JP2002518389A - １，３−オキサゾリンおよび１，３−チアゾリン誘導体、それらの製造、並びに農薬としてのそれらの使用 - Google Patents
１，３−オキサゾリンおよび１，３−チアゾリン誘導体、それらの製造、並びに農薬としてのそれらの使用Info
- Publication number
- JP2002518389A JP2002518389A JP2000554726A JP2000554726A JP2002518389A JP 2002518389 A JP2002518389 A JP 2002518389A JP 2000554726 A JP2000554726 A JP 2000554726A JP 2000554726 A JP2000554726 A JP 2000554726A JP 2002518389 A JP2002518389 A JP 2002518389A
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl
- halogen
- alkoxy
- cyano
- 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
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 title claims abstract description 31
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical class C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 title description 27
- 239000000575 pesticide Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 63
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 25
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 230000000895 acaricidal effect Effects 0.000 claims abstract description 9
- 230000000749 insecticidal effect Effects 0.000 claims abstract description 8
- 239000001301 oxygen Substances 0.000 claims abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 4
- 239000011593 sulfur Substances 0.000 claims abstract description 4
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 4
- -1 cyano, formyl Chemical group 0.000 claims description 127
- 239000000203 mixture Substances 0.000 claims description 72
- 229910052736 halogen Inorganic materials 0.000 claims description 48
- 150000002367 halogens Chemical class 0.000 claims description 46
- 239000013543 active substance Substances 0.000 claims description 38
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 35
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 25
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 22
- 239000000126 substance Substances 0.000 claims description 20
- 125000004414 alkyl thio group Chemical group 0.000 claims description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 17
- 238000009472 formulation Methods 0.000 claims description 17
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 16
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 13
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 12
- 241000238631 Hexapoda Species 0.000 claims description 11
- 241000244206 Nematoda Species 0.000 claims description 11
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 10
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 9
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 9
- 125000006554 (C4-C8) cycloalkenyl group Chemical group 0.000 claims description 9
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 8
- 125000002071 phenylalkoxy group Chemical group 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 6
- 241000233866 Fungi Species 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 230000000855 fungicidal effect Effects 0.000 claims description 6
- 239000000417 fungicide Substances 0.000 claims description 6
- 239000003755 preservative agent Substances 0.000 claims description 6
- 241000238876 Acari Species 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 241000237852 Mollusca Species 0.000 claims description 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 4
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 239000005068 cooling lubricant Substances 0.000 claims description 3
- 238000005553 drilling Methods 0.000 claims description 3
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 230000001069 nematicidal effect Effects 0.000 claims description 3
- 230000003032 phytopathogenic effect Effects 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 229910052718 tin Inorganic materials 0.000 claims description 3
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 2
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims description 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
- 125000006553 (C3-C8) cycloalkenyl group Chemical group 0.000 claims description 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000006356 alkylene carbonyl group Chemical group 0.000 claims description 2
