methyl (e)-α-methoxyimino-2-[(e)-1-(3-trifluoromethylphenyl)ethylidenaminooxymethyl]phenylacetate
Trifloxystrobin
CAS: 141517-21-7
Molecular Formula: C20H19F3N2O4
methyl (e)-α-methoxyimino-2-[(e)-1-(3-trifluoromethylphenyl)ethylidenaminooxymethyl]phenylacetate - Names and Identifiers
| Name | Trifloxystrobin |
| Synonyms | TEGA FLINT STRATEGO TRIFLOXYSTROBIN Trifloxystrobin trifloxystrobin (bsi, pa iso) methyl (e)-α-methoxyimino-2-[(e)-1-(3-trifluoromethylphenyl)ethylidenaminooxymethyl]phenylacetate Methyl (2Z)-2-methoxyimino-2-[2-[[1-[3-(trifluoromethyl)phenyl]ethylideneamino]oxymethyl]phenyl]acetate methyl (2Z)-(methoxyimino)(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)ethanoate methyl (2E)-(methoxyimino)(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)ethanoate alpha-(Methoxyimino)-2-[[[(E)-[1-[3-(trifluoromethyl)phenyl]ethylidene]amino]oxy]methylbenzene acetic acid, (E,E)-Methyl ester Benzeneacetic acid, .alpha.-(methoxyimino)-2-(E)-1-3-(trifluoromethyl)phenylethylideneaminooxymethyl-, methyl ester, (.alpha.E)- |
| CAS | 141517-21-7 |
| EINECS | 480-070-0 |
| InChI | InChI=1/C20H19F3N2O4/c1-13(14-8-6-9-16(11-14)20(21,22)23)24-29-12-15-7-4-5-10-17(15)18(25-28-3)19(26)27-2/h4-11H,12H2,1-3H3/b24-13+,25-18+ |
| InChIKey | MGNJFZURPQVGJE-BWAHOGKJSA-N |
methyl (e)-α-methoxyimino-2-[(e)-1-(3-trifluoromethylphenyl)ethylidenaminooxymethyl]phenylacetate - Physico-chemical Properties
| Molecular Formula | C20H19F3N2O4 |
| Molar Mass | 408.37 |
| Density | 1.21±0.1 g/cm3(Predicted) |
| Melting Point | 72.9° |
| Boling Point | bp~312° |
| Flash Point | >70°C |
| Vapor Presure | 0mmHg at 25°C |
| Appearance | neat |
| Storage Condition | Sealed in dry,2-8°C |
| Refractive Index | 1.511 |
| Physical and Chemical Properties | Storage Conditions: 0-6 ℃ |
methyl (e)-α-methoxyimino-2-[(e)-1-(3-trifluoromethylphenyl)ethylidenaminooxymethyl]phenylacetate - Risk and Safety
| Risk Codes | R43 - May cause sensitization by skin contact R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S24 - Avoid contact with skin. S37 - Wear suitable gloves. S46 - If swallowed, seek medical advice immediately and show this container or label. S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| UN IDs | UN3077 9/PG 3 |
| WGK Germany | 2 |
| Toxicity | LD50 in rats (mg/kg): >5000 orally; >2000 dermally; LC50 by inhalation in rats (mg/m3): >4646; LC50 in bobwhite quail (mg/kg): >2000; LC50 in rainbow trout (mg/l): 0.015 (Margot) |
methyl (e)-α-methoxyimino-2-[(e)-1-(3-trifluoromethylphenyl)ethylidenaminooxymethyl]phenylacetate - Reference Information
| fungicide for plants | trifloxystrobin is a kind of fungicide, with the discovery of such natural-methoxy acrylate derivatives, a new class of broad-spectrum, high-efficiency and low-toxicity bactericides has been developed. Trifloxystrobin is a methoxyacrylate fungicide developed by Syngenta company and Bayer company in Germany. It has a broad-spectrum bactericidal effect on almost all fungal diseases such as powdery mildew, rust, downy mildew, both Botrytis cinerea and rice blast have obvious inhibitory effect, and have the advantages of resistance to rain erosion, long-lasting efficacy and environmental friendliness. The development of trifloxystrobin has injected fresh vitality into the world pesticide market. The fungicide has excellent performance, long-lasting control effect and unique Sterilization Method, and its market potential is huge. In addition, through a large number of animal experiments and studies, it is found that its mechanism of action is unique, and there is no interactive resistance to the existing fungicides, strains resistant to dicarboxamide and benzimidazole pesticides are still effective. The toxicity of trifloxystrobin is very small, if absorbed into the body, most will be excreted, there will be only a small residue. The pharmacological experiments of trifloxystrobin showed that it had no teratogenicity and mutagenicity to fetus, so the fungicide had high safety. And trifloxystrobin fast dissolution, easy hydrolysis, but also in plants in the soil and water degradation, very low toxicity to animals and plants, friendly to the environment, is a green fungicide. It is strongly adsorbed by the plant wax layer, Provides excellent protective activity on the plant surface. Mainly used for grapes, apples, wheat, peanuts, bananas, vegetables, such as stem and leaf treatment, control. Therefore, the emergence of trifloxystrobin is of great significance to improve the structure of pesticides in China, reduce pesticide residues and reduce the adverse effects on the ecological environment. Trifloxystrobin is a methoxy acrylic fungicide, pure appearance is tasteless white to gray crystalline powder; Melting point 72.9 ℃; Boiling point of about 312 ℃; Vapor pressure (25 ℃)3.4*10-6Pa; solubility in water (25 ° C) 0.61mg/L; Solubility in organic solvents (g/L,25 ° C): acetone, dichloromethane ethyl acetate> 500, toluene 500, 11 in n-hexane, 18 in octanol and 76 in methanol. The ratio of N-octanol/water was LogPow = 4.5(20 ℃), under alkaline conditions, the hydrolysis rate increases with the increase of pH, which is non-corrosive to stainless steel and polyethylene. |
