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Certified Crop Science Consultant Program

Appendix 3-E

Herbicide, Insecticide, and Fungicide Groups Based on Mode of Action

Table 3E-1. Groups Based on Mode of Action

Group Mode of Action Chemical Family Active Ingredient 1 Inhibitors of acetyl CoA Aryloxyphenoxy propionate clodinafop-propargyl, cyhalofop-butyl, carboxylase (ACCase) ‘FOPs’ diclofop-methyl, fenoxaprop-P-ethyl, -P-butyl, haloxyfop-R-methyl, propaquizafop, quizalofop-P-ethyl

Cyclohexanedione alloxydim, butroxydim, clethodim, ‘DIMs’ cyclosydim, profoxydim, , tepraloxydim, tralkoxydim 2 Inhibit acetolactate synthase Sulfonylureas amidosulfuron, azimsulfuron, (ALS) also called bensulfuron-methyl, chlorimuron-ethyl, acetohydroxy-acid synthase chlorsulfuron, cinosulfuron, (AHAS) cyclosulfamuron, ethametsulfuron-methyl, ethoxysulfuron, , flupyrsulfuron-methyl-Na, foramsulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, mesosulfuron, metsulfuron- methyl, nicosulfuron, oxasulfuron, primisulfuron-methyl, prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron-methyl, tritosulfuron Imidazoilinone , imazamethabenz-methyl, imazamox, , imazaquin, imazethapyr Triazolopyrimidines cloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam Pyrimidinyl(thio)benzoates bispyribac-Na, , pyriftalid, pyrithiobac-Na, pyriminobac-methyl Sulfonylaminocarbonyl- flucarbazone-Na, procarbazone-Na triazolinones Certified Crop Science Consultant 2

Table 3E-1. Herbicide Groups Based on Mode of Action

Group Mode of Action Chemical Family Active Ingredient 3 Inhibit microtubule assembly Dinitroanilines benefin = butralin dinitramine ethalfluralin oryzalin

Phosphoroamidates amiprophos-methyl, butamiphos , thiazopyr Benzamides propyzamide = pronamide tebutam Benzoic acids DCPA = chlorthal-dimethyl 4 Synthetic (mimic Phenoxy-carboxylic-acids clomeprop, 2,4-D, 2,4-DB, = IAA) 2,4-DP, MCPA, MCPB, = MCPP = CMPP Benzoic acids , , TBA , , , carboxylic acids Quinoline carboxylic acids , quinmerac Others benazolin-ethyl 5 Inhibit photosynthesis Triazines ametryne, , , at photosystem II desmetryne, dimethametryne, , Site A prometryne, propazine, , simetryne, terbumeton, , terbutryne, trietazine Triazinones , metamitron,

Triazolinone amicarbazone

Uracils bromacil. lenacil, terbacil

Pyridazinones pyrazon = chloridazon

Phenyl-carbamates desmedipham, phenmedipham

6 Similar to Group 5 Nitriles bromofenoxim, , but different binding behavior ioxynil

Benzothiadiazinone

Phenyl-pyridazines pyridate, pyridafol Certified Crop Science Consultant 3

Table 3E-1. Herbicide Groups Based on Mode of Action

Group Mode of Action Chemical Family Active Ingredient 7 Inhibit photosynthesis at chlorobromuron, chlorotoluron, photosystem II Site B , dimefuron, diuron, ethidimuron, fenuron, fluometuron, isoproturon, isouron, , methabenzthiazuron, metobromuron, metoxuron, , neburon, siduron,

Amides , pentanochlor

8 Inhibit lipid synthesis (not Thiocarbamates butylate, cycloate, dimepiperate, EPTC, ACCase inhibition) esprocarb, molinate, orbencarb, pebulate, prosulfocarb, thiobencarb = benthiocarb, tiocarbazil, triallate, vernolate

