CN87103623A - 杀真菌剂 - Google Patents
杀真菌剂 Download PDFInfo
- Publication number
- CN87103623A CN87103623A CN87103623.1A CN87103623A CN87103623A CN 87103623 A CN87103623 A CN 87103623A CN 87103623 A CN87103623 A CN 87103623A CN 87103623 A CN87103623 A CN 87103623A
- Authority
- CN
- China
- Prior art keywords
- compound
- replace
- selecting
- methyl
- group
- 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
- 239000000417 fungicide Substances 0.000 title abstract description 3
- 239000000203 mixture Substances 0.000 claims abstract description 99
- 238000000034 method Methods 0.000 claims abstract description 46
- 241000238631 Hexapoda Species 0.000 claims abstract description 14
- 230000008635 plant growth Effects 0.000 claims abstract description 13
- 230000000855 fungicidal effect Effects 0.000 claims abstract description 10
- 241000244206 Nematoda Species 0.000 claims abstract description 6
- 239000005645 nematicide Substances 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 181
- -1 nitro, amino Chemical group 0.000 claims description 61
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
- 239000002585 base Substances 0.000 claims description 42
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 39
- 239000001301 oxygen Substances 0.000 claims description 39
- 229910052760 oxygen Inorganic materials 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 32
- 229910052801 chlorine Inorganic materials 0.000 claims description 30
- 239000000460 chlorine Substances 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 21
- 229910052731 fluorine Inorganic materials 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 239000011737 fluorine Substances 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 229910052751 metal Inorganic materials 0.000 claims description 15
- 239000002184 metal Substances 0.000 claims description 15
- 239000003513 alkali Substances 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 239000000470 constituent Substances 0.000 claims description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 11
- 229910052723 transition metal Inorganic materials 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 150000003624 transition metals Chemical class 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 7
- 125000003368 amide group Chemical group 0.000 claims description 7
- 229940031815 mycocide Drugs 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 4
- 230000000749 insecticidal effect Effects 0.000 claims description 4
- 230000001069 nematicidal effect Effects 0.000 claims description 4
- 125000001820 oxy group Chemical group [*:1]O[*:2] 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
- 125000001424 substituent group Chemical group 0.000 claims description 4
- AOWPVIWVMWUSBD-RNFRBKRXSA-N [(3r)-3-hydroxybutyl] (3r)-3-hydroxybutanoate Chemical compound C[C@@H](O)CCOC(=O)C[C@@H](C)O AOWPVIWVMWUSBD-RNFRBKRXSA-N 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- 230000002371 mycocidal effect Effects 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- VBQCHPIMZGQLAZ-UHFFFAOYSA-N phosphorane Chemical compound [PH5] VBQCHPIMZGQLAZ-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 38
- 241000233866 Fungi Species 0.000 abstract description 11
- 150000001252 acrylic acid derivatives Chemical class 0.000 abstract description 3
- 239000005648 plant growth regulator Substances 0.000 abstract description 3
- 230000001276 controlling effect Effects 0.000 abstract description 2
- 239000002917 insecticide Substances 0.000 abstract description 2
- 230000008569 process Effects 0.000 abstract description 2
- 230000001105 regulatory effect Effects 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 111
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 63
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 57
- 239000000243 solution Substances 0.000 description 56
- 241000196324 Embryophyta Species 0.000 description 47
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 43
- 238000006243 chemical reaction Methods 0.000 description 35
- 239000007788 liquid Substances 0.000 description 32
- 238000000605 extraction Methods 0.000 description 26
- 238000003756 stirring Methods 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 23
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 23
- 238000010586 diagram Methods 0.000 description 21
- 238000005160 1H NMR spectroscopy Methods 0.000 description 20
- 239000000126 substance Substances 0.000 description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- 238000002329 infrared spectrum Methods 0.000 description 17
- 239000003921 oil Substances 0.000 description 17
- 201000010099 disease Diseases 0.000 description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- 235000015320 potassium carbonate Nutrition 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- 238000012360 testing method Methods 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 238000005406 washing Methods 0.000 description 15
- 239000000284 extract Substances 0.000 description 14
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 13
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 13
- 238000001035 drying Methods 0.000 description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 12
- 230000009467 reduction Effects 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- 150000002431 hydrogen Chemical group 0.000 description 11
- 238000009834 vaporization Methods 0.000 description 11
- 230000008016 vaporization Effects 0.000 description 11
- 238000004891 communication Methods 0.000 description 10
- 230000006854 communication Effects 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- 239000003480 eluent Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 235000013339 cereals Nutrition 0.000 description 8
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 235000019439 ethyl acetate Nutrition 0.000 description 7
- 238000003810 ethyl acetate extraction Methods 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 125000001188 haloalkyl group Chemical group 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 238000005507 spraying Methods 0.000 description 7
- 238000010561 standard procedure Methods 0.000 description 7
- 238000010792 warming Methods 0.000 description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 6
- 241000675108 Citrus tangerina Species 0.000 description 6
- 241000371644 Curvularia ravenelii Species 0.000 description 6
- 241000221785 Erysiphales Species 0.000 description 6
- 241001533598 Septoria Species 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 239000012452 mother liquor Substances 0.000 description 6
- 239000012266 salt solution Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 239000000375 suspending agent Substances 0.000 description 6
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- CRZQGDNQQAALAY-UHFFFAOYSA-N Methyl benzeneacetate Chemical compound COC(=O)CC1=CC=CC=C1 CRZQGDNQQAALAY-UHFFFAOYSA-N 0.000 description 5
- 238000013375 chromatographic separation Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000003337 fertilizer Substances 0.000 description 5
- 230000012010 growth Effects 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 150000004702 methyl esters Chemical class 0.000 description 5
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 5
- 235000013311 vegetables Nutrition 0.000 description 5
- 239000000080 wetting agent Substances 0.000 description 5
- 244000025254 Cannabis sativa Species 0.000 description 4
- 240000005979 Hordeum vulgare Species 0.000 description 4
- 235000007340 Hordeum vulgare Nutrition 0.000 description 4
- 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 4
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 4
- 241000220225 Malus Species 0.000 description 4
- 235000011430 Malus pumila Nutrition 0.000 description 4
- 235000015103 Malus silvestris Nutrition 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- 241000233679 Peronosporaceae Species 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 240000003768 Solanum lycopersicum Species 0.000 description 4
- 238000011097 chromatography purification Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 4
- 229910000474 mercury oxide Inorganic materials 0.000 description 4
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 150000002825 nitriles Chemical class 0.000 description 4
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229960001866 silicon dioxide Drugs 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 235000017060 Arachis glabrata Nutrition 0.000 description 3
- 244000105624 Arachis hypogaea Species 0.000 description 3
- 235000010777 Arachis hypogaea Nutrition 0.000 description 3
- 235000018262 Arachis monticola Nutrition 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 241001157813 Cercospora Species 0.000 description 3
- 241000207199 Citrus Species 0.000 description 3
- 240000008067 Cucumis sativus Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000223218 Fusarium Species 0.000 description 3
- 241000243785 Meloidogyne javanica Species 0.000 description 3
- 241000047703 Nonion Species 0.000 description 3
- 241000896238 Oidium Species 0.000 description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 241001361634 Rhizoctonia Species 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 3
- 235000020971 citrus fruits Nutrition 0.000 description 3
- 239000004927 clay Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- 239000003924 oil dispersant Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 235000020232 peanut Nutrition 0.000 description 3
- 229940049953 phenylacetate Drugs 0.000 description 3
- 229960003424 phenylacetic acid Drugs 0.000 description 3
- 239000003279 phenylacetic acid Substances 0.000 description 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 229920005552 sodium lignosulfonate Polymers 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- LDPXUTOXMVCPSC-UHFFFAOYSA-N (2-hydroxyphenyl)methyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1O LDPXUTOXMVCPSC-UHFFFAOYSA-N 0.000 description 2
- RRGUMJYEQDVBFP-UHFFFAOYSA-N (Methanesulfinylsulfanyl)methane Chemical compound CSS(C)=O RRGUMJYEQDVBFP-UHFFFAOYSA-N 0.000 description 2
- VGPIBGGRCVEHQZ-UHFFFAOYSA-N 1-(biphenyl-4-yloxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)OC(C=C1)=CC=C1C1=CC=CC=C1 VGPIBGGRCVEHQZ-UHFFFAOYSA-N 0.000 description 2
- QSSXJPIWXQTSIX-UHFFFAOYSA-N 1-bromo-2-methylbenzene Chemical compound CC1=CC=CC=C1Br QSSXJPIWXQTSIX-UHFFFAOYSA-N 0.000 description 2
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 241000223600 Alternaria Species 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- 241001480061 Blumeria graminis Species 0.000 description 2
- 241000123650 Botrytis cinerea Species 0.000 description 2
- 239000005746 Carboxin Substances 0.000 description 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 2
- 241000510928 Erysiphe necator Species 0.000 description 2
- 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 2
