KR20040105250A - 아미디닐페닐 화합물 및 그의 살진균제로서의 용도 - Google Patents
아미디닐페닐 화합물 및 그의 살진균제로서의 용도 Download PDFInfo
- Publication number
- KR20040105250A KR20040105250A KR20047017646A KR20047017646A KR20040105250A KR 20040105250 A KR20040105250 A KR 20040105250A KR 20047017646 A KR20047017646 A KR 20047017646A KR 20047017646 A KR20047017646 A KR 20047017646A KR 20040105250 A KR20040105250 A KR 20040105250A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- compound
- optionally substituted
- alkenyl
- formula
- 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- Withdrawn
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 174
- 239000000417 fungicide Substances 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 49
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 48
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 48
- 239000000203 mixture Substances 0.000 claims abstract description 45
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 43
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 31
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims abstract description 28
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims abstract description 25
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims abstract description 25
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 20
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 19
- 125000004665 trialkylsilyl group Chemical group 0.000 claims abstract description 19
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 16
- 201000010099 disease Diseases 0.000 claims abstract description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 16
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 12
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 6
- 244000000004 fungal plant pathogen Species 0.000 claims abstract description 6
- 125000006413 ring segment Chemical group 0.000 claims abstract description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 4
- -1 C 1 -C 4 alkylthio Chemical group 0.000 claims description 84
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 24
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 239000007787 solid Substances 0.000 claims description 18
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 17
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 17
- 125000004429 atom Chemical group 0.000 claims description 16
- 239000003085 diluting agent Substances 0.000 claims description 15
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 14
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 14
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 125000004702 alkoxy alkyl carbonyl group Chemical group 0.000 claims description 13
- 125000005389 trialkylsiloxy group Chemical group 0.000 claims description 13
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 12
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 10
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 230000000855 fungicidal effect Effects 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- 239000004094 surface-active agent Substances 0.000 claims description 10
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 9
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 9
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 9
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 9
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 9
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 9
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 8
- 230000009471 action Effects 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- 241000196324 Embryophyta Species 0.000 description 24
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 238000002360 preparation method Methods 0.000 description 22
- LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 description 19
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 18
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 18
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 18
