CN102432546B - Pyridazinone compound and synthesis method thereof - Google Patents
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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 inhibitor and synthetic method thereof, especially relate to a kind of pyridazinone compound and synthetic 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 life-time service process, pest resistance to insecticide constantly strengthens.Its application in agricultural is restricted.
Summary of the invention
Object of the present invention is exactly to provide a kind of technical process simple in order to overcome the defect of above-mentioned prior art existence, pyridazinone compound applied widely and synthetic method thereof.
Object of the present invention can be achieved through the following technical solutions: a kind of pyridazinone compound, it is characterized in that, and this compound molecule formula is as follows:
Wherein, R
1for alkyl or halogen or hydrogen, R
2for alkyl or halogen or the hydrogen of 1-4 carbon atom, R
3for piperidines or morpholine or imidazoles.
A preparation method for pyridazinone compound, is characterized in that, the method comprises the following steps:
The preparation of (1) 4,5-bis-chloro-3 (2H) pyridazinone
Two-chloro butylene aldehydic acid and hydrazonium sulfate are condensed into 4,5-bis-chloro-3 (2H) pyridazinone under the katalysis of sodium-acetate;
(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 gram acylation reaction of paying through an intermediary in a business deal;
(3) 2-replaces the preparation of-3 (2H)-pyridazinones
Step (1) is made 4, α halo-fragrant fatty mixed ketone that chloro-3 (2H) pyridazinones of 5-bis-and step (2) make is in solvent under the katalysis of alkaline reagents, condensation reaction is prepared into 2-and replaces-3 (2H)-pyridazinones;
(4) preparation of pyridazinone compound
Step (3) gained 2-is replaced to-3 (2H)-pyridazinones and in solvent, synthesize pyridazinone compound with cyclammonium generation substitution reaction.
The mol ratio of two-chloro butylene aldehydic acid that step (1) is described and hydrazonium sulfate, sodium-acetate is 1: (1-2): (1-2).
The temperature of reaction that two-chloro butylene aldehydic acid that step (1) is described and hydrazonium sulfate are condensed into 4,5-bis-chloro-3 (2H) pyridazinone under the katalysis of sodium-acetate is 80-100 ℃, and the reaction times is 1-3 hour.
The substituted arene that step (2) is described and the mol ratio of α halogeno-benzene formyl halide are 1: 1, and the described condition of paying gram acylation reaction is: at AlCl
3katalysis under, 0 ℃ 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.
Described in step (3) 4, the mol ratio of chloro-3 (2H) pyridazinones of 5-bis-and α halo-fragrant fatty mixed ketone is 1: 1, the add-on of described solvent is 20-25ml/g4,5-bis-chloro-3 (2H) pyridazinone, the add-on of described alkaline reagents and 4, the mass ratio of 5-bis-chloro-3 (2H) pyridazinone 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 DMF, ethylene dichloride, chloroform, tetracol phenixin, 1,2-ethylene dichloride or ethanol; Described alkaline reagents comprises salt of wormwood, sodium carbonate, saleratus, sodium bicarbonate, potassium 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 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 morpholine or piperidines or imidazoles, and described solvent is DMF, ethylene dichloride, chloroform, tetracol phenixin, 1,2-ethylene dichloride or ethanol, and 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, applied widely, be suitable for use in sanitary insect pest if fly, mosquito, flea etc. and Agricultural pests are as in the controls such as rice water first, beet armyworm, mythimna separata, can suppress the particularly performance of growth of mosqito larva of insect, be the sterilant that a class has application prospect.
Embodiment
Below in conjunction with specific embodiment, the present invention is described in detail.
Embodiment 1
A pyridazinone compound, this compound molecule formula is as follows
R
1for methyl, R
2for hydrogen, R
3for morpholine, the synthetic method of this pyridazinone compound comprises the following steps:
The preparation of (1) 4,5-bis-chloro-3 (2H) pyridazinone
In 250mL there-necked flask, add the rare aldehydic acid of 50g dichloro-fourth and a small amount of water, stir, make the aqueous solution, then add 39g hydrazonium sulfate, 38.2g sodium-acetate, is heated to 80-100 ℃, reacts 2 hours.Cooling after complete reaction, reaction solution is poured in cold water, occurs a large amount of faint yellow precipitations, and suction filtration is dry.Products therefrom carries out recrystallization with dehydrated alcohol, productive rate 89.5%.
(2) preparation of the bromo-p-methyl aceto phenone of 2-
In the 250mL there-necked flask with condensation and drying installation, add 70mL toluene, the anhydrous AlCl of 26.6g
3, stir, under frozen water is cooling, slowly drip alpha-brominated acetyl bromide, low-temp reaction 2 hours.Then be warming up to 35 ℃, insulation reaction 3 hours.After complete reaction, reaction solution is poured in 200mL cold water, and constantly stirred.Separate organic phase, organic phase washes with water to neutrality, and anhydrous MgSO4 is dry.Slough organic phase, obtain solid matter, productive rate 88.9%.
The chloro-2-[2-of (3) 4,5-bis-(4-tolyl)-2-oxo-ethyl] preparation of-2H-pyridazin-3-one
In the there-necked flask of 250mL of being furnished with drying installation, add 3g 4,5-bis-chloro-3 (2H) pyridazinone, 5.7g anhydrous sodium carbonate, 70mL dry DMF, stirs.Dropping is dissolved in the solution after dry DMF by 4.5g 2-is bromo-to toluene ethyl ketone, and normal-temperature reaction 5 hours is poured reaction solution in 150mL frozen water into after complete reaction, stirs, and after standing for some time, occurs precipitation in a large number, and suction filtration, obtains faint yellow solid, productive rate 90.40%
(4) the chloro-2-[2-of 5-morpholinyl-4-(4-tolyl)-2-oxo-ethyl] preparation of-2H-pyridazin-3-one
In the 250mL there-necked flask with condensation and drying installation, add 3g 4, the chloro-2-[2-of 5-bis-(4-tolyl)-2-oxo-ethyl]-2H-pyridazin-3-one, 40mL dehydrated alcohol, stirs, and slowly drips 10mL containing the ethanol solution of 1.5g morpholine, reflux 5 hours, cooling after complete reaction, reaction solution is poured in 150mL cold water, stir, after standing for some time, there is precipitation in a large number, suction filtration, obtain faint yellow solid 3.21g, productive rate 85.6%.
Embodiment 2
A pyridazinone compound, this compound molecule formula is as follows
R
1for chlorine, R
2for ethyl, R
3for piperidines, the synthetic method of this pyridazinone compound comprises the following steps:
(1) preparation of the bromo-1-rubigan-1-of 2-butanone
In close the 250ml there-necked flask of drying installation with condensation, add 60ml chlorobenzene, 26g anhydrous AlCl3, stirs, and under frozen water is cooling, slowly drips 2-bromine butyryl bromide, low-temp reaction 2 hours.Then rise to 35oC, insulation reaction 3 hours.Reaction solution is poured in 200ml frozen water, constantly stirred.Separate organic phase, organic phase washes with water 6～7 times, and anhydrous MgSO4 is dry.Slough chlorobenzene, underpressure distillation, collects the cut of 162-164 ℃, yield 78.2%
The chloro-2-[2-of (2) 4,5-bis-(the chloro-phenyl of 4-)-2-oxo-ethyl] preparation of-1-ethyl-2H-pyridazin-3-one
In the 250ml there-necked flask with drying installation, add 3g3 (2H) pyridazinone, 6g Anhydrous potassium carbonate, 60ml dry DMF, stir, drip 1,89g chlorobenzene butanone, under normal temperature, react 5 hours, reaction solution is poured in 150ml frozen water, there are a large amount of sticky solid, with ethyl acetate and sherwood oil recrystallization, yield 85.3%;
(3) the chloro-2-[2-of 5-piperidyl-4-(the chloro-phenyl of 4-)-2-oxo-ethyl] preparation of-1-ethyl-2H-pyridazin-3-one
In the 250mL there-necked flask with condensation and drying installation, add 2g4, the chloro-2-[2-of 5-bis-(the chloro-phenyl of 4-)-2-oxo-ethyl]-1-ethyl-2H-pyridazin-3-one, 40mL dehydrated alcohol, stirs, and slowly drips 10mL containing the ethanol solution of 2g piperidines, reflux 5 hours, cooling after complete reaction, reaction solution is poured in 100mL cold water, stir, after standing for some time, there is yellow sticky solid, after solidifying, with ethyl acetate and sherwood oil recrystallization, yield 78.95%.
Embodiment 3
A preparation method for pyridazinone compound, comprises the following steps:
The preparation of (1) 4,5-bis-chloro-3 (2H) pyridazinone
By two-chloro butylene aldehydic acid and hydrazonium sulfate, be to mix at 1: 1 in molar ratio, under the katalysis of sodium-acetate, at 80 ℃, condensation reaction 1 hour, makes 4,5-bis-chloro-3 (2H) pyridazinone, 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 is to mix at 1: 1 with alpha-brominated acetyl bromide in molar ratio, at AlCl
3katalysis under, at 0 ℃, pay gram acylation reaction and within 2 hours, generate α halo-fragrant fatty mixed ketone, described AlCl
3add-on for the mol ratio of ethylbenzene be 1: 1;
(3) 2-replaces the preparation of-3 (2H)-pyridazinones
Step (1) is made 4, α halo-fragrant fatty mixed ketone that chloro-3 (2H) pyridazinones of 5-bis-and step (2) make is to be blended in N at 1: 1 in molar ratio, in dinethylformamide, under the katalysis of alkaline reagents saleratus, in 30 ℃, condensation reaction is prepared into 2-for 24 hours and replaces-3 (2H)-pyridazinones, N wherein, the add-on of dinethylformamide is 20ml/g4,5-bis-chloro-3 (2H) pyridazinone, the mass ratio of the add-on of described alkaline reagents and 4,5-bis-chloro-3 (2H) pyridazinone is 1.5: 1;
(4) preparation of pyridazinone compound
Step (3) gained 2-is replaced to-3 (2H)-pyridazinones to be mixed with morpholine for 1: 1.2 in molar ratio, at N, in dinethylformamide, at 30 ℃, there are substitution reaction 15 hours, synthetic pyridazinone compound, the add-on of described DMF is 25ml/g morpholine.
Embodiment 4
A preparation method for pyridazinone compound, comprises the following steps:
The preparation of (1) 4,5-bis-chloro-3 (2H) pyridazinone
By two-chloro butylene aldehydic acid and hydrazonium sulfate, be to mix at 1: 2 in molar ratio, under the katalysis of sodium-acetate, at 100 ℃, condensation reaction 2 hours, make 4,5-bis-chloro-3 (2H) pyridazinone, 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 is to mix at 1: 1 with 2-bromine butyryl bromide in molar ratio, at AlCl
3katalysis under, at 0 ℃, pay gram acylation reaction and within 4 hours, generate α halo-fragrant fatty mixed ketone, described AlCl
3add-on for the mol ratio of ethylbenzene be 1: 1;
(3) 2-replaces the preparation of-3 (2H)-pyridazinones
Step (1) is made 4, α halo-fragrant fatty mixed ketone that chloro-3 (2H) pyridazinones of 5-bis-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 is prepared into 2-for 5 hours and replaces-3 (2H)-pyridazinones, wherein the add-on of ethylene dichloride is 25ml/g4,5-bis-chloro-3 (2H) pyridazinone, the mass ratio of the add-on of described alkaline reagents and 4,5-bis-chloro-3 (2H) pyridazinone is 2: 1;
(4) preparation of pyridazinone compound
Step (3) gained 2-is replaced to-3 (2H)-pyridazinones to be mixed with piperidines for 1: 1.8 in molar ratio, in ethylene dichloride, at 120 ℃, there are substitution reaction 3 hours, synthetic pyridazinone compound, the add-on of described ethylene dichloride is 35ml/g piperidines.
Embodiment 5
A preparation method for pyridazinone compound, comprises the following steps:
The preparation of (1) 4,5-bis-chloro-3 (2H) pyridazinone
By mucochloric acid and hydrazonium sulfate, be to mix at 1: 1.5 in molar ratio, under the katalysis of sodium-acetate, at 90 ℃, condensation reaction 2 hours, make 4,5-bis-chloro-3 (2H) pyridazinone, 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 is to mix at 1: 1 with 2-bromine butyryl bromide in molar ratio, at AlCl
3katalysis under, at 0 ℃, pay gram acylation reaction and within 2 hours, generate α halo-fragrant fatty mixed ketone, described AlCl
3add-on for the mol ratio of bromobenzene be 1: 1;
(3) 2-replaces the preparation of-3 (2H)-pyridazinones
Step (1) is made 4, α halo-fragrant fatty mixed ketone that chloro-3 (2H) pyridazinones of 5-bis-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 is prepared into 2-for 6 hours and replaces-3 (2H)-pyridazinones, wherein the add-on of chloroform is 22ml/g4,5-bis-chloro-3 (2H) pyridazinone, the mass ratio of the add-on of described alkaline reagents and 4,5-bis-chloro-3 (2H) pyridazinone is 1.8: 1;
(4) preparation of pyridazinone compound
Step (3) gained 2-is replaced to-3 (2H)-pyridazinones and within 1: 1.5 in molar ratio, mix with imidazoles, in chloroform, at 60 ℃, substitution reaction 7 hours occur, synthetic pyridazinone compound, the add-on of described ethylene dichloride is 30ml/g piperidines.
The embodiment of the present invention adopts Toxicity Determination method to carry out performance test.
The experimental technique of Toxicity Determination is:
Medicament preparation and test method
First with electronic balance, accurately take each medicament 20mg, with a small amount of DMF, dissolve respectively, after sample dissolution, with the aqueous solution of the tensio-active agent containing 0.05%, be diluted to 200mg/L stand-by.
Test method
Mythimna separata: adopt leaf of Semen Maydis to soak medicine method, maize leaf is flooded in liquid to 5s and take out, after liquid dries naturally, clip leaf of Semen Maydis, 3 instar larvaes of feeding, 4 repetitions are established in every processing, respectively at checking dead borer population after 48h and 72h, calculate mortality ratio.
Wriggler: adopt larva immersion method.With culex pipiens pollens 3 instar larvaes, a certain amount of liquid and pure water are mixed with to the liquid of 200mg/L, access wriggler, every processing arranges 4 repetitions.
Test-results is:
Sample is the test result to mythimna separata and wriggler at 200mg/L
| 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 (9)
1. a pyridazinone compound, is characterized in that, this structural formula of compound is as follows:
Wherein, R
1for methyl or chlorine, R
2for ethyl or hydrogen, R
3for piperidines or morpholine or imidazoles.
2. a preparation method for pyridazinone compound as claimed in claim 1, is characterized in that, the method comprises the following steps:
The preparation of (1) 4,5-bis-chloro-3 (2H) pyridazinone
Mucochloric acid and hydrazonium sulfate are condensed into 4,5-bis-chloro-3 (2H) pyridazinone under the katalysis of sodium-acetate;
(2) preparation of α halo-fragrant fatty mixed ketone
Substituted arene and alpha-brominated acetyl bromide or 2-bromine butyryl bromide generate α halo-fragrant fatty mixed ketone through gram acylation reaction of paying through an intermediary in a business deal;
(3) 2-replaces the preparation of-3 (2H)-pyridazinones
Step (1) is made 4, α halo-fragrant fatty mixed ketone that chloro-3 (2H) pyridazinones of 5-bis-and step (2) make is in solvent under the katalysis of alkaline reagents, condensation reaction is prepared into 2-and replaces-3 (2H)-pyridazinones;
(4) preparation of pyridazinone compound
Step (3) gained 2-is replaced to-3 (2H)-pyridazinones and in solvent, synthesize pyridazinone compound with cyclammonium generation substitution reaction;
Described substituted arene is selected from toluene or chlorobenzene; Described cyclammonium is selected from morpholine or piperidines or imidazoles.
3. the preparation method of pyridazinone compound according to claim 2, is characterized in that, the mol ratio of the mucochloric acid that step (1) is described 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, described mucochloric acid and the hydrazonium sulfate of step (1) is condensed into 4 under the katalysis of sodium-acetate, the temperature of reaction of 5-bis-chloro-3 (2H) pyridazinone 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 substituted arene that step (2) is described and the mol ratio of α halogeno-benzene formyl halide are 1: 1, and the described condition of paying gram acylation reaction is: at AlCl
3katalysis under, 0 ℃ reaction 4 hours, described AlCl
3add-on for the mol ratio of substituted arene be 1: 1.
6. the preparation method of pyridazinone compound according to claim 2, it is characterized in that, described in step (3) 4, the mol ratio of chloro-3 (2H) pyridazinones of 5-bis-and α halo-fragrant fatty mixed ketone is 1: 1, the add-on of described solvent is 20-25ml/g4,5-bis-chloro-3 (2H) pyridazinone, the add-on of described alkaline reagents and 4, the mass ratio of 5-bis-chloro-3 (2H) pyridazinone is 1.5-2: 1, the temperature of described condensation reaction is 20-100 ℃, and the time is 5-24 hour.
7. according to the preparation method of the pyridazinone compound described in claim 2 or 6, it is characterized in that, the described solvent of step (3) is DMF, ethylene dichloride, chloroform, tetracol phenixin or ethanol; Described alkaline reagents is selected from salt of wormwood, sodium carbonate, saleratus, sodium bicarbonate, potassium hydroxide, sodium hydroxide or triethylamine; The temperature of described condensation reaction is 30-60 ℃, and the time is 6 hours.
8. 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 25-35ml/g cyclammonium, and the temperature of reaction of described substitution reaction is 30-120 ℃, and the reaction times is 3-15 hour.
9. according to the preparation method of the pyridazinone compound described in claim 2 or 8, 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 solvent is that DMF, ethylene dichloride, oxygen are imitative, tetracol phenixin or ethanol, and the temperature of reaction of described substitution reaction is 50-80 ℃, and the reaction times is 7 hours.
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