CN105175336B - 一种3‑(3,3‑二氯烯丙氧基)‑1‑苯基吡唑‑5‑甲酰胺衍生物及其制备方法 - Google Patents
一种3‑(3,3‑二氯烯丙氧基)‑1‑苯基吡唑‑5‑甲酰胺衍生物及其制备方法 Download PDFInfo
- Publication number
- CN105175336B CN105175336B CN201510495921.4A CN201510495921A CN105175336B CN 105175336 B CN105175336 B CN 105175336B CN 201510495921 A CN201510495921 A CN 201510495921A CN 105175336 B CN105175336 B CN 105175336B
- Authority
- CN
- China
- Prior art keywords
- phenylpyrazole
- preparation
- phenyl
- bis
- added
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 40
- WITMXBRCQWOZPX-UHFFFAOYSA-N 1-phenylpyrazole Chemical compound C1=CC=NN1C1=CC=CC=C1 WITMXBRCQWOZPX-UHFFFAOYSA-N 0.000 title 1
- 150000003857 carboxamides Chemical class 0.000 title 1
- 239000000575 pesticide Substances 0.000 claims abstract description 19
- -1 2- p-fluorophenyl phenyl Chemical group 0.000 claims description 64
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 238000004440 column chromatography Methods 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 239000003208 petroleum Substances 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000003480 eluent Substances 0.000 claims description 9
- 239000000741 silica gel Substances 0.000 claims description 9
- 229910002027 silica gel Inorganic materials 0.000 claims description 9
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000012141 concentrate Substances 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 235000002639 sodium chloride Nutrition 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- JFEVIPGMXQNRRF-UHFFFAOYSA-N 1,1,3-trichloroprop-1-ene Chemical class ClCC=C(Cl)Cl JFEVIPGMXQNRRF-UHFFFAOYSA-N 0.000 claims description 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical class CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 claims description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 3
- 239000008346 aqueous phase Substances 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 239000012153 distilled water Substances 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- 150000003217 pyrazoles Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical class ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 2
- 238000006482 condensation reaction Methods 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 6
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 claims 3
- 125000004494 ethyl ester group Chemical group 0.000 claims 3
- 235000019253 formic acid Nutrition 0.000 claims 3
- 229960001866 silicon dioxide Drugs 0.000 claims 3
- MKMDCEXRIPLNGJ-UHFFFAOYSA-N 2-phenyl-1h-pyrazol-5-one Chemical class N1=C(O)C=CN1C1=CC=CC=C1 MKMDCEXRIPLNGJ-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 230000003292 diminished effect Effects 0.000 claims 2
- 235000019441 ethanol Nutrition 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- 235000015424 sodium Nutrition 0.000 claims 2
- 235000011054 acetic acid Nutrition 0.000 claims 1
- 150000001243 acetic acids Chemical class 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 125000005909 ethyl alcohol group Chemical group 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- GFAUNYMRSKVDJL-UHFFFAOYSA-N formyl chloride Chemical class ClC=O GFAUNYMRSKVDJL-UHFFFAOYSA-N 0.000 claims 1
- 239000004519 grease Substances 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 150000004031 phenylhydrazines Chemical class 0.000 claims 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 238000005292 vacuum distillation Methods 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 8
- 201000010099 disease Diseases 0.000 abstract description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 6
- 241000238631 Hexapoda Species 0.000 abstract description 2
- 241000700605 Viruses Species 0.000 abstract description 2
- 241000607479 Yersinia pestis Species 0.000 abstract description 2
- 238000003898 horticulture Methods 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000005828 Pyrimethanil Substances 0.000 description 6
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 6
- ZICSNTBKDUHAMA-UHFFFAOYSA-N ethyl 5-oxo-2-phenyl-1h-pyrazole-3-carboxylate Chemical compound CCOC(=O)C1=CC(=O)NN1C1=CC=CC=C1 ZICSNTBKDUHAMA-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 4
- 239000000417 fungicide Substances 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- XUNYDVLIZWUPAW-UHFFFAOYSA-N (4-chlorophenyl) n-(4-methylphenyl)sulfonylcarbamate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)OC1=CC=C(Cl)C=C1 XUNYDVLIZWUPAW-UHFFFAOYSA-N 0.000 description 3
- 239000005893 Diflubenzuron Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003899 bactericide agent Substances 0.000 description 3
- 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 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 229940019503 diflubenzuron Drugs 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 229960000490 permethrin Drugs 0.000 description 3
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 3
- WCXDHFDTOYPNIE-RIYZIHGNSA-N (E)-acetamiprid Chemical compound N#C/N=C(\C)N(C)CC1=CC=C(Cl)N=C1 WCXDHFDTOYPNIE-RIYZIHGNSA-N 0.000 description 2
- 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 2
- UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical compound ClC1=NC=CC=N1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- 239000005875 Acetamiprid Substances 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 239000005734 Benalaxyl Substances 0.000 description 2
- 239000005874 Bifenthrin Substances 0.000 description 2
- 229940123208 Biguanide Drugs 0.000 description 2
- 239000005740 Boscalid Substances 0.000 description 2
- 239000005747 Chlorothalonil Substances 0.000 description 2
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 2
- 239000005894 Emamectin Substances 0.000 description 2
- 239000005958 Fenamiphos (aka phenamiphos) Substances 0.000 description 2
- 239000005795 Imazalil Substances 0.000 description 2