- 244000166102 Eucalyptus leucoxylon Species 0.000 description 2
- 235000016623 Fragaria vesca Nutrition 0.000 description 2
- 240000009088 Fragaria x ananassa Species 0.000 description 2
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 2
- 241001149475 Gaeumannomyces graminis Species 0.000 description 2
- 229930191978 Gibberellin Natural products 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- 241001330975 Magnaporthe oryzae Species 0.000 description 2
- 241000243786 Meloidogyne incognita Species 0.000 description 2
- 240000005561 Musa balbisiana Species 0.000 description 2
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- NWBJYWHLCVSVIJ-UHFFFAOYSA-N N-benzyladenine Chemical compound N=1C=NC=2NC=NC=2C=1NCC1=CC=CC=C1 NWBJYWHLCVSVIJ-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- 244000061176 Nicotiana tabacum Species 0.000 description 2
- 241001223281 Peronospora Species 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 241001123583 Puccinia striiformis Species 0.000 description 2
- 241000813090 Rhizoctonia solani Species 0.000 description 2
- 241001515786 Rhynchosporium Species 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 241000722133 Tilletia Species 0.000 description 2
- 241000221566 Ustilago Species 0.000 description 2
- 241000228452 Venturia inaequalis Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical group 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 229960000892 attapulgite Drugs 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- GYSSRZJIHXQEHQ-UHFFFAOYSA-N carboxin Chemical compound S1CCOC(C)=C1C(=O)NC1=CC=CC=C1 GYSSRZJIHXQEHQ-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000002361 compost Substances 0.000 description 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 229940045803 cuprous chloride Drugs 0.000 description 2
- YPHMISFOHDHNIV-FSZOTQKASA-N cycloheximide Chemical compound C1[C@@H](C)C[C@H](C)C(=O)[C@@H]1[C@H](O)CC1CC(=O)NC(=O)C1 YPHMISFOHDHNIV-FSZOTQKASA-N 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000010413 gardening Methods 0.000 description 2
- 239000003448 gibberellin Substances 0.000 description 2
- IXORZMNAPKEEDV-OBDJNFEBSA-N gibberellin A3 Chemical class C([C@@]1(O)C(=C)C[C@@]2(C1)[C@H]1C(O)=O)C[C@H]2[C@]2(C=C[C@@H]3O)[C@H]1[C@]3(C)C(=O)O2 IXORZMNAPKEEDV-OBDJNFEBSA-N 0.000 description 2
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 238000011081 inoculation Methods 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- CPIKEDMPXDEUED-UHFFFAOYSA-N methyl 2-(2-phenylmethoxyphenyl)acetate Chemical class COC(=O)CC1=CC=CC=C1OCC1=CC=CC=C1 CPIKEDMPXDEUED-UHFFFAOYSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000006053 organic reaction Methods 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- 229910052625 palygorskite Inorganic materials 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000003375 plant hormone Substances 0.000 description 2
- 229920001983 poloxamer Polymers 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 125000004436 sodium atom Chemical group 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-UHFFFAOYSA-N 0.000 description 2
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- JLIDBLDQVAYHNE-YKALOCIXSA-N (+)-Abscisic acid Chemical compound OC(=O)/C=C(/C)\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C JLIDBLDQVAYHNE-YKALOCIXSA-N 0.000 description 1
- YNWVFADWVLCOPU-MDWZMJQESA-N (1E)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1/C(C(O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-MDWZMJQESA-N 0.000 description 1
- UDPGUMQDCGORJQ-UHFFFAOYSA-N (2-chloroethyl)phosphonic acid Chemical compound OP(O)(=O)CCCl UDPGUMQDCGORJQ-UHFFFAOYSA-N 0.000 description 1
- SAPGTCDSBGMXCD-UHFFFAOYSA-N (2-chlorophenyl)-(4-fluorophenyl)-pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(F)C=C1 SAPGTCDSBGMXCD-UHFFFAOYSA-N 0.000 description 1
- RYAUSSKQMZRMAI-ALOPSCKCSA-N (2S,6R)-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1C[C@H](C)O[C@H](C)C1 RYAUSSKQMZRMAI-ALOPSCKCSA-N 0.000 description 1
- URDNHJIVMYZFRT-KGLIPLIRSA-N (2r,3r)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pentan-3-ol Chemical compound C([C@H]([C@H](O)C(C)(C)C)N1N=CN=C1)C1=CC=C(Cl)C=C1Cl URDNHJIVMYZFRT-KGLIPLIRSA-N 0.000 description 1
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- RMOGWMIKYWRTKW-UONOGXRCSA-N (S,S)-paclobutrazol Chemical compound C([C@@H]([C@@H](O)C(C)(C)C)N1N=CN=C1)C1=CC=C(Cl)C=C1 RMOGWMIKYWRTKW-UONOGXRCSA-N 0.000 description 1
- CKPCAYZTYMHQEX-NBVRZTHBSA-N (e)-1-(2,4-dichlorophenyl)-n-methoxy-2-pyridin-3-ylethanimine Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(=N/OC)/CC1=CC=CN=C1 CKPCAYZTYMHQEX-NBVRZTHBSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 1
- JWUCHKBSVLQQCO-UHFFFAOYSA-N 1-(2-fluorophenyl)-1-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanol Chemical compound C=1C=C(F)C=CC=1C(C=1C(=CC=CC=1)F)(O)CN1C=NC=N1 JWUCHKBSVLQQCO-UHFFFAOYSA-N 0.000 description 1
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 1
- RKLCNSACPVMCDV-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-methyl-1-pyrimidin-5-ylpropan-1-ol Chemical compound C=1N=CN=CC=1C(O)(C(C)C)C1=CC=C(Cl)C=C1 RKLCNSACPVMCDV-UHFFFAOYSA-N 0.000 description 1
- SLRVNRROEYCAHO-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,6-dimethyl-2-oxopyridine-3-carboxylic acid Chemical compound O=C1C(C(O)=O)=C(C)C=C(C)N1C1=CC=C(Cl)C=C1 SLRVNRROEYCAHO-UHFFFAOYSA-N 0.000 description 1
- WKBPZYKAUNRMKP-UHFFFAOYSA-N 1-[2-(2,4-dichlorophenyl)pentyl]1,2,4-triazole Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CN1C=NC=N1 WKBPZYKAUNRMKP-UHFFFAOYSA-N 0.000 description 1
- PZBPKYOVPCNPJY-UHFFFAOYSA-N 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=C)CN1C=NC=C1 PZBPKYOVPCNPJY-UHFFFAOYSA-N 0.000 description 1
- MGNFYQILYYYUBS-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1CCCCC1 MGNFYQILYYYUBS-UHFFFAOYSA-N 0.000 description 1
- KPNPDRFFWQBXGT-UHFFFAOYSA-N 1-dimethoxyphosphorylsulfanyl-2-ethylsulfanylethane;2-ethylsulfanylethoxy-dimethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCSCCOP(=S)(OC)OC.CCSCCSP(=O)(OC)OC KPNPDRFFWQBXGT-UHFFFAOYSA-N 0.000 description 1
- YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 description 1
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- ZMZGFLUUZLELNE-UHFFFAOYSA-N 2,3,5-triiodobenzoic acid Chemical compound OC(=O)C1=CC(I)=CC(I)=C1I ZMZGFLUUZLELNE-UHFFFAOYSA-N 0.000 description 1
- SVPKNMBRVBMTLB-UHFFFAOYSA-N 2,3-dichloronaphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(Cl)=C(Cl)C(=O)C2=C1 SVPKNMBRVBMTLB-UHFFFAOYSA-N 0.000 description 1
- BTTNYQZNBZNDOR-UHFFFAOYSA-N 2,4-dichloropyrimidine Chemical compound ClC1=CC=NC(Cl)=N1 BTTNYQZNBZNDOR-UHFFFAOYSA-N 0.000 description 1
- STMIIPIFODONDC-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)(CCCC)CN1C=NC=N1 STMIIPIFODONDC-UHFFFAOYSA-N 0.000 description 1
- IWSGKSUCFVOWQU-UHFFFAOYSA-N 2-(2-bromophenyl)-1,3-dioxolane Chemical compound BrC1=CC=CC=C1C1OCCO1 IWSGKSUCFVOWQU-UHFFFAOYSA-N 0.000 description 1
- IEORSVTYLWZQJQ-UHFFFAOYSA-N 2-(2-nonylphenoxy)ethanol Chemical compound CCCCCCCCCC1=CC=CC=C1OCCO IEORSVTYLWZQJQ-UHFFFAOYSA-N 0.000 description 1
- HZJKXKUJVSEEFU-UHFFFAOYSA-N 2-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)hexanenitrile Chemical compound C=1C=C(Cl)C=CC=1C(CCCC)(C#N)CN1C=NC=N1 HZJKXKUJVSEEFU-UHFFFAOYSA-N 0.000 description 1
- BAZVFQBTJPBRTJ-UHFFFAOYSA-N 2-chloro-5-nitropyridine Chemical compound [O-][N+](=O)C1=CC=C(Cl)N=C1 BAZVFQBTJPBRTJ-UHFFFAOYSA-N 0.000 description 1
- OWDLFBLNMPCXSD-UHFFFAOYSA-N 2-chloro-N-(2,6-dimethylphenyl)-N-(2-oxotetrahydrofuran-3-yl)acetamide Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)C1C(=O)OCC1 OWDLFBLNMPCXSD-UHFFFAOYSA-N 0.000 description 1
- CHZCERSEMVWNHL-UHFFFAOYSA-N 2-hydroxybenzonitrile Chemical class OC1=CC=CC=C1C#N CHZCERSEMVWNHL-UHFFFAOYSA-N 0.000 description 1
- CBQDTCDOVVBGMN-UHFFFAOYSA-N 2-methyl-3-octylphenol Chemical compound CCCCCCCCC1=CC=CC(O)=C1C CBQDTCDOVVBGMN-UHFFFAOYSA-N 0.000 description 1
- RZCJYMOBWVJQGV-UHFFFAOYSA-N 2-naphthyloxyacetic acid Chemical compound C1=CC=CC2=CC(OCC(=O)O)=CC=C21 RZCJYMOBWVJQGV-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- ZRDUSMYWDRPZRM-UHFFFAOYSA-N 2-sec-butyl-4,6-dinitrophenyl 3-methylbut-2-enoate Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)C=C(C)C ZRDUSMYWDRPZRM-UHFFFAOYSA-N 0.000 description 1
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 1
- FSCWZHGZWWDELK-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)-5-ethenyl-5-methyl-2,4-oxazolidinedione Chemical compound O=C1C(C)(C=C)OC(=O)N1C1=CC(Cl)=CC(Cl)=C1 FSCWZHGZWWDELK-UHFFFAOYSA-N 0.000 description 1
- DXBQEHHOGRVYFF-UHFFFAOYSA-N 3-pyridin-4-ylpentane-2,4-dione Chemical group CC(=O)C(C(C)=O)C1=CC=NC=C1 DXBQEHHOGRVYFF-UHFFFAOYSA-N 0.000 description 1
- ABZSPJVXTTUFAA-UHFFFAOYSA-N 4-acetamido-N-(2-amino-5-thiophen-2-ylphenyl)benzamide Chemical compound C1=CC(NC(=O)C)=CC=C1C(=O)NC1=CC(C=2SC=CC=2)=CC=C1N ABZSPJVXTTUFAA-UHFFFAOYSA-N 0.000 description 1
- ZOMKCDYJHAQMCU-UHFFFAOYSA-N 4-butyl-1,2,4-triazole Chemical group CCCCN1C=NN=C1 ZOMKCDYJHAQMCU-UHFFFAOYSA-N 0.000 description 1
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 1
- FFISWZPYNKWIRR-UHFFFAOYSA-N 5-oxidophenazin-5-ium Chemical compound C1=CC=C2[N+]([O-])=C(C=CC=C3)C3=NC2=C1 FFISWZPYNKWIRR-UHFFFAOYSA-N 0.000 description 1
- DIYHCWVDDMVIKD-UHFFFAOYSA-N 6-methyl-2h-pyridin-3-one Chemical compound CC1=NCC(=O)C=C1 DIYHCWVDDMVIKD-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 244000291564 Allium cepa Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000193738 Bacillus anthracis Species 0.000 description 1
- 239000005734 Benalaxyl Substances 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 239000005739 Bordeaux mixture Substances 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- 241000233685 Bremia lactucae Species 0.000 description 1
- 239000005489 Bromoxynil Substances 0.000 description 1
- 239000005742 Bupirimate Substances 0.000 description 1
- 239000005885 Buprofezin Substances 0.000 description 1
- ZZVVDIVWGXTDRQ-BSYVCWPDSA-N Buthiobate Chemical compound C=1C=CN=CC=1\N=C(/SCCCC)SCC1=CC=C(C(C)(C)C)C=C1 ZZVVDIVWGXTDRQ-BSYVCWPDSA-N 0.000 description 1
- XXZMYVZZRKURAL-UHFFFAOYSA-N C(#N)C1=NC=CC=C1.[O] Chemical compound C(#N)C1=NC=CC=C1.[O] XXZMYVZZRKURAL-UHFFFAOYSA-N 0.000 description 1
- GKRYOTUQPZKDFB-UHFFFAOYSA-N C1=CC=CC=C1C(=O)OO.[Cl] Chemical compound C1=CC=CC=C1C(=O)OO.[Cl] GKRYOTUQPZKDFB-UHFFFAOYSA-N 0.000 description 1
- XJARZOBCDFTNAE-UHFFFAOYSA-N C[AsH](O)=O.N.[Fe+2] Chemical compound C[AsH](O)=O.N.[Fe+2] XJARZOBCDFTNAE-UHFFFAOYSA-N 0.000 description 1
- 241000345998 Calamus manan Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- 241001065113 Cercosporidium Species 0.000 description 1
- 239000005944 Chlorpyrifos Substances 0.000 description 1
- 240000007154 Coffea arabica Species 0.000 description 1
- 241000219112 Cucumis Species 0.000 description 1
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- KRZUZYJEQBXUIN-UHFFFAOYSA-N Cyprofuram Chemical compound ClC1=CC=CC(N(C2C(OCC2)=O)C(=O)C2CC2)=C1 KRZUZYJEQBXUIN-UHFFFAOYSA-N 0.000 description 1
