SK107499A3 - 2,4-diamino-1,3,5-triazines, the manufacture and use thereof as herbicides and plant growth regulators - Google Patents

Info

Publication number

SK107499A3

SK107499A3 SK1074-99A SK107499A SK107499A3 SK 107499 A3 SK107499 A3 SK 107499A3 SK 107499 A SK107499 A SK 107499A SK 107499 A3 SK107499 A3 SK 107499A3

Authority

SK

Slovakia

Prior art keywords

group

carbon atoms

alkyl

substituted

radicals

Prior art date

1997-02-10

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• 239000004009 herbicide Substances 0.000 title claims abstract description 9
• 239000005648 plant growth regulator Substances 0.000 title claims abstract description 5
• VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical class NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 title claims description 10
• 238000004519 manufacturing process Methods 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 88
• 150000003839 salts Chemical class 0.000 claims abstract description 41
• 238000000034 method Methods 0.000 claims abstract description 20
• 230000002363 herbicidal effect Effects 0.000 claims abstract description 19
• 230000008635 plant growth Effects 0.000 claims abstract description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 408
• 125000004432 carbon atom Chemical group C* 0.000 claims description 380
• -1 alkyl radical Chemical class 0.000 claims description 240
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 201
• 125000000217 alkyl group Chemical group 0.000 claims description 196
• 150000003254 radicals Chemical class 0.000 claims description 101
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 79
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 77
• 229910052736 halogen Inorganic materials 0.000 claims description 76
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 74
• 150000002367 halogens Chemical class 0.000 claims description 70
• 229910052757 nitrogen Inorganic materials 0.000 claims description 64
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 62
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 61
• 125000003545 alkoxy group Chemical group 0.000 claims description 58
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 55
• 125000005842 heteroatom Chemical group 0.000 claims description 50
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 49
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 45
• 229910052760 oxygen Inorganic materials 0.000 claims description 45
• 239000001301 oxygen Chemical group 0.000 claims description 45
• 125000000623 heterocyclic group Chemical group 0.000 claims description 42
• 125000006413 ring segment Chemical group 0.000 claims description 40
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 38
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 34
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 33
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 32
• 125000003282 alkyl amino group Chemical group 0.000 claims description 31
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 30
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 30
• 125000001188 haloalkyl group Chemical group 0.000 claims description 30
• 229910052717 sulfur Chemical group 0.000 claims description 30
• 239000011593 sulfur Chemical group 0.000 claims description 30
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 28
• 229910052739 hydrogen Inorganic materials 0.000 claims description 28
• 239000000203 mixture Substances 0.000 claims description 28
• 125000005843 halogen group Chemical group 0.000 claims description 27
• 239000001257 hydrogen Substances 0.000 claims description 27
• 239000002253 acid Substances 0.000 claims description 26
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 26
• 125000004414 alkyl thio group Chemical group 0.000 claims description 24
• 125000004043 oxo group Chemical group O=* 0.000 claims description 24
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 23
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 23
• 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 23
• 125000004122 cyclic group Chemical group 0.000 claims description 21
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 20
• 125000000304 alkynyl group Chemical group 0.000 claims description 20
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 20
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
• 125000003342 alkenyl group Chemical group 0.000 claims description 19
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 19
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 19
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 18
• 229930195733 hydrocarbon Natural products 0.000 claims description 18
• 125000001424 substituent group Chemical group 0.000 claims description 18
• 239000004215 Carbon black (E152) Substances 0.000 claims description 17
• 125000002837 carbocyclic group Chemical group 0.000 claims description 17
• 238000009472 formulation Methods 0.000 claims description 17
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
• 125000002252 acyl group Chemical group 0.000 claims description 16
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 15
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 15
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
• 239000000460 chlorine Substances 0.000 claims description 14
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 14
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 13
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
• 229910052801 chlorine Inorganic materials 0.000 claims description 12
• 125000004468 heterocyclylthio group Chemical group 0.000 claims description 12
• 125000003277 amino group Chemical group 0.000 claims description 11
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
• 125000004442 acylamino group Chemical group 0.000 claims description 10
• 125000002947 alkylene group Chemical group 0.000 claims description 10
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 10
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 9
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 9
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 9
• 238000002360 preparation method Methods 0.000 claims description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
• 230000008569 process Effects 0.000 claims description 9
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 8
• 125000002015 acyclic group Chemical group 0.000 claims description 8
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 8
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 8
• 125000004429 atom Chemical group 0.000 claims description 8
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 8
• 125000000232 haloalkynyl group Chemical group 0.000 claims description 8
• 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 8
• ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 8
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 7
• 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 7
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 7
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 7
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
• 125000005347 halocycloalkyl group Chemical group 0.000 claims description 7
• 150000002430 hydrocarbons Chemical class 0.000 claims description 7
• 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 7
• 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims description 6
• 229910052794 bromium Inorganic materials 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 6
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000001072 heteroaryl group Chemical group 0.000 claims description 5
• 229910052740 iodine Inorganic materials 0.000 claims description 5
• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 4
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 4
• 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 4
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
• 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 4
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
• 150000001412 amines Chemical class 0.000 claims description 4
• 229910052799 carbon Inorganic materials 0.000 claims description 4
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
• 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 4
• 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 4
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
• 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 3
• RFMQOHXWHFHOJF-UHFFFAOYSA-N cyano thiocyanate Chemical compound N#CSC#N RFMQOHXWHFHOJF-UHFFFAOYSA-N 0.000 claims description 3
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 3
• 239000011630 iodine Substances 0.000 claims description 3
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 3
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
• 125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 claims description 2
• 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 2
• 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 2
• 150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
• 125000005357 cycloalkylalkynyl group Chemical group 0.000 claims description 2
• 125000001153 fluoro group Chemical group F* 0.000 claims description 2
• 125000000524 functional group Chemical group 0.000 claims description 2
• 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 2
• 125000005203 haloalkylcarbonyloxy group Chemical group 0.000 claims description 2
• NWBNORAVIXIZTL-UHFFFAOYSA-N nitro thiocyanate Chemical compound [O-][N+](=O)SC#N NWBNORAVIXIZTL-UHFFFAOYSA-N 0.000 claims description 2
• 125000002092 orthoester group Chemical group 0.000 claims description 2
• 125000001589 carboacyl group Chemical group 0.000 claims 9
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
• 125000006644 (C2-C6) haloalkynyl group Chemical group 0.000 claims 1
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
• 125000004103 aminoalkyl group Chemical group 0.000 claims 1
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 1
• 125000004995 haloalkylthio group Chemical group 0.000 claims 1
• 239000000126 substance Substances 0.000 abstract description 13
• 230000001105 regulatory effect Effects 0.000 abstract description 3
• HBIJVSRSYFCTCY-UHFFFAOYSA-N 2-n-(2-phenoxyethyl)-1,3,5-triazine-2,4-diamine Chemical group NC1=NC=NC(NCCOC=2C=CC=CC=2)=N1 HBIJVSRSYFCTCY-UHFFFAOYSA-N 0.000 abstract description 2
• 238000005481 NMR spectroscopy Methods 0.000 description 264
• 125000001309 chloro group Chemical group Cl* 0.000 description 93
• 241000196324 Embryophyta Species 0.000 description 50
• 229920000728 polyester Polymers 0.000 description 22
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
• 239000002585 base Substances 0.000 description 19
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
• 238000006243 chemical reaction Methods 0.000 description 18
• 150000002148 esters Chemical class 0.000 description 16
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
• 239000002904 solvent Substances 0.000 description 15
• 239000004480 active ingredient Substances 0.000 description 13
• 239000003960 organic solvent Substances 0.000 description 13
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
• 239000013543 active substance Substances 0.000 description 11
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 11
• 239000008187 granular material Substances 0.000 description 11
• 239000000843 powder Substances 0.000 description 11
• 239000007921 spray Substances 0.000 description 11
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
• 150000007513 acids Chemical class 0.000 description 10
• 150000001340 alkali metals Chemical class 0.000 description 10
• 238000009835 boiling Methods 0.000 description 10
• 230000035784 germination Effects 0.000 description 10
• 238000012360 testing method Methods 0.000 description 10
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 10
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 229910052783 alkali metal Inorganic materials 0.000 description 9
• 230000012010 growth Effects 0.000 description 9
• 239000002689 soil Substances 0.000 description 9
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
• 244000038559 crop plants Species 0.000 description 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
• 240000007594 Oryza sativa Species 0.000 description 7
• 235000007164 Oryza sativa Nutrition 0.000 description 7
• 239000004495 emulsifiable concentrate Substances 0.000 description 7
• 235000009566 rice Nutrition 0.000 description 7
• 239000004562 water dispersible granule Substances 0.000 description 7
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
• 150000001342 alkaline earth metals Chemical class 0.000 description 6
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
• 239000003995 emulsifying agent Substances 0.000 description 6
• 239000000839 emulsion Substances 0.000 description 6
• 150000003460 sulfonic acids Chemical class 0.000 description 6
• SCZNXLWKYFICFV-UHFFFAOYSA-N 1,2,3,4,5,7,8,9-octahydropyrido[1,2-b]diazepine Chemical compound C1CCCNN2CCCC=C21 SCZNXLWKYFICFV-UHFFFAOYSA-N 0.000 description 5
• 241000192043 Echinochloa Species 0.000 description 5
• 229910000288 alkali metal carbonate Inorganic materials 0.000 description 5
• 150000008041 alkali metal carbonates Chemical class 0.000 description 5
• 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 5
• 125000003118 aryl group Chemical group 0.000 description 5
• 235000019441 ethanol Nutrition 0.000 description 5
• 238000005469 granulation Methods 0.000 description 5
• 230000003179 granulation Effects 0.000 description 5
• 238000011065 in-situ storage Methods 0.000 description 5
• 239000000543 intermediate Substances 0.000 description 5
• 238000002156 mixing Methods 0.000 description 5
• 239000004094 surface-active agent Substances 0.000 description 5
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 5
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
• 150000008044 alkali metal hydroxides Chemical class 0.000 description 4
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
• WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
• 239000003054 catalyst Substances 0.000 description 4
• 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 4
• 239000012141 concentrate Substances 0.000 description 4
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
• 230000000694 effects Effects 0.000 description 4
• 239000011737 fluorine Substances 0.000 description 4
• PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 4
• 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 4
• 239000000463 material Substances 0.000 description 4
• 150000004702 methyl esters Chemical class 0.000 description 4
• 150000007530 organic bases Chemical class 0.000 description 4
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
• 229920000151 polyglycol Polymers 0.000 description 4
• 239000010695 polyglycol Substances 0.000 description 4
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
• 159000000000 sodium salts Chemical class 0.000 description 4
• 125000000547 substituted alkyl group Chemical group 0.000 description 4
• 239000004546 suspension concentrate Substances 0.000 description 4
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
• 239000005995 Aluminium silicate Substances 0.000 description 3
• 241000234653 Cyperus Species 0.000 description 3
• 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 3
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
• 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 3
• 239000004372 Polyvinyl alcohol Substances 0.000 description 3
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• 240000006694 Stellaria media Species 0.000 description 3
• 125000005133 alkynyloxy group Chemical group 0.000 description 3
• 235000012211 aluminium silicate Nutrition 0.000 description 3
• 150000001735 carboxylic acids Chemical class 0.000 description 3
• 239000003795 chemical substances by application Substances 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 description 3
• 239000000084 colloidal system Substances 0.000 description 3
• 239000002270 dispersing agent Substances 0.000 description 3
• 239000006185 dispersion Substances 0.000 description 3
• OSUHJPCHFDQAIT-UHFFFAOYSA-N ethyl 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoate Chemical group C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-UHFFFAOYSA-N 0.000 description 3
• 239000003337 fertilizer Substances 0.000 description 3
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 3
• 239000003921 oil Substances 0.000 description 3
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