CN114728930A - 7-嘧啶-2-基-氧基-吲唑衍生物及其作为除草剂的用途 - Google Patents
7-嘧啶-2-基-氧基-吲唑衍生物及其作为除草剂的用途 Download PDFInfo
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- CN114728930A CN114728930A CN202080079108.8A CN202080079108A CN114728930A CN 114728930 A CN114728930 A CN 114728930A CN 202080079108 A CN202080079108 A CN 202080079108A CN 114728930 A CN114728930 A CN 114728930A
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- DNUAYCRATWAJQE-UHFFFAOYSA-N flufenpyr-ethyl Chemical group C1=C(Cl)C(OCC(=O)OCC)=CC(N2C(C(C)=C(C=N2)C(F)(F)F)=O)=C1F DNUAYCRATWAJQE-UHFFFAOYSA-N 0.000 description 1
- FOUWCSDKDDHKQP-UHFFFAOYSA-N flumioxazin Chemical compound FC1=CC=2OCC(=O)N(CC#C)C=2C=C1N(C1=O)C(=O)C2=C1CCCC2 FOUWCSDKDDHKQP-UHFFFAOYSA-N 0.000 description 1
- RZILCCPWPBTYDO-UHFFFAOYSA-N fluometuron Chemical compound CN(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 RZILCCPWPBTYDO-UHFFFAOYSA-N 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 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
- BGZZWXTVIYUUEY-UHFFFAOYSA-N fomesafen Chemical compound C1=C([N+]([O-])=O)C(C(=O)NS(=O)(=O)C)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 BGZZWXTVIYUUEY-UHFFFAOYSA-N 0.000 description 1
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- 230000035784 germination Effects 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- KKLBEFSLWYDQFI-UHFFFAOYSA-N halauxifen Chemical compound COC1=C(Cl)C=CC(C=2N=C(C(Cl)=C(N)C=2)C(O)=O)=C1F KKLBEFSLWYDQFI-UHFFFAOYSA-N 0.000 description 1
- KDHKOPYYWOHESS-UHFFFAOYSA-N halauxifen-methyl Chemical group NC1=C(Cl)C(C(=O)OC)=NC(C=2C(=C(OC)C(Cl)=CC=2)F)=C1 KDHKOPYYWOHESS-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000006341 heptafluoro n-propyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 150000002473 indoazoles Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-O isopropylaminium Chemical compound CC(C)[NH3+] JJWLVOIRVHMVIS-UHFFFAOYSA-O 0.000 description 1
- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 description 1
- ITGSCCPVERXFGN-UHFFFAOYSA-N isoxadifen Chemical compound C1C(C(=O)O)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 ITGSCCPVERXFGN-UHFFFAOYSA-N 0.000 description 1
- MWKVXOJATACCCH-UHFFFAOYSA-N isoxadifen-ethyl Chemical group C1C(C(=O)OCC)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 MWKVXOJATACCCH-UHFFFAOYSA-N 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
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- 239000011777 magnesium Substances 0.000 description 1
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- KPUREKXXPHOJQT-UHFFFAOYSA-N mesotrione Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O KPUREKXXPHOJQT-UHFFFAOYSA-N 0.000 description 1
- VHCNQEUWZYOAEV-UHFFFAOYSA-N metamitron Chemical compound O=C1N(N)C(C)=NN=C1C1=CC=CC=C1 VHCNQEUWZYOAEV-UHFFFAOYSA-N 0.000 description 1
- STEPQTYSZVCJPV-UHFFFAOYSA-N metazachlor Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)CN1N=CC=C1 STEPQTYSZVCJPV-UHFFFAOYSA-N 0.000 description 1
- JCHMGYRXQDASJE-UHFFFAOYSA-N metcamifen Chemical compound C1=CC(NC(=O)NC)=CC=C1S(=O)(=O)NC(=O)C1=CC=CC=C1OC JCHMGYRXQDASJE-UHFFFAOYSA-N 0.000 description 1
- MFSWTRQUCLNFOM-UHFFFAOYSA-N methyl 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical group C1=CC(OC(C)C(=O)OC)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl MFSWTRQUCLNFOM-UHFFFAOYSA-N 0.000 description 1
- ZTYVMAQSHCZXLF-UHFFFAOYSA-N methyl 2-[[4,6-bis(difluoromethoxy)pyrimidin-2-yl]carbamoylsulfamoyl]benzoate Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC(F)F)=CC(OC(F)F)=N1 ZTYVMAQSHCZXLF-UHFFFAOYSA-N 0.000 description 1
- QPTPZPIXUPELRM-UHFFFAOYSA-N methyl 3-[2-[2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]phenyl]sulfanylpropanoylamino]propanoate Chemical compound C1=C(Cl)C(SC(C)C(=O)NCCC(=O)OC)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F QPTPZPIXUPELRM-UHFFFAOYSA-N 0.000 description 1
- RTAXDHMFSZODHZ-UHFFFAOYSA-N methyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1h-indol-6-yl)pyridine-2-carboxylate Chemical compound NC1=C(Cl)C(C(=O)OC)=NC(C=2C(=C3NC=CC3=CC=2)F)=C1F RTAXDHMFSZODHZ-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 1
- RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 description 1
- 239000011785 micronutrient Substances 0.000 description 1
- 235000013369 micronutrients Nutrition 0.000 description 1
- AIMMSOZBPYFASU-UHFFFAOYSA-N n-(4,6-dimethoxypyrimidin-2-yl)-n'-[3-(2,2,2-trifluoroethoxy)pyridin-1-ium-2-yl]sulfonylcarbamimidate Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)OCC(F)(F)F)=N1 AIMMSOZBPYFASU-UHFFFAOYSA-N 0.000 description 1
- GBHVIWKSEHWFDD-UHFFFAOYSA-N n-[2-(4,6-dimethoxy-1,3,5-triazine-2-carbonyl)-6-fluorophenyl]-1,1-difluoro-n-methylmethanesulfonamide Chemical compound COC1=NC(OC)=NC(C(=O)C=2C(=C(F)C=CC=2)N(C)S(=O)(=O)C(F)F)=N1 GBHVIWKSEHWFDD-UHFFFAOYSA-N 0.000 description 1
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- 125000006095 n-butyl sulfinyl group Chemical group 0.000 description 1
- 125000006126 n-butyl sulfonyl group Chemical group 0.000 description 1
