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| | FENTRAZAMIDE Basic information |
| Product Name: | FENTRAZAMIDE | | Synonyms: | FENTRAZAMIDE;4-(2-CHLOROPHENYL)-N-CYCLOHEXYL-N-ETHYL-4,5-DIHYDRO-5-OXO-1H-TETRAZOLE-1-CARBOXAMIDE;fentrazamide(bsi,pa iso);yrc 2388;Fentrazamide@1000 μg/mL in Acetonitrile;Fentrazamide Standard;Fentrazamide Solution;1H-Tetrazole-1-carboxamide, 4-(2-chlorophenyl)-N-cyclohexyl-N-ethyl-4,5-dihydro-5-oxo- | | CAS: | 158237-07-1 | | MF: | C16H20ClN5O2 | | MW: | 349.82 | | EINECS: | 605-140-1 | | Product Categories: | | | Mol File: | 158237-07-1.mol |  |
| | FENTRAZAMIDE Chemical Properties |
| Melting point | 79° | | Boiling point | 434.4±47.0 °C(Predicted) | | density | d20 1.30 | | vapor pressure | 0-0Pa at 20-25℃ | | storage temp. | 0-6°C | | pka | -1.03±0.20(Predicted) | | Henry's Law Constant | 5.1×104 mol/(m3Pa) at 25℃, Ebert et al. (2023) | | Major Application | agriculture
environmental | | InChI | 1S/C16H20ClN5O2/c1-2-20(12-8-4-3-5-9-12)15(23)22-16(24)21(18-19-22)14-11-7-6-10-13(14)17/h6-7,10-12H,2-5,8-9H2,1H3 | | InChIKey | LLQPHQFNMLZJMP-UHFFFAOYSA-N | | SMILES | CCN(C1CCCCC1)C(=O)N2N=NN(C2=O)c3ccccc3Cl | | LogP | 3.6 at 20℃ | | Surface tension | 66-69mN/m at 700-1800μg/L and 20℃ |
| Hazard Codes | N | | Risk Statements | 50/53 | | Safety Statements | 60-61 | | RIDADR | UN3077 9/PG 3 | | WGK Germany | 2 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Aquatic Acute 1 | | Toxicity | LD50 in rats (mg/kg): >5000 orally, >5000 dermally; LC50 in rats (mg/m3): >5000 by inhalation; LC50 (48 hr) in carp, rainbow trout (mg/l): 3.2, 3.4 (Yasui) |
| | FENTRAZAMIDE Usage And Synthesis |
| Description | Fentrazamide is a tetrazolinone herbicide for use in rice. It has a very low aqueous solubility, is relatively volatile and very persistent in water systems but much less so in soil. It has a low mammalian toxicity, however there is little reported information on human health effects. It is moderately toxic to birds, most aquatic organisms and earthworms but is not toxic to honeybees. | | Uses | Herbicide. | | Uses | Fentrazamide is a useful herbicide for proteomics research. | | Definition | ChEBI: Fentrazamide is a member of tetrazoles. | | Preparation | The synthetic pathway employed in the production of fentrazamide is shown in Figure 6. The reaction of 2-chlorophenyl isocyanate 8 and sodium azide in the presence of a catalytic amount of aluminum trichloride in dimethylformamide produces 1-(2-chlorophenyl)-5(4H)-tetrazolinone 9 in high yields. The tetrazolinone 9 is then mixed with N-cyclohexyl-N-ethylcarbamoyl chloride 10 in the presence of potassium carbonate and a catalytic amount of 1-dimethylaminopyridine (DMAP) in toluene to afford fentrazamide in high yields.
Following the disclosure of fentrazamide, several companies entered the herbicidal tetrazolinone chemistry race, and as a consequence many compounds of this class were prepared. The main agents included carbamoyl tetrazolinones with either a heterocycle group, a cycloalkyl group, or a heterocycle methyloxy group at the 1-position of the tetrazolinone ring, thiocarbamoyl tetrazolinones, carbamoyl tetrazolinones with tetrahydro-2H-pyran-4-yl group in the carbamoyl moiety, and hydrazine carbamoyl tetrazolinones. To date, none of these compounds have achieved commercial status. | | Agricultural Uses | Fentrazamide is highly effective in the control of annual grass weeds (Echinochloa spp., C. difformis, S. juncoides) and broadleaf weeds (L. pyxidaria, M. vaginalis). It controls barnyard grass of zero- to three-leaf stage at application rates of 200– 300 g ha−1. This compound is also characterized by a long-term residual activity and shows excellent safety toward both transplanted rice and seeded paddy rice. Indeed, based on these properties, fentrazamide became the first paddy herbicide to be used as simultaneous treatment at the time of transplanting. The mixture partners of fentrazamide in one-shot paddy herbicides include sulfonylureas such as bensulfuron-methyl (Innova®) or pyrazosulfuron-ethyl (Doublestar®) and 4-HPPD inhibitors such as benzobicyclon (Smart®). In Southeast Asian countries, fentrazamide is used as a mixture with propanil (Lecspro®) to treat direct-seeded rice. | | Mechanism of action | Selective. Inhibition of very long chain fatty acids (VLCFA, inhibition of cell division) | | Pesticide Type | Herbicide |
| | FENTRAZAMIDE Preparation Products And Raw materials |
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