N-methylbis(2,4-xylyliminomethyl)amine
Amitraz
CAS: 33089-61-1
Molecular Formula: C19H23N3
N-methylbis(2,4-xylyliminomethyl)amine - Names and Identifiers
| Name | Amitraz |
| Synonyms | RACET Mitac TAKTIC SENDER Amitraz Amitraze r.d.27419 methyl-bis(2,4-xylyliminomethyl)amine N-methylbis(2,4-xylyliminomethyl)amine N-Methyl bis(2,4-Xylyliminomethyl)amine n-methyl-bis(2,4-xylyliminomethyl)amine 1,5-di(2,4-dimethylphenyl)-3-methyl-1,3,5-triazapenta-1,4-diene 1,5-bis(2,4-dimethylphenyl)3-methyl-1,3,5-triazapenta-1,4-diene n'-(2,4-dimethylphenyl)-n-(((2,4-dimethylphenyl)imino)methyl)-n-methylmethan N'-(2,4-Dimethylphenyl)N-(((2,4-dimethylphenyl) imino)methyl)N-methylmethanimidamide N'-(2,4-dimethylphenyl)-N-{(E)-[(2,4-dimethylphenyl)imino]methyl}-N-methylimidoformamide (non-preferred name) N'-(2,4-Dimethylphenyl)-N-[[(2,4-dimethylphenyl-imino]methyl]-N-methylmethanimidamide,N-Methylbis(2,4-xylyliminoethyl)amine |
| CAS | 33089-61-1 |
| EINECS | 251-375-4 |
| InChI | InChI=1/C19H23N3/c1-14-6-8-18(16(3)10-14)20-12-22(5)13-21-19-9-7-15(2)11-17(19)4/h6-13H,1-5H3/b20-12+,21-13+ |
| InChIKey | QXAITBQSYVNQDR-ZIOPAAQOSA-N |
N-methylbis(2,4-xylyliminomethyl)amine - Physico-chemical Properties
| Molecular Formula | C19H23N3 |
| Molar Mass | 293.41 |
| Density | 1.1280 |
| Melting Point | 86-87°C |
| Boling Point | 425.25°C (rough estimate) |
| Flash Point | 226.4°C |
| Water Solubility | 0.08 mg l-1 |
| Solubility | Slightly soluble in water, soluble in xylene, acetone and methanol and other organic solvents. |
| Vapor Presure | 3.4×10-4 Pa (25 °C) |
| Appearance | White needle crystal |
| Color | White |
| Maximum wavelength(λmax) | ['247nm(lit.)'] |
| Merck | 14,486 |
| pKa | 4.2 (weak base) |
| Storage Condition | Sealed in dry,Store in freezer, under -20°C |
| Sensitive | Sensitive to light |
| Refractive Index | 1.5892 (estimate) |
| MDL | MFCD00069396 |
| Physical and Chemical Properties | Melting point 86-87°C |
| Use | Broad-spectrum acaricide, mainly used for fruit trees, cotton, vegetables and other crops to control mites, can also be used for cattle, sheep and other livestock to control tick mites |
N-methylbis(2,4-xylyliminomethyl)amine - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R43 - May cause sensitization by skin contact R48/22 - Harmful danger of serious damage to health by prolonged exposure if swallowed. R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S22 - Do not breathe dust. S24 - Avoid contact with skin. S36/37 - Wear suitable protective clothing and 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. |
| UN IDs | UN 3077 |
| WGK Germany | 3 |
| RTECS | ZF0480000 |
| HS Code | 29252900 |
| Hazard Class | 9 |
| Packing Group | III |
| Toxicity | LD50 in male rats, female mice, rabbits, guinea pigs, bobwhite quail (mg/kg): 800, >1600, >100, >400, 788 orally; LD50 in rabbits, male rats (mg/kg): >200, >1600 dermally; LC50 (48 hr) in rainbow trout, Japanese carp: 3.3, 1.2 ppm (Labonne) |
N-methylbis(2,4-xylyliminomethyl)amine - Upstream Downstream Industry
N-methylbis(2,4-xylyliminomethyl)amine - Introduction
The solubility per liter of solvent at room temperature is: water is 1mg, acetone or toluene is more than 300g. Unstable in acidic media. Long-term storage in wet conditions will slowly decompose.
