DE10354607A1 - Siylierte Carboxamide - Google Patents
Siylierte Carboxamide Download PDFInfo
- Publication number
- DE10354607A1 DE10354607A1 DE10354607A DE10354607A DE10354607A1 DE 10354607 A1 DE10354607 A1 DE 10354607A1 DE 10354607 A DE10354607 A DE 10354607A DE 10354607 A DE10354607 A DE 10354607A DE 10354607 A1 DE10354607 A1 DE 10354607A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- alkoxy
- carbonyl
- formula
- haloalkyl
- 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.)
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- 150000003857 carboxamides Chemical class 0.000 title claims abstract description 18
- 244000005700 microbiome Species 0.000 claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 56
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 55
- 239000000460 chlorine Chemical group 0.000 claims description 55
- 229910052801 chlorine Inorganic materials 0.000 claims description 55
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 48
- 239000011737 fluorine Chemical group 0.000 claims description 48
- 229910052731 fluorine Inorganic materials 0.000 claims description 48
- 239000001257 hydrogen Substances 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- 125000001246 bromo group Chemical group Br* 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 30
- 125000005843 halogen group Chemical group 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 19
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 15
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 239000011593 sulfur Substances 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 6
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000011630 iodine Substances 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000006413 ring segment Chemical group 0.000 claims description 6
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 2
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004419 alkynylene group Chemical group 0.000 claims description 2
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 28
- -1 anilide radical Chemical group 0.000 description 100
- 241000196324 Embryophyta Species 0.000 description 73
- 150000002431 hydrogen Chemical group 0.000 description 24
- 239000004480 active ingredient Substances 0.000 description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 239000000203 mixture Substances 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 14
- 230000001965 increasing effect Effects 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 12
- 240000008042 Zea mays Species 0.000 description 11
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
- 241000233866 Fungi Species 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 9
- 239000003995 emulsifying agent Substances 0.000 description 9
- 230000001681 protective effect Effects 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 229920000742 Cotton Polymers 0.000 description 8
- 244000299507 Gossypium hirsutum Species 0.000 description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 8
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- 238000009472 formulation Methods 0.000 description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 7
- 108090000623 proteins and genes Proteins 0.000 description 7
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 244000068988 Glycine max Species 0.000 description 6
- 235000010469 Glycine max Nutrition 0.000 description 6
- 206010061217 Infestation Diseases 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 6
- 235000005822 corn Nutrition 0.000 description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 6
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 6
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 5
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 235000009973 maize Nutrition 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 4
