JP4520299B2 - フェニルベンズアミド - Google Patents
フェニルベンズアミド Download PDFInfo
- Publication number
- JP4520299B2 JP4520299B2 JP2004518548A JP2004518548A JP4520299B2 JP 4520299 B2 JP4520299 B2 JP 4520299B2 JP 2004518548 A JP2004518548 A JP 2004518548A JP 2004518548 A JP2004518548 A JP 2004518548A JP 4520299 B2 JP4520299 B2 JP 4520299B2
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- plants
- formula
- benzamide
- species
- 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.)
- Expired - Fee Related
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- GTKIGDZXPDCIKR-UHFFFAOYSA-N 2-phenylbenzamide Chemical compound NC(=O)C1=CC=CC=C1C1=CC=CC=C1 GTKIGDZXPDCIKR-UHFFFAOYSA-N 0.000 title claims description 20
- -1 1,3-dimethylbutyl Chemical group 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 32
- 241000233866 Fungi Species 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 230000003032 phytopathogenic effect Effects 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- IOIRBHLKTRPQBR-UHFFFAOYSA-N 2-bromo-n-[2-(4-methylpentan-2-yl)phenyl]benzamide Chemical compound CC(C)CC(C)C1=CC=CC=C1NC(=O)C1=CC=CC=C1Br IOIRBHLKTRPQBR-UHFFFAOYSA-N 0.000 claims description 3
- IESUPPBKWJHHEW-UHFFFAOYSA-N 2-chloro-n-[2-(4-methylpentan-2-yl)phenyl]benzamide Chemical compound CC(C)CC(C)C1=CC=CC=C1NC(=O)C1=CC=CC=C1Cl IESUPPBKWJHHEW-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- GMMOMHSLRVQSRX-UHFFFAOYSA-N 2-iodo-n-[2-(4-methylpentan-2-yl)phenyl]benzamide Chemical compound CC(C)CC(C)C1=CC=CC=C1NC(=O)C1=CC=CC=C1I GMMOMHSLRVQSRX-UHFFFAOYSA-N 0.000 claims description 2
- 239000004067 bulking agent Substances 0.000 claims description 2
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- 241000196324 Embryophyta Species 0.000 description 73
- 150000001875 compounds Chemical class 0.000 description 71
- 238000012360 testing method Methods 0.000 description 30
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- 230000000694 effects Effects 0.000 description 20
- 238000009472 formulation Methods 0.000 description 18
- 238000004519 manufacturing process Methods 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 14
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- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- LPZZJKBLKQOBMZ-UHFFFAOYSA-N 2-(4-methylpentan-2-yl)aniline Chemical compound CC(C)CC(C)C1=CC=CC=C1N LPZZJKBLKQOBMZ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
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- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
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- MXIUWSYTQJLIKE-UHFFFAOYSA-N 2-(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC=CC=C1C(Cl)=O MXIUWSYTQJLIKE-UHFFFAOYSA-N 0.000 description 4
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NZCKTGCKFJDGFD-UHFFFAOYSA-N 2-bromobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Br NZCKTGCKFJDGFD-UHFFFAOYSA-N 0.000 description 3
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- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/45—Monoamines
- C07C211/48—N-alkylated amines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10229595A DE10229595A1 (de) | 2002-07-02 | 2002-07-02 | Phenylbenzamide |
| PCT/EP2003/006512 WO2004005242A1 (de) | 2002-07-02 | 2003-06-20 | Phenylbenzamide |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006503809A JP2006503809A (ja) | 2006-02-02 |
| JP2006503809A5 JP2006503809A5 (https=) | 2006-08-03 |
| JP4520299B2 true JP4520299B2 (ja) | 2010-08-04 |
Family
ID=29723619
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004518548A Expired - Fee Related JP4520299B2 (ja) | 2002-07-02 | 2003-06-20 | フェニルベンズアミド |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US7314958B2 (https=) |
| EP (1) | EP1519913A1 (https=) |
| JP (1) | JP4520299B2 (https=) |
| KR (1) | KR101025742B1 (https=) |
| CN (1) | CN1324005C (https=) |
| AR (1) | AR039743A1 (https=) |
| AU (1) | AU2003245975A1 (https=) |
| BR (1) | BR0312407B1 (https=) |
| CA (1) | CA2491368A1 (https=) |
| DE (1) | DE10229595A1 (https=) |
| EA (1) | EA009884B1 (https=) |
| IL (1) | IL165925A (https=) |
| MX (1) | MXPA05000114A (https=) |
| PL (1) | PL374466A1 (https=) |
| TW (1) | TW200413284A (https=) |
| UA (1) | UA78340C2 (https=) |
| WO (1) | WO2004005242A1 (https=) |
| ZA (1) | ZA200500014B (https=) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10349501A1 (de) | 2003-10-23 | 2005-05-25 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| DE10354607A1 (de) | 2003-11-21 | 2005-06-16 | Bayer Cropscience Ag | Siylierte Carboxamide |
| DE102004005317A1 (de) * | 2003-12-18 | 2005-07-21 | Bayer Cropscience Ag | Optisch aktive Carboxamide |
| KR20060126713A (ko) * | 2003-12-18 | 2006-12-08 | 바이엘 크롭사이언스 아게 | 광학적 활성 카복사미드 및 원치않는 미생물을 구제하기위한 그의 용도 |
| DE102004005786A1 (de) * | 2004-02-06 | 2005-08-25 | Bayer Cropscience Ag | Haloalkylcarboxamide |
| DE102004005785A1 (de) * | 2004-02-06 | 2005-08-25 | Bayer Cropscience Ag | 2-Halogenfuryl/thienyl-3-carboxamide |
| DE102004029972A1 (de) * | 2004-06-21 | 2006-01-05 | Bayer Cropscience Ag | Beizmittel zur Bekämpfung von phytopathogenen Pilzen |
| DE102005015850A1 (de) | 2005-04-07 | 2006-10-12 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| CN101203135B (zh) * | 2005-04-28 | 2014-06-11 | 拜尔农作物科学股份公司 | 农药活性物质结合物 |
| DE102005022147A1 (de) * | 2005-04-28 | 2006-11-02 | Bayer Cropscience Ag | Wirkstoffkombinationen |
| DE102005026482A1 (de) | 2005-06-09 | 2006-12-14 | Bayer Cropscience Ag | Wirkstoffkombinationen |
| EA201270781A1 (ru) | 2005-06-09 | 2013-09-30 | Байер Кропсайенс Аг | Комбинации биологически активных веществ |
| DE102005035300A1 (de) * | 2005-07-28 | 2007-02-01 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| DE102006023263A1 (de) * | 2006-05-18 | 2007-11-22 | Bayer Cropscience Ag | Synergistische Wirkstoffkombinationen |
| EP2109362A2 (en) * | 2007-02-14 | 2009-10-21 | Basf Se | Method of inducing virus tolerance of plants |
| ATE528278T1 (de) | 2007-08-30 | 2011-10-15 | Albemarle Corp | Herstellung von 2-(1,3-dimethylbutyl)anilin und anderen verzweigten, alkylsubstituierten anilinen |
| DE102007045920B4 (de) | 2007-09-26 | 2018-07-05 | Bayer Intellectual Property Gmbh | Synergistische Wirkstoffkombinationen |
| JP2011511033A (ja) | 2008-02-05 | 2011-04-07 | ビーエーエスエフ ソシエタス・ヨーロピア | 植物体健康組成物 |
| EA023545B1 (ru) * | 2008-10-21 | 2016-06-30 | Басф Се | Применение карбоксамида флуопирама на культивируемых растениях |
| MX2011009732A (es) | 2009-03-25 | 2011-09-29 | Bayer Cropscience Ag | Combinaciones de principios activos sinergicas. |
| KR20120051015A (ko) | 2009-07-16 | 2012-05-21 | 바이엘 크롭사이언스 아게 | 페닐 트리아졸을 함유하는 상승적 활성 물질 배합물 |
| US8748342B2 (en) | 2009-12-08 | 2014-06-10 | Basf Se | Pesticidal mixtures |
| NZ600886A (en) | 2009-12-08 | 2013-06-28 | Basf Se | An agrochemical pesticidal mixture for increasing the yield and health of a plant |
| ES2567266T3 (es) | 2010-05-28 | 2016-04-21 | Basf Se | Mezclas de pesticidas |
| US8551746B2 (en) * | 2011-09-21 | 2013-10-08 | Coskata, Inc. | Method for controlling undesirable byproducts formation caused by contaminating organisms in the production of ethanol from syngas |
| KR102339016B1 (ko) | 2013-11-29 | 2021-12-14 | 프로이오닉 게엠베하 | 마이크로파 조사에 의한 접착제 경화 방법 |
| EP2910126A1 (en) | 2015-05-05 | 2015-08-26 | Bayer CropScience AG | Active compound combinations having insecticidal properties |
| WO2018069841A1 (en) | 2016-10-14 | 2018-04-19 | Pi Industries Ltd | 4-substituted phenylamine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms |
| CA3040408A1 (en) | 2016-10-14 | 2018-04-19 | Pi Industries Ltd | 4-amino substituted phenylamidine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms |
| CN116918810B (zh) * | 2022-06-22 | 2026-01-30 | 河北艾林化工科技有限公司 | 一种杀虫剂组合物及其应用 |
| CN118985618B (zh) * | 2024-07-05 | 2025-10-10 | 云南大学 | 一种苯甲酰胺类化合物在防治植物根结线虫中的应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2730620A1 (de) | 1977-07-07 | 1979-01-25 | Bayer Ag | Neue n-aryl-n'-alkyl-s-alkyl- isothioharnstoffe, verfahren zu ihrer herstellung sowie ihre verwendung als mittel zur bekaempfung von tierischen und pflanzlichen schaedlingen |
| JPS58140054A (ja) | 1982-02-10 | 1983-08-19 | Sumitomo Chem Co Ltd | インダニルベンツアミド誘導体、その製造法およびこれらを有効成分として含有する農園芸用殺菌剤 |
| IL103614A (en) * | 1991-11-22 | 1998-09-24 | Basf Ag | Carboxamides for controlling botrytis and certain novel such compounds |
| DE19629828A1 (de) * | 1996-07-24 | 1998-01-29 | Bayer Ag | Carbanilide |
| JP3982879B2 (ja) * | 1996-08-15 | 2007-09-26 | 三井化学株式会社 | 置換カルボン酸アニリド誘導体およびこれを有効成分とする植物病害防除剤 |
| JP2001072508A (ja) * | 1999-09-03 | 2001-03-21 | Mitsui Chemicals Inc | 植物病害防除剤組成物 |
| JP2001072510A (ja) * | 1999-09-03 | 2001-03-21 | Mitsui Chemicals Inc | 植物病害防除剤組成物 |
| US7105565B2 (en) * | 2000-11-08 | 2006-09-12 | Syngenta Crop Protection, Inc. | Pyrrolcarboxamides and pyrrolcarbothioamides and their agrochemical uses |
| DE10136065A1 (de) | 2001-07-25 | 2003-02-13 | Bayer Cropscience Ag | Pyrazolylcarboxanilide |
-
2002
- 2002-07-02 DE DE10229595A patent/DE10229595A1/de not_active Withdrawn
-
2003
- 2003-06-20 JP JP2004518548A patent/JP4520299B2/ja not_active Expired - Fee Related
- 2003-06-20 US US10/518,446 patent/US7314958B2/en not_active Expired - Fee Related
- 2003-06-20 PL PL03374466A patent/PL374466A1/xx not_active Application Discontinuation
- 2003-06-20 KR KR1020047021497A patent/KR101025742B1/ko not_active Expired - Fee Related
- 2003-06-20 EA EA200500037A patent/EA009884B1/ru not_active IP Right Cessation
- 2003-06-20 BR BRPI0312407-0A patent/BR0312407B1/pt not_active IP Right Cessation
- 2003-06-20 CN CNB038208121A patent/CN1324005C/zh not_active Expired - Fee Related
- 2003-06-20 EP EP03738073A patent/EP1519913A1/de not_active Withdrawn
- 2003-06-20 MX MXPA05000114A patent/MXPA05000114A/es active IP Right Grant
- 2003-06-20 UA UAA200500915A patent/UA78340C2/uk unknown
- 2003-06-20 AU AU2003245975A patent/AU2003245975A1/en not_active Abandoned
- 2003-06-20 CA CA002491368A patent/CA2491368A1/en not_active Abandoned
- 2003-06-20 WO PCT/EP2003/006512 patent/WO2004005242A1/de not_active Ceased
- 2003-06-25 AR ARP030102277A patent/AR039743A1/es unknown
- 2003-07-01 TW TW092117901A patent/TW200413284A/zh unknown
-
2004
- 2004-12-22 IL IL165925A patent/IL165925A/en not_active IP Right Cessation
-
2005
- 2005-01-03 ZA ZA200500014A patent/ZA200500014B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1678567A (zh) | 2005-10-05 |
| AU2003245975A1 (en) | 2004-01-23 |
| EP1519913A1 (de) | 2005-04-06 |
| MXPA05000114A (es) | 2005-04-08 |
| BR0312407B1 (pt) | 2014-03-25 |
| KR20050016657A (ko) | 2005-02-21 |
| DE10229595A1 (de) | 2004-01-15 |
| IL165925A0 (en) | 2006-01-15 |
| UA78340C2 (en) | 2007-03-15 |
| CA2491368A1 (en) | 2004-01-15 |
| US20060211771A1 (en) | 2006-09-21 |
| WO2004005242A1 (de) | 2004-01-15 |
| CN1324005C (zh) | 2007-07-04 |
| EA200500037A1 (ru) | 2005-06-30 |
| AR039743A1 (es) | 2005-03-09 |
| US7314958B2 (en) | 2008-01-01 |
| JP2006503809A (ja) | 2006-02-02 |
| IL165925A (en) | 2009-12-24 |
| KR101025742B1 (ko) | 2011-04-04 |
| ZA200500014B (en) | 2006-06-28 |
| EA009884B1 (ru) | 2008-04-28 |
| BR0312407A (pt) | 2005-04-26 |
| TW200413284A (en) | 2004-08-01 |
| PL374466A1 (en) | 2005-10-31 |
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