Group 1: Acetylcholinesterase (AChE) inhibitors (Only major representatives of the groups are shown) Group 15: Inhibitors of chitin

Group 15: Inhibitors of chitin biosynthesis, type 0

CH3
Mode of Action Classification
CH3 CH(CH3)2
OCO N S N[(CH2)3CH3]2 SCH3 N CON(CH3)2 F Cl Cl
Cl F
OCO N S NCH2CH2CO2CH2CH3 N Cl F
O CH3 CH3NHCO2N C (CH3)3C CONHCONH O CF3
CF3 O NHCONHCO
O CH3 N N CF3OCHFCF2O NHCONHCO
CF3O NHCONHCO
CH3 SCH2CO2C2H5 F Cl F F
CH3 O F F F F
CH3 CH3 Cl
OCONHCH3
CH3NH C O
CH3
O
CH3NCO2N C Triazamate Chlorfluazuron F

CH3 SCH3 F O O
Flufenoxuron Cl F
CH3S C CH NOCONHCH3 Benfuracarb Carbosulfan Methomyl S F C N O
CH2 NHCONHCO
Cl
F
Novaluron Triflumuron
N F
SCH3 N
CH3 H H F F NHCONHCO
CH3 CH3 CH3 Cl F CF3CHFCF2O NHCONHCO
CH3NCO2N C F
Cl
F
SCH3 CH3 Cl Cl F F
OCONHCH3 O
F F

Carbofuran CH3NHC O CH3 Bistrifluron Flucycloxuron O

Teflubenzuron
Aldicarb CHCH2CH3
Methiocarb Thiodicarb Cl F
Lufenuron Cl F O C
Cl NHCONHCO C NH
(CH3)2NCOC NOCONHCH3 CHF2CF2O NHCONHCO
CF3CHFCF2O NH F

SCH3 F Cl F
Cl

Carbaryl Fenobucarb Oxamyl 1A Carbamates Diflubenzuron Hexaflumuron Noviflumuron

15 Benzoylureas

S Group 16: Inhibitors of Group 17: Moulting

Cl N OP(OCH2CH3)2
S S
chitin biosynthesis, Group 18: Ecdysone receptor agonists
Cl Cl
(CH3O)2PS CHCH2CO2CH2CH3
CO2CH2CH3
O2N OP(OCH3)2
Insecticide Resistance Action Committee type 1
disruptor, Dipteran
O
CH3
O S
Chlorpyrifos Malathion (CH3O)2P O H Parathion-methyl S
N OP(OCH2CH3)2 C C
CH3SP NHCOCH3 (CH3)3CSCH2S P(OCH2CH3)2 O O
N CH3 CONHCH3 C(CH3)3 CH
O 3 C(CH3)3 CH
3
OCH3 (CH3)2CH
O (E )
HN N NH N
O CH3 CH3O CH3
O O
S P OCH CH H2N N NH O
Acephate Diazinon CH3OPSCH3 Monocrotophos 2 3 Terbufos S CH3 CH3
N NC(CH3)3
Cl SCH2CH2CH3

The Key to Resistance Management

N N
CH3NHCOCH2SP(OCH3)2 NH2
Br N Chromafenozide O
Cl C(CH3)3 Methoxyfenozide O
O CH(CH3)2 NH2 CH3CH2 C(CH3)3 CH
3
HN N HN N

Dimethoate Methamidophos Profenofos Buprofezin Cyromazine O O

1B Organophosphates 18 Diacyl-
CH3

Halofenozide Tebufenozide
16 Buprofezin 17 Cryomazine hydrazines
Group 2: GABA-gated chloride channel antagonists
More information on IRAC and the Mode of Action Classification is available from: Group 19: Octopamine Group 20: Mitochondrial complex III electron
Cl
CH3CH2SO CN
Cl
receptor agonists transport inhibitors
Cl
Cl
Cl
Cl

Cl
Cl
Cl
O
SO
H2N
Cl
N
N

Cl
F3C N
N CN
O
www.irac-online.org or enquiries@irac-online.org
Cl Cl S
Cl Cl O Cl NH2 O
CF3 O O
Cl Cl CH CF3 COCH3 CF3
CH3 CH3 CH
CF3 CH3 CH3 NH CH O C
O
CH3
N CH3
N N C (CH2)11CH3 CH2
CH3 N CH N CH N CH3 CH
Chlordane Endosulfan Ethiprole Fipronil CH3 NH CH O O N O
CH3
CH3
CH CF3

