A: Nucleic Acid Synthesis

S C: Respiration
C:
A1: RNA synthesis
A1 th i
> RNA polymerase I
# 4: PA-fungicides (PhenylAmides)
A2: purine
A2 i metabolism
t b li
> adenosin-deaminase
# 8: hydroxy (2-amino)-pyrimidines
M d off Action
Mode A ti n off Fungicides
F i id C1: iinhibition
C1 hibiti off complex
NADH Oxido-reductase
l I

# 39 pyrimidinamines
C4 iinhibition
C4: hibi i off complex
> cytochrome bc1(ubiquinone reductase) at Qi site
# 21 QiI fungicides
># f i id (Q(Quinone
i inside
l III
i id Inhibitors)
I hibit )
C6: iinhibitors
C6 hibit
of oxidative
phosphorylation,
p p y ,

FRAC classification on mode of

o action 2009 (www
(www.frac.info)
frac info)
acylalanines
y N ATP synthase
y
HO O
O HO O
O N N
# 30 organo
g tins
F O O
S N
O
Cl O S N O
O Cl N
O N O N H F O F
N S
N N
HO O O N
O
S N N
N
O N

B Mitosis
B: Mit i and
d Cell
C ll Division
Di i i C Respiration
C: R i ti
O N N Br

benalaxyl metalaxyl HN diflumetorim cyazofamid

y amisulbrom
Sn
O

furalaxyl b ii t
bupirimate O
O HO O
HO O
B1 > ß-tubulin
B1: ß t b lin assembl
assembly in mitosis C2: inhibition of complex II: C3: iinhibition
C3 hibiti off complex
l III C5 uncouplers
C5: l off fentin acetate
O N O N
HO
# 1:
1 MBC ffungicides
i id ((= Methyl
M th l Benzimidazole
B i id l Carbamates)
C b t ) > succinate-dehydrogenase
succinate dehydrogenase > cytochrome
t h b
bc1
1 ((ubiquinol
bi i l oxidase)
id ) att Q
Qo site
it ((cytt b gene)) oxidative
id ti
chiral
# 7 SDHI (Succinate DeHydrogenase Inhibitors) # 11 QoI fungicides ( Quinone outside Inhibitors )
N N phosphorylation
benalaxyl-M metalaxyl-M N Pyrazole carboxamides # 29
O
S
H
N O thi h
thiophanates
t methoxy- oximino- oxazolidine- Sn
N O
N O acrylates acetamides diones Cl

oxazolidinones dimethirimol N
butyrolactones N
H NH
S
O
O F O
F
NH
Cl O F F
N N H N
H
O O N O fentin chloride
Cl O O O O O H
H N
H
N
H
O S N O
N N N
H F
N oximino- methoxy
methoxy- O
O O
O
O
H N
N HO
benomyl
N
H N N
thiophanate NH O N O
N
N
H N N
acetates carbamates N
+

O
N O N fuberidazole S O Cl O O O O
O N N
HO N N N N O O Cl O O H
H S S N N O +

O N N N O bixafen F sedaxane N O N f
famoxadone
d N
NH H H H furametpyr N H
O
O
O O
Sn
O
N F
thiophanate- N H N bi
binapacryl
l O O OH

N H O
ofurace oxadixyl ethirimol carbendazim thiabendazole methyl F N azoxystrobin orysastrobin Cl
N O imidazolinones +
O
N
N
benzimidazoles F F O O O N O- fentin hydroxide
thiaz
zole penthiopyrad
thi d i
isopyrazam
N O
N
carboxaamides Pyridinyl-ethyl O O -
O O+

b
benzamides
id F
F kresoxim- NH meptyll di
dinocap
O
N O
methyl pyraclostrobin
py ac ost ob S N O
oxathiin
thii F

A3: DNA / RNA synthesis (prop

(prop.)) A4: DNA supercoiling B2: B3: B4: B5: F F
carboxamides
O O
N
O N

F F

# 32: heteroaromatics > DNA topoisomerase type II (gyrase) > ß-tubulin

ß tubulin >ß tubulin
>ß-tubulin cell division (prop
(prop.)) delocalisation F
F O
Br O

F
F
F
F
Cl
O
F
F
F
phenyl-
h l
O O

F
NH Cl
Cl
F C7: ATP p
C production
oduct o
F dimoxystrobin
(prop.)
O F
N
picoxystrobin
p y
of spectrin
spectrin-like
like
O
# 31: carboxylic acids # 20 phenylureas benzamides
assembly assembly
N O N
S
H
Br N N F N F fenamidone O HN O
H N
# 38 thiophene
thiophene-
+ +
O
O O N N N

i mitosis*
in it i * i mitosis
in it i proteins O
S
O

N
O O
N
O
O
N
O
benzylcarbamates
O O

carboxamides
isoxazoles isothiazolones thifluzamide N Cl
# 10 N-phenyl
N h l # 22 toluamides
t l id # 43 acylpicolides H
fl
fluopyram F
H Cl N
O F F
O trifloxystrobin O F
carbamates pyridi
idiine
i ffuran F F O
mepronil
N O
H
N O
fluoxastrobin O Cl fluazinam
O O
carboxammides oxycarboxin carboxamides N O
O N
O N
H O O O O H
H
O
N
O
HO
F
dihydro-
O O O
N N O
O
O F
Cl metomino- dioxazines
S O
Cl F O enestrobin N
N
H
Cl N N H O
flutolanil strobin O
N
H
O N
H
O
O
H N O O N H
S
N N N
N Si
oxolinic acid Cl H H S N N
O Cl N H
hymexazol octhilinone (bactericide)
Cl
N Cl H N pyribencarb
py N
O H
diethofencarb fluopicolide O I
zoxamide pencycuron
p y silthiofam
Cl
benodanil
ferimzone
b
bosca
alid
lid carboxin fenfuram
* negative cross-resistance to B1

D: Amino Acid and Protein Synthesis E: Signal Transduction F: Lipid and Membrane Synthesis
D1: methionine biosynthesis D2: D3: E1: G-proteins
p in early
y cell signalling
g g E3: Osmotic signal transduction F2: phospholipid biosynthesis F3: lipid peroxidation (prop.) F4: cell membrane F5: p
phospholipid
p p biosynthesis
y and F6: microbial
((cgs
g ggene)) (p
(prop.)
p) protein synthesis
p y protein synthesis
p y (prop.)
(p p) > MAP / histidine kinase ((os-1,, Daf1)) > methyltransferase
y # 14 aromatic hydrocarbons & heteroaromatics permeability,
p y, cell wall deposition (prop.) disrupters of
# 9 Anilino-Pyrimidines # 23 enopyranuronic acid # 24 hexopyranosyl antibiotics #13 quinolines # 2 dicarboximides # 6 phosphorothiolates & dithiolanes fatty acids (prop.) # 40 CAA fungicides
g (Carboxylic
( y Acid Amides)) pathogen cell
( AP fungicides ) O + O
# 28 carbamates
membranes
N
OH nitrobenzenes
HN
O
O
# 44 Bacillus sp.
sp
H2N
H
N
H2N NH F Cl Cl cinnamic acid mandelic acid
H
OH
N
phosphorothiolates O + O
NH2
O + O
O
amides amides
N S N N
N N O O Cl O O
OH NH2
NH2 P O
O HO OH N O Cl Cl Cl Cl
N N
H N NH2 O NH O N
O
O dicloran
HO
O N F
OH
HO OH Cl N N Cl Cl Cl Cl
O O
O N N Cl
OH Cl H
cyprodinil
N
pyrazophos O Cl O
Bacillus subtilis
blasticidin-S kasugamycin quinoxyfen Cl
O S
P
O
tecnazene quintozene dimethomorph O O

N O
O O N
O
(TCNB) ((PCNB)) propamocarb
O
H

O Cl O O St i QST 713
Strain
O O
iprodione O

NH
N
iprobenfos S
O
thiophosphate mandipropamid
N N
D4: protein synthesis D5: protein synthesis E2: Osmotic signal transduction P S flumorph
O
benzenes
# 25 glucopyranosyl # 41 tetracycline antibiotics > MAP / histidine-
histidine kinase (os-2,
(os 2 HOG1) Cl Cl O
Cl
Cl O

antibiotics # 12 PhenylPyrroles (PP-

(PP fungicides) chlozolinate
O
N
O
O
S
O biphenyl
O
O N
H valinamide
mepanipyrim edifenphos P I

O
O carbamates
O
Cl Cl
O Cl Cl
HO O S
iodocarb H
O O O
O H
O O N
HO O Chiral N
vinclozolin tolclofos- chloroneb N
H
O N
N
H H S H
O
HO O
methyl Cl O O
OH O OH O O N N
NH O Cl
HO
O
OH Cl Cl
O Cl Cl
OH N N
NH NH2 O
N N O OH
NH2 Cl
F O iso-
iso N N i
iprovalicarb
li b O S F valifenalate
lif l t
OH
HN N NH OH OH N F
procymidone
p y dithiolanes prothiolane
p S
S N
H
N O
H
N
N
H O H N
Cl
pyrimethanil HN
OH
NH2
O O

oxytetracycline
t t li
streptomycin fenpiclonil fludioxonil thiadiazoles
((bactericide)) etridiazole prothiocarb
p ot oca b
(b t i id )
(bactericide) benthiavalicarb