- 239000005802 Mancozeb Substances 0.000 description 2
- 239000005807 Metalaxyl Substances 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- 229930182764 Polyoxin Natural products 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 239000005931 Spirotetramat Substances 0.000 description 2
- 239000005842 Thiophanate-methyl Substances 0.000 description 2
- 239000005843 Thiram Substances 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- OMFRMAHOUUJSGP-IRHGGOMRSA-N bifenthrin Chemical compound C1=CC=C(C=2C=CC=CC=2)C(C)=C1COC(=O)[C@@H]1[C@H](\C=C(/Cl)C(F)(F)F)C1(C)C OMFRMAHOUUJSGP-IRHGGOMRSA-N 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 229940118790 boscalid Drugs 0.000 description 2
- WYEMLYFITZORAB-UHFFFAOYSA-N boscalid Chemical compound C1=CC(Cl)=CC=C1C1=CC=CC=C1NC(=O)C1=CC=CN=C1Cl WYEMLYFITZORAB-UHFFFAOYSA-N 0.000 description 2
- 229960005286 carbaryl Drugs 0.000 description 2
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 2
- IRUJZVNXZWPBMU-UHFFFAOYSA-N cartap Chemical compound NC(=O)SCC(N(C)C)CSC(N)=O IRUJZVNXZWPBMU-UHFFFAOYSA-N 0.000 description 2
- CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 2
- FBOUIAKEJMZPQG-BLXFFLACSA-N diniconazole-M Chemical compound C1=NC=NN1/C([C@H](O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1Cl FBOUIAKEJMZPQG-BLXFFLACSA-N 0.000 description 2
- GCKZANITAMOIAR-XWVCPFKXSA-N dsstox_cid_14566 Chemical compound [O-]C(=O)C1=CC=CC=C1.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H]([NH2+]C)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 GCKZANITAMOIAR-XWVCPFKXSA-N 0.000 description 2
- 229960002125 enilconazole Drugs 0.000 description 2
- VMNULHCTRPXWFJ-UJSVPXBISA-N enoxastrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)\C=C\C1=CC=C(Cl)C=C1 VMNULHCTRPXWFJ-UJSVPXBISA-N 0.000 description 2
- ZCJPOPBZHLUFHF-UHFFFAOYSA-N fenamiphos Chemical compound CCOP(=O)(NC(C)C)OC1=CC=C(SC)C(C)=C1 ZCJPOPBZHLUFHF-UHFFFAOYSA-N 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- 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 2
- 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 2
- YTYGAJLZOJPJGH-UHFFFAOYSA-N noviflumuron Chemical compound FC1=C(Cl)C(OC(F)(F)C(C(F)(F)F)F)=C(Cl)C=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F YTYGAJLZOJPJGH-UHFFFAOYSA-N 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 2
- 229940067157 phenylhydrazine Drugs 0.000 description 2
- 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 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- CLSVJBIHYWPGQY-GGYDESQDSA-N spirotetramat Chemical compound CCOC(=O)OC1=C(C=2C(=CC=C(C)C=2)C)C(=O)N[C@@]11CC[C@H](OC)CC1 CLSVJBIHYWPGQY-GGYDESQDSA-N 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound 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](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 2
- 229960002447 thiram Drugs 0.000 description 2
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 description 1
- KAATUXNTWXVJKI-NSHGMRRFSA-N (1R)-cis-(alphaS)-cypermethrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-NSHGMRRFSA-N 0.000 description 1
- ZXQYGBMAQZUVMI-RDDWSQKMSA-N (1S)-cis-(alphaR)-cyhalothrin Chemical compound CC1(C)[C@H](\C=C(/Cl)C(F)(F)F)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-RDDWSQKMSA-N 0.000 description 1
- XERJKGMBORTKEO-VZUCSPMQSA-N (1e)-2-(ethylcarbamoylamino)-n-methoxy-2-oxoethanimidoyl cyanide Chemical compound CCNC(=O)NC(=O)C(\C#N)=N\OC XERJKGMBORTKEO-VZUCSPMQSA-N 0.000 description 1
- AMNAZJFEONUVTD-KEWDHRJRSA-N (2s,3s,4s,5r,6r)-6-(4-amino-2-oxopyrimidin-1-yl)-4,5-dihydroxy-3-[[(2s)-3-hydroxy-2-[[2-(methylamino)acetyl]amino]propanoyl]amino]oxane-2-carboxamide Chemical compound O1[C@H](C(N)=O)[C@@H](NC(=O)[C@H](CO)NC(=O)CNC)[C@H](O)[C@@H](O)[C@@H]1N1C(=O)N=C(N)C=C1 AMNAZJFEONUVTD-KEWDHRJRSA-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
- PGOOBECODWQEAB-UHFFFAOYSA-N (E)-clothianidin Chemical compound [O-][N+](=O)\N=C(/NC)NCC1=CN=C(Cl)S1 PGOOBECODWQEAB-UHFFFAOYSA-N 0.000 description 1
- BKBSMMUEEAWFRX-NBVRZTHBSA-N (E)-flumorph Chemical compound C1=C(OC)C(OC)=CC=C1C(\C=1C=CC(F)=CC=1)=C\C(=O)N1CCOCC1 BKBSMMUEEAWFRX-NBVRZTHBSA-N 0.000 description 1
- CFRPSFYHXJZSBI-DHZHZOJOSA-N (E)-nitenpyram Chemical compound [O-][N+](=O)/C=C(\NC)N(CC)CC1=CC=C(Cl)N=C1 CFRPSFYHXJZSBI-DHZHZOJOSA-N 0.000 description 1
- XGWIJUOSCAQSSV-XHDPSFHLSA-N (S,S)-hexythiazox Chemical compound S([C@H]([C@@H]1C)C=2C=CC(Cl)=CC=2)C(=O)N1C(=O)NC1CCCCC1 XGWIJUOSCAQSSV-XHDPSFHLSA-N 0.000 description 1
- QNBTYORWCCMPQP-JXAWBTAJSA-N (Z)-dimethomorph Chemical compound C1=C(OC)C(OC)=CC=C1C(\C=1C=CC(Cl)=CC=1)=C/C(=O)N1CCOCC1 QNBTYORWCCMPQP-JXAWBTAJSA-N 0.000 description 1
- HOKKPVIRMVDYPB-UVTDQMKNSA-N (Z)-thiacloprid Chemical compound C1=NC(Cl)=CC=C1CN1C(=N/C#N)/SCC1 HOKKPVIRMVDYPB-UVTDQMKNSA-N 0.000 description 1
- ZAIDIVBQUMFXEC-UHFFFAOYSA-N 1,1-dichloroprop-1-ene Chemical compound CC=C(Cl)Cl ZAIDIVBQUMFXEC-UHFFFAOYSA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical group C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-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
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 1
- HVQHXBNMBZJPLK-UHFFFAOYSA-N 1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-[(2-methylprop-2-en-1-yl)amino]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound CC(=C)CNC1=C([S+]([O-])C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl HVQHXBNMBZJPLK-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
- 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
- PFFIDZXUXFLSSR-UHFFFAOYSA-N 1-methyl-N-[2-(4-methylpentan-2-yl)-3-thienyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound S1C=CC(NC(=O)C=2C(=NN(C)C=2)C(F)(F)F)=C1C(C)CC(C)C PFFIDZXUXFLSSR-UHFFFAOYSA-N 0.000 description 1
- LEZWWPYKPKIXLL-UHFFFAOYSA-N 1-{2-(4-chlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl}imidazole Chemical compound C1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 LEZWWPYKPKIXLL-UHFFFAOYSA-N 0.000 description 1