- 125000005237 alkyleneamino group Chemical group 0.000 claims description 2
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 2
- 239000003973 paint Substances 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims 2
- 239000010730 cutting oil Substances 0.000 claims 2
- 230000002335 preservative effect Effects 0.000 claims 2
- 229910052796 boron Inorganic materials 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 239000000314 lubricant Substances 0.000 claims 1
- 239000003223 protective agent Substances 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
- 239000000565 sealant Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 13
- 230000009471 action Effects 0.000 abstract description 7
- 238000001228 spectrum Methods 0.000 abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 25
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 229910052731 fluorine Inorganic materials 0.000 description 20
- 239000011737 fluorine Substances 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 18
- 239000002243 precursor Substances 0.000 description 16
- 241000196324 Embryophyta Species 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000460 chlorine Substances 0.000 description 14
- 239000008187 granular material Substances 0.000 description 14
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000004587 chromatography analysis Methods 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- BTHSKBNIIDWPDA-UHFFFAOYSA-N 4-(4-bromophenyl)-2-(2,6-difluorophenyl)-4,5-dihydro-1,3-oxazole Chemical compound FC1=CC=CC(F)=C1C1=NC(C=2C=CC(Br)=CC=2)CO1 BTHSKBNIIDWPDA-UHFFFAOYSA-N 0.000 description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
- 241000607479 Yersinia pestis Species 0.000 description 9
- 238000000605 extraction Methods 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- 235000015097 nutrients Nutrition 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 230000018109 developmental process Effects 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 230000009261 transgenic effect Effects 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000001414 amino alcohols Chemical class 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- KTNHFPRYCCCOQV-UHFFFAOYSA-N 2-amino-2-(4-bromophenyl)ethanol Chemical compound OCC(N)C1=CC=C(Br)C=C1 KTNHFPRYCCCOQV-UHFFFAOYSA-N 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- OEUJXHRHHARJJG-UHFFFAOYSA-N [4-[2-(2,6-difluorophenyl)-4,5-dihydro-1,3-oxazol-4-yl]phenyl]-trimethylstannane Chemical compound C1=CC([Sn](C)(C)C)=CC=C1C1N=C(C=2C(=CC=CC=2F)F)OC1 OEUJXHRHHARJJG-UHFFFAOYSA-N 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 125000003282 alkyl amino group Chemical group 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 235000013601 eggs Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- QCAWEPFNJXQPAN-UHFFFAOYSA-N methoxyfenozide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(C)C=C(C)C=2)C(C)(C)C)=C1C QCAWEPFNJXQPAN-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- ZFLPXVODVSLZIU-UHFFFAOYSA-N (6-ethoxypyridin-3-yl)-trimethylstannane Chemical compound CCOC1=CC=C([Sn](C)(C)C)C=N1 ZFLPXVODVSLZIU-UHFFFAOYSA-N 0.000 description 3
- WJQAPGSCDBSIOO-UHFFFAOYSA-N 5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-2-(2,2,2-trifluoroethoxy)pyridine Chemical compound O1CC(C)(C)COB1C1=CC=C(OCC(F)(F)F)N=C1 WJQAPGSCDBSIOO-UHFFFAOYSA-N 0.000 description 3
- 241001425390 Aphis fabae Species 0.000 description 3
- 241000258924 Ctenocephalides felis Species 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 241000256248 Spodoptera Species 0.000 description 3
- 241001454293 Tetranychus urticae Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- HPNSNYBUADCFDR-UHFFFAOYSA-N chromafenozide Chemical compound CC1=CC(C)=CC(C(=O)N(NC(=O)C=2C(=C3CCCOC3=CC=2)C)C(C)(C)C)=C1 HPNSNYBUADCFDR-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- IXSZQYVWNJNRAL-UHFFFAOYSA-N etoxazole Chemical compound CCOC1=CC(C(C)(C)C)=CC=C1C1N=C(C=2C(=CC=CC=2F)F)OC1 IXSZQYVWNJNRAL-UHFFFAOYSA-N 0.000 description 3
