CN114728916A - 除草化合物 - Google Patents
除草化合物 Download PDFInfo
- Publication number
- CN114728916A CN114728916A CN202080079072.3A CN202080079072A CN114728916A CN 114728916 A CN114728916 A CN 114728916A CN 202080079072 A CN202080079072 A CN 202080079072A CN 114728916 A CN114728916 A CN 114728916A
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- China
- Prior art keywords
- compound
- formula
- chloro
- methyl
- methylsulfanyl
- Prior art date
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- Pending
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 110
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- 239000000203 mixture Substances 0.000 claims abstract description 86
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- 238000000034 method Methods 0.000 claims abstract description 17
- -1 alkyl radical Chemical class 0.000 claims description 113
- 238000009472 formulation Methods 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 239000004009 herbicide Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
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- 229910052801 chlorine Inorganic materials 0.000 claims description 7
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- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
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- GTKOKCQMHAGFSM-UHFFFAOYSA-N 1-methyltetrazol-5-amine Chemical compound CN1N=NN=C1N GTKOKCQMHAGFSM-UHFFFAOYSA-N 0.000 description 6
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- LMPIFZSJKLLOLM-UHFFFAOYSA-N 1,1,3-trioxo-1,2-benzothiazole-2-carbaldehyde Chemical compound C1=CC=C2S(=O)(=O)N(C=O)C(=O)C2=C1 LMPIFZSJKLLOLM-UHFFFAOYSA-N 0.000 description 5
- DJBPMDMHHBJIAM-UHFFFAOYSA-N 4-bromo-3-chloro-2-methylsulfanylphenol Chemical compound CSc1c(O)ccc(Br)c1Cl DJBPMDMHHBJIAM-UHFFFAOYSA-N 0.000 description 5
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- MUKYLHIZBOASDM-UHFFFAOYSA-N 2-[carbamimidoyl(methyl)amino]acetic acid 2,3,4,5,6-pentahydroxyhexanoic acid Chemical compound NC(=N)N(C)CC(O)=O.OCC(O)C(O)C(O)C(O)C(O)=O MUKYLHIZBOASDM-UHFFFAOYSA-N 0.000 description 2
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- 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
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- 125000005843 halogen group Chemical group 0.000 description 1
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- 229910052740 iodine Inorganic materials 0.000 description 1
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- JJWLVOIRVHMVIS-UHFFFAOYSA-O isopropylaminium Chemical compound CC(C)[NH3+] JJWLVOIRVHMVIS-UHFFFAOYSA-O 0.000 description 1
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- 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
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
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- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium;hydroxide;hydrate Chemical compound [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical class [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
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- 235000011160 magnesium carbonates Nutrition 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
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- 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
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
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- 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
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- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 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
