Group 1: Acetylcholinesterase inhibitors (Only major representatives of the groups are shown) Group 16: Inhibitors of chitin Group

Group 16: Inhibitors of chitin Group 17: Moulting disruptor, Dipteran

biosynthesis, type 1, Homopteran
CH 3
CH3 CH(CH3) 2
OCO N S N[(CH 2) 3CH 3] 2 SCH3
OCO N S NCH2CH2 CO2 CH2CH3
O CH3 CH3 NHCO 2 N C N N
C O N (C H 3 )2
O CH3 (C H 3) 3 C
CH3 N S C H 2 C O 2 C H 2 C H 3

CH3 O S H2 N N NH
CH3 CH 3
OCONHCH3 N N C(C H 3 )3
CH 3 NH C O CH3NCO2N C N N
CH 3 N
O CH3 SCH3 Triazamate
CH 3 S C CH N OC ONHCH 3 Benfuracarb Carbosulfan Methomyl S O CH(CH 3 )2 NH 2
CH3 SCH3
CH 3 CH 3 CH 3

Mode of Action Classification

CH3NCO2N C
SCH 3 CH 3 Buprofezin Cyromazine
OCONHCH3 O
CH 3NHC O CH 3
Aldicarb Carbofuran Methiocarb Thiodicarb
CHCH 2 CH3
(CH 3)2 NCOC NOCONHCH 3
SCH 3
The key to Insecticide Resistance Management
Carbaryl Fenobucarb Oxamyl
1A Carbamates Group 18: Ecdysone agonists moulting disruptors

Group 8: Unknown or non specific - fumigants O O O C

O
CO 2 CH 3
C(CH3 ) 3 CH 3 O CH 3
S
O Cl C(CH 3) 3 C(CH 3 ) 3 CH C(C H 3 ) 3 C H O O OH O
3 C H3C H2 3 CH3 CH3
S HN N
S HN N NH N HN N HO
Cl N OP(OCH2 CH3 )2 CH 3
CH 3 O CH 3
O CH 3O
O
(CH3 O) 2PS CHCH2CO 2CH2 CH3 O2N OP(OCH3 )2 O O CH 3 C O OH
O O
O CH 3
CH 3 CH 3 CH3 OC
H
O
Cl Cl O
CO2 CH2 CH3
F S F
O CH 3
S (CH3 O) 2P
O
O H Parathion-methyl
CH3 Br Cl3 C NO 2 Chromafenozide Halofenozide Methoxyfenozide Tebufenozide 18A Diacyl- Azadirachtin
Chlorpyrifos Malathion S O
CH3S P NHCOCH 3 N OP(OCH2CH 3)2 C C
( CH3)3 CSCH2 S P(OCH2CH3) 2 hydrazines 18B
N CH3 CONHCH3
Methyl Sulfuryl
OCH3 (CH3) 2CH
O (E )
Chloropicrin
O O bromide 8A Alkyl halides 8B Chloropicrin fluoride 8C Sulfuryl fluoride
S CH3O PSCH 3 P OCH 2C H 3
Acephate Diazinon Monocrotophos Terbufos
Cl SCH 2 CH 2 CH 3
CH3 NHCOCH2 SP(OCH3) 2 NH 2 Br
Group 19: Octopaminergic Group 20: Coupling site II electron
agonists transport inhibitors (Complex III)
Dimethoate Methamidophos Profenofos
1B Organophosphates Group 9: Unknown or Non specific – selective feeding blockers
N O
O O
CH CF 3 COCH 3 CF3
CH CF 3 CH3
CH 3
C H3 CH
CH 3
O C
CH
CH 3
NH (CH 2 ) 11 CH 3 O N CH 3
F
Group 2: GABA-gated chloride channel antagonists 3N a
F
F
Al
F
F
CH 3
N
N
CONHCH 2 CN
CH 3