- FMTFEIJHMMQUJI-NJAFHUGGSA-N 102130-98-3 Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C FMTFEIJHMMQUJI-NJAFHUGGSA-N 0.000 description 1
- HUTNOYOBQPAKIA-UHFFFAOYSA-N 1h-pyrazin-2-one Chemical compound OC1=CN=CC=N1 HUTNOYOBQPAKIA-UHFFFAOYSA-N 0.000 description 1
- YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-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
- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 description 1
- MNHVNIJQQRJYDH-UHFFFAOYSA-N 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-1,2-dihydro-1,2,4-triazole-3-thione Chemical compound N1=CNC(=S)N1CC(C1(Cl)CC1)(O)CC1=CC=CC=C1Cl MNHVNIJQQRJYDH-UHFFFAOYSA-N 0.000 description 1
- AZJQQNWSSLCLJN-UHFFFAOYSA-N 2-ethoxyquinoline Chemical compound C1=CC=CC2=NC(OCC)=CC=C21 AZJQQNWSSLCLJN-UHFFFAOYSA-N 0.000 description 1
- IDPWXVBDDIYDKT-UHFFFAOYSA-N 2-phenoxyquinoline Chemical compound C=1C=C2C=CC=CC2=NC=1OC1=CC=CC=C1 IDPWXVBDDIYDKT-UHFFFAOYSA-N 0.000 description 1
- NNWTYSZJLCDUDC-UHFFFAOYSA-N 2-propoxyquinoline Chemical compound C1=CC=CC2=NC(OCCC)=CC=C21 NNWTYSZJLCDUDC-UHFFFAOYSA-N 0.000 description 1
- BUQPTOSHKHYHHB-UHFFFAOYSA-N 3,5-dichloropyridine-4-carboxylic acid Chemical compound OC(=O)C1=C(Cl)C=NC=C1Cl BUQPTOSHKHYHHB-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
- XTDZGXBTXBEZDN-UHFFFAOYSA-N 3-(difluoromethyl)-N-(9-isopropyl-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl)-1-methylpyrazole-4-carboxamide Chemical compound CC(C)C1C2CCC1C1=C2C=CC=C1NC(=O)C1=CN(C)N=C1C(F)F XTDZGXBTXBEZDN-UHFFFAOYSA-N 0.000 description 1
- OQEBBZSWEGYTPG-UHFFFAOYSA-N 3-aminobutanoic acid Chemical compound CC(N)CC(O)=O OQEBBZSWEGYTPG-UHFFFAOYSA-N 0.000 description 1
- NMWKWBPNKPGATC-UHFFFAOYSA-N 4,5,6,7-tetrachloro-2-benzofuran-1(3H)-one Chemical compound ClC1=C(Cl)C(Cl)=C2COC(=O)C2=C1Cl NMWKWBPNKPGATC-UHFFFAOYSA-N 0.000 description 1
- NHHQOYLPBUYHQU-UHFFFAOYSA-N 4-methylthiadiazole-5-carboxylic acid Chemical compound CC=1N=NSC=1C(O)=O NHHQOYLPBUYHQU-UHFFFAOYSA-N 0.000 description 1
- ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 description 1
- IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 description 1
- WONPUYDAAHCRKZ-UHFFFAOYSA-N 9,10-dioxoanthracene-1,2-dicarbonitrile Chemical compound C1=CC(C#N)=C(C#N)C2=C1C(=O)C1=CC=CC=C1C2=O WONPUYDAAHCRKZ-UHFFFAOYSA-N 0.000 description 1
- 239000005660 Abamectin Substances 0.000 description 1
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 1
- 241000213004 Alternaria solani Species 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 235000016425 Arthrospira platensis Nutrition 0.000 description 1
- 240000002900 Arthrospira platensis Species 0.000 description 1
- 239000005730 Azoxystrobin Substances 0.000 description 1
- 239000005884 Beta-Cyfluthrin Substances 0.000 description 1
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 description 1
- QCFYJCYNJLBDRT-UHFFFAOYSA-N Bis(2-chloro-1-methylethyl)ether Chemical compound ClCC(C)OC(C)CCl QCFYJCYNJLBDRT-UHFFFAOYSA-N 0.000 description 1
- 239000005738 Bixafen Substances 0.000 description 1
- 239000005739 Bordeaux mixture Substances 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- LVDKZNITIUWNER-UHFFFAOYSA-N Bronopol Chemical compound OCC(Br)(CO)[N+]([O-])=O LVDKZNITIUWNER-UHFFFAOYSA-N 0.000 description 1
- 239000005885 Buprofezin Substances 0.000 description 1
- 239000005745 Captan Substances 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- 239000005886 Chlorantraniliprole Substances 0.000 description 1
- 239000005944 Chlorpyrifos Substances 0.000 description 1
- 239000005888 Clothianidin Substances 0.000 description 1
- JJLJMEJHUUYSSY-UHFFFAOYSA-L Copper hydroxide Chemical compound [OH-].[OH-].[Cu+2] JJLJMEJHUUYSSY-UHFFFAOYSA-L 0.000 description 1
- 239000005750 Copper hydroxide Substances 0.000 description 1
- 239000005752 Copper oxychloride Substances 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 239000005889 Cyantraniliprole Substances 0.000 description 1
- 239000005756 Cymoxanil Substances 0.000 description 1
- 239000005946 Cypermethrin Substances 0.000 description 1
- 239000005757 Cyproconazole Substances 0.000 description 1
- 239000005758 Cyprodinil Substances 0.000 description 1
- 239000005892 Deltamethrin Substances 0.000 description 1
- 239000005760 Difenoconazole Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 239000005947 Dimethoate Substances 0.000 description 1
- 239000005761 Dimethomorph Substances 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 239000005897 Etoxazole Substances 0.000 description 1
- 239000005776 Fenhexamid Substances 0.000 description 1
- 239000005777 Fenpropidin 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
- 239000005899 Fipronil Substances 0.000 description 1
- 239000005780 Fluazinam Substances 0.000 description 1
- 239000005901 Flubendiamide Substances 0.000 description 1
- 239000005781 Fludioxonil Substances 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 239000005784 Fluoxastrobin Substances 0.000 description 1
- 239000005788 Fluxapyroxad Substances 0.000 description 1
- 239000005789 Folpet Substances 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000223195 Fusarium graminearum Species 0.000 description 1
- FEACDOXQOYCHKU-UHFFFAOYSA-N Gougerotin Natural products CNCC(=O)NC1=NC(=O)N(C=C1)C2OC(C(O)C(NC(=O)C(N)CO)C2O)C(=O)N FEACDOXQOYCHKU-UHFFFAOYSA-N 0.000 description 1
- 239000005661 Hexythiazox Substances 0.000 description 1
- 239000005794 Hymexazol Substances 0.000 description 1
- 239000005906 Imidacloprid Substances 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- 239000005867 Iprodione Substances 0.000 description 1
- 239000005799 Isopyrazam Substances 0.000 description 1
- 239000005912 Lufenuron Substances 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 239000005951 Methiocarb Substances 0.000 description 1
- 239000005917 Methoxyfenozide Substances 0.000 description 1
