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

Group 15: Inhibitors of chitin biosynthesis, type 0, Lepidopteran

CH3 CH(CH3) 2
CH 3
Mode of Action Classification
OCO N S N[(CH 2) 3CH 3] 2 SCH3 N CON(CH3)2 F Cl Cl
Cl F Cl F
OCO N S NCH2CH2 CO2 CH2CH3 N
O CH3 CH3 NHCO 2 N C (CH3)3C CONHCONH O C F3
C F3 O NH CONH CO C F3 O CH FC F2 O N HC ON H CO
O N C F 3O N HC ON HC O
CH3 N
CH3 SCH2CO2C2H5 F Cl
F F
CH3 O F F F F
CH3 CH 3 Cl
OCONHCH3
CH 3
CH 3NH C O CH3NCO2N C Triazamate Chlorfluazuron F

O CH3 F O O
Flufenoxuron Cl F
Benfuracarb Carbosulfan Methomyl S
SCH3
F C N O
CH 2 NH CONH CO
Cl
F Novaluron Triflumuron
CH 3 S C CH N OC ONHCH 3 N N F
SCH3 H H F F NH CO NHC O
CH3 CH3 CH 3 Cl F Cl
CF 3CHF CF 2O NHCONHCO
CH 3 CH3NCO2N C F F

SCH 3 Cl Cl F F
O CH 3
OCONHCH3 F F
CH3NHC O CH3 Bistrifluron Flucycloxuron O
Teflubenzuron
Aldicarb Carbofuran Methiocarb Thiodicarb Cl F Lufenuron Cl F O C
CHCH2 CH3 Cl NHCONHCO C NH
(CH 3)2 NCOC NOCONHCH 3 CH F2 CF2 O NHCO NHCO
CF 3 CHF CF2 O NH F
F Cl F
SCH3 Cl

1A Carbamates Diflubenzuron Hexaflumuron Noviflumuron

15 Benzoylureas
Carbaryl Fenobucarb Oxamyl

Group 16: Chitin bio-

Group 17: Moulting
S
S S
synthesis inhibitors
disruptor, Dipteran
Group 18: Ecdysone receptor agonists
Cl N OP(OCH2CH3 )2
(CH3 O)2 PS CHCH2 CO2 CH2 CH3 O2N OP(OCH3 )2 type 1, Homopteran

O
Cl Cl
CH 3
S
CO 2 CH2 CH3

(CH3 O) 2P
O
O Parathion-methyl
Insecticide Resistance Action Committee
Chlorpyrifos Malathion H S
N OP(OCH2CH 3)2 C C O
CH3S P NHCOCH 3 ( CH3)3 CSCH2 S P(OCH2CH3) 2 O C(CH 3 )3 C H
O
C (CH 3 )3 CH 3
N CH3 CONHCH3 3
HN N NH N
OCH3 (CH3) 2CH
O (E ) CH 3 C H3 O C H3
O O H2N N NH O O
S
S CH3 OPSCH 3 Monocrotophos P OCH 2C H 3 CH 3 CH 3
Acephate Diazinon Terbufos N NC(CH 3 )3 N N
Chromafenozide O

The Key to Resistance Management

CH3 NHCOCH2 SP(OCH3) 2 Br Cl SCH 2 CH 2 CH 3 N
C(CH 3) 3 Methoxyfenozide
NH 2 O CH(CH 3 )2 NH 2 Cl
C H 3C H2
O
C(CH 3 )3 CH 3
HN N HN N

Buprofezin Cyromazine O O
Dimethoate Methamidophos Profenofos C H3

1B Organophosphates 18 Diacyl- Halofenozide Tebufenozide

hydrazines
Group 2: GABA-gated chloride channel antagonists
Group 19: Octopamine Group 20: Mitochondrial complex III electron
CH 3 CH 2 SO CN
More information on IRAC and the Mode of Action Classification is available from: receptor agonists transport inhibitors (Coupling site II)
Cl Cl Cl
Cl
Cl
Cl

