CN108884074A - 除草哒嗪酮化合物 - Google Patents
除草哒嗪酮化合物 Download PDFInfo
- Publication number
- CN108884074A CN108884074A CN201780023236.9A CN201780023236A CN108884074A CN 108884074 A CN108884074 A CN 108884074A CN 201780023236 A CN201780023236 A CN 201780023236A CN 108884074 A CN108884074 A CN 108884074A
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- Prior art keywords
- compound
- formula
- methyl
- oxo
- compounds
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- -1 pyridazinone compound Chemical class 0.000 title claims description 122
- 238000009333 weeding Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 200
- 241000196324 Embryophyta Species 0.000 claims abstract description 30
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 229910052701 rubidium Inorganic materials 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims description 129
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 239000004009 herbicide Substances 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 238000009472 formulation Methods 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 9
- 125000005594 diketone group Chemical group 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 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 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 239000011591 potassium Substances 0.000 claims description 6
- 229910052700 potassium Inorganic materials 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000000575 pesticide Substances 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052705 radium Inorganic materials 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 239000010949 copper Substances 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 244000038559 crop plants Species 0.000 abstract description 19
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 390
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 53
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- 239000000243 solution Substances 0.000 description 41
- 239000011541 reaction mixture Substances 0.000 description 32
- 238000002360 preparation method Methods 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 22
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 22
- OPGCOAPTHCZZIW-UHFFFAOYSA-N diethyl 1-(2,4-dichlorophenyl)-5-methyl-4h-pyrazole-3,5-dicarboxylate Chemical group CCOC(=O)C1(C)CC(C(=O)OCC)=NN1C1=CC=C(Cl)C=C1Cl OPGCOAPTHCZZIW-UHFFFAOYSA-N 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 238000005160 1H NMR spectroscopy Methods 0.000 description 14
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 13
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 12
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
- OAWUUPVZMNKZRY-UHFFFAOYSA-N cyprosulfamide Chemical compound COC1=CC=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NC2CC2)C=C1 OAWUUPVZMNKZRY-UHFFFAOYSA-N 0.000 description 11
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- COYBRKAVBMYYSF-UHFFFAOYSA-N heptan-2-yl [(5-chloroquinolin-8-yl)oxy]acetate Chemical group C1=CN=C2C(OCC(=O)OC(C)CCCCC)=CC=C(Cl)C2=C1 COYBRKAVBMYYSF-UHFFFAOYSA-N 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- WMSPXQIQBQAWLL-UHFFFAOYSA-N cyclopropanesulfonamide Chemical compound NS(=O)(=O)C1CC1 WMSPXQIQBQAWLL-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 239000004094 surface-active agent Substances 0.000 description 10
- WVQBLGZPHOPPFO-LBPRGKRZSA-N (S)-metolachlor Chemical compound CCC1=CC=CC(C)=C1N([C@@H](C)COC)C(=O)CCl WVQBLGZPHOPPFO-LBPRGKRZSA-N 0.000 description 9
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
- 239000005489 Bromoxynil Substances 0.000 description 9
- PQKBPHSEKWERTG-UHFFFAOYSA-N Fenoxaprop ethyl Chemical group C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 PQKBPHSEKWERTG-UHFFFAOYSA-N 0.000 description 9
- 239000005578 Mesotrione Substances 0.000 description 9
- 239000005586 Nicosulfuron Substances 0.000 description 9
- 239000005597 Pinoxaden Substances 0.000 description 9
- 239000005617 S-Metolachlor Substances 0.000 description 9
- 240000008042 Zea mays Species 0.000 description 9
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 9
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
- 229910052794 bromium Inorganic materials 0.000 description 9
- JBDHZKLJNAIJNC-LLVKDONJSA-N clodinafop-propargyl Chemical group C1=CC(O[C@H](C)C(=O)OCC#C)=CC=C1OC1=NC=C(Cl)C=C1F JBDHZKLJNAIJNC-LLVKDONJSA-N 0.000 description 9
- 238000004440 column chromatography Methods 0.000 description 9
- 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 9
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- MGOHCFMYLBAPRN-UHFFFAOYSA-N pinoxaden Chemical compound CCC1=CC(C)=CC(CC)=C1C(C1=O)=C(OC(=O)C(C)(C)C)N2N1CCOCC2 MGOHCFMYLBAPRN-UHFFFAOYSA-N 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- WBDLZWMPSRTAJU-RRKGBCIJSA-N (4R)-1-(5-tert-butyl-1,2-oxazol-3-yl)-4-ethoxy-5-hydroxy-3-methylimidazolidin-2-one Chemical compound C(C)(C)(C)C1=CC(=NO1)N1C(N([C@@H](C1O)OCC)C)=O WBDLZWMPSRTAJU-RRKGBCIJSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000005621 Terbuthylazine Substances 0.000 description 8
- 239000003112 inhibitor Substances 0.000 description 8
- 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 8
- 239000004530 micro-emulsion Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 8
- JLYFCTQDENRSOL-UHFFFAOYSA-N 2-chloro-N-(2,4-dimethylthiophen-3-yl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound COCC(C)N(C(=O)CCl)C=1C(C)=CSC=1C JLYFCTQDENRSOL-UHFFFAOYSA-N 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 239000013058 crude material Substances 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 239000000080 wetting agent Substances 0.000 description 7
- MAYMYMXYWIVVOK-UHFFFAOYSA-N 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-4-(methanesulfonamidomethyl)benzoic acid Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=C(CNS(C)(=O)=O)C=2)C(O)=O)=N1 MAYMYMXYWIVVOK-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000005472 Bensulfuron methyl Substances 0.000 description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
- JUJFQMPKBJPSFZ-UHFFFAOYSA-M Iodosulfuron-methyl-sodium Chemical compound [Na+].COC(=O)C1=CC=C(I)C=C1S(=O)(=O)[N-]C(=O)NC1=NC(C)=NC(OC)=N1 JUJFQMPKBJPSFZ-UHFFFAOYSA-M 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- 239000005577 Mesosulfuron Substances 0.000 description 6
