CN102432546A - Pyridazinone compound and synthesis method thereof - Google Patents
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- CN102432546A CN102432546A CN2011103882166A CN201110388216A CN102432546A CN 102432546 A CN102432546 A CN 102432546A CN 2011103882166 A CN2011103882166 A CN 2011103882166A CN 201110388216 A CN201110388216 A CN 201110388216A CN 102432546 A CN102432546 A CN 102432546A
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- YDCXEISZZSUBMZ-UHFFFAOYSA-N CCC(C(c(cc1)ccc1[ClH]C)=O)Br Chemical compound CCC(C(c(cc1)ccc1[ClH]C)=O)Br YDCXEISZZSUBMZ-UHFFFAOYSA-N 0.000 description 1
- YNLQIQLTJFNBSS-UHFFFAOYSA-N [NH-][NH+](C1=O)N=CC(Cl)=C1Cl Chemical compound [NH-][NH+](C1=O)N=CC(Cl)=C1Cl YNLQIQLTJFNBSS-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention relates to a pyridazinone compound and a synthesis method thereof. The synthesis method comprises the following steps: subjecting a substituted aromatic hydrocarbon and alpha halogen-benzoic acyl halide to Friedel-Crafts acylation to generate alpha halogen aromatic-aliphatic mixed ketone; reacting the alpha halogen aromatic-aliphatic mixed ketone with 4,5-dichloro-3(2H) pyridazinone, and then subjecting the alpha halogen aromatic-aliphatic mixed ketone and cyclamine to substitution reaction in solvent under the catalysis of alkaline reagent to synthesize the pyridazinone compound. Compared with the prior art, the pyridazinone compound is simple in process flow, wide in application range and applicable to the prevention and the treatment of pests such as flies, mosquitoes, fleas and the like and agricultural insects such as rice water weevil, beet armyworm, armyworm and the like, has the performance for inhibiting the growth of insects and particularly larva of the mosquitoes and is an insecticide with a wide application prospect.
Description
Technical field
The present invention relates to a kind of suppressor factor and compound method thereof, especially relate to a kind of pyridazinone compound and compound method thereof.
Background technology
Pyridazinone compound is widely used in the control of sanitary insect pest and crop pests, obtained many commercial pesticide species, but in the life-time service process, pest resistance to insecticide strengthens constantly.Its application on agricultural is restricted.
Summary of the invention
The object of the invention is exactly to provide a kind of technical process simple for the defective that overcomes above-mentioned prior art existence, pyridazinone compound that the scope of application is extensive and compound method thereof.
The object of the invention can be realized through following technical scheme: a kind of pyridazinone compound is characterized in that this compound molecule formula is following:
Wherein, R
1Be alkyl or halogen or hydrogen, R
2Be alkyl or the halogen or the hydrogen of 1-4 carbon atom, R
3Be piperidines or morpholine or imidazoles.
A kind of preparation method of pyridazinone compound is characterized in that, this method may further comprise the steps:
The preparation of (1) 4,5-two chloro-3 (2H) pyridazinones
Two-chloro butylene aldehydic acid and hydrazonium sulfate are condensed into 4 under the katalysis of sodium-acetate, 5-two chloro-3 (2H) pyridazinones;
(2) preparation of α halo-fragrant fatty mixed ketone
Substituted arene and α halogeno-benzene formyl halide generate α halo-fragrant fatty mixed ketone through the gram acylation reaction of paying through an intermediary in a business deal;
(3) 2-replaces the preparation of-3 (2H)-pyridazinones
With step (1) make 4, under the katalysis of alkaline reagents, condensation reaction is prepared into 2-and replaces-3 (2H)-pyridazinones α halo-fragrant fatty mixed ketone that 5-two chloro-3 (2H) pyridazinones and step (2) make in solvent;
(4) preparation of pyridazinone compound
Step (3) gained 2-is replaced-3 (2H)-pyridazinones in solvent, synthesize pyridazinone compound with cyclammonium generation substitution reaction.
The mol ratio of step (1) described two-chloro butylene aldehydic acid and hydrazonium sulfate, sodium-acetate is 1: (1-2): (1-2).
