N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide
Diflubenzuron
CAS: 35367-38-5
Molecular Formula: C14H9ClF2N2O2
N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide - Names and Identifiers
| Name | Diflubenzuron |
| Synonyms | Largon Dimilin oms1804 difluron OMS 1804 PH 60-40 pdd6040i Micromite DU 112307 PDD 6040-I Diflubenzuron Diflubenzuron E.C. 1-(4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea 3-(2,6-Difluorobenzoyl)-1-(4-chlorophenyl)urea N-[(4-chlorophenyl)carbamoyl]-2,6-difluorobenzamide N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide N-(((4-chlorophenyl)amino)carbonyl)-2,6-difluorobenzamide |
| CAS | 35367-38-5 |
| EINECS | 252-529-3 |
| InChI | InChI=1/C14H9ClF2N2O2.C12H6Cl4O2S/c15-8-4-6-9(7-5-8)18-14(21)19-13(20)12-10(16)2-1-3-11(12)17;13-7-1-3-8(4-2-7)19(17,18)12-6-10(15)9(14)5-11(12)16/h1-7H,(H2,18,19,20,21);1-6H |
N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide - Physico-chemical Properties
| Molecular Formula | C14H9ClF2N2O2 |
| Molar Mass | 310.68 |
| Density | 1.4301 (estimate) |
| Melting Point | 230-232°C |
| Water Solubility | 0.008 g/100 mL |
| Vapor Presure | 1.2 x l0-4 mPa (25 °C) |
| Appearance | Solid |
| Merck | 13,3166 |
| BRN | 2162461 |
| pKa | 8.78±0.46(Predicted) |
| Storage Condition | 0-6°C |
| Physical and Chemical Properties | Pure white crystals, m.p.230 ~ 232 °c. The relative density is 1.56, and the vapor pressure is 1.32 × 10-5pa (50 ° C.). Soluble in acetonitrile, dimethyl sulfoxide, soluble in ethyl acetate, ethanol, dichloromethane, slightly soluble in ether, benzene, petroleum ether, acetone solubility of 6.5g/L, in water for 0.1mg/L. Light, Heat more stable, stable storage at room temperature, alkali or acid easily decomposed, can be decomposed by soil microorganisms. Industrial products are white to light yellow crystals, m.p.210 ~ 230 ℃. |
| Use | Used to kill armyworm on corn and wheat |
N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide - Risk and Safety
| Risk Codes | 50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | 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 | 3077 |
| WGK Germany | 2 |
| RTECS | YS6200000 |
| Hazard Class | 9 |
| Packing Group | III |
| Toxicity | LD50 in mice, rats (formulation with 50% kaolin) (g/kg): 4.64, >10 orally (Mulder, Gijswijt) |
N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide - Upstream Downstream Industry
N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide - Nature
Open Data Verified Data
pure white crystals, melting point 230~232 deg C. The original drug (more than 95%) is white to light yellow crystals, the melting point is 210~230. The relative density is 1. 56 and the vapor pressure (50 ℃) is 1.32 × 10-s Pa. Soluble in acetonitrile, dimethyl sulfoxide, soluble in ethyl acetate, ethanol dichloromethane. Slightly soluble in ether, benzene, petroleum ether, water solubility (20 C) about 0.2 x 10-6. Stable to light and heat, stable storage at room temperature, easy to decompose in case of alkali or strong acid, and can be decomposed by soil microorganisms.
Last Update：2024-01-02 23:10:35
N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide - Preparation Method
Open Data Verified Data
2,6-= fluorobenzonitrile is prepared from 2,6-= chlorobenzonitrile in the presence of solvent and potassium fluoride, and is hydrolyzed at 65-70 ℃ in the presence of sulfuric acid to prepare 2,6-= fluoroaniline, and then with 4 chlorophenyl isocyanate reaction can be prepared dicarbamide. Alternatively, 2,6-= fluorobenzamide is reacted with phosgene to produce 2,6-= fluorophenyl isocyanate, which is then added to p-chloroaniline to produce dimethuron.
Last Update：2022-01-01 10:11:45
N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide - Use
Open Data Verified Data
benzoylurea insecticides. Can inhibit the synthesis of chitin in insects. The main effect is gastric toxicity, and has the effect of killing. The residual period is longer, but the efficacy is slow. For the prevention and control of Lepidoptera a variety of pests, especially on the larvae of the effect is better, the crops, natural enemies safety. Such as the prevention and control of diamondback moth, beet armyworm, Spodoptera litura, etc., in the egg incubation period to 1~2 instar larvae, with 25% suspension 500~1000 times liquid spray. Control of corn borer, corn iron beetle, in the early larval incubation period or spawning peak, with 20% suspension of 1000 to 2000 times the liquid spray, can kill eggs and larvae. Control of armyworm, in the larval peak period, with 20% per hectare of suspension 75 ~ 150g into the water spray 750kg. Prevention and Control of citrus leaf moth, in the early stage of shooting, egg incubation period, with 25% suspension 2000 times liquid spray. It can also be used for the prevention and control of picrophagia pear, Dendrolimus punctatus, poisonous moth, leaf roller, etc.
