alpha,alpha,alpha-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine
trifluralin
CAS: 1582-09-8
Molecular Formula: C13H16F3N3O4
alpha,alpha,alpha-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine - Names and Identifiers
| Name | trifluralin |
| Synonyms | L36352 treflam TREFLAN IPERSAN Trifurex TRIFLUREX TREFLAN(R) trilin 4ec Trifiuralin trifluralin agreflan 24 4-DIPROPYLAMINO-3,5-DINITROBENZO-TRIFLUORIDE 2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)aniline A,A,A-TRIFLUORO-2,6-DINITRO-N,N-DIPROPYL-P-TOLUIDINE 2,6-Dinitro-N,N-dipropyl-4-(trifluoromethyl)-benzamine 4-(Di-n-propylamino)-3,5-dinitro-1-trifluoromethylbenzene alpha,alpha,alpha-Trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine alpha,alpha,alpha-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine |
| CAS | 1582-09-8 |
| EINECS | 216-428-8 |
| InChI | InChI=1/C13H16F3N3O4/c1-3-5-17(6-4-2)12-10(18(20)21)7-9(13(14,15)16)8-11(12)19(22)23/h7-8H,3-6H2,1-2H3 |
alpha,alpha,alpha-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine - Physico-chemical Properties
| Molecular Formula | C13H16F3N3O4 |
| Molar Mass | 335.28 |
| Density | 1.294 |
| Melting Point | 48.5°C |
| Boling Point | 139°C |
| Flash Point | 100°C |
| Solubility | Insoluble in water, soluble in most organic solvents. |
| Vapor Presure | 1.97 at 30 °C (effusion method, DePablo, 1976) |
| Appearance | Yellow-orange crystalline solid |
| Color | Bright orange |
| Merck | 13,9757 |
| BRN | 1893555 |
| pKa | -1.45±0.50(Predicted) |
| Storage Condition | APPROX 4°C |
| Refractive Index | 1.527 |
| MDL | MFCD00055241 |
| Physical and Chemical Properties | Density 1.294 melting point 48.5°C boiling point 139°C water solubility <0.01g/100 mL at 22.5°C |
| Use | A pre-emergence herbicide used to control annual weeds in cotton and legume fields |
alpha,alpha,alpha-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine - Risk and Safety
| Risk Codes | R36 - Irritating to the eyes R43 - May cause sensitization by skin contact R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R11 - Highly Flammable R40 - Limited evidence of a carcinogenic effect |
| Safety Description | S2 - Keep out of the reach of children. S24 - Avoid contact with skin. S37 - Wear suitable gloves. 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. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S16 - Keep away from sources of ignition. S46 - If swallowed, seek medical advice immediately and show this container or label. S36/37 - Wear suitable protective clothing and gloves. |
| UN IDs | UN 2588 |
| WGK Germany | 2 |
| RTECS | XU9275000 |
| HS Code | 29214300 |
| Hazard Class | 9 |
| Packing Group | III |
| Toxicity | LD50 orally in rats: 500 mg/kg (Goldenthal) |
alpha,alpha,alpha-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine - Reference
| Reference Show more | 1. [IF=4.407] Huanan Han et al."Generation of a high-efficiency adenine base editor with TadA8e for developing wheat dinitroaniline-resistant germplasm."Crop J. 2021 Aug;: |
alpha,alpha,alpha-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine - Preparation Method
Open Data Verified Data
toluene is prepared by catalytic chlorotoluene, and then under the photocatalysis, chloro-benzyl trichloride is prepared, then p-chloro-trifluorotoluene is prepared by reaction with hydrogen fluoride, by nitration into 4-trifluoromethyl-2, 4-= nitrochlorobenzene. On the other hand, Propylene aldehyde is synthesized from ethylene by carbonyl group, propanol is reduced, and dipropylamine is prepared by reaction with ammonia. The above obtained 4-trifluoromethyl -2,4-nitrochlorobenzene and dipropylamine were reacted at 100 ° C. For 2H, and post-processed to obtain trifluralin.
Last Update：2024-01-02 23:10:35
alpha,alpha,alpha-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine - Use
Open Data Verified Data
a broad spectrum of dryland pre-emergence herbicides. Can be used for cotton, soybean, pea, rape, peanut, potato, winter wheat, barley, Castor, sunflower, sugarcane, vegetables, fruit trees, etc., mainly used for the control of monocotyledon weeds and annual Broad-leaved weeds, such as humulus, big thrush, Horse Tang, Setaria, Kentucky bluegrass, Kentucky bluegrass, gold, corn grass, maimian, Wild Oats, etc., can also control the small seeds of Portulaca oleracea, breeding and other dicotyledonous weeds. The control effect of Solanum nigrum, Xanthium sibiricum, hemp and other perennial weeds is poor or basically ineffective. Ineffective against adult weeds. Sorghum, millet and other sensitive crops can not be used; Sugar beet, tomato, potato, cucumber and other resistance is not strong.
Last Update：2022-01-01 10:13:14
alpha,alpha,alpha-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine - Introduction
Insecticide single component standard solution
Last Update：2022-10-16 17:14:11
alpha,alpha,alpha-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine - Safety
Open Data Verified Data
rat oral LD50>lOOOOmg/kg, Mouse 5000mg/kg, dog> 2000mg/kg. Rabbit percutaneous LD50>2000mg/kg; 2000 mg/kg dose feeding rats for 2 years, no adverse effects; Greater toxicity to fish, carp LC50 4. 2mg/L(48h), goldfish 0.59mg/L. Blue gill fish is 0. 058mg/L; The lethal dose of the bee was 24mg/only.
