UA73173C2

UA73173C2 - Substituted iminoazines

Substituted iminoazines Download PDF

Info

Publication number: UA73173C2
Authority: UA; Ukraine
Prior art keywords: group; carbon atoms; substituted; unsubstituted; chlorine
Prior art date: 2000-05-19

Application number

UA20021210277A

Other languages

English (en)

Ukrainian (uk)

Priority date

2000-05-19

Filing date

2001-08-05

Publication date

2005-06-15

2001-08-05 Application filed filed Critical

2005-06-15 Publication of UA73173C2 publication Critical patent/UA73173C2/uk

Links

150000001875 compounds Chemical class 0.000 claims abstract description 46
239000004009 herbicide Substances 0.000 claims abstract description 8
-1 alkylideneamino Chemical group 0.000 claims description 175
125000004432 carbon atom Chemical group C* 0.000 claims description 136
229910052801 chlorine Inorganic materials 0.000 claims description 78
239000000460 chlorine Substances 0.000 claims description 72
229910052731 fluorine Inorganic materials 0.000 claims description 62
239000011737 fluorine Substances 0.000 claims description 62
125000004093 cyano group Chemical group *C#N 0.000 claims description 58
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 56
125000000217 alkyl group Chemical group 0.000 claims description 54
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 38
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 37
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 37
229910052794 bromium Inorganic materials 0.000 claims description 36
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 34
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 32
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 30
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 28
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 28
125000001153 fluoro group Chemical group F* 0.000 claims description 27
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 26
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
229910052736 halogen Inorganic materials 0.000 claims description 18
150000002367 halogens Chemical class 0.000 claims description 18
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 17
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 17
125000006125 ethylsulfonyl group Chemical group 0.000 claims description 16
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 16
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 16
125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 16
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 16
125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 15
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
125000004434 sulfur atom Chemical group 0.000 claims description 15
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 15
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 15
125000003118 aryl group Chemical group 0.000 claims description 14
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 13
125000005843 halogen group Chemical group 0.000 claims description 13
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 13
125000004430 oxygen atom Chemical group O* 0.000 claims description 13
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 13
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 12
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 12
125000004414 alkyl thio group Chemical group 0.000 claims description 12
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 12
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 12
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 12
229910052717 sulfur Inorganic materials 0.000 claims description 12
CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical group FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 11
125000001188 haloalkyl group Chemical group 0.000 claims description 11
125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 11
125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
125000000623 heterocyclic group Chemical group 0.000 claims description 9
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 8
125000003277 amino group Chemical group 0.000 claims description 8
125000003710 aryl alkyl group Chemical group 0.000 claims description 8
125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 8
125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims description 8
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 8
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 claims description 8
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 8
125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 8
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 8
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 8
125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 8
125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 8
125000004995 haloalkylthio group Chemical group 0.000 claims description 8
125000000547 substituted alkyl group Chemical group 0.000 claims description 8
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 7
125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
ARPVECYSCGKGPQ-UHFFFAOYSA-N N1[ClH]C=CC=C1 Chemical class N1[ClH]C=CC=C1 ARPVECYSCGKGPQ-UHFFFAOYSA-N 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000003282 alkyl amino group Chemical group 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
230000002363 herbicidal effect Effects 0.000 claims description 5
125000003302 alkenyloxy group Chemical group 0.000 claims description 4
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 4
125000005530 alkylenedioxy group Chemical group 0.000 claims description 4
125000001769 aryl amino group Chemical group 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 4
125000006310 cycloalkyl amino group Chemical group 0.000 claims description 4
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 4
125000004663 dialkyl amino group Chemical group 0.000 claims description 4
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
125000006437 ethyl cyclopropyl group Chemical group 0.000 claims description 4
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
125000000842 isoxazolyl group Chemical group 0.000 claims description 4
125000006431 methyl cyclopropyl group Chemical group 0.000 claims description 4
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
125000002950 monocyclic group Chemical group 0.000 claims description 4
230000007935 neutral effect Effects 0.000 claims description 4
125000002971 oxazolyl group Chemical group 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
125000003226 pyrazolyl group Chemical group 0.000 claims description 4
125000006513 pyridinyl methyl group Chemical group 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
125000000168 pyrrolyl group Chemical group 0.000 claims description 4
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
125000000335 thiazolyl group Chemical group 0.000 claims description 4
125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 claims description 4
125000001544 thienyl group Chemical group 0.000 claims description 4
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
125000006317 cyclopropyl amino group Chemical group 0.000 claims description 3
239000000945 filler Substances 0.000 claims description 3
125000002541 furyl group Chemical group 0.000 claims description 3
125000000262 haloalkenyl group Chemical group 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 claims description 2
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 2
125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
WATNXVHKRRTUFK-UHFFFAOYSA-N n-[[1-(2-methoxyphenyl)indazol-5-yl]methyl]-2-propylpentanamide Chemical compound N1=CC2=CC(CNC(=O)C(CCC)CCC)=CC=C2N1C1=CC=CC=C1OC WATNXVHKRRTUFK-UHFFFAOYSA-N 0.000 claims 1
239000004094 surface-active agent Substances 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
238000000034 method Methods 0.000 abstract description 44
241000196324 Embryophyta Species 0.000 description 46
239000000126 substance Substances 0.000 description 32
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
239000000203 mixture Substances 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
239000013543 active substance Substances 0.000 description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
229940088623 biologically active substance Drugs 0.000 description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 12
239000003085 diluting agent Substances 0.000 description 11
230000003993 interaction Effects 0.000 description 11
239000002904 solvent Substances 0.000 description 11
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
238000002844 melting Methods 0.000 description 10
230000008018 melting Effects 0.000 description 10
229910052708 sodium Inorganic materials 0.000 description 10
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000011734 sodium Substances 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
150000003254 radicals Chemical class 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
235000011152 sodium sulphate Nutrition 0.000 description 8
239000000243 solution Substances 0.000 description 8
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
239000003995 emulsifying agent Substances 0.000 description 7
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000002689 soil Substances 0.000 description 6
238000003828 vacuum filtration Methods 0.000 description 6
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
230000006378 damage Effects 0.000 description 5
239000008187 granular material Substances 0.000 description 5
239000007858 starting material Substances 0.000 description 5
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
235000019441 ethanol Nutrition 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
238000012360 testing method Methods 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
IYFGQORJZNOKNF-UHFFFAOYSA-M 2-chloro-5-methyl-1-[3-(trifluoromethyl)phenyl]pyridin-1-ium;chloride Chemical compound [Cl-].CC1=CC=C(Cl)[N+](C=2C=C(C=CC=2)C(F)(F)F)=C1 IYFGQORJZNOKNF-UHFFFAOYSA-M 0.000 description 3
PLMQFHAKZKHJAT-UHFFFAOYSA-N 5-methyl-1-[3-(trifluoromethyl)phenyl]pyridin-2-one Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC(C(F)(F)F)=C1 PLMQFHAKZKHJAT-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
239000000370 acceptor Substances 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
235000013312 flour Nutrition 0.000 description 3
IANUJLZYFUDJIH-UHFFFAOYSA-N flufenacet Chemical compound C=1C=C(F)C=CC=1N(C(C)C)C(=O)COC1=NN=C(C(F)(F)F)S1 IANUJLZYFUDJIH-UHFFFAOYSA-N 0.000 description 3
239000007789 gas Substances 0.000 description 3
150000003840 hydrochlorides Chemical class 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
235000011181 potassium carbonates Nutrition 0.000 description 3
239000000843 powder Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
239000007787 solid Substances 0.000 description 3
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