CN105198918A - Bis[tris(2-methyl-2-phenyl)propyl]tin o-phenyldioxyacetate as well as preparation method and application thereof - Google Patents
Bis[tris(2-methyl-2-phenyl)propyl]tin o-phenyldioxyacetate as well as preparation method and application thereof Download PDFInfo
- Publication number
- CN105198918A CN105198918A CN201510752634.7A CN201510752634A CN105198918A CN 105198918 A CN105198918 A CN 105198918A CN 201510752634 A CN201510752634 A CN 201510752634A CN 105198918 A CN105198918 A CN 105198918A
- Authority
- CN
- China
- Prior art keywords
- phenyl
- tin
- methyl
- propyl group
- adjacent benzene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Abstract
The invention discloses bis[tris(2-methyl-2-phenyl)propyl]tin o-phenyldioxyacetate. Bis[tris(2-methyl-2-phenyl)propyl]tin o-phenyldioxyacetate is a complex with a structural formula (I) shown in the specification, wherein Ph in the formula is phenyl. The invention also discloses a preparation method of the complex and an application of the complex in biological weed control activity.
Description
Technical field
The present invention relates to two [three (2-methyl-2-phenyl) propyl group] tin adjacent benzene dioxy acetic ester and preparation method thereof, and the application of the adjacent benzene dioxy acetic ester of this two [three (2-methyl-2-phenyl) propyl group] tin in plant growth regulating.
Background technology
In agriculture weeding, use a kind of weedicide or its composition for a long time, in a large number, weeds can develop immunity to drugs, and therefore, weedicide needs continuous innovation.People are in order to find the good herbicidal compound of high reactivity, highly selective and Environmental compatibility, and one of fruitful approach utilizes the activated compound of tool for guide's developing new drug thing.As everyone knows, since discovery 2,4-dichlorphenoxyacetic acid has efficiently, after the weeding of highly selective and biological regulation effect, phenoxy carboxylic acid herbicides is because structure is simple, activity is high, cost is low, is the class weedicide that output is maximum, usable floor area is the widest always.
Phenoxy acetic acid is not only widely used, and structure is special, different from general phenylformic acid, lipid acid, its alkoxyl group with rigidity phenyl ring, flexibility and the carboxyl of strong coordination, there is the feature of the organometallic complex of the coordination mode flexible and changeable with metal and the changeable formation different structure of sterie configuration, the new compound with novel structure and property can be constructed.
Organotin and derivative thereof not only have good biological activity, are used as desinsection, sterilization and cancer therapy drug, and antifouling paint, wood preservation etc.Some organo-tin compounds, also have the weeding activity being better than or being equivalent to 2,4 dichlorophenoxyacetic acid.Their low phytotoxicities, general low to the toxicity of non-target tissues, in environment under light, heat and biological action, easily can be transformed into the less compound of toxicity quickly, finally be degraded into nontoxic tindioxide residue, have desinsection, the multiple effect of sterilization concurrently as weedicide, demonstrate good Development volue.Therefore, with phenoxy acetic acid and organo-tin compound for precursor, organotin phenoxy acetic acid ester is formed with the key effect that becomes of tin by carboxyl, or form title complex by the coordination of carbonyl and tin, the compounds two classes with weeding activity is integrated, seek that drug effect is better, selectivity be better, the weedicide new variety of use safety, significant.
Document (Chinese Journal of Inorganic Chemistry, 2006,22:656-660) is reported, the synthetic method of dialkyl tin Chlorlacetic Acid ester.
Document (organic chemistry, 2006,11:1571-1575) report, series of new is containing aryloxyacetic acid ester group triadimefon compound, the weeding activity test result of this series compound shows, substituting groups different on phenyl ring has obvious impact to weeding activity.
Document (chemical journal, 1995,53:1034-1040) report, the synthetic method of mixed trialkylated tin derivative methyldicyclohexyl tin (replacement) phenoxy acetic acid ester and biological activity, research shows, these compounds, except there being good acaricidal activity, also have certain sterilization, weeding and Plant Hormone Action.
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.
Document (JournalofOrganometallicChemistry, 2014,758:19-24) is reported, the synthetic method of di-n-butyl tin isophthalic dioxy acetic ester.
