CN104817585A - Tri-n-butyl tin 1, 6-naphthyl dioxo-acetate coordination polymer and preparation method and application thereof - Google Patents
Tri-n-butyl tin 1, 6-naphthyl dioxo-acetate coordination polymer and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a tri-n-butyl tin 1, 6-naphthyl dioxo-acetate coordination polymer which is shown in a structural formula (I), and Bu is normal-butyl. The invention further discloses a preparation method of the tri-n-butyl tin 1, 6-naphthyl dioxo-acetate coordination polymer. Good growth inhibiting functions are shown on purslane, semen cassiae, amaranthus spinosus, red round-leaf edible amaranth, alfalfa and the like by means of the tri-n-butyl tin 1, 6-naphthyl dioxo-acetate coordination polymer, the tri-n-butyl tin 1, 6-naphthyl dioxo-acetate coordination polymer has the advantages of high herbicidal activity, low costs, simple preparation method and the like, and a new path is provided for developing novel herbicides. The formula (I) is (img file=' DDA0000699889340000011. TIF' wi=' 1248' he=' 870'/).
Description
Technical field
The present invention relates to a kind of tri-n-butyl tin 1,6-naphthalene dioxy acetic ester ligand polymer and preparation method thereof, and the application of tri-n-butyl tin 1,6-naphthalene dioxy acetic ester in plant-growth regulator.
Background technology
Organotin and derivative thereof have good biological activity, are used as desinsection, sterilization and cancer therapy drug, and antifouling paint, wood preservation etc.Some organo-tin compound also has weeding activity, their low phytotoxicities, general low to the toxicity of non-target tissues, the less compound of toxicity easily can be transformed into quickly in the environment to light, heat and biology, finally be degraded into nontoxic inorganic tindioxide residue, have desinsection, the multiple effect of sterilization concurrently as weedicide, demonstrate good Development volue.Phenoxy carboxylic acid herbicides is the class weedicide that output is maximum, usable floor area is the widest always, this weedicide structure is simple, activity is high, cost is low, but this type of compound structure is modified, by itself and organo-tin compound generation coordination, seek that drug effect is better, selectivity is better, weedicide new variety that are use safety have great Research Significance.
Document (Chinese Journal of Inorganic Chemistry, 2010,26:1507-1510) is reported, the synthetic method of tri-n-butyl tin 2,4 dichlorophenoxyacetic acid ester and its structure.
Document (chemical research and application, 2010,22:926-929) is reported, the synthetic method of siliceous dialkyl tin phenoxy acetic acid title complex.
Document (organic chemistry, 1991,11:82-87) is reported, the synthetic method of Tricyclohexyltin aromatoxyacetate and kill mite and the effect to plant-growth regulator.
US Patent No. 3723089 discloses the plant-growth regulator effect of a kind of organo-tin compound to plant such as leaf mustard, lamb's-quarters, lady's-grass, corn, wheat, cotton, peas.
US Patent No. 4260552 discloses the weeding activity of a series of polysubstituted organo-tin compound to plant such as lamb's-quarters, thorn apple, morning glory, lady's-grass, paddy green bristlegrass and barnyard grasses, and the growth inhibition ratio of most compounds to tested plant reaches 100%.
The experiment proved that material plant to growth regulating effect based on trialkylated tin aryloxyacetic acid ester compound, the present invention selects the organotin of three normal-butyl stannic oxide, 1,6-naphthalene two fluoroacetic acid is part, react under certain condition, synthesis obtains the compound stronger to the growth regulating effect of purslane, Semen Cassiae, thorn amaranth, red roundleaf three-coloured amaranth, clover, provides new approach for developing new plant-growth regulator agent.
Summary of the invention
The first object of the present invention there is provided a kind of tri-n-butyl tin 1,6-naphthalene dioxy acetic ester ligand polymer.
The second object of the present invention is to provide the preparation method of above-mentioned tri-n-butyl tin 1,6-naphthalene dioxy acetic ester ligand polymer.
The third object of the present invention is to provide the application of above-mentioned tri-n-butyl tin 1,6-naphthalene dioxy acetic ester ligand polymer in plant-growth regulator.
