Clodinafop-propargyl
Herbicide
HRAC A3 WSSA 1; aryloxyphenoxypropionate
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NOMENCLATURE
clodinafop-propargyl
Common
name
clodinafop-propargyl
IUPAC
name
prop-2-ynyl
(R)-2-[4-(5-chloro-3-fluoropyridin-2-yloxy)phenoxy]propionate
Chemical
Abstracts name
propynyl
(R)-2-[4-[(5-chloro-3-fluoro-2-pyridinyl)oxy]phenoxy]propanoate
CAS
RN
[105512-06-9] Development
codes
CGA
184927 (Ciba-Geigy)
clodinafop
Common
name
clodinafop
(BSI, pa E-ISO)
CAS
RN
[114420-56-3]
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PHYSICAL
CHEMISTRY
clodinafop-propargyl
Composition
(R)-
isomer.
Mol.
wt.
349.8 M.f.
C17H13ClFNO4 Form
Colourless
crystals.
M.p.
59.5
ºC; (tech., 48.2-57.1 ºC)
V.p.
3.19
´
10-3
mPa (25 ºC) (OECD 104)
KOW
logP
= 3.9 (25 ºC)
Henry
2.79
´
10-4
Pa m3
mol-1
(calc.)
S.g./density
1.37
(20 ˇăC)
Solubility
In
water 4.0 mg/l (25 ºC). In ethanol 97,
acetone 880, toluene 690, n-hexane 0.0086,
n-octanol 25 (all in g/l, 25 ºC). Stability
Relatively
stable in acidic media at 50 ºC, hydrolyses
in alkaline media; DT50
(25 ºC) 64 h (pH 7), 2.2 h (pH 9).
COMMERCIALISATION
History
Reported
by J. Amrein et al. (Proc. Br. Crop
Prot. Conf. - Weeds, 1989, 1, 71-76).
Introduced by Ciba-Geigy AG (now Syngenta AG)
and first marketed in 1990.
Patents
EP
B 0083556, US 4713109
Manufacturers
Syngenta
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APPLICATIONS
clodinafop-propargyl
Biochemistry
Fatty
acid synthesis inhibitor, by inhibition of acetyl
CoA carboxylase (ACCase). Mode
of action
Post-emergence,
systemic grass herbicide. Phytotoxic symptoms
appear within 1-3 weeks, affecting meristematic
tissue.
Uses
Used
for post-emergence control of annual grasses,
including Avena,
Lolium,
Setaria,
Phalaris
and Alopecurus,
in cereals, at 30-60 g/ha.
Phytotoxicity
Low
toxicity to spring and winter wheat.
Formulation
types
EC;
WP. Compatibility
Mainly
used in combination with the safener cloquintocet-mexyl. Selected
tradenames: mixtures:
'Celio'
(+ cloquintocet-mexyl)
(France) (Syngenta);
'Topik' (+ cloquintocet-mexyl)
(Syngenta)
OTHER
TRADENAMES
clodinafop-propargyl
'Conduct'
(Syngenta);
'Discover' (Syngenta);
'Magestan' (Syngenta)
mixtures:
'Amazon'
(+ diflufenican)
(Syngenta);
'Hawk' (+ trifluralin)
(Syngenta);
'Horizon' (+ cloquintocet-mexyl)
(Canada) (Syngenta);
'Lucifer' (+ diflufenican)
(Aventis)
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| ANALYSIS
Details
available from Syngenta. |
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MAMMALIAN
TOXICOLOGY
clodinafop-propargyl
Oral
Acute
oral LD50
for rats 1829, mice >2000 mg/kg.
Skin
and eye
Acute
percutaneous LD50
for rats >2000 mg/kg. Non-irritating to eyes
and skin (rabbits). May cause skin sensitisation
(guinea pigs).
Inhalation
LC50
(4 h) for rats 2.325 mg/l air.
NOEL
(2
y) for rats 0.35, (18 mo) for mice 1.2, (1 y)
for dogs 3.3 mg/kg b.w. daily.
ADI
0.004
mg/kg b.w.
Toxicity
class
WHO
(a.i.) III
EC
hazard
(R22,
R43)
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ECOTOXICOLOGY
clodinafop-propargyl
Birds
LD50
(8 d) for mallard ducks >2000, bobwhite quail
>1455 mg/kg. Fish
LC50
(96 h) for rainbow trout 0.39, carp 0.46, catfish
0.43 mg/l. Daphnia
LC50
(48 h) >74 mg/l.
Algae
EC50
(96-120 h) for Scenedesmus subspicatus
25, Microcystis >65.5, Navicula
6.8 mg/l.
Bees
LD50
(48 h, oral and contact) >100 mg/bee. Worms
LC50
for earthworms 210 mg/kg.
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ENVIRONMENTAL
FATE
Animals
Hydrolysed
to the corresponding acid.
Plants
In
plants, rapidly degraded to the acid derivative
as major metabolite. Soil/Environment
In
soil, undergoes rapid degradation to the free
acid (DT50
<2 h) and then further to phenyl and pyridine
moieties which are bound to the soil and mineralised.
The free acid is mobile in soil, but is further
degraded with DT50
5-20 d; in practice, there is a negligible leaching
potential. |
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Products--ˇ·HERBICIDES