CS198105B2 - Process for preparing 1-/mono-o-subst.benzoyl/-3-/subst.pyrazinyl/ureas - Google Patents

Process for preparing 1-/mono-o-subst.benzoyl/-3-/subst.pyrazinyl/ureas Download PDF

Info

Publication number: CS198105B2
Authority: CS; Czechoslovakia
Prior art keywords: formula; group; temperature; hydrogen; amino
Prior art date: 1977-07-27

Application number

CS788519A

Other languages

Czech (cs)

English (en)

Inventor

Riaz F Abdulla

Norman H Terando

Original Assignee

Lilly Co Eli

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.)

1977-07-27

Filing date

1978-06-21

Publication date

1980-05-30

1978-06-21 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1980-05-30 Publication of CS198105B2 publication Critical patent/CS198105B2/cs

Links

235000013877 carbamide Nutrition 0.000 title claims description 11
150000003672 ureas Chemical class 0.000 title claims description 9
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 title claims description 5
125000003373 pyrazinyl group Chemical group 0.000 title claims description 3
238000004519 manufacturing process Methods 0.000 title description 5
238000000034 method Methods 0.000 claims abstract description 36
238000006243 chemical reaction Methods 0.000 claims abstract description 18
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims abstract description 12
150000001412 amines Chemical class 0.000 claims abstract description 6
AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 claims abstract description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 12
239000007858 starting material Substances 0.000 claims description 11
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical group [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 10
-1 alkyl lithium Chemical compound 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 8
239000012442 inert solvent Substances 0.000 claims description 8
229910052744 lithium Inorganic materials 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
239000011737 fluorine Chemical group 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
206010012239 Delusion Diseases 0.000 claims 1
231100000868 delusion Toxicity 0.000 claims 1
150000008047 benzoylureas Chemical class 0.000 abstract description 6
239000002917 insecticide Substances 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
239000000243 solution Substances 0.000 description 25
239000000203 mixture Substances 0.000 description 20
239000000543 intermediate Substances 0.000 description 15
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
239000002904 solvent Substances 0.000 description 12
239000000047 product Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 8
150000001875 compounds Chemical class 0.000 description 8
150000002923 oximes Chemical class 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
230000000749 insecticidal effect Effects 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 6
239000007787 solid Substances 0.000 description 6
SJYCYRJOUJAQFB-UHFFFAOYSA-N 5-(4-bromophenyl)-6-methylpyrazin-2-amine Chemical compound CC1=NC(N)=CN=C1C1=CC=C(Br)C=C1 SJYCYRJOUJAQFB-UHFFFAOYSA-N 0.000 description 5
150000003216 pyrazines Chemical class 0.000 description 5
150000003252 quinoxalines Chemical class 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
241000238631 Hexapoda Species 0.000 description 4
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 4
241000607479 Yersinia pestis Species 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
YOWAEZWWQFSEJD-UHFFFAOYSA-N quinoxalin-2-amine Chemical compound C1=CC=CC2=NC(N)=CN=C21 YOWAEZWWQFSEJD-UHFFFAOYSA-N 0.000 description 4
JVSDZAGCHKCSGR-UHFFFAOYSA-N 2,5-dichloropyrazine Chemical compound ClC1=CN=C(Cl)C=N1 JVSDZAGCHKCSGR-UHFFFAOYSA-N 0.000 description 3