- NQRFDNJEBWAUBL-UHFFFAOYSA-N N-[cyano(2-thienyl)methyl]-4-ethyl-2-(ethylamino)-1,3-thiazole-5-carboxamide Chemical compound S1C(NCC)=NC(CC)=C1C(=O)NC(C#N)C1=CC=CS1 NQRFDNJEBWAUBL-UHFFFAOYSA-N 0.000 description 1
- XQJQCBDIXRIYRP-UHFFFAOYSA-N N-{2-[1,1'-bi(cyclopropyl)-2-yl]phenyl}-3-(difluoromethyl)-1-methyl-1pyrazole-4-carboxamide Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1C(C2CC2)C1 XQJQCBDIXRIYRP-UHFFFAOYSA-N 0.000 description 1
- UIQMVEYFGZJHCZ-SSTWWWIQSA-N Nalorphine Chemical compound C([C@@H](N(CC1)CC=C)[C@@H]2C=C[C@@H]3O)C4=CC=C(O)C5=C4[C@@]21[C@H]3O5 UIQMVEYFGZJHCZ-SSTWWWIQSA-N 0.000 description 1
- 241000315044 Passalora arachidicola Species 0.000 description 1
- 239000005813 Penconazole Substances 0.000 description 1
- 239000005816 Penthiopyrad Substances 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
- 239000005818 Picoxystrobin Substances 0.000 description 1
- 239000005923 Pirimicarb Substances 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 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
- 239000005825 Prothioconazole Substances 0.000 description 1
- 239000005925 Pymetrozine Substances 0.000 description 1
- 239000005869 Pyraclostrobin Substances 0.000 description 1
- 239000005663 Pyridaben Substances 0.000 description 1
- 239000005927 Pyriproxyfen Substances 0.000 description 1
- 241001361634 Rhizoctonia Species 0.000 description 1
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 description 1
- UBSLUHFMLMKCCB-UHFFFAOYSA-N S1C=NC=C1.[P] Chemical compound S1C=NC=C1.[P] UBSLUHFMLMKCCB-UHFFFAOYSA-N 0.000 description 1
- 241000221696 Sclerotinia sclerotiorum Species 0.000 description 1
- 239000005834 Sedaxane Substances 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 239000005664 Spirodiclofen Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005935 Sulfuryl fluoride Substances 0.000 description 1
- 239000005839 Tebuconazole Substances 0.000 description 1
- 239000005937 Tebufenozide Substances 0.000 description 1
- 239000005658 Tebufenpyrad Substances 0.000 description 1
- 239000005940 Thiacloprid Substances 0.000 description 1
- 239000005941 Thiamethoxam Substances 0.000 description 1
- 239000005845 Tolclofos-methyl Substances 0.000 description 1
- 239000005857 Trifloxystrobin Substances 0.000 description 1
- QQODLKZGRKWIFG-RUTXASTPSA-N [(R)-cyano-(4-fluoro-3-phenoxyphenyl)methyl] (1S)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(Cl)Cl)[C@@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-RUTXASTPSA-N 0.000 description 1
- WJEIYVAPNMUNIU-UHFFFAOYSA-N [Na].OC(O)=O Chemical class [Na].OC(O)=O WJEIYVAPNMUNIU-UHFFFAOYSA-N 0.000 description 1
- 229950008167 abamectin Drugs 0.000 description 1
- YASYVMFAVPKPKE-UHFFFAOYSA-N acephate Chemical compound COP(=O)(SC)NC(C)=O YASYVMFAVPKPKE-UHFFFAOYSA-N 0.000 description 1
- 238000012271 agricultural production Methods 0.000 description 1
- QGLZXHRNAYXIBU-WEVVVXLNSA-N aldicarb Chemical compound CNC(=O)O\N=C\C(C)(C)SC QGLZXHRNAYXIBU-WEVVVXLNSA-N 0.000 description 1
- 229940024113 allethrin Drugs 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- WFDXOXNFNRHQEC-GHRIWEEISA-N azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000009286 beneficial effect Effects 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
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- LDLMOOXUCMHBMZ-UHFFFAOYSA-N bixafen Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=C(F)C=C1C1=CC=C(Cl)C(Cl)=C1 LDLMOOXUCMHBMZ-UHFFFAOYSA-N 0.000 description 1
- 229930189065 blasticidin Natural products 0.000 description 1
- TXODBIOSWNNKJM-UHFFFAOYSA-N bromophene Chemical compound OC1=C(Br)C=C(Br)C=C1C1=CC(Br)=CC(Br)=C1O TXODBIOSWNNKJM-UHFFFAOYSA-N 0.000 description 1
- 229960003168 bronopol Drugs 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
- JHRWWRDRBPCWTF-OLQVQODUSA-N captafol Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)C(Cl)Cl)C(=O)[C@H]21 JHRWWRDRBPCWTF-OLQVQODUSA-N 0.000 description 1
- 229940117949 captan Drugs 0.000 description 1
- BHKTVMNUHSVTFH-UHFFFAOYSA-N carbamic acid;1h-pyrazole Chemical compound NC(O)=O.C=1C=NNC=1 BHKTVMNUHSVTFH-UHFFFAOYSA-N 0.000 description 1
- JNPZQRQPIHJYNM-UHFFFAOYSA-N carbendazim Chemical compound C1=C[CH]C2=NC(NC(=O)OC)=NC2=C1 JNPZQRQPIHJYNM-UHFFFAOYSA-N 0.000 description 1
- 239000006013 carbendazim Substances 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
- 230000010261 cell growth Effects 0.000 description 1
- PSOVNZZNOMJUBI-UHFFFAOYSA-N chlorantraniliprole Chemical compound CNC(=O)C1=CC(Cl)=CC(C)=C1NC(=O)C1=CC(Br)=NN1C1=NC=CC=C1Cl PSOVNZZNOMJUBI-UHFFFAOYSA-N 0.000 description 1
- CWFOCCVIPCEQCK-UHFFFAOYSA-N chlorfenapyr Chemical compound BrC1=C(C(F)(F)F)N(COCC)C(C=2C=CC(Cl)=CC=2)=C1C#N CWFOCCVIPCEQCK-UHFFFAOYSA-N 0.000 description 1
- HKMOPYJWSFRURD-UHFFFAOYSA-N chloro hypochlorite;copper Chemical compound [Cu].ClOCl HKMOPYJWSFRURD-UHFFFAOYSA-N 0.000 description 1
- AJPXTSMULZANCB-UHFFFAOYSA-N chlorohydroquinone Chemical compound OC1=CC=C(O)C(Cl)=C1 AJPXTSMULZANCB-UHFFFAOYSA-N 0.000 description 1
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical group CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 1
- 229910001956 copper hydroxide Inorganic materials 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 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
- 229940112669 cuprous oxide Drugs 0.000 description 1
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 1
- DVBUIBGJRQBEDP-UHFFFAOYSA-N cyantraniliprole Chemical compound CNC(=O)C1=CC(C#N)=CC(C)=C1NC(=O)C1=CC(Br)=NN1C1=NC=CC=C1Cl DVBUIBGJRQBEDP-UHFFFAOYSA-N 0.000 description 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N cyclobenzothiazole Natural products C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
- 229960001591 cyfluthrin Drugs 0.000 description 1
- QQODLKZGRKWIFG-QSFXBCCZSA-N cyfluthrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-QSFXBCCZSA-N 0.000 description 1
