CN100551238C - Thio-ether type compounds plant growth regulator - Google Patents
Thio-ether type compounds plant growth regulator Download PDFInfo
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- CN100551238C CN100551238C CNB2006101307101A CN200610130710A CN100551238C CN 100551238 C CN100551238 C CN 100551238C CN B2006101307101 A CNB2006101307101 A CN B2006101307101A CN 200610130710 A CN200610130710 A CN 200610130710A CN 100551238 C CN100551238 C CN 100551238C
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- plant growth
- ether type
- type compounds
- growth regulator
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Abstract
A kind of thio-ether type compounds plant growth regulator belongs to the chemical pesticide steroids.Solve the synthetic complexity of existing root-inducing promoter, cost an arm and a leg, safety in utilization is the problem of shortcoming relatively.This plant growth regulator is that the general formula that contains effective dose is the composition that the compound of following formula (II) is formed, n=1 in the formula, 2,3 ... R=halogen, alkyl, nitro, hydroxyl, alkoxyl, ester group, aryl, described composition comprise that agricultural goes up the acceptable carrier.The present invention has good plant growth regulating activity, and the activity of taking root is obvious especially, can be used as root-inducing promoter.The present invention has characteristics such as consumption is few, drug effect is high, synthesize easily, cost is low, safe and convenient to use.Application of the present invention is with an amount of present composition conventional method seed soaking, and is easy to use.
Description
[technical field]:
The invention belongs to the chemical pesticide steroids, relate to the application of thioether (sulfone) compounds aspect plant growth regulator, this compounds can be used as root-inducing promoter.
[background technology]:
Plant growth regulator has developed into the big class of one in the agricultural chemicals.The adjustable plant growth of plant growth regulator makes its volume increase, increases income, improves quality; And the plant growth regulator consumption is little, pollutes and lacks, and does not have the pesticide resistance problem, and therefore, the research of plant growth regulator enjoys researcher's concern.
Common root-inducing promoter has growth hormone, gibberellin, ethene, the basic element of cell division and abscisic acid five big classes at present; concrete kind only has 3-indolyl acetic acid, methyl; ethrel etc. a few; but this compounds synthesizes complexity, costs an arm and a leg; safety in utilization is short of relatively, can not satisfy agriculture requirement of growing and the environmental protection requirement to greening, artificial afforestration.
Therefore, low price, drug effect height, novel root-inducing promoter that safety in utilization is good are starved of, especially at aspects such as desert treatment, afforestation, flowers and plants transplanting.
[summary of the invention]:
The objective of the invention is to solve the synthetic complexity of existing root-inducing promoter, cost an arm and a leg, safety in utilization is the problem of shortcoming relatively, and a kind of thio-ether type compounds plant growth regulator is provided.
Thio-ether type compounds plant growth regulator provided by the invention is to contain the composition of the general formula of effective dose for the compound composition of (II):
N=1 in the formula, 2,3..., R=halogen, alkyl, nitro, hydroxyl, alkoxyl, ester group, aryl, described composition comprises that agricultural goes up the acceptable carrier, for example clay, diatomite, water, hydro carbons etc., and the preparation of said composition is simply pulverized and is stirred or dissolving gets final product by conventional.
The compound of said effective dose is meant its sylvite or sodium salt or quaternary ammonium salt.
The compound water solution of said effective dose specifically is the 0.1-30ppm aqueous solution of the compound of effective dose as the plant establishment agent.As root-growing agent the time, Mr.'s salify water is again made solvent.
Advantage of the present invention and effect:
Thio-ether type compounds provided by the invention has good plant growth regulating activity, and the activity of taking root is obvious especially, can be used as root-inducing promoter.The present invention has characteristics such as consumption is few, drug effect is high, synthesize easily, cost is low, safe and convenient to use.
Application of the present invention is with an amount of present composition conventional method seed soaking, and is easy to use.
[embodiment]:
Embodiment 1
(1) thio-ether type compounds II (R=4-OCH
3, n=1) synthetic:
The substituted benzene thiophenol of 11mmol phthalide, 10mmol, 1.03g Anhydrous potassium carbonate, oil bath is heated to 100 ℃, keeps this stability heating 1-2 hour, cooling, be dissolved in the water of 150ml, solid is dissolved in the water of 150ml, filters, filtrate is used the acidifying of HCl solution, suction filtration gets solid, with the mixed solution recrystallization of ethanol and water, get pale solid, productive rate 74.8%.Mp：120℃-122℃。
(2) thio-ether type compounds II (R=3-Br, n=2) synthetic:
The replacement thiophenol of 10mmol isochromanome, 10mmol, the anhydrous K of 10mmol
2CO
3, 170 ℃ of reactions of temperature control are reacted and are stopped after 7 hours, cooling, solid is dissolved in the 50ml water, the acidifying of HCl solution produces a large amount of precipitations, suction filtration, after the washing crude product, be recrystallized faint yellow solid, productive rate 74.2%.MP：126℃-128℃。
2. biological activity test
II obviously promotes isolated cucumber cotyledon to take root in the general sieve of biologically active, is further showing that root elongation and root fresh weight are also had facilitation in the research.Promote primary root elongation and root fresh weight to increase with its sylvite or the soup seed soaking cucumber seeds of sodium salt preparation.II valid density is lower, and is safe in utilization.
Experimental technique:
The cucumber cotyledons rooting method: select for use cucumber seeds (Cucumis Sativns L.) Tianjin to grind No. 4, being sowed on 0.7% agar after 2 hours of soaking seed, cultivated 72 hours in 25 ℃ of darkrooms, and it is standby to win cotyledon.Get 10 cotyledons and be placed in the diameter 6cm culture dish, in have a filter paper and 30ml to treat test solution, cultivated 5 days in 25 ℃ of darkrooms, surveys petiole base and take root, and surveyed the long and root fresh weight of root on the 6th day.
