CN108432746A - α-naphthylacetic acid aliphatic alcohol ester W/O lotions and its preparation method and application method and nanoemulsions - Google Patents
α-naphthylacetic acid aliphatic alcohol ester W/O lotions and its preparation method and application method and nanoemulsions Download PDFInfo
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/10—Aromatic or araliphatic carboxylic acids, or thio analogues thereof; Derivatives thereof
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- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
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Abstract
The invention discloses a kind of αnaphthylacetate aliphatic alcohol ester W/O lotions and its preparation method and application method and nanoemulsions, and with the total weight of αnaphthylacetate aliphatic alcohol ester W/O lotions, which includes：4 8wt% of αnaphthylacetate aliphatic alcohol ester, 1 2wt% of vegetable oil, 20 25wt% of 40 45wt% of emulsifier, 20 25wt% of propylene glycol and water.The αnaphthylacetate aliphatic alcohol ester W/O lotions of the present invention realize the duplicate protection to αnaphthylacetate; the embedding effect of slow release αnaphthylacetate and W/O lotions is hydrolyzed by αnaphthylacetate aliphatic alcohol ester; the slowly releasing effect of αnaphthylacetate is improved by duplicate protection, and then improves the lasting period of action of agricultural chemicals.
Description
Technical field
The invention belongs to field of pesticide preparation, more particularly, to a kind of α-naphthylacetic acid aliphatic alcohol ester W/O lotions and its system
Preparation Method and methods for using them and nanoemulsions.
Background technology
α-naphthylacetic acid is a kind of broad spectrum type plant growth regulator, with endogenous auxins heteroauxin work having the same
With feature and physiological function, can promote cell division and expansion, induced synthesis adventitious root, promote growth, prevent fruit drop and
Form s.m.p fruit, enhancing plant fighting drought, salt resistance alkali, lodging tolerance.In order to promote the solubility of α-naphthylacetic acid in water,
Often it is reacted with alkali in practical application and is prepared into sodium salt, sylvite or ammonium salt etc., to prepare its common aqua.
In recent years, with the needs of the raising of environmental consciousness and sustainable development, the requirement to the formulations of pesticide is higher and higher,
Especially develop towards the direction of synergy, sustained release, safety, then to the transformation that traditional formulations of pesticide upgrade, invention
The cry of novel form is higher and higher.Although the aqua of α-naphthylacetic acid salt has a wide range of applications, because not having sustained release performance
And the lasting period is caused not grow, therefore, how the dosage form of α-naphthylacetic acid active compound is optimized, in particular how improves and had
There is the novel form of sustained release performance, safety and environmental protection to be a technical problem to be solved urgently.
Invention content
The purpose of the present invention is overcoming the deficiencies of existing technologies, a kind of α-naphthylacetic acid aliphatic alcohol ester W/O lotions are provided.
To achieve the goals above, the first aspect of the present invention provides a kind of α-naphthylacetic acid aliphatic alcohol ester W/O lotions, with α-
The total weight of methyl α-naphthyl acetate aliphatic alcohol ester W/O lotions, the lotion include：α-naphthylacetic acid aliphatic alcohol ester 4-8wt%, vegetable oil 1-
2wt%, emulsifier 40-45wt%, propylene glycol 20-25wt% and water 20-25wt%.
The second aspect of the present invention provides a kind of preparation method of above-mentioned α-naphthylacetic acid aliphatic alcohol ester W/O lotions, the preparation
Method includes：The α-naphthylacetic acid aliphatic alcohol ester, vegetable oil, emulsifier, propylene glycol and water are uniformly mixed, the α-naphthalene is obtained
Acetic acid aliphatic alcohol ester W/O lotions.
The third aspect of the present invention provides a kind of application process of above-mentioned α-naphthylacetic acid aliphatic alcohol ester W/O lotions, this method
Including：It is used after the α-naphthylacetic acid aliphatic alcohol ester W/O lotions are diluted with water；The α-naphthylacetic acid aliphatic alcohol ester W/O lotions
Volume ratio with water is preferably 1:40-2000.
The fourth aspect of the present invention provides a kind of nanoemulsions, and the nanoemulsions are by above-mentioned α-naphthylacetic acid aliphatic alcohol ester W/O
Lotion dilutes to obtain, and the grain size of nano-particle is preferably 15-25nm in the nanoemulsions.
Technical scheme of the present invention is had following beneficial compared with the existing direct dosage form prepared using α-naphthylacetic acid molecule
Effect：
(1) α-naphthylacetic acid aliphatic alcohol ester W/O lotions of the invention realize the duplicate protection to α-naphthylacetic acid, that is, pass through α-
Methyl α-naphthyl acetate aliphatic alcohol ester hydrolyzes the embedding effect of slow release α-naphthylacetic acid and W/O lotions, and α-naphthalene is improved by duplicate protection
The slowly releasing effect of acetic acid, and then improve the lasting period of action of agricultural chemicals；
(2) the α-naphthylacetic acid aliphatic alcohol ester W/O lotions prepared by the present invention can form O/W type nanoemulsions after dilution,
Dispersion degree of the α-naphthylacetic acid aliphatic alcohol ester in lotion is improved, and then improves the effective rate of utilization of α-naphthylacetic acid, is reduced
Pesticide residue and environmental pollution.
(3) each ingredient used in α-naphthylacetic acid aliphatic alcohol ester W/O lotions of the invention does not cause damages to environment, green
Environmental protection.
(4) preparation process of α-naphthylacetic acid aliphatic alcohol ester W/O lotions of the invention is simple, favorable reproducibility, industry can be achieved
Metaplasia is produced.
Other features and advantages of the present invention will be described in detail in subsequent specific embodiment part.
Specific implementation mode
The preferred embodiment of the present invention is described in more detail below.Although the following describe the preferred implementations of the present invention
Mode, however, it is to be appreciated that may be realized in various forms the present invention without should be limited by embodiments set forth herein.Phase
Instead, these embodiments are provided so that the present invention is more thorough and complete, and can be by the scope of the present invention completely
It is communicated to those skilled in the art.
The first aspect of the present invention provides a kind of α-naphthylacetic acid aliphatic alcohol ester W/O lotions, with α-naphthylacetic acid aliphatic alcohol ester
The total weight of W/O lotions, the lotion include：α-naphthylacetic acid aliphatic alcohol ester 4-8wt%, vegetable oil 1-2wt%, emulsifier 40-
45wt%, propylene glycol 20-25wt% and water 20-25wt%.
In the present invention, propylene glycol can be used as a kind of cosurfactant, maintain the stabilization of W/O emulsion systems.Wherein, W/
O emulsion systems are water-in-oil emulsion system.
In accordance with the present invention it is preferred that the quality of the α-naphthylacetic acid aliphatic alcohol ester and vegetable oil quality sum and emulsifier
Than being 1：4-8；The mass ratio of the α-naphthylacetic acid aliphatic alcohol ester and vegetable oil is 2-4：1.
In accordance with the present invention it is preferred that the preparation method of the α-naphthylacetic acid aliphatic alcohol ester includes：In organic solvent and condensation
In the presence of agent, α-naphthylacetic acid and fatty alcohol are subjected to haptoreaction, obtain the α-naphthylacetic acid aliphatic alcohol ester.
In accordance with the present invention it is preferred that the organic solvent is dichloromethane, chloroform, acetonitrile, ethyl acetate, acetic acid
At least one of butyl ester, tetrahydrofuran, N-Methyl pyrrolidone and N,N-dimethylformamide；The condensing agent is 4- diformazans
Aminopyridine and dicyclohexylcarbodiimide；The fatty alcohol is butanol, hexanol, octanol, certain herbaceous plants with big flowers alcohol, lauryl alcohol, tetradecyl alchohol, 16
At least one of alcohol, octadecyl alcolol, eicosanol and docosanol.
In accordance with the present invention it is preferred that the catalytic temperature is 0-50 DEG C, time 0.5-10h；The α-naphthalene second
Acid, fatty alcohol, 4-dimethylaminopyridine and dicyclohexylcarbodiimide molar ratio be 1：1-2：0.025-0.1：1-2；Reaction
After successively through suction filtration, freezing, again filter and purifying obtain the α-naphthylacetic acid aliphatic alcohol ester.
In the present invention, cryogenic temperature is preferably 0-4 DEG C；Purifying is that silica gel column chromatography purifies.
In accordance with the present invention it is preferred that the vegetable oil is soybean oil, rapeseed oil, cottonseed oil, castor oil, turpentine oil, olive
At least one of oil, palm oil, corn oil and biodiesel.
Emulsifier in the present invention can be the conventional emulsifier of the Environmental security of any suitable present invention, preferably polyoxy
At least one of ethylene bay ether, Span, tween and polyvinylpyrrolidone.
The second aspect of the present invention provides a kind of preparation method of above-mentioned α-naphthylacetic acid aliphatic alcohol ester W/O lotions, the preparation
Method includes：The α-naphthylacetic acid aliphatic alcohol ester, vegetable oil, emulsifier, propylene glycol and water are uniformly mixed, the α-naphthalene is obtained
Acetic acid aliphatic alcohol ester W/O lotions.
Preferably, the preparation method of above-mentioned α-naphthylacetic acid aliphatic alcohol ester W/O lotions includes：(1) by the α-naphthalene
Acetic acid aliphatic alcohol ester, vegetable oil and emulsifier are uniformly mixed, and obtain oil phase；(2) propylene glycol and water are uniformly mixed, obtain water
Phase；(3) oil phase and the water phase are uniformly mixed, obtain the α-naphthylacetic acid aliphatic alcohol ester W/O lotions.Wherein, step
(1) in, mixing time 5-15min.
The third aspect of the present invention provides a kind of application process of above-mentioned α-naphthylacetic acid aliphatic alcohol ester W/O lotions, this method
Including：It is used after the α-naphthylacetic acid aliphatic alcohol ester W/O lotions are diluted with water；The α-naphthylacetic acid aliphatic alcohol ester W/O lotions
Volume ratio with water is preferably 1:40-2000.
The α-naphthylacetic acid aliphatic alcohol ester W/O lotions of the present invention in use, can be as needed according to different dilutions
Multiple is diluted, to form the O/W type nanoemulsions of various concentration.
The fourth aspect of the present invention provides a kind of nanoemulsions, and the nanoemulsions are by above-mentioned α-naphthylacetic acid aliphatic alcohol ester W/O
Lotion dilutes to obtain, and the grain size of nano-particle is preferably 15-25nm in the nanoemulsions.
The nanoemulsions of the present invention are O/W types nanoemulsions (oil-in-water type nano-emulsion liquid), and which raises α-naphthylacetic acid fat
Dispersion degree of the fatty alcohol in lotion, and then the effective rate of utilization of α-naphthylacetic acid is improved, it is dirty with environment to reduce pesticide residue
Dye.
It further illustrates the present invention by the following examples：
Preparation example 1：The preparation of α-naphthylacetic acid n-octyl alcohol ester
It weighs α-naphthylacetic acid (0.03mol, 5.58 grams) and n-octyl alcohol (0.03mol, 3.90 grams) is dissolved in anhydrous methylene chloride
(50mL) is then sequentially added into 4-dimethylaminopyridine (0.0015mol, 0.18 gram) and dicyclohexyl at ambient temperature
Carbodiimide (0.03mol, 6.18 grams) filters after reaction being stirred at room temperature 6 hours, and filtrate filters again after being freezed at 2 DEG C, filtrate
With silica gel column chromatography (ethyl acetate：Petroleum ether=1:15) α-naphthylacetic acid n-octyl alcohol ester, light yellow oil, yield are obtained after purification
92%,1H NMR(DMSO-d6,400MHz)：δ7.86-7.95(m,3H),7.44-7.53(m,4H),4.13(s,2H),3.93
(s, 2H), 1.41 (s, 2H), 1.08-1.15 (m, 10H), 0.75 (t, J=8.0Hz, 3H)；13CNMR(DMSO-d6,400MHz)：
δ171.21,133.35,131.76,131.11,128.49,128.04,127.60,126.13,125.72,125.50,
123.85,66.10,38.40,38.15,29.69,28.22,23.12,22.38,13.87,10.76.
Preparation example 2：The preparation of α-naphthylacetic acid n-dodecanol ester
It weighs α-naphthylacetic acid (0.03mol, 5.58 grams) and n-dodecanol (0.03mol, 5.58 grams) is dissolved in anhydrous dichloromethane
Alkane (50mL) is then sequentially added into 4-dimethylaminopyridine (0.0015mol, 0.18 gram) and two hexamethylenes at ambient temperature
Base carbodiimide (0.03mol, 6.18 grams) filters after reaction being stirred at room temperature 5 hours, and filtrate filters again after being freezed at 2 DEG C, filter
Liquid silica gel column chromatography (ethyl acetate：Petroleum ether=1：15) α-naphthylacetic acid n-dodecanol ester is obtained after purification, and light yellow oil is received
Rate 94%.1H NMR(DMSO-d6,400MHz)：δ7.86-7.94(m,3H),7.45-7.53(m,4H),4.13(s,2H),4.01
(s, 2H), 1.49 (s, 2H), 1.15-1.23 (m, 18H), 0.86 (t, J=8.0Hz, 3H；13C NMR(DMSO-d6,400MHz)：
δ171.19,133.34,131.77,131.10,128.49,128.06,127.61,126.15,125.73,125.52,
123.87,64.20,38.27,31.35,29.07,29.04,28.94,28.77,28.57,28.09,22.15,13.99.
Embodiment 1
The present embodiment provides a kind of α-naphthylacetic acid aliphatic alcohol ester W/O lotions, specific preparation method is：Weigh 1.20g tweens-
80 in sample bottle, and 0.24g α-naphthylacetic acid n-octyl alcohol esters (preparation example 1) and 0.06g soybean oils is added, and stirs 10 minutes, until equal
Even admixture；Propylene glycol is 1 with water quality ratio：1, it is uniformly mixed, prepares water phase；1.50g water phases are taken to be added to sample bottle
In, stirring forms α-naphthylacetic acid n-octyl alcohol ester W/O lotions.
Embodiment 2
The present embodiment provides a kind of α-naphthylacetic acid aliphatic alcohol ester W/O lotions, specific preparation method is：Weigh 1.25g tweens-
80 in sample bottle, and 0.20g α-naphthylacetic acid n-octyl alcohol esters (preparation example 1) and 0.05g soybean oils is added, and stirs 10 minutes, until equal
Even admixture；Propylene glycol is 1 with water quality ratio：1, it is uniformly mixed, prepares water phase；1.5g water phases are taken to be added to sample bottle
In, stirring forms α-naphthylacetic acid n-octyl alcohol ester W/O lotions.
Embodiment 3
The present embodiment provides a kind of α-naphthylacetic acid aliphatic alcohol ester W/O lotions, specific preparation method is：Weigh 1.34g tweens-
80 in sample bottle, and 0.134g α-naphthylacetic acid n-octyl alcohol esters (preparation example 1) and 0.033g soybean oils is added, and stirs 10 minutes, until
Uniform admixture；Propylene glycol is 1 with water quality ratio：1, it is uniformly mixed, prepares water phase；1.5g water phases are taken to be added to sample bottle
In, stirring forms α-naphthylacetic acid n-octyl alcohol ester W/O lotions.
Embodiment 4
The present embodiment provides a kind of α-naphthylacetic acid aliphatic alcohol ester W/O lotions, specific preparation method is：Weigh 1.25g tweens-
80 in sample bottle, and 0.2g α-naphthylacetic acid n-dodecanol esters (preparation example 2) and 0.05g soybean oils is added, and stirs 10 minutes, until equal
Even admixture；Propylene glycol is 1 with water quality ratio：1, it is uniformly mixed, prepares water phase；1.5g water phases are taken to be added to sample bottle
In, stirring forms α-naphthylacetic acid n-dodecanol ester W/O lotions.
Embodiment 5
The present embodiment provides a kind of α-naphthylacetic acid aliphatic alcohol ester W/O lotions, specific preparation method is：Weigh 1.34g tweens-
80 in sample bottle, and 0.134g α-naphthylacetic acid n-dodecanol esters (preparation example 2) and 0.033g soybean oils is added, and stirs 10 minutes,
To uniform admixture；Propylene glycol is 1 with water quality ratio：1, it is uniformly mixed, prepares water phase；1.5g water phases are taken to be added to sample
In bottle, stirring forms α-naphthylacetic acid n-dodecanol ester W/O lotions.
Test case
α-naphthylacetic acid aliphatic alcohol ester W/O lotions prepared by embodiment 1-5 are diluted with water respectively, obtain nano-emulsion
Liquid；Test the grain size and polymer dispersity index (PDI) of the α-naphthylacetic acid aliphatic alcohol ester in nanoemulsions；Specific test result is shown in
Table 1；Wherein, it is 1 that extension rate, which refers to α-naphthylacetic acid aliphatic alcohol ester W/O lotions and the volume ratio of water, in following table：Multiple.
Wherein, the present invention in test all samples grain size and monodispersity index (PDI) use Malvern ParticleSizer into
Row test.Its measurement method is：It takes the sample after 1.5 milliliters of corresponding multiples of dilution in cuvette, cuvette is positioned over
In Malvern ParticleSizer, it is dispersed phase, time 60s to impose a condition as 25 DEG C of room temperature, water, duplicate measurements sample under the conditions of this
Grain size and PDI three times, the relative standard deviation ＜ 10% between measurement result illustrates the repeatability of sample measurement result
Preferably.Finally using the average of three groups of data as the grain size and PDI for measuring sample.
Table 1
Various embodiments of the present invention are described above, above description is exemplary, and non-exclusive, and
It is not limited to disclosed each embodiment.Without departing from the scope and spirit of illustrated each embodiment, for this skill
Many modifications and changes will be apparent from for the those of ordinary skill in art field.
Claims (10)
1. a kind of α-naphthylacetic acid aliphatic alcohol ester W/O lotions, which is characterized in that with the gross weight of α-naphthylacetic acid aliphatic alcohol ester W/O lotions
Gauge, the lotion include：α-naphthylacetic acid aliphatic alcohol ester 4-8wt%, vegetable oil 1-2wt%, emulsifier 40-45wt%, propylene glycol
20-25wt% and water 20-25wt%.
2. α-naphthylacetic acid aliphatic alcohol ester W/O lotions according to claim 1, wherein the α-naphthylacetic acid aliphatic alcohol ester with
The mass ratio of vegetable oil quality sum and emulsifier is 1：4-8；The mass ratio of the α-naphthylacetic acid aliphatic alcohol ester and vegetable oil is
2-4：1.
3. α-naphthylacetic acid aliphatic alcohol ester W/O lotions according to claim 1, wherein the α-naphthylacetic acid aliphatic alcohol ester
Preparation method includes：In the presence of organic solvent and condensing agent, α-naphthylacetic acid and fatty alcohol are subjected to haptoreaction, obtain institute
State α-naphthylacetic acid aliphatic alcohol ester.
4. α-naphthylacetic acid aliphatic alcohol ester W/O lotions according to claim 3, wherein the organic solvent be dichloromethane,
In chloroform, acetonitrile, ethyl acetate, butyl acetate, tetrahydrofuran, N-Methyl pyrrolidone and N,N-dimethylformamide
It is at least one；The condensing agent is 4-dimethylaminopyridine and dicyclohexylcarbodiimide；The fatty alcohol be butanol, hexanol,
At least one of octanol, certain herbaceous plants with big flowers alcohol, lauryl alcohol, tetradecyl alchohol, hexadecanol, octadecyl alcolol, eicosanol and docosanol.
5. α-naphthylacetic acid aliphatic alcohol ester W/O lotions according to claim 4, wherein the catalytic temperature is 0-
50 DEG C, time 0.5-10h；Mole of the α-naphthylacetic acid, fatty alcohol, 4-dimethylaminopyridine and dicyclohexylcarbodiimide
Than being 1：1-2：0.025-0.1：1-2；Process filters successively after reaction, freezing, suction filtration and purifying obtain the α-again
Methyl α-naphthyl acetate aliphatic alcohol ester.
6. α-naphthylacetic acid aliphatic alcohol ester W/O lotions according to claim 1, wherein the vegetable oil is soybean oil, vegetable seed
At least one of oil, cottonseed oil, castor oil, turpentine oil, olive oil, palm oil, corn oil and biodiesel.
7. α-naphthylacetic acid aliphatic alcohol ester W/O lotions according to claim 1, wherein the emulsifier is the polyoxyethylene moon
At least one of osmanthus ether, Span, tween and polyvinylpyrrolidone.
8. the preparation method of the α-naphthylacetic acid aliphatic alcohol ester W/O lotions described in any one of claim 1-7, feature exist
In the preparation method includes：The α-naphthylacetic acid aliphatic alcohol ester, vegetable oil, emulsifier, propylene glycol and water are uniformly mixed, obtained
To the α-naphthylacetic acid aliphatic alcohol ester W/O lotions.
9. the application process of the α-naphthylacetic acid aliphatic alcohol ester W/O lotions described in any one of claim 1-7, feature exist
In this method includes：It is used after the α-naphthylacetic acid aliphatic alcohol ester W/O lotions are diluted with water；The α-naphthylacetic acid fatty alcohol
Ester W/O lotions and the volume ratio of water are preferably 1:40-2000.
10. a kind of nanoemulsions, the nanoemulsions are by the α-naphthylacetic acid aliphatic alcohol ester W/ described in any one of claim 1-7
O lotions dilute to obtain, and the grain size of nano-particle is preferably 15-25nm in the nanoemulsions.
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