214 24-D

'
Herbicide

2,4-0

HO,
CH-CH3
CH2
HO NH!..cH2
CH·CHz CH-CH 3
CH; .Hd

2,4-0-triisopropanotammonium
NOMENCLATURE: 2.4-0
Common name 2.1-0 {SS. E-ISO, (m) F-ISO. WSSA): 2.<1-PA (JMAF)
IUPAC 03me (2.4-dicNon>phenox)acctK acid
O.emr::.l AbstnCIS name (2.1-<ktlloropi>enoxy)acedc add
CAS l\N {9~75-7] EC no. 202-361-1 Development code< L208 (Mor1<s)
2. 4 .{).<,u[Ofy/
IUPAC name 2-butoxyethyl (2,4-<llchlorophenoxy)acetare
CAS RN {1 929 71-3] EC no. 217-680-1
2....~
IUPAC name O<Jty' (2.'1-<ilchloropnenoxy)acetate
CAS RN (94-80-4} EC no. 202-364-8
ot' l.4~
IU'AC name dimechylammonium (2.~ute
CAS RN (2008-39-1] EC no. 217-91.>-6
2,4..Q.dioloml~ (2,4-D-<iierhanolanvnonium)
IUPAC n:amo bis(2-h)'droxyeltlyr)ammon1um (2.4-dlchlorophenoxy)acetate
CAS RN (5741-19-8] EC no. 227-256-S
l.4-~thyl
IUPAC name ethyl (2.'1-<lichlorophenoxy)u:etate
\• 2. +C>-2-t<J1)'/hexyl
IUPAC 03me 2-ethyl>ex'/I (2.1-dichlorophelloxy)ace<ate
~names 2.1-D 2-&IE CAS l\N (1928-43-4/ EC no. 217-673-3
. o....clopmetl( code> N208 (Matb)

l 2. "-0 269
 : 2,4-0-isobutyl
_;. luPAC name 2·mothytpropyt (l,1-dichloropl>enol()')•cetatc
0.S RN (1713- 15-f] EC no. 216-992- S
.t 2.~,.,
~ IUPAC name octyl (2.4·d'cilloro~noxy)¥e<•ue (mixed oct)'I isomer<)
• O.S RN (25 168-21>-7), formerly {1260-20-2/ EC no. 246-704-l
2, 4-D./so/Jfopyl
IUPAC name isopropyl (2,4· dkh .orophe<loxy)acmte
O.S RN (94-11-1) EC no. 102-30~
2. 4-D-Isopropyfommoniim
,. CAS RN (5742- 17-6]. forme r1y [31489-36~)
2.4·0-sO<Jium
IUPAC name sodium (2.4· dlchlorophenoxy)acetate
" CAS RN (2 701-7 l-9} EC no. 220-290-4
l,4·D·triisoproponolommonlum
Chemical Absncts Mme (2.1-dichloropheno><y)acetk acid. 1,1',1"·n1D'ilotrh{2·proponoij ult (1 :1)
CAS RN {1858-4-79-7]. formerly [2945~~}. (3734 f-80-JJ
2, 4-D-UOO..r;n. (2,~rhonolarmonium)
IUPAC name D'i>(2-hydroxyelhyt)~ (2.'klKh!orophenoxy).ce"te
CAS RN (2569-01 - 9] EC no. 11'-911-1
PHYSICAL CHEMISTRY: 2,4..0
Composition Tech. Is ~6" ~ Md wt. 211.0 M.f. CeHfl203 Fonn Colourless powder.
with a ilight phenol" odovr. M.p. H0.5°C V.p. 1.86 x 10- mf'a (l.5°C/ (OECO 104)
i<_ logP ; 2.SS-2.83 (pH 1). o.o•~.JJ (pH S) Henry 1.32 x 10·• Pa m mol" ' (c.lc.)
S.g./density 1.508 (20°C) Soklbllity In water 311 (pH 1), 20031 (pH 5), 23180 (pH 7). 34196
(pH 9) (all in mg/I, 15 •q. In ethnnol 1150. dlethyl echer 243, heptane 1.1. toluene 6. 7, xylene 5.8
(all In gl kg. 20°C); in octanol 120 g/I (25 °C). Insoluble ln petroleum oils. Mono·n·bu1y1am1ne salt ·
In water 18 g/I (30 •q . Stabllty 1,4·0 I• • strong acid, and rorms w~ter·soluble salts wlch al<ali
metals and amines. Hard water lends co prec\pltatlon of the ddum and masneslum salts, but a
sequestering •genL Is included In formulations co prevent this, Phocolylic OT50 (ilmulated sunlight)
75 d. pKa 2.73
2.~utotyf
Mol. wt. 321 .2 MJ. C,.H,.020•
2.4-0-butyf
Mol wt. 277.1 M.f C.1H,.020,
2.~)lcmnot1um
Mol. wt. 266.1 MJ. C 1cH1 ,O,N01 M.p. decomp. c. 120 °C SoWity In water 3 kg/I {20 •q.
Soluble in alcohol• Md acctont. Insoluble In kerosene and diesel oil
2,4-Q.diolomine (2.4·0-diethcndornmo!llum}
Mot WI. 326.2 MJ. c,,H,,.CliNOs
2. 4·0.ethyl
Mol. we. 249.1 MJ. C10H10Cl20l
2, 4-D-2·elhylhexyl
Composition Isomeric with 2. 4-D <soctyl; sometimes these names >re used Interchangeably.

