WO2000029398A1 - Isothiazolecarboxylic acid derivatives - Google Patents
Isothiazolecarboxylic acid derivatives Download PDFInfo
- Publication number
- WO2000029398A1 WO2000029398A1 PCT/EP1999/008355 EP9908355W WO0029398A1 WO 2000029398 A1 WO2000029398 A1 WO 2000029398A1 EP 9908355 W EP9908355 W EP 9908355W WO 0029398 A1 WO0029398 A1 WO 0029398A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- chloro
- alkyl
- methyl
- group
- phenyl
- Prior art date
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- BMPVWNJQCJQBFW-UHFFFAOYSA-N 1,2-thiazole-3-carboxylic acid Chemical class OC(=O)C=1C=CSN=1 BMPVWNJQCJQBFW-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 150000001875 compounds Chemical class 0.000 claims abstract description 76
- 238000000034 method Methods 0.000 claims abstract description 51
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- FGGLAFQQOCBWMY-UHFFFAOYSA-N 1,2-thiazole-3-carbonyl chloride Chemical class ClC(=O)C=1C=CSN=1 FGGLAFQQOCBWMY-UHFFFAOYSA-N 0.000 claims abstract description 9
- -1 substituted-phenyl Chemical group 0.000 claims description 249
- 125000000217 alkyl group Chemical group 0.000 claims description 69
- 125000001424 substituent group Chemical group 0.000 claims description 47
- 125000000623 heterocyclic group Chemical group 0.000 claims description 45
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 39
- 229910052736 halogen Inorganic materials 0.000 claims description 33
- 229910052757 nitrogen Inorganic materials 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
- 125000001188 haloalkyl group Chemical group 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 25
- 229910052760 oxygen Inorganic materials 0.000 claims description 25
- 239000001301 oxygen Chemical group 0.000 claims description 25
- 125000005842 heteroatom Chemical group 0.000 claims description 24
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 22
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 22
- 125000001153 fluoro group Chemical group F* 0.000 claims description 21
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
- 239000005864 Sulphur Chemical group 0.000 claims description 19
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 11
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 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 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 9
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 8
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 8
- 244000005700 microbiome Species 0.000 claims description 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 8
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 7
- 150000001298 alcohols Chemical class 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 239000003701 inert diluent Substances 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 5
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 5
- 239000003377 acid catalyst Substances 0.000 claims description 5
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 5
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 claims description 4
- 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 4
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 230000003115 biocidal effect Effects 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000003444 phase transfer catalyst Substances 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
- 125000005999 2-bromoethyl group Chemical group 0.000 claims description 3
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 3
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- 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 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000012320 chlorinating reagent Substances 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- 125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 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
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 2
- 125000004675 pentylcarbonyl group Chemical group C(CCCC)C(=O)* 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
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 2
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 14
- 125000005843 halogen group Chemical group 0.000 claims 11
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 239000003139 biocide Substances 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- 238000009472 formulation Methods 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 238000012360 testing method Methods 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000003085 diluting agent Substances 0.000 description 13
- 239000008187 granular material Substances 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 150000002431 hydrogen Chemical group 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 11
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- CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 0.000 description 1
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- 239000011575 calcium Substances 0.000 description 1
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- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
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- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- UPRXAOPZPSAYHF-UHFFFAOYSA-N lithium;cyclohexyl(propan-2-yl)azanide Chemical compound CC(C)N([Li])C1CCCCC1 UPRXAOPZPSAYHF-UHFFFAOYSA-N 0.000 description 1
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- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
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- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
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- 239000013225 prussian blue Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 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
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- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- BGQMOFGZRJUORO-UHFFFAOYSA-M tetrapropylammonium bromide Chemical compound [Br-].CCC[N+](CCC)(CCC)CCC BGQMOFGZRJUORO-UHFFFAOYSA-M 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/12—Powders or granules
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
-
- 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
- A01N43/80—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 1,2
-
- 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
- C07D417/12—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 linked by a chain containing hetero atoms as chain links
Definitions
- the present invention relates to novel isothiazolecarboxylic acid derivatives, to processes for their preparation and to their use as biocides.