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
- QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 4
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- 244000070406 Malus silvestris Species 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 244000061456 Solanum tuberosum Species 0.000 description 4
- 235000002595 Solanum tuberosum Nutrition 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
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- 150000001408 amides Chemical class 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
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- 239000010949 copper Substances 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
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- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 4
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- 238000012546 transfer Methods 0.000 description 1
- DDVNRFNDOPPVQJ-HQJQHLMTSA-N transfluthrin Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=CC(F)=C1F DDVNRFNDOPPVQJ-HQJQHLMTSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- JWXZLCFGVKMEEK-UHFFFAOYSA-N triarathene Chemical compound C1=CC(Cl)=CC=C1C1=CC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)S1 JWXZLCFGVKMEEK-UHFFFAOYSA-N 0.000 description 1
- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- HYWCXWRMUZYRPH-UHFFFAOYSA-N trimethyl(prop-2-enyl)silane Chemical compound C[Si](C)(C)CC=C HYWCXWRMUZYRPH-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 241000701447 unidentified baculovirus Species 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- LESVOLZBIFDZGS-UHFFFAOYSA-N vamidothion Chemical compound CNC(=O)C(C)SCCSP(=O)(OC)OC LESVOLZBIFDZGS-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 239000005943 zeta-Cypermethrin Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10354607A DE10354607A1 (de) | 2003-11-21 | 2003-11-21 | Siylierte Carboxamide |
| JP2006540234A JP4745979B2 (ja) | 2003-11-21 | 2004-11-06 | シリル化カルボキサミド |
| AT04797688T ATE478878T1 (de) | 2003-11-21 | 2004-11-06 | Silylierte carboxamide |
| BRPI0416200-5A BRPI0416200B1 (pt) | 2003-11-21 | 2004-11-06 | Carboxamidas sililadas, seu processo de preparação e seu emprego, agente e seu processo de preparação , e processo para combate de microorganismos indesejados |
| CA002546638A CA2546638A1 (en) | 2003-11-21 | 2004-11-06 | Silylated carboxamides |
| EP04797688A EP1687315B1 (de) | 2003-11-21 | 2004-11-06 | Silylierte carboxamide |
| MXPA06005529A MXPA06005529A (es) | 2003-11-21 | 2004-11-06 | Carboxamidas sililadas. |
| CNB2004800341871A CN100567306C (zh) | 2003-11-21 | 2004-11-06 | 甲硅烷基化甲酰胺 |
| KR1020067010445A KR20060120176A (ko) | 2003-11-21 | 2004-11-06 | 실릴화 카복사미드 |
| DE502004011589T DE502004011589D1 (de) | 2003-11-21 | 2004-11-06 | Silylierte carboxamide |
| US10/579,033 US7598389B2 (en) | 2003-11-21 | 2004-11-06 | Silylated carboxamides |
| PCT/EP2004/012590 WO2005049624A1 (de) | 2003-11-21 | 2004-11-06 | Silylierte carboxamide |
| ES04797688T ES2350486T3 (es) | 2003-11-21 | 2004-11-06 | Carboxamidas sililadas. |
| PL04797688T PL1687315T3 (pl) | 2003-11-21 | 2004-11-06 | Sililowane karboksyamidy |
| ARP040104218A AR046843A1 (es) | 2003-11-21 | 2004-11-16 | Carboxamidas sililadas |
| TW093135510A TW200526117A (en) | 2003-11-21 | 2004-11-19 | Silylated carboxamides |
| JP2011022336A JP2011144176A (ja) | 2003-11-21 | 2011-02-04 | シリル化カルボキサミド |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10354607A DE10354607A1 (de) | 2003-11-21 | 2003-11-21 | Siylierte Carboxamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10354607A1 true DE10354607A1 (de) | 2005-06-16 |
Family
ID=34585242
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10354607A Withdrawn DE10354607A1 (de) | 2003-11-21 | 2003-11-21 | Siylierte Carboxamide |
| DE502004011589T Expired - Lifetime DE502004011589D1 (de) | 2003-11-21 | 2004-11-06 | Silylierte carboxamide |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE502004011589T Expired - Lifetime DE502004011589D1 (de) | 2003-11-21 | 2004-11-06 | Silylierte carboxamide |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7598389B2 (enExample) |
| EP (1) | EP1687315B1 (enExample) |
| JP (2) | JP4745979B2 (enExample) |
| KR (1) | KR20060120176A (enExample) |
| CN (1) | CN100567306C (enExample) |
| AR (1) | AR046843A1 (enExample) |
| AT (1) | ATE478878T1 (enExample) |
| BR (1) | BRPI0416200B1 (enExample) |
| CA (1) | CA2546638A1 (enExample) |
| DE (2) | DE10354607A1 (enExample) |
| ES (1) | ES2350486T3 (enExample) |
| MX (1) | MXPA06005529A (enExample) |
| PL (1) | PL1687315T3 (enExample) |
| TW (1) | TW200526117A (enExample) |
| WO (1) | WO2005049624A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0207253D0 (en) * | 2002-03-27 | 2002-05-08 | Syngenta Participations Ag | Chemical compounds |
| KR20060009917A (ko) * | 2003-05-21 | 2006-02-01 | 바이엘 크롭사이언스 아게 | 요오도피라졸릴 카복스아닐리드 |
| DE10354607A1 (de) | 2003-11-21 | 2005-06-16 | Bayer Cropscience Ag | Siylierte Carboxamide |
| DE102004005785A1 (de) * | 2004-02-06 | 2005-08-25 | Bayer Cropscience Ag | 2-Halogenfuryl/thienyl-3-carboxamide |
| DE102004005786A1 (de) * | 2004-02-06 | 2005-08-25 | Bayer Cropscience Ag | Haloalkylcarboxamide |
| DE102004005787A1 (de) * | 2004-02-06 | 2005-08-25 | Bayer Cropscience Ag | Carboxamide |
| DE102004012901A1 (de) * | 2004-03-17 | 2005-10-06 | Bayer Cropscience Ag | Silylierte Carboxamide |
| DE102005022147A1 (de) * | 2005-04-28 | 2006-11-02 | Bayer Cropscience Ag | Wirkstoffkombinationen |
| AR064563A1 (es) * | 2007-01-03 | 2009-04-08 | Bayer Cropscience Ag | Derivados de n-alquinilbenzamida, un procedimiento para su preparacion, una composicion fungicida que lo comprende y su uso en un metodo para combatir hongos fitopatogenos. |
| WO2012065947A1 (en) | 2010-11-15 | 2012-05-24 | Bayer Cropscience Ag | 5-halogenopyrazolecarboxamides |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU664392B2 (en) * | 1991-10-18 | 1995-11-16 | Monsanto Technology Llc | Fungicides for the control of take-all disease of plants |
| IL103614A (en) | 1991-11-22 | 1998-09-24 | Basf Ag | Carboxamides for controlling botrytis and certain novel such compounds |
| US5223526A (en) | 1991-12-06 | 1993-06-29 | Monsanto Company | Pyrazole carboxanilide fungicides and use |
| DE4231517A1 (de) * | 1992-09-21 | 1994-03-24 | Basf Ag | Carbonsäureanilide, Verfahren zu ihrer Herstellung und sie enthaltende Mittel zur Bekämpfung von Schadpilzen |
| DE4231519A1 (de) | 1992-09-21 | 1994-03-24 | Basf Ag | Cyclohex(en)ylcarbonsäureamide, Verfahren zu ihrer Herstellung und sie enthaltende Mittel zur Bekämpfung von Schadpilzen |
| US5486621A (en) | 1994-12-15 | 1996-01-23 | Monsanto Company | Fungicides for the control of take-all disease of plants |
| GB9510459D0 (en) | 1995-05-24 | 1995-07-19 | Zeneca Ltd | Bicyclic amines |
| DE19629828A1 (de) * | 1996-07-24 | 1998-01-29 | Bayer Ag | Carbanilide |
| GB9624611D0 (en) | 1996-11-26 | 1997-01-15 | Zeneca Ltd | Bicyclic amine compounds |
| ID22349A (id) | 1996-11-26 | 1999-09-30 | Zeneca Ltd | Turunan dari 8-azabisiklo [3.2.1] oktana-, 8-azabisiklo [3.2.1] okt-6-ena-, 9-azabisiklo-[3.3.1] nonana-, 9-aza-3-oksabisiklo [3.3.1] nonana- dan 9-aza-3-tiobisiklo [3.3.1] nonana, pembuatannya dan penggunaannya sebagai insektisida |
| JP2001072510A (ja) * | 1999-09-03 | 2001-03-21 | Mitsui Chemicals Inc | 植物病害防除剤組成物 |
| US6476034B2 (en) | 2000-02-22 | 2002-11-05 | Bristol-Myers Squibb Company | Antiviral azaindole derivatives |
| MXPA03000688A (es) | 2000-07-24 | 2004-11-01 | Bayer Cropscience Ag | Bifenilcarboxiamidas. |
| RU2266285C2 (ru) * | 2001-05-31 | 2005-12-20 | Нихон Нохияку Ко.,Лтд. | Замещенное анилидное производное, его промежуточное соединение, химикаты для борьбы с вредителями сельскохозяйственных и плодовых культур и их использование |
| DE10136065A1 (de) | 2001-07-25 | 2003-02-13 | Bayer Cropscience Ag | Pyrazolylcarboxanilide |
| GB0207253D0 (en) * | 2002-03-27 | 2002-05-08 | Syngenta Participations Ag | Chemical compounds |
| DE10219035A1 (de) | 2002-04-29 | 2003-11-13 | Bayer Cropscience Ag | Biphenylcarboxamide |
| DE10229595A1 (de) | 2002-07-02 | 2004-01-15 | Bayer Cropscience Ag | Phenylbenzamide |
| PL375353A1 (en) | 2002-08-22 | 2005-11-28 | Syngenta Participations Ag | Chemical compounds |
| DE10258314A1 (de) | 2002-12-13 | 2004-06-24 | Bayer Cropscience Ag | Biphenyloximether |
| DE602004016141D1 (de) | 2003-05-07 | 2008-10-09 | Syngenta Participations Ag | 3-carbonylaminothiophene und ihrer verwendung als fungizide |
| DE10325439A1 (de) | 2003-05-21 | 2004-12-09 | Bayer Cropscience Ag | Iodpyrazolylcarboxanilide |
| BRPI0412486A (pt) | 2003-07-10 | 2006-09-19 | Bayer Cropscience Ag | piridinilanilidas |
| DE10354607A1 (de) | 2003-11-21 | 2005-06-16 | Bayer Cropscience Ag | Siylierte Carboxamide |
| DE102004005786A1 (de) | 2004-02-06 | 2005-08-25 | Bayer Cropscience Ag | Haloalkylcarboxamide |
| DE102004005785A1 (de) | 2004-02-06 | 2005-08-25 | Bayer Cropscience Ag | 2-Halogenfuryl/thienyl-3-carboxamide |
| DE102004012901A1 (de) | 2004-03-17 | 2005-10-06 | Bayer Cropscience Ag | Silylierte Carboxamide |
| DE102005060462A1 (de) | 2005-12-17 | 2007-06-28 | Bayer Cropscience Ag | Biphenylcarboxamide |
-
2003
- 2003-11-21 DE DE10354607A patent/DE10354607A1/de not_active Withdrawn
-
2004
- 2004-11-06 JP JP2006540234A patent/JP4745979B2/ja not_active Expired - Fee Related
- 2004-11-06 MX MXPA06005529A patent/MXPA06005529A/es active IP Right Grant
- 2004-11-06 ES ES04797688T patent/ES2350486T3/es not_active Expired - Lifetime
- 2004-11-06 PL PL04797688T patent/PL1687315T3/pl unknown
- 2004-11-06 CN CNB2004800341871A patent/CN100567306C/zh not_active Expired - Fee Related
- 2004-11-06 US US10/579,033 patent/US7598389B2/en not_active Expired - Fee Related
- 2004-11-06 KR KR1020067010445A patent/KR20060120176A/ko not_active Ceased
- 2004-11-06 BR BRPI0416200-5A patent/BRPI0416200B1/pt not_active IP Right Cessation
- 2004-11-06 AT AT04797688T patent/ATE478878T1/de not_active IP Right Cessation
- 2004-11-06 WO PCT/EP2004/012590 patent/WO2005049624A1/de not_active Ceased
- 2004-11-06 CA CA002546638A patent/CA2546638A1/en not_active Abandoned
- 2004-11-06 DE DE502004011589T patent/DE502004011589D1/de not_active Expired - Lifetime
- 2004-11-06 EP EP04797688A patent/EP1687315B1/de not_active Expired - Lifetime
- 2004-11-16 AR ARP040104218A patent/AR046843A1/es not_active Application Discontinuation
- 2004-11-19 TW TW093135510A patent/TW200526117A/zh unknown
-
2011
- 2011-02-04 JP JP2011022336A patent/JP2011144176A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ES2350486T3 (es) | 2011-01-24 |
| US20070191454A1 (en) | 2007-08-16 |
| JP2011144176A (ja) | 2011-07-28 |
| TW200526117A (en) | 2005-08-16 |
| CN100567306C (zh) | 2009-12-09 |
| EP1687315A1 (de) | 2006-08-09 |
| MXPA06005529A (es) | 2006-08-17 |
| ATE478878T1 (de) | 2010-09-15 |
| WO2005049624A1 (de) | 2005-06-02 |
| AR046843A1 (es) | 2005-12-28 |
| DE502004011589D1 (de) | 2010-10-07 |
| KR20060120176A (ko) | 2006-11-24 |
| US7598389B2 (en) | 2009-10-06 |
| BRPI0416200B1 (pt) | 2015-07-14 |
| JP4745979B2 (ja) | 2011-08-10 |
| BRPI0416200A (pt) | 2006-12-26 |
| JP2007511555A (ja) | 2007-05-10 |
| CN1882596A (zh) | 2006-12-20 |
| EP1687315B1 (de) | 2010-08-25 |
| PL1687315T3 (pl) | 2011-02-28 |
| CA2546638A1 (en) | 2005-06-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |