HRP940499A2 - Butric acid derivatives - Google Patents
Butric acid derivatives Download PDFInfo
- Publication number
- HRP940499A2 HRP940499A2 HRP-1571/90A HRP940499A HRP940499A2 HR P940499 A2 HRP940499 A2 HR P940499A2 HR P940499 A HRP940499 A HR P940499A HR P940499 A2 HRP940499 A2 HR P940499A2
- Authority
- HR
- Croatia
- Prior art keywords
- chloro
- acid
- alkyl
- hydrogen
- formula
- Prior art date
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- 239000002253 acid Substances 0.000 title claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 64
- 239000001257 hydrogen Substances 0.000 claims abstract description 64
- IPOKNZMIBAYSRN-UHFFFAOYSA-N 4-chloro-4,4-difluorobutanoic acid Chemical class OC(=O)CCC(F)(F)Cl IPOKNZMIBAYSRN-UHFFFAOYSA-N 0.000 claims abstract description 56
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 27
- 239000001301 oxygen Substances 0.000 claims abstract description 27
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 26
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 26
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 8
- 241000238631 Hexapoda Species 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 109
- -1 nitro, cyano, benzoyl Chemical group 0.000 claims description 100
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 43
- 239000003054 catalyst Substances 0.000 claims description 34
- 239000000460 chlorine Substances 0.000 claims description 30
- 229910052801 chlorine Inorganic materials 0.000 claims description 30
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical class BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 29
- 229910052794 bromium Inorganic materials 0.000 claims description 29
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 28
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 239000011737 fluorine Substances 0.000 claims description 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical group 0.000 claims description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 12
- 125000004494 ethyl ester group Chemical group 0.000 claims description 12
- 125000001495 ethyl group Chemical class [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 11
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000002496 methyl group Chemical class [H]C([H])([H])* 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 241000607479 Yersinia pestis Species 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 8
- 241000238876 Acari Species 0.000 claims description 8
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 238000005809 transesterification reaction Methods 0.000 claims description 7
- SYSGILZVMLQQMP-OWOJBTEDSA-N (e)-4-chloro-4,4-difluorobut-2-enoic acid Chemical class OC(=O)\C=C\C(F)(F)Cl SYSGILZVMLQQMP-OWOJBTEDSA-N 0.000 claims description 6
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 230000006378 damage Effects 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical class FC(F)(F)* 0.000 claims description 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 4
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- IMOJBLQVFVIPEK-UHFFFAOYSA-N benzyl 4-chloro-4,4-difluorobutanoate Chemical compound FC(F)(Cl)CCC(=O)OCC1=CC=CC=C1 IMOJBLQVFVIPEK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 4
- 238000007112 amidation reaction Methods 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 claims description 3
- YUHKVUFACBAHNU-UHFFFAOYSA-N (4-nitrophenyl) 4-chloro-4,4-difluorobutanoate Chemical compound [O-][N+](=O)C1=CC=C(OC(=O)CCC(F)(F)Cl)C=C1 YUHKVUFACBAHNU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 2
- MDUBXQAAANRCKO-UHFFFAOYSA-N 2-(4-phenoxyphenoxy)ethyl 4-chloro-4,4-difluorobutanoate Chemical compound O(C1=CC=CC=C1)C1=CC=C(OCCOC(CCC(F)(F)Cl)=O)C=C1 MDUBXQAAANRCKO-UHFFFAOYSA-N 0.000 claims description 2
- VWJQDAGIPSDMEW-UHFFFAOYSA-N 2-[4-(4-fluorophenoxy)phenoxy]ethyl 4-chloro-4,4-difluorobutanoate Chemical compound FC1=CC=C(OC2=CC=C(OCCOC(CCC(F)(F)Cl)=O)C=C2)C=C1 VWJQDAGIPSDMEW-UHFFFAOYSA-N 0.000 claims description 2
- FQJDQNWABFLPTA-UHFFFAOYSA-N 4-chloro-4,4-difluoro-n-phenylbutanamide Chemical compound FC(F)(Cl)CCC(=O)NC1=CC=CC=C1 FQJDQNWABFLPTA-UHFFFAOYSA-N 0.000 claims description 2
- IBYBUKDBVOBNOQ-UHFFFAOYSA-N 4-chloro-4,4-difluorobutanamide Chemical compound NC(=O)CCC(F)(F)Cl IBYBUKDBVOBNOQ-UHFFFAOYSA-N 0.000 claims description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 2
- KBHFEVAZUMXIDE-UHFFFAOYSA-N [4-(3,5-difluorophenoxy)phenyl] 4-chloro-4,4-difluorobutanoate Chemical compound FC=1C=C(OC2=CC=C(C=C2)OC(CCC(F)(F)Cl)=O)C=C(C1)F KBHFEVAZUMXIDE-UHFFFAOYSA-N 0.000 claims description 2
- KKHFIEVYWDMZAF-UHFFFAOYSA-N [4-(4-fluorophenoxy)phenyl] 4-chloro-4,4-difluorobutanoate Chemical compound FC1=CC=C(OC2=CC=C(C=C2)OC(CCC(F)(F)Cl)=O)C=C1 KKHFIEVYWDMZAF-UHFFFAOYSA-N 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 2
- BWXJMDBMDHJORT-UHFFFAOYSA-N cyclohexyl 4-chloro-4,4-difluorobutanoate Chemical compound FC(F)(Cl)CCC(=O)OC1CCCCC1 BWXJMDBMDHJORT-UHFFFAOYSA-N 0.000 claims description 2
- MXYIKXWCNAUVLB-UHFFFAOYSA-N cyclohexylmethyl 4-chloro-4,4-difluorobutanoate Chemical compound FC(F)(Cl)CCC(=O)OCC1CCCCC1 MXYIKXWCNAUVLB-UHFFFAOYSA-N 0.000 claims description 2
- 125000006331 halo benzoyl group Chemical group 0.000 claims description 2
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical group FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims description 2
- WAWFXGSJMWXCEY-UHFFFAOYSA-N methyl 4-chloro-4,4-difluorobutanoate Chemical compound COC(=O)CCC(F)(F)Cl WAWFXGSJMWXCEY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 claims description 2
- FRJCZGKDRPRLLE-UHFFFAOYSA-N propan-2-yl 4-chloro-4,4-difluorobutanoate Chemical compound CC(C)OC(=O)CCC(F)(F)Cl FRJCZGKDRPRLLE-UHFFFAOYSA-N 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 2
- GCSPSGQVZXMPKU-UHFFFAOYSA-N 2-fluorobutanoic acid Chemical compound CCC(F)C(O)=O GCSPSGQVZXMPKU-UHFFFAOYSA-N 0.000 claims 1
- 150000001804 chlorine Chemical class 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 230000003071 parasitic effect Effects 0.000 claims 1
- 230000003032 phytopathogenic effect Effects 0.000 claims 1
- AWUUSRDYIUYOKV-UHFFFAOYSA-N tert-butyl 4-chloro-4,4-difluorobutanoate Chemical compound CC(C)(C)OC(=O)CCC(F)(F)Cl AWUUSRDYIUYOKV-UHFFFAOYSA-N 0.000 claims 1
- 238000003809 water extraction Methods 0.000 claims 1
- 239000000575 pesticide Substances 0.000 abstract description 2
- 241000239223 Arachnida Species 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 64
- 230000000694 effects Effects 0.000 description 52
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
- 239000000203 mixture Substances 0.000 description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 30
- 239000013543 active substance Substances 0.000 description 29
- 239000002904 solvent Substances 0.000 description 29
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- 235000019441 ethanol Nutrition 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 241000196324 Embryophyta Species 0.000 description 19
- 125000000217 alkyl group Chemical group 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- 235000013601 eggs Nutrition 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 239000000839 emulsion Substances 0.000 description 15
- 239000007921 spray Substances 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000009835 boiling Methods 0.000 description 12
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
- 229960004132 diethyl ether Drugs 0.000 description 12
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- 239000012230 colorless oil Substances 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 10
- 150000002170 ethers Chemical class 0.000 description 10
- 239000004094 surface-active agent Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 241000256244 Heliothis virescens Species 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
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- 150000001408 amides Chemical class 0.000 description 7
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 7
- 229940052303 ethers for general anesthesia Drugs 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
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- 235000019198 oils Nutrition 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
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- 239000012085 test solution Substances 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- 241000238814 Orthoptera Species 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
- ATCJSWLXGFYZPN-UHFFFAOYSA-N ethyl 4-chloro-4,4-difluorobutanoate Chemical compound CCOC(=O)CCC(F)(F)Cl ATCJSWLXGFYZPN-UHFFFAOYSA-N 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 229910000510 noble metal Inorganic materials 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 238000010410 dusting Methods 0.000 description 5
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- 229930195729 fatty acid Natural products 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 150000008282 halocarbons Chemical class 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 230000017448 oviposition Effects 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 4
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 240000001307 Myosotis scorpioides Species 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 241001556089 Nilaparvata lugens Species 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
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- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Polymers CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 229940105847 calamine Drugs 0.000 description 1
- NKWPZUCBCARRDP-UHFFFAOYSA-L calcium bicarbonate Chemical compound [Ca+2].OC([O-])=O.OC([O-])=O NKWPZUCBCARRDP-UHFFFAOYSA-L 0.000 description 1
- 229910000020 calcium bicarbonate Inorganic materials 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical class OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 125000004787 chlorofluoromethoxy group Chemical group ClC(O*)F 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 239000007931 coated granule Substances 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000006841 cyclic skeleton Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- 230000012173 estrus Effects 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- JDLCRXYIKUWXLP-ONEGZZNKSA-N ethyl (e)-4-chloro-4,4-difluorobut-2-enoate Chemical compound CCOC(=O)\C=C\C(F)(F)Cl JDLCRXYIKUWXLP-ONEGZZNKSA-N 0.000 description 1
- CCTVPQCMPJAQLU-UHFFFAOYSA-N ethyl 2,2,4-trichloro-4,4-difluorobutanoate Chemical compound CCOC(=O)C(Cl)(Cl)CC(F)(F)Cl CCTVPQCMPJAQLU-UHFFFAOYSA-N 0.000 description 1
- HYIRMWJEPKDKCR-UHFFFAOYSA-N ethyl 2,2-dichloro-3,3,3-trifluoropropanoate Chemical compound C(C)OC(C(C(F)(F)F)(Cl)Cl)=O HYIRMWJEPKDKCR-UHFFFAOYSA-N 0.000 description 1
- GNIHHXXGPFTJTL-UHFFFAOYSA-N ethyl 2,4-dichloro-4,4-difluoro-2-(trifluoromethyl)butanoate Chemical compound C(C)OC(C(CC(F)(F)Cl)(C(F)(F)F)Cl)=O GNIHHXXGPFTJTL-UHFFFAOYSA-N 0.000 description 1
- ZWEDFBKLJILTMC-UHFFFAOYSA-N ethyl 4,4,4-trifluoro-3-hydroxybutanoate Chemical compound CCOC(=O)CC(O)C(F)(F)F ZWEDFBKLJILTMC-UHFFFAOYSA-N 0.000 description 1
- GTKMGBBVOAFSQY-UHFFFAOYSA-N ethyl 4-chloro-4,4-difluoro-3-hydroxybutanoate Chemical compound CCOC(=O)CC(O)C(F)(F)Cl GTKMGBBVOAFSQY-UHFFFAOYSA-N 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 150000005452 ethyl sulfates Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000005283 haloketone group Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 230000000974 larvacidal effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- VHWYCFISAQVCCP-UHFFFAOYSA-N methoxymethanol Chemical group COCO VHWYCFISAQVCCP-UHFFFAOYSA-N 0.000 description 1
- GLUJPOMOBNXQOD-UHFFFAOYSA-N methyl 2,2,4-trichloro-4,4-difluorobutanoate Chemical compound COC(C(CC(F)(F)Cl)(Cl)Cl)=O GLUJPOMOBNXQOD-UHFFFAOYSA-N 0.000 description 1
- 150000005451 methyl sulfates Chemical class 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 230000001617 migratory effect Effects 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- PPHQUIPUBYPZLD-UHFFFAOYSA-N n-ethyl-n-methylaniline Chemical compound CCN(C)C1=CC=CC=C1 PPHQUIPUBYPZLD-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UYDLBVPAAFVANX-UHFFFAOYSA-N octylphenoxy polyethoxyethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCOCCO)C=C1 UYDLBVPAAFVANX-UHFFFAOYSA-N 0.000 description 1
- 150000002888 oleic acid derivatives Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- NCAIGTHBQTXTLR-UHFFFAOYSA-N phentermine hydrochloride Chemical compound [Cl-].CC(C)([NH3+])CC1=CC=CC=C1 NCAIGTHBQTXTLR-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Chemical class 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical group CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- CPYIZQLXMGRKSW-UHFFFAOYSA-N zinc;iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+3].[Fe+3].[Zn+2] CPYIZQLXMGRKSW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
-
- 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
- A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
-
- 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
- A01N37/12—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, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
-
- 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
-
- 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
- A01N37/20—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 containing the group, wherein Cn means a carbon skeleton not containing a ring; Thio analogues thereof
-
- 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
-
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Description
Predloženi se pronalazak odnosi na nove derivate 4-klor-4,4-difluormaslačne kiseline, na postupak i međuprodukte za njihovu pripravu, na sredstva za uništavanje štetočina koja sadrže te spojeve, kao i na njihovu uporabu u kontroli štetočina.
Derivati 4-klor-4,4-difluormaslačne kiseline prema pronalasku odgovaraju formuli 1
[image]
u kojoj su R1 i R2 neovisno jedan o drugom vodik, C1-C4-alkil ili C1-C4-halogenalkil,
R3 vodik ili organski ostatak i X kisik ili -NR4-,
pri čemu je R4 vodik ili C1-C6-alkil.
Iz literature je poznat red polihalogeniranih klorida maslačne kiseline kao produkata za piretroidne haloketone iz Helv.Chim.Acta 63, str. 1947-1957 (1980).
U definiciji za R3 imenovani organski ostatak označava bilo koji organski ostatak, koji se može vezati u obliku alkohola ili amina na karbonilnu skupinu 4-klor-4,4-difluormaslačne kiseline. Ponajprije je alkoholna ili amino skupina tog organskog ostatka vezana na ugljikov atom. Time je ostatak R3 ponajprije vezan preko ugljikovog atoma na skupinu -CO-X. R3 označava npr. svagda supstituiran ili nesupstituiran C1-C20-alkil, C3-C7-cikloalkil, C3-C20-alkenil, C3-C20-alkinil, benzil ili aril. U okviru predloženog izuma R3 ponajprije označava C1-C20 alkil, C3-C7-cikloalkil, C3-C20-alkenil, C3-C20-alkinil, aril, C3-C20 halogenalkenil, C3- C20-halogenalkinil; C3-C7-cikloalkil supstituiran s halogenom ili C1-C4-alkilom; halogen, C1-C4-alkil, C1-C4-halogenalkil, C1-C12-alkoksi, C1-C4-halogenalkoksi, C1-C4-alldltio, nitro, cijano, benzoil, halogenbenzoil, fenoksi, halogenfenoksi, C1-C4-alkilfenoksi, C1-C4-halogenalkilfenoksi, tri-C1-C4-alkilsilil, N-pirolidinil, N-piperidinil, N-pirolidin-2-onil, N-piperidm-2-onil, C1-C4-alkilamino, di-C1-C4- alkilamino, anilino, N-C1-C4-alkilanilino, N-formilanilino, N-C1-C6-alkilkarbonilanilino, feniltio ili halogenfeniltio supstituiran aril; fenil supstituiran s preko kisika ili sumpora vezanim nesupstituiranim ili supstituiranim aromatskim ili nearomatsldm, mono- ili bicikličkim heterociklom, pri čemu je kako heterociklički tako i fenilni prsten svagda supstituiran s halogenom, C1-C4-alkilom;nitro, C1-C4-halogenalkilom, C1-C4-halogenalkoksi, C1-C4-alkoksi, C1-C4-alkiltio ili cikloprilom; ili C1-C20-alkil supstituiran s hidroksi, halogenom, di-C1-C4-alkilamino, C1-C4-alkoksi, C1-C4 halogenalkoksi, C2-C6-alkoksialkoksi, C1-C4-halogenalkiltio, C1-C4-alkiltio, C1-C4-alkilsulfinilom, C1-C4-alkilsulfoniloksi, C1-C4- alkilkarbonilom, C1-C4-alkoksikarbonilom, C1-C6-alkilkarboni1oksi, C3-C7-cikloalkilom, arilom, ariloksi, ariltio, arilsulfonilom, arilsulfinilom, arilsulfoniloksi, arilkarbonilom ili piridilom, pri čemu arilne i piridilnc skupine mogu svagda biti supstituirane s halogenom, C1-C4-alkilom, C1-C4-halogenalkilom, C1-C4-alkoksi, C1-C4-ha1ogenalkoksi, C1-C4-alkiltio, nitro, cijano, fenoksi, halogenfenoksi, feniltio ili halogenfeniltio.
