insektycydy2009 IRAC MoA poster Nieznany

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Triazamate

Methomyl

Aldicarb

Carbofuran

Carbaryl

Thiodicarb

Benfuracarb

Carbosulfan

Oxamyl

Methiocarb

Fenobucarb

O

CH

3

CH

3

OCONHCH

3

CH

3

NHCO

2

N

C

SCH

3

CH

3

CH

3

CH

3

C

CH

CH

3

S

NOCONHCH

3

OCONHCH

3

CH

3

NCO

2

N C

SCH

3

CH

3

S

CH

3

NCO

2

N C

SCH

3

CH

3

O

OCO

CH

3

CH

3

CH

3

N S

NCH

2

CH

2

CO

2

CH

2

CH

3

CH(CH

3

)

2

O

CH

3

CH

3

OCO

CH

3

N S N[(CH

2

)

3

CH

3

]

2

(CH

3

)

2

NCOC

NOCONHCH

3

SCH

3

O

C

O

CH

3

NH

SCH

3

CH

3

CH

3

O

CHCH

2

CH

3

CH

3

CH

3

NHC

O

1A Carbamates

1B Organophosphates

Chlorpyrifos

Dimethoate

Profenofos

Monocrotophos

Acephate

Malathion

Methamidophos

Terbufos

Parathion-methyl

Diazinon

N

Cl

Cl

Cl

OP(OCH

2

CH

3

)

2

S

CH

3

NHCOCH

2

SP(OCH

3

)

2

S

O

CH

3

SP

OCH

3

NHCOCH

3

S

(CH

3

O)

2

PS

CO

2

CH

2

CH

3

CHCH

2

CO

2

CH

2

CH

3

O

NH

2

CH

3

OPSCH

3

(E )

CONHCH

3

O

(CH

3

O)

2

P

O

H

C

C

CH

3

S

P(OCH

2

CH

3

)

2

(CH

3

)

3

CSCH

2

S

O

2

N

OP(OCH

3

)

2

S

N

N

CH

3

(CH

3

)

2

CH

OP(OCH

2

CH

3

)

2

S

SCH

2

CH

2

CH

3

P

O

Br

Cl

OCH

2

CH

3

O

Group 1: Acetylcholinesterase (AChE) inhibitors

(Only major representatives of the groups are shown)

Group 2: GABA-gated chloride channel antagonists

2B Phenylpyrazoles (Fiproles)

2A Cyclodiene Organochlorines

Cl

Cl

Cl

Cl

Cl

Cl

Cl

Cl

Chlordane

Cl

Cl

Cl

Cl

Cl

Cl

O

SO

O

Endosulfan

F

3

C

N

Cl

Cl

N

CN

S

O

CF

3

NH

2

Fipronil

N

N

Cl

Cl

CF3

H2N

CN

CH3CH2SO

Ethiprole

3A Pyrethroids

Pyrethrins

Deltamethrin

Lambda-

cyhalothrin

Cypermethrin

Bifenthrin

Alpha-

cypermethrin

Esfenvalerate

Tefluthrin

Cyfluthrin

Zeta-

cypermethrin

Etofenprox

CN

O

C

H

CO

2

CH

3

CH

3

C

Br

Br

CH

H

H

(Z)-(1R)-cis -

(Z)-(1S)-cis -

(R)

(S)

CH

3

CH

3

CH

C

C

F

3C

Cl

H

H

O

2

C

CN

O

H

CH

3

C

CH

CH

3

C

F

3C

Cl

H

H

CN

O

2

C

H

O

C

CH

Cl

Cl

CH

3

CH

3

CO

2CH

O

CN

(Z)-(1R)-cis-

(Z)-(1S)-cis-

CH

3

H

2

CO

2C

CH

3

CH

3

CH

C

F

3C

Cl

H

H

CO

2C

CH

C

F

3C

Cl

CH

3

CH

3

H

H

CH

3

H

2

(1R)-cis -

(1S)-cis -

(R)

(S)

CH

3

CH

3

CH

C

C

Cl

Cl

H

H

O

2

C

CN

O

H

CH

3

C

CH

CH

3

C

Cl

Cl

H

H

CN

O

O

2

C

H

O

C

CN

O

C

CH(CH

3)2

Cl

O

H

H

(Z)-(1S)-cis-

(Z)-(1R)-cis-

C CH

F

3C

Cl

CH

3

CH

3

H

H

F

F

F

F

CH

3

CO

2CH2

CH

3

CH

3

CO

2CH2

F

F

F

F

CH

3

H

H

CH

F

3C

Cl

C

O

CH

CN

F

CH

3

CH

3

CH

C

Cl

Cl

CO

2

O

CH

3

CH

3

CO

2CH

CH

C

Cl

Cl

CN

CH

3

CH

2

O

C

CH

3

CH

2

OCH

2

CH

3

O

Pyrethrins

(Pyrethrum)

DDT

Methoxychlor

Cl

CH

CCl

3

Cl

CH

3

O

CH

CCl

3

OCH

3

R = -CH3 (chrysanthemates) or -CO2CH3 (pyrethrates)
R1 = -CH=CH2 (pyrethrin) or -CH3 (cinerin) or -CH2CH3 (jasmolin)

H

CH3 CH3

C

CH

H

O

O H

CH3

O

CH2 C

C

R1

H

H

C

CH3

R

3B DDT,

Methoxychlor

Group 3: Sodium channel modulators

(Only major representatives of group 3A are shown)

4A Neonicotinoids

Acetamiprid

N

C

CH

3

CH

3

N

CN

CH

2

N

Cl

Clothianidin

N

Cl

CH

2

NH

H
N

CH

3

N

S

NO

2

Dinotefuran

O

H
N

H
N

CH

3

N

NO

2

Imidacloprid

N

Cl

CH

2

N

N

N

NO

2

H

Nitenpyram

N

C

CH2CH3

CH3NH

C

NO2

CH2

N

Cl

H

Thiacloprid

S

N

N

Cl

CH

2

N

CN

Thiamethoxam

S

N

CH

2

N

O

N

Cl

N

CH

3

NO

2

Group 4: Nicotinic acetylcholine receptor (nAChR) agonists

4B Nicotine

N

CH

3

N

H

Nicotine

5 Spinosyns

Group 5: Nicotinic acetylcholine

receptor (nAChR) allosteric modulators

Spinosad

O

O

O

CH3

(CH3)2N

CH3

CH3CH2

HH

H H

R

H

O

O

O

O

OCH3

OCH3

CH3

OCH3

spinosyn A, R = H-

spinosyn D, R = CH3-

Spinetoram

Group 6: Chloride channel activators

6 Avermectins, Milbemycins

Abamectin

O

CH3

CH3

CH3

O

O

O

OH

CH3

OH

O

O

H

H

H

OCH3

O

CH3

O

OCH3

HO

O

CH3

CH3

H

H

R

(i) R = -CH2CH3 (avermectin B1a)

(ii) R = -CH3 (avermectin B1b)

Emamectin

benzoate

NH2

CH3

O

O

O

CH3

CH3

O

O

O

OH

CH3

HO

O

H

H

O

CH3

R

CH3

H

O

CH3

CH3

OCH3

CH3O

CO2

B1a R = CH3CH2-

B1b R = CH3-

Milbemectin

CH3

CH3

O

O

CH3

R

O

O

O

CH3

OH

OH

H

H

H

H

Milbemycin A3: R = -CH3
Milbemycin A4: R = -CH2CH3

7A Juvenile hormone analogues

7B Fenoxycarb

7C Pyriproxyfen

C

C

C

C

CH2

CH

CH2

CH2

CH2

CH

CH3

CH3

CH3

CH3

H

H

H

CO2CH2CH3

Hydroprene

Kinoprene

C

C

C

C

CH2

CH

CH2

CH2

CH2

CH

CH3

CH3

CH3

CH3

H

H

H

CO2CH2C CH

Methoprene

Fenoxycarb

Pyriproxyfen

O

OCH

2

CH

2

NHCO

2

CH

2

CH

3

N

O

CH

CH

3

CH

2

O

O

CH

2

C C

C C

CH

3

CO

2

CH(CH

3

)

2

H

H

H

CH

(CH

2

)

3

CH

3

(CH

3

)

2

C

OCH

3

8A Alkyl halides

8B Chloropicrin

8C Sulfuryl fluoride

CH

3

Br

Cl

3

C NO

2

S

O

O

F

F

Chloropicrin

Sulfuryl

fluoride

Methyl

bromide

Tartar emetic

Borax

Na B O 10H O

O

O

Sb

O

O

O

O

O

O

Sb

O

O

O

O

.
2K+ .3H

2O

-

-

-

-

-

-

-

-

3+

3+

8D Borax

8E Tartar emetic

Group 9: Selective homopteran

feeding blockers

9B Pymetrozine

9C Flonicamid

N

CH

N

N

N
H

N

CH3

O

N

CF3

CONHCH2CN

Pymetrozine

Flonicamid

10A Clofentezine

10B Etoxazole

Group 10: Mite growth inhibitors

10A Hexythiazox

Cl

N N

N

N

Cl

N

S

O

Cl

CH3

NH

C

O

CH2CH3

O

C(CH3)3

F

F

O

N

Clofentezine

Hexythiazox

Etoxazole

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

Group 7: Juvenile hormone mimics

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

12C

Propargite

12D

Tetradifon

12B Organotin

miticides

Group 12: Inhibitors of mitochondrial ATP synthase

Diafenthiuron

Azocyclotin

Cyhexatin

Fenbutatin

oxide

Propargite

Tetradifon

O

CH(CH

3

)

2

NHCSNHC(CH

3

)

3

CH(CH

3

)

2

Sn

N

N

N

OH

Sn

C CH2

CH3

CH3

C

CH2

CH3

CH3

Sn O Sn

3

3

C(CH

3

)

3

O

OSO

2

CH

2

C CH

Cl

SO

2

Cl

Cl

Cl

12A

Diafenthiuron

Bensultap

SO

2

S CH

2

CH

CH

2

S

N(CH

3

)

2

SO

2

CH

2

CH

2

H

2

NCOS

CH

H

2

NCOS

N(CH

3

)

2

.HCl

S

S

S

(CH

3

)

2

N

CH

CH

2

SSO

3

Na

CH

2

SSO

3

Na

CH

3

N

CH

3

Thiocyclam

Thiosultap-

sodium

Cartap

hydrochloride

Group 13: Uncouplers of oxidative phos-

phorylation via disruption of proton gradient

Chlorfenapyr

DNOC

N

CH2OCH2CH3

CF3

Br

CN

Cl

O

2

N

OH

CH

3

NO

2

Group 14: Nicotinic acetylcholine

receptor (nAChR) channel blockers

14 Nereistoxin

analogues

Group 16: Inhibitors of

chitin biosynthesis,

type 1

N

N

S

NC(CH

3

)

3

CH(CH

3

)

2

O

Buprofezin

Group 17: Moulting

disruptor, Dipteran

N

N

N

H

2

N

NH

2

NH

Cyromazine

HN N

O

O

C(CH

3

)

3

CH

3

CH

3

CH

3

O

Chromafenozide

CH

3

O

CH

3

NH N

O

O

C(CH

3

)

3

CH

3

CH

3

HN N

O

O

C(CH3)3

Cl

HN N

O

O

C(CH

3

)

3

CH

3

CH

3

CH

3

CH

2

Halofenozide

Methoxyfenozide

Tebufenozide

18 Diacyl-
hydrazines

Group 18: Ecdysone receptor agonists

Group 20: Mitochondrial complex III electron

transport inhibitors

CF

3

CH

CH

C

CH

CH

N

N

NH

NH

CH

3

CH

3

CF

3

CH

3

N

CH

3

CH

CH

CH

3

CH

3

CH

3

N

N

Amitraz

Hydramethylnon

20A

20B

O

O

O

(CH

2

)

11

CH

3

COCH

3

Acequinocyl

C

CH

O

O

O

CH

3

CH

2

O

N

N

CF

3

O

CH

CH

3

CH

3

CH

3

20C

Fluacrypyrim

Fenazaquin

Fenpyroximate

Pyrimidifen

Pyridaben

Tebufenpyrad

Tolfenpyrad

Rotenone

CH

3

O

OCH

3

O

O

O

C

CH

3

CH

2

O

H

H

CH2

C

NH

O

N

N

CH3

CH3CH2

Cl

O

CH3

CH2

C

NH

O

C(CH3)3

N

N

CH3CH2

Cl

CH3

(CH

3

)

3

C

CH

2

S

N

N

Cl

O

C(CH

3

)

3

N

N

CH3CH2

Cl

CH3

CH3

(CH2)2OCH2CH3

CH2

O

NH

CH2

C

O

N

C

N

N

CH

3

O

CH

3

H

O

CH

2

O C(CH

3

)

3

N

N

O

CH2

CH2

C(CH3)3

Group 21: Mitochondrial complex I electron transport inhibitors

21A METI acaricides and insecticides

21B Rotenone

Indoxacarb

O

N N

N

O

CO

2

CH

3

CO

2

CH

3

Cl

OCF

3

Group 23: Inhibitors of acetyl

CoA carboxylase

Metaflumizone

22A Indoxacarb

22B Metaflumizone

23 Tetronic & Tetramic acid derivatives

Spirodiclofen

Spiromesifen

C

CH2

C(CH3)3

O

O

O

O

CH3

CH3

CH3

O

O

O

C

O

Cl

Cl

CH3 CH

2CH3

CH3

Group 24: Mitochondrial complex IV electron transport inhibitors

24A

Phosphine

Aluminium
Phosphide

24B Cyanide

Cyanide

CN-

PH

3

Calcium

Phosphide

Zinc

Phosphide

Phosphine

Al PH

3

Zn PH

3

Ca PH

3

O

OH

CO

2

CH

3

O

O

CH

3

OC

O

O

OH

C

CH

3

CH

3

O

CH

3

O

O

O

HO

CH3

H

O

CH

3

C

Azadirachtin

Pyridalyl

Dicofol

Chinomethionat

Benzoximate

O

O

O

N

Cl

Cl

CF

3

Cl

Cl

Cl

C

OH

CCl3

Cl

N

N

S

S

O

CH

3

C

C

NOCH2CH3

OCH3

Cl

CH3O

O

O

Bifenazate

NHNH

OCH

3

COOCH(CH

3

)

2

Al

F

F

F

F

F

F

3Na

Cryolite

Group UN: Compounds of unknown or uncertain mode of action

15 Benzoylureas

Group 15: Inhibitors of chitin biosynthesis, type 0

Flucycloxuron

Flufenoxuron

Hexaflumuron

Lufenuron

Novaluron

Noviflumuron

Teflubenzuron

Triflumuron

CH2

F

F

NHCONHCO

O

N

C

Cl

F

F

F

NHCONHCO

O

CF3

Cl

Cl

F

F

NHCONHCO

Cl

CHF

2

CF

2

O

Cl

CF

3

CHFCF

2

O

Cl

F

F

NHCONHCO

Cl

CF3OCHFCF2O

F

F

NHCONHCO

NH

C

O

NH

C

O

F

F

CF

3

CHFCF

2

O

F

Cl

Cl

Cl

F

F

F

F

NHCONHCO

Cl

NHCONHCO

Cl

CF

3

O

Chlorfluazuron

Diflubenzuron

Cl

F

F

NHCONHCO

CONHCONH

F

F

O

N

CF

3

Cl

Cl

Cl

Bistrifluron

Group 19: Octopamine

receptor agonists

Mode of Action Classification

Insecticide Resistance Action Committee

The Key to Resistance Management

Guidance on the use of Sub-Groups:

• 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.

• 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.

• 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.

•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.

More information on IRAC 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

Poster Version 2.5, July 2009. Based on the Mode of Action Classification - Version 6.3

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

N

CF

3

N

H

N

H

O

O

CF

3

NC

N

H

O

O

N

H

F

F

Cl

F

F

F

F F

F

B.t.

israelensis

B.t.

aizawai

B.t.

aizawai

B.

sphaericus

B.t.

kurstaki

B.t.

tenebrionis

Cry1Ab

Cry1Ac

Cry1Fa

Cry2Ab

mCry3A

Cry3Ab

Cry3Bb

Cry34/35Ab1

Spirotetramat

N

H

O

O

O

O

CH

2

C

H

3

O

C

H

3

C

H

3

CH

3

O

O

O

O

O

N

O

O

O

O

O

H

H

H

H

H

R

5

6

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

-

=

Group 22: Voltage-dependent

sodium channel blockers

N

N

N

(CH

3

)

3

C

CON(CH

3

)

2

SCH

2

CO

2

C

2

H

5

13 Pyrroles, Dinitrophenols

16 Buprofezin

17 Cryomazine

19 Amitraz

25 Cyenopyrafen

Group 25: Mitochondrial

complex II electron
transport inhibitors

Cyenopyrafen

Cyflumetofen

Group 28: Ryanodine

receptor modulators

Chlorantraniliprole

28

Diamides

N

H

CH

3

O

Cl

O

N

N

N

Cl

Br

N

H

C

H

3

S

O

O

I

O

N

H

N

H

O

CF

3

CF

3

F

Flubendiamide

CF

3

C

C

O

NC

C(CH

3

)

3

O

O

H

2

C

CH

2

O

CH

3

C

C

CN

C(CH

3

)

3

N

N

O

H

3

C

CH

3

H

3

C

C(CH

3

)

3

O


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