Step (1) described two-chloro butylene aldehydic acid and hydrazonium sulfate are condensed into 4 under the katalysis of sodium-acetate, the temperature of reaction of 5-two chloro-3 (2H) pyridazinones is 80-100 ℃, and the reaction times is 1-3 hour.
The mol ratio of described substituted arene of step (2) and α halogeno-benzene formyl halide is 1: 1, and the condition of described pair of gram acylation reaction is: at AlCl
3Katalysis under, 0 ℃ the reaction 4 hours, described AlCl
3Add-on for the mol ratio of substituted arene be 1: 1.
Described substituted arene comprises toluene, ethylbenzene, chlorobenzene or bromobenzene, and described α halogeno-benzene formyl halide comprises alpha-brominated acetyl bromide or 2-bromine butyryl bromide.
Step (3) described 4; The mol ratio of 5-two chloro-3 (2H) pyridazinones and α halo-fragrant fatty mixed ketone is 1: 1, and the add-on of described solvent is 20-25ml/g4,5-two chloro-3 (2H) pyridazinones; The add-on of described alkaline reagents and 4; The mass ratio of 5-two chloro-3 (2H) pyridazinones is (1.5-2): 1, and the temperature of described condensation reaction is 20-100 ℃, the time is 5-24 hour.
The described solvent of step (3) is N, dinethylformamide, ethylene dichloride, chloroform, tetracol phenixin, 1,2-ethylene dichloride or ethanol; Described alkaline reagents comprises salt of wormwood, yellow soda ash, saleratus, sodium hydrogencarbonate, Pottasium Hydroxide, sodium hydroxide or triethylamine; The temperature of described condensation reaction is 30-60 ℃, and the time is 6 hours.
The mol ratio that the described 2-of step (4) replaces-3 (2H)-pyridazinones and cyclammonium is 1: (1-1.8); The add-on of described solvent is the 25-35ml/g cyclammonium, and the temperature of reaction of described substitution reaction is 30-120 ℃, and the reaction times is 3-15 hour.
The mol ratio that the described 2-of step (4) replaces-3 (2H)-pyridazinones and cyclammonium is 1: 1.2; Described cyclammonium comprises morphine quinoline or piperidines or imidazoles, and described solvent is N, dinethylformamide, ethylene dichloride, chloroform, tetracol phenixin, 1, and 2-ethylene dichloride or ethanol, the temperature of reaction of described substitution reaction is 50-80 ℃, the reaction times is 7 hours.
Compared with prior art; Technical process of the present invention is simple; The scope of application is extensive; Being suitable for use in the controls such as sanitary insect pest such as fly, mosquito, flea etc. and Agricultural pests such as rice water first, beet armyworm, mythimna separata, can suppressing the particularly performance of growth of mosqito larva of insect, is one type of sterilant with application prospect.
Embodiment
Below in conjunction with specific embodiment the present invention is elaborated.
Embodiment 1
A kind of pyridazinone compound, this compound molecule formula is following
R
1Be methyl, R
2Be hydrogen, R
3Be morpholine, the compound method of this pyridazinone compound may further comprise the steps:
The preparation of (1) 4,5-two chloro-3 (2H) pyridazinones
In the 250mL there-necked flask, add 50g rare aldehydic acid of dichloro-fourth and less water, stir, process the aqueous solution, add the 39g hydrazonium sulfate then, the 38.2g sodium-acetate is heated to 80-100 ℃, reacts 2 hours.Complete reaction postcooling, reaction solution are poured in the cold water, a large amount of faint yellow depositions occur, suction filtration, drying.Products therefrom carries out recrystallization with absolute ethyl alcohol, productive rate 89.5%.
(2) preparation of 2-bromo-p-methyl aceto phenone
In having the 250mL there-necked flask of condensation and drying installation, add 70mL toluene, the anhydrous AlCl of 26.6g
3, stir, under the frozen water cooling, slowly drip alpha-brominated acetyl bromide, low-temp reaction 2 hours.Be warming up to 35 ℃ then, insulation reaction 3 hours.After the complete reaction reaction solution is poured in the 200mL cold water, and constantly stirred.Tell organic phase, the organic phase water is washed till neutrality, and anhydrous MgSO4 is dry.Slough organic phase, obtain solid matter, productive rate 88.9%.
