JP2017522318A - 除草性ピリダジノン誘導体 - Google Patents
除草性ピリダジノン誘導体 Download PDFInfo
- Publication number
- JP2017522318A JP2017522318A JP2017502578A JP2017502578A JP2017522318A JP 2017522318 A JP2017522318 A JP 2017522318A JP 2017502578 A JP2017502578 A JP 2017502578A JP 2017502578 A JP2017502578 A JP 2017502578A JP 2017522318 A JP2017522318 A JP 2017522318A
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- JP
- Japan
- Prior art keywords
- alkyl
- alkoxy
- haloalkyl
- methyl
- compound according
- 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.)
- Granted
Links
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 34
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 99
- 239000000203 mixture Substances 0.000 claims abstract description 77
- -1 benzyloxy-substituted phenyl-dioxo-thiazinone Chemical class 0.000 claims abstract description 55
- 238000000034 method Methods 0.000 claims abstract description 13
- 230000008635 plant growth Effects 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 35
- 150000002367 halogens Chemical class 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 239000004009 herbicide Substances 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000001188 haloalkyl group Chemical group 0.000 claims description 15
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 14
- 238000009472 formulation Methods 0.000 claims description 12
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 6
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
- 241000607479 Yersinia pestis Species 0.000 claims description 6
- MYKHANQTTIRZJK-UHFFFAOYSA-N pyridazine-3,4-dione Chemical group O=C1C=CN=NC1=O MYKHANQTTIRZJK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000002757 morpholinyl group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 3
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 3
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims description 3
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 3
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 3
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 3
- 150000001204 N-oxides Chemical class 0.000 claims description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 241000196324 Embryophyta Species 0.000 abstract description 28
- 238000002360 preparation method Methods 0.000 abstract description 5
- 244000038559 crop plants Species 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
- 125000003545 alkoxy group Chemical group 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 239000008187 granular material Substances 0.000 description 11
- 229910052740 iodine Inorganic materials 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000001309 chloro group Chemical group Cl* 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 239000004094 surface-active agent Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 240000008042 Zea mays Species 0.000 description 8
- 239000004530 micro-emulsion Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 7
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 7
- 235000005822 corn Nutrition 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
- QIRNGVVZBINFMX-UHFFFAOYSA-N 2-allylphenol Chemical compound OC1=CC=CC=C1CC=C QIRNGVVZBINFMX-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000000575 pesticide Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000080 wetting agent Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000000304 alkynyl group Chemical group 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 235000021391 short chain fatty acids Nutrition 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000004546 suspension concentrate Substances 0.000 description 5
- 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- OGGXGZAMXPVRFZ-UHFFFAOYSA-N dimethylarsinic acid Chemical compound C[As](C)(O)=O OGGXGZAMXPVRFZ-UHFFFAOYSA-N 0.000 description 4
- 239000004491 dispersible concentrate Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000007857 hydrazones Chemical class 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 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
- 239000004563 wettable powder Substances 0.000 description 4
- 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 3
- AOVOFDFDAFHJPH-UHFFFAOYSA-N 4-(3,6-dichloro-2-phenylmethoxyphenyl)-2,6-dimethylpyridazine-3,5-dione Chemical compound C(C1=CC=CC=C1)OC1=C(C(=CC=C1Cl)Cl)C1C(N(N=C(C1=O)C)C)=O AOVOFDFDAFHJPH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 241000219318 Amaranthus Species 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 244000166102 Eucalyptus leucoxylon Species 0.000 description 3
- 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 150000001263 acyl chlorides Chemical class 0.000 description 3
- 150000004703 alkoxides Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 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
- 229910052791 calcium Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 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 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 229910052717 sulfur Chemical group 0.000 description 3
- 239000011593 sulfur Chemical group 0.000 description 3
- 239000000375 suspending agent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 230000009261 transgenic effect Effects 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- QWWHRELOCZEQNZ-UHFFFAOYSA-N 2,2-dichloro-1-(1-oxa-4-azaspiro[4.5]decan-4-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCOC11CCCCC1 QWWHRELOCZEQNZ-UHFFFAOYSA-N 0.000 description 2
- UEMDTQCVOKUEAI-UHFFFAOYSA-N 2-(3,6-dichloro-2-phenylmethoxyphenyl)acetic acid Chemical compound OC(=O)Cc1c(Cl)ccc(Cl)c1OCc1ccccc1 UEMDTQCVOKUEAI-UHFFFAOYSA-N 0.000 description 2