Last Update：2022-10-16 17:24:40
N-methylbis(2,4-xylyliminomethyl)amine - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| broad-spectrum acaricide | amitraz is also known as mite, diworm amidine, and fruit mite killing. It is a broad-spectrum formamidine acaricide, which is a moderately toxic acaricide. In 1971, Palmer (B.H.Palmer) and others reported its acaricide activity. In 1973, Boots Co.Ltd. recommended it as an acaricide. Chemical name: 1, 5-bis-(2, 4-dimethylphenyl)-3-methyl -1,3, 5-triazopentadiene -1,4, the original drug is white or yellow needle-like crystal, with the taste of some carbon amine, the density is 0.3, the melting point is 86~87 ℃, the vapor pressure is 506.6 × 10-7Pa at 20 ℃, and it is slightly soluble in water, soluble in various organic solvents such as xylene, acetone and methanol. It is stable to temperature and light under anhydrous conditions. Unstable under acidity. Non-flammable, non-explosive, long-term storage in humid places easy to decompose and deteriorate. It has the effects of contact killing, food rejection and repellent, as well as certain stomach poison, fumigation and internal absorption. It is effective for various insect states of Tetranychidae, but it is less effective for overwintering eggs. The efficacy period can reach 40~50 days. It is mainly used for fruit trees, vegetables, tea, cotton, soybeans, sugar beets and other crops to control various harmful mites. It also has a good control effect on psyllids, and is effective on some lepidopteran pest eggs. It also has a certain treatment effect on scales, aphids, cotton bollworms, red bollworms, etc., and can also prevent cattle, goats and bee mites. Amitraz can be mixed with organophosphorus, pyrethroids, abamectin and other pesticides, which has a synergistic effect and can expand the insecticidal spectrum. The mixed preparation includes 10.8% Avi Shuangjia EC. |
| Monoformamidine | Monoformamidine is also known as mite killing amidine, mite lick, monoformamidine hydrochloride, egg mite double net, Tianhuan mite clear, Mite net, is an organic nitrogen broad-spectrum maim acaricide, which is a homolog of amitraz. Chemical name: N-(2, 4-xylenyl)-N′-methylformamidine. The products sold on the market are mostly monoformamidine hydrochloride, with a light yellow or brown liquid appearance, a density of 1.090~1.105, a pH value of less than 1, no combustion, and corrosive to metals. Pure product is white needle-like crystal with melting point of 163~165 ℃, soluble in water, acidic aqueous solution, slightly soluble in low molecular weight alcohol, insoluble in organic solvents such as benzene and petroleum ether. Stable to light and heat. It has contact killing and fumigation effects on harmful mites, and is effective on the insect state of each stage of the spider mite family. The efficacy is better at high temperature (above 22 ℃). The effect on overwintering eggs is poor. It mainly inhibits the activity of monoamine oxidase and induces excitation on non-cholinergic synapses of the central nervous system. Mites that are resistant to other acaricides are also effective. Monoformamidine can be mixed with organophosphorus and pyrethroid pesticides, which has a synergistic effect and can expand the insecticidal spectrum. It is mainly used to control plant-eating leaf mites and cotton aphids on various crops such as fruit trees, tea, cotton, vegetables, etc.; it can also be used to control livestock lice and bee mites. Poisoning to humans and animals, poisonous to fish. |
| mechanism of action | amitraz has a variety of toxic mechanisms, mainly inhibiting the activity of monoamine oxidase, and inducing excitatory effects on non-cholinergic synapses in the central nervous system of mites. Harmful mites that are resistant to other acaricides also have higher activity. |
| control object | is mainly used for fruit trees, vegetables, tea, cotton, soybeans, sugar beets and other crops to control a variety of harmful mites. It also has good efficacy against homoptera pests such as pear yellow wood lice and orange yellow whitefly, and can also be effective against the eggs of pear heart feeding worms and various noctuid pests. It also has a certain effect on aphids, cotton bollworm, red bollworm and other pests. It is effective for adult, mite, and summer eggs, but not for winter eggs. |
| usage | (1) control of fruit, tea tree mites and pests. Apple spider mites, apple aphids, citrus red spiders, citrus rust mites, wood lice, tea tarsal mites, with 20% amitraz emulsifiable concentrate 1000~1500 times spray (100~200 mg/kg). The duration is 1 to 2 months. The tea half tarsal mites should be administered again 5 days after the first application to kill the young mites that are hatching. (2) control of vegetable mites. Eggplant, beans and red spiders are sprayed with 20% emulsifiable concentrate 1000~2000 times (effective concentration 100~200 mg/kg) when nymphs are in full bloom. Watermelon and wax gourd red spiders were sprayed with 20% emulsifiable concentrate 2000~3000 times (67~100 mg/kg) during the peak period of mites. (3) control of cotton mites. Cotton red spider was sprayed with 20% emulsifiable concentrate 1000~2000 times (effective concentration 100~200 mg/kg) during the peak period of eggs and mites. 0.1~0.2 mg/kg (equivalent to 2000~1000 times 20% EC). Used in the middle and late stages of cotton growth, it can also treat cotton bollworm and red bollworm. (4) Control of in vitro ticks and other pests in livestock. In vitro tick mites of livestock are sprayed or soaked with 2000~4000 times of 20% amitraz emulsifiable concentrate. Bovine scabies (except horses) can be rubbed with 20% amitraz emulsifiable concentrate 400~1000 times and washed. One time and two times of medicine bath, the interval is 7 days, the effect is good. Bee mites are sprayed with 20% emulsifiable concentrate 4000~5000 times. Spray 1000 times of 20% emulsifiable concentrate for environmental damage mites. |
| precautions | (1) amitraz is used in high temperature and sunny weather, and the efficacy is poor when the temperature is lower than 25 ℃. (2) should not be mixed with alkaline pesticides (such as Bordeaux mixture, sulfur mixture, etc.). The crop is used up to 2 times per season. Do not mix with parathion for apple or pear trees to avoid medicinal damage. (3) stop using citrus 21 days before harvest, with a maximum usage of 1000 times. Cotton was stopped 7 days before harvest, with a maximum usage of 3L/hm2 (20% amitraz emulsifiable concentrate). (4) If the skin is in contact, it should be washed with soap and water immediately. (5) It is harmful to leaf burning on short fruit branches and golden crown apples. It is safer for natural enemies of pests and bees. |
| toxicity | the original drug has an acute oral LD50 of 600mg/kg(800mg/kg) to rats, 1600mg/kg to mice, 1600mg/kg to rats (female> 4640mg/kg), 200mg/kg to rabbits, and 65mg/l to rats. No irritation to animal skin and eyes. The subacute oral dose of rats is 3~12 mg/kg per day, while the chronic oral dose of rats is 2.5~10 mg/kg per day. No carcinogenic, teratogenic and mutagenic effects were found in animal experiments. Toxic to fish, carp LC50 is 1.17mg/L (48h), rainbow trout is 2.7~4mg/L (48h). Low toxicity to natural enemies such as bees and birds. |
| use | broad-spectrum acaricide is mainly contact killing, has stomach poison, fumigation, anti-feeding and repellent effects, has certain osmotic and internal absorption to plants, is effective to juvenile mites, adult mites and mite eggs, and is effective to harmful mites resistant to other acaricides, with good quick effect and strong holding effect. Mainly used to control cotton red spider and cotton bollworm, red bollworm, apple and hawthorn red spider, citrus leaf mites, wood lice, rust ticks, cattle, sheep, pigs in vitro lice, ticks, scabies and tsutsugamushi, tea tree tarsal mites, beans, eggplant red spider, etc. For example, to control cotton red spider, spray 1000~2000 times of 20% emulsifiable concentrate evenly from the full incubation period of eggs to the full