Last Update：2022-01-01 10:13:14
alpha,alpha,alpha-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine - Reference Information
| Henry's Law Constant | 10.19 and 14.89 in distilled water and 33.3‰ NaCl at 20 °C, respectively (wetted-wall column,Rice et al., 1997a) |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| (IARC) carcinogen classification | 3 (Vol. 53) 1991 |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| toxicity | acute oral LD50 in rats> 10000mg/kg, 5000mg/kg in mice, 2000mg/kg in dogs and 2000mg/kg in rabbits. Rats were fed with a dose of 2000 mg/kg for 2 years without any adverse effects. The toxicity to fish is relatively high, carp LC50 is 4.2mg/L (48h), goldfish is 0.59mg/L, blue gill fish is 0.058mg/L. The lethal dose of bees is 24mg/bee. |
| use | broad-spectrum dryland pre-bud herbicide. It can be used for cotton, soybeans, peas, rape, peanuts, potatoes, winter wheat, barley, castor, sunflower, sugar cane, vegetables, fruit trees, etc., and is mainly used to control monocotyledonous weeds and annual broad-leaved weeds, such as barnyard grass, big thrush, horse Tang, Setaria, crickets, bluegrass, thousand gold, oxen, beak, wild oats, etc, it can also control dicotyledonous weeds such as quinoa, amaranth, purslane, chickweed, and polygonum from small seeds. Generally, it is used before sowing or bud, the dosage is 5.6~11.3g of active ingredient/100 m2, 0.6~4.5kg of water is added and sprayed on the land, and then raked into the soil within 8 hours to prevent light decomposition, and the grass killing effect reaches 95%. If it is used for transplanting cotton seedbed, it shall be used after sowing and covering soil, and the soil surface shall be sprayed with 48% emulsifiable concentrate of 11~15mL/100 m2, or the soil shall be sprayed first and then covered after planting. For example, to prevent and remove barnyard grass in dry rice fields, spray water with 48% emulsifiable concentrate 30~60mL/100m2 at the 2~3 leaf stage of rice emergence. If it is used for soybean, use 48% emulsifiable concentrate 19~23mL/100 m2, spray topsoil on water, then mix soil, sow in the southern region every other day, and sow in the northern region after 5~7 days. It is a pre-bud herbicide, used to control annual weeds in cotton and forage legume fields Used as a herbicide for fruits, cotton, soybeans and other crops Excellent dry field herbicide. Mainly used in cotton, soybeans, peanuts, sunflowers, cabbage, peppers, beans, orchards, etc., and can also be used in wheat fields and dry rice fields to control many weeds and certain broad-leaved weeds of annual gramineous and seed reproduction Weeds, such as barnyard grass, Setaria, Matang, Kanmai Niang, cricket grass, thousand gold, bluegrass, brome, wild oats, finch, quinoa, amaranth, millet grass, chow, wood, ground skin, pursla, etc. It has poor or basically ineffective control effect on perennial weeds such as Solanum nigrum, Xanthium, and Abutilon. Not effective for adult weeds. Sensitive crops such as sorghum and millet cannot be used; sugar beets, tomatoes, potatoes, cucumbers, etc. are not resistant and can be used as transplanting fields. The world's annual consumption reaches 10,000 tons and levels. |
| Production method | p-chlorotrifluorotoluene is nitrated with mixed acid to generate 3, 5-dinitro-4-chlorotrifluorotoluene, and then amination with di-n-propylamine and soda ash solution to generate 3, 5-dinitro-4-di-n-propyltrifluorotolamine. Raw material consumption quota: p-chlorotrifluorotoluene (98%)740 kg/t, fuming nitric acid (96%)1010 kg/t, concentrated sulfuric acid (96%)330 kg/t, fuming sulfuric acid (SO 320%)40 kg/t, din-propylamine (98%)310 kg/t, sodium carbonate (98%)200 kg/t. Preparation of 4-Trifluoromethyl-2, 4-dinitrochlorobenzene Toluene is catalyzed to obtain chlorotoluene, and then chlorinated under photocatalysis to obtain benzyl chloride trichloride, and then with Hydrogen fluoride reacts to obtain p-chlorotrifluorotoluene, and finally nitration to 4-trifluoromethyl-2, 4-dinitrochlorobenzene. There are many synthesis methods for 4-trifluoromethyl-2, 4-dinitrochlorobenzene, and the synthesis route is as follows. Preparation of dipropylamine Ethylene is synthesized by carbonyl to obtain propanal, reduced to propanol, and then reacts with ammonia to obtain dipropylamine. Synthesis of trifluralin 4-trifluoromethyl -2, 4-dinitrochlorobenzene and dipropylamine were reacted at 100 ℃ for 2h, and trifluralin was obtained after post-treatment. |
| category | pesticide |
| toxicity classification | poisoning |
| acute toxicity | oral-rat LD50: 1930 mg/kg; Oral-mouse LD50: 3197 mg/kg |
| flammability hazard characteristics | Combustion produces toxic nitrogen oxides and fluoride gases |
| storage and transportation characteristics | warehouse ventilation and low temperature drying; separate from food raw materials storage and transportation |
| fire extinguishing agent | dry powder, foam, sand |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:01:54
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