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| | Mepanipyrim Basic information |
| Product Name: | Mepanipyrim | | Synonyms: | 4-methyl-n-phenyl-6-(1-propynyl)-2-pyrimidinamin;FRUPICA;4-METHYL-N-PHENYL-6-(1-PROPYNYL)-2-PYRIMIDINAMINE;mepanipyrim (bsi, draft e-iso);MEPANIPYRIM STANDARD;N-(4-Methyl-6-prop-1-ynylpyrimidin-2-yl)-aniline;4-methyl-N-phenyl-6-(prop-1-ynyl)pyrimidin-2-amine;Mepanioyrim | | CAS: | 110235-47-7 | | MF: | C14H13N3 | | MW: | 223.27 | | EINECS: | 432-140-7 | | Product Categories: | | | Mol File: | 110235-47-7.mol |  |
| | Mepanipyrim Chemical Properties |
| Melting point | 125-126° (Maeno); also reported as 132.8° (Hayashi) | | Boiling point | 418.2±47.0 °C(Predicted) | | density | 1.16±0.1 g/cm3(Predicted) | | vapor pressure | 2.32 x l0-5 Pa (20 °C) | | Fp | 131 °C | | storage temp. | 0-6°C | | solubility | Chloroform (Slightly), Methanol (Slightly) | | pka | 4.5 (est. base) | | Water Solubility | 3.1 mg l-1(20 °C) | | color | White to Off-White | | Henry's Law Constant | 6.0×102 mol/(m3Pa) at 25℃, Maniere et al. (2011) | | Major Application | agriculture
environmental | | InChI | 1S/C14H13N3/c1-3-7-13-10-11(2)15-14(17-13)16-12-8-5-4-6-9-12/h4-6,8-10H,1-2H3,(H,15,16,17) | | InChIKey | CIFWZNRJIBNXRE-UHFFFAOYSA-N | | SMILES | CC#Cc1cc(C)nc(Nc2ccccc2)n1 | | LogP | 3.280 | | EPA Substance Registry System | Mepanipyrim (110235-47-7) |
| Hazard Codes | N,Xn | | Risk Statements | 51/53-50/53-40 | | Safety Statements | 60-61-46-36/37 | | RIDADR | UN3077 9/PG 3 | | WGK Germany | 2 | | RTECS | UV6261540 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Aquatic Acute 1
Aquatic Chronic 1
Carc. 2 | | Toxicity | LD50 in mice, rats, bobwhite, mallard (mg/kg): >5000, >5000, >2250, >2250 orally; in rats (mg/kg): >2000 dermally; LC50 in bluegill, rainbow trout (mg/l): 3.8, 3.1 (Maeno) |
| | Mepanipyrim Usage And Synthesis |
| Chemical Properties | Light yellow crystalline powder, melting point 125～126℃, vapor pressure 1.33mPa at 20℃, solubility 5.58mg/L in water at 20℃, soluble in most organic solvents. kow2600. stable at pH4～θ. Toxicity: Acute oral LD50>5000mg/kg for rat and mouse, acute percutaneous LD50>2000mg/kg for rat, no irritation to rabbit's skin and eyes, no sensitization to guinea pig's skin, no mutagenicity in Ames test. Acute oral LD50>2250mg/kg in quail and duck, LC50 >3.8mg/L in bluegill, LC503.1mg/L in rainbow trout. | | Uses | Mepanipyrim is a non-systemic fungicide that provides preventative
control of diseases in pome fruits (scab), vines, strawberries, tomatoes
and cucumbers (grey mould) and peaches (brown rots) caused by Botrytis
cinerea, Venturia inaequaris and Monilinia fructicola. | | Uses | Mepanipyrim is an anilinopyrimidine fungicide which have been used in the management of fungal diseases in strawberries. | | Uses | Agricultural fungicide. | | Definition | ChEBI: A member of the class of aminopyrimidines that is N-phenylpyrimidin-2-amine carrying additional methyl and 1-propynyl substituents at positions 4 and 6 respectively. A fungicide used to control a wide range of diseases including grey mou
d on strawberries, tomatoes and cucumabers, and scab on apples and pears. | | Production Methods | The industrial production of mepanipyrim begins with the synthesis of a substituted pyrimidine core, typically derived from 2-amino-4,6-dimethylpyrimidine. This intermediate undergoes acylation with 4-methylbenzoyl chloride to form a key amide linkage. The reaction is carried out under controlled conditions using organic solvents like dichloromethane and a base such as triethylamine to neutralize by-products and drive the reaction to completion. The resulting compound, mepanipyrim, is then purified through crystallisation or solvent extraction to ensure high chemical purity. | | Mechanism of action | Non-systemic with preventative action. Inhibits protein synthesis. | | Metabolic pathway | By tomato seedlings, 14C-mepanipyrim is
biotransformed via the pathways including elimination
of the phenyl group, hydroxylation of the propynyl
moiety, and hydroxylation at the phenyl ring to yield
several kinds of metabolite, and 2- and 4-[4-methyl-6-
(1-propynyl)pyrimidin-2-ylamino]phenols, 1-(2-anilino-6-
methylpyrimidin-4-yl)-2-propanol, and 4-methyl-6-(1-
propynyl)pyrimidin-2-ylamine are tentatively identified
as major metabolites. In soils under laboratory
conditions, 14C-mepanipyrim undergoes degradation to
give the degradation products and the main pathway
is elimination of the phenyl group. | | Degradation | Mepanipyrim (1) is stable to hydrolytic degradation in the pH range
4-9 with a DT50 >1 year. It decomposed rapidly in water when exposed
to light (DT50 13 days) (PM). | | Pesticide Type | Fungicide; Other susbtance |
| | Mepanipyrim Preparation Products And Raw materials |
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