Group 8: Miscellaneous non-specific (multi-site) inhibitors

Amitraz Hydramethylnon Acequinocyl Fluacrypyrim
2A Cyclodiene Organochlorines 2B Phenylpyrazoles (Fiproles)
O
Group 3: Sodium channel modulators (Only major representatives of group 3A are shown)
O O
19 Amitraz 20A Hydramethylnon 20B Acequinocyl 20C Fluacrypyrim
CH3Br F S F - +
O 3 O
- -
O 3+ O -
Cl3C NO2 Na 2 B 4 O 7 . 10H 2O
-
O
Sb
O
- -
O
Sb
O-
.2K+ .3H O
2

O
O H
CH3
CH2 C
H
Sulfuryl
O O
Group 21: Mitochondrial complex I electron transport inhibitors
CH3 H C O C H Methyl Borax Tartar emetic
Cl CH3 CN
O
C
O
C
CN
O
R
C CH H
CH3 CH3
O R1
bromide Chloropicrin fluoride
C CH CO2CH O Cl H H
R = -CH3 (chrysanthemates) or -CO2CH3 (pyrethrates)
Cl CH(CH3)2 R1 = -CH=CH2 (pyrethrin) or -CH3 (cinerin) or -CH2CH3 (jasmolin) Cl CH Cl
CH3

F3C
(Z)-(1R)-cis-
CH3
F3C

Cl
(S) (Z)-(1R)-cis -

C CH CH3 C O2
C
CN
O
CCl3 8A Alkyl halides 8B Chloropicrin 8C Sulfuryl fluoride 8D Borax 8E Tartar emetic N
C(CH3)3
N
N CH2 CH2
NH O CH3
Cl
O
CH3CH2
Cl
C CH CH3 CO2C H2
H H
CN
H
CH3
H H
Pyrethrins CH3CH2 Cl CH3 N N
C
NH CH2
CH3 Cypermethrin Cl
CH3
CO2CH O Esfenvalerate H CH3 H
(Pyrethrum) DDT N
(CH2)2OCH2CH3
CH3
C CH Cl C(CH3)3
CN
H CH3 H Cl CH3 C CH C O2 O CH2
Cl CH3
F3C CH3 C O CH2 CH3
C CH CO2C H2 H CH3 N CH3 C CH2
Group 9: Selective homopteran N
CH3 (S) (1R)-cis -
F3C Cl (R) (Z)-(1S)-cis -

(Z)-(1S)-cis-
Cl
C CH CH3 C O

H
2

H
H
C
CN
O Zeta- CH3CH2O
Lambda-
Group 10: Mite growth inhibitors Fenazaquin H C O
Pyrimidifen N
N
C(CH3)3
Tebufenpyrad CH3CH2 Cl
O
O
O
H
O O

Bifenthrin Cl
H
CH3

CH3 H
cypermethrin
O
cyhalothrin feeding blockers O
N

CH2 C
O (CH3)3C CH2S O
N
N
CH3
C
NH CH2 CH3
H
C O2
Cl O
C CH CN
O C(CH3)3 CH3O
C O
Cl CH3
H CH3 C CH2OCH2 CH3O CH OCH3 OCH3
(Z)-(1S)-cis-
F F
(R) (1S)-cis - CH3 F3C CCl3 N
Alpha- Cl
C CH CH3 CO CH
2 2 CH3 Fenpyroximate Pyridaben Tolfenpyrad Rotenone
H H
CN Br F F
Cl O
Cl
CH3 cypermethrin C CH CH3 CO2 CN Etofenprox CH3
CH CF3 S O F O CH2CH3
C CH CO2CH O Br
H H H
C O
H CH3 F F Methoxychlor N N
21B Rotenone
H
Cl CH3 N Cl N C N
21A METI acaricides and insecticides
CH3 CH3 Cl
F C CH CO2CH2 CH3 C(CH3)3
N CONHCH2CN NH
F3C CH3
F F
N N O
N CH3
(Z)-(1R)-cis-
N
Cyfluthrin Deltamethrin Tefluthrin 3A Pyrethroids 3B DDT, N
H
O Cl F