As a kind of tri-n-butyl tin 1,6-naphthalene dioxy acetic ester ligand polymer of a first aspect of the present invention, it is the polymkeric substance of structural formula (I)
Wherein Bu is normal-butyl.
Tri-n-butyl tin 1,6-naphthalene dioxy acetic ester ligand polymer of the present invention is through ultimate analysis, infrared spectra, nuclear magnetic resonance spectrum and the structural analysis of X-ray single crystal diffraction, and result is as follows:
Ultimate analysis (C
38h
64o
6sn
2): theoretical value: C 53.42, H 7.55; Measured value: C 53.43, H7.54.
IR(KBr,cm
-1)：2956.8(s),2922.1(s)，1604.7(s)，1581.6(s)，1411.8(s)，775.3(m)，669.3(m)，516.9(w)，491.8(w)。
1H NMR(CDCl
3,500MHz),δ(ppm)：0.90～1.64(m，54H，Bu-H)，4.71(s,2H,-OCH
2-)，4.76(s,2H,-OCH
2-)，6.91(d,1H,Ph-H)，7.03(d,1H,Ph-H)，7.23(m,1H,Ph-H)，7.30(d,2H,Ph-H)，8.31(d,1H,Ph-H)。
13C NMR(CDCl
3,125MHz)，δ(ppm)：173.57(-COO)，103.23～156.69(Ph-C)，66.11(-OCH
2-)，13.63～27.75(Bu-C)。
Tri-n-butyl tin 1,6-naphthalene dioxy acetic ester ligand polymer of the present invention is crystalline structure, and its crystal is oblique system, spacer P2
1/ n, a=1.05002 (7) nm, b=2.40920 (15) nm, c=1.75054 (11) nm, α=γ=90 °, β=92.1150 (10) °, Z=4, V=4.4253 (5) nm
3.
Tri-n-butyl tin 1 of the present invention, the constructional feature of 6-naphthalene dioxy acetic ester ligand polymer is: in molecule each tin atom all with the carboxyl oxygen coordination of another molecule, form two-dimension netted ligand polymer, center tin atom is pentacoordinate distortion trigonal bipyramid configuration.
As a kind of tri-n-butyl tin 1 of a second aspect of the present invention, the preparation method of 6-naphthalene dioxy acetic ester ligand polymer, in the reaction vessel having nitrogen protection, add 1,6-naphthalene two fluoroacetic acid, three normal-butyl stannic oxide and reaction solvents in order successively, under stirring and refluxing, react 4 ~ 12h; Cooling, filters; At pressure 0.004 ~ 0.01MPa, temperature is under 30 ~ 55 DEG C of conditions, with Rotary Evaporators evaporate to dryness filtrate, obtain beige solid, with methylene chloride-methanol mixed solvent recrystallization, under 10 ~ 35 DEG C of conditions, control solvent evaporates crystallization, obtain beige crystal, be tri-n-butyl tin 1,6-naphthalene dioxy acetic ester ligand polymer.
In a preferred embodiment of the invention, the mass ratio of the material of described 1,6-naphthalene two fluoroacetic acid and three normal-butyl stannic oxide is 1:1 ~ 1:1.2.
In a preferred embodiment of the invention, the consumption of described reaction solvent is that every mmole three normal-butyl stannic oxide adds 10 ~ 25 milliliters.
In a preferred embodiment of the invention, described reaction solvent is dehydrated alcohol or anhydrous methanol or dry-out benzene.
In a preferred embodiment of the invention, in described methylene chloride-methanol mixed solvent, the volume ratio of methylene dichloride and methyl alcohol is 1:10 ~ 1:20.
As the application of a kind of tri-n-butyl tin 1,6-naphthalene dioxy acetic ester ligand polymer in plant-growth regulator of a third aspect of the present invention.
Applicant is to above-mentioned tri-n-butyl tin 1,6-naphthalene dioxy acetic ester ligand polymer has carried out weeding activity research, confirm tri-n-butyl tin 1,6-naphthalene dioxy acetic ester ligand polymer has plant growth regulation, that is the purposes of above-mentioned ligand polymer is preparing the application in plant-growth regulator, is exactly the application in preparation purslane or Semen Cassiae or thorn amaranth or Red Garden leaf three-coloured amaranth or alfalfa plant growth regulator specifically.
