CN115362147A - 除草化合物 - Google Patents
除草化合物 Download PDFInfo
- Publication number
- CN115362147A CN115362147A CN202180025259.XA CN202180025259A CN115362147A CN 115362147 A CN115362147 A CN 115362147A CN 202180025259 A CN202180025259 A CN 202180025259A CN 115362147 A CN115362147 A CN 115362147A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- compound
- formula
- group
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 124
- 230000002363 herbicidal effect Effects 0.000 title claims description 22
- 239000000203 mixture Substances 0.000 claims abstract description 77
- 241000196324 Embryophyta Species 0.000 claims abstract description 38
- 239000004009 herbicide Substances 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 238000009472 formulation Methods 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 239000000575 pesticide Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 168
- 239000011541 reaction mixture Substances 0.000 description 87
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 69
- -1 methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, i-butylthio, S-butylthio Chemical group 0.000 description 69
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 64
- 235000019439 ethyl acetate Nutrition 0.000 description 58
- 239000007787 solid Substances 0.000 description 58
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 47
- 239000000243 solution Substances 0.000 description 35
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- 239000012071 phase Substances 0.000 description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 24
- 238000005481 NMR spectroscopy Methods 0.000 description 20
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 20
- 239000012074 organic phase Substances 0.000 description 20
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 239000008346 aqueous phase Substances 0.000 description 18
- 239000013058 crude material Substances 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 244000038559 crop plants Species 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- 238000005160 1H NMR spectroscopy Methods 0.000 description 14
- 238000003818 flash chromatography Methods 0.000 description 14
- 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 13
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 12
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000004094 surface-active agent Substances 0.000 description 12
- 239000002585 base Substances 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 11
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000003112 inhibitor Substances 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
- 240000008042 Zea mays Species 0.000 description 8
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 239000004530 micro-emulsion Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- GTKOKCQMHAGFSM-UHFFFAOYSA-N 1-methyltetrazol-5-amine Chemical compound CN1N=NN=C1N GTKOKCQMHAGFSM-UHFFFAOYSA-N 0.000 description 7
- 239000005711 Benzoic acid Substances 0.000 description 7
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 7
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 7
- 235000010233 benzoic acid Nutrition 0.000 description 7
- 239000004495 emulsifiable concentrate Substances 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 241000894007 species Species 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- OWDSZHXKDQAOMA-UHFFFAOYSA-N 3-bromo-2-chloro-6-(trifluoromethoxy)aniline Chemical compound Nc1c(Cl)c(Br)ccc1OC(F)(F)F OWDSZHXKDQAOMA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 238000010353 genetic engineering Methods 0.000 description 6
- IOAJPJQTAMEEBD-UHFFFAOYSA-N methyl 3-amino-2-chloro-4-(trifluoromethoxy)benzoate Chemical compound COC(=O)c1ccc(OC(F)(F)F)c(N)c1Cl IOAJPJQTAMEEBD-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
- 239000005909 Kieselgur Substances 0.000 description 5
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 5
- 235000019270 ammonium chloride Nutrition 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
- 235000019253 formic acid Nutrition 0.000 description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
- 235000009973 maize Nutrition 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000004546 suspension concentrate Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 230000009261 transgenic effect Effects 0.000 description 5
- 239000000080 wetting agent Substances 0.000 description 5
- 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 4
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 4
- JHRIPENGTGSNPJ-UHFFFAOYSA-N 2-amino-4-bromophenol Chemical compound NC1=CC(Br)=CC=C1O JHRIPENGTGSNPJ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 235000005781 Avena Nutrition 0.000 description 4
- 244000075850 Avena orientalis Species 0.000 description 4
- 241000611157 Brachiaria Species 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 241000209082 Lolium Species 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 235000005775 Setaria Nutrition 0.000 description 4
- 241000232088 Setaria <nematode> Species 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical group [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 235000002634 Solanum Nutrition 0.000 description 4
- 241000207763 Solanum Species 0.000 description 4
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 4
- 239000012346 acetyl chloride Substances 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000004491 dispersible concentrate Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 4
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000003053 toxin Substances 0.000 description 4
- 231100000765 toxin Toxicity 0.000 description 4
- 108700012359 toxins Proteins 0.000 description 4
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 4
- 239000004562 water dispersible granule Substances 0.000 description 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 3
- XBNGYFFABRKICK-UHFFFAOYSA-N 2,3,4,5,6-pentafluorophenol Chemical compound OC1=C(F)C(F)=C(F)C(F)=C1F XBNGYFFABRKICK-UHFFFAOYSA-N 0.000 description 3
- 241000219144 Abutilon Species 0.000 description 3
- 241000219318 Amaranthus Species 0.000 description 3
- 244000025254 Cannabis sativa Species 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- 235000003445 Pistacia Nutrition 0.000 description 3
- 241000543704 Pistacia Species 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 244000098338 Triticum aestivum Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 238000009395 breeding Methods 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 230000002441 reversible effect Effects 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 239000000375 suspending agent Substances 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- HKELWJONQIFBPO-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-(trichloromethyl)-1,2,4-triazole-3-carboxylic acid Chemical compound N1=C(C(=O)O)N=C(C(Cl)(Cl)Cl)N1C1=CC=C(Cl)C=C1Cl HKELWJONQIFBPO-UHFFFAOYSA-N 0.000 description 2
- XEJNEDVTJPXRSM-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-methyl-4,5-dihydro-1H-pyrazole-3,5-dicarboxylic acid Chemical compound OC(=O)C1(C)CC(C(O)=O)=NN1C1=CC=C(Cl)C=C1Cl XEJNEDVTJPXRSM-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- 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
- SEZRREGFJFZQQD-UHFFFAOYSA-N 2-fluoropropanoyl chloride Chemical compound CC(F)C(Cl)=O SEZRREGFJFZQQD-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- RXTOMDFSTRZTTA-UHFFFAOYSA-N 3-amino-2-chloro-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C(Cl)=C1N RXTOMDFSTRZTTA-UHFFFAOYSA-N 0.000 description 2
- GVNTVQTVSUZWPB-UHFFFAOYSA-N 3-chloro-1-methoxy-4-methyl-2-nitrobenzene Chemical compound COC1=CC=C(C)C(Cl)=C1[N+]([O-])=O GVNTVQTVSUZWPB-UHFFFAOYSA-N 0.000 description 2
- VCBOOMGORINFOQ-UHFFFAOYSA-N 3-chloro-4-methyl-2-nitrophenol Chemical compound CC1=CC=C(O)C([N+]([O-])=O)=C1Cl VCBOOMGORINFOQ-UHFFFAOYSA-N 0.000 description 2
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 241000743339 Agrostis Species 0.000 description 2
- 241000743985 Alopecurus Species 0.000 description 2
- 241000428811 Alternanthera Species 0.000 description 2
- 241000223600 Alternaria Species 0.000 description 2
- 244000237956 Amaranthus retroflexus Species 0.000 description 2
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000193388 Bacillus thuringiensis Species 0.000 description 2
- 239000005472 Bensulfuron methyl Substances 0.000 description 2
- AORUMRNTAIWGKS-UHFFFAOYSA-N BrC=1C(=C(N(C)C)C(=CC=1)OC(F)(F)F)Cl Chemical compound BrC=1C(=C(N(C)C)C(=CC=1)OC(F)(F)F)Cl AORUMRNTAIWGKS-UHFFFAOYSA-N 0.000 description 2
- AVSOGNPDBSLELM-UHFFFAOYSA-N BrC=1C(=C(NC)C(=CC=1)OC(F)(F)F)Cl Chemical compound BrC=1C(=C(NC)C(=CC=1)OC(F)(F)F)Cl AVSOGNPDBSLELM-UHFFFAOYSA-N 0.000 description 2
- 235000006008 Brassica napus var napus Nutrition 0.000 description 2
- 241000209200 Bromus Species 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- 239000005492 Carfentrazone-ethyl Substances 0.000 description 2
- 241000209120 Cenchrus Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- YIZPGCGCVHBERQ-UHFFFAOYSA-N ClC1=C(C(=O)O)C=CC(=C1NC(=O)C1=NC=CC=C1)OC(F)(F)F Chemical compound ClC1=C(C(=O)O)C=CC(=C1NC(=O)C1=NC=CC=C1)OC(F)(F)F YIZPGCGCVHBERQ-UHFFFAOYSA-N 0.000 description 2
- QVLDPCSLXCLSNF-UHFFFAOYSA-N ClC1=C(C(=O)O)C=CC(=C1NC(=O)C1CC1)OC(F)(F)F Chemical compound ClC1=C(C(=O)O)C=CC(=C1NC(=O)C1CC1)OC(F)(F)F QVLDPCSLXCLSNF-UHFFFAOYSA-N 0.000 description 2
- IDYQXTSIFBKIAR-UHFFFAOYSA-N ClC1=C(C(=O)O)C=CC(=C1NC(CC)=O)OC(F)(F)F Chemical compound ClC1=C(C(=O)O)C=CC(=C1NC(CC)=O)OC(F)(F)F IDYQXTSIFBKIAR-UHFFFAOYSA-N 0.000 description 2
- VZDKVVVLWJBNOR-UHFFFAOYSA-N ClC1=C(C(=O)O)C=CC(=C1[N+](=O)[O-])OC Chemical compound ClC1=C(C(=O)O)C=CC(=C1[N+](=O)[O-])OC VZDKVVVLWJBNOR-UHFFFAOYSA-N 0.000 description 2
- CKANLXQJAVYIEA-UHFFFAOYSA-N ClC1=C(C(=O)OCC)C=CC(=C1[N+](=O)[O-])OC Chemical compound ClC1=C(C(=O)OCC)C=CC(=C1[N+](=O)[O-])OC CKANLXQJAVYIEA-UHFFFAOYSA-N 0.000 description 2
- 241000234653 Cyperus Species 0.000 description 2
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
- 235000017896 Digitaria Nutrition 0.000 description 2
- 241001303487 Digitaria <clam> Species 0.000 description 2
- 241000192043 Echinochloa Species 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 239000005562 Glyphosate Substances 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- DFFLOYGGGJLVGQ-UHFFFAOYSA-N NC=1C(=C(C(=O)OC2=C(C(=C(C(=C2F)F)F)F)F)C=CC=1OC)Cl Chemical compound NC=1C(=C(C(=O)OC2=C(C(=C(C(=C2F)F)F)F)F)C=CC=1OC)Cl DFFLOYGGGJLVGQ-UHFFFAOYSA-N 0.000 description 2
- YGGQQJBBZDKCOD-UHFFFAOYSA-N NC=1C(=C(C(=O)OCC)C=CC=1OC)Cl Chemical compound NC=1C(=C(C(=O)OCC)C=CC=1OC)Cl YGGQQJBBZDKCOD-UHFFFAOYSA-N 0.000 description 2
- 235000019502 Orange oil Nutrition 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000005662 Paraffin oil Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 241000589540 Pseudomonas fluorescens Species 0.000 description 2
- 240000009132 Sagittaria sagittifolia Species 0.000 description 2
- 241000202758 Scirpus Species 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 241000209072 Sorghum Species 0.000 description 2
- 241000819233 Tribulus <sea snail> Species 0.000 description 2
- 241001506766 Xanthium Species 0.000 description 2
- 101100339555 Zymoseptoria tritici HPPD gene Proteins 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 229960000892 attapulgite Drugs 0.000 description 2
- 229940097012 bacillus thuringiensis Drugs 0.000 description 2
- 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 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- SCKYRAXSEDYPSA-UHFFFAOYSA-N ciclopirox Chemical compound ON1C(=O)C=C(C)C=C1C1CCCCC1 SCKYRAXSEDYPSA-UHFFFAOYSA-N 0.000 description 2
- 229960003749 ciclopirox Drugs 0.000 description 2
- ICJSJAJWTWPSBD-UHFFFAOYSA-N cloquintocet Chemical compound C1=CN=C2C(OCC(=O)O)=CC=C(Cl)C2=C1 ICJSJAJWTWPSBD-UHFFFAOYSA-N 0.000 description 2
- BIKACRYIQSLICJ-UHFFFAOYSA-N cloransulam-methyl Chemical group N=1N2C(OCC)=NC(F)=CC2=NC=1S(=O)(=O)NC1=C(Cl)C=CC=C1C(=O)OC BIKACRYIQSLICJ-UHFFFAOYSA-N 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000013270 controlled release Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- URAZVWXGWMBUGJ-UHFFFAOYSA-N di(propan-2-yl)azanium;chloride Chemical compound [Cl-].CC(C)[NH2+]C(C)C URAZVWXGWMBUGJ-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- MLKCGVHIFJBRCD-UHFFFAOYSA-N ethyl 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-4-fluorophenyl}propanoate Chemical group C1=C(Cl)C(CC(Cl)C(=O)OCC)=CC(N2C(N(C(F)F)C(C)=N2)=O)=C1F MLKCGVHIFJBRCD-UHFFFAOYSA-N 0.000 description 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 229940097068 glyphosate Drugs 0.000 description 2