Cl
Cl
Cl
O
SO
H 2N
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 NH 2 CF3 O
Cl Cl O O
CH CF 3 C OCH 3 CF 3
CF 3 CH 3 CH 3 CH
CH 3
CH3 C H3 CH O C
NH O N CH 3
(CH 2 ) 11 CH 3
Chlordane Endosulfan Ethiprole Fipronil CH 3 N CH N CH N CH 3
CH 3 NH
N N C
O
CH 2
O N O
CH
CH CH 3
CH3
CH CF 3

2A Cyclodiene Organochlorines 2B Phenylpyrazoles (Fiproles) Group 8: Miscellaneous non-specific (multi-site) inhibitors Amitraz Hydramethylnon Acequinocyl Fluacrypyrim
20A 20B 20C
Group 3: Sodium channel modulators (Only major representatives of group 3A are shown) O O O

CH3 Br F S F - +
O 3 O
- -
O 3+ O - Group 21: Mitochondrial complex I electron transport inhibitors
Cl3 C NO 2 Na B O 10H O -
O
Sb
O
- - Sb
O-
.2K+ .3H O
2

CH 3
CH 2 C
H O O

O H
H C O C H O O
CH 3
O O
CN
C CH H
O R1
Sulfuryl
Cl CH3 CN C C O
R CH 3 CH 3
Methyl Borax Tartar emetic C(CH 3)3
Cl
C CH C O2CH O Cl H

CH(C H3 )2
H
R = -CH 3 (chrysanthemates) or - CO 2CH 3 ( pyrethr ates)
Cl CH Cl bromide Chloropicrin fluoride N N
N C H2 CH 2
NH O CH 3
Cl
O
R 1 = - CH=CH 2 ( pyr ethr in) or - CH 3 ( cinerin) or -CH 2CH 3 ( jasmol in) C H 3 CH 2
CH3 C CH 3
(S) (Z)-(1R)-cis - C H3 C H2 Cl C H3 N N NH C H 2
F3C CCl3 N C CH 2

8C Sulfuryl fluoride
CH 3

8B Chloropicrin
CH 3 C O CN

8D Borax 8E Tartar emetic

(Z)-(1R)-cis- C CH
F3C

8A Alkyl halides (CH 2 ) 2 OCH 2 CH3 H

2
CH 3 C O C (C H 3 ) 3
Cl O
C CH C H3 CO 2C H 2
CN
H
CH 3
H H
Pyrethrins O
CH 2
CH 2 O
O
Cl H
C H3
H
Cypermethrin Cl
CH3
C O 2CH O Esfenvalerate H CH 3 H
(Pyrethrum) DDT C H3 N
N
CH3
C CH Cl H
C CH CO 2 CN O
Cl
H

C CH
C H3 H

CO 2C H 2
CH 3
Cl CH3
F3C CH 3
H
C O
Fenazaquin H C O Pyrimidifen N
N
C(CH 3 )3
Tebufenpyrad C H 3 CH 2 Cl
O
O
C H 3O
OCH 3
(S ) (1R)-cis - N
Group 9: Selective homopteran
F3C C H3 Cl (R) (Z)-(1S)-cis - N C
CH 3 C O O O (CH 3) 3C CH 2S O N NH CH 2 CH 3
C CH CN
Zeta- Rotenone
Group 10: Mite growth inhibitors
2
Cl C O CH 2 C Cl CH 3
(Z )-(1S)-cis - H H
H CH 3CH 2 O Lambda- O C(C H3 )3
Bifenthrin
Cl
H
CH 3

CH 3 H
cypermethrin
O
cyhalothrin feeding blockers 21A METI
C CH C O2 CN Fenpyroximate Pyridaben Tolfenpyrad
acaricides 21B Rotenone
C O
Cl CH 3
H CH 3 C CH 2 OCH 2 CH 3 O CH OCH 3
(Z)-(1S)-cis-
F F
(R) (1S)-cis - CH 3 F3C CCl 3
C CH CH 3 CO CH CH 3 N
Alpha- Br
Cl
H
2

