BE586728A - - Google Patents
Info
- Publication number
- BE586728A BE586728A BE586728DA BE586728A BE 586728 A BE586728 A BE 586728A BE 586728D A BE586728D A BE 586728DA BE 586728 A BE586728 A BE 586728A
- Authority
- BE
- Belgium
- Prior art keywords
- substituted
- dinitro
- dinitrobenzamide
- parasiticides
- lower alkyl
- Prior art date
Links
- -1 methoxy, methyl Chemical group 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- KIMCGLHTSSZPNS-UHFFFAOYSA-N 2,3-dinitrobenzamide Chemical class NC(=O)C1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O KIMCGLHTSSZPNS-UHFFFAOYSA-N 0.000 claims description 16
- 230000000590 parasiticidal Effects 0.000 claims description 14
- 230000002363 herbicidal Effects 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000003368 amide group Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 239000002297 parasiticide Substances 0.000 claims description 12
- 239000004009 herbicide Substances 0.000 claims description 11
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- ZEFNOZRLAWVAQF-UHFFFAOYSA-N Dinitolmide Chemical compound CC1=C(C(N)=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O ZEFNOZRLAWVAQF-UHFFFAOYSA-N 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 5
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 4
- 238000005755 formation reaction Methods 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 4
- DMLZFSSWWLRVHC-UHFFFAOYSA-N [N+](=O)([O-])C=1C(=C(C(=O)NC(C)=O)C=C(C1)[N+](=O)[O-])C Chemical compound [N+](=O)([O-])C=1C(=C(C(=O)NC(C)=O)C=C(C1)[N+](=O)[O-])C DMLZFSSWWLRVHC-UHFFFAOYSA-N 0.000 claims description 3
- HRMGJMRTYMVUSZ-UHFFFAOYSA-N [N+](=O)([O-])C=1C=C(C(=O)NC(C)=O)C=C(C1)[N+](=O)[O-] Chemical compound [N+](=O)([O-])C=1C=C(C(=O)NC(C)=O)C=C(C1)[N+](=O)[O-] HRMGJMRTYMVUSZ-UHFFFAOYSA-N 0.000 claims description 3
- 230000000855 fungicidal Effects 0.000 claims description 3
- 239000000417 fungicide Substances 0.000 claims description 3
- 230000000749 insecticidal Effects 0.000 claims description 3
- 239000002917 insecticide Substances 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- HNPLOEQTHLPNCL-UHFFFAOYSA-N CN(C(C)=O)C(=O)C1=C(C)C(=CC(=C1)[N+]([O-])=O)[N+]([O-])=O Chemical compound CN(C(C)=O)C(=O)C1=C(C)C(=CC(=C1)[N+]([O-])=O)[N+]([O-])=O HNPLOEQTHLPNCL-UHFFFAOYSA-N 0.000 claims 2
- OJFCQFOGGULEEI-UHFFFAOYSA-N [N+](=O)([O-])C=1C=C(C(=O)NC(CC)=O)C=C(C1)[N+](=O)[O-] Chemical compound [N+](=O)([O-])C=1C=C(C(=O)NC(CC)=O)C=C(C1)[N+](=O)[O-] OJFCQFOGGULEEI-UHFFFAOYSA-N 0.000 claims 2
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- JPBGTKCKPYAUHI-UHFFFAOYSA-N [N+](=O)([O-])C=1C(=C(C(=O)NC(CC)=O)C=C(C1)[N+](=O)[O-])C Chemical compound [N+](=O)([O-])C=1C(=C(C(=O)NC(CC)=O)C=C(C1)[N+](=O)[O-])C JPBGTKCKPYAUHI-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 239000000047 product Substances 0.000 description 18
- 239000002253 acid Substances 0.000 description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 230000000875 corresponding Effects 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 8
- UUKWKUSGGZNXGA-UHFFFAOYSA-N 3,5-dinitrobenzamide Chemical class NC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 UUKWKUSGGZNXGA-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 150000001805 chlorine compounds Chemical class 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N Propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 3