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- XMQFTWRPUQYINF-UHFFFAOYSA-N bensulfuron-methyl Chemical group COC(=O)C1=CC=CC=C1CS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 XMQFTWRPUQYINF-UHFFFAOYSA-N 0.000 description 6
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 6
- 235000005822 corn Nutrition 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 239000004546 suspension concentrate Substances 0.000 description 6
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 5
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 description 5
- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 description 5
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 5
- 239000005558 Fluroxypyr Substances 0.000 description 5
- 239000005561 Glufosinate Substances 0.000 description 5
- 239000005562 Glyphosate Substances 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 239000005583 Metribuzin Substances 0.000 description 5
- 239000007832 Na2SO4 Substances 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000002619 bicyclic group Chemical group 0.000 description 5
- VQFAIAKCILWQPZ-UHFFFAOYSA-N bromoacetone Chemical compound CC(=O)CBr VQFAIAKCILWQPZ-UHFFFAOYSA-N 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- MEFQWPUMEMWTJP-UHFFFAOYSA-N fluroxypyr Chemical compound NC1=C(Cl)C(F)=NC(OCC(O)=O)=C1Cl MEFQWPUMEMWTJP-UHFFFAOYSA-N 0.000 description 5
- 238000010353 genetic engineering Methods 0.000 description 5
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 description 5
- 229940097068 glyphosate Drugs 0.000 description 5
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- XSKZXGDFSCCXQX-UHFFFAOYSA-N thiencarbazone-methyl Chemical compound COC(=O)C1=CSC(C)=C1S(=O)(=O)NC(=O)N1C(=O)N(C)C(OC)=N1 XSKZXGDFSCCXQX-UHFFFAOYSA-N 0.000 description 5
- WLDJYTHPKXFPTN-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-6-methyl-3-oxopyridazine-4-carboxylic acid Chemical compound COC=1C=C(C=CC=1OC)N1N=C(C=C(C1=O)C(=O)O)C WLDJYTHPKXFPTN-UHFFFAOYSA-N 0.000 description 4
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 4
- 108010068327 4-hydroxyphenylpyruvate dioxygenase Proteins 0.000 description 4
- FZKHSYGHLYDGKC-UHFFFAOYSA-N 6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxopyridazine-4-carboxylic acid Chemical compound C1(CC1)C=1C=C(C(N(N=1)C1=CC(=C(C=C1)OC)OC)=O)C(=O)O FZKHSYGHLYDGKC-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- 239000005504 Dicamba Substances 0.000 description 4
- 239000005507 Diflufenican Substances 0.000 description 4
- 239000005531 Flufenacet Substances 0.000 description 4
- 241000209219 Hordeum Species 0.000 description 4
- 239000005584 Metsulfuron-methyl Substances 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 4
- WYEHFWKAOXOVJD-UHFFFAOYSA-N diflufenican Chemical compound FC1=CC(F)=CC=C1NC(=O)C1=CC=CN=C1OC1=CC=CC(C(F)(F)F)=C1 WYEHFWKAOXOVJD-UHFFFAOYSA-N 0.000 description 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 4
- 239000004491 dispersible concentrate Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- IANUJLZYFUDJIH-UHFFFAOYSA-N flufenacet Chemical compound C=1C=C(F)C=CC=1N(C(C)C)C(=O)COC1=NN=C(C(F)(F)F)S1 IANUJLZYFUDJIH-UHFFFAOYSA-N 0.000 description 4
- 125000004438 haloalkoxy group Chemical group 0.000 description 4
- 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 4
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- 125000006341 heptafluoro n-propyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052806 inorganic carbonate Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052816 inorganic phosphate Inorganic materials 0.000 description 1
- 229910052920 inorganic sulfate Inorganic materials 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000006229 isopropoxyethyl group Chemical group [H]C([H])([H])C([H])(OC([H])([H])C([H])([H])*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- CONWAEURSVPLRM-UHFFFAOYSA-N lactofen Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)C(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 CONWAEURSVPLRM-UHFFFAOYSA-N 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
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- 238000005259 measurement Methods 0.000 description 1
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- HYYBABOKPJLUIN-UHFFFAOYSA-N mefenamic acid Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1C HYYBABOKPJLUIN-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 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
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- VWGAYSCWLXQJBQ-UHFFFAOYSA-N methyl 4-iodo-2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]benzoate Chemical group COC(=O)C1=CC=C(I)C=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 VWGAYSCWLXQJBQ-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 description 1
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- JAYUDPKFDQGKFQ-UHFFFAOYSA-N n,n-diethylethanamine;ethanol Chemical compound CCO.CCN(CC)CC JAYUDPKFDQGKFQ-UHFFFAOYSA-N 0.000 description 1
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- 125000006095 n-butyl sulfinyl group Chemical group 0.000 description 1
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- 125000001624 naphthyl group Chemical group 0.000 description 1
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- 150000002825 nitriles Chemical class 0.000 description 1
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical compound NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
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- NVGOPFQZYCNLDU-UHFFFAOYSA-N norflurazon Chemical compound O=C1C(Cl)=C(NC)C=NN1C1=CC=CC(C(F)(F)F)=C1 NVGOPFQZYCNLDU-UHFFFAOYSA-N 0.000 description 1
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- 239000012053 oil suspension Substances 0.000 description 1
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- 150000007530 organic bases Chemical class 0.000 description 1
- UCDPMNSCCRBWIC-UHFFFAOYSA-N orthosulfamuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)NC=2C(=CC=CC=2)C(=O)N(C)C)=N1 UCDPMNSCCRBWIC-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
- 239000011236 particulate material Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 108091033319 polynucleotide Proteins 0.000 description 1
- 102000040430 polynucleotide Human genes 0.000 description 1