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- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- OLZQTUCTGLHFTQ-UHFFFAOYSA-N octan-2-yl 2-(4-amino-3,5-dichloro-6-fluoropyridin-2-yl)oxyacetate Chemical group CCCCCCC(C)OC(=O)COC1=NC(F)=C(Cl)C(N)=C1Cl OLZQTUCTGLHFTQ-UHFFFAOYSA-N 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
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- 159000000001 potassium salts Chemical class 0.000 description 1
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- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
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- 125000006239 protecting group Chemical group 0.000 description 1
- 125000002577 pseudohalo group Chemical group 0.000 description 1
- 239000008262 pumice Substances 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
- YYXSCUSVVALMNW-FOWTUZBSSA-N pyriminostrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1COC1=CC(C(F)(F)F)=NC(NC=2C(=CC(Cl)=CC=2)Cl)=N1 YYXSCUSVVALMNW-FOWTUZBSSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- BBKDWPHJZANJGB-IKJXHCRLSA-N quizalofop-P-tefuryl Chemical group O=C([C@H](OC=1C=CC(OC=2N=C3C=CC(Cl)=CC3=NC=2)=CC=1)C)OCC1CCCO1 BBKDWPHJZANJGB-IKJXHCRLSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 235000009736 ragweed Nutrition 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000004576 sand Substances 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
- 150000004760 silicates Chemical class 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- JKPSVOHVUGMYGH-UHFFFAOYSA-M sodium;(4,6-dimethoxypyrimidin-2-yl)-[[3-methoxycarbonyl-6-(trifluoromethyl)pyridin-2-yl]sulfonylcarbamoyl]azanide Chemical compound [Na+].COC(=O)C1=CC=C(C(F)(F)F)N=C1S(=O)(=O)NC(=O)[N-]C1=NC(OC)=CC(OC)=N1 JKPSVOHVUGMYGH-UHFFFAOYSA-M 0.000 description 1
- RUQIYMSRQQCKIK-UHFFFAOYSA-M sodium;2,3-di(propan-2-yl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(C(C)C)C(C(C)C)=CC2=C1 RUQIYMSRQQCKIK-UHFFFAOYSA-M 0.000 description 1
- NHQVTOYJPBRYNG-UHFFFAOYSA-M sodium;2,4,7-tri(propan-2-yl)naphthalene-1-sulfonate Chemical compound [Na+].CC(C)C1=CC(C(C)C)=C(S([O-])(=O)=O)C2=CC(C(C)C)=CC=C21 NHQVTOYJPBRYNG-UHFFFAOYSA-M 0.000 description 1
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- 150000008163 sugars Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- IUQAXCIUEPFPSF-UHFFFAOYSA-N tembotrione Chemical compound ClC1=C(COCC(F)(F)F)C(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O IUQAXCIUEPFPSF-UHFFFAOYSA-N 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- GLDAZAQRGCSFNP-UHFFFAOYSA-N thiencarbazone Chemical compound O=C1N(C)C(OC)=NN1C(=O)NS(=O)(=O)C1=C(C)SC=C1C(O)=O GLDAZAQRGCSFNP-UHFFFAOYSA-N 0.000 description 1
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 1
- IYMLUHWAJFXAQP-UHFFFAOYSA-N topramezone Chemical compound CC1=C(C(=O)C2=C(N(C)N=C2)O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 IYMLUHWAJFXAQP-UHFFFAOYSA-N 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- 229940047183 tribulus Drugs 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 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
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 238000006692 trifluoromethylation reaction Methods 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 1
- 241001478887 unidentified soil bacteria Species 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
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Abstract
本发明涉及具有式(I)的化合物或所述化合物的农艺学上可接受的盐,其中X、Y1、Y2、Z1、Z2、R1、R2、R5、R6和n是如本文所定义的。本发明进一步涉及包含具有式(I)的化合物的除草组合物,以及具有式(I)的化合物用于控制杂草(特别是在有用植物作物中)的用途。
Description
本发明涉及新颖的除草化合物、其制备方法、包含这些新颖的化合物的除草组合物、以及其用于控制杂草(特别是在有用植物作物中)的用途或用于抑制植物生长的用途。
EP0448206A2公开了各种取代的苯并咪唑和吲唑衍生物及其作为除草剂的用途。EP0367242A2公开了各种芳氧基苯并三唑及其作为除草剂的用途。本发明涉及提供另外的除草化合物。因此,根据本发明,提供了一种具有式(I)的化合物:
或其农艺学上可接受的盐,
其中
X选自由以下组成的组:CH2、O或S(O)p;
Y1是N或CR3;
Y2是N或CR4;
前提是Y1和Y2不都是N;
Z1是N或CR7;
Z2是N或CR8;
每个R1独立地选自由以下组成的组:卤素、-CN、硝基、C1-C4烷基、C2-C4烯基、C2-C4炔基、C1-C4卤代烷基、C1-C4烷氧基-、C1-C4卤代烷氧基-、-S(O)pC1-C4烷基和-S(O)pC1-C4卤代烷基;
R2选自由以下组成的组:C3-C8烷基、C3-C8烯基、C3-C8炔基、C3-C8卤代烷基、C3-C8卤代烯基、C3-C8卤代炔基、C1-C4烷氧基-C1-C3烷基-、C1-C4卤代烷氧基-C1-C3烷基-、C1-C4烷氧基-C1-C3卤代烷基-和-(CH2)mR9;
R3选自由以下组成的组:氢、卤素、-CN、硝基、C1-C4烷基、C2-C4烯基-、C2-C4炔基-、C1-C4卤代烷基-、C1-C4烷氧基-、C1-C4卤代烷氧基-和-S(O)nC1-C4烷基;
R4选自由以下组成的组:氢、卤素、-CN、硝基、C1-C4烷基、C2-C4烯基-、C2-C4炔基-、C1-C4卤代烷基-、C1-C4烷氧基-、C1-C4卤代烷氧基-和-S(O)nC1-C4烷基;
R5选自由以下组成的组:氢、卤素、C1-C3烷基和C1-C3卤代烷基;
R6选自由以下组成的组:氢、卤素、C1-C3烷基、C1-C3卤代烷基、C1-C3烷基和C1-C3卤代烷氧基;
R7选自由以下组成的组:氢、卤素、-CN、C1-C4烷基、C1-C4卤代烷基-和C1-C4烷氧基-;
R8选自由以下组成的组:氢、卤素、-CN、C1-C4烷基、C1-C4卤代烷基-和C1-C4烷氧基-;
R9选自C3-C6环烷基、苯基和包含1至4个杂原子的5或6元杂芳基,每个杂原子独立地选自由氧、氮和硫组成的组,并且其中所述苯基或杂芳基任选地被独立地选自由以下组成的组的一个、两个或三个取代基取代:卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基和C1-C4卤代烷氧基;
m是1、2、3或4
n=0、1或2;并且
p=0、1或2。
C1-C4烷基-包括例如甲基(Me、CH3)、乙基(Et、C2H5)、正丙基(n-Pr)、异丙基(i-Pr)、正丁基(n-Bu)、异丁基(i-Bu)、仲丁基和叔丁基(t-Bu)。C1-C2烷基是甲基(Me,CH3)或乙基(Et,C2H5)。
卤素(或卤代)包括例如氟、氯、溴或碘。上述情况对应地适用于其他定义背景下的卤素,如卤代烷基。
C1-C6卤代烷基-包括例如氟甲基、二氟甲基、三氟甲基、氯甲基、二氯甲基、三氯甲基、2,2,2-三氟乙基、2-氟乙基、2-氯乙基、五氟乙基、1,1-二氟-2,2,2-三氯乙基、2,2,3,3-四氟丙基和2,2,2-三氯乙基、七氟正丙基和全氟正己基。C1-C4卤代烷基-和C1-C2卤代烷基包括例如氟甲基、二氟甲基、三氟甲基、氯甲基、二氯甲基、三氯甲基、2,2,2-三氟乙基、2-氟乙基、2-氯乙基、五氟乙基、或1,1-二氟-2,2,2-三氯乙基。
C1-C4烷氧基和C1-C2烷氧基包括例如甲氧基和乙氧基。