G: Sterol Biosynthesis
y in membranes H: Glucan Synthesis
y I: Melanin Synthesis
y in Cell Wall P: Host Defence Inducer M: Multi Site Action
G1: Sterol Biosynthesis Inhibitor (SBI) class I: DMI fungicides G2: SBI class II: Amines H3: trehalase and I1: > reductase in melanin biosynthesis P1: salicylic pathway P2: #M9 anthraquinones #M5 chloronitriles
# P: host defence induction
>C14 demethylase (erg11/cyp51) > Δ -reductase
14 reductase (erg24) and Δ8→ Δ7-isomerase
isomerase (erg2) inositol biosynthesis # 16.1
16 1 Melanin Biosynthesis Inhibitors (MBI-R) # P: host defence induction
# 3 DeMethylation Inhibitors (=DMI fungicides) # 5 amines # 26 glucopyranosyl antibiotic #M1/2 inorganics O
N
N

Cl Cl S
O Cl Cl
O isobenzofuranone
f pyrroloquinolione triazolobenzothiazole O S O
triazoles
O
piperazines
p p
S
S
N
S O
S
N
N
Cl

O N Cl
N Cl N O
Cl
N HN
piperidines
Cl
O sulphur dithianon chlorothalonil
O Cl N
HO
Cl
morpholines
h li OH
OH HO
Cl
.
etaconazole N N acibenzolar-
Cu
HO O OH N O N
O
O N
N N
S-methyl probenazole
N N HO
O
HO OH
Cl
N S
N N Cl H
N
Cl Cl
NH HO
OH OH Cl
copper #M8 triazines #M4 phthalimides
N Cl
Cl
Cl preparations
azaconazole N ipconazole
p pyridines triforine
O
(CH2)n N O O N
validamycin fthalide pyroquilon tricyclazole #M6 sulphamides
p

OH N
Cl HO
n= 11
fenpropidin Cl
O P3: P4: (proposed) H
Cl O

N Cl N N
N N
N
Cl Cl Cl # P: host defence induction # P: host defence induction N S
Cl Cl
O
N
O N
pyridines
idi aldimorph N #M3 dithiocarbamates & relatives N N
Cl S S
N N fenbuconazole tebuconazole O Cl N
N O Cl O
N Cl
N N
O piperalin
H4: chitin synthesis I2 > dehydratase
I2: d h d t in
i melanin
l i bibiosynthesis
th i N
Cl
F
OH N
F
fenpropi- # 16.2
16 2 Melanin
M l i Biosynthesis
Bi th i Inhibitors
I hibit (MBI-D)
(MBI D) anilazine captan
> chitin synthase S S S
CH2OH
HO
Cl Cl Cl Cl O HO

N F O 1-6 Glucose n
O O N morphh S
N OH O Fe
F (CH2)n N O
bitertanol F metconazole pyrifenox # 19 polyoxins N HOH2C HOH2C
N S S dichlofluanid
N F spiroketal- cyclopropane H HO
O
O HO
O
O HO
O
O
O
*

O
*

Cl OH OH OH

N N n= 10 to 13
amines carboxamide carboxamide propionamide
Cl Cl
S N
N N NHCH
C 2CH
C 2NHCS
CS2- O
N n=12: ~ 70% HS N S Cl N
N Cl S S
Br N
t id
tridemorph
h isotianil laminarin ferbam 2+
2
O pyrimidines
i idi Cl Mn SH Cl N
O
fluquinconazole tetraconazole N O N NH 2 Cl NHCH2CH2NHCS2-
O Cl Cl
F
Cl O HS Cl
N O
OH
N N
O O HO
O H Cl 2+
Zn S
SH
N
N
Cl F N
O HO
H2N N OH
O H H
N
H
H S captafol
O N
H
N Cl O
N O N N
O H S H S mancozeb S
N O OH dodemorph OH

Cl N
S
N
N S N S
bromuconazole Si myclobutanil N N F
O N
O O Cl H Zn (NH3)- Mn tolylfluanid
HN N N S N S
O
F Cl H S 3 H S
N S
N
N spiroxamine O OH x H H S
N
N polyoxin B carpropamid diclocymet fenoxanil 2+
S H N S
Cl Zn N Cl
Cl N Cl N Cl
tiadinil metiram S maneb Cl
nuarimol OH S O Cl
HO
flusilazole triadimefon Cl
H
N
N H
N Cl S
N OH N folpet
N S S S NH2
N F N

U k
Unknown M
Mode
d off Action
A ti
propineb
p op eb
cyproconazole F
N
penconazole O i id
imidazoles
l fenarimol G3: SBI class III: G4: SBI class IV: U Recent
U: R t Molecules*
M l l * NC : N
Not Cl
Classified
ifi d N S
S N N S
Zn
S N
HN N
H
NH

N
HO N N
hydroxyanilides > squalene epoxidase S H S
HN
H
N

Cl N
Cl
N Cl Cl
3 k t reductase
>3-keto d t # 18 thiazole
thi l phenyl Mode of action of fungicides based N S mixture of
NH2
H
N Cl carboxamides acetamides on the FRAC fungicide
g list (p
(published thiram ziram iminoctadine iminoctadine H2N N
O phosphorous
s Zn
O flutriafol Cl
triadimenol O
in C4-demethylation cyanoacetamide- ethyl-
acid
phthalamic at www.frac.info/publications ) and other NH2
+

O O O oxime phosphonates acid N S O

N N # 17 hydroxyanilides N O The ggroupings
p g can change g when new H S polyamines
N Cl N O
F
Cl Cl N N
O F F
Mineral oils, organic oils, results become known. Yellow zones #M7 guanidines
N N HO HN zineb dodine
OH allylamines
ll l i HO O N potassium bicarbonate, represent accepted mode of action guazatine
difenoconazole propiconazole N imazalil O Cl O O
O
H3PO3 O N H
O
N
PH S S
N
material of biological groups or in cases where resistance
N N Cl
N
O N N O
OH
N
H
Cl
N F origin is known, cross resistance groups. In
N N H H H
N
N
Cl
N AlH3
Cl Cl
Cl
# U5 F
# U6 spite of this general classification,
classification
F F
N OH O O N # 33 cases of incomplete or even lacking
OH Cl Cl ethaboxam cyflufenamid
L
Legend:
d
F Cl
hexaconazole triticonazole triflumizole # 27 # 33 phosphorou
us # 34 cross resistance are known within
N
terbinafine
N N
N cymoxanil fosetyl Al
fosetyl-Al acid tecloftalam some groups with some pathogens.
pathogens
N Cl N Cl O Cl (
(antimycotic)
y )
HO
mode of action g
group
p
C Respiration
C:
N O O
Cl N N
N
H S benzene- benzophenone Although details presented herein are
Cl
prothio
prothio-
quinazolinone accurate to our knowledge at the time
diniconazole
Cl N
H b
benzotriazines
ti i sulfonamides
lf id pyridazinon
id i nes thiocarbamates sub-group
b
N S
conazole pefurazoate Cl naftifine thiocarbamates of publication, neither FRAC nor its
O
F N
N N
( ti y ti )
(antimycotic) member companies make any C2: inhibition of complex II: > target site of action
N
HO Si N O representation or warranty with (where known) or putative
N
Cl O f h
fenhexamid
id O
+
Cl
H O F Cl O
O O
regard to the content of this > succinate-dehydrogenase
i t d h d
Cl
O O N N O N
N Cl
N F O I
Br O target
g site (=( proposed)
p p )
i ib
imibenconazole
l N N oxpoconazole
l S
O O
S N presentation,
i i particular
in i l with i h regard
d
O F
O
N N O N
S
N
N N O
N
+
Cl
N N
S N O
O O to its correctness and completeness. # 7 SDHI (Succinate DeHydrogenase FRAC code no.
no (#)
N N O Cl Cl H N
Cl N
O Cl H Neither FRAC nor its member and group
g p name
N
# 42 # U7 # U8 companiesi assume any liability
li bilit for
f Inhibitors)
F # 35 # 36 # 37 metrafenone
py
pyributicarb methasulfocarb proquinazid the content of this presentation or its chemical (sub
(sub-)) group
epoxiconazole
i l simeconazole
i l prochloraz triazoxide flusulfamide diclomezine
(
(herbicide)) use.
thiazole carboxamides
•Temporary status; information on mode of action and
•/ or resistance risk is still uncertain

FRAC Mode of Action Poster ©

June 2009