- 239000002157 polynucleotide Substances 0.000 description 1
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- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
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- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 150000003141 primary amines Chemical class 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
- FROBCXTULYFHEJ-OAHLLOKOSA-N propaquizafop Chemical compound C1=CC(O[C@H](C)C(=O)OCCON=C(C)C)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 FROBCXTULYFHEJ-OAHLLOKOSA-N 0.000 description 1
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- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
- 125000005494 pyridonyl group Chemical group 0.000 description 1
- ZLIBICFPKPWGIZ-UHFFFAOYSA-N pyrimethanil Chemical compound CC1=CC(C)=NC(NC=2C=CC=CC=2)=N1 ZLIBICFPKPWGIZ-UHFFFAOYSA-N 0.000 description 1
- USSIUIGPBLPCDF-KEBDBYFISA-N pyriminobac-methyl Chemical group CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC USSIUIGPBLPCDF-KEBDBYFISA-N 0.000 description 1
- 229910052611 pyroxene Inorganic materials 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
- 235000009736 ragweed Nutrition 0.000 description 1
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- GNHDVXLWBQYPJE-UHFFFAOYSA-N saflufenacil Chemical compound C1=C(Cl)C(C(=O)NS(=O)(=O)N(C)C(C)C)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F GNHDVXLWBQYPJE-UHFFFAOYSA-N 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
- 238000004062 sedimentation Methods 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
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 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
- 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
- RVULBHWZFCBODE-UHFFFAOYSA-M sodium;5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical compound [Na+].C1=C([N+]([O-])=O)C(C(=O)[O-])=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 RVULBHWZFCBODE-UHFFFAOYSA-M 0.000 description 1
- CWTLTFQJQXGTTP-UHFFFAOYSA-M sodium;n'-(2-iodophenyl)sulfonyl-n-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamimidate Chemical compound [Na+].COC1=NC(C)=NC(NC(=O)[N-]S(=O)(=O)C=2C(=CC=CC=2)I)=N1 CWTLTFQJQXGTTP-UHFFFAOYSA-M 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
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- 238000005507 spraying Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000010189 synthetic method Methods 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
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 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
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000003971 tillage Methods 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
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 241001478887 unidentified soil bacteria Species 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having 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
- C07D237/14—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
-
- 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
- C07D403/06—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 carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
本发明涉及具有式(I)的化合物,或所述化合物的农学上可接受的盐,其中A1、R1、Ra、Rb、Rc和Rd是如本文所定义的。本发明进一步涉及除草组合物,其包含具有式(I)的化合物,涉及用于产生具有式(I)的化合物的中间体化合物,涉及用于产生具有式(I)的化合物的方法及涉及具有式(I)的化合物用于控制杂草,特别是在有用植物的作物中的用途。
Description
本发明涉及新颖的除草化合物、涉及用于制备它们的方法、涉及包含这些新颖的化合物的除草组合物、并且涉及其用于特别是在有用植物作物中控制杂草或用于抑制植物生长的用途。
除草哒嗪酮化合物在WO 2012/136703中进行了披露。显示这些化合物对各种有问题的杂草物种提供有效的杂草控制。本发明涉及新颖除草哒嗪酮化合物,其展示出另外的改进特性。特别地,本发明化合物展示出改进的作物选择性。也就是说,它们继续提供有效水平的杂草控制,同时展示出不希望的作物植物毒性的减少。
因此,根据本发明,提供了一种具有式(I)的化合物:
或其农学上可接受的盐,
其中
R1选自下组,该组由以下组成:氢、卤素、氰基、硝基、C1-C6烷基-、C3-C6环烷基-、C2-C6-烯基-、C2-C6炔基-、C1-C6卤代烷基-、C1-C6烷氧基-、C1-C3卤代烷氧基-、C1-C6烷氧基-C1-C3烷基-、C1-C6烷基-S(O)p-和C1-C6卤代烷基-S(O)p-;
A1选自下组,该组由以下组成:O、C(O)和(CReRf);
Ra、Rb、Rc、Rd、Re和Rf各自独立地选自下组,该组由以下组成:氢和C1-C4烷基-,其中Ra和Rc可以一起形成C1-C3亚烷基链;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)。
C2-C6-烯基-包括,例如,-CH=CH2(乙烯基)和-CH2-CH=CH2(丙烯基)。
C2-C6炔基-包括,例如,-C≡CH(乙炔基)和-CH2-C≡CH(炔丙基)。
卤素(或卤代)包括,例如,氟、氯、溴或碘。同样的情况对应地适用于在其他定义的背景中的卤素,例如卤烷基。
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-C6烷氧基-包括,例如,甲氧基、乙氧基、丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基或叔丁氧基或戊氧基或己氧基异构体,优选地是甲氧基和乙氧基。
C1-C3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,优选地是二氟甲氧基、2-氯乙氧基或三氟甲氧基。
C1-C6烷基-S-(烷基硫基)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,优选地是甲硫基或乙硫基。C1-C6卤代烷基-S-(卤代烷基硫基)涉及其卤化衍生物。
C1-C6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,优选地是甲基亚磺酰基或乙基亚磺酰基。C1-C6卤代烷基-S(O)-(卤代烷基亚磺酰基)涉及其卤化衍生物。
C1-C6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,优选地是甲基磺酰基或乙基磺酰基。C1-C6卤代烷基-S(O)2-(卤代烷基磺酰基)涉及其卤化衍生物。
C1-C6烷氧基-C1-C3烷基-包括,例如,甲氧基甲基、甲氧基乙基、乙氧基甲基、乙氧基乙基、正丙氧基甲基、正丙氧基乙基、异丙氧基甲基或异丙氧基乙基。
C3-C6环烷基-包括,例如,环丙基(c-丙基(c-Pr))、环丁基(c-丁基(c-Bu))、环戊基(c-戊基)和环己基(c-己基)。
在本发明的一个优选实施例中,提供了具有式(I)的化合物,其中R1是C1-C6烷基-(优选甲基)或C3-C6环烷基-(优选环丙基)。在一个更优选的实施例中,R1是甲基或环丙基。
在本发明的一个优选实施例中,提供了具有式(I)的化合物,其中A1是CReRf并且Re和Rf是氢。
在本发明的另一个优选的实施例中,提供了具有式(I)的化合物,其中A1是CReRf并且Ra、Rb、Rc、Rd、Re和Rf是氢。
在本发明的另一个优选的实施例中,提供了具有式(I)的化合物,其中A1是CReRf;Ra、Rb、Rc、Rd和Re是氢并且Rf是甲基。
在本发明的另一个优选的实施例中,提供了具有式(I)的化合物,其中A1是CReRf;Ra、Rb、Rc、Rd是氢并且Re和Rf是甲基。
在本发明的另一个优选的实施例中,提供了具有式(I)的化合物,其中A1是CReRf;Rb、Rd、Re和Rf是氢,并且Ra和Rc一起形成乙烯基(-CH2-CH2-)链。
在本发明的另一个优选的实施例中,提供了具有式(I)的化合物,其中A1是C=O并且Ra、Rb、Rc和Rd是甲基。
在本发明的另一个优选的实施例中,提供了具有式(I)的化合物,其中A1是O且Ra、Rb、Rc和Rd是甲基。
具有式(I)的化合物可以包含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,或其中存在多于一个不对称中心,包含所有可能比率的非对映异构体。通常,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。
类似地,在存在经双取代的或经三取代的烯烃的地方,这些能以E或Z形式或作为任何比例下的二者的混合物而存在。
此外,具有式(I)的化合物可以与可替代的互变异构形式相平衡。因此,同时描述具有式(I)的化合物处于酮形式,但它们也可能处于可替代烯醇形式,如下式(I')中所描述的。
所有互变异构形式(单一互变异构体或其混合物)、外消旋混合物和单一异构体被包括在本发明的范围内。
表C1–本发明的除草化合物的实例。
本发明还提供了具有式(I)的化合物的农业上可接受的盐。优选具有式(I)的化合物可与如下形成的盐:胺类,包括伯、仲和叔胺(例如氨、二甲胺和三乙胺),碱金属和碱土金属碱类,过渡金属或季铵碱类。特别优选具有式(I)的化合物的铝、钙、钴、铜(铜(I)、铜(II))、铁(铁(II)、铁(III))、镁、钾、钠或锌盐;尤其优选铜、钾和钠。
根据本发明的具有式(I)的化合物可以自身被用作除草剂,但是通常使用共配制品(如载体、溶剂、表面活性剂(SAA)和佐剂)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,该除草组合物包括根据以上权利要求中任一项所述的除草化合物和农业上可接受的共配制品。该组合物可以处于浓缩物的形式,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。
这些除草组合物总体上包括按重量计从0.1%到99%,尤其是按重量计从0.1%到95%的具有式I的化合物以及按重量计从1%到99.9%的共配制品,该共配制品优选地包括按重量计从0到25%的表面活性物质。
该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)、油分散体(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)、ZC(SC和CS的组合)和可溶性颗粒剂(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)的化合物和任何另外的成分的物理、化学和生物学特性。