C1-C6卤代烷氧基-和C1-C4卤代烷氧基-包括例如氟甲氧基、二氟甲氧基、三氟甲氧基、2,2,2-三氟乙氧基、1,1,2,2-四氟乙氧基、2-氟乙氧基、2-氯乙氧基、2,2-二氟乙氧基或2,2,2-三氯乙氧基,优选二氟甲氧基、2-氯乙氧基或三氟甲氧基。
C2-C4烯基-包括例如-CH=CH2(乙烯基)和-CH2-CH=CH2(烯丙基)。
C2-C4炔基-是指仅由碳原子和氢原子组成的直链或支链的烃链基团,该烃链基团含有至少一个三键,具有从二至四个碳原子,并且通过单键附接至分子的其余部分。C2-C4炔基的实例包括但不限于丙-1-炔基、炔丙基(丙-2-炔基)和丁-1-炔基。
C1-C4烷基-S-(烷硫基)包括例如甲硫基、乙硫基、丙硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基或叔丁硫基,优选甲硫基或乙硫基。
C1-C4烷基-S(O)-(烷基亚磺酰基)包括例如甲基亚磺酰基、乙基亚磺酰基、丙基亚磺酰基、异丙基亚磺酰基、正丁基亚磺酰基、异丁基亚磺酰基、仲丁基亚磺酰基或叔丁基亚磺酰基,优选甲基亚磺酰基或乙基亚磺酰基。
C1-C4烷基-S(O)2-(烷基磺酰基)包括例如甲基磺酰基、乙基磺酰基、丙基磺酰基、异丙基磺酰基、正丁基磺酰基、异丁基磺酰基、仲丁基磺酰基或叔丁基磺酰基,优选甲基磺酰基或乙基磺酰基。
在本发明的一个实施例中,提供了具有式(I)的化合物,其中X是O或S(O)p。在本发明的另一实施例中,提供了具有式(I)的化合物,其中X是O。在本发明的另一个实施例中,提供了具有式(I)的化合物,其中X是S(O)p(例如S、S(O)或S(O)2)。
在本发明的一个实施例中,提供了具有式(I)的化合物,其中Y1是CR3并且Y2是N(在该实施例中,R5和R6优选地是氢)或Y1是CR3并且Y2是CR4(在该实施例中,R5和R6优选地是氢)或Y1是N并且Y2是CR4(在该实施例中,R5优选地是氢并且R6是C1-C3烷基或C1-C3烷氧基,更优选地是甲基或甲氧基)。
在本发明的另一个实施例中,提供了具有式(I)的化合物,其中Z1是CR7并且Z2是N或Z1是N并且Z2是N或Z1是N并且Z2是CR8。在更优选的实施例中,Z1是CR7并且Z2是N。
在本发明的另一个实施例中,提供了具有式(I)的化合物,其中n=0。在本发明的另一个实施例中,提供了具有式(I)的化合物,其中n=1,更优选其中R1是6位上的取代基,并且其中更优选6-卤(尤其是氟或氯)或6-CN。
在本发明的另一个实施例中,提供了具有式(I)的化合物,其中R2是C3-C8烷基或C3-C8卤代烷基,更优选C3-C8氟烷基(例如CF3CH2CH2CH2-)。
在本发明的另一个实施例中,提供了具有式(I)的化合物,其中R3是卤素,优选是氯。
在本发明的另一个实施例中,提供了具有式(I)的化合物,其中R4选自由以下组成的组:氢、卤素(例如氟)和-CN。在本发明的另一个实施例中,提供了具有式(I)的化合物,其中R4是氢。
在本发明的另一个实施例中,提供了具有式(I)的化合物,其中R5是氢。
在本发明的另一个实施例中,提供了具有式(I)的化合物,其中R6选自由以下组成的组:氢、C1-C4烷基(优选是甲基)和C1-C3烷氧基(优选是甲氧基)。
在本发明的另一个实施例中,提供了具有式(I)的化合物,其中R7是氢或卤素(优选是氯)。
在本发明的另一个实施例中,提供了具有式(I)的化合物,其中R8是氢。
在本发明的特别优选的实施例中,提供了具有式(I)的化合物,其中X是O,Y1是CR3(其中R3优选是氯),并且Y2是N,R5和R6是氢,Z1是CR7(其中R7优选是氢或卤素(优选是氯))并且Z2是N。在该实施例中,优选n是0或1(其中R1=6-F、6-Cl或6-CN)并且R2是C3-C8氟烷基,例如CF3CH2CH2CH2-。
具有式(I)的化合物可以含有不对称中心并且可以作为单一对映异构体、以任何比例的对映异构体对而存在,或在存在多于一个不对称中心的情况下,含有所有可能比率的非对映异构体。典型地,与其他可能性相比,这些对映异构体之一具有增强的生物活性。
本发明还提供了具有式(I)的化合物的农艺学上可接受的盐。优选具有式(I)的化合物可与以下项形成的盐:胺,包括伯、仲和叔胺(例如氨、二甲胺和三乙胺),碱金属碱和碱土金属碱,过渡金属碱或季铵碱。
根据本发明的具有式(I)的化合物可以自身被用作除草剂,但是通常使用配制辅助剂(如载体、溶剂和表面活性剂(SAA))将它们配制成除草组合物。因此,本发明进一步提供了一种除草组合物,该除草组合物包含根据前述权利要求中任一项所述的除草化合物和农业上可接受的配制辅助剂。组合物可以呈浓缩物的形式,在使用前稀释这些浓缩物,尽管也可以制成即用型组合物。最终稀释通常用水进行,但是可以替代水或除了水之外使用例如液体肥料、微量营养素、生物有机体、油或溶剂进行。
除草组合物总体上包含按重量计从0.1%至99%、尤其是按重量计从0.1%至95%的具有式I的化合物和按重量计从1%至99.9%的配制辅助剂,该配制辅助剂优选地包括按重量计从0%至25%的表面活性物质。
组合物可以选自许多配制品类型。这些包括乳液浓缩物(EC)、悬浮液浓缩物(SC)、悬乳液(SE)、胶囊悬浮液(CS)、水可分散性颗粒剂(WG)、可乳化性颗粒剂(EG)、油包水型乳液(EO)、水包油型乳液(EW)、微乳液(ME)、油分散剂(OD)、油悬剂(OF)、油溶性液剂(OL)、可溶性浓缩物(SL)、超低容量悬浮液(SU)、超低容量液剂(UL)、母药(TK)、可分散性浓缩物(DC)、可溶性粉剂(SP)、可湿性粉剂(WP)以及可溶性颗粒剂(SG)。在任何情况下,所选择的配制品类型将取决于所设想的具体目的以及具有式(I)的化合物的物理、化学和生物特性。
可溶性粉剂(SP)可以通过以下方式制备:将具有式(I)的化合物与一种或多种水溶性无机盐(如碳酸氢钠、碳酸钠或硫酸镁)或一种或多种水溶性有机固体(如多糖)以及任选地一种或多种湿润剂、一种或多种分散剂或所述试剂的混合物进行混合,以改进水分散性/水溶性。然后将混合物研磨成细粉末。也可以将类似的组合物颗粒化以形成水溶性颗粒剂(SG)。
可湿性粉剂(WP)可以通过将具有式(I)的化合物与一种或多种固体稀释剂或载体、一种或多种湿润剂以及优选地,一种或多种分散剂,以及任选地,一种或多种悬浮剂混合来制备以促进在液体中的分散。然后将混合物研磨成细粉末。也可以将类似的组合物颗粒化以形成水可分散性颗粒剂(WG)。
可以这样形成颗粒剂(GR):通过将具有式(I)的化合物与一种或多种粉状固体稀释剂或载体的混合物颗粒化形成,或者通过将具有式(I)的化合物(或其在合适的试剂中的溶液)吸收进多孔颗粒材料(如浮石、凹凸棒石粘土、漂白土、硅藻土(kieselguhr)、硅藻土(diatomaceous earths)或玉米芯粉),或通过将具有式(I)的化合物(或其在合适的试剂中的溶液)吸附到硬芯材料(如沙、硅酸盐、矿物碳酸盐、硫酸盐或磷酸盐)上并且如果必要的话,进行干燥来由预成型的空白颗粒形成。通常用于帮助吸收或吸附的试剂包括溶剂(如脂肪族和芳香族石油溶剂、醇、醚、酮以及酯)和粘着剂(如聚乙酸乙烯酯、聚乙烯醇、糊精、糖以及植物油)。一种或多种其他添加剂也可以包含在颗粒剂中(例如乳化剂、湿润剂或分散剂)。
可分散性浓缩物(DC)可以通过将具有式(I)的化合物溶于水或有机溶剂(如酮、醇或二醇醚)中来制备。这些溶液可以包含表面活性剂(例如以改善水稀释或防止喷洒罐中的结晶)。
可乳化性浓缩物(EC)或水包油乳液(EW)可以通过将具有式(I)的化合物溶于有机溶剂(任选地含有一种或多种湿润剂、一种或多种乳化剂或者所述试剂的混合物)中来制备。在EC中使用的合适的有机溶剂包括芳香族烃(如烷基苯或烷基萘,以SOLVESSO 100、SOLVESSO 150和SOLVESSO 200为例;SOLVESSO是注册商标)、酮(如环己酮或甲基环己酮)和醇(如苯甲醇、糠醇或丁醇)、N-烷基吡咯烷酮(如N-甲基吡咯烷酮或N-辛基吡咯烷酮)、脂肪酸的二甲基酰胺(如C8-C10脂肪酸二甲基酰胺)和氯化烃。EC产品可以在添加到水中时自发地乳化,从而产生具有足够稳定性的乳液,以允许通过适当设备进行喷洒施用。
EW的制备涉及获得作为液体(如果它在室温下不是液体,则它可以在典型地低于70℃的合适温度下熔化)或处于溶液中(通过将它溶于适当的溶剂中)的具有式(I)的化合物,并且然后在高剪切下将所得液体或溶液乳化进含有一种或多种SAA的水中,以产生乳液。在EW中使用的合适的溶剂包括植物油、氯化烃(如氯苯)、芳香族溶剂(如烷基苯或烷基萘)以及在水中具有低溶解度的其他适当的有机溶剂。
微乳液(ME)可以通过将水与一种或多种溶剂和一种或多种SAA的共混物混合来制备,以自发地产生热力学稳定的各向同性的液体配制品。具有式(I)的化合物最初就存在于水中或溶剂/SAA共混物中。在ME中使用的合适的溶剂包括上文描述的在EC或EW中使用的那些。ME可以是水包油体系或油包水体系(存在哪种体系可以通过电导率测量来测定)并且可以适用于在同一配制品中混合水溶性的和油溶性的杀有害生物剂。ME适用于稀释到水中,保持为微乳液或形成常规的水包油乳液。
悬浮浓缩物(SC)可以包括具有式(I)的化合物的精细分散的不溶固体颗粒的水性或非水性悬浮液。SC可以通过将具有式(I)的固体化合物任选地与一种或多种分散剂在合适的介质中球磨或珠磨来制备,以产生该化合物的细颗粒悬浮液。在组合物中可以包含一种或多种湿润剂,并且可以包含悬浮剂以降低颗粒沉降的速率。可替代地,可以干磨具有式(I)的化合物并且将其添加到含有上文描述的试剂的水中,以产生希望的最终产物。
气溶胶配制品包含具有式(I)的化合物和合适的推进剂(例如正丁烷)。还可将具有式(I)的化合物溶于或分散于合适的介质(例如水或可与水混溶的液体,如正丙醇)中以提供在不加压的手动喷洒泵中使用的组合物。
胶囊悬浮液(CS)可以通过与制备EW配制品类似的方式来制备,但具有另外的聚合阶段,使得获得油滴的水性分散体,其中每个油滴被聚合物壳所包裹并且含有具有式(I)的化合物以及任选地用于该油滴的载体或稀释剂。聚合物壳可以通过界面缩聚反应或通过凝聚程序产生。这些组合物可以提供具有式(I)的化合物的受控释放并且它们可以用于种子处理。具有式(I)的化合物还可以配制在可生物降解的聚合物基质中以提供该化合物的缓慢的、受控的释放。
组合物可以包含一种或多种添加剂以改善该组合物的生物学性能,例如通过改善在表面上的湿润性、保持力或分布;被处理表面上的抗雨水性;或具有式(I)的化合物的吸收或流动。此类添加剂包括表面活性剂(SAA),基于油的喷洒添加剂,例如某些矿物油或天然植物油(如大豆和菜籽油),改性的植物油(如甲基化菜籽油(MRSO)),以及这些与其他生物增强辅助剂(可帮助或改变具有式(I)的化合物的作用的成分)的共混物。
湿润剂、分散剂和乳化剂可以是阳离子类型、阴离子类型、两性类型或非离子类型的SAA。
合适的阳离子类型的SAA包括季铵化合物(例如鲸蜡三甲基溴化铵)、咪唑啉以及胺盐。
合适的阴离子SAA包括脂肪酸的碱金属盐、硫酸的脂肪族单酯的盐(例如月桂硫酸钠)、磺化的芳香族化合物的盐(例如十二烷基苯磺酸钠、十二烷基苯磺酸钙、丁基萘磺酸盐以及二-异丙基-萘磺酸钠和三-异丙基-萘磺酸钠的混合物)、醚硫酸盐、醇醚硫酸盐(例如月桂醇聚醚-3-硫酸钠)、醚羧酸盐(例如月桂醇聚醚-3-羧酸钠)、磷酸酯(来自一种或多种脂肪醇与磷酸(主要是单酯)或与五氧化二磷(主要是二酯)之间反应的产物,例如月桂醇与四磷酸之间的反应;另外这些产物可以被乙氧基化)、磺基琥珀酰胺酸盐、石蜡或烯烃磺酸盐、牛磺酸盐、木质磺酸盐以及三苯乙烯基酚的磷酸盐/硫酸盐。
合适的两性类型的SAA包括甜菜碱、丙酸盐和甘氨酸盐。
合适的非离子类型的SAA包括环氧烷(如环氧乙烷、环氧丙烷、环氧丁烷或其混合物)与脂肪醇(如油醇或鲸蜡醇)或与烷基酚(如辛基酚、壬基酚或辛基甲酚)的缩合产物;衍生自长链脂肪酸或己糖醇酐的偏酯;所述偏酯与环氧乙烷的缩合产物;嵌段聚合物(包含环氧乙烷和环氧丙烷);烷醇酰胺;单酯(例如脂肪酸聚乙二醇酯);胺氧化物(例如月桂基二甲基氧化胺);卵磷脂和脱水山梨糖醇及其酯,烷基多糖苷和三苯乙烯基酚。