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- CNKHSLKYRMDDNQ-UHFFFAOYSA-N halofenozide Chemical compound C=1C=CC=CC=1C(=O)N(C(C)(C)C)NC(=O)C1=CC=C(Cl)C=C1 CNKHSLKYRMDDNQ-UHFFFAOYSA-N 0.000 description 3
- 244000000013 helminth Species 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- 244000144972 livestock Species 0.000 description 3
- 230000002013 molluscicidal effect Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000007790 solid phase Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 description 2
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 description 2
- CFRPSFYHXJZSBI-DHZHZOJOSA-N (E)-nitenpyram Chemical compound [O-][N+](=O)/C=C(\NC)N(CC)CC1=CC=C(Cl)N=C1 CFRPSFYHXJZSBI-DHZHZOJOSA-N 0.000 description 2
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- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
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- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- HDWHGDDNMJOCCU-UHFFFAOYSA-N trimethyl(pyridin-2-yl)stannane Chemical compound C[Sn](C)(C)C1=CC=CC=N1 HDWHGDDNMJOCCU-UHFFFAOYSA-N 0.000 description 1
- APTGLCZIVXEHLK-UHFFFAOYSA-N trimethyl-(6-propoxypyridin-3-yl)stannane Chemical compound CCCOC1=CC=C([Sn](C)(C)C)C=N1 APTGLCZIVXEHLK-UHFFFAOYSA-N 0.000 description 1
- DBRNUXFCQQBVHV-UHFFFAOYSA-N trimethyl-[6-(2,2,2-trifluoroethoxy)pyridin-3-yl]stannane Chemical compound C[Sn](C)(C)C1=CC=C(OCC(F)(F)F)N=C1 DBRNUXFCQQBVHV-UHFFFAOYSA-N 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin 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-IMTORBKUSA-N 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19826671.5 | 1998-06-16 | ||
| DE19826671A DE19826671A1 (de) | 1998-06-16 | 1998-06-16 | 1,3-Oxazolin- und 1,3-Thiazolin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel |
| PCT/EP1999/003776 WO1999065901A1 (de) | 1998-06-16 | 1999-06-01 | 1,3-oxazolin- und 1,3-thiazolin-derivate, verfahren zu ihrer herstellung und ihre verwendung als schädlingsbekämpfungsmittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002518389A true JP2002518389A (ja) | 2002-06-25 |
| JP2002518389A5 JP2002518389A5 (https=) | 2006-07-20 |
Family
ID=7870979
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000554726A Pending JP2002518389A (ja) | 1998-06-16 | 1999-06-01 | １，３−オキサゾリンおよび１，３−チアゾリン誘導体、それらの製造、並びに農薬としてのそれらの使用 |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US6265350B1 (https=) |
| EP (1) | EP1087967B1 (https=) |
| JP (1) | JP2002518389A (https=) |
| KR (1) | KR20010052959A (https=) |
| CN (1) | CN1305476A (https=) |
| AR (1) | AR018673A1 (https=) |
| AT (1) | ATE252578T1 (https=) |
| AU (1) | AU750324B2 (https=) |
| BR (1) | BR9911358A (https=) |
| CA (1) | CA2335352A1 (https=) |
| CO (1) | CO5050288A1 (https=) |
| DE (2) | DE19826671A1 (https=) |
| ES (1) | ES2209451T3 (https=) |
| HU (1) | HUP0102360A3 (https=) |
| ID (1) | ID26652A (https=) |
| IL (1) | IL140236A (https=) |
| PL (1) | PL345041A1 (https=) |
| TR (1) | TR200003690T2 (https=) |
| WO (1) | WO1999065901A1 (https=) |
| ZA (1) | ZA200007301B (https=) |
Cited By (9)
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| JP2001342102A (ja) * | 2000-06-01 | 2001-12-11 | Nissan Chem Ind Ltd | 安定化される農薬組成物 |
| JP2013526541A (ja) * | 2010-05-12 | 2013-06-24 | バーテックス ファーマシューティカルズ インコーポレイテッド | Ａｔｒキナーゼ阻害剤として有用な化合物 |
| US9334244B2 (en) | 2010-05-12 | 2016-05-10 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| US9365557B2 (en) | 2008-12-19 | 2016-06-14 | Vertex Pharmaceuticals Incorporated | Substituted pyrazin-2-amines as inhibitors of ATR kinase |
| US9791456B2 (en) | 2012-10-04 | 2017-10-17 | Vertex Pharmaceuticals Incorporated | Method for measuring ATR inhibition mediated increases in DNA damage |
| US9862709B2 (en) | 2011-09-30 | 2018-01-09 | Vertex Pharmaceuticals Incorporated | Processes for making compounds useful as inhibitors of ATR kinase |
| US10478430B2 (en) | 2012-04-05 | 2019-11-19 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase and combination therapies thereof |
| US10813929B2 (en) | 2011-09-30 | 2020-10-27 | Vertex Pharmaceuticals Incorporated | Treating cancer with ATR inhibitors |
| US11464774B2 (en) | 2015-09-30 | 2022-10-11 | Vertex Pharmaceuticals Incorporated | Method for treating cancer using a combination of DNA damaging agents and ATR inhibitors |
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| DE10039477A1 (de) * | 2000-08-08 | 2002-02-21 | Aventis Cropscience Gmbh | Heterocyclylalkylazol-Derivate und ihre Verwendung als Schädlingsbekämpfungsmittel |
| DE10104871A1 (de) * | 2001-02-03 | 2002-08-08 | Aventis Cropscience Gmbh | Verfahren zur Kontrolle von Schadorganismen in Nutzpflanzenkulturen |
| DE60215644T2 (de) * | 2001-06-22 | 2007-02-15 | Dow Agrosciences Llc, Indianapolis | 2-(2,6-disubstituierte phenyl)-4-aryl-5-alkyl-1,3-oxazoline derivate zur verwendung als insektizide und acarizide |
| WO2003059884A1 (en) | 2001-12-21 | 2003-07-24 | X-Ceptor Therapeutics, Inc. | Modulators of lxr |
| US7482366B2 (en) | 2001-12-21 | 2009-01-27 | X-Ceptor Therapeutics, Inc. | Modulators of LXR |
| RS52392B (sr) * | 2002-02-14 | 2013-02-28 | Pharmacia Corporation | Supstituisani piridinoni kao modulatori p38 map kinaze |
| US6573286B1 (en) | 2002-06-21 | 2003-06-03 | Dow Agrosciences Llc | 2-(2,6-disubstituted phenyl)-4-aryl-5-alkyl-1,3-oxazoline compounds |
| US20040156742A1 (en) * | 2003-02-11 | 2004-08-12 | Milan Jolanda Bianca | Synergistically-effective cyclohexylethan-1-yl ester mixtures as malodour counteractants as measured physiologically and psychometrically and methods for using same |
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| CA2591413A1 (en) | 2004-12-16 | 2006-06-22 | Vertex Pharmaceuticals Incorporated | Pyrid-2-ones useful as inhibitors of tec family protein kinases for the treatment of inflammatory, proliferative and immunologically-mediated diseases |
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| RU2492170C9 (ru) | 2007-11-14 | 2013-12-27 | Орто-Макнейл-Янссен Фармасьютикалз, Инк. | Имидазо[1,2-а]пиридиновые производные и их применение в качестве положительных аллостерических модуляторов рецепторов mglur2 |
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| JP2024506858A (ja) | 2021-02-02 | 2024-02-15 | リミナル・バイオサイエンシーズ・リミテッド | Ｇｐｒ８４アンタゴニストおよびその使用 |
| US12128035B2 (en) | 2021-03-19 | 2024-10-29 | Novo Nordisk Health Care Ag | Activating pyruvate kinase R |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996022283A1 (en) * | 1995-01-20 | 1996-07-25 | E.I. Du Pont De Nemours And Company | Insecticidal and acaricidal oxazolines and thiazolines |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4977171A (en) | 1988-06-09 | 1990-12-11 | Yashima Chemical Industrial Co., Ltd. | Oxa- or thia-zoline derivative |
| AU634608B2 (en) | 1989-12-09 | 1993-02-25 | Kyoyu Agri Co., Ltd. | 2-substituted phenyl-2-oxazoline or thiazoline derivatives, process for producing the same and insectides and acaricides containing the same |
| EP0646111B1 (en) | 1992-05-26 | 1997-08-20 | E.I. Du Pont De Nemours And Company | Arthropodicidal oxazolines and thiazolines |
| TW259693B (https=) * | 1993-08-04 | 1995-10-11 | Du Pont | |
| DE4401098A1 (de) | 1994-01-17 | 1995-07-20 | Bayer Ag | Diphenyloxazolin-Derivate |
| DE19528778A1 (de) | 1995-08-04 | 1997-02-06 | Bayer Ag | 4-Alkyl-1,3-oxa(thia)zolin-Derivate |
| DE19548419A1 (de) | 1995-12-22 | 1997-06-26 | Bayer Ag | Substituierte Thiazoline |
-
1998
- 1998-06-16 DE DE19826671A patent/DE19826671A1/de not_active Withdrawn
-
1999
- 1999-06-01 DE DE59907464T patent/DE59907464D1/de not_active Expired - Fee Related
- 1999-06-01 HU HU0102360A patent/HUP0102360A3/hu unknown
- 1999-06-01 AT AT99927818T patent/ATE252578T1/de not_active IP Right Cessation
- 1999-06-01 KR KR1020007014344A patent/KR20010052959A/ko not_active Withdrawn
- 1999-06-01 JP JP2000554726A patent/JP2002518389A/ja active Pending
- 1999-06-01 BR BR9911358-9A patent/BR9911358A/pt not_active Application Discontinuation
- 1999-06-01 IL IL14023699A patent/IL140236A/xx not_active IP Right Cessation
- 1999-06-01 ES ES99927818T patent/ES2209451T3/es not_active Expired - Lifetime
- 1999-06-01 WO PCT/EP1999/003776 patent/WO1999065901A1/de not_active Ceased
- 1999-06-01 EP EP99927818A patent/EP1087967B1/de not_active Expired - Lifetime
- 1999-06-01 AU AU45038/99A patent/AU750324B2/en not_active Ceased
- 1999-06-01 PL PL99345041A patent/PL345041A1/xx not_active Application Discontinuation
- 1999-06-01 TR TR2000/03690T patent/TR200003690T2/xx unknown
- 1999-06-01 CA CA002335352A patent/CA2335352A1/en not_active Abandoned
- 1999-06-01 CN CN99807444A patent/CN1305476A/zh active Pending
- 1999-06-01 ID IDW20002618A patent/ID26652A/id unknown
- 1999-06-11 AR ARP990102820A patent/AR018673A1/es active IP Right Grant
- 1999-06-14 US US09/332,225 patent/US6265350B1/en not_active Expired - Fee Related
- 1999-06-16 CO CO99037535A patent/CO5050288A1/es unknown
-
2000
- 2000-12-08 ZA ZA200007301A patent/ZA200007301B/en unknown
-
2001
- 2001-06-21 US US09/886,551 patent/US6670307B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996022283A1 (en) * | 1995-01-20 | 1996-07-25 | E.I. Du Pont De Nemours And Company | Insecticidal and acaricidal oxazolines and thiazolines |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001342102A (ja) * | 2000-06-01 | 2001-12-11 | Nissan Chem Ind Ltd | 安定化される農薬組成物 |
| US9365557B2 (en) | 2008-12-19 | 2016-06-14 | Vertex Pharmaceuticals Incorporated | Substituted pyrazin-2-amines as inhibitors of ATR kinase |
| US9701674B2 (en) | 2008-12-19 | 2017-07-11 | Vertex Pharmaceuticals Incorporated | Substituted pyrazines as ATR kinase inhibitors |
| US10961232B2 (en) | 2008-12-19 | 2021-03-30 | Vertex Pharmaceuticals Incorporated | Substituted pyrazines as ATR kinase inhibitors |
| US10479784B2 (en) | 2008-12-19 | 2019-11-19 | Vertex Pharmaceuticals Incorporated | Substituted pyrazin-2-amines as inhibitors of ATR kinase |
| JP2013526541A (ja) * | 2010-05-12 | 2013-06-24 | バーテックス ファーマシューティカルズ インコーポレイテッド | Ａｔｒキナーゼ阻害剤として有用な化合物 |
| US9334244B2 (en) | 2010-05-12 | 2016-05-10 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| US9630956B2 (en) | 2010-05-12 | 2017-04-25 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase |
| US10208027B2 (en) | 2011-09-30 | 2019-02-19 | Vertex Pharmaceuticals Incorporated | Processes for preparing ATR inhibitors |
| US9862709B2 (en) | 2011-09-30 | 2018-01-09 | Vertex Pharmaceuticals Incorporated | Processes for making compounds useful as inhibitors of ATR kinase |
| US10813929B2 (en) | 2011-09-30 | 2020-10-27 | Vertex Pharmaceuticals Incorporated | Treating cancer with ATR inhibitors |
| US10822331B2 (en) | 2011-09-30 | 2020-11-03 | Vertex Pharmaceuticals Incorporated | Processes for preparing ATR inhibitors |
| US10478430B2 (en) | 2012-04-05 | 2019-11-19 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase and combination therapies thereof |
| US11110086B2 (en) | 2012-04-05 | 2021-09-07 | Vertex Pharmaceuticals Incorporated | Compounds useful as inhibitors of ATR kinase and combination therapies thereof |
| US9791456B2 (en) | 2012-10-04 | 2017-10-17 | Vertex Pharmaceuticals Incorporated | Method for measuring ATR inhibition mediated increases in DNA damage |
| US11464774B2 (en) | 2015-09-30 | 2022-10-11 | Vertex Pharmaceuticals Incorporated | Method for treating cancer using a combination of DNA damaging agents and ATR inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2209451T3 (es) | 2004-06-16 |
| DE59907464D1 (de) | 2003-11-27 |
| US6265350B1 (en) | 2001-07-24 |
| DE19826671A1 (de) | 1999-12-23 |
| IL140236A (en) | 2005-08-31 |
| TR200003690T2 (tr) | 2001-06-21 |
| CA2335352A1 (en) | 1999-12-23 |
| HUP0102360A2 (hu) | 2001-10-28 |
| EP1087967B1 (de) | 2003-10-22 |
| AU4503899A (en) | 2000-01-05 |
| ID26652A (id) | 2001-01-25 |
| EP1087967A1 (de) | 2001-04-04 |
| AR018673A1 (es) | 2001-11-28 |
| BR9911358A (pt) | 2001-03-13 |
| ZA200007301B (en) | 2002-02-08 |
| IL140236A0 (en) | 2002-02-10 |
| AU750324B2 (en) | 2002-07-18 |
| US6670307B2 (en) | 2003-12-30 |
| ATE252578T1 (de) | 2003-11-15 |
| HUP0102360A3 (en) | 2002-03-28 |
| CO5050288A1 (es) | 2001-06-27 |
| CN1305476A (zh) | 2001-07-25 |
| WO1999065901A1 (de) | 1999-12-23 |
| US20020068828A1 (en) | 2002-06-06 |
| PL345041A1 (en) | 2001-11-19 |
| KR20010052959A (ko) | 2001-06-25 |
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