Document (SCI, 1991,12:1186-1189) is reported, the synthesis of tributyl tin hydrocarbon fluoroacetate and weeding activity, and the weeding activity of this compounds is better than or close to weedicide 2,4 dichlorophenoxyacetic acid.
Document (chemical journal, 1995,53:721-728) is reported, mixing tributyl tin carboxylicesters is to the weeding activity of the test materialss such as oat, barnyard grass, lady's-grass, rape, clover, three-coloured amaranth, and part of compounds has good inhibition.
Mixed trialkylated tin derivative pesticide disclosed in Chinese patent CN1097546A has very strong sterilization, desinsection, kills the two or more biological activity such as mite and weeding.
US Patent No. 3723089 discloses the plant growth regulation 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 organotin of selective oxidation of the present invention two [three (2-methyl-2-phenyl) propyl group tin], adjacent benzene two fluoroacetic acid is part, react under certain condition, synthesis obtains the compound stronger to the growth regulating effect of purslane, Amaranthus retroflexus, Semen Cassiae, thorn amaranth, red roundleaf three-coloured amaranth, clover, provides new approach for developing new plant-growth regulator.
Summary of the invention
The first object of the present invention there is provided a kind of two [three (2-methyl-2-phenyl) propyl group] tin adjacent benzene dioxy acetic ester.
The second object of the present invention is to provide the preparation method of above-mentioned two [three (2-methyl-2-phenyl) propyl group] tin adjacent benzene dioxy acetic ester.
The third object of the present invention is to provide the application of the adjacent benzene dioxy acetic ester of above-mentioned two [three (2-methyl-2-phenyl) propyl group] tin in plant-growth regulator.
As one two [three (2-methyl-2-phenyl) propyl group] the tin adjacent benzene dioxy acetic ester of first aspect present invention, the compound for following structural formula (I):
Wherein Ph represents phenyl.
Two [three (2-methyl-2-phenyl) propyl group] of the present invention tin adjacent benzene dioxy acetic ester is through ultimate analysis, Infrared spectroscopy and nuclear magnetic resonance spectrum structural analysis, and result is as follows:
Ultimate analysis (C
70h
86o
6sn
2): theoretical value: C66.68, H7.61; Measured value: C66.65, H7.60.
IR(KBr,cm
-1)：2960.7(s)，1695.4(m)，1494.8(s)，767.6(s)，698.2(s)，555.5(w)，507.2(w)，447.4(w)。
1HNMR(CDCl
3,500MHz),δ(ppm)：1.02～1.23(m，48H，-C
H 2C(C
H 3)
2)，4.44(s,4H,-OC
H 2-)，6.51～7.31(m,34H,Ph-
H)。
13CNMR(CDCl
3,125MHz),δ(ppm)：172.43(-
COO)，99.94～159.37(Ph-
C)，65.94(-O
CH
2-)，32.68～39.32(-
CH
2 C(
CH
3)
2)。
As the preparation method of one two [three (2-methyl-2-phenyl) propyl group] the tin adjacent benzene dioxy acetic ester of second aspect present invention, be in the reaction vessel having nitrogen protection, add adjacent benzene two fluoroacetic acid, bis oxide [three (2-methyl-2-phenyl) propyl group tin] and reaction solvent in order successively, under stirring and refluxing, react 8 ~ 25h; Cooling, filter, at pressure 0.004 ~ 0.011MPa, under temperature 28 ~ 50 DEG C of conditions, with Rotary Evaporators evaporate to dryness filtrate, obtain the thick product of the adjacent benzene dioxy acetic ester of two [three (2-methyl-2-phenyl) propyl group] tin, with methylene chloride-methanol mixed solvent recrystallization, under 14 ~ 35 DEG C of conditions, control solvent evaporates crystallization, obtain white solid, be two [three (2-methyl-2-phenyl) propyl group] tin adjacent benzene dioxy acetic ester.
In a preferred embodiment of the invention, the amount of substance of described adjacent benzene two fluoroacetic acid and bis oxide [three (2-methyl-2-phenyl) propyl group tin] is than being 1:1 ~ 1:1.2.