- NOQGZXFMHARMLW-UHFFFAOYSA-N Daminozide Chemical compound CN(C)NC(=O)CCC(O)=O NOQGZXFMHARMLW-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- MTBZIGHNGSTDJV-UHFFFAOYSA-N Ditalimfos Chemical compound C1=CC=C2C(=O)N(P(=S)(OCC)OCC)C(=O)C2=C1 MTBZIGHNGSTDJV-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000005765 Dodemorph Substances 0.000 description 1
- 239000005766 Dodine Substances 0.000 description 1
- OQOULEWDDRNBSG-UHFFFAOYSA-N Fenapanil Chemical compound C=1C=CC=CC=1C(CCCC)(C#N)CN1C=CN=C1 OQOULEWDDRNBSG-UHFFFAOYSA-N 0.000 description 1
- 239000005777 Fenpropidin Substances 0.000 description 1
- 239000005778 Fenpropimorph Substances 0.000 description 1
- PNVJTZOFSHSLTO-UHFFFAOYSA-N Fenthion Chemical compound COP(=S)(OC)OC1=CC=C(SC)C(C)=C1 PNVJTZOFSHSLTO-UHFFFAOYSA-N 0.000 description 1
- 239000005786 Flutolanil Substances 0.000 description 1
- 239000005787 Flutriafol Substances 0.000 description 1
- 239000005791 Fuberidazole Substances 0.000 description 1
- 239000005562 Glyphosate Substances 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 235000008694 Humulus lupulus Nutrition 0.000 description 1
- 239000005795 Imazalil Substances 0.000 description 1
- PFDCOZXELJAUTR-UHFFFAOYSA-N Inabenfide Chemical compound C=1C(Cl)=CC=C(NC(=O)C=2C=CN=CC=2)C=1C(O)C1=CC=CC=C1 PFDCOZXELJAUTR-UHFFFAOYSA-N 0.000 description 1
- 239000005867 Iprodione Substances 0.000 description 1
- FAIXYKHYOGVFKA-UHFFFAOYSA-N Kinetin Natural products N=1C=NC=2N=CNC=2C=1N(C)C1=CC=CO1 FAIXYKHYOGVFKA-UHFFFAOYSA-N 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- BGRDGMRNKXEXQD-UHFFFAOYSA-N Maleic hydrazide Chemical compound OC1=CC=C(O)N=N1 BGRDGMRNKXEXQD-UHFFFAOYSA-N 0.000 description 1
- OKIBNKKYNPBDRS-UHFFFAOYSA-N Mefluidide Chemical compound CC(=O)NC1=CC(NS(=O)(=O)C(F)(F)F)=C(C)C=C1C OKIBNKKYNPBDRS-UHFFFAOYSA-N 0.000 description 1
- 206010027146 Melanoderma Diseases 0.000 description 1
- 241001143352 Meloidogyne Species 0.000 description 1
- 239000005807 Metalaxyl Substances 0.000 description 1
- 239000005811 Myclobutanil Substances 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical class [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- VJAWBEFMCIINFU-UHFFFAOYSA-N Nitrothal-isopropyl Chemical compound CC(C)OC(=O)C1=CC(C(=O)OC(C)C)=CC([N+]([O-])=O)=C1 VJAWBEFMCIINFU-UHFFFAOYSA-N 0.000 description 1
- VSKDLKJOZFLQQZ-UHFFFAOYSA-M O[Sn] Chemical compound O[Sn] VSKDLKJOZFLQQZ-UHFFFAOYSA-M 0.000 description 1
- 241001668536 Oculimacula yallundae Species 0.000 description 1
- 239000005985 Paclobutrazol Substances 0.000 description 1
- 241000315044 Passalora arachidicola Species 0.000 description 1
- 239000005813 Penconazole Substances 0.000 description 1
- 239000005814 Pencycuron Substances 0.000 description 1
- 241001507673 Penicillium digitatum Species 0.000 description 1
- 241000122123 Penicillium italicum Species 0.000 description 1
- 239000006002 Pepper Substances 0.000 description 1
- 244000025272 Persea americana Species 0.000 description 1
- 235000008673 Persea americana Nutrition 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000233622 Phytophthora infestans Species 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 235000016761 Piper aduncum Nutrition 0.000 description 1
- 240000003889 Piper guineense Species 0.000 description 1
- 235000017804 Piper guineense Nutrition 0.000 description 1
- 235000008184 Piper nigrum Nutrition 0.000 description 1
- 241001281803 Plasmopara viticola Species 0.000 description 1
- 241001337928 Podosphaera leucotricha Species 0.000 description 1
- 229930182764 Polyoxin Natural products 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000005820 Prochloraz Substances 0.000 description 1
- 239000005821 Propamocarb Substances 0.000 description 1
- 239000005822 Propiconazole Substances 0.000 description 1
- 239000005823 Propineb Substances 0.000 description 1
- 241001281805 Pseudoperonospora cubensis Species 0.000 description 1
- 241000342307 Pseudoperonospora humuli Species 0.000 description 1
- 241001123559 Puccinia hordei Species 0.000 description 1
- 241001123569 Puccinia recondita Species 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 241000220324 Pyrus Species 0.000 description 1
- 229910003691 SiBr Inorganic materials 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 241000579741 Sphaerotheca <fungi> Species 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 239000005842 Thiophanate-methyl Substances 0.000 description 1
- 239000005843 Thiram Substances 0.000 description 1
- 239000005845 Tolclofos-methyl Substances 0.000 description 1
- 239000005846 Triadimenol Substances 0.000 description 1
- CNFMJLVJDNGPHR-UKTHLTGXSA-N Triapenthenol Chemical compound C1=NC=NN1/C(C(O)C(C)(C)C)=C/C1CCCCC1 CNFMJLVJDNGPHR-UKTHLTGXSA-N 0.000 description 1
- 241000223261 Trichoderma viride Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229930195482 Validamycin Natural products 0.000 description 1
- CVQODEWAPZVVBU-UHFFFAOYSA-N XMC Chemical compound CNC(=O)OC1=CC(C)=CC(C)=C1 CVQODEWAPZVVBU-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
- XGCDHPDIERKJPT-UHFFFAOYSA-N [F].[S] Chemical compound [F].[S] XGCDHPDIERKJPT-UHFFFAOYSA-N 0.000 description 1
- CITUKXWBRAWXJQ-UHFFFAOYSA-N [P].[S].O1N=CC=C1 Chemical compound [P].[S].O1N=CC=C1 CITUKXWBRAWXJQ-UHFFFAOYSA-N 0.000 description 1
- UEDBHEFYEKZZBA-UHFFFAOYSA-N ac1np5zy Chemical compound C1=CC=[C+]=C[CH]1 UEDBHEFYEKZZBA-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- QKPZVFHXEGECIX-UHFFFAOYSA-N acetic acid;guanidine Chemical class CC(O)=O.CC(O)=O.CC(O)=O.NC(N)=N QKPZVFHXEGECIX-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- IMHBYKMAHXWHRP-UHFFFAOYSA-N anilazine Chemical compound ClC1=CC=CC=C1NC1=NC(Cl)=NC(Cl)=N1 IMHBYKMAHXWHRP-UHFFFAOYSA-N 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 1
- VGPYEHKOIGNJKV-UHFFFAOYSA-N asulam Chemical compound COC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VGPYEHKOIGNJKV-UHFFFAOYSA-N 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 238000000498 ball milling Methods 0.000 description 1
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 description 1
- UGYRYNXDEOFIQB-UHFFFAOYSA-N benzene thiophene Chemical compound S1C=CC=C1.C1=CC=CC=C1.C1=CC=CC=C1 UGYRYNXDEOFIQB-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
- 229960004217 benzyl alcohol Drugs 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 125000001743 benzylic group Chemical group 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 229920002988 biodegradable polymer Polymers 0.000 description 1
- 239000004621 biodegradable polymer Substances 0.000 description 1
- OIPMQULDKWSNGX-UHFFFAOYSA-N bis[[ethoxy(oxo)phosphaniumyl]oxy]alumanyloxy-ethoxy-oxophosphanium Chemical compound [Al+3].CCO[P+]([O-])=O.CCO[P+]([O-])=O.CCO[P+]([O-])=O OIPMQULDKWSNGX-UHFFFAOYSA-N 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- DSKJPMWIHSOYEA-UHFFFAOYSA-N bupirimate Chemical compound CCCCC1=C(C)N=C(NCC)N=C1OS(=O)(=O)N(C)C DSKJPMWIHSOYEA-UHFFFAOYSA-N 0.000 description 1
- PRLVTUNWOQKEAI-VKAVYKQESA-N buprofezin Chemical compound O=C1N(C(C)C)\C(=N\C(C)(C)C)SCN1C1=CC=CC=C1 PRLVTUNWOQKEAI-VKAVYKQESA-N 0.000 description 1
- JIJAYWGYIDJVJI-UHFFFAOYSA-N butyl naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)OCCCC)=CC=CC2=C1 JIJAYWGYIDJVJI-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- HCWYXKWQOMTBKY-UHFFFAOYSA-N calcium;dodecyl benzenesulfonate Chemical compound [Ca].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 HCWYXKWQOMTBKY-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 0.000 description 1
- QNEFNFIKZWUAEQ-UHFFFAOYSA-N carbonic acid;potassium Chemical compound [K].OC(O)=O QNEFNFIKZWUAEQ-UHFFFAOYSA-N 0.000 description 1
- JLQUFIHWVLZVTJ-UHFFFAOYSA-N carbosulfan Chemical compound CCCCN(CCCC)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 JLQUFIHWVLZVTJ-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 1
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000016213 coffee Nutrition 0.000 description 1
- 235000013353 coffee beverage Nutrition 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- LSFUGNKKPMBOMG-UHFFFAOYSA-N cycloprothrin Chemical compound ClC1(Cl)CC1(C=1C=CC=CC=1)C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 LSFUGNKKPMBOMG-UHFFFAOYSA-N 0.000 description 1
- 239000004062 cytokinin Substances 0.000 description 1
- UQHKFADEQIVWID-UHFFFAOYSA-N cytokinin Natural products C1=NC=2C(NCC=C(CO)C)=NC=NC=2N1C1CC(O)C(CO)O1 UQHKFADEQIVWID-UHFFFAOYSA-N 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- PBGGNZZGJIKBMJ-UHFFFAOYSA-N di(propan-2-yl)azanide Chemical compound CC(C)[N-]C(C)C PBGGNZZGJIKBMJ-UHFFFAOYSA-N 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- WURGXGVFSMYFCG-UHFFFAOYSA-N dichlofluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=CC=C1 WURGXGVFSMYFCG-UHFFFAOYSA-N 0.000 description 1
- BIXZHMJUSMUDOQ-UHFFFAOYSA-N dichloran Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl BIXZHMJUSMUDOQ-UHFFFAOYSA-N 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- UWQMKVBQKFHLCE-UHFFFAOYSA-N diclomezine Chemical compound C1=C(Cl)C(C)=C(Cl)C=C1C1=NNC(=O)C=C1 UWQMKVBQKFHLCE-UHFFFAOYSA-N 0.000 description 1
- 229940004812 dicloran Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- FWCBATIDXGJRMF-UHFFFAOYSA-N dikegulac Natural products C12OC(C)(C)OCC2OC2(C(O)=O)C1OC(C)(C)O2 FWCBATIDXGJRMF-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- WNNFQQLMCDOJMQ-UHFFFAOYSA-L disodium;2-phenylacetate Chemical compound [Na+].[Na+].[O-]C(=O)CC1=CC=CC=C1.[O-]C(=O)CC1=CC=CC=C1 WNNFQQLMCDOJMQ-UHFFFAOYSA-L 0.000 description 1
- PYZSVQVRHDXQSL-UHFFFAOYSA-N dithianon Chemical compound S1C(C#N)=C(C#N)SC2=C1C(=O)C1=CC=CC=C1C2=O PYZSVQVRHDXQSL-UHFFFAOYSA-N 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JMXKCYUTURMERF-UHFFFAOYSA-N dodemorph Chemical compound C1C(C)OC(C)CN1C1CCCCCCCCCCC1 JMXKCYUTURMERF-UHFFFAOYSA-N 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- AWZOLILCOUMRDG-UHFFFAOYSA-N edifenphos Chemical compound C=1C=CC=CC=1SP(=O)(OCC)SC1=CC=CC=C1 AWZOLILCOUMRDG-UHFFFAOYSA-N 0.000 description 1
- 229960002125 enilconazole Drugs 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- DWRKFAJEBUWTQM-UHFFFAOYSA-N etaconazole Chemical compound O1C(CC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 DWRKFAJEBUWTQM-UHFFFAOYSA-N 0.000 description 1
- CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- BBXXLROWFHWFQY-UHFFFAOYSA-N ethirimol Chemical compound CCCCC1=C(C)NC(NCC)=NC1=O BBXXLROWFHWFQY-UHFFFAOYSA-N 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- KQTVWCSONPJJPE-UHFFFAOYSA-N etridiazole Chemical compound CCOC1=NC(C(Cl)(Cl)Cl)=NS1 KQTVWCSONPJJPE-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 description 1
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 1