可溶性粉剂(SP)可以通过将具有式(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来制备以改进水分散性/水溶性。然后将该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,一种或多种的悬浮剂混合来制备以促进在液体中的分散。然后将该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来形成,或者通过将具有式(I)的化合物(或其在一种适合试剂中的溶液)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(或其在适合试剂中的溶液)吸附到硬芯材料(如沙、硅酸盐、无机碳酸盐、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)。这些颗粒剂中也可包括一种或多种其他的添加剂(例如乳化剂、润湿剂或分散剂)。
可分散的浓缩物(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(任选地包含一种或多种湿润剂、一种或多种乳化剂或者所述试剂的混合物)中来制备。在EC中使用的适合的有机溶剂包括芳香族烃类(如烷基苯或烷基萘,例如SOLVESSO100、SOLVESSO 150和SOLVESSO 200;SOLVESSO是注册商标)、酮类(如环己酮或甲基环己酮)和醇类(如苯甲醇、糠醇或丁醇)、和脂肪酸的二甲基酰胺(如C8-C10脂肪酸二甲基酰胺)。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一种液体(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,然后在高剪切下将所得液体或溶液乳化进包含一种或多种SAA的水中,以产生乳液。在EW中使用的适合的溶剂包括植物油、芳香族溶剂(如烷基苯或烷基萘)以及其他在水中具有低溶解度的适当的有机溶剂。
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)的化合物一开始就存在于水中或溶剂/SAA共混物中。在ME中使用的适合的溶剂包括此前描述的在EC或EW中使用的那些。ME可以是水包油系统或油包水系统(存在哪种系统可以通过电导率测量来确定)并且可以适合用于在相同配制品中混合水溶性的和油溶性的杀有害生物剂。ME适合于稀释到水中,同时保持为微乳液或者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可以任选地使用一种或多种分散剂通过在适合的介质中球磨或珠磨具有式(I)的固体化合物来制备,以产生该化合物的精细颗粒悬浮液。在该组合物中可以包括一种或多种湿润剂,并且可以包括悬浮剂以降低颗粒的沉降速率。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试剂的水中,以产生希望的终产物。
气溶胶配制品包括具有式(I)的化合物和适合的推进剂(例如,正丁烷)。也可以将具有式(I)的化合物溶于或分散于适合的介质(例如水或可与一种水混溶的液体,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)可以通过以与制备EW配制品类似的方式来制备,但具有额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其载体或稀释剂。该聚合物壳可以通过界面缩聚反应或通过凝聚程序来制备。这些组合物可以提供具有式(I)的化合物的受控释放。具有式(I)的化合物也可以被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释放。
可溶性浓缩物(SL)可以通过将活性成分溶解在任选地包含一种或多种润湿剂和/或一种或多种缓冲剂的水性液体中来制备。
组合物可以包括一或多种添加剂以改进组合物的生物学性能,例如通过改进在表面上的湿润性,保持力或分布;被处理表面上的防雨;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(如大豆和油菜籽油),改性的植物油(如甲基化油菜籽油(MRSO))以及这些与其他生物增强佐剂(可帮助或改变具有式(I)的化合物的作用的成分)的掺合物。
共配制品的实例包括:-
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。
适合的阳离子类型的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。
适合的阴离子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)、硫代琥珀酰胺酸盐、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酯/硫酸酯。
适合的两性型的SAA包括甜菜碱、丙酸盐和甘氨酸盐。
适合的非-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)的缩合产物;来自长链脂肪酸或己糖醇酐的偏酯;所述的偏酯与环氧乙烷的缩合产物;嵌段聚合物(含有环氧乙烷和环氧丙烷);烷醇酰胺;单酯(例如脂肪酸聚乙烯乙二醇酯);胺氧化物(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。
适合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)。
本发明的组合物可以进一步包含一种或多种另外的杀有害生物剂。例如,根据本发明的化合物也可以与其他除草剂或植物生长调节剂组合使用。因此,在一个优选实施例中,提供了除草组合物,该组合物包含(A)具有式(I)的化合物和(B)一种或多种选自下组的除草剂,该组由以下组成:乙草胺、三氟羧草醚(三氟羧草醚钠)、苯草醚、甲草胺、禾草灭、莠灭净、氨唑草酮、酰嘧磺隆、环丙嘧啶酸、氯氨基吡啶酸、杀草强、莎稗磷、磺草灵、莠去津、氟丁酰草胺、氟草氨、氟草胺、苄嘧磺隆(包括苄嘧磺隆-甲基)、噻草平、二环吡喃酮、治草醚、双草醚钠、除草定、溴苯腈、丁草胺、丁苯草酮、氟丙嘧草酯、唑草胺、唑酮草酯(包括唑酮草酯-乙基)、氯酯磺草胺酸、氯嘧磺隆(包括氯嘧磺隆-乙基)、绿麦隆、氯磺隆、醚磺隆、吲哚酮(包括吲哚酮草酯)、烯草酮、炔草酯(包括炔草酯-炔丙基)、异噁草酮、二氯吡啶酸、噻草酮、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)、杀草隆、甜菜安、麦草畏(包括其铝、氨丙基、二-氨基丙基甲基、胆碱、滴丙酸、二甘醇胺、二甲胺、二甲基胺、钾和钠盐)、禾草灵(包括禾草灵-甲基)、双氯磺草胺、野燕枯、吡氟酰草胺、氟吡草腙、二甲草胺、二甲吩草胺、敌草快二溴化物、敌草隆、EPTC、戊草丹、胺苯磺隆、甜菜呋、精噁唑禾草灵(包括精噁唑禾草灵-乙基)、芬奎崔顿、啶嘧磺隆、双氟磺草胺、精噁氟禾草灵(包括精噁氟禾草灵-丁基)、氟酮磺隆(包括氟酮磺隆钠)、氟噻草胺、氟节胺、唑嘧磺草胺、fluormeturon、乙羧氟草醚、丙炔氟草胺、氟啶嘧磺隆(包括氟啶嘧磺隆-甲基钠)、氟草烟(包括氯氟吡氧乙酸)、呋草酮、嗪草酸(包括嗪草酸甲酯)、氟磺胺草醚、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(包括氟氯吡啶酯-甲基)、氯吡嘧磺隆(包括氯吡嘧磺隆-甲基)、氟吡禾灵(包括氟吡甲禾灵)、环嗪酮、咪草酸、甲氧咪草烟、甲咪唑烟酸、灭草烟、咪唑喹啉酸、咪草烟、茚嗪氟草胺、碘甲磺隆(包括碘甲磺隆甲酯钠盐)、iofensulfuron(包括iofensulfuron钠)、碘苯腈、ipfencarbazone、异丙隆、异噁酰草胺、异噁唑草酮、乳氟禾草灵、利谷隆、MCPA、高2甲4氯丙酸、苯噻酰草胺、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、秀谷隆、异丙甲草胺、甲氧隆、嗪草酮、甲磺隆、草达灭、敌草胺、烟嘧磺隆、达草灭、嘧苯胺磺隆、丙炔噁草酮、噁草酮、环氧嘧磺隆、噁嗪草酮、乙氧氟草醚、百草枯二氯化物、二甲戊乐灵、五氟磺草胺、烯草胺、甜菜宁、毒莠定、氟吡酰草胺、唑啉草酯、丙草胺、氟嘧磺隆、氨氟乐灵、扑草净、毒草安、敌稗、喔草酯、苯胺灵、丙苯磺隆、戊炔草胺、苄草丹、氟丙磺隆、吡草醚(包括吡草醚-乙基)、磺酰草吡唑、吡唑特、吡嘧磺隆(包括吡嘧磺隆-乙基)、嘧啶肟草醚、哒草特、环酯草醚、嘧草硫醚、罗克杀草砜、啶磺草胺、二氯喹啉酸、喹禾灵(包括精喹禾灵)、砜嘧磺隆、嘧啶肟草醚、稀禾定、西草净、S-异丙甲草胺、磺草酮、甲磺草胺、嘧磺隆(包括甲嘧磺隆)、磺酰磺隆、丁噻隆、特呋三酮、环磺酮、吡喃草酮、特丁津、去草净、噻酮磺隆、噻吩磺隆、地芬纳噻、托比利特、苯吡唑草酮、三甲苯草酮、氟酮磺草胺、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)、三氟地杀嗪、氟乐灵、三氟甲磺隆、4-氨基-3-氯-6-(4-氯-2-氟-3-甲氧基苯基)-5-氟吡啶-2-羧酸酯(化合物B1)、4-羟基-1-甲氧基-5-甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑烷-2-酮(化合物B2)、4-羟基-1,5-二甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑烷-2-酮(化合物B3)、5-乙氧基-4-羟基-1-甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑烷-2-酮(化合物B4)、4-羟基-1-甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑烷-2-酮(化合物B5)、4-羟基-1,5-二甲基-3-[1-甲基-5-(三氟甲基)吡唑-3-基]咪唑烷-2-酮(化合物B6)、(4R)1-(5-叔丁基异噁唑-3-基)-4-乙氧基-5-羟基-3-甲基-咪唑烷-2-酮(化合物B7),具有式B8的化合物,
其中,
R1是H、C1-C6烷基、C1-C6卤代烷基或C4-C8环烷基;
R6是H、C1-C6烷基、或C1-C6烷氧基;
Q1是任选地经取代的环系统,所述环系统选自下组,该组由以下组成:苯基、噻吩基、吡啶基、苯并二氧杂环戊烯基、萘基、萘基、苯并呋喃基、呋喃基、苯并苯硫基、和吡唑基,其中当经取代的所述环系统被1至3个R4所取代时;
Q2是任选地经取代的环系统,所述环系统选自下组,该组由以下组成:苯基、吡啶基、苯并二氧杂环戊烯基、吡啶酮基、噻二唑基、噻唑基、和噁唑基,其中当经取代的所述环系统被1至3个R5所取代时;
每个R4独立地是卤素、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C3-C8环烷基、氰基、C1-C6烷基硫基、C1-C6烷基亚磺酰基、C1-C6烷基磺酰基、SF5、NHR8、任选地被1-3个R7取代的苯基、或任选地被1-3个R7取代的吡唑基;
每个R5独立地是卤素、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基、C1-C6卤代烷氧基、氰基、硝基、C1-C6烷基硫基、C1-C6烷基亚磺酰基、或C1-C6烷基磺酰基;
每个R7独立地是C1-C6烷基、卤素、或C1-C6卤代烷基;并且
R8是C1-C4烷氧基羰基;
和具有式B9的化合物,
其中,
R11是H、C1-C6烷基、C1-C6卤代烷基或C4-C8环烷基;
n是0、1、2或3中的整数;
p是0、1、2或3中的整数;
每个R2独立地是卤素、C1-C6卤代烷基、或C1-C6卤代烷氧基;并且
每个R3独立地是卤素、C1-C6卤代烷基、C1-C6卤代烷氧基。
更优选地,(B)是一种或多种选自下组的除草剂,该组由以下组成:乙草胺、甲草胺、莠灭净、氨唑草酮、莠去津、二环吡喃酮、溴苯腈、丁草胺、绿麦隆、炔草酯-炔丙基、二氯吡啶酸、2,4-D(包括其胆碱盐和2-乙基己基酯)、麦草畏(包括其铝、氨丙基、双氨基丙基甲基、胆碱盐、二甘醇胺、二甲胺、二甲基铵、钾和钠盐)、吡氟酰草胺、二甲草胺、二甲吩草胺、敌草隆、氟吡甲禾灵、芬奎崔顿、双氟磺草胺、吡氟禾草灵、氟氯比、氟酮磺隆钠、氟噻草胺、甲酰胺磺隆、草铵膦(包括其铵盐)、氟磺胺草醚、草甘膦(包括其二铵、异丙基铵和钾盐)、氟氯吡啶酯-甲基、碘甲磺隆甲酯钠盐、异噁唑草酮、异丙隆、利谷隆、MCPA、高2甲4氯丙酸、甲基二磺隆-甲基、甲基磺草酮、吡唑草胺、S-异丙甲草胺、嗪草酮、甲磺隆、烟嘧磺隆、二甲戊乐灵、烯草胺、唑啉草酯、扑草净、苄草丹、氟丙磺隆、磺酰草吡唑、哒草特、罗克杀草砜、啶磺草胺、砜嘧磺隆、西玛津、磺草酮、甲磺草胺、环磺酮、特丁津、去草净、噻酮磺隆、托比利特、苯吡唑草酮、醚苯磺隆和三氟地杀嗪。
甚至更优选地,(B)是一种或多种选自下组的除草剂,该组由以下组成:莠去津、二环吡喃酮、溴苯腈、炔草酯-炔丙基、吡氟酰草胺、精噁唑禾草灵-乙基、双氟磺草胺、氟噻草胺、氟氯比、草铵膦(包括其铵盐)、草甘膦(包括其二铵、异丙基铵和钾盐)、氟氯吡啶酯-甲基、碘甲磺隆甲酯钠、MCPA、甲基二磺隆-甲基、甲基磺草酮、嗪草酮、甲磺隆、烟嘧磺隆、S-异丙甲草胺、唑啉草酯、苄草丹、啶磺草胺和特丁津。
在一个实施例中,其中组分B是具有式B8的化合物,优选的是R11是H、C1-C6烷基或C1-C6卤代烷基,更优选甲基、乙基或CHF2,和仍更优选H或甲基。
优选地,R6是H。优选Q1是苯基环或吡啶基环,其中每一个任选地被1至3个R4取代。优选地,Q1是被1至2个R4取代的苯基环。优选地,Q2是任选地被1在3个R5取代的苯基环。更优选Q1是被1-3个R5取代的苯基。优选地,每个R4独立地是卤素、C1-C4烷基、C1-C3卤代烷基、C1-C3烷氧基、或C1-C3卤代烷氧基;更优选地氯、氟、溴、C1-C2卤代烷基、C1-C2卤代烷氧基、或C1-C2烷氧基。优选地,每个R5独立地是卤素、C1-C4烷基、C1-C3卤代烷基、C1-C3烷氧基、或C1-C3卤代烷氧基;更优选地氯、氟、溴、C1-C2卤代烷基、C1-C2卤代烷氧基、或C1-C2烷氧基;仍更优选地氟。
特别优选的用作本发明的组合物中的组分B的具有式B8的化合物如下表B8中的化合物B801至B815所示。
表B8用于本文描述的组合物的具有式(B8)的化合物。