U definiciji spojeva formule I u- smislu izuma pojedinačni generični pojmovi imaju sljedeće značenje:
Supstituenti koji se pojavljuju kao halogeni atomi su fluor i klor, kao i brom i jod, pri čemu ponajprije fluor, klor i brom. Pod halogenom se pritom podrazumijeva bilo samostalan supstituent ili dio supstituenta kao u halogenciklo, halogenalkil, halogenallđltio, halogenalkoksi, halogenfeniltio ili halogenfenoksi.
Supstituenti koji dolaze u obzir kao alkil-, alkiltio, alkoksialkoksi- i alkoksi ostatci mogu biti ravnolančani ili razgranati. Kao primjeri takvih alkila poznati su metil, etil, propil, izopropil, butil, i-butil, sek-butil, tert-butil ili pentil, heksil, oktil, decil, dodecil i njihovi izomeri. Kao primjere alkoksi ostataka mogu se među ostalim spomenuti: metoksi, etoksi, propoksi, izopropoksi ili butoksi i njihovi izomeri. Alkiltio stoji primjerice za metiltio, etiltio, izopropiltio, propiltio ili izomere butiltio.
Ako su supstituenti koji se pojavljuju kao alkilne, alkoksi, alkenilne, alkinilne ili arilne skupine supstituirani s halogenom, mogu biti djelomice ili sasvim perhalogenirani. Pritom za halogen, alkil i alkoksi vrijede gore navedene definicije. Primjeri za alkilne elemente tih skupina su jedanput do triput supstituiran metil s fluorom, klorom i /ili bromom, kao npr. CHF2 ili CF3; od jednostruko do peterostruko s fluorom, klorom i/ili bromom supstituiran etil, primjerice CH2CF3, CF2CF3, CF2CCl3, CF2CHCl2 CF2CHF2, CF2CHF2, CH2CHBr2, CH2CHClF, CH2CHBrF ili CClFCHClF; jedanput do sedam puta s fluorom, klorom i/ili bromom supstituiran propil ili izopropil, primjerice CH2CHBrCH2Br, CF2CHFCF5, CH2CF2CF3 ili CH(CF3)2; jedanput do devet puta s fluorom, klorom i/ili bromom supstituiran bulil ili neki njegov izomer, primjence CF(CF3)CHFCF3 ili CH2 (CF2)2CF3.
Kada su s R3 definirane alkilne, cikloalkilne ili arilne skupine supstituirane s drugim supstituentima, mogu biti jednostruko ili višestruko supstituirane bilo s jednakim ili s različitim nabrojenim supstituentima. Izuzetno su u supstituiranim skupinama jedan ili dva sljedeća supstituenta.
Supstituenti koji se pojavljuju kao cikloalkilni ostatci označuju npr. ciklopropil, ciklobutil, ciklopentil ili cikloheksil.
Alkenilne i alkinilne skupine imaju jednu ili više, po mogućnosti ne više od tri nezasićene veze ugljik-ugljik. Dvostruke ili trostruke veze su na mjestu vezanja odvojene mostom X s najmanje jednim zasićenim ugljikovim atomom. Tipični zastupnici su alil, metalil, 2-butenil, 3-butenil, propargil, 2-butmil ili 3-butinil.
Aril označava aromatski ugljikovodični ostatak. Ponajprije pod arilom podrazumijevamo fenil ili naftil.
Primjeri za alkoksialkoksi ostatke su metoksimetoksi, metoksietoksi, etoksietoksi, etoksimetoksi, propoksimetoksi, etoksimetoksi, propoksietoksi, metoksipropoksi, butoksimetoksi ili propoksietoksi.
Primjeri za alkoksikarbonilne ostatke su metoksikarbonil, etoksikarbonil, propoksikarbonil, izopropoksikarbonil ili butoksikarbonil. Alkilkarbonil označava npr. acetil, propionil, butini ili valeril, kao i njihove izomere. Alkilkarboniloksi označava npr. acetoksi, propioniloksi ili butiriloksi.
Primjeri za aromatske i nearomatske, mono ili bicikličke heterocikle koji su na fenilne jezgre definirane s R3, vezani preko kisikovog ili sumpornog atoma, sljedeći su temeljni ciklički kosturi: piridin, pirazin, piridazin, pirimidin, piridolin, tiazol, tiadiazol, oksazol, benzotiazol, triazin, oksadiazol, kinolin, kmoksalin, kinazolin, izokinolin, ftalazin, naftiridin, cinolin, pteridin, triazol, piperidin ili benzoksazol. Ti su heterocikli ponajprije vezani preko kisikovog ili sumpornog mosta na položaju 4 fenilnog prstena. Kisikov ili sumporni most sam nosi ugljikov atom heterocikličkog heterocikla. Kako fenilna jezgra, tako i heterociklička, može nositi još supstituenata, primjerice do tri ostatka iz skupine halógena, alíala, halogenalkila i alkoksi, ili svagda jednog ili dva supstituenta iz skupine nitro, halogenalkoksi, alkiltio i cikloalkila. Ukupan broj supstituenata na fenilnom prstenu i heterociklu u pravilu nije veći od četiri.Uglavnom te skupine nose najviše tri daljnja supstituenta iz skupine klora, broma, metila, etila i trifluormetila, a povezani su preko kisikovog atoma.
Među tim spojevima vrijedni su spomena prije svega takvi u kojima R3 označava na položaju 4 preko kisika vezane aromatske mono ili bicikličke heterocikle iz skupine piridina, pirimidina ili benzotiazola supstituirane na fenil, pri čemu su oba aromatska prstena nesupstituiraiia ili zajedno nose najviše tri daljnja supstituenta iz skupine klora, broma, metila, etila i trifluormetila.
Prije svega, od pojedinačnog su značenja sljedeći po definiciji za R3. s heterociklom preko kisika ili sumpora supstituirani fenilni ostatci:
-4-(3-metiltiadiazol-5-iloksi)-fenil,
-4-(4-bromtiazol-2-iloksi)-fenil,
-4-(5-trifluormetilpirid-2-iloksi)-fenil,
-4-(3,5-diklorpirid-2-iloksi)-fenil,
-4-(3-klor-5-trifluormetilpirid-2-üoksi)-fenil,
-3-(5-trifluormetilpirid-2-iloksi)-fenil,
2,6-dimetil-4-(4-trifluormetilfenoksi)-fenil,
2,6-diizopropil-4-(N-formilanilino)-fenil,
2,6-diizopropil-4-(N-metilanilino)-fenil,
-4-(feniltio)-fenil,
-4-(2-ciklopropil-4-trifluometü-pirimidin-6-iloksi)-fenil,
-4-(2-terc.butil-4-trifluonnetü-pirimidin-6-iloksi)-fenil,
-4-(2-metiltio-4-metil-pirimidin-6-iloksi)-fenil,
-4-(2-metü-4-trifluormetü-pirimidin-6-iloksi)-fenil,
-4-(6-trifluormetoksi-benzotiazol-2-iloksi)-fenil,
-4-(6-klorbenzotiazol-2-iloksi)-fenil,
-4-(6-nitrobenzotiazol-2-iloksi)-fenil,
-4-(6-metoksibenzotiazol-2-iloksi)-fenil,
-4-(5-trifluorometil-benzotiazol-2-iloksi)-fenil,
-3,5-diklor-4-(3-klor-5-trifluorometilpirid-2-iloksi)-fenil,
-2,6-dimetil-4-(3-klor-5-trifluorometilpirid-2-iloksi)-fenil,
-4-klor-3-(3,5-bis-trifluorometilpirid-2-iloksi)-fenil,
-4-klor-3-(5-klor-3-fluorpirid-2-iloksi)-fenil,
2,6-dimetil-4-[3-klor-5-(2,2-diklor-14,2trifluoretil)-pirid-2-iloksi]-fenil,
-4-[3-kIor-5-(2,2-diklor-l,l,2-trifluoretil)-pirid-2-floksi]-fenil,
-4-(N-acetil-pirid-3-ilamino)-fenil,
-2,4-diklor-3-(3-klor-5-trifluonnetilpirid-2-iloksi)-fenil,
-4-etoksikarbonil-3-(3-klor-5-trifluormetilpirid-2-iloksi)-fenil,
-3-metil-4-(3-klor-5-trifluormetilpirid-2-iloksi)-fenil,
-3,5-diklor-4-(5-trifluormetilpirid-2-iloksi)-fenil,
-4-(6-klor-4-trifluormetilpirid-2-iloksi)-fenil,
-4-brom-3-(3-klor-5-trifluormetilpirid-2-iloksi)-fenil,
-3-(5-trifluormetilpirid-2-iloksi)-fenil,
-2,6-dimetil-4-(3,5-diklorpirid-2-iltio)-fenil,
-2,6-dimetil-4-(2-klorpiridazin-6-floksi)-fenil,
-2,6-dimetil-4-(pirimidin-2-iloksi)-fenil,
-2,6-dimetil-4-(pirazin-2-iloksi)-fenil,
-2,6-dimetil-4-(6-klor-kinoksalin-2-iloksi)-fenil,
-2,6-dimetil-4-(6-trifluormetfl-ldnoksalin-2-floksi)-fenil,
-2,6-dimetil-4-(kinolin-2-iloksi)-fenil,
-4-klor-2-fluor-5-(3-metil-1,2,4-tiadiazol-5-iloksi)-fenil,
-2,6-dimetil-4-(4-brom-tiazol-2-iloksi)fenil ali
-4-metil-3-(3-klor-5-trifluorometilpirid-2-iloksi)-fenil.
Među spojevima formule I prije svega su takve podskupine, u kojima
a) R1 i R2 neovisno jedan 0 drugom znače vodik ili C1-C4-alkil, ili
b) X označava kisik, -NH-, -NCH3- ili NC2H5-, ili
c) R3 označava vodik, C1-C20-alkil, C3-C7-cikloa.lkil, C3-C20-alkenil, C3-C20-alkinil, fenil, naftil, C3-C20-halogenalkenil, C3-C20-halogenalkinil; fluorom, klorom, bromom ili C1-C3-alki1om supstituiran C3-C7-eikloalkil; lluorom, klorom, bromom ili C1-C3-alkilom, C1-C3-halogenalkilom, C1-C3-alkoksi, C1-C3-halogenalkoksi, C1-C3-alkiltio, nitro, cijano, fenoksi, halogenfenoksi, C1-C4-alkilfenoksi, C1-C4-halogenalkiifenoksi, tri-C1-C4-alkilsil, N-pirolidinil, N-piperidinilom, N-pirolidin-2-onilom, N-piperidin-2-onilom, C1-C4-alkilamino, di-C1-C4-alikilamino, anilino, N-C1-C4-alkilanilmo, N-formilanilino, N-C1-C6-alikilkarbonilanilino, feniltio ili halogenfeniltio supstituiran fenil ili naftil ili s hidroksi, fluoro, kloro, bromo, di-C1-C4-alkilamino, C1-C4-alkoksi, C1-C4-halogenalkoksi, C2-C6-alkoksialkoksi, C1 -C4-halogenalkiltio, C1-C4-alkiltio, C1-C4-alkilsulfinilnom, C1-C4-alkilsulfonilom, C1-C4-alkilsuifoniloksi, C1-C4-alkilkarboni1om, C1-C4-alkoksikarbonilom, C1-C6 alkilkarboniloksi, C3-C7-cikloalkilom, fenilom, fenoksi, feniltio, fenilsulfoniloksi ili piridilom supstituiran C1-C20-alkil, pri čemu se fenilne i piridilne skupine uvijek mogu supstituirati s fluorom, klorom, bromom, C1-C3-alkilom, C1-C3-halogenalkilom, C1-C3-alkoksi, C1-C3-halogenalkoksi, C1-C3-alkiltio, nitro, cijano, fenoksi, halogenfenoksi, feniltio ili halogenfeniltio, ili
d) R3 označava fenil supstituiran u položaju 4 preko kisika vezanim aromatskim mono ili bicikličkim heterociklom iz vrste piridina, pirimidina ili benzotiazola, pri čemu su oba aromatska prstena nesupstituirana ili zajedno imaju najviše tri daljnja supstituenta iz skupine klora, broma, metila etila i trifluormetila.
Među spojevima podskupine a) ponajprije su oni u kojima R1, i R2 označavaju vodik.
U spojeva podskupine b) ponajprije su oni u kojih X označava kisik ili -NH-.
Posebno izuzetna skupina djelotvornih tvari formule I važna je po tome da R1 i R2 neovisno jedan o drugom označavaju vodik ili C1-C4-alkil., X kisik ili NR4 i R4 vodik, metil ili etil. Kada R1 i R2 označavaju vodik, karakterizirani su osobito važni spojevi formule I.
Iz podskupine spojeva c) formule I sjedne su strane u prednosti oni u kojih R3 označava fenil, benzil, naftil, 3-piridilmetil ili svagda s fluorom, klorom, bromom, C1-C3-alkilom, C1-C3-halogenalkilom, C1-C3-alkoksi, C1-C3-halogenal kok si, C1-C3-alkiltio, nitro, cijano, fenoksi, halogenfenoksi, feniltio ili halogenfeniltio supstituiran fenil, benzil, naftil ili 3-piridilnietil. Od tih su spojeva opet u prednosti oni, gdje R1 i R2 neovisno jedan o drugom označavaju vodik ili C1-C4-alkil, X kisik ili -NR4 i R4 vodile, metil ili etil.
S druge su strane u podskupini c) spojeva formule I u prednosti oni u kojima R3 označava C1-C12-alkil, ili s hidroksi, fluorom, klorom, bromom, dimetilamino, metoksi, etoksi, metoksietoksi, etoksietoksi, metiltio, etiltio, ciklopropilom, ciklopentilom, cikloheksilom, fenilom ili fenoksi supstituiran C1-C12-alkil, pri čemu fenilni ili fenoksi ostatak mogu biti supstituirani s fluorom, klorom, bromom, fenoksi, halogenfenoksi ili feniltio. Od te skupine spojeva u prednosti su oni u kojih R1 i R2 neovisno jedan o drugom označavaju vodik ili C1-C4-alki1, X kisik ili -NR4 i R4 vodik ili C1-C4alkil. Posebne oznake R1 i R2 u izvedbenim oblicima koji su u prednosti označavaju svagda vodik.
