A: Nucleic Acid Synthesis C: Respiration

## 4:
4: PA-fungicides
A1:
>
A1: RNA
> RNA
RNA synthesis
synthesis
RNA polymerase
polymerase II
PA-fungicides (phenylamides)
(phenylamides) ## 8:
A2:
A2: purine
>
purine metabolism
metabolism
> adenosin-deaminase
adenosin-deaminase
8: hydroxy
hydroxy (2-amino)-pyrimidines
(2-amino)-pyrimidines
Mode of Action of Fungicides >#
># 21
21 QiI
C4:
C4: inhibition
>
inhibition of
> cytochrome
of complex
cytochrome bc1
QiI fungicides
fungicides (Quinone
complex III
bc1 at
(Quinone inside
at Qi
III
Qi site
site
inside Inhibitors)
Inhibitors)
C6:
C6: inhibitors
of
inhibitors
of oxydative
oxydative
phosporylation,
phosporylation,

FRAC classification on mode of action 2007 (www.frac.info)

N ATP
ATP synthase
synthase
acylalanines ## 30
O
N
O
N
O
30 organo
organo tins
tins
N
S Cl O S N O
N
O N S
F N
O HO O N
O
O
S
N

B: Mitosis and Cell Division C: Respiration

HO N O N N Br

chiral HN cyazofamid
cyazofamid amisulbrom
amisulbrom
Sn
HO O O HO O O
bupirimate
bupirimate O
metalaxyl-M
metalaxyl-M
B1:
B1: >
> ß-tubulin
ß-tubulin assembly
assembly in
in mitosis C1: C2:
C2: inhibition
inhibition of
of complex
complex II: C3:
C3: inhibition
inhibition of
of complex
complex III C5:
C5: uncouplers
uncouplers of
HO N
mitosis C1: II: III of
HO N

fentin
fentin acetate
acetate
O OH
## 1:
1: MBC
MBC fungicides
fungicides (=
(= Methyl
Methyl Benzimidazole
Benzimidazole Carbamates)
Carbamates) inhibition
inhibition of
of >
> succinate-dehydrogenase
succinate-dehydrogenase > cytochrome
> cytochrome bc1
bc1 (ubiquinol
(ubiquinol oxidase)
oxidase) at
at Qo
Qo site
site oxidative
oxidative
HO
HO
benalaxyl
N
O
metalaxyl
metalaxyl N N complex
complex II ## 77 carboxamides
carboxamides ## 11
11 QoI
QoI fungicides
fungicides (( Quinone
Quinone outside
outside Inhibitors
Inhibitors )) phosphorylation
phosphorylation
N
O
(prop.)
(prop.) furan methoxy- oximino- oxazolidine-
## 29
29
H
thiophanates Sn
N O S N O
## 39
39 pyrimidin-
pyrimidin- benzamides carboxamides acrylates acetamides diones Cl
butyrolactones oxazolidinones dimethirimol
dimethirimol
N
N O
F

furalaxyl
N
H NH
S
O
O amines
amines O
NH
furalaxyl N F F O
fentin
fentin chloride
H N
N N O O
chloride
Cl HO O
O H N
H
N
H
O
S
H
N O
H
N
H
O oximino- methoxy- O
O O
O
O
O O I
O
HO
N
H N N NH O
O O N N acetates carbamates N
+

N
benomyl
benomyl N fuberidazole
fuberidazole thiophanate
thiophanate S O
O
HO N N O O O O O
O N
N N H
O
N
S
N N
benodanil
benodanil O flutolanil O
N
H
O O
N N
H +
O
H
H H
N
O
N N
N
O famoxadone
famoxadone O
N
O
NH N Sn
H O O
O
thiophanate-
thiophanate- binapacryl
binapacryl
O O OH

carbendazim thiabendazole thiazole fenfuram azoxystrobin

O N
+

ofurace
ofurace oxadixyl
oxadixyl ethirimol
ethirimol carbendazim thiabendazole methyl
methyl azoxystrobin orysastrobin
orysastrobin Cl
N O imidazolinones O

benzimidazoles carboxamides mepronil O O N

mepronil N O N
O
fentin
fentin hydroxide
hydroxide
O N
+
O
O O
oxathiin pyrazole dinocap
dinocap
kresoxim-
kresoxim- NH
F F carboxamides carboxamides F
F
methyl O pyraclostrobin
pyraclostrobin N
F O
Br O
F
N O
methyl S O