如本文描述的具有式B8的化合物可以如WO 2015/084796和WO 2016/094117中所描述制备。
在另外的实施例中,其中组分B是具有式B9的化合物,优选的是p是1、2、或3,更优选地1或2。优选地,n是1、2或3,更优选是1或2。优选地,R1是H或C1-C6烷基,更优选地是H或甲基。在一组实施例中,R11是H。
优选地,每个R2独立地是氯、氟、C1-C3卤代烷基、或C1-C3卤代烷氧基,更优选地氯、氟、C1-氟烷基(即氟甲基、二氟甲基、三氟甲基)C1-氟烷氧基(即三氟甲氧基、二氟甲氧基、氟甲氧基)。优选地,每个R3独立地是氯、氟、C1-C3卤代烷基、或C1-C3卤代烷氧基,更优选地氯、氟、C1-氟烷基(即氟甲基、二氟甲基、三氟甲基)C1-氟烷氧基(即三氟甲氧基、二氟甲氧基、氟甲氧基)。特别优选的用作本发明的组合物中的组分B的具有式B9的化合物如下表B9中所示。
表B9.用于本文描述的组合物中的具有式B9的化合物(除非另外说明,所有化合物处于外消旋形式)。
如本文描述的具有式B9的化合物可以如WO 2016/003997中所描述制备。
在一个实施例中,参考上文提及的组合物,组分(A)是化合物1.1。在另一个实施例中,参考上文提及的组合物,组分(A)是化合物1.2。在另一个实施例中,参考上文提及的组合物,组分(A)是化合物1.3。在另一个实施例中,参考上文提及的组合物,组分(A)是化合物1.4。在另一个实施例中,参考上文提及的组合物,组分(A)是化合物1.5。在另一个实施例中,参考上文提及的组合物,组分(A)是化合物1.6。在另一个实施例中,参考上文提及的组合物,组分(A)是化合物1.7。在另一个实施例中,参考上文提及的组合物,组分(A)是化合物1.8。在另一个实施例中,参考上文提及的组合物,组分(A)是化合物1.9。在另一个实施例中,参考上文提及的组合物,组分(A)是化合物1.10。在另一个实施例中,参考上文提及的组合物,组分(A)是化合物1.11。在另一个实施例中,参考上文提及的组合物,组分(A)是化合物1.12。在另一个实施例中,参考上文提及的组合物,组分(A)是化合物1.13。在另一个实施例中,参考上文提及的组合物,组分(A)是化合物1.14。
本发明的另外的实例组合物包含:
化合物1.1+乙草胺、化合物1.1+氟锁草醚钠、化合物1.1+苯草醚、化合物1.1+甲草胺、化合物1.1+禾草灭、化合物1.1+莠灭净、化合物1.1+氨唑草酮、化合物1.1+酰嘧磺隆、化合物1.1+环丙嘧啶酸、化合物1.1+氯氨吡啶酸、化合物1.1+杀草强、化合物1.1+黄草灵、化合物1.1+莠去津、化合物1.1+氟丁酰草胺、化合物1.1+氟草胺、化合物1.1+苄嘧磺隆甲酯、化合物1.1+灭草松、化合物1.1+氟吡草酮、化合物1.1+治草醚、化合物1.1+双草醚钠、化合物1.1+丁溴啶、化合物1.1+溴草腈、化合物1.1+丁草胺、化合物1.1+丁苯草酮、化合物1.1+氟丙嘧草酯、化合物1.1+唑草胺、化合物1.1+唑酮草酯、化合物1.1+氯酯磺草胺酸、化合物1.1+氯嘧磺隆乙酯、化合物1.1+绿麦隆、化合物1.1+氯磺隆、化合物1.1+醚磺隆、化合物1.1+吲哚酮草酯、化合物1.1+烯草酮、化合物1.1+炔草酯、化合物1.1+广灭灵、化合物1.1+二氯吡啶酸、化合物1.1+噻草酮、化合物1.1+氰氟草酯、化合物1.1+2,4-D(包括其胆碱盐和2-乙基己基酯)、化合物1.1+杀草隆、化合物1.1+甜菜安、化合物1.1+麦草畏(包括其铝、氨丙基、双氨基丙基甲基、胆碱、二甘醇胺、二甲胺、二甲基铵、钾和钠盐)、化合物1.1+禾草灵甲酯、化合物1.1+双氯磺草胺、化合物1.1+野燕枯、化合物1.1+吡氟酰草胺、化合物1.1+氟吡草腙、化合物1.1+二甲草胺、化合物1.1+二甲吩草胺、化合物1.1+敌草快二溴化物、化合物1.1+敌草隆、化合物1.1+禾草畏、化合物1.1+胺苯磺隆、化合物1.1+乙氧呋草黄、化合物1.1+精噁唑禾草灵-乙酯、化合物1.1+芬奎崔顿、化合物1.1+四唑酰草胺、化合物1.1+啶嘧磺隆、化合物1.1+双氟磺草胺、化合物1.1+吡氟禾草灵丁酯、化合物1.1+氟酮磺隆钠、化合物1.1+氟噻草胺、化合物1.1+氟节胺、化合物1.1+唑嘧磺草胺、化合物1.1+丙炔氟草胺、化合物1.1+氟啶嘧磺隆-甲基钠、化合物1.1+氟氯比、化合物1.1+呋草酮、化合物1.1+氟噻甲草酯、化合物1.1+氟磺胺草醚、化合物1.1+甲酰胺磺隆、化合物1.1+草铵膦(包括其铵盐)、化合物1.1+草甘膦(包括其二铵盐、异丙基铵盐和钾盐)、化合物1.1+氟氯吡啶酯、化合物1.1+氯吡嘧磺隆、化合物1.1+吡氟氯禾灵、化合物1.1+环嗪酮、化合物1.1+咪草酯、化合物1.1+甲氧咪草烟、化合物1.1+甲咪唑烟酸、化合物1.1+灭草烟、化合物1.1+灭草喹、化合物1.1+咪草烟、化合物1.1+三嗪茚草胺、化合物1.1+碘甲磺隆钠、化合物1.1+碘磺隆、化合物1.1+碘磺隆钠、化合物1.1+碘苯腈、化合物1.1+三唑酰草胺、化合物1.1+异丙隆、化合物1.1+异噁酰草胺、化合物1.1+异噁唑草酮、化合物1.1+乳氟禾草灵、化合物1.1+利谷隆、化合物1.1+MCPA、化合物1.1+氯丙酸、化合物1.1+苯噻酰草胺、化合物1.1+甲基二磺隆、化合物1.1+甲基二磺隆甲酯、化合物1.1+硝磺草酮、化合物1.1+苯嗪草酮、化合物1.1+吡草胺、化合物1.1+莠谷隆、化合物1.1+异丙甲草胺、化合物1.1+甲氧隆、化合物1.1+赛克嗪、化合物1.1+甲磺隆、化合物1.1+草达灭、化合物1.1+敌草胺、化合物1.1+烟嘧磺隆、化合物1.1+达草灭、化合物1.1+嘧苯胺磺隆、化合物1.1+丙炔噁草酮、化合物1.1+噁草酮、化合物1.1+环氧嘧磺隆、化合物1.1+噁嗪草酮、化合物1.1+乙氧氟草醚、化合物1.1+百草枯二氯化物、化合物1.1+二甲戊乐灵、化合物1.1+五氟磺草胺、化合物1.1+烯草胺、化合物1.1+甜菜宁、化合物1.1+毒莠定、化合物1.1+氟吡酰草胺、化合物1.1+唑啉草酯、化合物1.1+丙草胺、化合物1.1+氟嘧磺隆甲酯、化合物1.1+氨氟乐灵、化合物1.1+扑草净、化合物1.1+扑草胺、化合物1.1+敌稗、化合物1.1+喔草酯、化合物1.1+苯胺灵、化合物1.1+丙苯磺隆、化合物1.1+拿草特、化合物1.1+苄草丹、化合物1.1+氟磺隆、化合物1.1+磺酰草吡唑、化合物1.1+吡唑特、化合物1.1+吡嘧磺隆乙酯、化合物1.1+嘧啶肟草醚、化合物1.1+哒草特、化合物1.1+环酯草醚、化合物1.1+嘧硫草醚、化合物1.1+罗克杀草砜、化合物1.1+甲氧磺草胺、化合物1.1+快杀稗、化合物1.1+精喹禾灵、化合物1.1+砜嘧磺隆、化合物1.1+苯嘧磺草胺、化合物1.1+稀禾定、化合物1.1+S-异丙甲草胺、化合物1.1+磺草酮、化合物1.1+甲磺草胺、化合物1.1+嘧磺隆甲酯、化合物1.1+磺酰磺隆、化合物1.1+丁噻隆、化合物1.1+特呋三酮、化合物1.1+环磺酮、化合物1.1+特丁津、化合物1.1+去草净、化合物1.1+噻酮磺隆、化合物1.1+噻吩磺隆、化合物1.1+tiafenacil、化合物1.1+托比利特、化合物1.1+苯吡唑草酮、化合物1.1+肟草酮、化合物1.1+氟酮磺草胺、化合物1.1+野麦畏、化合物1.1+醚苯磺隆、化合物1.1+苯磺隆甲酯、化合物1.1+绿草定、化合物1.1+三氟啶磺隆钠、化合物1.1+三氟地杀嗪、化合物1.1+氟乐灵、化合物1.1+三氟甲磺隆以及化合物1.1+4-氨基-3-氯-6-(4-氯-2-氟-3-甲氧基苯基)-5-氟吡啶-2-甲酸酯;(化合物B1)、1.1+4-羟基-1-甲氧基-5-甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑烷-2-酮(化合物B2)、1.1+4-羟基-1,5-二甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑烷-2-酮(化合物B3)、1.1+5-乙氧基-4-羟基-1-甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑烷-2-酮(化合物B4)、1.1+4-羟基-1-甲基-3-[4-(三氟甲基)-2-吡啶基]咪唑烷-2-酮(化合物B5)、1.1+4-羟基-1,5-二甲基-3-[1-甲基-5-(三氟甲基)吡唑-3-yl]咪唑烷-2-酮(化合物B6)、1.1+(4R)1-(5-叔丁基异噁唑-3-基)-4-乙氧基-5-羟基-3-甲基-咪唑烷-2-酮(化合物B7);
化合物1.1+N-(2-氟苯基)-2-氧代-4-[3-(三氟甲基)苯基]-吡咯烷-3-甲酰胺(化合物B801)、化合物1.1+N-(2,3-二氟苯基)-2-氧代-4-[3-(三氟甲基)苯基]吡咯烷-3-甲酰胺(化合物B802)、化合物1.1+2-氧代-4-[3-(三氟甲基)苯基]-N-(2,3,4-三氟苯基)吡咯烷-3-甲酰胺(化合物B803)、化合物1.1+N-(2-氟苯基)-1-甲基-2-氧代-4-[3-(三氟甲基)苯基]吡咯烷-3-甲酰胺(化合物B804)、化合物1.1+N-(2-氟苯基)-2-氧代-4-[4-(三氟甲基)苯基]吡咯烷-3-甲酰胺(化合物B805)、化合物1.1+N-(2-氟苯基)-1-甲基-2-氧代-4-[4-(三氟甲基)苯基]吡咯烷-3-甲酰胺(化合物B806)、化合物1.1+N-(2,3-二氟苯基)-2-氧代-4-[4-(三氟甲基)苯基]吡咯烷-3-甲酰胺(化合物B807)、化合物1.1+N-(2,3-二氟苯基)-1-甲基-2-氧代-4-[4-(三氟甲基)苯基]吡咯烷-3-甲酰胺(化合物B808)、化合物1.1+2-氧代-4-[4-(三氟甲基)苯基]-N-(2,3,4-三氟苯基)吡咯烷-3-甲酰胺(化合物B809)、化合物1.1+N-(2-氟苯基)-4-(4-氟苯基)-1-甲基-2-氧代-吡咯烷-3-甲酰胺(化合物B810)、化合物1.1+N-(2,3-二氟苯基)-4-(3,4-二氟苯基)-2-氧代-吡咯烷-3-甲酰胺(化合物B811)、化合物1.1+4-(3,4-二氟苯基)-N-(2-氟苯基)-2-氧代-吡咯烷-3-甲酰胺(化合物B812)、化合物1.1+N-(2,4-二氟苯基)-4-(3,5-二氟苯基)-2-氧代-吡咯烷-3-甲酰胺(化合物B813)、化合物1.1+N-(2,3-二氟苯基)-4-(3-异丙基苯基)-2-氧代-吡咯烷-3-甲酰胺(化合物B814)、化合物1.1+N-(2,3-二氟苯基)-2-氧代-4-[6-(三氟甲基)-3-吡啶基]吡咯烷-3-甲酰胺(化合物B815);
化合物1.1+4-(3,4-二氟苯基)-2-氧代-N-[2-(三氟甲基)苯基]-哌啶-3-甲酰胺(化合物B901)、化合物1.1+N-(2,3-二氟苯基)-2-氧代-4-[3-(三氟甲基)苯基]哌啶-3-甲酰胺(化合物B902)、化合物1.1+2-氧代-N-[2-(三氟甲基)苯基]-4-[3-(三氟甲基)苯基]哌啶-3-甲酰胺(化合物B903)、化合物1.1+N-(2-氯苯基)-2-氧代-4-[4-(三氟甲基)苯基]哌啶-3-甲酰胺(化合物B904)、化合物1.1+N-(2-氟苯基)-2-氧代-4-[4-(三氟甲基)苯基]哌啶-3-甲酰胺(化合物B905)、化合物1.1+(3R,4S)-N-(2,3-二氟苯基)-2-氧代-4-[3-(三氟甲基)苯基]哌啶-3-甲酰胺(化合物B906)、化合物1.1+(3R,4S)-N-(2,3-二氟苯基)-2-氧代-4-[4-(三氟甲基)苯基]哌啶-3-甲酰胺(化合物B907)、化合物1.1+(3R,4S)-N-(3-氯-2-氟-苯基)-2-氧代-4-[3-(三氟甲基)苯基]哌啶-3-甲酰胺(化合物B908)、化合物1.1+(3R,4S)-2-氧代-4-[3-(三氟甲基)苯基]-N-(2,3,4-三氟苯基)哌啶-3-甲酰胺(化合物909)、化合物1.1+N-(2,3-二氟苯基)-2-氧代-4-苯基-哌啶-3-甲酰胺(化合物B910)、化合物1.1+N-(2-氟苯基)-2-氧代-4-[3-(三氟甲氧基)苯基]哌啶-3-甲酰胺(化合物B911)、化合物1.1+2-氧代-4-[3-(三氟甲氧基)苯基]-N-[2-(三氟甲基)苯基]哌啶-3-甲酰胺(化合物B912)、化合物1.1+N-(2,3-二氟苯基)-2-氧代-4-[3-(三氟甲氧基)苯基]哌啶-3-甲酰胺(化合物B913)、化合物1.1+(3R,4S)-4-(3-氯苯基)-N-(2,3-二氟苯基)-2-氧代-哌啶-3-甲酰胺(化合物B914)、化合物1.1+4-[3-(二氟甲基)苯基]-2-氧代-N-(2,3,4-三氟苯基)哌啶-3-甲酰胺(化合物B915)、化合物1.1+4-[3-(二氟甲基)苯基]-N-(2-氟苯基)-2-氧代-哌啶-3-甲酰胺(化合物B916)、化合物1.1+4-[3-(二氟甲基)苯基]-N-(2,3-二氟苯基)-2-氧代-哌啶-3-甲酰胺(化合物B917)、化合物1.1+(3R,4S)-N-(2,3-二氟苯基)-4-(4-氟苯基)-2-氧代-哌啶-3-甲酰胺(化合物B918)、和化合物1.1+(3R,4S)-4-(4-氟苯基)-2-氧代-N-[2-(三氟甲基)苯基]哌啶-3-甲酰胺(化合物B919)。
在另一个实施例中,参考上文提及的组合物,组分化合物1.1被化合物1.2替代。在另一个实施例中,参考上文提及的组合物,组分化合物1.1被化合物1.3替代。在另一个实施例中,参考上文提及的组合物,组分化合物1.1被化合物1.4替代。在另一个实施例中,参考上文提及的组合物,组分化合物1.1被化合物1.5替代。在另一个实施例中,参考上文提及的组合物,组分化合物1.1被化合物1.6替代。在另一个实施例中,参考上文提及的组合物,组分化合物1.1被化合物1.7替代。在另一个实施例中,参考上文提及的组合物,组分化合物1.1被化合物1.8替代。在另一个实施例中,参考上文提及的组合物,组分化合物1.1被化合物1.9替代。在另一个实施例中,参考上文提及的组合物,组分化合物1.1被化合物1.10替代。在另一个实施例中,参考上文提及的组合物,组分化合物1.1被化合物1.11替代。在另一个实施例中,参考上文提及的组合物,组分化合物1.1被化合物1.12替代。在另一个实施例中,参考上文提及的组合物,组分化合物1.1被化合物1.13替代。在另一个实施例中,参考上文提及的组合物,组分化合物1.1被化合物1.14替代。
具有式(I)的化合物与混合配伍物B的混合比可以根据一种或多种混合配伍物的性质而变化。典型的比例包括,例如,从1:100至1000:1,从1:50至50:1,或从1:10至10:1。
尽管具有式(I)的化合物与另一种除草剂的二元混合物明确地在上文进行披露,本领域的普通技术人员将理解本发明扩展到三元,以及另外的包含上述二元混合物的多种组合。特别地,本发明提供了包含下表1中列出的三元混合物的组合物(CMP=化合物:参见表C1):
表1
本发明进一步提供如下表2至14中所定义的组合物。
表2.包含上表1中列出的三元混合物的组合物,其中化合物1.1被化合物1.2替代(参见表C1)。
表3.包含上表1中列出的三元混合物的组合物,其中化合物1.1被化合物1.3替代(参见表C1)。
表4.包含上表1中列出的三元混合物的组合物,其中化合物1.1被化合物1.4替代(参见表C1)。
表5.包含上表1中列出的三元混合物的化合物,其中化合物1.1被化合物1.5替代(参见表C1)。
表6.包含上表1中列出的三元混合物的化合物,其中化合物1.1被化合物1.6替代(参见表C1)。
表7.包含上表1中列出的三元混合物的化合物,其中化合物1.1被化合物1.7替代(参见表C1)。
表8.包含上表1中列出的三元混合物的化合物,其中化合物1.1被化合物1.8替代(参见表C1)。
表9.包含上表1中列出的三元混合物的化合物,其中化合物1.1被化合物1.9替代(参见表C1)。
表10.包含上表1中列出的三元混合物的化合物,其中化合物1.1被化合物1.10替代(参见表C1)。
表11.包含上表1中列出的三元混合物的化合物,其中化合物1.1被化合物1.11替代(参见表C1)。
表12.包含上表1中列出的三元混合物的化合物,其中化合物1.1被化合物1.12替代(参见表C1)。
表13.包含上表1中列出的三元混合物的化合物,其中化合物1.1被化合物1.13替代(参见表C1)。
表14.包含上表1中列出的三元混合物的化合物,其中化合物1.1被化合物1.14替代(参见表C1)。
本发明的组合物可以进一步包括一种或多种安全剂。特别地,特别优选以下安全剂:AD 67(MON 4660)、解草嗪、解毒喹、解草胺腈、环丙磺酰胺、二氯丙烯胺、二环酮(dicyclonon)、二乙醇化物(dietholate)、解草唑、解草啶、解草安、肟草安、解草噁唑、甲呋烟腙、双苯噁唑酸、吡唑解草酯、甲酚盐(mephenate)、解草腈、萘二甲酸酐(CAS RN 81-84-5)、TI-35、N-异丙基-4-(2-甲氧基-苯甲酰基氨磺酰基)-苯甲酰胺(CAS RN 221668-34-4)和N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺。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。
特别优选的安全剂是解毒喹、环丙磺酰胺、双苯噁唑酸、吡唑解草酯和N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺。
本发明的优选组合物和安全剂包括:
化合物1.1、莠去津和解毒喹;化合物1.1、莠去津和环丙磺酰胺;化合物1.1、莠去津和双苯噁唑酸;化合物1.1、莠去津和吡唑解草酯;化合物1.1、莠去津和N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺。
化合物1.1、特丁津和解毒喹;化合物1.1、特丁津和环丙磺酰胺;化合物1.1、特丁津和双苯噁唑酸;化合物1.1、特丁津和吡唑解草酯;化合物1.1、特丁津和N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺。
化合物1.1、甲基磺草酮和解毒喹;化合物1.1、甲基磺草酮和环丙磺酰胺;化合物1.1、甲基磺草酮和双苯噁唑酸;化合物1.1、甲基磺草酮和吡唑解草酯;化合物1.1、甲基磺草酮和N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺。
化合物1.1、二环吡喃酮和解毒喹;化合物1.1、二环吡喃酮和环丙磺酰胺;化合物1.1、二环吡喃酮和双苯噁唑酸;化合物1.1、二环吡喃酮和吡唑解草酯;化合物1.1、二环吡喃酮和N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺。
化合物1.1、烟嘧磺隆和解毒喹;化合物1.1、烟嘧磺隆和环丙磺酰胺;化合物1.1、烟嘧磺隆和双苯噁唑酸;化合物1.1、烟嘧磺隆和吡唑解草酯;化合物1.1、烟嘧磺隆和N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺。
化合物1.1、S-异丙甲草胺和解毒喹;化合物1.1、S-异丙甲草胺和环丙磺酰胺;化合物1.1、S-异丙甲草胺和双苯噁唑酸;化合物1.1、S-异丙甲草胺和吡唑解草酯;化合物1.1、S-异丙甲草胺和N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺。
化合物1.1、溴苯腈和解毒喹,化合物1.1、溴苯腈和环丙磺酰胺,化合物1.1、溴苯腈和双苯噁唑酸,化合物1.1、溴苯腈和吡唑解草酯,化合物1.1、溴苯腈和N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺。
化合物1.1、唑啉草酯和解毒喹,化合物1.1、唑啉草酯和环丙磺酰胺,化合物1.1、唑啉草酯和双苯噁唑酸,化合物1.1、唑啉草酯和吡唑解草酯,化合物1.1、唑啉草酯和N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺。
化合物1.1、炔草酯-炔丙基和解毒喹,化合物1.1、炔草酯-炔丙基和环丙磺酰胺,化合物1.1、炔草酯-炔丙基和双苯噁唑酸,化合物1.1、炔草酯-炔丙基和吡唑解草酯,化合物1.1、炔草酯-炔丙基和N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺。
化合物1.1、精噁唑禾草灵-乙基和解毒喹,化合物1.1、精噁唑禾草灵-乙基和环丙磺酰胺,化合物1.1、精噁唑禾草灵-乙基和双苯噁唑酸,化合物1.1、精噁唑禾草灵-乙基和吡唑解草酯,化合物1.1、精噁唑禾草灵-乙基和N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺。
化合物1.1、甲基二磺隆和解毒喹,化合物1.1、甲基二磺隆和环丙磺酰胺,化合物1.1、甲基二磺隆和双苯噁唑酸,化合物1.1、甲基二磺隆和吡唑解草酯,化合物1.1、甲基二磺隆和N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺。
化合物1.1、碘甲磺隆甲酯钠和解毒喹,化合物1.1、碘甲磺隆甲酯钠和环丙磺酰胺,化合物1.1、碘甲磺隆甲酯钠和双苯噁唑酸,化合物1.1、碘甲磺隆甲酯钠和吡唑解草酯,化合物1.1、碘甲磺隆甲酯钠和N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺。
化合物1.1、噻酮磺隆和解毒喹,化合物1.1、噻酮磺隆和环丙磺酰胺,化合物1.1、噻酮磺隆和双苯噁唑酸,化合物1.1、噻酮磺隆和吡唑解草酯,化合物1.1、噻酮磺隆和N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺。
化合物1.1、化合物B2和解毒喹,化合物1.1、化合物B2和环丙磺酰胺,化合物1.1、化合物B2和双苯噁唑酸,化合物1.1、化合物B2和吡唑解草酯,化合物1.1、化合物B2和N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺。
化合物1.1、化合物B3和解毒喹,化合物1.1、化合物B3和环丙磺酰胺,化合物1.1、化合物B3和双苯噁唑酸,化合物1.1、化合物B3和吡唑解草酯,化合物1.1、化合物B3和N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺。
化合物1.1、化合物B4和解毒喹,化合物1.1、化合物B4和环丙磺酰胺,化合物1.1、化合物B2和双苯噁唑酸,化合物1.1、化合物B4和吡唑解草酯,化合物1.1、化合物B4和N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺。
化合物1.1、化合物B5和解毒喹,化合物1.1、化合物B5和环丙磺酰胺,化合物1.1、化合物B5和双苯噁唑酸,化合物1.1、化合物B5和吡唑解草酯,化合物1.1、化合物B5和N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺。
化合物1.1、化合物B6和解毒喹,化合物1.1、化合物B6和环丙磺酰胺,化合物1.1、化合物B6和双苯噁唑酸,化合物1.1、化合物B6和吡唑解草酯,化合物1.1、化合物B6和N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺。
化合物1.1、化合物B7和解毒喹,化合物1.1、化合物B7和环丙磺酰胺,化合物1.1、化合物B7和双苯噁唑酸,化合物1.1、化合物B7和吡唑解草酯,化合物1.1、化合物B7和N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺。
本发明进一步优选的组合物和安全剂包括上面定义的组合物,其中化合物1.1被化合物1.2取代。本发明进一步优选的组合物和安全剂包括上面定义的组合物,其中化合物1.1被化合物1.3取代。本发明进一步优选的组合物和安全剂包括上面定义的组合物,其中化合物1.1被化合物1.4取代。本发明进一步优选的组合物和安全剂包括上面定义的组合物,其中化合物1.1被化合物1.5取代。本发明进一步优选的组合物和安全剂包括上面定义的组合物,其中化合物1.1被化合物1.6取代。本发明进一步优选的组合物和安全剂包括上面定义的组合物,其中化合物1.1被化合物1.7取代。本发明进一步优选的组合物和安全剂包括上面定义的组合物,其中化合物1.1被化合物1.8取代。本发明进一步优选的组合物和安全剂包括上面定义的组合物,其中化合物1.1被化合物1.9取代。本发明进一步优选的组合物和安全剂包括上面定义的组合物,其中化合物1.1被化合物1.10取代。本发明进一步优选的组合物和安全剂包括上面定义的组合物,其中化合物1.1被化合物1.11取代。本发明进一步优选的组合物和安全剂包括上面定义的组合物,其中化合物1.1被化合物1.12取代。本发明进一步优选的组合物和安全剂包括上面定义的组合物,其中化合物1.1被化合物1.13取代。本发明进一步优选的组合物和安全剂包括上面定义的组合物,其中化合物1.1被化合物1.14取代。
具有式I的化合物还可以在具有其他农用化学品(如杀真菌剂、杀线虫剂或杀昆虫剂)的混合物中使用,这些农用化学品的实例在The Pesticide Manual[杀有害生物剂手册],第十六版,英国作物保护委员会,2012中给出。
本发明仍进一步提供了一种在场所处控制杂草的方法,所述方法包括向该场所施用杂草控制量的包含具有式(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杂草控制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)的化合物的除草效果。优选的作物植物包括玉米、小麦、大麦和水稻。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,可能的是该作物植物经由基因工程而赋予对4-羟苯丙酮酸二加氧酶(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WO 0246387中所已知的。因此,在一个甚至更优选的实施例中,该作物植物关于一种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酶的一个DNA序列,该HPPD抑制剂抗性的HPPD酶衍生自一种细菌(更具体地说,来自荧光假单胞菌(Pseudomonas fluorescens)或希瓦氏菌(Shewanella colwelliana))、或来自一种植物(更具体地说,衍生自单子叶植物或还更具体地说,来自大麦、玉米、小麦、稻、臂形草属、蒺藜草属(Cenchrus)、黑麦草属、羊茅属、狗尾草属、蟋蟀草属、高粱属或燕麦属物种)。若干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。因此,本发明的除草化合物已广泛施用于许多作物植物,包括谷物,例如大麦和小麦、棉花、油菜籽油菜、向日葵、玉米、水稻、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。
具有式I的化合物的施用率可以在宽范围之内变化并且取决于土壤的性质、施用方法(出苗前或出苗后;拌种;施用至种子垄沟;免耕施用等)、作物植物、有待控制的杂草、主要气候条件、以及受施用方法支配的其他因素、施用时间以及目标作物。根据本发明的式I的化合物通常以从10到2000g/ha,尤其是从25到1000g/ha,更尤其是从25到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、以及ACC酶-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夏季油菜(卡诺拉(canola))。通过基因工程方法已经赋予其对除草剂的耐受性的作物的实例包括例如草甘膦和草铵膦抗性玉米品种,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其对有害昆虫有抗性的那些农作物,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描述于EP-A-451 878、EP-A-374 753、WO 93/07278、WO 95/34656、WO 03/052073以及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(玉米)、(玉米)、(棉花)、(棉花)、(马铃薯)、以及其植物作物或种子材料均可以是抗除草剂的并且同时是抗昆虫摄食(“叠加的”转基因事件)。例如,种子可以在具有表达杀虫的Cry3蛋白的能力的同时是耐草甘膦的。
作物植物还应被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(例如改进的储存稳定性、更高的营养价值以及改进的香味)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。
本发明的这些化合物可以根据以下方案进行制备。
具有式(I)的化合物的制备类似于已知方法进行,并包括使具有式(IIc)的化合物:
其中R1的定义与式(I)相同,并且LG是合适的离去基团,例如卤素原子,如氯,或烷氧基或芳氧基基团,如4-硝基苯氧基,在惰性有机溶剂中,例如二氯甲烷或乙腈,在碱如三乙胺存在下,与式(III)的二酮反应
