CN1903838A - Preparation method of benzoyl area kind derivative - Google Patents
Preparation method of benzoyl area kind derivative Download PDFInfo
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- CN1903838A CN1903838A CN 200610052765 CN200610052765A CN1903838A CN 1903838 A CN1903838 A CN 1903838A CN 200610052765 CN200610052765 CN 200610052765 CN 200610052765 A CN200610052765 A CN 200610052765A CN 1903838 A CN1903838 A CN 1903838A
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Abstract
The present invention relates to a preparation method of benzoyl urea derivative. In particular, it relates to a chemical synthesis method for preparing benzoyl urea derivative by using bis (trichloromethyl) carbonate instead of phosgene, diphosgene or oxalyl chloride to directly react with substituted aniline and substituted benzamide. Its reaction temperature is 20-200deg.C and reaction time is 1-20h.
Description
(1) technical field
The present invention relates to a kind of preparation method of benzoyl area kind derivative, particularly substitute phosgene, trichloromethylchloroformate or oxalyl chloride directly and the chemical synthesis process of substituted aniline and substituted benzamide prepared in reaction benzoyl area kind derivative with two (trichloromethyl) carbonic ethers.
(2) background technology
Before the present invention, the existing technology of chemosynthesis benzoyl area kind derivative is by substituted benzamide photoreactive gas or the synthesizing substituted formyl isocyanic ester of oxalyl chloride, and then generates benzoyl area kind derivative with the substituted aniline reaction.For example: US4622340 (1986), US 6022882 (2000), chemical engineer, 2005,115 (4): 55 etc.At present in the suitability for industrialized production, with substituted benzamide and excessive oxalyl chloride 1, reflux in the 2-ethylene dichloride after a few hours, underpressure distillation removes desolvates and unreacted oxalyl chloride obtains the substituted benzene formyl isocyanic ester, add freshly 1 again, the 2-ethylene dichloride slowly drips substituted aniline, room temperature reaction a few hours, filter and obtain benzoyl area kind derivative.Production technique is carried out in two steps, and it is big to consume a large amount of solvents, complex operation, labour intensity.Simultaneously, oxalyl chloride is colourless fuming liquid, and pungent pungent taste is arranged, and meets water or alcohol and is vigorous reaction and decomposites hydrogenchloride, poisonous and corrodibility.And the price of oxalyl chloride is higher, is 6～7 times of two (trichloromethyl) carbonic ethers, makes that the production cost of present benzoyl area kind derivative is very high.Comprehensively above-mentioned, existing benzoyl area kind derivative production technique exist production cost height, equipment corrosion serious, consume problems such as a large amount of high toxicities, strong carcinogenic solvent, complicated operation, complex operation, labour intensity are big, potential safety hazard is big.Also useful phosgene of suitability for industrialized production and trichloromethylchloroformate substitute the industrialized producing technology of oxalyl chloride at present.But phosgene is the hypertoxic gas of strict in the world control and limit production and use, the volatility height, and severe toxicity, all there are very big potential safety hazard in preparation, storage, transportation.Trichloromethylchloroformate is a liquid, and security is better than phosgene, can resolve into phosgene but run into gac, iron or organic amine etc., thereby still has bigger potential safety hazard in use and transportation.
(3) summary of the invention
The objective of the invention is for overcome traditional technology production cost height, equipment corrosion serious, use problems such as a large amount of high toxicities, strong carcinogenic solvent, complicated operation, potential safety hazard are big, provide one simple to operate, production safety is reliable, reaction yield is high, production cost is low, the chemical synthesis process of eco-friendly benzoyl area kind derivative.
The technical solution used in the present invention is as follows:
A kind of preparation method suc as formula the benzoyl area kind derivative shown in (I), by the substituted aniline shown in the formula (II) and the substituted benzamide shown in two (trichloromethyl) carbonic ethers and the formula (III) in organic solvent, in 20～200 ℃ of reaction 1～20h, obtain described benzoyl area kind derivative
Wherein, R
1And R
2Independent separately is hydrogen or halogen, R
3, R
4, R
5, R
6And R
7Independent separately be the aryl ether group of the alkoxyl group of the alkyl of hydrogen, halogen, C1～C5 or substituted alkyl, C1～C5 or substituted alkoxy, C6～C10 or replacement aryl ether group, substituted heterocycle aryl ether group, and described organic solvent is an aprotic solvent.
