Pdf-moa Structure Poster V1.14

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

CH(CH3) 2

OCO N S O

CH 3 S

C

CH

O

O

CH3 NHCO 2 N

CH3

Methomyl CH3

CH 3

CH3

CH3NHC O

Carbofuran

CH3NCO2N C

SCH 3

O

OCONHCH3

Aldicarb

S

CON(CH3)2

(CH 3)2 NCOC

Cl CONHCONH

Cl

Fenobucarb

S Cl

N

O

N H

Cl

F

F

O

CO 2 CH2 CH3 CH 3

Chlorpyrifos

S

N

CH3S P NHCOCH 3

C

F F

(CH3 O) 2P

Malathion

O

Cl

F

Bistrifluron Cl

Acephate

Diazinon

CH3 NHCOCH2 SP(OCH3) 2

Cl

NHCONHCO

Methamidophos

F

Teflubenzuron

Cl

15 Benzoylureas

Noviflumuron

Group 17: Moulting disruptor, Dipteran

Group 18: Ecdysone receptor agonists

S O

( CH3)3 CSCH2 S P(OCH2CH3) 2 O P OCH 2C H 3 Cl SCH 2 CH 2 CH 3

Br

F O C C NH NH F

F O

Cl CF 3 CHF CF2 O

F

F

Insecticide Resistance Action Committee Terbufos

Profenofos

H2N

S N

The Key to Resistance Management

NC(CH 3 )3

N

N O

N

C (CH 3 )3 CH 3

HN N CH 3 O

NH

Chromafenozide

CH 3

O

Methoxyfenozide

C(CH 3) 3

Cl

O C(CH 3 )3 CH 3

C H 3C H2

HN N

Cyromazine

Buprofezin

NH N C H3 O

C H3 O CH 3

N NH 2

CH(CH 3 )2

O

C(CH 3 )3 C H 3

O

O

Monocrotophos

Cl

Hexaflumuron

Group 16: Chitin biosynthesis inhibitors type 1, Homopteran

Triflumuron

NH CO NHC O

F

NHCO NHCO Cl

Diflubenzuron

OP(OCH3 )2

CONHCH3

Cl

F

Cl F

Lufenuron

F

CH F2 CF2 O

(E )

NH 2

Dimethoate

Flucycloxuron

NHCONHCO

1A Carbamates

N HC ON HC O

C F 3O F

Cl

C

CH3

O CH3 OPSCH 3

N HC ON H CO

Novaluron

F

CF 3CHF CF 2O

F

Parathion-methyl

H C

OP(OCH2CH 3)2

(CH3) 2CH

S

F

C F3 O CH FC F2 O F

F

CH 3

O

N

OCH3

Cl

NH CONH CO F

Flufenoxuron

NH CONH CO

N O

Cl

S O2N

F O

F CH 2

N H

SCH3

Oxamyl

(CH3 O)2 PS CHCH2 CO2 CH2 CH3 Cl

C F3

Chlorfluazuron

O

NOCONHCH 3

S

OP(OCH2CH3 )2

Cl

C F3

Cl

F F F

F

SCH3

Carbaryl

Cl

O

F

SCH2CO2C2H5

Triazamate

SCH3

Thiodicarb

Methiocarb

CHCH2 CH3

CH 3

F

N

N

CH3NCO2N C

Carbosulfan

CH3

N

(CH3)3C

CH3

CH 3NH C O

CH3

CH 3

N

C

O

CH3

OCONHCH3

Benfuracarb

N OC ONHCH 3

SCH3

OCO N S N[(CH 2) 3CH 3] 2

NCH2CH2 CO2 CH2CH3 CH3 CH3

CH 3

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

Mode of Action Classification

CH 3 CH3

HN N O

O

18 Diacylhydrazines

1B Organophosphates

C H3

Halofenozide

Tebufenozide

Group 2: GABA-gated chloride channel antagonists Cl Cl

O

Cl

Cl

Cl

Cl

Cl

Cl

CH 3 CH 2 SO

Cl

Cl

H 2N

SO

Cl

Cl

CN N

Cl

Cl

F3C

Cl

N

O

S

O

Cl

Cl

NH 2

Cl

CF3

O CH 3

CH3

Fipronil

CH 3

N

CH

N

N

CH

C H3

NH

CH 3

NH

N

2A Cyclodiene Organochlorines

2B Phenylpyrazoles (Fiproles)