- 229940126657 Compound 17 Drugs 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 17
- 229940125851 compound 27 Drugs 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000725 suspension Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 229930182558 Sterol Natural products 0.000 description 11
- 229940125904 compound 1 Drugs 0.000 description 11
- 229940125782 compound 2 Drugs 0.000 description 11
- 229940126214 compound 3 Drugs 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 150000003432 sterols Chemical class 0.000 description 11
- 235000003702 sterols Nutrition 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- 238000009472 formulation Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 description 8
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 8
- 101150065749 Churc1 gene Proteins 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- 102100038239 Protein Churchill Human genes 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- YLEIFZAVNWDOBM-ZTNXSLBXSA-N ac1l9hc7 Chemical compound C([C@H]12)C[C@@H](C([C@@H](O)CC3)(C)C)[C@@]43C[C@@]14CC[C@@]1(C)[C@@]2(C)C[C@@H]2O[C@]3(O)[C@H](O)C(C)(C)O[C@@H]3[C@@H](C)[C@H]12 YLEIFZAVNWDOBM-ZTNXSLBXSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- ASQOQJYHIYYTEJ-GBESFXJTSA-N (1r,7s,9as)-7-decyl-2,3,4,6,7,8,9,9a-octahydro-1h-quinolizin-1-ol Chemical compound O[C@@H]1CCCN2C[C@@H](CCCCCCCCCC)CC[C@H]21 ASQOQJYHIYYTEJ-GBESFXJTSA-N 0.000 description 7
- 239000005730 Azoxystrobin Substances 0.000 description 7
- 150000001204 N-oxides Chemical class 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- WFDXOXNFNRHQEC-GHRIWEEISA-N azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 description 7
- 229940125898 compound 5 Drugs 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- ZMYFCFLJBGAQRS-IAGOWNOFSA-N (2S,3R)-epoxiconazole Chemical compound C1=CC(F)=CC=C1[C@]1(CN2N=CN=C2)[C@@H](C=2C(=CC=CC=2)Cl)O1 ZMYFCFLJBGAQRS-IAGOWNOFSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000005869 Pyraclostrobin Substances 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 229940100198 alkylating agent Drugs 0.000 description 6
- 239000002168 alkylating agent Substances 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 230000006696 biosynthetic metabolic pathway Effects 0.000 description 6
- WXUZAHCNPWONDH-DYTRJAOYSA-N dimoxystrobin Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1COC1=CC(C)=CC=C1C WXUZAHCNPWONDH-DYTRJAOYSA-N 0.000 description 6
- FQKUGOMFVDPBIZ-UHFFFAOYSA-N flusilazole Chemical compound C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 FQKUGOMFVDPBIZ-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- SHAHPWSYJFYMRX-GDLCADMTSA-N (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C[C@@H]1[C@@H](O)CCC1 SHAHPWSYJFYMRX-GDLCADMTSA-N 0.000 description 5
- YCIPQJTZJGUXND-UHFFFAOYSA-N Aglaia odorata Alkaloid Natural products C1=CC(OC)=CC=C1C1(C(C=2C(=O)N3CCCC3=NC=22)C=3C=CC=CC=3)C2(O)C2=C(OC)C=C(OC)C=C2O1 YCIPQJTZJGUXND-UHFFFAOYSA-N 0.000 description 5
- 239000005868 Metconazole Substances 0.000 description 5
- TZYWCYJVHRLUCT-VABKMULXSA-N N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal Chemical compound CC(C)C[C@@H](C=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)OCC1=CC=CC=C1 TZYWCYJVHRLUCT-VABKMULXSA-N 0.000 description 5
- 239000005822 Propiconazole Substances 0.000 description 5
- 241000209140 Triticum Species 0.000 description 5
- 235000021307 Triticum Nutrition 0.000 description 5
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 125000001188 haloalkyl group Chemical group 0.000 description 5
- 239000002917 insecticide Substances 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- XWPZUHJBOLQNMN-UHFFFAOYSA-N metconazole Chemical compound C1=NC=NN1CC1(O)C(C)(C)CCC1CC1=CC=C(Cl)C=C1 XWPZUHJBOLQNMN-UHFFFAOYSA-N 0.000 description 5
- HIIRDDUVRXCDBN-OBGWFSINSA-N metominostrobin Chemical compound CNC(=O)C(=N\OC)\C1=CC=CC=C1OC1=CC=CC=C1 HIIRDDUVRXCDBN-OBGWFSINSA-N 0.000 description 5
- 238000007344 nucleophilic reaction Methods 0.000 description 5
- 244000052769 pathogen Species 0.000 description 5