In a preferred embodiment of the invention, the consumption of described reaction solvent is that adjacent benzene two fluoroacetic acid of every mmole adds 10 ~ 30 milliliters.
In a preferred embodiment of the invention, described reaction solvent is anhydrous methanol or dehydrated alcohol 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 1:3 ~ 1:15.
As the application of the adjacent benzene dioxy acetic ester of one two [three (2-methyl-2-phenyl) propyl group] tin in plant-growth regulator of third aspect present invention.
Applicant has carried out plant growth regulating activity to above-mentioned two [three (2-methyl-2-phenyl) propyl group] tin adjacent benzene dioxy acetic ester and has confirmed research, confirm that compound has plant growth regulation, that is the purposes of above-claimed cpd is the application in plant growth regulating, is exactly specifically the application in preparation purslane or Amaranthus retroflexus or Semen Cassiae or thorn amaranth or red roundleaf three-coloured amaranth or alfalfa plant growth regulator.
Two [three (2-methyl-2-phenyl) propyl group] of the present invention tin adjacent benzene dioxy acetic ester demonstrates good Developing restraint effect to purslane, Amaranthus retroflexus, Semen Cassiae, thorn amaranth, red roundleaf three-coloured amaranth, clover etc., the features such as two [three (2-methyl-2-phenyl) propyl group] of the present invention tin adjacent benzene dioxy acetic ester weeding activity is high, cost is low, preparation method is simple, provide new way for developing new weedicide.
Accompanying drawing explanation
Fig. 1 is the IR spectrogram of two [three (2-methyl-2-phenyl) propyl group] tin adjacent benzene dioxy acetic ester.
Fig. 2 is two [three (2-methyl-2-phenyl) propyl group] tin adjacent benzene dioxy acetic ester
1hNMR spectrogram.
Fig. 3 is two [three (2-methyl-2-phenyl) propyl group] tin adjacent benzene dioxy acetic ester
13cNMR spectrogram.
Embodiment
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 two [three (2-methyl-2-phenyl) propyl group] tin adjacent benzene dioxy acetic ester:
50mL has in the there-necked flask of nitrogen protection, add 0.226g (1.0mmol) adjacent benzene two fluoroacetic acid, 1.053g (1.0mmol) bis oxide [three (2-methyl-2-phenyl) propyl group tin], 30mL dry-out benzene, stirring heating backflow 12h, after having reacted, be cooled to room temperature, filter, at pressure 0.006MPa, temperature is under 40 DEG C of conditions, with Rotary Evaporators evaporate to dryness filtrate, obtain the thick product of the adjacent benzene dioxy acetic ester of two [three (2-methyl-2-phenyl) propyl group] tin, with methylene chloride-methanol mixed solvent recrystallization, wherein the volume ratio of methylene dichloride and methyl alcohol is 1:10, under 14 ~ 35 DEG C of conditions, control solvent evaporates crystallization, obtain white solid, be two [three (2-methyl-2-phenyl) propyl group] of the present invention tin adjacent benzene dioxy acetic ester.Productive rate: 50.4%.Fusing point: 67 DEG C ~ 68 DEG C.
Ultimate analysis (C
70h
86o
6sn
2): theoretical value: C66.68, H7.61; Measured value: C66.65, H7.60.
