CA2243591C - Halogen pyrimidines and its use thereof as parasite abatement means - Google Patents
Halogen pyrimidines and its use thereof as parasite abatement means Download PDFInfo
- Publication number
- CA2243591C CA2243591C CA002243591A CA2243591A CA2243591C CA 2243591 C CA2243591 C CA 2243591C CA 002243591 A CA002243591 A CA 002243591A CA 2243591 A CA2243591 A CA 2243591A CA 2243591 C CA2243591 C CA 2243591C
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- methyl
- halogen
- nmr
- diyl
- 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.)
- Expired - Lifetime
Links
- 229910052736 halogen Inorganic materials 0.000 title claims abstract description 24
- -1 Halogen pyrimidines Chemical class 0.000 title claims description 150
- 244000045947 parasite Species 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 110
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000005843 halogen group Chemical group 0.000 claims abstract description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000005864 Sulphur Chemical group 0.000 claims abstract description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- 241000607479 Yersinia pestis Species 0.000 claims abstract 3
- 238000002360 preparation method Methods 0.000 claims description 53
- 238000000034 method Methods 0.000 claims description 51
- 239000000203 mixture Substances 0.000 claims description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 239000000460 chlorine Chemical group 0.000 claims description 19
- 150000002367 halogens Chemical group 0.000 claims description 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 239000011737 fluorine Substances 0.000 claims description 15
- 239000003085 diluting agent Substances 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 150000002440 hydroxy compounds Chemical class 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- CEBDRQUBQYQBEV-UHFFFAOYSA-N 2-phenoxypyrimidine Chemical compound N=1C=CC=NC=1OC1=CC=CC=C1 CEBDRQUBQYQBEV-UHFFFAOYSA-N 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 150000001923 cyclic compounds Chemical class 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 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 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000000575 pesticide Substances 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
- 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000004983 dialkoxyalkyl group Chemical group 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 229910052740 iodine Chemical group 0.000 claims description 2
- 239000011630 iodine Chemical group 0.000 claims description 2
- 125000005394 methallyl group Chemical group 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 125000005188 oxoalkyl group Chemical group 0.000 claims description 2
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000004344 phenylpropyl group Chemical group 0.000 claims description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical group [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 claims 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 1
- 125000005336 allyloxy group Chemical group 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims 1
- 125000005202 dialkylaminocarbonyloxy group Chemical group 0.000 claims 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000004660 phenylalkylthio group Chemical group 0.000 claims 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 abstract description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 76
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
- 241000196324 Embryophyta Species 0.000 description 46
- 239000002904 solvent Substances 0.000 description 31
- 239000003995 emulsifying agent Substances 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 239000007858 starting material Substances 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 230000001681 protective effect Effects 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- 125000002877 alkyl aryl group Chemical group 0.000 description 14