- ZXQYGBMAQZUVMI-UNOMPAQXSA-N cyhalothrin Chemical compound CC1(C)C(\C=C(/Cl)C(F)(F)F)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-UNOMPAQXSA-N 0.000 description 1
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 1
- 229960005424 cypermethrin Drugs 0.000 description 1
- HAORKNGNJCEJBX-UHFFFAOYSA-N cyprodinil Chemical compound N=1C(C)=CC(C2CC2)=NC=1NC1=CC=CC=C1 HAORKNGNJCEJBX-UHFFFAOYSA-N 0.000 description 1
- 229960002483 decamethrin Drugs 0.000 description 1
- OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 description 1
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 1
- 229950001327 dichlorvos Drugs 0.000 description 1
- GJQPMPFPNINLKP-UHFFFAOYSA-N diclofenamide Chemical compound NS(=O)(=O)C1=CC(Cl)=C(Cl)C(S(N)(=O)=O)=C1 GJQPMPFPNINLKP-UHFFFAOYSA-N 0.000 description 1
- 229960005081 diclofenamide Drugs 0.000 description 1
- CDCTYRNLXFEDHC-UHFFFAOYSA-N diethyl (5-methyl-1h-pyrazol-3-yl) phosphate Chemical compound CCOP(=O)(OCC)OC=1C=C(C)NN=1 CDCTYRNLXFEDHC-UHFFFAOYSA-N 0.000 description 1
- BQYJATMQXGBDHF-UHFFFAOYSA-N difenoconazole Chemical compound O1C(C)COC1(C=1C(=CC(OC=2C=CC(Cl)=CC=2)=CC=1)Cl)CN1N=CN=C1 BQYJATMQXGBDHF-UHFFFAOYSA-N 0.000 description 1
- BDYYDXJSHYEDGB-UHFFFAOYSA-N diloxanide furoate Chemical compound C1=CC(N(C(=O)C(Cl)Cl)C)=CC=C1OC(=O)C1=CC=CO1 BDYYDXJSHYEDGB-UHFFFAOYSA-N 0.000 description 1
- 229960003497 diloxanide furoate Drugs 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- YKBZOVFACRVRJN-UHFFFAOYSA-N dinotefuran Chemical compound [O-][N+](=O)\N=C(/NC)NCC1CCOC1 YKBZOVFACRVRJN-UHFFFAOYSA-N 0.000 description 1
- 229960003913 econazole Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- AHPXTXGCMLOXGA-UHFFFAOYSA-N ethyl 4-methylthiadiazole-5-carboxylate Chemical compound CCOC(=O)C=1SN=NC=1C AHPXTXGCMLOXGA-UHFFFAOYSA-N 0.000 description 1
- IXSZQYVWNJNRAL-UHFFFAOYSA-N etoxazole Chemical compound CCOC1=CC(C(C)(C)C)=CC=C1C1N=C(C=2C(=CC=CC=2F)F)OC1 IXSZQYVWNJNRAL-UHFFFAOYSA-N 0.000 description 1
- VDLGAVXLJYLFDH-UHFFFAOYSA-N fenhexamid Chemical compound C=1C=C(O)C(Cl)=C(Cl)C=1NC(=O)C1(C)CCCCC1 VDLGAVXLJYLFDH-UHFFFAOYSA-N 0.000 description 1
- XQUXKZZNEFRCAW-UHFFFAOYSA-N fenpropathrin Chemical compound CC1(C)C(C)(C)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 XQUXKZZNEFRCAW-UHFFFAOYSA-N 0.000 description 1
- 229940013764 fipronil Drugs 0.000 description 1
- UZCGKGPEKUCDTF-UHFFFAOYSA-N fluazinam Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=NC=C(C(F)(F)F)C=C1Cl UZCGKGPEKUCDTF-UHFFFAOYSA-N 0.000 description 1
- ZGNITFSDLCMLGI-UHFFFAOYSA-N flubendiamide Chemical compound CC1=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=C1NC(=O)C1=CC=CC(I)=C1C(=O)NC(C)(C)CS(C)(=O)=O ZGNITFSDLCMLGI-UHFFFAOYSA-N 0.000 description 1
- 229960004884 fluconazole Drugs 0.000 description 1
- RFHAOTPXVQNOHP-UHFFFAOYSA-N fluconazole Chemical compound C1=NC=NN1CC(C=1C(=CC(F)=CC=1)F)(O)CN1C=NC=N1 RFHAOTPXVQNOHP-UHFFFAOYSA-N 0.000 description 1
- MUJOIMFVNIBMKC-UHFFFAOYSA-N fludioxonil Chemical compound C=12OC(F)(F)OC2=CC=CC=1C1=CNC=C1C#N MUJOIMFVNIBMKC-UHFFFAOYSA-N 0.000 description 1
- MBHXIQDIVCJZTD-RVDMUPIBSA-N flufenoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=C(C(F)(F)F)C=C1Cl MBHXIQDIVCJZTD-RVDMUPIBSA-N 0.000 description 1
- UFEODZBUAFNAEU-NLRVBDNBSA-N fluoxastrobin Chemical compound C=1C=CC=C(OC=2C(=C(OC=3C(=CC=CC=3)Cl)N=CN=2)F)C=1C(=N/OC)\C1=NOCCO1 UFEODZBUAFNAEU-NLRVBDNBSA-N 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
- SXSGXWCSHSVPGB-UHFFFAOYSA-N fluxapyroxad Chemical compound FC(F)C1=NN(C)C=C1C(=O)NC1=CC=CC=C1C1=CC(F)=C(F)C(F)=C1 SXSGXWCSHSVPGB-UHFFFAOYSA-N 0.000 description 1
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical compound C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- KGVPNLBXJKTABS-UHFFFAOYSA-N hymexazol Chemical compound CC1=CC(O)=NO1 KGVPNLBXJKTABS-UHFFFAOYSA-N 0.000 description 1
- 229940056881 imidacloprid Drugs 0.000 description 1
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-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
- WLPCAERCXQSYLQ-UHFFFAOYSA-N isotianil Chemical compound ClC1=NSC(C(=O)NC=2C(=CC=CC=2)C#N)=C1Cl WLPCAERCXQSYLQ-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
- 239000005910 lambda-Cyhalothrin Substances 0.000 description 1
- 229960000521 lufenuron Drugs 0.000 description 1
- PWPJGUXAGUPAHP-UHFFFAOYSA-N lufenuron Chemical compound C1=C(Cl)C(OC(F)(F)C(C(F)(F)F)F)=CC(Cl)=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F PWPJGUXAGUPAHP-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- YFBPRJGDJKVWAH-UHFFFAOYSA-N methiocarb Chemical compound CNC(=O)OC1=CC(C)=C(SC)C(C)=C1 YFBPRJGDJKVWAH-UHFFFAOYSA-N 0.000 description 1
- QCAWEPFNJXQPAN-UHFFFAOYSA-N methoxyfenozide Chemical compound COC1=CC=CC(C(=O)NN(C(=O)C=2C=C(C)C=C(C)C=2)C(C)(C)C)=C1C QCAWEPFNJXQPAN-UHFFFAOYSA-N 0.000 description 1
- YNKFZRGTXAPYFD-UHFFFAOYSA-N n-[[2-chloro-3,5-bis(trifluoromethyl)phenyl]carbamoyl]-2,6-difluorobenzamide Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1Cl YNKFZRGTXAPYFD-UHFFFAOYSA-N 0.000 description 1
- 229940079888 nitenpyram Drugs 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- PZXOQEXFMJCDPG-UHFFFAOYSA-N omethoate Chemical compound CNC(=O)CSP(=O)(OC)OC PZXOQEXFMJCDPG-UHFFFAOYSA-N 0.000 description 1
- 229960003483 oxiconazole Drugs 0.000 description 1
- QRJJEGAJXVEBNE-MOHJPFBDSA-N oxiconazole Chemical compound ClC1=CC(Cl)=CC=C1CO\N=C(C=1C(=CC(Cl)=CC=1)Cl)\CN1C=NC=C1 QRJJEGAJXVEBNE-MOHJPFBDSA-N 0.000 description 1
- 235000020232 peanut Nutrition 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
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960003562 phentermine Drugs 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- IBSNKSODLGJUMQ-SDNWHVSQSA-N picoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC(C(F)(F)F)=N1 IBSNKSODLGJUMQ-SDNWHVSQSA-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
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 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
- WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-UHFFFAOYSA-N 0.000 description 1
- ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-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
- QHMTXANCGGJZRX-WUXMJOGZSA-N pymetrozine Chemical compound C1C(C)=NNC(=O)N1\N=C\C1=CC=CN=C1 QHMTXANCGGJZRX-WUXMJOGZSA-N 0.000 description 1
- HZRSNVGNWUDEFX-UHFFFAOYSA-N pyraclostrobin Chemical compound COC(=O)N(OC)C1=CC=CC=C1COC1=NN(C=2C=CC(Cl)=CC=2)C=C1 HZRSNVGNWUDEFX-UHFFFAOYSA-N 0.000 description 1
- DWFZBUWUXWZWKD-UHFFFAOYSA-N pyridaben Chemical compound C1=CC(C(C)(C)C)=CC=C1CSC1=C(Cl)C(=O)N(C(C)(C)C)N=C1 DWFZBUWUXWZWKD-UHFFFAOYSA-N 0.000 description 1
- 239000011677 pyridoxine Substances 0.000 description 1
- 235000008160 pyridoxine Nutrition 0.000 description 1
- NHDHVHZZCFYRSB-UHFFFAOYSA-N pyriproxyfen Chemical compound C=1C=CC=NC=1OC(C)COC(C=C1)=CC=C1OC1=CC=CC=C1 NHDHVHZZCFYRSB-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 229960000329 ribavirin Drugs 0.000 description 1
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 description 1
- 108010048734 sclerotin Proteins 0.000 description 1
- CGVZLUQEQGUVML-UHFFFAOYSA-M sodium;4-methylthiadiazole-5-carboxylate Chemical compound [Na+].CC=1N=NSC=1C([O-])=O CGVZLUQEQGUVML-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- DTDSAWVUFPGDMX-UHFFFAOYSA-N spirodiclofen Chemical compound CCC(C)(C)C(=O)OC1=C(C=2C(=CC(Cl)=CC=2)Cl)C(=O)OC11CCCCC1 DTDSAWVUFPGDMX-UHFFFAOYSA-N 0.000 description 1
- 229940082787 spirulina Drugs 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
- QYPNKSZPJQQLRK-UHFFFAOYSA-N tebufenozide Chemical compound C1=CC(CC)=CC=C1C(=O)NN(C(C)(C)C)C(=O)C1=CC(C)=CC(C)=C1 QYPNKSZPJQQLRK-UHFFFAOYSA-N 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
- QSOHVSNIQHGFJU-UHFFFAOYSA-L thiosultap disodium Chemical compound [Na+].[Na+].[O-]S(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O QSOHVSNIQHGFJU-UHFFFAOYSA-L 0.000 description 1
- MBNMHBAJUNHZRE-UHFFFAOYSA-M thiosultap monosodium Chemical compound [Na+].OS(=O)(=O)SCC(N(C)C)CSS([O-])(=O)=O MBNMHBAJUNHZRE-UHFFFAOYSA-M 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
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 229940011671 vitamin b6 Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
- C07D231/26—1-Phenyl-3-methyl-5- pyrazolones, unsubstituted or substituted on the phenyl ring
-
- 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
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
本发明属于农药技术领域，具体涉及一种3‑(3,3‑二氯烯丙氧基)‑1‑苯基吡唑‑5‑甲酰胺衍生物及其制备方法和包含上述衍生物的农药组合物。本发明3‑(3,3‑二氯烯丙氧基)‑1‑苯基吡唑‑5‑甲酰胺衍生物抑菌活性高，适用于农业领域、林业领域以及园艺领域的植物病害和病毒病害的防治，有效的防治农作物病虫害。
Description
技术领域
本发明属于农药技术领域，具体涉及一种3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物及其制备方法和包括上述衍生物的农药组合物。
背景技术
含氮杂环类化合物具有较高的生理和药理活性，在农药的开发中具有重要价值，其中吡唑为含有两个氮原子的1,2-二氮唑五元杂环。含吡唑环的化合物具有较高的生物活性，从1946年Thmaposon第一次报道了2-吡唑-5-酮可以抑制生物生长及1949年美国Rubber公司合成了吡唑类的叶面喷洒杀菌剂之后，吡唑类化合物在农药领域取得了飞速发展，例如Geigy.s. A.公司于1952年把吡唑环引入氨基甲酸酯、有机磷制备了吡唑威、异索威、吡唑硫磷、吡唑氧磷和敌蝇威等农用杀虫剂。
而近年，商品化或即将商品化的含吡唑杂环的农药品种更加众多，特别是近年迅猛发展起来的吡唑酰胺类杀菌剂，拜耳司开发的吡唑酰胺杀菌剂Bixafen,先正达发现并开发的 Isopyrazam,巴斯夫公司公布的化合物fluxapyroxad和先正达处于研究开发后期的杀菌剂 Sedaxane(张一宾，世界农药，2014,4(36):31-33.)，这些农药品种的共同特点是含有吡唑杂环的酰胺类化合物，具有较高的杀菌活性。
发明内容
本发明的目的之一在于提供一种3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物，生物活性高。
本发明的目的之二在于提供上述的3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物的制备方法。
本发明的目的之三还在于提供一种农药组合物，包括上述的3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-苯酰胺衍生物。
为实现上述目的，本发明采用如下技术方案：
一种3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物，化学结构通式如下：
其中，R为异丙基、环己基、3-甲基苯基、4-甲基苯基、3-甲氧基苯基、4-甲氧基苯基、2-氟苯基、3-氟苯基、4-溴苯基、4-三氟甲基苯基、吡啶-2-基或者2-对氟苯基苯基。
一种上述的3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物的制备方法，包括以下步骤：
(1)5-氧代吡唑烷-2-苯基-3-羧酸乙酯的制备：
a.向三口圆底烧瓶中加入35～45mL无水乙醇，分批加入25～35mmol金属钠，搅拌10～15min，形成乙醇钠溶液，接着加入28～32mmol苯肼形成黄色悬浊液，加热60～70 ℃至回流，回流状态下滴加28～32mmol马来酸二乙酯，滴毕，继续回流0.8～1.2h；
b.反应结束后，反应液冷却至35～45℃，加入25～35mmol冰乙酸，反应液浓缩至干，即得5-氧代吡唑烷-2-苯基-3-羧酸乙酯；
(2)1-苯基-3-羟基-吡唑-5-甲酸乙酯的制备：
向单口圆底烧瓶中加入40～45mmol 5-氧代吡唑烷-2-苯基-3-羧酸乙酯，90～110mL乙腈，3～5mL 98wt％浓硫酸，搅拌5～10min，之后加入45～52mmol K2S2O8，搅拌回流5～5.5h，冷却至室温，得到褐色溶液，浓缩，所得残余物柱层析纯化，得到黄色固体1-苯基-3-羟基-吡唑-5-甲酸乙酯；
(3)3-(3,3-二氯丙烯氧基)-1-苯基吡唑5-甲酸乙酯的制备：
将0.8～1.2mmol 1-苯基-3-羟基吡唑-5-甲酸乙酯，1.2～1.5mmol 1,1,3-三氯丙烯，丙酮 3～5mL混合，碱性条件下室温缩合反应12～16h，过滤，浓缩，所得残余物柱层析纯化，得到红棕色油状物3-(3,3-二氯丙烯氧基)-1-苯基吡唑5-甲酸乙酯；
(4)3-(3,3-二氯丙烯氧基)-1-苯基吡唑-5-甲酸的制备：
c.向0.8～1.0mmol 3-(3,3-二氯丙烯氧基)-1-苯基吡唑5-甲酸乙酯中加入2～3mmol氢氧化锂，用5～8mL的甲醇溶液溶解，室温搅拌回流10～15h；
d.反应结束后，浓缩，加入蒸馏水，减压过滤除去无机盐，水相用盐酸酸化至pH3.8～4.2，有白色沉淀生成，减压过滤，将滤饼干燥，即的产物3-(3,3-二氯丙烯氧基)-1-苯基吡唑-5-甲酸；
(5)3-(3,3-二氯丙烯氧基)-1-苯基-吡唑-5-甲酰氯的制备：
将0.5～0.7mmol3-(3,3-二氯丙烯氧基)-1-苯基吡唑-5-甲酸加入圆底烧瓶中，加入4～6 mL氯仿，滴加0.15～0.25mL氯化亚砜，50～60℃搅拌3～4h，反应结束后减压蒸馏，得到淡黄色固体3-(3,3-二氯丙烯氧基)-1-苯基-吡唑-5-甲酰氯；
(6)3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物的制备：
e.将0.8～1.2mmol 3-(3,3-二氯丙烯氧基)-1-苯基-吡唑-5-甲酰氯的溶解在1.5～2.5mL 四氢呋喃溶液中，在反应瓶中加入1.1～1.3mmol对应的有机胺、4～6mL二氯甲烷、1.5～ 1.7mmol三乙胺，冷却至-2～0℃，惰性气体保护下滴加上述四氢呋喃溶液，滴加完毕逐渐升至室温，搅拌1～1.5h；
f.反应结束后，反应液用8～12mL二氯甲烷稀释，洗涤，干燥，浓缩，所得残余物胶柱层析纯化，得到3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物。
根据上述的3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物的制备方法，步骤(3) 所述的碱性条件为：1.5～2mmol K2CO3和0.01～0.05mmol KI。
根据上述的3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物的制备方法，步骤(2) 所述的柱层析条件为：200～300目硅胶柱，洗脱剂为石油醚和乙酸乙酯的混合物，两者的体积比为3:1。
根据上述的3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物的制备方法，步骤(3) 所述的柱层析条件为：200～300目硅胶柱，洗脱剂为石油醚和乙酸乙酯的混合物，两者的体积比为5:1。
根据上述的3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物的制备方法，步骤(6) 所述的柱层析条件为：200～300目硅胶硅，洗脱剂为石油醚和乙酸乙酯的混合物，两者的体积比为3:1～10:1。
根据上述的3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物的制备方法，所述的石油醚沸点为60～90℃。
根据上述的3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物的制备方法，步骤(6) 所述的洗涤溶液为稀盐酸、饱和碳酸氢钠溶液和饱和食盐水。
上述制备方法的反应通式表示如下：
一种农药组合物，包括上述的3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物。