Pyrethrins Methoxychlor Pymetrozine Flonicamid Clofentezine Hexythiazox Etoxazole Group 22: Voltage-dependent Group 23: Inhibitors of acetyl
9B Pymetrozine 9C Flonicamid sodium channel blockers CoA carboxylase
10A Clofentezine, Hexythiazox 10B Etoxazole
Group 4: Nicotinic acetylcholine receptor (nAChR) agonists H3C
Cl O
CH2
O H3C
Group 11: Microbial disruptors of insect midgut membranes and derived toxins Cl CO2CH3
O N
O
O
CF3 Cl
CH3 CH3
O
C(CH3)3
O
O

CH3NH NO2 OCF3 N N O

O O C O
H NO2 N N
H H
CH3 C CH2 CH3
C C NC
N N Cl N N O
CH3 CH2 N H O CO2CH3 CF3 CH3 CH CH CH3 O H3C H
S 2 3 O O
NH CH2CH3
N B.t. B.t. Indoxacarb Metaflumizone Spiromesifen Spirotetramat
CH3 CN CH2 N CH3 B.t. Spirodiclofen
aizawai tenebrionis Cry1Ac B.t.
Cry3Ab
C N NO2
Cl N N israelensis Cry2Ab Cry34/35Ab1
CH2 N O N NO2 CH3 aizawai
CH3
Clothianidin
N
N Nitenpyram N
CH2
N
B. B.t.
22A Indoxacarb 22B Metaflumizone 23 Tetronic & Tetramic acid derivatives
Cl CH2 N N H S H Cry1Ab Cry1Fa mCry3A Cry3Bb
N sphaericus kurstaki
Cl S CN
Cl N
N
H H N Nicotine Group 25: Mitochondrial
Acetamiprid O N N Imidacloprid Thiamethoxam
CH3 CH2
Group 24: Mitochondrial complex IV electron transport inhibitors complex II electron
N
NO2
N
transport inhibitors
Cl
Dinotefuran Thiacloprid 4A Neonicotinoids 4B Nicotine Group 12: Inhibitors of mitochondrial ATP synthase
C(CH3)3

C(CH3)3 O
C(CH3)3
Al P Zn 3P2 H3C O
Cl
Group 5: Nicotinic acetylcholine Group 6: Chloride channel activators
CH(CH3)2
Sn
Zinc
CN- N
N C
C
CH3 CH3
O Cl SO2 Cl Aluminium CN
receptor (nAChR) allosteric modulators O NHCSNHC(CH3)3

CH(CH3)2 N
N
N
C CH2
CH3
Sn O Sn CH2 C
CH3
3
OSO2CH2C CH Phosphide Phosphide
H3C
CH3
3
Cl
Ca3 P2 PH 3 Cyanide Cyenopyrafen
Fenbutatin
Spinosad
-
C5 C6, R = H HO
OCH3

OCH3
CH3O
O
CH3 O CH3
H
R
CH3
CH3 H
CH3
Diafenthiuron Azocyclotin Sn
oxide Propargite Tetradifon 24A Calcium
C5 = C6, R = CH3
CH3 O
OH
Phosphine Phosphide
O O O O O
CH3 O
N CH3 O R
Phosphine 24B Cyanide 25 Cyenopyrafen
CH3 CH3
O O O
H CH3
NH2
OCH3 H

12A 12D
(CH3)2N CH3 O CH3 CH3
O OCH3CH CH3
CH3 O
O O O O

12B Organotin 12C

O 3 O O CO2
CH3 OCH3 H HO H O O
OCH3 H R
O CH3
O O OH H Milbemycin A3: R = -CH3
O H H O
O
Milbemycin A4: R = -CH2CH3
H H OH H O CH3
O O O

Diafenthiuron Tetradifon
(i) R = -CH2CH3 (avermectin B1a) H
B1a R = CH3CH2- OH
Cyhexatin
miticides Propargite
CH3CH2 O O
HH H O H H 5 6
H
O CH3 B1b R = CH3-
CH3
O (ii) R = -CH3 (avermectin B1b) H H OH
R R OH

spinosyn A, R = H- Emamectin Group 28: Ryanodine

spinosyn D, R = CH3- Spinetoram Abamectin benzoate Milbemectin
receptor modulators
Group UN: Compounds of unknown or uncertain mode of action
5 Spinosyns 6 Avermectins, Milbemycins Group 13: Uncouplers of oxidative phos- Group 14: Nicotinic acetylcholine H Br
phorylation via disruption of proton gradient receptor (nAChR) channel blockers H3C
N O
H
N
N CH3
C
O
CO2CH3
N O O OH O Cl
CH3 CH3 F O O
Group 7: Juvenile hormone mimics Cl
O
CH3 N
Cl
O CH3O
HO