- Y represents -O-Z, -S-Z 1 , or
- heterocyclyl with 1 to 3 heteroatoms selected from nitrogen, oxygen and/or sulphur, which heterocyclyl groups may be substituted by 1 to 3 substituents selected from halogen, C j . 4 alkyl, oxo and/or thioxo,
- Z represents phenyl optionally substituted by 1 or 2 substituents selected from the group consisting of fluoro, chloro, bromo, methyl, ethyl, n-propyl, tert- butyl, trifluoromethyl, trifluoromethoxy, tetrafluoroethoxy, phenoxy, phenyl, carboxy, methoxycarbonyl, ethoxycarbonyl, cyano, nitro, dimethylamino and diethylamino,
- Z 2 represents substituted alkyl having 1 to 4 carbon atoms and 1 to 4 substituents selected from the group consisting of fluoro, chloro, hydroxy, methoxy, methylthio, N-formylmethylamino, N-formylethylamino, N-formylpropyl- amino, N-acetylmethylamino, N-benzoylmethylamino, phenyl optionally substituted by 1 to 2 substituents selected from the group consisting of fluoro, chloro, methyl, ethyl, n-propyl, isopropyl, tert-butyl, trifluoromethyl, trifluoromethoxy, sulfamoyl, dimethylaminomethyl, diethylamino-methyl, phenyl and phenoxy, wherein the two last-mentioned radicals may be substituted by 1 or 2 substituents selected from the group consisting of fluoro, chloro, methyl, ethyl
- N,N-diethylaniline pyridine, 4-dimethylaminopyridine (DMAP), 1 ,4-diazabicyclo- [2,2,2]octane (DABCO) and l,8-diazabicyclo[5,4,0]undec-7-ene (DBU) etc.
- organo- lithium compounds such as methyl lithium, n-butyl lithium, sec-butyl lithium, tert- butyl lithium, phenyl lithium, dimethyl copper lithium, lithium diisopropylamide, lithium cyclohexyl isopropylamide, lithium dicyclohexylamide, n-butyl lithium.DBACO, n-butyl lithium.DBU, n-butyl lithium.TMEDA etc.
- reaction temperatures can be varied within a substantially wide range.
- the reaction is generally carried out at a temperature between about -78°C and about +100°C, preferably between about 0°C and about +30°C.
- Process (b) according to the invention is generally carried out under atmospheric pressure but, if desired, can also be carried out under elevated or reduced pressure.
- the above-mentioned amounts of active compound, carrier and emulsifier are crushed and mixed to make a wettable powder.
- a portion of the wettable powder comprising the prescribed amount of active compound is diluted with water and used for testing.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Toxicology (AREA)
- Dispersion Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020017005568A KR20010083945A (en) | 1998-11-13 | 1999-11-02 | Isothiazolecarboxylic acid derivatives |
AU12684/00A AU1268400A (en) | 1998-11-13 | 1999-11-02 | Isothiazolecarboxylic acid derivatives |
JP2000582385A JP2002530277A (en) | 1998-11-13 | 1999-11-02 | Isothiazolecarboxylic acid derivative |
EP99955940A EP1129083A1 (en) | 1998-11-13 | 1999-11-02 | Isothiazolecarboxylic acid derivatives |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP10/323696 | 1998-11-13 | ||
JP32369698 | 1998-11-13 | ||
JP11/54260 | 1999-03-02 | ||
JP11054260A JP2000204085A (en) | 1998-11-13 | 1999-03-02 | Isothiazole carboxylic acid derivative and disease controlling agent |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000029398A1 true WO2000029398A1 (en) | 2000-05-25 |
Family
ID=26395008
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1999/008355 WO2000029398A1 (en) | 1998-11-13 | 1999-11-02 | Isothiazolecarboxylic acid derivatives |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP1129083A1 (en) |