125000004098 2,6-dichlorobenzoyl group Chemical group O=C([*])C1=C(Cl)C([H])=C([H])C([H])=C1Cl 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000255925 Diptera Species 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HRYILSDLIGTCOP-UHFFFAOYSA-N N-benzoylurea Chemical compound NC(=O)NC(=O)C1=CC=CC=C1 HRYILSDLIGTCOP-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
238000003756 stirring Methods 0.000 description 3
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 2
RUIZBQQGWNBRFH-UHFFFAOYSA-N 1-oxidopyrazin-1-ium Chemical compound [O-][N+]1=CC=NC=C1 RUIZBQQGWNBRFH-UHFFFAOYSA-N 0.000 description 2
JHSPCUHPSIUQRB-UHFFFAOYSA-N 2,6-dichlorobenzamide Chemical compound NC(=O)C1=C(Cl)C=CC=C1Cl JHSPCUHPSIUQRB-UHFFFAOYSA-N 0.000 description 2
NHUFIOMPICRXFX-UHFFFAOYSA-N 5,6-dichloropyrazin-2-amine Chemical compound NC1=CN=C(Cl)C(Cl)=N1 NHUFIOMPICRXFX-UHFFFAOYSA-N 0.000 description 2
HWCKAMAVEWVBDO-UHFFFAOYSA-N 5-chloropyrazin-2-amine Chemical compound NC1=CN=C(Cl)C=N1 HWCKAMAVEWVBDO-UHFFFAOYSA-N 0.000 description 2
YQUJKPWSJHLFEU-UHFFFAOYSA-N 7-chloroquinoxalin-2-amine Chemical compound C1=CC(Cl)=CC2=NC(N)=CN=C21 YQUJKPWSJHLFEU-UHFFFAOYSA-N 0.000 description 2
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
150000004987 o-phenylenediamines Chemical class 0.000 description 2
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
238000012746 preparative thin layer chromatography Methods 0.000 description 2
125000004076 pyridyl group Chemical group 0.000 description 2
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
OVGLVOLWBBGQHS-RQOWECAXSA-N (1z)-1-hydroxyiminopropan-2-one Chemical compound CC(=O)\C=N/O OVGLVOLWBBGQHS-RQOWECAXSA-N 0.000 description 1
UYABSLBMZAYXNN-UHFFFAOYSA-N (2,4-dinitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C([N+]([O-])=O)=C1 UYABSLBMZAYXNN-UHFFFAOYSA-N 0.000 description 1
HOIDKJFWEVIJAT-UHFFFAOYSA-N 1-(4-bromophenyl)butan-1-one Chemical compound CCCC(=O)C1=CC=C(Br)C=C1 HOIDKJFWEVIJAT-UHFFFAOYSA-N 0.000 description 1
UOMOSYFPKGQIKI-UHFFFAOYSA-N 1-(4-bromophenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(Br)C=C1 UOMOSYFPKGQIKI-UHFFFAOYSA-N 0.000 description 1
BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 description 1
NDQMJZCPBOBKQB-UHFFFAOYSA-N 1-hydroxyiminobutan-2-one Chemical compound CCC(=O)C=NO NDQMJZCPBOBKQB-UHFFFAOYSA-N 0.000 description 1
SKYXZSVBBFFJQQ-UHFFFAOYSA-N 1-methyl-2h-pyrazine Chemical compound CN1CC=NC=C1 SKYXZSVBBFFJQQ-UHFFFAOYSA-N 0.000 description 1
KZKYRHRAVGWEAV-UHFFFAOYSA-N 2,3-dichlorobenzamide Chemical compound NC(=O)C1=CC=CC(Cl)=C1Cl KZKYRHRAVGWEAV-UHFFFAOYSA-N 0.000 description 1
CGNBQYFXGQHUQP-UHFFFAOYSA-N 2,3-dinitroaniline Chemical class NC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O CGNBQYFXGQHUQP-UHFFFAOYSA-N 0.000 description 1
GXHSCFXDSHCSNW-UHFFFAOYSA-N 2,6-dichloro-n-[(3,4-dichlorophenyl)carbamoyl]benzamide Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(=O)NC(=O)C1=C(Cl)C=CC=C1Cl GXHSCFXDSHCSNW-UHFFFAOYSA-N 0.000 description 1
VLODIDZJSPFCHG-UHFFFAOYSA-N 2,6-dichloro-n-[[3-(trifluoromethyl)phenyl]carbamoyl]benzamide Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC(=O)C=2C(=CC=CC=2Cl)Cl)=C1 VLODIDZJSPFCHG-UHFFFAOYSA-N 0.000 description 1
XRFJRBAHPTZBOI-UHFFFAOYSA-N 2,6-dichloro-n-[[4-(trifluoromethyl)phenyl]carbamoyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(=O)NC(=O)C1=C(Cl)C=CC=C1Cl XRFJRBAHPTZBOI-UHFFFAOYSA-N 0.000 description 1
XZWNQJDHECYSFD-UHFFFAOYSA-N 2,6-dichloro-n-[[6-(trifluoromethyl)pyrazin-2-yl]carbamoyl]benzamide Chemical compound FC(F)(F)C1=CN=CC(NC(=O)NC(=O)C=2C(=CC=CC=2Cl)Cl)=N1 XZWNQJDHECYSFD-UHFFFAOYSA-N 0.000 description 1
PKOJEWPOJBLORB-UHFFFAOYSA-N 2-(4-chlorophenyl)pyrazine Chemical compound C1=CC(Cl)=CC=C1C1=CN=CC=N1 PKOJEWPOJBLORB-UHFFFAOYSA-N 0.000 description 1
OEHNVKBOQOXOJN-UHFFFAOYSA-N 2-(4-nitrophenyl)phenol Chemical compound OC1=CC=CC=C1C1=CC=C([N+]([O-])=O)C=C1 OEHNVKBOQOXOJN-UHFFFAOYSA-N 0.000 description 1