O
NHNH COOCH(CH3)2
3Na
F
Al
F
Cl
Cl

O Cl
N
CF3
CH3C O
H
OH OCH3 F F
CH3OC O F
O
Chlorantraniliprole
CN
OH SO2 S CH2
CH N(CH3)2
S
S 28 Azadirachtin Bifenazate Cryolite Pyridalyl
OCH3
O2N CH3 S
Diamides
CH3 CO2CH2C CH
Br
CH3
H C C (CH3)2C (CH2)3
SO2 S CH2 (CH3)2N
C C H
CH3 CH3 H CH3
CH CH2 H
CH CH2 H Cl
C C H
CF3 N
CH CH2 CH C C CO2CH2CH3 CH3 CH2 CH2 CH3 N O O O O
CH3 CH2 CH2 CH2 C C CH CH2 H C C O OCH2CH2NHCO2CH2CH3 CH CH2 S
CH2OCH2CH3 NO2 H2NCOS CH2 I HN C(CH3)3
H H CH3 CH3 CO2CH(CH3)2
CH3 O Bensultap Thiocyclam CH3
CH2SSO3Na O CF3 O
O
CH N(CH3)2 .HCl N CH C NOCH2CH3
N
CH3 O
O C OCH3 S OH C
Chlorfenapyr DNOC H2NCOS CH2 CH2SSO3Na O C
Hydroprene Kinoprene Methoprene Fenoxycarb Pyriproxyfen
HN
CH3O Cl CH3 N S
Cl C Cl NC O

14 Nereistoxin Cartap
hydrochloride
Thiosultap-
CF3
F
CF3
CCl3 O H2C CH2

sodium O CH3

7A Juvenile hormone analogues 7B Fenoxycarb 7C Pyriproxyfen 13 Pyrroles, Dinitrophenols analogues Flubendiamide

Benzoximate Chinomethionat Dicofol Cyflumetofen

Guidance on the use of Sub-Groups: • In the absence of other alternatives, it may be possible to rotate compounds between sub-groups if it is clear that cross- • 3A & 3B - If there are no other alternatives, compounds may be rotated in situations where cross-resistance mechanisms (e.g.
resistance mechanisms do not exist in the target populations. kdr) are known to be absent in the insect populations to be treated. DDT is no longer used in agriculture and therefore this is
• Represent distinct structural classes believed to have the same mode of action. only applicable for the control of human disease vectors such as mosquitoes, because of a lack of alternatives.
• Provides differentiation between compounds that may bind at the same target site. • Not all of the current groupings are based on knowledge of a shared target protein. For further information please refer to the
IRAC Mode of Action Classification document. •10A - Clofentezine & Hexythiazox are grouped because they commonly exhibit cross-resistance even though they are structurally
• Are structurally different such that risk of metabolic cross-resistance is lower than for close chemical analogs. distinct, and the target site for neither compound is known.
• Are likely to be metabolized by different enzymes - may bind differently enough within the target site that the chance of •1A & 1B - If there are no other alternatives, compounds may be rotated in situations where cross-resistance mechanisms are
• 22A & 22B - Although these compounds are believed to have the same target site, they have been sub-grouped because they
selection for metabolic/target-site resistance is reduced compared to close analogs. known to be absent in the insect populations to be treated.
are chemically distinct, and current evidence indicates that the risk of metabolic cross-resistance is low.

Structures, reproduced from the Pesticide Manual, are with permission from the British Crop Protection Council The poster is for educational purposes only. Details presented are accurate to the best of our knowledge at the time of publication but IRAC or its member companies cannot accept Poster Version 2, October 2009. Based on the Mode of Action Classification - Version 6.3
responsibility for how this information is used or interpreted. Advice should always be sought from local experts or advisors and health and safety recommendations followed.