根据上述的农药组合物，还包括农药杀虫剂，所述的农药杀虫剂为毒死蜱、地亚哝、啶虫脒、甲氨基阿维菌素、弥拜菌素、阿维菌素、多杀菌素、氰戊菊酯、高效氰戊菊酯、氯氰菊酯、高效氯氰菊酯、三氟氯氰菊酯、溴氰菊酯、甲氰菊酯、Beta-氟氯氰菊酯、氟氯氰菊酯、Lambda-三氟氯氰菊酯、二氯苯醚菊酯、苄氯菊酯、丙烯菊酯、功夫菊酯、联苯菊酯、氯菊酯、醚菊酯、氟氯苯菊酯、氯氟胺氰戊菊酯、吡虫啉、啶虫脒、烯啶虫胺、氯噻啉、噻虫啉、噻虫嗪、噻虫胺、呋虫胺、可尼丁、达特南、除虫脲、灭幼脲、伏虫隆、除虫隆、氟铃脲、氟虫脲、啶虫隆、虱螨脲、毒虫脲、氟幼脲、Noviflumuron即多氟脲、氟螨脲、 Novaluron即双苯氟脲、氟啶脲、Bay sir 6874即{1-[(3.5-二氯-4)4-硝基苯氧基苯基3-3-(2-氯苯)-脲}、Bay SIR-8514即[1-(4-三氟甲氧基苯基)-3-(2-氯苯)-脲]、嗪虫脲、Bistrifluron即双三氟虫脲、呋喃虫酰肼、虫酰肼、氯虫酰肼、甲氧虫酰肼、环虫酰肼、乐果、氧化乐果、敌敌畏、乙酰甲胺磷、三唑磷、喹硫磷、哒嗪硫磷、氯唑磷、叶蝉散、西维因、抗蚜威、速灭威、异丙威、杀螟丹、仲丁威、叶飞散、甲萘威、丙硫克百威、丁硫克百威、杀螟丹、溴螨酯、噻螨酮、唑螨酯、哒螨酮、四螨嗪、炔螨特、丁醚脲、丙硫克百威、吡蚜酮、螺螨酯、螺虫酯、螺虫乙酯、丁烯氟虫腈、三唑锡、噻嗪酮、灭线磷、氟虫腈、杀虫单、杀虫双、氯虫酰胺、氟虫酰胺、氟氰虫酰胺、氰虫酰胺、唑虫酰胺、吡螨胺、溴虫腈、吡嗪酮、乙螨唑、吡螨胺、哒幼酮、吡丙醚、埃玛菌素中一种或几种的混合。
根据上述的农药组合物，还包括农药杀菌剂，所述的农药杀菌剂为苯并噻二唑、噻酰菌胺、噻酰胺、甲噻诱胺、4-甲基-1,2,3-噻二唑-5-甲酸、4-甲基-1,2,3-噻二唑-5-甲酸钠、4-甲基-1,2,3-噻二唑-5-甲酸乙酯、DL-β-氨基丁酸、异噻菌胺、病毒唑、安托芬、宁南霉素或水杨酸、霜脲氰、福美双、福美锌、代森锰锌、乙磷铝、甲基硫菌灵、百菌清、敌可松、腐霉利、苯锈啶、甲基托布津、托布津、精甲霜灵、水杨酸、氟吗啉、烯酰吗啉、高效甲霜灵、高效苯霜灵、双氯氰菌胺、磺菌胺、甲磺菌胺、噻氟菌胺、氟酰胺、叶枯酞、环丙酰菌胺、环氟菌胺、环酰菌胺、氰菌胺、硅噻菌胺、呋吡菌胺、吡噻菌胺、双炔酰菌胺、苯酰菌胺、甲呋酰胺、萎锈灵、乙菌利、异菌脲、嘧菌酯、醚菌胺、氟嘧菌酯、醚菌酯、苯氧菌胺、肟醚菌胺、啶氧菌酯、唑菌胺酯、肟菌酯、烯肟菌酯、烯肟菌胺、氧环唑、糠菌唑、环丙唑醇、苯醚甲环唑、烯唑醇、高效烯唑醇、氟环唑、腈苯唑、氟喹唑、氟硅唑、粉唑醇、己唑醇、亚胺唑、种菌唑、叶菌唑、腈菌唑、戊菌唑、丙环唑、丙硫菌唑、硅氟唑、戊唑醇、四氟醚唑、三唑醇、灭菌唑、联苯三唑醇、噻菌灵、麦穗宁、抑霉唑、高效抑霉唑、咪鲜胺、氟菌唑、氰霜唑、咪唑菌酮、噁咪唑、稻瘟酯、噁唑菌酮、啶菌噁唑、噁霉灵、噁霜灵、噻唑菌胺、土菌灵、辛噻酮、苯噻硫氰、十二环吗啉、丁苯吗啉、十三吗啉、拌种咯、咯菌腈、氟啶胺、啶斑肟、环啶菌胺、啶酰菌胺、氟啶酰菌胺、啶菌胺、嘧菌环胺、氟嘧菌胺、嘧菌腙、嘧菌胺、嘧霉胺、氯苯嘧啶醇、氟苯嘧啶醇、灭螨猛、二氰蒽醌、乙氧喹啉、羟基喹啉、丙氧喹啉、苯氧喹啉、乙霉威、异丙菌胺、苯噻菌胺、霜霉威、磺菌威、敌瘟磷、异稻瘟净、吡菌磷、甲基立枯磷、灭瘟素、春雷霉素、多抗霉素、多氧霉素、有效霉素、井冈霉素、链霉素、甲霜灵、呋霜灵、苯霜灵、呋酰胺、灭锈胺、多菌灵、苯菌灵、甲基硫菌灵、三唑酮、乙嘧酚磺酸酯、二甲嘧酚、乙嘧酚、敌菌丹、克菌丹、灭菌丹、乙烯菌核利、氟氯菌核利、菌核净、百菌清、稻瘟灵、稻瘟净、叶枯唑、五氯硝基苯、代森锰锌、丙森锌、三乙膦酸铝、硫磺、波尔多液、硫酸铜、氧氯化铜、氧化亚铜、氢氧化铜、苯菌酮、戊菌隆、哒菌酮、四氯苯酞、咯喹酮、螺环菌胺、三环唑、嗪胺灵、多果啶、双胍辛盐、双胍辛胺、氯硝胺、苯磺菌胺、甲苯磺菌胺、吲哚酯、敌磺钠、喹菌酮、烯丙苯噻唑、溴硝醇、碘甲烷、威百亩、敌线酯、棉隆、二氯异丙醚、噻唑磷、硫线磷、丰索磷、虫线磷、苯线磷、灭线磷、除线磷、氯唑磷、丁硫环磷、杀线威、涕灭威、克百威、硫酰氟、二氯丙烯、二氯异烟酸、烯丙异噻唑等其它已知任何可作为杀菌剂中的任意一种或几种的混合。
本发明的积极有益效果：
本发明3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物抑菌活性高，适用于农业领域、林业领域以及园艺领域的植物病害和病毒病害的防治，有效的防治农作物病虫害。
本发明3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物化学收率高，纯度高，制备方法简单，生产成本低，易于操作。
具体实施方式
实施例1
一种3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物，化学结构通式I如下：
其中，R为异丙基。
上述的3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物的制备方法包括以下步骤：
(1)5-氧代吡唑烷-2-苯基-3-羧酸乙酯的制备：
a.向三口烧瓶中加入40mL无水乙醇，分批加入30mmol金属钠，搅拌10min，形成乙醇钠溶液，接着加入30mmol苯肼形成黄色悬浊液，加热70℃至回流，回流状态下滴加30mmol马来酸二乙酯，滴毕，继续回流1h；
b.反应结束后，反应液冷却至40℃，加入30mmol冰乙酸，反应液浓缩至干，即得 5-氧代吡唑烷-2-苯基-3-羧酸乙酯，收率90％，纯度≥93％；
(2)1-苯基-3-羟基-吡唑-5-甲酸乙酯的制备：
向单口圆底烧瓶中加入43mmol 5-氧代吡唑烷-2-苯基-3-羧酸乙酯，100mL乙腈，4mL 98wt％浓硫酸，搅拌5min，之后加入48mmol K2S2O8，搅拌回流5h，冷却至室温，得到褐色溶液，浓缩，所得残余物柱层析纯化，洗脱，得到黄色固体1-苯基-3-羟基-吡唑-5-甲酸乙酯，收率75％，纯度≥95％，1H NMR(400MHz,CDCl3)：δ:7.47(d,J＝7.5Hz,4H),7.44– 7.35(m,3H),7.26(s,2H),6.32(s,1H),4.22(d,J＝7.1Hz,2H),1.22(t,J＝7.1Hz,3H)；
(3)3-(3,3-二氯丙烯氧基)-1-苯基吡唑5-甲酸乙酯的制备：
将1mmol 1-苯基-3-羟基吡唑-5-甲酸乙酯，1.2mmol 1,1,3-三氯丙烯，丙酮4mL混合，碱性条件下室温缩合反应15h，过滤，浓缩，所得残余物柱层析纯化，洗脱，得到红棕色油状物3-(3,3-二氯丙烯氧基)-1-苯基吡唑5-甲酸乙酯，收率80％，纯度≥95％，1H NMR(400MHz,CDCl3)：δ:7.98–7.32(m,9H),7.26(s,1H),6.42(s,1H),6.24(t,J＝6.5Hz,1H),4.86(d,J ＝6.5Hz,3H),4.23(q,J＝7.1Hz,3H),1.24(t,J＝8.9,5.4Hz,3H)；
(4)3-(3,3-二氯丙烯氧基)-1-苯基吡唑-5-甲酸的制备：
c.向0.9mmol 3-(3,3-二氯丙烯氧基)-1-苯基吡唑5-甲酸乙酯中加入2.5mmol氢氧化锂，用5mL的甲醇溶液溶解，室温搅拌回流12h；
d.反应结束后，浓缩除去大部分溶剂，加入蒸馏水，减压过滤除去无机盐，水相用1mol/L的盐酸酸化至pH为4，有白色沉淀生成，减压过滤，将滤饼干燥，即的产物3-(3,3- 二氯丙烯氧基)-1-苯基吡唑-5-甲酸，收率90％，纯度≥95％，1H NMR(400MHz,CDCl3)：δ:7.98–7.32(m,9H),7.26(s,1H),6.42(s,1H),6.24(t,J＝6.5Hz,1H),4.86(d,J＝6.5Hz,3H), 4.23(q,J＝7.1Hz,3H),1.24(t,J＝8.9,5.4Hz,3H)；
(5)3-(3,3-二氯丙烯氧基)-1-苯基-吡唑-5-甲酰氯的制备：
将0.6mmol3-(3,3-二氯丙烯氧基)-1-苯基吡唑-5-甲酸加入圆底烧瓶中，加入5mL氯仿，滴加0.2mL氯化亚砜，50℃搅拌3h，反应结束后减压蒸馏，得到淡黄色固体3-(3,3- 二氯丙烯氧基)-1-苯基-吡唑-5-甲酰氯；
(6)3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物的制备：
e.将1.0mmol 3-(3,3-二氯丙烯氧基)-1-苯基-吡唑-5-甲酰氯的溶解在2mL四氢呋喃溶液中，在反应瓶中加入1.2mmol对应的有机胺、5mL二氯甲烷、1.5mmol三乙胺，冷却至0 ℃，惰性气体保护下滴加上述四氢呋喃溶液，滴加完毕逐渐升至室温，搅拌1h；
f.反应结束后，反应液用10mL二氯甲烷稀释，洗涤，干燥，浓缩，所得残余物柱层析纯化，洗脱，得到3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物，产品纯度≥97％。
步骤(3)所述的碱性条件为：1.5mmol K2CO3和0.05mmol KI。
步骤(2)所述的柱层析条件为：200～300目硅胶柱，洗脱剂为石油醚和乙酸乙酯的混合物，两者的体积比为3:1。
步骤(3)所述的柱层析条件为：200～300目硅胶柱，洗脱剂为石油醚和乙酸乙酯的混合物，两者的体积比为5:1。
步骤(6)所述的柱层析条件为：200～300目硅胶柱，洗脱剂为石油醚和乙酸乙酯的混合物，两者的体积比为5:1。
所述的石油醚沸点为60～90℃。
步骤(6)所述的洗涤溶液为稀盐酸、饱和碳酸氢钠溶液和饱和食盐水。
实施例2～12与上述实施例基本原理类似，不重述，有些不同的是：R分别为环己基、 3-甲基苯基、4-甲基苯基、3-甲氧基苯基、4-甲氧基苯基、2-氟苯基、3-氟苯基、4-溴苯基、 4-三氟甲基苯基、吡啶-2-基、2-对氟苯基苯基。
实施例2～12的3-(3,3-二氯烯丙氧基)-1-甲基吡唑-5-甲酰胺衍生物的制备方法与实施例 1相似，相同之处不重述，有些不同的是，步骤(6)所述的有机胺R-NH2分别与所述的R 基团相对应。
上述实施例1～12制备的3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物的理化参数见表1。
表1本发明实施例1～12制备的3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物理化参数
本发明的实施例1～12所述的3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物抑制病原真菌生长活性的测定实验：
测试方法：菌体生长率测定法。
具体过程是：(1)取5mg实施例1～12任意所述的3-(3,3-二氯烯丙氧基)-1-苯基吡唑- 5-甲酰胺衍生物溶解在适量二甲基甲酰胺内，然后用含有一定量吐温20乳化剂水溶液稀释至500μg/mL的药剂，将供试药剂在无菌条件下各吸取1mL注入培养皿内，再分别加入9毫升培养基，摇匀后制成50μg/mL含药平板，以添加1mL灭菌水的平板做空白对照。
(2)用直径4mm的打孔器沿菌丝外缘切取菌盘，移至含药平板上，呈等边三角形摆放，每处理重复3次，将培养皿放在24±1℃恒温培养箱内培养，待对照菌落直径扩展到2～3cm后，调查各处理菌盘扩展直径，求平均值，与空白对照比较，计算相对抑菌率。
供试菌种：代表农业生产中田间发生的大部分病原菌的种属，AS：番茄早疫病菌(Alternaria solani)；BC：黄瓜灰霉病菌(Botrytis cinerea)；CA：花生褐斑病菌(Cercospora arachidicola)；GZ：小麦赤霉病菌(Gibberella zeae)；PI：马铃薯晚疫病菌(Phytophthora infestans(Mont.)de Bary)；PP：苹果轮纹病菌(Physalosporapiricola)；PS：水稻纹枯病菌 (Pellicularia sasakii)；RC：禾谷丝核菌(Rhizoctoniacerealis)；SS：油菜菌核病菌(Sclerotinia sclerotiorum)。
实验结果见表2。
表2 3-(3,3-二氯烯丙氧基)-1-甲基吡唑-5-甲酰胺衍生物的抑菌率检测结果/％
| 化合物 | PI | CA | AS | BC | GZ | PP | SS | RC | PS |
| Mg-P-01 | 33 | 44 | 29 | 67 | 45 | 443 | 32 | 66 | 34 |
| Mg-P-02 | 22 | 57 | 28 | 69 | 12 | 37 | 10 | 23 | 13 |
| Mg-P-03 | 66 | 43 | 22 | 38 | 50 | 39 | 50 | 59 | 13 |
| Mg-P-04 | 17 | 71 | 61 | 38 | 23 | 30 | 0 | 45 | 19 |
| Mg-P-05 | 24 | 50 | 22 | 38 | 26 | 45 | 5 | 77 | 13 |
| Mg-P-06 | 32 | 71 | 39 | 58 | 38 | 46 | 15 | 41 | 19 |
| Mg-P-07 | 56 | 57 | 56 | 73 | 12 | 39 | 25 | 27 | 13 |
| Mg-P-08 | 7 | 36 | 11 | 19 | 53 | 33 | 25 | 32 | 13 |
| Mg-P-09 | 7 | 21 | 28 | 35 | 47 | 39 | 30 | 41 | 13 |
| Mg-P-10 | 15 | 43 | 11 | 19 | 47 | 46 | 55 | 82 | 25 |
| Mg-P-11 | 55 | 60 | 34 | 56 | 45 | 60 | 60 | 54 | 43 |
| Mg-P-12 | 47 | 63 | 50 | 63 | 23 | 34 | 50 | 37 | 30 |