CH3
N CH N CH N CH 3
CH 3 NH
N N C
CH
O
CH 2
O N O
CH
CH 3
CH CF 3
F N N
N O
CH 3 CH 2 SO CN H
Amitraz Hydramethylnon Acequinocyl Fluacrypyrim
Fluacrypyrim
Cl Cl
Cl Cl Cl Cl
Cryolite
9A Cryolite Pymetrozine Flonicamid 20A 20B 20C
Cl
Cl
Cl
Cl
Cl
O
SO Cl Cl
H 2N N
N
F 3C N
N CN
9B Pymetrozine 9C Flonicamid
Cl Cl Cl Cl O
Cl Cl O S
Cl Cl Cl NH 2
Cl Cl CF 3
CF 3
gamma-HCH
Chlordane Endosulfan (Lindane) Ethiprole Fipronil
Group 10: Unknown or Non specific – Mite Growth Inhibitors Group 21: Coupling site I electron transport inhibitors
2A Cyclodiene Organochlorines 2B Phenylpyrazoles (Fiproles) CH 3

Cl
S
O
O F
9C: Flonicamid
O C H 2 CH 3
C(CH 3)3
N CH2 CH 2
CH 3 CH 2
Cl

C
O
H
O O
C CH 2

N N Cl
N
N NH O CH3 N N NH CH 2 O
N C N CH 3
NH C(CH 3 )3 N CH 3 C(CH 3)3
CH 3CH 2 Cl
Group 3: Sodium channel modulators (Only major representatives of the groups are shown)
Cl
N N CH3
F
O
O
CH 2
CH 2 (CH2 )2OCH 2 CH 3
C H 3O
OCH 3
H
O

CH 3 N CH 3
N

O H
CH 3
CH 2 C
H Clofentezine 10A Clofentezine Hexythiazox 10A Hexythiazox Etoxazole 10B Etoxazole Fenazaquin H C O Pyrimidifen N
N
C(CH 3 )3
Tebufenpyrad CH 3 CH 2 Cl
O
O
Rotenone
CH 3 H C O C H N N C
CN O R1 O O (CH 3) 3C CH2 S O N CH 3
O O
C CH H NH CH 2
Cl CH3 CN C C O
R CH 3 CH 3 CH 2 C Cl CH 3
C CH CO 2CH O Cl H H O C(CH 3 ) 3
Cl
CH3
CH(CH 3) 2

F3C
(S) (Z)-(1R)-cis -
R = -CH 3 (chrysanthemates) or - CO 2CH 3 ( pyrethr ates)
R 1 = - CH=CH 2 ( pyr ethr in) or - CH 3 ( cinerin) or -CH 2CH 3 ( jasmol in)

Fenpyroximate Pyridaben Tolfenpyrad

21 METI acaricides
& Rotenone
(Z)-(1R)-cis- C CH CH 3 C O CN
F3C CH 3 2
Cl C O
C CH C H3 CO 2C H 2 H H H
Pyrethrins
Cl H
C H3
H
Cypermethrin Cl
C CH
CH3
CO 2CH
CN
O Esfenvalerate
Cl
H
CH 3

CH 3 H
(Pyrethrum)
Group 11: Microbial disruptors of insect mid-gut membranes - includes transgenic crops
CN

expressing Bacillus thuringiensis toxins. B.t. subspecies shown

H C H3 H Cl CH3 C CH CO 2
Cl CH 3 CH 3 C O
F3C
C CH CO 2C H 2 H
C H3 (S) (1R)-cis -
F3C Cl (R) (Z)-(1S)-cis -
C CH CH 3 C O
CN CH 3 O CH OCH 3
Cl
H
2
C O Zeta-
(Z )-(1S)-cis - H
CH 3CH 2 O
Lambda-
Group 23: Inhibitors of
H CCl 3
Bifenthrin
Cl
H
CH 3

CH 3 H
cypermethrin
O
cyhalothrin Group 22: Voltage dependent
lipid synthesis
C CH C O2 CN
Cl CH 3
H

(R) (1S)-cis -
C O
CH 3 C
CH 3
CH 2 OCH 2
F3C
(Z)-(1S)-cis-
F F Methoxychlor sodium channel blockers
Alpha- Cl
C CH CH 3 CO CH

H
2 2

H
CH 3
B.t. israelensis Bacillus.sphaericus B.t. aizawai B.t. kurstaki B.t. tenebrionis
Br F F
CN
Cl
C CH
CH 3
CO 2CH O
cypermethrin Br
C CH CH 3 CO 2
C
CN
O
Etofenprox CH 3
Cl O
Cl
H H H H CH 3
H F F Cl CH Cl
CH 3 CH 3 Cl
O
F
F 3C
C CH
CH 3
CO 2CH 2 CH 3
CCl3

11B2
Cl CO 2 CH 3 Cl O 23 Tetronic
(Z)-(1R)-cis-
F F

11A1 11A2 11B1 11C O O

O
CH 3 CH 3 C
O
C(CH 3 ) 3
CH 2
Cyfluthrin Deltamethrin Tefluthrin DDT N N
OCF 3
CH 3 C
acid
3 Pyrethroids O
N
CO 2 CH 3
CH 3 CH CH
2 3
CH 3
O
O
derivatives
Indoxacarb Spirodiclofen Spiromesifen

Group 12: Inhibitors of oxidative phosphorylation, disruptors of ATP formation (inhibitors

Group 4: Nicotinic acetylcholine receptor agonists/antagonists of ATP synthase)
CH 3
CH 3
C N
CN
CH 3 NH NO 2 N
N NO 2
C(CH 3)3
Group 24: Mitochondrial complex IV Group 25: Neuronal inhibitors
H H C C O
CH 2 N
CH 3
O N N
CH 3
CH2 N H
CH2 CH3
N
CH 2
C H(CH 3) 2
Sn CH 3 CH 3
Cl
electron transport inhibitors (unknown mode of action)
S O
O NH CSNH C(CH 3 )3 N C C H2 Sn O Sn CH 2 C Cl SO2 Cl
N N N CN N CH 3 CH 3 OSO2 CH 2 C CH
NO 2 S Cl
Cl NO 2 Cl N C H(CH 3) 2 N 3 3
H NO 2 N Cl
N N Fenbutatin
CH 3 N Cl N Thiamethoxam
Acetamiprid S Dinotefuran N Nitenpyram CH 2 Diafenthiuron Azocyclotin oxide Propargite Tetradifon
NH Cl CH 2 N N H Sn N HNH C OOC H(C H 3 )2
N
CH 2 OH PH 3 CN- PH 3 OCH 3
N
Cl
12B Organotin 12C 12C
Clothianidin Imidacloprid Thiacloprid
4A Neonicotinoids 12A Diafenthiuron Cyhexatin
miticides Propargite Tetradifon Phosphides
24A Cyanide
24B Phosphine
24C Bifenazate

N CH 3
SO 2 S CH 2
H 2 NCOS CH2 S CH 3
CH 2 SSO 3Na Group 13: Uncouplers of oxidative phos- Group 28: Ryanodine
N
CH N(CH 3 )2 CH N(CH 3 ) 2 .HCl S
CH 3
N CH
Group 14: Unallocated Group 26:Aconitase Group 27: Synergists
H SO 2 S CH 2 H 2 NCOS CH2 (CH 3)2N
S CH 2 SSO 3Na phorylation via disruption of H proton gradient receptor modulator
Cartap
inhibitors
Thiosultap-
Nicotine Bensultap hydrochloride Thiocyclam sodium
OH
O O
CN CH 3
4C Bensultap 4C Cartap
S

4B Nicotine 4C Nereistoxin analogues Br

Cl
O2N
o O
I HN

O
S (CH 2 )3 CH 3 O
CF 3 N F CH 3(CH 2)3 OCH 2CH 2OCH 2CH 2OCH 2 P
CH2 OCH 2CH 3 NO 2 O
CH 3 (C H 2) 3S HN
S(CH 2 )3 CH 3
o- CH 3(CH 2)2 O
C F3

Group 5: Nicotinic acetylcholine

F
Chlorfenapyr DNOC CF3
Piperonyl
Group 6: Chloride channel activators Fluoroacetate butoxide DEF Flubendiamide
receptor agonists (not 4)
Spinosad
27A P450-dependent 27B Esterase
HO

CH 3
OCH 3

O O
OCH 3

CH 3 CH 3 O
CH 3 O
O
CH 3
O
O
CH 3
O
H
R

O
CH 3
CH 3
C H3 H
O
O R
CH3

Group 15: Inhibitors of chitin biosynthesis, type 0, Lepidopteran monooxygenase inhibitors inhibitors
CH 3
( CH 3)2 N O O O
H CH 3
NH2
OCH 3 H
OCH 3 CH 3 O CH 3 CH 3
CH 3 O O
CH 3
O O
C H3
CH 3 O CH 3 O
H
CO 2
O O

6
O CH 3 HO H
H R
HH
CH 3
OH H M ilbem ycin A3: R = -CH 3
O O O O
O OH H O CH 3
M ilbem ycin A4: R = -CH 2CH3
(i) R = -CH 2 CH 3 (avermectin B1 a) H
CH 3CH 2 O B1a R = CH 3CH2 - OH
HH H O CH3

5 Spinosyns Avermectins
O CH 3 B1 b R = CH 3-
R (ii) R = -CH 3 (avermectin B1b ) H H OH
OH F
Cl
Emamectin
Group NS: Miscellaneous non
spi no syn A, R = H-
CONHC ONH O F
Abamectin Milbemectin
benzoate & Milbemycins Group UN: Compounds with unknown mode of action
spi no syn D, R = CH 3 - Cl
F N
Cl C F3 C F 3O N HC ON HC O

specific (multi-site) inhibitors

CF 3CHFCF2O NHCONHCO
F
Cl Cl
F
O
F Cl Cl Fluazuron Cl F Lufenuron Cl F O
C NH
C
Triflumuron
CONHCONH O C F3 C F3 O N HCON HCO C F3 CHFCF 2O NH F

Group 7: Juvenile hormone mimics F Cl

N
F F Cl

F
UNA N S
O
UNC Cl
Cl
O O
O

- + - - 3+ O -
O

O 3 O O
N
OC H 3
Chlorfluazuron C N O
CH 2 NH CONH CO

F
Flufenoxuron Cl F
Noviflumuron CH 3 N S Cl O Cl CF 3
Na2 B4 O7 10H2 O -
O
Sb
O
- -
O
Sb
O-
.2K + .3H O
2

CF3O CHFCF2O NHCO NHCO

(CH 3 )2 C (CH 2) 3
CH 3 C O 2C H2 C CH Cl O O
H C C CH CH2 H
F O
C H3 C C H
CH 3 C C H C NOCH 2CH 3
CH3
CH CH2 CH
CH3
C C
H C H3
CO 2 CH 2 C H 3 CH 3 C H2 C H2
CH C H2 H
H C C N O O O C OCH3 Chinomethionat OH Pyridalyl Borax Tartar emetic
CH3 CH 2 C H2 CH 2 C C C H CH 2 CH 3 C O 2 C H(CH 3) 2 O O C H 2C H 2N H C O 2C H 2C H 3 CH C H 2 F Cl F
H H CH 3
CH 3 O
Flucycloxuron Cl F
Novaluron CH 3O Cl
Cl C Cl
Cl NHCONHCO CHF 2CF 2O NHCO NHCO F NH CO NHC O CC l 3

Hydroprene Kinoprene Methoprene Fenoxycarb

F
Cl F
Cl F F UNB UND NSA NSB
Pyriproxyfen Benzoximate Dicofol
Diflubenzuron Hexaflumuron Teflubenzuron
15 Benzoylureas
7A Juvenile hormone analogues 7B Fenoxycarb 7C Pyriproxyfen

More information on the Insecticide Resistance Action Committee and the Mode of Action Classification is available from: www.irac-online.org or enquiries@irac-online.org
Structures are reproduced from the Pesticide Manual with permission from the British Crop Protection Council Details presented are accurate to the best of our knowledge at the time of publication but IRAC or its member companies cannot accept responsibility for how this information is used or interpreted Poster Version 1, October 2005. Based on the Mode of Action Classification - Version 5.1