270 2,4-0
 -·- - -··~~------iiiiiioiiOiiiiiii ................·....:---;;-.;; ; .; .;.;.........
..._. .... Miiii
Mol. wt. 333.3 M.f. C16H21Cl-,03 Fonn Golden yel:Ow, non-viscous Hquid, with a sweet. slighdy
pungent odour. M.p. <-37 'C B.p. >300'C (decomp.) V.p. 47.9 mPa (25 °C)
K,,., logP = S.78 (25 'C) Henry 1.8 Pa m3 roo1- 1 (calc.) S.g./densiLy 1.148 (20°C) Solubilh.y In
water 0.086 mg/I (25 'C). Mlscibie with most organic solvents. Stabaity Hydrolysis DT.so <1 h.
Stable co light, DT,. > 100 d. Stable at 54 •c. F.p. 171 •c (Cleveland open cup)
Z, 4-D-isobutyl
Mol. wc 277.1 M.f. C11H,.c1,o,
2, 4-D-isociyl
Composition Isomeric ...11th 2.4-0-1-ethylhexyl; somer.lme.s these n2mes are used Interchangeably.
Mol. wt. 333.3 M.f. c,.HnCl,O, Form Yellowish..IJ<own liquid. With a phenolic odour. \
B.p. 317°C 5'1:.ldensity 1.14-1.17 g/ml (20°C) Solubility In water 10 mg/I. F.p. 171 •c
Z,4-D-isopropy/
Mol. wt. 263.1 MJ. C11 H 12ci,o, Form Colourless liquid. M.p. 5-10°C and 20-25°C (two
rorms) B.p. 130°C/1 mmHg V.p. 1.4 Pa (25 •q Solubnlty Practically Insoluble in Water. Soluble
In alcohols and most o<ls.
2. 4-D~sopropylomrnonium
Mol. wt. 280.2 M.f. C11 H 1 sC'1_N03
2. 4-D-sodium
Mol. wt. 243.0 M.f. C.H3Cl2Na03 Solubility In water 18 g/I (20 °C),
2. 4-D-r:tiisoproponolcrrimonium
Mol. wt. 412.3 M.f. C11H21Cf1NO•
2, 4-D-!!iisopropylammonium
Mol. WC 330.2 M.f. c ,,H,,O,NO,
2. 4-D-rrolomine (2. 4-0-tTieO>anolommonium)
Mol. we 370.2 M.f. C 14Hl 102NO• M.p. 142-144°C Solubility In waw 4.4 kg/I (30°C).
COMMEROAUSATION: History The potent effec:r.s of its s.lc• on pl•nt growth were first
described by P. W. Zimmerman & A. E. Hitchcock (Convib. &yce Thompsot1 Inst.. 1942, 12. 321).
and Its early history Is covered in The Hormone WeedkJ/lers. Maoofacturers Agrochem: Ar><:om:
Atanor: Arul: CAC: Chemrura: Crystal: Dow AgroSdences: Krlshl Rasayan: Marks: Nlttokerrlla;
Nofarm GrnbH; Nufarm Ltd; Nufarm UK; Proficol: R.ainbow; Red Sun: Sannong; Sha1\dong
Qiaochang; Sharda: Sundal
APPLICATIONS: Biochemistry Synd>etic auxin (acting like lndol ylacetlc acid).
Mode of action Selective systemic herbklde. Salt$ ilre readily absorbed by che roots, whilst est~s
are readily absorbed by the Collage. Transtocaclon occurs, \Vlth accumulation prlndpally at the
meristematic regions of shoots and roots. Acts as a growth lnhlb3:tor. Uses Post·emergence
control of ~nnual and perennial broad-leaved weeds in cereals, maiie, sorghum, gra5siand,
established turf. gn:ss seed crops., orchards. (pome fruit aOO stone fruit), Cl'anbenies. asparagvs.
sugar cane, ric.e. (orescry. and on non-crop land (including areas adjacent to water}, ar
0.28-2.3 kg/ha. Control o r broad-leaved aquatic weeds. The isopropyl ester can also be used as a
plant growth regulator to prevent premature fruit fall in citrus fruit. Phytotoxidty Phytotoxic lO
most broad-leaved crops. e.special!y canon, vines. tomatoes. ornamentals, fruit trees. oilseed rape
and bee t.
1.4-D
formulation types EC; GR; SL: SP; WP. Compatibility Co;npatibllity depends upon the particular
formulaclon. Selected producu 'Agrtcom D' (FCC): 'Capri" (Makhteshim-Agani:

