DE2841824A1 - Essigsaeureanilide, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes fungizides mittel - Google Patents
Essigsaeureanilide, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes fungizides mittelInfo
- Publication number
- DE2841824A1 DE2841824A1 DE19782841824 DE2841824A DE2841824A1 DE 2841824 A1 DE2841824 A1 DE 2841824A1 DE 19782841824 DE19782841824 DE 19782841824 DE 2841824 A DE2841824 A DE 2841824A DE 2841824 A1 DE2841824 A1 DE 2841824A1
- Authority
- DE
- Germany
- Prior art keywords
- furyl
- oxoperhydro
- deep
- anilide
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims description 30
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 title claims description 5
- 230000000855 fungicidal effect Effects 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000003931 anilides Chemical class 0.000 claims description 66
- -1 dimethylthiocarbamoyl group Chemical group 0.000 claims description 64
- 239000002253 acid Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 239000011593 sulfur Chemical group 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 239000000417 fungicide Substances 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- 239000000969 carrier Substances 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- KIUYINLYNRFJLM-UHFFFAOYSA-N chlorothiourea Chemical compound NC(=S)NCl KIUYINLYNRFJLM-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- LBYCVBUCBKMKPB-UHFFFAOYSA-N CC(OCC(N(C(CCO1)C1=O)C1=C(C)C=CC=C1C)=O)=O Chemical compound CC(OCC(N(C(CCO1)C1=O)C1=C(C)C=CC=C1C)=O)=O LBYCVBUCBKMKPB-UHFFFAOYSA-N 0.000 claims description 2
- CQABKVQVZHOCGR-UHFFFAOYSA-N CC1=C(N(C(CC(C)C)=S)C2C(OCC2)=O)C(=CC=C1)C Chemical compound CC1=C(N(C(CC(C)C)=S)C2C(OCC2)=O)C(=CC=C1)C CQABKVQVZHOCGR-UHFFFAOYSA-N 0.000 claims description 2
- FIAHXUROOGMDPR-UHFFFAOYSA-N CC1=C(N(C(CS(=O)(=O)C(C)C)=O)C2C(OCC2)=O)C(=CC=C1)C Chemical compound CC1=C(N(C(CS(=O)(=O)C(C)C)=O)C2C(OCC2)=O)C(=CC=C1)C FIAHXUROOGMDPR-UHFFFAOYSA-N 0.000 claims description 2
- YALDBMRHFGSWGQ-UHFFFAOYSA-N CCC(=S)N(C1CCOC1=O)C2=C(C=CC=C2C)C Chemical compound CCC(=S)N(C1CCOC1=O)C2=C(C=CC=C2C)C YALDBMRHFGSWGQ-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- ITRPUMGWMLDMKO-UHFFFAOYSA-N [2-(2,6-dimethyl-N-(2-oxooxolan-3-yl)anilino)-2-oxoethyl] N,N-dimethylcarbamodithioate Chemical compound CC1=C(N(C(=O)CSC(N(C)C)=S)C2C(OCC2)=O)C(=CC=C1)C ITRPUMGWMLDMKO-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims description 2
- 125000004803 chlorobenzyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004802 cyanophenyl group Chemical group 0.000 claims description 2
- 125000004188 dichlorophenyl group Chemical group 0.000 claims description 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000006178 methyl benzyl group Chemical group 0.000 claims description 2
- IPQNZYVMLHLAOK-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-methoxy-n-(2-oxooxolan-3-yl)acetamide Chemical compound CC=1C=CC=C(C)C=1N(C(=O)COC)C1CCOC1=O IPQNZYVMLHLAOK-UHFFFAOYSA-N 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical class CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 1