Among the preparation method of described benzoyl area kind derivative, described substituted aniline: two (trichloromethyl) carbonic ether: the amount of substance ratio of substituted benzamide is 1: 0.3～1.5: 1.0～1.5, be preferably 1: 0.4～1.0: 1.0～1.2, most preferably be 1: 0.4～0.5: 1.0～1.1.
Aprotic organic solvent described in the method is one of following: the halogenated alkane of benzene, substituted benzene, C1～C5, the fatty ester of C2～C8, ether solvent, tetrahydrofuran (THF) or tetramethylene sulfone, described substituted benzene are methyl substituted benzene, nitro substituted benzene, halogen substituted benzene;
Further, it is one of following that organic solvent is preferably: benzene,toluene,xylene, chlorobenzene, orthodichlorobenzene, Meta Dichlorobenzene, santochlor, oil of mirbane, methylene dichloride, chloroform, tetracol phenixin, 1,1-ethylene dichloride, 1,2-ethylene dichloride, methyl-formiate, ethyl formate, propyl formate, butyl formate, ethyl acetate, methyl acetate, propyl acetate, butylacetate, ether, dibutyl ether, dioxane, tetrahydrofuran (THF), tetramethylene sulfone.
Further again, described organic solvent is one of following: toluene, dimethylbenzene, chlorobenzene, oil of mirbane, chloroform, tetracol phenixin, 1,2-ethylene dichloride, tetramethylene sulfone, the consumption of described organic solvent be the reactant gross weight 0.5-5 doubly.
Among the preparation method of described benzoyl area kind derivative, one of described substituted aniline is preferred following: 3,5-two chloro-2,4 difluorobenzene amine, 3,4-dichlorphenamide bulk powder, 4-chloroaniline, 4-5-trifluoromethylaniline, 4-trifluoro-methoxyaniline or 3,5-two chloro-4-(1,1-two fluoro-2, the 2-difluoroethoxy) aniline, described substituted benzamide preferred 2,6-difluorobenzamide or 2, the 6-dichloro-benzamide.
Comparatively concrete, the preparation method of benzoyl area kind derivative is: according to substituted aniline: two (trichloromethyl) carbonic ether: the amount of substance ratio of substituted benzamide is 1: 0.4～0.5: 1.0～1.1, under the ice bath cooling, two (trichloromethyl) carbonic ethers are dissolved in the organic solvent, mixed solution with substituted aniline and organic solvent slowly adds again, dropwise at 20～200 ℃ and react 0.5～10h down, be cooled to room temperature, the mixed solution of substituted benzamide and organic solvent is added, react 0.5～10h down at 20～200 ℃, naturally cooling filters, and vacuum-drying promptly gets the product benzoyl area kind derivative.
Preferably, described substituted aniline is 50～150 ℃ of reactions 1～7 hour with two (trichloromethyl) carbonic ethers in temperature, more preferably 80～100 ℃ of reactions 2～5 hours, it is 70～160 ℃ of reactions 3～10 hours in temperature that the substituted benzene formyl amine aqueous solution adds the back, better at 100～120 ℃ of reaction 5～8h.
Concrete, the preparation method of benzoyl area kind derivative is according to substituted aniline: two (trichloromethyl) carbonic ether: the amount of substance ratio of substituted benzamide is 1: 0.4～0.5: 1.0～1.1, under the ice bath cooling, two (trichloromethyl) carbonic ethers are dissolved in the organic solvent, again with 3,5-two chloro-2, the mixed solution of 4-difluoroaniline or 4-5-trifluoromethylaniline and organic solvent slowly adds, dropwise at 80～100 ℃ and react 2～5h down, be cooled to room temperature, 2,6-difluorobenzamide or 2, the mixing solutions of 6-dichloro-benzamide and organic solvent adds, and reacts 5～8h, naturally cooling down at 100～120 ℃, filter, vacuum-drying promptly gets product, and described organic solvent is toluene or dimethylbenzene, and total consumption is 1.5 times of reactant gross weight.
The present invention compared with prior art, its beneficial effect is embodied in:
Oxalyl chloride, phosgene or the trichloromethylchloroformate of having used two (trichloromethyl) carbonic ethers to substitute in the existing technology are reacted, two (trichloromethyl) carbonic ether claims solid phosgene again, be stable solid chemical compound (77～83 ℃ of fusing points, 205～206 ℃ of boiling points), even when boiling, also only because decomposite the phosgene of trace, thereby it is very safe in transportation, storage and use, convenient, only when general toxic substance processing, its price only is 1/7～1/6 of an oxalyl chloride, a little more than phosgene and triphosgene.Therefore generally speaking, the present invention is simple to operate, reactions steps is few, solvent loss is little, environmental friendliness, production safety is reliable, production cost is low, the reaction yield height, and toxicity is little, and corrodibility is little, has big industrialization potentiality and economic results in society.
(4) embodiment:
Below with specific embodiment technical scheme of the present invention is described, but protection scope of the present invention is not limited thereto:
Embodiment 1
In the 500mL there-necked flask, the reflux condensing tube and the thermometer of dress dropping funnel, band calcium chloride tube are used magnetic stirrer.In there-necked flask, add 100mL dimethylbenzene and 59.5g (0.2mol) two (trichloromethyl) carbonic ether (BTC), ice bath is cooled to below 0 ℃, stir, with 99.0g (0.5mol) 3,5-two chloro-2, the mixed solution of 4-difluoroaniline and 50mL dimethylbenzene slowly splashes into, and 5～10 ℃ of control dropping temperatures dropwise and are warming up to 90 ℃ of reaction 3h.Naturally cooling slowly adds 78.6g (0.5mol) 2, the mixed solution of 6-difluorobenzamide and 50mL dimethylbenzene; dropwise and be warming up to 100 ℃ of reaction 7h, stopped reaction, naturally cooling; filter, vacuum-drying gets white needles solid 181.2g; be product 1-(3; 5-two chloro-2,4 difluorobenzene bases)-3-(2, the 6-difluoro benzoyl) urea; yield is 93.5%, is 98.3% through efficient liquid phase chromatographic analysis purity.
Embodiment 2
The amount of substance ratio that feeds intake is 3, and 5-two chloro-2,4 difluorobenzene amine: two (trichloromethyl) carbonic ether is 1: 0.5, and other is operated with embodiment 1.Yield is 94.2%, is 98.6% through efficient liquid phase chromatographic analysis purity.
Embodiment 3
The amount of substance ratio that feeds intake is 3, and 5-two chloro-2,4 difluorobenzene amine: two (trichloromethyl) carbonic ether is 1: 0.6, and other is operated with embodiment 1.Yield is 94.7%, is 98.7% through efficient liquid phase chromatographic analysis purity.
Embodiment 4
The amount of substance ratio that feeds intake is 3, and 5-two chloro-2,4 difluorobenzene amine: two (trichloromethyl) carbonic ether is 1: 1.2, and other is operated with embodiment 1.Yield is 96.2%, is 99.1% through efficient liquid phase chromatographic analysis purity.
Embodiment 5
The amount of substance ratio that feeds intake is 3,5-two chloro-2,4 difluorobenzene amine: 2, and the 6-difluorobenzamide is 1: 1.1, other is operated with embodiment 1.Yield is 93.6%, is 98.5% through efficient liquid phase chromatographic analysis purity.
Embodiment 6
The amount of substance ratio that feeds intake is 3,5-two chloro-2,4 difluorobenzene amine: 2, and the 6-difluorobenzamide is 1: 1.2, other is operated with embodiment 1.Yield is 93.9%, is 98.8% through efficient liquid phase chromatographic analysis purity.
Embodiment 7
The amount of substance ratio that feeds intake is 3,5-two chloro-2,4 difluorobenzene amine: 2, and the 6-difluorobenzamide is 1: 1.5, other is operated with embodiment 1.Yield is 94.3%, is 99.0% through efficient liquid phase chromatographic analysis purity.
Embodiment 8
With 3,5-two chloro-2,4 difluorobenzene amine aqueous solutions dropwise the afterreaction temperature and change 80 ℃ into, and other is operated with embodiment 1.Yield is 93.1%, is 98.0% through efficient liquid phase chromatographic analysis purity.
Embodiment 9
3,5-two chloro-2,4 difluorobenzene amine aqueous solutions dropwise the afterreaction temperature and change 100 ℃ into, and other is operated with embodiment 1.Yield is 93.9%, is 98.9% through efficient liquid phase chromatographic analysis purity.
Embodiment 10
2,6-difluorobenzamide solution dropwises the afterreaction temperature and changes 110 ℃ into, and other is operated with embodiment 1.Yield is 94.3%, is 98.6% through efficient liquid phase chromatographic analysis purity.
Embodiment 11
2,6-difluorobenzamide solution dropwises the afterreaction temperature and changes 120 ℃ into, and other is operated with embodiment 1.Yield is 94.6%, is 98.7% through efficient liquid phase chromatographic analysis purity.
Embodiment 12
3,5-two chloro-2,4 difluorobenzene amine aqueous solutions dropwise the afterreaction time and change 4h into, and other is operated with embodiment 1.Yield is 94.3%, is 99.1% through efficient liquid phase chromatographic analysis purity.
Embodiment 13
3,5-two chloro-2,4 difluorobenzene amine aqueous solutions dropwise the afterreaction time and change 5h into, and other is operated with embodiment 1.Yield is 94.8%, is 99.3% through efficient liquid phase chromatographic analysis purity.
Embodiment 14
2,6-difluorobenzamide solution dropwises the afterreaction time and changes 6h into, and other is operated with embodiment 1.Yield is 93.7%, is 98.8% through efficient liquid phase chromatographic analysis purity.
Embodiment 15
2,6-difluorobenzamide solution dropwises the afterreaction time and changes 8h into, and other is operated with embodiment 1.Yield is 94.4%, is 98.9% through efficient liquid phase chromatographic analysis purity.
Embodiment 16
Solvent xylene changes chlorobenzene into, and other is operated with embodiment 1.Yield is 92.8%, is 97.8% through efficient liquid phase chromatographic analysis purity.
Embodiment 17
Solvent xylene changes 1 into, the 2-ethylene dichloride, and other is operated with embodiment 1.Yield is 92.8%, is 97.8% through efficient liquid phase chromatographic analysis purity.
Embodiment 18
Solvent xylene changes toluene into, and other is operated with embodiment 1.Yield is 93.1%, is 98.5% through efficient liquid phase chromatographic analysis purity.
Embodiment 19
3,5-two chloro-2,4 difluorobenzene amine change 3 into, the 4-dichlorphenamide bulk powder, and 2, the 6-difluorobenzamide changes 2 into, the 6-dichloro-benzamide, other is operated with embodiment 1.Obtain product 1-(3, the 4-dichlorophenyl)-3-(2,6-dichloro-benzoyl base) urea 178.4g, yield is 94.1%, is 99.7% through efficient liquid phase chromatographic analysis purity.
Embodiment 20
3,5-two chloro-2,4 difluorobenzene amine change the 4-chloroaniline into, and other is operated with embodiment 1.Obtain product 1-(4-chloro-phenyl-)-3-(2, the 6-difluoro benzoyl) urea 148.5g, yield is 93.8%, is 98.1% through efficient liquid phase chromatographic analysis purity.
Embodiment 21
3,5-two chloro-2,4 difluorobenzene amine change the 4-chloroaniline into, and 2, the 6-difluorobenzamide changes 2 into, the 6-dichloro-benzamide, other is operated with embodiment 1.Obtain product 1-(4-chloro-phenyl-)-3-(2,6-dichloro-benzoyl base) urea 160.7g, yield is 92.3%, is 98.7% through efficient liquid phase chromatographic analysis purity.
Embodiment 22
3,5-two chloro-2,4 difluorobenzene amine change the 4-5-trifluoromethylaniline into, and other is operated with embodiment 1.Obtain product 1-(4-trifluoromethyl)-3-(2, the 6-difluoro benzoyl) urea 165.9g, yield is 95.3%, is 98.9% through efficient liquid phase chromatographic analysis purity.
Embodiment 23
3,5-two chloro-2,4 difluorobenzene amine change the 4-trifluoro-methoxyaniline into, and other is operated with embodiment 1.Obtain product 1-(4-Trifluoromethoxyphen-l)-3-(2, the 6-difluoro benzoyl) urea 175.4g, yield is 95.6%, is 98.2% through efficient liquid phase chromatographic analysis purity.