Tri-n-butyl tin 1 of the present invention, 6-naphthalene dioxy acetic ester ligand polymer demonstrates good Developing restraint effect to purslane, Semen Cassiae, thorn amaranth, red roundleaf three-coloured amaranth, clover etc., tri-n-butyl tin 1 of the present invention, the features such as 6-naphthalene dioxy acetic ester ligand polymer weeding activity is high, cost is low, preparation method is simple, provide new way for developing new weedicide.
Accompanying drawing explanation
Fig. 1 is tri-n-butyl tin 1,6-naphthalene dioxy acetic ester structure iron.
Fig. 2 is the two-dimensional network structure figure of tri-n-butyl tin 1,6-naphthalene dioxy acetic ester ligand polymer.
Fig. 3 is the IR spectrogram of tri-n-butyl tin 1,6-naphthalene dioxy acetic ester ligand polymer.
Fig. 4 is tri-n-butyl tin 1,6-naphthalene dioxy acetic ester ligand polymer
1h NMR spectrogram.
Fig. 5 is tri-n-butyl tin 1,6-naphthalene dioxy acetic ester ligand polymer
13c NMR spectrogram.
Specific implementation method
Further describe the present invention by following examples, but scope of the present invention should be noted not by any restriction of these embodiments.
Embodiment 1:
The preparation of tri-n-butyl tin 1,6-naphthalene dioxy acetic ester ligand polymer:
50mL has in the there-necked flask of nitrogen protection, add 0.274g (1mmol) 1, 6-naphthalene two fluoroacetic acid, 0.596g (1mmol) three normal-butyl stannic oxide, 20ml anhydrous methanol, stirring and refluxing 6h, after having reacted, be cooled to room temperature, filter, at pressure 0.004MPa, temperature is under 30 DEG C of conditions, with Rotary Evaporators evaporate to dryness filtrate, obtain beige solid, with methylene chloride-methanol mixed solvent recrystallization, wherein the volume ratio of methylene dichloride and methyl alcohol is 1:20, under 10 ~ 35 DEG C of conditions, control solvent evaporates crystallization, obtain beige crystal, be tri-n-butyl tin 1 of the present invention, 6-naphthalene dioxy acetic ester ligand polymer.Productive rate: 45.6%.Fusing point: 130 DEG C ~ 131 DEG C.
Ultimate analysis (C
38h
64o
6sn
2): theoretical value: C 53.42, H 7.55; Measured value: C 53.43, H7.54.
IR(KBr,cm
-1)：2956.8(s),2922.1(s)，1604.7(s)，1581.6(s)，1411.8(s)，775.3(m)，669.3(m)，516.9(w)，491.8(w)。
1H NMR(CDCl
3,500MHz),δ(ppm)：0.90～1.64(m，54H，Bu-H)，4.71(s,2H,-OCH
2-)，4.76(s,2H,-OCH
2-)，6.91(d,1H,Ph-H)，7.03(d,1H,Ph-H)，7.23(m,1H,Ph-H)，7.30(d,2H,Ph-H)，8.31(d,1H,Ph-H)。
13C NMR(CDCl
3,125MHz)，δ(ppm)：173.57(-COO)，103.23～156.69(Ph-C)，66.11(-OCH
2-)，13.63～27.75(Bu-C)。
Crystallographic data: oblique system, spacer P2
1/ n, a=1.05002 (7) nm, b=2.40920 (15) nm, c=1.75054 (11) nm, α=γ=90 °, β=92.1150 (10) °, Z=4, V=4.4253 (5) nm
3.
Embodiment 2:
The preparation of tri-n-butyl tin 1,6-naphthalene dioxy acetic ester ligand polymer:
25mL has in the there-necked flask of nitrogen protection, add 0.274g (1mmol) 1, 6-naphthalene two fluoroacetic acid, 0.655g (1.1mmol) three normal-butyl stannic oxide, 11ml dehydrated alcohol, stirring and refluxing 4h, after having reacted, be cooled to room temperature, filter, at pressure 0.005MPa, temperature is under 35 DEG C of conditions, with Rotary Evaporators evaporate to dryness filtrate, obtain beige solid, with methylene chloride-methanol mixed solvent recrystallization, wherein the volume ratio of methylene dichloride and methyl alcohol is 1:12, under 10 ~ 35 DEG C of conditions, control solvent evaporates crystallization, obtain beige crystal, be tri-n-butyl tin 1 of the present invention, 6-naphthalene dioxy acetic ester ligand polymer.Productive rate: 45.9%.Fusing point: 130 DEG C ~ 131 DEG C.
