1
B5: delocalisation of spectrin-like proteins # 43 benzamides C5: uncouplers of oxidative phosphorylation # 29 C7: ATP production (prop.) # 38 thiophene- carboxamides silthiofam D2: protein synthesis # 23 enopyranuronic acid D1: methionine biosynthesis (cgs gene) (prop.) # 9 Anilino-Pyrimidines ( AP fungicides ) D3: protein synthesis # 24 hexopyranosyl antibiotics E2: osmotic signal transduction MAP / histidine- kinase (os-2, HOG1) # 12 p henylp yrroles (PP- fungicides) E1: signal transduction (mechanism unknown) #13 azanaphthalenes fenpiclonil fludioxonil D4: protein synthesis # 25 glucopyranosyl antibiotics kasugamycin N H NH O N H 2 O O H O H OH OH OH O OH cyprodinil mepanipyrim pyrimethanil F4: cell membrane permeability, fatty acids (prop.) # 28 carbamates I1: reductase in melanin biosynthesis # 16.1 M elanin B iosynthesis I nhibitors: Reductase (MBI-R) Mode of action of fungicides based on the FRAC fungicide list (published at www.frac.info/publications ) 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. 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. P01: salicylic pathway acibenzolar- S-methyl fthalide tricyclazole pyroquilon C2: inhibition of complex II: succinate-dehydrogenase # 7 SDHI (Succinate dehydrogenase inhibitors) mode of action group sub-group target site of action (where known) or putative target site (=prop.) FRAC code no. (#) and group name Legend: thiazole carboxamides chemical (sub-) group Mode of Action of Fungicides FRAC classification on mode of action 2017 (www.frac.info) P02: probenazole FRAC Mode of Action Poster © Updated March 2017 fluazinam binapacryl N + O O N + O O O O C6: inhibitors of oxidative phosphorylation, ATP synthase # 30 organo tins fentin acetate fentin chloride fentin hydroxide E3: osmotic signal transduction MAP / histidine kinase (os-1, Daf1) # 2 dicarboximides P03: tiadinil N H O Cl S N N C4: inhibition of complex III cytochrome bc1(ubiquinone reductase) at Qi site # 21 QiI fungicides (Q uinone i nside I nhibitors) cyazofamid N N Cl N S O O N C1: inhibition of complex I NADH Oxido-reductase # 39 pyrimidinamines pyrazole-MET1 diflumetorim Temporary status; information on mode of action and / or resistance risk is still uncertain D5: protein synthesis # 41 tetracycline antibiotics NH N N C2: inhibition of complex II: succinate-dehydrogenase # 7 SDHI (S uccinate D eH ydrogenase I nhibitors) benodanil fenfuram flutolanil mepronil O N H I N H O O O O N H F F F O N H O S sulphur . Cu copper preparations thiram zineb metiram chlorothalonil S N S S N S #M03 dithiocarbamates & relatives dichlofluanid #M06 sulphamides mixture of iminoctadine and other polyamines guazatine iminoctadine guanidines N H NH 2 N H N H N H NH 2 NH #M04 phthalimides #M01/02 inorganics #M05 chloronitriles anilazine N H Cl N N N Cl Cl #M08 triazines dithianon #M09 anthraquinones N H S S N H S S Zn (NH 3 )- 3 N H S S N H S S x # U12 dodine N H N H 2 NH 2 + O O tolylfluanid N N Cl S F Cl S O O captan captafol blasticidin-S streptomycin (bactericide) oxytetracycline (bactericide) O OH OH N OH O OH O OH NH 2 OH Chiral propamocarb iodocarb prothiocarb # U6 cyflufenamid C3: inhibition of complex III cytochrome bc1 (ubiquinol oxidase) at Qo site (cyt b gene) # 11 QoI fungicides ( Q uinone o utside I nhibitors ) azoxystrobin O N N O O O O N picoxystrobin enoxastrobin O O O Cl N O methoxy- acrylates pyraclostrobin fenamidone imidazolinones methoxy- carbamates orysastrobin dimoxystrobin N O N H O O oximino- acetamides metominostrobin kresoxim-methyl oximino- acetates O N O O O trifloxystrobin G1: C14-demethylase in sterol biosynthesis (erg11/cyp51) # 3 DMI-fungicides (D eM ethylation Inhibitors) (SBI: Class I) G2: 14 -reductase and 8 7 -isomerase in sterol biosynthesis (erg2, erg 24) # 5 Amines(“Morpholines”) (SBI: Class II) G3:3-keto reductase in C4-de-methylation (erg27) # 17 (SBI :Class III) G4: squalene epoxidase in sterol biosynthesis (erg1) # 18 (SBI class IV) pyributicarb (herbicide) thiocarbamates O O N N S allylamines spiroxamine N O O aldimorph tridemorph fenpropidin N morpholines spiroketal- amines piperidines piperalin O O Cl Cl N fenpropimorph dodemorph O N N O azaconazole bitertanol bromuconazole cyproconazole O H N Cl N N Cl Cl O N N N Br difenoconazole diniconazole Cl OH N Cl N N