| Identification | More | [Name]
Cinmethylin | [CAS]
87818-31-3 | [Synonyms]
1-Methyl-4-(1-methylethyl)-2-((2-methylphenyl)methoxy)-7-oxabicyclo[2.2.1]heptane
CINMETHYLIN
(+-)-exo-1-methyl-4-(1-methylethyl)-2-((2-methylphenyl)methoxy)-7-oxabicyclo
(2.2.1)heptane
1-methyl-4-(1-methylethyl)-2-[(2-methylphenyl)methoxy]-exo-(±)-7-Oxabicyclo[2.2.1]heptane
7-oxabicyclo(2.2.1)heptane,1-methyl-4-(1-methylethyl)-2-((2-methylphenyl)metho
argold
cinch
cinch(cinmethylin)
exo-(+-)-7-oxabicyclo(2.2.1)heptan
exo-(+-)-xy)
sd95481
(1RS,2RS,4RS)-1,4-epoxy-p-menth-2-yl-2-metnyl-benzyl ether
exo-(±)-1-methyl-4-(1-methyl ethyl)-2-((2-methyl phenyl)methoxy)-7-oxabicyclo(2,2,1)heptane
Cinmethylin mixture of isomers PESTANAL
cinmethylin (bsi, draft e-iso, ansi, wssa)
Caswell No. 731G
(1RS,2RS,4RS)-1,4-Epoxy-p-menth-2-yl-2-methyl benzyl ether
exo-(+/-)-1-methyl-2-(2-methylbenzyloxy)-4-isopropyl-7-oxabicyclo(2.2.1)heptane
（1RS， 2SR， 4SR）-1-，4-epoxy-p-menth-2-yl-2-methyl benzyl ehter | [EINECS(EC#)]
402-410-9 | [Molecular Formula]
C18H26O2 | [MDL Number]
MFCD01632785 | [Molecular Weight]
274.4 | [MOL File]
87818-31-3.mol |
| Chemical Properties | Back Directory | [Melting point ]
25°C | [Boiling point ]
313°C | [density ]
d20 1015 kg/m3 | [refractive index ]
1.4800 (estimate) | [Fp ]
147 °C | [storage temp. ]
0-6°C | [form ]
neat | [Henry's Law Constant]
1.3×101 mol/(m3Pa) at 25℃, Ebert et al. (2023) | [Major Application]
agriculture
environmental | [InChI]
1S/C18H26O2/c1-13(2)18-10-9-17(4,20-18)16(11-18)19-12-15-8-6-5-7-14(15)3/h5-8,13,16H,9-12H2,1-4H3/t16-,17+,18-/m1/s1 | [InChIKey]
QMTNOLKHSWIQBE-FGTMMUONSA-N | [SMILES]
CC(C)[C@]12CC[C@](C)(O1)[C@@H](C2)OCc3ccccc3C | [CAS DataBase Reference]
87818-31-3(CAS DataBase Reference) | [EPA Substance Registry System]
87818-31-3(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,N | [Risk Statements ]
R20:Harmful by inhalation.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S22:Do not breathe dust . | [RIDADR ]
UN3082 9/PG 3 | [WGK Germany ]
3 | [RTECS ]
RN8762000 | [REACH Registrations]
Inactive | [HS Code ]
29321900 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Acute Tox. 4 Inhalation
Aquatic Chronic 2 | [Toxicity]
LD50 orally in rats: 4.5 g/kg; LD50 dermally in rabbits: >2 g/kg (Lee) |
| Hazard Information | Back Directory | [Description]
Cinmethylinwas developed by Shell Chemical
Company in the early 1980s as a weed control agent for
monocotyledonous species. This herbicide controls important
grasses such as green foxtail (Setaria viridis) and
barnyardgrass (Echinochloa crus-galli) and suppresses
the growth of several broadleaf weeds such as prickly
sida (Sida spinosa) and velvetleaf (Abutilon theophrasti). | [Uses]
Cinmethylin is used as pre-emergence grass herbicide. Cinmethylin is member of the cineole eucalyptol family. | [Uses]
Herbicide. | [Definition]
ChEBI: Exo-(+)-cinmethylin is a 1-methyl-2-[(2-methylbenzyl)oxy]-4-(propan-2-yl)-7-oxabicyclo[2.2.1]heptane that is the exo-(+)-isomer of cinmethylin. It is an enantiomer of an exo-(-)-cinmethylin. | [Production Methods]
Cinmethlyn is commercially synthesised through a multi-step process involving the construction of a 7-oxabicyclo[2.2.1]heptane ring system. The production begins with the formation of the bicyclic ether core, followed by selective alkylation and etherification steps to introduce the methyl, isopropyl, and methoxybenzyl substituents. These reactions are carried out under controlled conditions to ensure stereoselectivity and purity, with final purification achieved through distillation or crystallisation. | [Mechanism of action]
Selective, systemic, absorbed by roots and translocated. Disrupts the meristemic development in shoots and roots of susceptible weeds. | [Pharmacology]
Cinmethylin is active on several important grasses in
rice (Echinochloa spp., Cyperus spp., and Monochoria
vaginalis) at rates from 25 to 100 g ai/ha (5). Its chemical
and toxicological features (low persistence in environment
and low mammalian toxicity) generated a significant level
of interest in its use as a rice herbicide. | [Metabolic pathway]
When rats are administered 14C-cinmethylin orally, the
major route of its elimination is via urinary excretion. A
complex degradation pattern of cinmethylin is
observed and the metabolic pathways involve
hydroxylation, oxidation at the benzyl and cineol
portions, conjugation with glucuronic acid and glycine,
and cleavage of the ether linkage. When rats are
administered 14C-cinmethylin by stomach incubation,
two minor metabolites are identified as o-
(acetoxymethyl)benzoic acid and 9-(acetoxymethyl)-a-
carboxycinmethylin. | [Pesticide Type]
Herbicide |
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