Ultimate analysis (C
38h
64o
6sn
2): theoretical value: C 53.42, H 7.55; Measured value: C 53.43, H7.54.
IR(KBr,cm
-1)：2956.8(s),2922.1(s)，1604.7(s)，1581.6(s)，1411.8(s)，775.3(m)，669.3(m)，516.9(w)，491.8(w)。
1H NMR(CDCl
3,500MHz),δ(ppm)：0.90～1.64(m，54H，Bu-H)，4.71(s,2H,-OCH
2-)，4.76(s,2H,-OCH
2-)，6.91(d,1H,Ph-H)，7.03(d,1H,Ph-H)，7.23(m,1H,Ph-H)，7.30(d,2H,Ph-H)，8.31(d,1H,Ph-H)。
13C NMR(CDCl
3,125MHz)，δ(ppm)：173.57(-COO)，103.23～156.69(Ph-C)，66.11(-OCH
2-)，13.63～27.75(Bu-C)。
Crystallographic data: oblique system, spacer P2
1/ n, a=1.05002 (7) nm, b=2.40920 (15) nm, c=1.75054 (11) nm, α=γ=90 °, β=92.1150 (10) °, Z=4, V=4.4253 (5) nm
3.
Embodiment 3:
The preparation of tri-n-butyl tin 1,6-naphthalene dioxy acetic ester ligand polymer:
50mL has in the there-necked flask of nitrogen protection, add 0.274g (1mmol) 1, 6-naphthalene two fluoroacetic acid, 0.715g (1.2mmol) three normal-butyl stannic oxide, 30ml dry-out benzene, stirring and refluxing 12h, after having reacted, be cooled to room temperature, filter, at pressure 0.01MPa, temperature is under 55 DEG C of conditions, with Rotary Evaporators evaporate to dryness filtrate, obtain beige solid, with methylene chloride-methanol mixed solvent recrystallization, wherein the volume ratio of methylene dichloride and methyl alcohol is 1:15, under 10 ~ 35 DEG C of conditions, control solvent evaporates crystallization, obtain beige crystal, be tri-n-butyl tin 1 of the present invention, 6-naphthalene dioxy acetic ester ligand polymer.Productive rate: 46.1%.Fusing point: 130 DEG C ~ 131 DEG C.
Ultimate analysis (C
38h
64o
6sn
2): theoretical value: C 53.42, H 7.55; Measured value: C 53.43, H7.54.
IR(KBr,cm
-1)：2956.8(s),2922.1(s)，1604.7(s)，1581.6(s)，1411.8(s)，775.3(m)，669.3(m)，516.9(w)，491.8(w)。
1H NMR(CDCl
3,500MHz),δ(ppm)：0.90～1.64(m，54H，Bu-H)，4.71(s,2H,-OCH
2-)，4.76(s,2H,-OCH
2-)，6.91(d,1H,Ph-H)，7.03(d,1H,Ph-H)，7.23(m,1H,Ph-H)，7.30(d,2H,Ph-H)，8.31(d,1H,Ph-H)。
13C NMR(CDCl
3,125MHz)，δ(ppm)：173.57(-COO)，103.23～156.69(Ph-C)，66.11(-OCH
2-)，13.63～27.75(Bu-C)。
Crystallographic data: oblique system, spacer P2
1/ n, a=1.05002 (7) nm, b=2.40920 (15) nm, c=1.75054 (11) nm, α=γ=90 °, β=92.1150 (10) °, Z=4, V=4.4253 (5) nm
3.
