CN1287665C - Sex-attractant for cane stripe pyralid, and application thereof - Google Patents
Sex-attractant for cane stripe pyralid, and application thereof Download PDFInfo
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- CN1287665C CN1287665C CN 200410015484 CN200410015484A CN1287665C CN 1287665 C CN1287665 C CN 1287665C CN 200410015484 CN200410015484 CN 200410015484 CN 200410015484 A CN200410015484 A CN 200410015484A CN 1287665 C CN1287665 C CN 1287665C
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- sex attractant
- cane
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- pyralids
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Abstract
The present invention provides a sex attractant for cane stripe pyralids, which relates to the technical field of insect sex pheromone synthesis. The present invention is characterized in that the present invention is synthesized by the component and the mixture ratios of 35 to 45% of cis-11-hexadeceneol acetate. 5 to 15% of cis-13-octadecaneol and 40 to 60% of cis-13-octadeceneol acetate. The present invention also provides a rubber sheet used for the prediction and the forecast of the cane stripe pyralids and an isotropic tube used for the prevention and the cure of the cane stripe pyralids. The present invention is characterized in that the preparation process of the sex attractant is simple, raw materials are sufficient, and conditions are viable; the sex attractant for the cane stripe pyralids are used for the prediction and the forecast of the occurrence of the cane stripe pyralids, and has the advantage of accurate prediction; the sex attractant has strong singleness, so the cane stripe pyralids can not produce resistance, and the sex attractant has no damage effect on natural enemies; the sex attractant has the advantages of no poison on people and livestock, no environment pollution, strong stress resistance, wind resistance, rain prevention, solarization resistance, long effective period and convenient use.
Description
Technical field
The present invention relates to insect property telergone synthesis technical field.
Background technology
Article sugarcane borer is one of the primary pest of sugarcane of causing harm, and causes spike top or borer pest joint with larva moth food sugarcane, seriously reduces sugarcane yield and contains sugared part.Produce at present and go up except utilization cultural control, physical control, also useful oophagous trichogrammae control, but mainly still use chemical pesticide control.
Because insect is very strong to the pesticide resistance of agricultural chemicals, use chemical pesticide to prevent and treat article sugarcane borer and seem that more and more effect is not good enough, the sex pheromone that discharges according to the female moth that lives has the principle of very strong attracting ability to male moth of the same race, and prophylactico-therapeutic measures the most reliably at present is that to utilize the secreted property telergone of the female moth of article sugarcane borer be that sex attractant is blocked mating and realized.
Summary of the invention
We are in the process of test, and the activity of the thick extract that discovery extracts from the sexual gland body of female moth is the same with the female moth that lives, and male moth is also had very strong attracting ability.We carry out chemical analysis and Instrumental Analysis with thick extract, preliminary definite each component and structural formula, and synthetic, again synthetic is taken then and lured the test of surveying male moth between sugarcane field, give birth to test through repetitious field and test, finally determined the key component of article sugarcane borer sex pheromone.
Producing the article sugarcane borer sex attractant with the method for synthetic is main purpose of the present invention.
Another object of the present invention is a kind of prediction methods that the article sugarcane borer sex attractant is used for the article sugarcane borer generation of design.
Another purpose of the present invention is a kind of method that the article sugarcane borer sex attractant is used for directly preventing and treating article sugarcane borer of design.
The present invention can realize by following scheme:
A kind of preparation method of article sugarcane borer sex attractant, it basic composition is:
1. suitable-11-hexadecylene alcohol acetate
Its molecular formula is: CH
3(CH
2)
3CH=CH (CH
2)
9CHOOCCH
3
Its structural formula is:
2. suitable-the 13-oleic alcohol
Its molecular formula is: CH
3(CH
2)
3CH=CH (CH
2)
11CH
2OH
Its structural formula is:
3. suitable-13-oleic alcohol acetate
Its molecular formula is: CH
3(CH
2)
3CH=CH (CH
2)
11CHOOCCH
3
Its structural formula is:
Above-mentioned three kinds of components are mixed in following ratio and proper amount of solvent (acetone or organic solvents such as normal heptane, carrene) make the article sugarcane borer sex attractant, proportioning (percentage by weight) is:
Suitable-11-hexadecylene alcohol acetate 35-45%
Suitable-13-oleic alcohol 5-15%
Suitable-13-oleic alcohol acetate 40-60%
A kind of film that is used for the article sugarcane borer prediction is characterized in that: each about 3cm
2Film in contain 150-250 μ g sex attractant, it is by being impregnated into the film carrier again behind every 100ml dissolution with solvents 150-250mg article sugarcane borer sex attractant.