- NUPJIGQFXCQJBK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-5-(methoxymethyl)nicotinic acid Chemical compound OC(=O)C1=CC(COC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 NUPJIGQFXCQJBK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- RDUKRQJHXBCYIY-UHFFFAOYSA-N 3,6-dichloro-2-prop-2-enylphenol Chemical compound OC1=C(Cl)C=CC(Cl)=C1CC=C RDUKRQJHXBCYIY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- MBFHUWCOCCICOK-UHFFFAOYSA-N 4-iodo-2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]benzoic acid Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=C(I)C=2)C(O)=O)=N1 MBFHUWCOCCICOK-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- 241001621841 Alopecurus myosuroides Species 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 244000281762 Chenopodium ambrosioides Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 241000234653 Cyperus Species 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000005562 Glyphosate Substances 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 239000005566 Imazamox Substances 0.000 description 2
- 239000005568 Iodosulfuron Substances 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 235000011999 Panicum crusgalli Nutrition 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 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
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000004996 alkyl benzenes Chemical class 0.000 description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229960000892 attapulgite Drugs 0.000 description 2
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- LINPVWIEWJTEEJ-UHFFFAOYSA-N methyl 2-chloro-9-hydroxyfluorene-9-carboxylate Chemical group C1=C(Cl)C=C2C(C(=O)OC)(O)C3=CC=CC=C3C2=C1 LINPVWIEWJTEEJ-UHFFFAOYSA-N 0.000 description 1
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- NDNKHWUXXOFHTD-UHFFFAOYSA-N metizoline Chemical compound CC=1SC2=CC=CC=C2C=1CC1=NCCN1 NDNKHWUXXOFHTD-UHFFFAOYSA-N 0.000 description 1
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- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- AIMMSOZBPYFASU-UHFFFAOYSA-N n-(4,6-dimethoxypyrimidin-2-yl)-n'-[3-(2,2,2-trifluoroethoxy)pyridin-1-ium-2-yl]sulfonylcarbamimidate Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)OCC(F)(F)F)=N1 AIMMSOZBPYFASU-UHFFFAOYSA-N 0.000 description 1
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- 125000006126 n-butyl sulfonyl group Chemical group 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 description 1
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- NVGOPFQZYCNLDU-UHFFFAOYSA-N norflurazon Chemical compound O=C1C(Cl)=C(NC)C=NN1C1=CC=CC(C(F)(F)F)=C1 NVGOPFQZYCNLDU-UHFFFAOYSA-N 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
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- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