IR(KBr,cm
-1)：2960.7(s)，1695.4(m)，1494.8(s)，767.6(s)，698.2(s)，555.5(w)，507.2(w)，447.4(w)。
1HNMR(CDCl
3,500MHz),δ(ppm)：1.02～1.23(m，48H，-C
H 2C(C
H 3)
2)，4.44(s,4H,-OC
H 2-)，6.51～7.31(m,34H,Ph-
H)。
13CNMR(CDCl
3,125MHz),δ(ppm)：172.43(-
COO)，99.94～159.37(Ph-
C)，65.94(-O
CH
2-)，32.68～39.32(-
CH
2 C(
CH
3)
2)。
Embodiment 2:
The preparation of two [three (2-methyl-2-phenyl) propyl group] tin adjacent benzene dioxy acetic ester:
50mL has in the there-necked flask of nitrogen protection, add 0.226g (1.0mmol) adjacent benzene two fluoroacetic acid, 1.264g (1.2mmol) bis oxide [three (2-methyl-2-phenyl) propyl group tin], 30mL anhydrous methanol, stirring heating backflow 8h, after having reacted, be cooled to room temperature, filter, at pressure 0.004MPa, temperature is under 28 DEG C of conditions, with Rotary Evaporators evaporate to dryness filtrate, obtain the thick product of the adjacent benzene dioxy acetic ester of two [three (2-methyl-2-phenyl) propyl group] tin, with methylene chloride-methanol mixed solvent recrystallization, wherein the volume ratio of methylene dichloride and methyl alcohol is 1:5, under 14 ~ 35 DEG C of conditions, control solvent evaporates crystallization, obtain white solid, be two [three (2-methyl-2-phenyl) propyl group] of the present invention tin adjacent benzene dioxy acetic ester.Productive rate: 53.0%.Fusing point: 67 DEG C ~ 68 DEG C.
Ultimate analysis (C
70h
86o
6sn
2): theoretical value: C66.68, H7.61; Measured value: C66.65, H7.60.
IR(KBr,cm
-1)：2960.7(s)，1695.4(m)，1494.8(s)，767.6(s)，698.2(s)，555.5(w)，507.2(w)，447.4(w)。
1HNMR(CDCl
3,500MHz),δ(ppm)：1.02～1.23(m，48H，-C
H 2C(C
H 3)
2)，4.44(s,4H,-OC
H 2-)，6.51～7.31(m,34H,Ph-
H)。
13CNMR(CDCl
3,125MHz),δ(ppm)：172.43(-
COO)，99.94～159.37(Ph-
C)，65.94(-O
CH
2-)，32.68～39.32(-
CH
2 C(
CH
3)
2)。
Embodiment 3:
The preparation of two [three (2-methyl-2-phenyl) propyl group] tin adjacent benzene dioxy acetic ester:
150mL has in the there-necked flask of nitrogen protection, add 1.130g (5.0mmol) adjacent benzene two fluoroacetic acid, 5.791g (5.5mmol) bis oxide [three (2-methyl-2-phenyl) propyl group tin], 75mL dehydrated alcohol, stirring heating backflow 15h, after having reacted, be cooled to room temperature, filter, at pressure 0.008MPa, temperature is under 44 DEG C of conditions, with Rotary Evaporators evaporate to dryness filtrate, obtain the thick product of the adjacent benzene dioxy acetic ester of two [three (2-methyl-2-phenyl) propyl group] tin, with methylene chloride-methanol mixed solvent recrystallization, wherein the volume ratio of methylene dichloride and methyl alcohol is 1:3, under 14 ~ 35 DEG C of conditions, control solvent evaporates crystallization, obtain white solid, be two [three (2-methyl-2-phenyl) propyl group] of the present invention tin adjacent benzene dioxy acetic ester.Productive rate: 52.2%.Fusing point: 67 DEG C ~ 68 DEG C.
Ultimate analysis (C
70h
86o
6sn
2): theoretical value: C66.68, H7.61; Measured value: C66.65, H7.60.
IR(KBr,cm
-1)：2960.7(s)，1695.4(m)，1494.8(s)，767.6(s)，698.2(s)，555.5(w)，507.2(w)，447.4(w)。
1HNMR(CDCl
3,500MHz),δ(ppm)：1.02～1.23(m，48H，-C
H 2C(C
H 3)
2)，4.44(s,4H,-OC
H 2-)，6.51～7.31(m,34H,Ph-
H)。
13CNMR(CDCl
3,125MHz),δ(ppm)：172.43(-
COO)，99.94～159.37(Ph-
C)，65.94(-O
CH
2-)，32.68～39.32(-
CH
2 C(
CH
3)
2)。
Embodiment 4:
The preparation of two [three (2-methyl-2-phenyl) propyl group] tin adjacent benzene dioxy acetic ester:
250mL has in the there-necked flask of nitrogen protection, add 2.260g (10.0mmol) adjacent benzene two fluoroacetic acid, 12.109g (11.5mmol) bis oxide [three (2-methyl-2-phenyl) propyl group tin], 150mL dry-out benzene, stirring heating backflow 24h, after having reacted, be cooled to room temperature, filter, at pressure 0.011MPa, temperature is under 50 DEG C of conditions, with Rotary Evaporators evaporate to dryness filtrate, obtain the thick product of the adjacent benzene dioxy acetic ester of two [three (2-methyl-2-phenyl) propyl group] tin, with methylene chloride-methanol mixed solvent recrystallization, wherein the volume ratio of methylene dichloride and methyl alcohol is 1:8, under 14 ~ 35 DEG C of conditions, control solvent evaporates crystallization, obtain white solid, be two [three (2-methyl-2-phenyl) propyl group] of the present invention tin adjacent benzene dioxy acetic ester.Productive rate: 51.8%.Fusing point: 67 DEG C ~ 68 DEG C.