- 238000011081 inoculation Methods 0.000 description 14
- 229920000151 polyglycol Polymers 0.000 description 14
- 239000010695 polyglycol Substances 0.000 description 14
- 239000000725 suspension Substances 0.000 description 14
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 238000005507 spraying Methods 0.000 description 12
- 239000012141 concentrate Substances 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 9
- 238000011534 incubation Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 241001459558 Monographella nivalis Species 0.000 description 8
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 241000209140 Triticum Species 0.000 description 6
- 235000021307 Triticum Nutrition 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 235000011181 potassium carbonates Nutrition 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- 239000000370 acceptor Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 235000011118 potassium hydroxide Nutrition 0.000 description 5
- 229940093932 potassium hydroxide Drugs 0.000 description 5
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 241000221787 Erysiphe Species 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
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- 241000221300 Puccinia Species 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 4
- 239000000417 fungicide Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 229940083608 sodium hydroxide Drugs 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 description 4
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 3
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- AQKOJKCYBNUFLU-UHFFFAOYSA-N 4,5,6-trifluoropyrimidine Chemical compound FC1=NC=NC(F)=C1F AQKOJKCYBNUFLU-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- 241001668536 Oculimacula yallundae Species 0.000 description 3
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- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 3
- 241000233626 Plasmopara Species 0.000 description 3
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- 206010037888 Rash pustular Diseases 0.000 description 3
- 241000579741 Sphaerotheca <fungi> Species 0.000 description 3
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 3
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 3
- 150000008046 alkali metal hydrides Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 239000003899 bactericide agent Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
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- NKNFWVNSBIXGLL-UHFFFAOYSA-N triazamate Chemical compound CCOC(=O)CSC1=NC(C(C)(C)C)=NN1C(=O)N(C)C NKNFWVNSBIXGLL-UHFFFAOYSA-N 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
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- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Indole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19602095.6 | 1996-01-22 | ||
| DE19602095A DE19602095A1 (de) | 1996-01-22 | 1996-01-22 | Halogenpyrimidine |
| PCT/EP1997/000151 WO1997027189A1 (de) | 1996-01-22 | 1997-01-15 | Halogenpyrimidine und ihre verwendung als schädlingsbekämpfungsmittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2243591A1 CA2243591A1 (en) | 1997-07-31 |
| CA2243591C true CA2243591C (en) | 2004-07-27 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002243591A Expired - Lifetime CA2243591C (en) | 1996-01-22 | 1997-01-15 | Halogen pyrimidines and its use thereof as parasite abatement means |
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| DE19706396A1 (de) | 1996-12-09 | 1998-06-10 | Bayer Ag | Verfahren zur Herstellung von 3-(l-Hydroxiphenyl-l-alkoximinomethyl)dioxazinen |
| DE19739982A1 (de) * | 1996-12-10 | 1998-06-18 | Bayer Ag | Fungizide Wirkstoffkombinationen |
| RU2192743C2 (ru) * | 1996-12-10 | 2002-11-20 | Байер Акциенгезелльшафт | Композиции из веществ с фунгицидной активностью |
| DE19713762A1 (de) * | 1997-04-03 | 1998-10-08 | Bayer Ag | Methoximinomethyldioxazine |
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| US6297236B1 (en) | 1998-04-06 | 2001-10-02 | Bayer Aktiengesellschaft | Fungicide active substance combinations |
| CA2291026A1 (en) | 1997-06-05 | 1998-12-10 | Takeda Chemical Industries, Ltd. | Heterocyclic compounds, their production and use |
| DE19744705A1 (de) | 1997-10-10 | 1999-04-15 | Bayer Ag | Verfahren zur Herstellung gegebenenfalls substituierter Benzofuranone |
| DE19819828A1 (de) | 1998-05-04 | 1999-11-11 | Bayer Ag | Methoximinomethyloxathiazine |
| EP0972770B1 (en) * | 1998-07-14 | 2001-09-19 | Basf Aktiengesellschaft | Acaricidal and insecticidal substituted pyrimidines and a process for the preparation thereof |
| DE19939841A1 (de) * | 1998-11-20 | 2000-05-25 | Bayer Ag | Fungizide Wirkstoffkombinationen |
| DE19857963A1 (de) * | 1998-12-16 | 2000-06-21 | Bayer Ag | Agrochemische Formulierungen |
| AU2661800A (en) | 1999-01-13 | 2000-08-01 | Basf Aktiengesellschaft | Azadioxacycloalkenes and their use for combating harmful fungi and animal pests |
| EP1228050A1 (de) * | 1999-11-12 | 2002-08-07 | Basf Aktiengesellschaft | Azadioxacycloalkene |
| PL200668B1 (pl) * | 1999-12-13 | 2009-01-30 | Bayer Ag | Kombinacje substancji aktywnych, zastosowanie tych kombinacji i sposób wytwarzania środków grzybobójczych |
| DE10014607A1 (de) | 2000-03-24 | 2001-09-27 | Bayer Ag | Verfahren zur Herstellung von unsymmetrischen 4,6-Bis(aryloxy pyrimidin-Derivaten |
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| DE10049804A1 (de) * | 2000-10-09 | 2002-04-18 | Bayer Ag | Wirkstoffkombinationen mit fungiziden und akariziden Eigenschaften |
| DE10059605A1 (de) | 2000-12-01 | 2002-06-06 | Bayer Ag | Fungizide Wirkstoffkombinationen |
| DE10209145A1 (de) * | 2002-03-01 | 2003-09-04 | Bayer Cropscience Ag | Halogenbenzole |
| BR0308831A (pt) * | 2002-04-05 | 2005-01-25 | Basf Ag | Mistura fungicida, processo para combater fungos nocivos, e, agente fungicida |
| ATE496536T1 (de) * | 2002-04-10 | 2011-02-15 | Basf Se | Verfahren zur erhöhung der widerstandskraft von pflanzen gegen die phytotoxizität von agrochemikalien |
| DE10228104A1 (de) * | 2002-06-24 | 2004-01-15 | Bayer Cropscience Ag | Fungizide Wirkstoffkombination |
| CN102558155A (zh) | 2003-01-14 | 2012-07-11 | 阿伦纳药品公司 | 作为代谢调节剂的芳基和杂芳基衍生物及其所涉及的疾病如糖尿病和高血糖症的预防和治疗 |
| AR045047A1 (es) | 2003-07-11 | 2005-10-12 | Arena Pharm Inc | Derivados arilo y heteroarilo trisustituidos como moduladores del metabolismo y de la profilaxis y tratamiento de desordenes relacionados con los mismos |
| DE10337885A1 (de) | 2003-08-18 | 2005-03-24 | Bayer Cropscience Ag | Verfahren zur Herstellung von α-Fluormalonsäuredialkylestern |
| DE10343872A1 (de) * | 2003-09-23 | 2005-04-21 | Bayer Cropscience Ag | Suspensionskonzentrate |
| DE10347090A1 (de) | 2003-10-10 | 2005-05-04 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| DE10349501A1 (de) | 2003-10-23 | 2005-05-25 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| EP2255630A3 (de) | 2004-04-30 | 2012-09-26 | Basf Se | Fungizide Mischungen |
| DE102004033525A1 (de) * | 2004-07-08 | 2006-02-02 | Lanxess Deutschland Gmbh | Verbessertes Verfahren zur Herstellung kernfluorierter Aromaten |
| DE102004040702B4 (de) | 2004-08-23 | 2019-03-28 | Bayer Cropscience Aktiengesellschaft | Verfahren zur Herstellung eines Dioxazin-Derivats |
| DE102004049761A1 (de) * | 2004-10-12 | 2006-04-13 | Bayer Cropscience Ag | Fungizide Wirkstoffkombinationen |
| DOP2006000010A (es) | 2005-01-10 | 2006-07-31 | Arena Pharm Inc | Procedimiento para preparar eteres aromáticos |
| MY148521A (en) | 2005-01-10 | 2013-04-30 | Arena Pharm Inc | Substituted pyridinyl and pyrimidinyl derivatives as modulators of metabolism and the treatment of disorders related thereto |