2.4-0 271
l
'Oamire" (Agnphor): 'Oeferon· (Mll<!nia); "Dikamln" (NitrokEmia): "Dymec' (PSI/Gordon):
'Herbextra" (amine salt) (Baocheng): 'Kay-0' (mixl\Jf<! of >odl\lm and amine salts w~h etlr)'I ester)
(Knshl R.asayan); 'Palor-mone' (Unlcrop); ·sunGold' (Sundat); ·u 46 D' (Nufarm Ltd):
0
Yer1>1s.or (amine salt} (lngenieru Industrial): mlxwres 'R~e· (+ butachlor} (Monsanto).
2, 4-0-bmocyl
Formulation types EC. Selected produccs 'Erbltox LV·~· (Slapa).
2.4-0-dimeth~""'
Formulation types SL: SP. Sclected products 'Ba<oo" (Nufarm l:<f): 'Dcd-Weed' (Chemtura):
'Oloweed' (United Phosphorus Ltd): "OMA-~' (Dow AgroSciences); "OMA 6' {Dow AgroSclences):
'H•ybob II" (Barclay): "Sonaphen O' (SL) (Dow AgroSciences): 'Sprlo:·Hormln' (Nufarm GmbH):
·suw (Headland); mixtures "Erbicox Comb!' (+ MCPA-<l•nethylammonium) (S.apo}: ·u 46 Combi
fluid' (+ MCPAo0imemylammoolom) (Nufarm Ltd).
2.4·0-diolomlnc (2,4-0.d/olhonalcmmonlum)
fonnulatio<I types SL
2, 4-0.ethyl
Selected proc~JCt.< 'Smash' (Naiarjuna Agnchem).
) •4.0-2~!l>yllluyl
Formulation types EC. Selected p<oducts "Esteron 6E" (Dow ~roScienc10<): "Esteton 99C' (Dow
AgroSdentes): 'Lentemul' (Nufarm GmbH): mixtures 'Sansac" (+ metosulam) (Bayer
Co·opScienco, Dow AgroSclences): 'Maes1ro D" (+ b romoxynil oc1>noar:e) (Nufarm Americas).
1.4·0-isodyf
Fom1'llarlon t:ypeS EC. Sclccted products ' Enordefore' (Vapco): 'Sanaphen 0 " (EC) (Dow
AjJroSdences).
2.4-0.~
Selected p<oducu ·airus Fix" (Amvac).
2. 4-D-isopropylammonium
Fonnularlon type< SL
2. 4-()..$Qdium
formulotion rypes SL Seleal'CI products 'Safnya' (Oevidnya~:
mixwr·es 'Ducxluoshou' (+sodium 1-naphth)'lacetate +sodium p-nitrophenolate +sodium
o-n.trepher.olatc) ~').
2. 4·0-triisoprg))c>1olommonium
Formulation types SL
ANALYSIS: Product an>lysls oJ 2.4-0. ,.,'t;,
l!S••.rs '110 mixed comblNtion products by acld·base
trtraoon. by glc (Ol'AC Honclbool<. 1985. 1C, 20«I, 2257: 1994. F. 292-319). by rplc (AOAC No<chods,
17"' F.<I.. 971,07, 976.03. 978.05. 984.07; CIPAC Hondbool<, 1985. 1C, 2060: 1900, 0 , 51). by hplc
(ibid•• 1983, 1757}. or by i.r. spectrometry (Ibid., 1'998, H. 131). Free phenol impunty determined by
gtc (OPAC l-londlook. 1~. F. 197). by hplc (Ibid.. 1994, f, 362) or el«.tnochemlcaUy (Obid.• 1994. F.
368). Resld\ie.< determined by glc of derivadvcs (Pesrk. Anal. Mo.o.. 1979.1. 201-0: Anol Mechods
Pesdc. Plane Growlll Reg"I" 1972, 6, 630) or by hpk (M. Meier et al.. Fresenivs Z. Anal. Chem.. 1989.
334. 235). In dmkifig warer. by conversion co methyl ester wit!\ dlalometh•ne. thQn gk with ECD
(AOl\C Mtlllods. I 7"' Ed . 992.32).
'TOXICOLOGICAL. & ENVIRONMENTAL REVIEWS: EHC 29 (1984), 84 (1989); tile lacer report
deals primarily~ environmental aspectS.jMPR Mtg. 92 (2001);JMPR Evaln. 181 (1997).