The preparation of (3) 4,5-two chloro-2-[2-(4-tolyl)-2-oxo-ethyl]-2H-pyridazin-3-one
In the there-necked flask of the 250mL that is furnished with drying installation, add 3g 4,5-two chloro-3 (2H) pyridazinones, the 5.7g soda ash light, the 70mL dry DMF stirs.Dropping is dissolved in the solution after the dry DMF by 4.5g 2-bromo-to the toluene ethyl ketone, and normal-temperature reaction 5 hours is poured reaction solution in the 150mL frozen water into after the complete reaction, stirs, leave standstill for some time after, deposition in a large number appears, suction filtration obtains faint yellow solid, productive rate 90.40%
(4) preparation of 5-morpholinyl-4-chloro-2-[2-(4-tolyl)-2-oxo-ethyl]-2H-pyridazin-3-one
In having the 250mL there-necked flask of condensation and drying installation, add 3g 4,5-two chloro-2-[2-(4-tolyl)-2-oxo-ethyl]-2H-pyridazin-3-one, 40mL absolute ethyl alcohol; Stir, slowly drip the ethanol solution that 10mL contains 1.5g morphine quinoline, reflux 5 hours, complete reaction postcooling; Reaction solution is poured in the 150mL cold water, is stirred, leave standstill for some time after, deposition in a large number appears; Suction filtration gets faint yellow solid 3.21g, productive rate 85.6%.
Embodiment 2
A kind of pyridazinone compound, this compound molecule formula is following
R
1Be chlorine, R
2Be ethyl, R
3Be piperidines, the compound method of this pyridazinone compound may further comprise the steps:
(1) preparation of 2-bromo-1-rubigan-1-butanone
Close in the 250ml there-necked flask of drying installation having condensation, add the 60ml chlorobenzene, the 26g anhydrous AlCl3 stirs, and under the frozen water cooling, slowly drips 2-bromine butyryl bromide, low-temp reaction 2 hours.Rise to 35oC then, insulation reaction 3 hours.Reaction solution is poured in the 200ml frozen water, constantly stirred.Tell organic phase, organic phase is with washing 6～7 times, and anhydrous MgSO4 is dry.Slough chlorobenzene, underpressure distillation is collected 162-164 ℃ cut, yield 78.2%
The preparation of (2) 4,5-two chloro-2-[2-(4-chloro-phenyl)-2-oxo-ethyl]-1-ethyl-2H-pyridazin-3-one
In having the 250ml there-necked flask of drying installation, add 3g3 (2H) pyridazinone, the 6g Anhydrous potassium carbonate; The 60ml dry DMF stirs, and drips 1; The 89g chlorobenzene butanone, normal temperature reacted 5 hours down, poured reaction solution in the 150ml frozen water into; A large amount of sticky solid appear, with ETHYLE ACETATE and sherwood oil recrystallization, yield 85.3%;
(3) preparation of 5-piperidyl-4-chloro-2-[2-(4-chloro-phenyl)-2-oxo-ethyl]-1-ethyl-2H-pyridazin-3-one
In having the 250mL there-necked flask of condensation and drying installation, add 2g4,5-two chloro-2-[2-(4-chloro-phenyl)-2-oxo-ethyl]-1-ethyl-2H-pyridazin-3-one, 40mL absolute ethyl alcohol; Stir, slowly drip the ethanol solution that 10mL contains the 2g piperidines, reflux 5 hours, complete reaction postcooling; Reaction solution is poured in the 100mL cold water, is stirred, leave standstill for some time after, yellow sticky solid appears; After the curing, with ETHYLE ACETATE and sherwood oil recrystallization, yield 78.95%.
Embodiment 3
A kind of preparation method of pyridazinone compound may further comprise the steps:
The preparation of (1) 4,5-two chloro-3 (2H) pyridazinones
With two-chloro butylene aldehydic acid and hydrazonium sulfate is to mix at 1: 1 in molar ratio, and under the katalysis of sodium-acetate, at 80 ℃, condensation reaction 1 hour makes 4,5-two chloro-3 (2H) pyridazinones, and wherein the mol ratio of two-chloro butylene aldehydic acid and sodium-acetate is 1: 1;
(2) preparation of α halo-fragrant fatty mixed ketone
Substituted arene ethylbenzene and alpha-brominated acetyl bromide are to mix at 1: 1 in molar ratio, at AlCl
3Katalysis under, pay the gram acylation reaction at 0 ℃ and generated α halo-fragrant fatty mixed ketone, described AlCl in 2 hours
3Add-on for the mol ratio of ethylbenzene be 1: 1;
(3) 2-replaces the preparation of-3 (2H)-pyridazinones
With step (1) make 4, α halo-fragrant fatty mixed ketone that 5-two chloro-3 (2H) pyridazinones and step (2) make is to be blended in N at 1: 1 in molar ratio, in the dinethylformamide; Under the katalysis of alkaline reagents saleratus; In 30 ℃, condensation reaction was prepared into 2-in 24 hours and replaces-3 (2H)-pyridazinone, wherein N; The add-on of dinethylformamide is 20ml/g4; 5-two chloro-3 (2H) pyridazinones, the add-on of described alkaline reagents and 4, the mass ratio of 5-two chloro-3 (2H) pyridazinones is 1.5: 1;
(4) preparation of pyridazinone compound
Step (3) gained 2-is replaced-3 (2H)-pyridazinones mixed in 1: 1.2 in molar ratio, at N, in the dinethylformamide with the morphine quinoline; Under 30 ℃, substitution reaction 15 hours takes place, synthetic pyridazinone compound; Described N, the add-on of dinethylformamide is a 25ml/g morphine quinoline.
Embodiment 4
A kind of preparation method of pyridazinone compound may further comprise the steps:
The preparation of (1) 4,5-two chloro-3 (2H) pyridazinones
With two-chloro butylene aldehydic acid and hydrazonium sulfate is to mix at 1: 2 in molar ratio, and under the katalysis of sodium-acetate, at 100 ℃, condensation reaction 2 hours makes 4,5-two chloro-3 (2H) pyridazinones, and wherein the mol ratio of two-chloro butylene aldehydic acid and sodium-acetate is 1: 2;
(2) preparation of α halo-fragrant fatty mixed ketone
Substituted arene bromobenzene and 2-bromine butyryl bromide are to mix at 1: 1 in molar ratio, at AlCl
3Katalysis under, pay the gram acylation reaction at 0 ℃ and generated α halo-fragrant fatty mixed ketone, described AlCl in 4 hours
3Add-on for the mol ratio of ethylbenzene be 1: 1;
(3) 2-replaces the preparation of-3 (2H)-pyridazinones
With step (1) make 4, α halo-fragrant fatty mixed ketone that 5-two chloro-3 (2H) pyridazinones and step (2) make is to be blended in ethylene dichloride at 1: 1 in molar ratio, under the katalysis of alkaline reagents saleratus; In 60 ℃; Condensation reaction was prepared into 2-in 5 hours and replaces-3 (2H)-pyridazinones, and wherein the add-on of ethylene dichloride is 25ml/g4,5-two chloro-3 (2H) pyridazinones; The add-on of described alkaline reagents and 4, the mass ratio of 5-two chloro-3 (2H) pyridazinones is 2: 1;
(4) preparation of pyridazinone compound
Step (3) gained 2-is replaced-3 (2H)-pyridazinones mixed in 1: 1.8 in molar ratio, in ethylene dichloride, under 120 ℃, substitution reaction 3 hours takes place with piperidines, synthetic pyridazinone compound, the add-on of described ethylene dichloride is the 35ml/g piperidines.