Vrlo zanimljiva skupina spojeva iz podskupine c) formule I ističe se po tome da R3 označava C3-C12-alkenil, C3-C12-alkinil, ili svagda fluorom, klorom ili bromom supstituiran C3-C12 alkenil ili C3-C12-alkinil. Iz te skupine spojeva istaknuti su oni u kojih R1, i R2 neovisno jedan o drugom označavaju vodik ili C1-C4-alkil, X kisik ili -NR4 i R4 vodik ili C1-C4-alkil. Osobito je u prednosti oznaka R1 i R2 za vodik.
U prednosti su sljedeći pojedinačni spojevi formule I:
metilester 4-klor-4,4-dirluoromaslačne kiseline,
etilester 4-klor-4,4-difluormaslačne kiseline,
izopropilester 4-klor-4,4-diiluoromaslačnc kiseline,
tert-butilester 4-klor-4,4-difluoromaslačne kiseline,
n-butilester 4-klor-4,4-difluoromaslačne kiseline.
(2,2-dirnetilpropil)-ester 4-klor-4,4- difluoromaslačne kiseline,
benzilester 4-klor-4,4-difIuoromaslačne kiseline,
fenilesler 4-klor-4,4-difluoromaslačne kiseline,
[2-(4-fenoksifenoksi)-etil]ester 4-klor-4,4-difluoro maslačne kiseline, cikloheksilester 4klor-4,4-difluoromaslačne kiseline, cikloheksilmetilester 4-klor-4,4 difluoromaslačne kiseline, ciklopropilmetilester 4-klor-4,4 difluoromaslačne kiseline, etilester 4-klor-4,4-difluorometilmaslačne kiseline,
N-metilamid 4-klor-4,4-difluormaslačne kiseline,
N,N-dimetilamid 4-klor-4,4- difluoromaslačne kiseline,
N,N-diheksilamid 4-klor-4,4-difluoromaslačne kiseline,
N-etilamid 4klor-4,4-difluoromaslačne kiseline,
N-izopropilamid 4-klor-4,4-difluormaslačne kiseline,
N-butilamid 4-klor-4,4-difluoromaslačne kiseline,
N-tert-butilamid 4-klor-4,4difIuoromaslačne kiseline,
N-benzilamid 4-klor-4,4difluormaslačne kiseline,
anilid 4-klor-4,4ditluoromaslačne kiseline,
N-metil-N-pirid-3ilmetilamid 4-klor-4.4-ditluoromaslačne kiseline,
N-pirid-3-ilmetilamid 4-klor-4,4-difluoromaslačne kiseline,
(4-klor-anilid) 4-klor-4,4-difluoromaslačne kiseline,
(4-fenoksi-anilid) 4-klor-4,4-difluoromaslačne kiseline,
(4-klor-anilid) 4-klor-4,4-difluoromaslačne kiseline,
(4-metoksi-anilid) 4-klor-4,4-dilluoromaslačnc kiseline,
(4-metil-anilid) 4-klor-4,4-difluormaslačne kiseline,
(3-metilmerkaplo-anilid) 4-klor-4,4difluoromaslačne kiseline,
(4-f1uor-anilid) 4-klor-4,4-dilluoromaslačne kiseline,
(4-klor-2-nitro-anilid) 4-klor-4,4-dirluoromaslačne kiseline,
(3-fenoksi-benzil)-ester 4-klor-4,4-difluoromaslačne kiseline,
[4-(4-fluor-fenoksi)-fenil]-ester 4-klor-4,4-difluoro maslačne kiseline,
[4-(4-fluor-fenoksi)-fenoksi-etil]-ester 4-klor-4,4-difluormaslačne kiseline,
(4-nitro-fenil)-ester 4-klor-4,4-difluoromaslačne kiseline,
[4-(3,5-difluor-fenoksi)-fenil]-ester 4-klor-4,4-difluoromaslaene kiseline,
[4-(5-trifluonTietil-pirid-2-iloksi)-fenil]ester 4-klor-4,4difluoro maslačne kiseline,
4-klor-4,4-difluoromaslačne kiseline
i amid 4-klor-4,4-difluoromaslačne kiseline.
Spojeve formule I u smislu pronalaska može se pripraviti po analogiji s poznatim postupcima.
Spojeve formule I dobijemo primjerice tako, da
a) halogenid 4-klor-4,4-difluoromaslačne kiseline formule II
[image]
koji ima R1 i R2 značenja navedenog pri formuli I i Hal koji označava halogen, ponajprije klor ili brom, pretvorimo u prisutnosti baze, reakcijom sa spojem formule III
[image]
koji imaju X i R3 značenja navedenog pri formuli I, ili
b) 4-klor-4,4-dilflouoromaslačnu kiselinu formule Ic
[image]
koji imaju R1 i R2 značenja navedenog pri formuli I, pretvorimo u nazočnosti sredstva koje izvlači vodu, reakcijom sa spojem formule III.
Pretvorba u postupku a) (II + III = I) teče ponajprije u inertnom otapalu bez hisdroksilnih skupina u nazočnosti organske baze, primjerice piridina, 4-dimetilaminopiridina, lutidina, kolidira, trialkilamina, N,N-dialkilamlina ili biciklične nenukleofilne baze kao l,4-diazabiciklo[2.2.2]-oktana (DABCO), l,5-diazabiciklo[4.3.0]non-5-ena (DBN) ili 1,8-diazabiciklo[5.4.0]undec-7-ena.(l,5-5) (DBU). Reakciju izvodimo općenito pri temperaturama od -30 do +, uglavnom od -10 do +. Mom radimo smišljeno u nazočnosti otapala ili smjese otapala koja su inertna za reakciju. U tu su svrhu prikladni primjerice alifatski i aromatski ugljikovodici kao benzen, toluen, ksilen, petroleter, heksan; halogenirani ugljikovodici kao klorbenzen, metilenklorid, etilenklonđ, kloroform, telraklorugljik, tetrakloroetilen; eter i eterski spojevi kao dialkiletcr (dietileter, diizopropileter, tert-butilmetileter, itd.), anisol, dioksan, tetrahidrofuran; nitrili kao acetonitril, propionitril; esleri kao etilacetat (etilester octene kiseline), propilacetat ili butilacetat; ketoni kao aceton, dietilketon, metiletilketon; spojevi kao dimetilsulfoksid (DMSO), dimetilformamid (DMF), i smjese takvih otapala. Reakcija se može provoditi i u suvišku gore navedenih baza, a kada je spoj formule III amin (X = NR4) može se umjesto baze upotrijebiti i drugi ekvivalent ili pak veći suvišak spoja formule III.
U načinu postupka b) (Ic +III = I) reakciju valjano izvodimo u nazočnosti uobičajenog reagensa za esterifikaciju koji izvlači vodu, primjerice u nazočnosti karbodiimida |dicikloheksilkarbodiimida (DCC)] ili 1-alkil-2-halogen piridinijeve soli kao 1-metil-2-halogen piridinijeve soli, npr. 1-metil-2-klorpiridinijevog jodida. Radimo smišljeno u nazočnosti otapala koje je inertno u reakciji, ili smjesi otapala, pri temperaturama od -30 do +, uglavnom -10 do +. Radimo uglavnom u prisutnosti baze, primjerice u prisutnosti organskog arama kao trialkilamina (trimetilamina, trietilamina, tripropilamina ili diizopropi1eti1amina), piridina (piridina samog, 4-dimetilaminopiridina ili 4-pirolidinopiridina), morfolina (N-metilmorfolina) ili N,N-dialldlanilina (N,N-dimetilanilina ili N-metil-N-etilanilina). Kao otapala prikladni su primjerice alifatski i aromatski ugljikovodici, kao benzen, toluen, ksilen, petroleter, heksan; halogenirani ugljikovodici kao klorbenzen, metilenklorid, etilenklorid, kloroform, tetraklorugljik, tetrakloretilen; eter i eterski spojevi kao dialkileter (dietileter, diizopropileter, tert-butilmetileter), anisol, dioksan, tetrahidroftiran; nitrili kao acetonitril, propionitril; esteri kao etilacetat (etilester octene kiselline), propilacetat ili butilacetat; i međusobne smjese takvih otapala.
Predstavlja li spoj formule III alkohol (X = O) može se varijanta, postupka b) izvesti i u nazočnosti kiselinskog katalizatora kao npr. H2SO4, HCl ili sulfonske kiseline, kao metansulfonske kiseline ili p-toluensulfonske kiseline. Pritom uspješno radimo uz suvišak alkohola formule III. U tom postupku možemo oslobođenu vodu kontinuirano uklanjati iz reakcijske smjese. Uobičajena metoda pritom za uklanjanje vode iz reakcijskog produkta je destilacija azeotropa s vodom. Stoga su prikladna otapala kao benzen, toluen, ksilcn, metilenklorid ili kloroform. U osnovi je različite derivate formule I moguće dobiti i preesterifikacijom ili amidiranjem iz lako dostupnog nižeg alkilnog estera 4-klor-4,4-diiluormaslačne kiseline.
Derivate esterskog tipa formule I (X = O) moguće je dobiti baznom ili kiselinskom kataliziranom preesterifikacijom nižih alkilnih estera formule la
[image]
s alkoholima formule lila
[image]
gdje R3 ima, uz izuzetak C1-C4-alkila, značenje navedeno pri formuli I. Kao kiselinski katalizatori posebno su prikladni HCl, H2SQ4 ili sulfonska kiselina. U bazno kataliziranoj preesterifikaciji upotrebljavamo ponajprije kao baze natrijeve ili kalijeve alkoholate alkohola formule lila, koje je moguće dobiti iz lila npr. dodatkom natrijevog ili kalijevog hidrida. Reakciju preesterifikacije ponajprije izvodimo pri temperaturama od -20 do +, a osobito od 0 do . Alkoholnu komponentu lila upotrebljavamo uspješno u suvišku. Kao otapala dolaze u obzir eteri, kao dietileter, diizopropileter, dioksan ili tetrahidrofuran, halogcnirani ugljikovodici ili alifatski ili aromatski ugljikovodici.
Derivati amidnog tipa formule I (X = NR4) mogu se dobiti iz nižih alkilnih estera formule I a reakcijom s amidom formule Illb
[image]
koji imaju R3 i R4 značenja navedenog pri formuli I. Reakciju am i diranja izvodimo pri temperaturama između 0 i +. Reaktanti uspješno reagiraju u inertnom otapalu ili smjesi otapala. Pritom su prikladni primjerice osobito alifatski i aromatski ugljikovodici kao benzen, toluen, ksilen, petroleter, heksan; halogenirani ugljikovodici kao klorbenzen, metilenklorid, etilenklorid, kloroform, tetraklorugljik, tetrakloretilen; eteri i eterski spojevi kao dialkileter (dietileter, diizopropileter, tertbutilmetileter itd.), anisol, dioksan, tetrahidrofuran; nitrili kao acetonitril, propionitril; alkoholi kao metanol, etanol, propanol, izopropanol; ili voda. Aminsku komponentu Illb uspješno upotrebljavamo u suvišku.
Spojevi formule III poznati su i mogu se lako nabaviti na tržištu ili se mogu pripraviti prema analognim postupcima priprave.
Kiselinske halogenide formule II možemo upotrijebiti na uobičajen način u reakciji sa sredstvom za halogeniranje iz 4-kloro-4,4-difluormaslačne kiseline formule Ic. Kao sredstvo za halogeniranje osobito su prikladni SOCl2-, oksalilklorid, PCl3 POCl3 ili PCl5. Pritom se općenito radi pri temperaturama između -20 i +, uglavnom između 0 i +. Reakcija može teći bez otapala ili u smjesi s otapalom koje je inertno u reakciji. Kao otapala su pritom prikladni npr. aromatski ugljikovodici kao benzen ili toluen, ili halogenirani ugljikovodici kao metilenklorid, kloroform ili klorbenzen. Reakciju često izvodimo uz dodatak katalitičkih količina DMF.
Međuprodukti formule II su novi. Bili su razvijeni posebice za sinteze djelotvornih tvari formule I. Time tvore predmet predloženog pronalaska.
4-klor-4,4-difluoromaslačna kiselina formule Ic može se dobiti iz spojeva Ia kiselom ili bazičnom hidrolizom. Reakciju općenito izvodimo pri temperaturama između -20 i +, poglavito između +10 i +. U kiseloj hidrolizi upotrebljavamo ponajprije HCl ili H2SO4, a u bazičnoj hidrolizi NaOH ili KOH Pritom oprezno radimo u vodi ili smjesi vode i organskog otapala. Kao organska otapala osobito su prikladni alkoholi kao metanol ili etanol; eteri kao dioksan ili tetrahidrofuran; dimetilsulfoksid; ili dimctilformamid.
Spojevi formule I a koji predstavljaju podskupinu spojeva formule I i istodobno služe kao međuprodukti za pripravu različitih eterskih i amidnih tipova formule I mogu se dobiti prema sljedećim postupcima:
Spojeve formule Ia možemo dobiti pretvorbom estera a-halogen-4-klor-4,4-difluomaslačne kiseline formule IV
[image]
koja ima R1 i R2 značenja navedenog pri formuli I,aY označava klor ili brom, katalitičkim dehalogeniranjem s vodikom u položaju α.
Spojeve navedene podformulom lb
[image]
koji imaju R1 značenja navedenog pri formuli I, možemo pripraviti katalitičkim α-dehalogeniranjem s vodikom iz α,α-dihalogen-4klor-4,4-difluormaslačne kiseline formule V
[image]
gdje R1 ima značenje navedeno pri formuli I, a X i Z neovisno jedan o drugom označavaju klor ili brom.
Pri prikladnom odabiru katalizatora i reakcijskih uvjeta također je moguće α-halogene atome Y i Z zamijeniti vodikom. Tako možemo mono-α-dehalogeniranjem pripraviti spojeve formule IV, gdje R2 označava, vodik iz spojeva formule V.
