RU96120208A - SPECIAL FUNGICIDES INTENDED TO COMBAT TROUBLESHOOTING - Google Patents
SPECIAL FUNGICIDES INTENDED TO COMBAT TROUBLESHOOTINGInfo
- Publication number
- RU96120208A RU96120208A RU96120208/04A RU96120208A RU96120208A RU 96120208 A RU96120208 A RU 96120208A RU 96120208/04 A RU96120208/04 A RU 96120208/04A RU 96120208 A RU96120208 A RU 96120208A RU 96120208 A RU96120208 A RU 96120208A
- Authority
- RU
- Russia
- Prior art keywords
- compound
- formula
- solvent
- ethyl
- values
- Prior art date
Links
- 239000000417 fungicide Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 8
- 239000002904 solvent Substances 0.000 claims 8
- -1 1-methyl-1- cyclopentyl Chemical group 0.000 claims 7
- 229910052744 lithium Inorganic materials 0.000 claims 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 6
- 229910052700 potassium Inorganic materials 0.000 claims 6
- 229910052708 sodium Inorganic materials 0.000 claims 6
- 239000011734 sodium Substances 0.000 claims 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 6
- 229910052801 chlorine Inorganic materials 0.000 claims 5
- 239000000460 chlorine Substances 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- 238000010992 reflux Methods 0.000 claims 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 229910052740 iodine Inorganic materials 0.000 claims 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N t-BuOH Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 4
- 238000011065 in-situ storage Methods 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 3
- 239000011591 potassium Substances 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 2
- 239000000010 aprotic solvent Substances 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- YVUBWJOBCFNMES-UHFFFAOYSA-N formamide;pyridine Chemical compound NC=O.C1=CC=NC=C1 YVUBWJOBCFNMES-UHFFFAOYSA-N 0.000 claims 2
- 230000003993 interaction Effects 0.000 claims 2
- 230000016507 interphase Effects 0.000 claims 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 2
- 239000011630 iodine Chemical group 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000002689 soil Substances 0.000 claims 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims 1
- ACFNQMUZNUYGSH-UHFFFAOYSA-N 2-chloro-6-(2,3-dimethylbutan-2-ylamino)-N-ethylbenzamide Chemical compound CCNC(=O)C1=C(Cl)C=CC=C1NC(C)(C)C(C)C ACFNQMUZNUYGSH-UHFFFAOYSA-N 0.000 claims 1
- FYNHBOOKJMTNKO-UHFFFAOYSA-N 2-chloro-6-(2-methylbutan-2-ylamino)-N-propylbenzamide Chemical compound CCCNC(=O)C1=C(Cl)C=CC=C1NC(C)(C)CC FYNHBOOKJMTNKO-UHFFFAOYSA-N 0.000 claims 1
- XRJPHMLCPMWNMF-UHFFFAOYSA-N 2-chloro-N-ethyl-6-(3-methylpentan-3-ylamino)benzamide Chemical group CCNC(=O)C1=C(Cl)C=CC=C1NC(C)(CC)CC XRJPHMLCPMWNMF-UHFFFAOYSA-N 0.000 claims 1
- MSXVEPNJUHWQHW-UHFFFAOYSA-N Tert-Amyl alcohol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 0 Cc1c(*)c(C(N)=O)c(C)cc1 Chemical compound Cc1c(*)c(C(N)=O)c(C)cc1 0.000 description 4
Claims (16)
в которой R2 - этил, изопропил, пропил или аллил;
A - N(CH3)1-nHnR5 или OR6, где n означает O или 1, R5 представляет (CH3)m (CH3CH2)3-mC, 1-метил-1-циклопентил, 1-метил-1-циклогексил или 2,3-диметил-2-бутил, где m означает 0, 1, 2 или 3, а R6 независимо представляет R5 или 2,3,3-триметил-2-бутил;
R3 представляет H или независимо R4; и
