EP2445907A1 - Dérivés de thiazolylpipéridine comme fongicides - Google Patents
Dérivés de thiazolylpipéridine comme fongicidesInfo
- Publication number
- EP2445907A1 EP2445907A1 EP10725040A EP10725040A EP2445907A1 EP 2445907 A1 EP2445907 A1 EP 2445907A1 EP 10725040 A EP10725040 A EP 10725040A EP 10725040 A EP10725040 A EP 10725040A EP 2445907 A1 EP2445907 A1 EP 2445907A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- substituents
- alkyl
- methyl
- phenyl
- 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.)
- Withdrawn
Links
- 239000000417 fungicide Substances 0.000 title description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 157
- 150000003839 salts Chemical class 0.000 claims abstract description 57
- 241000233866 Fungi Species 0.000 claims abstract description 38
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- -1 carbonylthio Chemical group 0.000 claims description 591
- 125000001424 substituent group Chemical group 0.000 claims description 170
- 239000000203 mixture Substances 0.000 claims description 77
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 77
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 76
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 63
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 60
- 229910052736 halogen Inorganic materials 0.000 claims description 53
- 150000002367 halogens Chemical class 0.000 claims description 53
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 49
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 46
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 44
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 42
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 42
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 40
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 37
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 33
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 30
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 30
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 28
- 239000003795 chemical substances by application Substances 0.000 claims description 27
- 230000003032 phytopathogenic effect Effects 0.000 claims description 26
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 25
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 25
- 238000002360 preparation method Methods 0.000 claims description 22
- 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 description 21
- 230000009261 transgenic effect Effects 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
- 239000013543 active substance Substances 0.000 claims description 14
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
- 239000011593 sulfur Substances 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 10
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 8
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 8
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 8
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 8
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 8
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims description 8
- 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 claims description 8
- 125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 claims description 8
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims description 8
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 8
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 8
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 8
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 8
- 239000004606 Fillers/Extenders Substances 0.000 claims description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
- 125000001793 isothiazol-3-yl group Chemical group [H]C1=C([H])C(*)=NS1 0.000 claims description 7
- 125000004500 isothiazol-4-yl group Chemical group S1N=CC(=C1)* 0.000 claims description 7
- 125000004501 isothiazol-5-yl group Chemical group S1N=CC=C1* 0.000 claims description 7
- 125000004284 isoxazol-3-yl group Chemical group [H]C1=C([H])C(*)=NO1 0.000 claims description 7
- 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 claims description 7
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 7
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 7
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 6
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims description 6
- KIWSYRHAAPLJFJ-DNZSEPECSA-N n-[(e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enyl]pyridine-3-carboxamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/CNC(=O)C1=CC=CN=C1 KIWSYRHAAPLJFJ-DNZSEPECSA-N 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 6
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 6
- 125000001607 1,2,3-triazol-1-yl group Chemical group [*]N1N=NC([H])=C1[H] 0.000 claims description 5
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims description 5
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 5
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 5
- 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 125000004537 indazol-5-yl group Chemical group N1N=CC2=CC(=CC=C12)* 0.000 claims description 5
- 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims description 5
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims description 5
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 5
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 5
- 125000004254 isoquinolin-1-yl group Chemical group [H]C1=C([H])C2=C([H])C([H])=C([H])C([H])=C2C(*)=N1 0.000 claims description 5
- 125000004552 isoquinolin-4-yl group Chemical group C1=NC=C(C2=CC=CC=C12)* 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 claims description 5
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 claims description 5
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims description 5
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 5
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- MGHNDJJPPOAIHK-UHFFFAOYSA-N 1H-inden-1-yl Chemical group C1=CC=C2[CH]C=CC2=C1 MGHNDJJPPOAIHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 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 claims description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004130 indan-2-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])(*)C2([H])[H] 0.000 claims description 4
- 125000004536 indazol-1-yl group Chemical group N1(N=CC2=CC=CC=C12)* 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004551 isoquinolin-3-yl group Chemical group C1=NC(=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 3
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 3
- 125000006765 (C2-C6) haloalkenyloxy group Chemical group 0.000 claims description 2
- 125000006767 (C2-C6) haloalkynyloxy group Chemical group 0.000 claims description 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 2
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims description 2
- 125000004245 indazol-3-yl group Chemical group [H]N1N=C(*)C2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 claims description 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims description 2
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 10
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 6
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 1
- 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 claims 1
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims 1
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- 125000005322 morpholin-1-yl group Chemical group 0.000 claims 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 228
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
- 238000006243 chemical reaction Methods 0.000 description 71
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- 238000009472 formulation Methods 0.000 description 38
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- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 239000003161 ribonuclease inhibitor Substances 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 230000002786 root growth Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000004544 spot-on Substances 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- RDZWXODJIWMJPE-UHFFFAOYSA-N tert-butyl 4-[4-(hydroxymethyl)-1,3-thiazol-2-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1=NC(CO)=CS1 RDZWXODJIWMJPE-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000006007 trichloroethoxy group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000000169 tricyclic heterocycle group Chemical group 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 125000002348 vinylic group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
L'invention concerne des dérivés de thiazolylpipéridine de la formule (I), dans laquelle les symboles A, G, Y, n, R1, R2, R3, R4, et R5 ont la signification indiquée dans la description ainsi que des sels de ceux-ci agrochimiquement efficaces et leur utilisation dans la lutte contre des champignons parasites pathogènes ainsi qu'un procédé de fabrication de composés de la formule (I).
