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The World of Herbicides According to HRAC classification on mode of action 2010 HERBICIDES AFFECTING: Light Processes Cell Metabolism Growth/Cell Division C2 C3 C1 C Inhibition ofphotosynthesis at PS II B Inhibition of ALS (branched)chain amino acid synth.) K1 Inhibition of microtubule assembly K2 Inhibition of microtubule organisation M Uncoupler (membrane disruption) E Inhibition ofprotoporphyrinogen oxidase D PS-I-electron diversion F Inhibition of pigmentsynthesis (bleaching) N Lipid synthesis inhibition(not ACCase) A Lipid synthesis inhibition(inhibition of ACCase) K3 Inhibition of cell division (inhibition of VLCFAs) L Inhibition ofcellulose synthesis F1 Inhibition of PDS F4 Inhibition of DOXP synthase F3 Unknown target F2 Inhibition of4-HPPD I DHP-inhibition Z Unknown modeof action O Synthetic Auxins P Auxin transportinhibition H Glutamine synthetase inhibition G Inhibition ofEPSP synthase Phenyl-pyridazines Diphenyl ethers Thiadiazoles Diphenylether Pyrimidinediones Cyclohexanediones (DIMs) Chlorocarb. acids Others Glycines Others Others Ureas Uracils Amides Triazolinone Triazines Phenylpyrazoles Imidazolinones Triazolopyrimidines Chloroacetamides Pyridine-carboxylic acids Benzoic acids Phenoxy-carboxylic acids Tetrazolinones Acetamides Semicarbazone Phthalamate Benzamide Alkylazines Nitriles Pyridines Phosphoroamidates Dinitrophenols Bipyridyliums Phosphorodithioate Benzofuranes Quinolinecarboxylic acids Phosphinic acids Carbamate Sulfonylamino-carbonyl -triazolinones Sulfonylureas Pyrimidinyl (thio) benzoates Oxadiazoles Triazinones Triazolinones Pyridazinone Nitriles Phenylcarbamates N-Phenyl-phthalimides Oxazolidinedione Benzothiadiazinone Benzoic acid Carbamates Dinitroanilines Benzamides Oxyacetamides Aryloxyphenoxy- propionates (FOPs) www.hracglobal.com Thiocarbamates Phenylpyrazoline (DEN) Arylaminopropionic acid Triazolocarboxamide O O N H Cl Cl Clomeprop O OH O Cl Cl Dichlorprop=2,4-DP O OH O Cl Cl 2,4-D O OH OCl MCPA O Cl Cl OH O 2,4-DB OCl OH O MCPB OCl OH O Mecoprop = MCPP = CMPP FF N N N O NH2 Cl O F F F Flupoxam NCl Cl Cl O OH O Triclopyr NCl Cl O OH Clopyralid NF Cl Cl O OH O NH2 Fluroxypyr NCl Cl Cl NH2 O OH Picloram NCl Cl NH2 O OH Aminopyralid N H NO O O O Isoxaben Cl Cl NH2 OHO Chloramben OHO O Cl Cl Dicamba OHO Cl Cl Cl TBA Cl Cl CN Dichlobenil Cl Cl SNH2 Chlorthiamid N H O OH O Naptalam N OOH Cl Quinmerac N Cl OOH Cl Quinclorac O O N NN H N H O F F Na Diflufenzopyr-sodium N S O Cl O O Benazolin-ethyl + N N N NH2 F N H O Triaziflam Indaziflam N N N NH2 F CH3 CH3 N H CH3 N N N NH N H S Desmetryne N N N Cl N H N H Propazine N N N NH N H S Ametryne N N N N H N H Cl Atrazine N N N NH S N H Dimethametryn N N N N H N H Cl Simazine N N N N H N H Cl Terbuthylazine N N N N H N H S Terbutryne N N N N H N H S SimetryneN N N N H N H O PrometonN N N N H N H Cl CN Cyanazine N N N N H N H S Prometryne N N N N H N H O