Ultimate analysis (C
70h
86o
6sn
2): theoretical value: C66.68, H7.61; Measured value: C66.65, H7.60.
IR(KBr,cm
-1)：2960.7(s)，1695.4(m)，1494.8(s)，767.6(s)，698.2(s)，555.5(w)，507.2(w)，447.4(w)。
1HNMR(CDCl
3,500MHz),δ(ppm)：1.02～1.23(m，48H，-C
H 2C(C
H 3)
2)，4.44(s,4H,-OC
H 2-)，6.51～7.31(m,34H,Ph-
H)。
13CNMR(CDCl
3,125MHz),δ(ppm)：172.43(-
COO)，99.94～159.37(Ph-
C)，65.94(-O
CH
2-)，32.68～39.32(-
CH
2 C(
CH
3)
2)。
Embodiment 5:
The preparation of two [three (2-methyl-2-phenyl) propyl group] tin adjacent benzene dioxy acetic ester:
250mL has in the there-necked flask of nitrogen protection, add 2.260g (10.0mmol) adjacent benzene two fluoroacetic acid, 11.056g (10.5mmol) bis oxide [three (2-methyl-2-phenyl) propyl group tin], 100mL dehydrated alcohol, stirring heating backflow 25h, after having reacted, be cooled to room temperature, filter, at pressure 0.006MPa, temperature is under 36 DEG C of conditions, with Rotary Evaporators evaporate to dryness filtrate, obtain the thick product of the adjacent benzene dioxy acetic ester of two [three (2-methyl-2-phenyl) propyl group] tin, with methylene chloride-methanol mixed solvent recrystallization, wherein the volume ratio of methylene dichloride and methyl alcohol is 1:15, under 14 ~ 35 DEG C of conditions, control solvent evaporates crystallization, obtain white solid, be two [three (2-methyl-2-phenyl) propyl group] of the present invention tin adjacent benzene dioxy acetic ester.Productive rate: 51.9%.Fusing point: 67 DEG C ~ 68 DEG C.
Ultimate analysis (C
70h
86o
6sn
2): theoretical value: C66.68, H7.61; Measured value: C66.65, H7.60.
IR(KBr,cm
-1)：2960.7(s)，1695.4(m)，1494.8(s)，767.6(s)，698.2(s)，555.5(w)，507.2(w)，447.4(w)。
1HNMR(CDCl
3,500MHz),δ(ppm)：1.02～1.23(m，48H，-C
H 2C(C
H 3)
2)，4.44(s,4H,-OC
H 2-)，6.51～7.31(m,34H,Ph-
H)。
13CNMR(CDCl
3,125MHz),δ(ppm)：172.43(-
COO)，99.94～159.37(Ph-
C)，65.94(-O
CH
2-)，32.68～39.32(-
CH
2 C(
CH
3)
2)。
Embodiment 6:
The preparation of two [three (2-methyl-2-phenyl) propyl group] tin adjacent benzene dioxy acetic ester:
500mL has in the there-necked flask of nitrogen protection, add 4.520g (20.0mmol) adjacent benzene two fluoroacetic acid, 22.640g (21.5mmol) bis oxide [three (2-methyl-2-phenyl) propyl group tin], 200mL anhydrous methanol, stirring heating backflow 16h, after having reacted, be cooled to room temperature, filter, at pressure 0.007MPa, temperature is under 38 DEG C of conditions, with Rotary Evaporators evaporate to dryness filtrate, obtain the thick product of the adjacent benzene dioxy acetic ester of two [three (2-methyl-2-phenyl) propyl group] tin, with methylene chloride-methanol mixed solvent recrystallization, wherein the volume ratio of methylene dichloride and methyl alcohol is 1:14, under 14 ~ 35 DEG C of conditions, control solvent evaporates crystallization, obtain white solid, be two [three (2-methyl-2-phenyl) propyl group] of the present invention tin adjacent benzene dioxy acetic ester.Productive rate: 52.7%.Fusing point: 67 DEG C ~ 68 DEG C.