| ES2653317T3 (es) | 2005-02-22 | 2018-02-06 | Basf Se | Composición y método para mejorar la fitosanidad |
| DE102005015677A1 (de) | 2005-04-06 | 2006-10-12 | Bayer Cropscience Ag | Synergistische fungizide Wirkstoffkombinationen |
| EA201270781A1 (ru) | 2005-06-09 | 2013-09-30 | Байер Кропсайенс Аг | Комбинации биологически активных веществ |
| DE102005026482A1 (de) | 2005-06-09 | 2006-12-14 | Bayer Cropscience Ag | Wirkstoffkombinationen |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8903019D0 (en) * | 1989-02-10 | 1989-03-30 | Ici Plc | Fungicides |
| JPH02233602A (ja) | 1989-03-08 | 1990-09-17 | Hokko Chem Ind Co Ltd | 除草剤 |
| JP3188286B2 (ja) | 1991-08-20 | 2001-07-16 | 塩野義製薬株式会社 | フェニルメトキシイミノ化合物およびそれを用いる農業用殺菌剤 |
| GB9307247D0 (en) | 1993-04-07 | 1993-06-02 | Zeneca Ltd | Fungicidal compounds |
| DE4408005A1 (de) * | 1993-08-11 | 1995-02-16 | Bayer Ag | Substituierte Azadioxacycloalkene |
| ZW8594A1 (en) * | 1993-08-11 | 1994-10-12 | Bayer Ag | Substituted azadioxacycbalkenes |
| DE19501842A1 (de) * | 1995-01-23 | 1996-07-25 | Bayer Ag | Substituierte Arylazadioxacycloalkene |
| DE19526047C1 (de) | 1995-07-17 | 1997-03-06 | Hoechst Ag | Verfahren zur Herstellung sekundärer Arylphosphane |
-
1996
- 1996-01-22 DE DE19602095A patent/DE19602095A1/de not_active Withdrawn
-
1997
- 1997-01-15 DK DK97900603T patent/DK0882043T3/da active
- 1997-01-15 CA CA002243591A patent/CA2243591C/en not_active Expired - Lifetime
- 1997-01-15 RU RU98116047/04A patent/RU2191186C2/ru active
- 1997-01-15 CZ CZ19982310A patent/CZ295548B6/cs not_active IP Right Cessation
- 1997-01-15 KR KR19980705067A patent/KR100383906B1/ko not_active Expired - Lifetime
- 1997-01-15 PT PT97900603T patent/PT882043E/pt unknown
- 1997-01-15 BR BR9707160A patent/BR9707160A/pt not_active IP Right Cessation
- 1997-01-15 WO PCT/EP1997/000151 patent/WO1997027189A1/de not_active Ceased
- 1997-01-15 ES ES97900603T patent/ES2180021T3/es not_active Expired - Lifetime
- 1997-01-15 SK SK989-98A patent/SK283815B6/sk not_active IP Right Cessation
- 1997-01-15 PL PL32792497A patent/PL187756B1/pl unknown
- 1997-01-15 DE DE59708129T patent/DE59708129D1/de not_active Expired - Lifetime
- 1997-01-15 IL IL12497497A patent/IL124974A/en not_active IP Right Cessation
- 1997-01-15 UA UA98084522A patent/UA56156C2/uk unknown
- 1997-01-15 EP EP97900603A patent/EP0882043B1/de not_active Expired - Lifetime
- 1997-01-15 TR TR1998/01392T patent/TR199801392T2/xx unknown
- 1997-01-15 US US09/101,791 patent/US6103717A/en not_active Expired - Lifetime
- 1997-01-15 CN CN97191795A patent/CN1072223C/zh not_active Expired - Lifetime
- 1997-01-15 AU AU13121/97A patent/AU720066B2/en not_active Expired
- 1997-01-15 JP JP52648497A patent/JP3262277B2/ja not_active Expired - Lifetime
- 1997-01-15 HU HU9900582A patent/HU227488B1/hu unknown
- 1997-01-15 CN CNB031598080A patent/CN1213037C/zh not_active Expired - Lifetime
- 1997-01-15 IN IN113DE1997 patent/IN187450B/en unknown
- 1997-01-15 MX MX9805742A patent/MX203302B/es unknown
- 1997-01-15 TW TW86100357A patent/TW349001B/zh not_active IP Right Cessation
- 1997-01-15 AT AT97900603T patent/ATE223407T1/de active
- 1997-01-15 NZ NZ325869A patent/NZ325869A/xx not_active IP Right Cessation
- 1997-01-21 ID IDP970165A patent/ID15839A/id unknown
- 1997-01-21 ZA ZA9700478A patent/ZA97478B/xx unknown
- 1997-01-21 CO CO97002475A patent/CO4770925A1/es unknown
-
1998
- 1998-07-10 BG BG102622A patent/BG64178B1/bg unknown
-
2000
- 2000-04-27 US US09/560,021 patent/US6407233B1/en not_active Expired - Lifetime
- 2000-06-01 IN IN551DE2000 patent/IN187520B/en unknown
- 2000-12-27 CN CNB00138063XA patent/CN1146550C/zh not_active Expired - Lifetime
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2002
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2006
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