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- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- JZPKLLLUDLHCEL-UHFFFAOYSA-N pentoxazone Chemical compound O=C1C(=C(C)C)OC(=O)N1C1=CC(OC2CCCC2)=C(Cl)C=C1F JZPKLLLUDLHCEL-UHFFFAOYSA-N 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- IDOWTHOLJBTAFI-UHFFFAOYSA-N phenmedipham Chemical compound COC(=O)NC1=CC=CC(OC(=O)NC=2C=C(C)C=CC=2)=C1 IDOWTHOLJBTAFI-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 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
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- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 description 1
- CWKFPEBMTGKLKX-UHFFFAOYSA-N picolinafen Chemical compound C1=CC(F)=CC=C1NC(=O)C1=CC=CC(OC=2C=C(C=CC=2)C(F)(F)F)=N1 CWKFPEBMTGKLKX-UHFFFAOYSA-N 0.000 description 1
- MGOHCFMYLBAPRN-UHFFFAOYSA-N pinoxaden Chemical compound CCC1=CC(C)=CC(CC)=C1C(C1=O)=C(OC(=O)C(C)(C)C)N2N1CCOCC2 MGOHCFMYLBAPRN-UHFFFAOYSA-N 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
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- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
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- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- OYJMHAFVOZPIOY-UHFFFAOYSA-N propan-2-yl 2-chloro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1 OYJMHAFVOZPIOY-UHFFFAOYSA-N 0.000 description 1
- FKLQIONHGSFYJY-UHFFFAOYSA-N propan-2-yl 5-[4-bromo-1-methyl-5-(trifluoromethyl)pyrazol-3-yl]-2-chloro-4-fluorobenzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(C=2C(=C(N(C)N=2)C(F)(F)F)Br)=C1F FKLQIONHGSFYJY-UHFFFAOYSA-N 0.000 description 1
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- WJNRPILHGGKWCK-UHFFFAOYSA-N propazine Chemical compound CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 WJNRPILHGGKWCK-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 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 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
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- ABOOPXYCKNFDNJ-SNVBAGLBSA-N quizalofop-P Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 ABOOPXYCKNFDNJ-SNVBAGLBSA-N 0.000 description 1
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- GNHDVXLWBQYPJE-UHFFFAOYSA-N saflufenacil Chemical compound C1=C(Cl)C(C(=O)NS(=O)(=O)N(C)C(C)C)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F GNHDVXLWBQYPJE-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
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- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 229960002218 sodium chlorite Drugs 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 229940057950 sodium laureth sulfate Drugs 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- JKPSVOHVUGMYGH-UHFFFAOYSA-M sodium;(4,6-dimethoxypyrimidin-2-yl)-[[3-methoxycarbonyl-6-(trifluoromethyl)pyridin-2-yl]sulfonylcarbamoyl]azanide Chemical compound [Na+].COC(=O)C1=CC=C(C(F)(F)F)N=C1S(=O)(=O)NC(=O)[N-]C1=NC(OC)=CC(OC)=N1 JKPSVOHVUGMYGH-UHFFFAOYSA-M 0.000 description 1
- 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
- JRQGDDUXDKCWRF-UHFFFAOYSA-M sodium;n-(2-methoxycarbonylphenyl)sulfonyl-4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carboximidate Chemical compound [Na+].O=C1N(C)C(OCCC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1C(=O)OC JRQGDDUXDKCWRF-UHFFFAOYSA-M 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 description 1
- VFNGKCDDZUSWLR-UHFFFAOYSA-M sulfo sulfate Chemical compound OS(=O)(=O)OS([O-])(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-M 0.000 description 1
- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 235000001508 sulfur Nutrition 0.000 description 1
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- 239000012730 sustained-release form Substances 0.000 description 1
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- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- IUQAXCIUEPFPSF-UHFFFAOYSA-N tembotrione Chemical compound ClC1=C(COCC(F)(F)F)C(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O IUQAXCIUEPFPSF-UHFFFAOYSA-N 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 125000000335 thiazolyl group Chemical group 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
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000002053 thietanyl group Chemical group 0.000 description 1
- LOQQVLXUKHKNIA-UHFFFAOYSA-N thifensulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(O)=O)=N1 LOQQVLXUKHKNIA-UHFFFAOYSA-N 0.000 description 1
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 1
- 238000003971 tillage Methods 0.000 description 1
- IYMLUHWAJFXAQP-UHFFFAOYSA-N topramezone Chemical compound CC1=C(C(=O)C2=C(N(C)N=C2)O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 IYMLUHWAJFXAQP-UHFFFAOYSA-N 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical class C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
- RVKCCVTVZORVGD-UHFFFAOYSA-N trinexapac-ethyl Chemical group O=C1CC(C(=O)OCC)CC(=O)C1=C(O)C1CC1 RVKCCVTVZORVGD-UHFFFAOYSA-N 0.000 description 1
- KVEQCVKVIFQSGC-UHFFFAOYSA-N tritosulfuron Chemical compound FC(F)(F)C1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(F)(F)F)=N1 KVEQCVKVIFQSGC-UHFFFAOYSA-N 0.000 description 1
- 241001478887 unidentified soil bacteria Species 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/14—Oxygen atoms
- C07D237/16—Two oxygen atoms
-
- A—HUMAN NECESSITIES
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Abstract
Description
の化合物、またはその塩もしくはN−オキシドが提供される。
E=ハロゲン
X=ハロゲン
E=ハロゲン
E=ハロゲン
実施例1 4−(2−ベンジルオキシ−3,6−ジクロロ−フェニル)−2,6−ジメチル−ピリダジン−3,5−ジオンの調製
2−アリルオキシ−1,4−ジクロロ−ベンゼン(1.0g、4.9mmol、1.0当量)とDMF(0.1mL)との混合物を、220℃の外部温度で1時間加熱した。混合物を室温に冷まし、減圧下で濃縮したところ、2−アリル−3,6−ジクロロ−フェノールが褐色の油(0.99g、99%)として得られた。
臭化ベンジル(3.2mL、27mmol、1.1当量)を、アセトン(49mL)中の2−アリル−3,6−ジクロロ−フェノール(5.0g、25mmol、1.0当量)および炭酸カリウム(3.7g、27mmol、1.1当量)の懸濁液に加え、混合物を、6時間にわたって還流状態で加熱した。混合物を室温に冷まし、ろ過した。ろ液を減圧下で濃縮し、粗生成物を、フラッシュカラムクロマトグラフィーによって精製したところ、2−アリル−3−ベンジルオキシ−1,4−ジクロロ−ベンゼン(4.031g、56%)が無色油として得られた。
3つ口フラスコ中、ジクロロメタン(650mL)中の2−アリル−3−ベンジルオキシ−1,4−ジクロロ−ベンゼン(38.1g、130mmol、1.00当量)の溶液を−78℃に冷却した。1つの側管を、KIの水溶液(100mL、15% w/w)を含むDreshel瓶に連結した。2−アリル−3−ベンジルオキシ−1,4−ジクロロ−ベンゼンが完全に消費されるまで(4時間)オゾンをこの溶液に通してバブリングした。空気を10分間にわたってこの溶液に通してバブリングして、過剰なオゾンを除去した。この溶液に通すガスのバブリングを停止し、硫化ジメチル(95.4mL、1300mmol、10.0当量)を加えた。混合物を室温に温め、12時間撹拌した。混合物を塩水(2×200mL)で洗浄し、有機抽出物を疎水性フリット(hydrophobic frit)に通した。混合物を減圧下で濃縮したところ、黄色の油(43g)が得られた。残渣を、tert−ブタノール(260mL)および水(130mL)中の混合物に溶解させ、次に、0℃に冷却した。2−メチルブタ−2−エン(135mL、1300mmol、10.0当量)、リン酸二水素ナトリウム(62.4g、520mmol、4.00当量)および亜塩素酸ナトリウム(44.1g、390mmol、3.00当量)を加えた。混合物を2時間撹拌し、次に、塩水(300mL)および2.0Mの塩酸(300mL)で希釈した。混合物をEtOAc(3×200mL)で抽出した。組み合わされた有機抽出物を、メタ重亜硫酸ナトリウムの飽和水溶液(200mL)で洗浄し、次に、疎水性フリットに通し、減圧下で濃縮したところ、淡黄色の固体(41.4g)が得られた。残渣をH2O(200mL)中で懸濁させ、NaOHの水溶液(30mL、2.0M)を加えて、透明な溶液を得た。混合物をEt2O(100mL)で洗浄し、水層を、濃HCl(20mL)の添加によって酸性化したところ、沈殿物が形成された。混合物をろ過し、ろ液を減圧下で乾燥させたところ、2−(2−ベンジルオキシ−3,6−ジクロロ−フェニル)酢酸(29.2g、72%)が白色の固体として得られた。
撹拌子、滴下漏斗および温度計を備えた500mLの3つ口フラスコを、N2雰囲気下に置いた。クロロホルム(60mL)、2−オキソプロパン酸エチル(12.9g、111mmol)および硫酸マグネシウム(13.3g、111mmol)を、撹拌しながら容器に充填した。得られたスラリーを0℃(氷浴)に冷却した。次に、滴下漏斗に、クロロホルム(20mL)およびメチルヒドラジン(5.00g、109mmol)を充填した。次に、メチルヒドラジン溶液を、10℃未満の温度を保つように添加の速度を設定しながら撹拌された反応混合物に滴下して加えた。添加の完了後、反応物を周囲温度に温め、次に、さらに16時間撹拌した。
2−(2−ベンジルオキシ−3,6−ジクロロ−フェニル)酢酸(1.32mmol、0.41g)を、撹拌しながらN2下でジクロロメタン(10mL)に溶解させた。塩化オキサリル(3.95mmol、0.50g、0.34mL)を加えた。2分後、N,N−ジメチルホルムアミド(0.13mmol、0.01mL)を滴下して加えた。泡立ちが観察された。周囲温度で1時間撹拌した後、MeOH中にクエンチされた一定分量のLC/MS分析により、酸出発材料からメチルエステルへの完全な転化(塩化アシルの形成を裏付ける)が示された。
マイクロ波バイアルに、エチル2−[[2−(2−ベンジルオキシ−3,6−ジクロロ−フェニル)アセチル]−メチル−ヒドラゾノ]プロパノエート(0.46mmol、0.20g)、アセトニトリル(4mL)および1,8−ジアザビシクロ[5.4.0]ウンデカ−7−エン(0.98mmol、0.15g、0.15mL)を充填した。LC/MS分析により完全な反応が示されるまで、混合物を、50分間にわたって125℃で、マイクロ波照射下で加熱した。反応混合物を酢酸エチル(20mL)および水(10mL)で希釈し、希塩酸を用いてpH4〜5になるまで酸性化した。有機物を分離し、飽和塩化アンモニウム水溶液(2×10mL)、次に塩水(10mL)でさらに洗浄した。次に、有機物を相分離カートリッジに通し、減圧下で濃縮したところ、粗製の黄色のガムが得られた。フラッシュカラムクロマトグラフィー(シリカ、溶離剤 ヘキサン0〜25%の酢酸エチルの勾配)により、所望の生成物4−(2−ベンジルオキシ−3,6−ジクロロ−フェニル)−2,6−ジメチル−ピリダジン−3,5−ジオン(0.11g、61%)が淡黄色のガムとして得られた。
B1 出芽後の有効性
様々な試験種の種子を、ポット中の標準的な土壌に播種する:−イヌホオズキ(Solanum nigrum)(SOLNI)、アオゲイトウ(Amaranthus retoflexus)(AMARE)、アキノエノコログサ(Setaria faberi)(SETFA)、ノスズメノテッポウ(Alopecurus myosuroides)(ALOMY)、イヌビエ(Echinochloa crus−galli)(ECHCG)、アメリカアサガオ(Ipomoea hederacea)(IPOHE)、ホソムギ(Lolium perenne)(LOLPE)。温室における制御された条件(24/16℃、昼間/夜間;14時間の照明;65%の湿度)下での栽培から8日後(出芽後)、0.5%のTween 20(ポリオキシエチレンソルビタンモノラウレート、CAS RN 9005−64−5)を含有するアセトン/水(50:50)溶液中の技術的な活性成分の製剤に由来する散布水溶液を植物に散布する。化合物を、1000g/haで施用する。次に、試験植物を、温室における制御された条件(24/16℃、昼間/夜間;14時間の照明;65%の湿度)下で温室において成長させ、1日2回水をやる。13日後、植物に生じたダメージのパーセンテージについて試験を評価する。生物学的活性が、5段階評価で評価される(5=80〜100%;4=60〜79%;3=40〜59%;2=20〜39%;1=0〜19%)。
本発明のまた別の態様は、以下のとおりであってもよい。
〔1〕式(I)
(R 1 が、C 1 〜C 4 アルキル、C 3 〜C 6 シクロアルキル、C 3 〜C 6 アルコキシ、C 1 〜C 2 アルコキシ−C 1 〜C 2 アルキル、C 2 〜C 4 アルケニル、C 1 〜C 4 ハロアルキル、シアノ−C 1 〜C 4 アルキル、C 2 〜C 4 ハロアルケニル、C 2 〜C 4 アルキニルおよびC 2 〜C 4 ハロアルキニルからなる群から選択され;
R 2 が、水素、ハロゲン、シアノ、C 1 〜C 6 アルキル、C 1 〜C 6 ハロアルキル、C 1 〜C 6 ハロアルコキシ、C 1 〜C 3 ハロアルコキシ−C 1 〜C 3 アルキル−、C 1 〜C 6 アルコキシ、C 1 〜C 3 アルコキシ−C 1 〜C 3 アルキル、C 1 〜C 3 アルコキシ−C 1 〜C 3 アルコキシ−C 1 〜C 3 アルキル−、C 3 〜C 6 シクロアルキル、C 2 〜C 6 アルケニル、C 2 〜C 6 ハロアルケニル、C 2 〜C 6 アルキニル、C 1 〜C 6 ヒドロキシアルキル−、C 1 〜C 6 アルキルカルボニル−、C 1 〜C 6 アルキル−S(O) m −、アミノ、C 1 〜C 6 アルキルアミノ、C 1 〜C 6 ジアルキルアミノ、−C(C 1 〜C 3 アルキル)=N−O−C 1 〜C 3 アルキルおよびC 2 〜C 6 ハロアルキニルからなる群から選択され;
Gが、水素、またはC(O)R 3 であり;
XおよびYがそれぞれ独立して、水素、C 1 〜C 3 アルキル、C 1 〜C 3 アルコキシ、C 1 〜C 3 ハロアルキル、C 1 〜C 3 ハロアルコキシ、またはハロゲンであり;
Zが、C 1 〜C 3 アルキル、C 1 〜C 3 アルコキシ、C 1 〜C 3 ハロアルキル、C 1 〜C 3 ハロアルコキシ、またはハロゲンであり;
mが、0、1、または2の整数であり;
nが、0、1、2、3、4、または5の整数であり;
R 3 が、C 1 〜C 6 アルキル、C 1 〜C 6 アルコキシ、C 1 〜C 6 アルケニル、C 1 〜C 6 アルキニル、C 1 〜C 6 アルキル−S−、−NR 4 R 5 および1つ以上のR 6 で任意に置換されるフェニルからなる群から選択され;
R 4 およびR 5 が、独立して、C 1 〜C 6 アルキルおよびC 1 〜C 6 アルコキシからなる群から選択され、またはR 4 およびR 5 が一緒にモルホリニル環を形成することができ;
R 6 が、ハロゲン、シアノ、ニトロ、C 1 〜C 3 アルキル、C 1 〜C 3 ハロアルキル、C 1 〜C 3 アルコキシおよびC 1 〜C 3 ハロアルコキシからなる群から選択される)
の化合物、またはその塩もしくはN−オキシド。
〔2〕Gが、水素またはC(O)R 3 であり、ここで、R 3 が、イソプロピル、t−ブチル、メチル、エチル、プロパルギル、メトキシ、エトキシ、またはtert−ブトキシである、前記〔1〕に記載の化合物。
〔3〕Gが水素であり、またはR 3 がイソプロピルである、前記〔2〕に記載の化合物。
〔4〕Xが、水素、ハロゲン、またはC 1 ハロアルキルである、前記〔1〕〜〔3〕のいずれか一項に記載の化合物。
〔5〕Yが、水素、C 1 〜C 3 アルキル、C 1 〜C 3 ハロアルキル、またはハロゲンである、前記〔1〕〜〔4〕のいずれか一項に記載の化合物。
〔6〕Xが、ピリダジノン/ピリダジン−ジオン部分に対してオルトである、前記〔1〕〜〔5〕のいずれか一項に記載の化合物。
〔7〕Yが、前記ベンジルオキシ部分に対してオルトである、前記〔1〕〜〔6〕のいずれか一項に記載の化合物。
〔8〕R 1 が、メチル、エチル、n−プロピル、シクロプロピル、プロパルギル、またはC 1 ハロアルキルである、前記〔1〕〜〔7〕のいずれか一項に記載の化合物。
〔9〕R 2 が、水素、C 1 〜C 6 アルキル、C 1 〜C 6 ハロアルキル、C 1 〜C 6 アルコキシ、C 1 〜C 3 アルコキシ−C 1 〜C 3 アルキル、C 3 〜C 6 シクロアルキル、C 2 〜C 6 アルケニル、C 2 〜C 6 ハロアルケニル、C 2 〜C 6 アルキニルおよびC 2 〜C 6 ハロアルキニルからなる群から選択される、前記〔1〕〜〔8〕のいずれか一項に記載の化合物。
〔10〕R 2 が、メチル、エチル、シクロプロピル、トリフルオロメチルおよびメトキシメチルからなる群から選択される、前記〔1〕〜〔9〕のいずれか一項に記載の化合物。
〔11〕R 2 が、シクロプロピルまたはメチルである、前記〔1〕〜〔10〕のいずれか一項に記載の化合物。
〔12〕nが、0、1、または2である、前記〔1〕〜〔11〕のいずれか一項に記載の化合物。
〔13〕各Zが、独立して、ハロゲン、メチル、メトキシ、およびトリフルオロメチルから選択される、前記〔1〕〜〔12〕のいずれか一項に記載の化合物。
〔14〕前記〔1〕〜〔13〕のいずれか一項に記載の除草性化合物と、農学的に許容できる製剤助剤とを含む除草性組成物。
〔15〕少なくとも1種の追加の有害生物防除剤をさらに含む、前記〔14〕に記載の除草性組成物。
〔16〕前記追加の有害生物防除剤が、除草剤または除草剤緩和剤である、前記〔15〕に記載の除草性組成物。
〔17〕望ましくない植物の成長を制御する方法であって、前記〔1〕〜〔13〕のいずれか一項に記載の式(I)の化合物、または前記〔14〕〜〔16〕のいずれか一項に記載の除草性組成物を、前記望ましくない植物またはその場所に施用する工程を含む方法。
〔18〕除草剤としての前記〔1〕〜〔13〕のいずれか一項に記載の式(I)の化合物の使用。
Claims (18)
- 式(I)
R2が、水素、ハロゲン、シアノ、C1〜C6アルキル、C1〜C6ハロアルキル、C1〜C6ハロアルコキシ、C1〜C3ハロアルコキシ−C1〜C3アルキル−、C1〜C6アルコキシ、C1〜C3アルコキシ−C1〜C3アルキル、C1〜C3アルコキシ−C1〜C3アルコキシ−C1〜C3アルキル−、C3〜C6シクロアルキル、C2〜C6アルケニル、C2〜C6ハロアルケニル、C2〜C6アルキニル、C1〜C6ヒドロキシアルキル−、C1〜C6アルキルカルボニル−、C1〜C6アルキル−S(O)m−、アミノ、C1〜C6アルキルアミノ、C1〜C6ジアルキルアミノ、−C(C1〜C3アルキル)=N−O−C1〜C3アルキルおよびC2〜C6ハロアルキニルからなる群から選択され;
Gが、水素、またはC(O)R3であり;
XおよびYがそれぞれ独立して、水素、C1〜C3アルキル、C1〜C3アルコキシ、C1〜C3ハロアルキル、C1〜C3ハロアルコキシ、またはハロゲンであり;
Zが、C1〜C3アルキル、C1〜C3アルコキシ、C1〜C3ハロアルキル、C1〜C3ハロアルコキシ、またはハロゲンであり;
mが、0、1、または2の整数であり;
nが、0、1、2、3、4、または5の整数であり;
R3が、C1〜C6アルキル、C1〜C6アルコキシ、C1〜C6アルケニル、C1〜C6アルキニル、C1〜C6アルキル−S−、−NR4R5および1つ以上のR6で任意に置換されるフェニルからなる群から選択され;
R4およびR5が、独立して、C1〜C6アルキルおよびC1〜C6アルコキシからなる群から選択され、またはR4およびR5が一緒にモルホリニル環を形成することができ;
R6が、ハロゲン、シアノ、ニトロ、C1〜C3アルキル、C1〜C3ハロアルキル、C1〜C3アルコキシおよびC1〜C3ハロアルコキシからなる群から選択される)
の化合物、またはその塩もしくはN−オキシド。 - Gが、水素またはC(O)R3であり、ここで、R3が、イソプロピル、t−ブチル、メチル、エチル、プロパルギル、メトキシ、エトキシ、またはtert−ブトキシである、請求項1に記載の化合物。
- Gが水素であり、またはR3がイソプロピルである、請求項2に記載の化合物。
- Xが、水素、ハロゲン、またはC1ハロアルキルである、請求項1〜3のいずれか一項に記載の化合物。
- Yが、水素、C1〜C3アルキル、C1〜C3ハロアルキル、またはハロゲンである、請求項1〜4のいずれか一項に記載の化合物。
- Xが、ピリダジノン/ピリダジン−ジオン部分に対してオルトである、請求項1〜5のいずれか一項に記載の化合物。
- Yが、前記ベンジルオキシ部分に対してオルトである、請求項1〜6のいずれか一項に記載の化合物。
- R1が、メチル、エチル、n−プロピル、シクロプロピル、プロパルギル、またはC1ハロアルキルである、請求項1〜7のいずれか一項に記載の化合物。
- R2が、水素、C1〜C6アルキル、C1〜C6ハロアルキル、C1〜C6アルコキシ、C1〜C3アルコキシ−C1〜C3アルキル、C3〜C6シクロアルキル、C2〜C6アルケニル、C2〜C6ハロアルケニル、C2〜C6アルキニルおよびC2〜C6ハロアルキニルからなる群から選択される、請求項1〜8のいずれか一項に記載の化合物。
- R2が、メチル、エチル、シクロプロピル、トリフルオロメチルおよびメトキシメチルからなる群から選択される、請求項1〜9のいずれか一項に記載の化合物。
- R2が、シクロプロピルまたはメチルである、請求項1〜10のいずれか一項に記載の化合物。
- nが、0、1、または2である、請求項1〜11のいずれか一項に記載の化合物。
- 各Zが、独立して、ハロゲン、メチル、メトキシ、およびトリフルオロメチルから選択される、請求項1〜12のいずれか一項に記載の化合物。
- 請求項1〜13のいずれか一項に記載の除草性化合物と、農学的に許容できる製剤助剤とを含む除草性組成物。
- 少なくとも1種の追加の有害生物防除剤をさらに含む、請求項14に記載の除草性組成物。
- 前記追加の有害生物防除剤が、除草剤または除草剤緩和剤である、請求項15に記載の除草性組成物。
- 望ましくない植物の成長を制御する方法であって、請求項1〜13のいずれか一項に記載の式(I)の化合物、または請求項14〜16のいずれか一項に記載の除草性組成物を、前記望ましくない植物またはその場所に施用する工程を含む方法。
- 除草剤としての請求項1〜13のいずれか一項に記載の式(I)の化合物の使用。
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JP2021509919A (ja) * | 2018-01-09 | 2021-04-08 | シンジェンタ パーティシペーションズ アーゲー | 除草性化合物 |
JP2022510438A (ja) * | 2018-12-04 | 2022-01-26 | シンジェンタ パーティシペーションズ アーゲー | 除草性組成物 |
WO2023189602A1 (ja) * | 2022-03-30 | 2023-10-05 | 石原産業株式会社 | ピリダジノン系化合物又はその塩及びそれらを含有する有害生物防除剤 |
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GB201507464D0 (en) * | 2015-04-30 | 2015-06-17 | Syngenta Participations Ag | Herbicidal compounds |
GB2546336A (en) * | 2016-01-18 | 2017-07-19 | Syngenta Participations Ag | Intermediate compounds |
GB201800894D0 (en) * | 2018-01-19 | 2018-03-07 | Syngenta Participations Ag | Improvements in or relating to organic compounds |
JP7063231B2 (ja) * | 2018-10-26 | 2022-05-09 | 住友化学株式会社 | ジピリダジニルエーテル化合物及びその用途 |
GB201910291D0 (en) | 2019-07-18 | 2019-09-04 | Syngenta Crop Protection Ag | Herbicidal compounds |
GB201910290D0 (en) | 2019-07-18 | 2019-09-04 | Syngenta Crop Protection Ag | Herbicidal compounds |
GB202012651D0 (en) | 2020-08-13 | 2020-09-30 | Syngenta Crop Protection Ag | Herbicidal compositions |
GB202116307D0 (en) | 2021-11-12 | 2021-12-29 | Syngenta Crop Protection Ag | Herbicide resistance |
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