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP10725040A EP2445907A1 (fr) | 2009-06-23 | 2010-06-10 | Dérivés de thiazolylpipéridine comme fongicides |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP09163473A EP2272846A1 (fr) | 2009-06-23 | 2009-06-23 | Dérivés de thiazolylpipéridine en tant que fongicide |
EP10725040A EP2445907A1 (fr) | 2009-06-23 | 2010-06-10 | Dérivés de thiazolylpipéridine comme fongicides |
PCT/EP2010/003499 WO2010149275A1 (fr) | 2009-06-23 | 2010-06-10 | Dérivés de thiazolylpipéridine comme fongicides |
Publications (1)
Publication Number | Publication Date |
---|---|
EP2445907A1 true EP2445907A1 (fr) | 2012-05-02 |
Family
ID=41203840
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP09163473A Withdrawn EP2272846A1 (fr) | 2009-06-23 | 2009-06-23 | Dérivés de thiazolylpipéridine en tant que fongicide |
EP10725040A Withdrawn EP2445907A1 (fr) | 2009-06-23 | 2010-06-10 | Dérivés de thiazolylpipéridine comme fongicides |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP09163473A Withdrawn EP2272846A1 (fr) | 2009-06-23 | 2009-06-23 | Dérivés de thiazolylpipéridine en tant que fongicide |
Country Status (17)
Country | Link |
---|---|
US (3) | US20110046178A1 (fr) |
EP (2) | EP2272846A1 (fr) |
JP (1) | JP2012530734A (fr) |
KR (1) | KR20120050434A (fr) |
CN (2) | CN102459254A (fr) |
AR (1) | AR077066A1 (fr) |
BR (1) | BRPI1014077A8 (fr) |
CA (1) | CA2766199A1 (fr) |
CL (1) | CL2011003180A1 (fr) |
CO (1) | CO6480909A2 (fr) |
EA (1) | EA201270059A1 (fr) |
IL (1) | IL216344A0 (fr) |
MX (1) | MX2011013706A (fr) |
PE (1) | PE20121047A1 (fr) |
TW (1) | TW201111377A (fr) |
WO (1) | WO2010149275A1 (fr) |
ZA (1) | ZA201109365B (fr) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
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PL2516426T3 (pl) | 2009-12-21 | 2016-03-31 | Bayer Cropscience Ag | Bis(difluorometylo)pirazole jako fungicydy |
BR112012027762B1 (pt) | 2010-04-28 | 2018-06-05 | Bayer Intellectual Property Gmbh | Derivados de cetoheteroarilpiperidina e - piperazina como fungicidas |
JP2013528169A (ja) | 2010-05-27 | 2013-07-08 | バイエル・クロップサイエンス・アーゲー | 殺菌剤としてのピリジニルカルボン酸誘導体 |
CA2815716C (fr) | 2010-10-27 | 2019-06-11 | Bayer Intellectual Property Gmbh | Heteroarylpiperidine et derives d'heteroarylpiperidine comme fongicide |
JP6326231B2 (ja) | 2011-02-01 | 2018-05-16 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングBayer Intellectual Property GmbH | 殺菌剤としてのヘテロアリールピペリジン誘導体及びヘテロアリールピペラジン誘導体 |
US10004232B2 (en) | 2011-09-15 | 2018-06-26 | Bayer Intellectual Property Gmbh | Piperidine pyrazoles as fungicides |
CN104093715B (zh) | 2012-02-02 | 2017-04-26 | 埃科特莱茵药品有限公司 | 4‑(苯并咪唑‑2‑基)‑噻唑化合物及相关氮杂衍生物 |
JP5931291B2 (ja) | 2012-08-30 | 2016-06-08 | 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 | 3,5−ビス(ハロアルキル)−ピラゾール−4−カルボン酸誘導体の脱カルボキシル化手順 |
WO2015011099A1 (fr) | 2013-07-22 | 2015-01-29 | Actelion Pharmaceuticals Ltd | Dérivés de 1-(pipérazin-1-yl)-2-([1,2,4]triazol-1-yl)-éthanone |