A3:
A3: DNA
DNA // RNA
RNA synthesis
synthesis (prop.)
(prop.) A4:
A4: DNA
DNA supercoiling
supercoiling B2:
B2: B3:
B3: B4:
B4: B5:
B5: F
F
F O O
N
O N

F F

C7:
C7: ATP
ATP production
N NH

production
O O

delocalisation
N
delocalisation
H
32: heteroaromatics
## 32: >
> DNA
DNA topoisomerase
topoisomerase type
type IIII (gyrase) >
> ß-tubulin >ß-tubulin cell
cell division
division (prop.)
Cl
heteroaromatics (gyrase) ß-tubulin >ß-tubulin (prop.) O F S F
Br Cl
Cl F
dimoxystrobin
(prop.)
F
dimoxystrobin
(prop.)
H O O
of
of spectrin-like picoxystrobin
F O

spectrin-like
O
## 31:
31: carboxylic
carboxylic acids assembly assembly ## 20
20 phenylureas picoxystrobin
N S O N
acids assembly assembly phenylureas fenamidone
O F
S F N
fenamidone O HN O
thifluzamide
thifluzamide N N
38 thiophene-
## 38
+ +
N N O
thiophene-
N N H N N
proteins
N

in
in mitosis* in
in mitosis proteins H O O O

isoxazoles isothiazolones
mitosis* mitosis pyridine
O N
F
O O
N
O
N
O
benzylcarbamates Cl carboxamides
carboxamides
## 10
10 N-phenyl
N-phenyl ## 22
22 benzamides
benzamides ## 43
43 acylpicolides
acylpicolides diflumetorim
diflumetorim F F
Cl N
O F F
carboxamides trifloxystrobin
trifloxystrobin
carbamates oxycarboxin
oxycarboxin penthiopyrad
penthiopyrad N O
fluoxastrobin
F

O O
carbamates O
O
H
N O
fluoxastrobin O Cl fluazinam
fluazinam
N
O O O N
H O O H
O
N
O
HO
O dihydro-
O O O
N
O N O
O
O Cl OH Cl O Cl O
enestrobin
metomino-
metomino- dioxazines
S Cl N
H enestrobin strobin
N

O N O
N
H
Cl N N N S
N N
strobin O
N
N
H
H H N Cl H
H O HN F H N H N N S
Si
oxolinic
oxolinic acid
acid Cl Cl
F
O N O N
Cl
hymexazol
hymexazol octhilinone
octhilinone (bactericide)
(bactericide)
F pyribencarb
pyribencarb
N
Cl
diethofencarb
diethofencarb zoxamide
zoxamide pencycuron
pencycuron fluopicolide
fluopicolide boscalid
boscalid carboxin
carboxin furametpyr
furametpyr silthiofam
silthiofam
ferimzone
ferimzone
** negative
negative cross-resistance
cross-resistance to
to B1
B1

D: Amino Acid and Protein Synthesis E: Signal Transduction F: Lipid and Membrane Synthesis, Cell Wall Deposition
D1:
D1: methionine
methionine biosynthesis
biosynthesis D2:
D2: D3:
D3: E1:
E1: G-proteins
G-proteins in
in early
early cell
cell signalling
signalling E3:
E3: Osmotic
Osmotic signal
signal transduction
transduction F2:
F2: phospholipid
phospholipid biosynthesis
biosynthesis F3:
F3: lipid
lipid peroxidation
peroxidation (prop.)
(prop.) F4:
F4: cell
cell membrane
membrane permeability,
permeability, F5:
F5: phospholipid
phospholipid biosynthesis
biosynthesis and
and
(cgs
(cgs gene)
gene) (prop.)
(prop.) protein
protein synthesis
synthesis protein
protein synthesis
synthesis (prop.)
(prop.) >
> MAP
MAP // histidine
histidine kinase
kinase (os-1,
(os-1, Daf1)
Daf1) >
> methyltransferase
methyltransferase ## 14
14 aromatic
aromatic hydrocarbons
hydrocarbons &
& heteroaromatics
heteroaromatics fatty
fatty acides
acides (prop.)
(prop.) cell
cell wall
wall deposition
deposition (prop.)
(prop.)
## 99 Anilino-Pyrimidines
Anilino-Pyrimidines ## 23
23 enopyranuronic
enopyranuronic acid
acid ## 24
24 hexopyranosyl
hexopyranosyl antibiotics
antibiotics #13
#13 quinolines
quinolines ## 22 dicarboximides
dicarboximides ## 66 phosphorothiolates
phosphorothiolates &
& dithiolanes
dithiolanes ## 28
28 carbamates
carbamates ## 40 Carboxylic Acid
40 Carboxylic Acid Amides
Amides
(( AP
AP fungicides
fungicides )) O
N
+ O
(CAA
(CAA fungicides)
fungicides)
OH nitrobenzenes
HN
H2N
H
N
O
OH
H2 N NH F Cl Cl O
N
OH NH2 phosphorothiolates NH2 O cinnamic acid mandelic acid
N O O O O
amides amides
O NH2 + +
S N N
NH N O O Cl O O O
H N NH2 P O
HO OH N O Cl Cl Cl Cl
HN NH
HO OH
O NH O N
O
O dicloran
dicloran O N
H
N
N
F
HO OH Cl N Cl Cl Cl Cl O
N Cl
O
OH Cl

cyprodinil
cyprodinil
N
pyrazophos
pyrazophos O
propamocarb dimethomorph
dimethomorph
O
blasticidin-S
blasticidin-S kasugamycin
kasugamycin quinoxyfen
quinoxyfen O S O
tecnazene quintozene propamocarb Cl O

O
Cl P
tecnazene quintozene N
O

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

O Cl

O O
iprodione
iprodione
O

NH N
iprobenfos
iprobenfos S
O
thiophosphate flumorph
D4:
D4: protein
protein synthesis D5:
D5: protein
protein synthesis E2:
E2: Osmotic
Osmotic signal
signal transduction
O
flumorph mandipropamid
N N synthesis synthesis transduction P
O
S

benzenes O N
mandipropamid

## 25
25 glucopyranosyl
glucopyranosyl ## 41
41 tetracycline
tetracycline antibiotics
antibiotics >
> MAP
MAP // histidine-
histidine- kinase
kinase (os-2,
(os-2, HOG1)
H
HOG1) Cl Cl O Cl
I
O
antibiotics
antibiotics ## 12 chlozolinate
chlozolinate
O
N
O Cl
biphenyl
phenylpyrroles (PP-
12 phenylpyrroles (PP- fungicides)
S
fungicides) O O biphenyl
mepanipyrim
mepanipyrim edifenphos
edifenphos P
iodocarb valinamide
O iodocarb O

Cl Cl Cl
O Cl
O
carbamates
O O O
H H
O O N O N
HO S N N
O O
Chiral N
vinclozolin
vinclozolin tolclofos-
tolclofos- chloroneb
H H
HO O
H H S chloroneb O O

NH O
HO
OH O OH O O N N
O
methyl
methyl Cl O
Cl

HO OH O Cl Cl
O
O Cl Cl S N N
N N OH N N
NH2
NH H
iprovalicarb
iprovalicarb O S F valiphenal
valiphenal
O OH
NH2
OH
Cl
F O iso-
iso- N N
O
H
N

HN N NH OH OH N F
procymidone
procymidone dithiolanes prothiolane
prothiolane
S
O
N
H N
H O O
Cl
pyrimethanil
pyrimethanil HN
OH
NH2 prothiocarb
prothiocarb
oxytetracycline
oxytetracycline
streptomycin
streptomycin fenpiclonil
fenpiclonil fludioxonil
fludioxonil thiadiazoles benthiavalicarb
benthiavalicarb
(bactericide)
(bactericide) etridiazole
etridiazole
(bactericide)
(bactericide)

G: Sterol Biosynthesis Inhibitors (SBI fungicides) H: Glucan Synthesis I: Melanin Synthesis in Cell Wall P: Host Defence Inducer M: Multi Site Action
G1:
G1: SBI
SBI class
class I:
I: DMI
DMI fungicides
fungicides G2:
G2: SBI
SBI class
class II:
II: Amines
Amines H3: trehalase and I1:
I1: >
> reductase
reductase in
in melanin
melanin biosynthesis
biosynthesis P1:
P1: salicylic
salicylic pathway
pathway anthraquinones chloronitriles

> P: host
## P: defence induction
host defence
>C14
C14 demethylase
demethylase (erg11/cyp51)
(erg11/cyp51) > 14-reductase
> ∆∆14 -reductase (erg24) and ∆∆88→
(erg24) and → ∆∆77-isomerase
-isomerase (erg2)
(erg2) inositol biosynthesis ## 16.1 Melanin Biosynthesis
16.1 Melanin Biosynthesis Inhibitors
Inhibitors (MBI-R)
(MBI-R) induction
DeMethylation Inhibitors
## 33 DeMethylation Inhibitors (=DMI
(=DMI fungicides)
fungicides) ## 55 amines
amines # 26 glucopyranosyl antibiotic inorganics O
N
N

O S S
Cl Cl
isobenzofuranone pyrroloquinolione triazolobenzothiazole
triazoles piperazines S S
S O
S
N
N
Cl
N
Cl
O N
Cl
Cl
HN
piperidines
Cl
O sulphur
sulphur dithianon
dithianon chlorothalonil
chlorothalonil
O Cl
HO
N
Cl morpholines OH
OH HO
Cl
N acibenzolar-
acibenzolar- ..
Cu
N O
Cu
HO
O
N
N
O OH
O N
N S-methyl
S-methyl
N N N O Cl
N N HO HO
Cl Cl
N OH S
H
N Cl NH
OH OH Cl
copper triazines phthalimides
Cl Cl
Cl
HO
copper
O preparations
preparations
pyridines (CH2 )n N O
validamycin
validamycin fthalide
fthalide pyroquilon
pyroquilon tricyclazole
tricyclazole sulphamides
azaconazole
azaconazole N
Cl
ipconazole
ipconazole
HO
triforine
triforine
n= 11
fenpropidin
fenpropidin
O N PP22:: uncle
uncl
uncleear
uncle ar path
pat
pathhwwaayy
path PP33:: uncle
uncl
uncleeaarr pathw
uncle pat
pathway
pathw ay
hway
ay Cl O
OH N
N
N
Cl
O ## P:
P: hos
host
hosttt def
hos defe
eennccee in
defe
def induc
duct
ductttiioonn
induc
in ## P:
P: hos
host
hosttt def
hos defe
eennccee in
defe
def induc
duct
ductttiioonn
induc
in Cl N
H
N
N N Cl N S
Cl Cl
O N
pyridines aldimorph
aldimorph N
Cl
dithiocarbamates & relatives N N
Cl Cl
O
N
O Cl S S
N N
fenbuconazole tebuconazole
tebuconazole N
O Cl N
I2:
I2: >
> dehydratase
dehydratase in
in melanin
melanin biosynthesis
O
biosynthesis
N O
Cl
piperalin
piperalin
Cl
H4:
H4: chitin
chitin synthesis
N F
synthesis
N N OH
O
N F
fenpropi- ## 16.2 Melanin Biosynthesis
16.2 Melanin Biosynthesis Inhibitors
Inhibitors (MBI-D)
(MBI-D) S N
anilazine captan
captan
Cl Cl
O F
O
Cl Cl
N
(CH2)n N O
fenpropi-
morph
morph > chitin
> chitin synthase
synthase N
H
N
S S S
anilazine
bitertanol metconazole pyrifenox ## 19
O
19 polyoxins
F Fe
bitertanol N
F
F pyrifenox spiroketal- polyoxins cyclopropane
O Cl Cl
N S S dichlofluanid
dichlofluanid
S
O
N N Cl n= 10 to 13
n=12: ~ 70%
amines carboxamide carboxamide propionamide
N
isotianil
S N
N
N N
N isotianil NHCH2CH2NHCS2- N S
O HS Cl O
N
Br O
pyrimidines tridemorph
tridemorph Cl ferbam
ferbam Mn SH
2+
Cl
Cl
S S
N

Cl fluquinconazole tetraconazole
tetraconazole N O NH2 Cl NHCH2CH2NHCS2-
O Cl
Cl
N
O
N O HS Cl F
N OH
N
O
O HO
N N 2+
H Cl Zn SH
N Cl O
HO
O
N probenazole
probenazole O
N
F N
N
O Cl O
H2 N N
H
OH
O H H H S captafol
captafol
N N N Cl N N H S
OH
dodemorph
dodemorph
O
OH O H H S
N S
H S mancozeb
mancozeb N S
N N S
bromuconazole Cl
O N
bromuconazole Si myclobutanil O F
HN
O O
Zn (NH3)-
Mn tolylfluanid
tolylfluanid
F N N Cl N S N S N S O
N H S 3 H S H S
spiroxamine
O OH
N N
spiroxamine polyoxin
x
N N polyoxin BB carpropamid
carpropamid diclocymet
diclocymet fenoxanil
fenoxanil tiadinil N S
N Cl
Cl
Cl tiadinil H
S H
Cl
Cl
OH metiram Zn
2+
N maneb
maneb Cl
Cl
HO flusilazole triadimefon
triadimefon nuarimol
nuarimol Cl S
H
S
O