Embodiment 24
3,5-two chloro-2,4 difluorobenzene amine change 3 into, 5-two chloro-4-(1,1-two fluoro-2,2-difluoroethoxy) aniline, and other is operated with embodiment 1.Obtain product 1-[3,5-two chloro-4-(1,1-two fluoro-2,2-difluoroethoxy) phenyl]-3-(2, the 6-difluoro benzoyl) urea 218.0g, yield is 91.5%, is 96.8% through efficient liquid phase chromatographic analysis purity.
Embodiment 25
Solvent xylene changes 1 into, the 1-ethylene dichloride, and other is operated with embodiment 1.Yield is 87.6%, is 98.7% through efficient liquid phase chromatographic analysis purity.
Embodiment 26
Solvent xylene changes ethyl formate into, and other is operated with embodiment 1.Yield is 98.7%, is 98.2% through efficient liquid phase chromatographic analysis purity.
Embodiment 27
Solvent xylene changes dioxane into, and other is operated with embodiment 1.Yield is 98.4%, is 98.9% through efficient liquid phase chromatographic analysis purity.
Embodiment 28
Solvent xylene changes tetramethylene sulfone into, and other is operated with embodiment 1.Yield is 99.1%, is 98.8% through efficient liquid phase chromatographic analysis purity.
Claims (10)
1. preparation method suc as formula the benzoyl area kind derivative shown in (I), it is characterized in that described method be by the substituted aniline shown in the formula (II) and the substituted benzamide shown in two (trichloromethyl) carbonic ethers and the formula (III) in organic solvent, in 20～200 ℃ of reaction 1～20h, obtain described benzoyl area kind derivative
Wherein, R
1And R
2Independent separately is hydrogen or halogen, R
3, R
4, R
5, R
6And R
7Independent separately be the aryl ether group of the alkoxyl group of the alkyl of hydrogen, halogen, C1～C5 or substituted alkyl, C1～C5 or substituted alkoxy, C6～C10 or replacement aryl ether group, substituted heterocycle aryl ether group, and described organic solvent is an aprotic solvent.
2. the preparation method of benzoyl area kind derivative as claimed in claim 1, it is characterized in that described substituted aniline: two (trichloromethyl) carbonic ether: the amount of substance ratio of substituted benzamide is 1: 0.3～1.5: 1.0～1.5.
3. the preparation method of benzoyl area kind derivative as claimed in claim 2, it is characterized in that described substituted aniline: two (trichloromethyl) carbonic ether: the amount of substance ratio of substituted benzamide is 1: 0.4～1.0: 1.0～1.2.
4. the preparation method of benzoyl area kind derivative as claimed in claim 1, it is characterized in that described organic solvent is one of following: the halogenated alkane of benzene, substituted benzene, C1～C5, the fatty ester of C2～C8, ether solvent, tetrahydrofuran (THF) or tetramethylene sulfone, described substituted benzene are methyl substituted benzene, nitro substituted benzene, halogen substituted benzene.
5. the preparation method of benzoyl area kind derivative as claimed in claim 4, it is characterized in that described organic solvent is one of following: benzene,toluene,xylene, chlorobenzene, orthodichlorobenzene, Meta Dichlorobenzene, santochlor, oil of mirbane, methylene dichloride, chloroform, tetracol phenixin, 1,1-ethylene dichloride, 1,2-ethylene dichloride, methyl-formiate, ethyl formate, propyl formate, butyl formate, ethyl acetate, methyl acetate, propyl acetate, butylacetate, ether, dibutyl ether, dioxane, tetrahydrofuran (THF), tetramethylene sulfone.
6. the preparation method of benzoyl area kind derivative as claimed in claim 5, it is characterized in that described organic solvent is one of following: toluene, dimethylbenzene, chlorobenzene, oil of mirbane, chloroform, tetracol phenixin, 1,2-ethylene dichloride, tetramethylene sulfone, the consumption of described organic solvent are 0.5-5 times of reactant gross weight.
7. the preparation method of benzoyl area kind derivative as claimed in claim 1, it is characterized in that described substituted aniline is one of following: 3,5-two chloro-2,4 difluorobenzene amine, 3,4-dichlorphenamide bulk powder, 4-chloroaniline, 4-5-trifluoromethylaniline, 4-trifluoro-methoxyaniline or 3,5-two chloro-4-(1,1-two fluoro-2, the 2-difluoroethoxy) aniline, described substituted benzamide is 2,6-difluorobenzamide or 2, the 6-dichloro-benzamide.