AR099789A1 (es) | 2014-03-24 | 2016-08-17 | Actelion Pharmaceuticals Ltd | Derivados de 8-(piperazin-1-il)-1,2,3,4-tetrahidro-isoquinolina |
WO2016024350A1 (fr) | 2014-08-13 | 2016-02-18 | 株式会社エス・ディー・エス バイオテック | Composés cycliques à 11 éléments condensés et fongicides pour l'agriculture et l'horticulture les contenant |
TR201900680T4 (tr) | 2015-01-15 | 2019-02-21 | Idorsia Pharmaceuticals Ltd | CXCR3 Reseptör modülatörleri olarak hidroksialkil- piperazin türevleri. |
AR103399A1 (es) | 2015-01-15 | 2017-05-10 | Actelion Pharmaceuticals Ltd | Derivados de (r)-2-metil-piperazina como moduladores del receptor cxcr3 |
JP6407457B2 (ja) | 2016-02-08 | 2018-10-17 | 株式会社エス・ディー・エス バイオテック | 1,2−ベンゼンジメタノール化合物の製造方法 |
US11903387B2 (en) | 2016-02-08 | 2024-02-20 | Gowan Company, L.L.C. | Fungicidal composition |
CN106083707B (zh) * | 2016-06-01 | 2018-10-26 | 温州大学 | 一种非对称杂芳基硫醚的合成方法 |
CN107646855B (zh) * | 2017-08-02 | 2020-07-07 | 浙江工业大学 | 一种含哌啶噻唑类化合物在制备杀菌剂中的应用及其制备方法 |
CN114502551B (zh) | 2019-11-01 | 2023-08-22 | 优迈特株式会社 | 含氟嘧啶化合物及其制备方法 |
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US4245432A (en) | 1979-07-25 | 1981-01-20 | Eastman Kodak Company | Seed coatings |
WO1987005296A1 (fr) | 1986-03-07 | 1987-09-11 | Pfizer Inc. | 2-[(2-pyridyl)methylsulfinyl]thienoimidazoles et composes apparentes utilises en tant qu'agents de traitement ou de prevention des ulceres |
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ATE342968T1 (de) | 1995-04-20 | 2006-11-15 | Basf Ag | Auf basis ihrer struktur entworfene herbizid resistente produkte |
US5876739A (en) | 1996-06-13 | 1999-03-02 | Novartis Ag | Insecticidal seed coating |
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US20020134012A1 (en) | 2001-03-21 | 2002-09-26 | Monsanto Technology, L.L.C. | Method of controlling the release of agricultural active ingredients from treated plant seeds |
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PE20060426A1 (es) | 2004-06-02 | 2006-06-28 | Schering Corp | DERIVADOS DE ACIDO TARTARICO COMO INHIBIDORES DE MMPs, ADAMs, TACE Y TNF-alfa |
DE102005031583A1 (de) * | 2005-07-06 | 2007-01-25 | Bayer Cropscience Gmbh | Verfahren zur Herstellung von von 3-Arylmethylthio- und 3-Heteroarylmethylthio-4,5-dihydro-isoxazolin-Derivaten |
TW200738701A (en) | 2005-07-26 | 2007-10-16 | Du Pont | Fungicidal carboxamides |
BRPI0614834A2 (pt) * | 2005-08-18 | 2011-04-19 | Hoffmann La Roche | compostos, processo para a sua manufatura, composições farmacêuticas que os compreendem e usos destas |
ATE544861T1 (de) | 2005-08-24 | 2012-02-15 | Pioneer Hi Bred Int | Verfahren und zusammensetzungen für den ausdruck eines polynukleotid von interesse |
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KR101130380B1 (ko) | 2006-06-13 | 2012-04-23 | 상하이 인스티튜트 오브 마테리아 메디카 차이니즈 아카데미 오브 싸이언시즈 | 헤테로시클릭 비뉴클레오시드 화합물, 그의 제조방법, 약학적 조성물 및 항바이러스성 약제로서의 용도 |
DE102006031143A1 (de) * | 2006-07-04 | 2008-01-24 | Merck Patent Gmbh | Fluortenside |
WO2008013622A2 (fr) | 2006-07-27 | 2008-01-31 | E. I. Du Pont De Nemours And Company | Amides azocycliques fongicides |
US7638541B2 (en) * | 2006-12-28 | 2009-12-29 | Metabolex Inc. | 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine |
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-
2009
- 2009-06-23 EP EP09163473A patent/EP2272846A1/fr not_active Withdrawn
-
2010
- 2010-06-10 CA CA2766199A patent/CA2766199A1/fr not_active Abandoned
- 2010-06-10 MX MX2011013706A patent/MX2011013706A/es not_active Application Discontinuation
- 2010-06-10 WO PCT/EP2010/003499 patent/WO2010149275A1/fr active Application Filing
- 2010-06-10 EP EP10725040A patent/EP2445907A1/fr not_active Withdrawn
- 2010-06-10 BR BRPI1014077A patent/BRPI1014077A8/pt not_active IP Right Cessation
- 2010-06-10 PE PE2011002105A patent/PE20121047A1/es not_active Application Discontinuation
- 2010-06-10 EA EA201270059A patent/EA201270059A1/ru unknown
- 2010-06-10 JP JP2012516547A patent/JP2012530734A/ja not_active Ceased
- 2010-06-10 CN CN2010800282506A patent/CN102459254A/zh active Pending
- 2010-06-10 CN CN201410064480.8A patent/CN104059059A/zh active Pending
- 2010-06-10 KR KR1020127001619A patent/KR20120050434A/ko not_active Application Discontinuation
- 2010-06-11 AR ARP100102067A patent/AR077066A1/es not_active Application Discontinuation
- 2010-06-22 TW TW099120173A patent/TW201111377A/zh unknown
- 2010-06-23 US US12/822,037 patent/US20110046178A1/en not_active Abandoned
-
2011
- 2011-11-14 IL IL216344A patent/IL216344A0/en unknown
- 2011-12-15 CL CL2011003180A patent/CL2011003180A1/es unknown
- 2011-12-16 CO CO11174006A patent/CO6480909A2/es not_active Application Discontinuation
- 2011-12-20 ZA ZA2011/09365A patent/ZA201109365B/en unknown
-
2012
- 2012-09-05 US US13/603,473 patent/US20130090476A1/en not_active Abandoned
- 2012-09-05 US US13/603,474 patent/US20130090477A1/en not_active Abandoned
Non-Patent Citations (1)
Title |
---|
See references of WO2010149275A1 * |
Also Published As
Publication number | Publication date |
---|---|
US20130090476A1 (en) | 2013-04-11 |
KR20120050434A (ko) | 2012-05-18 |
US20110046178A1 (en) | 2011-02-24 |
US20130090477A1 (en) | 2013-04-11 |
BRPI1014077A2 (pt) | 2015-08-25 |
TW201111377A (en) | 2011-04-01 |
PE20121047A1 (es) | 2012-08-02 |
CN104059059A (zh) | 2014-09-24 |
IL216344A0 (en) | 2012-01-31 |
MX2011013706A (es) | 2012-02-22 |
CO6480909A2 (es) | 2012-07-16 |
EP2272846A1 (fr) | 2011-01-12 |
CL2011003180A1 (es) | 2012-06-15 |
CN102459254A (zh) | 2012-05-16 |
WO2010149275A1 (fr) | 2010-12-29 |
ZA201109365B (en) | 2013-02-27 |
CA2766199A1 (fr) | 2010-12-29 |
AR077066A1 (es) | 2011-07-27 |
EA201270059A1 (ru) | 2012-08-30 |
BRPI1014077A8 (pt) | 2016-05-24 |
JP2012530734A (ja) | 2012-12-06 |
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