Embodiment 5
A kind of preparation method of pyridazinone compound may further comprise the steps:
The preparation of (1) 4,5-two chloro-3 (2H) pyridazinones
With mucochloric acid and hydrazonium sulfate is to mix at 1: 1.5 in molar ratio, and under the katalysis of sodium-acetate, at 90 ℃, condensation reaction 2 hours makes 4,5-two chloro-3 (2H) pyridazinones, and wherein the mol ratio of two-chloro butylene aldehydic acid and sodium-acetate is 1: 1.5;
(2) preparation of α halo-fragrant fatty mixed ketone
Substituted arene bromobenzene and 2-bromine butyryl bromide are to mix at 1: 1 in molar ratio, at AlCl
3Katalysis under, pay the gram acylation reaction at 0 ℃ and generated α halo-fragrant fatty mixed ketone, described AlCl in 2 hours
3Add-on for the mol ratio of bromobenzene be 1: 1;
(3) 2-replaces the preparation of-3 (2H)-pyridazinones
With step (1) make 4, α halo-fragrant fatty mixed ketone that 5-two chloro-3 (2H) pyridazinones and step (2) make is to be blended in chloroform at 1: 1 in molar ratio, under the katalysis of alkaline reagents saleratus; In 30-60 ℃; Condensation reaction was prepared into 2-in 6 hours and replaces-3 (2H)-pyridazinones, and wherein the add-on of chloroform is 22ml/g4,5-two chloro-3 (2H) pyridazinones; The add-on of described alkaline reagents and 4, the mass ratio of 5-two chloro-3 (2H) pyridazinones is 1.8: 1;
(4) preparation of pyridazinone compound
Step (3) gained 2-is replaced-3 (2H)-pyridazinones mixed in 1: 1.5 in molar ratio, in chloroform, under 60 ℃, substitution reaction 7 hours takes place with imidazoles, synthetic pyridazinone compound, the add-on of described ethylene dichloride is the 30ml/g piperidines.
The embodiment of the invention adopts the Toxicity Determination method to carry out performance test.
The experimental technique of Toxicity Determination is:
Medicament preparation and TP
Earlier accurately take by weighing each medicament 20mg with electronic balance, respectively with a small amount of DMF dissolving, after the sample dissolution, it is for use that the aqueous solution that usefulness contains 0.05% tensio-active agent is diluted to 200mg/L.
TP
Mythimna separata: adopt leaf of Semen Maydis to soak the medicine method, maize leaf is flooded 5s take out in soup, after soup dries naturally, the clip leaf of Semen Maydis, 3 instar larvaes of feeding, 4 repetitions are established in every processing, respectively at the dead borer population of inspection behind 48h and the 72h, calculate mortality ratio.
Wriggler: adopt the larva immersion method.With culex pipiens pollens 3 instar larvaes, a certain amount of soup and pure water are mixed with the soup of 200mg/L, insert wriggler, every processing is provided with 4 repetitions.
Test-results is:
Sample is in the test result of 200mg/L to mythimna separata and wriggler
| Sample number into spectrum | Mythimna separata (lethality rate %) | Wriggler (lethality rate %) |
| Embodiment 1 | 56.0 | 44.0 |
| Embodiment 2 | 43.0 | 32.0 |
| Embodiment 3 | 78.0 | 88.0 |
| Embodiment 4 | 76.0 | 64.0 |
| Embodiment 5 | 82.0 | 76.0 |
Claims (10)
1. a pyridazinone compound is characterized in that, this compound molecule formula is following:
Wherein, R
1Be alkyl or halogen or hydrogen, R
2Be alkyl or the halogen or the hydrogen of 1-4 carbon atom, R
3Be piperidines or morpholine or imidazoles.
2. the preparation method of a pyridazinone compound as claimed in claim 1 is characterized in that, this method may further comprise the steps:
The preparation of (1) 4,5-two chloro-3 (2H) pyridazinones
Two-chloro butylene aldehydic acid and hydrazonium sulfate are condensed into 4 under the katalysis of sodium-acetate, 5-two chloro-3 (2H) pyridazinones;
(2) preparation of α halo-fragrant fatty mixed ketone
Substituted arene and α halogeno-benzene formyl halide generate α halo-fragrant fatty mixed ketone through the gram acylation reaction of paying through an intermediary in a business deal;
(3) 2-replaces the preparation of-3 (2H)-pyridazinones
With step (1) make 4, under the katalysis of alkaline reagents, condensation reaction is prepared into 2-and replaces-3 (2H)-pyridazinones α halo-fragrant fatty mixed ketone that 5-two chloro-3 (2H) pyridazinones and step (2) make in solvent;
(4) preparation of pyridazinone compound
Step (3) gained 2-is replaced-3 (2H)-pyridazinones in solvent, synthesize pyridazinone compound with cyclammonium generation substitution reaction.
3. the preparation method of pyridazinone compound according to claim 2 is characterized in that, the mol ratio of step (1) described two-chloro butylene aldehydic acid and hydrazonium sulfate, sodium-acetate is 1: (1-2): (1-2).