Ultimate analysis (C
70h
86o
6sn
2): theoretical value: C66.68, H7.61; Measured value: C66.65, H7.60.
IR(KBr,cm
-1)：2960.7(s)，1695.4(m)，1494.8(s)，767.6(s)，698.2(s)，555.5(w)，507.2(w)，447.4(w)。
1HNMR(CDCl
3,500MHz),δ(ppm)：1.02～1.23(m，48H，-C
H 2C(C
H 3)
2)，4.44(s,4H,-OC
H 2-)，6.51～7.31(m,34H,Ph-
H)。
13CNMR(CDCl
3,125MHz),δ(ppm)：172.43(-
COO)，99.94～159.37(Ph-
C)，65.94(-O
CH
2-)，32.68～39.32(-
CH
2 C(
CH
3)
2)。
Test example:
Two [three (2-methyl-2-phenyl) propyl group] of the present invention tin adjacent benzene dioxy acetic ester, its Herbicidal is realized by Plating experimental technique.
Plating:
Plating is adopted to measure two [three (2-methyl-2-phenyl) propyl group] tin adjacent benzene dioxy acetic ester of embodiment 1 preparation to the weeding activity of common weed in the farm crop such as purslane, Amaranthus retroflexus, 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, Amaranthus retroflexus, 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, Amaranthus retroflexus, Semen Cassiae, thorn amaranth, red roundleaf three-coloured amaranth, clovers, conclusion is that two [three (2-methyl-2-phenyl) propyl group] tin adjacent benzene dioxy acetic ester demonstrates good Developing restraint effect to purslane, Amaranthus retroflexus, Semen Cassiae, thorn amaranth, red roundleaf three-coloured amaranth, clover etc.
The weeding activity experimental data (growth inhibition ratio %) of table 1 two [three (2-methyl-2-phenyl) propyl group] tin adjacent benzene dioxy acetic ester.
Two [three (2-methyl-2-phenyl) propyl group] tin adjacent benzene dioxy acetic ester prepared by all the other embodiments is with the same test example of weeding activity testing method of Plating to crop seeds such as purslane, Amaranthus retroflexus, Semen Cassiae, thorn amaranth, red roundleaf three-coloured amaranth, clovers, and test result and table 1 are substantially identical.
Claims (10)
1. two [three (2-methyl-2-phenyl) propyl group] tin adjacent benzene dioxy acetic ester, the compound for following structural formula (I):
Wherein Ph represents phenyl.
2. two [three (2-methyl-2-phenyl) propyl group] tin as claimed in claim 1 adjacent benzene dioxy acetic ester, its infrared data: IR (KBr, cm
-1): 2960.7 (s), 1695.4 (m), 1494.8 (s), 767.6 (s), 698.2 (s), 555.5 (w), 507.2 (w), 447.4 (w).
3. two [three (2-methyl-2-phenyl) propyl group] tin as claimed in claim 1 adjacent benzene dioxy acetic ester, its nuclear magnetic data:
1hNMR (CDCl
3, 500MHz), δ (ppm): 1.02 ~ 1.23 (m, 48H ,-C
h 2c (C
h 3)
2), 4.44 (s, 4H ,-OC
h 2-), 6.51 ~ 7.31 (m, 34H, Ph-
h);
13cNMR (CDCl
3, 125MHz), δ (ppm): 172.43 (-
coO), 99.94 ~ 159.37 (Ph-
c), 65.94 (-O
ch
2-), 32.68 ~ 39.32 (-
ch
2 c(
ch
3)
2).