Embodiment 4:
The preparation of tri-n-butyl tin 1,6-naphthalene dioxy acetic ester ligand polymer:
250mL has in the there-necked flask of nitrogen protection, add 2.74g (10mmol) 1, 6-naphthalene two fluoroacetic acid, 6.44g (10.8mmol) three normal-butyl stannic oxide, 110ml dry-out benzene, stirring and refluxing 10h, after having reacted, be cooled to room temperature, filter, at pressure 0.007MPa, temperature is under 50 DEG C of conditions, with Rotary Evaporators evaporate to dryness filtrate, obtain beige solid, with methylene chloride-methanol mixed solvent recrystallization, wherein the volume ratio of methylene dichloride and methyl alcohol is 1:18, under 10 ~ 35 DEG C of conditions, control solvent evaporates crystallization, obtain beige crystal, be tri-n-butyl tin 1 of the present invention, 6-naphthalene dioxy acetic ester ligand polymer.Productive rate: 46.7%.Fusing point: 130 DEG C ~ 131 DEG C.
Ultimate analysis (C
38h
64o
6sn
2): theoretical value: C 53.42, H 7.55; Measured value: C 53.43, H7.54.
IR(KBr,cm
-1)：2956.8(s),2922.1(s)，1604.7(s)，1581.6(s)，1411.8(s)，775.3(m)，669.3(m)，516.9(w)，491.8(w)。
1H NMR(CDCl
3,500MHz),δ(ppm)：0.90～1.64(m，54H，Bu-H)，4.71(s,2H,-OCH
2-)，4.76(s,2H,-OCH
2-)，6.91(d,1H,Ph-H)，7.03(d,1H,Ph-H)，7.23(m,1H,Ph-H)，7.30(d,2H,Ph-H)，8.31(d,1H,Ph-H)。
13C NMR(CDCl
3,125MHz)，δ(ppm)：173.57(-COO)，103.23～156.69(Ph-C)，66.11(-OCH
2-)，13.63～27.75(Bu-C)。
Crystallographic data: oblique system, spacer P2
1/ n, a=1.05002 (7) nm, b=2.40920 (15) nm, c=1.75054 (11) nm, α=γ=90 °, β=92.1150 (10) °, Z=4, V=4.4253 (5) nm
3.
Embodiment 5:
The preparation of tri-n-butyl tin 1,6-naphthalene dioxy acetic ester ligand polymer:
250mL has in the there-necked flask of nitrogen protection, add 2.74g (10mmol) 1, 6-naphthalene two fluoroacetic acid, 6.85g (11.5mmol) three normal-butyl stannic oxide, 150ml anhydrous methanol, stirring and refluxing 8h, after having reacted, be cooled to room temperature, filter, at pressure 0.008MPa, temperature is under 38 DEG C of conditions, with Rotary Evaporators evaporate to dryness filtrate, obtain beige solid, with methylene chloride-methanol mixed solvent recrystallization, wherein the volume ratio of methylene dichloride and methyl alcohol is 1:10, under 10 ~ 35 DEG C of conditions, control solvent evaporates crystallization, obtain beige crystal, be tri-n-butyl tin 1 of the present invention, 6-naphthalene dioxy acetic ester ligand polymer.Productive rate: 46.9%.Fusing point: 130 DEG C ~ 131 DEG C.
Ultimate analysis (C
38h
64o
6sn
2): theoretical value: C 53.42, H 7.55; Measured value: C 53.43, H7.54.
IR(KBr,cm
-1)：2956.8(s),2922.1(s)，1604.7(s)，1581.6(s)，1411.8(s)，775.3(m)，669.3(m)，516.9(w)，491.8(w)。
1H NMR(CDCl
3,500MHz),δ(ppm)：0.90～1.64(m，54H，Bu-H)，4.71(s,2H,-OCH
2-)，4.76(s,2H,-OCH
2-)，6.91(d,1H,Ph-H)，7.03(d,1H,Ph-H)，7.23(m,1H,Ph-H)，7.30(d,2H,Ph-H)，8.31(d,1H,Ph-H)。
13C NMR(CDCl
3,125MHz)，δ(ppm)：173.57(-COO)，103.23～156.69(Ph-C)，66.11(-OCH
2-)，13.63～27.75(Bu-C)。
Crystallographic data: oblique system, spacer P2
1/ n, a=1.05002 (7) nm, b=2.40920 (15) nm, c=1.75054 (11) nm, α=γ=90 °, β=92.1150 (10) °, Z=4, V=4.4253 (5) nm
3.