8. the preparation method of benzoyl area kind derivative as claimed in claim 1, it is characterized in that described method is: according to substituted aniline: two (trichloromethyl) carbonic ether: the amount of substance ratio of substituted benzamide is 1: 0.4～0.5: 1.0～1.1, under the ice bath cooling, two (trichloromethyl) carbonic ethers are dissolved in the organic solvent, mixed solution with substituted aniline and organic solvent slowly adds again, dropwise at 20～200 ℃ and react 0.5～10h down, be cooled to room temperature, the mixed solution of substituted benzamide and organic solvent is added, react 0.5～10h down at 20～200 ℃, naturally cooling, filter, vacuum-drying promptly gets described substituted benzoyl urea derivative.
9. the preparation method of benzoyl area kind derivative as claimed in claim 8, it is characterized in that described substituted aniline and two (trichloromethyl) carbonic ethers are 50～150 ℃ of reactions 1～7 hour in temperature, it is 70～160 ℃ of reactions 3～10 hours in temperature that the substituted benzene formyl amine aqueous solution adds the back.
10. the preparation method of benzoyl area kind derivative as claimed in claim 9, it is characterized in that described method is according to substituted aniline: two (trichloromethyl) carbonic ether: the amount of substance ratio of substituted benzamide is 1: 0.4～0.5: 1.0～1.1, under the ice bath cooling, two (trichloromethyl) carbonic ethers are dissolved in the organic solvent, again with 3,5-two chloro-2,4-difluoroaniline or 4-5-trifluoromethylaniline) and the mixed solution of organic solvent slowly add, dropwise at 80～100 ℃ and react 2～5h down, be cooled to room temperature, with 2,6-difluorobenzamide or 2, the mixed solution of 6-dichloro-benzamide and organic solvent adds, react 5～8h down at 100～120 ℃, naturally cooling filters, vacuum-drying promptly gets product, and described organic solvent is toluene or dimethylbenzene.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102532062A (en) * | 2010-12-08 | 2012-07-04 | 上海工程技术大学 | Benzoyl urea compound and synthesis method thereof |
| CN112876384A (en) * | 2021-01-20 | 2021-06-01 | 安阳市安林生物化工有限责任公司 | Synthesis process and application of diflubenzuron |
| CN113773230A (en) * | 2021-09-07 | 2021-12-10 | 京博农化科技有限公司 | Method for synthesizing diflubenzuron by one-pot method |
| CN114380719A (en) * | 2022-01-06 | 2022-04-22 | 坛墨质检科技股份有限公司 | Preparation method of stable isotope labeled chlorbenzuron internal standard reagent |
| CN115108974A (en) * | 2022-07-15 | 2022-09-27 | 重庆医药高等专科学校 | 2, 6-difluorobenzoylurea derivative and preparation method and application thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3161657D1 (en) * | 1980-11-22 | 1984-01-19 | Celamerck Gmbh & Co Kg | Urea derivatives, preparation and use |
-
2006
- 2006-08-02 CN CNB2006100527655A patent/CN100564355C/en not_active Expired - Fee Related
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102532062A (en) * | 2010-12-08 | 2012-07-04 | 上海工程技术大学 | Benzoyl urea compound and synthesis method thereof |
| CN102532062B (en) * | 2010-12-08 | 2013-12-04 | 上海工程技术大学 | Benzoyl urea compound and synthesis method thereof |
| CN112876384A (en) * | 2021-01-20 | 2021-06-01 | 安阳市安林生物化工有限责任公司 | Synthesis process and application of diflubenzuron |
| CN113773230A (en) * | 2021-09-07 | 2021-12-10 | 京博农化科技有限公司 | Method for synthesizing diflubenzuron by one-pot method |
| CN114380719A (en) * | 2022-01-06 | 2022-04-22 | 坛墨质检科技股份有限公司 | Preparation method of stable isotope labeled chlorbenzuron internal standard reagent |
| CN115108974A (en) * | 2022-07-15 | 2022-09-27 | 重庆医药高等专科学校 | 2, 6-difluorobenzoylurea derivative and preparation method and application thereof |
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| CN100564355C (en) | 2009-12-02 |
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