- WDQNIWFZKXZFAY-UHFFFAOYSA-M fentin acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 WDQNIWFZKXZFAY-UHFFFAOYSA-M 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- FQKUGOMFVDPBIZ-UHFFFAOYSA-N flusilazole Chemical compound C=1C=C(F)C=CC=1[Si](C=1C=CC(F)=CC=1)(C)CN1C=NC=N1 FQKUGOMFVDPBIZ-UHFFFAOYSA-N 0.000 description 1
- PTCGDEVVHUXTMP-UHFFFAOYSA-N flutolanil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C(F)(F)F)=C1 PTCGDEVVHUXTMP-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000004345 fruit ripening Effects 0.000 description 1
- ZEYJIQLVKGBLEM-UHFFFAOYSA-N fuberidazole Chemical compound C1=COC(C=2N=C3[CH]C=CC=C3N=2)=C1 ZEYJIQLVKGBLEM-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 1
- 229940097068 glyphosate Drugs 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 239000000122 growth hormone Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 239000003501 hydroponics Substances 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 1
- JTEDVYBZBROSJT-UHFFFAOYSA-N indole-3-butyric acid Chemical compound C1=CC=C2C(CCCC(=O)O)=CNC2=C1 JTEDVYBZBROSJT-UHFFFAOYSA-N 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- FCOAHACKGGIURQ-UHFFFAOYSA-N iprobenfos Chemical compound CC(C)OP(=O)(OC(C)C)SCC1=CC=CC=C1 FCOAHACKGGIURQ-UHFFFAOYSA-N 0.000 description 1
- ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 description 1
- QBSJMKIUCUGGNG-UHFFFAOYSA-N isoprocarb Chemical compound CNC(=O)OC1=CC=CC=C1C(C)C QBSJMKIUCUGGNG-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- UFHLMYOGRXOCSL-UHFFFAOYSA-N isoprothiolane Chemical compound CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1 UFHLMYOGRXOCSL-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- PVTHJAPFENJVNC-MHRBZPPQSA-N kasugamycin Chemical compound N[C@H]1C[C@H](NC(=N)C(O)=O)[C@@H](C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O PVTHJAPFENJVNC-MHRBZPPQSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- QANMHLXAZMSUEX-UHFFFAOYSA-N kinetin Chemical compound N=1C=NC=2N=CNC=2C=1NCC1=CC=CO1 QANMHLXAZMSUEX-UHFFFAOYSA-N 0.000 description 1
- 229960001669 kinetin Drugs 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 235000012204 lemonade/lime carbonate Nutrition 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 150000002641 lithium Chemical group 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- YKSNLCVSTHTHJA-UHFFFAOYSA-L maneb Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S YKSNLCVSTHTHJA-UHFFFAOYSA-L 0.000 description 1
- 229920000940 maneb Polymers 0.000 description 1
- BCTQJXQXJVLSIG-UHFFFAOYSA-N mepronil Chemical compound CC(C)OC1=CC=CC(NC(=O)C=2C(=CC=CC=2)C)=C1 BCTQJXQXJVLSIG-UHFFFAOYSA-N 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- ZWJNEYVWPYIKMB-UHFFFAOYSA-N methfuroxam Chemical compound CC1=C(C)OC(C)=C1C(=O)NC1=CC=CC=C1 ZWJNEYVWPYIKMB-UHFFFAOYSA-N 0.000 description 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
- CNTVWMRWECWTRT-UHFFFAOYSA-N methyl 2,5-dichloro-4-methoxybenzoate Chemical compound COC(=O)C1=CC(Cl)=C(OC)C=C1Cl CNTVWMRWECWTRT-UHFFFAOYSA-N 0.000 description 1
- LINPVWIEWJTEEJ-UHFFFAOYSA-N methyl 2-chloro-9-hydroxyfluorene-9-carboxylate Chemical compound C1=C(Cl)C=C2C(C(=O)OC)(O)C3=CC=CC=C3C2=C1 LINPVWIEWJTEEJ-UHFFFAOYSA-N 0.000 description 1
- ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 description 1
- CJPQIRJHIZUAQP-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)alaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)CC1=CC=CC=C1 CJPQIRJHIZUAQP-UHFFFAOYSA-N 0.000 description 1
- CIEXPHRYOLIQQD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-2-furoylalaninate Chemical compound CC=1C=CC=C(C)C=1N(C(C)C(=O)OC)C(=O)C1=CC=CO1 CIEXPHRYOLIQQD-UHFFFAOYSA-N 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- BLCKKNLGFULNRC-UHFFFAOYSA-L n,n-dimethylcarbamodithioate;nickel(2+) Chemical compound [Ni+2].CN(C)C([S-])=S.CN(C)C([S-])=S BLCKKNLGFULNRC-UHFFFAOYSA-L 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 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
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- AMEKQAFGQBKLKX-UHFFFAOYSA-N oxycarboxin Chemical compound O=S1(=O)CCOC(C)=C1C(=O)NC1=CC=CC=C1 AMEKQAFGQBKLKX-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000024241 parasitism Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 235000021017 pears Nutrition 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- OGYFATSSENRIKG-UHFFFAOYSA-N pencycuron Chemical compound C1=CC(Cl)=CC=C1CN(C(=O)NC=1C=CC=CC=1)C1CCCC1 OGYFATSSENRIKG-UHFFFAOYSA-N 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
- XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000005359 phenoxyalkyl group Chemical group 0.000 description 1
- XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 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
- 229920001084 poly(chloroprene) Polymers 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
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- TVLSRXXIMLFWEO-UHFFFAOYSA-N prochloraz Chemical compound C1=CN=CN1C(=O)N(CCC)CCOC1=C(Cl)C=C(Cl)C=C1Cl TVLSRXXIMLFWEO-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
- 230000000644 propagated effect Effects 0.000 description 1
- WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-UHFFFAOYSA-N 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
- 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- YRRBXJLFCBCKNW-UHFFFAOYSA-N prothiocarb Chemical compound CCSC(=O)NCCCN(C)C YRRBXJLFCBCKNW-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 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
- 235000012950 rattan cane Nutrition 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 230000002786 root growth Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- DEWVPZYHFVYXMZ-QCILGFJPSA-M sodium;(3ar,4as,8ar,8bs)-2,2,7,7-tetramethyl-4a,5,8a,8b-tetrahydro-[1,3]dioxolo[3,4]furo[1,3-d][1,3]dioxine-3a-carboxylate Chemical compound [Na+].O([C@H]12)C(C)(C)OC[C@@H]1O[C@]1(C([O-])=O)[C@H]2OC(C)(C)O1 DEWVPZYHFVYXMZ-QCILGFJPSA-M 0.000 description 1
- HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- QTENRWWVYAAPBI-YCRXJPFRSA-N streptomycin sulfate Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O QTENRWWVYAAPBI-YCRXJPFRSA-N 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- ROZUQUDEWZIBHV-UHFFFAOYSA-N tecloftalam Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(=O)NC1=CC=CC(Cl)=C1Cl ROZUQUDEWZIBHV-UHFFFAOYSA-N 0.000 description 1
- 239000004308 thiabendazole Substances 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
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical group COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 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
- 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
- 238000012546 transfer Methods 0.000 description 1
- 230000009466 transformation Effects 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
- 150000003852 triazoles Chemical class 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- AISMNBXOJRHCIA-UHFFFAOYSA-N trimethylazanium;bromide Chemical compound Br.CN(C)C AISMNBXOJRHCIA-UHFFFAOYSA-N 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin 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-IMTORBKUSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- CHNQZRKUZPNOOH-UHFFFAOYSA-J zinc;manganese(2+);n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[Zn+2].[S-]C(=S)NCCNC([S-])=S.[S-]C(=S)NCCNC([S-])=S CHNQZRKUZPNOOH-UHFFFAOYSA-J 0.000 description 1
- AMHNZOICSMBGDH-UHFFFAOYSA-L zineb Chemical compound [Zn+2].[S-]C(=S)NCCNC([S-])=S AMHNZOICSMBGDH-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—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
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
- C07D213/66—One oxygen atom attached in position 3 or 5 having in position 3 an oxygen atom and in each of the positions 4 and 5 a carbon atom bound to an oxygen, sulphur, or nitrogen atom, e.g. pyridoxal
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/68—One oxygen atom attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/69—Two or more oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
- C07D213/71—Sulfur atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
-
- 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
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
- C07D239/10—Oxygen or sulfur atoms
-
- 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
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
-
- 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
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
-
- 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
-
- 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
-
- 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
- C07D239/58—Two sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/80—Oxygen atoms
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
本发明涉及适合农用,具有式(I)的丙烯酸衍生物(尤其可作为杀真菌剂,但也可作为植物生长调节剂、杀虫剂及杀线虫剂),制备它们的方法,含有它们的农用(特别是杀真菌)组合物以及用其消除真菌(特别是在植物中传染的真菌)的方法,调节植物生长的方法及杀灭或控制昆虫或线虫的方法。其中A,W,X,Y,Z,R1和R2和说明书相同。
Description
本发明涉及适合农用的丙烯酸衍生物(尤其可作为杀真菌剂,但也可作为植物生长调节剂、杀虫剂及杀线虫剂),制备它们的方法,含有它们的农用(特别是杀真菌)组合物以及用其消除真菌(特别是在植物中传染的真菌)的方法,调节植物生长的方法及杀灭或控制昆虫或线虫的方法。
本发明提供了化合物(Ⅰ),其立体异构体及其金属配合物,
其中:
W是取代的吡啶基或取代的嘧啶基,并通过它们的任一环碳原子连接到A上;A是氧原子或S(O)n,这里的n为0、1或2;X、Y和Z可以相同或不同,它们可为氢原子或卤原子,或羟基、有选择取代的烷基(包括卤代烷基)、有选择取代的链烯基、有选择取代的炔基、有选择取代的烷氧基(包括卤代烷氧基)、有选择取代的烷硫基、有选择取代的芳氧基、有选择取代的芳烷氧基、有选择取代的酸基、有选择取代的氨基、有选择取代的酰氨基、硝基、氰基、-CO2R3、-CONR4R5、-COR6或-S(O)mR7(其中m为0、1或2),或当X、Y和Z中任意两个基团在苯环上处于相邻位置时,该两个基团可连接起来形成稠环,所说稠环或为芳香族的或为脂肪族的,可以有选择地含一个或多个杂原子;R1和R2可以相同或不同,它们可以是有选择取代的烷基(包括氟代烷基),其条件是W是5-三氟甲基吡啶-2-基,A是氧,X是氢,并且在R1和R2均为甲基,Y和Z不都是氢,Y不是F、Cl、甲基、硝基、5-CF3、5-SCH3或4-(CH3)2N时,其条件是Z是氢,Y和Z不同时是3-硝基-5-氯、3,5-二硝基、4,5-二甲氧基或4,5-亚甲二氧基;R3、R4、R5、R6和R7可以相同或不同,它们可以是氢原子或有选择取代的烷基、有选择取代的环烷基、有选择取代的环烷基烷基、有选择取代的链烯基、有选择取代的炔基、有选择取代的芳基或有选择取代的芳烷基。
本发明的化合物至少含有一个碳-碳双键,并且常常是以其几何异构体混合物的形式制得。然而这些异构体混合物可分离成单一的异构体,本发明也包含这样的异构体及其按各种比例的混合物,这包括基本上是由(Z)异构体组成的混合物和基本上是由(E)异构体组成的混合物。
一般用术语“E”和“Z”表示不对称取代丙烯酸酯双键而产生的异构体,这些术语是按Cahnlngold-Prelog系统来定义的,在文献〔请参见如J March“高等有机化学”(Advanced organic Chemistry)第三版,Wiley-Interscience 109页等〕中对此系统有详细叙述。
通常其中一种异构体一般比另一种异构体杀真菌的活性要高,相对于苯环而言,活性较高的异构体其中的-OR2基团在此双键同一例。在本发明化合物中,即为(E)异构体,(E)异构体构成本发明较好的实施方案。
本说明书将用式
代表丙烯酸酯双键的两个几何异构体可分的混合物,即
各烷基(无论是作为一个基团还是作为如“烷氧基”、“烷硫基”和“芳烷基”中的烷基部分)可以是直链的或支链的,并优选含1至6个碳原子的,最好选用含1至4个碳原子的,如甲基、乙基、丙基(正或异丙基)和丁基(正丁基、仲丁基、异丁基或叔丁基)。
有选择取代的烷基R1和R2优先选用有选择取代的C1-4、最好选用C1-2的烷基,优选的取代基可以是一个或多个氟原子。最优选的情况是R1和R2均为甲基,或者一个或两个甲基有选择地为一个、两个或三个氟原子所取代。
涉及的卤原子具体地讲是氟、氯或溴原子,特别是氟或氯原子。
优选的环烷基是C3-6环烷基,例如环己基,而优选的环烷基烷基是C3-6环烷基(C1-4)烷基,例如,环丙基乙基。优选的链烯基和炔基是含2-6、较好是含2-4个碳原子的直链或支链的链烯基或炔基,例如,乙烯基、烯丙基及炔丙基。优选的芳基是苯基,优选的芳烷基是苄基、苯乙基或苯基正丙基。有选择取代的烷基特别包括:卤代烷基、羟烷基、烷氧基烷基、有选择取代的芳烷基,尤其是有选择取代的苯烷基、有选择取代的芳氧基烷基,特别是有选择取代的苯氧基烷基;有选择取代的链烯基包括:有选择取代的苯链烯基,尤其是有选择取代的苯乙烯基;有选择取代的芳氧基包括有选择取代的苯氧基;有选择取代的芳烷氧基包括有选择取代的苄氧基。对于“烷氧基”和“烷硫基”的有选择的取代基包括上面对于“烷基”所述的取代基。
可存在于任何有选择取代的芳基或杂芳基部分的取代基包括下述的一个或多个基团:卤素、羟基、C1-4烷基(尤其是甲基和乙基)、C1-4烷氧基(特别是甲氧基)、卤代(C1-4)烷基(尤其是三氟甲基)、卤代(C1-4)烷基(尤其是三氟甲基)、卤代(C1-4)烷氧基(尤其是三氟甲氧基)、C1-4烷硫基(尤其是甲硫基)、(C1-4)烷氧基(C1-4)烷基、C3-6环烷基、C3-6环烷基(C1-4)烷基、芳基(尤其是苯基)、芳氧基(特别是苯氧基)、芳基(C1-4)烷基(特别是苄基、苯乙基和苯基正丙基)、芳基C1-4烷氧基(特别是苄氧基)、芳氧基(C1-4)烷基(特别是苯氧基甲基)、酰氧基(尤其是乙酰氧基和苯甲酰氧基)、氰基、氰硫基、硝基、-NR′R″、-NHCOR′、-NHCONR′R″、-CONR′R″、-COOR′、-OSO2R′、-SO2R′、-COR′、-OCOR′、-CR′=NR″或-N=CR′R″、(其中R′和R″可独立地为氢)、C1-4烷基、C1-4芳氧基、C1-4烷硫基、C3-6环烷基、C3-6环烷基(C1-4)烷基、苯基或苄基,所说的苯基或苄基可以用卤素、C1-4烷基或C1-4烷氧基有选择的取代。有选择取代的氨基、酰氨基和酰氧基包括:-NR′R″、-NHCOR′和-OCOR′,其中R′和R″的定义和上述相同。