Embodiment 6:
The preparation of tri-n-butyl tin 1,6-naphthalene dioxy acetic ester ligand polymer:
100mL has in the there-necked flask of nitrogen protection, add 2.74g (10mmol) 1, 6-naphthalene two fluoroacetic acid, 6.08g (10.2mmol) three normal-butyl stannic oxide, 61ml dehydrated alcohol, stirring and refluxing 12h, after having reacted, be cooled to room temperature, filter, at pressure 0.009MPa, temperature is under 45 DEG C of conditions, with Rotary Evaporators evaporate to dryness filtrate, obtain beige solid, with methylene chloride-methanol mixed solvent recrystallization, wherein the volume ratio of methylene dichloride and methyl alcohol is 1:16, under 10 ~ 35 DEG C of conditions, control solvent evaporates crystallization, obtain beige crystal, be tri-n-butyl tin 1 of the present invention, 6-naphthalene dioxy acetic ester ligand polymer.Productive rate: 47.3%.Fusing point: 130 DEG C ~ 131 DEG C.
Ultimate analysis (C
38h
64o
6sn
2): theoretical value: C 53.42, H 7.55; Measured value: C 53.43, H7.54.
IR(KBr,cm
-1)：2956.8(s),2922.1(s)，1604.7(s)，1581.6(s)，1411.8(s)，775.3(m)，669.3(m)，516.9(w)，491.8(w)。
1H NMR(CDCl
3,500MHz),δ(ppm)：0.90～1.64(m，54H，Bu-H)，4.71(s,2H,-OCH
2-)，4.76(s,2H,-OCH
2-)，6.91(d,1H,Ph-H)，7.03(d,1H,Ph-H)，7.23(m,1H,Ph-H)，7.30(d,2H,Ph-H)，8.31(d,1H,Ph-H)。
13C NMR(CDCl
3,125MHz)，δ(ppm)：173.57(-COO)，103.23～156.69(Ph-C)，66.11(-OCH
2-)，13.63～27.75(Bu-C)。
Crystallographic data: oblique system, spacer P2
1/ n, a=1.05002 (7) nm, b=2.40920 (15) nm, c=1.75054 (11) nm, α=γ=90 °, β=92.1150 (10) °, Z=4, V=4.4253 (5) nm
3.
Test example:
Tri-n-butyl tin 1,6-naphthalene dioxy acetic ester of the present invention, its Herbicidal is realized by Plating experimental technique.
Plating:
Plating is adopted to measure tri-n-butyl tin 1, the 6-naphthalene dioxy acetic ester of embodiment 1 preparation to the weeding activity of common weed in the farm crop such as purslane, Semen Cassiae, thorn amaranth, red roundleaf three-coloured amaranth, clover.
Test process: weigh a certain amount of testing sample with analytical balance, adds a small amount of DMF and dissolves, and drip 1 emulsifying agent (tween-80), it is stand-by that adding distil water is diluted to desired concn respectively.
With the culture dish of diameter 9cm, built-in two layers of filter paper and 10 have exposed the seeds such as the white purslane of bud, Semen Cassiae, thorn amaranth, red roundleaf three-coloured amaranth, clover, and adding 5mL said sample solution is respectively nutrient solution, directly makes blank with distilled water as nutrient solution, incubation growth in growth cabinet is positioned over after process, keep temperature 25 DEG C, humidity 80%RH, illumination 30%, periodicity of illumination daytime/night=16/8 culture condition, cultivate 6 days, measurement result, each test parallel testing three times.
Data processing: measure the stem of plant and the length of root with ruler, get its mean value, calculates the inhibiting rate of medicament.Result is for just to illustrate that medicament is inhibited, for negative, result illustrates that medicament has promoter action.
Inhibiting rate=[(blank mean length-process mean length)/blank mean length] * 100%
As shown in table 1 with the weeding activity test result of Plating to seeds such as purslane, Semen Cassiae, thorn amaranth, red roundleaf three-coloured amaranth, clovers, experiment shows, along with the concentration of compound increases, good Developing restraint effect is demonstrated to purslane, Semen Cassiae, thorn amaranth, red roundleaf three-coloured amaranth and clover.