Postupci katalitičkog dehalogeniranja protječu pomoću vodika (IV —> I a, V —> lb i V —> IV) s vodikom u prisutnosti katalizatora od plemenitih metala ili Ranayevog nikla u danom primjeru u prisutnosti hvatača halogenovodika i otapala pri temperaturama od 0 do i pri normalnom tlaku ili tlaku do 150 bara. Otapala su ponajprije odabrana iz skupine ugljikovodika, halogenugljikovodika, etera, ketona, alkohola, estera kaboksilnih kiselina, sulfona, amida, N,N-dialkilkarboksilne kiseline, N-alkillaktama i laktona. Kao primjeri za to su petroleter, pentan, heksan, cikloheksan, metilcikloheksan, benzen, toluen, ksilen, klorbenzen, metilenklorid, kloroform, 1,2-dikloroetan, 1,1,2,2-tetrakloroetan, dietileter, dibutileter, etilenglikoldimetileter, tetrahidrofuran,dioksan, aceton, metilizobutilketon, etil ili metilester octene kiseline,tetrametilsulfon, dimetilformamid, N-metilpirolidon, γ-valerotakton, butirolakton, metanol, etanol ili izopropanol. U prednosti je otapalo polarne prirode. Posebice prikladna otapala su etilester octene kiseline, tetrahidrofuran ili alkohol. Količinu otapala moguće je odabrati u širokim granicama. Oprezno se može upotrijebiti ista ili deseterostruka količina otapala u odnosu na količinu spoja IV ili V. Hvatači halogenovodika su općenito poznati. Pritom vrijedi za tercijarne baze dušika ponajprije ukupno 3 do 20, osobito 3 do 12 ugljikovih atoma, za alkalijske ili zemnoalkalijske soli organskih kiselina ili karboksilne kiseline, ili za okside ili hidrokside alkalijskih ili zemnoalkalijskih metala. Neki primjeri su natrijev karbonat, natrijev ili kalcijev hidrokarbonat, natrijev acetat, NaOH, KOH, MgO i CaO; ili aromatske, alifatske ili cikličke tercijarne dušikove baze, kao trimetil-, trietil-, tripropil-, tributil-, trietanol- ili butildimetilamin, piridin, 2,6-dimetilpiridin, N-metilpirolin i N-metilmorfolin. U prednost kao hvatači halogenovodika su tercijarne dušikove baze i MgO. Osobito prikladan je 2,6-dimetilpiridin. Hvataće ugljikovodika možemo dodati u neznatnom manjku ili u suvišku glede količine spojeva formule IV ili V. Najbolje je upotrijebiti ekvimolarne količine. Primjeri plemenitih metala kao katalizatora su iridij, rodij, platina, rutenij i paladij. Osobitu prednost pri upotrebi ima paladij. Plemeniti metali imaju prednost kao katalizatori na nosaču. Primjeri za nosače su BaSO4,SiO2, Al2O3 i osobito aktivni ugljen.Upotrijebljeni katalizator sadrži osim nosača općenito 0.1 do 20 mas. % plemenitog metala. Možemo upotrijebiti i katalizatore koji sadrže sumpor. Dodana količina može iznositi 0.1 do 20 /mas. % glede količine spoja formule IV ili V. Oprezno možemo dodati u reakciju regeneriran ili neupotrijebljen katalizator. Reakcijska temperatura iznosi uglavnom između 0 i +, a osobito 0 do +. U prednosti je tlak do 20 bara. Uglavnom se izvodi reakcija pri normalnom tlaku.
Spojevi formule V poznati su iz EP-A-2206, ili ih možemo dobiti prema analognim tamo opisanim postupcima. Međuprodukti formule IV mogu se pripraviti pretvorbom estera kloroctene kiseline formule VI
[image]
gdje R2 ima značenje navedeno pri formuli I, a Y označava klor ili brom, u prisutnosti Cu-(I) katalizatora 1,1-difluoroetilena formule VII
[image]
Taj je postupak opisan za Y = klor u Helv. Chim. Acta 63, str. 1947-1957 (1980).
Dodani katalizatori sadrže kao bitan element bakar u oksidacijskom stupnju 1. Primjeri za to su bakrov(I) klorid i bromid (CuCl, CuBr), bakrov cijanid (CuCN). U prednosti su CuCl i CuBr kao i njihove smjese. Katalizatore uporabljujemo općenito u količinama od oko 0.01 do 10 mol % u odnosu na spoj formule VII. Pretvorbu izvodimo u organskom otapalu. Prikladna organska otapala su takva u kojima su katalizatori dobro topljivi ili mogu s katalizatorima tvoriti komplekse koji su inertni u odnosu na spojeve formula VI i VII. Primjeri takvih otapala su alkilnitril, osobito oni s 2 do 5 ugljikovih atoma, kao acetonitril, propionitril i butironitril; 3-alkoksipropionitril s 1 do 2 ugljikova atoma u alkoksilnom dijelu, kao 3-metoksipropionitril 3-etoksipropionitril; aromatski nitrili, prije svega benzonitril; alifatski ketoni s ukupno 3 do 8 ugljikovih atoma, kao aceton, dietilketon, metil-izopropilketon, -di-izopropilketon, metil-tert-butilketon; alkilni i alkoksi ester alifatskih monokarboksilnih kiselina s ukupno 2 do 6 ugljikovih atoma, kao metilni i etilni ester mravlje kiseline, metilni i etilni, n-butilni i izobutilni ester octene kiseline, kao l-acetoksi-2-metoksietan;ciklički eter, kao tetrahidrofuran, tetrahidropiran i dioksan; dialkileter s 1 do 4 ugljikova atoma u alki Inom dijelu, kao dietileter, di-n-propileter i di-izopropileter; N,N-dialkilamidi alifatskih monokarboksilnih kiselina s 1 do 3 ugljikova atoma u kiselinskom dijelu, kao N,N-dimetilformamid, N,N- dimetilacetamid, N,N-dietilacetamid i N,N-dimetilmetoksi acetamid; etilenglikol i dietilenglikoldietileter s 1 do 4 ugljikova atoma u alkilnom dijelu, kac etilenglikodimetil, dietil i di-n-butileter, dietilenglikoldietil i di-n-buli1eter ili triamid heksametilfosforne kiseline. Otapala koja su u prednosti su alkilnitril s 2 do 6 ugljikova atoma i 3-a.lkoksipropionitnli s I do 2 ugljikova atoma u alkoksilnom dijelu, osobito aeetonitril i 3-metoksipropionitril. R tlakom ili bez tlaka. Spojevi uže formule Id
[image]
gdje R1, R2 i X imaju značenje navedeno pri formuli I a R označava vodik ili C1-C6-alkil, mogu se pripraviti katalitičkim hidrogeniranjem vodikom iz 4-klor-4,4-difIuorkrotonske kiseline formule VIII
[image]
gdje R1, R2 i X imaju značenje navedeno pri formuli I, a R označava vodik ili C1-C6-alkiI.
Tako dobiveni produkti užih podformula. Ia, lb, Ic i Id mogu se prevesti u derivate opisane formulom I uobičajenim reakcijama derivatiziranja, kao hidrolizom, preesterifikacijom ili preamidiranjem.
Katalitičko hidrogeniranje krotonske kiseline formule VIII može se izvesti pri uvjetima uobičajenim za taj reakcijski tip. Tako reakciju izvodimo u prisutnosti katalizatora od plemenitog metala ili Raneyevog nikla, po mogućnosti u inertnom otapalu, u vodikovoj atmosferi pri tlaku od 1 do 150 bara.
Primjeri katalizatora od plemenitih metala su npr. iridij, rodij, platina, rutenij i paladij. Osobito prikladna je upotreba paladij a. Plemeniti metali se uglavnom nanose kao katalizator na nosaču. Primjeri nosača su BaSO4, SiO2, Al2O3 i osobito aktivni ugljen. Upotrijebljeni katalizator sadrži osim nosača općenito 0.1 do 20 mas. % plemenitog metala. Možemo ga upotrijebiti i kao sulfidirane katalizatore. Upotrijebljena količina iznosi od 0.1 do 20 mas. % glede količine spoja formule VIII. Oprezno u reakciju dodamo regeneriran ili neupotrijebljen katalizator. Reakcijska temperatura iznosi uglavno 0 do +, najbolje 0 do +. Tlak iznosi najpogodnije do 20 bara. Najbolje je izvoditi reakciju pri normalnom tlaku. Prednost imaju otapala iz skupine ugljikovodika, halogenugljikovodika, etera, ketona, estera karboksilne kiseline, sulfona, amida N,N-dialkilkarboksilne kiseline, N-alkilaktama i laktona. Pojedinačni primjeri su petroleter, pentan, heksan, cikloheksan, metilciklobeksan, benzen, toluen, ksilen, klorbenzen, metilenklorid, kloroform, 1,2-dikloretan, 1,1,2,2-tetrakloretan, dietileter, dibutileter, etilenglikoldimetileter, tetrahidrofuran, dioksan, aceton, metilizobutilketon, etil ili metilester octene kiseline, tetrametilensulfon, dimetilformamid, N-metilpirolidon, γ-valerolakton, butirolakton, metanol. U prednosti su otapala polarne prirode. Osobito prikladna otapala su etilester octene kiseline i tetrahidrofuran. Količina otapala može se odabrati u širokim granicama. Korisno je upotrijebiti jednaku količinu do deseterostruki suvišak otapala glede količine spoja formule VIII.
Spojevi formule VIII novi su, uz izuzetak 4-k1or-4,4-difluorokrotonske kiseline. Ti su spojevi bili razvijeni posebice za sintezu spojeva formule I kao međuprodukti. Time postaju dijelom predloženog pronalaska. Nove spojeve formule VIII možemo pripraviti analogno opisanom postupku priprave jednostavne kiseline (Izvestiya Akademii nauk SSSR, Ser. Khim. 2 (1965) 300-307) ili se mogu pripraviti iz tih produkata uobičajenim reakcijama derivatiziranja, kao esterifikacijom, preesterifikacijom ili amidiranjem.
Spojevi formule VIII u kojima R1 i R2 označavaju vodik mogu se dobiti iz spojeva formule IX
[image]
gdje A označava vodik ili acilnu skupinu, ß-eliminacijom prema poznatim metodama, npr. Houben Weyl 6/1 b 939 (1984).
Spojeve formule IX možemo pripraviti iz spojeva formule X
[image]
redukcijom, primjerice katalitičkom s vodikom prema Reuben G. Jones u J.Amer.Chem.Soc. 70 (1984) 144, po tamo opisanim metodama.
Spojevi formule X djelomice su poznati ili ih je moguće pripraviti prema poznatim metodama kao npr. Claisenova kondenzacija (1 luang Weiynan et al; Huaxne Huebau 1983, 41(8) 723; C.A. 100 (1984) 22308s).
Nadalje, spojeve formule X moguće je dobiti tako da klordifluoracetilklorid ClF2C-CO-Cl reagira s ketonom H2C:=C=O, dobiveni klorid 4-klor-4,4-difluoroctene kiseline formule XI
[image]
hidroliziramo do jednostavne kiseline i prevedemo u reakciji s priklanim alkoholom ili aminom u ester ili amid formule X. Uspješno se ovi esteri i amidi mogu dobiti i direktno pretvorbom kiselinskog klorida formule XI s alkoholom ili aminom.
Primjerice, sintezu spojeva formule 1, gdje su R1 i R2 vodik, X kisik, a R3 alkil, izvodimo prema sljedećoj shemi 1:
Shema 1:
[image]
Sada smo utvrdili da su spojevi formule 1, u smislu pronalaska, uz prikladnu podnošljivost za toplokrvna bića, ribe i biljke, dragocjene tvari pri uništavanju štetočina. Osobito je dobra upotreba tvari u smislu pronalaska za insekte i pauke koji se pojavljuju na korisnim i ukrasnim biljkama u poljodjelstvu, a poglavito u nasadima pamuka, povrća i voćaka, u šumama i zaštiti uskladištenih materijala, kao i u sektoru higijene, osobito u kućnih i korisnih životinja. Djelotvorne su protiv svih ili pojedinačnim razvojnim stadijem normalno osjetljivih ili pak otpornih vrsta. Pritom se njihov učinak može pokazati neposredno pogibijom štetočina ili tek nakon određenog vremena, npr. u mijenjanju kože ili u smanjenom odlaganju jaja i/ili udjelu mijenjanja kože. U gore spomenute štetočine spadaju:
iz reda Lepidoptera npr.
Acleris spp., Adoxophyes spp., Aegeria spp., Agrotis spp., Alabama argillaceae, Amylois spp., Anticarsia gemmatalis, Archips spp., Argyrotaenia spp., Autographa spp., Busseola fusca, Cadra cautella, Carposina niponensis, Chilo spp., Choristoneura spp., Clysia ambiguella, Cnaphalosrosis spp., Cnephasia spp., Cochylis spp., Coleophora spp., Crocidolomia bonotalis, Cryptophlebia leucotreta, Cydia spp., Diatraea spp., diparopsis castanea, Earias spp., Ephestia spp., Eucosma spp., Eupoecilia amgibuella, Euproctis spp., Euxoa spp., Grapholita spp., Hedya nubiferana, Heliothis spp., Hellula undalis, Hyphantria cunea, Keiferia lycopersicella, Leucoptera scitella, Lithocollethis spp., Lobesia botrana, Lymantria spp., Lyonetia spp., Malacosoma spp., Maraestra brassicae, Manduca sextâ, Operophtera spp., Ostrinia nubilalis, Pammene spp., Pandemis spp., Panolis flammea, Pectinophora gossypiella, Phthorimaea opercullella, Pieris rapae, Pieris spp., Plutella xylostella, Prays spp., Scirpophaga spp., Sesamia spp., Sparganothis spp., Spodoptera spp., Synan-thedon spp., Thaumetopoea spp., Tortri spp., Trichoplusia in Yponomeuta spp.;
iz reda Coleoptera npr.
Agriotes spp., Anthonomus spp., Atomaria linearis, Chaetochema tibialis, Cosmopolites spp., Curculio spp., Dermestes spp., Diabrotica spp., Epilachna spp., Erem-nus spp., Leptinotarsa decemlineata, Lissorhoptrus spp., Melolontha spp., Orycaephilus spp., Otiorhynchus spp., Phlyctinus spp., Popillia spp., Psylliodes spp., Rhizopertha spp., Scarabeidae, Sitophilus spp., Sitotroga spp., Tenebrio spp., Tribolium spp., in Trogoderma spp.,
iz reda Orthoptera npr.
Blatta spp., Blattella spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Periplaneta spp., in Schistocerca spp.,
iz reda Isoptera npr.
Reticulitermes spp.,
iz reda Psocoptera npr.
Liposcelis spp.,
iz reda Anoplura npr.
Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp., in Phylloxera spp.,
iz reda Mallophaga npr.
Damalinea spp., in Trichodectes spp.,
iz reda Thysanoptera npr.
Frankliniella spp., Hercinothrips spp., Taeniothrips spp., Thrips palmi, Thips tabaci in Scirtothrips auranti;
iz reda Heteroptera npr.
cimex spp., Distantiella theobroma, Dysdercus spp., Euchistus spp., Euiygaster spp., leptocorisa spp., Nezara spp., Piesma spp., Rhodnius spp., Sahlbergella singularis, Scotinophara spp., in Triatoma spp.,
iz reda Homoptera npr.
Aleurothrixus floccosus, Aleyrodes brassicae, Aonidiella spp., Aphididae, aphis spp., Aspidiotus spp., Bemisia tabaci, Ceroplaster spp., Chrysomphalus aonidium, Chrysomphalus dictyospermi, Coccus hesperidum, Empoasca spp., Eriosoma larigerum, Erythroneura spp., Gascardia spp., Laodelphax spp., Lecanium corni, Lepidosaphes spp., Macrosiphus spp., Myzus spp., Nephotettix spp., Nilaparvata spp., Paratoria spp., Pemphigus spp., Planococcus spp., Pseudaulacaspis spp., Pseudococcus spp., Psylla spp., Pulvinaria aethiopica, Quadraspidiotus spp., Rhopalosiphum spp., Saissetia spp., Scaphoideus spp., Schizaphis spp., Sitobion spp., Trialeurodes vaporariorum, Trioza erytreae in Unaspis citri;
iz reda Hymenoptera npr.
Acromyrmex, Atta spp., Cephus spp., Diprion spp., Diprionidae, gilpinia polytoma, Hoplocampa spp., Lasius spp., Monomorium pharaonis, Neodiprion spp., Solenopsis spp., in Vespa spp.,
iz reda Diptera npr.
Aedes spp., Antherigona soccata, Bibio hortulanus, Calliphora erythrocephala, Ceratitis spp., Chrysomyia spp., Culex spp. Dacus spp., Drosophilamelanogaster, Fannia spp., Gastrophilus spp., Glossina spp., Hypoderma spp., Hyppobosca spp., Liriomyza spp., Lucilia spp., Melanagromyza spp., Musca spp., Oestrus spp., Orseolia spp., Oscinella frit, Pegomyia hyoscyami, Phoriba spp., Rhagoletis pomonella, Sciara spp., Stomoxys spp., Tabanus spp., Tannia spp., in Tipula spp.,
iz reda Siphonaptera npr.
Ceratophyllus spp., Xenopsylla cheopis,
iz reda Acarina npr.
Acarus siro, Aceria sheldoni, Aculus schlechtendali, Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Calipitrimerus spp., Chorioptes spp., Dermanyssus gallinae, Eotetranychus carpini, Eriophyes spp., Hyalomma spp., Ixodes spp., Olygonychus pratensis, ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Carcoptes spp., Tarsonemus spp., in Tetarnychus spp., in
iz reda Thysanura npr.
Lepisma saccharina.
Dobar pesticidni učinak spojeva formule I u smislu pronalaska odgovara zahtjevu za stupnjem uništenja (smrtnosti) najmanje 50-60 % spomenutih štetočina.
Učinak spojeva u smislu pronalaska, odnosno sredstava, koja ih sadrže može se bitno proširiti i prilagoditi danim okolnostima dodatkom drugih insekticida i/ili akaricida. Kao dodaci dolaze u obzir primjerice sljedeći razredi djelotvornih tvari: organski fosforovi spojevi", nitrofenoli i derivati, formamidini, karbamati, piretroidi, klorirani ugljikovodici i preparati Bacillusa thurmgiensisa.
Spojeve formule I upotrebljavamo u nepromijenjenom obliku ili poglavito s pomoćnim sredstvima koja su uobičajena u tehnici formuliranja, te ih je zato moguće preraditi na poznat način u emulzijske koncentrate, otopine koje se mogu izravno raspršivati ili razrijeđivati, razrijeđene emulzije, praške za prskanje, topljive praške, sredstva za zaprašivanje, granulate, a također i za izradbu kapsula, npr. u poiimcrnim tvarima. Postupak primjene, kao raspršivanje, zamagljivanje, zaprašivanje, posipanje ili polijevanje odabire se jednako kao i sredstva, ovisno o željenom cilju i postojećim okolnostima.
Formuliranje, tj. sredstva, pripravci i sastavi koji sadrže djelotvornu tvar formule 1, odnosno kombinacije tih tvari s drugim insekticidima ili akaricidima, i u danom primjeru čvrstu ili tekuću dodatnu osnovu, pripravljamo na poznat način, npr. temeljitim miješanjem i/ili mljevenjem djelotvorne tvari s puni lim a kao što su otapala, čvrste nosive osnove, i u danom primjeru površinski aktivni spojevi (tenzidi).
Kao otapala mogu doći u obzir aromatski ugljikovodici, poglavito frakcije C8-C12, kao npr. smjese ksilola ili supstituirani naftalini, esteri ftalne kiseline kao dibutilili dioktil-ftalat, alifatski ugljikovodici kao cikloheksan, parafini, alkoholi i glikoli kao i njihovi eteri i esteri. kao etanol, etilenglikol, metilenglikolmonometil- ili ctileter, kctoni kao cikloheksan on, jako polarna otapala kao N-metil-2-pirolidon. dimetilsulfoksid ili dimetilformamid, kao i u danom primjeru epoksidirana biljna ulja, kao spoksidira.no ulje kokosovih oraha ili sojino ulje, ili voda.
Kao čvrste osnove nosača, npr. u sredstvima za zaprašivanje i disperzibilnim prascima upotrebljavaju se u pravilu brašna prirodnih stijena, kao kalcita, talka, kaolina,, tnontmorilonita i atapuigita. Za poboljšanje fizikalnih osobina možemo dodati i visokodisperznu kremenastu zemlju ili visokodisperzne polimerizate koji imaju sposobnost upijanja. Kao zrnasti adsorptivni nositelji za granulate dolaze u obzir porozne vrste, kao npr. plovučac, zdrobljena opeka, sepiolit ili bcntinit, kao nosivi materijali koji nemaju sposobnost upijanja npr. kalcit ili pijesak. Osim toga mogu se upotrebljavati mnogi granulirani materijali anorganske ili organske prirode, a osobito dolomit ili zdrobljeni biljni ostaci.
Kao površinski aktivne tvari u obzir dolaze, ovisno o vrsti djelotvorne tvari formule i koju treba formulirati, ili kombinacije tih tvari s drugim insekticidima ili akaricidima, neionogeni, kationski i/ili anionski aktivni tenzidi dobrih emulgatorskih, disperznih i vlažnih svojstava. Pod tenzidima se podrazumijevaju i smjese tenzida.
Prikladni anionski tenzidi mogu biti takozvani u vodi topljivi sapuni kao i u vodi topljivi sintetički površinski aktivni spojevi.
Kao sapuni prikladne su alkalijske, zemnoalkalijske ili u danom primjeru supstituirane amonijeve soli viših masnih kiselina (C10-C22), primjerice Na ili K soli oleinske ili stearinske kiseline, ili prirodne smjese masnih kiselina koje je moguće dobiti npr. iz ulja, kokosovih oraha ili biljnog ulja. Nadalje kao tenzide treba spomenuti i metil-taurinske soli masnih kiselina kao i modificirane i nemodificirane fosfolipide.
Često se upotrebljavaju takozvani sintetički tenzidi, osobito masni sulfonati, masni sulfati, sulfonirani benzimidazolovi derivati ili alkilarilsulfonati.
Masni sulfonati ili sulafati pojavljuju se u pravilu kao alkalijske, zemnoalkalijske ili u danom primjeru kao supstituirane amonijeve soli, te imaju općenito alkilni ostatak s 8 do 22 ugljikova atoma, pri čemu alkil uključuje i alkilni dio acilnih ostataka, npr. Na ili Ca sol ligninsulfonske kiseline, estera dodecilsumporne kiseline ili smjese sulfata masnih alkohola pripravljene iz prirodnih masnih kiselina. Tu spadaju i soli estera sumporne kiseline i sulfonskih kiselina etilenoksidnih adukata masnih alkohola. Sulfonirani benzimidazolovi derivati sadrže poglavito 2 skupine sulfonske kiseline i jedan ostatak masne kiseline s oko 8 do 22 ugljikova atoma. Alkilarilsulfonati su npr. Na, Ca ili trietanolaminske soli dodecilbenzensulfonske kiseline, dibutilnaftalinsulfonske kiseline ili kondenzacijskog produkta naftalinsulfonske kiseline i formaldehida. Dalje dolaze u obzir i odgovarajući fosfati, kao soli estera fosforne kiseline p-nonilfenol -(4-14)-eti1 enoksidnog adukta.
Kao neionski tenzidi u obzir dolaze ponajprije poliglikoeterski derivati alifatskih ili cikloalifatskih alkohola zasićenih ili nezasićenih masnih kiselina i alkilfenola, koji mogu sadržavati 3 do 30 glikoeterskih skupina i 8 do 20 ugljikovih atoma u (alifatskom) ugljikovodičnom ostatku i 6 oo 18 ugljikovih atoma u alkilnom ostatku alkilfenola. Nadalje, prikladni neionski tenzidi su topljivi u vodi polietilenoksidni adukti, koji imaju 20 do 250 etilenglikoleterskih skupina i 10 do 100 propilenglikoleterskih skupina, sa polipropilenglikolom, etilendiaminopolipropilenglikolom i alkilpolipropilenglikolom, koji sadrže 1 do 10 ugljikovih atoma u alkilnom lancu. Navedeni spojevi sadrže obično 1 do 5 etilenglikolnih jedinica po jedinici propilcnglikola.
Kao primjere neionskih tenzida spomenimo nonilfenolpolietoksietanole, poliglikoletere ricinusovog ulja, tioksilat ricinusovog ulja, polipropilen-polietilen-oksidne adukte, tributilfenoksipolietoksietanol, polietilenglikol i oktilfenoksipolietoksietanol. Nadalje, u obzir dolaze i esteri masnih kiselina polioksieti1 ensorbitana, kao polioksietilensorbitan-trioleat.
Kationski tenzidi su prije svega kvarterne amonijeve soli koje sadrže kao supstituente najmanje jedan alkilni ostatak s 8 do 22 ugljikova atoma i koji imaju kao daljnje supstituente niže, u danom primjeru halogenirane alkilne, benzilne ili niže hidroksialkilne ostatke. Soli se pojavljuju ponajprije kao halogenidi, metilsulfati ili etilsulfati, npr. steariltrimetil amonijev klorid ili benzil-di-(2-kloroetol)-etilamonijev bromid.
U tehnici formuliranja uobičajeni tenzidi među ostalim su opisani npr. u narednim publikacijama.
"1985 International Me Cutcheon's Emulsifiers & Detergents", Glen Rock NJ USA, 1985",
"H. Stäche, "Tensid Taschenbuch", 2. Aufl., C. Hanser Verlag Muenchcn, Wien 1981,
M. i J. Ash. "Encyclopedia of Surfactants", Vol. Chemical
Publishing Co., New York, 1980-1981.
Pesticidni pripravci sadrže u pravilu 0.1 do 99 %, osobito 0.1 do 95 % djelotvorne tvari formule I ili kombinacije te tvari s drugim insekticidima ili akaricidima, 1 do 99,9 % čvrste ili tekuće dodatne osnove i 0 do 25 %, osobito 0,1 do 20 % tenzida. Međutim, kako su kao tržišna roba povoljnija koncentrirana sredstva, upotrebljava konačni potrošač u pravilu razrijeđene pripravke koji imaju bitno manje koncentracije djelotvorne tvari. Karakteristične uporabne koncentracije iznose između 0.1 i 1000 ppm, ponajprije između 0.1 i 500 ppm. Uporabne količine na hektar iznose općenito 1 do djelotvorne tvari na hektar, poglavito 25 do 500 g/ha.
Ponajbolje formulacije sastavljene su ovako:
(% = mas. postotak)
Emulzibilni koncentrali
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Prašci
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Suspenzijski koncentrati
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Prašci za namakanje
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Granulati
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Sredstva mogu sadržavati daljnje dodatke, kao stabilizatore, sredstva za razaranje pjene, konzervirajuća sredstva, regulatore viskoznosti, veziva, obuhvatna sredstva kao i gnojiva ili druge tvari za postizanje posebnih učinaka.
Sljedeći primjeri služe za objašnjenje pronalaska. Ne ograničavaju pronalazak.
Primjeri priprave
Primjer H1: etilester 4-klor-4,4-difluor-2-trifluormetil-maslačne kiseline
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a) etilester 2,4-diklor-4,4-dirluor-2-trifluomietilmaslačne kiseline
etilestera 2,2-diklor-3,3,3-trifluor-propionske kiseline stavimo s Cu(I)-klorida i 100 ml acetonitrila u autoklav. Tome dodamo pod tlakom 1,1-difluoretilena i smjesu zagrijavamo 8 sati na +. Nakon hlađenja reakcijsku smjesu oslobodimo otapala i preostalo ulje rektificiramo u vakuumu. Dobijemo etilestera 2,4-diklor-4,4-difluor-2-trilluormetilmaslaene kiseline u obliku bezbojnog ulja vrelišta 54-55 °C/11 mbar.
Analiza: C7H7ClF5O2 (289,03)
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b) etilestera 2,4-diklor-4,4-difluor-2-trimetil-maslačne kiseline obradimo u 200 ml etanola u prisutnosti 5 %-tne platine na ugljiku pri normalnom tlaku i sobnoj temperaturi s plinovitim vodikom, do vezivanja jednog ekvivalenta vodika. Nakon filtriranja katalizatora otapalo uklonimo destilacijom pri normalnom tlaku i ostatak rektificiramo.
Dobivamo etilestera 4-klor- 4,4-difluor-2-trilluorometilmaslačnc kiseline u obliku bezbojnog ulja vrelišta 41 -43 °C/16 mbara.
Analiza: C7H8ClF5O2 (254,58)
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Primjer H2: etilester 4-klor-4,4-difluormaslačne kiseline
ClF2C-CH2-CH2-COOC2H5
etilestera 2,4-diklor-4,4-difluoromasla5ne kiseline otopimo u 200 ml aps. etanola. Nakon dodatka bezvodnog natrijevog acetata i 5 %-tnog katalizatora platina/ugljik uvodimo pri normalnom tlaku plin vodik do vezivanja 100 % teorijskog iznosa. Nakon filtriranja katalizatora i uklanjanja etanola destilacijom preostalo ulje izlijemo u vodu, organsku fazu odvojimo, sušimo natrijevim sulfatom, filtriramo i rektificiramo pri normalnom tlaku. Dobijemo estera 4-klor-4,4-difluoromaslačne kiseline u obliku bezbojnog ulja vrelišta 154-.
Analiza: C6H9ClF2O2 (186,59)
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Primjer H3: Etilester 4-klor-4,4-difluoromaslačne kiseline
ClF2C-CH2-CH2-COOC2H5
etilestera 2,4-diklor-4,4-dirTuormaslačne kiseline otopimo u 100 ml aps. tetrahidrofurana. Nakon dodatka 2,6-dimetilpiridina i 5 %-tnog katalizatora paladij/ugljik uvodimo pri normalnom tlaku plin vodik do vezivanja 100 % teor. iznosa. Nakon filtriranja katalizatora i uklanjanja tetrahidrofurana destilacijom, preostalo ulje izlijemo u vodu, organsku fazu odvojimo, sušimo s natrijevim sulfatom, filtriramo i rektificiramo pri normalnom tlaku. Dobijemo etilestera 4-klor-4,4~ difluoromaslačne kiseline u obliku bezbojnog ulja vrelišta 154-.
Analiza: C6H9ClF2O2 (186,59)
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Primjer H4: etilester 4-klor-4,4-dilluoromaslačne kiseline
ClF2C-CH2-CH2-COOC2H5
etilestera 2,2,4-triklor-4,4-ditluoromaslačne kiseline otopimo u 200 ml aps. etanola. Nakon dodatka bezvodnog natrijevog acetata 1 5 %-tnog katalizatora platina/ugljik uvodimo plin vodik pri normalnom tlaku do vezivanja koje iznosi 2 ekvivalenta.. Nakon filtriranja katalizatora i uklanjanja etanola destilacijom preostalo ulje izlijemo u vodu, organsku fazu odvojimo, sušimo natrijevim sulfatom, filtriramo i rektificiramo pri normalnom tlaku. Dobijemo etilestera 4-klor-4,4-difluoromaslačne kiseline u obliku bezbojnog ulja vrelišta 154-.
Analiza: C6H9ClF2O2 (186,59)
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Primjer H5 : N-metilamid 4-klor-4,4-difluormaslačne kiseline
ClF2-CH2-CH2-CO-NH-CH3
etilestera 4-klor-4,4-difluoromaslačne kiseline otopimo pri u 10 ml 33 %-tne otopine metilamina u etanolu. Dobivenu reakcijsku smjesu miješamo 3 dana pri sobnoj temperaturi, nakon toga ju uparimo. Dobiveni ostatak prekristaliziramo iz heksana. Dobijemo N-metilamida 4 klor-4,4-difluormaslačne kiseline tališta 61-.
Primjer H6: benzilester 4-k1or-4,4-difluomaslačne kiseline
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a) 4-kl or-4,4-difluormaslačna kiselina
etilestera 4-klor-4,4-difluormaslačnc kiseline miješamo s 100 ml 2 N NaOH pri sobnoj temperaturi dok ne nastane homogena otopina. Otopinu zatim ulijemo u 150 ml 2 N HCl. Izlučenu organsku fazu preuzmemo u dietileter, sušimo natrijevim sulfatom i nakon uklanjanja etera destilacijom, rektifieiramo u vakuumu. Dobijemo 4-klor-4,4-difluoromaslačnu kiselinu u obliku bezbojnog ulja vrelišta 88-90 °C/mbara.
Analiza: C4M5ClF2O2 (158,53)
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b) klorid 4-klor-4,4-difluormaslačne kiseline
4-ldor-4,4-difluormaslačne kiseline izmiješamo s 50 ml tionilklorida i 0,2 ml dimetilformamida, te zagrijavamo 2 sata na + i još 30 minuta održavamo pri temperaturi od +. Reakcijsku smjesu rektificiramo u vakuumu i hvatamo tekućinu koja izlazi pri vrelištu od 35-37 °C/21 mbar. Dobijemo klorida 4-klor-4,4-difluormaslačne kiseline u obliku bistre bezbojne tekućine.
Analiza: C4H4Cl2F2O (176,98)
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c) Otopini klorida 4-kior-4,4-difluormaslačne kiseline u 15 ml benzena dodajemo pri kroz 30 minuta otopinu od benzilalkohola i piriđina u 6 ml metilenklorida. Dobivenu reakcijsku smjesu miješamo 16 sati pri , zatim ulijemo u 50 ml 1 N HCl i ekstrahiramo s 150 ml dietiletcra. Organsku fazu isperemo s 50 ml zasićene otopine NaHC03 i 50 ml zasićene otopine NaCl, sušimo magnezijevim sulfatom i uparimo. Dobiveni sirovi proizvod destiliramo u kugličnoj cijevi pri 190-210 °C/120 mbara. Dobijemo benzilcstera 4-klor-4,4-difluormaslačne kiseline.
MS: m/e: 248 (M+ , CHClFO)
Primjer H7: N-izopropilamid 4- klor-4,4-difluormaslačne kiseline
ClF2C-CH2-CH2-CO-NH-C3H7-i
Otopini klorida 4-kl or-4,4-difl uorm asl ačne kiseline u 15 ml toluena dodamo pri otopinu izopropilamina u 5 ml metilenklonda. Dobivenu reakcijsku smjesu miješamo 16 sati pri , zatim ulijemo u 50 ml zasićene otopine NaHCO3 i ekstrahiramo sa 150 ml dietiletera. Organsku fazu isperemo s 50 ml zasićene otopine NaCl, sušimo s magnezijevim sulfatom i uparimo. Dobijemo N-izopropilamida 4-klor-4,4-difluoromasl ačne kiseline, tal. 84-.
Primjer H8: metilester 2,4-diklor-4,4-difluormaslačne kiseline
ClF2C-CH2-CHC1-COOCH3
Otopinu metilestera 2,2,4-triklor-4,4-ditluormaslačne kiseline hidrogeniziramo u 20 ml aps. etanola uz dodatak 5 %-tnog katalizatora platina/ugljik do reakcije 1 ekvivalenta vodika pri sobnoj temperaturi (oko 1 sat). Nakon filtriranja katalizatora dobiveni sirovi produkt destiliramo u kugličnoj cijevi pri 4-70 °C/20 mbara. Dobijemo metilestera 2,4-diklor-4,4-difluormaslačne kiseline kao bezbojnog ulja.
Primjer H9: 4-kior-4,4-difIuormaslačna kiselina
ClF2C-CH2-CH2-COOH
4-klor-4,4-difluorkrotonske kiseline otopimo u 160 ml tetrahidrofurana i nakon dodatka 5%-tnog katalizatora Pd/BaSCO4 obradimo pri sobnoj temperaturi i normalnom tlaku s plinovitim vodikom do reakcije s vodikom u 100 % teorijskom iznosu. Nakon filtriranja katalizatora i uklanjanja otapala destilacijom preostalo ulje rektificiramo u vakuumu. Dobijemo bezbojnog ulja vrelišta 88-90 °C/11 mbara, koje je identično 4-klor-4,4-difiuormasIačnoj kiselini pripravljenoj u primjeru H6a.
Primjer H10: etilester 4-klor-4,4-difluor-3-hidroksimaslačne kiseline
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etilestera 4-k1or-4,4-dif1uor-octene kiseline otopimo u 200 ml tetrahidrofurana i nakon dodatka 5 %tnog katalizatora rodij/Al2O3 hidriramo pri normalnom tlaku i sobnoj temperaturi s vodikom do vezivanja teorijske množine vodika. Eventualno je u tijeku hidrogeniziranja potrebito dodati još svježeg katalizatora. Zatim katalizator odfiltriramo i otopinu uparimo uz vakuum vodene sisaljke. Rektifikacijom sirovog produkta dobije se čistog etilestera 4-klor-4,4-difluor-3-hidroksi-maslačne kiseline u obliku ulja vrelišta 93- i 17 mbara, koje prijeđe u čvrsto stanje u obliku dugih iglica.
Analiza: C6H9ClF2O3 (202,6)
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Primjer H11: etilester 4-klor-4,4- difluor-3-acetoksi-maslačne kiseline
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etilestera 4-klor-4,4-difluor-3-hidroksi-maslačane kiseline i bezvodnog natrijevog acetata otopimo u 50 ml acetanhidrida pri + i miješamo 1 sat pri toj temperaturi. Nakon ulijevanja reakcijske smjese u 150 ml vode produkt preuzmemo u dietileter. Etersku fazu sušimo natrijevim sulfatom i zatim uparimo eter u vakuumu. Rektifikacijom sirovog produkta dobije se etilestera 4-klor-4,4-difluor-3-acetoksi-maslačne kiseline u obliku bezbojnog ulja vrelišta pri 95- i 17 mbara.
Analiza: C8H11ClF2O4 (244,6)
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Primjer H12: etilester 4-klor-4,4-difiuor-kroton.ske kiseline
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etilestera 4-klor-4,4-difluor-3-acetoksimaslačne kiseline i 40 ml kinolina pomiješamo i zagrijavamo u aparaturi za destilaciju. Pri temperaturi kupelji od približno destilira bezbojno ulje oštrog mirisa, vrelišta pri 140-. Sirovi produkt preuzmemo u dietileter, isperemo s 1 N solnom kiselinom i vodom. Nakon sušenja eterske faze natrijevim sulfatom i odparavanja etera dobijemo etilestera 4-k1or-4,4-difluorkrotonsice kiseline u obliku bezbojnog ulja vrelišta pri 41- i 12 mbara.
Analiza: C6H7ClF2O2 (184,6)
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Isti produkt dobivamo ako etilester 4-klor-4,4-difluor-3 hidroksi-maslačne kiseline obradimo s fosforpentoksidom prema metodi McBee et al. u J.Amer.Chem.Soc. 76 (1954) 3722, navedenoj za etilester 4,4,4-trifluor-3-hidroksimaslačnu kiselinu.
Primjer H13: etilester 4-klor-4,4-dirluormaslačne kiseline
ClF2C-CH2-CH2-COOC2H5
etilestera 4-klor-4,4-difluor-krotonske kiseline otopimo u 200 ml etilestera octene kiseline i nakon dodatka 5 %-tnog katalizatora paladij/barijev sulfat obradimo s plinovitim vodikom pri normalnom tlaku i sobnoj temperaturi. Hidrogenizacija je ubrzo završena. Nakon filtriranja katalizatora otapalo se odpari u vakuumu i ostatak se rektificira. Produkt, koji destilira pri 154- identičan je etilesteru 4-klor-4,4-difluormaslačne kiseline, pripravljenom prema primjerima H2, 113 i H4. Analogno opisanim radnim postupcima pripravili smo još sljedeće spojeve, navedene u tablicama.
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Tablica 1 (nastavak)
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Tablica 1 (nastavak)
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Tablica 1 (nastavak)
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Tablica 1 (nastavak)
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Tablica 1 (nastavak)
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Tablica 1 (nastavak)
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Tablica 1 (nastavak)
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Tablica 1 (nastavak)
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Tablica 1 (nastavak)
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Tablica 1 (nastavak)
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Tablica 2 (nastavak)
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Tablica 2 (nastavak)
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Tablica 2 (nastavak)
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Tablica 2 (nastavak)
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Tablica 2 (nastavak)
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Tablica 2 (nastavak)
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Tablica 2 (nastavak)
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Tablica 2 (nastavak)
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Tablica 2 (nastavak)
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Tablica 2 (nastavak)
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Tablica 2 (nastavak)
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Tablica 2 (nastavak)
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Tablica 2 (nastavak)
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Tablica 2 (nastavak)
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Formulirani primjeri (% = mas.%)
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Iz takvih se koncentracija mogu pripraviti razrjeđenjem s vodom emulzije bilo koje željene koncentracije.
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Otopine su prikladne za uporabu u obliku najmanjih kapljica.
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Djelotvornu tvar otopimo u metilenkloridu, poškropimo nosač, a otapalo zatim uparimu u vakuumu.
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Temeljitim miješanjem nosača s djelotvornom tvari dobivamo pripravljena sredstva za zaprašivanje.
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Djelotvornu tvar pomiješamo s dodatcima i dobro sameljemo prikladnim mlinom. Dobijemo praške za raspršivanje koji se vodom mogu razrijediti u suspenzijesvake željene koncentracije.
Primjer F6: Emulzijski koncentrati
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Iz takvog se koncentrata može razrijeđenjem s vodom pripraviti emulzija svake željene koncentracije.
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Sredstvo za zaprašivanje pripravljeno za uporabu dobivamo miješanjem djelotvorne tvari i nosača, te mljevenjem u prikladnom mlinu.
Primjer F8: Istisnuti (ekstrudirani) granulat
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Djelotvornu tvar pomiješamo s dodatcima, sameljemo i navlažimo vodom. Tu smjesu istisnemo, granuliamo i zatim sušimo uz protok zraka.
Primjer F9: Prevučeni granulati
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U miješalu dobro promiješanu djelotvornu tvar jednolično nanesemo na polietilenglikolom navlažen kaolin. Na taj način dobijemo prevučene granulate bez praha.
Primjer F10: Suspenzijski koncentrat
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Fino samljevenu djelotvornu tvar temeljito pomiješamo s dodatcima. Tako dobijemo suspenzijski koncentrat iz kojega se razrijeđenjem s vodom mogu pripraviti suspenzije svake željene koncentracije.
Biološki primjeri
Primjer B1: Učinak protiv Boophilus microplus
Odrasle ženke krpelja, do sitog napijene, prilijepimo na ploču od PVC i prekrijemo grumenom vate. Pri obradi prelijemo testirane životinje s 10 ml testirane otopine koja sadrži 125 ppm ispitivane djelotvorne tvari. Zatim uklonimo grumen vate i krpelje inkubiramo 4 tjedna za leženje jajašaca. Učinak protiv Boophilus microplus se očituje u ženka bilo kao mortalitet ili kao sterilitet, ili u jajašaca kao ovicidan učinak.
Spojevi u smislu tablice 1 i 2 pokazuju u tom testu dobar učinak protiv Boophilus microplus. Osobito spojevi 1.01, 1.04, 1.05, 1.06, 1.10, 1.18, 1.21, 1.22,1.30, 1.31, 1.33, 1.35, 1.36, 1.37, 1.38, 1.39, 1.40, 1.45, 1.46, 2.01, 2.02, 2.05, 2.07, 1.08, 2.09, 2.24, 2.28, 2.30, 2.31, 2.32, 2.33 i 2.35 imaju učinak veći od 80%.
Primjer B2: Ovicidni učinak na Heliotbis vircseens
Jajašca Heliothis virescens izležena na filtrir papiru potopimo kratkotrajno u acetonsko-vodenu testnu otopinu koja sadrži 400 ppm ispitivane djelotvorne tvari. Nakon sušenja testne otopine jajašca inkubiramo u Petrijevim zdjelicama. Poslije 6 dana odredimo postotak izleženih jajašaca prema neobrađenim kontrolnim nasadima (% smanjenja leženja) Spojevi u smislu tablice 1. i 2. pokazuju u tom testu dobar učinak protiv Helieothis virescens. Osobito spojevi 1.01, 1.02, 1.04, 1.06, 1.10, 1.22, 1.31, 1.36, 1.40, 1.45, 1.46, 2.01, 2.02, 2.05, 2.07, 2.08, 2.24 i 2.28 imaju više od 80% tni učinak.
Primjer B3: Učinak protiv Aonidiella aurantii
Gomolje krumpira naselimo s migracijskim ličinkama ("crawler" Aodiniella aurantii, crvena limunska košenilka). Nakon oko 2 tjedna potopimo krumpire u vodenu emulziju odnosno suspenziju smjese za raspršivanje koja sadrži ispitivanu djelotvornu tvar u koncentraciji od 400 ppm. Nakon sušenja tako obrađene gomolje krumpira inkubiramo u posudi od umjetnih materijala. Za procjenu uspoređujemo 10 do 12 tjedana kasnije stupanj preživljenja migracijskih Učinaka prve uzastopne generacije obrađene populacije košenilka s onima u neobrađenim kontrolnim nasadima.
Spojevi u smislu tablice 1. i 2. pokazuju u tom testu dobar učinak protiv Aonidiella aurantii. Osobito spojevi 1.18, 1.21, 1.2, 1.30, 1.31, 1.32, 1.33, 1.35, 1.37, i .38. 1.39, 1.48, 1.49, 2.01, 2.05, 2.07, 2.08, 2.30, 2.37, 2.42, 2.43, 2.44, 2.45, 2.46 i 2.48 imaju učinak veći od 80%.
Primjer B4: Učinak protiv Nilaparvata lugens
Rižine biljke obrađujemo s vodenom emulzijskom smjesom za raspršivanje koja sadrži 400 ppm djelotvorne tvari. Nakon sušenja raspršenog sloja nasadimo rižine biljke s ličinkama cvrčaka u 2. i 3. stadiju. Nakon 21 dan obavlja se procjena. Prema usporedbi broja preživjelih cvrčaka na obrađenim i na neobrađenim biljkama određuje se postotno smanjenje populacije (% učinka).
Spojevi iz tablice 1. i 2. pokazuju dobar učinak protiv Nilaparvata lugens pri tom testu. Osobito spojevi 1.10, 1.22, 1.30, 1.31, 1.33, 1.35, 1.36, 1.37, 1.38, 1.39, 1.40, 1.45, 1.48, 1.49, 2.05, 2.07, 2.08, 2,24, 2.28, 2.30, 2.31, 2.32, 2.35, 2.36, 2.39, 2.41, 2.42, 2.43, 2.45, 2.46 i 2.47 imaju učinak preko 80%.
Primjer B5: Učinak protiv Tetranychus urticae
Mlade biljke graha nasadimo miješanom populacijom Tetranychus urticae i 1 dan kasnije poškropimo vodenom emulzijskom smjesom za raspršivanje koja sadrži 400 ppm djelotvorne tvari. Biljke zatim inkubiramo kroz 6 dana pri i potom procjenjujemo. Usporedbom broja uginulih jajašaca, ličinaka i odraslih na obrađenim i na neobrađenim biljkama određujemo postotno smanjenje populacije (% učinka).
Spojevi iz tablice 1. i 2. pokazuju dobar učinak protiv Tetranychus urticae pri tom testu. Osobito spojevi 1.30, 1.33, 1.35, 1.36, 1.38, 1.39, 2.28, 2,39, 2.41, 2.43 12.44 pokazuju više od 80%-tni učinak.
Primjer B6: Učinak protiv Anthonomus grandis (adulti)
Mlade biljke pamuka poprskamo vodenom emulzijskom smjesom za raspršivanje koja sadrži 400 ppm djelotvorne tvari. Nakon sušenja raspršenog sloja nasadimo biljke pamuka s 10 odraslih Anthonomus grandis i stavimo u posudu od umjetnog materijala. Procjena se obavlja 3 dana kasnije.
Spojevi iz tablice 1. i 2. pokazuju u tom testu dobar učinak protiv Anthonomus grandis. Posebice spojevi 1.22, 1.36, 1.37, 1.49, 2.28, 2.32, 2.38 i 2.39 imaju učinak veći od 80%.
Primjer B7: Učinak protiv Aphis craccivora
Sadnice graha inficiramo s Aphis craccivora i zatim poškropimo smjesom za raspršivanje koja sadrži 400 ppm djelotvorne tvari, te inkubiramo pri . 3 i 6 dana kasnije obavlja se procjena. Usporedbom broja uginulih lisnih uši na obra|enim biljkama i onih na neobrađenim izračunamo postotno smanjenje populacije (% učinka).
Spojevi iz tablice 1. i 2. pokazuju u tom testu dobar učinak protiv Aphis accivora. Posebice spojevi 2.05, 2.07, 2.08, 2.24, 2.28, 2.35 i 2.39 imaju učinak veći od 80%.
Primjer B8: Sustavni učinak protiv Myzus persicae
Sadnice graha inficiramo s Myzus pesicae, zatim ih stavimo s korjenom u smjesu za raspršivanje koja sadrži 400 ppm djelotvorne tvari, te inkubiramo pri . 3 do 6 dana kasnije obavlja se procjena. Usporedbom broja uginulih lisnih uši na obrađenim i na neobrađenim biljkama odredimo postotno smanjenje populacije (% učinka).
Spojevi iz tablice 1. i 2. pokazuju dobar učinak u tom testu protiv Mvzus persicae. Posebice spojevi 2.05, 2.24 i 2.28 imaju učinak veći od 80%.
Primjer B9: Sustavan učinak protiv Nilaparvata lugens
Lonac s rižinom biljkama stavimo u vodenu emulzijsku otopinu koja sadrži 400 ppm djelotvorne tvari. Zatim rižine biljke nasadimo ličinkama u 2. i 3. stadiju. 6 dana kasnije obavlja se procjena. Usporedbom broja cvrčaka na obrađenim i onoga na neobrađenim biljkama odredimo postotno smanjenje populacije (% učinka).
Spojevi iz tablice 1. i 2. imaju u tom testu dobar učinak protiv Nilaparvata lugens. Posebice spojevi 1.01, 1.02, 1.04, 1.05, 1.06, 1.10, 1.18, 1.21, 1.22, 1.30, 1.31, 1.33, 1.35, 1.36, 1.37, 1.38, 1.39, 1.40, 1.45, 1.46, 1.48, 1.49,2.01,2.05, 2.07, 2.08, 2.09, 2.24, 2.28, 2.30, 2.31, 2.32, 2.33,2.35, 2.36, 2.37, 2.38, 2.39, 2.40, 2.41, 2.42, 2.43, 2.44, 2.45, 2.46, 2.47 i 2.48 imaju već pri 112,5 ppm učinak preko 80%.
Primjer B10: Ovicidni učinak protiv Adoxophyes reticulana
Jajašca Adoxopfyes reticulana izležena na filtrir papiru kratkotrajno potopimo u acetonsko vodenu testnu otopinu koja sadrži 400 ppm djelotvorne tvari. Nakon sušenja testne otopine jajašca inkubiramo u Petrijevim zdjelicama. 6 dana kasnije procjenjujemo postotno leženje jajašaca usporedbom s neobrađenim kontrolnim zametcima (% smanjenja leženja)
Spojevi iz tablice 1. i 2. pokazuju u tora testu dobar učinak protiv Adoxophyes reticulana. Posebice spojevi 1.02, 1.22, 1.31, 1.36, 2.05, 2.07, 2.08 i 2.35 imaju učinak veći od 80%.
Primjer B11: Ovo/larvicidni učinak na Heliothis virescens
Jajašca Heliothis virescens izležena na pamuku poškropimo s vodenom emulzijskom smjesom za raspršivanje koja sadrži 400 ppm djelotvorne tvari. Nakon 8 dana procijenimo postotak izleženih jajašaca i stupanj preživljenja gusjenica u usporedbi s neobrađenim kontrolnim nasadom (% smanjenja populacije).
Spojevi iz tablice 1. i 2. pokazuju u tom testu dobar učinak protiv Heliothis virescens. Posebice spojevi 1.01, 1.02 1.04, 1.05, 1.06, 1.08,1.09, 1.10, 1.18, 1.21, 1.22, 1.30, 1.31, 1.32, 1.33, 1.35, 1.36, 1.37, 1.38, 1.39, 1.40, 1.45, 1.46, 1.48, 1.49, 20.1, 2.02, 2.05, 2.07, 2.08, 2.09, 2.24, 2.28, 2.30, 2.31, 2.32, 2.33, 2.35, 2.36, 2.37, 2.38, 2.39, 2.40, 2.41, 2.42, 2.43, 2.44, 2.45, 2.46, 2.47 i 2.48 imaju učinak veći od 80 %.
Primjer B12: Učinak protiv Dermanyssus gallinae
U staklenu posudu odozgo otvorenu dodamo 2 do otopine koja sadrži 10 ppm djelotvorne tvari oko 200 grinja u različitim razvojnim stadijima. Zatim posudu zatvorimo grudom vate, deset minuta protresemo do potpunog namakanja grinja i kratkotrajno okrenemo da vata preume preostalu testnu otopinu. Nakon 3 dana utvrđujemo mortalitet grinja.
Spojevi iz tablice 1. i 2. pokazuju u tom testu dobar učinak protiv Dermanvssus galinae. Posebice spojevi 1.04, 1.06, 1.10, 1.2, 1.31, 1.36, 1.40, 1.45, 2.01 i 2.02 imaju učinak veći od 80%.
Primjer B13: Učinak protiv gusjenica Heliothis virescens
Mlade sojine biljke poškropimo vodenom emulzijskom smjesom za raspršivanje koja sadrži 400 ppm djelotvorne smjese. Nakon sušenja raspršene smjese nasadimo sojine biljke s 10 gusjenica prvog stadija Heliothis virescens, te ih stavimo u posudu od umjetnog materijala. Procjenjuje se 6 dana kasnije. Pomoću usporedbe broja uginulih gusjenica i štete zbog pojedenih obrađenih biljaka s onima neobrađenih utvrđujemo postotno smanjenje populacije, odnosno postotno smanjenje štete zbog pojedenih biljaka (% učinka).
Spojevi iz tablice 1. i 2. pokazuju u tom testu dobar učinak protiv Heliothis virescens. Posebice spojevi 2.01, 2.07, 2.24 i 2.33 imaju učinak veći od 80%.
Primjer B14: Ovicidni učinak na Cydia pomonella
Jajašca Cydia pomonella izležena na filtrir papir kratkotrajno namočimo u acetonsko-vodenu testnu otopinu koja sadrži 400 ppm ispitivane djelotvorne tvari. Nakon sušenja testne otopine jajašca inkubiramo u Petrijevim zdjelicama. 6 dana kasnije procjenjujemo postotno leženje jajašaca u usporedbi s neobrađenim kontrolnim zametcima (% smanjenja leženja).
Spojevi iz tablice 1. i 2. imaju u tom testu dobar učinak protiv Cydia pomonella.
Primjer B15: Učinak protiv Nephotettix cincticeps
Rižine biljke obradimo vodenom emulzijskom smjesom za raspršivanje koja sadrži 400 ppm djelotvorne tvari. Nakon sušenja raspršenog sloja nasadimo rižine biljke ličinkama cvrčaka 2. i 3. stadija. Procjenjujemo 21 dan kasnije. Usporedbom broja preživjelih cvrčaka na obrađenim biljkama i onih na neobrađenim, odredimo postotno smanjenje populacije (% učinka).
Spojevi iz tablice 1. i 2. pokazuju dobar učinak u tom testu protiv Nephoteuix cincticeps. Posebice spojevi 1.33, 1.37, 1.38, 1.39 i 2.48 imaju učinak veći od 80%.
Primjer B16: Učinak protiv Ctenocephalides felis
20 do 25 buhinjih jajašaca stavimo u horizontalnu stojeću staklenku sa staničnom kulturom u koju smo prethodno stavili hranjivog sredstva za buhinje ličinke, a koje sadrži 400 ppm ispitivane djelotvorne tvari. Testne staklenke smo inkubirali u inkubatoru pri 26 do i 60-70 % vlage u zraku. Nakon 21 dana kontroliramo nazočnost odraslih buha, neizleženih buba i ličinaka.
Spojevi iz tablice 1. i 2. pokazuju u tom testu dobar učinak protiv Ctenocephalides felis.
Primjer B17: Učinak protiv jajašaca Diabrotica balteata
20 do 50 jajašaca Diabrotica balteata izleženih na filtru od tkanine stavimo u Petrijevu zdjelicu i obradimo vodenom emulzijskom raspršenom smjesom koja sadrži 400 ppm djelotvorne smjese. Petrijeve zdjelice inkubiramo pri . Nakon 7 dana procjenjujemo postotno leženje jajašaca usporedbom s neobrađenim kontrolnim nasadima (% smanjenja leženja.).
Spojevi iz tablice 1. i 2. pokazuju u tom testu dobar učinak protiv Diabrotica balteata. Posebice spojevi 2.05, 2.08 i 2.24 imaju učinak veći od 80%.
Primjer B18: Učinak protiv jajašaca Bemisia tabaci
Biljke grmovitoga graha stavimo u kaveze od gaze i na. njih nasadimo odrasle Bemisia tabaci (bijela muha). Nakon završetka leženja jajašaca uklonimo sve odrasle i 2 dana kasnije obradimo biljke s nimfama koje se na njima nalaze, vodenom emulzijskom smjesom za raspršivanje ispitivane otopine (koncentracija 400 ppm). Procjenjuje se 10 dana nakon nanošenja djelotvorne tvari s obzirom na postotak leženja usporedbom s neobrađenim kontrolnim; nasadima.
Spojevi iz tablice 1. i 2. pokazuju u tom testu dobar učinak protiv Bemisia. tabaci.
Claims (21)
1. Derivati 4-klor-4,4-difluonri asl acne kiseline formule I
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naznačeni time, da su
R1 i R2 neovisno jedan o drugom vodik, C1-C4-alkil ili C1-C4-halogenalkil,
R3 vodik ili organski ostatak i X kisik ili -NR4-,
pri čemu R4 označava vodik ili C1-C6-alkil.
2. Spojevi prema zahtjevu 1, naznačeni time, da R3 označava vodik ili svagda supstituiran ili nesupstituiran C1-C20-alkil, C3-C7-cikloalkil, C3-C20-alkenil, C3-C20-alkinil, benzil ili aril.
3. Spojevi prema zahtjevu 1, naznačeni time, da R3 označava supstituiran ili nesupstituiran C1-C20-alkil, C3-C7-cikloalkil, C3-C20-alkenil, C3-C20 alkinil, benzil ili aril. Ponajprije R3 označava u okviru predloženog pronalaska C1-C20-alkil, C3-C7-cikloaikil, C3-C20-alkenil, C3-C20-alkinil, aril, C3-C20-halogenalkenil, C3-C20-halogenalkinil; s halogenom ili C1-C4 alkilom supstituiran C3-C7-cikloalkil; s halogenom, C1-C4-alkil, C1-C4-halogenalkil, C1-C12-alkoksi, C1-C4-halogcnalkoksi, C1-C4-alkiltio, nitro, cijano, benzoilom, halogenbenzoilom, fenoksi, halogenfenoksi, C1-C4-alkilfenoksi, C1-C4-halogenalkilfenoksi, tri-C1-C4-alkilsililom, N-pirolidinilom, N-piperidinilom, N-pirolidin-2-onilom, N-piperidin-2-onilom, C1-C4-alikilamino, di-C1-C4-alki1amino, anilino, N-C1-C4-alkilanilino, N-formilanilino, N-C1-C6-alkilkarbonilanilino, feniltio ili halogenfeniltio supstituiran aril; preko kisika ili sumpora vezanim nesupstituiranim ili supstituiranim aromatskim ili nearomatskim mono- ili bicikličkim heterociklom supstituiran fenil, pri čemu može kako heterociklički, tako i fenilni prsten biti svagda supstituiran s halogenom, C1-C4-alkilom, nitro, C1-C4-halogenalkilom, C1-C4-halogenalkoksi, C1-C4-alkoksi, C1-C4-alkiltio, ili eikloprilom; ili s hidroksi, halogenom, di-C1-C4-alkilamino, C1-C4-alkoksi, C1-C4-halogenalkoksi, C2-C6-alkoksialkoksi, C1-C4halogenalkiltio, C1-C4-alkiltio, C1-C4-alkilsulfimlom, C1-C4-alkilsulfoniloksi, C1-C4-a1kilkarbonilom, C1-C4-alkoksikarbonilom, C1-C6-alkilkarboniloksil, C3-C7-cikloalkilom, arilom, ariloksi, ariltio, arilsulfonilom, arilsulfinilom, arilsulfoniloksi, arilkarbonilom ili piridilom supstituiran C1-C20-alkil, pri čemu arilne i piridilne skupine mogu svagda biti supstituirane s halogenom, C1-C4-alkilom, C1-C4-halogenalkilom, C1-C4-alkoksi, C1-C4-halogenalkoksi, C1-C4-alkiltio, nitro, cijano, fenoksi, halogenfenoksi, ieniltio ili halogenfeniltio.
4. Spojevi prema zahtjevu 1, naznačeni time, da R1 i R2 neovisno jedan o drugom označavaju vodik ili C1-C4-alkil, ponajprije vodik.
5. Spojevi prema zahtjevu 1, naznačeni time, da X označava kisik, -NH-, -NCH3- ili -NC2H5-, ponajprije kisik ili -NH-.
6. Spojevi prema zahtjevu 3, naznačeni time, da R3 označava fenil supstituiran u položaju 4, preko kisika vezanim aromatskim mono- ili bicikličkim heterociklom iz reda piridina, pirimidina ili benzotiazola, pri čemu su oba aromatska prstena nesupstituirana ili zajedno imaju najviše tri daljnja supstituenta iz niza klora, broma, metila, etila i trifluormetila.
7. Spojevi prema zahtjevu 3, naznačeni time, da R1 i R2 neovisno jedan o drugom označavaju vodik ili C1-C4-alkil, X kisik ili -NH4- i R4 vodik, metil ili etil, a R3 označava vodik, C1-C20-alkil, C3-C7-cikloalkil, C3-C20-alkenil, C3-C20-alkinil, fenil, naftil, C3-C20-halogenalkenil, C3-C20-halogenalkinil; s fluorom, klorom, bromom ili C1-C3-alkilom supstituiran C3-C7-cikloalkil; s fluorom, klorom, bromom ili C1-C3-alkilom, C1-C3-halogenalkilom, C1-C3-alkoksi, C1-C3-halogenalkoksi, C1-C3-alkiltio, nitro, cijano, fenoksi, halogenfenoksi, C1-C4-alkilfenoksi, C1-C4-halogenalki1fenoksi, tri-C1-C4-alkilsilil, N-pirolidinil, N-piperidimlom, N-pirolidin-2-onilom, N-piperidin-2-onilom, C1-C4-alkilamino, di-C1-C4-alkilamino, anilino, N-C1-C4-alkilanilino, N-formilanilino, N-C1-C6-alkilkarbonilanilino, feniltio ili halogenfeniltio supstituiran fenil ili naftil, ili s hidroksi, fluoro, kloro, bromo, di-C1-C4-alkilamino, C1-C4-alkoksi, C1-C4-halogenalkoksi, C2-C6-a1koksialkoksi, C1-C4-halogenalkiltio, C1-C4-alkiltio, C1-C4-alkilsulfinilom, C1-C4-alkilsulfonilom, C1-C4-alkilsulfoniloksi, alkilkarbonilom, C1-C4-alkoksikarbonilom, C1-C6-alkilkarboniioksi, C3-C7-cikloalkilom, feniiom,fenoksi, feniltio, fenilsulfoniloksi ili piridilom supstituiran C1-C20-alkil, pri čemu fenilne i piridilne skupine svagda mogu biti supstituirane fluorom, klorom, bromom, C1-C3-alkilom, C1-C3-halogenalkilom, C1-C3-alkoksi, C1-C3-halogenalkoksi, C1-C3-alkiltio, nitro, cijano, fenoksi, halogenfenoksi, feniltio ili halogenfeniltio.
8. Spojevi prema zahtjevul, naznačeni time da. R1 i R2 neovisno jedan o drugom označavaju vodik ili C1-C4-alkil, X kisik ili -NR4-, R4 vodik, metil ili etil, R3 fenil, benzil, naftil, 3-pfridilmetiI ili svagda fluorom, klorom, bromom, C1-C3-alkilom, C1-C3-halogenalkilom, C1-C3-alkoksi, C3-C3-halogenalkoksi, C1-C3-alkilito, nitro, cijano, fenoksi, halogenfenoksi, feniltio ili halogenfeniltio supstituiran fenil, benzil, naftil ili 3-piridilmctil.
9. Spojevi prema zahtjevu i, naznačeni time da R1 i R2 neovisno jedan o drugom označavaju vodik ili C1-C4-alkil, X kisik ili -NR4-, R4 vodik ili C1-C4-alkil, R3 C1-C12-alkil ili hidroksi, fluorom, klorom, bromom, dimetilamino, metoksi, etoksi, metoksietoksi, etoksietoksi, metiltio, etiltio, ciklopropilom, ciklopentilom, cikloheksilom, fenilom ili fenoksi supstituiran C1-C12-alkil, pri čemu fenilni ili fenoksi ostatak svagda može biti supstituiran fluorom, klorom, bromom, fenoksi, halogenfenoksi ili feniltio.
10. Spojevi prema zahtjevu 1, naznačeni time da R1 i R2neovisno jedan o drugom označavaju vodik ili C1-C4-alkil, X kisik ili -NR4-, R4 vodik ili C1-C4-alkil, R3 C3-C12-alkenil, C3-C]2-alkinil, ili svagda fluorom, klorom ili bromom supstituiran C3-C12-aikenil ili C3-C12-alkinil.
11. Spojevi prema zahtjevu 3, naznačeni time, da R1 i R2 označavaju vodik a X kisik, -NH-, -NCH3- ili -NC2H5-.
12. Spojevi prema zahtjevu 1, naznačeni time, odabrani iz skupine koju sastavljaju:
metilester 4-klor-4,4-difluoromaslačne kiseline,
etilester 4-klor-4,4-dilluoromaslačne kiseline,
izopropilester 4-klor-4,4-difluoromaslačne kiseline,
tert-butilester 4-klor-4,4-ditluoromaslačne kiseline,
n-butilester 4-klor-4,4-di(luoromaslačne kiseline,
(2,2dimetilpropil)-ester 4-klor-4,4-difluoromaslačne kiseline,
benzilester 4-klor-4,4-difluoromaslačne kiseline,
fenilester 4-klor-4,4-difluoromaslačne kiseline,
[2-(4-fenoksifenoksi)-etil]ester 4-klor-4,4difluoromaslačne kiseline,
cikloheksilester 4-klor-4,4-difluoromaslačne kiseline,
cikloheksilmetilester 4-klor-4,4-difluoromaslačne kiseline,
ciklopropilmetilester 4-klor-4,4-difluoromaslačne kiseline,
etilester 4-klor-4,4-difluorometilmaslačne kiseline,
N-metilamid 4-klor-4,4-difluoromaslaene kiseline,
N,N-dimetilamid 4-klor-4,4-difluoromas1ačne kiseline,
N,N-diheksilamid 4-klor-4,4-difluoromaslačne kiseline,
N-etilamid 4-klor-4,4-difluoromaslačne kiseline,
N-izopropilamid 4-klor-4,4-dofluoromaslačnc kiseline,
N-butilamid 4klor-4,4-dilfuoromaslačne kiseline,
N-tertbutilamid 4-klor-4,4-difluoromaslačne kiseline,
N-benzilamid 4-klor-4,4-difluoromaslačne kiseline,
anilid 4-klor-4,4-difluoromaslačne kiseline,
N-metil-N-pirid-3ilmetilarnid 4-klor-4,4-difIuoromaslačne kiseline,
N-metil -3-ilmetilamid 4-klor-4,4-difluoromaslačne kiseline,
(4klor-anilid) 4-k1or-4,4-difluormaslačne kiseline,
(4-fenoksianilid) 4-klor-4,4-difluoromaslačne kiseline,
(4-klor-anilid) 4-klor-4,4-difluoromaslačrte kiseline,
(4-metoksi-anilid) 4klor-4,4-difiuoromasfacne kiseline,
(4-metil-anilid) 4-klor4,4-difluoromaslačne kiseline,
(3-merkapto-anilid) 4-klor-4,4difluoromaslačne kiseline,
(4-fluor-anilid) 4-klor-4,4difluoromaslačne kiseline,
(4-klor-2-nitro-anilid) 4-klor-4,4difluoromaslaene kiseline,
(3-fenoksi-benzil)-ester 4-klor-4,4difluoromas1ačne kiseline,
[4-(4-fluor-fenoksi)-fenil]-ester 4klor-4,4-difluoromaslačne kiseline,
[4-(4-fluor-fenoksi)-fenoksi-etil]-ester 4-klor-4,4-difluoro maslačne kiseline,
(4-nitro-fenil)-ester 4-klor-4,4-difluoromaslačne kiseline,
[4(3,5-difluor-fenoksi)-fenil]-ester 4-klor-4,4-dif1uoromaslačne kiseline,
[4-(5-trifluor-metil-pirid-2-iloksi)-fenil]ester 4klor-4,4-difluoromaslačne kiseline,
4-klor-4,4-difluoromaslačne kiseline i
amid 4-klor-4,4-dilluormaslačne kiseline.
13. Postupak: za pripravu spojeva formule i, prema zahtjevu 1, naznačen time, da bilo
a) halogenid 4-klor-4,4-difluormaslačnc kiseline formule II
[image]
gdje R1 i imaju značenja navedena pri formuli I, a Hal označava halogen, ponajprije klor ili brom, pretvorimo u nazočnosti baze pomoću spoja formule III
[image]
gdje su X i R:; značenja navedenog pri formuli I, ili
b) 4-klor-4,4-difluoromasla.čnu kiselinu formule Ic
[image]
u kojoj R1 i R2 imaju značenja navedena pri formuli 1, pretvorimo u nazočnosti sredstva za izvlačenje vode pomoću spoja formule III.
14. Sredstvo za uništavanje štetočina naznačeno time, da sadrži kao aktivnu komponentu barem jedan spoj formule I prema zahtjevu 1.
15. Sredstvo prema zahtjevu 14, naznačeno time, da sadrži barem još jedan nosač.
16. Uporaba spoja formule 1, prema zahtjevu 1, naznačena time, za uništavanje štetočina na životinjama i biljkama.
17. Uporaba prema zahtjevu 16, naznačena time, da vrijedi u štetočina za fitopatogene insekte i grinje.
18. Postupak za uništavanje životinjskih parazitskih i fitoparazitskih insekata i grinja, prema zahtjevu 1 naznačen time, da obradimo štetočine ili njihov životni prostor djelotvornom količinom spoja formule I.
19. Balogenidi 4-klor-4,4-diflouormaslačne kiseline formule II
[image]
naznačeni time, da R1 i R2 neovisno jedan o drugom označavaju vodik, C1-C4- alkil ili C1-C4-halogenalkil, a Hal halogen, ponajprije klor ili brom.
20. Derivati 4-klor-4,4-difluorkrotonske kiseline formule VIII
[image]
naznačeni time, da su
R C1-C6-alkil,
R1 i R2 neovisno jedan o drugom vodik, C1-C4-alkil ili C1-C4-halogenalkil,
X kisik ili -NR4,
pri čemu R4 označava vodik ili C1-C6-alkil.
21. Postupak za pripravu spojeva formule I, naznačen time, da, derivat 4-klor-4,4,-diffuorlkrotonske kiseline formule VIII
[image]
u kojoj označavaju R vodik ili C1-C6-alkil,
R1 i R2 neovisno jedan o drugom vodik, C1-C4-alkili C1-C4-halogenalkil,
R3 vodik ili organski ostatak i X kisik ili -NR4-,
pri čemu R4 označava vodik ili C1-C6-alkil, hidriramo vodikom u nazočnosti katalizatora, te dobivene spojeve formule Id
[image]
gdje R1, R2, X i R imaju gore navedeno značenje, pretvorimo hidrolizom, reakcijom preesterifikacije ili reakcijom amidiranja u preostale spojeve formule I, prema zahtjevu 1.
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CH301289 | 1989-08-18 | ||
CH72790 | 1990-03-07 | ||
YU157190A YU157190A (sh) | 1989-08-18 | 1990-08-15 | Derivati maslene kisline |
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HRP940499A2 true HRP940499A2 (en) | 1997-06-30 |
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HRP-1571/90A HRP940499A2 (en) | 1989-08-18 | 1994-09-08 | Butric acid derivatives |
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EP (1) | EP0413666B1 (hr) |
JP (1) | JPH0390045A (hr) |
KR (1) | KR910004530A (hr) |
CN (1) | CN1049495A (hr) |
AT (1) | ATE104267T1 (hr) |
AU (1) | AU639708B2 (hr) |
BG (1) | BG60379B1 (hr) |
BR (1) | BR9004075A (hr) |
CA (1) | CA2023464A1 (hr) |
DE (1) | DE59005332D1 (hr) |
DK (1) | DK0413666T3 (hr) |
EG (1) | EG19084A (hr) |
ES (1) | ES2063324T3 (hr) |
HR (1) | HRP940499A2 (hr) |
HU (1) | HUT56053A (hr) |
IE (1) | IE63504B1 (hr) |
IL (1) | IL95346A0 (hr) |
MY (1) | MY106449A (hr) |
NZ (1) | NZ234935A (hr) |
TR (1) | TR25930A (hr) |
YU (1) | YU157190A (hr) |
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FR2658818B1 (fr) * | 1990-02-27 | 1993-12-31 | Adir Cie | Nouveaux derives a structure naphtalenique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
IL102676A0 (en) * | 1991-08-07 | 1993-01-14 | Ciba Geigy Ag | Butyric acid amides |
ATE155128T1 (de) * | 1991-11-01 | 1997-07-15 | Ciba Geigy Ag | Buttersäurederivate, verfahren zu ihrer herstellung und ihre verwendung als schädlingsbekämpfung |
ATE149482T1 (de) * | 1993-11-11 | 1997-03-15 | Basf Ag | P-hydroxyanilinderivate, verfahren zu ihrer herstellung und ihre verwendung zur bekämpfung von schadpilzen oder schädlingen |
DK0653417T3 (da) * | 1993-11-11 | 1998-03-30 | Basf Ag | P-Hydroxyanilinderivater, fremgangsmåde til deres fremstilling og deres anvendelse til bekæmpelse af skadelige svampe eller skadedyr |
JP2006223647A (ja) * | 2005-02-18 | 2006-08-31 | Hiroyasu Yamamoto | 速走力を増進させるためのトレーニング機 |
JP2007143748A (ja) * | 2005-11-25 | 2007-06-14 | Sharp Corp | 画像認識装置、フィットネス支援装置、フィットネス支援システム、フィットネス支援方法、制御プログラムおよび可読記録媒体 |
KR20110122188A (ko) * | 2009-02-19 | 2011-11-09 | 솔베이 플루오르 게엠베하 | 불소치환된 알칸산의 에스테르 조성물 |
CN106132923B (zh) * | 2014-03-17 | 2019-11-15 | 日产化学工业株式会社 | 低聚苯胺衍生物、电荷传输性清漆以及有机电致发光元件 |
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1990
- 1990-08-09 ES ES90810603T patent/ES2063324T3/es not_active Expired - Lifetime
- 1990-08-09 EP EP90810603A patent/EP0413666B1/de not_active Expired - Lifetime
- 1990-08-09 DK DK90810603.2T patent/DK0413666T3/da not_active Application Discontinuation
- 1990-08-09 AT AT90810603T patent/ATE104267T1/de not_active IP Right Cessation
- 1990-08-09 DE DE59005332T patent/DE59005332D1/de not_active Expired - Fee Related
- 1990-08-10 IL IL95346A patent/IL95346A0/xx unknown
- 1990-08-15 YU YU157190A patent/YU157190A/sh unknown
- 1990-08-16 NZ NZ234935A patent/NZ234935A/en unknown
- 1990-08-16 MY MYPI90001388A patent/MY106449A/en unknown
- 1990-08-16 BG BG92701A patent/BG60379B1/xx unknown
- 1990-08-16 CA CA002023464A patent/CA2023464A1/en not_active Abandoned
- 1990-08-16 TR TR90/0842A patent/TR25930A/xx unknown
- 1990-08-16 KR KR1019900012574A patent/KR910004530A/ko not_active Application Discontinuation
- 1990-08-17 HU HU905061A patent/HUT56053A/hu unknown
- 1990-08-17 JP JP2216953A patent/JPH0390045A/ja active Pending
- 1990-08-17 IE IE299090A patent/IE63504B1/en not_active IP Right Cessation
- 1990-08-17 AU AU61097/90A patent/AU639708B2/en not_active Ceased
- 1990-08-17 CN CN90107131A patent/CN1049495A/zh active Pending
- 1990-08-17 BR BR909004075A patent/BR9004075A/pt not_active Application Discontinuation
- 1990-08-18 EG EG48790A patent/EG19084A/xx active
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Also Published As
Publication number | Publication date |
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TR25930A (tr) | 1993-11-01 |
EP0413666B1 (de) | 1994-04-13 |
IE902990A1 (en) | 1991-02-27 |
ES2063324T3 (es) | 1995-01-01 |
CN1049495A (zh) | 1991-02-27 |
ATE104267T1 (de) | 1994-04-15 |
EG19084A (en) | 1994-09-29 |
KR910004530A (ko) | 1991-03-28 |
BG92701A (bg) | 1993-12-24 |
MY106449A (en) | 1995-05-30 |
AU6109790A (en) | 1991-02-21 |
EP0413666A1 (de) | 1991-02-20 |
BR9004075A (pt) | 1991-09-03 |
YU157190A (sh) | 1993-05-28 |
BG60379B1 (en) | 1995-01-03 |
CA2023464A1 (en) | 1991-02-19 |
NZ234935A (en) | 1991-12-23 |
AU639708B2 (en) | 1993-08-05 |
DE59005332D1 (de) | 1994-05-19 |
JPH0390045A (ja) | 1991-04-16 |
HU905061D0 (en) | 1991-01-28 |
IE63504B1 (en) | 1995-05-03 |
DK0413666T3 (da) | 1994-05-16 |
IL95346A0 (en) | 1991-06-30 |
HUT56053A (en) | 1991-07-29 |
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