272 2,4-0
 64 (1998), 93 (7.001 ): Jit!PR Evaln. II 79 (1 996), 82 (1 997). To•.lclty and ha<ards to rnan, dcmesoc
arimals and wildlife hav• been ~viewed (J. M. Way, Residue Rev., 1%9. 26, 37),
91/4'14/t.C Annex I S!3!lJs Included, 2001/103/EC.
MAMMALIAN TOXICOLOGY: IARC ref. 15, 41; Suppl. 7; class Chlorophenoxy herbicides
classified as 2B, bas~d on epidemiology of production. More recent evidence (f"I. Kogevinas et ol..
Am.} Epid"'1"iol.. 1997. HS(12}. 1061) relates this to dioxin contamination of early production. Not
relevant to current proc.e:sses.
2,4-D
Oral Acute oral LOso for rats 639-764, mice 138 mg/ kg. Skin and eye Acute p<>r<:utaneous LDso
for raLS >1600. rabbits >2400 .-ng/ kg. Skin and eye irritant (rabbits). A skin sensitiser (guinea
pigs). Inhalation LCso (24 h) fo r rats > 1.79 mg/I. NOEL (2 y) for rats and mice 5 mg/kg b.w.;
(1 y) for dogs 1 mg/ kg b.w. ADI (JMPR) 0.0·1 mg/kg b.w. [2001, ·1997]; O.Q'I mg/kg b.w. (1996}
(sum of 2,4·D and its salts and esters, as 2.4·D): (EEC) 0.05 mg/kg b.w. [2001].
Water GV 30 11g/I (based on AOI), Toxicity class W HO (a.i.) II; EPA (formulation) II.
EC classification Xn: R22! Xi; R.37. R41I R431 RS2, R53: (for salts Xn; R221 Xi: R11 1 R131 N; R51.
R53; for esters Xn; R221 R431 N: RSO, R53).
Z,4·~imet11ylommon1um
Oral Acute oral LD so for rats 9 49 mg/kg. Skin and eye LD50 for rats >2000mg/kg. Not a s!,>jn
irriwic (rabbits): sever• irritant to e)'<O< (rabbits). lnhalatioo LCso (4 h) for rats > 3.5 mg/I air
2. 4-D-2-e<hylhexyl
Oral Acute oral LDso for rau 896 mg/kg. Skin and eye Dermal LD50 for rabbits > 2000 mg/kg.
Slight eye irritant. A skin sensitiser (guklca pigs). Inhalation LCso (1 h) for rats > 5.4 mg/ I air.
ADI Due to toxicological equlv:alence to 2,4·D. ADI is assumed co be equivalent to that fer
2.4·0.
2. 4-D-lsoayl
Oral Acute oral LDso for rau 650 n-glkg. Skin and eye Acute pen:uta.1eous LDso for rats
>3000 mg/ kg. NOEL for rats 1250. dogs 500 mg/kg diet.
2,4-().;sopropyl
Oral Acute oral LD50 fo r rm 700 rr.g/kg.
2, 4-D-soclitJ1n
Or.ii Acute oral LDso fo r rats 666-805 mg/kg.
ECOTOXICOLOGY: 2,W
B;rds Acute oral-LDso fo r wild ducks >1000. Japcnese quail 668, pigeons 668. pheasants
472 mg/kg. LCso (96 h) fo r mallard ducks > 5620 mg/I. Fish Some f0<mulations (e.g. esters) are
toxic to f~ h. whilst others are not. LCso (96 h) for rainbow ttout >100 mg/I. Daplll\ia LC,0 (21 d)
235 mg/I. Algae EC5-0 (5 d) fo r Selemmrum copricorrwtum 33.2 mg/I. Other aquatic spp. ECio
(14 d) for Lem110 gibba 0.58 rng/1. B~s Not toxic to bees: LD50 (o ral) 104.5 1.1g/bee.
Worms LCsa (7 d) SoOmg/ l<g: NOEC (11d) 100g/kg. Other beneficial spp. Hal'mless to
Tr;chogrommo cocoedae, Poecilus cuprws. Aloochoca billneoto.
){ 2.4·D.dimed1ylammoni1.1m
Bircls A<ute oral LD so for bobwhioe qoall 500 mg/kg. O ral LC 5o for bob....tllte quall > 5620 ppm.
foh LC so (96 h) for rainbow o'tlut 100 mg/I. Algae ECso for SelerlOSttum caprlcomutum
51.2 mg/I. Bees LDso {contact) > 100 µg/ bee; (oral) c. 94 µg/ bee.
2, 4·D·2·ethylh<!xyt
Birds Acute oral l Dso for mallard ducks 663 mg/ kg. Dietary LC50 (5 d) for bobwhite quail ard

