JP2001504107A - 有害生物防除剤としてのハロゲンピリミジニルアリール(チオ)エーテル - Google Patents
有害生物防除剤としてのハロゲンピリミジニルアリール(チオ)エーテルInfo
- Publication number
- JP2001504107A JP2001504107A JP52209498A JP52209498A JP2001504107A JP 2001504107 A JP2001504107 A JP 2001504107A JP 52209498 A JP52209498 A JP 52209498A JP 52209498 A JP52209498 A JP 52209498A JP 2001504107 A JP2001504107 A JP 2001504107A
- Authority
- JP
- Japan
- Prior art keywords
- halogen
- carbon atoms
- alkyl
- formula
- methyl
- 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.)
- Granted
Links
- -1 Halogen pyrimidinyl aryl (thio) ethers Chemical class 0.000 title claims abstract description 180
- 229910052736 halogen Inorganic materials 0.000 title claims abstract description 29
- 241000607479 Yersinia pestis Species 0.000 title claims description 5
- 238000000034 method Methods 0.000 claims abstract description 33
- 150000001875 compounds Chemical class 0.000 claims description 90
- 125000004432 carbon atom Chemical group C* 0.000 claims description 38
- 150000002367 halogens Chemical group 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 229910052731 fluorine Inorganic materials 0.000 claims description 19
- 239000011737 fluorine Substances 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 229910052717 sulfur Chemical group 0.000 claims description 10
- 239000011593 sulfur Chemical group 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- CEBDRQUBQYQBEV-UHFFFAOYSA-N 2-phenoxypyrimidine Chemical compound N=1C=CC=NC=1OC1=CC=CC=C1 CEBDRQUBQYQBEV-UHFFFAOYSA-N 0.000 claims description 5
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 5
- 125000001188 haloalkyl group Chemical group 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 4
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 4
- CMNFLGHNTOEAQH-UHFFFAOYSA-N 2-(2-hydroxyphenyl)-2-methoxyiminoacetamide Chemical compound CON=C(C(N)=O)C1=CC=CC=C1O CMNFLGHNTOEAQH-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 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
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 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
- 125000005916 2-methylpentyl group Chemical group 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- 125000005917 3-methylpentyl group Chemical group 0.000 claims description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 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
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 2
- 125000005087 alkynylcarbonyl group Chemical group 0.000 claims description 2
- 125000005336 allyloxy group Chemical group 0.000 claims description 2
- 125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 239000004067 bulking agent Substances 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000004983 dialkoxyalkyl group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 2
- 125000005202 dialkylaminocarbonyloxy group Chemical group 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 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
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000005188 oxoalkyl group Chemical group 0.000 claims description 2
- 125000004660 phenylalkylthio group Chemical group 0.000 claims description 2
- 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 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
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 7
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 230000000361 pesticidal effect Effects 0.000 claims 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 claims 1
- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 claims 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 1
- 125000005133 alkynyloxy group Chemical group 0.000 claims 1
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 229910052740 iodine Chemical group 0.000 claims 1
- 239000011630 iodine Chemical group 0.000 claims 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims 1
- 125000005702 oxyalkylene group Chemical group 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 27
- 239000000575 pesticide Substances 0.000 abstract description 2
- 241000196324 Embryophyta Species 0.000 description 37
- 238000012360 testing method Methods 0.000 description 29
- 239000002904 solvent Substances 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- 239000003995 emulsifying agent Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
- 239000007921 spray Substances 0.000 description 13
- 239000007858 starting material Substances 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 11
- 125000002877 alkyl aryl group Chemical group 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 238000011081 inoculation Methods 0.000 description 11
- 229920000151 polyglycol Polymers 0.000 description 11
- 239000010695 polyglycol Substances 0.000 description 11
- 230000003449 preventive effect Effects 0.000 description 11
- 241000894007 species Species 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 10
- 208000015181 infectious disease Diseases 0.000 description 10
- 238000005507 spraying Methods 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- 239000012141 concentrate Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 241000228453 Pyrenophora Species 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 230000000069 prophylactic effect Effects 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000000370 acceptor Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000000417 fungicide Substances 0.000 description 5