The weeding activity experimental data (growth inhibition ratio %) of table 1 tri-n-butyl tin 1,6-naphthalene dioxy acetic ester.
Tri-n-butyl tin 1,6-naphthalene dioxy acetic ester prepared by all the other embodiments is with the same test example of weeding activity testing method of Plating to seeds such as purslane, Semen Cassiae, thorn amaranth, red roundleaf three-coloured amaranth, clovers, and result and table 1 are substantially identical.
Claims (9)
1. tri-n-butyl tin 1, a 6-naphthalene dioxy acetic ester ligand polymer, the compound for following structural formula (I):
Wherein Bu is normal-butyl.
2. tri-n-butyl tin 1,6-naphthalene dioxy acetic ester as claimed in claim 1, wherein, described tri-n-butyl tin 1,6-naphthalene dioxy acetic ester is crystalline structure, its crystallographic data: oblique system, spacer P2
1/ n, a=1.05002 (7) nm, b=2.40920 (15) nm, c=1.75054 (11) nm, α=γ=90 °, β=92.1150 (10) °, Z=4, V=4.4253 (5) nm
3.
3. the tri-n-butyl tin 1 described in claim 1 or 2, the preparation method of 6-naphthalene dioxy acetic ester, it is characterized in that in the reaction vessel having nitrogen protection, add 1,6-naphthalene two fluoroacetic acid, three normal-butyl stannic oxide and reaction solvents in order successively, under stirring and refluxing, react 4 ~ 12h; Cooling, filters; At pressure 0.004 ~ 0.01MPa, temperature is under 30 ~ 55 DEG C of conditions, with Rotary Evaporators evaporate to dryness filtrate, obtain beige solid, with methylene chloride-methanol mixed solvent recrystallization, under 10 ~ 35 DEG C of conditions, control solvent evaporates crystallization, obtain beige crystal, be tri-n-butyl tin 1,6-naphthalene dioxy acetic ester.
4. preparation method as claimed in claim 3, it is characterized in that, the mass ratio of the material of described 1,6-naphthalene two fluoroacetic acid and three normal-butyl stannic oxide is 1:1 ~ 1:1.2.
5. preparation method as claimed in claim 3, it is characterized in that, the consumption of described reaction solvent is that every mmole three normal-butyl stannic oxide adds 10 ~ 25 milliliters.
6. the preparation method as described in claim 3 or 5, is characterized in that, described reaction solvent is dehydrated alcohol or anhydrous methanol or dry-out benzene.
7. preparation method as claimed in claim 3, it is characterized in that, in described methylene chloride-methanol mixed solvent, the volume ratio of methylene dichloride and methyl alcohol is 1:10 ~ 1:20.
8. the application of tri-n-butyl tin 1,6-naphthalene dioxy acetic ester in plant-growth regulator described in claim 1 or 2.
9. application according to claim 8, wherein said plant is purslane, Semen Cassiae, thorn amaranth, red roundleaf three-coloured amaranth or clover.
Priority Applications (1)
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| CN103087115A (en) * | 2013-02-04 | 2013-05-08 | 衡阳师范学院 | Ferrocenyl-containing tributyltin benzoate coordination polymer, and preparation method and application thereof |
| CN103087325A (en) * | 2013-02-04 | 2013-05-08 | 衡阳师范学院 | Ferrocenyl-containing tricyclohexyltin coordination polymer, and preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103087115A (en) * | 2013-02-04 | 2013-05-08 | 衡阳师范学院 | Ferrocenyl-containing tributyltin benzoate coordination polymer, and preparation method and application thereof |
| CN103087325A (en) * | 2013-02-04 | 2013-05-08 | 衡阳师范学院 | Ferrocenyl-containing tricyclohexyltin coordination polymer, and preparation method and application thereof |
Non-Patent Citations (2)
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| ABOUBACAR SIDIKI SOUGOULE等，: "A novel macrocyclic organotin carboxylate containing a penta-nuclear", 《JOURNAL OF ORGANOMETALLIC CHEMISTRY》 * |
| 谢庆兰等，: "三环己基锡芳氧乙酸盐的合成及其结构表征", 《有机化学》 * |
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