87818-31-3

Basic information

• Product Name: Cinmethylin
• 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;exo-(±)-1-methyl-4-(1-methyl ethyl)-2-((2-methyl phenyl)methoxy)-7-oxabicyclo(2,2,1)heptane;Cinmethylin mixture of isomers PESTANAL
• CAS NO: 87818-31-3
• Molecular Formula: C18H26O2
• Molecular Weight: 274.4
• EINECS: 402-410-9
• Product Categories: Herbicide;Agro-Products;Aromatics;Heterocycles
• Mol File: 87818-31-3.mol

Chemical Properties

• Melting Point: 25°C
• Boiling Point: 313°C
• Flash Point: 147 °C
• Appearance: /
• Density: d20 1015 kg/m3
• Vapor Pressure: 0.000939mmHg at 25°C
• Refractive Index: 1.4800 (estimate)
• Storage Temp.: 0-6°C
• CAS DataBase Reference: Cinmethylin(CAS DataBase Reference)
• NIST Chemistry Reference: Cinmethylin(87818-31-3)
• EPA Substance Registry System: Cinmethylin(87818-31-3)

Safety Data

• Hazard Codes: Xn,N
• Statements: 20-51/53
• Safety Statements: 23-61-22
• RIDADR: UN3082 9/PG 3
• WGK Germany: 3
• RTECS: RN8762000
• Hazardous Substances Data: 87818-31-3(Hazardous Substances Data)

Usage

Uses

Used in Agriculture:
Cinmethylin is used as a pre-emergence grass herbicide for controlling important grasses such as green foxtail (Setaria viridis) and barnyardgrass (Echinochloa crus-galli). It is also effective in suppressing the growth of several broadleaf weeds, including prickly sida (Sida spinosa) and velvetleaf (Abutilon theophrasti). This makes it a valuable tool in managing weed populations and maintaining healthy crop growth.

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.

InChI:InChI=1/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

Upstream product

• 158353-15-2 1-(3-chloro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-yl)-5-(methyl-2-propynylamino)-1H-pyrazole-4-carbonitrile 
• 552-45-4 1-chloromethyl-2-methylbenzene 
• 22555-57-3 2-exo-hydroxy-1-methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane 
• 562-74-3 TERPINEN-4-OL 
• 89-92-9 2-methylbenzyl bromide 

Relevant articles and documents

Herbicidal activity of cineole derivatives

Essential oils and their constituents have potential as ecologically acceptable pesticides that may also have novel modes of action. In this work hydroxy and ester derivatives of the naturally occurring monoterpenoids 1,8-cineole 3, the main component in

A PROCESS FOR PREPARING AN OPTICALLY ACTIVE CINEOLE DERIVATIVE

The present invention relates to a process for preparing optically active 1,4-cineole derivatives by enzymatic resolution and enantiomerically pure optically active 1,4-cineole derivatives of purity greater than 99.9 % that have been prepared by this proc

A METHOD FOR SEPARATING OPTICALLY ACTIVE HYDROXY CINEOLE DERIVATIVES

The present invention relates to a method for separating an optically active hydroxy cineole derivatives by lixiviation and crystallization and enantiomerically pure optically active hydroxy cineole derivatives of purity greater than 99.5 % that have been

PROCESS FOR PREPARING 2-EXO-(2-METHYLBENZYLOXY)-1-METHYL-4-ISOPROPYL-7-OXABICYCLO[2.2.1]HEPTANE

This invention relates to a process for preparing (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-isopropyl-7-oxabicyclo[2.2.1]heptane of the formula (I) (I), any of its individual enantiomers or any non-racemic mixture thereof, comprising the step of reacting (

PROCESS FOR PREPARING 2-EXO-(2-METHYLBENZYLOXY)-1-METHYL-4-ISOPROPYL-7-OXABICYCLO[2.2.1]HEPTANE

This invention relates to a process for preparing (±)-2-exo-(2-Methylbenzyloxy)-1 -methyl-4-iso- propyl-7-oxabicyclo[2.2.1]heptane of the formula (I), (I) any one of its individual enantiomers or any non-racemic mixture thereof comprising the steps of (a)

PROCESS FOR PREPARING 2-EXO-(2-METHYLBENZYLOXY)-1-METHYL-4-ISOPROPYL-7-OXABICYCLO[2.2.1]HEPTANE

This invention relates to a process for preparing (±)-2-exo-(2-Methylbenzyloxy)-1-methyl-4-iso- propyl-7-oxabicyclo[2.2.1]heptane of the formula (I), any of its individual enantiomers or any non-racemic mixture thereof, comprising the steps of (a) reactin

Synergistic herbicidal mixtures

PCT No. PCT/EP96/04935 Sec. 371 Date May 1, 1998 Sec. 102(e) Date May 1, 1998 PCT Filed Nov. 12, 1996 PCT Pub. No. WO97/17852 PCT Pub. Date May 22, 1997A synergistically active herbicidal composition which comprises, as active components, a mixture of 1-(3-chloro-4,5,6,7-tetrahydropyrazolo-[1,5-a]-pyridin-2-yl)-5-(methylpropargylamino)-4-pyrazolylcarbonitrile [Component (A)] and a herbicide selected from the group consisting of bentazone, molinate, daimuron, thiobencarb, butachlor, pretilachlor, dimepiperate, fenoxaprop-ethyl, clomeprop, cinmethylin, bromobutide, quinclorac, mefenacet, pyrazosulfuron-ethyl, esprocarb, cinosulfuron, thenylchlor, cumyluron, MK 243, naproanilide, anilofos, benfuresate, bifenox, CH-900, MCPA, nitrofen, oxadiazon, pendimethalin, simetryn, sulcotrione (ICIA0051), trifluralin, piperophos, pyributicarb, ethoxysulfuron, bensulfuronmethyl, pyrazolate, pyrazoxyfen, benzofenap, cyclosulfamuron, cyhalofop-butyl, NBA-061, azimsulfuron, propanil or imazosulfuron [Component (B)] and which are suitable for controlling undesirable plants in rice cultivation.

Selective method-of-use of oxabicycloalkanes

This invention relates to a method for controlling the growth of undesired vegetation in paddy rice crops by applying an effective amount of an oxabicycloalkane herbicidal compound to the locus of paddy rice.

Oxabicycloalkane herbicides

Compounds of the formula STR1 wherein X is (--CR4 R4 --)m in which m is 0 or 1; Y is (--CR5 R6 --)n in which n is 0, 1 or 2; Z is (--CR7 R7 --)p in which p is 1, 2, or 3; the sum of m+n+p is an integer of 2 to 5, inclusive; R2 and R3 each is H or alkyl, and the like; R1 is H or alkyl; and W is an unsaturated moiety, are useful as plant growth regulators and herbicides.

Oxabicycloalkane herbicides

Certain substituted 3-cyclohexene-1-ol are intermediates to herbicides and plant growth.