The compound that is synthesized has been carried out the test of plant growth regulating as stated above, wherein effective compound has been carried out more detailed biological test, test result sees Table 1, table 2.
Biologically active data under the table 1 part of compounds 10ppm concentration
| Numbering | n | Substituent R | Biologically active (%) |
| II-1 | n＝1 | 4-chlorine | 106.3 |
| II-2 | n＝1 | The 4-methoxyl group | 100.0 |
| II-3 | n＝1 | 2, the 5-diethyl | 127.4 |
| II-4 | n＝1 | The 3-bromine | 100.0 |
| II-5 | n＝1 | The 4-hydroxyl | 25.6 |
| II-6 | n＝1 | The 3-ethyl | 106.7 |
| II-7 | n＝1 | 2-chlorine | 100.0 |
| II-8 | n＝2 | The 4-methoxyl group | 76.1 |
| II-9 | n＝2 | The 4-methyl | 70.6 |
| II-10 | n＝2 | 3, the 4-dichloro | 92.8 |
| II-11 | n＝2 | The 3-bromine | 88.9 |
| II-12 | n＝2 | 2, the 4-difluoro | 122.2 |
Annotate: 1, A level:＞150; B level: 100-150; C level: 50-100; D level:＜50
2, the activity data of this table only is the promotion percentage of number that cucumber cotyledons is taken root.
Table 1 compound integral body has shown very excellent plant growth regulating activity, and the activity of part of compounds has surpassed the A level.
Active basic the comparison on average of series II (n=2) compound.
Biologically active data under the table 2 part n level compound variable concentrations
Table 2 shows that compound concentration is reduced to 1ppm even 0.1ppm, and these B level reactive compounds under 10ppm concentration still have plant growth regulating activity, and radical or root length are more or less had certain facilitation.
Claims (4)
1, a kind of thio-ether type compounds plant growth regulator is characterized in that it being the composition that contains the thio-ether type compounds of effective dose, and described thio-ether type compounds is that general formula is compound or its sylvite, sodium salt or the quaternary ammonium salt of (II):
In the formula, n=1, R=4-methoxyl group, 2,5-diethyl, 3-ethyl, 4-chlorine, 2-chlorine, 3-bromine or 4-hydroxyl;
N=2, R=4-methyl, 4-methoxyl group, 3,4-dichloro, 3-bromine or 2,4-difluoro;
Described composition comprises that agricultural goes up the acceptable carrier.
2,, it is characterized in that the thio-ether type compounds of said effective dose is meant that general formula is sylvite, sodium salt or the quaternary ammonium salt of the compound of (II) according to the said thio-ether type compounds plant growth regulator of claim 1.
3,, it is characterized in that the thio-ether type compounds of said effective dose is made the aqueous solution as the plant establishment agent according to the said thio-ether type compounds plant growth regulator of claim 1.
4,, it is characterized in that the concentration of the aqueous solution that the thio-ether type compounds of said effective dose is made is 0.1-30ppm according to the said thio-ether type compounds plant growth regulator of claim 3.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006101307101A CN100551238C (en) | 2006-12-30 | 2006-12-30 | Thio-ether type compounds plant growth regulator |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006101307101A CN100551238C (en) | 2006-12-30 | 2006-12-30 | Thio-ether type compounds plant growth regulator |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN100998328A CN100998328A (en) | 2007-07-18 |
| CN100551238C true CN100551238C (en) | 2009-10-21 |
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| Application Number | Title | Priority Date | Filing Date |
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| CNB2006101307101A Expired - Fee Related CN100551238C (en) | 2006-12-30 | 2006-12-30 | Thio-ether type compounds plant growth regulator |
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Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102440245A (en) * | 2010-10-14 | 2012-05-09 | 南开大学 | Neighbor-(2-chlorine) benzylthio benzoic acid preparation, preparation method and application |
| CN102731354A (en) * | 2012-07-10 | 2012-10-17 | 南开大学 | Preparation and plant growth-regulating activity of water-oil soluble o-(4-chloro) benzylthio-benzoate derivatives |
| CN110963931B (en) * | 2019-11-12 | 2022-11-01 | 河南省科学院高新技术研究中心 | 2- (2-methoxy-5-nitro-phenoxy) ethyl triethyl ammonium halide and preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1031744A (en) * | 1961-12-21 | 1966-06-02 | Sandoz Ag | Improvements in or relating to dibenzthiepin derivatives |
| DE1294970B (en) * | 1961-09-28 | 1969-05-14 | Boehringer & Soehne Gmbh | Process for the preparation of substituted 6, 11-dihydrodibenzo [b, e] -oxepin- or -thiepin-11-ones |
-
2006
- 2006-12-30 CN CNB2006101307101A patent/CN100551238C/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1294970B (en) * | 1961-09-28 | 1969-05-14 | Boehringer & Soehne Gmbh | Process for the preparation of substituted 6, 11-dihydrodibenzo [b, e] -oxepin- or -thiepin-11-ones |
| GB1031744A (en) * | 1961-12-21 | 1966-06-02 | Sandoz Ag | Improvements in or relating to dibenzthiepin derivatives |
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| CN100998328A (en) | 2007-07-18 |
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Assignee: Tianjin Youlong Technological Development Co., Ltd. Assignor: Nankai University Contract record no.: 2010120000053 Denomination of invention: Thio-ether type compounds plant growth regulator Granted publication date: 20091021 License type: Exclusive License Open date: 20070718 Record date: 20100507 |
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Granted publication date: 20091021 Termination date: 20171230 |
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