4. the preparation method of two [three (2-methyl-2-phenyl) propyl group] tin according to claim 1 adjacent benzene dioxy acetic ester, be in the reaction vessel having nitrogen protection, add adjacent benzene two fluoroacetic acid, bis oxide [three (2-methyl-2-phenyl) propyl group tin] and reaction solvent in order successively, under stirring and refluxing, react 8 ~ 25h; Cooling, filter, at pressure 0.004 ~ 0.011MPa, under temperature 28 ~ 50 DEG C of conditions, with Rotary Evaporators evaporate to dryness filtrate, obtain the thick product of the adjacent benzene dioxy acetic ester of two [three (2-methyl-2-phenyl) propyl group] tin, with methylene chloride-methanol mixed solvent recrystallization, under 14 ~ 35 DEG C of conditions, control solvent evaporates crystallization, obtain white solid, be two [three (2-methyl-2-phenyl) propyl group] tin adjacent benzene dioxy acetic ester.
5. preparation method as claimed in claim 4, is characterized in that, the amount of substance of described adjacent benzene two fluoroacetic acid and bis oxide [three (2-methyl-2-phenyl) propyl group tin] is than being 1:1 ~ 1:1.2.
6. preparation method as claimed in claim 4, is characterized in that, the consumption of described reaction solvent is that adjacent benzene two fluoroacetic acid of every mmole adds 10 ~ 30 milliliters.
7. the preparation method as described in claim 4 or 6, is characterized in that, described reaction solvent is anhydrous methanol or dehydrated alcohol or dry-out benzene.
8. preparation method as claimed in claim 4, it is characterized in that, in described methylene chloride-methanol mixed solvent, the volume ratio of methylene dichloride and methyl alcohol is 1:3 ~ 1:15.
9. the application of the adjacent benzene dioxy acetic ester of two [three (2-methyl-2-phenyl) propyl group] tin described in claim 1 or 4 in plant growth regulating.
10. application according to claim 9, wherein said plant is purslane, Amaranthus retroflexus, Semen Cassiae, thorn amaranth, red roundleaf three-coloured amaranth or clover.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510752634.7A CN105198918A (en) | 2015-11-09 | 2015-11-09 | Bis[tris(2-methyl-2-phenyl)propyl]tin o-phenyldioxyacetate as well as preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510752634.7A CN105198918A (en) | 2015-11-09 | 2015-11-09 | Bis[tris(2-methyl-2-phenyl)propyl]tin o-phenyldioxyacetate as well as preparation method and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105198918A true CN105198918A (en) | 2015-12-30 |
Family
ID=54946908
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510752634.7A Pending CN105198918A (en) | 2015-11-09 | 2015-11-09 | Bis[tris(2-methyl-2-phenyl)propyl]tin o-phenyldioxyacetate as well as preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105198918A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106279253A (en) * | 2016-08-15 | 2017-01-04 | 衡阳师范学院 | A kind of double [three (2 methyl 2 phenyl) propyl group stannum] 5 nitroisophthalic acid ester coordination compounds and preparation method and application |
| CN110128466A (en) * | 2019-05-31 | 2019-08-16 | 衡阳师范学院 | Three (2- methyl -2- phenyl) propyl tin 3- indolebutyric acid ester complexs of one kind and preparation method and application |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104230979A (en) * | 2014-08-18 | 2014-12-24 | 衡阳师范学院 | Bis[tris(2-methyl-2-phenyl)propyl tin] oxalate as well as preparation method and application thereof |
| CN104817587A (en) * | 2015-04-15 | 2015-08-05 | 衡阳师范学院 | Tricyclohexanyl-tin o-phenylenedioxydiacetic acid ester and preparation method and application thereof |
-
2015
- 2015-11-09 CN CN201510752634.7A patent/CN105198918A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104230979A (en) * | 2014-08-18 | 2014-12-24 | 衡阳师范学院 | Bis[tris(2-methyl-2-phenyl)propyl tin] oxalate as well as preparation method and application thereof |
