DD250452A5 - Unkrautbekaempfungsmittel - Google Patents

Unkrautbekaempfungsmittel Download PDF

Info

Publication number: DD250452A5
Authority: DD; German Democratic Republic
Prior art keywords: chloro; fluoro; dioxo; benzoic acid; methyl
Prior art date: 1985-03-20

Application number

DD28799386A

Other languages

German (de)

English (en)

Inventor

Jean Wenger

Paul Winternitz

Original Assignee

F. Hoffmann-La Roche Und Co. Ag,Ch

Priority date (The priority date 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 date listed.)

1985-03-20

Filing date

1986-03-18

Publication date

1987-10-14

1986-03-18 Application filed by F. Hoffmann-La Roche Und Co. Ag,Ch filed Critical F. Hoffmann-La Roche Und Co. Ag,Ch

1987-10-14 Publication of DD250452A5 publication Critical patent/DD250452A5/de

Links

241000196324 Embryophyta Species 0.000 claims abstract description 40
238000002360 preparation method Methods 0.000 claims abstract description 25
-1 pyrimidin-3-yl Chemical group 0.000 claims description 113
150000001875 compounds Chemical class 0.000 claims description 78
239000000203 mixture Substances 0.000 claims description 69
238000000034 method Methods 0.000 claims description 42
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 30
239000001257 hydrogen Substances 0.000 claims description 29
229910052739 hydrogen Inorganic materials 0.000 claims description 29
239000003795 chemical substances by application Substances 0.000 claims description 28
239000002253 acid Substances 0.000 claims description 27
239000005711 Benzoic acid Substances 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 19
150000002431 hydrogen Chemical class 0.000 claims description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
235000010233 benzoic acid Nutrition 0.000 claims description 14
239000000460 chlorine Substances 0.000 claims description 14
229910052801 chlorine Inorganic materials 0.000 claims description 14
238000009472 formulation Methods 0.000 claims description 13
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
125000003342 alkenyl group Chemical group 0.000 claims description 12
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
229910052794 bromium Inorganic materials 0.000 claims description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
150000002148 esters Chemical class 0.000 claims description 10
229910052731 fluorine Inorganic materials 0.000 claims description 10
239000011737 fluorine Substances 0.000 claims description 10
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 9
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 8
239000001301 oxygen Substances 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 7
125000005997 bromomethyl group Chemical group 0.000 claims description 7
125000001589 carboacyl group Chemical group 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
239000011593 sulfur Substances 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
125000001153 fluoro group Chemical group F* 0.000 claims description 5
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 4
125000000858 thiocyanato group Chemical group *SC#N 0.000 claims description 4
XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 3
LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 3
IICVIASQDQQHIN-UHFFFAOYSA-N ethyl 2-chloro-5-(1-methyl-2,4-dioxo-6,7-dihydro-5h-cyclopenta[d]pyrimidin-3-yl)benzoate Chemical compound C1=C(Cl)C(C(=O)OCC)=CC(N2C(N(C)C=3CCCC=3C2=O)=O)=C1 IICVIASQDQQHIN-UHFFFAOYSA-N 0.000 claims description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
239000002671 adjuvant Substances 0.000 claims 3
238000006213 oxygenation reaction Methods 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
TVOGCGQYTHYFMQ-UHFFFAOYSA-N propan-2-yl 2,4-dichloro-5-(1-methyl-2,4-dioxo-6,7-dihydro-5h-cyclopenta[d]pyrimidin-3-yl)benzoate Chemical class C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(N(C)C=3CCCC=3C2=O)=O)=C1Cl TVOGCGQYTHYFMQ-UHFFFAOYSA-N 0.000 claims 1
VEGKFBWVULWKCQ-UHFFFAOYSA-N propan-2-yl 2-chloro-4-fluoro-5-(5-fluoro-3,4-dimethyl-2,6-dioxopyrimidin-1-yl)benzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(N(C)C(C)=C(F)C2=O)=O)=C1F VEGKFBWVULWKCQ-UHFFFAOYSA-N 0.000 claims 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
150000003839 salts Chemical class 0.000 abstract description 23
239000007858 starting material Substances 0.000 abstract description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 111
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 91
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 78
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 56
239000000243 solution Substances 0.000 description 54
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 47
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
238000006243 chemical reaction Methods 0.000 description 37
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
229910052708 sodium Inorganic materials 0.000 description 36
239000011734 sodium Substances 0.000 description 36
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 35
239000011541 reaction mixture Substances 0.000 description 34
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
239000002904 solvent Substances 0.000 description 31
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 28
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 26
LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 25
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 21
239000012074 organic phase Substances 0.000 description 21
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 19
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical class O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 18
238000005160 1H NMR spectroscopy Methods 0.000 description 17
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
229960000583 acetic acid Drugs 0.000 description 16
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 15
229910052740 iodine Inorganic materials 0.000 description 15
238000003756 stirring Methods 0.000 description 15
125000001931 aliphatic group Chemical group 0.000 description 14
239000000047 product Substances 0.000 description 14
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 13
239000004480 active ingredient Substances 0.000 description 13
229910052783 alkali metal Inorganic materials 0.000 description 13
150000004292 cyclic ethers Chemical class 0.000 description 13
239000003960 organic solvent Substances 0.000 description 13
229910000104 sodium hydride Inorganic materials 0.000 description 13
239000012312 sodium hydride Substances 0.000 description 13
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
239000002585 base Substances 0.000 description 12
239000003085 diluting agent Substances 0.000 description 12
239000002270 dispersing agent Substances 0.000 description 12
239000003480 eluent Substances 0.000 description 12
229910002027 silica gel Inorganic materials 0.000 description 12
239000000741 silica gel Substances 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
238000010992 reflux Methods 0.000 description 11
159000000000 sodium salts Chemical class 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
238000004587 chromatography analysis Methods 0.000 description 10
229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
235000017557 sodium bicarbonate Nutrition 0.000 description 10
238000005481 NMR spectroscopy Methods 0.000 description 9
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 9
JHZPNBKZPAWCJD-UHFFFAOYSA-N ethyl 2-oxocyclopentane-1-carboxylate Chemical compound CCOC(=O)C1CCCC1=O JHZPNBKZPAWCJD-UHFFFAOYSA-N 0.000 description 9
230000002363 herbicidal effect Effects 0.000 description 9
UAHXBOAKPTWXNS-UHFFFAOYSA-N propan-2-yl 2-chloro-4-fluoro-5-isocyanatobenzoate Chemical compound CC(C)OC(=O)C1=CC(N=C=O)=C(F)C=C1Cl UAHXBOAKPTWXNS-UHFFFAOYSA-N 0.000 description 9
239000007787 solid Substances 0.000 description 9
239000004094 surface-active agent Substances 0.000 description 9
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 8
229910017604 nitric acid Inorganic materials 0.000 description 8
150000001340 alkali metals Chemical class 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 7
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 7
239000003054 catalyst Substances 0.000 description 7
150000004820 halides Chemical class 0.000 description 7
UODFVRFFBKXHHV-UHFFFAOYSA-N propan-2-yl 5-(carbamoylamino)-2-chloro-4-fluorobenzoate Chemical compound CC(C)OC(=O)C1=CC(NC(N)=O)=C(F)C=C1Cl UODFVRFFBKXHHV-UHFFFAOYSA-N 0.000 description 7
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
238000009835 boiling Methods 0.000 description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
239000003995 emulsifying agent Substances 0.000 description 6
MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
239000011630 iodine Substances 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
JDBGXEHEIRGOBU-UHFFFAOYSA-N 5-hydroxymethyluracil Chemical compound OCC1=CNC(=O)NC1=O JDBGXEHEIRGOBU-UHFFFAOYSA-N 0.000 description 5
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
125000004414 alkyl thio group Chemical group 0.000 description 5
150000003863 ammonium salts Chemical class 0.000 description 5
239000011230 binding agent Substances 0.000 description 5
125000001309 chloro group Chemical group Cl* 0.000 description 5
239000006185 dispersion Substances 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
229910052500 inorganic mineral Inorganic materials 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
239000002184 metal Substances 0.000 description 5
235000010755 mineral Nutrition 0.000 description 5
239000011707 mineral Substances 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
150000007530 organic bases Chemical class 0.000 description 5
239000000725 suspension Substances 0.000 description 5
RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 5
ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
230000010933 acylation Effects 0.000 description 4
238000005917 acylation reaction Methods 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
230000029936 alkylation Effects 0.000 description 4
238000005804 alkylation reaction Methods 0.000 description 4
239000000969 carrier Substances 0.000 description 4
239000013078 crystal Substances 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
239000004495 emulsifiable concentrate Substances 0.000 description 4
UZKLYQQFSMXNOK-UHFFFAOYSA-N ethyl 5-(carbamoylamino)-2-chlorobenzoate Chemical compound CCOC(=O)C1=CC(NC(N)=O)=CC=C1Cl UZKLYQQFSMXNOK-UHFFFAOYSA-N 0.000 description 4
150000007529 inorganic bases Chemical class 0.000 description 4
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 4
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
239000008096 xylene Substances 0.000 description 4
HEOSHABIIONPMW-UHFFFAOYSA-N 2-chloro-4-fluoro-5-(1-methyl-2,4-dioxo-6,7-dihydro-5h-cyclopenta[d]pyrimidin-3-yl)benzoic acid Chemical compound O=C1N(C)C=2CCCC=2C(=O)N1C1=CC(C(O)=O)=C(Cl)C=C1F HEOSHABIIONPMW-UHFFFAOYSA-N 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 3
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000013543 active substance Substances 0.000 description 3
229910000288 alkali metal carbonate Inorganic materials 0.000 description 3
150000008041 alkali metal carbonates Chemical class 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
150000001558 benzoic acid derivatives Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000001816 cooling Methods 0.000 description 3
JJEOYGOCVGCAES-UHFFFAOYSA-N ethyl 2-chloro-5-(2,4-dioxo-1,5,6,7-tetrahydrocyclopenta[d]pyrimidin-3-yl)benzoate Chemical compound C1=C(Cl)C(C(=O)OCC)=CC(N2C(C=3CCCC=3NC2=O)=O)=C1 JJEOYGOCVGCAES-UHFFFAOYSA-N 0.000 description 3
125000003709 fluoroalkyl group Chemical group 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
238000011065 in-situ storage Methods 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
239000011591 potassium Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
YRHRBZBQGSBWMJ-UHFFFAOYSA-N propan-2-yl 2-chloro-4-fluoro-5-(6-methyl-2,4-dioxo-1h-pyrimidin-3-yl)benzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(NC(C)=CC2=O)=O)=C1F YRHRBZBQGSBWMJ-UHFFFAOYSA-N 0.000 description 3
GWAUKYSXTLUDLP-UHFFFAOYSA-N propan-2-yl 2-chloro-5-(3,4-dimethyl-2,6-dioxopyrimidin-1-yl)-4-fluorobenzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(N(C)C(C)=CC2=O)=O)=C1F GWAUKYSXTLUDLP-UHFFFAOYSA-N 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
238000005809 transesterification reaction Methods 0.000 description 3
239000000080 wetting agent Substances 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
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239000000642 acaricide Substances 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
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150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
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150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
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239000002168 alkylating agent Substances 0.000 description 1
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BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
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150000008064 anhydrides Chemical class 0.000 description 1
LNTHITQWFMADLM-UHFFFAOYSA-N anhydrous gallic acid Natural products OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 1
150000001449 anionic compounds Chemical class 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
159000000009 barium salts Chemical class 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
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SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
229960002130 benzoin Drugs 0.000 description 1
239000012965 benzophenone Substances 0.000 description 1
150000008366 benzophenones Chemical class 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
JIJAYWGYIDJVJI-UHFFFAOYSA-N butyl naphthalene-1-sulfonate Chemical class C1=CC=C2C(S(=O)(=O)OCCCC)=CC=CC2=C1 JIJAYWGYIDJVJI-UHFFFAOYSA-N 0.000 description 1
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 1
239000004202 carbamide Substances 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
229940071162 caseinate Drugs 0.000 description 1
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229920002678 cellulose Polymers 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
150000008422 chlorobenzenes Chemical class 0.000 description 1
150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
238000007865 diluting Methods 0.000 description 1
IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical class Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
KWABLUYIOFEZOY-UHFFFAOYSA-N dioctyl butanedioate Chemical compound CCCCCCCCOC(=O)CCC(=O)OCCCCCCCC KWABLUYIOFEZOY-UHFFFAOYSA-N 0.000 description 1
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
229940043264 dodecyl sulfate Drugs 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
CTIIDKOCCAZEDV-ONEGZZNKSA-N ethyl (e)-3-amino-2,4,4,4-tetrafluorobut-2-enoate Chemical compound CCOC(=O)C(\F)=C(/N)C(F)(F)F CTIIDKOCCAZEDV-ONEGZZNKSA-N 0.000 description 1
ITQFPVUDTFABDH-AATRIKPKSA-N ethyl (e)-3-ethoxyprop-2-enoate Chemical compound CCO\C=C\C(=O)OCC ITQFPVUDTFABDH-AATRIKPKSA-N 0.000 description 1
NYXCYAPPHIFZPQ-SREVYHEPSA-N ethyl (z)-3-amino-2-ethylbut-2-enoate Chemical compound CCOC(=O)C(\CC)=C(\C)N NYXCYAPPHIFZPQ-SREVYHEPSA-N 0.000 description 1
AHHWYDQKFSHGNI-WAYWQWQTSA-N ethyl (z)-3-amino-2-methylbut-2-enoate Chemical compound CCOC(=O)C(\C)=C(\C)N AHHWYDQKFSHGNI-WAYWQWQTSA-N 0.000 description 1
YPMPTULBFPFSEQ-PLNGDYQASA-N ethyl (z)-3-aminobut-2-enoate Chemical compound CCOC(=O)\C=C(\C)N YPMPTULBFPFSEQ-PLNGDYQASA-N 0.000 description 1
DRSWQTAUJVBNNL-UHFFFAOYSA-N ethyl 2-chloro-4-fluoro-5-(1-methyl-2,4-dioxo-6,7-dihydro-5h-cyclopenta[d]pyrimidin-3-yl)benzoate Chemical compound C1=C(Cl)C(C(=O)OCC)=CC(N2C(N(C)C=3CCCC=3C2=O)=O)=C1F DRSWQTAUJVBNNL-UHFFFAOYSA-N 0.000 description 1
LJBUSCBYXBEZOV-UHFFFAOYSA-N ethyl 2-chloro-5-(1-methyl-2,4-dioxo-5,7-dihydrothieno[3,4-d]pyrimidin-3-yl)benzoate Chemical compound C1=C(Cl)C(C(=O)OCC)=CC(N2C(N(C)C=3CSCC=3C2=O)=O)=C1 LJBUSCBYXBEZOV-UHFFFAOYSA-N 0.000 description 1
FRTVMHRMNFJVRR-UHFFFAOYSA-N ethyl 2-chloro-5-(2,4-dioxo-5,6,7,8-tetrahydro-1h-quinazolin-3-yl)benzoate Chemical compound C1=C(Cl)C(C(=O)OCC)=CC(N2C(C=3CCCCC=3NC2=O)=O)=C1 FRTVMHRMNFJVRR-UHFFFAOYSA-N 0.000 description 1
ZPNCGIOHTUUOEA-UHFFFAOYSA-N ethyl 2-chloro-5-[(2-ethoxycarbonylcyclohexen-1-yl)carbamoylamino]benzoate Chemical compound C1CCCC(C(=O)OCC)=C1NC(=O)NC1=CC=C(Cl)C(C(=O)OCC)=C1 ZPNCGIOHTUUOEA-UHFFFAOYSA-N 0.000 description 1
UCTCAINNLQKIAB-UHFFFAOYSA-N ethyl 2-chloro-5-[(3-ethoxy-3-oxoprop-1-enyl)carbamoylamino]benzoate Chemical compound CCOC(=O)C=CNC(=O)NC1=CC=C(Cl)C(C(=O)OCC)=C1 UCTCAINNLQKIAB-UHFFFAOYSA-N 0.000 description 1
QGCRXOCDMMWNEJ-UHFFFAOYSA-N ethyl 2-chloro-5-[(4-ethoxy-3-methyl-4-oxobut-2-en-2-yl)carbamoylamino]benzoate Chemical compound CCOC(=O)C(C)=C(C)NC(=O)NC1=CC=C(Cl)C(C(=O)OCC)=C1 QGCRXOCDMMWNEJ-UHFFFAOYSA-N 0.000 description 1
IYKLWZYWCIHUDR-UHFFFAOYSA-N ethyl 2-chloro-5-[(4-ethoxy-4-oxobut-2-en-2-yl)carbamoylamino]benzoate Chemical compound CCOC(=O)C=C(C)NC(=O)NC1=CC=C(Cl)C(C(=O)OCC)=C1 IYKLWZYWCIHUDR-UHFFFAOYSA-N 0.000 description 1
HRKQIAHAOPDWPE-UHFFFAOYSA-N ethyl 2-chloro-5-isocyanatobenzoate Chemical compound CCOC(=O)C1=CC(N=C=O)=CC=C1Cl HRKQIAHAOPDWPE-UHFFFAOYSA-N 0.000 description 1
QQBXZMMFTNAWHY-UHFFFAOYSA-N ethyl 3-amino-2-methylpent-2-enoate Chemical compound CCOC(=O)C(C)=C(N)CC QQBXZMMFTNAWHY-UHFFFAOYSA-N 0.000 description 1
KQWWVLVLVYYYDT-UHFFFAOYSA-N ethyl 3-oxohexanoate Chemical compound CCCC(=O)CC(=O)OCC KQWWVLVLVYYYDT-UHFFFAOYSA-N 0.000 description 1
IBPRYCJJTSWUEI-UHFFFAOYSA-N ethyl 5-(carbamoylamino)-2-nitrobenzoate Chemical compound CCOC(=O)C1=CC(NC(N)=O)=CC=C1[N+]([O-])=O IBPRYCJJTSWUEI-UHFFFAOYSA-N 0.000 description 1
WMKCNMYOUKMTJN-UHFFFAOYSA-N ethyl 5-[(2-ethoxycarbonylcyclopenten-1-yl)carbamoylamino]-2-nitrobenzoate Chemical compound C1CCC(C(=O)OCC)=C1NC(=O)NC1=CC=C([N+]([O-])=O)C(C(=O)OCC)=C1 WMKCNMYOUKMTJN-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
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239000000417 fungicide Substances 0.000 description 1
229940074391 gallic acid Drugs 0.000 description 1
235000004515 gallic acid Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
235000019382 gum benzoic Nutrition 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002391 heterocyclic compounds 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
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
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239000004615 ingredient Substances 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
150000008040 ionic compounds Chemical class 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
VRNINGUKUJWZTH-UHFFFAOYSA-L lead(2+);dithiocyanate Chemical compound [Pb+2].[S-]C#N.[S-]C#N VRNINGUKUJWZTH-UHFFFAOYSA-L 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
239000006028 limestone Substances 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
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229910052749 magnesium Inorganic materials 0.000 description 1
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239000000155 melt Substances 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
GQCSFXKMZSVVLS-UHFFFAOYSA-N methyl 2-chloro-5-(1-methyl-2,4-dioxo-6,7-dihydro-5h-cyclopenta[d]pyrimidin-3-yl)benzoate Chemical compound C1=C(Cl)C(C(=O)OC)=CC(N2C(N(C)C=3CCCC=3C2=O)=O)=C1 GQCSFXKMZSVVLS-UHFFFAOYSA-N 0.000 description 1
XEQYPQHAQCSASZ-UHFFFAOYSA-N methyl 3-methoxy-2-methylprop-2-enoate Chemical compound COC=C(C)C(=O)OC XEQYPQHAQCSASZ-UHFFFAOYSA-N 0.000 description 1
BNRZIYYGGBNQCD-UHFFFAOYSA-N methyl 4-[(4-chloro-3-ethoxycarbonylphenyl)carbamoylamino]-2,5-dihydrothiophene-3-carboxylate Chemical compound C1=C(Cl)C(C(=O)OCC)=CC(NC(=O)NC=2CSCC=2C(=O)OC)=C1 BNRZIYYGGBNQCD-UHFFFAOYSA-N 0.000 description 1
LEAKUJFYXNILRB-UHFFFAOYSA-N methyl 4-oxothiolane-3-carboxylate Chemical compound COC(=O)C1CSCC1=O LEAKUJFYXNILRB-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
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XBCXJKGHPABGSD-UHFFFAOYSA-N methyluracil Natural products CN1C=CC(=O)NC1=O XBCXJKGHPABGSD-UHFFFAOYSA-N 0.000 description 1
238000003801 milling Methods 0.000 description 1
238000002156 mixing Methods 0.000 description 1
VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
230000000802 nitrating effect Effects 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
150000002829 nitrogen Chemical group 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
238000012856 packing Methods 0.000 description 1
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150000002989 phenols Chemical class 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
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229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
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235000019422 polyvinyl alcohol Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
DZFBWUNVCCIDAI-UHFFFAOYSA-N propan-2-yl 2,4-dibromo-5-(1-methyl-2,4-dioxo-6,7-dihydro-5h-cyclopenta[d]pyrimidin-3-yl)benzoate Chemical compound C1=C(Br)C(C(=O)OC(C)C)=CC(N2C(N(C)C=3CCCC=3C2=O)=O)=C1Br DZFBWUNVCCIDAI-UHFFFAOYSA-N 0.000 description 1
LAZUGTWSBFMDGI-UHFFFAOYSA-N propan-2-yl 2,4-dibromo-5-(carbamoylamino)benzoate Chemical compound CC(C)OC(=O)C1=CC(NC(N)=O)=C(Br)C=C1Br LAZUGTWSBFMDGI-UHFFFAOYSA-N 0.000 description 1
YGGGSOIYSVYPGV-UHFFFAOYSA-N propan-2-yl 2-bromo-4-chloro-5-(1-methyl-2,4-dioxo-6,7-dihydro-5h-cyclopenta[d]pyrimidin-3-yl)benzoate Chemical compound C1=C(Br)C(C(=O)OC(C)C)=CC(N2C(N(C)C=3CCCC=3C2=O)=O)=C1Cl YGGGSOIYSVYPGV-UHFFFAOYSA-N 0.000 description 1
FMDDTCWIHMNDAQ-UHFFFAOYSA-N propan-2-yl 2-bromo-4-chloro-5-(2,4-dioxo-1,5,6,7-tetrahydrocyclopenta[d]pyrimidin-3-yl)benzoate Chemical compound C1=C(Br)C(C(=O)OC(C)C)=CC(N2C(C=3CCCC=3NC2=O)=O)=C1Cl FMDDTCWIHMNDAQ-UHFFFAOYSA-N 0.000 description 1
DUCCAOMNLFKZGR-UHFFFAOYSA-N propan-2-yl 2-bromo-4-chloro-5-[(2-ethoxycarbonylcyclopenten-1-yl)carbamoylamino]benzoate Chemical compound C1CCC(C(=O)OCC)=C1NC(=O)NC1=CC(C(=O)OC(C)C)=C(Br)C=C1Cl DUCCAOMNLFKZGR-UHFFFAOYSA-N 0.000 description 1
CNERKJSQTUHHGE-UHFFFAOYSA-N propan-2-yl 2-bromo-4-fluoro-5-(1-methyl-2,4-dioxo-6,7-dihydro-5h-cyclopenta[d]pyrimidin-3-yl)benzoate Chemical compound C1=C(Br)C(C(=O)OC(C)C)=CC(N2C(N(C)C=3CCCC=3C2=O)=O)=C1F CNERKJSQTUHHGE-UHFFFAOYSA-N 0.000 description 1
QNTFQLIFUREQQX-UHFFFAOYSA-N propan-2-yl 2-bromo-5-(carbamoylamino)-4-chlorobenzoate Chemical compound CC(C)OC(=O)C1=CC(NC(N)=O)=C(Cl)C=C1Br QNTFQLIFUREQQX-UHFFFAOYSA-N 0.000 description 1
KFKFYNTUGKRCNZ-UHFFFAOYSA-N propan-2-yl 2-bromo-5-(carbamoylamino)-4-fluorobenzoate Chemical compound CC(C)OC(=O)C1=CC(NC(N)=O)=C(F)C=C1Br KFKFYNTUGKRCNZ-UHFFFAOYSA-N 0.000 description 1
YNRFCEOXDYMTRT-UHFFFAOYSA-N propan-2-yl 2-chloro-4-fluoro-5-(1-methyl-2,4-dioxo-5,6,7,8-tetrahydroquinazolin-3-yl)benzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(N(C)C=3CCCCC=3C2=O)=O)=C1F YNRFCEOXDYMTRT-UHFFFAOYSA-N 0.000 description 1
QNXCPNHSPBFWBQ-UHFFFAOYSA-N propan-2-yl 2-chloro-4-fluoro-5-(1-methyl-2,4-dioxo-5,6-dihydrofuro[2,3-d]pyrimidin-3-yl)benzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(N(C)C=3OCCC=3C2=O)=O)=C1F QNXCPNHSPBFWBQ-UHFFFAOYSA-N 0.000 description 1
UONKVUFHTNSPDQ-UHFFFAOYSA-N propan-2-yl 2-chloro-4-fluoro-5-(1-methyl-2,4-dioxo-6,7-dihydrothieno[3,2-d]pyrimidin-3-yl)benzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(N(C)C=3CCSC=3C2=O)=O)=C1F UONKVUFHTNSPDQ-UHFFFAOYSA-N 0.000 description 1
GMSMERODUZSDTM-UHFFFAOYSA-N propan-2-yl 2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-propylpyrimidin-1-yl)benzoate Chemical compound O=C1N(C)C(CCC)=CC(=O)N1C1=CC(C(=O)OC(C)C)=C(Cl)C=C1F GMSMERODUZSDTM-UHFFFAOYSA-N 0.000 description 1
GRGDEJSZGYGRQT-UHFFFAOYSA-N propan-2-yl 2-chloro-4-fluoro-5-(5-iodo-6-methyl-2,4-dioxo-1h-pyrimidin-3-yl)benzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(C(I)=C(C)NC2=O)=O)=C1F GRGDEJSZGYGRQT-UHFFFAOYSA-N 0.000 description 1
NZCFZHIPXYSRAW-UHFFFAOYSA-N propan-2-yl 2-chloro-4-fluoro-5-(6-methyl-2,4-dioxo-5-thiocyanato-1h-pyrimidin-3-yl)benzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(C(SC#N)=C(C)NC2=O)=O)=C1F NZCFZHIPXYSRAW-UHFFFAOYSA-N 0.000 description 1
SSXCPXOJTFKEJO-UHFFFAOYSA-N propan-2-yl 2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F SSXCPXOJTFKEJO-UHFFFAOYSA-N 0.000 description 1
IRVJGUROUAFVLD-UHFFFAOYSA-N propan-2-yl 2-chloro-4-fluoro-5-[5-(hydroxymethyl)-3,4-dimethyl-2,6-dioxopyrimidin-1-yl]benzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(N(C)C(C)=C(CO)C2=O)=O)=C1F IRVJGUROUAFVLD-UHFFFAOYSA-N 0.000 description 1
ISYDZDYKSRWTGH-UHFFFAOYSA-N propan-2-yl 2-chloro-4-fluoro-5-[5-fluoro-6-(fluoromethyl)-2,4-dioxo-1h-pyrimidin-3-yl]benzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(C(F)=C(CF)NC2=O)=O)=C1F ISYDZDYKSRWTGH-UHFFFAOYSA-N 0.000 description 1
SPYXYNBNGSBBDB-UHFFFAOYSA-N propan-2-yl 2-chloro-5-(1-methyl-2,4-dioxo-5,6,7,8-tetrahydroquinazolin-3-yl)benzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(N(C)C=3CCCCC=3C2=O)=O)=C1 SPYXYNBNGSBBDB-UHFFFAOYSA-N 0.000 description 1
QYXTVLPPDJYXQL-UHFFFAOYSA-N propan-2-yl 2-chloro-5-(2,4-dioxo-1,5,6,7-tetrahydrocyclopenta[d]pyrimidin-3-yl)-4-fluorobenzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(C=3CCCC=3NC2=O)=O)=C1F QYXTVLPPDJYXQL-UHFFFAOYSA-N 0.000 description 1
KQLHKNUXJMWDDD-UHFFFAOYSA-N propan-2-yl 2-chloro-5-(2,4-dioxo-5,6,7,8-tetrahydro-1h-quinazolin-3-yl)-4-fluorobenzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(C=3CCCCC=3NC2=O)=O)=C1F KQLHKNUXJMWDDD-UHFFFAOYSA-N 0.000 description 1
QNNAEJPEXIAWBN-UHFFFAOYSA-N propan-2-yl 2-chloro-5-(2,4-dioxo-5,6,7,8-tetrahydro-1h-quinazolin-3-yl)benzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(C=3CCCCC=3NC2=O)=O)=C1 QNNAEJPEXIAWBN-UHFFFAOYSA-N 0.000 description 1
XVEGYBCXDHQSAI-UHFFFAOYSA-N propan-2-yl 2-chloro-5-(2,4-dioxo-5,7-dihydro-1h-thieno[3,4-d]pyrimidin-3-yl)-4-fluorobenzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(C=3CSCC=3NC2=O)=O)=C1F XVEGYBCXDHQSAI-UHFFFAOYSA-N 0.000 description 1
MSLGLASZPLEDMX-UHFFFAOYSA-N propan-2-yl 2-chloro-5-(2,4-dioxo-6,7-dihydro-1h-thieno[3,2-d]pyrimidin-3-yl)-4-fluorobenzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(C=3SCCC=3NC2=O)=O)=C1F MSLGLASZPLEDMX-UHFFFAOYSA-N 0.000 description 1
GUYQYPQNFXIXCM-UHFFFAOYSA-N propan-2-yl 2-chloro-5-(4-ethyl-3,5-dimethyl-2,6-dioxopyrimidin-1-yl)-4-fluorobenzoate Chemical compound O=C1N(C)C(CC)=C(C)C(=O)N1C1=CC(C(=O)OC(C)C)=C(Cl)C=C1F GUYQYPQNFXIXCM-UHFFFAOYSA-N 0.000 description 1
GJJXNGQDZVOXPH-UHFFFAOYSA-N propan-2-yl 2-chloro-5-(4-oxo-2-sulfanylidene-1,5,6,7-tetrahydrocyclopenta[d]pyrimidin-3-yl)benzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(C=3CCCC=3NC2=S)=O)=C1 GJJXNGQDZVOXPH-UHFFFAOYSA-N 0.000 description 1
IEXUZNKVYANJSB-UHFFFAOYSA-N propan-2-yl 2-chloro-5-(5-cyano-6-methyl-2,4-dioxo-1h-pyrimidin-3-yl)-4-fluorobenzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(C(C#N)=C(C)NC2=O)=O)=C1F IEXUZNKVYANJSB-UHFFFAOYSA-N 0.000 description 1
VQKYNRDKAQEMKO-UHFFFAOYSA-N propan-2-yl 2-chloro-5-(5-ethyl-6-methyl-2,4-dioxo-1h-pyrimidin-3-yl)-4-fluorobenzoate Chemical compound O=C1C(CC)=C(C)NC(=O)N1C1=CC(C(=O)OC(C)C)=C(Cl)C=C1F VQKYNRDKAQEMKO-UHFFFAOYSA-N 0.000 description 1
DWSONJKLANDHBY-UHFFFAOYSA-N propan-2-yl 2-chloro-5-(6-ethyl-2,4-dioxo-1h-pyrimidin-3-yl)-4-fluorobenzoate Chemical compound O=C1NC(CC)=CC(=O)N1C1=CC(C(=O)OC(C)C)=C(Cl)C=C1F DWSONJKLANDHBY-UHFFFAOYSA-N 0.000 description 1
VZLJCDVRGAQGDJ-UHFFFAOYSA-N propan-2-yl 2-chloro-5-[(1-ethoxy-1-oxohex-2-en-3-yl)carbamoylamino]-4-fluorobenzoate Chemical compound CCOC(=O)C=C(CCC)NC(=O)NC1=CC(C(=O)OC(C)C)=C(Cl)C=C1F VZLJCDVRGAQGDJ-UHFFFAOYSA-N 0.000 description 1
VHJGMSYZBGEDRW-UHFFFAOYSA-N propan-2-yl 2-chloro-5-[(1-ethoxy-2-methyl-1-oxopent-2-en-3-yl)carbamoylamino]-4-fluorobenzoate Chemical compound CCOC(=O)C(C)=C(CC)NC(=O)NC1=CC(C(=O)OC(C)C)=C(Cl)C=C1F VHJGMSYZBGEDRW-UHFFFAOYSA-N 0.000 description 1
QYXAIGVMNXISPP-UHFFFAOYSA-N propan-2-yl 2-chloro-5-[(2-ethoxycarbonylcyclopenten-1-yl)carbamothioylamino]benzoate Chemical compound C1CCC(C(=O)OCC)=C1NC(=S)NC1=CC=C(Cl)C(C(=O)OC(C)C)=C1 QYXAIGVMNXISPP-UHFFFAOYSA-N 0.000 description 1
RJZWCGGBJRUXIO-UHFFFAOYSA-N propan-2-yl 2-chloro-5-[(2-ethoxycarbonylcyclopenten-1-yl)carbamoylamino]-4-fluorobenzoate Chemical compound C1CCC(C(=O)OCC)=C1NC(=O)NC1=CC(C(=O)OC(C)C)=C(Cl)C=C1F RJZWCGGBJRUXIO-UHFFFAOYSA-N 0.000 description 1
BAJVINVCTUCRKZ-UHFFFAOYSA-N propan-2-yl 2-chloro-5-[(4-ethoxy-1,1,1-trifluoro-4-oxobut-2-en-2-yl)carbamothioylamino]benzoate Chemical compound CCOC(=O)C=C(C(F)(F)F)NC(=S)NC1=CC=C(Cl)C(C(=O)OC(C)C)=C1 BAJVINVCTUCRKZ-UHFFFAOYSA-N 0.000 description 1
MYGOPQOWISVNAR-UHFFFAOYSA-N propan-2-yl 2-chloro-5-[(4-ethoxy-1,3-difluoro-4-oxobut-2-en-2-yl)carbamoylamino]-4-fluorobenzoate Chemical compound CCOC(=O)C(F)=C(CF)NC(=O)NC1=CC(C(=O)OC(C)C)=C(Cl)C=C1F MYGOPQOWISVNAR-UHFFFAOYSA-N 0.000 description 1
STJGONUXDFSWLX-UHFFFAOYSA-N propan-2-yl 2-chloro-5-[(4-ethoxy-3-fluoro-4-oxobut-2-en-2-yl)carbamoylamino]-4-fluorobenzoate Chemical compound CCOC(=O)C(F)=C(C)NC(=O)NC1=CC(C(=O)OC(C)C)=C(Cl)C=C1F STJGONUXDFSWLX-UHFFFAOYSA-N 0.000 description 1
QSVIBQMZHNVVSH-UHFFFAOYSA-N propan-2-yl 2-chloro-5-[(4-ethoxy-4-oxobut-2-en-2-yl)carbamothioylamino]benzoate Chemical compound CCOC(=O)C=C(C)NC(=S)NC1=CC=C(Cl)C(C(=O)OC(C)C)=C1 QSVIBQMZHNVVSH-UHFFFAOYSA-N 0.000 description 1
COSBNVAHJWHDBT-UHFFFAOYSA-N propan-2-yl 2-chloro-5-[2,4-dioxo-6-(trifluoromethyl)-1h-pyrimidin-3-yl]-4-fluorobenzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(NC(=CC2=O)C(F)(F)F)=O)=C1F COSBNVAHJWHDBT-UHFFFAOYSA-N 0.000 description 1
MFDGCTJSBREUAC-UHFFFAOYSA-N propan-2-yl 2-chloro-5-[5-(chloromethyl)-3,4-dimethyl-2,6-dioxopyrimidin-1-yl]-4-fluorobenzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(N(C)C(C)=C(CCl)C2=O)=O)=C1F MFDGCTJSBREUAC-UHFFFAOYSA-N 0.000 description 1
ZPHYOAGWQGGEQU-UHFFFAOYSA-N propan-2-yl 4-bromo-5-(carbamoylamino)-2-fluorobenzoate Chemical compound CC(C)OC(=O)C1=CC(NC(N)=O)=C(Br)C=C1F ZPHYOAGWQGGEQU-UHFFFAOYSA-N 0.000 description 1
MGKNSMUBUXSOSI-UHFFFAOYSA-N propan-2-yl 5-(5-bromo-6-methyl-2,4-dioxo-1h-pyrimidin-3-yl)-2-chloro-4-fluorobenzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(C(Br)=C(C)NC2=O)=O)=C1F MGKNSMUBUXSOSI-UHFFFAOYSA-N 0.000 description 1
SWCVKUUFDFMMKS-UHFFFAOYSA-N propan-2-yl 5-(carbamoylamino)-2,4-dichlorobenzoate Chemical compound CC(C)OC(=O)C1=CC(NC(N)=O)=C(Cl)C=C1Cl SWCVKUUFDFMMKS-UHFFFAOYSA-N 0.000 description 1
GJSLFZSHNRYBBJ-UHFFFAOYSA-N propan-2-yl 5-[(2-ethoxycarbonylcyclopenten-1-yl)carbamoylamino]-2,4-difluorobenzoate Chemical compound C1CCC(C(=O)OCC)=C1NC(=O)NC1=CC(C(=O)OC(C)C)=C(F)C=C1F GJSLFZSHNRYBBJ-UHFFFAOYSA-N 0.000 description 1
GBANXCUVRXCIFS-UHFFFAOYSA-N propan-2-yl 5-[5-(bromomethyl)-3-methyl-2,6-dioxopyrimidin-1-yl]-2-chloro-4-fluorobenzoate Chemical compound C1=C(Cl)C(C(=O)OC(C)C)=CC(N2C(N(C)C=C(CBr)C2=O)=O)=C1F GBANXCUVRXCIFS-UHFFFAOYSA-N 0.000 description 1
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000000344 soap Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 1
229920005552 sodium lignosulfonate Polymers 0.000 description 1
RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
VQXJDPNCRCDAPG-UHFFFAOYSA-M sodium;2-chloro-5-(1-methyl-2,4-dioxo-5,6,7,8-tetrahydroquinazolin-3-yl)benzoate Chemical compound [Na+].O=C1N(C)C=2CCCCC=2C(=O)N1C1=CC=C(Cl)C(C([O-])=O)=C1 VQXJDPNCRCDAPG-UHFFFAOYSA-M 0.000 description 1
GGHPAKFFUZUEKL-UHFFFAOYSA-M sodium;hexadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O GGHPAKFFUZUEKL-UHFFFAOYSA-M 0.000 description 1
NWZBFJYXRGSRGD-UHFFFAOYSA-M sodium;octadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOS([O-])(=O)=O NWZBFJYXRGSRGD-UHFFFAOYSA-M 0.000 description 1
WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000003860 storage Methods 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
238000003419 tautomerization reaction Methods 0.000 description 1
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 1
ZRWLIJOSVOKNIS-UHFFFAOYSA-N tert-butyl 2-chloro-5-(1-methyl-2,4-dioxo-6,7-dihydro-5h-cyclopenta[d]pyrimidin-3-yl)benzoate Chemical compound O=C1N(C)C=2CCCC=2C(=O)N1C1=CC=C(Cl)C(C(=O)OC(C)(C)C)=C1 ZRWLIJOSVOKNIS-UHFFFAOYSA-N 0.000 description 1
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
229940035893 uracil Drugs 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

DD28799386A 1985-03-20 1986-03-18 Unkrautbekaempfungsmittel DD250452A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH124085		1985-03-20

Publications (1)

Publication Number	Publication Date
DD250452A5 true DD250452A5 (de)	1987-10-14

Family

ID=4205753

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD28799386A DD250452A5 (de)	1985-03-20	1986-03-18	Unkrautbekaempfungsmittel

Country Status (7)

Country	Link
JP (1)	JPS61221178A (lt)
BR (1)	BR8601232A (lt)
DD (1)	DD250452A5 (lt)
ES (3)	ES8708212A1 (lt)
GR (1)	GR860718B (lt)
LT (1)	LT3377B (lt)
ZA (1)	ZA861892B (lt)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU627906B2 (en)	1989-07-14	1992-09-03	Nissan Chemical Industries Ltd.	Uracil derivatives and herbicides containing the same as active ingredient
JP3089621B2 (ja) *	1990-12-17	2000-09-18	日産化学工業株式会社	ウラシル誘導体
AU2448292A (en) *	1992-08-21	1994-03-15	Nissan Chemical Industries Ltd.	Pyrimidine derivative and weedkiller

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3235363A (en)	1964-05-01	1966-02-15	Du Pont	Method for the control of undesirable vegetation
FR2251267A1 (en)	1973-11-15	1975-06-13	Fahlberg List Veb	Herbicidal compsns. - contg. 3-cyclo hexyl-5,6-trimethylene -uracil and 3-carbamoyloxy-acylanilines

1986
- 1986-03-13 ZA ZA861892A patent/ZA861892B/xx unknown
- 1986-03-18 DD DD28799386A patent/DD250452A5/de not_active IP Right Cessation
- 1986-03-18 GR GR860718A patent/GR860718B/el unknown
- 1986-03-19 JP JP61061933A patent/JPS61221178A/ja active Pending
- 1986-03-19 BR BR8601232A patent/BR8601232A/pt active Search and Examination
- 1986-12-01 ES ES557230A patent/ES8708212A1/es not_active Expired
- 1986-12-01 ES ES557233A patent/ES8800174A1/es not_active Expired
- 1986-12-01 ES ES557232A patent/ES8800173A1/es not_active Expired
1993
- 1993-04-13 LT LTIP485A patent/LT3377B/lt not_active IP Right Cessation

Also Published As

Publication number	Publication date
ZA861892B (en)	1987-08-26
BR8601232A (pt)	1986-12-02
LTIP485A (en)	1994-10-25
LT3377B (en)	1995-08-25
ES557233A0 (es)	1987-10-16
ES557230A0 (es)	1987-10-01
JPS61221178A (ja)	1986-10-01
GR860718B (en)	1986-07-21
ES8708212A1 (es)	1987-10-01
ES557232A0 (es)	1987-10-16
ES8800173A1 (es)	1987-10-16
ES8800174A1 (es)	1987-10-16

Legal Events

Date	Code	Title	Description
1993-04-01	NPI	Change in the person, name or address of the patentee (addendum to changes before extension act)
1996-04-25	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0195346B1 (de)	1992-06-24	3-Aryluracile und deren Verwendung zur Unkrautbekämpfung
EP0436680B1 (de)	1994-09-07	Heterocyclische verbindungen
EP0323487B1 (de)	1993-03-31	Heterocyclische verbindungen
EP0344232B1 (de)	1993-03-24	3-Aryluracile zur Unkrautbekämpfung
EP0260621A2 (de)	1988-03-23	3-Aryluracil-enoläther und deren Verwendung zur Unkrautbekämpfung
WO1989002891A1 (fr)	1989-04-06	Composes heterocycliques
EP0473551A1 (de)	1992-03-04	3-Aryluracil-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende Unkrautbekämpfungsmittel
EP0255047A1 (de)	1988-02-03	3-Aryluracile und deren Verwendung zur Unkrautbekämpfung
EP0262096A1 (de)	1988-03-30	Aminopyrazinone und Aminotriazinone
EP0542685A1 (de)	1993-05-19	Neue 3-Aryluracil-Derivate und deren Verwendung zur Unkrautbekämpfung
EP0338465A1 (de)	1989-10-25	1-Chlorpyrimidinyl-1H-1,2,4-triazol-3-sulfonsäureamide, Verfahren zu ihrer Herstellung und ihre Verwendung als Mittel mit herbizider Wirkung
CH617833A5 (lt)	1980-06-30
EP0388873B1 (de)	1994-05-11	Herbizide [[1,3,5-Triazin-2-yl) aminocarbonyl] aminsulfonyl] benzoesäureester, Verfahren zu ihrer Herstellung und ihre Verwendung
EP0114575B1 (de)	1988-02-03	2,4-Diamino-6-halogen-5-trifluormethylpyrimidine mit herbizider Wirkung
EP0139612B1 (de)	1988-02-10	Herbizide Mittel
DD250452A5 (de)	1987-10-14	Unkrautbekaempfungsmittel
EP0378092B1 (de)	1994-05-11	Herbizide Sulfonylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung
EP0109575A2 (de)	1984-05-30	Benzoesäurederivate, Verfahren und Mittel zu deren Herstellung
EP0409369A2 (de)	1991-01-23	Substituierte Pyrimidinyloxy-(thio)- und Triazinyloxy(thio)-acrylsäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Mittel mit herbizider, fungizider und pflanzenwachstumsregulierender Wirkung
DE4237920A1 (en)	1993-05-19	3-Aryl-uracil derivs. - are effective against weeds, act as dessicants, and facilitate harvesting of cotton, potato or rape
DE1567016A1 (de)	1970-04-16	Heterocyclische Verbindungen und ihre Anwendung
EP0084758B1 (de)	1986-02-12	Als Schädlingsbekämpfungsmittel wirksame Pyrimidin Derivate
EP0024260B1 (de)	1985-05-22	Neue Pyrimidin-Verbindungen, deren Herstellung, Zwischenprodukte dazu und herbizide Mittel, welche die Pyrimidinverbindungen als Wirkstoffe enthalten
EP0168352B1 (de)	1989-01-04	Verfahren zur Herstellung von Aminotriazinon-Derivaten
EP0476403B1 (de)	1996-02-28	Herbizide[[(1,3,5-Triazin-2-yl)aminocarbonyl]aminosulfonyl]benzoesäureester, Verfahren zu ihrer Herstellung und ihre Verwendung