R4 представляет галоген или CH3;
при условии, что когда A является N(CH3)1-nHnR5, где n означает 0 или 1, R3 - H и R5 - 1-метил-1-циклогексил или (CH3)m(CH2CH3)3-mC, где m означает 0 или 3, или если R3 - галоген и R5 является (CH3)m(CH2CH3)3-mC, где m означает 3, тогда R2 не может быть этилом;
а также при условии, что, когда A представляет OR6, то m является целым числом, равным или меньше 2, и если R3 - H или галоген, а R2 - этил или изопропил, тогда R6 является (CH3)m(CH3CH2)3-mC, где m означает 1; или его сельскохозяйственно-приемлемая соль.1. The compound of formula (I)
in which R 2 is ethyl, isopropyl, propyl or allyl;
A is N (CH 3 ) 1-n H n R 5 or OR 6 , where n is O or 1, R 5 is (CH 3 ) m (CH 3 CH 2 ) 3-m C, 1-methyl-1- cyclopentyl, 1-methyl-1-cyclohexyl or 2,3-dimethyl-2-butyl, where m is 0, 1, 2 or 3, and R 6 independently represents R 5 or 2,3,3-trimethyl-2-butyl ;
R 3 is H or independently R 4 ; and
R 4 is halogen or CH 3 ;
provided that when A is N (CH 3 ) 1-n H n R 5 where n is 0 or 1, R 3 is H and R 5 is 1-methyl-1-cyclohexyl or (CH 3 ) m (CH 2 CH 3 ) 3-m C, where m is 0 or 3, or if R 3 is halogen and R 5 is (CH 3 ) m (CH 2 CH 3 ) 3-m C, where m means 3, then R 2 cannot be ethyl;
and also provided that when A is OR 6 , then m is an integer equal to or less than 2, and if R 3 is H or halogen, and R 2 is ethyl or isopropyl, then R 6 is (CH 3 ) m (CH 3 CH 2 ) 3-m C, where m is 1; or its agriculturally acceptable salt.
в которой A - OR6, где R6 независимо представляет R5 или 2,3,3-триметил-2-бутил;
R2 - этил, изопропил, пропил или аллил;
R3 - представляет H или независимо R4;
R4 - галоген или CH3;
соединением формулы R2X, в которой R2 имеет указанные выше значения, а X представляет хлор, бром, иод или OS O2(OR2), в присутствии основания, или соединением формулы R2X, в которой R2 и X имеют указанные выше значения, в присутствии основания и межфазового катализатора межфазового переноса с целью получения соединения формулы 1 по п.1, в которой A представляет OR6, где R6 имеет указанные выше значения.7. The method of processing compounds of formula (V)
in which A is OR 6 , wherein R 6 is independently R 5 or 2,3,3-trimethyl-2-butyl;
R 2 is ethyl, isopropyl, propyl or allyl;
R 3 - represents H or independently R 4 ;
R 4 is halogen or CH 3 ;
a compound of the formula R 2 X, in which R 2 is as defined above, and X is chlorine, bromine, iodine or OS O 2 (OR 2 ), in the presence of a base, or a compound of the formula R 2 X, in which R 2 and X have the above values, in the presence of a base and an interphase transfer phase catalyst for the purpose of preparing a compound of formula 1 according to claim 1, wherein A is OR 6 , where R 6 is as defined above.
в которой A, R3 и R4 имеют указанные выше значения;
NaOH, H2O2, H2O и этанолом; или
путем кипячения с обратным холодильником вместе с КОН в трет-бутаноле или третичном амиловом спирте, с получением соединения формулы Y по пункту 7.8. The method according to p. 7, characterized in that it includes processing of the compounds of formula (IV)
in which A, R 3 and R 4 have the above values;
NaOH, H 2 O 2 , H 2 O and ethanol; or
by boiling under reflux with KOH in tert-butanol or a tertiary amyl alcohol to obtain the compound of formula Y according to item 7.
в которой Q представляет фтор или хлор, а R3 и R4 имеют указанные выше значения;
с соединением формулы MA, в которой M является Li, Na или К, в растворителе или с эквивалентом соединения MA, полученным in situ путем кипячения с обратным холодильником лития, натрия или калия в избытке AH, где A имеет указанные выше значения, с получением соединения формулы IY по п.8.9. The method according to p. 8, characterized in that it includes the interaction of the compounds of formula (III)
in which Q represents fluorine or chlorine, and R 3 and R 4 have the above values;
with a compound of the formula MA, in which M is Li, Na or K, in a solvent or with an equivalent of compound MA, obtained in situ by refluxing lithium, sodium or potassium in excess of AH, where A is as defined above, to give the compound Formula IV under item 8.
соединением (COCl)2 или тионилхлоридом в присутствии пиридина и диметилформамида в апротонном растворителе, а затем соединением H2NR2 с получением соединения формулы I по пункту 1, в которой A - OR6, а R6 независимо от других элементов представляет R5 или 2,3,3-триметил-2-бутил.10. The method of processing compounds of formula (Y1)
compound (COCl) 2 or thionyl chloride in the presence of pyridine and dimethylformamide in an aprotic solvent, and then the compound H 2 NR 2 to obtain the compound of formula I in paragraph 1, in which A is OR 6 and R 6 independently of other elements represents R 5 or 2,3,3-trimethyl-2-butyl.
в которой A, R3 и R4 имеют указанные выше значения;
соединением Hal (изобутил)2 в растворителе, представляющем собой толуол или метиленхлорид, с последующим взаимодействием с КМnO4 в спиртовом растворителе, KH2PO4, H2O с показателями рН 5 - 9, с получением соединения формулы YI по п.10.11. The method according to p. 10 processing compounds of formula (IY)
in which A, R 3 and R 4 have the above values;
Hal (isobutyl) 2 in a solvent that represents toluene or methylene chloride, followed by reaction with KM n O 4 in an alcohol solvent, KH 2 PO 4 , H 2 O with pH values of 5 - 9, to obtain the compound of formula YI according to claim ten.
в которой Q имеет указанные выше значения от других элементов, R3 и R4 также имеют указанные выше значения;
соединением формулы МА в растворителе, где М представляет Li, Na или K, либо его эквивалентом, приготовленным in situ путем кипячения с обратным холодильником лития, натрия или калия в избытке АН, где А имеет указанные выше значения; с целью получения соединения формулы IY по п.11.12. The method according to claim 11 for treating a compound of formula (III)
in which Q has the above values from other elements, R 3 and R 4 also have the above values;
a compound of the formula MA in a solvent, where M is Li, Na or K, or its equivalent, prepared in situ by refluxing lithium, sodium or potassium in excess of AN, where A has the values indicated above; in order to obtain the compounds of formula IY according to claim 11.
в которой Q- фтор или хлор, а R3 и R4 имеют указанные выше значения;
с соединением формулы МА, в которой М является Li, Na или K, или с эквивалентом соединения МА, полученным in situ путем кипячения с обратным холодильником лития, натрия или калия в избытке АН, где А имеет указанные выше значения, с целью получения соединения формулы (IY)
в которой A, R3 и R4 имеют указанные выше значения; а затем либо стадию 2)а), нагревания соединения формулы IY с NaOH, H2O2, H2O и этанолом; либо стадию 2) b), кипячения с обратным холодильником соединения формулы IY с КОН в растворителе;
с получением соединения формулы (Y)
в которой A, R3 и R4 имеют указанные выше значения; стадию 3) обработки соединения формулы Y соединением формулы R2X, в которой X - бром, хлор, иод или -OSO2(OR2), в присутствии основания, или стадию 3), обработки соединения формулы Y соединением формулы R2X, в которой R2 и X имеют указанные выше значения, в присутствии основания содержащего гидроксигруппу и катализатора межфазового переноса;
с целью получения соединения формулы I, в которой A представляет OR6 и R6 имеет указанные выше значения; или стадию 2) взаимодействия указанного выше соединения формулы IY а) с Hal (изобутил)2 в растворителе таком как толуол или метиленхлорид, а затем b) с KMnO4 в таком спиртовом растворителе, как этанол или трет-бутанол, KH2PO4, H2O с показателем рН примерно 5 - 9, с получением соединения формулы (YI)
в которой A, R3 и R4 имеют указанные выше значения, и стадию 3') обработки соединения формулы YI a) тионилхлоридом или (COCl)2 в присутствии пиридина и диметилформамида в апротонном растворителе, таком как ацетонитрил, метиленхлорид или дихлорэтан; b) а затем H2NR2
с целью получения вышеуказанного соединения формулы I, в которой A представляет OR6 и R6 имеет указанные выше значения.13. The method of obtaining the compound according to claim 1 of formula 1, in which A represents OR 6 and R 6 has the above values, characterized in that it includes step 1), the interaction in the solvent of the compound of formula (III)
in which Q is fluoro or chloro, and R 3 and R 4 are as defined above;
with a compound of the formula MA, in which M is Li, Na or K, or with an equivalent of compound MA, obtained in situ by refluxing lithium, sodium or potassium in excess of AN, where A is as defined above, in order to obtain the compound of formula (IY)
in which A, R 3 and R 4 have the above values; and then either stage 2) a), heating the compound of formula IY with NaOH, H 2 O 2 , H 2 O, and ethanol; or step 2) b), refluxing the compound of formula IV with KOH in a solvent;
to form a compound of formula (Y)
in which A, R 3 and R 4 have the above values; step 3) of treating a compound of formula Y with a compound of formula R 2 X, in which X is bromine, chlorine, iodine or -OSO 2 (OR 2 ), in the presence of a base, or step 3), treating the compound of formula Y with a compound of formula R 2 X, in which R 2 and X have the above values, in the presence of a base containing a hydroxy group and an interphase transfer catalyst;
in order to obtain a compound of formula I, in which A is OR 6 and R 6 is as defined above; or step 2) reacting the above compound of formula IY a) with Hal (isobutyl) 2 in a solvent such as toluene or methylene chloride, and then b) with KM n O 4 in an alcohol solvent such as ethanol or tert-butanol, KH 2 PO 4 , H 2 O with a pH of about 5 to 9, to obtain the compounds of formula (YI)
wherein A, R 3 and R 4 are as defined above, and step 3 ′) treating a compound of formula YI a) with thionyl chloride or (COCl) 2 in the presence of pyridine and dimethylformamide in an aprotic solvent such as acetonitrile, methylene chloride or dichloroethane; b) and then H 2 NR 2
in order to obtain the above compound of formula I, in which A is OR 6 and R 6 is as defined above.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/207,508 | 1994-03-08 | ||
| US08/207.508 | 1994-03-08 | ||
| US08/207,508 US5482974A (en) | 1994-03-08 | 1994-03-08 | Selected fungicides for the control of take-all disease of plants |
| PCT/US1995/002193 WO1995024380A1 (en) | 1994-03-08 | 1995-02-21 | Selected benzamide fungicides for the control of take-all disease of plants |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU96120208A true RU96120208A (en) | 1999-01-27 |
| RU2144023C1 RU2144023C1 (en) | 2000-01-10 |
Family
ID=22770881
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU96120208/04A RU2144023C1 (en) | 1994-03-08 | 1995-02-21 | Substituted benzamides, method of their synthesis, intermediate compounds, composition and method of control of plant sweating out sickness |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5482974A (en) |
| EP (1) | EP0749416B1 (en) |
| CN (1) | CN1105704C (en) |
| AT (1) | ATE174904T1 (en) |
| AU (1) | AU678702B2 (en) |
| CA (1) | CA2184260A1 (en) |
| CZ (1) | CZ290847B6 (en) |
| DE (1) | DE69506849T2 (en) |
| DK (1) | DK0749416T3 (en) |
| ES (1) | ES2126258T3 (en) |
| GR (1) | GR3029760T3 (en) |
| HU (1) | HU222568B1 (en) |
| NZ (1) | NZ281514A (en) |
| PL (1) | PL179549B1 (en) |
| RU (1) | RU2144023C1 (en) |
| UA (1) | UA44270C2 (en) |
| WO (1) | WO1995024380A1 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2190400A (en) * | 1998-12-16 | 2000-07-03 | Northwestern University | Inhibitors of beta-lactamases and uses therefor |
| EP1200393B1 (en) | 1999-08-13 | 2003-12-10 | Monsanto Technology LLC | Oxime amides and hydrazone amides having fungicidal activity |
| US7687434B2 (en) | 2000-12-22 | 2010-03-30 | Monsanto Technology, Llc | Method of improving yield and vigor of plants |
| US6992047B2 (en) * | 2001-04-11 | 2006-01-31 | Monsanto Technology Llc | Method of microencapsulating an agricultural active having a high melting point and uses for such materials |
| MXPA04002942A (en) | 2001-09-27 | 2004-06-21 | Monsanto Technology Llc | Fungicidal compositions and their applications in agriculture. |
| CN103102263A (en) * | 2013-02-18 | 2013-05-15 | 青岛农业大学 | 3-bromine-4-methoxybenzoic acid preparation method and agricultural biological activity |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4060637A (en) * | 1971-06-21 | 1977-11-29 | Pierre Fabre Sa | Medicaments having psychotropic properties |
| JPS6034542B2 (en) * | 1977-10-04 | 1985-08-09 | 塩野義製薬株式会社 | New isothiocyanate phenyl esters |
| US4485105A (en) * | 1978-10-12 | 1984-11-27 | American Cyanamid Company | Method of treating hyperlipidemia with 4-(monoalkylamino)benzoic acid amides |
| GB8609452D0 (en) * | 1986-04-17 | 1986-05-21 | Ici Plc | Fungicides |
| US5283352A (en) * | 1986-11-28 | 1994-02-01 | Orion-Yhtyma Oy | Pharmacologically active compounds, methods for the preparation thereof and compositions containing the same |
| JPS63284164A (en) * | 1987-05-15 | 1988-11-21 | Ube Ind Ltd | 2-methyl-4-amino-5-aminomethylpyrimidine carbonate and its production |
| US4997836A (en) * | 1988-11-11 | 1991-03-05 | Takeda Chemical Industries, Ltd. | Trisubstituted piperazine compounds, their production and use |
| IE62559B1 (en) * | 1989-02-02 | 1995-02-08 | Ici Plc | Fungicides |
| CA2119155C (en) * | 1991-10-18 | 1999-06-15 | Dennis Paul Phillion | Fungicides for the control of take-all disease of plants |
-
1994
- 1994-03-08 US US08/207,508 patent/US5482974A/en not_active Expired - Fee Related
-
1995
- 1995-02-21 HU HU9602456A patent/HU222568B1/en active IP Right Grant
- 1995-02-21 DE DE69506849T patent/DE69506849T2/en not_active Expired - Lifetime
- 1995-02-21 EP EP95910319A patent/EP0749416B1/en not_active Expired - Lifetime
- 1995-02-21 DK DK95910319T patent/DK0749416T3/en active
- 1995-02-21 NZ NZ281514A patent/NZ281514A/en unknown
- 1995-02-21 ES ES95910319T patent/ES2126258T3/en not_active Expired - Lifetime
- 1995-02-21 AT AT95910319T patent/ATE174904T1/en active
- 1995-02-21 UA UA96103816A patent/UA44270C2/en unknown
- 1995-02-21 CN CN95192848A patent/CN1105704C/en not_active Expired - Fee Related
- 1995-02-21 CA CA002184260A patent/CA2184260A1/en not_active Abandoned
- 1995-02-21 CZ CZ19962559A patent/CZ290847B6/en not_active IP Right Cessation
- 1995-02-21 RU RU96120208/04A patent/RU2144023C1/en not_active IP Right Cessation
- 1995-02-21 WO PCT/US1995/002193 patent/WO1995024380A1/en active IP Right Grant
- 1995-02-21 PL PL95316141A patent/PL179549B1/en not_active IP Right Cessation
- 1995-02-21 AU AU18478/95A patent/AU678702B2/en not_active Ceased
-
1999
- 1999-03-22 GR GR990400846T patent/GR3029760T3/en unknown
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