Group 3: Sodium channel modulators

CH 3

Cl

O

CN

CH3 CH

C

O

C

Cl

O

C O2CH

H

Cl

R

H

Cl

Cypermethrin

Cl

C H3 H

H C CH

F3C

C

CO 2C H 2 C H3

Cl

C CH Cl

CH 3 C O 2

H

H

H

CH 3 H

CH 3

C

CH 3

O

CH

CH 3

CO 2CH

O

CH 3

Borax

8A Alkyl halides

8B Chloropicrin

8C Sulfuryl fluoride

8D Borax

Cl

DDT

C

-

Na B O 10H O

-

+ O 3 O Sb O

-

O

O O

3+ O Sb O-

CH 3 C

CH 2 OCH 2

CH 3

F3C Cl

Br C

CH

Br

CH 3 CO 2 H H

H

C

CN

F

C(CH 3)3

CCl 3

H

CH 3

F

H

Deltamethrin

F

F

F

CH 2

CH3

N

N N

N H

CONHCH 2 CN

Pymetrozine

N

O C NH

Clofentezine

N

F

CH3

N CH 2

N

H

N

N (CH 3) 3C

O

Tebufenpyrad

C(CH 3 )3 N

C H 3 CH 2

Cl

C H 3O

O

O

C

N

CH 3

NH CH 2

Rotenone

CH 3

Cl

O C(C H3 )3

Tolfenpyrad

Pyridaben

O

OCH 3

O N

CH 2S

C

Fenpyroximate

10B Etoxazole

Cl

CO 2 CH 3 O

O

O N

OCF3

21B Rotenone

Group 23: Inhibitors of acetyl CoA carboxylase

N H

N CO 2 CH 3

CH 2

O

O O

2

CH 3 O

CH 3 CH CH 2 3

Metaflumizone

H 3C

O

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

CH 3

O O CH 3 C

CF3

Indoxacarb

H 3C

O

Cl

CF3

N H

NC

22A Indoxacarb

N H

N

S CN

S

H N

O

O

O

N N

CH3 N N NO2 N CH 2

O

Nitenpyram

N

Cl

H N

H

C (C H 3 ) 3

Pyrimidifen

O

H C

Cl

H

N

Cl

O

CH 3 C CH 2

CH 3

Etoxazole

Group 11: Microbial disruptors of insect midgut membranes and derived toxins

Cl

NO2

Clothianidin

Acetamiprid

N

Group 22: Voltage dependent sodium channel blockers

C(CH 3 )3

O

Hexythiazox

10A Clofentezine 10A Hexythiazox

9C Flonicamid

O CH 2 C H 3

F

CH2CH3

N

N

N

CH3

N

CH 2

CH3

Cl

Flonicamid

9B Pymetrozine

S Cl

N N

N

O

NO 2

CH2 N

S

C N CH2 N

20C

CH3

O

H 3C

O

O

Spirotetramat

Spiromesifen

Spirodiclofen

N H

C C

Cl

NH CH 2

CN

CH3

20B

O C NH C H 2

C H 3 CH 2

C H3 (CH 2 ) 2 OCH 2 CH3

N

C H3

21A METI acaricides

O

CH 3NH

20A

O

Cl N N

N

CH 3

3B DDT, Methoxychlor

3A Pyrethroids Pyrethrins

Tefluthrin

NO 2

CH 3 CH CH 3

Cl

CH 3

Cl

CH 2

O

Group 10: Mite growth inhibitors

CF3

CH

Methoxychlor CH 3

Group 4: Nicotinic acetylcholine receptor agonists H N

O

F

F

CO 2CH 2 CH 3

(Z)-(1 R)-cis-

N N

N

CH 3

CH 3 H C CH

N C H3 C H2

N O

C H2 CH 2 O NH

N

N

8E Tartar emetic

OCH 3

Cl F 3C

Cyfluthrin

F

CH 3 CO CH 2 2

H

Etofenprox

O

CH 3

F

C CH

CH

CH 3 O CH 2 O

.3H O 2

Fenazaquin

Group 9: Selective homopteran feeding blockers CH 3 O

CF 3

CH

Fluacrypyrim

Group 21: Mitochondrial complex I electron transport inhibitors .2K+

H

(Z)-(1S)-cis-

Acequinocyl

O

Tartar emetic

O

O

Alphacypermethrin

CN C

Sulfuryl fluoride

CN

H

(R) (1S)-cis -

Cl

Pyrethrins (Pyrethrum)