4. the preparation method of pyridazinone compound according to claim 2; It is characterized in that; Step (1) described two-chloro butylene aldehydic acid and hydrazonium sulfate are condensed into 4 under the katalysis of sodium-acetate, the temperature of reaction of 5-two chloro-3 (2H) pyridazinones is 80-100 ℃, and the reaction times is 1-3 hour.
5. the preparation method of pyridazinone compound according to claim 2 is characterized in that, the mol ratio of described substituted arene of step (2) and α halogeno-benzene formyl halide is 1: 1, and the condition of described pair of gram acylation reaction is: at AlCl
3Katalysis under, 0 ℃ the reaction 4 hours, described AlCl
3Add-on for the mol ratio of substituted arene be 1: 1.
6. according to the preparation method of claim 2 or 5 described pyridazinone compounds, it is characterized in that described substituted arene comprises toluene, ethylbenzene, chlorobenzene or bromobenzene, described α halogeno-benzene formyl halide comprises alpha-brominated acetyl bromide or 2-bromine butyryl bromide.
7. the preparation method of pyridazinone compound according to claim 2 is characterized in that, step (3) described 4; The mol ratio of 5-two chloro-3 (2H) pyridazinones and α halo-fragrant fatty mixed ketone is 1: 1, and the add-on of described solvent is 20-25ml/g4,5-two chloro-3 (2H) pyridazinones; The add-on of described alkaline reagents and 4; The mass ratio of 5-two chloro-3 (2H) pyridazinones is (1.5-2): 1, and the temperature of described condensation reaction is 20-100 ℃, the time is 5-24 hour.
8. according to the preparation method of claim 2 or 7 described pyridazinone compounds, it is characterized in that the described solvent of step (3) is N, dinethylformamide, ethylene dichloride, chloroform, tetracol phenixin, 1,2-ethylene dichloride or ethanol; Described alkaline reagents comprises salt of wormwood, yellow soda ash, saleratus, sodium hydrogencarbonate, Pottasium Hydroxide, sodium hydroxide or triethylamine; The temperature of described condensation reaction is 30-60 ℃, and the time is 6 hours.
9. the preparation method of pyridazinone compound according to claim 2 is characterized in that, the mol ratio that the described 2-of step (4) replaces-3 (2H)-pyridazinones and cyclammonium is 1: (1-1.8); The add-on of described solvent is the 25-35ml/g cyclammonium, and the temperature of reaction of described substitution reaction is 30-120 ℃, and the reaction times is 3-15 hour.
10. according to the preparation method of claim 1 or 9 described pyridazinone compounds, it is characterized in that the mol ratio that the described 2-of step (4) replaces-3 (2H)-pyridazinones and cyclammonium is 1: 1.2; Described cyclammonium comprises morphine quinoline or piperidines or imidazoles, and described solvent is N, dinethylformamide, ethylene dichloride, chloroform, tetracol phenixin, 1, and 2-ethylene dichloride or ethanol, the temperature of reaction of described substitution reaction is 50-80 ℃, the reaction times is 7 hours.
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| CN103864769A (en) * | 2012-12-14 | 2014-06-18 | 上海工程技术大学 | Oxadiazole compound and preparation method thereof |
| CN103980268A (en) * | 2014-04-29 | 2014-08-13 | 上海工程技术大学 | Thiadiazole compound and synthesis method thereof |
| CN108503590A (en) * | 2017-02-24 | 2018-09-07 | 上海工程技术大学 | A kind of pyridazinone compound and its synthetic method |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103864769A (en) * | 2012-12-14 | 2014-06-18 | 上海工程技术大学 | Oxadiazole compound and preparation method thereof |
| CN103864769B (en) * | 2012-12-14 | 2016-11-02 | 上海工程技术大学 | A kind of diazole compounds and preparation method thereof |
| CN103694179A (en) * | 2013-12-04 | 2014-04-02 | 上海工程技术大学 | Bishydrazide compound and preparation method thereof |
| CN103980268A (en) * | 2014-04-29 | 2014-08-13 | 上海工程技术大学 | Thiadiazole compound and synthesis method thereof |
| CN103980268B (en) * | 2014-04-29 | 2016-08-24 | 上海工程技术大学 | A kind of thiadiazole compound and synthetic method thereof |
| CN108503590A (en) * | 2017-02-24 | 2018-09-07 | 上海工程技术大学 | A kind of pyridazinone compound and its synthetic method |
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