Last Update：2022-01-01 10:11:46
N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide - Safety
Open Data Verified Data
The oral LD50 of the original drug on rats and mice was greater than 4640mg/kg, the percutaneous LD50 of rabbits was> 2000mg/kg, and the inhalation LCso was> 300mg/L. It has mild irritation to clear eyes and skin of rabbits. The oral no-effect dose in rats was 125mg/kg per day. No teratogenic and mutagenic effects were observed in the experimental dose. Low toxicity to birds, quail acute oral LD50>4640mg/kg. Salmon LC50 0.3mg/L(30d).
Last Update：2022-01-01 10:11:46
N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Insecticide | Insecticide is a specific low-toxic insecticide, belonging to benzoyl, which has stomach toxicity and contact killing effects on pests. By inhibiting the synthesis of insect chitin, the larvae cannot form a new epidermis when molting, and the worm body is deformed and dies, but the drug effect is slow. The medicine has special effects on lepidopteran pests. It is safe to use and has no adverse effects on fish, bees and natural enemies. |
| mode of action | stomach poison and contact killing, no systemic nature, dewort urea is a growth regulator of benzoylurea insects. The mechanism of action is to inhibit the synthesis of pest chitin, effective for a variety of lepidopteran pests, no phytotoxicity to plants under effective dosage, and beneficial organisms such as birds, fish, shrimps, frogs, bees, ladybugs, armour, spiders, lacewings, Trichogramma, ants, parasitic wasps, etc. have no adverse effects, and the efficacy of pests is slow. |
| control object | has special effects on lepidopteran pests, has good control effects on various pests such as Coleoptera and Diptera, and has no obvious adverse effects on beneficial organisms and natural enemies. Mainly used in apples, pears, citrus, corn, rice and cruciferous vegetables and other crops, control apple leaf moth, beet armyworm, pear heartworm, pear wood lice, corn, wheat armyworm, citrus wood lice, rapae and other pests. |
| usage | rust ticks: control citrus rust ticks from the full incubation period to the nymphal period, spray 60-80 mg/kg. Tea geometrid: spray 100-200mg/kg to prevent tea geometrid from the full incubation period to the 3th instar. Leaf miner: control citrus leaf miner 60-125mg.kg spray. armyworm: active ingredient 15~30g/hm, in the first generation of armyworm 3~4 instar, 2 generations of egg hatching peak, 3 generations of armyworm 2 ~# instar, spray on water. Corn borer: during the initial incubation or peak spawning period, 100~200mg/L is used for heart filling or spraying. Rice leaf roller: before the 1~3 instar of the larvae, spray with 25mg/L. Cabbage and Plutella xylostella: spray with active ingredient 150~225g/hm or 25mg/L liquid medicine at the early stage of larval occurrence. Spodoptera exigua and Spodoptera litura: spray with 100mg/kg liquid medicine at the initial stage of incubation. Helicoverpa armigera: spray with 3~4mg/L liquid medicine at the peak of spawning. Citrus woodlice: spray with 100mg/L liquid medicine during nymphal stage. Pine caterpillars, caterpillars, and poplar moths: spray water with the active ingredient 30~45g/hm ² at the low instar of the larvae. The drug has a killing effect on these pests. Mosquito larvae: active ingredient 25~40g/hm² water surface area spraying. Rope larvae: active ingredient 0.5~1g/hm surface area spraying. The drug is effective against termites, ants, cockroaches and storage pests. |
| toxicity | the original drug has an acute oral LD50 of rats> 46401 mg/kg (also reported to rats> 1500 mg/kg). Acute percutaneous LD50>2000mg/kg in rabbits and acute inhalation LC50>30mg/L. It has mild irritation to rabbit eyes and skin. The oral dose of rats was 125mg/kg per day. No animal teratogenic or mutagenic effect was found in the test dose. Acute oral LD50 of quail> 4640mg/kg, LC50 of salmon is 0.3mg/L (30d), and LD50 of bee exposure <30 μg/animal. According to my country's pesticide toxicity classification standards, dewort is a low-toxic insecticide. Toxicity to aquatic organisms LC50(96 hours, mg/L): rainbow trout 140, blue-gill sunfish 135, harmless to bees LD50 (oral, transdermal)>100 μg/peak; toxicity to natural enemies LC50(8-day diet): North American quail and mallard> 4640mg/L diet, no harm to carnivorous insects. Acute oral LD50>4640mg/L in rats and mice, acute percutaneous LD50>2 g/kg in rabbits, 10 g/kg in rats, and acute inhalation of LC50>2.88mg/L in rats. It has irritation to rabbit eyes and no irritation to skin. This drug has no obvious accumulation effect in animals and can be metabolized quickly. Under the experimental conditions, no mutagenic, teratogenic and carcinogenic effects were found. Two years of feeding rats with no effect dose of 40mg/L, mice 50mg/L. Salmon was fed experimental LC500.3mg/L for 30 days. Low toxicity to bees, acute exposure LD50>100 μg/head; Low toxicity to birds, 8-day feeding test, acute oral LD50 of wild ducks and quails> 4640mg/L; Daphnia LC50(48 hours) 7.1 μg/L. |