结果分析：由表2可以看出，本发明实施例1～12的3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物抑菌效果好。
Claims (9)
1.一种3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物，化学结构通式如下：
R为异丙基、环己基、3-甲基苯基、3-甲氧基苯基、4-甲氧基苯基、3-氟苯基、4-三氟甲基苯基、吡啶-2-基或者2-对氟苯基苯基。
2.一种权利要求1所述的3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物的制备方法，包括以下步骤：
(1)5-氧代吡唑烷-2-苯基-3-羧酸乙酯的制备：
a.向三口圆底烧瓶中加入35～45mL无水乙醇，分批加入25～35mmol金属钠，搅拌10～15min，形成乙醇钠溶液，接着加入28～32mmol苯肼形成黄色悬浊液，加热60～70℃至回流，回流状态下滴加28～32mmol马来酸二乙酯，滴毕，继续回流0.8～1.2h；
b.反应结束后，反应液冷却至35～45℃，加入25～35mmol冰乙酸，反应液浓缩至干，即得5-氧代吡唑烷-2-苯基-3-羧酸乙酯；
(2)1-苯基-3-羟基-吡唑-5-甲酸乙酯的制备：
向单口圆底烧瓶中加入40～45mmol 5-氧代吡唑烷-2-苯基-3-羧酸乙酯，90～110mL乙腈，3～5mL 98wt％浓硫酸，搅拌5～10min，之后加入45～52mmol K2S2O8，搅拌回流5～5.5h，冷却至室温，得到褐色溶液，浓缩，所得残余物柱层析纯化，得到黄色固体1-苯基-3-羟基-吡唑-5-甲酸乙酯；
(3)3-(3,3-二氯丙烯氧基)-1-苯基吡唑5-甲酸乙酯的制备：
将0.8～1.2mmol 1-苯基-3-羟基吡唑-5-甲酸乙酯，1.2～1.5mmol 1,1,3-三氯丙烯，丙酮3～5mL混合，碱性条件下室温缩合反应12～16h，过滤，浓缩，所得残余物柱层析纯化，得到红棕色油状物3-(3,3-二氯丙烯氧基)-1-苯基吡唑5-甲酸乙酯；
(4)3-(3,3-二氯丙烯氧基)-1-苯基吡唑-5-甲酸的制备：
c.向0.8～1.0mmol 3-(3,3-二氯丙烯氧基)-1-苯基吡唑5-甲酸乙酯中加入2～3mmol氢氧化锂，用5～8mL的甲醇溶液溶解，室温搅拌回流10～15h；
d.反应结束后，浓缩，加入蒸馏水，减压过滤除去无机盐，水相用盐酸酸化至pH 3.8～4.2，有白色沉淀生成，减压过滤，将滤饼干燥，即得产物3-(3,3-二氯丙烯氧基)-1-苯基吡唑-5-甲酸；
(5)3-(3,3-二氯丙烯氧基)-1-苯基-吡唑-5-甲酰氯的制备：
将0.5～0.7mmol3-(3,3-二氯丙烯氧基)-1-苯基吡唑-5-甲酸加入圆底烧瓶中，加入4～6mL氯仿，滴加0.15～0.25mL氯化亚砜，50～60℃搅拌3～4h，反应结束后减压蒸馏，得到淡黄色固体3-(3,3-二氯丙烯氧基)-1-苯基-吡唑-5-甲酰氯；
(6)3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物的制备：
e.将0.8～1.2mmol 3-(3,3-二氯丙烯氧基)-1-苯基-吡唑-5-甲酰氯的溶解在1.5～2.5mL四氢呋喃溶液中，在反应瓶中加入1.1～1.3mmol对应的有机胺、4～6mL二氯甲烷、1.5～1.7mmol三乙胺，冷却至-2～0℃，惰性气体保护下滴加上述四氢呋喃溶液，滴加完毕逐渐升至室温，搅拌1～1.5h；
f.反应结束后，反应液用8～12mL二氯甲烷稀释，洗涤，干燥，浓缩，所得残余物柱层析纯化，得到3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物。
3.根据权利要求2所述的3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物的制备方法，其特征在于，步骤(3)所述的碱性条件为：1.5～2mmol K2CO3和0.01～0.05mmol KI。
4.根据权利要求2所述的3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物的制备方法，其特征在于，步骤(2)所述的柱层析条件为：200～300目硅胶柱，洗脱剂为石油醚和乙酸乙酯的混合物，两者的体积比为3:1。
5.根据权利要求2所述的3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物的制备方法，其特征在于，步骤(3)所述的柱层析条件为：200～300目硅胶柱，洗脱剂为石油醚和乙酸乙酯的混合物，两者的体积比为5:1。
6.根据权利要求2所述的3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物的制备方法，其特征在于，步骤(6)所述的柱层析条件为：200～300目硅胶柱，洗脱剂为石油醚和乙酸乙酯的混合物，两者的体积比为3:1～10:1。
7.根据权利要求4～6任一项所述的3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物的制备方法，其特征在于，所述的石油醚沸点为60～90℃。
8.根据权利要求2所述的3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物的制备方法，其特征在于，步骤(6)所述的洗涤溶液为稀盐酸、饱和碳酸氢钠溶液和饱和食盐水。
9.一种农药组合物，其特征在于，包括权利要求1所述的3-(3,3-二氯烯丙氧基)-1-苯基吡唑-5-甲酰胺衍生物。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510495921.4A CN105175336B (zh) | 2015-08-13 | 2015-08-13 | 一种3‑(3,3‑二氯烯丙氧基)‑1‑苯基吡唑‑5‑甲酰胺衍生物及其制备方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510495921.4A CN105175336B (zh) | 2015-08-13 | 2015-08-13 | 一种3‑(3,3‑二氯烯丙氧基)‑1‑苯基吡唑‑5‑甲酰胺衍生物及其制备方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105175336A CN105175336A (zh) | 2015-12-23 |
| CN105175336B true CN105175336B (zh) | 2017-11-03 |
Family
ID=54897857
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510495921.4A Expired - Fee Related CN105175336B (zh) | 2015-08-13 | 2015-08-13 | 一种3‑(3,3‑二氯烯丙氧基)‑1‑苯基吡唑‑5‑甲酰胺衍生物及其制备方法 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105175336B (zh) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110396079A (zh) * | 2019-06-12 | 2019-11-01 | 东南大学 | 一种氯虫苯甲酰胺中间体的制备方法及其应用 |
| CN115028582B (zh) * | 2022-06-23 | 2024-04-12 | 曲靖师范学院 | 一种n-芳基吡唑类药物e-52862的制备方法及其产品 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1711255A (zh) * | 2002-11-15 | 2005-12-21 | 杜邦公司 | 新的邻氨基苯甲酰胺杀虫剂 |
| WO2010003350A1 (zh) * | 2008-07-07 | 2010-01-14 | 中国中化集团公司 | 1-取代吡啶基-吡唑酰胺类化合物及其应用 |
| CN101659655A (zh) * | 2009-09-15 | 2010-03-03 | 南开大学 | 一类吡唑酰胺衍生物及其应用 |
| CN104725348A (zh) * | 2013-05-20 | 2015-06-24 | 江苏省农药研究所股份有限公司 | 邻氨基苯甲酰烷基异(硫)脲类化合物及其合成方法和应用 |
-
2015
- 2015-08-13 CN CN201510495921.4A patent/CN105175336B/zh not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1711255A (zh) * | 2002-11-15 | 2005-12-21 | 杜邦公司 | 新的邻氨基苯甲酰胺杀虫剂 |
| WO2010003350A1 (zh) * | 2008-07-07 | 2010-01-14 | 中国中化集团公司 | 1-取代吡啶基-吡唑酰胺类化合物及其应用 |
| CN101659655A (zh) * | 2009-09-15 | 2010-03-03 | 南开大学 | 一类吡唑酰胺衍生物及其应用 |
| CN104725348A (zh) * | 2013-05-20 | 2015-06-24 | 江苏省农药研究所股份有限公司 | 邻氨基苯甲酰烷基异(硫)脲类化合物及其合成方法和应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105175336A (zh) | 2015-12-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101522672B (zh) | 杀虫的异噁唑啉类化合物 | |
| CN105492432A (zh) | 四唑啉酮化合物及其用途 | |
| UA119972C2 (uk) | Заміщені бензаміди для боротьби з членистоногими | |
| CN107531700A (zh) | 介离子化合物 | |
| MX2009000144A (es) | Agente de control de plaga que contiene derivado de piridil-metanamina novedoso o su sal. | |
| CN105061396B (zh) | 一种酰胺衍生物及其制备方法 | |
| JP2012102089A (ja) | ピリミジン化合物およびその有害生物防除用途 | |
| CN110128419A (zh) | 一类二氟吡唑杂环甲酰胺类衍生物及其制备方法和用途 | |
| CN105175336B (zh) | 一种3‑(3,3‑二氯烯丙氧基)‑1‑苯基吡唑‑5‑甲酰胺衍生物及其制备方法 | |
| US20110195930A1 (en) | Pyridine derivative or its salt, pesticide containing it and process for its production | |
| TWI771410B (zh) | N-(4-吡啶基)菸鹼醯胺化合物或其鹽 | |
| CN105175335B (zh) | 一种3‑(3,3‑二氯烯丙氧基)‑1‑甲基吡唑‑5‑甲酰胺衍生物及其制备方法 | |
| WO2017222037A1 (ja) | Ｎ－（４－ピリジル）ベンズアミド化合物又はその塩、及び該化合物又はその塩を有効成分として含有する有害生物防除剤 | |
| JP7111731B2 (ja) | ピリドン化合物およびそれを有効成分とする農園芸用殺菌剤 | |
| CN104470897A (zh) | 吡啶化合物和农园艺用杀菌剂 | |
| TW201127291A (en) | Diaryltriazole derivative or its salt; insecticide, miticide, nematicide or soil pesticide containing it; and process for its production | |
| CN107602547A (zh) | 一类杂环三唑衍生物及其制备方法和用途 | |
| JP2016204325A (ja) | 有害生物防除剤 | |
| CN104031026B (zh) | 一类含n‑氰基砜(硫)亚胺的邻甲酰氨基苯甲酰胺衍生物及其制备方法和用途 | |
| JP2017008029A (ja) | Ｎ−（４−ピリジル）ピコリンアミド化合物又はその塩を有効成分として含有する有害生物防除剤 | |
| JP2019131470A (ja) | Ｎ−（４−ピリジル）ベンズアミド化合物又はその塩を有効成分として含有する有害生物防除剤 | |
| CN108640887B (zh) | 一类杂环吗啉类衍生物及其制备方法和用途 | |
| TW202000657A (zh) | 取代吡啶化合物或其鹽 | |
| JP2023137573A (ja) | チアゾールカルボン酸ヒドラジド化合物を含有する殺菌組成物 | |
| JP2018197192A (ja) | チエノピロール系化合物又はその塩を有効成分として含有する有害生物防除剤 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20171103 Termination date: 20180813 |