- 238000011534 incubation Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 241000233614 Phytophthora Species 0.000 description 4
- 241000233626 Plasmopara Species 0.000 description 4
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 230000000855 fungicidal effect Effects 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 241000223218 Fusarium Species 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000000975 dye Substances 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
- 150000002430 hydrocarbons Chemical group 0.000 description 3
- RONFGUROBZGJKP-UHFFFAOYSA-N iminoctadine Chemical compound NC(N)=NCCCCCCCCNCCCCCCCCN=C(N)N RONFGUROBZGJKP-UHFFFAOYSA-N 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
- AQKOJKCYBNUFLU-UHFFFAOYSA-N 4,5,6-trifluoropyrimidine Chemical compound FC1=NC=NC(F)=C1F AQKOJKCYBNUFLU-UHFFFAOYSA-N 0.000 description 2
- MCLDVUCSDZGNRR-UHFFFAOYSA-N 4,6-difluoropyrimidine Chemical compound FC1=CC(F)=NC=N1 MCLDVUCSDZGNRR-UHFFFAOYSA-N 0.000 description 2
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 2
- 239000005660 Abamectin Substances 0.000 description 2
- 241001480061 Blumeria graminis Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241001157813 Cercospora Species 0.000 description 2
- 241000371644 Curvularia ravenelii Species 0.000 description 2
- MDNWOSOZYLHTCG-UHFFFAOYSA-N Dichlorophen Chemical compound OC1=CC=C(Cl)C=C1CC1=CC(Cl)=CC=C1O MDNWOSOZYLHTCG-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 241000588921 Enterobacteriaceae Species 0.000 description 2
- 241000221787 Erysiphe Species 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000005780 Fluazinam Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000005867 Iprodione Substances 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 241000228457 Leptosphaeria maculans Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 241000736122 Parastagonospora nodorum Species 0.000 description 2
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- PZXOQEXFMJCDPG-UHFFFAOYSA-N omethoate Chemical compound CNC(=O)CSP(=O)(OC)OC PZXOQEXFMJCDPG-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
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- UWVQIROCRJWDKL-UHFFFAOYSA-N oxadixyl Chemical compound CC=1C=CC=C(C)C=1N(C(=O)COC)N1CCOC1=O UWVQIROCRJWDKL-UHFFFAOYSA-N 0.000 description 1
- KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 description 1
- PMCVMORKVPSKHZ-UHFFFAOYSA-N oxydemeton-methyl Chemical compound CCS(=O)CCSP(=O)(OC)OC PMCVMORKVPSKHZ-UHFFFAOYSA-N 0.000 description 1
- IWVCMVBTMGNXQD-PXOLEDIWSA-N oxytetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-PXOLEDIWSA-N 0.000 description 1
- 229960000625 oxytetracycline Drugs 0.000 description 1