- DKKFHLAFQFWBIF-UHFFFAOYSA-N BrC=1C=C(N(C(COC(CCl)=O)=O)C2C(OCC2)=O)C=CC1 Chemical compound BrC=1C=C(N(C(COC(CCl)=O)=O)C2C(OCC2)=O)C=CC1 DKKFHLAFQFWBIF-UHFFFAOYSA-N 0.000 claims 1
- UNBCZTUYJYQBDL-UHFFFAOYSA-N CC(C=CC=C1)=C1N(C(CCO1)C1=O)C(COC)=O Chemical compound CC(C=CC=C1)=C1N(C(CCO1)C1=O)C(COC)=O UNBCZTUYJYQBDL-UHFFFAOYSA-N 0.000 claims 1
- MPOQWQYGAIHNKM-UHFFFAOYSA-N CC(C=CC=C1)=C1N(C(CCO1)C1=O)C(COC1=CC=CC=C1)=O Chemical compound CC(C=CC=C1)=C1N(C(CCO1)C1=O)C(COC1=CC=CC=C1)=O MPOQWQYGAIHNKM-UHFFFAOYSA-N 0.000 claims 1
- MVJHZKGCXPVEHN-UHFFFAOYSA-N CC(C=CC=C1C)=C1N(C(CCO1)C1=O)C(COC(CCl)=O)=O Chemical compound CC(C=CC=C1C)=C1N(C(CCO1)C1=O)C(COC(CCl)=O)=O MVJHZKGCXPVEHN-UHFFFAOYSA-N 0.000 claims 1
- NLUIYWIGQZACCA-UHFFFAOYSA-N CC(C=CC=C1C)=C1N(C(CCO1)C1=O)C(COC1=CC=CC=C1)=O Chemical compound CC(C=CC=C1C)=C1N(C(CCO1)C1=O)C(COC1=CC=CC=C1)=O NLUIYWIGQZACCA-UHFFFAOYSA-N 0.000 claims 1
- UKKYMRZUZVPUGW-UHFFFAOYSA-N CC(C=CC=C1C)=C1N(C(CCO1)C1=O)C(CSCC1=CC=CC=C1)=O Chemical compound CC(C=CC=C1C)=C1N(C(CCO1)C1=O)C(CSCC1=CC=CC=C1)=O UKKYMRZUZVPUGW-UHFFFAOYSA-N 0.000 claims 1
- XCAHULGUDNPSFF-UHFFFAOYSA-N CC(CC1N(C(COC(CCl)=O)=O)C2=C(C)C=CC=C2C)OC1=O Chemical compound CC(CC1N(C(COC(CCl)=O)=O)C2=C(C)C=CC=C2C)OC1=O XCAHULGUDNPSFF-UHFFFAOYSA-N 0.000 claims 1
- QMOJWZIWHSGMFV-UHFFFAOYSA-N CC(CC1N(C(COC)=O)C2=CC(F)=CC=C2)OC1=O Chemical compound CC(CC1N(C(COC)=O)C2=CC(F)=CC=C2)OC1=O QMOJWZIWHSGMFV-UHFFFAOYSA-N 0.000 claims 1
- AFVYEGHNSIROTE-UHFFFAOYSA-N CC(OCC(N(C(CCO1)C1=O)C1=C(C)C(C)=CC=C1)=O)=O Chemical compound CC(OCC(N(C(CCO1)C1=O)C1=C(C)C(C)=CC=C1)=O)=O AFVYEGHNSIROTE-UHFFFAOYSA-N 0.000 claims 1
- OXIOVOKPZZRLHR-UHFFFAOYSA-N CC(OCC(N(C(CCO1)C1=O)C1=CC(Br)=CC=C1)=O)=O Chemical compound CC(OCC(N(C(CCO1)C1=O)C1=CC(Br)=CC=C1)=O)=O OXIOVOKPZZRLHR-UHFFFAOYSA-N 0.000 claims 1
- XUIAFTCDTOHWFW-UHFFFAOYSA-N CC(OCC(N(C(CCO1)C1=O)C1=CC(C#N)=CC=C1)=O)=O Chemical compound CC(OCC(N(C(CCO1)C1=O)C1=CC(C#N)=CC=C1)=O)=O XUIAFTCDTOHWFW-UHFFFAOYSA-N 0.000 claims 1
- CODIHVSIMILYFZ-UHFFFAOYSA-N CC(OCC(N(C(CCO1)C1=O)C1=CC(C)=CC=C1)=O)=O Chemical compound CC(OCC(N(C(CCO1)C1=O)C1=CC(C)=CC=C1)=O)=O CODIHVSIMILYFZ-UHFFFAOYSA-N 0.000 claims 1
- UXTJFQABODWXNS-UHFFFAOYSA-N CC(OCC(N(C(CCO1)C1=O)C1=CC(Cl)=CC=C1)=O)=O Chemical compound CC(OCC(N(C(CCO1)C1=O)C1=CC(Cl)=CC=C1)=O)=O UXTJFQABODWXNS-UHFFFAOYSA-N 0.000 claims 1
- FOWDXMABMKSIIV-UHFFFAOYSA-N CC(OCC(N(C(CCO1)C1=O)C1=CC(F)=CC=C1)=O)=O Chemical compound CC(OCC(N(C(CCO1)C1=O)C1=CC(F)=CC=C1)=O)=O FOWDXMABMKSIIV-UHFFFAOYSA-N 0.000 claims 1
- ZPIDIMFEUSANFK-UHFFFAOYSA-N CC1=C(N(C(CC2=CC=CC=C2)=S)C2C(OCC2)=O)C(=CC=C1)C Chemical compound CC1=C(N(C(CC2=CC=CC=C2)=S)C2C(OCC2)=O)C(=CC=C1)C ZPIDIMFEUSANFK-UHFFFAOYSA-N 0.000 claims 1
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- FYTLYPLMLQOAOF-UHFFFAOYSA-N COCC(=O)N(C1CCOC1=O)C2=CC=CC(=C2)C#N Chemical compound COCC(=O)N(C1CCOC1=O)C2=CC=CC(=C2)C#N FYTLYPLMLQOAOF-UHFFFAOYSA-N 0.000 claims 1