其中
A1和Ra、Rb、Rc、Rd是如前面关于式(I)所定义的;
以给出具有式(IV)的酯:
在合适的碱如三乙胺存在下,可以使用催化剂如4-二甲基氨基吡啶或丙酮合氰化氢,或金属氰化物盐如氰化钠重排,以给出具有式(I)的化合物。
因此,根据本发明的另外的方面,提供了具有式(II)的化合物
其中
R1是如前所定义的,并且R2选自下组,该组由以下组成:卤素、-OH、C1-C6烷氧基、芳氧基和N-连接的咪唑基。在本文中,芳氧基优选为苯环上任选地被1至5个基团取代的苯氧基基团,所述基团由以下组成:氟、氯、硝基、氰基、C1-C3烷基、C1-C3烷氧基和C1-C3卤代烷基。因此,优选的芳氧基的具体实例包括苯氧基、4-硝基苯氧基和2,3,4,5,6-五氟苯氧基。
表C2–本发明的化合物的实例。
式(III)的二酮可以是可商购的,或者在不可商购的情况下,通过文献中详述的方法制备。例如,二酮的制备(其中A1是C=O并且Ra、Rb、Rc和Rd均为甲基)详述于Tetrahedron[四面体]2013,8559-8563中。二酮的制备(其中A1是CH(乙基)并且Ra、Rb、Rc和Rd均为氢)详述于Tetrahedron[四面体]2000,4753-4758中。二酮的制备(其中A1是CH2,Ra-Rc是-CH2CH2-并且Rb和Rd均为氢)详述于Tetrahedron Lett.[四面体通讯]2013,557-561中。二酮的制备(其中A1是CH2并且Ra、Rb、Rc和Rd均为甲基)详述于US 5006150A1,1991中。
因此,根据本发明的另外的方面,提供产生具有式(I)的化合物的方法,所述方法包括(i)在惰性有机溶剂中和在碱存在下,使具有式(IIc)化合物:
其中R1的定义与式(I)相同,并且LG是合适的离去基团(例如卤素原子,如氯,或烷氧基或芳氧基,如4-硝基苯氧基),与式(III)的二酮反应
和(ii)将得到的产物重排成具有式(I)的化合物。
具有式(IIc)的化合物可以由具有式(IIb)的羧酸来制备。
例如,对于LG=氯,技术人员将认识到执行该转化的常用方法,例如在非极性溶剂(例如二氯甲烷或乙腈)中用1当量的草酰氯和催化量的N,N-二甲基甲酰胺处理羧酸。
式(IIb)的羧酸又可以通过在水和有机溶剂的混合物的合适溶剂体系中用醇盐碱如氢氧化锂处理,由具有式(IIa)的酯制备。合适的酯的实例是其中R2是C1-C6烷基-,例如甲基、乙基,正丙基和异丙基。合适的溶剂体系的实例是四氢呋喃/水(1:1)或乙醇/水(1:1)。
具有式(IIa)的酯可以由具有式(IV)的哒嗪酮与3,4-二甲氧基硼酸之间的Chan-Lam偶联制备。Chan-Lam反应详述于Tetrahedron Lett.[四面体通讯]1998,2933-2936中。这些反应使用铜(II)或铜(I)盐如乙酸铜(II),非极性溶剂如二氯甲烷或1,2-二氯乙烷和有机碱,如三乙胺或吡啶或三乙胺和吡啶的1:1混合物。可以使用超化学计量当量的铜(I)或铜(II)盐,通常1-3当量的乙酸铜(II)。可替代地,如果还添加>1当量的氧化剂,则可以使用催化量的铜催化剂,例如0.05至0.3摩尔当量的乙酸铜(II)。氧化剂的合适实例是吡啶-N-氧化物或空气或氧气鼓泡通过反应混合物。该反应通常可在室温下进行,以在2-16h内实现可接受的转化。
具有式(IV)的哒嗪酮可以通过用合适的氧化剂氧化具有式(VI)的二氢哒嗪酮来制备。合适的氧化剂的实例是在乙酸或二氯甲烷的溶液中的溴,或在异丙醇的溶液中的碘苯二乙酸酯。
具有式(VI)的二氢哒嗪酮可以通过在合适的溶剂如乙醇中在回流条件下用水合肼处理具有式(VII)的化合物来制备。
具有式(VII)的化合物可以通过在合适的碱(例如碳酸钾)存在下,在合适的溶剂(例如丙酮)中,通过将可商购的二烷基丙二酸酯(例如丙二酸二乙酯)用具有式(VIII)的溴酮的烷基化来制备。
具有式(VIII)的化合物可以是可商购的,或可替代地它们可以通过将可商购的具有式(IX)的甲基酮在合适的溶剂(如甲醇或水和冰醋酸的混合物(约5:1))中用溴处理溴化来制备。
以下非限制性实例提供了用于本发明的代表性化合物的具体合成方法,如上表C1中所示。
制备实例1:6-[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-1,3,5-三酮的(化合物1.11(参见表C1))制备。
步骤1. 2-溴-1-环丙基-乙酮的制备。
在0℃下,在1小时的时间段内,向1-环丙基乙酮(50g,595mmol)在MeOH(350mL)中的搅拌的溶液中(冰浴)逐滴添加溴(32mL,595mmol)(反应混合物初始的红色在结束添加溴时变为无色)。然后将得到的溶液在低于5℃下搅拌4小时,然后添加水(175mL),并且将反应混合物在室温下搅拌16小时。将反应混合物倒入水(1000mL)中并用CH2Cl2(2x 1000mL)萃取。将合并的有机层用饱和NaHCO3水溶液(500mL)、水(500mL)并且最终用盐水(500mL)洗涤。将有机层经Na2SO4干燥,过滤并在真空中浓缩以给出浅棕色油状物。在100℃下,通过将该粗油状物真空蒸馏获得纯的2-溴-1-环丙基-乙酮(59g,61%)。
1H NMR(400MHz,CDCl3)δ=4.01(s,2H),2.22-2.17(m,1H),1.14-1.11(m,2H),1.03-0.99(m,2H)。
步骤2.二乙基2-(2-环丙基-2-氧代-乙基)丙二酸酯的制备。
在室温下,向2-溴-1-环丙基-乙酮(50g,307mmol)在丙酮(450mL)中的搅拌的溶液中添加K2CO3(64g,460mmol)、碘化钾(1.5g,9.2mmol)和丙二酸二乙酯(54g,337mmol)并将得到的混合物在回流下(75℃)加热16小时。将反应混合物过滤,并且在真空中浓缩滤液。将粗材料通过柱色谱法,用在己烷中的8%EtOAc洗脱进行纯化以得到呈淡黄色油状物的二乙基2-(2-环丙基-2-氧代-乙基)丙二酸酯(40g,54%)。
1H NMR(400MHz,CDCl3)δ=4.24-4.13(m,4H),3.95(t,1H),3.18(d,2H),1.98-1.92(m,1H),1.26(t,6H),1.06-1.03(m,2H),0.93-0.88(m,2H)。
步骤3.乙基3-环丙基-6-氧代-4,5-二氢-1H-哒嗪-5-羧酸酯的制备。
在0℃-5℃之间(冰-水浴),向二乙基2-(2-环丙基-2-氧代-乙基)丙二酸酯(70g,289mmol)在EtOH(500mL)中的搅拌的溶液中逐滴添加水合肼(16mL,318mmol)并将得到的溶液在室温下搅拌20小时。在真空中从反应混合物除去全部挥发物以得到呈浓黄色油状物的粗品乙基3-环丙基-6-氧代-4,5-二氢-1H-哒嗪-5-羧酸酯(52g,粗品)。将该粗材料不经任何进一步纯化而用于下一步骤。
步骤4.乙基3-环丙基-6-氧代-1H-哒嗪-5-羧酸酯的制备。
在10℃-15℃之间,在30分钟的时间段内,向乙基3-环丙基-6-氧代-4,5-二氢-1H-哒嗪-5-羧酸酯(52g粗品,247mmol)在AcOH(500mL)中的搅拌的溶液中逐滴添加溴(20mL,317mmol)在AcOH(200mL)中的溶液。然后将所得溶液在室温下搅拌另外的30分钟。在真空中从反应混合物中除去AcOH。向残余物添加EtOAc(2000mL)和水(5000mL)并且将混合物充分振摇。然后将所有不溶性粒子通过硅藻土床过滤除去,并且然后分离滤液层。将该水层进一步用EtOAc(1000mL)萃取。将合并的EtOAc层用饱和NaHCO3水溶液(500mL)、饱和的Na2S2O3水溶液(500mL)和最终的盐水(500mL)洗涤。将有机层经Na2SO4干燥,过滤并且在真空中浓缩。将粗材料通过柱色谱法,用在己烷中的8%EtOAc洗脱进行纯化以得到呈淡黄色固体的所希望产物。将固体通过用EtOAc在己烷中的1%溶液研磨进一步纯化以得到呈灰白色固体的乙基3-环丙基-6-氧代-1H-哒嗪-5-羧酸酯(17g,28%经两步)。
1H NMR(400MHz,CDCl3)δ=11.17(s,1H),7.65(s,1H),4.40(q,2H),1.92-1.85(m,1H),1.38(t,3H),1.02-0.98(m,2H),0.92-0.88(m,2H)。
步骤5.乙基6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羧酸酯的制备。
向乙基3-环丙基-6-氧代-1H-哒嗪-5-羧酸酯(2.00g,9.61mmol)在二氯甲烷(70mL)的搅拌的溶液中添加分子筛(0.88g)、一水合乙酸铜(II)(4.01g,22.1mmol)、三乙胺(2.7mL,19.2mmol)和吡啶(1.6mL,19.2mmol)。然后经10分钟分批添加(3,4-二甲氧基苯基)硼酸(2.6g,14.4mmol)。将反应混合物在室温下搅拌4小时,伴随压缩空气鼓泡通过。4小时后,关闭压缩空气并继续搅拌另外的16小时。将反应混合物通过硅藻土过滤,用另外的CH2Cl2洗涤残余物。用2N HCl水溶液(2x 100mL)和饱和盐水溶液(100mL)洗涤滤液。将有机层经MgSO4干燥,过滤并且在真空中浓缩,以留下深黄色胶状物。通过柱色谱法进行纯化,用在异己烷中的0-100%EtOAc洗脱以得到呈亮黄色胶状物的乙基6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羧酸酯(2.46g,74%)。
1H NMR(400MHz,CDCl3)δ=7.55(s,1H),7.11(m,2H),6.91(d,1H),4.40(q,2H),3.94(s,3H),3.90(s,3H),1.97(m,1H),1.40(t,3H),1.04(m,2H),0.92(m,2H)。
步骤6. 6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羧酸的制备。
向乙基6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羧酸酯(2.40g,6.97mmol)在四氢呋喃(50mL)中的溶液添加水(25mL)随后添加氢氧化锂(0.45g,10.5mmol)。将所得溶液在室温下搅拌90分钟。在真空中除去THF并将残余的水混合物用水(25mL)稀释并用EtOAc(30mL)洗涤。将剧烈搅拌的水层用浓缩的HCl溶液酸化至pH=1-过程中形成黄色沉淀。通过过滤收集沉淀以得到呈黄色固体的6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羧酸(1.78g,81%)。
1H NMR(400MHz,CDCl3)δ=14.10(br.s,1H),8.06(s,1H),7.14(m,1H),7.10(m,1H),6.97(d,1H),3.95(s,3H),3.90(s,3H),2.10(m,1H),1.15(m,2H),1.00(m,2H)。
步骤7. 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(化合物1.11)的制备。
在氮气气氛下,向于100mL三颈圆底烧瓶中的6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羧酸(1.00g,3.16mmol)在二氯甲烷(无水的,20mL)中的溶液添加N,N-二甲基甲酰胺(无水的,0.012mL,0.158mmol)随后逐滴添加乙二酰氯(0.29mL,3.32mmol)并将反应混合物在室温下搅拌1小时。将反应混合物冷却至0℃(盐/冰浴)并且经15分钟逐滴添加三乙胺(1.77mL,12.7mmol),然后在0℃下搅拌5分钟,然后在经15分钟内逐滴添加溶解于最小量CH2Cl2中的2,2,4,4-四甲基环己烷-1,3,5-三酮(0.58g,3.17mmol)。在0℃下,将所得溶液搅拌5分钟然后在室温下搅拌1小时。将反应混合物冷却至0℃并且经10分钟逐滴添加三乙胺(1.77mL,12.7mmol)随后添加丙酮合氰化氢(0.044mL,0.475mmol)。将反应混合物0℃下搅拌5分钟,然后在回流(40℃)下加热90分钟。允许反应混合物冷却至室温,过滤并在真空中浓缩滤液。通过柱色谱法进行纯化,用20:8:4:4:1甲苯:二噁烷:EtOH:Et3N:水的混合溶剂系统洗脱以得到所希望化合物的三乙胺盐。将粗的油状物溶解于MeOH并将其负载到固相萃取SAX柱上。用3倍柱体积的MeOH冲洗柱子,并且然后用在MeOH中的1%甲酸释放所希望的产物,在真空中浓缩,以得到呈橙色挤压泡沫的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(0.31g,20%)。
1H NMR(400MHz,CDCl3)δ=7.13(s,1H),7.12-7.06(m,2H),6.91(d,1H),3.91(s,3H),3.88(s,3H),2.00-1.92(m,1H),1.52(br.s,6H),1.40(br.s,6H),1.05-0.98(m,2H),0.98-0.91(m,2H)。
制备实例2:2-[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(化合物1.8(参见表C1))的制备。
将6-环丙基-2-(3,4-二甲氧基苯基)-3-氧代-哒嗪-4-羧酸(1.00g,3.16mmol)添加至无水DCM(20mL)中并向其中添加一滴无水DMF。然后将草酰氯(0.35mL,4.11mmol)逐滴添加至混合物中并且搅拌1h。将反应混合物在氮气气氛下减压浓缩。然后将粗反应物质溶于无水DCM(15mL)中,添加活化的分子筛并将反应混合物在冰盐浴中冷却。然后经15分钟将三乙胺(1.23mL,9.48mmol)逐滴添加至反应混合物中。然后向反应混合物中逐滴添加在DCM(10mL)中的5-甲基-1,3-环己烷二酮(479mg,3.79mmol)。在室温下搅拌1小时。然后添加三乙胺(1.23mL,9.48mmol)和丙酮合氰化氢(0.22mL,2.37mmol)并将反应搅拌2.5h。将粗产物用DCM稀释并用1N HCl洗涤。通过柱色谱法进行纯化,用20:8:4:4:1甲苯:二噁烷:EtOH:Et3N:水的混合溶剂系统洗脱以得到呈棕色胶状物的所希望化合物的三乙胺盐。向其中加入水(25mL)和CH2Cl2(25mL),并且用2M HCl将其酸化至pH 1。将混合物搅拌5分钟,然后通过相分离柱分离各相,再用CH2Cl2洗涤。浓缩有机相,以得到所希望的产物,呈固体的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(850mg,2.00mmol,63%)。
1H NMR(400MHz,CDCl3)δ=7.14-7.10(2H,m),6.98(1H,s),6.89(1H,d),3.89(3H,s),3.87(3H,s),2.75-2.71(1H,m),2.53-2.39(2H,m),2.32-2.26(1H,m),2.18-2.12(1H,m),1.97-1.90(1H,m),1.08(3H,d),0.99-0.95(2H,m),0.93-0.87(2H,m)。
制备实例3:2-[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(化合物1.3(参见表C1))的制备。
步骤1. 1-溴丙烷-2-酮的制备。
将丙酮(150g,2.58mol)、水(480mL)和冰醋酸(90mL)在双颈圆底烧瓶中搅拌并且加热至回流(75℃)。将溴(73.2mL,2.84mol)分批添加溶液中。将反应混合物在75℃下继续加热直至其变为无色。然后将其冷却至0℃(冰浴),并添加水(100mL),然后添加充分的Na2CO3,直到它不再是酸性的。将反应混合物转移至分液漏斗中,并分离底部有机层,经Na2SO4干燥并过滤,以得到1-溴丙烷-2-酮(99.0g,28%)。
1H NMR(CDCl3,400MHz)δ=3.23(s,2H),1.67-1.72(m,3H)。
步骤2.二乙基2-丙酮基丙二酸酯的制备。
将1-溴丙烷-2-酮(90g,0.66mol)溶解在丙酮(740mL)中,并在氮气氛下,将丙二酸二乙酯(126mL,0.79mol)、K2CO3(136g,0.99mol)和KI(3.27g,19.7mmol)添加至搅拌的溶液中。将反应混合物在回流下加热16小时。将反应混合物过滤,并且在真空中浓缩滤液。将粗材料溶解于EtOAc中并用水洗涤,随后用盐水洗涤。将有机层经Na2SO4干燥,过滤且在真空中浓缩以得到一种液体。将粗材料通过柱色谱法,用在CH2Cl2中的0-5%MeOH洗脱进行纯化以得到呈浅黄色油状物的二乙基2-丙酮基丙二酸酯(80.0g,56%)。
1H NMR(CDCl3,400MHz)δ=4.21-4.04(m,4H),3.78(t,1H),2.99(d,2H),2.20-2.06(m,3H),1.27-1.13ppm(m,6H)。
步骤3.乙基3-甲基-6-氧代-4,5-二氢-1H-哒嗪-5-羧酸酯的制备。
将二乙基2-丙酮基丙二酸酯(80g,370mmol)溶解于无水乙醇(175mL)并冷却至0℃。向搅拌溶液中逐滴添加水合肼(20.4mL,407mmol)。允许将该混合物加温至室温并搅拌16小时。将反应混合物在真空中浓缩,并将所得粗品乙基3-甲基-6-氧代-4,5-二氢-1H-哒嗪-5-羧酸酯不经进一步纯化而直接用于下一步骤(61.0g粗品,90%)。
步骤4.乙基3-甲基-6-氧代-1H-哒嗪-5-羧酸酯的制备。
将溴(17mL,662mmol)在乙酸(140mL)中的溶液分批添加到乙基3-甲基-6-氧代-4,5-二氢-1H-哒嗪-5-羧酸酯(61g粗品,331mmol)在乙酸(1250mL)中的搅拌的溶液中。在室温下,将反应混合物搅拌1小时,然后在真空中浓缩。将粗材料溶解于EtOAc中并将该溶液用水洗涤,随后用盐水洗涤,经Na2SO4干燥,过滤并在真空中浓缩。将粗材料通过柱色谱法,用在CH2Cl2中的0-5%MeOH洗脱进行纯化以得到呈灰白色固体的乙基3-甲基-6-氧代-1H-哒嗪-5-羧酸酯(22.0g,37%)。
1H NMR(CDCl3,400MHz)δ=7.71(s,1H),4.40(q,2H),2.39(s,3H),1.39(t,3H)。
步骤5.乙基2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羧酸酯的制备。
向乙基3-甲基-6-氧代-1H-哒嗪-5-羧酸酯(5.0g,27.4mmol)在二氯甲烷(200mL)中的溶液添加一水合乙酸铜(II)(12.6g,63.1mmol)、分子筛、吡啶(4.4mL,54.9mmol)和三乙胺(7.7mL,54.9mmol)。经5分钟向搅拌悬浮液中分批添加(3,4-二甲氧基苯基)硼酸(7.0g,38.4mmol)并将反应混合物在室温下搅拌16小时。将反应混合物通过硅藻土过滤,用另外的CH2Cl2洗涤残余物。将滤液用2N HCl水溶液(2x 200mL)洗涤,经MgSO4干燥,过滤并在真空中浓缩。通过柱色谱法进行纯化,用在异己烷中的20%-100%EtOAc洗脱以得到呈浅黄色固体的乙基2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羧酸酯(5.10g,58%)。
1H NMR(400MHz,CDCl3)δ=7.66(s,1H),7.11(br.s,2H),6.93(d,1H),4.41(q,2H),3.92(s,3H),3.90(s,3H),2.44(s,3H),1.39(t,3H)。
步骤6. 2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羧酸的制备。
向冷却至0℃(冰浴)的乙基2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羧酸酯(12.0g,37.7mmol)在四氢呋喃(200mL)中的溶液添加氢氧化锂一水合物(2.37g,56.5mmol)在水(100mL)中的溶液。允许该反应混合物加温至室温并搅拌30分钟。在真空中除去THF,并且将含水混合物用CH2Cl2(3x 40mL)洗涤。将水溶液冷却至0℃,并且搅拌同时添加浓缩HCl溶液直至达到pH=1。在该过程中沉淀出亮黄色固体。通过过滤收集该固体。将固体溶解在CH2Cl2中并且将溶液经MgSO4干燥,过滤并在真空中浓缩,以得到呈亮黄色固体的2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羧酸(9.5g,87%)。
1H NMR(400MHz,CDCl3)δ=14.01(br.s,1H),8.18(s,1H),7.16(d,1H),7.08(br.s,1H),6.98(d,1H),3.94(app.d,6H),2.55(s,3H)。
步骤7. 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(化合物1.3)的制备。
向2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羧酸(1.00g,3.44mmol)在二氯甲烷(无水的,13mL)中的溶液中添加3滴N,N-二甲基甲酰胺(无水的),随后逐滴添加草酰氯(0.33mL,3.79mmol)。将反应混合物在室温下搅拌16小时。再添加DMF(1滴)和草酰氯(0.1mL)并在室温下继续搅拌1小时。向冷却的(0℃(冰浴))环己烷-1,3-二酮(0.41g,3.62mmol)在二氯甲烷(无水的,7.0mL)中的溶液中添加三乙胺(1.44mL,10.3mmol)。然后通过注射泵在经10分钟内(70mL/h)将酰基氯溶液添加至环己烷-1,3-二酮-三乙胺溶液中并且将反应混合物在0℃下再搅拌5分钟。添加另外的三乙胺(0.48mL,3.45mmol),随后添加丙酮合氰化氢(作为无水CH2Cl2中的储备溶液)(10mol%,0.34mmol)。将反应烧瓶转移至预热的油浴中并在回流(40℃)下搅拌加热6小时,并且然后在室温下再搅拌16小时。将该反应混合物在真空中浓缩,以得到黑色残余物。通过柱色谱法进行纯化,用20:8:4:4:1甲苯:二噁烷:EtOH:Et3N:水的混合溶剂系统洗脱以得到呈棕色胶状物的所希望化合物的三乙胺盐。向其中加入水(25mL)和CH2Cl2(25mL),并且用2M HCl将其酸化至pH 1。将混合物搅拌5分钟,然后通过相分离柱分离各相,再用CH2Cl2洗涤。浓缩有机相,以得到呈橙色泡沫的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(400mg,30%产率)。
1H NMR(400MHz,CDCl3)δ=16.14(1H,s),7.13(1H,dd),7.09(2H,m),6.92(1H,d),3.90(3H,s),3.89(3H,s),2.73(3H,t),2.46(3H,t),2.41(3H,s),2.04(2H,五重峰)。
制备实例4. 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(化合物1.1(参见表C1))的制备。
添加DMF(催化剂)和草酰氯(0.6mL)至2-(3,4-二甲氧基苯基)-6-甲基-3-氧代-哒嗪-4-羧酸(1.5g,5.172mmol)在DCM中的搅拌悬浮液(20mL)中。将反应混合物在室温下搅拌1.5h。TLC(用MeOH猝灭后)显示形成非极性斑点。将该反应物质在N2气氛下蒸发。添加DCM(20mL),然后添加一撮分子筛。将TEA(2.2mL)和二环[3.2.1]辛烷-2,4-二酮(0.86g,6.2mmol)添加到酰基氯溶液中。将该反应混合物在室温下搅拌1h。添加三乙胺(2.2mL)和25滴丙酮合氰化氢并搅拌2h。将反应物质通过色谱法,在20:8:4:4:1甲苯:二噁烷:EtOH:Et3N:水的混合溶剂系统中纯化,并且通过10%HCl溶液酸化,用DCM萃取。蒸发溶剂,得到粗化合物,将其通过色谱法用丙酮-DCM进一步纯化,以得到呈固体的所希望的产物,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(500mg,1.22mmol,24%)。
1H NMR(400MHz,CDCl3)δ=16.19(1H,s),7.16-7.09(3H,m),6.93(1H,d),3.91(6H,s),3.11(1H,t),2.94(1H,t),2.42(3H,s),2.26-2.06(3H,m),2.04-1.98(1H,m),1.83(1H,brm),1.72(1H,dt)。
生物学实例
将各种试验物种HORVW(Hordeum vulgare-大麦)、ABUTH(茼麻)、AMARE(反枝苋)和ECHCG(稗草)的种子播种在盆中的标准土壤中。在温室中的控制条件(24℃/16℃,白天/夜晚;14小时光照;65%湿度)下培养10天后,用一种水性喷洒溶液来喷洒这些植物,该水性喷洒溶液源自0.6ml丙酮和含有10.6%Emulsogen EL(登记号61791-12-6)、42.2%N-甲基吡咯烷酮、42.2%二丙二醇单甲醚(CAS RN 34590-94-8)和0.2%X-77(CAS RN 11097-66-8)的45ml配制品溶液中的工业级活性成分的配制品。
然后将测试植物在温室中的控制条件(在24℃/16℃,白天/夜晚;14小时光照;65%湿度)下生长,并每天浇水两次。14天之后,对测试进行评估(100=对植物完全性的损害;0=对植物没有损害)。
表B1
这些比较结果表明,与WO 2012/136703中特别披露的等效单甲氧基苯基化合物相比,本发明的二甲氧基苯基取代的哒嗪酮化合物令人惊讶地对作物植物(大麦-HORVW)的损害小,同时保持对代表性杂草物种(ECHCG、ABUTH、AMARE)的良好控制。
表B2
这些结果表明,当施用于作物植物(大麦-HORVW)时,本发明的化合物几乎没有任何损害,但仍然提供对代表性杂草物种(ECHCG、ABUTH、AMARE)的良好控制。
Claims (15)
1.一种具有式(I)的化合物:
或其农学上可接受的盐,
其中
R1选自下组,该组由以下组成:氢、卤素、氰基、硝基、C1-C6烷基-、C3-C6环烷基-、C2-C6-烯基-、C2-C6炔基-、C1-C6卤代烷基-、C1-C6烷氧基-、C1-C3卤代烷氧基-、C1-C6烷氧基-C1-C3烷基-、C1-C6烷基-S(O)p-和C1-C6卤代烷基-S(O)p-;
A1选自下组,该组由以下组成:O、C(O)和(CReRf);
Ra、Rb、Rc、Rd、Re和Rf各自独立地选自下组,该组由以下组成:氢和C1-C4烷基-,其中Ra和Rc可以一起形成C1-C3亚烷基链;并且
p是0、1或2。
2.根据权利要求1所述的化合物,其中R1是C1-C6烷基-或C3-C6环烷基-。
3.根据权利要求1或权利要求2所述的化合物,其中R1是甲基或环丙基-。
4.根据以上权利要求中任一项所述的化合物,其中A1是CReRf并且Re和Rf是氢。
5.根据以上权利要求中任一项所述的化合物,其中Ra、Rb、Rc和Rd是氢。
6.根据以上权利要求1至4中任一项所述的化合物,其中Ra和Rc一起形成–CH2-CH2-链并且Rb和Rd是氢。
7.根据以上权利要求1至3中任一项所述的化合物,其中A1是O和Ra、Rb、Rc和Rd是甲基。
8.根据以上权利要求中任一项所述的化合物,该化合物处于农业化学上可接受的盐的形式,其中该农业化学上可接受的盐选自下组,该组由以下组成:铝、钙、钴、铜、铁、镁、钾、钠和锌。
9.一种除草组合物,其包含根据以上权利要求中任一项所述的化合物和农业上可接受的配制佐剂。
10.根据权利要求9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。
11.根据权利要求10所述的除草剂组合物,其中该另外的杀有害生物剂是除草剂或除草剂安全剂。
12.一种在场所控制杂草的方法,该方法包括向该场所施用杂草控制量的根据权利要求9至11中任一项所述的组合物。
13.一种具有式(II)的化合物
其中
R1是如在权利要求1中定义的,并且
R2选自下组,该组由以下组成:卤素、–OH、C1-C6烷氧基-、芳氧基和N-连接的咪唑。
14.一种产生具有式(I)的化合物的方法,该方法包括:(i)在惰性有机溶剂中和在碱存在下,使具有式(IIc)化合物:
其中R1的定义与式(I)相同,并且LG是合适的离去基团,与式(III)的二酮反应
和(ii)将得到的产物重排成具有式(I)的化合物。
15.如在权利要求1中所定义的具有式(I)的化合物作为除草剂的用途。
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MX2018012303A (es) | 2019-01-14 |
PH12018502201A1 (en) | 2019-09-23 |
CL2018002931A1 (es) | 2018-12-14 |
US10813354B2 (en) | 2020-10-27 |
KR20180134353A (ko) | 2018-12-18 |
WO2017178582A1 (en) | 2017-10-19 |
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