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- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 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
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- 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
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- 159000000000 sodium salts Chemical class 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
- RLWYOEZLEULOLU-UHFFFAOYSA-M sodium;2,3,4-tri(propan-2-yl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=CC2=C(C(C)C)C(C(C)C)=C(C(C)C)C(S([O-])(=O)=O)=C21 RLWYOEZLEULOLU-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
- SXHLENDCVBIJFO-UHFFFAOYSA-M sodium;2-[2-(2-dodecoxyethoxy)ethoxy]ethyl sulfate Chemical compound [Na+].CCCCCCCCCCCCOCCOCCOCCOS([O-])(=O)=O SXHLENDCVBIJFO-UHFFFAOYSA-M 0.000 description 1
- MRTAVLDNYYEJHK-UHFFFAOYSA-M sodium;2-chloro-2,2-difluoroacetate Chemical compound [Na+].[O-]C(=O)C(F)(F)Cl MRTAVLDNYYEJHK-UHFFFAOYSA-M 0.000 description 1
- HFQQZARZPUDIFP-UHFFFAOYSA-M sodium;2-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HFQQZARZPUDIFP-UHFFFAOYSA-M 0.000 description 1
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- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 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
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- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 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
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical group ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 229960004394 topiramate Drugs 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
- 238000000844 transformation Methods 0.000 description 1
- 230000009466 transformation Effects 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
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 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
- 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
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical class C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
- 241001478887 unidentified soil bacteria Species 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
- C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
-
- 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
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P13/00—Herbicides; Algicides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/04—1,2,3-Oxadiazoles; Hydrogenated 1,2,3-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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Abstract
本发明涉及具有式(I)的化合物,其中Q、R2、R3和R4是如本文所定义的。本发明进一步涉及包含所述化合物的组合物,以及使用所述化合物和/或组合物控制杂草的方法。
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、以及其用于特别是在有用植物作物中控制杂草的用途或用于抑制植物生长的用途。
N-(四唑-5-基)-和N-(1,3,4-噁二唑-2-基)芳基甲酰胺分别披露于例如WO 2012/028579和WO 2012/126932中。本发明涉及新颖的芳基甲酰胺。
因此,根据本发明,提供了具有式(I)的化合物:
或其农艺学上可接受的盐,
其中:-
Q选自由以下组成的组:Q1和Q2:
R1选自由以下组成的组:C1-C4烷基-、C1-C4卤代烷基-、C1-C4烷氧基-C1-C4烷基-和C1-C4卤代烷氧基-C1-C4烷基-;
R2选自由以下组成的组:卤素、C1-C6烷基-、C1-C3烷氧基-、C1-C6卤代烷基-、C1-C3卤代烷氧基-和-S(O)pC1-C6烷基;
R3选自由以下组成的组:C1-C6烷基-、C3-C6环烷基-和C1-C6卤代烷基-;
R4是C1-C6卤代烷基;
并且
p是0、1或2。
C1-C6烷基和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)。
卤素(或卤代)涵盖了氟、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烷氧基C1-C3烷基-包括,例如,甲氧基乙基-和乙氧基甲基-。
如本文使用的,C3-C6环烷基是指稳定的单环基团,其是饱和的并且含有3至6个碳原子。C3-6环烷基的实例包括环丙基、环丁基、环戊基和环己基。
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-、2,2,3,3-四氟乙基-、2,2,2-三氯乙基-、七氟正丙基和全氟正己基。C1-C4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-、2,2,3,3-四氟乙基-、2,2,2-三氯乙基-和七氟正丙基-。
C1-C6烷基-S-(烷硫基)是,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-C6烷基-S(O)-(烷基亚磺酰基)是,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-C6烷基-S(O)2-(烷基磺酰基)是,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Q是Q1)(以下示出为具有式(Ia)的化合物)。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Q是Q2)(以下示出为具有式(Ib)的化合物)。
在本发明的优选实施例中,R1选自由以下组成的组:C1-C4烷基-(优选甲基、乙基或正丙基)、C1-C4卤代烷基-(2,2-二氟乙基或2,2,2-三氟乙基)和C1-C4烷氧基-C1-C4烷基-(优选甲氧基乙基-)。在更优选的实施例中,R1选自由以下组成的组:甲基、乙基和正丙基。在本发明的尤其优选的实施例中,R1是甲基。
在本发明的一个实施例中,R2选自由以下组成的组:卤素(优选氯)、C1-C6烷基-(优选甲基)、C1-C3烷氧基-(优选甲氧基-)、C1-C6卤代烷基-(优选-CF3)、C1-C3卤代烷氧基-(优选CF3O-)和-S(O)pC1-C6烷基(优选-SO2Me)。在尤其优选的实施例中,R2是氯。
在本发明的一个实施例中,R3选自由以下组成的组:C1-C6烷基-(优选甲基或乙基)、C3-C6环烷基(例如环丙基)和C1-C6卤代烷基-(例如-CF3)。在本发明的优选实施例中,R3是甲基或乙基,最优选地甲基。
在本发明的优选实施例中,R4选自由以下组成的组:CF3-、CHF2-、CH3CF2-、CF3CH2-、CF2HCF2-和CF3CHFCF2-。在更优选的实施例中,R4是CF3-或CHF2-,最优选地CF3-。
本发明还包括农艺学上可接受的盐,具有式(I)的化合物可以与胺(例如氨、二甲胺和三乙胺)、碱金属和碱土金属碱或季铵盐碱形成这些盐。在用作成盐物的碱金属和碱土金属氢氧化物、氧化物、醇化物以及碳酸氢盐和碳酸盐之中,强调的是锂、钠、钾、镁和钙的氢氧化物、醇化物、氧化物以及碳酸盐,但尤其是钠、镁和钙的那些。还可以使用对应的三甲基锍盐。
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(SFA))将它们配制成除草组合物。因此,本发明进一步提供了除草组合物,其包含本发明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。通常用水进行最终稀释,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。
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。
这些组合物可以选自多种配制品类型,这些配制品类型中的很多是从Manual onDevelopment and Use of FAO Specifications for Plant Protection Products[关于植物保护产物的FAO标准的发展和使用手册],第5版,1999中得知。这些包括可尘化粉剂(DP)、可溶性粉剂(SP)、水溶性颗粒剂(SG)、水可分散性颗粒剂(WG)、可湿性粉剂(WP)、颗粒剂(GR)(缓释或快释的)、可溶性浓缩物(SL)、可与油混溶的液体(OL)、超低体积液体(UL)、可乳化的浓缩物(EC)、可分散性浓缩物(DC)、乳液(水包油(EW)和油包水(EO)二者)、微乳液(ME)、悬浮液浓缩物(SC)、气溶胶、胶囊悬浮液(CS)以及种子处理配制品。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。
可尘化粉剂(DP)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固体稀释剂(例如,天然粘土、高岭土、叶蜡石、膨润土、氧化铝、蒙脱石、硅藻土(kieselguhr)、白垩土、硅藻土(diatomaceous earth)、磷酸钙、碳酸钙和碳酸镁、硫、石灰、面粉、滑石和其他有机和无机的固体载体)混合并将该混合物机械地碾磨成细粉末。
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药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(或其在合适的药剂中的溶液)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(或其在合适的药剂中的溶液)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药剂包括溶剂(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(例如乳化剂、湿润剂或分散剂)中。
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、醇或乙二醇醚)中来制备。这些溶液可以包含表面活性剂(例如以改进水稀释或防止喷雾罐中的结晶)。
可乳化的浓缩物(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药剂的混合物)中来制备。在EC中使用的合适的有机溶剂包括芳香族烃(例如烷基苯或烷基萘,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产物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℃的合理温度下熔化)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到含有一种或多种SFA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)可以通过以下方式制备:将水与一种或多种溶剂和一种或多种SFA的共混物混合,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)的化合物最初存在于水中或溶剂/SFA共混物中。在ME中使用的合适的溶剂包括此前描述的在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传导率测量来测定)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。
悬浮液浓缩物(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此前描述的药剂的水中,以产生希望的终产物。
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雾泵中使用的组合物。
胶囊悬浮液(CS)可以通过以与制备EW配制品类似的方式来制备,但具有另外的聚合阶段,这样使得获得油滴的水性分散体,其中每个油滴都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生物可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(SFA)、基于油的喷雾添加剂,例如某些矿物油或天然植物油(如大豆和油菜籽油),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SFA。
合适的阳离子类型的SFA包括季铵化合物(例如十六烷基三甲基溴化铵)、咪唑啉以及胺盐。
合适的阴离子型SFA包括脂肪酸的碱金属盐、脂肪族硫酸单酯的盐(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;另外这些产物可以是乙氧基化的)、硫代琥珀酰胺酸盐、石蜡或烯烃磺酸盐、牛磺酸盐以及木质磺酸盐。
合适的两性类型的SFA包括甜菜碱、丙酸盐和甘氨酸盐。
合适的非离子类型的SFA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);和卵磷脂。
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在具有一种或多种另外的除草剂和/或植物生长调节剂的混合物中使用。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、tetflupyrolimet、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(包括其农用化学上可接受的酯,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)的化合物还可以以与具有其他农用化学品(如杀真菌剂、杀线虫剂或杀昆虫剂)的混合物使用,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、解草酯(包括解毒喹)、环丙磺酰胺、二氯丙烯胺、解草唑(包括解草唑-乙基)、解草啶、氟草肟、解草噁唑、双苯噁唑酸(包括双苯噁唑酸-乙基)、吡唑解草酸(mefenpyr)(包括吡唑解草酸-二乙基)、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。对解毒喹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在场所控制杂草的方法,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,本发明进一步提供了在包括作物植物和杂草的场所选择性地控制杂草的方法,其中所述方法包括向所述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。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。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。然而,在一些情况下,可能需要将耐受性设计到作物植物中,例如通过基因工程。因此,可能的是作物植物经由基因工程而被赋予对HPPD-抑制剂的耐受性。赋予作物植物对HPPD-抑制剂的耐受性的方法是例如从WO0246387中已知的。因此,在甚至更优选的实施例中,作物植物关于多核苷酸是转基因的,该多核苷酸包含编码HPPD抑制剂抗性的HPPD酶的DNA序列,该HPPD抑制剂抗性的HPPD酶衍生自细菌(更特别地,衍生自荧光假单胞菌(Pseudomonas fluorescens)或希瓦氏菌(Shewanella colwelliana))、或衍生自植物(更特别地,衍生自单子叶植物或还更特别地,衍生自大麦、玉米、小麦、稻、臂形草属(Brachiaria)、蒺藜草属(Cenchrus)、黑麦草属(Lolium)、羊茅属(Festuca)、狗尾草属(Setaria)、蟋蟀草属(Eleusine)、高粱属(Sorghum)或燕麦属(Avena)物种)。几种HPPD耐受性大豆转基因“事件”是已知的,并且包括例如SYHT04R(WO 2012/082542)、SYHT0H2(WO 2012/082548)以及FG72。可用于提供耐受本发明化合物的植物的其他多核苷酸序列披露于例如WO 2010/085705和WO 2011/068567中。其中可以使用根据本发明的组合物的作物植物因此包括作物如谷物,例如大麦和小麦、棉花、油菜、向日葵、玉米、稻、大豆、甜菜、甘蔗以及草皮。
作物植物还可以包括树,如果树、棕榈树、椰子树或其他坚果。还包括藤本植物(如葡萄)、灌木果树、果实植物和蔬菜。
具有化学式I的化合物的施用率可以在宽的限度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、盛行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10g/ha至2000g/ha、尤其是从50g/ha至1000g/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)、滴加或浸湿。
作物植物应被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、ACC酶-抑制剂以及HPPD-抑制剂)的耐受性的那些作物植物。通过常规育种方法已经赋予其对咪唑啉酮(例如,甲氧咪草烟)的耐受性的作物的实例是Clearfield夏季油菜(卡诺拉(canola))。通过基因工程方法而赋予对除草剂的耐受性的作物的实例包括例如草甘膦和草丁膦抗性的玉米品种,这些玉米品种在RoundupReady和LibertyLink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其对有害昆虫的抗性的那些作物,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NK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剂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KnockOut(玉蜀黍)、Yield Gard(玉蜀黍)、NuCOTIN33B(棉花)、Bollgard(棉花)、NewLeaf(马铃薯)、NatureGard和Protexcta。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”转基因结果)。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香味)的那些。
其他有用的植物包括例如在高尔夫球场、草地、公园以及路旁的或者商业上种植用于草地的草皮草,以及观赏植物,如花卉或灌木。
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。杂草还可以包括可被认为是作物植物但是在作物区外生长的植物(‘野化植物(escape)’),或从先前栽培的不同作物留下的种子生长的植物(‘自生植物(volunteer)’)。此类自生植物或野化植物可以是抗某些其他除草剂的。
本发明进一步提供了具有式(Va)的化合物
其中R2、R3和R4是如上述权利要求1中所定义的并且R5是氢或C1-C4烷基。
本发明的化合物可以根据以下方案来制备。
具有式(I)的化合物(其中p=2或p=1)可以由具有式(I)的化合物(其中p=0)来制备。
如方案1所示,将具有式(I)的化合物(其中p=0)在合适的溶剂(例如二氯甲烷)中用合适的氧化剂(例如间氯过氧苯甲酸)处理,以给出具有式(I)的化合物(其中p=1)。可以通过在合适的溶剂(例如二氯甲烷)中用合适的氧化剂(例如间氯过氧苯甲酸)处理来将具有式(I)的化合物(其中p=1)进一步氧化为具有式(I)的化合物(其中p=2)。技术人员将认识到,具有式(I)的化合物(其中p=2)可以通过用至少2当量的氧化剂处理,由具有式(I)的化合物(其中p=0)在一个反应中制备。技术人员将认识到,与第一次氧化(从具有式(I)的化合物(其中p=0)到具有式(I)的化合物(其中p=1))相比,第二次氧化(从具有式(I)的化合物(其中p=1)到具有式(II)的化合物(其中p=2))需要更高的温度和更长的反应时间。因此,技术人员将能够控制氧化以给出他们所需的具有式(I)的化合物。
具有式(I)的酰胺(其中p=0)可以由具有式(II)的五氟苯酯和具有式(III)或具有式(IV)的胺制备。
将具有式(II)的五氟苯酯在合适的碱(例如2-叔丁基亚氨基-2-二乙基氨基-1,3-二甲基全氢-1,3,2-二吖磷英(diazaphosphorine))存在下和合适的溶剂(例如乙腈)中用具有式(III)的胺(Q=Q1)或具有式(IV)的胺(Q=Q2)处理。
具有式(II)的五氟苯酯可以由具有式(V)的苯甲酸制备。
将具有式(V)的苯甲酸在合适的溶剂(例如二氯甲烷)中与五氟苯酚和合适的酯偶联剂(例如1-乙基-3-(3-二甲基氨基丙基)碳二亚胺)反应。
在本发明的实施例中,R2是C1-C6烷基-、C1-C3烷氧基-、C1-C6卤代烷基-、C1-C3卤代烷氧基-和-S(O)pC1-C6烷基,具有式(V)的苯甲酸可以由具有式(VI)的酯制备。
将具有式(VI)的酯在乙醇+水溶剂中用氢氧化钠处理,以给出具有式(V)的苯甲酸。
在本发明的实施例中,R2是C1-C6烷基-、C1-C3烷氧基-、C1-C6卤代烷基-、C1-C3卤代烷氧基-或-S(O)pC1-C6烷基,具有式(VI)的化合物可以由具有式(VI)的化合物(其中R2是氯)制备。
在此步骤中,将氯取代基转化为具有式(VI)化合物的合适的R2取代基。此反应的方法将取决于R2的特性。技术人员将熟悉此类转化。例如,当R2是C1-C6烷基时,在合适的催化剂(例如[1,3-双(2,6-二异丙基苯基)咪唑-2-亚基](3-氯吡啶基)氯化钯(II))和合适的碱(例如碳酸钾)存在下,将具有式(IX)的化合物在合适的溶剂(例如1,4-二噁烷)中与C1-C6烷基硼酸或C1-C6烷基硼氧六环(例如三甲基硼氧六环,R2=甲基)反应。
具有式(VI)的化合物(其中R2=氯)可以由具有式(V)的化合物(其中R2=氯)制备。
将具有式(V)的化合物用乙醇和酸催化剂(例如硫酸)处理,以给出具有式(VI)的化合物。
具有式(V)的苯甲酸(其中R2=氯)可以由具有式(VII)的化合物制备。
将具有式(VII)的化合物在合适的溶剂(例如N-甲基吡咯烷酮和水)中用N-甲酰基糖精和合适的催化剂(例如乙酸钯(II)和Xantphos)以及合适的碱(例如三乙胺)处理。
具有式(VII)的化合物可以由具有式(VIII)的化合物和具有式(IX)的化合物制备。
将具有式(VIII)的化合物用二异丙基氨基锂(LDA)(在合适的溶剂(例如四氢呋喃)中)处理,然后用具有式(IX)的化合物处理。
在替代方法中,具有式(VII)的化合物可以由具有式(X)的苯酚制备。
将具有式X的苯酚用合适的卤烷基化试剂处理,该卤烷基化试剂将根据R4的特性而有所不同。例如,当R4是-CH2CF3时,将具有式X的苯酚用2,2,2-三乙基三氟甲基磺酸盐和碱(例如碳酸钾)处理。在另一个实例中,当R4是-CHF2时,将具有使(X)的苯酚用2-氯-2,2-二氟-乙酸钠和碱(例如碳酸钾)处理。
具有式(X)的苯酚可以由具有式(XI)的化合物制备。
将具有式(XI)的化合物在甲醇中用酸水溶液(例如2N盐酸)处理。
具有式(XI)的化合物可以由(2-((4-溴-3-氯苯氧基)甲氧基)乙基)三甲基硅烷制备。
将(2-((4-溴-3-氯苯氧基)甲基)乙基)三甲基硅烷用二异丙基氨基锂(LDA)(在溶剂(例如四氢呋喃)中)处理,然后用具有式(IX)的化合物处理。
(2-((4-溴-3-氯苯氧基)甲基)乙基)三甲基硅烷可以由4-溴-3-氯苯酚制备。
将4-溴-3-氯苯酚用2-(氯甲氧基)乙基-三甲基-硅烷和N,N-二异丙基乙胺处理。
以下非限制性实例提供了用于本发明代表性化合物(参考本文提供的表)的具体合成方法。
实例1.化合物1.001的制备。
步骤1
向含有4-溴-3-氯-苯酚(8g,38.6mmol)的烧瓶中添加DCM(40mL)和N,N-二异丙基乙胺(10g,13.5mL,77.1mmol)。在0℃下,逐滴添加2-(氯甲氧基)乙基-三甲基-硅烷(7.07g,7.4mL,42.4mmol)。将反应在室温下搅拌过夜。将反应通过添加水,然后添加饱和NaHCO3水溶液淬灭,将物质用乙酸乙酯萃取并将有机相在真空中浓缩,以给出呈橙色油状物的2-[(4-溴-3-氯-苯氧基)甲氧基]乙基-三甲基-硅烷(14.8g,定量%)。1H NMR(氯仿):7.47(d,1H),7.18(d,1H),6.83(dd,1H),5.18(s,2H),3.75(m,2H),0.94(m,2H),0.00(m,9H)
步骤2
向三颈烧瓶中添加THF(280mL)并将反应混合物吹扫并填充(用N2)。添加二异丙胺(6.78g,9.44mL,66.3mmol)。将反应在-78℃下搅拌30min。通过注射泵(10mL/min)来逐滴添加己烷中的正丁基锂(16g,2.5mol/L,23mL,58.0mmol)。将其搅拌1h,然后允许混合物升温至-40℃,然后再冷却至-78℃。通过注射泵(10mL/min)添加2-[(4-溴-3-氯-苯氧基)甲氧基]乙基-三甲基-硅烷(14g,41.5mmol)在23mL THF中的溶液并将反应混合物在-78℃下搅拌3h。逐滴添加(10mL/min)16mL THF中的二甲基二硫化物(7.89g,7.54mL,82.9mmol)并将混合物在-78℃下搅拌40min。通过将反应混合物彻底添加至搅拌的水溶液中来淬灭反应混合物。添加2M HCl直至混合物呈酸性并将混合物搅拌15min。用乙酸乙酯萃取物质,并将有机相在真空中浓缩,以给出呈橙色油状物的2-[(4-溴-3-氯-2-甲基硫烷基-苯氧基)甲氧基]乙基-三甲基-硅烷(14.4g,31.1mmol,75%)。1H NMR(氯仿):7.50(d,1H),7.01(d,1H),5.31(s,2H),3.79(m,2H),2.42(s,3H),0.95(m,2H),0.00(s,9H)
步骤3
向含有2-[(4-溴-3-氯-2-甲基硫烷基-苯氧基)甲氧基]乙基-三甲基-硅烷(14.4g,37.5mmol)的烧瓶中添加THF(188mL)、MeOH(113mL)和2M HCl水溶液(113mL)。将反应在70℃下搅拌1h。将反应混合物冷却至室温,然后在真空中浓缩。将粗物质用水稀释并用乙酸乙酯萃取,并将有机相在真空中浓缩。将物质通过快速色谱法(环己烷中的0%至20%的EtOAc)纯化,以给出呈白色晶体的4-溴-3-氯-2-甲基硫烷基-苯酚(8.28g,32.6mmol,87%)。1H NMR(氯仿):7.50(d,1H),7.09(s,1H),6.85(d,1H),2.34(s,3H)
步骤4
向含有4-溴-3-氯-2-甲基硫烷基-苯酚(2g,7.89mmol)的烧瓶中添加DMF(20mL)。添加K2CO3(1.38g,9.47mmol),随后添加2,2,2-三氟乙基三氟甲磺酸酯(2.20g,1.36mL,9.47mmol),并将反应混合物在室温下搅拌3.5h。将反应混合物通过添加水淬灭并将物质用乙酸乙酯萃取。将有机相用水洗涤并在真空中浓缩。将物质通过快速色谱法(环己烷中的0%至15%的EtOAc)纯化,以给出呈无色油状物的1-溴-2-氯-3-甲基硫烷基-4-(2,2,2-三氟乙氧基)苯(2.62g,7.81mmol,99%)。1H NMR(氯仿):7.54(d,1H),6.73(d,1H),4.42(q,2H),2.45(s,3H)
步骤5
向含有NMP(101mL)的容器中添加乙酸钯(II)(0.169g,0.751mmol)、XantPhos(0.896g,1.50mmol)、N-甲酰基糖精(3.57g,16.9mmol)和1-溴-2-氯-3-甲基硫烷基-4-(2,2,2-三氟乙氧基)苯(2.52g,7.51mmol)。向第二容器中添加三乙胺(3.57g,4.71mL,33.8mmol)、NMP(101mL)和水(5.04mL)。反应在Uniqsis FlowSyn中进行。将这两种溶液通过T型管泵送,并且然后围绕加热至170℃的20mL不锈钢盘管(stainless steel coil)。设定流速以使总停留时间为15min。将反应混合物冷却至室温,并用乙酸乙酯稀释。将有机相用2M HCl然后用水洗涤。将有机相在真空中浓缩。将物质通过快速色谱法(环己烷中的0%至100%的EtOAc)纯化,以给出呈橙色固体的2-氯-3-甲基硫烷基-4-(2,2,2-三氟乙氧基)苯甲酸(0.96g,2.87mmol,38%)。1H NMR(甲醇):7.78(d,1H),7.09(d,1H),4.71(q,2H),2.40(s,3H)
步骤6
向含有2-氯-3-甲基硫烷基-4-(2,2,2-三氟乙氧基)苯甲酸(0.816g,2.71mmol)的烧瓶中添加2,3,4,5,6-五氟苯酚(0.750g,4.07mmol)和DCM(16mL)。添加1-(3-二甲基氨基丙基)-3-乙基碳二亚胺盐酸盐(0.602g,2.99mmol)并且将反应在室温下搅拌2h。将反应混合物用DCM稀释并用饱和NaHCO3水溶液洗涤。将有机相在真空中浓缩。将物质通过快速色谱法(环己烷中的0%至10%的EtOAc)纯化以给出呈白色针状的(2,3,4,5,6-五氟苯基)2-氯-3-甲基硫烷基-4-(2,2,2-三氟乙氧基)苯甲酸酯(0.758g,1.62mmol,60%)。1H NMR(氯仿):8.07(d,1H),6.91(d,1H),4.54(q,2H),2.46(s,3H)
步骤7
向含有(2,3,4,5,6-五氟苯基)2-氯-3-甲基硫烷基-4-(2,2,2-三氟乙氧基)苯甲酸酯(0.379g,0.812mmol)的烧瓶中添加乙腈(7.6mL),并将混合物在室温下搅拌。添加1-甲基四唑-5-胺(88.5Mg,0.893mmol),随后添加2-叔丁基亚氨基-2-二乙基氨基-1,3-二甲基全氢-1,3,2-二吖磷英(0.506g,0.533mL,1.79mmol),并将反应混合物在室温下搅拌过夜。将反应混合物用水稀释并用2M HCl酸化。然后用乙酸乙酯萃取物质。将有机相在真空中浓缩。将物质通过快速色谱法(环己烷中的0%至70%的EtOAc)纯化以给出白色固体。将此物质从热甲醇中结晶以给出呈白色晶体的2-氯-3-甲基硫烷基-N-(1-甲基四唑-5-基)-4-(2,2,2-三氟乙氧基)苯甲酰胺(0.236g,0.544mmol,67%)。1H NMR(乙腈):7.65(d,1H),7.11(d,1H),4.71(q,2H),4.01(s,3H),2.46(s,3H)。
实例2.化合物1.005的制备。
步骤1
向三颈烧瓶中添加THF(22mL)并将反应混合物吹扫并填充(用N2)。添加二异丙胺(1.19g,1.65mL,11.6mmol)。将反应在-78℃下搅拌30min。逐滴添加己烷中的正丁基锂(2.8g,2.5mol/L,4.1mL,10.2mmol)。将其搅拌1h,然后允许混合物升温至-40℃,然后再冷却至-78℃。添加1-溴-2-氯-4-(三氟甲氧基)苯(2g,7.26mmol)在5mL的THF中的溶液并将反应混合物在-78℃下搅拌1.5h。逐滴添加二甲基二硫化物(1.38g,1.32mL,14.5mmol)并将混合物在-78℃下搅拌1h。通过将反应混合物彻底添加至搅拌的水溶液中来淬灭反应混合物。添加2M HCl直至混合物呈酸性并将混合物搅拌15min。用二乙醚萃取物质,并将有机相在真空中浓缩,以给出呈无色油状物的1-溴-2-氯-3-甲基硫烷基-4-(三氟甲氧基)苯(2.09g,6.50mmol,90%)。1H NMR(氯仿):7.62(d,1H),7.11(d,1H),2.46(s,3H)
步骤2
向含有NMP(47mL)的容器中添加乙酸钯(II)(0.082g,0.364mmol)、XantPhos(0.434g,0.728mmol)、N-甲酰基糖精(1.73g,8.19mmol)和1-溴-2-氯-3-甲基硫烷基-4-(三氟甲氧基)苯(1.17g,3.64mmol)。向第二容器中添加三乙胺(1.66g,2.28mL,16.4mmol)、NMP(47mL)和水(2.34mL)。反应在Uniqsis FlowSyn中进行。将这两种溶液通过T型管泵送,并且然后围绕加热至170℃的20mL不锈钢盘管。设定流速以使总停留时间为20min。将反应混合物冷却至室温,并用乙酸乙酯稀释。将有机相用2M HCl然后用水洗涤。将有机相在真空中浓缩。将物质通过快速色谱法(环己烷中的0%至100%的EtOAc)纯化,以给出呈黄色固体的2-氯-3-甲基硫烷基-4-(三氟甲氧基)苯甲酸(0.691g,2.41mmol,66%)。1H NMR(甲醇):7.82(d,1H),7.44(d,1H),2.46(s,3H)
步骤3
向含有2-氯-3-甲基硫烷基-4-(三氟甲氧基)苯甲酸(0.125g,0.436mmol)的烧瓶中添加2,3,4,5,6-五氟苯酚(88.2mg,0.480mmol)和DCM(2.5mL)。添加1-(3-二甲基氨基丙基)-3-乙基碳二亚胺盐酸盐(0.101g,0.501mmol)并将反应在室温下搅拌1h。将反应混合物用DCM稀释并用饱和NaHCO3水溶液洗涤。将有机相在真空中浓缩以给出呈淡黄色油状物的(2,3,4,5,6-五氟苯基)2-氯-3-甲基硫烷基-4-(三氟甲氧基)苯甲酸酯(0.197g,0.436mmol,100%),将其不经进一步纯化而按粗品使用。
步骤4
向含有(2,3,4,5,6-五氟苯基)3-氨基-2-氯-4-(三氟甲基)苯甲酸酯(0.197g,0.436mmol)的烧瓶中添加DMF(2mL)。添加1-甲基四唑-5-胺(47.5mg,0.480mmol),然后添加2-叔丁基亚氨基-2-二乙基氨基-1,3-二甲基全氢-1,3,2-二吖磷英(0.271g,0.286mL,0.959mmol),并将反应混合物在室温下搅拌过夜。将反应混合物用水稀释,并用2M HCl酸化。然后用乙酸乙酯萃取物质。将有机相在真空中浓缩。将物质通过快速色谱法(环己烷中的0%至100%的EtOAc)纯化,以给出呈灰白色固体的2-氯-3-甲基硫烷基-N-(1-甲基四唑-5-基)-4-(三氟甲氧基)苯甲酰胺(76.6mg,0.208mmol,48%)。1H NMR(甲醇):7.73(d,1H),7.52(d,1H),4.07(s,3H),2.48(s,3H)
实例3.化合物2.001的制备。
上述化合物1.001的程序中描述了起始材料酚的合成。
步骤1
向含有4-溴-3-氯-2-甲基硫烷基-苯酚(2g,7.89mmol)的烧瓶中添加DMF(20mL)。添加K2CO3(1.38g,9.47mmol),然后添加2-氯-2,2-二氟-乙酸钠(1.45g,9.47mmol)。在防爆罩(blast shield)后将反应混合物在100℃下搅拌45min。将混合物冷却至室温。将反应混合物用水稀释并用乙酸乙酯萃取。将有机相用水洗涤然后在真空中浓缩。将物质通过快速色谱法(环己烷中的0%至15%的EtOAc)纯化,以给出呈无色油状物的1-溴-2-氯-4-(二氟甲氧基)-3-甲基硫烷基-苯(1.46g,4.81mmol,61%)。1H NMR(氯仿):7.59(d,1H),7.02(d,1H),6.56(t,1H),2.46(s,3H)
步骤2
向含有NMP(55mL)的容器中添加乙酸钯(II)(0.101g,0.451mmol)、XantPhos(0.538g,0.903mmol)、N-甲酰基糖精(2.15g,10.1mmol)、和1-溴-2-氯-4-(二氟甲氧基)-3-甲基硫烷基-苯(1.37g,4.51mmol)。向第二容器中添加三乙胺(2.06g,2.83mL,20.3mmol)、NMP(55mL)和水(2.74mL)。反应在Uniqsis FlowSyn中进行。将这两种溶液通过T型管泵送,并且然后围绕加热至170℃的20mL不锈钢盘管。设定流速以使总停留时间为20min。将反应混合物冷却至室温,并用乙酸乙酯稀释。将有机相用2M HCl然后用水洗涤。将有机相在真空中浓缩。将物质通过快速色谱法(环己烷中的0%至100%的EtOAc)纯化,以给出呈黄色固体的2-氯-4-(二氟甲氧基)-3-甲基硫烷基-苯甲酸(0.953g,3.19mmol,70%)。1H NMR(氯仿):7.91(d,1H),7.18(d,1H),6.65(t,1H),2.47(s,3H)
步骤3
向含有2-氯-4-(二氟甲氧基)-3-甲基硫烷基-苯甲酸(0.65g,2.42mmol)的烧瓶中添加2,3,4,5,6-五氟苯酚(0.668g,3.63mmol)和DCM(13mL)。添加1-(3-二甲基氨基丙基)-3-乙基碳二亚胺盐酸盐(0.537g,2.66mmol)并将反应混合物在室温下搅拌2h。将反应混合物用DCM稀释并用饱和NaHCO3水溶液洗涤。将有机相在真空中浓缩以给出呈绿色油状物的(2,3,4,5,6-五氟苯基)2-氯-4-(二氟甲氧基)-3-甲基硫烷基-苯甲酸酯(1.3g,3.00mmol,124%),将其不经进一步纯化而按粗品使用。
步骤4
向含有(2,3,4,5,6-五氟苯基)3-[二环丙基甲基氨基甲酰基(甲氧基)氨基]-2-甲基-4-甲基磺酰基-苯甲酸酯(0.526g,1.21mmol)的烧瓶中添加乙腈(10mL)。添加5-甲基-1,3,4-噁二唑-2-胺(0.132g,1.33mmol),然后添加2-叔丁基亚氨基-2-二乙基氨基-1,3-二甲基全氢-1,3,2-二吖磷英(0.821g,0.866mL,2.90mmol)并将反应混合物在室温下搅拌过夜。将反应混合物用水稀释并用2M HCl酸化。然后用乙酸乙酯萃取物质。将有机相在真空中浓缩。
将物质通过快速色谱法(环己烷中的0%至75%的EtOAc)纯化,以给出呈灰白色固体的2-氯-4-(二氟甲氧基)-N-(5-甲基-1,3,4-噁二唑-2-基)-3-甲基硫烷基-苯甲酰胺(0.150g,0.399mmol,33%)。1H NMR(甲醇):7.67(d,1H),7.19(d,1H),6.64(t,1H),2.54(s,3H),2.46(s,3H)
实例4.化合物1.002的制备
起始材料是来自实例3的步骤3的产物。
步骤1
向含有(2,3,4,5,6-五氟苯基)2-氯-4-(二氟甲氧基)-3-甲基硫烷基-苯甲酸酯(0.23g,0.53mmol)的烧瓶中添加乙腈(4.6mL)、1-甲基四唑-5-胺(0.115g,1.16mmol)、和2-叔丁基亚氨基-2-二乙基氨基-1,3-二甲基全氢-1,3,2-二吖磷英(0.35mL,1.2mmol)。将反应混合物在室温下搅拌30min,然后在真空中浓缩(室温浴)。将残余物用水稀释并用乙酸乙酯洗涤。然后将水相用2M HCl酸化,并用乙酸乙酯x 2萃取。将合并的有机相干燥(MgSO4)并在减压下浓缩。经快速色谱法(环己烷中的0%至40%的乙酸乙酯),以给出呈白色固体的2-氯-4-(二氟甲氧基)-3-甲基硫烷基-N-(1-甲基四唑-5-基)苯甲酰胺(0.115g,0.329mmol,62%)。
实例5.化合物1.003的制备
起始材料是实施例4中制备的化合物1.002。
向含有2-氯-N-(5-甲基-1,3,4-噁二唑-2-基)-3-甲基硫烷基-4-(三氟甲氧基)苯甲酰胺(0.15g,0.4289mmol)的烧瓶中添加DCM(6mL)和3-氯过氧苯甲酸(0.24g,1.1mmol)。将反应在室温下搅拌16h。添加另一等分部分的3-氯过氧苯甲酸(0.10g,0.44mmol)。在再搅拌2.5h后,添加饱和焦亚硫酸钠水溶液淬灭反应混合物并分离各相。用DCM萃取水相并将合并的有机层干燥(MgSO4),并在减压下浓缩。经快速色谱法(环己烷中的0%至80%的乙酸乙酯),以给出呈白色固体的2-氯-4-(二氟甲氧基)-3-甲基磺酰基-N-(1-甲基四唑-5-基)苯甲酰胺(0.100g,0.263mmol,61%)。
实例6.化合物1.009的制备
起始材料是在来自实例1的步骤3中制备。
步骤1和2
向4-溴-3-氯-2-甲基硫烷基-苯酚(5.10g,20.1mmol)在DMSO(50mL)中的溶液中添加1,2-二溴-1,1,2,2-四氟-乙烷(7.84g,30.2mmol)和KOH(1.46g,26.1mmol)。将混合物在70℃下搅拌16h。将反应混合物冷却至室温,然后在真空中浓缩。将粗物质用水稀释并用乙酸乙酯萃取,并将有机相在真空中浓缩。将物质通过快速色谱法(PE)纯化,以得到呈无色油状物的1-溴-4-(2-溴-1,1,2,2-四氟-乙氧基)-2-氯-3-甲基硫烷基-苯和1-溴-2-氯-3-甲基硫烷基-4-(1,1,2,2-四氟乙氧基)苯的混合物(总:6.3g)。
将此混合物在以下步骤中按粗品使用:
向AcOH(15mL)中的1-溴-4-(2-溴-1,1,2,2-四氟-乙氧基)-2-氯-3-甲基硫烷基-苯和1-溴-2-氯-3-甲基硫烷基-4-(1,1,2,2-四氟乙氧基)苯混合物(总:6.3g)中添加Zn(3.81g,58.3mmol)。将混合物在70℃下搅拌3h。冷却至室温后,将粗物质用水(80ml)稀释并用乙酸乙酯(50ml)萃取,并将有机相用碳酸氢钠溶液(20ml x 3)洗涤并在真空中浓缩,以得到呈无色油状物的1-溴-2-氯-3-甲基硫烷基-4-(1,1,2,2-四氟乙氧基)苯(3.90g,11.0mmol,2步产率:55%)。
步骤3
向1-溴-2-氯-3-甲基硫烷基-4-(1,1,2,2-四氟乙氧基)苯(10.2g,28.8mmol)在乙醇(60mL)中的溶液中添加Pd(OAc)2(0.130g,0.577mmol)和1,1'-双(二苯基膦基)二茂铁(0.800g,1.44mmol)。向混合物中加入CO(2.0MPa)并在120℃下搅拌6h。在冷却至室温后,将粗物质在真空中浓缩并通过快速色谱法(石油醚:乙酸乙酯40:1至20:1)纯化,以得到呈黄色液体的2-氯-3-甲基硫烷基-4-(1,1,2,2-四氟乙氧基)苯甲酸乙酯(8.00g,23.1mmol,80%)。
步骤4
向2-氯-3-甲基硫烷基-4-(1,1,2,2-四氟乙氧基)苯甲酸乙酯(15.0g,43.3mmol)在THF(30mL)和水(30ml)中的溶液中添加LiOH·H2O(5.45g,130mmol)。将混合物在室温下搅拌并搅拌16h。添加稀盐酸调节pH至2。将混合物用乙酸乙酯(50ml)萃取,并将有机相在真空中浓缩并通过快速色谱法(石油醚:乙酸乙酯2:1至1:1)纯化,以得到呈白色固体的2-氯-3-甲基硫烷基-4-(1,1,2,2-四氟乙氧基)苯甲酸(11.5g,36.1mmol,83%)。
步骤5
在室温下,向2-氯-3-甲基硫烷基-4-(1,1,2,2-四氟乙氧基)苯甲酸(2.00g,6.28mmol)和2,3,4,5,6-五氟苯酚(1.27g,6.90mmol)在二氯甲烷(30mL)中的搅拌悬浮液中添加3-(乙基亚氨基亚甲基氨基)-N,N-二甲基-丙烷-1-胺盐酸盐(1.44g,7.51mmol)。将混合物在室温下搅拌。在添加EDC 5分钟后,混合物为均质溶液。将反应混合物在室温下搅拌过夜。通过添加饱和NaHCO3水溶液(100mL)来淬灭反应。将混合物在室温下再搅拌5分钟。将混合物通过相分离柱过滤并收集有机物。将滤液吸附到二氧化硅上,并将粗产物通过快速柱色谱法(环己烷中的0%-10%梯度的EtOAc)纯化,以得到呈淡黄色油状物的(2,3,4,5,6-五氟苯基)2-氯-3-甲基硫烷基-4-(1,1,2,2-四氟乙氧基)苯甲酸酯(3.42g,7.06mmol),将其静置结晶。
步骤6
在室温下,向(2,3,4,5,6-五氟苯基)2-氯-3-甲基硫烷基-4-(1,1,2,2-四氟乙氧基)苯甲酸酯(0.500g,1.03mmol)在乙腈(10mL)中的搅拌溶液中添加1-甲基四唑-5-胺(0.225g,2.270mmol),然后添加2-叔丁基亚氨基-N,N-二乙基-1,3-二甲基-1,3,2-二氮杂膦-2-胺(0.64g,0.68mL,2.3mmol)。将混合物在室温下搅拌过夜。通过添加2M HCl水溶液(100mL)来淬灭反应。将混合物在室温下再搅拌5分钟。将混合物用EtOAc(100mL)稀释。分离各相。将水相用EtOAc(100mL)萃取。将合并的有机相用盐水(100mL)洗涤,干燥(MgSO4)并通过反相色谱法纯化,以给出2-氯-3-甲基硫烷基-N-(1-甲基四唑-5-基)-4-(1,1,2,2-四氟乙氧基)苯甲酰胺(295mg,0.701mmol,68%)。1H NMR(400MHz,d4-甲醇):2.45(s,3H)4.07(s,3H)6.30-6.63(m,1H)7.49-7.55(m,1H)7.66-7.75(m,1H)。
实例7:化合物1.010的制备
起始材料与实例6的步骤4中产生的相同。
步骤1
向含有2-氯-3-甲基硫烷基-4-(1,1,2,2-四氟乙氧基)苯甲酸(3.00g,9.41mmol)的烧瓶中添加二氯甲烷(90mL)和3-氯过氧苯甲酸(6.32g,28.2mmol)。将反应在室温下搅拌16h。将反应混合物用饱和焦亚硫酸钠水溶液淬灭并分离各相。将水层用乙酸乙酯萃取。将合并的有机相浓缩并通过快速色谱法纯化,以给出呈白色固体的2-氯-3-甲基磺酰基-4-(1,1,2,2-四氟乙氧基)苯甲酸(2.46g,75%)。
步骤2
在室温下,向2-氯-3-甲基磺酰基-4-(1,1,2,2-四氟乙氧基)苯甲酸(2.5g,7.1mmol)和2,3,4,5,6-五氟苯酚(1.4g,7.6mmol)在二氯甲烷(30mL)中的搅拌悬浮液中添加3-(乙基亚氨基亚甲基氨基)-N,N-二甲基-丙烷-1-胺盐酸盐(1.6g,8.3mmol)。初始是多相的,然而,在添加EDC的5分钟内,混合物为均质溶液。将混合物在室温下搅拌3小时。通过添加饱和NaHCO3水溶液(100mL)来淬灭反应。将混合物在室温下再搅拌5分钟。将滤液吸附到二氧化硅上,并将粗产物通过快速柱色谱法(环己烷中的0%-10%梯度的EtOAc)纯化,以给出呈无色油状物的(2,3,4,5,6-五氟苯基)2-氯-3-甲基磺酰基-4-(1,1,2,2-四氟乙氧基)苯甲酸酯(3.42g,6.62mmol,93%)。
步骤3
在室温下,向(2,3,4,5,6-五氟苯基)2-氯-3-甲基磺酰基-4-(1,1,2,2-四氟乙氧基)苯甲酸酯(A,300mg,0.5806mmol,100质量%)在乙腈(8mL)中的搅拌溶液中添加1-甲基四唑-5-胺(0.127g,1.28mmol),然后添加2-叔丁基亚氨基-N,N-二乙基-1,3-二甲基-1,3,2-二氮杂膦-2-胺(0.36g,0.38mL,1.3mmol)。将混合物在室温下搅拌2h。通过添加水2M HCl水溶液(10mL)来淬灭反应。将混合物在室温下再搅拌5分钟。将混合物用EtOAc(20mL)稀释。分离各相。将水相用EtOAc(10mL)萃取。将合并的有机相吸附到C18-二氧化硅上,并将粗产物通过反相色谱法纯化。以给出呈白色固体的2-氯-3-甲基磺酰基-N-(1-甲基四唑-5-基)-4-(1,1,2,2-四氟乙氧基)苯甲酰胺(170mg,0.374mmol,64%)。
实例8:化合物1.007的制备
起始材料是实例1中步骤3的产物。
步骤1
将4-溴-3-氯-2-甲基硫烷基-苯酚(2.50g,9.86mmol)在氢氧化钠(水中的5%溶液)(8.87mL)中的溶液添加至二氯硫代羰基(9.86mmol,0.752mL,1.13g)在氯仿(6mL)中的冷却(冰浴)溶液中。将反应混合物通过漂白剂清洗并在0℃下搅拌2.5h。分离各相。将有机层洗涤(2M HCl水溶液,然后是水),干燥(MgSO4)并在真空下浓缩,以给出呈黄色液体的O-(4-溴-3-氯-2-甲基硫烷基-苯基)氯硫代甲酸酯(3.07g,9.24mmol,94%)。1H NMR(400MHz,CDCl3)δ=7.69(d,J=8.7Hz,1H),6.98(d,J=8.8Hz,1H),2.44(s,3H)。
步骤2
将烘箱干燥的烧瓶抽空并用氮气(x3)吹扫。添加O-(4-溴-3-氯-2-甲基硫烷基-苯基)氯硫代甲酸酯(3.00g,9.03mmol)在THF(90mL)中的溶液,然后添加氰化亚铜(I)二(氯化锂)络合物溶液(1M在THF中,9.94mL,9.94mmol)。将其冷却至-78℃。缓慢添加甲基溴化镁(3M溶液在THF中)(9.94mmol,3.31mL)(添加过程中温度保持低于-70℃)。在完成添加后,将其在-78℃下搅拌1h。将反应混合物温热至0℃,并将其在此温度下搅拌1h。通过添加饱和NH4Cl水溶液淬灭反应。将其用EtOAc(x3)萃取。将合并的EtOAc萃取物干燥(MgSO4)并在真空下浓缩。将残余物通过色谱法(环己烷中的0%至10%的EtOAc)纯化,以给出呈黄色油状物的O-(4-溴-3-氯-2-甲基硫烷基-苯基)硫代乙酸酯(1.5g,4.8mmol,53%)。1H NMR(400MHz,CDCl3)δ=7.65(d,J=8.7Hz,1H),6.86(d,J=8.7Hz,1H),2.38(s,3H)
步骤3
在氮气下,搅拌O-(4-溴-3-氯-2-甲基硫烷基-苯基)硫代乙酸酯(1.5g,4.8mmol)在二氯甲烷(19mL)中的溶液。将此溶液用氯化锑(III)(0.24mmol,0.055g),然后用甲苯中的Deoxo-Fluor 50%溶液(6.7mmol,3.4mL)处理。在氮气覆盖下,将反应混合物在室温下搅拌24h。通过添加饱和NaHCO3水溶液淬灭反应混合物。将其用EtOAc(x3)萃取。将合并的EtOAc萃取物干燥(MgSO4)并在真空下浓缩。将残余物通过色谱法(环己烷中的0%至10%的EtOAc在)纯化,以给出1-溴-2-氯-4-(1,1-二氟乙氧基)-3-甲基硫烷基-苯(0.867g,2.73mmol,57%产率)。1H NMR(400MHz,CDCl3)δ=7.56(d,J=8.9Hz,1H),7.15(td,J=1.3,8.9Hz,1H),2.42(s,3H),2.00(t,J=13.4Hz,3H)。
步骤4
向含有NMP(20mL)的容器中添加乙酸钯(II)(74mg,0.33mmol)、XantPhos(39mg,0.66mmol)、N-甲酰基糖精(1.57g,7.44mmol)、和1-溴-2-氯-4-(1,1-二氟乙氧基)-3-甲基硫烷基-苯(1.05g,3.31mmol)。向第二容器中添加三乙胺(2.07mL,14.9mmol)、NMP(20mL)、和水(2.1mL)。反应在Uniqsis FlowSyn中进行。将这两种溶液通过T型管泵送,并且然后围绕加热至170℃的20mL不锈钢盘管。设定流速以使总停留时间为15min。将反应混合物冷却至室温,并用乙酸乙酯稀释。将有机相用2M HCl然后用水洗涤。将有机相在真空中浓缩。将物质通过反相快速色谱法纯化,以给出呈黄色固体的2-氯-4-(1,1-二氟乙氧基)-3-甲基硫烷基-苯甲酸(0.565g,2.00mmol,60%)。1H NMR(d4-甲醇):7.74(d,1H),7.39(m,1H),2.43(s,3H),2.03(m,3H)。
步骤5
向含有2-氯-4-(1,1-二氟乙氧基)-3-甲基硫烷基-苯甲酸(0.565g,2.00mmol)的烧瓶中添加:二氯甲烷(11mL)和2,3,4,5,6-五氟苯酚(0.405g,2.20mmol)。添加3-(乙基亚氨基亚甲基氨基)-N,N-二甲基-丙烷-1-胺盐酸盐(0.464g,2.30mmol),并将反应搅拌1h。通过添加饱和碳酸氢钠水溶液来淬灭反应混合物,并将各相分离并用乙酸乙酯x 2萃取。将有机相合并,干燥(MgSO4)并在真空中浓缩。将粗材料通过快速色谱法(环己烷中的0%至10%的乙酸乙酯)纯化,以给出呈黄色固体的(2,3,4,5,6-五氟苯基)2-氯-4-(1,1-二氟乙氧基)-3-甲基硫烷基-苯甲酸酯(604mg,1.23mmol,63%)。1H NMR(CDCl3):8.01(d,1H),7.45(m,1H),2.45(s,3H),2.06(m,3H)。
步骤6
向含有(2,3,4,5,6-五氟苯基)2-氯-4-(1,1-二氟乙氧基)-3-甲基硫烷基-苯甲酸酯(0.400g,0.892mmol)的烧瓶中添加DCM(4mL)和3-氯过氧苯甲酸(chlorobenzenecarboperoxoic acid)(0.528g,2.14mmol)。搅拌5h后,添加另一份3-氯过氧苯甲酸(0.220g,0.892mmol)。搅拌24h后,通过添加饱和焦亚硫酸钠水溶液来淬灭反应混合物。分离各相并将水层用DCM萃取。将合并的有机层用饱和碳酸钠水溶液x 2洗涤,干燥(MgSO4)并在真空中浓缩,以给出呈淡黄色晶体的(2,3,4,5,6-五氟苯基)2-氯-4-(1,1-二氟乙氧基)-3-甲基磺酰基-苯甲酸酯(0.411g,0.8550mmol,96%)。1H NMR(CDCl3):8.14(d,1H),7.58(m,1H),3.36(s,3H),2.08(m,3H)。
步骤7
向含有(2,3,4,5,6-五氟苯基)2-氯-4-(1,1-二氟乙氧基)-3-甲基硫烷基-苯甲酸酯(0.21g,0.4369mmol)的烧瓶中添加乙腈(4.2mL),然后添加1-甲基四唑-5-胺(0.09524g,0.9611mmol)和2-叔丁基亚氨基-N,N-二乙基-1,3-二甲基-1,3,2-二氮杂膦-2-胺(0.272g,0.287mL,0.961mmol),并在室温下搅拌1h。将反应混合物在真空中浓缩,然后用2M HCl水溶液稀释并用乙酸乙酯萃取。将有机相干燥(MgSO4)4,浓缩并通过反相色谱法纯化,以给出呈白色固体的2-氯-3-甲基磺酰基-N-(1-甲基四唑-5-基)-4-(1,1,2,2-四氟乙氧基)苯甲酰胺(170mg,0.374mmol,64%)。
表1-本发明的除草化合物的实例。
表2-本发明的除草化合物的实例。
生物学实例
将多种测试物种的种子播种在盆中的标准土壤中(多年生黑麦草(Loliumperenne)(LOLPE)、反枝苋(Amaranthus retoflexus)(AMARE)、苘麻(Abutilontheophrasti)(ABUTH)、大狗尾草(Setaria faberi)(SETFA)、稗草(Echinochloa crus-galli)(ECHCG)、碗仔花(Ipomoea hederacea)(IPOHE))。在受控条件下、在温室(在24℃/16℃,白天/夜晚;14小时光照;65%湿度)中培养一天(出苗前)或8天(出苗后)之后,用水性喷雾溶液喷洒这些植物,该水性喷雾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 RN9005-64-5)。除非另外指出,否则化合物以125g/h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=80%-100%;4=60%-79%;3=40%-59%;2=20%-39%;1=0%-19%)。
表B1:出苗前施用
表B2:出苗后施用
*以250g/ha施用
进行对比实验以示出本发明化合物提供的优点。因此,代表性化合物1.004的生物学性能与化合物4-460(WO 2012/028579中提及的类型)。结果以观察到的植物毒性(%)给出。结果表明,本发明的化合物表现出极大改进的作物(ZEAMX/玉米)选择性,即在同等施用率下,本发明的化合物针对棘手的杂草种类提供了改进的控制,同时对作物几乎没有损害。
表B3:比较实验
Claims (16)
2.根据权利要求1所述的化合物,其中Q是Q1。
3.根据权利要求1所述的化合物,其中Q是Q2。
4.根据前述权利要求中任一项所述的化合物,其中R1是C1-C4烷基-。
5.根据权利要求4所述的化合物,其中R1是甲基。
6.根据前述权利要求中任一项所述的化合物,其中R2选自由以下组成的组:氯、甲基和CF3。
7.根据权利要求6所述的化合物,其中R2是氯。
8.根据前述权利要求中任一项所述的化合物,其中R3是C1-C6烷基-。
9.根据权利要求8所述的化合物,其中R3是甲基或乙基。
10.根据前述权利要求中任一项所述的化合物,其中R4是CF3或CHF2。
11.一种除草组合物,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。
12.根据权利要求11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。
13.根据权利要求12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。
14.一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11至13中任一项所述的组合物。
15.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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