OYCDPVNXUKEYBQ-UHFFFAOYSA-N 2-amino-2-hydroxybutanedinitrile;4-methylbenzenesulfonic acid Chemical compound N#CC(O)(N)CC#N.CC1=CC=C(S(O)(=O)=O)C=C1 OYCDPVNXUKEYBQ-UHFFFAOYSA-N 0.000 description 1
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
JTPXVCKCLBROOJ-UHFFFAOYSA-N 2-amino-6-chloropyrazine Chemical compound NC1=CN=CC(Cl)=N1 JTPXVCKCLBROOJ-UHFFFAOYSA-N 0.000 description 1
KZIVCQCZFMIHHH-UHFFFAOYSA-N 2-chloro-n-[[6-methyl-5-[3-(trifluoromethyl)phenyl]pyrazin-2-yl]carbamoyl]benzamide Chemical compound C=1N=C(C=2C=C(C=CC=2)C(F)(F)F)C(C)=NC=1NC(=O)NC(=O)C1=CC=CC=C1Cl KZIVCQCZFMIHHH-UHFFFAOYSA-N 0.000 description 1
BYHVGQHIAFURIL-UHFFFAOYSA-N 2-chloroquinoxaline Chemical compound C1=CC=CC2=NC(Cl)=CN=C21 BYHVGQHIAFURIL-UHFFFAOYSA-N 0.000 description 1
BSMGLVDZZMBWQB-UHFFFAOYSA-N 2-methyl-1-phenylpropan-1-one Chemical compound CC(C)C(=O)C1=CC=CC=C1 BSMGLVDZZMBWQB-UHFFFAOYSA-N 0.000 description 1
ATXBGHLILIABGX-UHFFFAOYSA-N 2-nitro-4-(trifluoromethyl)aniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O ATXBGHLILIABGX-UHFFFAOYSA-N 0.000 description 1
DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical class NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
ASONUAQLGIPYMA-UHFFFAOYSA-N 3,3-dimethyl-2-oxobutanal Chemical compound CC(C)(C)C(=O)C=O ASONUAQLGIPYMA-UHFFFAOYSA-N 0.000 description 1
CJXBBQKTUJXSGF-UHFFFAOYSA-N 3,6-dichloropyrazin-2-amine Chemical compound NC1=NC(Cl)=CN=C1Cl CJXBBQKTUJXSGF-UHFFFAOYSA-N 0.000 description 1
VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 description 1
VAZQKPXJSWRFOJ-UHFFFAOYSA-N 3-amino-6-(4-bromophenyl)-5-methylpyrazine-2-carbonitrile Chemical compound CC1=NC(N)=C(C#N)N=C1C1=CC=C(Br)C=C1 VAZQKPXJSWRFOJ-UHFFFAOYSA-N 0.000 description 1
ZSAQDEZPCNSGIS-UHFFFAOYSA-N 3-amino-6-(4-bromophenyl)-5-methylpyrazine-2-carboxylic acid Chemical compound CC1=NC(N)=C(C(O)=O)N=C1C1=CC=C(Br)C=C1 ZSAQDEZPCNSGIS-UHFFFAOYSA-N 0.000 description 1
LURGZVKKNLPCSQ-UHFFFAOYSA-N 3-amino-6-methylpyrazine-2-carbonitrile Chemical class CC1=CN=C(N)C(C#N)=N1 LURGZVKKNLPCSQ-UHFFFAOYSA-N 0.000 description 1
ZQDYILWQCQIWFL-UHFFFAOYSA-N 3-amino-6-methylpyrazine-2-carboxylic acid Chemical compound CC1=CN=C(N)C(C(O)=O)=N1 ZQDYILWQCQIWFL-UHFFFAOYSA-N 0.000 description 1
AZASWMGVGQEVCS-UHFFFAOYSA-N 4,4-dimethylpentan-2-one Chemical compound CC(=O)CC(C)(C)C AZASWMGVGQEVCS-UHFFFAOYSA-N 0.000 description 1
BXIXXXYDDJVHDL-UHFFFAOYSA-N 4-Chloro-ortho-phenylenediamine Chemical compound NC1=CC=C(Cl)C=C1N BXIXXXYDDJVHDL-UHFFFAOYSA-N 0.000 description 1
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
LOUMHCRSPDRZLU-UHFFFAOYSA-N 4-hydroxy-3-imino-6-methylpyrazine-2-carbonitrile Chemical compound CC1=CN(O)C(=N)C(C#N)=N1 LOUMHCRSPDRZLU-UHFFFAOYSA-N 0.000 description 1
ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 description 1
JTPCVJQUFYRJES-UHFFFAOYSA-N 5,6-dimethylpyrazin-2-amine Chemical compound CC1=NC=C(N)N=C1C JTPCVJQUFYRJES-UHFFFAOYSA-N 0.000 description 1
MEWMQKSSLANHCR-UHFFFAOYSA-N 5-chloro-2,3-dimethylpyrazine Chemical compound CC1=NC=C(Cl)N=C1C MEWMQKSSLANHCR-UHFFFAOYSA-N 0.000 description 1
ITXMRWYSIZIJDG-UHFFFAOYSA-N 5-ethylpyrazin-2-amine Chemical compound CCC1=CN=C(N)C=N1 ITXMRWYSIZIJDG-UHFFFAOYSA-N 0.000 description 1
ZNQOALAKPLGUPH-UHFFFAOYSA-N 5-methylpyrazin-2-amine Chemical compound CC1=CN=C(N)C=N1 ZNQOALAKPLGUPH-UHFFFAOYSA-N 0.000 description 1
KJAKXVBZQBPPOB-UHFFFAOYSA-N 5-phenylpyrazin-2-amine Chemical compound C1=NC(N)=CN=C1C1=CC=CC=C1 KJAKXVBZQBPPOB-UHFFFAOYSA-N 0.000 description 1
FMBKXKZEXQCCFM-UHFFFAOYSA-N 6-(trifluoromethyl)pyrazin-2-amine Chemical compound NC1=CN=CC(C(F)(F)F)=N1 FMBKXKZEXQCCFM-UHFFFAOYSA-N 0.000 description 1
OJEBWFGRUPIVSD-UHFFFAOYSA-N 6-chloro-1h-quinolin-2-one Chemical compound C1=C(Cl)C=CC2=NC(O)=CC=C21 OJEBWFGRUPIVSD-UHFFFAOYSA-N 0.000 description 1
OBVIIEVSLRCJSF-UHFFFAOYSA-N 6-chloroquinoxalin-2-amine Chemical compound C1=C(Cl)C=CC2=NC(N)=CN=C21 OBVIIEVSLRCJSF-UHFFFAOYSA-N 0.000 description 1
MZYZCCIXMLNATA-UHFFFAOYSA-N 6-methyl-5-[3-(trifluoromethyl)phenyl]pyrazin-2-amine Chemical compound CC1=NC(N)=CN=C1C1=CC=CC(C(F)(F)F)=C1 MZYZCCIXMLNATA-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
241000254173 Coleoptera Species 0.000 description 1
ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
241000258937 Hemiptera Species 0.000 description 1
241001508566 Hypera postica Species 0.000 description 1
241000255777 Lepidoptera Species 0.000 description 1
241000238814 Orthoptera Species 0.000 description 1
231100000674 Phytotoxicity Toxicity 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
LCISOMFIAQECOH-UHFFFAOYSA-N [4-(trifluoromethyl)phenyl] carbonochloridate Chemical compound FC(F)(F)C1=CC=C(OC(Cl)=O)C=C1 LCISOMFIAQECOH-UHFFFAOYSA-N 0.000 description 1
PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
150000003927 aminopyridines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229940054066 benzamide antipsychotics Drugs 0.000 description 1
150000003936 benzamides Chemical class 0.000 description 1
239000012267 brine Substances 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
244000038559 crop plants Species 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
QQQYTWIFVNKMRW-UHFFFAOYSA-N diflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C1 QQQYTWIFVNKMRW-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
244000078703 ectoparasite Species 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000002657 fibrous material Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
238000003898 horticulture Methods 0.000 description 1
150000002429 hydrazines Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000011835 investigation Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
230000001418 larval effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
150000002642 lithium compounds Chemical class 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
231100001225 mammalian toxicity Toxicity 0.000 description 1
JGAJCAJHSHUPGH-UHFFFAOYSA-N methyl 3-amino-6-chloropyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(Cl)=CN=C1N JGAJCAJHSHUPGH-UHFFFAOYSA-N 0.000 description 1
INCSQLZZXBPATR-UHFFFAOYSA-N methyl 3-aminopyrazine-2-carboxylate Chemical compound COC(=O)C1=NC=CN=C1N INCSQLZZXBPATR-UHFFFAOYSA-N 0.000 description 1
238000003541 multi-stage reaction Methods 0.000 description 1
GEHWGERCVXYQRY-UHFFFAOYSA-N n-(2-phenylphenyl)benzamide Chemical class C=1C=CC=CC=1C(=O)NC1=CC=CC=C1C1=CC=CC=C1 GEHWGERCVXYQRY-UHFFFAOYSA-N 0.000 description 1
YKSVRMFJBBAHBK-UHFFFAOYSA-N n-[[5-(4-bromophenyl)-6-methylpyrazin-2-yl]carbamoyl]-2,6-dichlorobenzamide Chemical compound C=1N=C(C=2C=CC(Br)=CC=2)C(C)=NC=1NC(=O)NC(=O)C1=C(Cl)C=CC=C1Cl YKSVRMFJBBAHBK-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 1
XFTQRUTUGRCSGO-UHFFFAOYSA-N pyrazin-2-amine Chemical group NC1=CN=CC=N1 XFTQRUTUGRCSGO-UHFFFAOYSA-N 0.000 description 1
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000001953 sensory effect Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000001665 trituration Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
- C07C275/48—Y being a hydrogen or a carbon atom
- C07C275/54—Y being a carbon atom of a six-membered aromatic ring, e.g. benzoylureas
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/20—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D241/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with nitrogen atoms directly attached to ring carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CS788519A 1977-07-27 1978-06-21 Process for preparing 1-/mono-o-subst.benzoyl/-3-/subst.pyrazinyl/ureas CS198105B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US05/819,639 US4133956A (en)	1977-07-27	1977-07-27	Preparation of benzoylureas

Publications (1)

Publication Number	Publication Date
CS198105B2 true CS198105B2 (en)	1980-05-30

Family

ID=25228664

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CS788519A CS198105B2 (en)	1977-07-27	1978-06-21	Process for preparing 1-/mono-o-subst.benzoyl/-3-/subst.pyrazinyl/ureas
CS788520A CS198106B2 (en)	1977-07-27	1978-06-21	Process for preparing 1-/mono-o-subst.benzoyl/-3-/subst.pyrazinyl/ureas

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CS788520A CS198106B2 (en)	1977-07-27	1978-06-21	Process for preparing 1-/mono-o-subst.benzoyl/-3-/subst.pyrazinyl/ureas

Country Status (10)

Country	Link
US (1)	US4133956A (pl)
CA (1)	CA1103251A (pl)
CS (2)	CS198105B2 (pl)
ES (1)	ES471879A1 (pl)
HU (1)	HU180726B (pl)
IE (1)	IE47001B1 (pl)
IL (1)	IL54928A (pl)
NZ (1)	NZ187621A (pl)
PL (1)	PL115711B1 (pl)
SU (1)	SU799662A3 (pl)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4399152A (en) *	1980-04-03	1983-08-16	Duphar International B.V.	Substituted benzoyl ureas as insecticides
US4425343A (en)	1980-10-24	1984-01-10	Nissan Chemical Industries, Ltd.	Benzoazine ether or thioether linkage containing urea compounds, process for producing same and insecticides containing said compounds
US4405552A (en) *	1981-03-03	1983-09-20	Eli Lilly And Company	1-Benzoyl-3-(arylphyridyl)urea compounds
US4366155A (en) *	1981-03-30	1982-12-28	Eli Lilly And Company	1-Benzoyl-3-(6-oxopyridazinyl)ureas, compositions, and insecticidal method
US5135953A (en) *	1984-12-28	1992-08-04	Ciba-Geigy	Use of acyl urea compounds for controlling endoparasites and ectoparasites of warm-blooded animals
AR029489A1 (es)	2000-03-10	2003-07-02	Euro Celtique Sa	Piridinas, pirimidinas, pirazinas, triazinas sustituidas por arilo, composiciones farmaceuticas y el uso de las mismas para la manufactura de un medicamento
EP1292580A1 (en) *	2000-05-17	2003-03-19	Universite Catholique De Louvain	Pyrazine and imidazopyrazine derivatives as antioxidants
AR036873A1 (es) *	2001-09-07	2004-10-13	Euro Celtique Sa	Piridinas aril sustituidas a, composiciones farmaceuticas y el uso de las mismas para la preparacion de un medicamento
AR037233A1 (es) *	2001-09-07	2004-11-03	Euro Celtique Sa	Piridinas aril sustituidas, composiciones farmaceuticas y el uso de dichos compuestos para la elaboracion de un medicamento

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL160809C (nl) *	1970-05-15	1979-12-17	Duphar Int Res	Werkwijze ter bereiding van benzoylureumverbindingen, alsmede werkwijze ter bereiding van insekticide prepara- ten op basis van benzoylureumverbindingen.

1977
- 1977-07-27 US US05/819,639 patent/US4133956A/en not_active Expired - Lifetime
1978
- 1978-06-15 IL IL54928A patent/IL54928A/xx unknown
- 1978-06-19 NZ NZ187621A patent/NZ187621A/xx unknown
- 1978-06-20 HU HU78EI793A patent/HU180726B/hu unknown
- 1978-06-21 CS CS788519A patent/CS198105B2/cs unknown
- 1978-06-21 SU SU782628947A patent/SU799662A3/ru active
- 1978-06-21 CS CS788520A patent/CS198106B2/cs unknown
- 1978-06-21 IE IE1242/78A patent/IE47001B1/en unknown
- 1978-06-22 PL PL1978207831A patent/PL115711B1/pl unknown
- 1978-07-19 ES ES471879A patent/ES471879A1/es not_active Expired
- 1978-07-25 CA CA308,083A patent/CA1103251A/en not_active Expired

Also Published As

Publication number	Publication date
IE47001B1 (en)	1983-11-30
CA1103251A (en)	1981-06-16
CS198106B2 (en)	1980-05-30
PL207831A1 (pl)	1979-11-19
PL115711B1 (en)	1981-04-30
SU799662A3 (ru)	1981-01-23
US4133956A (en)	1979-01-09
IE781242L (en)	1979-01-27
IL54928A (en)	1982-02-28
ES471879A1 (es)	1979-02-01
HU180726B (en)	1983-04-29
NZ187621A (en)	1980-11-28

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DE69119301T2 (de)	1996-10-17	Hydrazincarboxamidderivate, Verfahren für ihre Herstellung und ihre Verwendung
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BR0012224B1 (pt)	2010-12-28	derivado de ftalamida, inseticida agro-hortìcola, e, método para uso de um inseticida agro-hortìcola.
CA1070308A (en)	1980-01-22	1-(substituted benzolyl)-3-(substituted pyrazinyl) ureas
CA1164871A (en)	1984-04-03	Isoxazolylbenzamides
CS198105B2 (en)	1980-05-30	Process for preparing 1-/mono-o-subst.benzoyl/-3-/subst.pyrazinyl/ureas
EP0450359B1 (de)	1995-03-15	Herbizides Mittel
HU226428B1 (en)	2008-12-29	Process for producing guanidine derivatives, intermediates therefor and their production
JPH03169861A (ja)	1991-07-23	ジアミノエチレン誘導体、その製造法及びその殺虫組成物
FR2518547A1 (fr)	1983-06-24	Derives de l'acide propionique-2 phenoxy substitue et leur utilisation comme herbicides
EP0835865B1 (en)	2003-03-12	Dihydropyridazinones and pyridazinones and their use as fungicides and insecticides
USRE30563E (en)	1981-03-31	Preparation of benzoylureas
JPS6089465A (ja)	1985-05-20	新規なｎ‐（チオ）カルバモイルアリール（チオ）カルボキシイミド酸エステル、それらの製造方法およびそれらを含有する殺中剤
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FR2555579A1 (fr)	1985-05-31	Nouveaux derives de pyridylacetonitriles, leur preparation et leur utilisation comme antifongiques dans le domaine agricole
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JP2002501038A (ja)	2002-01-15	有機ニトリル誘導体およびその農薬としての使用
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