| use | benzoylurea insecticides. Inhibition of the synthesis of insect chitosan. It mainly has the effect of stomach poison and has the effect of contact killing. The residual effect period is longer, but the drug effect speed is slower. It is used to control various pests of Lepidoptera, especially for larvae, and is safe for crops and natural enemies. Such as the control of Plutella xylostella, Spodoptera litura, Spodoptera exigua, Pieris rapae, etc., in the egg incubation period to 1~2 instar larval period, with 25% suspension agent 500~1000 times liquid spray. To prevent and control corn borer and corn iron beetle, during the initial incubation period or peak spawning period of the larvae, 1000~2000 times of the 20% suspension agent is used to fill the heart leaves or spray the larvae, which can kill eggs and incubate the larvae. To control armyworms, spray 750kg of water with 20% suspending agent 75~150g/hm2 during the larval period. To prevent and control citrus leaf miner, spray 2000 times liquid with 25% suspending agent at the early stage of tip extraction and egg incubation. In addition, it can also control pear heartworms, poisonous moths, pine caterpillars, rice leaf roller, etc. It is used to kill armyworms on corn and wheat It has special effects on lepidopteran pests, and it is also effective on various pests of Coleoptera and Diptera Amuranophora is a new insecticide, It has gastric toxicity to the larvae of many important pests. It can cause insects to die by interfering with epidermal deposition. It can also inhibit the formation of epidermis during the embryonic development of insect eggs, so that the eggs cannot develop and hatch normally, and it also has a certain inhibitory effect on the fertility of insects. The product has a wide insecticidal spectrum, especially for Lepidoptera larvae. Due to its unique mechanism of action, it has low toxicity to humans and animals and little harm to natural enemies. It is a relatively good selective insecticide developed in recent years. |
| production method | 2, 6-difluorobenzamide and 4-chlorophenyl isocyanate are placed in xylene and heated and refluxed, and the reaction is completed. After cooling, the obtained crystals are washed and dried with xylene to obtain urapon. The preparation of 2, 6-difluorobenzamide is prepared by 2, 6-dichlorobenzonitrile through fluorination and nucleophilic addition reaction. Refer to the preparation method of fluaziride. The synthesis of pyridine can also be prepared by the reaction of 2, 6-difluorobenzamide and 4-chlorophenyl isocyanate. |
| 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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View History
N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide
Pyridine-2-carbaldoxime methochloride
Benzeneacetonitrile, α-[2-(dimethylamino)propyl]-α-ethyl-
1-Ethyl-1H-indazole-3-carboxylic acid
hexasodium 4-amino-3,6-bis[[4-[[4-chloro-6-[(4-sulphonatophenyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulphonatophenyl]azo]-5-hydroxynaphthalene-2,7-disulphonate
Acetamide, N-(butoxymethyl)-2-chloro-N-[2-ethyl-6-(1-methylpropyl)phenyl]-
benzyl N-[(1S)-1-[[(2S,5S)-3,3-difluoro-5-[[(2S)-3-methyl-2-phenylmeth oxycarbonylamino-butanoyl]amino]-4-oxo-1,6-diphenyl-hexan-2-yl]carbamo yl]-2-methyl-propyl]carbamate
1,5,10-Triazacyclopentadecane
Pyridine-2-carbaldoxime methochloride
Benzeneacetonitrile, α-[2-(dimethylamino)propyl]-α-ethyl-
1-Ethyl-1H-indazole-3-carboxylic acid
hexasodium 4-amino-3,6-bis[[4-[[4-chloro-6-[(4-sulphonatophenyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulphonatophenyl]azo]-5-hydroxynaphthalene-2,7-disulphonate
Acetamide, N-(butoxymethyl)-2-chloro-N-[2-ethyl-6-(1-methylpropyl)phenyl]-
benzyl N-[(1S)-1-[[(2S,5S)-3,3-difluoro-5-[[(2S)-3-methyl-2-phenylmeth oxycarbonylamino-butanoyl]amino]-4-oxo-1,6-diphenyl-hexan-2-yl]carbamo yl]-2-methyl-propyl]carbamate
1,5,10-Triazacyclopentadecane
Raw Materials for N-[[(4-chlorophenyl)amino]carbonyl]-2,6-difluorobenzamide