- NFLIVWBJEDGBLZ-UHFFFAOYSA-N [N+](=O)([O-])C=1C(=C(C(=O)NC(C)=O)C=C(C1)[N+](=O)[O-])OC Chemical compound [N+](=O)([O-])C=1C(=C(C(=O)NC(C)=O)C=C(C1)[N+](=O)[O-])OC NFLIVWBJEDGBLZ-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 239000011343 solid material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- UTESHVANCFLTQV-UHFFFAOYSA-N 2,4-dinitrobenzamide Chemical compound NC(=O)C1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UTESHVANCFLTQV-UHFFFAOYSA-N 0.000 description 2
- JIYLSGFLLWXHGN-UHFFFAOYSA-N 2-methoxy-3,5-dinitrobenzamide Chemical compound COC1=C(C(N)=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O JIYLSGFLLWXHGN-UHFFFAOYSA-N 0.000 description 2
- VYWYYJYRVSBHJQ-UHFFFAOYSA-N 3,5-Dinitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 VYWYYJYRVSBHJQ-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N Acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N Copper(I) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
- NHGVZTMBVDFPHJ-UHFFFAOYSA-N Formyl fluoride Chemical compound FC=O NHGVZTMBVDFPHJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N Phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 2
- 239000003729 cation exchange resin Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- HTWWKYKIBSHDPC-UHFFFAOYSA-N decanoyl decanoate Chemical compound CCCCCCCCCC(=O)OC(=O)CCCCCCCCC HTWWKYKIBSHDPC-UHFFFAOYSA-N 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- NLEUXPOVZGDKJI-UHFFFAOYSA-N nickel(2+);dicyanide Chemical compound [Ni+2].N#[C-].N#[C-] NLEUXPOVZGDKJI-UHFFFAOYSA-N 0.000 description 2
- 150000002829 nitrogen Chemical group 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LXQOQPGNCGEELI-UHFFFAOYSA-N 2,4-dinitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O LXQOQPGNCGEELI-UHFFFAOYSA-N 0.000 description 1
- IKCLCGXPQILATA-UHFFFAOYSA-N 2-Chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
- GUDFEGXIJXTNJG-UHFFFAOYSA-N 2-chloro-3,5-dinitrobenzamide Chemical class NC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1Cl GUDFEGXIJXTNJG-UHFFFAOYSA-N 0.000 description 1
- ZAMOEFQZCCUBBM-UHFFFAOYSA-N 2-methoxy-4,6-dinitrobenzamide Chemical class COC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1C(N)=O ZAMOEFQZCCUBBM-UHFFFAOYSA-N 0.000 description 1
- YTUKZWSMRTXUPV-UHFFFAOYSA-N 2-methyl-4,6-dinitrobenzamide Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1C(N)=O YTUKZWSMRTXUPV-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- FXXACINHVKSMDR-UHFFFAOYSA-N Acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 description 1
- 241000213004 Alternaria solani Species 0.000 description 1
- 235000007320 Avena fatua Nutrition 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N Butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- DBILDSAUKQVTJO-UHFFFAOYSA-N C(C)(=O)NC(C1=C(C=C(C=C1OC)[N+](=O)[O-])[N+](=O)[O-])=O Chemical compound C(C)(=O)NC(C1=C(C=C(C=C1OC)[N+](=O)[O-])[N+](=O)[O-])=O DBILDSAUKQVTJO-UHFFFAOYSA-N 0.000 description 1
- JUFRWFGZLSKLMF-UHFFFAOYSA-N C(CCC)(=O)NC(C1=C(C=C(C=C1CC)[N+](=O)[O-])[N+](=O)[O-])=O Chemical compound C(CCC)(=O)NC(C1=C(C=C(C=C1CC)[N+](=O)[O-])[N+](=O)[O-])=O JUFRWFGZLSKLMF-UHFFFAOYSA-N 0.000 description 1
- IRCKRBLMTRAJEB-UHFFFAOYSA-N CCCN(C(C)=O)C(=O)C1=C(C)C(=CC(=C1)[N+]([O-])=O)[N+]([O-])=O Chemical compound CCCN(C(C)=O)C(=O)C1=C(C)C(=CC(=C1)[N+]([O-])=O)[N+]([O-])=O IRCKRBLMTRAJEB-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 240000002533 Echinochloa frumentacea Species 0.000 description 1
- 235000008247 Echinochloa frumentacea Nutrition 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N Ethyl radical Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N Methyl radical Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 1
- 240000006745 Valeriana officinalis Species 0.000 description 1
- 235000013832 Valeriana officinalis Nutrition 0.000 description 1
- UKEPWLVMCJIPGC-UHFFFAOYSA-N [N+](=O)([O-])C1=C(C(=O)N)C(=CC(=C1)[N+](=O)[O-])CC Chemical compound [N+](=O)([O-])C1=C(C(=O)N)C(=CC(=C1)[N+](=O)[O-])CC UKEPWLVMCJIPGC-UHFFFAOYSA-N 0.000 description 1
- JNMVVCHIQIFBOY-UHFFFAOYSA-N [N+](=O)([O-])C1=C(C(=O)NC(C)=O)C(=CC(=C1)[N+](=O)[O-])C Chemical compound [N+](=O)([O-])C1=C(C(=O)NC(C)=O)C(=CC(=C1)[N+](=O)[O-])C JNMVVCHIQIFBOY-UHFFFAOYSA-N 0.000 description 1
- RULPONOSQJVCTD-UHFFFAOYSA-N [N+](=O)([O-])C1=C(C(=O)NC(CCCC)=O)C=CC(=C1)[N+](=O)[O-] Chemical compound [N+](=O)([O-])C1=C(C(=O)NC(CCCC)=O)C=CC(=C1)[N+](=O)[O-] RULPONOSQJVCTD-UHFFFAOYSA-N 0.000 description 1
- XHOUCQFZVMBNFF-UHFFFAOYSA-N [N+](=O)([O-])C1=C(C(=O)NCC)C(=CC(=C1)[N+](=O)[O-])C Chemical compound [N+](=O)([O-])C1=C(C(=O)NCC)C(=CC(=C1)[N+](=O)[O-])C XHOUCQFZVMBNFF-UHFFFAOYSA-N 0.000 description 1
- BCQMVBWLNVYVFD-UHFFFAOYSA-N [N+](=O)([O-])C=1C(=C(C(=O)NC(C(C)C)=O)C=C(C1)[N+](=O)[O-])C Chemical compound [N+](=O)([O-])C=1C(=C(C(=O)NC(C(C)C)=O)C=C(C1)[N+](=O)[O-])C BCQMVBWLNVYVFD-UHFFFAOYSA-N 0.000 description 1
- MGXCIKBOMKHHIC-UHFFFAOYSA-N [N+](=O)([O-])C=1C(=C(C(=O)NC(CC)=O)C=C(C1)[N+](=O)[O-])CC Chemical compound [N+](=O)([O-])C=1C(=C(C(=O)NC(CC)=O)C=C(C1)[N+](=O)[O-])CC MGXCIKBOMKHHIC-UHFFFAOYSA-N 0.000 description 1
- JEJVLPITNCKHFS-UHFFFAOYSA-N [N+](=O)([O-])C=1C(=C(C(=O)NC(CCC)=O)C=C(C1)[N+](=O)[O-])C Chemical compound [N+](=O)([O-])C=1C(=C(C(=O)NC(CCC)=O)C=C(C1)[N+](=O)[O-])C JEJVLPITNCKHFS-UHFFFAOYSA-N 0.000 description 1
- KCXRELBLRPGFSU-UHFFFAOYSA-N [N+](=O)([O-])C=1C(=C(C(=O)NC(CCCC)=O)C=C(C1)[N+](=O)[O-])C Chemical compound [N+](=O)([O-])C=1C(=C(C(=O)NC(CCCC)=O)C=C(C1)[N+](=O)[O-])C KCXRELBLRPGFSU-UHFFFAOYSA-N 0.000 description 1
- XTFXWYUQPUSGIP-UHFFFAOYSA-N [N+](=O)([O-])C=1C(=C(C(=O)NC=O)C=C(C1)[N+](=O)[O-])C Chemical compound [N+](=O)([O-])C=1C(=C(C(=O)NC=O)C=C(C1)[N+](=O)[O-])C XTFXWYUQPUSGIP-UHFFFAOYSA-N 0.000 description 1
- PXMPCRKQXVYXHN-UHFFFAOYSA-N [N+](=O)([O-])C=1C=C(C(=O)NC=O)C=C(C1)[N+](=O)[O-] Chemical compound [N+](=O)([O-])C=1C=C(C(=O)NC=O)C=C(C1)[N+](=O)[O-] PXMPCRKQXVYXHN-UHFFFAOYSA-N 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- 150000003936 benzamides Chemical class 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- IPIVAXLHTVNRBS-UHFFFAOYSA-N decanoyl chloride Chemical compound CCCCCCCCCC(Cl)=O IPIVAXLHTVNRBS-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- UCVODTZQZHMTPN-UHFFFAOYSA-N heptanoyl chloride Chemical compound CCCCCCC(Cl)=O UCVODTZQZHMTPN-UHFFFAOYSA-N 0.000 description 1
- DAPZDAPTZFJZTO-UHFFFAOYSA-N heptanoyl heptanoate Chemical compound CCCCCCC(=O)OC(=O)CCCCCC DAPZDAPTZFJZTO-UHFFFAOYSA-N 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000000968 intestinal Effects 0.000 description 1
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- NTQYXUJLILNTFH-UHFFFAOYSA-N nonanoyl chloride Chemical compound CCCCCCCCC(Cl)=O NTQYXUJLILNTFH-UHFFFAOYSA-N 0.000 description 1
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
- RAFYDKXYXRZODZ-UHFFFAOYSA-N octanoyl octanoate Chemical compound CCCCCCCC(=O)OC(=O)CCCCCCC RAFYDKXYXRZODZ-UHFFFAOYSA-N 0.000 description 1
- 244000045947 parasites Species 0.000 description 1
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002588 toxic Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 235000016788 valerian Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE586728A true BE586728A (xx) |
Family
ID=191624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE586728D BE586728A (xx) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE586728A (xx) |
-
0
- BE BE586728D patent/BE586728A/fr unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH631444A5 (fr) | Composes 5-trifluoromethylpyridine 2-substitues et procede pour la preparation de ceux-ci. | |
| EP0152360A2 (fr) | Nouveaux dérivés du cyano-2 benzimidazole, leur préparation et leur utilisation comme fongicides | |
| BE899207A (fr) | Nouvelles anilines substituees, leur preparation et leur utilisation comme herbicides | |
| FR2518547A1 (fr) | Derives de l'acide propionique-2 phenoxy substitue et leur utilisation comme herbicides | |
| EP0119892B1 (fr) | Nouveau dérivés de l'hydroxylamine, leur procédé de préparation, leur application comme facteur de croissance des végétaux et les compositions les renfermant | |
| EP0069033B1 (fr) | Herbicides à fonction amide et ester dérivés de la pyridine ainsi que leur procédé de préparation et leur application | |
| EP0265305B1 (fr) | Nouveaux dérivés de la 5-pyrazolone, leur procédé de préparation, leur utilisation comme herbicides et les compositions les renfermant | |
| BE586728A (xx) | ||
| FR2594437A1 (fr) | Nouveaux derives du cyano-2 benzimidazole, leur preparation, les compositions les contenant et leur utilisation comme fongicide | |
| EP0014167B1 (fr) | Produits dérivés de l'aniline ayant une activité antifongique ainsi que leur procédé de préparation | |
| EP0122206A2 (fr) | Nouveaux dérivés de cyano-2 imidazopyridine, leur préparation et leur utilisation comme fongicides | |
| FR2555579A1 (fr) | Nouveaux derives de pyridylacetonitriles, leur preparation et leur utilisation comme antifongiques dans le domaine agricole | |
| FR2587999A1 (fr) | Aryloxy-phenoxy-acyl-malonates, leur preparation et les compositions herbicides les contenant | |
| BE629779A (xx) | ||
| EP0016132A1 (fr) | Nouvelle phenyluree substituee herbicide | |
| FR2635776A1 (fr) | Derives amides, procede pour leur fabrication et compositions fongicides les contenant | |
| CH639374A5 (fr) | N-(4-pyrazolidinyl)-benzamides, presentant notamment des proprietes antiemetiques et de vidage gastrique. | |
| FR2467191A1 (fr) | Nouveaux 5-(2'-chloro-4'-trifluoromethylphenoxy)-2-nitrostyrenes, leur procede de production, composition herbicide les contenant et leur application a la destruction de vegetaux | |
| BE876077A (fr) | Derives de diphenylamine | |
| LU83355A1 (fr) | Ethers diphenyliques a activite herbicide | |
| FR2572889A1 (fr) | Nouveaux derives d'acide (trifluoromethyl)-phenoxy-benzoique, procede pour leur preparation et fongicides contenant ces composes comme ingredient actif. | |
| FR2543549A1 (fr) | Nouvelles anilines substituees, leur preparation et leur utilisation comme herbicides | |
| BE590259A (xx) | ||
| BE897034A (fr) | Nouveaux derives du benzene, leur preparation et leur utilisation comme medicaments | |
| BE559968A (xx) |