- SXXFWYIYBWROGV-UHFFFAOYSA-N ClC=1C(=C(N(C(COC)=O)C2C(OCC2)=O)C=CC1)C Chemical compound ClC=1C(=C(N(C(COC)=O)C2C(OCC2)=O)C=CC1)C SXXFWYIYBWROGV-UHFFFAOYSA-N 0.000 claims 1
- CYEZXINASDCBPY-UHFFFAOYSA-N ClC=1C=C(N(C(COC)=O)C2C(OC(C2)C)=O)C=CC1 Chemical compound ClC=1C=C(N(C(COC)=O)C2C(OC(C2)C)=O)C=CC1 CYEZXINASDCBPY-UHFFFAOYSA-N 0.000 claims 1
- NPKXFJDIGYRPFV-UHFFFAOYSA-N N-(2,6-dimethylphenyl)-2-methoxy-N-(5-methyl-2-oxooxolan-3-yl)acetamide Chemical compound CC=1C=CC=C(C)C=1N(C(=O)COC)C1CC(C)OC1=O NPKXFJDIGYRPFV-UHFFFAOYSA-N 0.000 claims 1
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 241000233614 Phytophthora Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000004927 clay Substances 0.000 description 6
- 238000004382 potting Methods 0.000 description 6
- 239000002361 compost Substances 0.000 description 5
- MAVJUNGOXMOQON-UHFFFAOYSA-N 2-(2-chloroacetyl)oxyacetic acid Chemical compound OC(=O)COC(=O)CCl MAVJUNGOXMOQON-UHFFFAOYSA-N 0.000 description 4
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 4
- 230000002538 fungal effect Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000017074 necrotic cell death Effects 0.000 description 4
- 239000003415 peat Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 240000004713 Pisum sativum Species 0.000 description 3
- 235000010582 Pisum sativum Nutrition 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
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- 150000003839 salts Chemical class 0.000 description 3
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- 240000004160 Capsicum annuum Species 0.000 description 2
- 235000000292 Gouania lupuloides Nutrition 0.000 description 2
- 244000299452 Gouania lupuloides Species 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
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- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
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- 241000233629 Phytophthora parasitica Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000918584 Pythium ultimum Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 240000006365 Vitis vinifera Species 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000001511 capsicum annuum Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 235000005489 dwarf bean Nutrition 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- HZDNNJABYXNPPV-UHFFFAOYSA-N (2-chloro-2-oxoethyl) acetate Chemical compound CC(=O)OCC(Cl)=O HZDNNJABYXNPPV-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GSFSVEDCYBDIGW-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-6-chlorophenol Chemical compound OC1=C(Cl)C=CC=C1C1=NC2=CC=CC=C2S1 GSFSVEDCYBDIGW-UHFFFAOYSA-N 0.000 description 1
- UQDYTUWNBVAHEE-UHFFFAOYSA-N 2-(2-aminophenyl)sulfanylacetic acid Chemical compound NC1=CC=CC=C1SCC(O)=O UQDYTUWNBVAHEE-UHFFFAOYSA-N 0.000 description 1
- AWLVTQRRKPBQEQ-UHFFFAOYSA-N 2-benzylsulfanylacetic acid Chemical compound OC(=O)CSCC1=CC=CC=C1 AWLVTQRRKPBQEQ-UHFFFAOYSA-N 0.000 description 1
- OWDLFBLNMPCXSD-UHFFFAOYSA-N 2-chloro-N-(2,6-dimethylphenyl)-N-(2-oxotetrahydrofuran-3-yl)acetamide Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)C1C(=O)OCC1 OWDLFBLNMPCXSD-UHFFFAOYSA-N 0.000 description 1
- JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 1
- IXOFPUCWZCAFJX-UHFFFAOYSA-N 2-phenylethanethioic s-acid Chemical compound SC(=O)CC1=CC=CC=C1 IXOFPUCWZCAFJX-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241001465180 Botrytis Species 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- 235000002567 Capsicum annuum Nutrition 0.000 description 1
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 1
- 241001633993 Cineraria Species 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 241001300479 Macroptilium Species 0.000 description 1
- 239000006002 Pepper Substances 0.000 description 1
- 241000410021 Pericallis cruenta Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 235000008376 Phaseolus vulgaris var nanus Nutrition 0.000 description 1
- 241000233616 Phytophthora capsici Species 0.000 description 1
- 241000233647 Phytophthora nicotianae var. parasitica Species 0.000 description 1
- 235000016761 Piper aduncum Nutrition 0.000 description 1
- 235000017804 Piper guineense Nutrition 0.000 description 1
- 244000203593 Piper nigrum Species 0.000 description 1
- 235000008184 Piper nigrum Nutrition 0.000 description 1
- 241000233626 Plasmopara Species 0.000 description 1
- 241001281803 Plasmopara viticola Species 0.000 description 1
- 241000233639 Pythium Species 0.000 description 1
- 241000232168 Sinningia Species 0.000 description 1
- 244000093304 Sinningia speciosa Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- ZXSBDSGRQIWJPM-UHFFFAOYSA-N dimethylcarbamothioic s-acid Chemical compound CN(C)C(S)=O ZXSBDSGRQIWJPM-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 244000013123 dwarf bean Species 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
- A01N47/14—Di-thio analogues thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (23)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782841824 DE2841824A1 (de) | 1978-09-22 | 1978-09-22 | Essigsaeureanilide, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes fungizides mittel |
| NL7905267A NL7905267A (nl) | 1978-09-22 | 1979-07-05 | Azijnzuuraniliden, werkwijzen ter bereiding van deze verbindingen alsmede deze verbindingen-bevattende fun- gicide preparaten. |
| DK346179A DK346179A (da) | 1978-09-22 | 1979-08-17 | Eddikesyreanilider og fremgangsmaade til fremstilling deraf samt fungicide midler indeholdende forbindelserne |
| CS795676A CS219905B2 (en) | 1978-09-22 | 1979-08-20 | Fungicide means and method of making the active agents |
| YU02048/79A YU204879A (en) | 1978-09-22 | 1979-08-21 | Process for obtaining anilides of acetic acid |
| IT25202/79A IT1165288B (it) | 1978-09-22 | 1979-08-21 | Anilidi dell'acido acetico,procedimento per la preparazione di questi composti e mezzi funghicidi che li contengono |
| BR7905455A BR7905455A (pt) | 1978-09-22 | 1979-08-24 | Anilidas de acido acetico, processo para a preparacao destes compostos, bem como composicoes fungicidas contendo os mesmos |
| ES483787A ES483787A1 (es) | 1978-09-22 | 1979-08-31 | Procedimiento para la preparacion de nuevas anilidas de aci-dos aceticos |
| DD79215492A DD145989A5 (de) | 1978-09-22 | 1979-09-12 | Fungizides mittel |
| GB7932156A GB2033379B (en) | 1978-09-22 | 1979-09-17 | Fungicidally active acetic acid anilides and their manufacture and use |
| IL58273A IL58273A0 (en) | 1978-09-22 | 1979-09-19 | Acetic acid anilides methods for their manufacture and useand preparations containing them |
| LU81703A LU81703A1 (de) | 1978-09-22 | 1979-09-20 | Essigsaeureanilide,verfahren zur herstellung dieser verbindungen sowie diese enthaltendes fungizides mittel |
| PL1979218428A PL119374B1 (en) | 1978-09-22 | 1979-09-20 | Fungicide |
| RO7998732A RO78587A (ro) | 1978-09-22 | 1979-09-21 | Procedeu pentru prepararea unor anilide ale acidului acetic |
| SU792817359A SU988191A3 (ru) | 1978-09-22 | 1979-09-21 | Способ получени анилидов уксусной кислоты |
| BG044915A BG30624A3 (en) | 1978-09-22 | 1979-09-21 | Fungicide means |
| AT0622679A AT365890B (de) | 1978-09-22 | 1979-09-21 | Fungizides mittel |
| JP12092979A JPS5545682A (en) | 1978-09-22 | 1979-09-21 | Acetic anilide*its manufacture and fungicide containing said anilide |
| ZA00795121A ZA795021B (en) | 1978-09-22 | 1979-09-21 | Fungicidally active acetic acid anilides and their manufacture and use |
| AU51076/79A AU5107679A (en) | 1978-09-22 | 1979-09-21 | Acetic acid anilides |
| BE0/197256A BE878924A (fr) | 1978-09-22 | 1979-09-21 | Anilides d'acide acetique, leur procede de preparation et leur utilisation |
| HU79SCHE692A HU182612B (en) | 1978-09-22 | 1979-09-22 | Fungicide compositions containing acetanilide derivatives as active agents, and process for producing these active agents |
| FR7923680A FR2436782A1 (fr) | 1978-09-22 | 1979-09-24 | Anilides d'acides acetiques substitues et produits fongicides qui en contiennent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782841824 DE2841824A1 (de) | 1978-09-22 | 1978-09-22 | Essigsaeureanilide, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes fungizides mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2841824A1 true DE2841824A1 (de) | 1980-04-03 |
Family
ID=6050476
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782841824 Withdrawn DE2841824A1 (de) | 1978-09-22 | 1978-09-22 | Essigsaeureanilide, verfahren zur herstellung dieser verbindungen sowie diese enthaltendes fungizides mittel |
Country Status (23)
| Country | Link |
|---|---|
| JP (1) | JPS5545682A (cs) |
| AT (1) | AT365890B (cs) |
| AU (1) | AU5107679A (cs) |
| BE (1) | BE878924A (cs) |
| BG (1) | BG30624A3 (cs) |
| BR (1) | BR7905455A (cs) |
| CS (1) | CS219905B2 (cs) |
| DD (1) | DD145989A5 (cs) |
| DE (1) | DE2841824A1 (cs) |
| DK (1) | DK346179A (cs) |
| ES (1) | ES483787A1 (cs) |
| FR (1) | FR2436782A1 (cs) |
| GB (1) | GB2033379B (cs) |
| HU (1) | HU182612B (cs) |
| IL (1) | IL58273A0 (cs) |
| IT (1) | IT1165288B (cs) |
| LU (1) | LU81703A1 (cs) |
| NL (1) | NL7905267A (cs) |
| PL (1) | PL119374B1 (cs) |
| RO (1) | RO78587A (cs) |
| SU (1) | SU988191A3 (cs) |
| YU (1) | YU204879A (cs) |
| ZA (1) | ZA795021B (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2845454A1 (de) * | 1977-11-01 | 1979-05-10 | Chevron Res | 3-(n-acyl-n-arylamino)- gamma -butyrolactone und - gamma -butyrothiolactone sowie fungizide mittel |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02124375U (cs) * | 1989-03-27 | 1990-10-12 |
-
1978
- 1978-09-22 DE DE19782841824 patent/DE2841824A1/de not_active Withdrawn
-
1979
- 1979-07-05 NL NL7905267A patent/NL7905267A/nl not_active Application Discontinuation
- 1979-08-17 DK DK346179A patent/DK346179A/da not_active Application Discontinuation
- 1979-08-20 CS CS795676A patent/CS219905B2/cs unknown
- 1979-08-21 YU YU02048/79A patent/YU204879A/xx unknown
- 1979-08-21 IT IT25202/79A patent/IT1165288B/it active
- 1979-08-24 BR BR7905455A patent/BR7905455A/pt unknown
- 1979-08-31 ES ES483787A patent/ES483787A1/es not_active Expired
- 1979-09-12 DD DD79215492A patent/DD145989A5/de unknown
- 1979-09-17 GB GB7932156A patent/GB2033379B/en not_active Expired
- 1979-09-19 IL IL58273A patent/IL58273A0/xx unknown
- 1979-09-20 PL PL1979218428A patent/PL119374B1/pl unknown
- 1979-09-20 LU LU81703A patent/LU81703A1/de unknown
- 1979-09-21 RO RO7998732A patent/RO78587A/ro unknown
- 1979-09-21 SU SU792817359A patent/SU988191A3/ru active
- 1979-09-21 BE BE0/197256A patent/BE878924A/fr not_active IP Right Cessation
- 1979-09-21 ZA ZA00795121A patent/ZA795021B/xx unknown
- 1979-09-21 BG BG044915A patent/BG30624A3/xx unknown
- 1979-09-21 AT AT0622679A patent/AT365890B/de not_active IP Right Cessation
- 1979-09-21 AU AU51076/79A patent/AU5107679A/en not_active Abandoned
- 1979-09-21 JP JP12092979A patent/JPS5545682A/ja active Pending
- 1979-09-22 HU HU79SCHE692A patent/HU182612B/hu unknown
- 1979-09-24 FR FR7923680A patent/FR2436782A1/fr active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2845454A1 (de) * | 1977-11-01 | 1979-05-10 | Chevron Res | 3-(n-acyl-n-arylamino)- gamma -butyrolactone und - gamma -butyrothiolactone sowie fungizide mittel |
Also Published As
| Publication number | Publication date |
|---|---|
| IL58273A0 (en) | 1979-12-30 |
| BR7905455A (pt) | 1980-05-20 |
| ES483787A1 (es) | 1980-05-16 |
| ZA795021B (en) | 1980-09-24 |
| CS219905B2 (en) | 1983-03-25 |
| IT1165288B (it) | 1987-04-22 |
| AU5107679A (en) | 1980-04-17 |
| BE878924A (fr) | 1980-03-21 |
| JPS5545682A (en) | 1980-03-31 |
| AT365890B (de) | 1982-02-25 |
| FR2436782B1 (cs) | 1983-07-22 |
| ATA622679A (de) | 1981-07-15 |
| FR2436782A1 (fr) | 1980-04-18 |
| BG30624A3 (en) | 1981-07-15 |
| GB2033379B (en) | 1982-12-22 |
| GB2033379A (en) | 1980-05-21 |
| DK346179A (da) | 1980-03-23 |
| HU182612B (en) | 1984-02-28 |
| PL218428A1 (cs) | 1980-07-14 |
| SU988191A3 (ru) | 1983-01-07 |
| RO78587A (ro) | 1982-03-24 |
| IT7925202A0 (it) | 1979-08-21 |
| DD145989A5 (de) | 1981-01-21 |
| NL7905267A (nl) | 1980-03-25 |
| LU81703A1 (de) | 1980-01-24 |
| PL119374B1 (en) | 1981-12-31 |
| YU204879A (en) | 1983-02-28 |
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