AU1878599A - Herbicides 3-(benzazol-4-yl)pyrimidine-dione-derivatives - Google Patents

Info

Publication number

AU1878599A

AU1878599A AU18785/99A AU1878599A AU1878599A AU 1878599 A AU1878599 A AU 1878599A AU 18785/99 A AU18785/99 A AU 18785/99A AU 1878599 A AU1878599 A AU 1878599A AU 1878599 A AU1878599 A AU 1878599A

Authority

AU

Australia

Prior art keywords

alkyl

butyl

ethyl

och

propyl

Prior art date

1997-12-17

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• Discuss

• 239000004009 herbicide Substances 0.000 title claims description 9
• -1 1,3-propylene, tetramethylene, pentamethylene Chemical group 0.000 claims description 911
• 239000000460 chlorine Substances 0.000 claims description 78
• 239000000203 mixture Substances 0.000 claims description 75
• 238000000034 method Methods 0.000 claims description 73
• 230000008569 process Effects 0.000 claims description 47
• 229910052739 hydrogen Inorganic materials 0.000 claims description 39
• 239000001257 hydrogen Substances 0.000 claims description 36
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 34
• BTRZCXUPKJCHIB-UHFFFAOYSA-N 3-(1h-indol-4-yl)-1h-pyrimidine-2,4-dione Chemical class O=C1C=CNC(=O)N1C1=CC=CC2=C1C=CN2 BTRZCXUPKJCHIB-UHFFFAOYSA-N 0.000 claims description 24
• 229910052736 halogen Inorganic materials 0.000 claims description 24
• 150000002367 halogens Chemical class 0.000 claims description 24
• 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 22
• 229910052801 chlorine Inorganic materials 0.000 claims description 20
• 150000003839 salts Chemical class 0.000 claims description 20
• 230000002363 herbicidal effect Effects 0.000 claims description 18
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
• 239000011737 fluorine Substances 0.000 claims description 15
• 229910052731 fluorine Inorganic materials 0.000 claims description 15
• 150000002431 hydrogen Chemical class 0.000 claims description 14
• 239000007787 solid Substances 0.000 claims description 14
• 125000000623 heterocyclic group Chemical group 0.000 claims description 12
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
• CCPHAMSKHBDMDS-UHFFFAOYSA-N Chetoseminudin B Natural products C=1NC2=CC=CC=C2C=1CC1(SC)NC(=O)C(CO)(SC)N(C)C1=O CCPHAMSKHBDMDS-UHFFFAOYSA-N 0.000 claims description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• 239000001301 oxygen Substances 0.000 claims description 7
• 238000002360 preparation method Methods 0.000 claims description 7
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
• 239000000126 substance Substances 0.000 claims description 6
• CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 5
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
• 239000007788 liquid Substances 0.000 claims description 3
• 239000004094 surface-active agent Substances 0.000 claims description 3
• 238000002156 mixing Methods 0.000 claims description 2
• UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 2
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
• 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
• RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Substances SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims 1
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 83
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 60
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 58
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 58
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
• 150000001875 compounds Chemical class 0.000 description 54
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
• 238000006243 chemical reaction Methods 0.000 description 43
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
• 239000011541 reaction mixture Substances 0.000 description 31
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
• 239000002585 base Substances 0.000 description 29
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
• 239000002904 solvent Substances 0.000 description 28
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
• 238000005481 NMR spectroscopy Methods 0.000 description 24
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
• 239000004480 active ingredient Substances 0.000 description 23
• 239000002253 acid Substances 0.000 description 22
• 125000005499 phosphonyl group Chemical group 0.000 description 22
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 21
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 20
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
• 239000000243 solution Substances 0.000 description 19
• 241000196324 Embryophyta Species 0.000 description 18
• URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 18
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 17
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
• 239000003085 diluting agent Substances 0.000 description 15
• 239000000047 product Substances 0.000 description 15
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 14
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 14
• 239000007858 starting material Substances 0.000 description 14
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 13
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 13
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 13
• 229910052794 bromium Inorganic materials 0.000 description 13
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
• 125000001931 aliphatic group Chemical group 0.000 description 12
• 238000009835 boiling Methods 0.000 description 12
• 239000003153 chemical reaction reagent Substances 0.000 description 12
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 12
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
• 229910052783 alkali metal Inorganic materials 0.000 description 11
• 239000003054 catalyst Substances 0.000 description 11
• 239000011734 sodium Substances 0.000 description 11
• 229910052708 sodium Inorganic materials 0.000 description 11
• 229910052938 sodium sulfate Inorganic materials 0.000 description 11
• 235000011152 sodium sulphate Nutrition 0.000 description 11
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 10
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 10
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 10
• 150000004292 cyclic ethers Chemical class 0.000 description 10
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
• 239000003480 eluent Substances 0.000 description 10
• 125000001153 fluoro group Chemical group F* 0.000 description 10
• 235000011167 hydrochloric acid Nutrition 0.000 description 10
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 10
• 229910017604 nitric acid Inorganic materials 0.000 description 10
• 239000002798 polar solvent Substances 0.000 description 10
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
• 239000012312 sodium hydride Substances 0.000 description 10
• 229910000104 sodium hydride Inorganic materials 0.000 description 10
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 9
• 230000002378 acidificating effect Effects 0.000 description 9
• 150000007513 acids Chemical class 0.000 description 9
• 150000001298 alcohols Chemical class 0.000 description 9
• 125000000217 alkyl group Chemical group 0.000 description 9
• 239000012043 crude product Substances 0.000 description 9
• 239000012074 organic phase Substances 0.000 description 9
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 8
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 8
• 239000003921 oil Substances 0.000 description 8
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 8
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
• 150000001448 anilines Chemical class 0.000 description 7
• 150000004649 carbonic acid derivatives Chemical class 0.000 description 7