Lambdacyhalothrin

CH 3CH 2 O O

C

CH CCl3

O

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

Zetacypermethrin

CN

H

C O2

C CH

Cl

CH 3

F3C

Cl Cl

Chloropicrin

Hydramethylnon

CN

CO 2

C CH

CH3

Cl

CN C

H H CH 3 CH 3 H

H

(S ) (1R)-cis -

Cl

(Z )-(1S)-cis -

Bifenthrin

CH 3 C O 2

H

Esfenvalerate

O

C O 2CH

CH

Cl

CH 3

CN

CH3

Cl

Cl3 C NO 2

C

CF 3

O

O

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

CH 3

H C H3

CH3 Br H

C R1

O

Methyl bromide

H CH 2 C

O

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) F3C

(Z)-(1R)-cisC CH C H3 CO 2C H 2

Cl

O H C O

H CH CH 3 CH 3

C

O

H

CH(C H3 )2

CH3 F3C

H

CH 3

CN C

O F S F O

(Only major representatives of group 3A are shown)

O O

O

CH CH

Amitraz

CH 3

(CH 2 ) 11 CH 3

C

CH3

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

C OCH 3

CH N

CH 3

O

CF 3

CH

CF 3

Ethiprole

Endosulfan

Chlordane

Group 20: Mitochondrial complex III electron transport inhibitors (Coupling site II)

Group 19: Octopamine receptor agonists

More information on IRAC and the Mode of Action Classification is available from: www.irac-online.org or [email protected]

CN

N

N

Cl

N N

Imidacloprid

CH 3

N

B.t. aizawai

B.t. israelensis

CH 3

B.t. tenebrionis

Cry1Ac

B.t. Cry3Ab aizawai

Cry2Ab

B. sphaericus

H

N

B.t. kurstaki

Cry1Ab

23 Tetronic & Tetramic acid derivatives

Group 24: Mitochondrial complex IV electron transport inhibitors

mCry3A

Cry1Fa

22B Metaflumizone

Cry34/35Ab1

N

Cry3Bb

Nicotine

Thiamethoxam

CH 2

NO 2

Al PH 3

Ca PH 3

Aluminium Phosphide

Calcium Phosphide

N Cl

Dinotefuran

4A Neonicotinoids

Thiacloprid

Group 12: Inhibitors of mitochondrial ATP synthase

4B Nicotine

Zn PH

CN-

PH 3

3

Zinc Phosphide

24A Phosphine

Phosphine

24B Cyanide

Cyanide

C(CH 3)3

Group 5: Nicotinic acetylcholine receptor allosteric activators

Cl

Group 6: Chloride channel activators

CH (C H 3) 2 O

Spinosad

CH 3CH 2

O

CH 3 HH

O O O

OCH 3 CH 3

O

O

HH

O

O CH 3 CH 3

O

CH 3 O

CH 3 O

H

H

5

O OH

H

6

O

O

H

H

CH 3 O

O CH 3

O HO

H

O

C H3

CH 3 CH 3

Diafenthiuron

CH3

H O O OH

O H

CH3 OH

O

B1 b R = CH 3-

H OH

Emamectin benzoate

H

CH 3 C CH 2 CH 3

N

Sn O Sn

CH 3 CH 2 C CH 3

O

Azocyclotin

Cl

S O2

OSO2 CH 2 C CH 3

3

Cl

Group 25: Vacant

Group 27: Vacant

Group 26: Vacant

Group 28: Ryanodine receptor modulators

Cl

Fenbutatin oxide

Propargite

Sn

R

Tetradifon

H3C

12D Tetradifon

Cl

H N

CH3

12A Diafenthiuron

Cyhexatin

12B Organotin miticides

12C Propargite

H N O CH3

Group 13: Uncouplers of oxidative phosphorylation via disruption of proton gradient

I

HN

N N N

S

O

O O

Cl HN

Group 25: Neuronal inhibitors 28 Flubendiamide (unknown mode of action) Diamides C F3

F CF3

Chlorantraniliprole

Milbemectin

Group 7: Juvenile hormone mimics

O

Br

O

OH

M ilbem ycin A3: R = -CH 3 M ilbem ycin A4: R = -CH 2CH3

6 Avermectins, Milbemycins

5 Spinosyns

N N

O C H3

O H

O

CH 3 OH

Abamectin

Spinetoram

CH 3

OCH3

B1a R = CH3 CH 2-

O (ii) R = -CH 3 (avermectin B1b )

R

CH 3 O CH 3 NH2 CO 2

O H

(i) R = -CH 2 CH 3 (avermectin B1 a)

H

O

H R

H

CH 3 O

H

O O

H R

H

O

O O

spi no syn A, R = Hspi no syn D, R = CH 3 -

O

OCH 3 CH 3

O

O CH 3 O CH 3

R

CH 3O

HO

O

O

CH 3 O

OCH 3

-

C5 C6, R = H C5 =C6, R = CH3

N

( CH 3)2 N

Sn

NHC SNHC (CH 3 )3 CH (C H 3) 2

Group 14: Nicotinic acetylcholine receptor channel blockers

Group UN: Compounds of unknown or uncertain mode of action O

CH3

H

C H3

C C CH2 CH C C H2 CH 2 C CH 2 H H

Hydroprene

CO 2 CH 2 C H 3

CO 2 CH2 C CH3 C C H CH 3 H C C CH CH 2 H CH 2 CH 2 CH CH 2 CH3

CH

CH3

Kinoprene

(CH 3 )2 C (CH 2) 3 CH CH2 H C C H CH 3 H C C CH 3 C O 2 C H(CH 3) 2

Br O

O C H 2C H 2N H C O 2C H 2C H 3

N

O

CH C H 2

Methoprene

7A Juvenile hormone analogues

Fenoxycarb

7B Fenoxycarb

Chlorfenapyr

Pyriproxyfen

• Represent distinct structural classes believed to have the same mode of action • Provides differentiation between compounds that may bind at the same target site • Are structurally different such that risk of metabolic cross-resistance is lower than for close chemical analogs • Are likely to be metabolized by different enzymes - may bind differently enough within the target site that the chance of selection for metabolic/target-site resistance is reduced compared to close analogs. Structures are reproduced from the Pesticide Manual with permission from the British Crop Protection Council

O

7C Pyriproxyfen

Guidance on the use of Sub-Groups:

CN

Cl CF 3 N CH2 OCH 2CH 3

O

CH 3

CH 3

O2N

S

SO 2 S CH 2

OH

OC H 3

CH3 CH CH3

CH

N(CH 3 ) 2

(CH 3)2N

S O 2 S CH 2

NO 2

C

CH3

S S

C H3

C O 2 CH 3 OH O O O C H3

Cl HO C H 3O

O CH 3 C O C H3 OC

H

N HNH C OOC H(C H 3 )2

3N a

O

OH

OCH 3

O

F F

F

Al F

O

Cl

F F

Cl

O

Cl

O N

CF 3

O

Bensultap

DNOC

14 Nereistoxin analogues

H 2 NCOS CH 2 CH N(CH3 ) 2 .HCl H 2 NCOS CH 2

Cartap hydrochloride

Thiocyclam

CH 3 N CH 3

CH 2 SSO 3Na CH CH 2SSO 3Na

Azadirachtin

•1A & 1B - If there are no other alternatives, compounds may be rotated in situations where cross-resistance mechanisms are known to be absent in the insect populations to be treated.

C O C

NOCH 2CH 3 O CH3

CH 3O

Thiosultapsodium

• In the absence of other alternatives, it may be possible to rotate compounds between sub-groups if it is clear that cross resistance mechanisms do not exist in the target populations. • 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.

O

Benzoximate

Cl

N

Bifenazate

S O

CH 3

N

S

Chinomethionat

Cryolite

Pyridalyl

OH Cl

C

Cl

CC l 3

Dicofol

• 3A & 3B - If there are no other alternatives, compounds may be rotated in situations where cross-resistance mechanisms (e.g. kdr) are known to be absent in the insect populations to be treated. DDT is no longer used in agriculture and therefore this is only applicable for the control of human disease vectors such as mosquitoes, because of a lack of alternatives. •10A - Clofentezine & Hexythiazox are grouped because they commonly exhibit cross-resistance even though they are structurally distinct, and the target site for neither compound is known. • 22A & 22B - Although these compounds are believed to have the same target site, they have been sub-grouped because they are chemically distinct, and current evidence indicates that the risk of metabolic cross-resistance is low.

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