- XDDAORKBJWWYJS-UHFFFAOYSA-M glyphosate(1-) Chemical compound OP(O)(=O)CNCC([O-])=O XDDAORKBJWWYJS-UHFFFAOYSA-M 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium;hydroxide;hydrate Chemical compound [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 2
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000004535 oil miscible liquid Substances 0.000 description 2
- 239000010502 orange oil Substances 0.000 description 2
- 229910052625 palygorskite Inorganic materials 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
- 239000005648 plant growth regulator Substances 0.000 description 2
- 108091033319 polynucleotide Proteins 0.000 description 2
- 102000040430 polynucleotide Human genes 0.000 description 2
- 239000002157 polynucleotide Substances 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 239000012286 potassium permanganate Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- YXIIPOGUBVYZIW-UHFFFAOYSA-N pyraflufen Chemical compound ClC1=C(OC(F)F)N(C)N=C1C1=CC(OCC(O)=O)=C(Cl)C=C1F YXIIPOGUBVYZIW-UHFFFAOYSA-N 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000004550 soluble concentrate Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
- 229960000278 theophylline Drugs 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 229940047183 tribulus Drugs 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- RFZZKBWDDKMWNM-GTBMBKLPSA-N (5s,7r,8s,9r)-8,9-dihydroxy-7-(hydroxymethyl)-6-oxa-1,3-diazaspiro[4.4]nonane-2,4-dione Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@]11C(=O)NC(=O)N1 RFZZKBWDDKMWNM-GTBMBKLPSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- WNTGYJSOUMFZEP-SSDOTTSWSA-N (R)-mecoprop Chemical compound OC(=O)[C@@H](C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-SSDOTTSWSA-N 0.000 description 1
- FFQPZWRNXKPNPX-INIZCTEOSA-N (S)-beflubutamid Chemical compound O([C@@H](CC)C(=O)NCC=1C=CC=CC=1)C1=CC=C(F)C(C(F)(F)F)=C1 FFQPZWRNXKPNPX-INIZCTEOSA-N 0.000 description 1
- QNBTYORWCCMPQP-JXAWBTAJSA-N (Z)-dimethomorph Chemical compound C1=C(OC)C(OC)=CC=C1C(\C=1C=CC(Cl)=CC=1)=C/C(=O)N1CCOCC1 QNBTYORWCCMPQP-JXAWBTAJSA-N 0.000 description 1
- XEPXTKKIWBPAEG-UHFFFAOYSA-N 1,1-dichloropropan-1-ol Chemical compound CCC(O)(Cl)Cl XEPXTKKIWBPAEG-UHFFFAOYSA-N 0.000 description 1
- 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 description 1
- PYCINWWWERDNKE-UHFFFAOYSA-N 1-(2-chloro-6-propylimidazo[1,2-b]pyridazin-3-yl)sulfonyl-3-(4,6-dimethoxypyrimidin-2-yl)urea Chemical compound N12N=C(CCC)C=CC2=NC(Cl)=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 PYCINWWWERDNKE-UHFFFAOYSA-N 0.000 description 1
- VQHHIQJPQOLZGF-UHFFFAOYSA-N 1-(2-iodophenyl)sulfonyl-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)I)=N1 VQHHIQJPQOLZGF-UHFFFAOYSA-N 0.000 description 1
- QNGFJGCALLNSDE-UHFFFAOYSA-N 1-(3-chloro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyridin-2-yl)-5-(cyclopropylmethylamino)pyrazole-4-carbonitrile Chemical compound ClC=1C(=NN2C=1CCCC2)N1N=CC(=C1NCC1CC1)C#N QNGFJGCALLNSDE-UHFFFAOYSA-N 0.000 description 1
- CUJMCPPBTUATEJ-UHFFFAOYSA-N 1-(3-methyl-4-oxido-1-oxoquinoxalin-1-ium-2-yl)ethanone Chemical compound C1=CC=C2[N+](=O)C(C(=O)C)=C(C)N([O-])C2=C1 CUJMCPPBTUATEJ-UHFFFAOYSA-N 0.000 description 1
- GHLCSCRDVVEUQD-UHFFFAOYSA-N 1-({1-ethyl-4-[3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoyl]-1H-pyrazol-5-yl}oxy)ethyl methyl carbonate Chemical compound CCN1N=CC(C(=O)C=2C(=C(OCCOC)C(=CC=2)S(C)(=O)=O)C)=C1OC(C)OC(=O)OC GHLCSCRDVVEUQD-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- KNGWEAQJZJKFLI-UHFFFAOYSA-N 2,2-dimethyl-4h-1,3-benzodioxine-6-carbaldehyde Chemical compound O=CC1=CC=C2OC(C)(C)OCC2=C1 KNGWEAQJZJKFLI-UHFFFAOYSA-N 0.000 description 1
- GBBSAMQTQCPOBF-UHFFFAOYSA-N 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane Chemical compound CB1OB(C)OB(C)O1 GBBSAMQTQCPOBF-UHFFFAOYSA-N 0.000 description 1
- 239000002794 2,4-DB Substances 0.000 description 1
- YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- HEXDMALBSZQQNG-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-5-ethoxycarbonyl-3-methyl-4H-pyrazole-3-carboxylic acid Chemical group OC(=O)C1(C)CC(C(=O)OCC)=NN1C1=CC=C(Cl)C=C1Cl HEXDMALBSZQQNG-UHFFFAOYSA-N 0.000 description 1
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 description 1
- SURCGQGDUADKBL-UHFFFAOYSA-N 2-(2-hydroxyethylamino)-5-nitrobenzo[de]isoquinoline-1,3-dione Chemical compound [O-][N+](=O)C1=CC(C(N(NCCO)C2=O)=O)=C3C2=CC=CC3=C1 SURCGQGDUADKBL-UHFFFAOYSA-N 0.000 description 1
- IRJQWZWMQCVOLA-ZBKNUEDVSA-N 2-[(z)-n-[(3,5-difluorophenyl)carbamoylamino]-c-methylcarbonimidoyl]pyridine-3-carboxylic acid Chemical compound N=1C=CC=C(C(O)=O)C=1C(/C)=N\NC(=O)NC1=CC(F)=CC(F)=C1 IRJQWZWMQCVOLA-ZBKNUEDVSA-N 0.000 description 1
- XLFWTPOBIOMCKS-UHFFFAOYSA-N 2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxopyridazine-4-carbonyl]-5,5-dimethylcyclohexane-1,3-dione Chemical compound COC=1C=C(C=CC=1OC)N1N=C(C=C(C1=O)C(=O)C1C(CC(CC1=O)(C)C)=O)C XLFWTPOBIOMCKS-UHFFFAOYSA-N 0.000 description 1
- ANQRDMDBJYHVII-UHFFFAOYSA-N 2-[2-(3,4-dimethoxyphenyl)-6-methyl-3-oxopyridazine-4-carbonyl]cyclohexane-1,3-dione Chemical compound COC=1C=C(C=CC=1OC)N1N=C(C=C(C1=O)C(=O)C1C(CCCC1=O)=O)C ANQRDMDBJYHVII-UHFFFAOYSA-N 0.000 description 1
- MPPOHAUSNPTFAJ-UHFFFAOYSA-N 2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 MPPOHAUSNPTFAJ-UHFFFAOYSA-N 0.000 description 1
- AETKKVFPFBHLEG-UHFFFAOYSA-N 2-[6-cyclopropyl-2-(3,4-dimethoxyphenyl)-3-oxopyridazine-4-carbonyl]cyclohexane-1,3-dione Chemical compound C1(CC1)C=1C=C(C(N(N=1)C1=CC(=C(C=C1)OC)OC)=O)C(=O)C1C(CCCC1=O)=O AETKKVFPFBHLEG-UHFFFAOYSA-N 0.000 description 1
- KPSTXQYTZBZXMM-UHFFFAOYSA-N 2-[8-chloro-4-(4-methoxyphenyl)-3-oxoquinoxaline-2-carbonyl]cyclohexane-1,3-dione Chemical compound C1=CC(OC)=CC=C1N1C(=O)C(C(=O)C2C(CCCC2=O)=O)=NC2=C(Cl)C=CC=C21 KPSTXQYTZBZXMM-UHFFFAOYSA-N 0.000 description 1
- VQRYVKJGEDNMNC-UHFFFAOYSA-N 2-[[2-chloro-3-[2-(1,3-dioxolan-2-yl)ethoxy]-4-methylsulfonylphenyl]-hydroxymethylidene]cyclohexane-1,3-dione Chemical compound ClC1=C(OCCC2OCCO2)C(S(=O)(=O)C)=CC=C1C(O)=C1C(=O)CCCC1=O VQRYVKJGEDNMNC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- IRCMYGHHKLLGHV-UHFFFAOYSA-N 2-ethoxy-3,3-dimethyl-2,3-dihydro-1-benzofuran-5-yl methanesulfonate Chemical compound C1=C(OS(C)(=O)=O)C=C2C(C)(C)C(OCC)OC2=C1 IRCMYGHHKLLGHV-UHFFFAOYSA-N 0.000 description 1
- NPSJHQMIVNJLNN-UHFFFAOYSA-N 2-ethylhexyl 4-nitrobenzoate Chemical compound CCCCC(CC)COC(=O)C1=CC=C([N+]([O-])=O)C=C1 NPSJHQMIVNJLNN-UHFFFAOYSA-N 0.000 description 1
- 239000004808 2-ethylhexylester Substances 0.000 description 1
- ZVZPFTCEXIGSHM-UHFFFAOYSA-N 2-fluoropropanoic acid Chemical compound CC(F)C(O)=O ZVZPFTCEXIGSHM-UHFFFAOYSA-N 0.000 description 1
- CBQDTCDOVVBGMN-UHFFFAOYSA-N 2-methyl-3-octylphenol Chemical compound CCCCCCCCC1=CC=CC(O)=C1C CBQDTCDOVVBGMN-UHFFFAOYSA-N 0.000 description 1
- LLWADFLAOKUBDR-UHFFFAOYSA-N 2-methyl-4-chlorophenoxybutyric acid Chemical compound CC1=CC(Cl)=CC=C1OCCCC(O)=O LLWADFLAOKUBDR-UHFFFAOYSA-N 0.000 description 1
- WRFWAYDBNCOWRA-UHFFFAOYSA-N 3,4-dichloro-1-(6-iodo-4-oxo-2-thiophen-2-ylquinazolin-3-yl)pyrrole-2,5-dione Chemical compound O=C1C(Cl)=C(Cl)C(=O)N1N1C(=O)C2=CC(I)=CC=C2N=C1C1=CC=CS1 WRFWAYDBNCOWRA-UHFFFAOYSA-N 0.000 description 1
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 description 1
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 1
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- FVXUPMANSGTQGV-UHFFFAOYSA-N 3-(ethylsulfonylmethyl)-N-(5-methyl-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide Chemical compound C(C)S(=O)(=O)CC1=NN=C2N1C(=CC=C2C(=O)NC=1OC(=NN=1)C)C(F)(F)F FVXUPMANSGTQGV-UHFFFAOYSA-N 0.000 description 1
- CASLETQIYIQFTQ-UHFFFAOYSA-N 3-[[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)pyrazol-4-yl]methylsulfonyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound CN1N=C(C(F)(F)F)C(CS(=O)(=O)C=2CC(C)(C)ON=2)=C1OC(F)F CASLETQIYIQFTQ-UHFFFAOYSA-N 0.000 description 1
- DROBGEUNIQOKBV-UHFFFAOYSA-N 3-ethylsulfanyl-N-(1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide Chemical compound C(C)SC1=NN=C2N1C(=CC=C2C(=O)NC=1OC=NN=1)C(F)(F)F DROBGEUNIQOKBV-UHFFFAOYSA-N 0.000 description 1
- CIPJEXPBJDLNIP-UHFFFAOYSA-N 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1h-indol-6-yl)pyridine-2-carboxylic acid Chemical compound OC(=O)C1=C(Cl)C(N)=C(F)C(C=2C(=C3NC=CC3=CC=2)F)=N1 CIPJEXPBJDLNIP-UHFFFAOYSA-N 0.000 description 1
- BCFOOQRXUXKJCL-UHFFFAOYSA-N 4-amino-4-oxo-2-sulfobutanoic acid Chemical class NC(=O)CC(C(O)=O)S(O)(=O)=O BCFOOQRXUXKJCL-UHFFFAOYSA-N 0.000 description 1
- FNFDZCUEUHQFNX-UHFFFAOYSA-N 4-hydroxy-1,5-dimethyl-3-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]imidazolidin-2-one Chemical compound OC1N(C(N(C1C)C)=O)C1=NN(C(=C1)C(F)(F)F)C FNFDZCUEUHQFNX-UHFFFAOYSA-N 0.000 description 1
- MHIGUUYBHJZBNW-UHFFFAOYSA-N 4-hydroxy-1,5-dimethyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one Chemical compound CC1C(O)N(C(=O)N1C)c1cc(ccn1)C(F)(F)F MHIGUUYBHJZBNW-UHFFFAOYSA-N 0.000 description 1
- DXPNWQHGOPWNTO-UHFFFAOYSA-N 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one Chemical compound CON1C(C)C(O)N(C1=O)c1cc(ccn1)C(F)(F)F DXPNWQHGOPWNTO-UHFFFAOYSA-N 0.000 description 1
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 1
- OPEJGICLTMWFNQ-UHFFFAOYSA-N 5-[(2,6-difluorophenyl)methoxymethyl]-5-methyl-3-(3-methylthiophen-2-yl)-4h-1,2-oxazole Chemical compound C1=CSC(C=2CC(C)(COCC=3C(=CC=CC=3F)F)ON=2)=C1C OPEJGICLTMWFNQ-UHFFFAOYSA-N 0.000 description 1
- FOJWHUFRHXEUBA-UHFFFAOYSA-N 5-bromo-2-(trifluoromethoxy)aniline Chemical compound NC1=CC(Br)=CC=C1OC(F)(F)F FOJWHUFRHXEUBA-UHFFFAOYSA-N 0.000 description 1
- CTSLUCNDVMMDHG-UHFFFAOYSA-N 5-bromo-3-(butan-2-yl)-6-methylpyrimidine-2,4(1H,3H)-dione Chemical compound CCC(C)N1C(=O)NC(C)=C(Br)C1=O CTSLUCNDVMMDHG-UHFFFAOYSA-N 0.000 description 1
- OKRUMSWHDWKGHA-UHFFFAOYSA-N 5-bromopentanoyl chloride Chemical compound ClC(=O)CCCCBr OKRUMSWHDWKGHA-UHFFFAOYSA-N 0.000 description 1
- PHZSPMUIHAUXQQ-UHFFFAOYSA-N 5-ethoxy-4-hydroxy-1-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one Chemical compound CCOC1C(O)N(C(=O)N1C)c1cc(ccn1)C(F)(F)F PHZSPMUIHAUXQQ-UHFFFAOYSA-N 0.000 description 1
- XPXWYVCQCNFIIJ-UHFFFAOYSA-N 5-methyl-1,3,4-oxadiazol-2-amine Chemical compound CC1=NN=C(N)O1 XPXWYVCQCNFIIJ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 description 1
- 239000002890 Aclonifen Substances 0.000 description 1
- 241001133760 Acoelorraphe Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 239000005468 Aminopyralid Substances 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000254175 Anthonomus grandis Species 0.000 description 1
- 241000219195 Arabidopsis thaliana Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 239000005476 Bentazone Substances 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 240000000385 Brassica napus var. napus Species 0.000 description 1
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BOASXMYCEVISDM-UHFFFAOYSA-N C1(CC1)C=1C=C(C(N(N=1)C1=CC(=C(C=C1)OC)OC)=O)C(=O)C1C(CC(CC1=O)(C)C)=O Chemical compound C1(CC1)C=1C=C(C(N(N=1)C1=CC(=C(C=C1)OC)OC)=O)C(=O)C1C(CC(CC1=O)(C)C)=O BOASXMYCEVISDM-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- 235000000509 Chenopodium ambrosioides Nutrition 0.000 description 1
- 244000098897 Chenopodium botrys Species 0.000 description 1
- 235000005490 Chenopodium botrys Nutrition 0.000 description 1
- 239000005494 Chlorotoluron Substances 0.000 description 1
- 239000005496 Chlorsulfuron Substances 0.000 description 1
- 239000004381 Choline salt Substances 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 244000189548 Chrysanthemum x morifolium Species 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- ZEMYGZXFYNKHBZ-UHFFFAOYSA-N ClC1=C(C(=CC=C1C(NC1=NN=NN1C)=O)OC(F)(F)F)NC(=O)C1=NC=CC=C1 Chemical compound ClC1=C(C(=CC=C1C(NC1=NN=NN1C)=O)OC(F)(F)F)NC(=O)C1=NC=CC=C1 ZEMYGZXFYNKHBZ-UHFFFAOYSA-N 0.000 description 1
- 239000005497 Clethodim Substances 0.000 description 1
- 239000005498 Clodinafop Substances 0.000 description 1
- 239000005499 Clomazone Substances 0.000 description 1
- 239000005500 Clopyralid Substances 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 241000132542 Conyza Species 0.000 description 1
- 241000190633 Cordyceps Species 0.000 description 1
- OFSLKOLYLQSJPB-UHFFFAOYSA-N Cyclosulfamuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)NC=2C(=CC=CC=2)C(=O)C2CC2)=N1 OFSLKOLYLQSJPB-UHFFFAOYSA-N 0.000 description 1
- 239000005502 Cyhalofop-butyl Substances 0.000 description 1
- TYIYMOAHACZAMQ-CQSZACIVSA-N Cyhalofop-butyl Chemical group C1=CC(O[C@H](C)C(=O)OCCCC)=CC=C1OC1=CC=C(C#N)C=C1F TYIYMOAHACZAMQ-CQSZACIVSA-N 0.000 description 1