Phosphorodithioates

Benzofuranes benfuresate, ethofumesate

Unknown Pyrazolium difenzoquat

9 Inhibit EPSP Glycines , sulfosate synthase

10 Inhibit glutamine Phosphinic acids -ammonium, = synthetase bilanaphos

11 Bleaching: Inhibit carotenoid Triazoles amitrole biosynthesis (unknown target)

12 Bleaching: Inhibit carotenoid Pyridazinones norflurozon synthesis at phytoene desaturase step (PDS) Pyridinecarboxamides diflufenican, picolinafen

Other beflubutamid, fluridone, flurochloridone, flurtamone

13 Bleaching: Inhibit ditrepenes Isoxazolidinone

Ureas fluometuron

Diphenylether

14 Inhibit protoporphyrinogen Diphenylethers acifluorfen-Na, , chlomethoxyfen, oxidase (PPO) fluoroglycofen-ethyl, , halosafen, , oxyfluorfen

Phenylpyrazoles fluazolate, pyraflufen-ethyl

N-phenylphthalimides cinidon-ethyl, flumioxazin, flumiclorac-pentyl

Thiadiazoles fluthiacet-methyl, thidiazimin

Oxadiazoles oxadiazon, oxadiargyl Certified Crop Science Consultant 4

Table 3E-1. Herbicide Groups Based on Mode of Action

Group Mode of Action Chemical Family Active Ingredient Triazolinones azafenidin, carfentrazone-ethyl,

Oxazolidinediones pentoxazone

Pyrimidindiones benzfendizone,

Others pyrazogyl, profluazol, flufenpyr

15 Inhibition of the synthesis of Chloroacetamides , , , very long chain fatty acids dimethachlor, dimethanamid, (VLCFAs) = inhibition of cell metazachlor, , pethoxamid, division pretilachlor, , propisochlor, thenylchlor

Acetamides diphenamid, napropamide, naproanilide

Oxyacetamides flufenacet, mefenacet

Tetrazolinones fentrazamide

Others anilofos, cafenstrole, piperophos

17 Unknown Organoarsenical (MSMA), DSMA

18 Inhibit DHP (dihydropteroate Carbamates ) synthase

19 Inhibit action of Phthalamates naptalam transport Semicarbazones diflufenzopyr-Na

20 Inhibit cell wall (cellulose) Nitriles dichlobenil, chlorthiamid synthesis

21 Inhibit cell wall (cellulose) Benzamide isoxaben synthesis Triazolocarboxamides flupoxam

22 Photosystem I-electron Bipyridyliums , diverters

23 Inhibit mitosis Carbamates chlorpropham, propham, carbetamide

24 Uncoupling membrane Dinitrophenols , dinoterb, DNOC disruptors

25 Unknown Arylaminopropionic flamprop-M-methyl

26 Inhibition of lipid synthesis – Chloro-Carbonic-acids TCA, dalapon, flupropanate not ACCase inhibition Certified Crop Science Consultant 5

Table 3E-1. Herbicide Groups Based on Mode of Action

Group Mode of Action Chemical Family Active Ingredient 27 Unknown Others bromobutide (chloro)-flurenol, cinmethylin, cumyluron, dazomet, dymron = daimuron methyl-dimuron = methyl- dymron, etobenzanid, fosamine, indanofan, metam, oxaziclomefone, oleic acid, pelargonic acid, pyributicarb

28 Bleaching: Inhibition of 4- Triketones , sulcotrione hydroxyphenyl-pyruvate- dioxygenase (4-HPPD) Isoxazoles isoxachlortole, isozaflutole

Pyrazoles benzofenap, pyrazolynate, pyrazoxyfen

Others benzobicyclon

Table 3E-2. Insecticide Groups Based on Mode of Action Group Mode of Action Chemical Group Active Ingredient 1 Inhibition of the enzyme Carbamates aldicarb, aminocarb, bendiocarb, acetylcholinesterase, carbaryl, carbofuran, formetanate, interrupting the methiocarb, methomyl, oxamyl, transmission of nerve pirimicarb, propoxur impulses Organo-phosphates acephate, azamethiphos, azinphos- methyl, chlorfenvinphos, chlorpyrifos, coumaphos, diazinon, dichlorvos/DDVP, dimethoate, disulfoton, ethion, fenitrothion, fensulfothion, fenthion, fonofos, malathion, methamidophos, methidathion, naled, oxydementon- methyl, parathion, phorate, phosalone, phosmet, pyrazophos, sulfotep, temephos, terbufos, tetrachlor- vinphos, trichlorphon

2 Interferes with the Organo-chlorines chlordecone, dicofol, dienochlor, transmission of the nerve endosulfan, lindane, methoxychlor impulse down the axon, leading to repetitive nervous discharges (e.g., DTT analogues) or causes excessive release of acetylcholine which leads to repetitive nervous discharges (e.g., lindane)

Certified Crop Science Consultant 6

Table 3E-2. Insecticide Groups Based on Mode of Action Group Mode of Action Chemical Group Active Ingredient 3 Acts as an axonic poison Synthetic Pyrethroids d-trans allethrin, allethrin, cyfluthrin, on both the peripheral and cypermethrin, deltamethrin, central nervous system fenvalerate, flucythrinate, fluvalinate- stimulating repetitive tau, permethrin, resmethrin, tefluthrin, nervous discharges, Pyrethrins tetramethrin, leading to paralysis Pyrethrins

4 Binds to nicotinic Chloronicotines Imidacloprid acetylcholine receptor, (nitroguanidines) disrupting nerve Nicotine nicotine transmission 5 Interferes with the GABA Avermectin ambamectin nerve receptor of insects

6 Juvenile hormone juvenile hormones which methoprene analogues prevent moulting from the larval to the adult stage

7 Unknown Fumigant methyl bromide

8 Unknown Fumigant aluminum phosphide

9 Organism has protein Microbial basillus thuringiensis var. kurstaki inclusions that are released in the gut of the target pest resulting in gut paralysis and a cessation of feeding

10 Inhibition of oxidative Organotin Miticides fenbutatin oxide phosphorylation at the site of dinitrophenol uncoupling, disrupting formation of ATP

11 Inhibit magnesium- Sulfite Ester Miticides propargite stimulated ATPase.

12 Unknown Tetrazine Ovicidal clofentezine Miticide

13 A2-adrenergic receptor Triazapentadiene amitraz agonist

14 IGR: interferes with Substituted benzoylurea diflubenzuron deposition of chitin.

Benzoic acid hydrazide tebufenozide Certified Crop Science Consultant 7

Table 3E-2. Insecticide Groups Based on Mode of Action Group Mode of Action Chemical Group Active Ingredient 15 IGR: interferes with Triazine cyromazine moulting process

16 Blocks ATP synthesis in ? Hydramethylnon mitochondria of insect cells.

17 Blocks electron transport Botanical rotenone in respiration

Table 3E-3. Fungicide Groups Based on Mode of Action Group Mode of Action Chemical Family Active Ingredient 1 Inhibit tubulin formation Benzimadazole benomyl, carbendazim, thiabendazole thiophanate-methyl 2 Affect cell division, Dicarboximide iprodione, vinclozolin RNA & DNA synthesis, and metabolism 3 DMI: Inhibition of sterol Morpholine Dodemorph synthesis Piperazine Triforine Triazole myclobutanil, propiconazole

4 Affect RNA synthesis Phenylamide metalaxyl 5 Affect mitochondrial Carboximide carbathiin, oxycarboxin transport chain M Multi-site activity Inorganic copper (hydroxide), copper (oxychloride) copper (sulphate), sulphur (wettable) mancozeb, maneb, metiram, zineb ethylenebis- ferbam, thiram ziram dithiocarbamates

Dialkyl-dithiocarbamate captan,chlorothalonil, folpet Phthalimide chloroneb, quintozene dichlone, dichloran Chlorophenyl Quinone Unspecified Carbamate propamocarb Certified Crop Science Consultant 8

Table 3E-3. Fungicide Groups Based on Mode of Action Group Mode of Action Chemical Family Active Ingredient Cinnamic acid Dimethomorph Guanidine Dodine Organic phosphorus fosetyl-aluminum Organophosphate dinocap Quinoxaline chinomethionat (oxythiquinox)

etridiazole

Thiadiazole anilazine Triazine