• 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 7
• 239000006185 dispersion Substances 0.000 description 7
• 239000003960 organic solvent Substances 0.000 description 7
• 238000001291 vacuum drying Methods 0.000 description 7
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
• 239000007864 aqueous solution Substances 0.000 description 6
• 235000013877 carbamide Nutrition 0.000 description 6
• 239000004359 castor oil Substances 0.000 description 6
• 235000019438 castor oil Nutrition 0.000 description 6
• 150000001768 cations Chemical class 0.000 description 6
• 239000012141 concentrate Substances 0.000 description 6
• 238000003379 elimination reaction Methods 0.000 description 6
• 150000002170 ethers Chemical class 0.000 description 6
• ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 6
• 150000008282 halocarbons Chemical class 0.000 description 6
• 239000005457 ice water Substances 0.000 description 6
• 229910052500 inorganic mineral Inorganic materials 0.000 description 6
• 235000010755 mineral Nutrition 0.000 description 6
• 239000011707 mineral Substances 0.000 description 6
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
• 150000007530 organic bases Chemical class 0.000 description 6
• 239000012071 phase Substances 0.000 description 6
• 229910000027 potassium carbonate Inorganic materials 0.000 description 6
• 238000003756 stirring Methods 0.000 description 6
• 238000012360 testing method Methods 0.000 description 6
• 238000011282 treatment Methods 0.000 description 6
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
• 239000013543 active substance Substances 0.000 description 5
• 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 5
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
• 150000001408 amides Chemical class 0.000 description 5
• 125000003118 aryl group Chemical group 0.000 description 5
• 230000008030 elimination Effects 0.000 description 5
• 239000000839 emulsion Substances 0.000 description 5
• 229910052751 metal Inorganic materials 0.000 description 5
• 239000002184 metal Substances 0.000 description 5
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
• 238000007363 ring formation reaction Methods 0.000 description 5
• 239000000741 silica gel Substances 0.000 description 5
• 229910002027 silica gel Inorganic materials 0.000 description 5
• 229910000029 sodium carbonate Inorganic materials 0.000 description 5
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
• 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 4
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
• YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical class ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
• 229910000102 alkali metal hydride Inorganic materials 0.000 description 4
• 150000008046 alkali metal hydrides Chemical class 0.000 description 4
• 150000001450 anions Chemical class 0.000 description 4
• ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
• 239000004202 carbamide Substances 0.000 description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
• 239000003795 chemical substances by application Substances 0.000 description 4
• 238000004587 chromatography analysis Methods 0.000 description 4
• 238000001816 cooling Methods 0.000 description 4
• 244000038559 crop plants Species 0.000 description 4
• HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 4
• 150000002148 esters Chemical class 0.000 description 4
• 238000003818 flash chromatography Methods 0.000 description 4
• 239000008187 granular material Substances 0.000 description 4
• 239000000543 intermediate Substances 0.000 description 4
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
• 239000012948 isocyanate Chemical class 0.000 description 4
• 150000002513 isocyanates Chemical class 0.000 description 4
• 235000012054 meals Nutrition 0.000 description 4
• 238000006396 nitration reaction Methods 0.000 description 4
• 150000002828 nitro derivatives Chemical class 0.000 description 4
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
• 229920000151 polyglycol Polymers 0.000 description 4
• 239000010695 polyglycol Substances 0.000 description 4
• 239000000843 powder Substances 0.000 description 4
• 238000000746 purification Methods 0.000 description 4
• 150000003254 radicals Chemical class 0.000 description 4
• 238000010992 reflux Methods 0.000 description 4
• 229920006395 saturated elastomer Polymers 0.000 description 4
• QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
• 238000005987 sulfurization reaction Methods 0.000 description 4
• GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical class NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 3
• 238000005160 1H NMR spectroscopy Methods 0.000 description 3
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
• NFTWSUWBQWIBSH-UHFFFAOYSA-N 3-chloro-5-fluoro-2-n-methylbenzene-1,2-diamine Chemical compound CNC1=C(N)C=C(F)C=C1Cl NFTWSUWBQWIBSH-UHFFFAOYSA-N 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
• 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 3
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
• IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• 229910021626 Tin(II) chloride Inorganic materials 0.000 description 3
• 230000009471 action Effects 0.000 description 3
• 150000001412 amines Chemical class 0.000 description 3
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
• 150000001733 carboxylic acid esters Chemical class 0.000 description 3
• 150000001735 carboxylic acids Chemical class 0.000 description 3
• 239000000969 carrier Substances 0.000 description 3
• 239000003638 chemical reducing agent Substances 0.000 description 3
• 230000006378 damage Effects 0.000 description 3
• 230000000694 effects Effects 0.000 description 3
• 239000000706 filtrate Substances 0.000 description 3
• 239000012442 inert solvent Substances 0.000 description 3
• 239000000463 material Substances 0.000 description 3
• 229910052987 metal hydride Inorganic materials 0.000 description 3
• 150000004681 metal hydrides Chemical class 0.000 description 3
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
• 239000002480 mineral oil Substances 0.000 description 3
• 235000010446 mineral oil Nutrition 0.000 description 3
• IQVDIWDSLGFLEL-UHFFFAOYSA-N n-(2-chloro-4-fluoro-6-nitrophenyl)-2,2,2-trifluoro-n-methylacetamide Chemical compound FC(F)(F)C(=O)N(C)C1=C(Cl)C=C(F)C=C1[N+]([O-])=O IQVDIWDSLGFLEL-UHFFFAOYSA-N 0.000 description 3
• 239000006072 paste Substances 0.000 description 3
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
• 125000006239 protecting group Chemical group 0.000 description 3
• 101150114085 soc-2 gene Proteins 0.000 description 3
• 239000011780 sodium chloride Substances 0.000 description 3
• 159000000000 sodium salts Chemical class 0.000 description 3
• 241000894007 species Species 0.000 description 3
• 230000007480 spreading Effects 0.000 description 3
• 235000011150 stannous chloride Nutrition 0.000 description 3
• 125000001424 substituent group Chemical group 0.000 description 3
• 239000000758 substrate Substances 0.000 description 3
• RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 3
• 239000000725 suspension Substances 0.000 description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
• AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
• CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 3
• YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 2
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
• NFAOATPOYUWEHM-UHFFFAOYSA-N 2-(6-methylheptyl)phenol Chemical compound CC(C)CCCCCC1=CC=CC=C1O NFAOATPOYUWEHM-UHFFFAOYSA-N 0.000 description 2
• BWYOQCGQOFJXOM-UHFFFAOYSA-N 2-chloro-4-fluoro-n-methyl-6-nitroaniline Chemical compound CNC1=C(Cl)C=C(F)C=C1[N+]([O-])=O BWYOQCGQOFJXOM-UHFFFAOYSA-N 0.000 description 2
• IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical class OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 2
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 2
• VQMYKSAQKCEGSP-UHFFFAOYSA-N 7-chloro-5-fluoro-1,2-dimethyl-4-nitrobenzimidazole Chemical compound FC1=CC(Cl)=C2N(C)C(C)=NC2=C1[N+]([O-])=O VQMYKSAQKCEGSP-UHFFFAOYSA-N 0.000 description 2
• OZYXGAWCQXJAEZ-UHFFFAOYSA-N 7-chloro-5-fluoro-1,2-dimethylbenzimidazol-4-amine Chemical compound FC1=CC(Cl)=C2N(C)C(C)=NC2=C1N OZYXGAWCQXJAEZ-UHFFFAOYSA-N 0.000 description 2
• UJDQNLBNEXKADP-UHFFFAOYSA-N 7-chloro-5-fluoro-1,2-dimethylbenzimidazole Chemical compound FC1=CC(Cl)=C2N(C)C(C)=NC2=C1 UJDQNLBNEXKADP-UHFFFAOYSA-N 0.000 description 2
• MCVDQIGIFAEZRS-UHFFFAOYSA-N 7-chloro-5-fluoro-1-methyl-2-(trifluoromethyl)benzimidazol-4-amine Chemical compound FC1=CC(Cl)=C2N(C)C(C(F)(F)F)=NC2=C1N MCVDQIGIFAEZRS-UHFFFAOYSA-N 0.000 description 2
• LYAHRTSQLUJLMX-UHFFFAOYSA-N 7-chloro-5-fluoro-1-methyl-2-(trifluoromethyl)benzimidazole Chemical compound FC1=CC(Cl)=C2N(C)C(C(F)(F)F)=NC2=C1 LYAHRTSQLUJLMX-UHFFFAOYSA-N 0.000 description 2
• SPRIQTWHGNQKRN-UHFFFAOYSA-N 7-chloro-5-fluoro-1-methyl-4-nitro-2-(trifluoromethyl)benzimidazole Chemical compound FC1=CC(Cl)=C2N(C)C(C(F)(F)F)=NC2=C1[N+]([O-])=O SPRIQTWHGNQKRN-UHFFFAOYSA-N 0.000 description 2
• WXAXUMGPAMZUEU-UHFFFAOYSA-N 7-chloro-5-fluoro-1-methyl-4-nitrobenzotriazole Chemical compound FC1=CC(Cl)=C2N(C)N=NC2=C1[N+]([O-])=O WXAXUMGPAMZUEU-UHFFFAOYSA-N 0.000 description 2
• CRLQOIGIIUAHIO-UHFFFAOYSA-N 7-chloro-5-fluoro-1-methylbenzotriazol-4-amine Chemical compound FC1=CC(Cl)=C2N(C)N=NC2=C1N CRLQOIGIIUAHIO-UHFFFAOYSA-N 0.000 description 2
• LTMQBZNDHBJRFA-UHFFFAOYSA-N 7-chloro-5-fluoro-1-methylbenzotriazole Chemical compound FC1=CC(Cl)=C2N(C)N=NC2=C1 LTMQBZNDHBJRFA-UHFFFAOYSA-N 0.000 description 2
• OVUJBIISCZCBDK-UHFFFAOYSA-N 7-chloro-5-fluoro-4-isocyanato-1,2-dimethylbenzimidazole Chemical compound FC1=CC(Cl)=C2N(C)C(C)=NC2=C1N=C=O OVUJBIISCZCBDK-UHFFFAOYSA-N 0.000 description 2
• 239000005995 Aluminium silicate Substances 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
• 235000021533 Beta vulgaris Nutrition 0.000 description 2
• 241000335053 Beta vulgaris Species 0.000 description 2
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
• KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
• 235000010469 Glycine max Nutrition 0.000 description 2
• 244000068988 Glycine max Species 0.000 description 2
• 244000299507 Gossypium hirsutum Species 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
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
• 240000007594 Oryza sativa Species 0.000 description 2
• 235000007164 Oryza sativa Nutrition 0.000 description 2
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
• 240000006394 Sorghum bicolor Species 0.000 description 2
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
• ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
• 244000098338 Triticum aestivum Species 0.000 description 2
• 240000008042 Zea mays Species 0.000 description 2
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
• 230000002411 adverse Effects 0.000 description 2
• 239000003513 alkali Substances 0.000 description 2
• 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
• 150000008041 alkali metal carbonates Chemical class 0.000 description 2
• 150000001340 alkali metals Chemical class 0.000 description 2
• 125000003342 alkenyl group Chemical group 0.000 description 2
• 150000008055 alkyl aryl sulfonates Chemical group 0.000 description 2
• 150000005215 alkyl ethers Chemical class 0.000 description 2
• 235000012211 aluminium silicate Nutrition 0.000 description 2
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
• 238000005576 amination reaction Methods 0.000 description 2
• 125000003277 amino group Chemical group 0.000 description 2
• DQPBABKTKYNPMH-UHFFFAOYSA-N amino hydrogen sulfate Chemical compound NOS(O)(=O)=O DQPBABKTKYNPMH-UHFFFAOYSA-N 0.000 description 2
• 239000000010 aprotic solvent Substances 0.000 description 2
• 230000015572 biosynthetic process Effects 0.000 description 2
• WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
• OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
• OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 2
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
• 239000007795 chemical reaction product Substances 0.000 description 2
• 238000002425 crystallisation Methods 0.000 description 2
• 230000008025 crystallization Effects 0.000 description 2
• 125000004122 cyclic group Chemical group 0.000 description 2
• 125000000753 cycloalkyl group Chemical group 0.000 description 2
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
• MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
• HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-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
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
• GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
• 239000002270 dispersing agent Substances 0.000 description 2
• 238000001035 drying Methods 0.000 description 2
• 239000003995 emulsifying agent Substances 0.000 description 2
• NXVKRKUGIINGHD-ARJAWSKDSA-N ethyl (z)-3-amino-4,4,4-trifluorobut-2-enoate Chemical compound CCOC(=O)\C=C(/N)C(F)(F)F NXVKRKUGIINGHD-ARJAWSKDSA-N 0.000 description 2
• HPXCGHQXKMRMSK-UHFFFAOYSA-N ethyl n-(7-chloro-5-fluoro-1-methylbenzotriazol-4-yl)carbamate Chemical compound CCOC(=O)NC1=C(F)C=C(Cl)C2=C1N=NN2C HPXCGHQXKMRMSK-UHFFFAOYSA-N 0.000 description 2
• 238000002474 experimental method Methods 0.000 description 2
• 150000002191 fatty alcohols Chemical class 0.000 description 2
• 238000001914 filtration Methods 0.000 description 2
• 238000009472 formulation Methods 0.000 description 2
• 125000002541 furyl group Chemical group 0.000 description 2
• 230000035784 germination Effects 0.000 description 2
• 125000005843 halogen group Chemical group 0.000 description 2
• 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
• 238000011065 in-situ storage Methods 0.000 description 2
• 239000003701 inert diluent Substances 0.000 description 2
• 150000007529 inorganic bases Chemical class 0.000 description 2
• 229910052742 iron Inorganic materials 0.000 description 2
• ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
• 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 2
• WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
• BWRDLNUQULVMAA-UHFFFAOYSA-N n-(2-chloro-4-fluorophenyl)-2,2,2-trifluoroacetamide Chemical compound FC1=CC=C(NC(=O)C(F)(F)F)C(Cl)=C1 BWRDLNUQULVMAA-UHFFFAOYSA-N 0.000 description 2
• 125000006606 n-butoxy group Chemical group 0.000 description 2
• 125000004708 n-butylthio group Chemical group C(CCC)S* 0.000 description 2
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
• 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 2
• 150000002790 naphthalenes Chemical class 0.000 description 2
• 230000000802 nitrating effect Effects 0.000 description 2
• 150000007524 organic acids Chemical class 0.000 description 2
• 235000005985 organic acids Nutrition 0.000 description 2
• 150000002905 orthoesters Chemical class 0.000 description 2
• 229910052763 palladium Inorganic materials 0.000 description 2
• FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
• 150000002989 phenols Chemical class 0.000 description 2
• WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
• XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 2
• 235000011007 phosphoric acid Nutrition 0.000 description 2
• 229910052698 phosphorus Inorganic materials 0.000 description 2