- 239000005503 Desmedipham Substances 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical class [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000005504 Dicamba Substances 0.000 description 1
- YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 description 1
- QNXAVFXEJCPCJO-UHFFFAOYSA-N Diclosulam Chemical compound N=1N2C(OCC)=NC(F)=CC2=NC=1S(=O)(=O)NC1=C(Cl)C=CC=C1Cl QNXAVFXEJCPCJO-UHFFFAOYSA-N 0.000 description 1
- 239000005507 Diflufenican Substances 0.000 description 1
- 239000005761 Dimethomorph Substances 0.000 description 1
- 239000005510 Diuron Substances 0.000 description 1
- 235000007351 Eleusine Nutrition 0.000 description 1
- 241000209215 Eleusine Species 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 239000005512 Ethofumesate Substances 0.000 description 1
- GMBRUAIJEFRHFQ-UHFFFAOYSA-N Fenchlorazole-ethyl Chemical group N1=C(C(=O)OCC)N=C(C(Cl)(Cl)Cl)N1C1=CC=C(Cl)C=C1Cl GMBRUAIJEFRHFQ-UHFFFAOYSA-N 0.000 description 1
- NRFQZTCQAYEXEE-UHFFFAOYSA-N Fenclorim Chemical compound ClC1=CC(Cl)=NC(C=2C=CC=CC=2)=N1 NRFQZTCQAYEXEE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 241000234642 Festuca Species 0.000 description 1
- 239000005561 Glufosinate Substances 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 241000904869 Hexacola Species 0.000 description 1
- RFZZKBWDDKMWNM-UHFFFAOYSA-N Hydantocidin Natural products OC1C(O)C(CO)OC11C(=O)NC(=O)N1 RFZZKBWDDKMWNM-UHFFFAOYSA-N 0.000 description 1
- XVOKUMIPKHGGTN-UHFFFAOYSA-N Imazethapyr Chemical compound OC(=O)C1=CC(CC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 XVOKUMIPKHGGTN-UHFFFAOYSA-N 0.000 description 1
- 238000012696 Interfacial polycondensation Methods 0.000 description 1
- 240000007218 Ipomoea hederacea Species 0.000 description 1
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 239000004117 Lignosulphonate Substances 0.000 description 1
- 240000004296 Lolium perenne Species 0.000 description 1
- 239000005574 MCPA Substances 0.000 description 1
- 239000005575 MCPB Substances 0.000 description 1
- 101150039283 MCPB gene Proteins 0.000 description 1
- 239000005576 Mecoprop-P Substances 0.000 description 1
- NMMIHXMBOZYNET-UHFFFAOYSA-N Methyl picolinate Chemical compound COC(=O)C1=CC=CC=N1 NMMIHXMBOZYNET-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 235000003990 Monochoria hastata Nutrition 0.000 description 1
- 240000000178 Monochoria vaginalis Species 0.000 description 1
- FDSYCBCTZKTQFU-UHFFFAOYSA-N N-(5-methyl-1,3,4-oxadiazol-2-yl)-3-(propan-2-ylsulfanylmethyl)-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide Chemical compound C(C)(C)SCC1=NN=C2N1C(=CC=C2C(=O)NC=1OC(=NN=1)C)C(F)(F)F FDSYCBCTZKTQFU-UHFFFAOYSA-N 0.000 description 1
- ODXFUPRPCAYZLK-UHFFFAOYSA-N N-(5-methyl-1,3,4-oxadiazol-2-yl)-3-(propan-2-ylsulfonylmethyl)-5-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide Chemical compound C(C)(C)S(=O)(=O)CC1=NN=C2N1C(=CC=C2C(=O)NC=1OC(=NN=1)C)C(F)(F)F ODXFUPRPCAYZLK-UHFFFAOYSA-N 0.000 description 1
- WPPOGHDFAVQKLN-UHFFFAOYSA-N N-Octyl-2-pyrrolidone Chemical compound CCCCCCCCN1CCCC1=O WPPOGHDFAVQKLN-UHFFFAOYSA-N 0.000 description 1
- NTBVTCXMRYKRTB-UHFFFAOYSA-N N-{2-[(4,6-dimethoxypyrimidin-2-yl)(hydroxy)methyl]-6-(methoxymethyl)phenyl}-1,1-difluoromethanesulfonamide Chemical compound COCC1=CC=CC(C(O)C=2N=C(OC)C=C(OC)N=2)=C1NS(=O)(=O)C(F)F NTBVTCXMRYKRTB-UHFFFAOYSA-N 0.000 description 1
- HEODQQKPYDRYFL-UHFFFAOYSA-N NC=1C(=C(C(=O)O)C=CC=1OCC(F)(F)F)Cl Chemical compound NC=1C(=C(C(=O)O)C=CC=1OCC(F)(F)F)Cl HEODQQKPYDRYFL-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 108091028043 Nucleic acid sequence Proteins 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 241001147398 Ostrinia nubilalis Species 0.000 description 1
- 239000005590 Oxyfluorfen Substances 0.000 description 1
- OQMBBFQZGJFLBU-UHFFFAOYSA-N Oxyfluorfen Chemical compound C1=C([N+]([O-])=O)C(OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 OQMBBFQZGJFLBU-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 241000287127 Passeridae Species 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 239000005615 Quizalofop-P-tefuryl Substances 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 240000003461 Setaria viridis Species 0.000 description 1
- 235000002248 Setaria viridis Nutrition 0.000 description 1
- 241000863429 Shewanella colwelliana Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- 241000131480 Solomonas Species 0.000 description 1
- 240000003829 Sorghum propinquum Species 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 239000005622 Thiencarbazone Substances 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 1
- 241000405217 Viola <butterfly> Species 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- YDHWWBZFRZWVHO-UHFFFAOYSA-N [hydroxy(phosphonooxy)phosphoryl] phosphono hydrogen phosphate Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(O)=O YDHWWBZFRZWVHO-UHFFFAOYSA-N 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- NUFNQYOELLVIPL-UHFFFAOYSA-N acifluorfen Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NUFNQYOELLVIPL-UHFFFAOYSA-N 0.000 description 1
- DDBMQDADIHOWIC-UHFFFAOYSA-N aclonifen Chemical compound C1=C([N+]([O-])=O)C(N)=C(Cl)C(OC=2C=CC=CC=2)=C1 DDBMQDADIHOWIC-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- RQVYBGPQFYCBGX-UHFFFAOYSA-N ametryn Chemical compound CCNC1=NC(NC(C)C)=NC(SC)=N1 RQVYBGPQFYCBGX-UHFFFAOYSA-N 0.000 description 1
- ORFPWVRKFLOQHK-UHFFFAOYSA-N amicarbazone Chemical compound CC(C)C1=NN(C(=O)NC(C)(C)C)C(=O)N1N ORFPWVRKFLOQHK-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- NIXXQNOQHKNPEJ-UHFFFAOYSA-N aminopyralid Chemical compound NC1=CC(Cl)=NC(C(O)=O)=C1Cl NIXXQNOQHKNPEJ-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 1
- 238000000498 ball milling Methods 0.000 description 1
- 238000010296 bead milling Methods 0.000 description 1
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 description 1
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 description 1
- GINJFDRNADDBIN-FXQIFTODSA-N bilanafos Chemical compound OC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](N)CCP(C)(O)=O GINJFDRNADDBIN-FXQIFTODSA-N 0.000 description 1
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 1
- 229920002988 biodegradable polymer Polymers 0.000 description 1
- 239000004621 biodegradable polymer Substances 0.000 description 1
- FUHMZYWBSHTEDZ-UHFFFAOYSA-M bispyribac-sodium Chemical compound [Na+].COC1=CC(OC)=NC(OC=2C(=C(OC=3N=C(OC)C=C(OC)N=3)C=CC=2)C([O-])=O)=N1 FUHMZYWBSHTEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- HKPHPIREJKHECO-UHFFFAOYSA-N butachlor Chemical compound CCCCOCN(C(=O)CCl)C1=C(CC)C=CC=C1CC HKPHPIREJKHECO-UHFFFAOYSA-N 0.000 description 1
- JEDYYFXHPAIBGR-UHFFFAOYSA-N butafenacil Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=CC=C(Cl)C(C(=O)OC(C)(C)C(=O)OCC=C)=C1 JEDYYFXHPAIBGR-UHFFFAOYSA-N 0.000 description 1
- CURLHBZYTFVCRG-UHFFFAOYSA-N butan-2-yl n-(3-chlorophenyl)carbamate Chemical compound CCC(C)OC(=O)NC1=CC=CC(Cl)=C1 CURLHBZYTFVCRG-UHFFFAOYSA-N 0.000 description 1
- JIJAYWGYIDJVJI-UHFFFAOYSA-N butyl naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)OCCCC)=CC=CC2=C1 JIJAYWGYIDJVJI-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- HCWYXKWQOMTBKY-UHFFFAOYSA-N calcium;dodecyl benzenesulfonate Chemical compound [Ca].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 HCWYXKWQOMTBKY-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- RIUXZHMCCFLRBI-UHFFFAOYSA-N chlorimuron Chemical compound COC1=CC(Cl)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 RIUXZHMCCFLRBI-UHFFFAOYSA-N 0.000 description 1
- NSWAMPCUPHPTTC-UHFFFAOYSA-N chlorimuron-ethyl Chemical group CCOC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(Cl)=CC(OC)=N1 NSWAMPCUPHPTTC-UHFFFAOYSA-N 0.000 description 1
- JXCGFZXSOMJFOA-UHFFFAOYSA-N chlorotoluron Chemical compound CN(C)C(=O)NC1=CC=C(C)C(Cl)=C1 JXCGFZXSOMJFOA-UHFFFAOYSA-N 0.000 description 1
- VJYIFXVZLXQVHO-UHFFFAOYSA-N chlorsulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 VJYIFXVZLXQVHO-UHFFFAOYSA-N 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 235000019417 choline salt Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- SILSDTWXNBZOGF-JWGBMQLESA-N clethodim Chemical compound CCSC(C)CC1CC(O)=C(C(CC)=NOC\C=C\Cl)C(=O)C1 SILSDTWXNBZOGF-JWGBMQLESA-N 0.000 description 1
- YUIKUTLBPMDDNQ-MRVPVSSYSA-N clodinafop Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=NC=C(Cl)C=C1F YUIKUTLBPMDDNQ-MRVPVSSYSA-N 0.000 description 1
- 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 1
- KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 description 1
- HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical compound OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 description 1
- 238000005354 coacervation Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000011162 core material Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
- WMSPXQIQBQAWLL-UHFFFAOYSA-N cyclopropanesulfonamide Chemical compound NS(=O)(=O)C1CC1 WMSPXQIQBQAWLL-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000013461 design Methods 0.000 description 1
- WZJZMXBKUWKXTQ-UHFFFAOYSA-N desmedipham Chemical compound CCOC(=O)NC1=CC=CC(OC(=O)NC=2C=CC=CC=2)=C1 WZJZMXBKUWKXTQ-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- KVBKAPANDHPRDG-UHFFFAOYSA-N dibromotetrafluoroethane Chemical compound FC(F)(Br)C(F)(F)Br KVBKAPANDHPRDG-UHFFFAOYSA-N 0.000 description 1
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 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 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical compound CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000004492 dustable powder Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000105 evaporative light scattering detection Methods 0.000 description 1
- ACDZDIIWZVQMIX-UHFFFAOYSA-N fenoxasulfone Chemical compound C1=C(Cl)C(OCC)=CC(Cl)=C1CS(=O)(=O)C1=NOC(C)(C)C1 ACDZDIIWZVQMIX-UHFFFAOYSA-N 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- XFZUQTKDBCOXPP-UHFFFAOYSA-N florpyrauxifen Chemical compound COC1=C(Cl)C=CC(C=2C(=C(N)C(Cl)=C(C(O)=O)N=2)F)=C1F XFZUQTKDBCOXPP-UHFFFAOYSA-N 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- KKLBEFSLWYDQFI-UHFFFAOYSA-N halauxifen Chemical compound COC1=C(Cl)C=CC(C=2N=C(C(Cl)=C(N)C=2)C(O)=O)=C1F KKLBEFSLWYDQFI-UHFFFAOYSA-N 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 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 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- ZJGIYAGVUVFEKW-UHFFFAOYSA-N hydrogen peroxide;lithium Chemical compound [Li].OO ZJGIYAGVUVFEKW-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- ATQYNBNTEXNNIK-UHFFFAOYSA-N imidazol-2-ylidene Chemical group [C]1NC=CN1 ATQYNBNTEXNNIK-UHFFFAOYSA-N 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- ITGSCCPVERXFGN-UHFFFAOYSA-N isoxadifen Chemical compound C1C(C(=O)O)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 ITGSCCPVERXFGN-UHFFFAOYSA-N 0.000 description 1
- MWKVXOJATACCCH-UHFFFAOYSA-N isoxadifen-ethyl Chemical group C1C(C(=O)OCC)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 MWKVXOJATACCCH-UHFFFAOYSA-N 0.000 description 1
- 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
- 230000002147 killing effect Effects 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
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 235000019357 lignosulphonate Nutrition 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000012669 liquid formulation Substances 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
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 235000011160 magnesium carbonates Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- JCHMGYRXQDASJE-UHFFFAOYSA-N metcamifen Chemical compound C1=CC(NC(=O)NC)=CC=C1S(=O)(=O)NC(=O)C1=CC=CC=C1OC JCHMGYRXQDASJE-UHFFFAOYSA-N 0.000 description 1
- 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
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000011785 micronutrient Substances 0.000 description 1
- 235000013369 micronutrients Nutrition 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- GBHVIWKSEHWFDD-UHFFFAOYSA-N n-[2-(4,6-dimethoxy-1,3,5-triazine-2-carbonyl)-6-fluorophenyl]-1,1-difluoro-n-methylmethanesulfonamide Chemical compound COC1=NC(OC)=NC(C(=O)C=2C(=C(F)C=CC=2)N(C)S(=O)(=O)C(F)F)=N1 GBHVIWKSEHWFDD-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000006095 n-butyl sulfinyl group Chemical group 0.000 description 1
- 125000006126 n-butyl sulfonyl group Chemical group 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- OLZQTUCTGLHFTQ-UHFFFAOYSA-N octan-2-yl 2-(4-amino-3,5-dichloro-6-fluoropyridin-2-yl)oxyacetate Chemical group CCCCCCC(C)OC(=O)COC1=NC(F)=C(Cl)C(N)=C1Cl OLZQTUCTGLHFTQ-UHFFFAOYSA-N 0.000 description 1
- GJYXGIIWJFZCLN-UHFFFAOYSA-N octane-2,4-dione Chemical compound CCCCC(=O)CC(C)=O GJYXGIIWJFZCLN-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- PENAXHPKEVTBLF-UHFFFAOYSA-L palladium(2+);prop-1-ene;dichloride Chemical compound [Pd+]Cl.[Pd+]Cl.[CH2-]C=C.[CH2-]C=C PENAXHPKEVTBLF-UHFFFAOYSA-L 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000011236 particulate material Substances 0.000 description 1
- XDRYMKDFEDOLFX-UHFFFAOYSA-N pentamidine Chemical compound C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 XDRYMKDFEDOLFX-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 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
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 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
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- ISYORFGKSZLPNW-UHFFFAOYSA-N propan-2-ylazanium;chloride Chemical compound [Cl-].CC(C)[NH3+] ISYORFGKSZLPNW-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 229910052903 pyrophyllite 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
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003248 quinolines 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
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 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
- CAQKQIYWKXZJGD-UHFFFAOYSA-M sodium;2-bromo-2,2-difluoroacetate Chemical compound [Na+].[O-]C(=O)C(F)(F)Br CAQKQIYWKXZJGD-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
- 238000001179 sorption measurement Methods 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000012258 stirred mixture 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
- FZMKKCQHDROFNI-UHFFFAOYSA-N sulfometuron Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 FZMKKCQHDROFNI-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- QQDYOLJZDUADHV-CJNGLKHVSA-N tetflupyrolimet Chemical compound FC1=C(C=CC=C1)NC(=O)[C@H]1C(N(C[C@@H]1C1=CC(=CC=C1)C(F)(F)F)C)=O QQDYOLJZDUADHV-CJNGLKHVSA-N 0.000 description 1
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 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
- 238000003971 tillage Methods 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
- AZHZOGYUMMIAOF-UHFFFAOYSA-N trifludimoxazin Chemical compound O=C1N(C)C(=S)N(C)C(=O)N1C(C(=C1)F)=CC2=C1OC(F)(F)C(=O)N2CC#C AZHZOGYUMMIAOF-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical class C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
- 238000001946 ultra-performance liquid chromatography-mass spectrometry Methods 0.000 description 1
- 241001478887 unidentified soil bacteria Species 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003643 water by type Substances 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
- 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
- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- 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
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
本发明涉及具有式(I)的化合物:或其农艺学上可接受的盐,其中Q、R2、R3、R4和R5是如本文所描述的。本发明进一步涉及包含所述化合物的组合物、使用所述组合物控制杂草的方法、以及具有式(I)的化合物作为除草剂的用途。
Description
本发明涉及新颖的除草化合物、其制备方法、包含这些新颖的化合物的除草组合物、以及其用于控制杂草(特别是在有用植物作物中)的用途或用于抑制植物生长的用途。
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WO2012/028579和WO2012/126932中。本发明涉及新颖的芳基甲酰胺。
因此,根据本发明,提供了一种具有式(I)的化合物:
或其农艺学上可接受的盐,
其中:-
Q是Q1或Q2;
R1a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-;
R1b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是C1-C6卤代烷基或C1-C6烷基;
R4选自由以下组成的组:C1-C6烷基-、C1-C6卤代烷基-、C1-C6烷基-C(O)-、C1-C6卤代烷基-C(O)-、C3-C6环烷基-、C3-C6环烷基-C1-C3烷基-、C3-C6环烷基-C(O)-、C1-C3烷氧基-C1-C3烷基-、C1-C3烷氧基-C1-C3烷基-C(O)-、-C(O)-苯基和-C(O)-杂芳基,其中苯基、杂芳基或C3-C6环烷基任选地被1、2或3个选自由卤素、C1-C6烷基(例如甲基)、C1-C6卤代烷基和C1-C6烷氧基组成的组的取代基取代;
R5选自由以下组成的组:氢、C1-C6烷基-、C1-C6卤代烷基和C1-C6环烷基;或者
R4和R5连同它们附接的氮原子一起形成任选地被氧代基取代的5元或6元饱和杂环;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)。
C3-C6环烷基-包括环丙基(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)。
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-、2,2-二氟乙基、1,1-二氟乙基、1,1,2,2-四氟乙基、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。
在本发明的优选实施例中,R1a和R1b选自由以下组成的组:甲基、乙基和正丙基。
在本发明的另一个实施例中,Q是Q1。因此,在该实施例中,具有式(I)的化合物是具有式(Ia)的化合物:
其中R1a、R2、R3、R4和R5是如关于具有式(I)的化合物所定义的。
在本发明的另一个实施例中,Q是Q2。因此,在本发明的该具体实施例中,提供了一种具有式(Ib)的化合物
其中R1b、R2、R3、R4和R5是如关于具有式(I)的化合物所定义的。
在本发明的优选实施例中,R2选自由以下组成的组:甲基、Cl、-CF3和-SO2甲基,更优选Cl。
在本发明的另一个优选实施例中,R3选自由以下组成的组:-CH3、-CF3、-CHF2和-CF2CF2H,更优选-CF3或-CHF2。
在本发明的一个实施例中,R4是-C(O)-杂芳基,其中杂芳基如先前所描述的任选地被取代并且选自由R4a、R4b、R4c、R4d、R4e、R4f、R4g和R4h组成的组:
在本发明的优选实施例中,杂芳基是R4c,其任选地被1、2或3个选自由以下组成的组的取代基取代:卤素、C1-C6烷基(例如甲基)、C1-C6卤代烷基和C1-C6烷氧基。在本发明还更优选的实施例中,杂芳基是R4c,其任选地被一个卤素、优选氟取代。
在本发明的另一个实施例中,R4选自由以下组成的组:C1-C6烷基-(优选甲基)、C1-C6烷基-C(O)-(优选CH3CH2C(O)-)和C3-C6环烷基-C(O)-(优选cPr-C(O)-)。
在本发明的另一个实施例中,R5是氢或C1-C6烷基-(优选甲基),最优选氢。
在本发明的一个实施例中,R4是甲基或CH3CH2C(O)-,并且R5是氢。在本发明的另一个实施例中,R4是-C(O)-杂芳基,其中杂芳基是任选地被一个卤素、优选氟取代的R4c,并且R5是氢。
在本发明的另一个实施例中,R4和R5一起形成任选地被选自由以下组成的组的氧代基取代的5元或6元饱和杂环:-C(O)-CH2CH2CH2CH2-、-CH2CH2OCH2CH2-、-C(O)CH2CH2CH2-、-CH2CH2CH2CH2CH2-和-CH2CH2CH2CH2-,优选-C(O)-CH2CH2CH2CH2-。
具有式(I)的化合物(以及用于合成具有式(I)的化合物的某些中间体化合物)可以包含不对称中心并且可以作为单一对映异构体、呈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,包含呈所有可能比率的非对映异构体。典型地,与其他可能性相比,这些对映异构体之一具有增强的生物活性。
本发明还包括具有式(I)的化合物的所有可能的几何和互变异构形式。
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一种除草组合物,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。最终稀释通常用水进行,但是可以替代水或除了水之外使用例如液体肥料、微量营养素、生物有机体、油或溶剂进行。
除草组合物总体上包含按重量计从0.1%至99%、尤其是按重量计从0.1%至95%的具有式I的化合物和按重量计从1%至99.9%的配制辅助剂,该配制辅助剂优选地包括按重量计从0至25%的表面活性物质。
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试剂的混合物进行混合,以改进水分散性/水溶性。然后将混合物研磨成细粉末。也可以将类似的组合物颗粒化以形成水溶性颗粒剂(SG)。
可湿性粉剂(WP)可以通过将具有式(I)的化合物与一种或多种固体稀释剂或载体、一种或多种湿润剂以及优选地,一种或多种分散剂,以及任选地,一种或多种悬浮剂混合来制备以促进在液体中的分散。然后将混合物研磨成细粉末。也可以将类似的组合物颗粒化以形成水可分散性颗粒剂(WG)。
可以这样形成颗粒剂(GR):通过将具有式(I)的化合物与一种或多种粉状固体稀释剂或载体的混合物颗粒化形成,或者通过将具有式(I)的化合物(或其在合适试剂中的溶液)吸收进多孔颗粒材料(如浮石、凹凸棒石粘土、漂白土、硅藻土(kieselguhr)、硅藻土(diatomaceous earths)或玉米芯粉),或通过将具有式(I)的化合物(或其在合适试剂中的溶液)吸附到硬芯材料(如沙、硅酸盐、矿物碳酸盐、硫酸盐或磷酸盐)上并且如果必要的话,进行干燥来由预成型的空白颗粒形成。通常用于帮助吸收或吸附的试剂包括溶剂(如脂肪族和芳香族石油溶剂、醇、醚、酮以及酯)和粘着剂(如聚乙酸乙烯酯、聚乙烯醇、糊精、糖以及植物油)。一种或多种其他添加剂也可以包含在颗粒剂中(例如乳化剂、湿润剂或分散剂)。
可分散性浓缩物(DC)可以通过将具有式(I)的化合物溶于水或有机溶剂(如酮、醇或二醇醚)中来制备。这些溶液可以含有表面活性剂(例如以改进水稀释或防止喷洒罐中的结晶)。
可乳化性浓缩物(EC)或水包油乳液(EW)可以通过将具有式(I)的化合物溶于有机溶剂(任选地含有一种或多种湿润剂、一种或多种乳化剂或者所述试剂的混合物)中来制备。在EC中使用的合适的有机溶剂包括芳香族烃(如烷基苯或烷基萘,例如SOLVESSO 100、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)、N-烷基吡咯烷酮类(如N-甲基吡咯烷酮或N-辛基吡咯烷酮)、脂肪酸的二甲基酰胺(如C8-C10脂肪酸二甲基酰胺)和氯化烃。EC产品可以在添加到水中时自发地乳化,从而产生具有足够稳定性的乳液,以允许通过适当设备进行喷洒施用。
EW的制备涉及获得作为液体(如果它在室温下不是液体,则它可以在典型地低于70℃的合理温度下熔化)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中使用的合适溶剂包括上文描述的在EC或EW中使用的那些。ME可以是水包油体系或油包水体系(存在哪种体系可以通过电导率测量来测定)并且可以适用于在同一配制品中混合水溶性的杀有害生物剂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上文描述的试剂的水中,以产生期望的最终产物。
气溶胶配制品包含具有式(I)的化合物和合适的推进剂(例如正丁烷)。还可以将具有式(I)的化合物溶于或分散于合适的介质(例如水或可与水混溶的液体,如正丙醇)中以提供在不加压的手动喷洒泵中使用的组合物。
胶囊悬浮液(CS)可以通过与制备EW配制品类似的方式来制备,但具有另外的聚合阶段,使得获得油滴的水性分散体,其中每个油滴被聚合物壳所包裹并且含有具有式(I)的化合物以及任选地用于该油滴的载体或稀释剂。聚合物壳可以通过界面缩聚反应或通过凝聚程序产生。这些组合物可以提供具有式(I)的化合物的受控释放并且它们可以用于种子处理。具有式(I)的化合物还可以配制在可生物降解的聚合物基质中以提供该化合物的缓慢的、受控的释放。
组合物可以包含一种或多种添加剂以改进该组合物的生物性能,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(例如月桂基硫酸钠)、磺化的芳香族化合物的盐(例如十二烷基苯磺酸钠、十二烷基苯磺酸钙、丁基萘磺酸盐以及二-异丙基-萘磺酸钠和三-异丙基-萘磺酸钠的混合物)、醚硫酸盐、醇醚硫酸盐(例如月桂醇聚醚-3-硫酸钠)、醚羧酸盐(例如月桂醇聚醚-3-羧酸钠)、磷酸酯(来自一种或多种脂肪醇与磷酸(主要是单酯)或与五氧化二磷(主要是二酯)之间反应的产物,例如月桂醇与四磷酸之间的反应;另外这些产物可以被乙氧基化)、磺基琥珀酰胺酸盐、石蜡或烯烃磺酸盐、牛磺酸盐以及木质素磺酸盐。
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)。
还可以将本发明的这些除草化合物以与一种或多种另外的除草剂和/或植物生长调节剂的混合物使用。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、甜菜安、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、苯吡菌胺(epyrifenacil)、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、氟草隆氟啶嘧磺隆(包括氟啶嘧磺隆-甲基-钠)、氟草烟(包括氯氟吡氧乙酸(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、高二甲四氯丙酸(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、吡丙醚(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、四氟吡咯烷酮(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、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、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)、3-乙基硫烷基-N-(1,3,4-噁二唑-2-基)-5-(三氟甲基)-[1,2,4]三唑并[4,3-a]吡啶-8-甲酰胺、3-(异丙基硫烷基甲基)-N-(5-甲基-1,3,4-噁二唑-2-基)-5-(三氟甲基)-[1,2,4]三唑并[4,3-a]吡啶-8-甲酰胺、3-(异丙基磺酰基甲基)-N-(5-甲基-1,3,4-噁二唑-2-基)-5-(三氟甲基)-[1,2,4]三唑并[4,3-a]吡啶-8-甲酰胺、3-(乙基磺酰基甲基)-N-(5-甲基-1,3,4-噁二唑-2-基)-5-(三氟甲基)-[1,2,4]三唑并[4,3-a]吡啶-8-甲酰胺和2-[[3-[[3-氯-5-氟-6-[3-甲基-2,6-二氧代-4-(三氟甲基)嘧啶-1-基]-2-吡啶基]氧基]乙酸乙酯。
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The PesticideManual[杀有害生物剂手册],第十六版,英国作物保护委员会(British Crop ProtectionCouncil),2012中所提到的。
具有式I的化合物还可以在与其他农用化学品(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这些配制品中(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(cloquintocet)(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)、除草剂安全剂(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、双苯噁唑酸乙酯、解毒喹和/或除草剂安全剂的混合物。
具有式I的化合物的安全剂还可以呈酯或盐的形式,如例如在杀有害生物剂手册,第16版(BCPC),2012中所提到的。提及解草喹还适用于其锂、钠、钾、钙、镁、铝、铁、铵、季铵、锍或鏻盐(如在WO 02/34048中披露的),并且对解草唑-乙基的提及还适用于解草唑,等。
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。
这些混合物可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的化合物与安全剂的对应混合物)。
本发明还进一步提供了一种在场所处控制杂草的方法,所述方法包括向所述场所施用控制杂草量的包含具有式(I)的化合物的组合物。此外,本发明进一步提供了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’意指植物在其中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,该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(更具体地说,衍生自荧光假单胞菌(Pseudomonas fluorescens)或希瓦氏菌(Shewanella colwelliana))、或衍生自植物(更具体地说,衍生自单子叶植物或还更具体地说,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(WO2012/082542)、SYHT0H2(WO2012/082548)和FG72。可以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WO2010/085705和WO2011/068567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、一种或多种有待控制的杂草、主要气候条件、以及受施用方法、施用时间以及目标作物支配的其他因素。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)、滴加或浸灌。
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。通过常规的育种方法已经赋予对咪唑啉酮(例如,甲氧咪草烟)的耐受性的作物的实例是Clearfield夏季油菜(卡诺拉(canola))。通过基因工程方法已经赋予对除草剂的耐受性的作物的实例包括例如具有草甘膦和草铵膦抗性的玉米品种,这些玉米品种在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对有害昆虫的抗性的那些,例如Bt玉米(对欧洲玉米螟有抗性)、Bt棉花(对棉铃象鼻虫有抗性)以及还有Bt马铃薯(对科罗拉多甲虫有抗性)。Bt玉米的实例是NK的Bt 176玉米杂交体(先正达种子公司(SyngentaSeeds))。Bt毒素是由苏芸金芽孢杆菌(Bacillus thuringiensis)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-374753、WO 93/07278、WO95/34656、WO 03/052073和EP-A-427 529中。包含一个或多个编码杀昆虫抗性和表达一种或多种毒素的基因的转基因植物的实例是KnockOut(玉米)、YieldGard(玉米)、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”转基因事件)。例如,种子可以具有表达杀昆虫的Cry3蛋白的能力,而同时对草甘膦是耐受的。
作物植物还应理解为包括通过常规的育种或基因工程的方法获得并且包含所谓的输出性状(例如改进的储存稳定性、更高的营养价值以及改进的风味)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物种,例如剪股颖属(Agrostis)、看麦娘属(Alopecurus)、燕麦属(Avena)、臂形草属(Brachiaria)、雀麦属(Bromus)、蒺藜草属(Cenchrus)、莎草属(Cyperus)、马唐属(Digitaria)、稗属(Echinochloa)、穇属(Eleusine)、黑麦草属(Lolium)、雨久花属(Monochoria)、筒轴茅属(Rottboellia)、慈姑属(Sagittaria)、藨草属(Scirpus)、狗尾草属(Setaria)以及高粱属(Sorghum),也可以是双子叶物种,例如苘麻属(Abutilon)、苋属(Amaranthus)、豚草属(Ambrosia)、藜属(Chenopodium)、菊属(Chrysanthemum)、白酒草属(Conyza)、拉拉藤属(Galium)、番薯属(Ipomoea)、旱金莲属(Nasturtium)、黄花稔属(Sida)、白芥属(Sinapis)、茄属(Solanum)、繁缕属(Stellaria)、婆婆纳属(Veronica)、堇菜属(Viola)以及苍耳属(Xanthium)。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。
本发明的化合物可以根据以下方案来制备。
具有式(I)的化合物可以由具有式(II)的化合物制备。
将具有式(II)的化合物用具有式(III)的胺(对于其中Q=Q1的本发明的实施例)或具有式(IV)的胺(对于其中Q=Q2的本发明的实施例)和N-甲酰基糖精和三乙胺,用N-甲基吡咯烷酮作为溶剂,用乙酸钯(II)催化剂和呫吨配体处理。反应可以使用连续流动反应器进行。
可替代地,具有式(I)的化合物可以由具有式(V)的苯甲酸制备。
在合适的溶剂(例如吡啶)中,用酰胺偶联试剂(例如亚硫酰氯和N-甲基咪唑)处理具有式(V)的苯甲酸和具有式(III)的胺(对于其中Q=Q1的本发明的实施例)或具有式(IV)的胺(对于其中Q=Q2的本发明的实施例)。
具有式(V)的化合物可以通过具有式(VI)的酯的水解来制备。
在合适的溶剂(例如乙醇:水的3:1混合物)中,用氢氧化钠处理具有式(VI)的酯,以得到具有式(V)的化合物。
在R2不是氯的情况下,具有式(VI)的化合物可以由其中R2是氯的具有式(VI)的化合物制备。
转化的方法将取决于R2的特性。技术人员将熟悉将氯基团转化为R2基团的方法。例如,在R2是甲基的情况下,进行Suzuki反应,其中用合适的催化剂(例如[1,3-双(2,6-二异丙基苯基)咪唑-2-亚基](3-氯吡啶基)二氯化钯(II))用三甲基环硼氧烷和碱(例如碳酸钾)处理R2=Cl的化合物。
其中R2=Cl的具有式(VI)的化合物可以由其中R2=Cl的具有式(II)的化合物制备。
使具有式(II)的化合物在具有一氧化碳气氛的高压釜中与碱(例如三乙胺)和钯催化剂(例如[1,1'-双(二苯基膦基)二茂铁]二氯化钯(II))在甲醇和乙腈的混合溶剂中反应。
在R5不是氢的情况下,其中R2=Cl的具有式(II)的化合物可以由具有式(VII)的化合物和具有式(VII)的化合物制备。
在合适的溶剂中,用具有式(VIII)的化合物(其中LG被定义为离去基团)处理具有式(VII)的化合物。该反应可以任选地需要碱。碱的要求和选择将是技术人员所熟悉的。例如,在R5是乙酰基的情况下,具有式(VIII)的化合物是乙酰氯。例如,在R5是甲基的情况下,具有式(VIII)的化合物是碘甲烷,并且碱是氢化钠。
具有式(VII)的化合物可以由具有式(IX)的化合物和具有式(X)的化合物制备。
在合适的溶剂中,用具有式(X)的化合物(其中LG被定义为离去基团)处理具有式(IX)的化合物。该反应可以任选地需要碱。碱的要求和选择将是技术人员所熟悉的。例如,在R4是乙酰基的情况下,具有式(X)的化合物是乙酰氯。例如,在R5是甲基的情况下,具有式(X)的化合物是碘甲烷,并且碱是氢化钠。
具有式(IX)的化合物可以由具有式(XI)的化合物制备。
用甲苯作为溶剂,用二氯二甲基乙内酰脲和催化量的异丙基氯化铵处理具有式(XI)的化合物,以得到具有式(IX)的化合物。
具有式(XI)的化合物可以是可商购的。可替代地,它们可以由2-氨基-4-溴-苯酚制备。
转化的方法将取决于R3的性质。例如,在R3是-CH2CF3的情况下,用碳酸钾和2,2,2-三氟乙基三氟甲磺酸酯处理2-氨基-4-溴-苯酚。例如,在R3是-CF2H的情况下,用溴二氟乙酸钠和碱(例如碳酸铯)处理2-氨基-4-溴-苯酚。
因此,根据本发明,进一步提供了一种具有式(II)的化合物
其中R2、R3、R4和R5是如以上在具有式(I)的化合物中所定义的。在优选实施例中,R2是Cl,并且R3是-CF3或-CHF2。
本发明进一步提供了一种具有式(V)的化合物
其中R2、R3、R4和R5是如以上在具有式(I)的化合物中所定义的。在优选实施例中,R2是Cl,并且R3是-CF3或-CHF2。
本发明还进一步提供了一种具有式(VIa)的化合物
其中“Alk”是C1-C6烷基(优选甲基),并且其中R2、R3、R4和R5是如以上在具有式(I)的化合物中所定义的。在优选实施例中,R2是Cl,并且R3是-CF3或-CHF2。
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。
制备实例1:化合物1.004
步骤1.