- 239000008188 pellet Substances 0.000 description 5
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 5
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 4
- 239000005740 Boscalid Substances 0.000 description 4
- 101000615488 Homo sapiens Methyl-CpG-binding domain protein 2 Proteins 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 102100021299 Methyl-CpG-binding domain protein 2 Human genes 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 239000005839 Tebuconazole Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- WYEMLYFITZORAB-UHFFFAOYSA-N boscalid Chemical compound C1=CC(Cl)=CC=C1C1=CC=CC=C1NC(=O)C1=CC=CN=C1Cl WYEMLYFITZORAB-UHFFFAOYSA-N 0.000 description 4
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000004495 emulsifiable concentrate Substances 0.000 description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
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- LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 description 1
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- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-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
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- A01N37/52—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 groups, e.g. carboxylic acid amidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
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- A—HUMAN NECESSITIES
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- 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
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
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- 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
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
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- 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
- A01N49/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof
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- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
- C07C257/12—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to hydrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
- C07C257/14—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/70—Compounds containing any of the groups, e.g. isoureas
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/33—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring
- C07C323/35—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group
- C07C323/36—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group the sulfur atom of the sulfide group being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/18—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/30—Isothioureas
- C07C335/36—Isothioureas having sulfur atoms of isothiourea groups bound to carbon atoms of six-membered aromatic rings
-
- 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
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Insects & Arthropods (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38009502P | 2002-05-03 | 2002-05-03 | |
| US60/380,095 | 2002-05-03 | ||
| PCT/US2003/013371 WO2003093224A1 (en) | 2002-05-03 | 2003-04-30 | Amidinylphenyl compounds and their use as fungicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20040105250A true KR20040105250A (ko) | 2004-12-14 |
Family
ID=29401625
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR20047017646A Withdrawn KR20040105250A (ko) | 2002-05-03 | 2003-04-30 | 아미디닐페닐 화합물 및 그의 살진균제로서의 용도 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20050182025A1 (enExample) |
| EP (1) | EP1501789A1 (enExample) |
| JP (1) | JP2005524706A (enExample) |
| KR (1) | KR20040105250A (enExample) |
| CN (1) | CN1649833A (enExample) |
| AU (1) | AU2003241327A1 (enExample) |
| BR (1) | BR0309599A (enExample) |
| IL (1) | IL164310A0 (enExample) |
| MX (1) | MXPA04010732A (enExample) |
| PL (1) | PL373618A1 (enExample) |
| RU (1) | RU2004135323A (enExample) |
| UA (1) | UA78039C2 (enExample) |
| WO (1) | WO2003093224A1 (enExample) |
Families Citing this family (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1570736A1 (en) * | 2004-03-05 | 2005-09-07 | Bayer CropScience S.A. | Fungicide composition comprising an arylamidine derivative and known fungicide compounds |
| EA200602287A1 (ru) * | 2004-06-03 | 2007-04-27 | Е. И. Дюпон Де Немур Энд Компани | Фунгицидные смеси амидинилфенильных соединений |
| CA2619059A1 (en) * | 2005-09-13 | 2007-03-22 | Bayer Cropscience Ag | Pesticide thiazolyloxy substituted phenylamidine derivatives |
| TW200804245A (en) * | 2005-11-23 | 2008-01-16 | Du Pont | Amidinylphenyl compounds and their use as fungicides |
| RU2532135C2 (ru) * | 2007-02-22 | 2014-10-27 | Зингента Партисипейшнс Аг | Производные иминопиридина и их применение в качестве микробиоцидов |
| EP1969930A1 (de) * | 2007-03-12 | 2008-09-17 | Bayer CropScience AG | Phenoxyphenylamidine und deren Verwendung als Fungizide |
| BRPI0808846A2 (pt) | 2007-03-12 | 2019-09-24 | Bayer Cropscience Ag | fenoxifenilamidinas 3-substituídas e seu uso como fungicidas |
| EP1969929A1 (de) | 2007-03-12 | 2008-09-17 | Bayer CropScience AG | Substituierte Phenylamidine und deren Verwendung als Fungizide |
| EP2120558B1 (de) | 2007-03-12 | 2016-02-10 | Bayer Intellectual Property GmbH | 3,4-Disubstituierte Phenoxyphenylamidin-Derivate und deren Verwendung als Fungizide |
| EP1969934A1 (de) | 2007-03-12 | 2008-09-17 | Bayer CropScience AG | 4-Cycloalkyl-oder 4-arylsubstituierte Phenoxyphenylamidine und deren Verwendung als Fungizide |
| EP1969931A1 (de) | 2007-03-12 | 2008-09-17 | Bayer CropScience Aktiengesellschaft | Fluoalkylphenylamidine und deren Verwendung als Fungizide |
| WO2008110279A1 (de) | 2007-03-12 | 2008-09-18 | Bayer Cropscience Ag | Dihalogenphenoxyphenylamidine und deren verwendung als fungizide |
| CA2684340A1 (en) * | 2007-04-19 | 2008-10-30 | Bayer Cropscience Ag | Thiadiazolyloxyphenylamidines and the use thereof as fungicides |
| KR20100093060A (ko) * | 2007-10-26 | 2010-08-24 | 바스프 에스이 | 살진균 화합물, 이의 제조 방법 및 유해 진균 방제를 위한 이의 용도, 및 이를 포함하는 조성물 |
| EP2072506A1 (de) | 2007-12-21 | 2009-06-24 | Bayer CropScience AG | Thiazolyloxyphenylamidine oder Thiadiazolyloxyphenylamidine und deren Verwendung als Fungizide |
| US7723528B2 (en) * | 2008-06-05 | 2010-05-25 | Am Chemicals Llc | Sulfur transfer reagents for oligonucleotide synthesis |
| CN102066347B (zh) | 2008-06-27 | 2016-06-08 | 拜耳知识产权有限责任公司 | 噻二唑氧苯基脒及其作为杀菌剂的应用 |
| CN102076674B (zh) | 2008-06-27 | 2018-04-24 | 拜耳知识产权有限责任公司 | 噻二唑基氧苯基脒类及其作为杀真菌剂的应用 |
| EP2223917A1 (de) | 2009-02-02 | 2010-09-01 | Bayer CropScience AG | Isothiazolyloxyphenylamidine und deren Verwendung als Fungizide |
| WO2010115758A2 (en) | 2009-04-03 | 2010-10-14 | Basf Se | Fungicidal compounds |
| US8552175B2 (en) | 2009-04-23 | 2013-10-08 | A.M. Chemicals, Inc. | Sulfur transfer reagents for oligonucleotide synthesis |
| EP2264010A1 (de) | 2009-06-03 | 2010-12-22 | Bayer CropScience AG | Hetarylamidine |
| EP2264012A1 (de) | 2009-06-03 | 2010-12-22 | Bayer CropScience AG | Heteroarylamidine und deren Verwendung als Fungizide |
| EP2264011A1 (de) | 2009-06-03 | 2010-12-22 | Bayer CropScience AG | Heteroarylamidine und deren Verwendung als Fungizide |
| WO2011006604A1 (de) | 2009-07-17 | 2011-01-20 | Bayer Cropscience Ag | Substituierte aminothiazole und deren verwendung als fungizide |
| BR112012005581B1 (pt) | 2009-09-16 | 2021-04-20 | Basf Se | método para reduzir emissão de óxido nitroso de solos |
| WO2011080044A2 (en) | 2009-12-16 | 2011-07-07 | Bayer Cropscience Ag | Active compound combinations |
| WO2011082941A1 (de) | 2009-12-16 | 2011-07-14 | Bayer Cropscience Ag | Benzylsubstituierte thiadiazolyloxyphenylamidiniumsalze als fungizide |
| WO2011120912A1 (en) | 2010-03-29 | 2011-10-06 | Basf Se | Fungicidal iminoderivatives |
| WO2012019998A1 (de) | 2010-08-10 | 2012-02-16 | Bayer Cropscience Ag | Herstellung von n'-(4-{[3-(4-chlorbenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-n-ethyl-n-methylimidoformamid |
| ITMI20101564A1 (it) | 2010-08-23 | 2012-02-24 | Isagro Ricerca Srl | Fenilammidine ad elevata attivita' fungicida e relativo uso |
| ITMI20101575A1 (it) * | 2010-08-26 | 2012-02-27 | Isagro Ricerca Srl | Fenilammidine ad elevata attivita' fungicida e relativo uso |
| WO2012060401A1 (ja) * | 2010-11-05 | 2012-05-10 | 大塚アグリテクノ株式会社 | エチニルフェニルアミジン化合物又はその塩、その製造方法及び農園芸用殺菌剤 |
| WO2012090969A1 (en) * | 2010-12-27 | 2012-07-05 | Sumitomo Chemical Company, Limited | Amidine compounds and use thereof for plant disease control |
| ITMI20120405A1 (it) | 2012-03-15 | 2013-09-16 | Chemtura Corp | "composizioni sinergiche ad attivita' fungicida e relativo uso" |
| US9309191B2 (en) | 2013-03-25 | 2016-04-12 | Sumitomo Chemical Company, Limited | Amidine compound and use thereof |
| WO2015055764A1 (en) | 2013-10-18 | 2015-04-23 | Syngenta Participations Ag | 3-methanimidamid-pyridine derivatives as fungicides |
| JP6543269B2 (ja) | 2014-04-11 | 2019-07-10 | シンジェンタ パーティシペーションズ アーゲー | 農業において使用される殺菌・殺カビ性n’−[2−メチル−6−[2−アルコキシ−エトキシ]−3−ピリジル]−n−アルキル−ホルムアミジン誘導体 |
| CN107074770B (zh) * | 2014-11-06 | 2021-03-09 | 先正达参股股份有限公司 | 新颖的杀真菌的吡啶脒 |
| US10252977B2 (en) | 2015-06-15 | 2019-04-09 | Bayer Cropscience Aktiengesellschaft | Halogen-substituted phenoxyphenylamidines and the use thereof as fungicides |
| JP2018522846A (ja) | 2015-06-15 | 2018-08-16 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | ハロゲン置換フェノキシフェニルアミジン類及び殺菌剤としてのそれらの使用 |
| AU2016289731B2 (en) * | 2015-07-08 | 2020-09-10 | Bayer Cropscience Aktiengesellschaft | Phenoxyhalogenphenylamidines and the use thereof as fungicides |
| HUE049099T2 (hu) | 2015-10-14 | 2020-09-28 | Syngenta Participations Ag | Fungicid hatású készítmények |
| BR112019007468B1 (pt) | 2016-10-14 | 2023-02-14 | Pi Industries Ltd | Derivados da fenilamina 4-substituídos e seu uso para proteger as culturas combatendo microrganismos fitopatogênicos indesejáveis |
| WO2018069842A1 (en) | 2016-10-14 | 2018-04-19 | Pi Industries Ltd | 4-amino substituted phenylamidine derivatives and their use to protect crops by fighting undesired phytopathogenic micoorganisms |
| WO2018109002A1 (en) | 2016-12-14 | 2018-06-21 | Bayer Cropscience Aktiengesellschaft | Active compound combinations |
| CA3046718A1 (en) | 2016-12-14 | 2018-06-21 | Bayer Cropscience Aktiengesellschaft | Phenylamidines and the use thereof as fungicides |
| EP3335559A1 (en) | 2016-12-14 | 2018-06-20 | Bayer CropScience Aktiengesellschaft | Active compound combinations |
| AU2017375006A1 (en) | 2016-12-14 | 2019-07-04 | Bayer Aktiengesellschaft | Phenoxyphenylamidines and the use thereof as fungicides |
| MX2019012468A (es) | 2017-04-20 | 2019-12-11 | Pi Industries Ltd | Nuevos compuestos de fenilamina. |
| CN110770210A (zh) | 2017-05-18 | 2020-02-07 | Pi工业有限公司 | 新颖的脒化合物 |
| JP2020523382A (ja) * | 2017-06-14 | 2020-08-06 | シンジェンタ パーティシペーションズ アーゲー | 殺菌・殺カビ性組成物 |
| WO2019202459A1 (en) | 2018-04-16 | 2019-10-24 | Pi Industries Ltd. | Use of 4-substituted phenylamidine compounds for controlling disease rust diseases in plants |
| AR115966A1 (es) | 2018-08-17 | 2021-03-17 | Pi Industries Ltd | Compuestos de fenilamidina y sus usos |
| UY38540A (es) * | 2019-01-14 | 2020-08-31 | Pi Industries Ltd | Compuestos de fenilamidina 3-sustituida, preparación y uso |
| WO2020237131A1 (en) * | 2019-05-23 | 2020-11-26 | Dow Agrosciences Llc | Fungicidal aryl amidines |
| AR120427A1 (es) | 2019-11-12 | 2022-02-16 | Pi Industries Ltd | Composición agroquímica que comprende compuestos de fenilamidina 4-sustituidos |
| EP3708565A1 (en) | 2020-03-04 | 2020-09-16 | Bayer AG | Pyrimidinyloxyphenylamidines and the use thereof as fungicides |
| TWI879751B (zh) * | 2020-03-23 | 2025-04-11 | 印度商皮埃企業有限公司 | 3-被取代的苯基脒化合物及其製備和用途 |
| EP4250926A1 (en) | 2020-11-30 | 2023-10-04 | PI Industries Ltd. | Agrochemical composition comprising 3-substituted phenylamidine compounds and use thereof |
| WO2022117650A1 (en) | 2020-12-02 | 2022-06-09 | Syngenta Crop Protection Ag | Fungicidal compositions |
| EP3915971A1 (en) | 2020-12-16 | 2021-12-01 | Bayer Aktiengesellschaft | Phenyl-s(o)n-phenylamidines and the use thereof as fungicides |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH432929A (de) * | 1962-03-08 | 1967-03-31 | Ciba Geigy | Schädlingsbekämpfungsmittel |
| US3911010A (en) * | 1970-06-13 | 1975-10-07 | Bayer Ag | Aminophenylamidines, their production and their pharmaceutical use |
| US3996247A (en) * | 1970-06-13 | 1976-12-07 | Bayer Aktiengesellschaft | Substituted 4-aminophenylamidines |
| DE2029298C3 (de) * | 1970-06-13 | 1980-04-17 | Bayer Ag, 5090 Leverkusen | Aminophenylamidine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
| US4013676A (en) * | 1970-06-13 | 1977-03-22 | Bayer Aktiengesellschaft | Aminophenylamidines, their production and their pharmaceutical use |
| US4018814A (en) * | 1970-06-13 | 1977-04-19 | Bayer Aktiengesellschaft | Aromatic amides and carbomates of phenylamidines |
| DE2113978A1 (de) * | 1971-03-23 | 1972-10-12 | Hoechst Ag | Herbizide Mittel |
| BE792407A (fr) * | 1971-12-07 | 1973-06-07 | Ciba Geigy | Phenylformamidines agissant sur la croissance des |
| DE2235935C3 (de) * | 1972-07-21 | 1979-07-26 | Lentia Gmbh | Neue Derivate von trijodierten Aminobenzolcarbonsäuren, ein Verfahren zu deren Herstellung und diese Verbindungen enthaltende Röntgenkontrastmittel |
| US4025550A (en) * | 1972-07-21 | 1977-05-24 | Chemie Linz Aktiengesellschaft | Derivatives of triiodo-aminobenzenecarboxylic acids and the preparation thereof |
| US4209319A (en) * | 1972-12-01 | 1980-06-24 | Ciba-Geigy Corporation | Herbicidally active phenylformamidine compounds |
| DE2321330A1 (de) * | 1973-04-27 | 1974-11-07 | Bayer Ag | Azolyl-amidine, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide |
| DE2628055A1 (de) * | 1976-06-23 | 1978-01-05 | Basf Ag | Verfahren zur herstellung von n-(2- cyanphenyl)-formamidinen |
| NL7713687A (nl) * | 1976-12-16 | 1978-06-20 | Ciba Geigy | Werkwijze voor de bereiding van amidinen. |
| JPS6019752B2 (ja) * | 1977-07-27 | 1985-05-17 | 日本曹達株式会社 | イミダゾ−ル誘導体、その製造方法及び農園芸用殺菌剤 |
| JP2984119B2 (ja) * | 1990-12-10 | 1999-11-29 | 三井化学株式会社 | イミダゾリジン誘導体、その製造法、それを有効成分として含有する殺虫剤および中間体 |
| US5177106A (en) * | 1991-06-21 | 1993-01-05 | Warner-Lambert Company | 4-amino substituted phenoxyalkyl carboxylic acid, ester, and alcohol derivatives as antihypercholesterolemic and antiatherosclerotic agents |
| CN1113242A (zh) * | 1994-04-04 | 1995-12-13 | 住友化学工业株式会社 | 亚氨基噻唑啉衍生物及含有它们作为活性成分的除草剂 |
| DE69928262D1 (de) * | 1998-07-30 | 2005-12-15 | Wyeth Corp | Substituierte chinazoline derivate |
| GB9902592D0 (en) * | 1999-02-06 | 1999-03-24 | Hoechst Schering Agrevo Gmbh | Fungicides |
-
2003
- 2003-04-30 US US10/510,083 patent/US20050182025A1/en not_active Abandoned
- 2003-04-30 MX MXPA04010732A patent/MXPA04010732A/es unknown
- 2003-04-30 RU RU2004135323/04A patent/RU2004135323A/ru not_active Application Discontinuation
- 2003-04-30 EP EP03731059A patent/EP1501789A1/en not_active Withdrawn
- 2003-04-30 KR KR20047017646A patent/KR20040105250A/ko not_active Withdrawn
- 2003-04-30 JP JP2004501364A patent/JP2005524706A/ja active Pending
- 2003-04-30 PL PL03373618A patent/PL373618A1/xx not_active Application Discontinuation
- 2003-04-30 WO PCT/US2003/013371 patent/WO2003093224A1/en not_active Ceased
- 2003-04-30 CN CNA038095149A patent/CN1649833A/zh active Pending
- 2003-04-30 AU AU2003241327A patent/AU2003241327A1/en not_active Abandoned
- 2003-04-30 BR BR0309599-1A patent/BR0309599A/pt not_active IP Right Cessation
- 2003-04-30 UA UA20041108970A patent/UA78039C2/uk unknown
-
2004
- 2004-09-27 IL IL16431004A patent/IL164310A0/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003241327A1 (en) | 2003-11-17 |
| RU2004135323A (ru) | 2005-07-20 |
| EP1501789A1 (en) | 2005-02-02 |
| MXPA04010732A (es) | 2005-03-07 |
| US20050182025A1 (en) | 2005-08-18 |
| IL164310A0 (en) | 2005-12-18 |
| WO2003093224A1 (en) | 2003-11-13 |
| UA78039C2 (en) | 2007-02-15 |
| JP2005524706A (ja) | 2005-08-18 |
| BR0309599A (pt) | 2005-03-01 |
| CN1649833A (zh) | 2005-08-03 |
| PL373618A1 (en) | 2005-09-05 |
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