在取代的吡啶环W或取代的嘧啶环W上的取代基可以是相同或不同的,其定义和上述的X、Y和Z相同。它们特别包括:卤原子、或羟基、有选择取代的烷基(包括卤代烷基),(尤其是C1-4烷基)、有选择取代的链烯基(尤其是C3-4链烯基)、有选择取代芳基、有选择取代的炔基(尤其是C3-4炔基)、有选择取代烷氧基(包括卤代烷氧基)(尤其是C1-4烷氧基)、有选择取代的芳氧基、有选择取代的杂环氧基(尤其是杂芳氧基)、有选择取代的芳基、有选择取代的杂环基,特别是五-和六-元碳-氮环,如
、硝基、氰基、-NR′R″、-NHCOR′、-CONR′R″、-OCOR′、-CO2R′、-COR′、-CH=NOR″、-CH2NR′R″、-CH2OR′、-CH2NHCOR′、-CH2OCOR′或S(O)mR′(其中m为0,1或2)、或在吡啶或嘧啶环上的任意两个取代基在此环上处于相邻位置时,这两个取代基可连起来形成有选择取代的稠环,该稠环为芳族的或为脂族的、可以有选择地含一个或多个杂原子;R′、R″、R3、R4、R5、R6和R7定义同上。
在适当位置上带有羟基取代基的吡啶或嘧啶还可以相应的互变异构的氧代形式存在,即分别为相应的吡啶酮类或嘧啶酮类。就是说,在吡啶或嘧啶环W上有羟基取代基的话,本发明就包括所有的这种互变异构形式及其各种混合物〔例如参见G R Newkome和W W Paudler现代杂环化学(Contemporary Heterocyclic Chemistry)Wiley-Interscience 236-241页〕。
优选的取代基卤代烷基和卤代烷氧基是卤代C1-4烷基和卤代(C1-4)烷氧基;卤代烷基尤其包括三卤甲基,最好是三氟甲基(另有说明除外)。
优选的芳基或芳基部分〔如芳氧基中的芳基〕是苯基,而在取代的氨基或氨基部分上的取代基优先选用C1-4烷基。
优选的杂环基团或杂环部分(例如在杂环或杂环氧基中的杂环)可以是2-、3-、或4-有选择取代的嘧啶类或2-、4-或5-有选择取代的嘧啶类。
一方面,本发明提供了化合物(Ⅰ)及其立体异构体,
在化合物(Ⅰ)中:W是取代的吡啶基或取代的嘧啶基,并通过它们的任意一个碳原子连接于A上,而其所带的取代基的定义同上;A是氧原子或S(O)n,其中n为0,1或2;X、Y和Z可以相同或不同,它们可以是氢、氟、氯或溴原子、或羟基、C1-4烷基、C2-5链烯基、C2-5炔基、苯基、C1-4卤代烷基、C1-4烷氧基、苯氧基、苄氧基、一或二烷基氨基,或此X、Y和Z中的任意两个基团在苯环上处于相邻位置时,这两个基团可以连接起来形成稠芳环;其中,上述任何基团的脂族部分可以有选择地由一个或多个下述基团所取代:C1-4烷氧基、氟、氯或溴原子、其本身为有选择取代的苯基、其本身为有选择取代的杂环(该杂环可以为芳族或非芳族的)、硝基、氨基、氰基、羟基或羧基;其中,上述的任何基团的苯基部分可以有选地由一个或多个下述基团取代:氟、氯或溴原子、苯基环、C1-4烷基、C1-4烷氧基、氰基、氨基、腈、羟基或羧基;R1和R2可以相同或不同,它们可以是C1-4烷基(尤其是均为甲基),所说的每一个烷基可以有选择地由一个、两个或三个卤原子(尤其是氟)所取代,其条件是W是5-三氟甲基吡啶-2-基,A是氧,X是氢,并且在R1和R2均为甲基,Y和Z不都为氢,Y不是氟、氯、甲基、硝基、5-CF3、5-SCH3或4-(CH3)2N时,其条件是Z是氢,Y和Z不同时是3-硝基-5-氯、3,5-二硝基、4,5-二甲氧基或4,5-亚甲二氧基。
当X、Y和Z中的一个或一个以上不是氢时,它们最好为简单的原子或为空间上小的基团,例如氟、氯、溴、羟基、甲基、甲氧基、三氟甲基、甲氨基和二甲氨基。更为优选的情况是,这类取代基之一在苯环的5位上(丙烯酸酯基连接于其1位上),因为对植物毒性而论,这可以有种种优点,尤其其中只有如氯这样简单的取代基存在时。
另一方面,本发明提供了化合物(Ⅰa)及其立体异构体,
其中,A是S(O)n,这里的n为0,1或2,或优先选用氧原子;W是取代的吡啶基或取代的嘧啶基,并通过它们的任意一个碳原子连接于A上,在吡啶或嘧啶环上的取代基可以相同或不同,可以为一个或多个卤原子、或羟基、有选择取代的烷基(包括卤代烷基)、有选择取代的链烯基、有选择取代的芳基、有选择取代的炔基、有选择取代的烷氧基(包括卤代烷氧基)、有选择取代的芳氧基、有选择取代的杂环氧基、有选择取代的杂环基、有选择取代的酰氧基、有选择取代的氨基、有选择取代酰氨基、硝基、氰基、-CO2R3、-CONR4R5、-COR6或S(O)mR7(其中m=0,1或2);如果W是5-三氟甲基吡啶-2-基,则A是氧和X是氢,并且在R1和R2都是甲基,Y和Z不都是氢,Y不是氟、氯、甲基、硝基、5-CF3、5-SCH3或4-(CH3)2N时,其条件是Z是氢,Y和Z不同时都是3-硝基-5-氯、3,5-二硝基、4,5-二甲氧基或4,5-亚甲二氧基;R3、R4、R5、R6和R7的定义同上。
在吡啶或嘧啶环上优选的取代基为氯、氟、溴、甲基、三氟甲基(另有说明除外)、三氯甲基和甲氧基。
再一个方面,本发明提供了化合物(Ⅰb),
(化合物Ⅰb见下页)
其中Q是甲基、三氟甲基(但不是5-三氟甲基)、甲氧基、溴、氟、或特别是氯。
Q在吡啶环上的优选位置是4-、5-或6-位,例如,当Q为甲基时,更优选的位置是在4-位上。
用列于下面表Ⅰ-Ⅲ中的化合物来说明本发明。
表Ⅳ
有选择的质子NMR数据
列于表Ⅳ中的数据是选自表Ⅰ、Ⅱ和Ⅲ中所述的油状或树胶状化合物的质子NMR数据。所测定的化学位移以ppm为单位,用的标准物质为四甲基硅烷,全都用氘氯仿作溶剂。其中应用如下缩写:
br=宽峰;s=单峰;d=二重峰;
t=三重峰;q=四重峰;m=多重峰;
ppm=百万分之一。
本发明的化合物(Ⅰ)可用取代的苯酚或苯硫酚(Ⅶ)按反应示意图Ⅰ所示的步骤来制备。在此图中,术语R1、R2、A、X、Y、Z和W的定义同上,L是卤原子或其他的易离去基团(往往可为硝基),R8是氢或金属原子(如钠原子)。
化合物(Ⅰ)可采用下述方法制备:于适宜的温度下、在适宜的溶剂(例如N,N-二甲基甲酰胺)中,用碱(如氢化钠或甲醇钠)和甲酸酯(如甲酸甲酯)处理乙酸苯酯(Ⅳ)〔图Ⅰ中的步骤(b)〕。所制得的化合物(Ⅰ)以几何异构体形式存在,这些几何异构体可用色谱法、分步结晶法或蒸馏法进行分离。如向此反应混合物中加入化合物R2-L(L的定义同上),便可得到化合物(Ⅰ)〔图Ⅰ中的步骤(a)〕;如向此反应混合物中加入亲质子酸,即得到其中R8是氢的化合物(Ⅲ);另一种办法是,将其中R8是金属原子(特别是如钠原子这类碱金属原子)的化合物(Ⅲ)本身从此反应混合物中分离出来。
于适宜的溶剂中,将化合物(Ⅲ)(其中的R8是金属原子)用R2-L(L定义同上)处理,则可将其转变为化合物(Ⅰ);于适宜的溶剂中,将其中R8是氢的化合物(Ⅲ)依次用碱(如碳酸钾)和R2-L处理,则可将其转变为化合物(Ⅰ)。
也可采用另一种办法制备化合物(Ⅰ),即用醛缩二醇(ⅩⅢ)作原料,于适宜的温度下、常于适宜的溶剂中,在酸性或碱性条件下,通过消除适当的链烷醇,可得到化合物(Ⅰ)〔图Ⅰ的步骤(C)〕。用于此转变的反应试剂或反应试剂混合物的例子有:二-异丙基氨基锂;硫酸氢钾〔例如参看T Yamada,H Hagiwara和H Uda化学协会化学通讯杂誌(J.Chem.Soc.,Chemical Communications)1980,838及其中的参考文献〕;三乙胺,常于四氯化钛这类路易氏酸存在下〔例如,参见K Nsunda和L Heresi,化学协会化学通讯杂志(J.Chem.Soc.,Chemical Communi-cations),1985,1000〕。
可用下述方法制备醛缩二乙醇(ⅩⅢ):于适宜的溶剂中、在一定的温度下,在诸如四氯化钛这类路易氏酸存在下,用单甲酸三烷基酯(R2O)3CH处理其中R是烷基的乙烯酮缩烷基甲硅烷基二乙醇(ⅩⅣ)〔如参见K Saigo,M osaki和T Mukaiyama,化学通讯(Chemistry Letters)1976,769〕。
乙烯酮缩烷基甲硅烷基二乙醇(ⅩⅣ)可用酯类(Ⅳ)来制备:于适宜的溶剂中、在一定的温度下,使式(Ⅳ)的酯与碱和三烷基硅烷基卤(其通式为R3SiCl或R3SiBr)反应,例如与三甲基硅烷基氯反应,或与碱和通式为R3Si-OSO2CF3的三烷基硅烷基三氟甲磺酸酯反应〔例如,参见C Ainsworth,F Chen和Y Kuo,有机金属化学杂志(J.Organometallic Chemistry),1972,46,59〕。
中间体(ⅩⅢ)和(ⅩⅣ)不一定总是需要分离;可于适宜的条件下以酯(Ⅳ)为原料,采用“一罐法”(“one pot”Seguence),通过相继加入上面所列的反应试剂制备化合物(Ⅰ)。
可用化学文献中所介绍的标准方法,将化合物(Ⅴ)进行酯化作用来制备化合物(Ⅳ)〔图Ⅰ中的步骤(d)〕。
化合物(Ⅴ)可用下述方法制备:于常用的溶剂(如N,N-二甲基甲酰胺)中、在碱(如碳酸钾)存在下,如有必要可用过渡金属或过渡金属盐作催化剂(如铜-青铜),将化合物(Ⅶ)与化合物(Ⅵ)反应〔图Ⅰ中的步骤(e)〕。
化合物(Ⅳ)还可用下述方法制备:于常用的溶剂(如N,N-二甲基甲酰胺)中、在碱(如碳酸钾)存在下,如需要的话,用过渡金属或过渡金属的盐作催化剂(如铜-青铜),将酯(Ⅷ)与化合物(Ⅵ)反应〔图Ⅰ中的步骤(f)〕。
按化学文献中所介绍的标准方法,将化合物(Ⅶ)进行酯化作用;即可制备酯(Ⅷ)〔图Ⅰ中的步骤(g)〕。
化合物(Ⅶ)可用化学文献中介绍的标准方法来制备〔例如,参见A.Clesse,W.Haefliger,D.Hauser,H.U.Gubler,B.Dewald和M.Baggiolini,药物化学杂志(J.med.Chem)1981,24,1465和P D Clark和D M Mckinnon,加拿大化学杂志(Can.J.Chem),1982 60.243及其中的参考文献〕。
可于适宜的温度下、适宜的溶剂中,用化学文献中所介绍的标准的氧化方法,例如用间-氯过苯甲酸之类的过酸,可以将其中A是硫的化合物(Ⅰ)转变为其中A是S(O)或S(O)2的化合物(Ⅰ)。
还可用乙酸苯酯(Ⅻ),按示意图Ⅱ中的步骤制备化合物(Ⅰ)。在示意图Ⅱ中,所有的术语R1、R2、R8、A、W、X、Y、Z和L定义同上,M是苯酚或苯硫酚的保护基团。
因此,可于常用的溶剂(如N,N-二甲基甲酰胺)中、在碱(如碳酸钾)存在下,如需要的话,可用过渡金属或过渡金属盐作催化剂,将化合物(Ⅸ)与化合物(Ⅵ)反应制备化合物(Ⅰ)〔图Ⅱ中的步骤(h)〕。
由经保护的苯酚或苯硫酚衍生物(Ⅹ),用化学文献中介绍的脱去保护的标准步骤来制备化合物(Ⅸ)〔图Ⅱ中的步骤(ⅰ)〕,例如,于适宜的催化剂存在下(如载于碳上的钯),将苄基醚(Ⅹ)(其中A是O,M是CH2Ph)进行氢解,便可制备其中A是0的苯酚(Ⅸ)。
于适宜的溶剂(如N,N-二甲基甲酰胺)中,适宜的温度下,用碱(如氢化钠或甲醇钠)和甲酸酯(如甲酸甲酯)处理乙酸苯酯(Ⅻ),即可制得其中的M是苯酚或苯硫酚标准的保护基团(如苄基)的化合物(Ⅹ)(图Ⅱ,步骤(k),然后在此反应混合物中加入R2-L(L定义同上),便可得到化合物(Ⅹ)〔图Ⅱ中的步骤(j)〕;如在此反应混合物中加入亲质子酸,便可得到其中R8是氢的化合物(Ⅺ);另外,可以使其中的R8是金属原子(特别是如钠原子这类的碱金属原子)的化合物(Ⅺ)本身从此反应混合物中分离出来。
于适宜的溶剂中,用R2-L进行处理,可以将其中R8是金属原子的化合物(Ⅺ)转变为化合物(Ⅹ)。相继用碱(如碳酸钾)和R2-L处理,则可将其中R8是氢的化合物(Ⅺ)转变为化合物(Ⅹ)。
可按化学文献中介绍的标准方法,用化合物(Ⅷ)制备化合物(Ⅻ)。
〔反应示意图Ⅰ、Ⅱ见46、47页〕
还可用取代的苯(ⅩⅠⅩ)按反应示意图Ⅲ的步骤来制备本发明化合物(Ⅰ),图Ⅲ中所用的术语R1、R2、A、W、X、Y和Z的定义同上,D是氢或卤素,E是金属原子(如锂原子)或为结合了-卤原子的金属原子(如MgI、MgBr或MgCl)。
可于诸如乙醚这类合适的溶剂中,用正膦(ⅩⅥ)处理酮酯(ⅩⅤ)来制备化合物(Ⅰ)〔例如,参见Ep-A-0044448和EP-A-0178826,图Ⅲ步骤(C)〕。
可于诸如乙醚或四氢呋喃这类适宜的溶剂中,用草酸酯(ⅩⅧ)处理金属取代的化合物(ⅩⅦ)即可制得酮酯(ⅩⅤ)。常用的优选办法是于搅拌下将金属取代的化合物(ⅩⅦ)的溶液慢慢地加入过量的草酸酯(ⅩⅧ)溶液中〔例如参看L M Weinstock,R B Currie和A V Lovell,合成通讯(Synthetic Communications)1981,11,943,和其中的参考文献〕〔反应示意图Ⅲ中的步骤(m)〕。
其中的E是MgI、MgBr或MgCl的金属取代的化合物(ⅩⅦ)(Grignard试剂)可按标准的方法,用其中的D分别是I、Br或Cl的相应的芳族卤化物(ⅩⅠⅩ)来制备。具有取代基X、Y和Z并且其中E是Li的金属取代的化合物(ⅩⅦ)可用强锂碱(诸如正丁基锂或二异丙酰胺基氨基锂)使其中D是氢的化合物(ⅩⅠⅩ)直接锂化来制备〔例如,参见H W Gschwend和H R Rodriguez,有机反应
反应示意图Ⅰ
反应示意图Ⅱ
(Organic Reactions)1979,26,1〕〔反应示意图Ⅲ步骤(n)〕。
可用化学文献中叙述的标准方法来制备化合物(ⅩⅠⅩ)。
反应示意图Ⅲ
还可用化学文献中所介绍的方法来制备酮酯化合物(ⅩⅤ)〔例如参见D C Atkinson,K E Godfrey,B Meek,J F Saville和M R Stillings,药物化学杂志(J.Med.Chem.)1983,26,1353;D Horne,J Gaudino和W J Thompson四面体通讯(Tetrahedron Lett.),1984,25,3529和G P Axiotis,四面体通讯,1981,22,1509〕。
反应示意图Ⅰ和Ⅱ中所述的制备本发明化合物(Ⅰ)的方法一般也适用于制备其中的W是取代的2-吡啶基,或2-或4-嘧啶基的化合物(Ⅰ),并且也适用于制备其中W是含强的吸电子取代基(如硝基、三氟甲基或氟)的4-吡啶基的化合物(Ⅰ)。然而,反应示意图Ⅱ中所示的方法一般不适用于制备其中W是取代的3-或4-吡啶基化合物(Ⅰ)。
同样,虽然其中W是取代的3-或4-吡啶基的化合物(Ⅰ)可用化合物(Ⅳ),按反应示意图Ⅰ中的(a)、(b)和(c)步骤来制备,然而,其中W是取代的3-或4-吡啶基的化合物(Ⅳ)一般不能按反应示意图Ⅰ中的(e)和(f)步骤制备,这样,需要用其他的方法来制备化合物(Ⅳ)。
通常,优先选用反应示意图Ⅳ的路线制备其中W是取代的3-或4-吡啶基的化合物(Ⅳ)。
因此,按反应示意图Ⅳ的合成路线,可以用其中W是取代的3-或4-吡啶基的化合物(ⅩⅩ)制备其中W是取代的3-或4-吡啶基的(Ⅳ)。
(反应示意图Ⅳ见下页)
在整个反应示意图Ⅳ中,A、X、Y、Z和L的定义和反应示意图Ⅰ至Ⅲ中相同,T是能按文献中介绍的标准方法,经一步或多步转变成如化合物(Ⅳ)所示的乙酸酯基-CH2COOR1侧链。例如,T可以是甲
反应示意图Ⅳ
酰基或是可以转变成甲酰基的任何基团,如可被酸性水溶液水解为甲酰基的甲酰基醛缩二醇,或可被金属氢化物还原为甲酰基的腈〔例如参见A E G Miller,J W Bliss和L H Schwartzmann,有机化学杂志,1959,24,627〕,或可被阮内合金在甲酸中还原为甲酰基的腈〔例如参见Van ES和Staskun,化学协会杂志1965,5775〕。如果T是甲酰基团,那么可将其与甲基甲基亚磺酰基甲基硫醚(CH3SOCH2SCH3)反应,转变为乙酸酯残基CH2COOR1〔例如,参见k Ogura和G Tsuchihashi,四面体通讯1972,1383-6〕,然后于酸(如盐酸)存在下,用醇R1OH进行水解。T还可以是能被卤化的甲基,例如被溴或N-溴丁二酰亚胺溴化,得到卤代甲基,然后该卤代甲基用氰化物离子处理,得到氰甲基,然后再用文献中已知的方法,将其水解为乙酸酯残基CH2COOR1;T还可以是能还原为羟甲基的羧酸或酯基团,再用文献中已知的方法,可将羟甲基转变为氰甲基。
在通常应用于已知的Ullmann合成的条件下,以其中L与反应示意图Ⅰ中定义相同的化合物(ⅩⅪ)为原料,用其中W是取代的3-吡啶基的化合物(ⅩⅫ)反应,可以制得其中W是取代的3-吡啶基的化合物(ⅩⅩ)。例如,于过渡金属催化剂(如铜-青铜或卤化铜)存在下、在50-250℃(最好100-180℃)下,不用溶剂或在诸如N,N-二甲基甲酰胺或二甲基亚砜之类的适宜溶剂中,用化合物(ⅩⅫ)的金属盐(最好用其钠或甲盐)来处理化合物(ⅩⅪ)。
化合物(ⅩⅪ)可用化学文献中介绍的一般方法制备。
其中的W是取代的4-吡啶基的化合物(ⅩⅩ)可以采用的制备方法是:在有选择的过渡金属催化剂(如铜-青铜或卤化铜)存在下、于20-200℃(最好在50-150℃)下,于合适的溶剂(例如N,N-二甲基甲酰胺或二甲基亚砜)中,将化合物(ⅩⅩⅢ)的金属盐(最好是钠或钾盐)与其中X是取代的4-吡啶基的化合物(Ⅵ)反应。
化合物(ⅩⅩ)还可用化合物(ⅩⅩⅤ)来制备,在(ⅩⅩⅤ)中P定义为通过其4位连接于A的N-氧化吡啶。P可以被化合物(Ⅰ)中定义的W取代基所取代,也可以不被其取代。如果化合物(ⅩⅩⅤ)中的P是被取代的,则用标准的方法(如用三氯化磷),将此N-氧化物进行脱氧化作用,可得到其中W是取代的4-吡啶基的化合物(ⅩⅩ)。如果化合物(ⅩⅩⅤ)中的P是被取代的或未被取代的,则可用众所周知的方法,将此N-氧化吡啶与磷酰卤或亚硫酰卤反应,在失去N-氧化物官能团的同时得到在其2-或6-位上含有另一个卤原子的化合物(ⅩⅩ)(例如,参见“杂环化合物化学:吡啶及其衍生物”“The chemistry of the Heterocyclic Compounds:Pyridine and Its Derivatives”,Ed.E Klingsberg,第二部分121页)
化合物(ⅩⅩⅤ)的制备方法如下:在有选择的过渡金属催化剂,如铜-青铜或卤化铜的存在下,于20-200℃(最好在50-150℃)下,在适宜溶剂(例如N,N-二甲基甲酰胺或二甲基亚砜)中,将化合物(ⅩⅩⅢ)的金属盐(最好是钠或钾盐)与其中P和L具有上述定义的化合物(ⅩⅩⅣ)反应。化合物(ⅩⅩⅢ)可用化学文献中的标准方法制备。
另一方面,本发明提供了制备本发明的化合物及其所用的中间体(Ⅲ)-(Ⅴ)、(Ⅸ)-(ⅩⅤ)、(ⅩⅦ)、(ⅩⅨ)、(ⅩⅩ)和(ⅩⅩⅤ)的方法。
本发明的化合物是一类有效的杀真菌剂,这些化合物可用于控制一种或多种下述病原体:稻瘟病病菌(Pyricularia oryzae)、小麦叶锈病病菌(Puccinia recondita)、麦类条锈病病菌(Puccinia Striiformis)和其他锈菌;大麦叶锈病病菌(Puccinia hordei)、麦类条锈病病菌(Puccinia Striiformis)和其他如咖啡、梨、苹果、花生、蔬菜和观赏植物之类寄主上的锈菌;大麦和小麦白粉病(Erysiphe graminis)(白粉菌)及其他各种寄主上的白粉病,如蛇麻子斑点单囊壳(Sphaerotheca macnlaris)、葫芦科植物如黄瓜白粉病(Spaerotheca fuliginea)、苹果白粉病(Podosphaera leucotricha)及藤苯科植物葡萄白粉病(uncinula necator);禾谷类长蠕孢属(Helminthosporium spp.),喙孢属(Rhynchosporium spp.)、壳针孢属(Septoria spp.)拟小麦根腐病菌(Pseudocercosporella herpotrichoides)和小麦全蚀病菌(Gaeumannomyces graminis);花生褐斑病(Cercospora arachidicola)和花生黑斑尾孢霉(Cercosporidium personata)和其他寄主如糖用甜菜、香蕉、大豆和水稻的其他尾孢菌属(Cercospora);西红柿、草莓、蔬菜、藤本科植物和其他寄主的灰葡萄孢(Botrytis Cinerea)(灰霉病);蔬菜(如黄瓜)、欧洲油用油菜(Oil Seedrape)、苹果、西红柿和其他寄主的链格孢属(Alternaria);苹果黑星病(Venturia inaequalis)(疮痂病)、藤本科植物葡萄霜霉病(Plasmopara Viticola);其它霜霉病如莴苣霜霉病(Bremialactucae)、大豆、烟草、洋葱和其他寄主的霜霉属(Peronos-Pora spp.)、蛇麻子葎草假霜霉病(Pseudoperonospora humuli)、葫芦科植物黄瓜霜霉病(Pseudoperonospora Cubensis)、土豆及西红柿晚疫病(Phytophthora infestans)及其他蔬菜、草莓、鳄梨、胡椒、观赏植物、烟草、可可和其他寄主的晚疫病;水稻瓜亡草菌(Thanatephorus Cucumeris)及诸如小麦、大麦、蔬菜、棉花和草皮之类寄主的其他丝核菌属(Rhizoctonia)。
本发明的某些化合物在试管内对真菌也表现出有广谱活性。这些化合物对水果成熟后的各种病害〔如柑桔缘霉病(Penicillium digitatum)和柑桔青霉病(Penicillium italicum)及柑桔缘木霉(Trichoderma Viride)和香蕉炭疽盘长孢菌(Gloesporium musarum)〕也有作用。
本发明中还有一些化合物可用于拌种,它们对禾谷类镰刀菌属(Fusarium spp.)、壳针孢属(Septoria spp.)腥黑粉菌属(Tilletia spp.)(腥黑穗病,小麦种子传播的)、黑粉菌属(Ustilago spp.)、禾谷类长蠕孢属(Helminthosporium spp.)、棉花立枯丝核菌(Rhizoctonia solani)及稻瘟病(Pyricularia oryzae)是有效的。
本发明的化合物在植物组织中能向顶运动。而且,它们在气相时的挥发性对寄生于植物上的真菌有足够的活性。
因此,本发明的另一方面是提供消灭真菌的方法,该方法包括将杀真菌有效量的化合物(Ⅰ)施用于植物、植物种子、植物和种子的所在地。
本发明的化合物也可作为工业上的杀真菌剂(和农用不同),例如用于防止真菌对木料、鲁皮、皮革、特别是涂料薄膜的侵害。
本发明的某些化合物具有杀虫及杀线虫的作用。
因此,本发明的另一方面是提供杀灭或控制昆虫或线虫的方法,该方法包括:于害虫或害虫所在场所投放杀虫或线虫有效量的化合物(Ⅰ)。
用于上述方面的本发明的一组优选的化合物,是其中X是取代的吡啶基的化合物(Ⅰ),而其中优选的取代基是卤素或卤代烷基。
在上述方法中,所用最好的化合物是列于表Ⅰ中的14、15号化合物。
同样,本发明的某些化合物也有调节植物生长的作用,按适当的用量比例可达到此目的。所以,本发明还有一个方面是提供调节植物生长的方法,该方法包括将有效量的调节植物生长的化合物(Ⅰ)施用于植物。
本发明的化合物可直接用于农用目的,但是用载体或稀释剂配制成组合物使用是比较合适的。因此,本发明的另一方面是提供杀真菌组合物、杀虫组合物/杀线虫组合物、植物生长调节剂组合物,所说组合物包括前面所定义的化合物(Ⅰ)和可以接受的载体或稀释剂。
作为杀真菌剂,可以有许多方式施用本发明化合物。例如,可将其配制或不配制直接施用于植物的叶、种子或植物正在生长的介质中或将要种植的介质中,或喷雾施药或喷粉施药,或配制成乳剂或糊剂使用,或配制成气雾剂使用,或配制成缓慢释放的粒剂使用。可将其用于植物的任何部分,包括叶、茎、枝或根,或根部周围的土壤,或播种前的种子,或者通常施于土壤,或稻田水中,或水栽培体系中。本发明的化合物也可注射于植物内,或用电动喷雾技术或其他少量喷雾的方法喷雾于植物上。
其中所用的术语“植物”包括禾苗、灌木和树木。而且,本发明杀真菌方法包括:保护性的施药、预防性的施药和根治性的施药。
本发明的化合物优先选用以组合物的形式用于农业或园艺。在任何情况下,所用的组合物的类型将由予计的具体目的而定。
本发明的组合物可以为能喷粉的粉剂或粒剂形式,它们包括有效成分(本发明的化合物)、固体稀释剂或载体,例如填料如高岭土、膨润土、硅藻土、白云石、碳酸钙、滑石、粉状氧化镁、漂白土、石膏、硅藻土(diatomaceous)和瓷土。可将这样的粒剂配制成适用于土壤而不再作进一步处理的粒剂。这种粒剂的制备方法是,用有效成分浸渍填料丸或将有效成分和粉状填料的混合物制成丸。拌种用的组合物可包括有助于此组合物粘附在种子上的试剂(如,矿物油);或用另一种方法,即用有柜溶剂将有效成分配制成作拌种用的液体,所说的有机溶剂有N-甲基吡咯烷酮、丙二醇或二甲基甲酰胺。组合物也可以为湿性粉剂或水可分散的粒剂的形式,它们其中包括有促进分散于液体中的湿润剂或分散剂。所说粉剂或粒剂还可以含填料及悬浮剂。
将有效成分溶于有选择地含有湿润剂或乳化剂的有机溶剂中,然后再把此混合物加入也含有湿润剂或乳化剂的水中,可以配制成乳油或乳剂。适宜的有机溶剂有:如烷基苯和烷基萘之类的芳族溶剂,如异佛尔酮、环己酮、甲基环己酮之类的酮类,如苄醇、氯苯、三氯乙烷之类的氯代烃类,如糠醇、丁醇和乙二醇醚之类的醇类。
借助球磨机,加入分散剂和阻止固体沉降的悬浮剂来配制含有大量不溶固体的悬浮液母液。
用作喷雾用的组合物可以是气雾剂的形式,其具体办法是,于加压下,在推进剂(如氟三氯甲烷或二氯二氟甲烷)存在下将制剂装入容器内。
本发明的化合物能够以干燥态与焰火混合物混合,形成在密闭空间产生含有本发明化合物烟雾的合适组合物。
还可将本发明化合物配制成微胶囊形式,也可将其配制成可生物降解的聚合物制剂,以使有效物质缓慢而有控制地释放。
通过加入适宜的助剂,例如在处理的表面上能改进分配性、粘着力和耐雨水性的各种添加剂,使不同的组合物更好地适合于各种用途。
本发明的化合物可与肥料一起作成混合物使用,这些肥料是含氮、钾或磷的肥料。优选仅含有颗粒状肥料与本发明的化合物混合,例如以本发明化合物包衣的组合物。按重量计,这样的颗粒含本发明化合物适宜的量可以直到25%。因此,本发明也提供了含肥料、化合物(Ⅰ)或其盐或其金属配合物的肥料组合物。
可湿润的粉剂、乳油和悬浮剂母液通常含有各种表面活化剂,例如湿润剂、分散剂、乳化剂或悬浮剂。这些试剂可以是阳离子试剂、阴离子试剂或非离子试剂。
适宜的阳离子试剂包括有季铵化合物,如十六烷基三甲铵溴化物。适宜的阴离子试剂有肥皂,硫酸脂族单酯盐(如十二烷基疏酸钠),磺酸芳族化合物的盐(如十二烷基苯磺酸钠、木素磺酸钠、钙或铵、丁基萘磺酸盐、二异丙基和三异丙基萘磺酸钠的混合物)。
适宜的非离子试剂有:环氧乙烷与脂肪醇(例如油醇或十六醇之类的醇的缩合物,或与烷基酚(例如辛或壬酚、辛基甲酚)的缩合物。其他的非离子试剂是由长链脂肪酸和己糖醇酐所产生的部分酯、该部分酯与环氧乙烷的缩合产物以及卵磷酯。适宜的悬浮剂为亲水胶体(例如聚乙烯吡咯烷酮及羧甲基纤维素钠)及膨胀粘土(Swelling Clays),如膨润土或硅镁土。
用作分散水液或乳剂的组合物一般为含有高比例的有效成分的母液,使用前用水稀释。该母液最好能够长期贮存,贮存后应能用水稀释,形成在足够长的时间里仍是均匀的水制剂,以便能用一般的喷雾设备进行喷雾。按重量计,该母液一般可含有效成分直到95%,适宜的情况是含10-85%,例如25-60%。稀释成水制剂后,该制剂含有效成分的量可以不等,而这要取决于预计的目的,但所用的水制剂按重量计,含有效成分的量为0.0005或0.01%至10%。
本发明的组合物可以含有其他具体生物活性的化合物,例如可以含有具有相似或互补的杀真菌作用或调节植生长、除莠或杀虫作用的化合物。
可存在于本发明组合物中的杀真菌化合物是能消灭禾本科植物(如小麦)穗病的化合物,这种穗病如壳针孢属(Septoria spp.)、赤霉素(Gibberella spp.)、长蠕孢属(Helminthosporium.spp.),能消灭种子和土壤传播的病害、葡萄霜霉病和白粉病、苹果等霜霉病和疮痂病的化合物。由于加入了其他的杀真菌剂,这种组合物比仅含化合物(Ⅰ)(有效成分)具有更广谱的活性。而且,这些其他杀真菌剂对于化合物(Ⅰ)的杀真菌作用具有协同效应。可包含于本发明组合物中的杀真菌剂的例子有:多菌灵、苯菌灵、甲基托布津、噻菌灵、麦穗宁、etridazole、抑菌灵、Cymoxahil、oxadixyl、Ofurace、metalaxyl、furalaxyl、4-氯-N-Cl-氰基-1-乙氧基甲基)苯甲酰胺、benalaxyl、fosetylaluminium、双氯苯嘧醇、iprodione、胺丙威、Procymidone、Vinclozolin、Penconazole、Myclobutanil、Propamocarb、Ro151297、diconazole、定菌灵、乙嘧醇、灭菌磷、buthiobate、环吗啉、嗪胺灵、nuarimol、triazbutyl、双辛胍胺、1,1′-亚氨基二(1,8-亚辛基)二胍三乙酸盐、Propiconazole、Prochloraz、flutriafol、hexaconazole、(2 RS,3RS)-2-(4-氯苯基)-3-环丙基-1-(1H-1,2,4-三唑-1-基)丁-2-醇、(RS)-1-(4-氯苯基)-4,4-二甲基-3-(1H-1,2,4-三唑-1-基甲基)戊-3-醇、flusilazole、三唑二甲酮、triadimenol、diclobutrazol、fenpropimorph、Pyrifenox、fenpropidin、Chlorozolinate、imazalil。-甲呋萎锈灵、萎锈灵、氧化萎锈灵、methfuroxam、环烷吗啉、BAS454、灭瘟素、春日霉素、克瘟散、异稻瘟净、放线菌酮、四氯苯酞、噻菌烯烯、稻瘟灵、三唑苯噻、Pyroquilon、Chlorbenzthiazone、甲胂酸铁铵、多氧霉素、有效霉素、Mepronil、flutolanil、Pencycuron、diclomezine、叶枯净、福美镍、techlofthalam、bitertanol、磺酸丁嘧啶、etaconazole、甲羟异噁唑、链霉素、Cyprofuram、biloxazol、甲基克杀螨、甲嘧醇、1-(2-氰基-2-甲氧基亚氨基乙酰基)-3-乙基脲、fenapanil、tolclofos-methyl、Proxyfur、代森联、代森锰、代森锰锌、敌菌丹、百菌清、敌菌灵、福美双、克菌丹、灭菌丹、代森锌、甲基代森锌、硫黄粉、消螨普、二氯萘醌、地戊散,乐杀螨、nitrothal-isopropyl、十二烷胍、二噻农、三苯羟基锡、乙酸三苯基锡、四氯硝基苯、五氯硝基苯、氯硝胺、诸如王铜、硫酸铜和波尔多液混合物这类含铜化合物和有机汞化合物。
化合物(1)可与土壤、泥炭或其他的根生长介质混合,以使植物免免受种子传播的、土壤传播的或叶的真菌的侵害。
适于加入本发明组合物中的杀虫药剂有:抗蚜威、乐果、甲基1059、安果、西维因、异丙威、二甲威、丁苯威、虫螨威、Carbosulfan、二嗪农、倍硫磷、杀螟松、稻丰散、毒死蜱、异噁唑硫磷、丙虫磷、久效磷、buprofezin、ethroproxyfen、Cycloprothrin。
调节植物生长的化合物是能抑制杂草或坯牙的形成,或能有选择地抑制不要的植物(如草叶)生长的化合物。
适宜与本发明的化合物一起使用以调节植物生长的化合物有:赤霉素(例如GA3、CG4或GA7);植物生长激素(例如,吲哚乙酸、吲哚丁酸、萘氧基乙酸或萘乙酸)、细胞分裂素类、(例如激动素、二苯脲、苯并咪唑、苄基腺嘌呤或苄基氨基嘌呤)、苯氧基乙酸(例如2,4-滴或2甲4氯)、取代的苯甲酸(如三碘苯甲酸)、整形素(例如Chlorfluoroecol)、马来酰肼、草甘膦、催熟膦、长链脂肪族醇和酸、dikegulac、Paclobutrazol、氟磺安、mefluidide、取代的季铵、取代的磷鎓化合物(如离子矮壮素、氯丁苄鏻或mepiguatehloride)、乙烯利、草威安、3,6-二氯茴香酸甲酯、二甲基琥珀酰肼、黄草灵、脱落酸、isopyrimol、1-(4-氯苯基)-4,6-二甲基-2-氧代-1,2-二氢吡啶-3-羧酸、羟基苄腈类(例如溴苯腈)、草吡唑、新燕灵、3,6-二氯吡啶甲酸、fenpentezol、inabenfide、triapenthenol和四氯硝基苯。
本发明将用下述实施例来说明。在下述实施例中:术语“醚”为乙醚;用硅胶作固相进行层析分离;用硫酸镁干燥溶液;凡涉及到对水、空气敏感的中间体的反应均在氮气中、无水溶剂中进行;列出的红外光谱和NMR数据都是有选择的,不打算列出每一个吸收峰的数据,除另有说明外,测定的核磁共振谱是以氘氯仿作标准液;所用缩写如下:
g=克 δ=化学位移
mmol=毫摩尔 CDCl3=氘氯仿
ml=毫升 S=单峰
mmHg=毫米汞柱压力 d=二重峰
t=三重峰
br=宽峰
DMF=N,N-二甲基甲酰胺
Max.=最大
HPLC=高效液相色谱
mp.=熔点
PPm.=百万分之一
NMR=核磁共振
实施例1
本实施例叙述了2-〔2′-(5″-氯吡啶-2″-基氧基)苯基〕-3-甲氧基丙烯酸甲酯(E)(表Ⅰ中的14号化合物)的制备
于160℃下、氮气流中,将2,5-二氯吡啶(7.70g,52.03mmol)、碳酸钾(14.01g,101.37mmol)和由邻-羟基苯乙酸制备的二钠盐(10.20g,52.58mol)的二甲基亚砜(50ml)溶液搅拌过夜。把此黑色反应混合物倒入水(100ml)中并用乙醚(3×75ml)萃取。用浓盐酸把水相酸化到pH6,然后再用乙酸乙酯(3×100ml)萃取。合併的有机相用盐水(2×100ml)洗涤、干燥、减压蒸发,得到暗棕色的液体〔2-(5′-氯吡啶-2′-基氧基)苯基〕乙酸(5.30g)(红外光谱的最大波数为,3500-2700,1700,1370,1440,750cm-1),不需要进一步纯化即可使用。于室温下、DMF(50ml)中,将2-(5′-氯吡啶-2′-基氧基)苯乙酸(5.20g,19.73mmol)、碳酸钾(5.53g,40mmol)和硫酸二甲酯(2.91g,23.07mmol)一起搅拌过夜。把此反应混合物倒入水(100ml)中,依次用乙酸乙酯(2×75ml)和乙醚(1×100ml)萃取,合併的有机相依次用水(3×75ml)和盐水(2×100ml)洗涤,干燥并减压蒸发,于152℃/0.1mmHg蒸馏得到深棕色的液体2-(5′-氯吡啶-2′基氧基)苯乙酸甲酯(4.18g)。
于-25℃、在搅拌下,向氢化钠(0.78g,分散于油中,50%)的DMF(40ml)悬浮液中滴加2-(5′-氯吡啶-2′-基氧基)苯乙酸甲酯(2.90g,10.45mmol)和甲酸甲酯(14.88g,过量)的DMF溶液。将此反应混合物在饱和碳酸钠溶液和乙醚之间进行分配。用浓盐酸将水相酸化到pH4-5(黄色沉淀),然后用乙酸乙酯(3×100ml)萃取,合併有机萃取液,干燥、减压蒸发,得到桔红色固体2-〔2′-(5″-氯吡啶-2″-基氧基)苯基〕-3-羟基丙烯酸甲酯(2.36g)。于室温下,将此固体物质(2.30g,7.54mmol)在DMF(50ml)中,同硫酸二甲酯(1.21g,9.59mmol)和碳酸钾(2.44g,17.6mmol)一道搅拌过夜。然后将此反应混合物倒入水中(100ml),用乙酸乙酯(3×100ml)萃取,合併的有机相依次用水(3×75ml)和盐水(2×100ml)洗涤,干燥,减压蒸发,得到棕色粘稠状液体。经HPLC(洗脱剂为乙醚∶石油醚50∶50)纯化,制得经放置便会结晶的浅黄色液体(2.14g)。用甲醇进行重结晶,得到2-〔2′-(5″-氯吡啶-2″-基氧基)苯基〕-3-甲氧基丙烯酸甲酯(E),熔点77-78℃。红外光谱的最大波数为,1700,1625,1260,1200cm-1;1H NMR δ(CDCl3)3.57(3H,S)、3.74(3H,S),6.75(1H,d),7.41(1H,S),8.10(1H,brs),7.1-7.6(m)ppm。
实施例2
本实施例叙述了2-〔2′,5″-氰基吡啶-2″-基氧基)苯基〕-3-甲氧基丙烯酸甲酯(E)(表Ⅰ中的127号化合物)的制备
于搅拌下,向氢氧化钾(2.26g,0.04mol)的甲醇(40ml)溶液中加入邻-羟基苯乙酸(3.08g,0.02mol),15分钟后将此溶液减压蒸发至干,固体残余物用DMF(50ml)制成浆状物。加入6-氯烟酸腈(3.08g,0.022mol)和铜-青铜(0.1g),于80℃-90℃搅拌1小时,冷却后浸入水(200ml)中。过滤此混合物,用盐酸将滤液的pH调到2-3。混合物用乙醚萃取(×3)。再用饱和碳酸氢钠溶液萃取合併的乙醚相。水相用盐酸酸化到pH2-3,得到焦油状固体,经少量甲醇研磨便能制得白色固体(1.27g,产率25%),用水重结晶,可得到白色固体状2-〔2′-(5″-氰基吡啶-2″-基氧基)苯基〕乙酸,熔点120℃。红外光谱的最大波数为1672cm-1;1H NMR(d6DMSO;60MHZ)δ3.45(2H,S);7.05-7.45(5H,m);8.25-8.35(m,1H);8.6(1H,d);6.3(brs,1H)ppm。
将上述制得的酸(3.0g,0.0118mol)置于含浓硫酸(0.1ml)的甲醇(50ml)中,在回流下搅拌3小时。冷却后加水(200ml),用乙醚(3×50ml)萃取。合併的乙醚萃取液依次用饱和碳酸氢钠溶液(30ml)、水(3×30ml)和饱和盐水(1×30ml)洗涤,干燥及过滤后,蒸发乙醚溶液,得到琥珀色的油状物2-〔2′-(5″-氰基吡啶-2″-基氧基)苯基〕乙酸甲酯(2.77g,产率87.5%);红外光谱的最大波数(薄膜)2200,1700cm-1;1H NMR(CDCl3)3.5(5H,S);6.8-7.3(5H,m);7.8(1H,q);8.3(1H,d)ppm。
于室温下,向三乙胺(0.65g,0.0064mol)的乙醚(10ml)溶液中滴加三氟甲基磺酸三甲基硅烷基酯(1.42g,0.0064mol)。将此混合物放置20分钟,于0~5℃,在15分钟内把此混合物滴加到搅拌着的2-〔2′-(5″-氰基吡啶氧基)苯基〕乙酸甲酯(1.15g,0.0043mol)的乙醚(10ml)溶液中。将此反应混合物温热到室温,搅拌11小时,即产生两相混合物,保留上层(溶液A)。
同时,于-70℃下,在搅拌下向原甲酸三甲酯(0.71g,0.0064mol)的二氯甲烷(10ml)溶液中滴入四氯化钛(1.22g,0.0064mol),搅拌此黄色沉淀物15分钟,并且在20分钟内,维持在-70℃下,将溶液A滴入。于-70℃下将混合物搅拌1小时后,让其温热到室温,并搅拌1小时。加入饱和碳酸钠溶液(50ml)后过滤,滤液用乙醚(3×20ml)萃取,用水(3×15ml)洗涤合併后的有机萃取液,再用饱和盐水(15ml)洗涤,干燥和过滤后,将此乙醚溶液减压蒸发至干,残余物用层析分离(己烷/乙醚为洗脱剂),得到玻璃状的标题化合物,经甲醇研磨,得到白色晶体(40mg,产率3%),熔点108.5-109.5℃。1H NMR δ 3.58(3H,S);3.75(3H,S);6.9(1H,d);7.1(1H,d);7.28-7.4(4H,m);7.45(1H,S);7.85(1H,q);8.45(1H,d)ppm。
实施例3
本实施例叙述了2-〔2′-(5″-硝基吡啶-2″-基氧基)苯基〕-3-甲氧基丙烯酸甲酯(E)(表Ⅰ中的133号化合物)的制备
向氯化氢的甲醇溶液〔由乙酰氯(25ml)和甲醇(250ml)制备〕中加入2-(羟基苯基)乙酸(50g)。将其于室温下搅拌3小时后放置过夜(15小时)。在进行减压浓缩后,将残余物溶于乙醚(250ml)中,用碳酸氢钠水溶液洗涤直至停止起泡沫,干燥乙醚溶液,再进行减压浓缩,将得到的固体用乙醚/汽油进行重结晶,得到白色粉末状晶体(2-羟基苯基)乙酸甲酯(50g;产率92%),熔点:70-72℃;红外光谱,最大波数(石蜡糊):3420,1715cm-1;1H NMR(90MHZ)δ3.70(2H,S),3.75(3H,S),6.80-6.95(2H,m),7.05-7.10(1H,m),7.15-7.25(1H,m),7.40(1H,S)ppm。
将(2-羟基苯基)乙酸甲酯(21.0g)溶于DMF(200ml)中,一批加入碳酸钾(19.35g)。于室温下,边搅拌边向此混合物中滴加苄基溴(23.94g)的DMF(50ml)溶液。18小时后,将此混合物倒入水(500ml)中,用乙醚(2×400ml)萃取。萃取液依次用水(3×150ml)和盐水(100ml)洗涤,干燥并经硅胶柱过滤(50g,merck60),减压浓缩,得到黄色油状物,于160℃、0.05mmHg下蒸馏,得无色透明的油状物2-苄氧基苯基乙酸甲酯(26.99g,产率83%),红外光谱,最大波数(薄膜):1730cm-1;1H NMR(90MHZ):δ3.60(3H,S);3.75(2H,S),4.10(2H,S),6.80-7.40(9H,m)ppm。
在0℃,于搅拌下向氢化钠(50%油分散剂,10.13g)的DMF(300ml)悬浮液中滴加2-苄氧基苯乙酸甲酯(26.99g)和甲酸甲酯(126.62g)与无水DMF(300ml)的混合物。在0℃搅拌2小时后,将此混合物倒入水(1000ml)中,用乙醚(2×150ml)洗涤,水相用6M盐酸酸化到pH4,然后用乙醚(2×350ml)萃取。萃取液经干燥、减压浓缩后,得到黄色油状粗品2-〔2′-苄氧基苯基〕-3-羟基丙烯酸甲酯。红外光谱,最大波数(薄膜):1720,1660cm-1。
将所得粗品2-〔2′-苄氧基苯基〕-3-羟基丙烯酸甲酯溶于无水DMF(100ml)中,一批加入碳酸钾(29.0g),然后边搅拌边加入硫酸二甲酯(16.00g)的无水DMF(10ml)溶液。90分钟后,加入水(300ml),溶液用乙醚(2×300ml)萃取。依次用水(3×150ml)和盐水洗涤后,干燥萃取液,减压浓缩,得到黄色油状物,经乙醚/汽油研磨可以固化。用无水甲醇进行重结晶,得到白色晶体2-(2′-苄氧基苯基)-3-甲氧基丙烯酸甲酯(E)(5.44g,产率17%,按2-苄氧基苯基乙酸甲酯进行计算),熔点76-77℃。红外光谱,最大波数(石蜡糊):1710,1640cm-1;1H NMR(90MHZ):δ3.63(3H,S),3.75(3H,S),5.05(2H,S),6.80-7.40(9H,m),7.50(1H,S)ppm。
将2-(2′-苄氧基苯基)-3-甲氧基丙烯酸甲酯(E)(5.44g)溶解在乙酸乙酯(50ml)中,加入5%的钯碳(0.25g)。于3个大气压下,边搅拌边将此混合物进行氢化,直至不再吸收氢,然后用硅藻土和硅胶(50g,Merck60)进行过滤,滤液进行碱压浓缩,得到白色晶体2-(2′-羟基苯基)-3-甲氧基丙烯酸甲酯(E)(3.76g,产率99%),熔点125-126℃;红外光谱,最大波数(石蜡糊):3400,1670cm-1
1H NMR(270MHZ):δ3.80(3H,S)3.90(3H,S),6.20(1H,S),6.80-7.00(2H,m),7.10-7.30(2H,m),7.60(1H,S)ppm。
于室温和氮气流中,将2-(2′-羟基苯基)-3-甲氧基丙烯酸甲酯(E)(0.30g,1.44mmol)、2-氯-5-硝基吡啶(0.40g,2.88mmol)和碳酸钾(0.40g,2.88mmol)在DMF(20ml)中一起进行搅拌。18小时后,将此反应混合物倒入水中,然后用乙醚萃取2次,合併的乙醚层用水和盐水洗涤两次,干燥,得到的溶液用硅胶柱过滤,浓缩后得到粉红色固体。经层析纯化(乙醚为洗脱剂)后,得到2-〔2′-(5″-硝基吡啶-2″-基氧基)苯基〕-3-甲氧基丙烯酸甲酯(E)(240mg),为黄色树胶状物,放置中即会结晶,熔点107-109℃;1H NMR:列于表Ⅳ中。
实施例4
本实施例叙述了2-〔2′-(4″-氯嘧啶-2″-基氧基)苯基〕-3-甲氧基丙烯酸甲酯(E)(表Ⅰ中的61号化合物)的制备
于室温下,将2-(2′-羟基苯基)-3-甲氧基丙烯酸甲酯(E)(0.63g)、2,4-二氯嘧啶(0.75g)和碳酸钾(0.69g)一起在DMF中搅拌。2小时后,将此反应混合物倒入水(50ml)中,用乙醚萃取2次,合併的乙醚相用水(×3)、盐水(×1)洗涤,再干燥,过滤后减压蒸发,得到透明油状物。经层析分离(乙醚为洗脱剂),得到2-〔2′-(4″-氯嘧啶-2″-基氧基)苯基〕-3-甲氧基丙烯酸甲酯(E)(0.35g),为油状物,经乙醚研磨结晶,m.p.为120-121.5℃。1H NMF δ3.60(3H,S);3.80(3H,S);6.60(1H,d,J=4HZ);7.40(1HH,S);8.40(1H,d,J=4HZ)ppm。
实施例5
本实施例叙述了2-〔2′-(5″-氯吡啶-2″-基硫代)苯基〕-3-甲氧基丙烯酸甲酯(E)(表Ⅱ中的14号化合物)的制备
向邻-巯基苯基乙酸二钠盐〔其制备是,将邻-巯基苯基乙酸(1.68g)于甲醇(10ml)中用氢氧化钠(0.8g)处理,接着将所得溶液的一半蒸发至干,再将其溶于DMF(10ml)中〕和铜-青铜的混合物中加入2,5-二氯吡啶的DMF(5ml)溶液。把此反应混合物于110-120℃加热90分钟,将其加入水中,酸化,用乙醚(×3)萃取。用2N的氢氧化钠(×1)萃取合併的乙醚层,用烯盐酸酸化所得的桔色水相。过滤悬浮液,固体用水充分洗涤,干燥,得到〔2′-(5″-氯吡啶-2″-基硫代)苯基〕乙酸(0.88g),为浅黄褐色固体,熔点为141-4℃。
在含有两滴浓硫酸的甲醇(15ml)中,将〔2′-(5″-氯吡啶-2″-基硫代)苯基〕乙酸(0.69g)加热至回流,90分钟后,将溶液冷却到室温,倒入水中,用乙醚(×2)萃取。依次用1M氢氧化钠溶液和水(×3)洗涤合併的有机相,然后干燥。减压浓缩,得到棕色油状物〔2′-(5″-氯吡啶-2″-基硫代)苯基〕乙酸甲酯(610mg),无需进一步纯化即可应用。
于搅拌下向冷却至2℃(冰/盐浴)的用己烷洗涤过的氢化钠(0.144g,50%油分散剂)的DMF悬浮液中,加入含〔2′-(5″-氯吡啶-2″-基硫代)-苯基〕乙酸甲酯(0.44g)和甲酸甲酯(1.8g)的DMF(10ml)溶液。将所得的反应混合物温热到室温。4.5小时后,通过小心地加入水将反应骤冷,用稀盐酸酸化,用乙醚萃取(×3)。合併桔色有机层用水洗涤、干燥,减压浓缩,得到含有2-〔2′-(5″-氯吡啶-2″-基硫代)苯基〕-3-羟基丙烯酸甲酯(0.40g)的粗混合物,为桔色树胶状物,(红外光谱,最大波数,1665cm-1)、可直接用于下一步反应。将此桔色树胶状物溶解在DMF(10ml)中,加入碳酸钾,把所得悬浮液冷却到0℃,然后5分钟内将硫酸二甲酯的DMF(2ml)溶液滴入。0℃下搅拌1小时后,将此反应混合物温热到室温,倒入水中,再用乙酸乙酯萃取(×4),用水洗涤合併的有机相(×2),干燥、减压浓缩,得到红色油状物(0.46g),经层析纯化(乙醚-己烷1∶1为洗脱剂)得到粘稠的树胶状标题化合物(0.085g),红外光谱,最大波数1700,1630cm-1,1H NMR见表Ⅳ中。
实施例6
本实施例叙述了2-〔2′-(5″-溴吡啶-2″-基硫代)苯基〕-3-甲氧基丙烯酸甲酯(E)(表Ⅱ中的15号化合物)、2-(2′-(5″-溴吡啶-2″-基亚硫酰基)苯基〕-3-甲氧基丙烯酸甲酯(E)(表Ⅲ中的1号化合物)、2-(2′-(5″-溴吡啶-2″-基磺酰基)苯基〕-3-甲氧基丙烯酸甲酯(E)(表Ⅲ中的2号化合物)的制备
于0℃下,无水二氯甲烷(10ml)中,用间-氯过苯甲酸(113mg)处理2-〔2′-(5″-溴吡啶-2″-基硫代)苯基〕-3-甲氧基丙烯酸甲酯(E)(200mg)(由2,5-二溴吡啶按实施例5的步骤制得)。于15分钟内此桔色溶液变为无色。搅拌30分钟后,将此反应混合物在碳酸氢钠水溶液中进行分配,有机层用第二份碳酸氢钠水溶液洗涤,再用水洗涤,干燥,减压去除溶剂,得到黄色树胶状物(0.14g),经层析纯化(乙醚为洗脱剂),得到树胶状的2-〔2′-(5″-溴吡啶-2″-基亚硫酰基)苯基〕-3-甲氧基丙烯酸甲酯(E)(30mg),1H NMR列于表Ⅳ;和非晶形的固体2-(2′-(5″-溴吡啶-2″-基磺酰基)苯基〕-3-甲氧基丙烯酸甲酯(E)(30mg),1H NMR列于表Ⅳ。
实施例7
本实施例叙述了2-〔2′-(5″-甲氧基羰基吡啶-2″-基氧基)苯基〕-3-甲氧基丙烯酸甲酯(E)(表Ⅰ的141号化合物)的制备
于氢氧化钾(1.0g,0.017mol)的水(30ml)溶液中,将2-〔2′-(5″-氰基吡啶-2″-基氧基)苯基〕乙酸甲酯(2.03g,0.008mol,其制备如按实施例2所述方法制备)加热回流16小时。冷却到室温,加入盐酸把PH调到2-3。滤出的沉淀用少量冰水洗涤,在95℃下干燥,将其用甲醇水溶液重结晶,得到白色晶体2-〔2′-(5″-羧基吡啶-2″-基氧基)苯基〕乙酸(1.83g);熔点187-188℃;红外光谱,最大波数,3400,2556,1710,1686cm-1,1H NMR(d6DMSO)δ3.42(2H,S);6.32(1H,brs);6.95-7.44(5H,m);8.1(1H,brs);8.27(1H,q);8.62(1H,d)ppm。
于室温下,将2-〔2′-(5″-羧基吡啶-2″-基氧基)苯基〕乙酸(1.46g,0.0053mol)、甲基碘(1.52g,0.00107mol)、碳酸钾(2.95g,0.021mol)和DMF的混合物搅拌3小时。把此反应混合物浸入水(100ml)中,用乙醚(2×40ml)萃取。用水(3×20ml)和饱和盐水(20ml)洗涤合併的有机萃取液。将滤液干燥后,蒸发乙醚溶液,得到2-〔2′-(5″-甲氧基羰基吡啶-2″-基氧基)苯基〕乙酸甲酯(0.73g),为油状物,1H NMR δ3.45(3H,S);3.47(2H,S);3.79(3H,S);6.73-7.3(5H,m);8.2(1H,q);8.7(1H,d)ppm。
于室温下,向三乙胺(0.37g,0.0036mol)的乙醚(10ml)溶液中滴加三氟甲磺酸三甲基硅酯(0.81g,0.0036mol)。放置20分钟后,0-5℃在20分钟内把所得溶液滴加(20分钟以上)到2-〔2′-(5-甲氧基羰基)吡啶-2″-基氧基)苯基〕乙酸甲酯的乙醚(10ml)溶液中。将此混合物搅拌并温热到室温3小时,保留此混合物的上层清液(溶液A)。
同时,于-70℃下,在另一烧瓶中,向原甲酸三甲酯(0.49,0.0036mol)的二氯甲烷(10ml)溶液中加入四氯化钛(0.69g,0.0036mol)的二氯甲烷(5ml)溶液。于-70℃下将所得黄色沉淀物搅拌15分钟。在10分钟内把溶液A滴加到此混合物中,并维持温度在-70℃下。搅拌此混合物1小时,放置16小时。加入饱和碳酸钠溶液(50ml),过滤此混合物。滤液用乙醚(3×20ml)萃取,用水(3×15ml)和饱和盐水(15ml)洗涤合併的有机萃取液。干燥和过滤后,蒸发此乙醚溶液,得到焦油状残余物,经层析分离(己烷为洗脱剂),从此残余物中分离出油状的标题化合物(20mg)。
1H NMRδ3.47(3H,s);3.62(3H,s);3.82(3H,s);6.75-7.3(5H,m);7.32(1H,s);8.15(1H,q);8.72(1H,d)ppm.
实施例8
本实施例叙述了2-〔2′-(5″-苄氧基羰基吡啶-2″-基氧基)苯基〕-3-甲氧基丙烯酸甲酯(E)(表Ⅰ中的184号化合物)的制备
将2-〔2′-(5″-羧基吡啶-2″-基氧基)苯基〕乙酸(1.5g,0.005mol,按实施例7所述的方法制备)与甲醇(50ml)和硫酸(0.1ml)一起加热回流8小时。蒸发浓缩此混合物到其体积的一半,冷却后,浸入水(100ml)中,用乙醚(2×30ml)萃取,用饱和碳酸氢钠溶液萃取合併的有机萃取液,用盐酸酸化此碱性萃取液到pH2.3,在冰水中冷却,过滤收集白色沉淀物,用水洗涤,在95℃下干燥,得到2-〔2′-(5″-羧基吡啶-2″-基氧基)苯基〕乙酸甲酯(0.63g);熔点。118℃;1H NMR δ3.52(3H,S);3.57(2H,S);6.88-7.4(5H,m);8.3(1H,q);8.88(1H,d)ppm。
室温下,将2-〔2′-(5″-羧基吡啶-2″-基氧基)苯基〕乙酸甲酯(0.63g,0.0022mol)、苄基溴(0.37g,0.0021mol)、碳酸钾(0.6g,0.0043mol)和DMF(30ml)的混合物搅拌1小时。把此混合物浸入水(100ml)中,用乙醚(2×30ml)萃取,合併的有机萃取液用水(3×15ml)和饱和盐水(15ml)洗涤,干燥和过滤后,蒸发此乙醚液,得到无色树胶状的2-〔2′-(5″-苄氧基羰基吡啶-2″-基氧基)苯基〕乙酸甲酯,经层析纯化(用己烷洗脱),得到无色固体(0.69g);熔点:56℃红外光谱,最大波数1735,1722cm-1;1H NMRδ 3.44(3H,S);3.5(2H,S);5.24(2H,S);6.76-7.4(5H,m);8.2(1H,q);8.76(1H,d)ppm。
于室温下,向三乙胺(0.277g,0.0027mol)的乙醚(5ml)溶液中滴入三氟甲基磺酸三甲硅酯(0.61g,0.0027mol)。将此混合物放置20分钟。在0-5℃于搅拌下,在15分钟内向2-〔2′-(5″-苄氧基羰基吡啶-2″-基氧基)苯基〕乙酸甲酯在乙醚(5ml)的混合物中加入(15分钟以上)所得溶液。搅拌此混合物,并温热到室温3小时,用二氯甲烷(5ml)稀释,并保留(A液)。
同时,在-70℃下,将四氯化钛(0.52g,0.0027mol)的二氯甲烷(2ml)溶液滴加到原甲酸三甲酯(0.301g,0.0028mol)的溶液中。于-70℃下,搅拌此黄色沉淀物15分钟,维持在-70℃下的同时,在30分钟内滴入溶液A。搅拌此混合物,并让其温热到室温1小时,然后放置15小时。加入饱和碳酸钠溶液(30ml)并进行搅拌,然后过滤。滤液用乙醚(3×15ml)萃取,合併的乙醚萃取液用水(3×10ml)和饱和盐水(10ml)洗涤。干燥和过滤后,蒸发此乙醚溶液得到树胶状物,经层析分离(用己烷洗脱)分离得标题化合物,为树胶状物。1H NMRδ3.55(3H,S);3.60(3H,S);5.53(2H,S);6.82(1H,d);7.18-7.48(m,包括在δ7.39处的一个质子单吸收峰);8.25(1H,q);8.25(1H,d)ppm。
实施例9
本实施例叙述了2-〔2′-(6″-甲基吡啶-3″-基氧基)苯基〕-3-甲氧基丙烯酸甲酯(E)(表Ⅰ中的45号化合物)的制备
将6-甲基-3-羟基吡啶(9.5g)悬浮于甲苯(30ml)中,再用氢氧化钾水溶液(4.9g,在8ml水中)处理。激烈搅拌此混合物15分钟,然后减压蒸发,于甲苯存在下,再重复蒸发以除去微量的水。用2-(2-溴苯基)-1,3-二氧戊环(10.0g)、氯化亚铜(60mg)和三〔2-(2-甲氧基乙氧基)乙基〕胺(0.194g)处理所形成的棕色半固体,为了增溶此铜盐,使反应在无水DMF(25ml)中进行。于氮气流中,边搅拌边将此混合物于155℃加热30小时,再加入氯化亚铜(60mg),并继续加热14小时。
将此混合物冷却后倒入水中,用乙酸乙酯萃取,萃取液用2N氢氧化钠水溶液和水洗涤,接着用2N盐酸萃取。此酸性萃取液用固体碳酸钾处理,直至PH8,然后用乙酸乙酯萃取,干燥该有机萃取液,然后减压蒸发,得到2-(6′-甲基吡啶-3′-基氧基)苯甲醛(2.2g),为油状物。红外光谱,最大波数(薄膜)1697,1606,1480cm-1;1H NMRδ2.58(3H,S);6.86(1H,S);7.28(3H,m);7.55(1H,t);7.95(1H,m);8.36(1H,m);10.53(1H,S)ppm。
将2-(6′-甲基吡啶-3′-基氧基)苯甲醛(2.08g)和甲基甲基亚磺酰甲基硫醚(1.21g)溶于无水THF(15ml)中,于室温下,边搅拌边慢慢滴加Triton B(1.5ml)。将其放置过夜,用水稀释并用乙酸乙酯萃取。萃取液干燥后减压蒸发,得到桔棕色油状物(3.2g),此油状物用氯化氢的甲醇溶液(25ml,2.6N)处理,并于室温下放置过夜,用水稀释,用碳酸钠把PH调至8,用乙酸乙酯萃取。将萃取液干燥、蒸发,得到棕色油状物(2.23g),用高效液相色谱纯化,(洗脱剂为乙酸乙酯∶己烷,1∶1)得到黄色油状物〔2-(6′-甲基吡啶-3′-基氧基)苯基〕乙酸甲酯(1.53g)。红外光谱,最大波数(薄膜)1747,1488,1237cm-1。1H NMRδ2.54(3H,S);3.63(3H,S);3.74(2H,S);6.84(1H,d);7.24(5H,m);8.3(1H,d)ppm。
于5℃,边搅拌边将〔2-(6′-甲基吡啶-3′-基氧基)苯基〕乙酸甲酯(1.3g)和甲酸甲酯(1.52g)在DMF(5ml)中的混合物滴加到氢化钠(316mg,50%油分散剂)在DMF(5ml)中的悬浮液内。搅拌4小时后,用水稀释,加入冰醋酸进行弱酸化(pH4-5),用乙酸乙酯萃取。干燥萃取液并进行减压蒸发,得到黄色油状的2-〔2′-(6″-甲基吡啶-3″-基氧基)苯基〕-3-羟基丙烯酸甲酯(1.15g)1H NMRδ2.53(3H,S);3.63(3H,S);6.89(1H,S);7.2(5H,m);8.21(1H,d)ppm。
将此油状物(1.14g)溶解于DMF(15ml)中,加入碳酸钾(1.1g),搅拌此混合物15分钟。将硫酸二甲酯(0.53g)溶解在DMF(5ml)中,并将该溶液加到混合物中,所得混合物搅拌30分钟,用水稀释,用乙酸乙酯萃取所得浮浊液,干燥萃取液,并进行减压蒸发,得到黄色油状物(2.06g),经高效液相色谱纯化(用乙酸乙酯洗脱),得浅黄色油状物2-〔2′-(6″-甲基吡啶-3″-基氧基)苯基〕-3-甲氧基丙烯酸甲酯(E)(0.73g)。红外光谱,最大波数(薄膜)1705,1642,1488cm-1;1H NMRδ2.52(3H,S);3.63(3H,S);3.81(3H,S);6.88(1H,d);7.04-7.32(5H,m);7.51(1H,S);8.26(1H,d)ppm。
下述实施例为适宜农用和园艺用的组合物的实例,这些组合物是用本发明的化合物配制的,这类组合物构成了本发明另一个方面的内容。
实施例10
将下述各成分混合并搅拌直至全部溶解,而可制得乳油
表Ⅰ中的61号化合物 10%
苄醇 30%
十二烷基苯磺酸钙 5%
壬基酚乙氧基化物(13mol环氧乙烷) 10%
烷基苯 45%
实施例11
将有效成分溶于二氯甲烷中,并将所制得的溶液喷于硅镁土粒上,再让溶剂蒸发,便制得粒状组合物。
表Ⅰ中的14号化合物 5%
粒状硅镁土 95%
实施例12
将下述三种成分研磨、混合,制得适宜作拌种用的组合物。
表Ⅰ中的61号化合物 50%
矿物油 2%
陶土 48%
实施例13
将有效成分与滑石一起研磨和混合,制得能用于喷粉的粉剂。
表Ⅰ中的61号化合物 5%
滑石 95%
实施例14
用球磨机研磨下述各成分,与水一起形成研磨混合物的水悬浮剂,即制得悬浮液母液。
表Ⅰ中的61号化合物 40%
木素磺酸钠 10%
膨润土 1%
水 49%
此制剂经水稀释后可作喷雾用,或直接用于种子。
实施例15
将下述各成分一起混合和研磨,直至各成分充分混合,制得可湿性粉剂。
表Ⅰ中的61号化合物 25%
十二烷基硫酸钠 2%
木素磺酸钠 5%
氧化硅 25%
陶土 43%
实施例16
试验本发明化合物对植物的各种叶真菌病害的作用。所用的方法叙述如下:
植物长在4cm直径的小盆中,施用的是John Innes盆栽堆肥(1或2号)。试验化合物既可借助球磨、用Dispersol T水溶液来配制,也可将其配制成丙酮或丙酮/乙醇溶液,在使用前立即将其稀释到所需的浓度。对于叶的病害,将组合物(100ppm有效成分)喷雾于叶上并将其施于土壤中植物的根部。喷雾要有最大的保持力并浸润根部,其最终浓度约等于40ppm有效成分/干土壤。如将其喷雾于禾谷类时,加入吐温20,以使最终浓度为0.05%。
对于大多数试验来讲,在植物接种病菌前一天或前两天,把本发明的化合物施用于土壤(根)及叶上(喷雾)。仅仅有一个例外,对于白粉病(Erysiphe graminis)的试验是在处理前24小时接种的。所施用的叶病菌,以孢子悬浮液的形式喷雾于试验植物叶上。接种后,把这些植物放在适当的环境中让其传染,并让其发展直至容易对此病害进行评价。在接种到评价之间的时间为4-14天不等,这取决于试验的病害和环境。
对于病害的控制分成下述级别
4=无病害
3=病害轻微~0.5%(未经处理的植物)
2=6-25%的病害(未经处理的植物)
1=26-59%的病害(未处理的植物)
0=60-100%的病害(未处理的植物)
这些结果列于表Ⅴ中
(表Ⅴ见下页)
实施例17
本实施例用以说明表Ⅰ中的14-16、22、61、132和138-140号化合物调节植物生长的性能。
对六种植物的生长调节作用以上述这些化合都对其进行筛选试验。用于该筛选试验的植物列于表Ⅵ中,在叶片阶段对其进行喷雾。
所施用的每种化合物的制剂其量为4000ppm(4kg/公顷,1000升/公顷),使用的是履带式喷雾器和SS8004E(T形)喷嘴。另外还对西红柿进行了试验,浓度为2000和500ppm。
喷雾后,将试验的植物放在温室〔25℃(白天)/22℃(夜间)〕中生长。除这些植物外,还于13-16℃(白天)/11-13℃(夜间)温度进行了小麦和大麦的生长试验。维持平均光照期为16小时(最小为14小时),如果低于这个平均植给以光照。
在温室中2-6周后(取决于植物的种类和当时的季节),用目视法
表Ⅴ
表Ⅴ(续)
表Ⅴ(续)
*25 ppm,只喷叶
**40 ppm只喷叶
评价这些植物的形态特征,并与喷以空白制剂的对照组植物进行比较。
结果列于表Ⅶ。
表Ⅵ
用于筛选试验的植物
JIP*John Innes盆栽堆肥。
表Ⅶ
注:*2000ppm+500ppm
1-3为迟延发育,这里的1=10-30%
2=21-60%
3=61-100%
G=绿色效应
A=顶端损伤
T=分蘖或侧面抽茎
空白即表示其效应低于10%
NT表示该化合物未对此种植物进行试验
实施例18
本实施例用以说明本发明化合物(Ⅰ)的某些杀虫性能。
用各种螨和线虫来测定每种化合物的作用,所用化合物为液态制剂的形式,按重量计,含100-500ppm的化合物。这些制剂的配制方法是,先将化合物溶于丙酮中,再用含有湿润剂(商品名称是:“SyNPeroNic”NX)0.1%(按重量计)的水稀释,直至该液体制剂浓度合乎要求为止。“SyNPeroNic”为注册的商品名。
对于每种害虫所采取的试验步骤基本上是相同的,这包括使许多害虫寄生在介质(一般是寄主植物)上或害虫要吃的食物上,再用所说的制剂处理这些害虫或处理这些介质,或将这两者均予处理。一般在处理后的一段时间(1-7天不等)里评价这些害虫的死亡率。
表Ⅸ给出了每种化合物的试验结果,在该表的第二栏中给出了用量比例(ppm),对死亡率的等级定有9、5或0,其中9表示其死亡率为80-100%和未处理介质的根结线虫病(Meloidogyne ineognita)比较,根结减少70-100%);5表示死亡率为50-79%(对于根结线虫病(Meloidogyne incognita),根结减少50-69%);0表示其死亡率低于50%〔对于根结线虫病(Meloidogyne incognita),根结减少〕。
在表Ⅸ中,试验用的害虫是以字母符号表示,试验所用的害虫种类、寄生的介质或食物以及试验的类型和持续的时间列于表Ⅷ中。
(表Ⅷ见下页)
表Ⅸ
勘误表
Claims (12)
1、具有式(Ⅰ)的化合物、它的立体异构体及其金属配合物,
在(Ⅰ)中:
W是取代的吡啶基或取代的嘧啶基,并通过它们的任一个环碳原子连接于A上,
A是氧原子或S(O)n,其中n=0,1或2,
X、Y和Z可以相同或不同,它们可以是氢或卤原子、或羟基、有选择取代的烷基、有选择取代的链烯基、有选择取代的芳基、有选择取代的炔基、有选择取代的烷氧基、有选择取代的烷硫基、有选择取代的芳氧基、有选择取代的芳烷氧基、有选择取代的酸基、有选择取代的氨基、有选择取代的酰氨基、硝基、氰基、-CO2R3、-CONR4R5、-COR6或-S(O)mR7(其中m=0,1或2),或X、Y和Z中,任意两个在苯环上处于相邻位置时,这两个基团连接起来形成稠环,该稠环或为芳香族的或为脂肪族的,可以有选择地含有一个或多个杂原子,
R1和R2可以相同或不同,它们可以是有选择取代的烷基,其条件是W5-三氟甲基吡啶-2-基,A是氧,X是氢,并且如果Z是氢,Y和Z不同时是3-硝基-5-氯、3,5-二硝基、4,5-二甲氧基或4,5-亚甲二氧基,则R1和R2均为甲基,Y和Z不都是氢,Y不是F、Cl、甲基、硝基、5-CF3、5-SCH3或4-(CH3)2N;
R3、R4、R5、R6和R7可以相同或不同,它们可以是氢原子或有选择取代的烷基、有选择取代的环烷基、有选择取代的环烷基烷基、有选择取代的链烯基、有选择取代的炔基、有选择取代的芳基或有选择取代的芳烷基。
2、具有式(Ⅰ)的化合物及其立体异构体,
其中
W是取代的吡啶基或取代的嘧啶基,并通过它们的任一碳原子连接于A上,而其所带有的取代基的定义同上;
A是氧原子或S(O)n,其中n=0,1或2;
X、Y和Z可以相同或不同,它们可以是氢、氟、氯或溴原子、或C1-4烷基、C2-5链烯基、C2-5炔基、苯基、C1-4卤代烷基、C1-4烷氧基、苯氧基、苄氧基或一或二烷基氨基,或X、Y和Z中任意两个在苯环上处于相邻位置时,这两个基团可连接起来形成稠芳环;
其中,上述任何基团的脂族部分可以有选择地由一个或多个下述基团所取代:C1-4烷氧基、氟、氯或溴原子、其本身是有选择取代的苯环、其本身为有选择取代的杂环(该杂环可以为芳族或非芳族的)、硝基、氨基、氰基、羟基或羧基,并且上述任何基团的苯基部分可以由一个或多个下述基团有选择地取代;氟、氯或溴原子、苯环、C1-4烷基、C1-4烷氧基、硝基、氨基、氰基、羟基或羧基;
R1和R2可以相同或不同,它们可以是C1-4烷基,各个烷基都可由一个、二个或三个卤原子有选择地取代,其条件是W是5-三氟甲基吡啶-2-基,A是氧,X是氢,并且如果Z是氢,Y和Z不同时是3-硝基-5-氯、3,5-二硝基、4,5-二甲氧基或4,5-亚甲二氧基,则R1和R2都为甲基,Y和Z不都是氢,Y不是F、Cl、甲基、硝基、5-CF3、5-SCH3或4-(CH3)2N。
3、具有式(Ⅰa)的化合物及其立体异构体,
其中:
A是S(O)n,这里n=0,1或2,或优先选用氧原子;
W是取代的吡啶基或取代的嘧啶基,并且通过它的任一个碳原子连接于A,吡啶或嘧啶环上的取代基可以相同或不同,它们可以是一个或多个卤原子、或羟基、有选择取代的烷基、有选择取代的链烯基、有选择取代的芳基、有选择取代的炔基、有选择取代的烷氧基(包括卤代烷氧基)、有选择取代的芳氧基、有选择取代的杂环氧基、有选择取代的芳基、有选择取代的杂环基、有选择取代的酸基、有选择取代的氨基、有选择取代的酰氨基、硝基、氰基、-CO2R3、-CONR4R5、-COR6或S(O)mR7(其中m=0,1或2),其条件是W是5-三氟甲基吡啶-2-基,A是氧,X是氢,并且如果Z是氢,Y和Z一起不同时是3-硝基-5-氯、3,5-二硝基、4,5-二甲氧基或4,5-亚甲二氧基,
则R1和R2都是甲基,Y和Z不都是氢,Y不是氟、氯、甲基、硝基、5-CF3、5-SCH3或4-(CH3)2N;
R3、R4、R5、R6和R7的定义同上。
5、制备权利要求1所述式(Ⅰ)化合物的方法,该方法包括:
(ⅰ)当式(Ⅲ)中的R8是金属原子时,于适宜溶剂中,用R2-L处理化合物(Ⅲ),
或当式(Ⅲ)中的R8是氢时,于适宜溶剂中,相继用碱或R2-L处理化合物(Ⅲ),
或(ⅱ)于酸或碱的条件下,从醛缩二醇(ⅩⅢ)中消除链烷醇R2OH,
或(ⅲ)于适宜的溶剂中,在碱和有选择的过渡金属或过渡金属盐催化剂存在下,将化合物(Ⅸ)与式W-L化合物反应,
(图Ⅸ见下页)
(图ⅩⅤ见下页)
其中,W、X、Y、Z、R1和R2的含义和权利要求1中的相同,L是卤原子或其他的易离去基团,Ph是苯基。
6、本说明书中所定义的中间体化合物(Ⅲ)-(Ⅴ)、(Ⅸ)-(ⅩⅤ)、(ⅩⅦ)、(ⅩⅨ)、(ⅩⅩ)和(ⅩⅩⅤ)。
7、杀真菌剂的组合物,该组合物包括作为有效成分的杀真菌有效量的权利要求1所述的化合物和杀真菌可以接受的载体或稀释剂。
8、杀真菌的方法,该方法包括将权利要求1所述的化合物或权利要求7所述的组合物施用于植物或种子,或它们所在的场所。
9、调节植物生长的组合物,该组合物包括作为有效成分的、其定义和权利要求1相同的、调节植物生长有效量的化合物(Ⅰ)及其可以接受的载体或稀释剂。
10、调节植物生长的方法,该方法包括将权利要求1所述的调节植物生长有效量的化合物(Ⅰ)施用于植物。
11、杀虫剂或杀线虫剂的组合物,该组合物包括权利要求1所述的杀虫或杀线虫化合物(Ⅰ)及载体或稀释剂。
12、消灭或控制昆虫和线虫的方法,该方法包括将权利要求1所定义的杀虫有效量的化合物(Ⅰ),或权利11所述的杀虫有效量的组合物投于害虫或这些害虫所在的场所。
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8609454 | 1986-04-17 | ||
GB868609454A GB8609454D0 (en) | 1986-04-17 | 1986-04-17 | Fungicides |
GB8630825 | 1986-12-23 | ||
GB868630825A GB8630825D0 (en) | 1986-12-23 | 1986-12-23 | Fungicides |
Publications (2)
Publication Number | Publication Date |
---|---|
CN87103623A true CN87103623A (zh) | 1988-02-24 |
CN1021720C CN1021720C (zh) | 1993-08-04 |
Family
ID=26290645
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN87103623A Expired - Lifetime CN1021720C (zh) | 1986-04-17 | 1987-04-17 | 含有丙烯酸衍生物作为活性成分的农用组合物,其应用和制备方法 |
Country Status (29)
Country | Link |
---|---|
US (4) | US5057146A (zh) |
EP (3) | EP0391451A1 (zh) |
JP (1) | JPH085860B2 (zh) |
KR (1) | KR950003925B1 (zh) |
CN (1) | CN1021720C (zh) |
AP (1) | AP26A (zh) |
AR (1) | AR245106A1 (zh) |
AU (1) | AU609035B2 (zh) |
BG (1) | BG61709B2 (zh) |
CA (1) | CA1297480C (zh) |
CS (1) | CS270561B2 (zh) |
DE (2) | DE3789683T2 (zh) |
DK (1) | DK169268B1 (zh) |
EG (1) | EG18551A (zh) |
ES (1) | ES2052556T3 (zh) |
GB (1) | GB8925342D0 (zh) |
GE (2) | GEP19971034B (zh) |
HK (1) | HK10192A (zh) |
HU (1) | HU203875B (zh) |
IE (1) | IE60727B1 (zh) |
IL (1) | IL82127A (zh) |
LV (2) | LV10240A (zh) |
MD (1) | MD420C2 (zh) |
PL (1) | PL151058B1 (zh) |
PT (1) | PT84698B (zh) |
RU (1) | RU2039044C1 (zh) |
SU (1) | SU1665875A3 (zh) |
TR (1) | TR22787A (zh) |
UA (1) | UA6304A1 (zh) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1803798B (zh) * | 1993-08-11 | 2010-06-16 | 拜尔公司 | 制备杀真菌组合物的方法 |
CN102276538A (zh) * | 2011-08-12 | 2011-12-14 | 河北威远生物化工股份有限公司 | 嘧菌酯及其关键中间体的制备方法 |
CN102126955B (zh) * | 2005-04-26 | 2012-12-12 | 先正达有限公司 | 用dabco作催化剂制备嘧菌酯的方法和用于该方法的新型中间体 |
CN104292102A (zh) * | 2014-07-29 | 2015-01-21 | 浙江颖欣化工有限公司 | 一种嘧菌酯中间体的制备方法 |
CN115868502A (zh) * | 2022-12-16 | 2023-03-31 | 山东海利尔化工有限公司 | 一种含新烟碱的农药组合物 |
Families Citing this family (64)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5229393A (en) * | 1985-08-22 | 1993-07-20 | Imperial Chemical Industries Plc | Fungicidal alpha substituted acrylates |
ES2053533T3 (es) * | 1986-04-17 | 1994-08-01 | Ici Plc | Derivados de esteres de acido piridil-acrilico, un proceso para su preparacion y su uso como fungicidas. |
EP0242070A3 (en) * | 1986-04-17 | 1988-12-28 | Imperial Chemical Industries Plc | Phenyl-acrylic acid ester derivatives, process for their preparation and their use as fungicides |
EP0391451A1 (en) * | 1986-04-17 | 1990-10-10 | Imperial Chemical Industries Plc | Fungicides |
GB2189485B (en) * | 1986-04-17 | 1990-11-28 | Ici Plc | Derivatives of acrylic acid useful in agriculture |
GB8620251D0 (en) * | 1986-08-20 | 1986-10-01 | Ici Plc | Fungicides |
GB8711538D0 (en) * | 1987-05-15 | 1987-06-17 | Ici Plc | Fungicides |
YU47288B (sh) * | 1987-07-11 | 1995-01-31 | Schering Agrochemicals Limited | Akrilatni fungicidi i postupak za njihovo dobijanje |
US5194438A (en) * | 1988-07-15 | 1993-03-16 | Basf Aktiengesellschaft | α-arylacrylates substituted by a trifluoromethylpyrimidinyloxy radical, fungicidal compositions and methods |
DE3823991A1 (de) * | 1988-07-15 | 1990-02-15 | Basf Ag | Heterocyclisch substituierte (alpha)-aryl-acrylsaeureester und fungizide, die diese verbindungen enthalten |
DE3836581A1 (de) * | 1988-10-27 | 1990-05-03 | Basf Ag | Heterocyclisch substituierte (alpha)-aryl-acrylsaeuremethylester und ihre verwendung |
DE3838094A1 (de) * | 1988-11-10 | 1990-05-17 | Nordmark Arzneimittel Gmbh | Feste pharmazeutische retardform |
US5264440A (en) * | 1989-02-10 | 1993-11-23 | Imperial Chemical Industries Plc | Fungicides |
US5145856A (en) * | 1989-02-10 | 1992-09-08 | Imperial Chemical Industries Plc | Fungicides |
GB8903019D0 (en) * | 1989-02-10 | 1989-03-30 | Ici Plc | Fungicides |
US5206266A (en) * | 1989-03-09 | 1993-04-27 | Basf Aktiengesellschaft | Substituted oxime ethers and fungicides which contain these compounds |
SK47590A3 (en) * | 1989-03-09 | 1997-08-06 | Basf Ag | Fungicidal agent and a method of producing its active substance |
GB8908875D0 (en) * | 1989-04-19 | 1989-06-07 | Ici Plc | Fungicides |
US5229391A (en) * | 1989-04-19 | 1993-07-20 | Imperial Chemical Industries Plc | Pyrimidine derivatives and their use as fungicidal agents |
DK0629609T3 (da) * | 1989-05-17 | 1996-12-23 | Shionogi & Co | Fremgangsmåde til fremstilling af alkoxyiminoacetamidderivater og et mellemprodukt dertil |
DE3919435A1 (de) * | 1989-06-14 | 1990-12-20 | Basf Ag | Salicylaldehyd- und salicylsaeurederivate sowie deren schwefelanaloge, verfahren zu ihrer herstellung als herbizide und bioregulatoren |
GB8914797D0 (en) * | 1989-06-28 | 1989-08-16 | Ici Plc | Fungicides |
DE4014940A1 (de) * | 1989-09-01 | 1991-03-07 | Bayer Ag | Substituierte acrylsaeureester |
GB8926630D0 (en) * | 1989-11-24 | 1990-01-17 | Ici Plc | Fungicides |
GB9016584D0 (en) * | 1990-07-27 | 1990-09-12 | Ici Plc | Fungicides |
IE74711B1 (en) | 1990-07-27 | 1997-07-30 | Ici Plc | Fungicides |
DE4025338A1 (de) * | 1990-08-10 | 1992-02-13 | Bayer Ag | Substituierte pyridine |
GB9023294D0 (en) * | 1990-10-25 | 1990-12-05 | Ici Plc | Fungicides |
GB9122430D0 (en) * | 1990-11-16 | 1991-12-04 | Ici Plc | Chemical process |
GB9307247D0 (en) * | 1993-04-07 | 1993-06-02 | Zeneca Ltd | Fungicidal compounds |
ZW8594A1 (en) * | 1993-08-11 | 1994-10-12 | Bayer Ag | Substituted azadioxacycbalkenes |
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 |
GB9415291D0 (en) * | 1994-07-28 | 1994-09-21 | Zeneca Ltd | Chemical process |
ES2162074T3 (es) * | 1995-06-28 | 2001-12-16 | Syngenta Ltd | Procedimiento para la preparacion de 2-(6-sustituido pirid-2-iloximetil)fenilacetato. |
DE19611653A1 (de) * | 1995-10-18 | 1997-04-24 | Bayer Ag | Fluormethoxyacrylsäurederivate |
WO1997014687A1 (de) | 1995-10-18 | 1997-04-24 | Bayer Aktiengesellschaft | Fluormethoxyacrylsäurederivate und ihre verwendung als schädlingsbekämpfungsmittel |
DE19648009A1 (de) | 1996-11-20 | 1998-05-28 | Bayer Ag | Glyoxylsäureamide |
DE19726201A1 (de) | 1997-06-20 | 1998-12-24 | Bayer Ag | Glyoxylsäureamide |
US20040136915A1 (en) * | 1997-10-01 | 2004-07-15 | Dugger Harry A. | Buccal, polar and non-polar spray containing atropine |
US5961479A (en) * | 1998-06-05 | 1999-10-05 | Dermalabs Inc. | Therapeutic mask |
US6133294A (en) * | 1998-09-16 | 2000-10-17 | Kirby; Neil V. | 2-methoxyimino-2-(pyridinyloxymethyl) phenyl acetamides with 5 membered heterocyclic rings on the pyridine ring |
WO2000040537A1 (fr) * | 1998-12-29 | 2000-07-13 | Nippon Soda Co., Ltd. | Procedes de production d'un derive d'acide acrylique |
GB0114408D0 (en) * | 2001-06-13 | 2001-08-08 | Syngenta Ltd | Chemical process |
ITMI20020814A1 (it) | 2002-04-17 | 2003-10-17 | Isagro Ricerca Srl | Nuovi analoghi delle strobilurine e loro uso quali acaricidi e insetticidi |
GB0619941D0 (en) * | 2006-10-09 | 2006-11-15 | Syngenta Ltd | Chemical process |
IL180134A0 (en) | 2006-12-17 | 2007-07-04 | David Ovadia | Process for the preparation of substituted cyanophenoxy-pyrimidinyloxy -phenyl acrylate derivatives |
IL181125A0 (en) | 2007-02-01 | 2007-07-04 | Maktheshim Chemical Works Ltd | Polymorphs of 3-(e)-2-{2-[6-(2- |
CN101311170B (zh) | 2007-05-25 | 2010-09-15 | 中国中化股份有限公司 | 取代嘧啶醚类化合物及其应用 |
CN100564362C (zh) * | 2007-10-24 | 2009-12-02 | 北京颖泰嘉和科技股份有限公司 | 嘧菌酯及其类似物的制备方法 |
NO2300013T3 (zh) | 2008-05-21 | 2018-02-03 | ||
US9273077B2 (en) | 2008-05-21 | 2016-03-01 | Ariad Pharmaceuticals, Inc. | Phosphorus derivatives as kinase inhibitors |
KR101219989B1 (ko) * | 2008-12-04 | 2013-01-08 | 금호석유화학 주식회사 | 광산발생제, 공중합체, 화학증폭형 레지스트 조성물 및 화학증폭형 레지스트 조성물을 이용한 패턴 형성 방법 |
CN101906075B (zh) | 2009-06-05 | 2012-11-07 | 中国中化股份有限公司 | 含取代苯胺基嘧啶基团的e-型苯基丙烯酸酯类化合物及其应用 |
US20100316728A1 (en) * | 2009-06-15 | 2010-12-16 | Rreeves William H | Therapeutic mask and Method of Treatment Employing the Same |
CA2822296A1 (en) | 2010-12-21 | 2012-06-28 | Bayer Cropscience Lp | Sandpaper mutants of bacillus and methods of their use to enhance plant growth, promote plant health and control diseases and pests |
EA201391626A1 (ru) | 2011-05-04 | 2014-03-31 | Ариад Фармасьютикалз, Инк. | Соединения для ингибирования клеточной пролиферации в egfr-стимулированных типах рака |
BR112014005654A2 (pt) | 2011-09-12 | 2017-03-28 | Bayer Cropscience Lp | métodos para melhorar a saúde e promover o crescimento de uma planta e/ou de melhorar o amadurecimento da fruta |
JP6469567B2 (ja) | 2012-05-05 | 2019-02-13 | アリアド・ファーマシューティカルズ・インコーポレイテッド | Egfr発動性がんの細胞増殖阻害用化合物 |
US9611283B1 (en) | 2013-04-10 | 2017-04-04 | Ariad Pharmaceuticals, Inc. | Methods for inhibiting cell proliferation in ALK-driven cancers |
TWI621614B (zh) | 2013-05-28 | 2018-04-21 | 科麥農股份有限公司 | 4,6-雙(芳氧基)嘧啶衍生物的製備方法 |
WO2016193267A1 (en) * | 2015-06-02 | 2016-12-08 | Syngenta Participations Ag | Mosquito vector control compositions, methods and products utilizing same |
EP3700893B1 (en) | 2017-10-27 | 2021-11-17 | Syngenta Participations AG | Vector control compositions, methods and products utilizing same |
CN108314656B (zh) | 2018-02-27 | 2020-10-27 | 浙江工业大学 | 不饱和烃嘧啶硫醚类化合物及其制备方法与应用 |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU535637B2 (en) * | 1977-09-13 | 1984-03-29 | Ici Australia Limited | 2-phenoxypyrimidines and their. use as herbicides |
JPS5562043A (en) * | 1978-11-01 | 1980-05-10 | Ihara Chem Ind Co Ltd | Preparation of phenoxycarboxylic acid derivative |
DE3025368A1 (de) | 1980-07-04 | 1982-01-28 | Hoechst Ag, 6000 Frankfurt | Verfahren zur synthese von strobilurin |
AU564214B2 (en) * | 1984-10-04 | 1987-08-06 | Mills, T.A. | Air jets on header fingers |
NZ213630A (en) | 1984-10-19 | 1990-02-26 | Ici Plc | Acrylic acid derivatives and fungicidal compositions |
DE3519280A1 (de) * | 1985-05-30 | 1986-12-04 | Basf Ag, 6700 Ludwigshafen | Stilbenderivate und fungizide, die diese verbindungen enthalten |
DE3519282A1 (de) * | 1985-05-30 | 1986-12-04 | Basf Ag, 6700 Ludwigshafen | Acrylsaeureester und fungizide, die diese verbindungen enthalten |
EP0242070A3 (en) * | 1986-04-17 | 1988-12-28 | Imperial Chemical Industries Plc | Phenyl-acrylic acid ester derivatives, process for their preparation and their use as fungicides |
EP0391451A1 (en) * | 1986-04-17 | 1990-10-10 | Imperial Chemical Industries Plc | Fungicides |
GB8617648D0 (en) * | 1986-07-18 | 1986-08-28 | Ici Plc | Fungicides |
GB8619236D0 (en) * | 1986-08-06 | 1986-09-17 | Ici Plc | Fungicides |
YU47288B (sh) * | 1987-07-11 | 1995-01-31 | Schering Agrochemicals Limited | Akrilatni fungicidi i postupak za njihovo dobijanje |
-
1987
- 1987-03-31 EP EP90109067A patent/EP0391451A1/en not_active Withdrawn
- 1987-03-31 DE DE3789683T patent/DE3789683T2/de not_active Expired - Lifetime
- 1987-03-31 EP EP90109068A patent/EP0387923B1/en not_active Expired - Lifetime
- 1987-03-31 DE DE3789117T patent/DE3789117T2/de not_active Expired - Fee Related
- 1987-03-31 ES ES87302795T patent/ES2052556T3/es not_active Expired - Lifetime
- 1987-03-31 EP EP87302795A patent/EP0242081B1/en not_active Expired - Lifetime
- 1987-04-01 IE IE84787A patent/IE60727B1/en not_active IP Right Cessation
- 1987-04-07 IL IL8212787A patent/IL82127A/en not_active IP Right Cessation
- 1987-04-08 AU AU71196/87A patent/AU609035B2/en not_active Expired
- 1987-04-10 DK DK187887A patent/DK169268B1/da not_active IP Right Cessation
- 1987-04-14 CS CS872656A patent/CS270561B2/cs not_active IP Right Cessation
- 1987-04-15 HU HU871653A patent/HU203875B/hu unknown
- 1987-04-15 AR AR87307314A patent/AR245106A1/es active
- 1987-04-16 TR TR261/87A patent/TR22787A/xx unknown
- 1987-04-16 AP APAP/P/1987/000061A patent/AP26A/en active
- 1987-04-16 UA UA4356041A patent/UA6304A1/uk unknown
- 1987-04-16 PT PT84698A patent/PT84698B/pt unknown
- 1987-04-16 PL PL1987265210A patent/PL151058B1/pl unknown
- 1987-04-17 CN CN87103623A patent/CN1021720C/zh not_active Expired - Lifetime
- 1987-04-17 KR KR1019870003675A patent/KR950003925B1/ko not_active IP Right Cessation
- 1987-04-17 JP JP9347887A patent/JPH085860B2/ja not_active Expired - Lifetime
- 1987-04-19 EG EG231/87A patent/EG18551A/xx active
- 1987-04-21 CA CA000535187A patent/CA1297480C/en not_active Expired - Lifetime
-
1988
- 1988-07-08 SU SU884356041A patent/SU1665875A3/ru active
-
1989
- 1989-11-09 GB GB898925342A patent/GB8925342D0/en active Pending
-
1990
- 1990-01-17 US US07/465,526 patent/US5057146A/en not_active Expired - Lifetime
-
1991
- 1991-12-10 RU SU915010295A patent/RU2039044C1/ru active
-
1992
- 1992-01-30 HK HK101/92A patent/HK10192A/xx unknown
- 1992-12-07 LV LV920264A patent/LV10240A/xx unknown
- 1992-12-24 LV LVP-92-488A patent/LV10241B/en unknown
-
1993
- 1993-07-20 GE GEAP19931073A patent/GEP19971034B/en unknown
- 1993-08-26 BG BG98074A patent/BG61709B2/bg unknown
-
1994
- 1994-05-09 US US08/239,845 patent/US5470819A/en not_active Expired - Lifetime
- 1994-07-12 MD MD95-0291A patent/MD420C2/ro unknown
- 1994-10-06 GE GEAP19942230A patent/GEP19981393B/en unknown
-
1995
- 1995-03-29 US US08/412,450 patent/US5602076A/en not_active Expired - Lifetime
- 1995-03-29 US US08/412,449 patent/US5633256A/en not_active Expired - Lifetime
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1803798B (zh) * | 1993-08-11 | 2010-06-16 | 拜尔公司 | 制备杀真菌组合物的方法 |
CN102126955B (zh) * | 2005-04-26 | 2012-12-12 | 先正达有限公司 | 用dabco作催化剂制备嘧菌酯的方法和用于该方法的新型中间体 |
CN102276538A (zh) * | 2011-08-12 | 2011-12-14 | 河北威远生物化工股份有限公司 | 嘧菌酯及其关键中间体的制备方法 |
CN102276538B (zh) * | 2011-08-12 | 2015-01-28 | 河北威远生化农药有限公司 | 嘧菌酯及其关键中间体的制备方法 |
CN104292102A (zh) * | 2014-07-29 | 2015-01-21 | 浙江颖欣化工有限公司 | 一种嘧菌酯中间体的制备方法 |
CN115868502A (zh) * | 2022-12-16 | 2023-03-31 | 山东海利尔化工有限公司 | 一种含新烟碱的农药组合物 |
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN1021720C (zh) | 含有丙烯酸衍生物作为活性成分的农用组合物,其应用和制备方法 | |
CN1021403C (zh) | 含丙烯酸衍生物的农用组合物 | |
CN1020901C (zh) | 杀真菌剂组合物其制备方法及用途 | |
CN1024005C (zh) | 杀真菌剂 | |
CN1038678C (zh) | 杀真菌组合物,其制备方法及应用 | |
CN1023600C (zh) | 杀菌剂组合物及其制法 | |
CN1036519C (zh) | 杀真菌组合物,其制备方法及应用 | |
CN85108235A (zh) | 杀菌剂的制备 | |
CN1020391C (zh) | 制备杀菌化合物的方法 | |
CN1054974A (zh) | 除草用的甲酰胺衍生物 | |
CN1022885C (zh) | 含有丙烯酸衍生物作为活性成分的农用组合物,其应用制备方法 | |
US5468747A (en) | Fungicidal compositions and methods of use employing pyrimidine derivatives | |
CN100336807C (zh) | 苯甲酰吡啶衍生物或其盐、含有它作为活性成分的杀真菌剂、它的产生方法以及用于产生它的中间体 | |
CN87105481A (zh) | 杀真菌剂及其制备方法和用途 | |
CN1065658A (zh) | 杀真菌剂 | |
CA2107084A1 (en) | Fungicides | |
CN1083810A (zh) | 4-[2-(4-(2-吡啶氧)苯基)乙氧基]喹唑啉及其类似物 | |
CN1080638A (zh) | 吡啶衍生物及其制备方法,含有该衍生物的除草组合物,以及杀杂草方法 | |
CN87102877A (zh) | 杀菌剂 | |
CN1065659A (zh) | N-苯基氨基甲酸酯化合物、其制备方法以及控制有害生物的杀虫剂组合物 | |
CN1074443A (zh) | 桥连的杂环杀真菌剂 | |
CN1083811A (zh) | 喹啉和喹唑啉的吡啶乙氧基、吡啶乙氨基和吡啶丙基衍生物 | |
CN1053232A (zh) | 杀真菌剂 | |
CN1048383A (zh) | 杀真菌剂及其制备方法 | |
CN1058019A (zh) | 杀真菌化合物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
C53 | Correction of patent of invention or patent application | ||
COR | Change of bibliographic data |
Free format text: CORRECT: APPLICANT; FROM: IMPERIAL CHEMICAL CORPORATION TO: ZENECA CO., LTD. |
|
ERR | Gazette correction |
Free format text: CORRECT: PATENTEE; FROM: ZENECA CO., LTD. TO: ZENECA LTD |
|
C15 | Extension of patent right duration from 15 to 20 years for appl. with date before 31.12.1992 and still valid on 11.12.2001 (patent law change 1993) | ||
C17 | Cessation of patent right |