| CN104817587A (en) * | 2015-04-15 | 2015-08-05 | 衡阳师范学院 | Tricyclohexanyl-tin o-phenylenedioxydiacetic acid ester and preparation method and application thereof |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106279253A (en) * | 2016-08-15 | 2017-01-04 | 衡阳师范学院 | A kind of double [three (2 methyl 2 phenyl) propyl group stannum] 5 nitroisophthalic acid ester coordination compounds and preparation method and application |
| CN106279253B (en) * | 2016-08-15 | 2019-05-03 | 衡阳师范学院 | Bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complexs of one kind and the preparation method and application thereof |
| CN110128466A (en) * | 2019-05-31 | 2019-08-16 | 衡阳师范学院 | Three (2- methyl -2- phenyl) propyl tin 3- indolebutyric acid ester complexs of one kind and preparation method and application |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103664808B (en) | A kind of aryl 3-triazole compounds containing chlorocyclopropane and preparation method thereof and application | |
| CN104804035B (en) | A kind of naphthalene dioxy acetic acid esters of Tricyclohexyltin 2,7 and its preparation method and application | |
| JPS61293956A (en) | Chloroacetamide compound and production thereof | |
| CN104817587B (en) | Adjacent benzene dioxy acetic acid esters of a kind of Tricyclohexyltin and its preparation method and application | |
| CN104193681A (en) | Preparation and application of 4-chlorine-3-ethyl-1-methyl-N'-(2-substituted phenoxy acetyl)-1H-pyrazol-5-carbohydrazide compounds | |
| CN105198918A (en) | Bis[tris(2-methyl-2-phenyl)propyl]tin o-phenyldioxyacetate as well as preparation method and application thereof | |
| CN105348317A (en) | Triphenyltin p-methoxy phenyloxyacetate, preparation method therefor and applications | |
| CN107200712A (en) | One class yl pyrimidines aryl containing substitution amidine compound, its preparation method and application | |
| CN104804037A (en) | Di-n-butyltin phenoxyacetic acid ester as well as preparation method and application thereof | |
| CN108191629A (en) | A kind of ferulic acid derivative and its application | |
| CN105348316A (en) | Triphenyltin o-phenyl dioxy acetate, preparation method therefor and applications | |
| CN105218578A (en) | A kind of Tricyclohexyltin is to anisole fluoroacetic acid ester and its preparation method and application | |
| CN105348315A (en) | Tributyltin o-phenyl dioxy acetate, preparation method therefor and applications | |
| JPH03173855A (en) | Herbicidal glutaramide acid and its derivative | |
| CN104370891B (en) | A kind of 5-(butylene lactone-3-ethylidene)-2-aminooimidazole quinoline ketone compounds, preparation method and applications | |
| CN104230979A (en) | Bis[tris(2-methyl-2-phenyl)propyl tin] oxalate as well as preparation method and application thereof | |
| CN105198920A (en) | Bis[tris(2-methyl-2-phenyl)propyltin]2,7-naphthalene dioxyacetate as well as preparation method and application thereof | |
| CN104804036B (en) | A kind of di-n-butyl tin o chlorophenoxyacetic acid ester and its preparation method and application | |
| CN105348314A (en) | Tricyclohexanyl-tin alpha-naphthyloxy acetate, preparation method therefor and applications | |
| CN105237561A (en) | Di-n-butyltin m-methyl phenoxy acetic ester and preparation method and application thereof | |
| CN105198919A (en) | Di-n-butyltin p-methoxyphenoxyacetate as well as preparation method and application thereof | |
| CN108794462A (en) | A kind of fluorine-containing cyanogen imines thiazolidine substitution oxadiazole class insecticidal bactericides | |
| CN104311598A (en) | Phosphate compound containing 1,2,3-triazole ring as well as preparation method and application thereof | |
| CN104817585B (en) | A kind of naphthalene dioxy acetic acid esters coordination polymer of tri-n-butyl tin 1,6 and its preparation method and application | |
| CN104860982B (en) | A kind of Tricyclohexyltin 3 (carboxymethyl of N, N bis-) amino phenoxy acetic acid ester coordination polymer and its preparation method and application |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WD01 | Invention patent application deemed withdrawn after publication | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20151230 |