合适的悬浮剂包括亲水性胶体(如多糖、聚乙烯吡咯烷酮或羧甲基纤维素钠)和膨胀性粘土(如膨润土或凹凸棒石)。
本发明的除草化合物还可以与一种或多种另外的除草剂和/或植物生长调节剂混合使用。此类另外的除草剂或植物生长调节剂的实例包括乙草胺、三氟羧草醚(包括三氟羧草醚-钠)、苯草醚、莠灭净、氨唑草酮、氯氨吡啶酸、杀草强、莠去津、氟丁酰草胺-M、苄嘧磺隆(包括苄嘧磺隆-甲基)、灭草松、二环吡喃酮、双丙氨膦、双草醚-钠、比克罗腙(bixlozone)、除草定、溴苯腈、丁草胺、氟丙嘧草酯、唑草酮(包括唑草酮-乙基)、氯酯磺草胺(包括氯酯磺草胺-甲基)、氯嘧磺隆(包括氯嘧磺隆-乙基)、绿麦隆、氯磺隆、环庚草醚、氯酰草膦(clacyfos)、烯草酮、炔草酸(包括炔草酯)、异噁草酮、二氯吡啶酸、环吡拉尼(cyclopyranil)、环吡瑞莫(cyclopyrimorate)、环丙嘧磺隆、氰氟草酯(包括氰氟草酯-丁基)、2,4-D(包括其胆碱盐和2-乙基己基酯)、2,4-DB、敌菜安、麦草畏(包括其铝、氨基丙基、双-氨基丙基甲基、胆碱、二氯丙、二甘醇胺、二甲胺、二甲基铵、钾盐和钠盐)、双氯磺草胺、吡氟酰草胺、氟吡草腙、二甲草胺、精二甲吩草胺、二溴敌草快、敌草隆、乙丁烯氟灵、乙氧呋草黄、噁唑禾草灵(包括精噁唑禾草灵-乙基)、苯磺噁唑草(fenoxasulfone)、芬奎崔顿(fenquinotrione)、四唑酰草胺、啶嘧磺隆、双氟磺草胺、氯氟吡啶酯(florpyrauxifen)(包括氯氟吡啶酯-苄基)、吡氟禾草灵(包括精吡氟禾草灵-丁基)、氟酮磺隆(包括氟酮磺隆-钠)、氟噻草胺、唑嘧磺草胺、丙炔氟草胺、伏草隆、氟啶嘧磺隆(包括氟啶嘧磺隆-甲基-钠)、氟草烟(包括氟草烟-甲基庚基酯(fluroxypyr-meptyl))、氟黄胺草醚、甲酰胺磺隆、草铵膦(包括其铵盐)、草甘膦(包括其联胺、异丙基铵和钾盐)、氟氯吡啶酯(halauxifen)(包括氟氯吡啶酯-甲基)、氟吡甲禾灵(包括氟吡甲禾灵-甲基)、环嗪酮、hydantocidin、甲氧咪草烟、甲咪唑烟酸、灭草烟、咪草烟、茚嗪氟草胺、碘甲磺隆(包括碘甲磺隆-甲基-钠)、iofensulfuron(包括iofensulfuron-钠)、碘苯腈、异丙隆、异噁唑草酮、lancotrione、MCPA、MCPB、高2-甲-4-氯丙酸(mecoprop-P)、甲基二磺隆(包括甲基二磺隆-甲基)、甲基磺草酮、苯嗪草酮、吡草胺、异噁噻草醚(methiozolin)、异丙甲草胺、磺草唑胺、嗪草酮、甲磺隆、敌草胺、烟嘧磺隆、达草灭、噁草酮、环氧嘧磺隆、乙氧氟草醚、二氯化百草枯、二甲戊乐灵、五氟磺草胺、苯敌草、毒莠定、唑啉草酯、丙草胺、氟嘧磺隆-甲基、扑草净、敌稗、喔草酯、丙嗪嘧磺隆(propyrisulfuron)、戊炔草胺、苄草丹、氟磺隆、双唑草腈、吡草醚(pyraflufen)(包括吡草醚-乙基)、磺酰草吡唑、哒草特、环酯草醚、嘧氯磺草胺(pyrimisulfan)、吡咯磺隆(pyroxasulfone)、啶磺草胺、二氯喹啉酸、氯甲喹啉酸、喹禾灵(包括精喹禾灵-乙基和喹禾糠酯(quizalofop-P-tefuryl))、砜嘧磺隆、嘧啶肟草醚、烯禾啶、西玛津、精异丙甲草胺、甲磺草胺、磺酰磺隆、丁噻隆、特呋三酮、环磺酮、特丁津、特丁净、tetflupyrolime、噻酮磺隆(thiencarbazone)、噻吩磺隆、氟嘧硫草酯(tiafenacil)、托比利特(tolpyralate)、苯吡唑草酮、三甲苯草酮、氟酮磺草胺(triafamone)、野麦畏、醚苯磺隆、苯磺隆(包括苯磺隆-甲基)、绿草定、三氟啶磺隆(包括三氟啶磺隆-钠)、三氟草嗪(trifludimoxazin)、氟乐灵、氟胺磺隆、2-[[3-[2-氯-4-氟-5-[3-甲基-2,6-二氧代-4-三氟甲基)嘧啶-1-基]苯氧基]-2-吡啶基]氧基]乙酸乙酯、3-(2-氯-4-氟-5-(3-甲基-2,6-二氧代-4-三氟甲基-3,6-二氢嘧啶-1(2H)-基)苯基)-5-甲基-4,5-二氢异噁唑-5-甲酸乙酯、4-羟基-1-甲氧基-5-甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑啉-2-酮、4-羟基-1,5-二甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑啉-2-酮、5-乙氧基-4-羟基-1-甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑啉-2-酮、4-羟基-1-甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑啉-2-酮、4-羟基-1,5-二甲基-3-[1-甲基-5-(三氟甲基)吡唑-3-基]咪唑啉-2-酮、(4R)1-(5-叔丁基异噁唑-3-基)-4-乙氧基-5-羟基-3-甲基-咪唑啉-2-酮、3-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]二环[3.2.1]辛烷-2,4-二酮、2-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]-5-甲基-环己烷-1,3-二酮、2-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]环己烷-1,3-二酮、2-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]-5,5-二甲基-环己烷-1,3-二酮、6-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]-2,2,4,4-四甲基-环己烷-1,3,5-三酮、2-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]-5-乙基-环己烷-1,3-二酮、2-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]-4,4,6,6-四甲基-环己烷-1,3-二酮、2-[6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羰基]-5-甲基-环己烷-1,3-二酮、3-[6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羰基]二环[3.2.1]辛烷-2,4-二酮、2-[6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羰基]-5,5-二甲基-环己烷-1,3-二酮、6-[6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羰基]-2,2,4,4-四甲基-环己烷-1,3,5-三酮、2-[6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羰基]环己烷-1,3-二酮、4-[2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羰基]-2,2,6,6-四甲基-四氢吡喃-3,5-二酮、4-[6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羰基]-2,2,6,6-四甲基-四氢吡喃-3,5-二酮和4-氨基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶-2-甲酸(包括其农业化学上可接受的酯,例如4-氨基-3-氯-5-氟-6-(7-氟-1H-吲哚-6-基)吡啶-2-甲酸甲酯)。
具有式(I)的化合物的混合配伍物还可以呈酯或盐的形式,如例如在ThePesticide Manual[杀有害生物剂手册],第十六版,英国作物保护委员会(British CropProtection Council),2012中所提到的。
具有式(I)的化合物还可以与其他农用化学品(如杀真菌剂、杀线虫剂或杀昆虫剂)混合使用,其实例在The Pesticide Manual[杀有害生物剂手册]中给出。
具有式(I)的化合物与混合配伍物的混合比优选地是从1:100至1000:1。
这些混合物可以有利地用于以上提到的配制品中(在这种情况下“活性成分”涉及具有式(I)的化合物与混合配伍物的对应混合物)。
本发明的化合物或混合物还可以与一种或多种除草剂安全剂组合使用。此类安全剂的实例包括解草嗪、解草酸(cloquintocet)(包括解草酯)、环丙磺酰胺、二氯丙烯胺、解草唑(包括解草唑乙酯)、解草啶、氟草肟、解草噁唑、双苯噁唑酸(包括双苯噁唑酸乙酯)、吡唑解草酸(mefenpyr)(包括吡唑解草酯)、metcamifen和解草腈。
特别优选的是具有式(I)的化合物与环丙磺酰胺、双苯噁唑酸-乙基、解毒喹和/或metcamifen的混合物。
具有式(I)的化合物的安全剂还可以呈酯或盐的形式,如例如在The PesticideManual[杀有害生物剂手册],第16版(BCPC),2012中所提到的。对解草酯的提及还适用于其锂、钠、钾、钙、镁、铝、铁、铵、季铵、锍或鏻盐(如在WO 02/34048中披露的)。
优选地,具有式(I)的化合物与安全剂的混合比是从100:1至1:10,尤其是从20:1至1:1。
本发明还进一步提供了一种在场所处控制杂草的方法,所述方法包括向所述场所施用控制杂草量的包含具有式(I)的化合物的组合物。此外,本发明可以进一步提供一种在包括作物植物和杂草的场所处选择性地控制杂草的方法,其中该方法包括向该场所施用控制杂草量的根据本发明的组合物。‘控制’意指杀死、减少或延迟生长或防止或减少发芽。应指出,与已知的结构类似的化合物相比,本发明的化合物示出很大改善的选择性。通常有待控制的植物是不想要的植物(杂草)。‘场所’意指其中植物正生长或将生长的区域。施用可以在作物植物的出苗前和/或出苗后施用至场所。一些作物植物可以固有地耐受具有式(I)的化合物的除草作用。优选的作物植物包括玉米、小麦、大麦和水稻。
具有式I的化合物的施用比率可以在宽的范围内变化并且取决于土壤的性质、施用的方法(出苗前或出苗后;种子拌种;施用于种子沟;免耕法施用等)、作物植物、待控制的一种或多种杂草、当时的气候条件和其他受施用方法、施用时间和目标作物支配的因素。根据本发明的具有式I的化合物通常以从10至2500g/ha,尤其是从25至1000g/ha,更尤其是从25至250g/ha的比率施用。
通常通过喷洒该组合物进行施用,典型地是通过用于大面积的装在拖拉机上的喷洒机,但是还可以使用其他方法如撒粉(针对粉末)、滴加或浸灌。
作物植物应理解为还包括通过常规的育种方法或通过基因工程已经赋予对其他除草剂或多种类别的除草剂(例如ALS-抑制剂、GS-抑制剂、EPSPS-抑制剂、PPO-抑制剂、HPPD-抑制剂、抑制剂-PDS以及ACC酶-抑制剂)的耐受性的那些作物植物。通过常规的育种方法已经赋予对咪唑啉酮(例如,甲氧咪草烟)的耐受性的作物的实例是夏季油菜(卡诺拉(canola))。通过基因工程方法已经赋予对除草剂的耐受性的作物的实例包括例如具有草甘膦和草铵膦抗性的玉米品种,这些玉米品种在和商标名下是可商购的。
作物植物还应理解为通过基因工程方法已经赋予对有害昆虫的抗性的那些,例如Bt玉米(对欧洲玉米螟有抗性)、Bt棉花(对棉铃象鼻虫有抗性)以及还有Bt马铃薯(对科罗拉多甲虫有抗性)。Bt玉米的实例是的Bt 176玉米杂交体(先正达种子公司(Syngenta Seeds))。Bt毒素是由苏芸金芽孢杆菌土壤细菌天然形成的蛋白质。毒素或能够合成此类毒素的转基因植物的实例被描述在EP-A-451 878、EP-A-374 753、WO 93/07278、WO 95/34656、WO 03/052073和EP-A-427 529中。包含一个或多个编码杀昆虫抗性和表达一种或多种毒素的基因的转基因植物的实例是(玉米)、Yield(玉米)、(棉花)、(棉花)、(马铃薯)、和植物作物或其种子材料均可以是抗除草剂的并且同时是抗昆虫摄食的(“叠加的”转基因事件)。例如,种子可以具有表达杀昆虫的Cry3蛋白的能力,而同时对草甘膦是耐受的。