JP (2) | JP2000204085A (en) |
KR (1) | KR20010083945A (en) |
CN (1) | CN1333761A (en) |
AU (1) | AU1268400A (en) |
WO (1) | WO2000029398A1 (en) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1275301A1 (en) * | 2001-07-10 | 2003-01-15 | Bayer CropScience S.A. | Trisubstituted heterocyclic compounds and their use as fungicides |
EP1400516A4 (en) * | 2001-05-31 | 2006-05-17 | Nihon Nohyaku Co Ltd | SUBSTITUTED ANALID DERIVATIVES, THEIR INTERMEDIATE PRODUCTS, CHEMICALS FOR AGRICULTURE AND GARDENING AND THEIR USE |
US7723345B2 (en) | 2005-12-29 | 2010-05-25 | Lexicon Pharmaceuticals, Inc. | Multicyclic amino acid derivatives and methods of their use |
WO2011009804A2 (en) | 2009-07-24 | 2011-01-27 | Basf Se | Pyridine derivatives compounds for controlling invertebrate pests |
US8642597B2 (en) | 2007-08-27 | 2014-02-04 | Basf Se | Pyrazole compounds for controlling invertebrate pests |
US8710056B2 (en) | 2009-07-06 | 2014-04-29 | Basf Se | Pyridazine compounds for controlling invertebrate pests |
US8729083B2 (en) | 2008-09-24 | 2014-05-20 | Basf Se | Pyrazole compounds for controlling invertebrate pests |
US9029639B2 (en) | 2009-07-06 | 2015-05-12 | Basf Se | Pyridazine compounds for controlling invertebrate pests |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004074252A1 (en) * | 2003-02-18 | 2004-09-02 | Nihon Nohyaku Co., Ltd. | Substituted heterocyclic amide derivatives, intermediates thereof, agricultural and horticultural chemicals and their usage |
JP2004269515A (en) * | 2003-02-18 | 2004-09-30 | Nippon Nohyaku Co Ltd | Substituted heterocyclic amide derivatives, intermediates thereof, agricultural and horticultural drugs, and methods of using the same |
CN106543167B (en) * | 2015-09-17 | 2021-12-03 | 沈阳中化农药化工研发有限公司 | Isothiazole compound and application thereof |
JP6913082B2 (en) * | 2015-09-30 | 2021-08-04 | 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 | Use of isothianil for zebra chip disease control |
Citations (6)
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US3155678A (en) * | 1961-11-14 | 1964-11-03 | Du Pont | Certain isothiazole compounds and their production |
US3393992A (en) * | 1965-10-01 | 1968-07-23 | Pennsalt Chemicals Corp | Process for contacting plants with growth effecting chemical |
EP0503410A1 (en) * | 1991-03-14 | 1992-09-16 | BASF Aktiengesellschaft | Isoxazol- and Isothiazol 5-carboxylic acids amids |
WO1992016514A1 (en) * | 1991-03-14 | 1992-10-01 | Basf Aktiengesellschaft | Isoxazol- and isothiazol-5-carboxylic acid amides |
US5240951A (en) * | 1990-09-20 | 1993-08-31 | Mitsui Toatsu Chemicals, Incorporated | Isothiazolecarboxylic acid derivatives, rice blast control agents containing the same as active ingredients, and rice blast control method applying the control agents |
EP0697409A1 (en) * | 1994-06-30 | 1996-02-21 | Nihon Nohyaku Co., Ltd. | Isothiazole derivatives containing (an) iodoalkylnyl group(s), their preparation and their use as fungicide and/or bactericide |
-
1999
- 1999-03-02 JP JP11054260A patent/JP2000204085A/en active Pending
- 1999-11-02 WO PCT/EP1999/008355 patent/WO2000029398A1/en not_active Application Discontinuation
- 1999-11-02 JP JP2000582385A patent/JP2002530277A/en active Pending
- 1999-11-02 CN CN99815487A patent/CN1333761A/en active Pending
- 1999-11-02 EP EP99955940A patent/EP1129083A1/en not_active Withdrawn
- 1999-11-02 KR KR1020017005568A patent/KR20010083945A/en not_active Withdrawn
- 1999-11-02 AU AU12684/00A patent/AU1268400A/en not_active Abandoned
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3155678A (en) * | 1961-11-14 | 1964-11-03 | Du Pont | Certain isothiazole compounds and their production |
US3393992A (en) * | 1965-10-01 | 1968-07-23 | Pennsalt Chemicals Corp | Process for contacting plants with growth effecting chemical |
US5240951A (en) * | 1990-09-20 | 1993-08-31 | Mitsui Toatsu Chemicals, Incorporated | Isothiazolecarboxylic acid derivatives, rice blast control agents containing the same as active ingredients, and rice blast control method applying the control agents |
EP0503410A1 (en) * | 1991-03-14 | 1992-09-16 | BASF Aktiengesellschaft | Isoxazol- and Isothiazol 5-carboxylic acids amids |
WO1992016514A1 (en) * | 1991-03-14 | 1992-10-01 | Basf Aktiengesellschaft | Isoxazol- and isothiazol-5-carboxylic acid amides |
EP0697409A1 (en) * | 1994-06-30 | 1996-02-21 | Nihon Nohyaku Co., Ltd. | Isothiazole derivatives containing (an) iodoalkylnyl group(s), their preparation and their use as fungicide and/or bactericide |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1400516A4 (en) * | 2001-05-31 | 2006-05-17 | Nihon Nohyaku Co Ltd | SUBSTITUTED ANALID DERIVATIVES, THEIR INTERMEDIATE PRODUCTS, CHEMICALS FOR AGRICULTURE AND GARDENING AND THEIR USE |
US7459477B2 (en) | 2001-05-31 | 2008-12-02 | Nihon Nohyaku, Co., Ltd. | Substituted N-phenyl-phenoxy nicotinic acid-(thio)amides and their use as herbicides |
EP1275301A1 (en) * | 2001-07-10 | 2003-01-15 | Bayer CropScience S.A. | Trisubstituted heterocyclic compounds and their use as fungicides |
US7723345B2 (en) | 2005-12-29 | 2010-05-25 | Lexicon Pharmaceuticals, Inc. | Multicyclic amino acid derivatives and methods of their use |
US8063057B2 (en) | 2005-12-29 | 2011-11-22 | Lexicon Pharmaceuticals, Inc. | Multicyclic amino acid derivatives and methods of their use |
US8629156B2 (en) | 2005-12-29 | 2014-01-14 | Lexicon Pharmaceuticals, Inc. | Tryptophan hydroxylase inhibitors |
US9204647B2 (en) | 2007-08-27 | 2015-12-08 | Basf Se | Pyrazole compounds for controlling invertebrate pests |
US8642597B2 (en) | 2007-08-27 | 2014-02-04 | Basf Se | Pyrazole compounds for controlling invertebrate pests |
US8729083B2 (en) | 2008-09-24 | 2014-05-20 | Basf Se | Pyrazole compounds for controlling invertebrate pests |
US9375008B2 (en) | 2008-09-24 | 2016-06-28 | Basf Se | Pyrazole compounds for controlling invertebrate pests |
US8710056B2 (en) | 2009-07-06 | 2014-04-29 | Basf Se | Pyridazine compounds for controlling invertebrate pests |
US9029639B2 (en) | 2009-07-06 | 2015-05-12 | Basf Se | Pyridazine compounds for controlling invertebrate pests |
US9125414B2 (en) | 2009-07-24 | 2015-09-08 | Basf Se | Pyridine derivatives compounds for controlling invertebrate pests |
EP2456308A2 (en) * | 2009-07-24 | 2012-05-30 | Basf Se | Pyridine derivatives for controlling invertrebate pests |
WO2011009804A2 (en) | 2009-07-24 | 2011-01-27 | Basf Se | Pyridine derivatives compounds for controlling invertebrate pests |
Also Published As
Publication number | Publication date |
---|---|
EP1129083A1 (en) | 2001-09-05 |
JP2002530277A (en) | 2002-09-17 |
AU1268400A (en) | 2000-06-05 |
JP2000204085A (en) | 2000-07-25 |
CN1333761A (en) | 2002-01-30 |
KR20010083945A (en) | 2001-09-03 |
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