S Zn
mixture mixture of of iminoctadine iminoctadine and and other other polyamines polyamines
ziram ziram
N S H S
guazatine guazatine
Legend:
C2: complex II: > succinate-dehydrogenase # 7 carboxamides
phthalimides
iminoctadine iminoctadine
mode of action group sub-group > target site of action (where known) or putative target site (=prop.) FRAC code no. (#) and group name
chemical (sub-) group
NH
H2N
H N +
NH2
guanidines
zineb
C: Respiration
N H H N NH2
O O
dodine dodine
## 4: 4: PA-fungicides PA-fungicides (phenylamides) (phenylamides)
## 8: 8: hydroxy hydroxy (2-amino)-pyrimidines (2-amino)-pyrimidines
HO
HO
O
O S
N
N
O
N
B: Mitosis and Cell Division
N HN
O
HO
HO
N
O
metalaxyl-M metalaxyl-M
N
O
OH HO
benalaxyl
O
bupirimate bupirimate
metalaxyl metalaxyl
N
N
O O
N
oxazolidinones
furalaxyl furalaxyl
dimethirimol dimethirimol
Cl
HO
N
O
O
O
O
O
HO
N
N
N
N H
N
NH
N N H
N
H N
N
fuberidazole fuberidazole
O
N
N H
O
oxadixyl oxadixyl
carbendazim carbendazim
ethirimol ethirimol
NH
B2: B2: > ß-tubulin > ß-tubulin assembly assembly in in mitosis* mitosis*
A4: A4: DNA DNA supercoiling supercoiling > > DNA DNA topoisomerase topoisomerase type type IIII (gyrase) (gyrase)
## 32: 32: heteroaromatics heteroaromatics
## 31: 31: carboxylic carboxylic acids acids
isoxazoles
isothiazolones O
H N
O
N
S
O
O
oxolinic oxolinic acid acid (bactericide) (bactericide)
octhilinone octhilinone
N N
N
N H
N
amisulbrom amisulbrom
## 20 20 phenylureas phenylureas
## 11 Quinone outside outside Inhibitors Inhibitors )) 11 QoI QoI fungicides fungicides (( Quinone
methoxyacrylates
O
flutolanil
O
N
## 99 Anilino-Pyrimidines Anilino-Pyrimidines (( AP AP fungicides fungicides ))
F O
F
H N
N
F
O Cl
Br
N
Cl
O
N H
O
Cl
N H
O
O
pyrazole carboxamides
oxathiin carboxamides
N H
Cl
N
O
F
N
O
O
O
S
O N H
pyridine carboxamides
N
F
zoxamide zoxamide
pencycuron pencycuron
O
N
O Cl
F
N N
O
F
O
Cl N H
boscalid boscalid
carboxin carboxin
binapacryl binapacryl
## 24 antibiotics hexopyranosyl antibiotics 24 hexopyranosyl
H2 N OH
O
NH
NH2
NH2
N H HO
NH
N
O
O
fenamidone fenamidone
F
O
benzylcarbamates
O
F
OH
N
O
blasticidin-S blasticidin-S
N
N
N H
O
O N O
N
O
N
N
## 25 25 glucopyranosyl glucopyranosyl antibiotics antibiotics
mepanipyrim mepanipyrim
E2: E2: Osmotic Osmotic signal signal transduction transduction > MAP // histidinehistidine- kinase kinase (os-2, (os-2, HOG1) HOG1) > MAP
## 41 41 tetracycline tetracycline antibiotics antibiotics
NH
HO
N
HO
OH O
O
NH
OH
OH NH2
HN
OH
OH
O
N H
H N
O
OH
O HN
pyrimethanil pyrimethanil
O
N
N
O
fenpiclonil fenpiclonil
O Cl
Cl
Cl
O
dicloran dicloran
+
N
O
O
Cl
Cl
Cl
Cl
O
O P
O
O
S
P
dimethomorph dimethomorph
O
O Cl
O
vinclozolin vinclozolin
Cl
O
S
O
S
S
benzenes
Cl
chloroneb chloroneb
Cl Cl N
Cl
S
N
N H
N
iprovalicarb iprovalicarb
OH
Cl
N
N
N
Cl
N Cl
Cl
bitertanol bitertanol
F
metconazole
O
F
F
pyrifenox pyrifenox
M: Multi Site Action anthraquinones
inorganics
F
O
triazolobenzothiazole
Si N
F
Cl
O O
O
nuarimol nuarimol
Cl
O Cl
O
OH
difenoconazole difenoconazole
triadimenol triadimenol
Cl
propiconazole
N
Cl
N
S
HO
O S N H
OH
N
propionamide
Cl
N
H H N
N
O
H N
N
S
S
Fe
O Cl
O
O
N H
diclocymet diclocymet
fenoxanil fenoxanil
cyanoacetamideoxime
N
U: Recent Molecules* thiazole carboxamides
phthalamic acid
H S S N
O O
N
O
Cl
N
O
Cl
oxpoconazole oxpoconazole
prochloraz prochloraz
O
O
N
N H
O
N H
H H33PO PO33
PH
AlH3
N H
thiocarbamates
naftifine naftifine (antimycotic) (antimycotic)
benzenesulfonamides
benzotriazines O
fenhexamid fenhexamid O
N
N
N
O
Cl
N
N
N
+
N
Cl
Cl O
+
H N
pyributicarb pyributicarb (herbicide) (herbicide)
N H
O
F
N N H
## 34 34 tecloftalam tecloftalam
O O
N Cl
## 37 37 diclomezine diclomezine
N H
## 42 42 methasulfocarb methasulfocarb
F
HN N
O
F F
## U5 U5 ethaboxam ethaboxam
## U6 U6 cyflufenamid cyflufenamid
I
O
O
Br
O
N N
O
## U7 U7 proquinazid proquinazid
O
O
## U8 U8 metrafenone metrafenone
O
NHCH2CH2NHCS2-
S
Cl
Cl
S
N
N O
O
Cl
Cl
Cl
Cl
N S 3 H S
S
S
S
N
S
N O
F
captafol captafol S
H S
2+
S H
tolylfluanid tolylfluanid
Mn N S H S
x
Zn
N
H S N
mancozeb mancozeb
H S N S Zn (NH3)-
S
O N
H N
maneb maneb
S N H
O
S
propineb propineb
S N
Zn
S
Cl Cl
folpet folpet
S S
S
Cl
NH2 HN
N HN
S
The groupings can change when new results become known. Yellow zones represent accepted mode of action groups or in cases where resistance is known, cross resistance groups. In spite of this general classification, cases of incomplete or even lacking cross resistance are known within some groups with some pathogens.
O
S
O
O S
N H
S
O S
F
F
quinazolinone
thiocarbamates
O N H
Cl Cl
Cl
Cl
F F Cl
## 36 36 flusulfamide flusulfamide
Cl
Cl
pyridazinones
S
O
N
O
## 35 35 triazoxide triazoxide
Cl
## 33 33 phosphorous phosphorous acid acid
## 33 33 fosetyl-Al fosetyl-Al
O
O
OH
N
## 27 27 cymoxanil cymoxanil
terbinafine terbinafine (antimycotic) (antimycotic)
O
O
HO
N
2+
Mn SH
metiram
N
Mode of action of fungicides based on the FRAC fungicide list (published at www.frac.info/publications )
phenyl acetamides
S F
dichlofluanid dichlofluanid
O
NHCH2CH2NHCS2-
HS
O
Cl
2+
N
tiadinil tiadinil
N
S
simeconazole simeconazole
phosphorous acid
ethylphosphonates
Cl Cl
Cl
Zn SH S
N S H S
carpropamid carpropamid
S
Cl
captan captan
N
O Cl
N O
S
S
ferbam ferbam
probenazole probenazole
* Temporary status; information on mode of action and / or resistance risk is still uncertain
FRAC Mode of Action Poster January 2007
Cl
S
isotianil isotianil
Cl
OH
## 18 18
N
HO
Cl
O
O
N N
F
©
S
chlorothalonil chlorothalonil
O
N
anilazine anilazine
HS
N O
OH
Unknown Mode of Action
G4: G4: SBI SBI class class IV: IV: > squalene epoxidase > squalene epoxidase
F
Cl
pefurazoate
Cl Cl
sulphamides
N
N N
Cl
O
S
carboxamide
N H
O
polyoxin polyoxin BB
F
Si
N
N
epoxiconazole epoxiconazole
F
O
Cl
N N
O HO N H
H2 N
O
N
triflumizole triflumizole O
N
Cl
Cl
N
N
imibenconazole imibenconazole O
OH
O
O
N
O N
N
N
N
N
O
Cl S
Cl
N
phthalimides
Cl
H N
N
Cl
Cl
HO
allylamines
Cl
N
N
prothioprothioconazole conazole
Cl
N
O
imazalil imazalil
N
triticonazole triticonazole N
N H
F
N
Cl
OH
N
Cl
cyclopropane carboxamide
NH2 O
O
## 17 hydroxyanilides 17 hydroxyanilides
N
Cl
diniconazole diniconazole
Cl
N
hexaconazole
N
N
triazines
Cl
N
O
N
HO
N
dithianon dithianon
copper copper preparations preparations
## P: host defe eennccee in induc duct P: hos hosttt def hos defe def induc in ductttiioonn
O
G3: G3: SBI SBI class class III: III: hydroxyanilides hydroxyanilides >3-keto >3-keto reductase reductase in in C4-demethylation C4-demethylation
fenarimol fenarimol
O
N
N
N OH
N
Cl
Cl
Cu Cu
PP33:: uncle uncl pat ay uncleeaarr pathw uncle pathway pathw hway ay
Cl
Cl
N
Cl
PP22:: uncle uncl pat uncleear uncle ar path pathhwwaayy path
## 16.2 Inhibitors (MBI-D) Biosynthesis Inhibitors (MBI-D) 16.2 Melanin Melanin Biosynthesis
N
N
Cl
N
tricyclazole tricyclazole
sulphur sulphur ..
N
imidazoles
O N
N
flutriafol
pyroquilon pyroquilon
I2: I2: > > dehydratase dehydratase in in melanin melanin biosynthesis biosynthesis
HN
N
N
fthalide fthalide
## 19 19 polyoxins polyoxins
spiroketalamines O
Cl
OH
penconazole
HO
N
N
S
Cl
OH
acibenzolaracibenzolarS-methyl S-methyl
N
OH
Cl
N
N F F
O
N
Cl
OH
N H
OH
H4: H4: chitin chitin synthesis synthesis > chitin synthase synthase > chitin
spiroxamine spiroxamine
N
triadimefon triadimefon N
N
HO
O
Cl N
N Cl
flusilazole
HO
cyproconazole cyproconazole
N
piperalin piperalin
fenpropifenpropimorph morph
N N
Cl
S O
dithiocarbamates & relatives
O
dodemorph dodemorph
F
O N
Cl
N
N
O
OH
myclobutanil
O
N
## P: host defe eennccee in induc duct P: hos hosttt def hos defe def induc in ductttiioonn
N
N
N
N
N
Cl
O
Cl
Cl
N
S
S S
Cl
N
tridemorph tridemorph
pyrimidines
O
N
chloronitriles N
O
S S
O
OH
validamycin validamycin
O
N
N
bromuconazole bromuconazole
N
Cl
HO
OH O
HO
n= 10 to 13 n=12: ~ 70%
N
tetraconazole tetraconazole
Cl
valiphenal valiphenal
N
## P: P: host host defence defence induction induction
## 16.1 Biosynthesis Inhibitors Inhibitors (MBI-R) (MBI-R) 16.1 Melanin Melanin Biosynthesis
Cl
N
O
Cl
N
N
(CH2)n
N
N
N
fluquinconazole N
N
N
aldimorph aldimorph
Cl
N
fenpropidin fenpropidin
N
Cl
Cl
F
S N H
benthiavalicarb benthiavalicarb
# 26 glucopyranosyl antibiotic
O
O
F
O Cl
N
OH
F
N N
N
Br
N
N
N O
(CH2 )n
Cl
Cl
pyridines N
N
tebuconazole tebuconazole
O
prothiocarb prothiocarb
P1: P1: salicylic salicylic pathway pathway
HO
O
n= 11
N
N
fenbuconazole
Cl
triforine triforine
HO
O N
N
H N
O
etridiazole etridiazole
P: Host Defence Inducer
pyrroloquinolione
O N H
O
O
I1: I1: > > reductase reductase in in melanin melanin biosynthesis biosynthesis
OH
O
O O
H N
O
N H
S O
I: Melanin Synthesis in Cell Wall
NH
Cl
pyridines
O
O
O
H3: trehalase and inositol biosynthesis
N
N
Cl
Cl Cl
ipconazole ipconazole
N
H N
O
tolclofostolclofosmethyl methyl
H: Glucan Synthesis
HO
N H
O
mandipropamid mandipropamid
valinamide carbamates
iodocarb iodocarb
O
thiadiazoles
piperidines
morpholines
Cl
O
O
O
N H
O I
O
biphenyl biphenyl
O
P O
isoisoprothiolane prothiolane
dithiolanes
Cl
N
N
Cl
N
azaconazole azaconazole
Cl
N
flumorph flumorph
O
Cl
isobenzofuranone
N
N
N
N
O
N
HN
HO
F O
O
Cl
Cl
Cl
piperazines
Cl
N
propamocarb propamocarb
thiophosphate
S
fludioxonil fludioxonil
## 55 amines amines
N Cl
quintozene quintozene (PCNB) (PCNB)
tecnazene tecnazene (TCNB) (TCNB) O
O
N
N H
O
mandelic acid amides
cinnamic acid amides
O
N
O
## 40 Acid Amides Amides 40 Carboxylic Carboxylic Acid (CAA (CAA fungicides) fungicides)
O
Cl S
iprobenfos iprobenfos
procymidone procymidone
G2: G2: SBI SBI class class II: II: Amines Amines 14-reductase > -reductase (erg24) -isomerase (erg2) → ∆∆77-isomerase > ∆∆14 (erg24) and (erg2) and ∆∆88→
## 33 DeMethylation Inhibitors (=DMI (=DMI fungicides) fungicides) DeMethylation Inhibitors
+
N
Cl
edifenphos edifenphos
O
N
Cl
G: Sterol Biosynthesis Inhibitors (SBI fungicides) G1: G1: SBI SBI class class I: I: DMI DMI fungicides fungicides > >C14 C14 demethylase demethylase (erg11/cyp51) (erg11/cyp51)
O
silthiofam silthiofam
F5: F5: phospholipid phospholipid biosynthesis biosynthesis and and cell cell wall wall deposition deposition (prop.) (prop.)
Cl NH2
O
N
F
Cl
oxytetracycline oxytetracycline (bactericide) (bactericide)
triazoles
Si
O
O
F
O
O
O
N Cl
OH OH OH
streptomycin streptomycin (bactericide) (bactericide)
F4: F4: cell cell membrane membrane permeability, permeability, fatty fatty acides acides (prop.) (prop.)
O
+
O
Cl
H N
NH2 NH2 NH
O
Cl
O
Cl
O
Chiral
O O
S
N N
## 28 carbamates 28 carbamates
Cl
chlozolinate chlozolinate
## 12 12 phenylpyrroles phenylpyrroles (PP(PP- fungicides) fungicides)
HO
N
F3: F3: lipid lipid peroxidation peroxidation (prop.) (prop.)
O
iprodione iprodione
O
N
Cl
HO
P O
N
pyrazophos pyrazophos
O
Cl
O O
D5: D5: protein protein synthesis synthesis
O
N
quinoxyfen quinoxyfen
kasugamycin kasugamycin
D4: D4: protein protein synthesis synthesis
N H
H N
ferimzone ferimzone
## 14 14 aromatic aromatic hydrocarbons hydrocarbons & & heteroaromatics heteroaromatics
N
O
O
NH
F
N
phosphorothiolates
S
O NH
O
Cl
OH
cyprodinil cyprodinil
O
F
pyribencarb pyribencarb
nitrobenzenes
Cl
OH
HO
## 38 38 thiophenethiophenecarboxamides carboxamides
+
N
fluazinam fluazinam
Cl
O
dihydrodioxazines
metominometominostrobin strobin
N O
N Cl
O
fluoxastrobin fluoxastrobin
O
+
O
O
N
HN
O
O
C7: C7: ATP ATP production production (prop.) (prop.)
F
O
## 66 phosphorothiolates phosphorothiolates & & dithiolanes dithiolanes
## 22 dicarboximides dicarboximides
F
O
HO
F
F
O NH
O
NH2
OH
fentin fentin hydroxide hydroxide
F: Lipid and Membrane Synthesis, Cell Wall Deposition F2: F2: phospholipid phospholipid biosynthesis biosynthesis > > methyltransferase methyltransferase
E3: E3: Osmotic Osmotic signal signal transduction transduction > > MAP MAP // histidine histidine kinase kinase (os-1, (os-1, Daf1) Daf1)
OH OH N
HN
#13 #13 quinolines quinolines
O
O
dinocap dinocap
N
Cl
N
N
OH
+
N
N
N
N
O
Sn
O O
O
NH S
furametpyr furametpyr
E: Signal Transduction E1: E1: G-proteins G-proteins in in early early cell cell signalling signalling (prop.) (prop.)