2,4-0 273
rrull!ard <l\>dtS >5620 ppm. Ash LC..,'"' lalhcid rnmows. blutglll surJ'ish and roiflbow :rout
&'""•- !Nn ~lty in wattto ~ ECIO (48 h) S.2 ~II. Algae EC 50 fO< Sl<eietonemo
costourn 0.23. NavioJfo pelforulow 4.1, Seienaswm cc;>rieomw.m and AllOboero llos'C<fua<
> )Omgll. Other aquatic spp. ECsc (1~ d) for Lemr<> gibba 0.5 m&ll. Bcco lDsc (contJct)
>10011g/bee: (oral) >100 µg / bee.
2,4-0..isocryl
Ash LCso (96 h) for cut-throat trout O.S-1.2 mJlll.
2. 4-D-<adium
8'rds Acute onJ LOsc for W!!d duclc$ >2015 ~/kg
ENVIRONMENTAL FATE: 1,'l-0
EHC 94 condudes that. when used as re<ommende<!. 2,4-D doeJ l\Ot • PP<'•' to produce direct
toxfc effecu on any animal s~del. Anlrn:lls In rats, following oral admlnlscraoon. eltmlnatlon is
rapid. and mainly as the uncnanged subuance. Followlng single doses ol up to 10 mg/kg. excre~on
is almost complete alter 2•1 hours. although. wh:h higher doses. complete elimlnadon takes lonaor.
The m;oornum concentr8lion in organs Is rtad'H!d after c. 12 hours. Pl<lnts In pl~nts, metaboUsm
involves hydroxylation. decarboxyladon. ti«••&• of the aad side·ch.,n, and ring opening.
Soil/Envirounent In soi. rncrobial de&radation inY<Wes hydl'Ol(}'bdon. decart>oxylation. deavag<o ol
tl\e acid side-char1. and nng opEnlng. OTso In soil <7 d Ko. c. 60 Rapid degndalion in <he soil
prevents Sigl\lncant downward movement under normal condition>.
2, 4-0.2-eltlylhexyl
Soii/Environm<>nt Rapidly hyd rolysed In soil and water to the parent acid: OTso < 1 d.

215 Dacnusa sibirica Biological agent

W8'p, pora<i<e or Jul minor~. used in protected crops. For lu" detalls see one l'.1onuc/ o(Sloaintrol
Agents, 3rd Ed. or The 8ioPesticide Manvol, entry: 3:223.

2.16 daimuron Herbicide

HRAC Z

<:H~~-NH-OCH3
- tH3
NOMENCLATURE: Common name ca.muron (Ml. draft E-150. draft (m) F~SO): clymro<\ (JMAF)
IUPAC name 1·(1·methyl-1 ~yle1hyl)-J.p-1olyturea: 1·{a.:x·dime<hy\benzyl)·3-p-tolyturea
Oiemical Abwacu name N-(~·methylphenylf-N' ·(1-methyl·1 ·phenyle!hyl)urea
CAS RN [42609- 52- 9) Dovolopment cod"' K-223: SK-23 (SOS Bloteeh KK}

274 doim.Jron