- 235000019366 oxytetracycline Nutrition 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- IOUNQDKNJZEDEP-UHFFFAOYSA-N phosalone Chemical compound C1=C(Cl)C=C2OC(=O)N(CSP(=S)(OCC)OCC)C2=C1 IOUNQDKNJZEDEP-UHFFFAOYSA-N 0.000 description 1
- RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- ATROHALUCMTWTB-OWBHPGMISA-N phoxim Chemical compound CCOP(=S)(OCC)O\N=C(\C#N)C1=CC=CC=C1 ATROHALUCMTWTB-OWBHPGMISA-N 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- YFGYUFNIOHWBOB-UHFFFAOYSA-N pirimicarb Chemical compound CN(C)C(=O)OC1=NC(N(C)C)=NC(C)=C1C YFGYUFNIOHWBOB-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- YEBIHIICWDDQOL-YBHNRIQQSA-N polyoxin Polymers O[C@@H]1[C@H](O)[C@@H](C(C=O)N)O[C@H]1N1C(=O)NC(=O)C(C(O)=O)=C1 YEBIHIICWDDQOL-YBHNRIQQSA-N 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- WHHIPMZEDGBUCC-UHFFFAOYSA-N probenazole Chemical compound C1=CC=C2C(OCC=C)=NS(=O)(=O)C2=C1 WHHIPMZEDGBUCC-UHFFFAOYSA-N 0.000 description 1
- QXJKBPAVAHBARF-BETUJISGSA-N procymidone Chemical compound O=C([C@]1(C)C[C@@]1(C1=O)C)N1C1=CC(Cl)=CC(Cl)=C1 QXJKBPAVAHBARF-BETUJISGSA-N 0.000 description 1
- QYMMJNLHFKGANY-UHFFFAOYSA-N profenofos Chemical compound CCCSP(=O)(OCC)OC1=CC=C(Br)C=C1Cl QYMMJNLHFKGANY-UHFFFAOYSA-N 0.000 description 1
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- 239000001294 propane Substances 0.000 description 1
- PWYIUEFFPNVCMW-UHFFFAOYSA-N propaphos Chemical compound CCCOP(=O)(OCCC)OC1=CC=C(SC)C=C1 PWYIUEFFPNVCMW-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
- KKMLIVYBGSAJPM-UHFFFAOYSA-L propineb Chemical compound [Zn+2].[S-]C(=S)NC(C)CNC([S-])=S KKMLIVYBGSAJPM-UHFFFAOYSA-L 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- FITIWKDOCAUBQD-UHFFFAOYSA-N prothiofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(Cl)C=C1Cl FITIWKDOCAUBQD-UHFFFAOYSA-N 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- QHMTXANCGGJZRX-WUXMJOGZSA-N pymetrozine Chemical compound C1C(C)=NNC(=O)N1\N=C\C1=CC=CN=C1 QHMTXANCGGJZRX-WUXMJOGZSA-N 0.000 description 1
- QHGVXILFMXYDRS-UHFFFAOYSA-N pyraclofos Chemical compound C1=C(OP(=O)(OCC)SCCC)C=NN1C1=CC=C(Cl)C=C1 QHGVXILFMXYDRS-UHFFFAOYSA-N 0.000 description 1
- JOOMJVFZQRQWKR-UHFFFAOYSA-N pyrazophos Chemical compound N1=C(C)C(C(=O)OCC)=CN2N=C(OP(=S)(OCC)OCC)C=C21 JOOMJVFZQRQWKR-UHFFFAOYSA-N 0.000 description 1
- 229940015367 pyrethrum Drugs 0.000 description 1
- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
- CXJSOEPQXUCJSA-UHFFFAOYSA-N pyridaphenthion Chemical compound N1=C(OP(=S)(OCC)OCC)C=CC(=O)N1C1=CC=CC=C1 CXJSOEPQXUCJSA-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 1
- 229960003811 pyrithione disulfide Drugs 0.000 description 1
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- 239000010453 quartz Substances 0.000 description 1
- MRUMAIRJPMUAPZ-UHFFFAOYSA-N quinolin-8-ol;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CN=C2C(O)=CC=CC2=C1 MRUMAIRJPMUAPZ-UHFFFAOYSA-N 0.000 description 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 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
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- SRCCECZAEZWOJX-UHFFFAOYSA-M sodium;2-[formyl(hydroxy)amino]propanoate Chemical compound [Na+].[O-]C(=O)C(C)N(O)C=O SRCCECZAEZWOJX-UHFFFAOYSA-M 0.000 description 1
- MWOAQIRSOWIARK-UHFFFAOYSA-N sodium;methanetetrathiol Chemical compound [Na+].SC(S)(S)S MWOAQIRSOWIARK-UHFFFAOYSA-N 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- XIUROWKZWPIAIB-UHFFFAOYSA-N sulfotep Chemical compound CCOP(=S)(OCC)OP(=S)(OCC)OCC XIUROWKZWPIAIB-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- 230000002195 synergetic effect Effects 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
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- 229950004921 temefos Drugs 0.000 description 1
- WWJZWCUNLNYYAU-UHFFFAOYSA-N temephos Chemical compound C1=CC(OP(=S)(OC)OC)=CC=C1SC1=CC=C(OP(=S)(OC)OC)C=C1 WWJZWCUNLNYYAU-UHFFFAOYSA-N 0.000 description 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 description 1
- UBCKGWBNUIFUST-YHYXMXQVSA-N tetrachlorvinphos Chemical compound COP(=O)(OC)O\C(=C/Cl)C1=CC(Cl)=C(Cl)C=C1Cl UBCKGWBNUIFUST-YHYXMXQVSA-N 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- OBZIQQJJIKNWNO-UHFFFAOYSA-N tolclofos-methyl Chemical compound COP(=S)(OC)OC1=C(Cl)C=C(C)C=C1Cl OBZIQQJJIKNWNO-UHFFFAOYSA-N 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- BAZVSMNPJJMILC-UHFFFAOYSA-N triadimenol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC1=CC=C(Cl)C=C1 BAZVSMNPJJMILC-UHFFFAOYSA-N 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- JARYYMUOCXVXNK-CSLFJTBJSA-N validamycin A Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-CSLFJTBJSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/56—One oxygen atom and one sulfur atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1. 一般式(I) [式中、 Zは、それぞれ場合によっては置換されるシクロアルキル、アリールもしくは ヘテロシクリルを表し、 Rは、水素もしくはアルキルを表し、 Qは、酸素もしくは硫黄を表し、そして Xは、ハロゲンを表し、 L1,L2,L3およびL4は、同じか異なっており、そして互いに独立して、各 々は、水素、ハロゲン、シアノ、ニトロ、それぞれ場合によってはハロゲン置換 されていてもよいアルキル、アルコキシ、アルキルチオ、アルキルスルフィニル もしくはアルキルスルホニルを表す] の化合物。 2. Zが、各場合、ハロゲン、アルキルもしくはヒドロキシルによって、場 合によっては一置換ないし二置換されてもよい、炭素原子3〜7個をもつシクロ アルキルを表すか; 炭素原子1〜4個をもつアルキルによって、場合によっては置換されてもよい 環員3〜7個をもつヘテロシクリルを表すか; または、各々が、同じか異なる置換基によって、場合によっては一置 換ないし四置換されてもよい、フェニルもしくはナフチルを表すが、可能な置換 基は、好ましくは、以下の群: ハロゲン、シアノ、ニトロ、アミノ、ヒドロキシル、ホルミル、カルボキシル 、カルバモイル、チオカルバモイル; 各場合炭素原子1〜8個をもつ、それぞれ直鎖または分枝のアルキル、ヒドロ キシアルキル、オキソアルキル、アルコキシ、アルコキシアルキル、アルキルチ オアルキル、ジアルコキシアルキル、アルキルチオ、アルキルスルフィニルもし くはアルキルスルホニル; 各場合炭素原子2〜6個をもつ、それぞれ直鎖または分枝のアルケニルもしく はアルケニルオキシ; 各場合炭素原子1〜6個と同じか異なるハロゲン原子1〜13個をもつ、それ ぞれ直鎖または分枝のハロゲノアルキル、ハロゲノアルコキシ、ハロゲノアルキ ルチオ、ハロゲノアルキルスルフィニルもしくはハロゲノアルキルスルホニル; 各場合炭素原子2〜6個と同じか異なるハロゲン原子1〜11個をもつ、それ ぞれ直鎖または分枝のハロゲノアルケニルもしくはハロゲノアルケニルオキシ; それぞれの炭化水素鎖に炭素原子1〜6個をもつ、それぞれ直鎖または分枝の アルキルアミノ、ジアルキルアミノ、アルキルカルボニル、アルキルカルボニル オキシ、アルコキシカルボニル、アルキルアミノカルボニル、ジアルキルアミノ カルボニル、アリールアルキルアミノカルボニル、ジアルキルアミノカルボニル オキシ、アルケニルカルボニルもしくはアルキニルカルボニル; 各場合炭素原子3〜6個をもつシクロアルキルもしくはシクロアルキ ルオキシ; 炭素原子3もしくは4個をもつアルキレン、炭素原子2もしくは3個をもつオ キシアルキレン、または炭素原子1もしくは2個をもつジオキシアルキレンであ って、これらの各々は、二つの結合をもち、そして各場合、フッ素、塩素、オキ ソ、メチル、トリフルオロメチルおよびエチルからなる群からの同じか異なる置 換基によって、場合によっては一置換ないし四置換されてもよい; または、基 [式中、A1は、水素、ヒドロキシル、または炭素原子1〜4個をもつアルキル 、または炭素原子1〜6個をもつシクロアルキルを表し、そして A2は、ヒドロキシル、アミノ、メチルアミノ、フェニル、ベンジルを表すか 、またはそれぞれ、場合によってはシアノ−、ヒドロキシル−、アルコキシ−、 アルキルチオ−、アルキルアミノ−、ジアルキルアミノ−もしくはフェニル−置 換されていてもよい、炭素原子1〜4個をもつアルキルもしくはアルコキシを表 すか、または各場合炭素原子2〜4個をもつアルケニルオキシもしくはアルキニ ルオキシを表す]、 ならびにフェニル、フェノキシ、フェニルチオ、ベンゾイル、ベンゾイルエテ ニル、シンナモイル、ヘテロシクリル、またはそれぞれのアルキル部分に、各場 合炭素原子1〜3個をもつフェニルアルキル、フェニルアルキルオキシ、フェニ ルアルキルチオもしくはヘテロシクリルアルキルであって、これらの各々は、ハ ロゲンおよび/または炭素原子1〜 4個をもつ直鎖または分枝のアルキルもしくはアルコキシによって、場合によっ ては環部分において一置換ないし三置換されてもよい; から選ばれるものであり、 Rが、水素もしくはメチルを表し、 Qが、酸素もしくは硫黄を表し、そして Xが、フッ素、塩素、臭素もしくはヨウ素を表し、 L1,L2,L3およびL4が、同じか異なっており、そして互いに独立して各々 は、水素、ハロゲン、シアノ、ニトロを表すか、または各場合炭素原子1〜6個 をもち、そして各場合場合によってはハロゲン原子1〜5個によって、場合によ っては置換されてもよいアルキル、アルコキシ、アルキルチオ、アルキルスルフ ィニルもしくはアルキルスルホニルを表す、 請求の範囲1記載の式(I)の化合物。 3. Zが各々がフッ素、塩素、メチル、エチルもしくはヒドロキシルによっ て、場合によっては一置換ないし二置換されてもよい、シクロペンチルもしくは シクロヘキシルを表すか; 場合によってはメチル−もしくはエチル−置換されていてもよいチエニル、ピ リジルもしくはフリルを表すか; または、各々が、同じか異なる置換基によって、場合によっては一置換ないし 四置換されてもよい、フェニルもしくはナフチルを表すが、可能な置換基は、好 ましくは、以下の群: フッ素、塩素、臭素、ヨウ素、シアノ、ニトロ、アミノ、ヒドロキシル、ホル ミル、カルボキシル、カルバモイル、チオカルバモイル、 メチル、エチル、n−もしくはi−プロピル、n−,i−,s−もし くはt−ブチル、1−,2−,3−,neo−ペンチル、1−,2−,3−,4 −(2−メチルブチル)、1−,2−,3−ヘキシル、1−,2−,3−,4− ,5−(2−メチルペンチル)、1−,2−,3−(3−メチルペンチル)、2 −エチルブチル)、1−,3−,4−(2,2−ジメチルブチル)、1−,2− (2,3−ジメチルブチル)、ヒドロキシメチル、ヒドロキシエチル、3−オキ ソブチル、メトキシメチル、ジメトキシメチル、 メトキシ、エトキシ、n−もしくはi−プロポキシ、 メチルチオ、エチルチオ、n−もしくはi−プロピルチオ、メチルスルフィニ ル、エチルスルフィニル、メチルスルホニルもしくはエチルスルホニル、 ビニル、アリル、2−メチルアリル、プロペン−1−イル、クロトニル、プロ パルギル、ビニルオキシ、アリルオキシ、2−メチルアリルオキシ、プロペン− 1−イルオキシ、クロトニルオキシ、プロパルギルオキシ、 トリフルオロメチル、トリフルオロエチル、 ジフルオロメトキシ、トリフルオロメトキシ、ジフルオロクロロメトキシ、ト リフルオロエトキシ、ジフルオロメチルチオ、トリフルオロメチルチオ、ジフル オロクロロメチルチオ、トリフルオロメチルスルフィニルもしくはトリフルオロ メチルスルホニル、 メチルアミノ、エチルアミノ、n−もしくはi−プロピルアミノ、ジメチルア ミノ、ジエチルアミノ、 アセチル、プロピオニル、メトキシカルボニル、エトキシカルボニル、メチル アミノカルボニル、エチルアミノカルボニル、ジメチルアミノカ ルボニル、ジエチルアミノカルボニル、ジメチルアミノカルボニルオキシ、ジエ チルアミノカルボニルオキシ、ベンジルアミノカルボニル、アクリロイル、プロ ピオロイル、 シクロペンチル、シクロヘキシル、 プロパンジイル、エチレンオキシ、メチレンジオキシ、エチレンジオキシであ って、各々は、二つの結合をもち、そして各場合、フッ素、塩素、オキソ、メチ ルおよびトリフルオロメチルからなる群からの同じか異なる置換基によって、場 合によっては一置換ないし四置換されてもよい、または、基 [式中、A1は、水素、メチルもしくはヒドロキシルを表し、そして A2は、ヒドロキシル、メトキシ、エトキシ、アミノ、メチルアミノ、フェニ ル、ベンジルもしくはヒドロキシエチルを表す]、 ならびにフェニル、フェノキシ、フェニルチオ、ベンゾイル、ベンゾイルエテ ニル、シンナモイル、ベンジル、フェニルエチル、フェニルプロピル、ベンジル オキシ、ベンジルチオ、5,6−ジヒドロ−1,4,2−ジオキサジン−3−イ ルメチル、トリアゾリルメチル、ベンズオキサゾル−2−イルメチル、1,3− ジオキサン−2−イル、ベンズイミダゾル−2−イル、ジオキソル−2−イル、 オキサゾリルであって、これらの各々は、ハロゲンおよび/または炭素原子1〜 4個をもつ直鎖または分枝のアルキルもしくはアルコキシによって、場合によっ ては環部分において一置換ないし三置換されてもよい: から選ばれるものであり、 Rが、水素もしくはメチルを表し、 Qが、酸素もしくは硫黄を表し、そして Xが、フッ素もしくは塩素を表し、そして L1,L2,L3およびL4が、同じか異なっており、そして互いに独立して各々 は、水素、フッ素、塩素、臭素、シアノ、ニトロ、メチル、エチル、n−もしく はi−プロピル、n−,i−,s−もしくはt−ブチル、メトキシ、エトキシ、 n−もしくはi−プロポキシ、メチルチオ、エチルチオ、メチルスルフィニル、 エチルスルフィニル、メチルスルホニルもしくはエチルスルホニル、トリフルオ ロメチル、トリフルオロエチル、ジフルオロメトキシ、トリフルオロメトキシ、 ジフルオロクロロメトキシ、トリフルオロエトキシ、ジフルオロメチルチオ、ジ フルオロクロロメチルチオ、トリフルオロメチルチオ、トリフルオロメチルスル フィニルもしくはトリフルオロメチルスルホニルを表す、 請求の範囲1記載の式(I)の化合物。 4. Qが酸素を表す、請求の範囲1記載の式(I)の化合物。 5. 請求の範囲1記載の式(I)の少なくとも1種の化合物を含有すること を特徴とする、有害生物防除剤。 6. 請求の範囲1記載の式(I)の化合物を、有害生物および/またはそれ らの生育場所に作用させることを特徴とする、有害生物の防除方法。 7. 有害生物を防除するための請求の範囲1〜4のいずれかに記載の式(I )の化合物の使用。 8. 請求の範囲1〜4のいずれかに記載の式(I)の化合物を、増量剤およ び/または界面活性剤と混合することを特徴とする、有害生物 防除剤の製造方法。 9.式(IV) [式中、 L1,L2,L3およびL4は、同じか異なっており、そして互いに独立して、各 々は、水素、ハロゲン、シアノ、ニトロ、それぞれ場合によってはハロゲン置換 されていてもよいアルキル、アルコキシ、アルキルチオ、アルキルスルフィニル もしくはアルキルスルホニルを表し、 Rは、水素もしくはアルキルを表し、 Xは、ハロゲンを表し、そして Y2は、ハロゲンを表す] の化合物。 10.式(I) [式中、 Zは、それぞれ場合によっては置換されていてもよいシクロアルキル、 アリールもしくはヘテロシクリルを表し、 Rは、水素もしくはアルキルを表し、 Qは、酸素もしくは硫黄を表し、そして Xは、ハロゲンを表し、 L1,L2,L3およびL4は、同じか異なっており、そして互いに独立して、各 々は、水素、ハロゲン、シアノ、ニトロ、それぞれ場合によってはハロゲン置換 されていてもよいアルキル、アルコキシ、アルキルチオ、アルキルスルフィニル もしくはアルキルスルホニルを表す] の化合物の製造方法であって、 a)式(II) [式中、R,L1,L2,L3およびL4は、各々先に定義されたとおりである] の2−(2−ヒドロキシフェニル)−2−メトキシイミノ−アセトアミドを、一 般式(III) [式中、Z,Q,RおよびXは、各々先に定義されたとおりであり、そして Y1は、ハロゲンを表す] の置換ハロゲノピリミジンと、 適当ならば希釈剤の存在下、適当ならば酸受容体の存在下、そして適当ならば 触媒の存在下で反応させるか、または b)一般式(IV) [式中、R,L1,L2,L3,L4およびXは、各々先に定義されたとおりであり 、そして Y2は、ハロゲンを表す] のフェノキシピリミジンを、一般式(V) Z−Q−H (V) [式中、ZおよびQは、各々先に定義されたとおりである] の環式化合物と、 適当ならば希釈剤の存在下、適当ならば酸受容体の存在下、そして適当ならば 触媒の存在下で反応させる、 ことを特徴とする方法。
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EP0647631B1 (de) * | 1993-10-12 | 2001-08-16 | BASF Aktiengesellschaft | Naphthylether, Verfahren zu ihrer Verwendung, sie enthaltende Mittel und ihre Verwendung als Fungizide |
DE4340181A1 (de) | 1993-11-25 | 1995-06-01 | Bayer Ag | 3-Methoxy-2-phenyl-acrylsäuremethylester |
GB9404375D0 (en) | 1994-03-07 | 1994-04-20 | Zeneca Ltd | Fungicides |
DE4443641A1 (de) * | 1994-12-08 | 1996-06-13 | Bayer Ag | Substituierte Carbonsäureamide |
-
1996
- 1996-11-11 DE DE19646407A patent/DE19646407A1/de not_active Withdrawn
-
1997
- 1997-10-28 TW TW086115864A patent/TW364903B/zh active
- 1997-10-29 IL IL12971397A patent/IL129713A/xx not_active IP Right Cessation
- 1997-10-29 HU HU9904257A patent/HUP9904257A3/hu unknown
- 1997-10-29 EA EA199900381A patent/EA002471B1/ru not_active IP Right Cessation
- 1997-10-29 ID IDW990320D patent/ID23374A/id unknown
- 1997-10-29 UA UA99063223A patent/UA59380C2/uk unknown
- 1997-10-29 WO PCT/EP1997/005954 patent/WO1998021189A1/de active IP Right Grant
- 1997-10-29 KR KR1020057015226A patent/KR20050090015A/ko not_active Application Discontinuation
- 1997-10-29 CN CN97181194A patent/CN1117084C/zh not_active Expired - Fee Related
- 1997-10-29 DE DE59712873T patent/DE59712873D1/de not_active Expired - Lifetime
- 1997-10-29 US US09/297,666 patent/US6235743B1/en not_active Expired - Fee Related
- 1997-10-29 JP JP52209498A patent/JP4190035B2/ja not_active Expired - Lifetime
- 1997-10-29 BR BRPI9713499-6A patent/BR9713499B1/pt not_active IP Right Cessation
- 1997-10-29 CZ CZ991681A patent/CZ168199A3/cs unknown
- 1997-10-29 AU AU50520/98A patent/AU728544B2/en not_active Ceased
- 1997-10-29 PL PL97333301A patent/PL333301A1/xx unknown
- 1997-10-29 KR KR1019990703984A patent/KR20000053069A/ko active Search and Examination
- 1997-10-29 AT AT97913182T patent/ATE369346T1/de not_active IP Right Cessation
- 1997-10-29 EP EP97913182A patent/EP0937050B1/de not_active Expired - Lifetime
- 1997-11-10 ZA ZA9710098A patent/ZA9710098B/xx unknown
-
1999
- 1999-05-04 BG BG103384A patent/BG103384A/xx unknown
-
2001
- 2001-03-30 US US09/822,680 patent/US6359133B2/en not_active Expired - Fee Related
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2004
- 2004-05-19 CL CL200401129A patent/CL2004001129A1/es unknown
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011102307A (ja) * | 2003-07-23 | 2011-05-26 | Bayer Cropscience Ag | 殺菌活性化合物組合せ剤 |
JP2006022105A (ja) * | 2004-07-08 | 2006-01-26 | Lanxess Deutschland Gmbh | 含フッ素環芳香環の改善された製造方法 |
Also Published As
Publication number | Publication date |
---|---|
IL129713A (en) | 2003-07-31 |
DE19646407A1 (de) | 1998-05-14 |
ATE369346T1 (de) | 2007-08-15 |
US6235743B1 (en) | 2001-05-22 |
CN1242766A (zh) | 2000-01-26 |
ZA9710098B (en) | 1998-05-25 |
AU5052098A (en) | 1998-06-03 |
EA002471B1 (ru) | 2002-06-27 |
CL2004001129A1 (es) | 2005-01-21 |
BG103384A (en) | 2000-01-31 |
BR9713499B1 (pt) | 2010-12-14 |
PL333301A1 (en) | 1999-11-22 |
IL129713A0 (en) | 2000-02-29 |
EP0937050B1 (de) | 2007-08-08 |
HUP9904257A2 (hu) | 2000-04-28 |
BR9713499A (pt) | 2000-02-29 |
US6359133B2 (en) | 2002-03-19 |
JP4190035B2 (ja) | 2008-12-03 |
KR20050090015A (ko) | 2005-09-09 |
WO1998021189A1 (de) | 1998-05-22 |
AU728544B2 (en) | 2001-01-11 |
HUP9904257A3 (en) | 2000-05-29 |
DE59712873D1 (de) | 2007-09-20 |
TW364903B (en) | 1999-07-21 |
ID23374A (id) | 2000-04-20 |
EA199900381A1 (ru) | 2000-04-24 |
UA59380C2 (uk) | 2003-09-15 |
US20010018442A1 (en) | 2001-08-30 |
KR20000053069A (ko) | 2000-08-25 |
EP0937050A1 (de) | 1999-08-25 |
CN1117084C (zh) | 2003-08-06 |
CZ168199A3 (cs) | 1999-08-11 |
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