epoxiconazole N N N O F Cl OH N O N N propiconazole penconazole N Cl N N Cl myclobutanil N Cl N N N fluquinconazole fenbuconazole F N N Cl Cl N N N O flusilazole F N Si N N F imibenconazole Cl N Cl N N N S Cl ipconazole N N N O H Cl metconazole hexaconazole tebuconazole tetraconazole OH N Cl N N Cl flutriafol O H N F N F N triazoles Cl N Cl N N O F F F F nuarimol fenarimol OH Cl N N Cl OH Cl N N F pyrimidines triforine NH N N H N Cl Cl Cl O O Cl Cl Cl piperazines pyridines pyrifenox Cl Cl N N O prochloraz imazalil pefurazoate Cl Cl N O N O O O N N N O N Cl N O Cl O N Cl triazolinthione O H N N N Cl N Cl N N N prothioconazole N N N F O H Si triadimefon triadimenol triticonazole Cl N O N N O H O H N N N Cl triflumizole oxpoconazole N Cl N N O F F F O N Cl N N O naftifine (antimycotic) terbinafine (antimycotic) fenhexamid pyridines G: Sterol Biosynthesis in Membranes C: Respiration F: Lipid Synthesis or Transport / Membrane Integrity or Function E: Signal Transduction D: Amino Acid and Protein Synthesis C: Respiration H:Cell Wall Biosynthesis I: Melanin Synthesis in Cell Wall P: Host Plant Defence Induction M: Chemicals with Multi-Site Activity # 35 triazoxide # 36 flusulfamide Cl Cl N H S O O N + O O F F F # 37 diclomezine # 34 teclofthalam # 27 cymoxanil # 42 methasulfocarb H 3 PO 3 # 33 phosphorous acid C: Respiration phenyl- benzamides furan - carboxamides boscalid N H O Cl N Cl thifluzamide S N O N H Br Br O F F F F F F Thiazole - carboxamides Pyridine - carboxamides oxycarboxin carboxin Oxathiin - carboxamides fluoxastrobin O N O N O O N N O Cl F dihydro- dioxazines oxazolidine- diones famoxadone benzyl-carbamates pyribencarb N O N Cl N H O O folpet A1: RNA polymerase I # 4: PA-fungicides (P henylA mides) A2: adenosin-deaminase # 8: hydroxy (2-amino)-pyrimidines bupirimate O N N N NH S O O dimethirimol ethirimol A4: DNA topoisomerase type II (gyrase) # 31: carboxylic acids oxolinic acid (bactericide) A3: DNA / RNA synthesis (prop.) # 32: heteroaromatics octhilinone hymexazole benalaxyl metalaxyl-M metalaxyl furalaxyl A: Nucleic Acid Synthesis acylalanines oxazolidinones butyrolactones isoxazoles isothiazolones F3: lipid peroxidation (prop.) # 14 aromatic hydrocarbons & heteroaromatics tolclofos- methyl etridiazole biphenyl chloroneb O Cl Cl O O S N N Cl Cl Cl Cl S O P O O Cl tecnazene (TCNB) dicloran quintozene (PCNB) isobenzo-furanone pyrrolo-quinolione triazolobenzo-thiazole chlozolinate procymidone O O N Cl Cl iprodione Cl O N N Cl O O NH Cl O O N O Cl O O vinclozolin Cl O N O Cl O maneb ziram H5: cellulose synthase # 40 C arboxylic A cid A mides (CAA fungicides) mandipropamid dimethomorph flumorph iprovalicarb O N H N H O O benthiavalicarb N H O N H O O N S F valifenalate O O N H O N H O O Cl cinnamic acid amides valinamide carbamates mandelic acid amides B1: ß-tubulin assembly in mitosis # 1: MBC fungicides (= M ethyl B enzimidazole C arbamates) B2: ß-tubulin assembly in mitosis* # 10 N-phenyl carbamates * negative cross-resistance to B1 B3: ß-tubulin assembly in mitosis # 22 benzamides and thiazole carboxamides B4: cell division (prop.) # 20 phenylureas zoxamide benomyl carbendazim fuberidazole thiophanate thiophanate- methyl thiabendazole N O N N H N H O O N H N N H O O N H N O N H N N S N H NH N H S N H O O O O S N H NH S N H N H S O O O O thiophanates pencycuron diethofencarb B: Cytoskeleton and Motor Proteins ethaboxam amisulbrom N N S O O N F Br S O O N N F2: phospholipid biosynthesis methyltransferase # 6 phosphorothiolates & dithiolanes iso- prothiolane pyrazophos iprobenfos edifenphos phosphorothiolates dithiolanes benzimidazoles # U08 metrafenone cyanoacetamide- oxime ethyl- phosphonates phosphorous acid phthalamic acid benzotriazines benzene- sulfonamides pyridazinones thiocarbamates phenyl acetamides quinazolinone Pyridinyl - ethyl - benzamides pyrazole - 4 - carboxamides fluopyram furametpyr penthiopyrad bixafen isopyrazam sedaxane etaconazole meptyl dinocap F6: microbial disrupters of pathogen cell membranes # 44 Microbial (Bacillus sp.) Bacillus amyloliquefaciens (synonym B. subtilis) strains: QST 713 FZB24 MBI600 D747 P04: NC : Not Classified arylphenyl ketones laminarin Mineral oils, organic oils, potassium bicarbonate, material of biological origin fluopicolide benalaxyl-M ofurace oxadixyl N O N H 2 