H
2

F F
Cl
CH 3
CN
cypermethrin C CH CH 3 CO 2 CN Etofenprox CH 3
Cl O
C CH CO 2CH O Br H H
C O
Methoxychlor CH CF3 S O CH 2 C H 3
CH 3
O F
N N
Group 22: Voltage dependent
H

Group 23: Inhibitors of acetyl

H H F F
Cl
Cl
CH 3
F CH 3
C CH CO 2CH 2 CH 3 CH 3 N Cl N C N
CH 3
N C(CH 3 )3
F 3C
CONHCH 2 CN NH
(Z)-(1 R)-cis-
F F

3A Pyrethroids 3B DDT, N
N O N Cl
N N
CH3
F
O sodium channel blockers CoA carboxylase
Cyfluthrin Deltamethrin Tefluthrin H

Pyrethrins Methoxychlor Pymetrozine Flonicamid Clofentezine Hexythiazox Etoxazole Cl O

H 3C
CH 2

Cl O
O H 3C
CO 2 CH 3 Cl O

9B Pymetrozine 9C Flonicamid 10A Clofentezine 10A Hexythiazox 10B Etoxazole O N

O CF3

O
CH 3 CH 3 C
O
C(CH 3 ) 3
O

Group 4: Nicotinic acetylcholine receptor agonists N N

OCF3
NC
N
H
N
H
CH 3 C
O O CH 2
O
CH3

N N O
O CF3 CH 3 CH CH CH 3 O H 3C H
CO 2 CH 3 2 3 O O

NO 2 CH 3NH NO 2
Group 11: Microbial disruptors of insect midgut membranes and derived toxins Indoxacarb Metaflumizone
Spirodiclofen Spiromesifen Spirotetramat
H
C C
N N Cl
CH3 CH2 N H
NH
S
N
CH2CH3 22A Indoxacarb 22B Metaflumizone 23 Tetronic & Tetramic acid derivatives
CH3 CN CH 2 N CH3 B.t. B.t. B.t.
Cl N aizawai Cry1Ac B.t.
Cry3Ab
C N NO2 N CH 3 israelensis tenebrionis Cry2Ab Cry34/35Ab1
CH2 N Clothianidin
O N NO2 aizawai
N Nitenpyram
CH3 N
N
CH 2
N
B. B.t.
Group 24: Mitochondrial complex IV electron transport inhibitors
Cl CH 2 N N H S H mCry3A
N
sphaericus kurstaki Cry1Ab Cry1Fa Cry3Bb
Cl S CN Cl
N N
H H N
Nicotine
Acetamiprid O N N Imidacloprid Thiamethoxam
CH 3 CH 2

N CN-
NO 2 Al PH 3 Ca PH 3 Zn PH PH 3
N 3
Cl
Dinotefuran Thiacloprid 4A Neonicotinoids 4B Nicotine Group 12: Inhibitors of mitochondrial ATP synthase Aluminium Calcium Zinc 24A 24B
Phosphide Phosphide Phosphide Phosphine Cyanide
Phosphine Cyanide
C(CH 3)3

Group 5: Nicotinic acetylcholine Group 6: Chloride channel activators

Cl
Group 27: Vacant Group 28: Ryanodine receptor modulators
CH (C H 3) 2
Sn CH 3 CH 3
O Group 25: Vacant Group 26: Vacant
receptor allosteric activators O NHC SNHC (CH 3 )3 N
N
C CH 2
CH 3
Sn O Sn CH 2 C
CH 3 OSO2 CH 2 C CH
Cl S O2 Cl

CH (C H 3) 2 N 3 3
Cl
O O
Fenbutatin H
N
Br
I HN
S
Spinosad OCH 3 R
Diafenthiuron Azocyclotin oxide Propargite Tetradifon H3C
O
CH 3O CH3 H
-
C5 C6, R = H
C5 =C6, R = CH3
HO
OCH 3
O
CH 3
O CH 3
H CH 3
CH 3
C H3 H
O
Sn N
N O