A kind of isotropic pipe that is used for article sugarcane borer control is characterized in that: mix being squeezed into plastic tube behind every 1L dissolution with solvents 180-250g article sugarcane borer sex attractant with plastic raw materials.
The feedstock production technological process of article sugarcane borer sex attractant of the present invention is as follows:
0, the preparation process of hexin-1:
(0.1) n-butanol and hydrobromic acid react under the effect of the concentrated sulfuric acid and generate positive n-butyl bromide:
(0.2) positive n-butyl bromide, acetylene and sodium metal are under the catalytic action of ferric nitrate, and generation hexin-1 reacts:
1, the synthesis step of suitable-11-hexadecylene alcohol acetate:
(1.1) 1,10-decanediols and hydrobromic acid heat in dimethylbenzene, and reaction generates 10-bromine decyl alcohol-1:
(1.2) under the effect of 10-bromine decyl alcohol-1, hexin and lithium THF reagent in the liquefied ammonia environment, reaction generates alkynes-11-hexadecanol:
(1.3) alkynes-11-hexadecanol and H
2Reaction generates suitable-11-hexadecylene alcohol:
(1.4) suitable-pure and mild aceticanhydride of 11-hexadecylene reacts in pyridine solution and generates suitable-11-hexadecylene alcohol acetate:
2, the synthesis step of suitable-13-oleic alcohol:
Reaction generates 12-bromine 12 carbon alcohol-1 to (2.1) 1,12-lauryl alcohols with hydrobromic acid in xylene solution:
(2.2) 12-bromine lauryl alcohol-1, lithium and hexin react under the effect of THF reagent and generate alkynes-13-octadecanol:
(2.3) alkynes-13-octadecanol and H
2Hydrogenation reaction takes place generate suitable-13-oleic alcohol:
3, the synthesis step of suitable-13-oleic alcohol acetate:
(3.1) suitable-13-oleic alcohol acetate of esterification generation takes place in suitable-13-oleic alcohol and aceticanhydride in pyridine solution:
The present invention compares with original technology, has following outstanding substantive distinguishing features and obvious improvement:
1. the present invention has found the prescription of the sex attractant that can effectively lure the male moth of article sugarcane borer, and its preparation technology is simple, the raw material abundance, and condition is feasible.
2. observe and predict accurately.The article sugarcane borer sex attractant was used for the generation of prediction article sugarcane borer, with the actual emergence period error of sugarcane field bar snout moth's larva only 1-2 days.
3. selectivity is strong, just just at article sugarcane borer, can not make the bar snout moth's larva produce resistance, and natural enemy is not had injury effect.
4. nontoxic to people and animals, environmentally safe.
5. strong stress resistance.Be not afraid of wind, drench with rain and Exposure to Sunlight.
6. the lasting period is long.Control efficiency can be kept 25-40 days, can effectively control a mating activity of adult from generation to generation.
7. easy to use.
Embodiment
Embodiment-: the preparation of article sugarcane borer sex attractant
0, the preparation of hexin-1
(0.1) preparation of positive n-butyl bromide
N-butanol 2.335kg, hydrobromic acid 7.5kg, three kinds of raw materials of concentrated sulfuric acid 1L are dropped in the reactor, added hot reflux 4 hours, thick product is distilled, with the concentrated sulfuric acid, water, diluted alkaline washing, use the anhydrous calcium chloride drying more respectively, steam product.Repeat average positive n-butyl bromide 3.31kg twice, content is greater than 99%, yield 75.9%.Standby.
(0.2) preparation of hexin-1
Lead to into about 8L liquefied ammonia in reactor, add an amount of ferric nitrate and make catalyzer under stirring, block-by-block adds sodium metal 280g under logical acetylene, add and continue logical acetylene after 2 hours, drip positive n-butyl bromide 1370g, finish about 2.5 hours, continue again to stir after several hours and handle.Hexin-1 product 612g, content is greater than 96%, yield 74.6%.Standby.
1, the preparation of suitable-11-hexadecylene alcohol acetate:
The preparation of (1.1) 1,10-bromine decyl alcohol-1
Drop into 1 in reactor, 10-decanediol 400g, 40% hydrobromic acid 465g, dimethylbenzene 7000ml reflux in stirring down heating on one side, divide water on one side, and cooling behind the stoichiometric number hour with diluted alkaline, water washing, concentrates recovery dimethylbenzene, decompression distillation.Repeat 10-bromine decyl alcohol-1 product 740g, content 85% twice 1.
(1.2) preparation of alkynes-11-hexadecanol
In reactor, feed about liquefied ammonia 8L, add several ferric nitrates as catalyzer in stirring down, slowly piecemeal adds lithium metal 70g, finish the mixed liquor that stirs Dropwise 5 60g hexin-1 and 800ml THF after 2 hours again, continue again to stir 3 hours, drip the mixed liquor of 680g10-bromine decyl alcohol-1 and 1200ml THF again, finish to stir and spend the night to next day.Well-established law is handled, and gets alkynes-11-hexadecanol 1030g.
(1.3) preparation of suitable-11-hexadecylene alcohol
With nickel acetate and potassium borohydride dissolve with ethanol, under stirring, be mixed with P-2Ni again, use the ethylenediamine passivation again after, add alkynes-11-hexadecanol, natural aspiration under the air-free state normal pressure is not till inhaling, elimination catalyzer, washing, concentrated, decompression distillation must suitable-11-hexadecylene alcohol.
(104) preparation of suitable-11-hexadecylene alcohol acetate
After under the room temperature suitable-11-hexadecylene alcohol, aceticanhydride, pyridine being mixed stirred for several hour, use extracted by ether, be washed till neutrality with diluted acid, diluted alkaline after, concentrated recovery ether, decompression distillation must suitable-11-hexadecylene alcohol acetate 830g.
2, the preparation of suitable-13-oleic alcohol:
(2.1) preparation of 12-bromine lauryl alcohol-1
With 1,12-lauryl alcohol 400g, 40% hydrobromic acid 400g, dimethylbenzene 7000ml drop in the reactor, and operating process repeats 3 times and gets 12-bromine lauryl alcohol-1 product 820g, content 67%, yield 52% with 10-bromine decyl alcohol-1;
(2.2) preparation of alkynes-13-octadecanol
To get alkynes-13-octadecanol 760g after 12-bromine 12 carbon alcohol-1 and lithium metal 78g, hexin-1763g and the THF reagent 2000ml reaction.
(2.3) preparation of suitable-13-oleic alcohol
With nickel acetate and potassium borohydride dissolve with ethanol, under stirring, be mixed with P-2Ni again, use the ethylenediamine passivation again after, add alkynes-13-octadecanol, natural aspiration under the air-free state normal pressure is not till inhaling, elimination catalyzer, washing, concentrated, decompression distillation must suitable-13-oleic alcohols.
3, the preparation of suitable-13-oleic alcohol acetate:
(3.1) under the room temperature suitable-13-oleic alcohol, aceticanhydride, pyridine mixed stirred for several hour after, use extracted by ether, be washed till neutrality with diluted acid, diluted alkaline after, concentrated recovery ether, decompression distillation must suitable-13-oleic alcohol acetate 830g.
The raw material that said process is obtained becomes the article sugarcane borer sex attractant in following ratio mixing and stirring:
Suitable-11-hexadecylene alcohol acetate 38g
Suitable-13-oleic alcohol 9g
Suitable-13-oleic alcohol acetate 53g
Acetone 100ml
Embodiment two, the article sugarcane borer sex attractant is used for prediction:
Simultaneously the female moth that lives is lured the moth comparative test respectively with article sugarcane borer sex attractant, light, the article sugarcane borer sex attractant adopts following prescription (percentage by weight) to be mixed with the film formulation:
Table 1 film form formula
| Component | Prescription 1 | Prescription 2 | ||
| Percentage (%) | Actual amount (mg) | Percentage (%) | Actual amount (mg) | |
| Suitable-11-hexadecylene alcohol acetate | 38 | 83.6 | 40 | 80 |
| Suitable-13-oleic alcohol acetate | 53 | 116.6 | 50 | 100 |
| Suitable-the 13-oleic alcohol | 9 | 19.8 | 10 | 20 |
| Acetone | 200ml | 200ml | ||
Suitable-11-hexadecylene alcohol acetate, suitable-the 13-oleic alcohol, suitable-13-oleic alcohol acetate are diluted, stir with solvent acetone, and each is filled a prescription 2000 film (about 3cm
2/) drop into and soak, be mixed with the film formulation that prediction is used.
Test method and effect:
(1) select sugar cane breed, growing way, rich water quality management term harmonization, area does the experimental field in the field of sugarcane in flakes more than 30 mu, central three sex attractants trappings basin, a lamp light trapping device and three female moth trappers of work is set evenly, as a repetition; Establish three repetitions altogether, randomized arrangement.
(2) control time and method: write down induced moth number every morning, see before to trap since winter generation adult beginning mid-March and end when third generation adult is finished to November.
(3) result of the test is as follows:
Table 2 sex attractant and light lure moth effect relatively (head/basin)
| From generation to generation | Lure the moth method | Prescription 1 | Prescription 2 | ||
| Induced moth number | The highest single basin induced moth number | Induced moth number | The highest single basin induced moth number | ||
| Overwinter generation | Sex attractant | 205 | 43 | 123 (12 days) | 48 |
| Light | 40 | 4 | 27 (12 days) | 9 | |
| A generation | Sex attractant | 114 | 16 | 211 | 28 |
| Light | 31 | 3 | 98 | 16 | |
| Two generations | Sex attractant | 409 | 43 | ||
| Light | 130 | 15 | |||
| The three generations | Sex attractant | 479 | 44 | ||
| Light | 189 | 19 | |||
Table 3 sex attractant lures moth effect relatively (head/basin) with the female moth that lives
| From generation to generation | Trapping method | Prescription 1 | Prescription 2 | ||
| Induced moth number | The highest single basin induced moth number | Induced moth number | The highest single basin induced moth number | ||
| Overwinter generation | Sex attractant | 103 | 42 | 203 | 54 |
| Female moth lives | 56 | 33 | 48 | 22 | |
(4) result of the test shows: the induced moth number of two assembly sides of bar snout moth's larva sex attractant and the highest single basin induced moth number all significantly are higher than light and the induced moth number of the female moth that lives, and this moth activity that lures that demonstrates the article sugarcane borer sex attractant will obviously be better than other two kinds.The film formulation of the article sugarcane borer sex attractant that utilization is determined is carried out the prediction of article sugarcane borer emergence period, lure moth active high, bar snout moth's larva decreasing and increasing law is obvious, observe and predict accurately, and the size that can also reflect all types of sugarcanes district bar snout moth's larva mouth density was with the actual emergence period error of sugarcane field bar snout moth's larva only 1-2 days.Present article sugarcane borer sex attractant prediction technology is the one preferred technique as the article sugarcane borer prediction in vast sugarcane producing region.
Embodiment three, utilize article sugarcane borer sex attractant control article sugarcane borer---" isotropic method " control
Be mixed with article sugarcane borer sex attractant " isotropic pipe " pipe with following prescription (percentage by weight):
Table 4 " isotropic pipe " form formula
| Component | Prescription 1 | Prescription 2 | Prescription 3 | |||
| Percentage % | Actual amount (g) | Percentage % | Actual amount (g) | Percentage % | Actual amount (g) | |
| Suitable-11-hexadecylene alcohol acetate | 37 | 74 | 39 | 78 | 40 | 80 |
| Suitable-the 13-oleic alcohol | 12 | 24 | 9 | 18 | 10 | 20 |
| Suitable-13-oleic alcohol acetate | 51 | 102 | 52 | 104 | 50 | 100 |
| Normal heptane | 1L | 1L | 1L | |||
| Plastics | 14kg | 14kg | 14kg | |||
Suitable-11-hexadecylene alcohol acetate, suitable-the 13-oleic alcohol, suitable-13-oleic alcohol acetate are dissolved, stir with the solvent normal heptane, pour in the plastic raw materials again and mix, after treating that sex attractant permeates substantially, pour in the extruding machine and process, pull into the hollow plastic cast, cut into biapiculate isotropic pipe.
Test method and effect:
(1) select that sugar cane breed, growing way, rich water quality management condition-cause, isolation condition are good, large tracts of land in flakes the sugarcane field of (more than 100 mu) as the experimental field; Contrast field piece and isotropic control field piece is relatively independent, and respectively establishes 9 in isotropic field and contrast field and lure moth monitoring basin, lures moth situation record the same with prediction.
(2) under the guidance of prediction, in article sugarcane borer each for first three day of Sheng phase moth beginning, " isotropic pipe " distributed in the sugarcane leaf layer of bar snout moth's larva adult mating activity 100 of every mu of intubate.
(3) the contrast field prevents and treats with conventional pesticide, and mu is executed the red 3-4 kilogram of furans.
(4) after in per generation,, basic the end took place in the bar snout moth's larva, the investigation prevention effect.
(5) result of the test is as follows:
Jamming rate investigation that table 5 is isotropic
| From generation to generation | Prescription 1 | Prescription 2 | Prescription 3 | ||||||
| The check plot lures moth number (head) | Isotropic district lures moth number (head) | Isotropic jamming rate (%) | The check plot lures moth number (head) | Isotropic district lures moth number (head) | Isotropic jamming rate (%) | The check plot lures moth number (head) | Isotropic district lures moth number (head) | Isotropic jamming rate (%) | |
| A generation | 700 | 12 | 98.3 | 654 | 18 | 97.2 | 803 | 5 | 99.4 |
| Two generations | 998 | 35 | 96.5 | 733 | 44 | 94 | 996 | 22 | 97.8 |
| The three generations | 813 | 11 | 98.6 | 1530 | 13 | 99.2 | 682 | 9 | 98.7 |
| Average isotropic jamming rate (%) | 97.8 | 96.8 | 98.6 | ||||||
The dead tail rate investigation of table 6 snout moth's larva
| Prescription | Prescription 1 | Prescription 2 | Prescription 3 | |
| Dead tail rate (%) | Isotropic district | 9.1 | 6.91 | 7.67 |
| The check plot | 27.7 | 18.1 | 25.37 | |
| Relative slip (%) | 67.1 | 61.8 | 69.8 | |
(6) result of the test shows: isotropic district lures moth quantity to have only tens, and obviously the induced moth number than the check plot lacks, the isotropic interference effect that is to say the article sugarcane borer sex attractant clearly, isotropic jamming rate all reaches more than 94%.After using the article sugarcane borer sex attractant to carry out isotropic control, the dead tail rate of the sugarcane in isotropic district all is lower than 10%, and with the dead tail rate in check plot of the red control of conventional pesticide furans still more than 18%, the dead tail of isotropic district sugarcane is compared with the check plot, the relative slip of its dead tail reaches more than 61%, and this explanation article sugarcane borer sex attractant control article sugarcane borer is an effective new technology of advanced person.
Description of drawings
Fig. 1 is an article sugarcane borer sex attractant synthetic line sketch of the present invention.
Claims (3)
1. the preparation method of an article sugarcane borer sex attractant, it basic composition is:
(1) suitable-11-hexadecylene alcohol acetate
(2) suitable-13-oleic alcohol
(3) suitable-13-oleic alcohol acetate
Above-mentioned three kinds of components are evenly made the article sugarcane borer sex attractant in following ratio and solvent, and its proportioning (percentage by weight) is:
Suitable-11-hexadecylene alcohol acetate 35～45%
Suitable-13-oleic alcohol 5～15%
Suitable-13-oleic alcohol acetate 40～60%
2. a film that is used for the article sugarcane borer prediction is characterized in that: every 3cm
2Film in contain 150-250 μ g sex attractant, described sex attractant is to obtain by the preparation method of the described article sugarcane borer sex attractant of claim 1, and this sex attractant is impregnated in the film carrier.
3. one kind is used for the isotropic pipe that article sugarcane borer is prevented and treated, it is characterized in that: the plastic tube of every 14kg contains the 180-250g sex attractant, described sex attractant is the preparation method's acquisition by the described article sugarcane borer sex attractant of claim 1, this sex attractant is mixed being crushed to plastic tube with plastic raw materials.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410015484 CN1287665C (en) | 2004-02-27 | 2004-02-27 | Sex-attractant for cane stripe pyralid, and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410015484 CN1287665C (en) | 2004-02-27 | 2004-02-27 | Sex-attractant for cane stripe pyralid, and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1559209A CN1559209A (en) | 2005-01-05 |
| CN1287665C true CN1287665C (en) | 2006-12-06 |
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|---|---|---|---|
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US9189605B2 (en) | 2005-04-22 | 2015-11-17 | Microsoft Technology Licensing, Llc | Protected computing environment |
| US9363481B2 (en) | 2005-04-22 | 2016-06-07 | Microsoft Technology Licensing, Llc | Protected media pipeline |
| US9436804B2 (en) | 2005-04-22 | 2016-09-06 | Microsoft Technology Licensing, Llc | Establishing a unique session key using a hardware functionality scan |
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| KR101353151B1 (en) * | 2010-05-19 | 2014-01-22 | 다이니혼 죠츄기쿠 가부시키가이샤 | Agent for attracting flying insect pests, Apparatus for attracting flying insect pests, and Method for attracting flying insect pests |
| CN103026930A (en) * | 2012-10-30 | 2013-04-10 | 扶绥县生产力促进中心 | Method for preventing and controlling diseases and pests of sugarcane |
| CN104472483B (en) * | 2014-12-31 | 2017-02-22 | 广州甘蔗糖业研究所 | Proceras venosatus sex pheromone microsphere and preparing method thereof |
| CN108124867B (en) * | 2017-12-20 | 2020-04-21 | 广东省生物工程研究所（广州甘蔗糖业研究所） | Striped rice borer sex pheromone liquid sustained-release agent and preparation method thereof |
| CN108383688A (en) * | 2018-03-30 | 2018-08-10 | 上海右肯医药科技有限公司 | A kind of striped rice borer, the composition principle and its processing technology of yellow rice borer pheromones |
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2004
- 2004-02-27 CN CN 200410015484 patent/CN1287665C/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9189605B2 (en) | 2005-04-22 | 2015-11-17 | Microsoft Technology Licensing, Llc | Protected computing environment |
| US9363481B2 (en) | 2005-04-22 | 2016-06-07 | Microsoft Technology Licensing, Llc | Protected media pipeline |
| US9436804B2 (en) | 2005-04-22 | 2016-09-06 | Microsoft Technology Licensing, Llc | Establishing a unique session key using a hardware functionality scan |
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| CN1559209A (en) | 2005-01-05 |
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Assignee: GUANGDONG PROVINCE WENGYUAN COUNTY MAOYUAN SUGAR CO., LTD. Assignor: Guangzhou Sugarcane Industry Research Institute Contract record no.: 2010440000535 Denomination of invention: Sex-attractant for cane stripe pyralid, and application thereof Granted publication date: 20061206 License type: Exclusive License Open date: 20050105 Record date: 20100520 |
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