N N
Cl H
N N N S
N
N OH N folpet
folpet NH2
N S S

Unknown Mode of Action U: Recent Molecules*

propineb
cyproconazole
cyproconazole F
F
penconazole
O imidazoles fenarimol
fenarimol G3:
G3: SBI
SBI class
class III:
III: G4:
G4: SBI
SBI class
class IV:
IV:
S
S N
propineb
N S
Zn
S N
HN N
H
NH
N N S
hydroxyanilides >
> squalene
squalene epoxidase
N

Cl
N
HO

N N
hydroxyanilides epoxidase S HN
H
N

>3-keto
>3-keto reductase ## 18 NH2
N
O
Cl Cl
Cl Cl reductase 18 Mode of action of fungicides based
on the FRAC fungicide list (published thiram
H S
N S ziram
ziram
mixture
mixture of
of
phosphorous thiazole iminoctadine
iminoctadine iminoctadine
iminoctadine
H
O
O
flutriafol O
Cl triadimenol
triadimenol O in
in C4-demethylation
C4-demethylation cyanoacetamide- ethyl-
acid
phthalamic
carboxamides
phenyl at www.frac.info/publications ) N S
Zn
and
and other
other
H2N N
+
O
oxime phosphonates acid acetamides H S NH2
O
N N ## 17
17 hydroxyanilides
hydroxyanilides polyamines
polyamines
N Cl
N N
N The groupings can change when new O
N Cl Cl N results become known. Yellow zones guanidines
HO
N O zineb dodine
OH
imazalil O Cl allylamines HO O F represent accepted mode of action guazatine dodine
difenoconazole
difenoconazole propiconazole N imazalil O
H
O F F guazatine
H33PO
O O O
N
N PH
PO33 HN
groups or in cases where resistance
N Cl N
N N N O N N O N Cl N H
O
is known, cross resistance groups. In
N N H H OH H N
N Cl S S
N
Cl
F F AlH3
Cl Cl spite of this general classification,
OH Cl O O F N ## 33
33 N
H
F
cases of incomplete or even lacking
Legend:
OH Cl Cl F
hexaconazole triticonazole
triticonazole triflumizole
triflumizole ## 27
27 ## 33
33 phosphorous
phosphorous ## 34
34 ## U5
U5 ## U6
U6 cross resistance are known within
N
N
terbinafine
terbinafine
N N cymoxanil
cymoxanil fosetyl-Al
fosetyl-Al acid
acid tecloftalam
tecloftalam ethaboxam
ethaboxam cyflufenamid
cyflufenamid some groups with some pathogens.
N Cl N Cl
N O
O Cl (antimycotic)
(antimycotic)
HO

C: Respiration
N
Cl N
H S
N
O mode of action group
benzene- Although details presented herein are sub-group
Cl
prothio-
prothio- Cl N
thiocarbamates quinazolinone accurate to our knowledge at the time
diniconazole
diniconazole N S
H
thiocarbamates benzotriazines sulfonamides pyridazinones
conazole
conazole pefurazoate O Cl naftifine
naftifine of publication, neither FRAC nor its > target site of action
F N
N N
N
(antimycotic)
(antimycotic) member companies make any (where known) or putative
C2: complex II:
N
N O
fenhexamid O representation or warranty with target site (=prop.)
HO Si fenhexamid +
Cl
Cl
O
O
Cl
Cl N Cl H O F
F O O regard to the content of this
> succinate-dehydrogenase
N N O Br O
imibenconazole
imibenconazole N
O oxpoconazole
oxpoconazole
O N N O S
F O O
S I
N presentation, in particular with regard
N O O
O
N N O
S
N
N N
N
+
N N O O to its correctness and completeness. FRAC code no. (#)
Cl N
N
N
N O Cl Cl
O
Cl H
Cl
N
H
S
N O
Neither FRAC nor its member # 7 carboxamides and group name
N
## 35 ## 36 ## 37 ## 42
42 ## U7
U7 ## U8
U8 companies assume any liability for
F 35 36 37
pyributicarb
pyributicarb triazoxide flusulfamide diclomezine methasulfocarb
methasulfocarb proquinazid
proquinazid metrafenone
metrafenone the content of this presentation or its
epoxiconazole
epoxiconazole simeconazole
simeconazole prochloraz
prochloraz triazoxide flusulfamide diclomezine
(herbicide)
(herbicide) use.
chemical (sub-) group
phthalimides
* Temporary status; information on mode of action and / or resistance risk is still uncertain

©
FRAC Mode of Action Poster
January 2007