| toxicological studies | Acute toxicity test: acute oral LD50>5000mg/kg in rats, acute percutaneous LD50 >2 000mg/kg, acute inhalation LC50 >4.65mg/L; Mild irritation to rabbit skin, mild to moderate irritation to the eyes; the results of guinea pig skin sensitization test showed no sensitization. Long-term toxicity test: Rats 3 months of sub-chronic feeding toxicity test maximum no effect dose: male rats 6.44mg/kg/d, female rats 6.76mg/kg/d. Mutagenicity test: Ames test, micronucleus test of mouse bone marrow cells, in vitro mammalian cell chromosome aberration test and other mutagenicity tests were negative, without mutagenicity. The second generation of reproduction and teratogenic test, carcinogenic test: The results showed no teratogenicity, carcinogenicity. Oxime Tebuconazole 75% Water Dispersible Granules rat acute oral LD50: Female> 5000mg/kg, male 3830mg/kg, acute percutaneous LD50>2000mg/kg; the eyes and skin of rabbits were not irritant, and the skin sensitization test of guinea pigs showed no sensitization. Trifloxystrobin and oxime Tebuconazole 75% Water Dispersible Granules were low toxicity fungicides. |
| Environmental safety evaluation | trifloxystrobin has low vapor pressure and low volatility. Under aerobic condition, DT50 <1 ~ 2d, and under neutral and weak acid condition, it was not easy to hydrolyze, but under alkaline condition, hydrolysis increased with the increase of pH; 25 ℃ pH = 7~9, the half-life of 15~40.8d; Water photolysis Half-Life of 31.5h(pH = 7,25 ℃), the half-life was 1.1d(pH = 5) and 1.7d(pH = 7), which could be rapidly degraded in soil and water. The LC50 of the original drug on rainbow trout (96H) was 0.015mg/L, carp (96H) LC50 0.039mg/L, freshwater algae (72h) erc500.016 mg/L, Daphnia magna (48h) ec500.025 mg/L; North American quail LD50 >2000mg/kg, Bee oral contact LC50>200g/Bee; Bombyx mori (96H) LC50 178mg/kg mulberry leaf; earthworm LC50 >1000mg/kg soil. Oxime bacteria Tebuconazole 75% Water Dispersible Granules on carp (96H) LC50 0.3168mg/L, tilapia (96H) LC50 0.536 mg/L; Green algae (72h)ErC50>150g/L, daphnia magna (48h)EC50 0.0138mg/L; North American quail LD50> 2000mg/kg; Bee oral LD50 406.16g/Bee, LD50 >133.5g/Bee; silkworm (96H) LC50>500 mg/kg mulberry leaves; In the earthworm, the dosage of 1310G/hm2, 28d no death. Trifloxystrobin has high toxicity and high risk to fish and aquatic organisms; It has low toxicity to birds, bees, silkworm and earthworms. During dispensing and application, care should be taken not to cause the medicament to contaminate the water source, and cleaning of the medicament applicator in water bodies such as river ponds is prohibited. |
| synthetic route | with O-methyl aniline as the starting material, the intermediate formed by methyl glyoxylate and hydroxylamine hydrochloride is diazotized and methylated, after Bromination and (E )-M-trifluoromethyl acetophenone oxime final reaction of trifloxystrobin, the specific synthesis route is as follows: |
| Application | trifloxystrobin is a methoxyacrylic fungicide with broad bactericidal spectrum and high activity, which has protective and therapeutic effects, it has good activity against fungi such as ascomycetes, unknown species, Basidiomycetes and oomycetes. It is a respiratory chain inhibitor that inhibits mitochondrial respiration by blocking the electron transfer between cytochrome B and C1. Because the action site of methoxyacrylic fungicides on the target pathogenic bacteria is single, it is easy to produce drug resistance, not used alone, but different from the chemical structure, the mechanism of action is also completely different triazole fungicide Tebuconazole mixed into a mixed preparation registration, use. The mixture of the two can expand the bactericidal spectrum, reduce the dosage, reduce the frequency of use, and delay the emergence of drug resistance. Tebuconazole 75% Water Dispersible Granules of oxime bacteria had higher activity and control effect on cucumber powdery mildew, anthracnose and tomato early blight. |
| usage and dosage | active ingredient 112.5~168.75ga. I./hm2 (the commercial volume of 75% Water Dispersible Granules is 150~225g/hm2 or 10~15g/667, and the dosage of 667m2 is generally diluted with water 45 ~ 75L), in the early stage of the disease, the foliar spray is applied 3 times in the growing season, and the interval is 7 days. Under the recommended dosage, it is safe for crops, and there is no damage to the plant: in cucumber and tomato on the highest dose of 15g/667, the maximum application of 3 times, the interval of 7 days 1 time, the safety interval is 5 days. The plant bactericide, toxicology research, environmental safety evaluation, application, usage, dosage and synthesis route of trifloxystrobin are edited and sorted by Xuyan. (2016-05-06) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 02:00:01
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