• 239000011574 phosphorus Substances 0.000 description 2
• 239000004033 plastic Substances 0.000 description 2
• 229920000137 polyphosphoric acid Polymers 0.000 description 2
• 239000011591 potassium Substances 0.000 description 2
• 229910052700 potassium Inorganic materials 0.000 description 2
• NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 2
• 229910000105 potassium hydride Inorganic materials 0.000 description 2
• TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
• 125000004076 pyridyl group Chemical group 0.000 description 2
• 125000000714 pyrimidinyl group Chemical group 0.000 description 2
• 230000009467 reduction Effects 0.000 description 2
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
• 238000000638 solvent extraction Methods 0.000 description 2
• 238000005507 spraying Methods 0.000 description 2
• 150000003462 sulfoxides Chemical class 0.000 description 2
• 125000005537 sulfoxonium group Chemical group 0.000 description 2
• 229910052717 sulfur Chemical group 0.000 description 2
• 239000011593 sulfur Chemical group 0.000 description 2
• 238000003786 synthesis reaction Methods 0.000 description 2
• 125000001544 thienyl group Chemical group 0.000 description 2
• 229910052718 tin Inorganic materials 0.000 description 2
• FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 2
• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
• PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
• 150000003672 ureas Chemical class 0.000 description 2
• 235000013311 vegetables Nutrition 0.000 description 2
• 239000002699 waste material Substances 0.000 description 2
• 229910052725 zinc Inorganic materials 0.000 description 2
• 239000011701 zinc Substances 0.000 description 2
• RLCUJBCFAPQEMA-UHFFFAOYSA-N (2-amino-4-hydroxy-3-nitrooxyphenyl) nitrate Chemical compound [N+](=O)([O-])OC1=C(C=CC(=C1N)O[N+](=O)[O-])O RLCUJBCFAPQEMA-UHFFFAOYSA-N 0.000 description 1
• WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
• SYYSBZOSEAUMEY-UHFFFAOYSA-N 1,1,1-trifluoro-2-$l^{1}-sulfanylethane Chemical group FC(F)(F)C[S] SYYSBZOSEAUMEY-UHFFFAOYSA-N 0.000 description 1
• AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
• 125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
• 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 description 1
• 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 description 1
• 125000004515 1,2,4-thiadiazol-3-yl group Chemical group S1N=C(N=C1)* 0.000 description 1
• 125000004516 1,2,4-thiadiazol-5-yl group Chemical group S1N=CN=C1* 0.000 description 1
• YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical class C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
• 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 1
• 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 description 1
• 125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 description 1
• 125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
• 125000004509 1,3,4-oxadiazol-2-yl group Chemical group O1C(=NN=C1)* 0.000 description 1
• 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 description 1
• 150000004869 1,3,4-thiadiazoles Chemical class 0.000 description 1
• 125000004317 1,3,5-triazin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=N1 0.000 description 1
• KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
• GVFQFZYSRBUPTG-UHFFFAOYSA-N 1-amino-3-[7-chloro-5-fluoro-1-methyl-2-(trifluoromethyl)benzimidazol-4-yl]-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound ClC1=CC(=C(C2=C1N(C(=N2)C(F)(F)F)C)N2C(N(C(=CC2=O)C(F)(F)F)N)=O)F GVFQFZYSRBUPTG-UHFFFAOYSA-N 0.000 description 1
• LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 description 1
• DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
• WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
• FKKAGFLIPSSCHT-UHFFFAOYSA-N 1-dodecoxydodecane;sulfuric acid Chemical class OS(O)(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC FKKAGFLIPSSCHT-UHFFFAOYSA-N 0.000 description 1
• 125000004736 1-ethyl-2-methylpropylthio group Chemical group C(C)C(C(C)C)S* 0.000 description 1
• 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
• HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 description 1
• 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
• 125000006018 1-methyl-ethenyl group Chemical group 0.000 description 1
• 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
• XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
• 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
• 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
• 125000004781 2,2-dichloro-2-fluoroethyl group Chemical group [H]C([H])(*)C(F)(Cl)Cl 0.000 description 1
• 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 1
• LMCBYQIBQXKCLN-UHFFFAOYSA-N 2,3-dibutylnaphthalene-1-sulfonic acid;naphthalene Chemical compound C1=CC=CC2=CC=CC=C21.C1=CC=C2C(S(O)(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 LMCBYQIBQXKCLN-UHFFFAOYSA-N 0.000 description 1
• CGNBQYFXGQHUQP-UHFFFAOYSA-N 2,3-dinitroaniline Chemical class NC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O CGNBQYFXGQHUQP-UHFFFAOYSA-N 0.000 description 1
• MHKBMNACOMRIAW-UHFFFAOYSA-N 2,3-dinitrophenol Chemical class OC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O MHKBMNACOMRIAW-UHFFFAOYSA-N 0.000 description 1
• PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
• VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical class NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 1
• KLGTXQOZQXTQPQ-UHFFFAOYSA-N 2-benzyl-1,2-oxazolidin-3-one Chemical class O=C1CCON1CC1=CC=CC=C1 KLGTXQOZQXTQPQ-UHFFFAOYSA-N 0.000 description 1
• CDMGNVWZXRKJNS-UHFFFAOYSA-N 2-benzylphenol Chemical class OC1=CC=CC=C1CC1=CC=CC=C1 CDMGNVWZXRKJNS-UHFFFAOYSA-N 0.000 description 1
• 125000005999 2-bromoethyl group Chemical group 0.000 description 1
• 125000004795 2-chloro-2,2-difluoroethoxy group Chemical group ClC(CO*)(F)F 0.000 description 1
• 125000004780 2-chloro-2,2-difluoroethyl group Chemical group [H]C([H])(*)C(F)(F)Cl 0.000 description 1
• 125000004779 2-chloro-2-fluoroethyl group Chemical group [H]C([H])(*)C([H])(F)Cl 0.000 description 1
• XRAKCYJTJGTSMM-UHFFFAOYSA-N 2-chloro-4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1Cl XRAKCYJTJGTSMM-UHFFFAOYSA-N 0.000 description 1
• VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical class ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 1
• 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
• KKZUMAMOMRDVKA-UHFFFAOYSA-N 2-chloropropane Chemical group [CH2]C(C)Cl KKZUMAMOMRDVKA-UHFFFAOYSA-N 0.000 description 1
• 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
• 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
• 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
• 125000005916 2-methylpentyl group Chemical group 0.000 description 1
• QBGQIMOGHUXVKB-UHFFFAOYSA-N 2-phenyl-4,5,6,7-tetrahydroisoindole-1,3-dione Chemical class O=C1C(CCCC2)=C2C(=O)N1C1=CC=CC=C1 QBGQIMOGHUXVKB-UHFFFAOYSA-N 0.000 description 1
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
• LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
• REEXLQXWNOSJKO-UHFFFAOYSA-N 2h-1$l^{4},2,3-benzothiadiazine 1-oxide Chemical class C1=CC=C2S(=O)NN=CC2=C1 REEXLQXWNOSJKO-UHFFFAOYSA-N 0.000 description 1
• JSIAIROWMJGMQZ-UHFFFAOYSA-N 2h-triazol-4-amine Chemical class NC1=CNN=N1 JSIAIROWMJGMQZ-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
• WLOOYFSUYWVINT-UHFFFAOYSA-N 3-(2-amino-4-chloro-6-fluoro-3-hydroxyphenyl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound O=C1N(C)C(C(F)(F)F)=CC(=O)N1C1=C(N)C(O)=C(Cl)C=C1F WLOOYFSUYWVINT-UHFFFAOYSA-N 0.000 description 1
• FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical compound COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 1
• NIJATWDPLGCTLL-UHFFFAOYSA-N 3-(7-chloro-5-fluoro-1-methylbenzotriazol-4-yl)-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound FC1=CC(Cl)=C2N(C)N=NC2=C1N1C(=O)C=C(C(F)(F)F)N(C)C1=O NIJATWDPLGCTLL-UHFFFAOYSA-N 0.000 description 1
• TZOPHJSFOFSQHO-UHFFFAOYSA-N 3-[7-chloro-5-fluoro-1-methyl-2-(trifluoromethyl)benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4-dione Chemical compound ClC1=CC(=C(C2=C1N(C(=N2)C(F)(F)F)C)N2C(N(C(=CC2=O)C(F)(F)F)C)=O)F TZOPHJSFOFSQHO-UHFFFAOYSA-N 0.000 description 1
• WVBBDVFFDAZSAZ-UHFFFAOYSA-N 3-[7-chloro-5-fluoro-1-methyl-2-(trifluoromethyl)benzimidazol-4-yl]-6-(trifluoromethyl)-1h-pyrimidine-2,4-dione Chemical compound FC1=CC(Cl)=C2N(C)C(C(F)(F)F)=NC2=C1N1C(=O)C=C(C(F)(F)F)NC1=O WVBBDVFFDAZSAZ-UHFFFAOYSA-N 0.000 description 1
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
• 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 125000005917 3-methylpentyl group Chemical group 0.000 description 1
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
• KUMDVKHIEVZRRL-UHFFFAOYSA-N 4,5,6-trifluoro-2-methyl-1h-benzimidazole Chemical compound FC1=C(F)C(F)=C2NC(C)=NC2=C1 KUMDVKHIEVZRRL-UHFFFAOYSA-N 0.000 description 1
• KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
• CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
• HVDYICGGRPSJNB-UHFFFAOYSA-N 7-chloro-5-fluoro-4-isocyanato-1-methyl-2-(trifluoromethyl)benzimidazole Chemical compound FC1=CC(Cl)=C2N(C)C(C(F)(F)F)=NC2=C1N=C=O HVDYICGGRPSJNB-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• 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 1
• QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
• 235000006760 Acer pensylvanicum Nutrition 0.000 description 1
• 235000005255 Allium cepa Nutrition 0.000 description 1
• 244000291564 Allium cepa Species 0.000 description 1
• 244000237956 Amaranthus retroflexus Species 0.000 description 1
• 239000004254 Ammonium phosphate Substances 0.000 description 1
• 235000011446 Amygdalus persica Nutrition 0.000 description 1
• 244000099147 Ananas comosus Species 0.000 description 1
• 235000007119 Ananas comosus Nutrition 0.000 description 1
• 244000105624 Arachis hypogaea Species 0.000 description 1
• 235000010777 Arachis hypogaea Nutrition 0.000 description 1
• 235000005340 Asparagus officinalis Nutrition 0.000 description 1
• 229910015900 BF3 Inorganic materials 0.000 description 1
• 241000894006 Bacteria Species 0.000 description 1
• 239000005711 Benzoic acid Substances 0.000 description 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
• 244000060924 Brassica campestris Species 0.000 description 1
• 235000005637 Brassica campestris Nutrition 0.000 description 1
• 244000178924 Brassica napobrassica Species 0.000 description 1
• 235000011297 Brassica napobrassica Nutrition 0.000 description 1
• 235000006008 Brassica napus var napus Nutrition 0.000 description 1
• 240000000385 Brassica napus var. napus Species 0.000 description 1
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
• FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
• DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
• 244000052707 Camellia sinensis Species 0.000 description 1
• 239000004215 Carbon black (E152) Substances 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
• 235000003255 Carthamus tinctorius Nutrition 0.000 description 1
• 244000020518 Carthamus tinctorius Species 0.000 description 1
• 244000068645 Carya illinoensis Species 0.000 description 1
• 235000009025 Carya illinoensis Nutrition 0.000 description 1
• 241000219312 Chenopodium Species 0.000 description 1
• 235000009344 Chenopodium album Nutrition 0.000 description 1
• 240000006122 Chenopodium album Species 0.000 description 1
• 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
• 235000005979 Citrus limon Nutrition 0.000 description 1
• 244000131522 Citrus pyriformis Species 0.000 description 1
• 235000009088 Citrus pyriformis Nutrition 0.000 description 1
• 235000005976 Citrus sinensis Nutrition 0.000 description 1
• 240000002319 Citrus sinensis Species 0.000 description 1
• 235000007460 Coffea arabica Nutrition 0.000 description 1
• 240000007154 Coffea arabica Species 0.000 description 1
• 241000228031 Coffea liberica Species 0.000 description 1
• 244000016593 Coffea robusta Species 0.000 description 1
• 235000002187 Coffea robusta Nutrition 0.000 description 1
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
• 229920000742 Cotton Polymers 0.000 description 1
• 235000009849 Cucumis sativus Nutrition 0.000 description 1
• 240000008067 Cucumis sativus Species 0.000 description 1
• 244000052363 Cynodon dactylon Species 0.000 description 1
• FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical class OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
• NDUPDOJHUQKPAG-UHFFFAOYSA-N Dalapon Chemical compound CC(Cl)(Cl)C(O)=O NDUPDOJHUQKPAG-UHFFFAOYSA-N 0.000 description 1
• 244000000626 Daucus carota Species 0.000 description 1
• 235000002767 Daucus carota Nutrition 0.000 description 1
• 240000003133 Elaeis guineensis Species 0.000 description 1
• 235000001950 Elaeis guineensis Nutrition 0.000 description 1
• KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
• 235000016623 Fragaria vesca Nutrition 0.000 description 1
• 244000307700 Fragaria vesca Species 0.000 description 1
• 241000233866 Fungi Species 0.000 description 1
• 240000005702 Galium aparine Species 0.000 description 1
• 235000014751 Gossypium arboreum Nutrition 0.000 description 1
• 240000001814 Gossypium arboreum Species 0.000 description 1
• 240000000047 Gossypium barbadense Species 0.000 description 1
• 235000009429 Gossypium barbadense Nutrition 0.000 description 1
• 235000004341 Gossypium herbaceum Nutrition 0.000 description 1
• 240000002024 Gossypium herbaceum Species 0.000 description 1
• 235000009432 Gossypium hirsutum Nutrition 0.000 description 1
• 235000003222 Helianthus annuus Nutrition 0.000 description 1
• 244000020551 Helianthus annuus Species 0.000 description 1
• 244000043261 Hevea brasiliensis Species 0.000 description 1
• 235000007340 Hordeum vulgare Nutrition 0.000 description 1
• 240000005979 Hordeum vulgare Species 0.000 description 1
• 235000008694 Humulus lupulus Nutrition 0.000 description 1
• 244000025221 Humulus lupulus Species 0.000 description 1
• 244000017020 Ipomoea batatas Species 0.000 description 1
• 235000002678 Ipomoea batatas Nutrition 0.000 description 1
• 235000009496 Juglans regia Nutrition 0.000 description 1
• 240000007049 Juglans regia Species 0.000 description 1
• 239000005909 Kieselgur Substances 0.000 description 1
• 241001484259 Lacuna Species 0.000 description 1
• 240000004322 Lens culinaris Species 0.000 description 1
• 235000010666 Lens esculenta Nutrition 0.000 description 1
• 229910010082 LiAlH Inorganic materials 0.000 description 1
• 235000019738 Limestone Nutrition 0.000 description 1
• 241000208204 Linum Species 0.000 description 1
• 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• 208000002720 Malnutrition Diseases 0.000 description 1
• 241000220225 Malus Species 0.000 description 1
• 240000003183 Manihot esculenta Species 0.000 description 1
• 235000004456 Manihot esculenta Nutrition 0.000 description 1
• 235000010624 Medicago sativa Nutrition 0.000 description 1
• 240000004658 Medicago sativa Species 0.000 description 1
• 241001465754 Metazoa Species 0.000 description 1
• 241000234295 Musa Species 0.000 description 1
• 229910002651 NO3 Inorganic materials 0.000 description 1
• PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
• 241000208134 Nicotiana rustica Species 0.000 description 1
• 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
• 244000061176 Nicotiana tabacum Species 0.000 description 1
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-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
• JZTPOMIFAFKKSK-UHFFFAOYSA-N O-phosphonohydroxylamine Chemical compound NOP(O)(O)=O JZTPOMIFAFKKSK-UHFFFAOYSA-N 0.000 description 1
• 235000002725 Olea europaea Nutrition 0.000 description 1
• 240000007817 Olea europaea Species 0.000 description 1
• 239000005642 Oleic acid Substances 0.000 description 1
• ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
• 229910019142 PO4 Inorganic materials 0.000 description 1
• 235000010617 Phaseolus lunatus Nutrition 0.000 description 1
• 244000100170 Phaseolus lunatus Species 0.000 description 1
• 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
• 244000046052 Phaseolus vulgaris Species 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
• 244000193463 Picea excelsa Species 0.000 description 1
• 235000008124 Picea excelsa Nutrition 0.000 description 1
• 235000005205 Pinus Nutrition 0.000 description 1
• 241000218602 Pinus <genus> Species 0.000 description 1
• 235000010582 Pisum sativum Nutrition 0.000 description 1
• 240000004713 Pisum sativum Species 0.000 description 1
• 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
• 239000004721 Polyphenylene oxide Substances 0.000 description 1
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
• 244000007021 Prunus avium Species 0.000 description 1
• 235000010401 Prunus avium Nutrition 0.000 description 1
• 240000005809 Prunus persica Species 0.000 description 1
• 235000014443 Pyrus communis Nutrition 0.000 description 1
• 240000001987 Pyrus communis Species 0.000 description 1
• 239000007868 Raney catalyst Substances 0.000 description 1
• 229910000564 Raney nickel Inorganic materials 0.000 description 1
• 241001506137 Rapa Species 0.000 description 1
• 244000281247 Ribes rubrum Species 0.000 description 1
• 235000016911 Ribes sativum Nutrition 0.000 description 1
• 240000000528 Ricinus communis Species 0.000 description 1
• 235000004443 Ricinus communis Nutrition 0.000 description 1
• 235000007201 Saccharum officinarum Nutrition 0.000 description 1
• 240000000111 Saccharum officinarum Species 0.000 description 1
• 235000007238 Secale cereale Nutrition 0.000 description 1
• 244000082988 Secale cereale Species 0.000 description 1
• 240000003768 Solanum lycopersicum Species 0.000 description 1
• 235000002595 Solanum tuberosum Nutrition 0.000 description 1
• 244000061456 Solanum tuberosum Species 0.000 description 1
• 235000007230 Sorghum bicolor Nutrition 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
• 229940100389 Sulfonylurea Drugs 0.000 description 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
• 235000006468 Thea sinensis Nutrition 0.000 description 1
• 244000299461 Theobroma cacao Species 0.000 description 1
• 235000009470 Theobroma cacao Nutrition 0.000 description 1
• 235000011941 Tilia x europaea Nutrition 0.000 description 1
• 206010044278 Trace element deficiency Diseases 0.000 description 1
• 235000015724 Trifolium pratense Nutrition 0.000 description 1
• 240000002913 Trifolium pratense Species 0.000 description 1
• 235000021307 Triticum Nutrition 0.000 description 1
• 235000007264 Triticum durum Nutrition 0.000 description 1
• 241000209143 Triticum turgidum subsp. durum Species 0.000 description 1
• ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical class O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 1
• 235000010749 Vicia faba Nutrition 0.000 description 1
• 240000006677 Vicia faba Species 0.000 description 1
• 235000014787 Vitis vinifera Nutrition 0.000 description 1
• 240000006365 Vitis vinifera Species 0.000 description 1
• 235000007244 Zea mays Nutrition 0.000 description 1
• 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
• 241001148683 Zostera marina Species 0.000 description 1
• KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 1
• CDYUXJBPCIBFNK-UHFFFAOYSA-N [O]C(=O)CC(F)(F)F Chemical group [O]C(=O)CC(F)(F)F CDYUXJBPCIBFNK-UHFFFAOYSA-N 0.000 description 1
• 239000002156 adsorbate Substances 0.000 description 1
• 244000193174 agave Species 0.000 description 1
• 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
• 229910001413 alkali metal ion Inorganic materials 0.000 description 1
• 150000001342 alkaline earth metals Chemical class 0.000 description 1
• 125000003302 alkenyloxy group Chemical group 0.000 description 1
• 125000005136 alkenylsulfinyl group Chemical group 0.000 description 1
• 125000005137 alkenylsulfonyl group Chemical group 0.000 description 1
• 125000005108 alkenylthio group Chemical group 0.000 description 1
• 125000003545 alkoxy group Chemical group 0.000 description 1
• 125000002877 alkyl aryl group Chemical group 0.000 description 1
• 125000005037 alkyl phenyl group Chemical group 0.000 description 1
• 150000008051 alkyl sulfates 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
• 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
• 125000004414 alkyl thio group Chemical group 0.000 description 1
• 239000002168 alkylating agent Substances 0.000 description 1
• 229940100198 alkylating agent Drugs 0.000 description 1
• 230000002152 alkylating effect Effects 0.000 description 1
• 125000000304 alkynyl group Chemical group 0.000 description 1
• 125000005133 alkynyloxy group Chemical group 0.000 description 1
• 125000005134 alkynylsulfinyl group Chemical group 0.000 description 1
• 125000005139 alkynylsulfonyl group Chemical group 0.000 description 1
• 125000005109 alkynylthio group Chemical group 0.000 description 1
• 125000005336 allyloxy group Chemical group 0.000 description 1
• 125000004103 aminoalkyl group Chemical group 0.000 description 1
• 125000005097 aminocarbonylalkyl group Chemical group 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
• 235000019289 ammonium phosphates Nutrition 0.000 description 1
• 150000003863 ammonium salts Chemical class 0.000 description 1
• BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
• 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
• 235000011130 ammonium sulphate Nutrition 0.000 description 1
• 150000008064 anhydrides Chemical class 0.000 description 1
• 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
• 150000003931 anilides Chemical class 0.000 description 1
• 239000012736 aqueous medium Substances 0.000 description 1
• 239000008346 aqueous phase Substances 0.000 description 1
• 239000003125 aqueous solvent Substances 0.000 description 1
• 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
• 125000004104 aryloxy group Chemical group 0.000 description 1
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 description 1
• 125000004273 azetidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])C1([H])* 0.000 description 1
• 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 description 1
• 125000004266 aziridin-1-yl group Chemical group [H]C1([H])N(*)C1([H])[H] 0.000 description 1
• 125000004267 aziridin-2-yl group Chemical group [H]N1C([H])([H])C1([H])* 0.000 description 1
• 229910052788 barium Inorganic materials 0.000 description 1
• DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
• 235000010233 benzoic acid Nutrition 0.000 description 1
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 1
• YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 1
• 230000001588 bifunctional effect Effects 0.000 description 1
• 239000004305 biphenyl Substances 0.000 description 1
• 235000010290 biphenyl Nutrition 0.000 description 1
• 125000006267 biphenyl group Chemical group 0.000 description 1
• 238000009395 breeding Methods 0.000 description 1
• 230000001488 breeding effect Effects 0.000 description 1
• 239000011575 calcium Substances 0.000 description 1
• 229910052791 calcium Inorganic materials 0.000 description 1
• 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
• 125000002837 carbocyclic group Chemical group 0.000 description 1
• 229910052799 carbon Inorganic materials 0.000 description 1
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
• 230000003197 catalytic effect Effects 0.000 description 1
• 239000001913 cellulose Substances 0.000 description 1
• 229920002678 cellulose Polymers 0.000 description 1
• 235000013339 cereals Nutrition 0.000 description 1
• 150000001805 chlorine compounds Chemical class 0.000 description 1
• 125000004789 chlorodifluoromethoxy group Chemical group ClC(O*)(F)F 0.000 description 1
• 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 1
• 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 1
• 239000004927 clay Substances 0.000 description 1
• 239000011280 coal tar Substances 0.000 description 1
• 239000007931 coated granule Substances 0.000 description 1
• 238000009833 condensation Methods 0.000 description 1
• 230000005494 condensation Effects 0.000 description 1
• 238000006482 condensation reaction Methods 0.000 description 1
• 229910052802 copper Inorganic materials 0.000 description 1
• 239000010949 copper Substances 0.000 description 1
• DMSZORWOGDLWGN-UHFFFAOYSA-N ctk1a3526 Chemical compound NP(N)(N)=O DMSZORWOGDLWGN-UHFFFAOYSA-N 0.000 description 1
• 125000004966 cyanoalkyl group Chemical group 0.000 description 1
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000006622 cycloheptylmethyl group Chemical group 0.000 description 1
• HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical class O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 1
• HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000006623 cyclooctylmethyl group Chemical group 0.000 description 1
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000004859 cyclopropyloxymethyl group Chemical group C1(CC1)OC* 0.000 description 1
• 238000000354 decomposition reaction Methods 0.000 description 1
• 230000035613 defoliation Effects 0.000 description 1
• 239000002274 desiccant Substances 0.000 description 1
• MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
• 150000004891 diazines Chemical class 0.000 description 1
• 150000004816 dichlorobenzenes Chemical class 0.000 description 1
• 125000004788 dichlorofluoromethoxy group Chemical group ClC(O*)(F)Cl 0.000 description 1
• 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 1
• 239000002283 diesel fuel Substances 0.000 description 1
• 235000014113 dietary fatty acids Nutrition 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
• RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
• 238000007865 diluting Methods 0.000 description 1
• 238000010790 dilution Methods 0.000 description 1
• 239000012895 dilution Substances 0.000 description 1
• 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
• OMBRFUXPXNIUCZ-UHFFFAOYSA-N dioxidonitrogen(1+) Chemical class O=[N+]=O OMBRFUXPXNIUCZ-UHFFFAOYSA-N 0.000 description 1
• GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 1
• LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
• 239000010459 dolomite Substances 0.000 description 1
• 229910000514 dolomite Inorganic materials 0.000 description 1
• 239000000428 dust Substances 0.000 description 1
• 238000010410 dusting Methods 0.000 description 1
• 150000002084 enol ethers Chemical class 0.000 description 1
• 229940052303 ethers for general anesthesia Drugs 0.000 description 1
• QPMJENKZJUFOON-PLNGDYQASA-N ethyl (z)-3-chloro-2-cyano-4,4,4-trifluorobut-2-enoate Chemical compound CCOC(=O)C(\C#N)=C(/Cl)C(F)(F)F QPMJENKZJUFOON-PLNGDYQASA-N 0.000 description 1
• RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
• LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
• 238000011156 evaluation Methods 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 239000000194 fatty acid Substances 0.000 description 1
• 229930195729 fatty acid Natural products 0.000 description 1
• 150000004665 fatty acids Chemical class 0.000 description 1
• 239000003337 fertilizer Substances 0.000 description 1
• 239000012530 fluid Substances 0.000 description 1
• 239000000499 gel Substances 0.000 description 1
• 238000010353 genetic engineering Methods 0.000 description 1
• 239000011521 glass Substances 0.000 description 1
• 235000002532 grape seed extract Nutrition 0.000 description 1
• 125000000262 haloalkenyl group Chemical group 0.000 description 1
• 125000004438 haloalkoxy group Chemical group 0.000 description 1
• 125000001188 haloalkyl group Chemical group 0.000 description 1
• 125000004440 haloalkylsulfinyl group Chemical group 0.000 description 1
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 description 1
• 125000004995 haloalkylthio group Chemical group 0.000 description 1
• 125000000232 haloalkynyl group Chemical group 0.000 description 1
• 150000003977 halocarboxylic acids Chemical class 0.000 description 1
• 125000001072 heteroaryl group Chemical group 0.000 description 1
• 125000005842 heteroatom Chemical group 0.000 description 1
• 125000004415 heterocyclylalkyl group Chemical group 0.000 description 1
• 150000004761 hexafluorosilicates Chemical class 0.000 description 1
• GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
• 238000004128 high performance liquid chromatography Methods 0.000 description 1
• 239000003864 humus Substances 0.000 description 1
• YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 1
• 150000007857 hydrazones Chemical class 0.000 description 1
• 150000004678 hydrides Chemical class 0.000 description 1
• 229930195733 hydrocarbon Natural products 0.000 description 1
• 150000002430 hydrocarbons Chemical class 0.000 description 1
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
• ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 1
• WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
• 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
• 150000002460 imidazoles Chemical class 0.000 description 1
• 125000002883 imidazolyl group Chemical group 0.000 description 1
• 229910010272 inorganic material Inorganic materials 0.000 description 1
• 239000011147 inorganic material Substances 0.000 description 1
• 229910052740 iodine Inorganic materials 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• 150000002500 ions Chemical class 0.000 description 1
• 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
• 238000002955 isolation Methods 0.000 description 1
• QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
• 125000001786 isothiazolyl group Chemical group 0.000 description 1
• 125000000842 isoxazolyl group Chemical group 0.000 description 1
• 239000003350 kerosene Substances 0.000 description 1
• 150000002576 ketones Chemical class 0.000 description 1
• CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
• 239000004571 lime Substances 0.000 description 1
• 239000006028 limestone Substances 0.000 description 1
• SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
• 229910000103 lithium hydride Inorganic materials 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• 239000000395 magnesium oxide Substances 0.000 description 1
• CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
• 235000019341 magnesium sulphate Nutrition 0.000 description 1
• AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
• 235000009973 maize Nutrition 0.000 description 1
• WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
• 239000002609 medium Substances 0.000 description 1
• 229910021645 metal ion Inorganic materials 0.000 description 1
• 150000002739 metals Chemical class 0.000 description 1
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
• NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
• 229920000609 methyl cellulose Polymers 0.000 description 1
• 239000001923 methylcellulose Substances 0.000 description 1
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
• 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 1
• 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 description 1
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
• 125000006126 n-butyl sulfonyl group Chemical group 0.000 description 1
• 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
• 125000004718 n-hexylthio group Chemical group C(CCCCC)S* 0.000 description 1
• 125000002412 n-penten-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000002504 n-penten-4-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
• 125000004712 n-pentylthio group Chemical group C(CCCC)S* 0.000 description 1
• 125000004888 n-propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 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
• 150000002825 nitriles Chemical class 0.000 description 1
• 239000012299 nitrogen atmosphere Substances 0.000 description 1
• 125000004433 nitrogen atom Chemical group N* 0.000 description 1
• LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
• 229910000510 noble metal Inorganic materials 0.000 description 1
• 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
• 239000012875 nonionic emulsifier Substances 0.000 description 1
• 231100001184 nonphytotoxic Toxicity 0.000 description 1
• SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
• 235000016709 nutrition Nutrition 0.000 description 1
• YLACRFYIUQZNIV-UHFFFAOYSA-N o-(2,4-dinitrophenyl)hydroxylamine Chemical group NOC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O YLACRFYIUQZNIV-UHFFFAOYSA-N 0.000 description 1
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
• 125000001477 organic nitrogen group Chemical group 0.000 description 1
• 150000004866 oxadiazoles Chemical class 0.000 description 1
• 125000001715 oxadiazolyl group Chemical group 0.000 description 1
• 125000002971 oxazolyl group Chemical group 0.000 description 1
• 125000004322 oxepan-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000004274 oxetan-2-yl group Chemical group [H]C1([H])OC([H])(*)C1([H])[H] 0.000 description 1
• 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 description 1
• 150000002924 oxiranes Chemical class 0.000 description 1
• 125000000466 oxiranyl group Chemical group 0.000 description 1
• 230000020477 pH reduction Effects 0.000 description 1
• 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
• 239000000575 pesticide Substances 0.000 description 1
• 229960003424 phenylacetic acid Drugs 0.000 description 1
• 239000003279 phenylacetic acid Substances 0.000 description 1
• 125000003884 phenylalkyl group Chemical group 0.000 description 1
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
• 150000008048 phenylpyrazoles Chemical class 0.000 description 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
• 239000010452 phosphate Substances 0.000 description 1
• 230000003032 phytopathogenic effect Effects 0.000 description 1
• SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 description 1
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
• 229910052697 platinum Inorganic materials 0.000 description 1
• 229920000570 polyether Polymers 0.000 description 1
• 229920001451 polypropylene glycol Polymers 0.000 description 1
• 238000001556 precipitation Methods 0.000 description 1
• 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 description 1
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
• 125000000177 propargylthio group Chemical group [H]C#CC([H])([H])S* 0.000 description 1
• 239000011814 protection agent Substances 0.000 description 1
• 239000003586 protic polar solvent Substances 0.000 description 1
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
• 150000003217 pyrazoles Chemical class 0.000 description 1
• 125000003226 pyrazolyl group Chemical group 0.000 description 1
• 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
• 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
• 150000004892 pyridazines Chemical class 0.000 description 1
• 125000002098 pyridazinyl group Chemical group 0.000 description 1
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
• 150000008512 pyrimidinediones Chemical class 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
• 239000000376 reactant Substances 0.000 description 1
• 235000013526 red clover Nutrition 0.000 description 1
• 230000004044 response Effects 0.000 description 1
• 235000009566 rice Nutrition 0.000 description 1
• 239000012266 salt solution Substances 0.000 description 1
• 239000004576 sand Substances 0.000 description 1
• 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 150000004760 silicates Chemical class 0.000 description 1
• 239000000377 silicon dioxide Substances 0.000 description 1
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 description 1
• 235000010288 sodium nitrite Nutrition 0.000 description 1
• 239000002689 soil Substances 0.000 description 1
• 239000012265 solid product Substances 0.000 description 1
• 239000011877 solvent mixture Substances 0.000 description 1
• 238000009331 sowing Methods 0.000 description 1
• 238000001228 spectrum Methods 0.000 description 1
• 230000002269 spontaneous effect Effects 0.000 description 1
• 239000007921 spray Substances 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1
• 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
• OKQKDCXVLPGWPO-UHFFFAOYSA-N sulfanylidenephosphane Chemical compound S=P OKQKDCXVLPGWPO-UHFFFAOYSA-N 0.000 description 1
• 229940124530 sulfonamide Drugs 0.000 description 1
• 150000003456 sulfonamides Chemical class 0.000 description 1
• 150000003460 sulfonic acids Chemical class 0.000 description 1
• 125000004434 sulfur atom Chemical group 0.000 description 1
• 230000002195 synergetic effect Effects 0.000 description 1
• 229920002994 synthetic fiber Polymers 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
• 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
• 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
• AHJWSRRHTXRLAQ-UHFFFAOYSA-N tetramethoxymethane Chemical compound COC(OC)(OC)OC AHJWSRRHTXRLAQ-UHFFFAOYSA-N 0.000 description 1
• QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
• 125000001113 thiadiazolyl group Chemical group 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• 125000004324 thiepan-2-yl group Chemical group [H]C1([H])SC([H])(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000004275 thietan-2-yl group Chemical group [H]C1([H])SC([H])(*)C1([H])[H] 0.000 description 1
• 125000006300 thietan-3-yl group Chemical group [H]C1([H])SC([H])([H])C1([H])* 0.000 description 1
• 125000001730 thiiranyl group Chemical group 0.000 description 1
• 239000011135 tin Substances 0.000 description 1
• FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
• 238000012546 transfer Methods 0.000 description 1
• 229910052723 transition metal Inorganic materials 0.000 description 1
• 150000003624 transition metals Chemical class 0.000 description 1
• 150000003918 triazines Chemical class 0.000 description 1
• 125000001425 triazolyl group Chemical group 0.000 description 1
• WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
• UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
• 150000003673 urethanes Chemical class 0.000 description 1
• 229910052720 vanadium Inorganic materials 0.000 description 1
• 238000005406 washing Methods 0.000 description 1
• 239000004562 water dispersible granule Substances 0.000 description 1
• 239000002023 wood Substances 0.000 description 1
• 239000008096 xylene Substances 0.000 description 1
• 150000003738 xylenes Chemical class 0.000 description 1