Terbumeton N N N N NH Cl Trietazine N H N O Fenuron S N N N HO Methabenzthiazuron N H Cl N O Chlorotoluron N H O N O Cl Chloroxuron N H N O F F F Fluometuron (also F3) Cl Cl N H N O Neburon N H N Cl N O O N O Dimefuron N H N O Isoproturon O Cl N H O N Metoxuron N H N H O Siduron N H Cl Cl N O Diuron N O N H N O Isouron Cl N H N O O Monolinuron N N S N O N H Tebuthiuron Br Cl N H N O O Chlorobromuron S NN NS O O N H O Ethidimuron Cl Cl N H N O O Linuron N S N H O O O Bentazone N N H O Br O Bromacil N N H O O Lenacil N N H O Cl O Terbacil N H O N H O O O Phenmedipham N NCl O O S Pyridate N N OH Cl Pyridafol N N OCl NH2 Chloridazon/Pyrazon N N NN O O Hexazinone N NN O NH2 Metamitron N N N O NH2 S Metribuzin N N N O NH2 O N H Amicarbazone N + N + Br Br N + N + Cl Cl Diquat Paraquat Cl Cl N H O Propanil Cl N H O Pentanochlor Br OH Br N O NO2 O2N Bromofenoxim (also M) I OH I CN Ioxynil (also M) Br OH Br CN Bromoxynil (also M) O N HO O N H O Desmedipham Br N H O N O Metobromuron O N NH O F F F F Picolinafen N O F F F Fluridone N N OCl N H F F F NorflurazonN O Cl Cl F F F Flurochloridone O ClNH2 O2N Aclonifen N H N O F F F Fluometuron (also C) NO Cl O Clomazone O N O Cl S O O Isoxachlortole N N OO Cl Cl O Pyrazoxyfen N N OOH S F F F O O Pyrasulfotole O O O Cl S O O O O Tefuryltrione O N H O F F F Flurtamone ON O N H F F F F F Diflufenican Beflubutamid F F F F O O N H Isoxaflutole O N O F F F S O O Benzofenap N N O O O Cl Cl Pyrazolynate N N O S O O Cl Cl O Sulcotrione ClOO O O S O O Mesotrione O O O N+ O O S O O Benzobicyclon S O Cl S O O Tembotrione O O O Cl O F F F S O O Topramezone O N N OH ON S OO O OH O N F F F O O Bicyclopyrone Amitrole (Inh. of lycopene cyclase) N H N N NH 2 N H O N H Dymron = Daimuron N H N O Methyldymron N H N H OCl Cumyluron OH O Pelargonic acid N N S S Dazomet (CH2)7CO2H (CH2)7CH3 Oleic Acid O N Cl Cl O Oxaziclomefone NH 2 P O O O OH Fosamine Cl Cl N H O OO Etobenzanid O O Cinmethylin N NO S O Pyributicarb DSMA As O O O Na+ Na+ MSMA As O OH O Na +Metam S S N H Na + Bromobutide N H O Br Difenzoquat Metilsulfate N N +CH3SO - 4 Indanofan O O O Cl Chlorflurenol OH OH O Cl N N O O N H N H OS O O N S O O Amidosulfuron N N O O N H N H OS O O N N N NN N Azimsulfuron N N O O N H N H OS O O O O Bensulfuron-methyl N N O N H N H OS O O O O Cl Chlorimuron-ethyl N N N O N H N H OS O O Cl Chlorsulfuron N N N O O N H N H OS O O O O Cinosulfuron N N O O N H N OS O O N O F F F Na+ Trifloxysulfuron-sodium N N O O N H N H OS O O N HO Cyclosulfamuron N N N O N H N H N H OS O O O O Ethametsulfuron-methyl N N O O N H N H OS O O O O Ethoxysulfuron N N O O N H N H OS O O N F F F Flazasulfuron N N O O N H N OS O O N O O F F F Na+ Flupyrsulfuron -methyl-sodium N N O O N H N H OS O O N N Cl OO Halosulfuron-methyl N N N O O N H N H OS O O N Cl Imazosulfuron N N N O N H N OS O O I O O Na+ Iodosulfuron -methyl-sodium N N N O N H N H OS O O O O Metsulfuron-methyl N N O O N H N H OS O O N H O N O H Foramsulfuron N N O O N H N H OS O O N O N Nicosulfuron N N N H N H OS O O O OO Oxasulfuron N N O O N H N H OS O O O F F F F O Primisulfuron-methyl N N N O N H N H OS O O F F F Prosulfuron N N O O N H N H OS O O O O N H S O O Mesosulfuron-methyl N N O O N H N H OS O O N N OO Pyrazosulfuron-ethyl N N O O N H N H OS O O N S O O Rimsulfuron N N N H N H OS O O O O Sulfometuron-methyl N N O O N H N H OS O O N N S O O Sulfosulfuron N N N O N H N H OS O O F F F F F F Tritosulfuron N N N O N H N H OS O O S O O Thifensulfuron-methyl N N N O N H N H OS O O O Cl Triasulfuron N N N O N N H OS O O O O Tribenuron-methyl N N N O N H N H OS O O O N O FF F Triflusulfuron-methyl N N O O N H N H OS O O O O N O F Flucetosulfuron N N O O N H N H OS O O N HN O Orthosulfamuron N H N O N OOH Imazapic N H N O N OOH Imazapyr N H N O OO N H N O OO + Imazamethabenz-methyl N H N O N OOH Imazaquin N H N O N OOH O Imazamox N H N O N OOH Imazethapyr OH NO2 NO2 DNOC OH NO2 NO2 Dinoterb OH NO2 NO2 Dinoseb O ON N N N O O O O O O Na + Bispyribac-sodium O ON N N N O O O O O O N Pyribenzoxim S N N O O O O Cl Na+ Pyrithiobac-sodium S N N O O O OPyriftalid O N N O O O O N O Pyriminobac-methyl NH N N O O OH O S OO F F Pyrimisulfan S NO O O N N N O O O O Na+ O S NO O O N N N O O F F F Na+ Flucarbazone-sodium Propoxycarbazone-sodium S S N H N O N N O O O O O O Thiencarbazone-methyl N N NN S N H Cl O O O O F O Cloransulam-methyl N N NN S N H Cl Cl O O F O Diclosulam N N NN S N H F F O O O F Florasulam N N NN S N H F F O O Flumetsulam N N NN S N H Cl Cl O O O O Metosulam N N NN N H S O O O O O F F F F F Penoxsulam N N NN N H S N O O O O O F F F Pyroxsulam OH P N H OH O O OH Glyphosate OH P N H OH O O O (CH3)3 S+ Sulfosate P OH O O NH2 O NH4 + Glufosinate-ammonium NH2 S N H O O O O Asulam Propyrisulfuron N N S N H N HO N NN Cl O OO O Bialaphos CH3 P O OH NH2 H N H O CH3 H N H O CH3 H O OH S N H S P O O S OO Bensulide S N O Tiocarbazil S N O Cl Thiobencarb = Benthiocarb S N O Esprocarb S N O Cycloate S N O EPTCNS O Dimepiperate N S O Molinate S N OCl Orbencarb S N O Pebulate S N O Prosulfocarb S N O Vernolate S N O Cl Cl Cl Tri-allate OH O Cl Cl Cl TCA OH O ClCl Dalapon OH O FF F F Flupropanate O O O O N O Alloxydim O O O N O Butroxydim Clethodim O OS N O Cl Cycloxydim O O N O S Sethoxydim O O N O S Profoxydim S O O N O O Cl Tepraloxydim O O O N O Cl Pinoxaden O N N O O O Tralkoxydim O O N O Cyhalofop-butyl O F N O O O CH3 H Diclofop-methyl Cl Cl O O O O Fluazifop-P-butyl N F F F O O O O CH3 H Fenoxaprop-P-ethyl Cl O N O O O O CH3H Metamifop O N Cl O O O N FCH3 Haloxyfop-P-methyl N F F F Cl O O O O CH3 Propaquizafop N N O Cl O CH3 O OO N Quizalofop-P-methyl N N O Cl O O O CH3 Quizalofop-P-tefuryl N N O Cl O O CH3OO Ethofumesate O O O S O OBenfuresate O OS O O Butylate S N O Clodinafop-propargyl N Cl F O O O O CH3 N Cl O Cl N O O Oxadiazon O Cl Cl N ON O Oxadiargyl N N O O O O O O F F F Benzfendizone Cl O N F O O O Pentoxazone N N F H O O F Cl N H S Cl O O Profluazol N N O F O Cl O O F F F Flufenpyr-ethyl S N N N O N O F Thidiazimin N ClF O Cl ON N O F F Carfentrazone-ethyl N N N O Cl Cl O Azafenidin N Cl O O Cl O O Cinidon-ethyl N O Cl O O F O O Flumiclorac-pentyl N O O F N O O Flumioxazin O Cl F F F OO N+ O ONa+ Acifluorfen-sodium O Cl Cl OO N + O O Bifenox O Cl F F F N + O O OO O O Fluoroglycofen-ethyl O Cl Cl O N + O O Chlomethoxyfen O F F F O N+ O O N H S O O Cl Fomesafen O F F F F Cl N H O S O O N+ O O Halosafen O Cl F F F N + O O OO O O Lactofen O Cl F F F O N + O O Oxyfluorfen O F F F Cl O O CH3 H O OCl Ethoxyfen-ethyl N N O O F F F Cl O O O O Butafenacil NN N N Cl CN N Pyraclonil N F Cl S O O N N S O Fluthiacet-methyl ClCl N N NN H S O O O F F Sulfentrazone N N FCl O O F F F Br Fluazolate N N FCl O O Cl F FO O Pyraflufen-ethyl Bencarbazone N N N O F FF F NH NH2 S S O O Saflufenacil N N O OF F F F Cl O N H S N O O N O Cl O Acetochlor N O Cl O Alachlor N O Cl Propachlor N O Cl O Butachlor N O Cl O Dimethachlor N O Cl S O Thenylchlor S N O Cl O Dimethenamid N O Cl N N Metazachlor N O Cl O Metolachlor N O Cl O Pretilachlor N O Cl O Propisochlor N O Cl O Pethoxamid Cl Cl ClCl O OO O Chlorthal-dimethyl = DCPA N NO2 NO2 SNH2 O O N NO2 NO2 F F F Ethalfluralin N H NO2 NO2 Pendimethalin N H NO2 NO2 Butralin Oryzalin N NO2 NO2 F F F Trifluralin N NO2 NO2 F F F NH2 Dinitramine N H O O Cl Chlorpropham N H O O Propham N NO2 NO2 F F F Benefin = Benfluralin S P N H O O NO2 S P N H O O NO2 Amiprofos-methyl Butamifos N H O Cl Cl Propyzamide = Pronamide N O Tebutam P S OS O N O Cl Anilofos N P S OS O O Piperophos S O O N N N N O Cafenstrole O N H O Naproanilide N O Diphenamid N S O S O F F F F F Dithiopyr N O O F F F F F S N Thiazopyr O N NN S O F F F F Flufenacet O N N S O Mefenacet N N NN N OO Cl Fentrazamide Carbetamide N H O O N H O H Napropamide O O N SN N ON OO O FF FF F Pyroxasulfone Ipfencarbazone F F N O O N N N CI CI Flamprop-m N Cl F C H3O H O O H A (1) Lipid synthesis inhibition (inh. of ACCase) B (2) Inhibition of ALS (branched chain amino acid synthesis) C (5, 6, 7) Inhibition of photosynthesis PS II D (22) PS I electron diversion E (14) Inhibition of protoporphyrinogen oxidase F Inhibition of pigment synthesis (bleaching) F1 (12) Inhibition of PDS F2 (27) Inhibition of 4-HPPD F3 (11, 13) Unknown target F4 Inhibition of DOXP synthase G (9) Inhibition of EPSP synthase H (10) Inhibiton of glutamine synthetase I (18) Inhibition of DHP K1 (3) Inhibition of microtubule assembly K2 (23) Inhibition of microtubule organisation K3 (15) Inhibition of cell division (VLCFA) L (20, 21) Inhibition of cellulose synthesis M (24) Uncoupler of oxidative phosphorylation N (8, 26) Inhibition of lipid synthesis (not ACCase) O (4) Synthetic auxin P (19) Auxin transport inhibition Z (17, 25,) Unknown mode of action ( ) WSSA Group A free copy of this poster can be downloaded from www.hracglobal.com Designed and produced by Syngenta 2010