N N H NH 2 O O N NH 2 NH O HO OH O O HO HO OH OH O OH O HO OH O OH O HO O OH O HO OH H n P O - O O H Al +++ 3 # 33 fosetyl-al isotianil pyrametostrobin pyraoxystrobin penflufen C8: inhibition of complex III cytochrome bc1(ubiquinone reductase) at Qo site stigmatellin binding sub site) # 45 QoSI-fungicide (stigmatellin binding type) ametoctradin N N N N NH 2 aryloxyquinoline #M07 guanidines N N H O O O N N N O O N O N H O O N O O O O N F F F N O O O N N O O N H N F F F Cl F F F N N O N H F F F S N N O N H F N N O N H Cl O N N O N H F F F Cl Cl N N O N H F F N F F F Cl N H O Cl Cl NH N N NH N N O O N N N Cl Cl O O N N N Cl Cl N N N O H Cl O O N N N Cl Cl O O N N N Cl O Cl Cl N O N N O N H O S Cl N N Cl N O (CH 2 ) C H 3 n = 10 to 13 n = 12: ~ 70% n N O (CH 2 ) C H 3 11 N + O O N + O O O O O N O O O O N O O O O N O O O N O O O N O O O Cl N O O O O N N O O O N H N H S S S S Zn 2+ N H N H S S S S Mn 2+ N S S 2 Zn 2+ N N Cl S F Cl S O O benzovindiflupyr fenaminstrobin triclopyricarb mandestrobin flufenoxystrobin aromatic hydrocarbons # U08 pyriofenone # U13 flutianil cyano-methylene thiazolidine pyrisoxazole dinitrophenyl crotonates 2,6-dinitro-aniline pyrimidinone- hydrazones quinoxyfen Cl Cl N O F proquinazid I N N O O fluxapyroxad # U14 ferimzone N N N H N F7: cell membrane disruption (prop.) # 46 plant extract Melaleuca alternifolia (Tea Tree Extract) O H N N N H S Cl Cl imidazoles simeconazole benzothiodiazole BTH benzothiazole thiadiazole carboxamide polysaccharide P05: Reynoutria sachalinensis (Giant Knotweed Extract) plant extract toluamide pyridinylmethyl-benzamide cyano-imidazole sulfamoyl-triazole 1,2,4-thiadiazole propineb mancozeb febram N H N H S S S S Zn 2+ N S S 3 Fe 3+ chinomethionat fluoroimide . #M10 quinoxalines #M11 maleimides pyrimorph fenpyrazamine hydroxyanilides amino-pyrazolinones ethylamino-thiazole carboxamide Unknown Mode of Action tolfenpyrad isofetamid Bacillus sp. and the fungicidal lipopeptides produced pyrimidinamine pyrazole -5-carboxamide phenyl-oxo-ethyl thiophene amide coumoxystrobin methoxy- acetamides # U16 tebufloquin 4-quinolyl acetate O O O O O Br O S S O P S O O O P N O N N O O O P S O O S S O O O N S N H O N H S N O O N H O O N O N H Cl Cl Cl N H O O Cl Cl O O N H O O NH 2 Cl Cl N + O O Cl Cl Cl Cl Cl N + O O Cl Cl Cl Cl N + O O O O N H N O S O O O N O O H N O H N NH N O H N N O S N O Cl Cl Cl O O N O O NH O S O O N H O O S N H O O S N H S O O O O O N N H O N H N Cl Cl Cl Cl Cl N H Cl O O O H Cl O N N H Cl N N Cl N N N + O O N H O H Cl Cl N N N N S O NH N O O O N N Cl O N N H O O N N H O S N H O O I O O NH O O NH N H OH O H OH OH O H O H N H NH 2 N H NH 2 O O H S N O O Cl Cl Cl Cl S N O O Cl Cl Cl S O S O N N Cl Cl Cl Cl N N N N Cl N H O F F Sn OH Sn O O Sn Cl Cl N N H Cl N + O O F F F F F F N + O O O N S O O N O N S N N Cl O Cl Cl Cl O S N N O S O O F F N H N Cl Cl N H N S Si O N H triazolo-pyrimidylamine # U17 picarbutrazox tetrazolyloxime dimethachlone I2: dehydratase in melanin biosynthesis # 16.2 M elanin B iosynthesis I nhibitors: Dehydratase (MBI-D) I3: polyketide synthase in melanin biosynthesis # 16.3 M elanin B iosynthesis I nhibitors: P olyketide synthase (MBI-P) fenoxanil Cl Cl O O N H N cyclopropane carboxamide carpropamid carboxamide Cl Cl N O Cl diclocymet Cl Cl N H O N propionamide tolprocarb trifluoroethyl-carbamate B6: actin/myosin/ fimbrin function e.g. in vesicle trafficking # 47 cyanoacrylates phenamacril aminocyanoacrylates pydiflumetofen N-methoxy-(penyl- ethyl)-pyrazole- carboxamides # U18 validamycin O O H OH OH O N H OH O H O H O H OH OH OH O H glucopyranosyl antibiotic zinc thiazole H4: chitin synthase # 19 Polyoxins Polyoxin B N O OH N H NH 2 OH N H OH O O H N H 2 OH O O O O O O H peptidyl pyrimidine nucleoside pyraziflumid pyrazine - carboxamides F9: lipid homeostasis and transfer/storage # 49 OSBPI Oxysterol binding protein homologue inhibition F8: ergosterol binding # 48 polyene oxathiapiprolin Plant oils (mixtures) eugenol, geraniol thymol natamycin (pimaricin) piperidinyl- thiazole - isoxazoline P06: BM : Biologicals with Multiple Modes of Action BM01: BM02: Bacillus mycoides (Isolate J) Bacillus cereus group polypeptide lectin Trichoderma spp. metabolites Extract from the cotyledons of lupine plantlets (BLAD) Trichoderma atroviride (strain SC1)

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Page 1: O N ON OHON SO H NO HN O NOSn Cl O NHO O Mode of …pesticidealbania.com/wp-content/uploads/2017/02/frac-moa-poster... · febram N H N H S S S S Zn 2+ N S S 3 Fe 3+ chinomethionat

B5:

delocalisation

of spectrin-like

proteins# 43 benzamides

ferbam

mancozeb

propineb

#M6 sulphamides

C5: uncouplers of oxidative phosphorylation# 29

C7: ATP production

(prop.)# 38 thiophene-

carboxamides

silthiofam

D2:

protein synthesis# 23 enopyranuronic acid

D1: methionine biosynthesis

(cgs gene) (prop.)# 9 Anilino-Pyrimidines

( AP fungicides )

D3:

protein synthesis# 24 hexopyranosyl antibiotics

E2: osmotic signal transduction

MAP / histidine- kinase (os-2, HOG1)# 12 phenylpyrroles (PP- fungicides)

E1: signal transduction (mechanism unknown)#13 azanaphthalenes

fenpiclonil fludioxonil

D4: protein synthesis# 25 glucopyranosyl

antibiotics

kasugamycin

NH

NH

O

NH2

O

OH

OH OH

OH

OH

O

OH

cyprodinil

mepanipyrim

pyrimethanil

F4: cell membrane

permeability,

fatty acids (prop.)# 28 carbamates

I1: reductase in

melanin biosynthesis# 16.1 Melanin Biosynthesis

Inhibitors:

Reductase (MBI-R)

Mode of action of fungicides based on the FRAC fungicide list

(published at www.frac.info/publications )

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.

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.

P01: salicylic pathway

acibenzolar-

S-methyl

fthalide

tricyclazole

pyroquilon

C2: inhibition of complex II:

succinate-dehydrogenase

# 7 SDHI (Succinate dehydrogenase

inhibitors)

mode of action group

sub-group

target site of action

(where known) or putative

target site (=prop.)

FRAC code no. (#)

and group name

Legend:

thiazole carboxamides

chemical (sub-) group

Mode of Action of FungicidesFRAC classification on mode of action 2017 (www.frac.info)

P02:

probenazole

FRAC Mode of Action Poster ©

Updated March 2017

fluazinam

binapacryl

N+

O

O

N+

O O

O

O

C6: inhibitors

of oxidative

phosphorylation,

ATP synthase# 30 organo tins

fentin acetate

fentin chloride

fentin hydroxide

E3: osmotic signal transduction

MAP / histidine kinase (os-1, Daf1)# 2 dicarboximides

P03:

tiadinil

NH

O

ClS

N

N

C4: inhibition of complex III cytochrome bc1(ubiquinone reductase) at Qi site

# 21 QiI fungicides (Quinone inside Inhibitors)

cyazofamid

N

N

Cl

N

SO

O

N

C1: inhibition of complex I

NADH Oxido-reductase# 39 pyrimidinamines pyrazole-MET1

diflumetorim

•Temporary status; information on mode of action and

/ or resistance risk is still uncertain

D5: protein synthesis# 41 tetracycline antibiotics

NH

NN

C2: inhibition of complex II: succinate-dehydrogenase# 7 SDHI (Succinate DeHydrogenase Inhibitors)

benodanil

fenfuram

flutolanil

mepronil

O

NH

I

NHO

O

O

O

NH

FF

F

O

NH

O

S

sulphur

.Cucopper

preparations

thiram

zineb

metiram

chlorothalonil

S

N SS N

S

#M03 dithiocarbamates & relatives

dichlofluanid

#M06 sulphamides

mixture of

iminoctadine

and other

polyamines

guazatine

iminoctadine

guanidines

NH

NH2

NH

NH

NH

NH2

NH

#M04 phthalimides

#M01/02 inorganics

#M05 chloronitriles

anilazine

NH

Cl

N

NN

Cl

Cl

#M08 triazinesdithianon

#M09 anthraquinones

NH

SS

NH

SS

Zn (NH3)-

3

NH

SS

NH S

S

x

# U12

dodine

NH

NH2

NH2

+

O

O

tolylfluanid

N

N

Cl

S

F

ClS

O

O

captan

captafol

blasticidin-S

streptomycin

(bactericide)

oxytetracycline

(bactericide)

OOH

OH

NOH

O

OH

OOH

NH2

OH

Chiral

propamocarb

iodocarb

prothiocarb

# U6

cyflufenamid

C3: inhibition of complex III

cytochrome bc1 (ubiquinol oxidase) at Qo site (cyt b gene)# 11 QoI fungicides ( Quinone outside Inhibitors )

azoxystrobin

O

N N

O

O

O

O

N

picoxystrobin

enoxastrobin

O O

O

Cl

NO

methoxy-

acrylates

pyraclostrobin

fenamidone

imidazolinones

methoxy-

carbamates

orysastrobin

dimoxystrobin

NO N

H

O

O

oximino-

acetamides

metominostrobin

kresoxim-methyl

oximino-

acetates

O

NO

O

O

trifloxystrobin

G1: C14-demethylase in sterol biosynthesis (erg11/cyp51)# 3 DMI-fungicides (DeMethylation Inhibitors)

(SBI: Class I)

G2:14-reductase and 8 7-isomerase in sterol

biosynthesis (erg2, erg 24)# 5 Amines(“Morpholines”) (SBI: Class II)

G3:3-keto reductase

in C4-de-methylation

(erg27)# 17 (SBI :Class III)

G4: squalene epoxidase in

sterol biosynthesis (erg1)# 18 (SBI class IV)

pyributicarb

(herbicide)

thiocarbamates

O ONN

S

allylamines

spiroxamine

NO

O

aldimorph

tridemorph

fenpropidin

N

morpholines

spiroketal-

amines

piperidines

piperalin

O

O

Cl

Cl

N

fenpropimorph

dodemorph

O

N

N

O

azaconazole

bitertanol

bromuconazole

cyproconazole

OH

N

Cl

N

N

Cl

Cl

O

N

N

N

Br

difenoconazole

diniconazole

ClOH

NCl

NN

epoxiconazole

NN

N

OF

Cl

OH

N

O

NN

propiconazole

penconazole

N

Cl

N

N

Cl

myclobutanilN

Cl

NN

N

fluquinconazole

fenbuconazole

FN

N

ClCl

N

N

N

O

flusilazole

F

N

Si

N

N

F

imibenconazole

Cl

N

Cl

N

N

N

S

Cl

ipconazole

N

N

N

OH

Cl

metconazole

hexaconazole

tebuconazole

tetraconazole

OH

N

Cl

NN

Cl

flutriafol

OH

N

F

N

F

N

triazoles

Cl

N

Cl

NN

OF

F

F

F

nuarimol

fenarimol

OH

Cl

N

N

Cl

OH

Cl

N

N

F

pyrimidines

triforine

NH

N

NH

N

Cl

ClCl

O

O

Cl

ClCl

piperazines

pyridines

pyrifenox

Cl Cl

N

N

O

prochloraz

imazalil

pefurazoate

Cl Cl

N

O

N

OO

O

N

NN O

N

Cl

N

O

ClO

N

Cl

triazolinthione

OH

N

N

N

ClN

Cl

NN

N

prothioconazole

N

NN

FOH

Si

triadimefon

triadimenol

triticonazole

Cl

N O

N

N

OH

OH

NN

N

Cl

triflumizole

oxpoconazole

N

Cl

NN

O

F F

F

O

N

Cl

NN

O

naftifine

(antimycotic)

terbinafine

(antimycotic)fenhexamid

pyridines

G: Sterol Biosynthesis in Membranes

C: Respiration

F: Lipid Synthesis or Transport / Membrane Integrity or FunctionE: Signal TransductionD: Amino Acid and Protein Synthesis

C: Respiration

H:Cell Wall Biosynthesis

I: Melanin Synthesis in Cell Wall

P: Host Plant Defence Induction M: Chemicals with Multi-Site Activity

# 35

triazoxide

# 36

flusulfamide

Cl

Cl

NH

S

O

O

N+

O

OF

FF

# 37

diclomezine

# 34

teclofthalam

# 27

cymoxanil

# 42

methasulfocarb

H3PO3

# 33

phosphorous

acid

Unknown Mode of Action

C: Respiration

phenyl-

benzamidesfuran -

carboxamidesboscalid

NH

O

Cl

N

Cl

thifluzamide

S

N

O

NH

Br

Br

OFF

F

F

F

F

Thiazole -

carboxamides

Pyridine -

carboxamides

oxycarboxin

carboxin

Oxathiin -

carboxamides

fluoxastrobin

O

NO

NO

O

NN

O

Cl F

dihydro-

dioxazines

oxazolidine-

diones

famoxadone

benzyl-carbamates

pyribencarb

N

ON

Cl

NH

O

O

folpet

A1: RNA polymerase I# 4: PA-fungicides (PhenylAmides)

A2: adenosin-deaminase# 8: hydroxy (2-amino)-pyrimidines

bupirimate

O

NNN

NH

S

O

O

dimethirimol

ethirimol

A4: DNA topoisomerase

type II (gyrase)# 31: carboxylic acids

oxolinic acid

(bactericide)

A3: DNA / RNA synthesis (prop.)# 32: heteroaromatics

octhilinonehymexazole

benalaxyl

metalaxyl-M

metalaxyl

furalaxyl

A: Nucleic Acid Synthesis

acylalanines

oxazolidinonesbutyrolactones

isoxazoles isothiazolones

F3: lipid peroxidation (prop.)# 14 aromatic hydrocarbons & heteroaromatics

tolclofos-

methyl

etridiazole

biphenyl

chloroneb

O

Cl

Cl

O

O

S

N N

Cl Cl

Cl

ClS

OP

O

OCl

tecnazene

(TCNB)

dicloran

quintozene

(PCNB)

isobenzo-furanone

pyrrolo-quinolione

triazolobenzo-thiazole

chlozolinate

procymidone

O ON

ClCl

iprodioneCl

ON

N

Cl

O

O

NH

Cl

O

O

N

O

Cl

O

O

vinclozolinCl

ON

O

Cl

O

maneb

ziram

H5: cellulose synthase# 40 Carboxylic Acid Amides

(CAA fungicides)

mandipropamid

dimethomorph

flumorph

iprovalicarb

O

NH

NH

O

O

benthiavalicarb

NH

O

NH

O

O N

S

Fvalifenalate

O

O

NH

O

NH

O

O

Cl

cinnamic acid

amides

valinamide

carbamates

mandelic acid

amides

B1: ß-tubulin assembly in mitosis # 1: MBC fungicides

(= Methyl Benzimidazole Carbamates)

B2:

ß-tubulin assembly

in mitosis*# 10 N-phenyl

carbamates

* negative cross-resistance to B1

B3:

ß-tubulin assembly in mitosis# 22 benzamides and

thiazole carboxamides

B4:

cell division

(prop.)# 20 phenylureas

zoxamide

benomyl

carbendazim

fuberidazole

thiophanate

thiophanate-

methyl

thiabendazole

N

O

N

NH

NH

O

O

NH

N

NH

O

O

NH

N O

NH

N N

SNH

NH

NH

S

NH

O

O

O

O

S

NH

NHS

NH

NH

S

O

O

OO

thiophanates

pencycuron

diethofencarb

B: Cytoskeleton and Motor Proteins

ethaboxam

amisulbrom

N

N

SO

O

N

F

Br

S

OO

N

N

F2: phospholipid biosynthesis

methyltransferase# 6 phosphorothiolates & dithiolanes

iso-

prothiolane

pyrazophos

iprobenfos

edifenphos

phosphorothiolates

dithiolanes

benzimidazoles

# U08

metrafenone

cyanoacetamide-

oxime

ethyl-

phosphonates

phosphorous

acid

phthalamic

acid

benzotriazines benzene-

sulfonamides

pyridazinones

thiocarbamates

phenyl

acetamides

quinazolinone

Pyridinyl - ethyl -

benzamides

pyrazole - 4 -

carboxamides

fluopyram

furametpyr

penthiopyrad

bixafen

isopyrazam

sedaxane

etaconazole

meptyl dinocap

F6: microbial disrupters of

pathogen cell membranes# 44 Microbial (Bacillus sp.)

Bacillus

amyloliquefaciens

(synonym B. subtilis)

strains:

QST 713

FZB24

MBI600

D747

P04:

NC : Not Classified

arylphenyl

ketones

laminarin

Mineral oils, organic oils,

potassium bicarbonate,

material of biological

origin

fluopicolide

benalaxyl-M

ofurace oxadixyl

N

O

NH2N

NH

NH2O

O

N

NH2

NH

OHO

OHO

OHO

HO

OH

OHO

OH

OHO

OH

O

OHO

HOO

OH

OHO

OH

H n

PO-O

O

HAl+++

3

# 33

fosetyl-al

isotianil

pyrametostrobin

pyraoxystrobin

penflufen

C8: inhibition of complex III cytochrome bc1(ubiquinone reductase)

at Qo site stigmatellin binding sub site)

# 45 QoSI-fungicide (stigmatellin binding type)

ametoctradin

N

NN

N

NH2

aryloxyquinoline

#M07 guanidines

NNH

O

O

ON

N

N

O

O

NO N

H

O

O

NO O

O

ON

F

F

F

NO

O

ONN

O

O

NH

N

F

F

F

ClFF

F

N

N

O

NH

FF

FS

N

N

O

NH

F

N

N

O

NH

ClO N

N

O

NH

FF

F

Cl

Cl

N

N

O

NH

FF

N

F

F

F

Cl

NH

OCl

Cl

NH

NN

NH

NN

O

O

N

N

NCl

Cl

O

O

N

N

NCl

Cl

N

N

N

OH

Cl

O

O

N

N

NCl

ClO

O

N

N

NCl

O

Cl

Cl

N O

N

N

O

NH

O

S

Cl

N

N Cl

N O(CH2)

CH3

n = 10 to 13n = 12: ~ 70%

n

N O(CH2)

CH3

11

N+

O O

N+

O

O

O

O

O

N

O O

O

O

N

O O

O

O

N

O

O

O

N

O

O

O

N

O

OO

Cl

N

OO

O

O

NN

OO

O

NH

NH

S

S

S

SZn

2+

NH

NH

S

S

S

SMn

2+

N

S

S

2

Zn2+

N

N

Cl

S

F

ClS

O

O

benzovindiflupyr

fenaminstrobin

triclopyricarb

mandestrobin

flufenoxystrobin

aromatic

hydrocarbons

# U08

pyriofenone

# U13

flutianil

cyano-methylene

thiazolidine

pyrisoxazole

dinitrophenyl crotonates2,6-dinitro-aniline

pyrimidinone-

hydrazones

quinoxyfen

Cl

Cl N

O

F

proquinazid

I

N

N

O

O

fluxapyroxad

# U14

ferimzone

NN

NH

N

F7: cell membrane

disruption (prop.)# 46 plant extract

Melaleuca

alternifolia

(Tea Tree Extract)

OH

N

N

NH

S

ClCl

imidazoles

simeconazole

benzothiodiazole BTH

benzothiazole

thiadiazole carboxamidepolysaccharide

P05:

Reynoutria

sachalinensis

(Giant Knotweed

Extract)

plant extract

toluamidepyridinylmethyl-benzamide

cyano-imidazole sulfamoyl-triazole

1,2,4-thiadiazole

propineb

mancozeb

febram

NH

NH

S

S

S

SZn

2+

N

S

S

3

Fe3+

chinomethionat

fluoroimide

.

#M10 quinoxalines

#M11 maleimides

pyrimorph

fenpyrazamine

hydroxyanilides

amino-pyrazolinones

ethylamino-thiazole

carboxamide

Unknown Mode of Action

tolfenpyrad

isofetamid

Bacillus sp. and

the fungicidal lipopeptides produced

pyrimidinamine pyrazole -5-carboxamide

phenyl-oxo-ethyl

thiophene amide

coumoxystrobin

methoxy-

acetamides

# U16

tebufloquin

4-quinolyl acetate

OO

O

OO

Br

O

S

S

O

P

S

OO

O

P

NO

N

N

O

OO

PS

O

O

S

S

O

O

O

N

S

NH

O

NH

S

N

O

O

NH

O

O

N

O

NH

Cl

Cl

Cl

NH

O

O

Cl

Cl

O

O

NH

O

O

NH2

ClCl

N+O O

Cl Cl

Cl

ClCl

N+O O

Cl Cl

ClCl

N+O O

OO

NH

NOS

O

O

ON

O

OH

N

OH

N

NH

N

OH

N

N

O

SN

O

Cl

Cl

Cl

OO

NO O

NH

O

S O

O

NH

O

O

S

NH

O

O

SNH

S

O

O

O

O

ON

NH

O

NH

N Cl

ClCl

Cl

Cl

NH

Cl

OOOH

Cl

O

NNH

Cl

N

NCl

NN

N+

O

O

NH

OH

Cl

Cl

N

N

N

NS O

NH

NO

O

ON

NCl

O

NNH

O

ONNH

O

S

NH

O

O

I

OO

NH

O

O

NH

NH

OH

OH

OH

OH

OH

OH

NH

NH2

NH

NH2

O

OH

SN

O

OCl

Cl

Cl

Cl

SN

O

OCl

Cl

Cl

S

O

S

ON

NCl Cl

Cl

Cl

N

N

NN

Cl

NH

O

F

F

Sn

OH

Sn

OO

Sn

Cl

Cl

NNH

Cl

N+

O

O

F

F F

F F

F

N+

O

O

O

N

S

OO

N O

N

S

N

N

Cl

O

Cl

Cl

Cl

O

S

N

N

O S

O

OF

F

NH

N

Cl

Cl

NH

N

SSi

O

NH

triazolo-pyrimidylamine

# U17

picarbutrazox

tetrazolyloxime

dimethachlone

I2: dehydratase in

melanin biosynthesis# 16.2 Melanin Biosynthesis

Inhibitors:

Dehydratase (MBI-D)

I3: polyketide

synthase in melanin

biosynthesis# 16.3 Melanin Biosynthesis

Inhibitors: Polyketide

synthase (MBI-P)

fenoxanil

Cl

Cl

O

O

NH

N

cyclopropane carboxamide

carpropamid

carboxamide

ClCl

N

O

Cl

diclocymet

Cl

Cl

NH

O

N

propionamide

tolprocarb

trifluoroethyl-carbamate

B6:

actin/myosin/

fimbrin function

e.g. in vesicle

trafficking# 47 cyanoacrylates

phenamacril

aminocyanoacrylates

pydiflumetofen

N-methoxy-(penyl-

ethyl)-pyrazole-

carboxamides

# U18

validamycin

O

OH

OH

OH

ONH

OH

OH

OH

OHOH

OH

OH

OH

glucopyranosyl

antibiotic

zinc thiazole

H4: chitin synthase # 19 Polyoxins

Polyoxin B

N

OOH

NH

NH2

OHNH

OH

O

OHNH

2

OH

O

O

O

O

OOH

peptidyl pyrimidine nucleoside

pyraziflumid

pyrazine -

carboxamides

F9: lipid homeostasis

and transfer/storage# 49 OSBPI

Oxysterol binding protein

homologue inhibition

F8: ergosterol

binding# 48 polyene

oxathiapiprolin

Plant oils (mixtures)

eugenol, geraniol

thymol natamycin

(pimaricin)piperidinyl-

thiazole -

isoxazoline

P06:

BM : Biologicals with Multiple Modes of ActionBM01: BM02:

Bacillus

mycoides

(Isolate J)

Bacillus cereus group

polypeptide lectin Trichoderma spp. metabolites

Extract from the

cotyledons of

lupine plantlets

(BLAD)

Trichoderma

atroviride

(strain SC1)