growth period of young mites. When red spiders are used concurrently with red bollworm or cotton bollworm, it can be used to treat both insects and mites to a certain extent, and it is safe for natural enemies such as ladybugs and lacewings in cotton fields. If citrus red spiders and apple spider mites are controlled, 20% emulsifiable concentrate is used to dilute the water to 1000~2000 times and spray it. To control citrus rust mites, spray 1000~1200 times of water with 20% emulsifiable concentrate, and spray 1500 times of water with wood lice. Control cattle, sheep and other animals tick mites, spray or soak at a concentration of 50~100mg/L. broad-spectrum acaricide, mainly used for fruit trees, cotton, vegetables and other crops to control mites, but also for cattle, sheep and other livestock to control acaricides the product is a broad-spectrum acaricide. Mainly used in fruit trees, flowers, strawberries and other agricultural and horticultural crops. Control of mites, especially citrus mites have a good effect. It is also used to control cotton bollworm and red bollworm; ticks, mites, scabies, etc. that control livestock parasites. Amitraz is a variety with better efficacy among acaricides. Calibration instruments and devices; evaluation methods; working standards; quality assurance/quality control; other. |
| production method | preparation method one N-2, preparation of 4-dimethylphenyl-N'-methylformamidine m-xylene is nitrated, reduced and separated to produce 2,4-dimethylaniline. Then acidify with hydrochloric acid to obtain the corresponding salt. Operation method: The mixture of 55.1g(0.35mol)2,4-dimethylaniline hydrochloride, 83.7g(0.4mol) p-toluenesulfonyl chloride and 150mL N-methylformamide was cooled and stirred. After the heating reaction is over, the mixture is stirred at room temperature for 4h, then all of it is injected into cold water, adjusted to alkaline with 10mol/L sodium hydroxide solution, and the temperature is kept below 10 ℃ during this period. Filtration, water washing, drying, and cyclohexane recrystallization to obtain N-2, 4-dimethylphenyl-N'-methylformamidine, melting point 75-76 ℃, yield 85%. Synthesis of amitraz 19.4g (0.12mol) N-2, 4-xylene-N'-methylformamidine, 0.3g p-toluenesulfonic acid, 195mL dry xylene mixture heated and refluxed for 48h to release methylamine. After the reaction, xylene was evaporated under reduced pressure, the residue was solidified, and recrystallized twice by isopropanol to obtain amitraz with a melting point of 88~89 ℃ and a yield of 90%. Or in the presence of benzonitrile, Cu2O is used as a catalyst for the reaction. Preparation method Triethyl diorthoformate reacts with 2, 4-dimethylaniline to prepare N-(2, 4-xyleneamino) ethyl formate (referred to as imine ester), and then dry The methylamine gas is passed into the imine ester to obtain monoformamidine (N-2, 4-xylene-N'-methylformamidine). Monoformamidine and imine ester are condensed to synthesize amitraz. Preparation method 3 2,4-dimethylaniline reacts with formic acid to prepare N-2,4-xylene formamide, and then reacts with phosgene to use triethylamine as acid binding agent to obtain 2,4-xylene. Pass the dry methylamine gas into the mixture of xylene and cuprous oxide, add cyclohexane while it is hot after the reaction, cool and filter out monoformamidine. Then react with xylene in benzene to obtain amitraz. It is prepared by the reaction of 2, 4-dimethylaniline, triethyl orthoformate and methylamine. Raw material consumption quota: 2,4-dimethylaniline (folded 100%)350kg/t, triethyl orthoformate (folded 100%)500kg/t, monomethylamine 70kg/t, xylene 750kg/t. |
| category | pesticide |
| toxicity classification | poisoning |
| acute toxicity | oral-rat LD50: 400 mg/kg; Oral-mouse LD50:1600 mg/kg |
| flammability hazard characteristics | combustion produces toxic nitrogen oxide gas |
| 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：2024-04-10 22:29:15
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Raw Materials for N-methylbis(2,4-xylyliminomethyl)amine