O
O
+
Cl
fluopicolide fluopicolide
+
+
O
N
O H N
enestrobin enestrobin N H
N
Cl
O
trifloxystrobin trifloxystrobin
N O
O
O S
N
O
O
O
O
N
penthiopyrad penthiopyrad
N
dimoxystrobin dimoxystrobin
O
F F
oxycarboxin oxycarboxin
N H
F
N
NH F
O O
O
O
imidazolinones
O
N
pyraclostrobin pyraclostrobin O
F
N H
N
Cl
N
Cl
O
O
picoxystrobin picoxystrobin
S
N
O
O
famoxadone famoxadone
O
O
O O
O
F
HN
Cl
N
orysastrobin orysastrobin
kresoximkresoximmethyl methyl
F
F
Br
thifluzamide thifluzamide
Cl
OH
Cl
N
H N O
O
Sn Cl
fentin fentin chloride chloride
O
O
N
O
O
O
O N H
N O
azoxystrobin azoxystrobin
mepronil mepronil
F
diflumetorim diflumetorim
O O
fenfuram
F
F
## 29 29
N
methoxycarbamates O
O
O
diethofencarb diethofencarb
HN
H N
H2N
O
fentin fentin acetate acetate
NH O
O
N
F
O
N H
S
N
N
## 43 43 acylpicolides acylpicolides
Cl
D3: D3: protein protein synthesis synthesis
## 23 acid 23 enopyranuronic enopyranuronic acid
Sn
oxazolidinediones
oximinoacetates
N
O
N H
O
N H
thiazole carboxamides
oximinoacetamides
O
O
benodanil benodanil
O
B5: B5: delocalisation delocalisation of of spectrin-like spectrin-like proteins proteins
B4: B4: cell cell division division (prop.) (prop.)
N H
I
O
N H
thiophanatethiophanatemethyl methyl
## 22 22 benzamides benzamides
D: Amino Acid and Protein Synthesis D2: D2: protein protein synthesis synthesis
O
S
** negative negative cross-resistance cross-resistance to to B1 B1
D1: D1: methionine methionine biosynthesis biosynthesis (cgs (cgs gene) gene) (prop.) (prop.)
## 30 30 organo organo tins tins
O
N
C5: C5: uncouplers uncouplers of of oxidative oxidative phosphorylation phosphorylation
F O
O N
O
O
hymexazol hymexazol
B3: B3: >ß-tubulin >ß-tubulin assembly assembly in in mitosis mitosis
## 10 10 N-phenyl N-phenyl carbamates carbamates
O
HO
O
cyazofamid cyazofamid
furan carboxamides
F F
F
A3: A3: DNA DNA // RNA RNA synthesis synthesis (prop.) (prop.)
F
C3: C3: inhibition inhibition of of complex complex III III > > cytochrome cytochrome bc1 bc1 (ubiquinol (ubiquinol oxidase) oxidase) at at Qo Qo site site
## 77 carboxamides carboxamides
benzamides
O
O O
S
N H
thiabendazole thiabendazole
benzimidazoles
H N
S
NH
ofurace ofurace
O O S
Cl
O
Br
C2: C2: inhibition inhibition of of complex complex II: II: > > succinate-dehydrogenase succinate-dehydrogenase
## 39 39 pyrimidinpyrimidinamines amines
O
thiophanate thiophanate
S
N H
O
thiophanates
O O
S
N H
benomyl benomyl N
H N
S
O
N H
N H
O
HO
N N
S
O
C1: C1: inhibition inhibition of of complex complex II (prop.) (prop.)
## 1: 1: MBC MBC fungicides fungicides (= (= Methyl Methyl Benzimidazole Benzimidazole Carbamates) Carbamates) N
butyrolactones
N O N
C: Respiration
B1: B1: > > ß-tubulin ß-tubulin assembly assembly in in mitosis mitosis
HO
O
N
C6: C6: inhibitors inhibitors of of oxydative oxydative phosporylation, phosporylation, ATP ATP synthase synthase
># inside Inhibitors) Inhibitors) ># 21 21 QiI QiI fungicides fungicides (Quinone (Quinone inside
O
chiral HO HO
C4: C4: inhibition inhibition of of complex complex III III > > cytochrome cytochrome bc1 bc1 at at Qi Qi site site
FRAC classification on mode of action 2007 (www.frac.info)
acylalanines O
C: Respiration
Mode of Action of Fungicides
A2: A2: purine purine metabolism metabolism > > adenosin-deaminase adenosin-deaminase
Although details presented herein are accurate to our knowledge at the time of publication, neither FRAC nor its member companies make any representation or warranty with regard to the content of this presentation, in particular with regard to its correctness and completeness. Neither FRAC nor its member companies assume any liability for the content of this presentation or its use.
thiram
H S N S Zn
mixture mixture of of iminoctadine iminoctadine and and other other polyamines polyamines
ziram ziram
N S H S
guazatine guazatine
Legend:
C2: complex II: > succinate-dehydrogenase # 7 carboxamides
phthalimides
iminoctadine iminoctadine
mode of action group sub-group > target site of action (where known) or putative target site (=prop.) FRAC code no. (#) and group name
chemical (sub-) group
NH
H2N
H N +
NH2
guanidines
zineb
C: Respiration
N H H N NH2
O O
dodine dodine
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