N O O
CH 3 O
O O O N O
CH 3
CH 3
H
CH 3
CH 3 OCH3
O
H
R
OH Cl
( CH 3)2 N O
O
CH 3 O O O CH 3 NH2 CH 3
C H3 O HN
CH 3 O
OCH 3 CH 3 O O O Cl CH3 N
12A
O

12D
O O CO 2
O O O

Group 25: Neuronal inhibitors

CH 3 O CH 3 H

12B Organotin 12C

HO H
H R
O CH 3 O CH 3
OH H M ilbem ycin A3: R = -CH 3 C F3
HH O O O

28
O O H O M ilbem ycin A4: R = -CH 2CH3
O O H O OH H CH3 F
(i) R = -CH 2 CH 3 (avermectin B1 a) H
B1a R = CH3 CH 2- OH CF3

Diafenthiuron Cyhexatin Tetradifon Chlorantraniliprole

CH 3CH 2 O O

(unknown mode of action)

Flubendiamide
H CH3

miticides Propargite
HH H O H 5 6 O CH 3 B1 b R = CH 3-
H (ii) R = -CH 3 (avermectin B1b )
R O H
OH
H OH

Diamides
R
spi no syn A, R = H- Emamectin
spi no syn D, R = CH 3 - Spinetoram Abamectin benzoate Milbemectin

5 Spinosyns 6 Avermectins, Milbemycins Group 13: Uncouplers of oxidative Group 14: Nicotinic acetylcholine
phosphorylation via disruption of proton receptor channel blockers Group UN: Compounds of unknown or uncertain mode of action
Group 7: Juvenile hormone mimics gradient
O
C C O 2 CH 3
S CH3
OC H 3 OH SO 2 S CH 2 O O OH O Cl
(CH 3 )2 C (CH 2) 3 CN S C H3 C H3
HO F O O
CH3 CO 2 CH2 C CH O2N CH 3 CH N(CH 3 ) 2 N HNH C OOC H(C H 3 )2 Cl
H C C CH CH2 H Br S O C H 3O F F
CH 3
C C H
CH 3 C C H S O 2 S CH 2 (CH 3)2N CH 3 C O OH
O
OCH 3
3N a Al Cl O Cl
N
CF 3
CH3 CH3 H C H3 CH CH 2 H
H C C
Cl H F F
CH CH2 CH C C CO 2 CH 2 C H 3 CH3 CH 2 CH 2 N O O C H3 OC O F
CH3 CH 2 C H2 CH 2 C C CH 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 CF 3 N O
H H CH3 CH2 OCH 2CH 3 NO 2
CH 3 O
Bensultap H 2 NCOS CH 2 Thiocyclam CH 2 SSO 3Na Azadirachtin O
CH 3 C NOCH 2CH 3 N S Pyridalyl
CH N(CH3 ) 2 .HCl N CH O C O CH3 Bifenazate O
Cryolite OH

Kinoprene Chlorfenapyr DNOC H 2 NCOS CH 2 CH 3 CH 2SSO 3Na Cl C Cl

Hydroprene Methoprene Fenoxycarb Pyriproxyfen CH 3O Cl
CH 3 N S
CC l 3

14 Nereistoxin Cartap
hydrochloride
Thiosultap-
sodium
7A Juvenile hormone analogues 7B Fenoxycarb 7C Pyriproxyfen analogues Benzoximate Chinomethionat Dicofol

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.
• Not all of the current groupings are based on knowledge of a shared target protein. For further information please refer to the
• Provides differentiation between compounds that may bind at the same target site •10A - Clofentezine & Hexythiazox are grouped because they commonly exhibit cross-resistance even though they are structurally
IRAC Mode of Action Classification document.
• 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 are reproduced from the Pesticide Manual 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 responsibility for how this information is used or interpreted Poster Version 2, September 2008. Based on the Mode of Action Classification - Version 6.1