作物植物还应理解为包括通过常规的育种或基因工程的方法获得并且包含所谓的输出性状(例如改善的储存稳定性、更高的营养价值以及改善的风味)的那些。
可以使用这些组合物来控制不想要的植物(统称为‘杂草’)。有待控制的杂草既可以是单子叶的物种,例如剪股颖属、看麦娘属、燕麦属、臂形草属、雀麦属、蒺藜草属、莎草属、马唐属、稗属、穇属、黑麦草属、雨久花属、筒轴茅属、慈姑属、藨草属、狗尾草属以及高粱属,也可以是双子叶的物种,例如苘麻属、苋属、豚草属、藜属、菊属、白酒草属、拉拉藤属、番薯属、旱金莲属、黄花稔属、白芥属、茄属、繁缕属、婆婆纳属、堇菜属以及苍耳属。
在本发明的另外的方面,提供了如本文所定义的具有式(I)的化合物作为除草剂的用途。
用于制备化合物(例如具有式(I)的化合物)(该化合物任选地可以是其农业化学上可接受的盐)的方法现在进行描述,并且构成本发明的另外的方面。
具有式I的化合物可以由具有式A的化合物通过与具有式B的化合物(其中LG表示合适的离去基团,如卤素或SO2R)任选地在合适的碱的存在下并且在合适的溶剂中反应制备。合适的碱可以包括K2CO3或Cs2CO3。合适的溶剂可以包括DMF。具有式B的化合物是可商购的或可以通过文献中已知的方法制备。
具有式A的化合物可以由具有式C的化合物(其中PG表示合适的保护基团,如Me)通过脱保护反应在合适的溶剂中使用合适的试剂制备。当PG=Me时,用于进行该脱保护的合适的试剂可以包括BBr3或十二烷基硫醇/LiOtBu。合适的溶剂可以包括DCM或DMF。
具有式C的化合物可以由具有式D的化合物通过与具有式E的化合物(其中LG表示合适的离去基团,如Cl、Br或I或磺酸盐衍生物如Oms、OTs或OTf),任选地在合适的碱的存在下并且在合适的溶剂中反应制备。合适的碱可以包括Cs2CO3、K2CO3或NaH。合适的溶剂可以包括DMF、THF或CH3CN。具有式D和具有式E的化合物是可商购的或可以通过文献中已知的方法制备。
可替代地,具有式Ia的化合物(具有式I的化合物,其中Z1=C-Hal(其中Hal表示卤素))可以由具有式Ib的化合物(具有式I的化合物,其中Z1=C-H)通过在合适的溶剂中与合适的试剂的卤化反应制备。合适的卤化试剂可以包括N-氯代琥珀酰亚胺。合适的溶剂可以包括CH3CN。
在替代方法中,具有式Ca的化合物(具有式C的化合物,其中Z1=C-CN)可以由具有式F的化合物通过氰化反应使用合适的氰化物源在合适的催化剂和合适的碱的存在下并且在合适的溶剂中制备。合适的氰化物源可以包括Zn(CN)2。合适的催化剂可以包括Cu(NO3)2。
合适的碱可以包括CsF。合适的溶剂可以包括MeOH/水混合物。
具有式F的化合物可以由具有式Cb的化合物(具有式C的化合物,其中Z1=C-H)通过硼基化反应在合适的硼试剂和合适的催化剂和合适的配体的存在下并且在合适的溶剂中制备。合适的硼试剂可以包括双(频哪醇合)二硼。合适的催化剂可以包括(1,5-环辛二烯)(甲氧基)铱(I)二聚体。合适的配体可以包括4,4'-二叔丁基-2,2'-联吡啶。合适的溶剂可以包括叔丁基甲基醚。
在又另一替代方法中,具有式Cc的化合物(具有式C的化合物,其中Z1=C-R3(其中R3=C1-4烷基))可以通过在合适的催化剂和合适的配体的存在下,任选地在合适的碱的存在下并且在合适的溶剂中,使具有式F的化合物与具有式G的化合物(其中Q表示合适的交叉偶联官能团,如卤素或拟卤素)反应制备。合适的催化剂可以包括Pd(OAc)2。合适的配体可以包括二叔丁基(甲基)鏻四氟硼酸盐。合适的碱可以包括K2CO3。合适的溶剂可以包括2-甲基-2-丁醇。
在再又另一替代方法中,具有式Cd的化合物(具有式C的化合物,其中Z1=C-CF3)可以通过任选地在合适的碱的存在下并且在合适的溶剂中使具有式F的化合物与合适的CF3试剂反应制备。合适的CF3试剂可以包括(1,10-菲咯啉)(三氟甲基)铜(I)。合适的碱可以包括KF。合适的溶剂可以包括DMF。
在又另一替代方法中,具有式Cd的化合物(具有式C的化合物,其中Z1和Z2=N)可以通过重氮化/环化反应使用合适的重氮化试剂并且在合适的酸的存在下制备。合适的重氮化试剂可以包括NaNO2。合适的酸可以包括盐酸。
具有式H的化合物可以由具有式J的化合物通过还原反应在合适的溶剂中制备。合适的还原条件可以包括H2/Pd-C。合适的溶剂可以包括EtOH或MeOH。
具有式J的化合物可以由具有式K的化合物(其中LG表示合适的离去基团如Cl或F)通过任选地在合适的碱的存在下并且在合适的溶剂中与具有式L的化合物的SN AR反应制备。合适的碱可以包括N,N-二异丙基乙胺。合适的溶剂可以包括NMP。具有式K和具有式L的化合物是可商购的或可以通过已知的方法制备。
在又另一替代方法中,具有式Ce的化合物(具有式C的化合物,其中X=O,PG=Me且R1=4-卤素)可以由具有式Cf的化合物(具有式C的化合物,其中X=O,PG=Me且n=0)通过在合适的溶剂中与合适的卤化试剂反应制备。合适的卤化试剂可以包括磺酰氯。合适的溶剂可以包括DCM。
在又另一替代方法中,具有式Ic的化合物(具有式I的化合物,其中Z1=C-ORa,其中Ra=C1-4烷基)可以由具有式Ia的化合物(具有式I的化合物,其中Z1=卤素,优选Br)通过在合适的催化剂和合适的碱的存在下并且在合适的溶剂中与具有式M的化合物反应制备。合适的催化剂可以包括Rockphos Pd G3。合适的碱可以包括碳酸铯。合适的溶剂可以包括1,4-二噁烷。具有式M的化合物是可商购的或可以通过已知的方法制备。
在还另一替代方法中,具有式Cg的化合物(具有式C的化合物,其中R1=4-CF3)可以由具有式Ch的化合物(具有式C的化合物,其中n=0)通过自由基三氟甲基化使用合适的CF3前体在合适的催化剂和合适的氧化剂的存在下,在合适的溶剂中并用合适的光照射制备。合适的三氟甲基前体可以包括(2,2,2-三氟乙酰基)2,2,2-三氟乙酸酯。合适的催化剂可以包括三(2,2'-联吡啶)二氯钌(II)六水合物。合适的氧化剂可以包括吡啶-N-氧化物。合适的溶剂可以包括乙腈。
在还又另一替代方法中,具有式Da的化合物(具有式D的化合物,其中Z1=C-R7并且Z2=N)可以由具有式N的化合物(其中LG表示合适的离去基团,如F或Cl)通过在合适的溶剂中与肼的流动环化制备。合适的溶剂可以包括1,4-二噁烷。
以下非限制性实例提供了用于本发明的代表性化合物(如下表中所提及的)的具体合成方法。
实例1:7-(5-氯嘧啶-2-基)氧基-1-(4,4,4-三氟丁基)吲唑(1.001)的合成
步骤1:7-甲氧基-1-(4,4,4-三氟丁基)吲唑的合成
将7-甲氧基-1H-吲唑(100mg,0.67mmol)、Cs2CO3(440mg,2.3mmol)和4-溴-1,1,1-三氟-丁烷(200mg,1.0mmol)在DMF(5mL)中的溶液在室温下搅拌30分钟并且然后在微波辐射下在80℃下加热30分钟。将反应混合物用水稀释并且用Et2O萃取。将合并的有机萃取物用水和盐水洗涤,经MgSO4干燥并且在减压下蒸发至干燥。将粗产物通过使用环己烷中的梯度EtOAc在硅胶上进行快速色谱法纯化,得到呈无色油状物的所需产物(150mg,86%)。
1H NMR(500MHz,CDCl3)δ7.92(s,1H)7.27(t,1H)7.04(t,1H)6.72(d,1H)4.72(t,2H)3.98(s,3H)2.21-2.03(m,4H)。
步骤2:1-(4,4,4-三氟丁基)吲唑-7-醇的合成
在室温下,在N2气氛下,向7-甲氧基-1-(4,4,4-三氟丁基)吲唑(1.9g,7.4mmol)在DMF(50mL)中的溶液中添加十二烷-1-硫醇(3.3mL,14mmol),然后添加叔丁醇锂溶液(1M,在THF中)(14mL,14mmol)。将反应在100℃下加热4小时,并且然后使其冷却至室温。将反应混合物用2M HCl稀释并萃取到Et2O中。将合并的有机萃取物用水和盐水洗涤,经MgSO4干燥并且在减压下蒸发至干燥。将粗产物通过使用环己烷中的梯度EtOAc在硅胶上进行快速色谱法纯化,得到呈白色蜡状固体的所需产物(1.70g,95%)。
1H NMR(400MHz,CDCl3)δ7.99(s,1H)7.29(t,1H)6.96(t,1H)6.70(d,1H)6.68(s,1H)4.78(t,2H)2.26-2.04(m,4H)。
步骤3:7-(5-氯嘧啶-2-基)氧基-1-(4,4,4-三氟丁基)吲唑(1.001)的合成
在室温下,向1-(4,4,4-三氟丁基)吲唑-7-醇(200mg,0.82mmol)在DMF(10mL)中的溶液中添加2,5-二氯嘧啶(140mg,0.91mmol)和K2CO3(300mg,2.1mmol)。将反应加热至80℃保持1小时并且然后使其冷却至室温。将反应混合物用2M HCl稀释并用Et2O萃取。将合并的有机萃取物用水和盐水洗涤,经MgSO4干燥并且在减压下蒸发至干燥。将粗产物通过使用环己烷中的梯度EtOAc在硅胶上进行快速色谱法纯化,得到呈淡黄色胶状物的所需产物(265mg,91%)。
1H NMR(400MHz,CDCl3)δ8.53(s,2H),8.05(s,1H),7.68-7.62(m,1H),7.20-7.15(m,2H),4.48(br t,2H),2.10-198(m,2H)。
实例2:3-氯-7-(5-氯嘧啶-2-基)氧基-1-(4,4,4-三氟丁基)吲唑(1.005)的合成
步骤1:3-氯-7-(5-氯嘧啶-2-基)氧基-1-(4,4,4-三氟丁基)吲唑(1.005)的合成
将7-(5-氯嘧啶-2-基)氧基-1-(4,4,4-三氟丁基)吲唑(0.67g,1.88mmol)和N-氯代琥珀酰亚胺(0.276g,2.07mmol)在CH3CN(17mL)中的溶液在微波辐射下在80℃下加热2小时。添加另外的N-氯代琥珀酰亚胺(200mg),并将反应在微波辐射下在80℃下再加热2小时。将反应混合物冷却到室温并且然后在减压下蒸发至干燥。将粗产物通过使用环己烷中的梯度0-80%EtOAc在硅胶上进行快速色谱法纯化,得到呈无色胶状物的所需产物(181mg,25%)。
1H NMR(400MHz,CDCl3)δ8.53(s,2H),7.62-7.57(m,1H),7.25-7.20(m,2H),4.42(br t,2H),2.10-1.98(m,4H)。
实例3:7-(5-氯嘧啶-2-基)氧基-1-(4,4,4-三氟丁基)吲唑-3-甲腈(1.007)的合成
步骤1:7-甲氧基-3-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)-1-(4,4,4-三氟丁基)吲唑的合成
向双(频哪醇合)二硼(0.596g,2.32mmol)、4,4’-二叔丁基-2,2’-联吡啶(0.032g,0.116mmol)和(1,5-环辛二烯)(甲氧基)铱(I)二聚体(0.039g,0.0581mmol)在叔丁基甲基醚(5.8mL)中的溶液中添加7-甲氧基-1-(4,4,4-三氟丁基)吲唑(0.50g,1.94mmol)。将反应在微波辐射下在80℃下加热1小时。将反应混合物在减压下蒸发至干燥,并将粗产物通过使用环己烷中的梯度0-10%EtOAc作为洗脱液在硅胶上进行快速色谱法纯化,得到呈无色胶状物的所需产物(0.45g,61%)。
1H NMR(400MHz,CDCl3)δ7.65(d,1H),7.09(t,1H),6.72(d,1H),4.79(t,2H),3.97(s,3H),2.23-2.05(m,4H),1.41(s,12H)。
步骤2:7-甲氧基-1-(4,4,4-三氟丁基)吲唑-3-甲腈的合成
将7-甲氧基-3-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)-1-(4,4,4-三氟丁基)吲唑(0.285g,0.742mmol)、Cu(NO3)2.3H2O(0.272g,1.11mmol)、Zn(CN)2(0.269g,2.23mmol)和CsF(0.114g,0.742mmol)在MeOH(3.7mL)和水(1.5mL)中的溶液在100℃下在微波辐射下加热1小时。将反应混合物用饱和氯化铵稀释并且用EtOAc萃取。将合并的有机物用水、盐水洗涤,经MgSO4干燥并且在减压下蒸发至干燥。将粗产物通过使用梯度0-20%EtOAc/环己烷作为洗脱液在硅胶上进行快速色谱法纯化,得到呈无色固体的所需产物(100mg,48%)。
1H NMR(400MHz,CDCl3)δ7.38(d,1H),7.25(t,1H),6.82(d,1H),4.78(t,2H),4.01(s,3H),2.27-2.07(m,4H)。
步骤3:7-羟基-1-(4,4,4-三氟丁基)吲唑-3-甲腈的合成
向7-甲氧基-1-(4,4,4-三氟丁基)吲唑-3-甲腈(0.100g,0.353mmol)和1-十二烷硫醇(0.146g,0.706mmol)在DMF(1mL)中的溶液中添加叔丁醇锂(1M,在THF中)(0.71mL,0.71mmol)。将反应在100℃加热2小时,冷却至室温并在减压下蒸发至干燥。将粗产物通过使用梯度0-30%EtOAc/环己烷作为洗脱液在硅胶上进行快速色谱法纯化,得到呈淡黄色油状物的不纯的所需产物(105mg),其不经进一步纯化即可使用。
1H NMR(400MHz,CDCl3)δ7.57(s,1H),7.34(d,1H),7.14(t,1H),6.81(d,1H),4.81(t,2H),2.31-2.08(m,4H)。
步骤4:7-(5-氯嘧啶-2-基)氧基-1-(4,4,4-三氟丁基)吲唑-3-甲腈(1.007)的合成
向7-羟基-1-(4,4,4-三氟丁基)吲唑-3-甲腈(105mg,0.390mmol)和K2CO3(108mg,0.78mmol)在DMF(1mL)中的混合物中添加2,5-二氯嘧啶(71mg,0.468mmol)。将反应在70℃下加热20小时,使其冷却至室温并在减压下蒸发至干燥。将粗产物通过使用梯度0-15%EtOAc/环己烷作为洗脱液在硅胶上进行快速色谱法纯化,呈无色固体(125mg,84%)。
1H NMR(400MHz,CDCl3)δ8.54(s,2H),7.76(dd,1H),7.37(t,1H),7.31(dd,1H),4.58(t,2H),2.17-2.05(m,4H)。
实例4:7-(5-氯嘧啶-2-基)氧基-3-甲基-1-(4,4,4-三氟丁基)吲唑(1.021)的合成
步骤1:7-甲氧基-3-甲基-1-(4,4,4-三氟丁基)吲唑的合成
将Pd(OAc)2(0.011g,0.0651mmol)、二叔丁基(甲基)鏻四氟硼酸盐(0.033g,0.130mmol)、K2CO3(0.216g,1.56mmol)和7-甲氧基-3-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)-1-(4,4,4-三氟丁基)吲唑(0.500g,1.30mmol)在2-甲基-2-丁醇(13mL)中的混合物脱气并用氮气吹扫三次。添加碘甲烷(0.371g,2.60mmol)并将反应在65℃加热24小时。将反应冷却至室温并在减压下蒸发至干燥。将粗产物通过使用梯度0-20%EtOAc/环己烷作为洗脱液在硅胶上进行快速色谱法纯化,得到呈与7-甲氧基-1-(4,4,4-三氟丁基)吲唑不可分离的混合物形式的所需产物,其不经进一步纯化即可用于下一步骤。
步骤2:3-甲基-1-(4,4,4-三氟丁基)吲唑-7-醇的合成
向粗7-甲氧基-3-甲基-1-(4,4,4-三氟丁基)吲唑(0.200g,0.734mmol)和1-十二烷硫醇(0.303g,1.47mmol)在DMF(2mL)中的溶液中添加LiOtBu(1M溶液,在THF中)(1.47mL,1.47mmol)。将反应在100℃下加热3小时然后使其冷却至室温。将反应用饱和氯化铵水溶液淬灭并且用EtOAc萃取。将合并的有机萃取物用盐水洗涤、经MgSO4干燥并在减压下蒸发至干燥。将粗产物通过使用梯度0-25%EtOAc/环己烷在硅胶上进行快速色谱法纯化,得到呈与1-(4,4,4-三氟丁基)吲唑-7-醇不可分离的混合物形式的所需产物,其不经进一步纯化即可用于下一步骤。
步骤3:7-(5-氯嘧啶-2-基)氧基-3-甲基-1-(4,4,4-三氟丁基)吲唑(1.021)的合成
向粗3-甲基-1-(4,4,4-三氟丁基)吲唑-7-醇(0.130g,0.503mmol)和K2CO3(0.139g,1.01mmol)在DMF(1.3mL)中的溶液中添加2,5-二氯嘧啶(0.091g,0.604mmol)。将反应在80℃下加热3小时,然后使其冷却至室温。将反应用水稀释并且用EtOAc萃取。将合并的有机萃取物用盐水洗涤、经MgSO4干燥并在减压下蒸发至干燥。将粗产物通过质量导向反相HPLC纯化,得到呈淡棕色固体的所需产物(0.116g,62%)。
1H NMR(400MHz,CDCl3)δ8.53(s,2H),7.58(dd,1H),7.21-7.14(m,2H),4.42(t,2H),2.59(s,3H)2.09-1.92(m,4H)。
实例5:7-(5-氯嘧啶-2-基)氧基-1-(4,4,4-三氟丁基)-3-(三氟甲基)吲唑(1.022)的合成
步骤1:7-甲氧基-1-(4,4,4-三氟丁基)-3-(三氟甲基)吲唑的合成
将7-甲氧基-3-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂环戊烷-2-基)-1-(4,4,4-三氟丁基)吲唑(0.500g,1.30mmol)、KF(0.076g,1.30mmol)和(1,10-菲咯啉)(三氟甲基)铜(I)(0.543g,1.56mmol)在DMF(13mL)中的搅拌溶液在50℃下加热3小时,并且然后使其冷却至室温。将反应混合物通过硅藻土垫过滤并用EtOAc洗涤。将滤液在减压下蒸发至干燥。将粗产物通过使用梯度0-5%EtOAc/环己烷作为洗脱液在硅胶上进行快速色谱法纯化,得到呈与7-甲氧基-1-(4,4,4-三氟丁基)吲唑不可分离的混合物形式的所需产物,其不经纯化即可用于下一步骤。
步骤2:1-(4,4,4--三氟丁基)-3-(三氟甲基)吲唑-7-醇的合成
向粗7-甲氧基-1-(4,4,4-三氟丁基)-3-(三氟甲基)吲唑(0.420g,1.29mmol)和1-十二烷硫醇(0.532g,2.58mmol)在DMF(4.2mL)中的搅拌溶液中添加LiOtBu(1M,在THF中)(2.58mL,2.58mmol)。将反应在100℃下搅拌3小时并且然后使其冷却至室温。将反应用饱和氯化铵水溶液淬灭并且用EtOAc萃取。将合并的有机物用盐水洗涤、经MgSO4干燥并在减压下蒸发至干燥。将粗产物通过使用梯度0-25%EtOAc/环己烷作为洗脱液在硅胶上进行快速色谱法纯化,得到呈淡黄色固体的所需产物(0.370g,92%)。
1H NMR(400MHz,CDCl3)δ7.39(d,1H),7.09(t,1H),6.74(d,1H),5.59(s,1H),4.78(t,2H),2.29-2.09(m,4H)。
步骤3:7-(5-氯嘧啶-2-基)氧基-1-(4,4,4-三氟丁基)-3-(三氟甲基)吲唑(1.022)的合成
向1-(4,4,4-三氟丁基)-3-(三氟甲基)吲唑-7-醇(0.145g,0.464mmol)和K2CO3(0.128g,0.929mmol)在DMF(1.45mL)中的搅拌溶液中添加2,5-二氯嘧啶(0.084g,0.557mmol)。将反应在80℃下加热4小时,使其冷却至室温并在减压下蒸发至干燥。将粗产物通过使用梯度0-5%EtOAc/环己烷作为洗脱液在硅胶上进行快速色谱法纯化,得到呈淡黄色胶状物的所需产物(0.178g,90%)。
1H NMR(400MHz,CDCl3)δ8.54(s,2H),7.75(d,1H),7.35-7.27(m,2H),4.55(t,2H),2.13-2.04(m,4H)。
实例6:7-(5-氯嘧啶-2-基)氧基-1-(4,4,4-三氟丁基)苯并三唑(1.020)的合成
步骤1:2-甲氧基-6-硝基-N-(4,4,4-三氟丁基)苯胺的合成
向2-氯-1-甲氧基-3-硝基-苯(0.5g,3.0mmol)在NMP(10mL)中的溶液中添加N,N-二异丙基乙胺(0.9mL,5.0mmol)和4,4,4-三氟丁胺(0.4mL,3.0mmol)。将反应在微波辐射下在185℃下加热1小时。将反应用水(15mL)稀释并且用EtOAc(3x 15mL)萃取。将粗产物通过使用梯度0-10%EtOAc/环己烷作为洗脱液在硅胶上进行快速色谱法纯化,得到呈橙色油状物的所需产物(0.318g,40%)。
1H NMR(400MHz,CDCl3)δ7.74(d,1H),7.62(br,1H),6.94(d,1H),6.68(t,1H),3.86(s,3H),3.61(q,2H),2.25-2.12(m,2H),1.90-1.82(m,2H)。
步骤2:3-甲氧基-N2-(4,4,4-三氟丁基)苯-1,2-二胺的合成
向2-甲氧基-6-硝基-N-(4,4,4-三氟丁基)苯胺(0.318g,1.14mmol)在MeOH(10mL)中的溶液中添加5%Pd/C(0.03g),并将反应在H2气氛下(2巴压力)搅拌45分钟。将反应物通过硅藻土过滤,进一步用MeOH洗涤并且然后在减压下蒸发至干燥,得到呈红棕色油状物的所需产物(0.283g,定量),其不经进一步纯化即可使用。
1H NMR(400MHz,CDCl3)δ6.85(t,1H),6.37(br d,1H),6.34(dd,1H),3.80(s,3H),2.98(t,2H),2.32-2.10(m,2H),1.82-1.71(m,2H)。
步骤3:7-甲氧基-1-(4,4,4-三氟丁基)苯并三唑的合成
在0℃下向3-甲氧基-N2-(4,4,4-三氟丁基)苯-1,2-二胺(0.283g,1.14mmol)在2M盐酸(24mL)中的搅拌溶液中经几分钟逐滴添加亚硝酸钠(0.118g,1.71mmol)在水(1mL)中的溶液,始终保持反应温度低于3℃。将混合物搅拌30分钟,然后使其加热至室温。1.5小时后,将搅拌的反应混合物通过添加饱和NaHCO3溶液至约pH 7缓慢淬灭,然后用EtOAc(3x15mL)萃取。将合并的有机萃取物用水(2x 10mL)洗涤并在减压下蒸发至干燥,得到红棕色油状物。将粗产物通过使用梯度0-100%EtOAc/环己烷在硅胶上进行柱色谱法纯化,得到静置时结晶的呈琥珀色油状物的产物(164mg,55%)。
1H NMR(400MHz,CDCl3)δ7.62(d,1H),7.27(dd,1H),6.81(d,1H),4.91(t,2H),4.01(s,3H),2.31-2.10(m,4H)。
步骤4:3-(4,4,4-三氟丁基)苯并三唑-4-醇的合成
在氮气气氛下,向7-甲氧基-1-(4,4,4-三氟丁基)苯并三唑(0.114g,0.440mmol)在DMF(1.2mL)中的溶液中添加十二烷-1-硫醇(0.211mL,0.880mmol),然后经几分钟逐滴添加叔丁醇锂(1M,在THF中)(0.880mL,0.880mmol)。然后将混合物温热至100℃保持2小时。将反应混合物冷却至室温,然后通过添加水(2mL),然后添加2N HCl至pH 6淬灭。将混合物用Et2O(4x 3mL)萃取并将合并的有机萃取物在减压下蒸发至干燥。将粗产物通过使用梯度0-100%EtOAc/环己烷在硅胶上进行柱色谱法纯化,得到呈浅米色粉末状固体的产物(96mg,89%)。
1H NMR(400MHz,CDCl3)δ7.62(d,1H),7.19(dd,1H),6.81(d,1H),6.26(br s,1H),4.96(t,2H),2.37-2.25(m,2H),2.25-2.13(m,2H)。
步骤5:7-(5-氯嘧啶-2-基)氧基-1-(4,4,4-三氟丁基)苯并三唑的合成
在室温下,向3-(4,4,4-三氟丁基)苯并三唑-4-醇(0.047g,0.19mmol)在DMF(1mL)中的溶液中添加K2CO3(0.04g,0.29mmol),然后添加2,5-二氯嘧啶(0.043g,0.29mmol)。将反应混合物搅拌10分钟,然后在室温下静置过夜。将反应混合物用水(10mL)稀释并且用CH2Cl2(3x 8mL)萃取。将合并的有机萃取物在减压下蒸发至干燥,并将粗材料通过使用梯度0-100%EtOAc/环己烷在硅胶上进行柱色谱法纯化,得到呈无色油状物的所需产物(62mg,91%)。
1H NMR(400MHz,CDCl3)δ8.54(s,2H),7.99(dd,1H),7.41(t,1H),7.32(dd,1H),4.71(t,2H),2.21-2.05(m,4H)。
实例7:5-溴-3-氯-7-(5-氯嘧啶-2-基)氧基-1-(4,4,4-三氟丁基)吲唑(1.010)的合成
步骤1:5-溴-7-甲氧基-2-(4,4,4-三氟丁基)吲唑的合成
向5-溴-7-甲氧基-1H-吲唑(1.00g,4.40mmol)在N,N-二甲基甲酰胺(16mL)中的溶液中添加4-溴-1,1,1-三氟-丁烷(0.865mL,7.05mmol),然后添加Cs2CO3(2.55g,13.2mmol)。将反应在微波辐射下在80℃下加热1小时。将反应混合物倾倒入水中并用EtOAc稀释。分离各相并且将水相萃取到EtOAc(x2)中。将合并的有机萃取物用盐水洗涤,经MgSO4干燥并且在真空中浓缩。将粗材料通过使用梯度0-70%EtOAc/环己烷在硅胶上进行柱色谱法纯化,得到呈黄色固体的所需产物(1.10g,74%)。
1H NMR(400MHz,CDCl3)δ7.85(s,1H),7.43(d,1H),6.80(d,1H),4.68(t,2H),3.97(s,3H),2.19-2.02(m,4H)。
步骤2:5-溴-1-(4,4,4-三氟丁基)吲唑-7-醇的合成
在室温和氮气下,向5-溴-7-甲氧基-1-(4,4,4-三氟丁基)吲唑(0.500g,1.48mmol)在N,N-二甲基甲酰胺(5mL)中的溶液中添加1-十二烷硫醇(0.725mL,2.97mmol),然后添加叔丁醇锂(1M,在THF中)(2.97mL,2.97mmol)。在完成添加之后,将反应混合物加热至100℃保持1小时。使反应混合物冷却至室温、用水淬灭并用EtOAc稀释。将混合物用2MHCl酸化至pH 1并分离各相。将水相萃取到EtOAc(x2)中。将合并的有机萃取物用盐水洗涤,经MgSO4干燥并在真空中浓缩,得到黄色液体。将粗产物通过使用梯度0-60%EtOAc/环己烷在硅胶上进行柱色谱法纯化,得到呈白色固体的所需产物(460mg,96%)。
1H NMR(400MHz,CDCl3)δ7.88(s,1H),7.44(d,1H),6.80(d,1H),6.50(br s,1H),4.72(t,2H),2.23-2.02(m,4H)。
步骤3:5-溴-7-(5-氯嘧啶-2-基)氧基-1-(4,4,4-三氟丁基)吲唑的合成
向5-溴-1-(4,4,4-三氟丁基)吲唑-7-醇(0.460g,1.42mmol)在DMF(23.0mL)中的溶液中添加2,5-二氯嘧啶(0.233g,1.57mmol),然后添加K2CO3(0.517g,3.70mmol)。将反应混合物加热至80℃保持1小时。使反应混合物冷却至室温、用水稀释并且然后用2M HCl酸化。添加EtOAc并分离各相,然后萃取到EtOAc中。将合并的有机物用盐水洗涤、经MgSO4干燥、过滤并浓缩,得到棕色液体。将粗产物通过使用环己烷中的梯度0-50%EtOAc在硅胶上进行柱色谱法纯化,得到呈黄色胶状物的所需产物(0.6g,97%),其在静置时凝固成灰白色固体。
1H NMR(400MHz,CDCl3)δ8.54(s,2H),7.98(s,1H),7.78(d,1H),7.32(d,1H),4.48(t,2H),2.09-1.97(m,4H)。
步骤4:5-溴-3-氯-7-(5-氯嘧啶-2-基)氧基-1-(4,4,4-三氟丁基)吲唑的合成
将5-溴-7-(5-氯嘧啶-2-基)氧基-1-(4,4,4-三氟丁基)吲唑(0.300g,0.689mmol)和N-氯代琥珀酰亚胺(0.193g,1.45mmol)在CH3CN(4.50mL)中的溶液在微波辐射下在80℃下加热2小时。将反应混合物在真空中浓缩,得到黄色胶状物。将粗产物通过使用环己烷中的梯度0-30%EtOAc在硅胶上进行柱色谱法纯化,得到黄色胶状物,其在静置时凝固成灰白色固体,将其通过质量导向反相HPLC进一步纯化。得到呈白色固体的所需产物(49mg,15%)。
1H NMR(400MHz,CDCl3)δ8.55(s,2H),7.74(d,1H),7.37(d,1H),4.42(t,2H),2.09-1.99(m,4H)。
实例8:3-氯-7-(5-氯嘧啶-2-基)氧基-6-甲基-1-(4,4,4-三氟丁基)吲唑(1.043)的合成
步骤1:3-氯-7-(5-氯嘧啶-2-基)氧基-6-甲基-1-(4,4,4-三氟丁基)吲唑(1.043)的合成
向6-溴-3-氯-7-(5-氯嘧啶-2-基)氧基-1-(4,4,4-三氟丁基)吲唑(0.100g,0.213mmol)、四(三苯基磷鎓基)钯(0.025g,0.021mmol)和K2CO3(0.148g,1.06mmol)在1,4-二噁烷(1.06mL)和水(0.355mL)的混合物中的溶液中添加三甲基环硼氧烷(0.045mL,0.319mmol)。将混合物在微波辐射下在140℃下加热1小时。将反应混合物倾倒入水中并用二氯甲烷稀释。用2M HCl将水相酸化至pH 1。分离各相,并将有机相在真空中浓缩,得到黄色胶状物。将粗产物通过使用环己烷中的梯度0-40%EtOAc在硅胶上进行柱色谱法纯化,得到呈白色固体的所需产物(45mg,51%)。
1H NMR(400MHz,CDCl3)δ8.51(s,2H),7.49(d,1H),7.11(d,1H),4.32(t,2H),2.23(s,3H),2.05-1.93(m,4H)。
实例9:4-氯-7-(5-氯嘧啶-2-基)氧基-1-(4,4,4-三氟丁基)吲唑(1.013)的合成
步骤1:4-氯-7-甲氧基-1-(4,4,4-三氟丁基)吲唑的合成
在0℃下在氮气气氛下向7-甲氧基-1-(4,4,4-三氟丁基)吲唑(100mg,0.39mmol)在DCM(3mL)中的溶液中逐滴添加硫酰氯(0.032mL,0.39mmol)在1mL DCM中的溶液。在完成添加后将反应混合物搅拌60分钟。将反应混合物倾倒入水中并萃取到DCM中。将有机物用盐水洗涤,分离,经MgSO4干燥并且浓缩。将粗反应混合物通过使用环己烷中的梯度EtOAc在硅胶上进行柱色谱法纯化,得到呈无色油状物的所需产物(84mg,74%产率)。
1H NMR(400MHz,CDCl3)δ7.99(s,1H),6.99(d,1H),6.62(d,1H),4.71(t,2H),3.96(s,3H),2.04-2.30(m,4H)。
步骤2:4-氯-1-(4,4,4-三氟丁基)吲唑-7-醇的合成
在氮气气氛下,向4-氯-7-甲氧基-1-(4,4,4-三氟丁基)吲唑(0.375g,1.28mmol)在DMF(9.38mL)中的溶液中添加十二烷-1-硫醇(0.583mL,2.43mmol)和叔丁醇锂(1M,在THF中)(2.43mL,2.43mmol)。将反应混合物加热至100℃保持1小时,使其冷却至室温然后倒入2M HCl中并用EtOAc萃取。将有机萃取物用盐水洗涤,经MgSO4干燥并且浓缩。将粗产物通过使用环己烷中的梯度0-95%EtOAc在硅胶上进行柱色谱法纯化,得到呈白色固体的所需产物(0.291g,82%产率)。
1H NMR(400MHz,CDCl3)δ8.03(s,1H),6.92(d,1H),6.59(d,1H),5.87(s,1H),4.75(t,2H),2.24-2.05(m,4H)。
步骤3:4-氯-7-(5-氯嘧啶-2-基)氧基-1-(4,4,4-三氟丁基)吲唑的合成
向4-氯-1-(4,4,4-三氟丁基)吲唑-7-醇(0.287g,1.03mmol)和2,5-二氯嘧啶(0.169g,1.13mmol)在DMF(14.4mL)中的溶液中添加K2CO3(0.374g,2.68mmol)。将反应加热至80℃保持1小时,然后使其冷却至室温、用水稀释并且然后用2M HCl酸化。添加EtOAc,并分离各相,然后萃取到EtOAc(X2)中。将合并的有机物用盐水洗涤,经MgSO4干燥,过滤并浓缩。将粗产物通过使用环己烷中的梯度0-100%EtOAc在硅胶上进行柱色谱法纯化,得到呈白色固体的所需产物(0.344g,85%)。
1H NMR(400MHz,CDCl3)δ8.53(s,2H),8.11(s,1H),7.13(d,1H),7.11(d,1H),4.52-4.43(m,2H),2.09-1.97(m,4H)。
实例10:3-氯-7-(5-氯嘧啶-2-基)氧基-1-(4,4,4-三氟丁基)吲唑-6-甲腈(1.041)的合成
步骤1:3-氯-7-(5-氯嘧啶-2-基)氧基-1-(4,4,4-三氟丁基)吲唑-6-甲腈的合成
向6-溴-3-氯-7-(5-氯嘧啶-2-基)氧基-1-(4,4,4-三氟丁基)吲唑(0.060g,0.13mmol)和Zn(CN)2(0.018g,0.15mmol)在DMF(1.3mL)中的溶液中添加四(三苯基膦)钯(0)(0.015g,0.013mmol)。将混合物在微波辐射下在125℃下加热90分钟。将反应混合物浓缩并通过使用环己烷中的梯度0-40%EtOAc在硅胶上进行柱色谱法纯化,得到呈白色固体的所需产物(15mg,28%)。
1H NMR(400MHz,CDCl3)δ8.55(s,2H),7.69(d,1H),7.43(d,1H),4.45(t,2H),2.10-1.97(m,4H)。
实例11:3-溴-7-(5-氯嘧啶-2-基)氧基-1-(4,4,4-三氟丁基)吲唑(1.006)和7-(5-氯嘧啶-2-基)氧基-3-甲氧基-1-(4,4,4-三氟丁基)吲唑(1.033)的合成
步骤1:3-溴-7-(5-氯嘧啶-2-基)氧基-1-(4,4,4-三氟丁基)吲唑的合成
向7-(5-氯嘧啶-2-基)氧基-1-(4,4,4-三氟丁基)吲唑(0.530g,1.49mmol)在乙腈(7.45mL)中的溶液中添加N-溴代琥珀酰亚胺(0.588g,3.27mmol)。将反应在微波辐射下在80℃下加热90分钟。将反应混合物浓缩并通过使用梯度0-20%EtOAc/环己烷在硅胶上进行柱色谱法纯化,得到呈无色油状物的所需产物(0.50g,77%)。
1H NMR(400MHz,CDCl3)δ8.53(s,2H),7.56-7.52(m,1H),7.25-7.21(m,2H),4.45(br t,2H),2.10-1.99(m,4H)。
步骤2:7-(5-氯嘧啶-2-基)氧基-3-甲氧基-1-(4,4,4-三氟丁基)吲唑(1.033)的合成。
将3-溴-7-(5-氯嘧啶-2-基)氧基-1-(4,4,4-三氟丁基)吲唑(0.100g,0.23mmol)、碳酸铯(0.075g,0.23mmol)、Rockphos Pd G3(0.01g,0.01mmol)和MeOH(0.074g,2.30mmol)在1,4-二噁烷(1mL)中的溶液在微波辐射下在90℃下加热1小时。将反应混合物用水稀释并用DCM萃取。将有机物经MgSO4干燥,过滤并在真空中浓缩,并通过质量导向反相HPLC纯化,得到呈棕色胶状物的所需产物(0.020g,23%)。
1H NMR(400MHz,CDCl3)δ8.52(s,2H),7.56(dd,1H),7.17-7.12(m,1H),7.09-7.03(m,1H),4.25(t,2H),4.08(s,3H),2.06-1.90(m,4H)。
实例12:3-氯-7-(5-氯嘧啶-2-基)氧基-1-(4,4,4-三氟丁基)-4-(三氟甲基)吲唑(1.079)的合成
步骤1:1H-吲唑-7-基三氟甲磺酸酯的合成
在4℃下向1H-吲唑-7-醇(25.0g,186mmol)在THF(500mL)中的溶液中添加Cs2CO3(60.8g,186mmol)。经30分钟向其中分批添加1,1,1-三氟-N-(2-吡啶基)-N-(三氟甲基磺酰基)甲磺酰胺(66.8g,186mmol)。将混合物在5℃下搅拌2小时,然后,在5℃下向反应混合物中添加水(200mL)。将混合物温热至20℃并在真空中除去THF。将所得水溶液萃取到EtOAc中,并将合并的有机萃取物用盐水洗涤,经硫酸镁干燥并在真空中浓缩。将粗材料通过使用环己烷中的梯度0-40%EtOAc在硅胶上进行柱色谱法纯化,得到呈米色固体的所需产物(42.87g,86%)。
1H NMR(400MHz,CDCl3)δ10.70(br s,1H),8.20(s,1H),7.80(d,1H),7.36(d,H),7.24-7.19(m,1H)。
步骤2:(3-氯-1H-吲唑-7-基)三氟甲磺酸酯的合成
在20℃下经10分钟向1H-吲唑-7-基三氟甲磺酸酯(42.8g,161mmol)在DMF(400mL)中的搅拌溶液中分批添加N-氯代琥珀酰亚胺(21.5g,161mmol)。将反应在30℃下加热18小时过夜。将反应混合物浓缩得到黄色液体并通过使用环己烷中的梯度0-40%EtOAc在硅胶上进行柱色谱法纯化,得到呈米色固体的所需产物(46.63g,97%)。
1H NMR(400MHz,CDCl3)δ10.50(br s,1H),7.75(d,1H),7.42(d,1H),7.31-7.24(m,1H)。
步骤3:[3-氯-1-(4,4,4-三氟丁基)吲唑-7-基]三氟甲磺酸酯的合成
在N2气氛下向(3-氯-1H-吲唑-7-基)三氟甲磺酸酯(0.500g,1.66mmol)在THF(5mL)中的搅拌溶液中添加(NE)-N-(哌啶-1-羰基亚氨基)哌啶-1-甲酰胺(0.441g,1.75mmol),然后添加4,4,4-三氟丁-1-醇(0.185mL,1.75mmol)。将反应冷却至0℃并逐滴添加三丁基膦(0.50mL,2.00mmol)。10分钟后,将反应混合物温热至室温并搅拌过夜。将反应混合物通过添加H2O淬灭并用EtOAc稀释,分离有机层并将水层用EtOAc再萃取。将合并的有机萃取物用饱和硫代硫酸钠水溶液洗涤,然后用盐水洗涤,经MgSO4干燥,过滤并在减压下浓缩。将粗材料通过使用梯度0-20%EtOAc/环己烷在硅胶上进行柱色谱法纯化,得到呈无色油状物的所需产物(0.356g,52%)。
1H NMR(400MHz,CDCl3)δ7.70(d,1H),7.40(d,1H),7.24(d,1H),4.60(m,2H),2.20(m,4H)。
步骤4:[3-氯-1-(4,4,4-三氟丁基)-4-(三氟甲基)吲唑-7-基]三氟甲磺酸酯的合成
向配备有搅拌棒的小瓶中装入吡啶-N-氧化物(0.29g,3.0mmol)、三(2,2’-联吡啶)二氯钌(II)六水合物(0.0075g,0.010mmol)和[3-氯-1-(4,4,4-三氟丁基)吲唑-7-基]三氟甲磺酸酯(0.41g,1.0mmol)和乙腈(2.5mL)。然后添加(2,2,2-三氟乙酰基)-2,2,2-三氟乙酸酯(0.83mL,6.0mmol),并将反应用蓝光照射18小时。将反应混合物用饱和碳酸氢钠水溶液淬灭并用EtOAc萃取。将合并的有机萃取物在真空中浓缩,并通过使用梯度0-20%EtOAc/环己烷在硅胶上进行柱色谱法纯化,得到呈无色油状物的所需产物(0.229g,48%)。
1H NMR(400MHz,CDCl3)δ7.63-7.58(m,1H),7.46(d,1H),4.67-4.56(m,2H),2.31-2.16(m,4H)。
步骤5:3-氯-7-(5-氯嘧啶-2-基)氧基-1-(4,4,4-三氟丁基)-4-(三氟甲基)吲唑的合成
向[3-氯-1-(4,4,4-三氟丁基)-4-(三氟甲基)吲唑-7-基]三氟甲磺酸酯(50mg,0.104mmol)在乙腈(0.4mL)中的溶液中添加Cs2CO3(101mg,0.522mmol),然后添加2,5-二氯嘧啶(23mg,0.157mmol)。然后将反应混合物在80℃下加热过夜。将粗反应混合物用2M HCl(10mL)淬灭并用EtOAc萃取。将合并的有机萃取物在真空中浓缩,并通过使用梯度10%-20%环己烷/EtOAc在硅胶上进行柱色谱法纯化,得到呈无色油状物的所需产物(21mg,44%)。
1H NMR(400MHz,CDCl3)δ8.58-8.54(m,2H),7.58(d,1H),7.29(d,1H),4.54(t,2H),2.12-2.03(m,4H)。
表1-本发明的除草化合物的实例。
生物学实例
将各种测试物种的种子播种在盆中的标准土壤中:反枝苋(AMARE)、稗草(ECHCG)、大狗尾草(SETFA)。在受控条件下在温室(24℃/16℃,白天/夜晚;14小时光照;65%湿度)中培养一天(出苗前)或培养8天(出苗后)之后,用喷洒水溶液喷洒这些植物,该喷洒水溶液源自工业级活性成分在丙酮/水(50:50)溶液中的配制品,含有0.5%TweenTM20(聚氧乙烯脱水山梨糖醇单月桂酸酯,CAS RN 9005-64-5)。除非另有说明,否则化合物以250g/ha施用。然后使测试植物在温室中在受控条件下在温室(24℃/16℃,白天/夜晚;14小时光照;65%湿度)中生长,并且每日浇水两次。出苗前和出苗后13天后,对测试给植物造成的损害百分比进行评估。下表中以五分制示出了生物活性(5=81%-100%;4=61%-80%;3=41%-60%;2=21%-40%;1=0%-20%)。
表B1出苗后测试
NT=未测试。
表B2出苗前测试
N1.T=未测试。
Claims (17)
1.一种具有式(I)的化合物:
或其农艺学上可接受的盐,
其中
X选自由以下组成的组:CH2、O或S(O)p;
Y1是N或CR3;
Y2是N或CR4;
前提是Y1和Y2不都是N;
Z1是N或CR7;
Z2是N或CR8;
每个R1独立地选自由以下组成的组:卤素、-CN、硝基、C1-C4烷基、C2-C4烯基、C2-C4炔基、C1-C4卤代烷基、C1-C4烷氧基-、C1-C4卤代烷氧基-、-S(O)pC1-C4烷基和-S(O)pC1-C4卤代烷基;
R2选自由以下组成的组:C3-C8烷基、C3-C8烯基、C3-C8炔基、C3-C8卤代烷基、C3-C8卤代烯基、C3-C8卤代炔基、C1-C4烷氧基-C1-C3烷基-、C1-C4卤代烷氧基-C1-C3烷基-、C1-C4烷氧基-C1-C3卤代烷基-和-(CH2)mR9;
R3选自由以下组成的组:氢、卤素、-CN、硝基、C1-C4烷基、C2-C4烯基-、C2-C4炔基-、C1-C4卤代烷基-、C1-C4烷氧基-、C1-C4卤代烷氧基-和-S(O)nC1-C4烷基;
R4选自由以下组成的组:氢、卤素、-CN、硝基、C1-C4烷基、C2-C4烯基-、C2-C4炔基-、C1-C4卤代烷基-、C1-C4烷氧基-、C1-C4卤代烷氧基-和-S(O)nC1-C4烷基;
R5选自由以下组成的组:氢、卤素、C1-C3烷基和C1-C3卤代烷基;
R6选自由以下组成的组:氢、卤素、C1-C3烷基、C1-C3卤代烷基、C1-C3烷基和C1-C3卤代烷氧基;
R7选自由以下组成的组:氢、卤素、-CN、C1-C4烷基、C1-C4卤代烷基-和C1-C4烷氧基-;
R8选自由以下组成的组:氢、卤素、-CN、C1-C4烷基、C1-C4卤代烷基-和C1-C4烷氧基-;
R9选自C3-C6环烷基、苯基和包含1至4个杂原子的5或6元杂芳基,每个杂原子独立地选自由氧、氮和硫组成的组,并且其中所述苯基或杂芳基任选地被独立地选自由以下组成的组的一个、两个或三个取代基取代:卤素、氰基、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基和C1-C4卤代烷氧基;
m是1、2、3或4
n=0、1或2;并且
p=0、1或2。
2.根据权利要求1所述的化合物,其中,Y1是CR3并且Y2是N或Y1是CR3并且Y2是CR4或Y1是N并且Y2是CR4。
3.根据权利要求1或权利要求2所述的化合物,其中,Z1是CR7并且Z2是N或Z1是N并且Z2是N或Z1是N并且Z2是CR8。
4.根据前述权利要求中任一项所述的化合物,其中,n=0。
5.根据权利要求1至3中任一项所述的化合物,其中,n=1并且R1是Cl或CN。
6.根据前述权利要求中任一项所述的化合物,其中,R2是C3-C8卤代烷基。
7.根据前述权利要求中任一项所述的化合物,其中,R3是卤素。
8.根据前述权利要求中任一项所述的化合物,其中,R4选自由以下组成的组:氢、卤素和-CN。
9.根据前述权利要求中任一项所述的化合物,其中,R5是氢。
10.根据前述权利要求中任一项所述的化合物,其中,R6选自由以下组成的组:氢、C1-C4烷基和C1-C3烷氧基。
11.根据前述权利要求中任一项所述的化合物,其中,R7是卤素。
12.根据前述权利要求中任一项所述的化合物,其中,R8是氢。
13.一种除草组合物,其包含根据前述权利要求中任一项所述的化合物和农业上可接受的配制辅助剂。
14.根据权利要求13所述的除草组合物,其进一步包含至少一种另外的杀有害生物剂。
15.根据权利要求14所述的除草组合物,其中,所述另外的杀有害生物剂是除草剂或除草剂安全剂。
16.一种在场所处控制杂草的方法,所述方法包括向所述场所施用控制杂草量的根据权利要求13至15中任一项所述的组合物。
17.根据权利要求1所述的具有式(I)的化合物作为除草剂的用途。
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- 2020-11-12 CN CN202080079108.8A patent/CN114728930A/zh active Pending
- 2020-11-12 US US17/773,911 patent/US20230002357A1/en active Pending
- 2020-11-12 WO PCT/EP2020/081842 patent/WO2021094416A1/en unknown
- 2020-11-12 EP EP20807322.1A patent/EP4058444A1/en active Pending
- 2020-11-12 BR BR112022009045A patent/BR112022009045A2/pt unknown
- 2020-11-13 UY UY0001038959A patent/UY38959A/es unknown
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Also Published As
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AR120426A1 (es) | 2022-02-16 |
UY38959A (es) | 2021-06-30 |
WO2021094416A1 (en) | 2021-05-20 |
EP4058444A1 (en) | 2022-09-21 |
GB201916601D0 (en) | 2020-01-01 |
US20230002357A1 (en) | 2023-01-05 |
BR112022009045A2 (pt) | 2022-08-09 |
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