向含有5-溴-2-(三氟甲氧基)苯胺(10g,39.1mmol)的烧瓶中添加甲苯(100mL)和二异丙基氯化铵(1.08g,7.81mmol)。将反应混合物用箔覆盖以避光。在0℃下,添加1,3-二氯-5,5-二甲基-咪唑烷-2,4-二酮(7.70g,39.1mmol),并允许反应混合物升温至室温并搅拌3小时。通过添加饱和亚硫酸氢钠水溶液将反应混合物淬灭,然后用水和乙酸乙酯稀释,并分离各相。将有机相干燥并在真空中浓缩。将粗材料通过正相快速色谱法(在环己烷中的0至5%乙酸乙酯)纯化,以得到呈淡黄色油状物的3-溴-2-氯-6-(三氟甲氧基)苯胺(7.07g,21.9mmol,56%)。1H NMR(甲醇):7.05(m,1H),6.99(d,1H)。
步骤2.
向含有3-溴-2-氯-6-(三氟甲氧基)苯胺(1.00g,3.40mmol)的烧瓶中添加乙腈(20mL),并将反应混合物置于氮气气氛下。添加5-溴戊酰氯(1.10g,0.79mL,5.90mmol)。将反应混合物在50℃下搅拌6小时。通过添加水将反应混合物淬灭并在真空中浓缩以去除乙腈溶剂。将反应残余物吸收在乙酸乙酯和水中并分离各相。将水相进一步用乙酸乙酯萃取。将有机相合并、干燥并在真空中浓缩。将粗材料通过正相快速色谱法(在环己烷中的0至30%乙酸乙酯)纯化,以得到呈淡黄色固体的不纯产物。将粗材料吸收在乙酸乙酯中并用2M氢氧化钠水溶液洗涤。将有机相干燥并在真空中浓缩以得到呈淡黄色固体的5-溴-N-[3-溴-2-氯-6-(三氟甲氧基)苯基]戊酰胺(1.44g,2.92mmol,85%)。1H NMR(氯仿):7.62(d,1H),7.16(m,1H),6.90(br s,1H),3.45(t,2H),2.47(br s,2H),2.02-1.87(m,4H)。
步骤3.
向含有N-[3-溴-2-氯-6-(三氟甲氧基)苯基]乙酰胺(1.44g,2.92mmol)的烧瓶中添加四氢呋喃(14mL)。将反应混合物在0℃下在氮气气氛下搅拌10min。向反应混合物中添加在石蜡油中的氢化钠(60质量%,0.129g,3.21mmol)。将反应混合物在室温下搅拌4.5小时。向反应混合物中再添加在石蜡油中的氢化钠(60质量%,0.0818g,2.04mmol)。将反应混合物在室温下搅拌2小时。通过添加水将反应混合物淬灭并在真空中浓缩以去除四氢呋喃溶剂。将残余物吸收在乙酸乙酯和水中,并分离各相。将水相进一步用乙酸乙酯萃取。将有机相合并、干燥并在真空中浓缩。将粗材料通过正相快速色谱法(在环己烷中的0至25%乙酸乙酯)纯化,以得到呈无色油状物的1-[3-溴-2-氯-6-(三氟甲氧基)苯基]哌啶-2-酮(1.03g,2.43mmol,83%)。1H NMR(氯仿):7.64(d,1H),7.17(dq,1H),3.64-3.50(m,1H),3.49-3.38(m,1H),2.58(dt,2H),2.07-1.88(m,4H)。
步骤4.
向含有1-[3-溴-2-氯-6-(三氟甲氧基)苯基]哌啶-2-酮(0.500g,1.34mmol)的容器中添加乙酸钯(II)(0.0301g,0.134mmol)、XantPhos(0.160g,0.268mmol)、N-甲酰基糖精(0.638g,3.02mmol)、1-甲基四唑-5-胺(1.20g,12.1mmol),并添加1-甲基-2-吡咯烷酮,使得容器的总体积是20mL。向含有三乙胺(0.611g,6.04mmol,0.842mL)的第二容器中添加1-甲基-2-吡咯烷酮,使得容器的总体积是20mL。将这两种溶液注入通过T型管泵送的样品环路中,并且然后围绕加热至170℃的20mL不锈钢盘管。设定流速使得总停留时间是15分钟。将反应混合物在真空中浓缩以去除溶剂1-甲基-2-吡咯烷酮。将残余物吸收在二氯甲烷和饱和碳酸钠水溶液中,并分离各相。将水相进一步用二氯甲烷萃取。将水相酸化至pH 5并用乙酸乙酯萃取。将有机相合并、干燥并在真空中浓缩。将粗材料通过正相快速色谱法(在甲醇中的0至10%二氯甲烷)纯化,以得到呈玻璃状固体的不纯产物。将粗材料吸收在乙酸乙酯中并用稀HCl水溶液洗涤。将有机相干燥并在真空中浓缩以得到呈发泡白色固体的3-乙酰胺基-2-氯-N-(5-甲基-1,3,4-噁二唑-2-基)-4-(三氟甲氧基)苯甲酰胺(化合物1.004)(0.0486g,0.116mmol,9%)。1H NMR(甲醇):7.82(d,1H),7.58(m,1H),4.06(s,3H),3.69-3.60(m,1H),3.59-3.50(m,1H),2.57(m,2H),2.10-1.93(dt,4H)
制备实例2:化合物1.006
如先前所描述的制备3-溴-2-氯-6-(三氟甲氧基)苯胺。
步骤1
向高压釜中装入3-溴-2-氯-6-(三氟甲氧基)苯胺(24g,76mmol)。添加甲醇(144mL)。添加三乙胺(23g,228mmol),并且然后添加烯丙基氯化钯(II)二聚体(1.13g,3.10mmol)和2,2'-双(二苯基膦基)-1,1'-联萘(2.44g,3.92mmol)。将高压釜用氮气冲洗3次,并且然后用一氧化碳冲洗3次。将反应加压至20巴CO并在100℃下加热4h。然后使其冷却至室温并用N2置换气氛。将内容物排放至锥形烧瓶中,并将反应混合物通过硅藻土过滤并蒸发。柱色谱法得到呈白色固体的3-氨基-2-氯-4-(三氟甲氧基)苯甲酸甲酯(16g,59mmol,78%)。
步骤2
向含有3-氨基-2-氯-4-(三氟甲氧基)苯甲酸甲酯(2.08g,7.70mmol)的烧瓶中添加乙腈(60mL)和环丙甲酰氯(2.41g,23.1mmol)。将反应混合物在60℃下搅拌。添加之后形成需要剧烈搅拌的白色固体。搅拌2h之后,使反应混合物冷却并将溶剂蒸发。将所获得的固体在环己烷(100ml)中搅拌并过滤,然后用环己烷洗涤,以得到呈白色固体的2-氯-3-(环丙烷羰基氨基)-4-(三氟甲氧基)苯甲酸甲酯(2.40g,7.12mmol,92%)。
步骤3
向2-氯-3-(环丙烷羰基氨基)-4-(三氟甲氧基)苯甲酸甲酯(A,0.35g,1.04mmol)在THF(9mL)和水(3mL)中的溶液中。添加氢氧化锂水合物(87mg,2.1mmol),并将反应混合物搅拌16h。将反应物浓缩以去除THF。向溶液中添加2M HCl直至白色固体沉淀,将其通过过滤分离以得到呈白色固体的2-氯-3-(环丙烷羰基氨基)-4-(三氟甲氧基)苯甲酸(0.296g,0.915mmol,88%)。1H NMR(400MHz,甲醇)δppm 7.87(d,1H)7.43(d,1H)1.85-1.96(m,1H)0.84-1.02(m,4H)。
步骤4
将在2-甲基吡啶(8mL)中的2-氯-3-(环丙烷羰基氨基)-4-(三氟甲氧基)苯甲酸(1.10g,3.4mmol)、1-甲基四唑-5-胺(400mg,4.1mmol)在氮气气氛下搅拌10min,然后添加1-甲基咪唑(280mg,3.4mmol),随后添加三乙胺(520mg,5.1mmol)并在室温下搅拌10min。然后使反应物质冷却至0℃并逐滴添加亚硫酰氯(810mg,6.8mmol)。将反应混合物在室温下搅拌16h。将反应物用2N HCl稀释并搅拌30min。将所获得的固体过滤,用乙醇洗涤并干燥,以得到呈白色固体的2-氯-3-(环丙烷羰基氨基)-N-(1-甲基四唑-5-基)-4-(三氟甲氧基)苯甲酰胺(820mg,2.08mmol,61%)。1H NMR(甲醇):7.73(d,1H),7.52(br d,1H),4.06(s,3H),1.91(m,1H),1.01-0.88(m,4H)。
制备实例3:化合物1.007
如先前所描述的制备3-氨基-2-氯-4-(三氟甲氧基)苯甲酸甲酯。
步骤1
向3-氨基-2-氯-4-(三氟甲氧基)苯甲酸甲酯(2.5g,9.3mmol)在乙腈(60mL)中的溶液中添加丙酰氯(2.6g,28mmol)。将反应混合物在60℃下搅拌2h。2h之后,使混合物冷却至室温并在减压下去除乙腈。将残余物吸收在乙酸乙酯中,然后用碳酸氢钠溶液洗涤,干燥(MgSO4)并在减压下浓缩。快速色谱法(0-30%EtOAc和环己烷)得到呈白色固体的2-氯-3-(丙酰基氨基)-4-(三氟甲氧基)苯甲酸甲酯(2.28g,7.00mmol,76%)。1H NMR(400MHz,d4-甲醇):7.87(d,1H)7.45(m,1H)3.93(s,3H)2.46(q,2H)1.24(t,3H)。
步骤2
向2-氯-3-(丙酰基氨基)-4-(三氟甲氧基)苯甲酸甲酯(27.7g,85.1mmol)在四氢呋喃(10mL)和甲醇(10mL)中的搅拌溶液中添加在水(10mL)中的氢氧化锂(6.11g,255mmol),并在室温下搅拌12小时。将反应物质在减压下浓缩并在1N HCl与乙酸乙酯之间分配。将有机层经硫酸钠干燥并浓缩,以得到呈白色固体的2-氯-3-(丙酰基氨基)-4-(三氟甲氧基)苯甲酸(25.7g,78.3mmol,92%)。1H NMR(400MHz,d6-DMSO):13.70(1H,s),9.82(1H,s),7.79(1H,d),7.51(1H,d),2.35n(2H,q),1.11(H,t)。
步骤3
在室温下在N2气氛下,向烧瓶中装入吡啶(50mL)和2-氯-3-(丙酰基氨基)-4-(三氟甲氧基)苯甲酸(5.00g,16.0mmol)。然后添加1-甲基四唑-5-胺(1.79g,17.7mmol)和1-甲基咪唑(1.33g,16.0mmol),并使反应混合物冷却至0℃。经3h逐滴添加亚硫酰氯(3.94g,32.1mmol),使用注射泵将温度维持在0℃-10℃下。添加完成之后,反应混合物的pH=5.7,并出现棕色沉淀物。移除冰浴并允许反应物在室温下搅拌,再过2h之后,反应混合物变成棕色溶液。再搅拌2h之后,使用冰浴将反应混合物冷却至0℃,并且然后在搅拌下添加25mL的水(pH=5.8-5.9)。使用2N HCl将反应混合物酸化至pH=1.5-2。在酸化期间,沉淀出粘性固体。用乙酸乙酯(50mL×3)萃取悬浮液。将合并的有机层用冷水(25mL)洗涤,干燥(Na2SO4)并在减压下浓缩,以得到浅橙色固体。将其通过使用色谱法(在环己烷中的30%-40%乙酸乙酯)纯化,以得到呈白色固体的2-氯-N-(1-甲基四唑-5-基)-3-(丙酰基氨基)-4-(三氟甲氧基)苯甲酰胺(2.59g,6.61mmol,41%)。1H NMR(400MHz,d6-DMSO):11.92(1H,s),9.90(1H,s),7.80(1H,d),7.61(1H,d),4.00(3H,s),2.37(2H,q),1.12(3H,t)。
制备实例4:化合物1.012
如先前所描述的制备3-氨基-2-氯-4-(三氟甲氧基)苯甲酸甲酯。
步骤1
将3-氨基-2-氯-4-(三氟甲氧基)苯甲酸甲酯(2.0g,7.4mmol)和吡啶-2-甲酸(1.1g,8.9mmol)溶解于吡啶(10mL)中。将溶液通过冰水冷却至0℃。经4分钟逐滴添加三氯氧磷(1.70g,11.1mmol),并且然后允许反应升温至室温并搅拌3h,此时出现白色沉淀物。将反应混合物缓慢淬灭到冷的(0℃)饱和碳酸氢钠水溶液中。添加之后,继续剧烈搅拌30min。过滤所获得的白色固体并用水洗涤3次,以得到呈白色固体的2-氯-3-(吡啶-2-羰基氨基)-4-(三氟甲氧基)苯甲酸甲酯(1.69g,4.51mmol,61%)。1H NMR(400MHz,d6-DMSO):10.69(1H,s),8.78(1H,d),8.15-8.06(2H,m),7.91(1H,d),7.73(1H,ddd),7.62(1H,d),3.90(3H,s)。
步骤2
向2-氯-3-(吡啶-2-羰基氨基)-4-(三氟甲氧基)苯甲酸甲酯(1.6g,4.3mmol)在四氢呋喃(32mL)中的溶液中添加羟基锂水合物(0.54g,13mmol)在水(8.0mL)中的溶液。将反应混合物在室温下搅拌16h。将反应物浓缩以去除THF。将水溶液用环己烷洗涤,然后冷却至0℃并用10%柠檬酸水溶液将pH调节至3。将水性混合物用乙酸乙酯萃取3次,并将合并的有机层经硫酸钠干燥并在减压下浓缩,以得到呈白色固体的2-氯-3-(吡啶-2-羰基氨基)-4-(三氟甲氧基)苯甲酸(1.6g,4.3mmol,100%)。1H NMR(400MHz,d6-DMSO):10.65(1H,d),8.77(1H,d),8.13(1H,d),8.05(1H,t),7.88(1H,d),7.69(1H,m),7.58(1H,d)。
步骤3
将在3-甲基吡啶(15mL)中的2-氯-3-(吡啶-2-羰基氨基)-4-(三氟甲氧基)苯甲酸(1.5g,4.2mmol)、1-甲基四唑-5-胺(500mg,5.0mmol)在氮气气氛下搅拌10分钟。添加三乙胺(630mg,6.2mmol),随后添加1-甲基咪唑(340mg,4.2mmol),并在室温下搅拌30min。然后使反应物质冷却至0℃并逐滴添加亚硫酰氯(990mg,8.3mmol)。在室温下搅拌16h之后,将反应混合物在0℃下用2N HCl淬灭至pH 1-2,同时剧烈搅拌30min。将水层用乙酸乙酯萃取3次,然后在减压下浓缩。将固体从乙酸乙酯/正戊烷中重结晶,以获得呈白色固体的N-[2-氯-3-[(1-甲基四唑-5-基)氨基甲酰基]-6-(三氟甲氧基)苯基]吡啶-2-甲酰胺(1.45g,3.17mmol,76%)。1H NMR(400MHz,d6-DMSO):12.00(1H,brs),10.77(1H,s),8.78(1H,d),8.16-8.05(2H,m),7.88(1H,d),7.72(1H,ddd),7.67(1H,dd),4.00(3H,s)。
制备实例5:化合物1.014
步骤1
在室温下,向15mL厚壁压力容器中添加2-氨基-4-溴-苯酚(564mg,3.00mmol)、KOH(0.218g,3.90mmol)、DMSO(10mL)和1,2-二溴四氟乙烷(1.17g,4.50mmol)。然后将反应烧瓶封闭并加热至80℃持续18h。使反应混合物冷却至室温。将混合物用H2O(200mL)洗涤并用乙酸乙酯(100mL×3)萃取。分离各层并经硫酸钠干燥。蒸发溶剂之后,将残余物通过色谱法(石油醚/乙酸乙酯=30:1)纯化,以得到呈棕色油状物的5-溴-2-(2-溴-1,1,2,2-四氟乙氧基)苯胺(0.215g,0.586mmol,19.5%)和呈棕色油状物的5-溴-2-(1,1,2,2-四氟乙氧基)苯胺(0.206g,0.715mmol,产率:23.8%)。5-溴-2-(1,1,2,2-四氟乙氧基)苯胺的1H NMR(400MHz,d6-DMSO):6.97-6.76(3H,m),6.65-6.62(1H,m),5.54(2H,brs)。
步骤2
将二异丙胺(0.973g,9.63mmol)添加至氯化铵(0.511g,9.63mmol)和乙醇(25mL)的混合物中。将混合物加热至回流持续4h。使反应混合物冷却并且然后浓缩,以得到白色固体,将其用另外的乙醇洗涤,然后在真空下干燥。在氮气下,向3颈烧瓶中添加5-溴-2-(1,1,2,2-四氟乙氧基)苯胺(18.5g,64.2mmol)、甲苯(300mL)和二异丙基氯化铵(1.4g)。将烧瓶用箔覆盖,然后冷却至0摄氏度。分批添加1,3-二氯-5,5-二甲基-咪唑烷-2,4-二酮(11.4g,57.8mmol),并将混合物在0摄氏度下搅拌2h。通过添加饱和亚硫酸氢钠水溶液将反应混合物淬灭,然后用水和乙酸乙酯稀释。将残余物通过色谱法(洗脱液:石油醚/乙酸乙酯=30:1)纯化,以得到呈黄色油状物的3-溴-2-氯-6-(1,1,2,2-四氟乙氧基)苯胺(9.00g,27.9mmol,43.5%)。1H NMR(400MHz,d6-DMSO):7.03(1H,d),3.92(1H,d),6.85(1H,tt),5.83(2H,brs)。
步骤3
在装配有20ml不锈钢回路的Flow syn中进行合成。向回路A中添加:在1-甲基-2-吡咯烷酮(190mL)中的乙酸钯(II)(694mg,3.10mmol)、XantPhos(3.59g,6.20mmol)、N-甲酰基糖精(14.7g,69.8mmol)和3-溴-2-氯-6-(1,1,2,2-四氟乙氧基)苯胺(10g,31.0mmol)。向回路B中添加三乙胺(19.4mL,139.54mmol)和1-甲基-2-吡咯烷酮(190mL)和水(20.1mL,1116.3mmol)。将温度设定至170分钟,并将时间设定至15分钟。在固定容器中,向输出的反应混合物中添加水(1000ml)和1M HCl(1000ml),随后添加乙酸乙酯(1000ml)并分离各相。将有机层在减压下浓缩。将粗材料通过反相色谱法纯化:(50%-70%MeCN在含有0.1%甲酸的H2O中的梯度),以得到呈白色固体的3-氨基-2-氯-4-(1,1,2,2-四氟乙氧基)苯甲酸(5.13g,17.8mmol,58%)。1H NMR(400MHz,甲醇)δppm6.25-6.62(m,1H)7.01-7.26(m,2H)。
步骤4
在室温下,向3-氨基-2-氯-4-(1,1,2,2-四氟乙氧基)苯甲酸(5.13g,17.8mmol)和2,3,4,5,6-五氟苯酚(3.61g,19.6mmol)在二氯甲烷(70mL)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-1-胺盐酸盐(4.1g,21mmol)。将混合物在室温下搅拌。最初是不均匀的,在添加EDC的5分钟内,混合物是均匀溶液。将反应混合物在室温下搅拌16h。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5min。将混合物通过相分离柱(phase separation cartridge)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(在环己烷中的0-10%梯度的EtOAc)纯化。将含有产物的级分合并,并在真空中浓缩,以得到呈无色油状物的(2,3,4,5,6-五氟苯基)3-氨基-2-氯-4-(1,1,2,2-四氟乙氧基)苯甲酸酯(6.36g,14.0mmol,79%),其在静置时结晶。LCMS:在ES-中,M+H=452.1。
步骤5
在室温下,向含有(2,3,4,5,6-五氟苯基)3-氨基-2-氯-4-(1,1,2,2-四氟乙氧基)苯甲酸酯(3.18g,7.01mmol)在乙腈(50mL)中的溶液的圆底烧瓶中添加1-甲基四唑-5-胺(1.53g,15.4mmol),随后添加2-叔丁基亚氨基-N,N-二乙基-1,3-二甲基-1,3,2λ5-二氮杂膦-2-胺(4.4g,4.6mL,15mmol)。将混合物在室温下搅拌过夜。通过添加水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。将混合物转移至分液漏斗中并用EtOAc(100mL)稀释。分离各相。将水相用EtOAc(100mL)萃取。将合并的有机物吸附到C18-二氧化硅上,并经由反相柱色谱法(40%-80%MeCN在含有0.1%甲酸的H2O中的梯度)纯化,以得到呈白色固体的3-氨基-2-氯-N-(1-甲基四唑-5-基)-4-(1,1,2,2-四氟乙氧基)苯甲酰胺(1.88g,4.84mmol,69%)。1H NMR(400MHz,甲醇)δppm 4.05(s,3H)6.28-6.62(m,1H)6.91-6.99(m,1H)7.22-7.30(m,1H)。
步骤6
在室温下,向3-氨基-2-氯-N-(1-甲基四唑-5-基)-4-(1,1,2,2-四氟乙氧基)苯甲酰胺(0.3g,0.81mmol)在乙腈(6mL)中的搅拌溶液中添加丙酰氯(0.23g,0.22mL,2.5mmol)。将搅拌的混合物加热至60℃过夜。使反应冷却至室温并通过缓慢添加水(2mL)淬灭。将混合物在室温下再搅拌5分钟。将混合物转移至分液漏斗中并用EtOAc(20mL)和水(20mL)稀释。分离各相。将水相用EtOAc(20mL)萃取。将合并的有机相干燥(MgSO4)并过滤。将滤液吸附到C18-二氧化硅上,并经由反相柱色谱法(30%-60%MeCN在含有0.1%甲酸的H2O中的梯度)纯化,以得到呈白色固体的2-氯-N-(1-甲基四唑-5-基)-3-(丙酰基氨基)-4-(1,1,2,2-四氟乙氧基)苯甲酰胺(280mg,0.626mmol,77%)。1H NMR(400MHz,d4-甲醇):1.16-1.28(m,3H)2.41-2.53(m,2H)4.06(s,3H)6.21-6.53(m,1H)7.49-7.57(m,1H)7.73(d,1H)。
制备实例6:化合物1.016
步骤1.
向含有3-氯-4-甲基-2-硝基-苯酚(5.33mmol,1.00g)的烧瓶中添加丙酮(20mL)、水(0.1mL)、碳酸钾(10.7mmol,1.47g)和三氟甲磺酸2,2,2-三氟乙酯(8.00mmol,1.86g)。将反应混合物在室温下搅拌过夜。将反应混合物在真空中浓缩以去除溶剂。将残余物溶解在水和乙酸乙酯中。分离各相,然后将水相进一步用乙酸乙酯萃取。将有机相合并,用水洗涤并在真空中浓缩,以得到呈橙色固体的2-氯-1-甲基-3-硝基-4-(2,2,2-三氟乙氧基)苯(5.39mmol,1.450g,定量%),其无需进一步纯化。1H NMR(氯仿):7.32(m,1H),6.91(d,1H),4.42(q,2H),2.39(s,3H)。
步骤2.
向含有2-氯-1-甲基-3-硝基-4-(2,2,2-三氟乙氧基)苯(10.0mmol,2.70g)的烧瓶中添加水(41mL)和吡啶(41mL)。将反应混合物在100℃下搅拌直至反应混合物为溶液。以4份添加高锰酸钾(40.0mmol,6.33g),间隔一小时。将反应混合物在100℃下再搅拌1小时,然后使其在室温下静置过夜。使反应混合物冷却至室温并将固体过滤出。将溶液用乙酸乙酯洗涤。将水相用2M HCl水溶液酸化,并将材料用乙酸乙酯萃取。将有机相合并,并在真空中浓缩,以得到呈白色固体的2-氯-3-硝基-4-(2,2,2-三氟乙氧基)苯甲酸(4.37mmol,1.31g),其无需进一步纯化。1H NMR(甲醇):8.13(d,1H),7.40(d,1H),4.84(m,2H)
步骤3
向含有2-氯-3-硝基-4-(2,2,2-三氟乙氧基)苯甲酸(4.37mmol,1.31g)的烧瓶中添加原甲酸三乙酯(60.1mmol,8.91g,10mL)。将反应混合物在140℃下搅拌1小时。将反应混合物在真空中浓缩以去除原甲酸三乙酯。将残余物用乙酸乙酯研磨,并将固体在真空中干燥,以得到呈橙色固体的2-氯-3-硝基-4-(2,2,2-三氟乙氧基)苯甲酸乙酯(4.23mmol,1.39g,97%),其无需进一步纯化。1H NMR(氯仿):8.05(d,1H),7.02(d,1H),4.52(m,2H),4.42(m,2H),1.41(m,3H)
步骤4
向含有2-氯-3-硝基-4-(2,2,2-三氟乙氧基)苯甲酸乙酯(2.44mmol,0.800g)的烧瓶中添加乙醇(8mL)、氯化铵(14.7mmol,0.784g)、水(8mL)和铁(7.33mmol,0.409g)。将反应混合物在95℃下搅拌1小时。使反应混合物冷却至室温并将固体通过硅藻土过滤,然后用水和乙酸乙酯洗涤。将溶液进一步用水和乙酸乙酯稀释。分离各相,然后将水相进一步用乙酸乙酯萃取。将有机相合并,用水洗涤,然后用盐水洗涤,并在真空中浓缩,以得到呈淡橙色固体的3-氨基-2-氯-4-(2,2,2-三氟乙氧基)苯甲酸乙酯(2.43mmol,0.723g,100%),其无需进一步纯化。1H NMR(氯仿):7.27(m,1H),6.70(d,1H),4.46-4.40(m,4H),4.37(m,2H),1.39(m,3H)
步骤5
向烧瓶中添加3-氨基-2-氯-4-(2,2,2-三氟乙氧基)苯甲酸乙酯(2.43mmol,0.723g)、乙醇(15mL)、氢氧化钠(7.29mmol,0.291g)和水(5mL)。将反应混合物在室温下搅拌6.5小时。将反应混合物在真空中浓缩以去除乙醇溶剂。将水相用浓HCl酸化至约pH 4,然后在真空中浓缩以去除水。将残余物用乙酸乙酯研磨并将所得固体在真空中干燥,以得到3-氨基-2-氯-4-(2,2,2-三氟乙氧基)苯甲酸(假定2.43mmol,假定定量%),其不经历进一步纯化,并以粗品形式呈现。
步骤6
向含有3-氨基-2-氯-4-(2,2,2-三氟乙氧基)苯甲酸(2.43mmol,0.655g)的烧瓶中添加2,3,4,5,6-五氟苯酚(2.79mmol,0.514g)、二氯甲烷(33mL)和1-3-(二甲基氨基丙基)-3-乙基碳二亚胺盐酸盐(2.79mmol,0.564g)。将反应混合物在室温下搅拌1小时。将反应混合物在真空中浓缩以去除溶剂。将反应残余物溶解在乙酸乙酯和水中。分离各相,然后将水相进一步用乙酸乙酯萃取。将有机相合并,并在真空中浓缩,以得到呈无色油状物的(2,3,4,5,6-五氟苯基)3-氨基-2-氯-4-(2,2,2-三氟乙氧基)苯甲酸酯(假定2.43mmol,假定定量%),其不经历进一步纯化并以粗品形式呈现。
步骤7
向含有(2,3,4,5,6-五氟苯基)3-氨基-2-氯-4-(2,2,2-三氟乙氧基)苯甲酸酯(2.43mmol,1.06g)的烧瓶中添加1-甲基四唑-5-胺(2.68mmol,0.265g)、乙腈(21mL),并且添加2-叔丁基亚氨基-2-二乙基氨基-1,3-二甲基全氢-1,3,2-二氮杂磷(5.35mmol,1.51g,1.60mL)。将反应混合物在室温下搅拌1.5小时。将反应混合物通过添加2M HCl水溶液淬灭,然后用乙酸乙酯萃取。将有机相合并,用水洗涤并在真空中浓缩以得到灰白色固体。将粗材料用二氯甲烷研磨,并将所得固体在真空中干燥,以得到呈白色固体的3-氨基-2-氯-N-(1-甲基四唑-5-基)-4-(2,2,2-三氟乙氧基)苯甲酰胺(1.87mmol,0.655g,77%)。1H NMR(甲醇):7.01(d,2H),4.69(m,2H),4.04(s,3H)
步骤8
向含有3-氨基-2-氯-N-(1-甲基四唑-5-基)-4-(2,2,2-三氟乙氧基)苯甲酰胺(0.570mmol,0.200g)的烧瓶中添加乙腈(4mL)和2-氟丙酰氯(1.43mmol,0.158g)。将反应混合物在60℃下搅拌1.5小时。将反应混合物在真空中浓缩以去除溶剂。将粗材料通过正相快速色谱法(在二氯甲烷中的0至5%甲醇)纯化,以得到呈白色固体的2-氯-3-(2-氟丙酰基氨基)-N-(1-甲基四唑-5-基)-4-(2,2,2-三氟乙氧基)苯甲酰胺(化合物1.016)(0.313mmol,0.133g,55%)。1H NMR(甲醇):7.71(d,1H),7.26(d,1H),5.25(m,0.5H),5.13(m,0.5H),4.68(m,2H),4.04(s,3H),1.68(d,1.5H),1.62(d,1.5H)。
制备实例7:化合物1.018
步骤1
如以上所描述的制备3-氨基-2-氯-N-(1-甲基四唑-5-基)-4-(2,2,2-三氟乙氧基)苯甲酰胺。
步骤2
向含有3-氨基-2-氯-N-(1-甲基四唑-5-基)-4-(2,2,2-三氟乙氧基)苯甲酰胺(0.428mmol,0.150g)的烧瓶中添加乙腈(6mL)和乙酰氯(1.28mmol,0.101g,0.092mL)。将反应混合物在60℃下搅拌1.5小时。将反应混合物在真空中浓缩以去除溶剂。将粗材料通过正相快速色谱法(在二氯甲烷中的0至5%甲醇)纯化,以得到呈白色固体的3-乙酰胺基-2-氯-N-(1-甲基四唑-5-基)-4-(2,2,2-三氟乙氧基)苯甲酰胺(化合物1.018)(0.357mmol,0.140g,83%)。1H NMR(甲醇):7.67(d,1H),7.25(d,1H),4.67(m,2H),4.04(s,3H),2.18(s,3H)。
制备实例8:化合物1.028
步骤1
向含有3-氯-4-甲基-2-硝基-苯酚(5.33mmol,1.00g)的烧瓶中添加丙酮(20mL)和水(0.1mL)。添加碳酸钾(8.00mmol,1.11g)和碘甲烷(10.7mmol,1.51g,0.664mL)。将反应混合物在室温下搅拌过夜。将反应混合物在真空中浓缩以去除丙酮溶剂。将残余物溶解在水和乙酸乙酯中。分离各相,然后将水相进一步用乙酸乙酯萃取。将有机相合并,并在真空中浓缩,以得到呈黄色固体的3-氯-1-甲氧基-4-甲基-2-硝基-苯(4.98mmol,1.00g,93%),其无需进一步纯化。1H NMR(氯仿):7.28(m,1H),6.87(d,1H),3.88(s,3H),2.36(s,3H)。
步骤2
向含有3-氯-1-甲氧基-4-甲基-2-硝基-苯(3.97mmol,0.800g)的烧瓶中添加水(16mL)和吡啶(16mL)。将反应混合物在100℃下搅拌直至反应混合物为溶液。以3份添加高锰酸钾(11.9mmol,1.88g),间隔一小时。将反应混合物在100℃下搅拌过夜。使反应混合物冷却至室温并将固体过滤出。将溶液用TBME洗涤。将水相用2M HCl水溶液酸化,并将材料用乙酸乙酯萃取。将有机相合并,并在真空中浓缩,以得到呈白色固体的2-氯-4-甲氧基-3-硝基-苯甲酸(2.20mmol,0.509g,55%),其无需进一步纯化。1H NMR(甲醇):8.11(d,1H),7.29(d,1H),4.00(s,3H)。
步骤3
向含有2-氯-4-甲氧基-3-硝基-苯甲酸(8.77mmol,2.03g)的烧瓶中添加原甲酸三乙酯(120mmol,17.8g,20mL)。将反应混合物在140℃下搅拌3小时。将反应混合物在真空中浓缩以去除原甲酸三乙酯。将残余物用乙酸乙酯研磨,并将固体在真空中干燥,以得到呈橙色固体的2-氯-4-甲氧基-3-硝基-苯甲酸乙酯(8.77mmol,2.28g,定量%),其无需进一步纯化。
步骤4
向含有2-氯-4-甲氧基-3-硝基-苯甲酸乙酯(3.85mmol,1.00g)的烧瓶中添加乙醇(10mL)、氯化铵(23.1mmol,1.24g)、水(10mL)和铁(11.6mmol,0.645g)。将反应混合物在95℃下搅拌1小时。使反应混合物冷却至室温并将固体通过硅藻土过滤,然后用水和乙酸乙酯洗涤。将溶液进一步用水和乙酸乙酯稀释。分离各相,然后将水相进一步用乙酸乙酯萃取。将有机相合并,用水洗涤,然后用盐水洗涤,并在真空中浓缩,以得到呈灰白色固体的3-氨基-2-氯-4-甲氧基-苯甲酸乙酯(3.76mmol,0.864g,98%),其无需进一步纯化。
步骤5
向含有3-氨基-2-氯-4-甲氧基-苯甲酸乙酯(3.76mmol,0.864g)的烧瓶中添加乙醇(15mL)、氢氧化钠(11.3mmol,0.451g)和水(5mL)。将反应混合物在室温下搅拌过夜。将反应混合物在真空中浓缩以去除乙醇溶剂。将水相用浓HCl酸化至约pH 4,然后在真空中浓缩以去除水。将残余物溶解在水和乙酸乙酯中,并分离各相。将有机相在真空中浓缩,以得到呈灰白色固体的3-氨基-2-氯-4-甲氧基-苯甲酸(3.67mmol,0.740g,98%),其无需进一步纯化。
步骤6
向含有3-氨基-2-氯-4-甲氧基-苯甲酸(3.70mmol,0.740g)的烧瓶中添加2,3,4,5,6-五氟苯酚(4.20mmol,0.780g)、二氯甲烷(37mL)和1-3-(二甲基氨基丙基)-3-乙基碳二亚胺盐酸盐(4.20mmol,0.850g)。将反应混合物在室温下搅拌30分钟。将反应混合物在真空中浓缩以去除溶剂。将反应残余物溶解在乙酸乙酯和水中。分离各相,然后将水相进一步用乙酸乙酯萃取。将有机相合并,并在真空中浓缩,以得到呈橙色油状物的(2,3,4,5,6-五氟苯基)3-氨基-2-氯-4-甲氧基-苯甲酸酯(假定3.70mmol,假定定量%),其不经历进一步纯化并以粗品形式呈现。
步骤7
向含有(2,3,4,5,6-五氟苯基)3-氨基-2-氯-4-甲氧基-苯甲酸酯(3.70mmol,1.36g)的烧瓶中添加1-甲基四唑-5-胺(4.07mmol,0.403g)、乙腈(27mL)、2-叔丁基亚氨基-2-二乙基氨基-1,3-二甲基全氢-1,3,2-二氮杂磷(8.14mmol,2.30g,2.43mL)。将反应混合物在室温下搅拌1小时。将反应混合物通过添加2M HCl水溶液淬灭,然后用乙酸乙酯萃取。将有机相合并,用水洗涤并在真空中浓缩以得到橙色油状物。将粗材料通过正相快速色谱法(在二氯甲烷中的0至10%甲醇)纯化,以得到呈淡橙色固体的3-氨基-2-氯-4-甲氧基-N-(1-甲基四唑-5-基)苯甲酰胺(2.21mmol,0.624g,60%)。1H NMR(甲醇):7.04(d,1H),6.91(d,1H),4.03(s,3H),3.94(s,3H)。
步骤8
向含有2-氟丙酸(10.9mmol,1.00g)的烧瓶中添加亚硫酰氯(23.5mmol,2.80g,1.68mL)。将反应混合物在60℃下搅拌4小时。将产物蒸馏以得到呈无色油状物的2-氟丙酰氯(6.81mmol,0.753g,63%)。1H NMR(氯仿):5.21(m,0.5H),5.08(m,0.5H),1.74(d,1.5H),1.68(d,1.5H)
步骤9
向含有3-氨基-2-氯-4-甲氧基-N-(1-甲基四唑-5-基)苯甲酰胺(0.707mmol,0.200g)的烧瓶中添加乙腈(8mL)和2-氟丙酰氯(1.41mmol,0.209g)。将反应混合物加热至60℃持续4小时。将反应混合物在真空中浓缩以去除溶剂。将粗材料通过正相快速色谱法(在二氯甲烷中的0至10%甲醇)纯化,以得到呈黄色固体的2-氯-3-(2-氟丙酰基氨基)-4-甲氧基-N-(1-甲基四唑-5-基)苯甲酰胺(化合物1.031)(0.555mmol,0.198g,79%)。1H NMR(甲醇):7.69(d,1H),7.17(d,1H),5.25(m,0.5H),5.13(m,0.5H),4.03(s,3H),3.92(s,3H),1.68(d,1.5H),1.61(d,1.5H)。
制备实例10:化合物1.030
步骤1
如以上所描述的制备3-氨基-2-氯-4-甲氧基-N-(1-甲基四唑-5-基)苯甲酰胺。
步骤2
向含有3-氨基-2-氯-4-甲氧基-N-(1-甲基四唑-5-基)苯甲酰胺(0.531mmol,0.150g)的烧瓶中添加乙腈(6mL)和乙酰氯(1.06mmol,0.0833g)。将反应混合物在60℃下搅拌2小时。将反应混合物在真空中浓缩以去除溶剂。将粗材料用乙酸乙酯研磨,并将固体在真空中干燥,以得到呈白色固体的3-乙酰胺基-2-氯-4-甲氧基-N-(1-甲基四唑-5-基)苯甲酰胺(化合物1.033)(0.490mmol,0.159g,92%)。1H NMR(甲醇):7.66(d,1H),7.16(d,1H),4.04(s,3H),3.92(s,3H),2.17(s,3H)。
制备实例11:化合物2.001
步骤1
如先前所概述的制备3-溴-2-氯-6-(三氟甲氧基)苯胺。
步骤2
向含有3-溴-2-氯-6-(三氟甲氧基)苯胺(2.00g,6.89mmol)的烧瓶中添加四氢呋喃(30mL)。将反应混合物置于氮气气氛下并在-78℃下搅拌30分钟。向反应混合物中逐滴添加正丁基锂(在己烷中2.5M,7.57mmol,3.00mL)。将反应混合物在-78℃下搅拌1小时。向反应混合物中添加碘甲烷(2.93g,20.7mmol,1.29mL)。允许反应混合物升温至0℃并搅拌3小时。通过将反应混合物缓慢添加到饱和氯化铵水溶液中来小心地淬灭反应混合物。将混合物在室温下搅拌15分钟,并将水相用乙酸乙酯萃取。将有机相合并、干燥并在真空中浓缩。将粗材料通过正相快速色谱法(在环己烷中的0至5%乙酸乙酯)纯化以得到不纯产物。将粗材料通过反相快速色谱法(在(水+0.1%甲酸)中的60%至100%(乙腈+0.1%甲酸))纯化,以得到呈棕色油状物的3-溴-2-氯-N-甲基-6-(三氟甲氧基)苯胺(0.587g,1.93mmol,28%)。1H NMR(氯仿):7.03-6.99(m,1H),6.99-6.94(m,1H),3.08(s,3H)。
步骤3
向含有3-溴-2-氯-N-甲基-6-(三氟甲氧基)苯胺(1.36g,4.47mmol)的烧瓶中添加四氢呋喃(41mL)。将反应混合物置于氮气气氛下并在-78℃下搅拌1小时。向反应混合物中逐滴添加正丁基锂(在己烷中2.5M,4.91mmol,2.00mL)。将反应混合物在-78℃下搅拌45分钟。向反应混合物中添加碘甲烷(1.90g,13.4mmol,0.834mL)。允许反应混合物升温至0℃并搅拌3.5小时。通过将反应混合物缓慢添加到冰冷却的饱和氯化铵水溶液中来小心地淬灭反应混合物。将混合物在0℃下搅拌15分钟,并将水相用乙酸乙酯萃取。将有机相合并、干燥并在真空中浓缩。将粗材料通过正相快速色谱法(在环己烷中的0至1%乙酸乙酯)纯化,以得到3-溴-2-氯-N,N-二甲基-6-(三氟甲氧基)苯胺(0.520g,1.63mmol,37%)。1H NMR(氯仿):7.35(d,J=8.9Hz,1H),7.01(m,1H),2.87(s,6H)。
步骤4
向含有3-溴-2-氯-N,N-二甲基-6-(三氟甲氧基)苯胺(0.520g,1.63mmol)的容器中添加乙酸钯(II)(0.0367g,0.163mmol)、XantPhos(0.195g,0.327mmol)、N-甲酰基糖精(0.776g,3.67mmol)、5-甲基-1,3,4-噁二唑-2-胺(1.46g,14.7mmol)和1-甲基-2-吡咯烷酮,使得容器的总体积是20mL。向含有三乙胺(0.743g,7.35mmol,1.02mL)的第二容器中添加1-甲基-2-吡咯烷酮,使得容器的总体积是20mL。反应在Uniqsis FlowSyn中进行。将这两种溶液注入通过T型管泵送的样品环路中,并且然后围绕加热至170℃的20mL不锈钢盘管。设定流速使得总停留时间是20分钟。将反应混合物在真空中浓缩以去除溶剂1-甲基-2-吡咯烷酮。将残余物通过反相HPLC纯化以得到不纯产物。将粗材料通过正相快速色谱法(在环己烷中的10%至80%乙酸乙酯)纯化,以得到呈淡黄色固体的2-氯-3-(二甲基氨基)-N-(5-甲基-1,3,4-噁二唑-2-基)-4-(三氟甲氧基)苯甲酰胺(化合物2.001)(0.174g,0.478mmol,29%)。1H NMR(甲醇):7.37-7.34(m,2H),2.90(s,6H),2.51(s,3H)。
表1-本发明的除草化合物的实例。
使用如所指示的NMR或使用以下条件的LCMS表征化合物。使用Sample Organizer(具有样品管理器FTN(Sample Manager FTN),H级QSM,柱管理器(Column Manager),2x柱管理器Aux,光电二极管阵列,ELSD和QDA SQD 2)在沃特斯(Waters)Aquity UPLC-MS(配备有沃特斯HSS C18柱(柱长度50mm,柱内径2.3mm,粒径1.8微米))。根据以下梯度表,使用四分钟运行时间进行分析:
溶剂A:具有0.05%TFA的H2O
溶剂B:具有0.05%TFA的CH3CN
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%吐温20(聚氧乙烯脱水山梨糖醇单月桂酸酯,CAS RN 9005-64-5)。除非另外指出,否则化合物以500g/h施用。然后使测试植物在温室中在受控条件(在24℃/16℃,白天/夜晚下;14小时光照;65%湿度)下生长,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价。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
*以125g/ha施用
表B2-对比测试
将测试物种的种子播种在盆中的标准土壤中。在温室中的受控条件(在24℃/16℃下,白天/夜晚;14小时光照;65%湿度)下培养一天之后,用水性喷雾溶液来喷雾这些植物,该水性喷雾溶液源自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 RN11097-66-8)的45ml配制品溶液中的工业级活性成分的配制品。
然后使测试植物在温室中在温室中的受控条件(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)。
测试物种:ABUTH(苘麻);BROTE(旱雀麦);ECHCG(稗草);SINAR(野芥)。
C1是WO2012/028579中所披露的化合物4-659。可以看出,用本发明的卤代烷氧基取代苯环上的4-氯取代基提供了所观察到的杂草控制的出乎意料的改善。
Claims (18)
1.一种具有式(I)的化合物:
或其农艺学上可接受的盐,
其中:-
Q是Q1或Q2;
R1a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-;
R1b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是C1-C6卤代烷基或C1-C6烷基;
R4选自由以下组成的组:C1-C6烷基-、C1-C6卤代烷基-、C1-C6烷基-C(O)-、C1-C6卤代烷基-C(O)-、C3-C6环烷基-、C3-C6环烷基-C1-C3烷基-、C3-C6环烷基-C(O)-、C1-C3烷氧基-C1-C3烷基-、C1-C3烷氧基-C1-C3烷基-C(O)-、-C(O)-苯基和-C(O)-杂芳基,其中所述苯基、杂芳基或C3-C6环烷基任选地被1、2或3个选自由以下组成的组的取代基取代:卤素、C1-C6烷基、C1-C6卤代烷基和C1-C6烷氧基;
R5选自由以下组成的组:氢、C1-C6烷基-、C1-C6卤代烷基和C1-C6环烷基;或者
R4和R5连同它们附接的氮原子一起形成任选地被氧代基取代的5元或6元饱和杂环;并且
p是0、1或2。
2.根据权利要求1所述的化合物,其中,R1a或R1b选自由以下组成的组:甲基、乙基和正丙基。
3.根据前述权利要求中任一项所述的化合物,其中,Q是Q1,并且R1a是甲基。
4.根据权利要求1或权利要求2所述的化合物,其中,Q是Q2,并且R1b是甲基。
5.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:甲基、Cl、-CF3和-SO2甲基。
6.根据权利要求5所述的化合物,其中,R2是Cl。
7.根据前述权利要求中任一项所述的化合物,其中,R3是-CF3或-CHF2。
8.根据前述权利要求中任一项所述的化合物,其中,R4选自由以下组成的组:C1-C6烷基-、C1-C6烷基-C(O)-和C3-C6环烷基-。
9.根据权利要求1至7中任一项所述的化合物,其中,R4是-C(O)-杂芳基,其中所述杂芳基任选地被1、2或3个选自由以下组成的组的取代基取代:卤素、C1-C6烷基、C1-C6卤代烷基和C1-C6烷氧基。
10.根据前述权利要求中任一项所述的化合物,其中,R5是氢或C1-C6烷基-。
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。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IN202011016632 | 2020-04-17 | ||
IN202011016632 | 2020-04-17 | ||
PCT/EP2021/059431 WO2021209383A1 (en) | 2020-04-17 | 2021-04-12 | Herbicidal compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
CN115362147A true CN115362147A (zh) | 2022-11-18 |
Family
ID=75530002
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202180025259.XA Pending CN115362147A (zh) | 2020-04-17 | 2021-04-12 | 除草化合物 |
Country Status (14)
Country | Link |
---|---|
US (1) | US20230219904A1 (zh) |
EP (1) | EP4136080B1 (zh) |
JP (1) | JP2023521170A (zh) |
KR (1) | KR20230004578A (zh) |
CN (1) | CN115362147A (zh) |
AR (1) | AR121840A1 (zh) |
AU (1) | AU2021255800A1 (zh) |
BR (1) | BR112022021014A2 (zh) |
CA (1) | CA3174955A1 (zh) |
CL (1) | CL2022002793A1 (zh) |
CO (1) | CO2022014495A2 (zh) |
MX (1) | MX2022012779A (zh) |
UY (1) | UY39173A (zh) |
WO (1) | WO2021209383A1 (zh) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2022233727A1 (en) * | 2021-05-07 | 2022-11-10 | Syngenta Crop Protection Ag | Herbicidal compounds |
Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012130685A1 (en) * | 2011-03-25 | 2012-10-04 | Bayer Cropscience Ag | Use of n-(tetrazol-4-yl)- or n-(triazol-3-yl)arylcarboxamides or their salts for controlling unwanted plants in areas of transgenic crop plants being tolerant to hppd inhibitor herbicides |
WO2013092834A1 (en) * | 2011-12-21 | 2013-06-27 | Syngenta Limited | Herbicidal compounds |
CN103282354A (zh) * | 2010-09-01 | 2013-09-04 | 拜耳知识产权有限责任公司 | N-(四唑-5-基)-和n-(三唑-5-基)芳基甲酰胺及其作为除草剂的用途 |
CN103596946A (zh) * | 2011-03-22 | 2014-02-19 | 拜耳知识产权有限责任公司 | N-(1,3,4-噁二唑-2-基)芳基甲酰胺及其作为除草剂的用途 |
CN103987701A (zh) * | 2011-12-13 | 2014-08-13 | 拜耳知识产权有限责任公司 | N-(1,2,5-噁二唑-3-基)-、n-(1,3,4-噁二唑-2-基)-、n-(四唑-5-基)-和n-(三唑-5-基)-芳基甲酰胺及其作为除草剂的用途 |
WO2014184015A1 (en) * | 2013-05-15 | 2014-11-20 | Basf Se | Substituted n-(tetrazol-5-yl)- and n-(triazol-5-yl)arylcarboxamide compounds and their use as herbicides |
CN104428297A (zh) * | 2012-04-27 | 2015-03-18 | 巴斯夫欧洲公司 | 取代的n-(四唑-5-基)-和n-(三唑-5-基)芳基羧酰胺化合物及其作为除草剂的用途 |
CN105592699A (zh) * | 2013-10-04 | 2016-05-18 | 拜耳作物科学股份公司 | 含有n-(1,3,4-噁二唑-2-基)芳基羧酸酰胺的除草剂-安全剂组合物 |
CN105636950A (zh) * | 2013-10-10 | 2016-06-01 | 巴斯夫欧洲公司 | 取代的n-(四唑-5-基)-和n-(三唑-5-基)芳基羧酰胺化合物及其作为除草剂的用途 |
WO2018234371A1 (en) * | 2017-06-20 | 2018-12-27 | Basf Se | BENZAMIDE COMPOUNDS AND THEIR USE AS HERBICIDES |
WO2019238067A1 (en) * | 2018-06-13 | 2019-12-19 | Beigene, Ltd. | Pyrrolo [2, 3-b] pyridines or pyrrolo [2, 3-b] pyrazines as hpk1 inhibitor and the use thereof |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR8600161A (pt) | 1985-01-18 | 1986-09-23 | Plant Genetic Systems Nv | Gene quimerico,vetores de plasmidio hibrido,intermediario,processo para controlar insetos em agricultura ou horticultura,composicao inseticida,processo para transformar celulas de plantas para expressar uma toxina de polipeptideo produzida por bacillus thuringiensis,planta,semente de planta,cultura de celulas e plasmidio |
EP0374753A3 (de) | 1988-12-19 | 1991-05-29 | American Cyanamid Company | Insektizide Toxine, Gene, die diese Toxine kodieren, Antikörper, die sie binden, sowie transgene Pflanzenzellen und transgene Pflanzen, die diese Toxine exprimieren |
DK0427529T3 (da) | 1989-11-07 | 1995-06-26 | Pioneer Hi Bred Int | Larvedræbende lactiner og planteinsektresistens baseret derpå |
UA48104C2 (uk) | 1991-10-04 | 2002-08-15 | Новартіс Аг | Фрагмент днк, який містить послідовність,що кодує інсектицидний протеїн, оптимізовану для кукурудзи,фрагмент днк, який забезпечує направлену бажану для серцевини стебла експресію зв'язаного з нею структурного гена в рослині, фрагмент днк, який забезпечує специфічну для пилку експресію зв`язаного з нею структурного гена в рослині, рекомбінантна молекула днк, спосіб одержання оптимізованої для кукурудзи кодуючої послідовності інсектицидного протеїну, спосіб захисту рослин кукурудзи щонайменше від однієї комахи-шкідника |
US5530195A (en) | 1994-06-10 | 1996-06-25 | Ciba-Geigy Corporation | Bacillus thuringiensis gene encoding a toxin active against insects |
AR031027A1 (es) | 2000-10-23 | 2003-09-03 | Syngenta Participations Ag | Composiciones agroquimicas |
EP2287292B1 (en) | 2000-12-07 | 2015-04-08 | Syngenta Limited | Plant derived hydroxy phenyl pyruvate dioxygneases (hppd) resistant against triketone herbicides and transgenic plants containing these dioxygenases |
WO2003052073A2 (en) | 2001-12-17 | 2003-06-26 | Syngenta Participations Ag | Novel corn event |
US9347046B2 (en) | 2009-01-22 | 2016-05-24 | Syngenta Participations Ag | Hydroxyphenylpyruvate dioxygenase polypeptides and methods of use |
ES2727575T3 (es) | 2009-01-22 | 2019-10-17 | Syngenta Participations Ag | Polipéptidos de Hidroxifenilpiruvato Dioxigenasa mutantes, y Métodos de uso |
TWI667347B (zh) | 2010-12-15 | 2019-08-01 | 瑞士商先正達合夥公司 | 大豆品種syht0h2及偵測其之組合物及方法 |
TW201231655A (en) | 2010-12-15 | 2012-08-01 | Syngenta Participations Ag | Soybean event SYHT04R and compositions and methods for detection thereof |
-
2021
- 2021-04-12 KR KR1020227039095A patent/KR20230004578A/ko active Search and Examination
- 2021-04-12 EP EP21718845.7A patent/EP4136080B1/en active Active
- 2021-04-12 US US17/996,310 patent/US20230219904A1/en active Pending
- 2021-04-12 BR BR112022021014A patent/BR112022021014A2/pt unknown
- 2021-04-12 AU AU2021255800A patent/AU2021255800A1/en active Pending
- 2021-04-12 CN CN202180025259.XA patent/CN115362147A/zh active Pending
- 2021-04-12 MX MX2022012779A patent/MX2022012779A/es unknown
- 2021-04-12 JP JP2022562033A patent/JP2023521170A/ja active Pending
- 2021-04-12 CA CA3174955A patent/CA3174955A1/en active Pending
- 2021-04-12 WO PCT/EP2021/059431 patent/WO2021209383A1/en unknown
- 2021-04-14 AR ARP210100983A patent/AR121840A1/es unknown
- 2021-04-15 UY UY0001039173A patent/UY39173A/es unknown
-
2022
- 2022-10-11 CL CL2022002793A patent/CL2022002793A1/es unknown
- 2022-10-12 CO CONC2022/0014495A patent/CO2022014495A2/es unknown
Patent Citations (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103282354A (zh) * | 2010-09-01 | 2013-09-04 | 拜耳知识产权有限责任公司 | N-(四唑-5-基)-和n-(三唑-5-基)芳基甲酰胺及其作为除草剂的用途 |
CN103596946A (zh) * | 2011-03-22 | 2014-02-19 | 拜耳知识产权有限责任公司 | N-(1,3,4-噁二唑-2-基)芳基甲酰胺及其作为除草剂的用途 |
US20140080705A1 (en) * | 2011-03-22 | 2014-03-20 | Bayer Intellectual Property Gmbh | N-(1,3,4-oxadiazol-2-yl)arylcarboxamides and use thereof as herbicides |
WO2012130685A1 (en) * | 2011-03-25 | 2012-10-04 | Bayer Cropscience Ag | Use of n-(tetrazol-4-yl)- or n-(triazol-3-yl)arylcarboxamides or their salts for controlling unwanted plants in areas of transgenic crop plants being tolerant to hppd inhibitor herbicides |
CN103987701A (zh) * | 2011-12-13 | 2014-08-13 | 拜耳知识产权有限责任公司 | N-(1,2,5-噁二唑-3-基)-、n-(1,3,4-噁二唑-2-基)-、n-(四唑-5-基)-和n-(三唑-5-基)-芳基甲酰胺及其作为除草剂的用途 |
WO2013092834A1 (en) * | 2011-12-21 | 2013-06-27 | Syngenta Limited | Herbicidal compounds |
CN104428297A (zh) * | 2012-04-27 | 2015-03-18 | 巴斯夫欧洲公司 | 取代的n-(四唑-5-基)-和n-(三唑-5-基)芳基羧酰胺化合物及其作为除草剂的用途 |
WO2014184015A1 (en) * | 2013-05-15 | 2014-11-20 | Basf Se | Substituted n-(tetrazol-5-yl)- and n-(triazol-5-yl)arylcarboxamide compounds and their use as herbicides |
CN105592699A (zh) * | 2013-10-04 | 2016-05-18 | 拜耳作物科学股份公司 | 含有n-(1,3,4-噁二唑-2-基)芳基羧酸酰胺的除草剂-安全剂组合物 |
CN105636950A (zh) * | 2013-10-10 | 2016-06-01 | 巴斯夫欧洲公司 | 取代的n-(四唑-5-基)-和n-(三唑-5-基)芳基羧酰胺化合物及其作为除草剂的用途 |
WO2018234371A1 (en) * | 2017-06-20 | 2018-12-27 | Basf Se | BENZAMIDE COMPOUNDS AND THEIR USE AS HERBICIDES |
WO2019238067A1 (en) * | 2018-06-13 | 2019-12-19 | Beigene, Ltd. | Pyrrolo [2, 3-b] pyridines or pyrrolo [2, 3-b] pyrazines as hpk1 inhibitor and the use thereof |
Non-Patent Citations (1)
Title |
---|
STN: "STN", 《STN》, pages 1 - 8 * |
Also Published As
Publication number | Publication date |
---|---|
AR121840A1 (es) | 2022-07-13 |
JP2023521170A (ja) | 2023-05-23 |
CO2022014495A2 (es) | 2022-10-31 |
EP4136080A1 (en) | 2023-02-22 |
UY39173A (es) | 2021-11-30 |
CL2022002793A1 (es) | 2023-04-21 |
US20230219904A1 (en) | 2023-07-13 |
MX2022012779A (es) | 2022-11-08 |
BR112022021014A2 (pt) | 2022-12-06 |
CA3174955A1 (en) | 2021-10-21 |
KR20230004578A (ko) | 2023-01-06 |
EP4136080B1 (en) | 2024-04-24 |
AU2021255800A1 (en) | 2022-11-03 |
WO2021209383A1 (en) | 2021-10-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP4132913B1 (en) | 5-haloalkoxy-pyrimidine compounds as herbicides | |
KR102664770B1 (ko) | 제초제로서 유용한 아미딘 치환된 벤조일 유도체 | |
EP4058438B1 (en) | Herbicidal compounds | |
CN115362147A (zh) | 除草化合物 | |
CN112823150A (zh) | 除草2-氮杂螺[3-5]壬烷化合物 | |
CN112313209A (zh) | 除草化合物 | |
AU2021391477B2 (en) | Herbicidal derivatives | |
WO2020079078A1 (en) | Herbicidal compounds | |
WO2020193322A1 (en) | Sulfonamides and their use as herbicides | |
KR20240006593A (ko) | 제초제로서 치환된 벤즈아미드 | |
CN117295719A (zh) | 除草化合物 | |
CN118119603A (zh) | 作为除草剂的取代的苯甲酰胺 | |
CN117222627A (zh) | 除草化合物 | |
WO2024046890A1 (en) | Herbicidal pyrazole compounds | |
CN116634873A (zh) | 除草四唑化合物 | |
TW202413349A (zh) | 除草化合物 | |
TW202408361A (zh) | 除草化合物 | |
BR112018071154B1 (pt) | Compostos de piridazinona herbicidas, composição herbicida, método de controle de plantas daninhas em um lócus, método de produção e uso de um composto |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination |