IL34788A - History of 01, 11-dihydrodibenzoazepine, process for their preparation and fungicidal mixtures containing them - Google Patents
History of 01, 11-dihydrodibenzoazepine, process for their preparation and fungicidal mixtures containing themInfo
- Publication number
- IL34788A IL34788A IL34788A IL3478870A IL34788A IL 34788 A IL34788 A IL 34788A IL 34788 A IL34788 A IL 34788A IL 3478870 A IL3478870 A IL 3478870A IL 34788 A IL34788 A IL 34788A
- Authority
- IL
- Israel
- Prior art keywords
- dihydrodibenzo
- azepine
- derivatives
- fjazepine
- fungicidal compositions
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 22
- 239000000203 mixture Substances 0.000 title claims description 22
- 230000000855 fungicidal effect Effects 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 8
- ILHYRNCXUBXJRW-UHFFFAOYSA-N 10,11-dihydro-9H-benzo[d][1]benzazepine Chemical class C1=CN=C2C=CC=CC2=C2CCCC=C21 ILHYRNCXUBXJRW-UHFFFAOYSA-N 0.000 title description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 36
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 18
- -1 alkyl radical Chemical class 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- ZSMRRZONCYIFNB-UHFFFAOYSA-N 6,11-dihydro-5h-benzo[b][1]benzazepine Chemical class C1CC2=CC=CC=C2NC2=CC=CC=C12 ZSMRRZONCYIFNB-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 239000003995 emulsifying agent Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 3
- 239000002270 dispersing agent Substances 0.000 claims description 3
- 238000009736 wetting Methods 0.000 claims description 3
- 239000000080 wetting agent Substances 0.000 claims description 3
- JQOTXDOJGISJCB-UHFFFAOYSA-N 6,11-dihydro-5h-benzo[b][1]benzazepin-5-amine Chemical compound NC1CC2=CC=CC=C2NC2=CC=CC=C12 JQOTXDOJGISJCB-UHFFFAOYSA-N 0.000 claims description 2
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical group [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 150000008040 ionic compounds Chemical class 0.000 claims 1
- FMWUJTZLEZNIFY-UHFFFAOYSA-N pentyl N-(6,11-dihydro-5H-benzo[b][1]benzazepin-5-yl)carbamate Chemical compound C(CCCC)OC(=O)NC1CC2=C(NC3=C1C=CC=C3)C=CC=C2 FMWUJTZLEZNIFY-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
- 239000000243 solution Substances 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 238000002844 melting Methods 0.000 description 25
- 230000008018 melting Effects 0.000 description 25
- 239000012153 distilled water Substances 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
- 239000003085 diluting agent Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- PWMOKXUOXHJSFP-UHFFFAOYSA-N 11-methyl-5,6-dihydrobenzo[b][1]benzazepin-5-amine Chemical compound C1C(N)C2=CC=CC=C2N(C)C2=CC=CC=C21 PWMOKXUOXHJSFP-UHFFFAOYSA-N 0.000 description 6
- 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 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- ZKHZWXLOSIGIGZ-UHFFFAOYSA-N 5-methoxy-11h-benzo[b][1]benzazepine Chemical compound COC1=CC2=CC=CC=C2NC2=CC=CC=C12 ZKHZWXLOSIGIGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910001023 sodium amalgam Inorganic materials 0.000 description 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- NRDQFWXVTPZZAZ-UHFFFAOYSA-N butyl carbonochloridate Chemical compound CCCCOC(Cl)=O NRDQFWXVTPZZAZ-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 2
- QQKDTTWZXHEGAQ-UHFFFAOYSA-N propyl carbonochloridate Chemical compound CCCOC(Cl)=O QQKDTTWZXHEGAQ-UHFFFAOYSA-N 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- MTQKMPGBALVEDL-ZPCKWCKBSA-N (z,12r)-12-hydroxy-2-sulfooctadec-9-enoic acid Chemical class CCCCCC[C@@H](O)C\C=C/CCCCCCC(C(O)=O)S(O)(=O)=O MTQKMPGBALVEDL-ZPCKWCKBSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- TWPNNPZIOICEQO-UHFFFAOYSA-N 11-ethyl-5,6-dihydrobenzo[b][1]benzazepin-5-amine Chemical compound C(C)N1C2=C(CC(C3=C1C=CC=C3)N)C=CC=C2 TWPNNPZIOICEQO-UHFFFAOYSA-N 0.000 description 1
- AFRLIBIVHBVGDG-UHFFFAOYSA-N 11-ethyl-5-methoxybenzo[b][1]benzazepine Chemical compound C1=C(OC)C2=CC=CC=C2N(CC)C2=CC=CC=C21 AFRLIBIVHBVGDG-UHFFFAOYSA-N 0.000 description 1
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
- 241001083847 Berberis Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CKHLYRVXXLSJLY-UHFFFAOYSA-N C(CC)N1C2=C(CC(C3=C1C=CC=C3)=NO)C=CC=C2 Chemical compound C(CC)N1C2=C(CC(C3=C1C=CC=C3)=NO)C=CC=C2 CKHLYRVXXLSJLY-UHFFFAOYSA-N 0.000 description 1
- MQCYUTHLGGBKSQ-UHFFFAOYSA-N C(CC)N1C2=C(CC(C3=C1C=CC=C3)NC(=O)OCC)C=CC=C2 Chemical compound C(CC)N1C2=C(CC(C3=C1C=CC=C3)NC(=O)OCC)C=CC=C2 MQCYUTHLGGBKSQ-UHFFFAOYSA-N 0.000 description 1
- DQPWJQULUWNRRR-UHFFFAOYSA-N CN1C2=C(CC(C3=C1C=CC=C3)NC(=O)OCC)C=CC=C2 Chemical compound CN1C2=C(CC(C3=C1C=CC=C3)NC(=O)OCC)C=CC=C2 DQPWJQULUWNRRR-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000682541 Erysiphe berberidis Species 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- CMNLDHQCAXJRCS-UHFFFAOYSA-N N-(11-ethyl-6H-benzo[b][1]benzazepin-5-ylidene)hydroxylamine Chemical compound C(C)N1C2=C(CC(C3=C1C=CC=C3)=NO)C=CC=C2 CMNLDHQCAXJRCS-UHFFFAOYSA-N 0.000 description 1
- XFLCOODLBRLMOM-UHFFFAOYSA-N N-(11-methyl-6H-benzo[b][1]benzazepin-5-ylidene)hydroxylamine Chemical compound CN1C2=C(CC(C3=C1C=CC=C3)=NO)C=CC=C2 XFLCOODLBRLMOM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019250 POS3 Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- ROUZHZJLIWBVFA-UHFFFAOYSA-N butyl N-(6,11-dihydro-5H-benzo[b][1]benzazepin-5-yl)carbamate Chemical compound C(CCC)OC(=O)NC1CC2=C(NC3=C1C=CC=C3)C=CC=C2 ROUZHZJLIWBVFA-UHFFFAOYSA-N 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- SATRZZYUXUGZIE-UHFFFAOYSA-N heptyl carbonochloridate Chemical compound CCCCCCCOC(Cl)=O SATRZZYUXUGZIE-UHFFFAOYSA-N 0.000 description 1
- KIWBRXCOTCXSSZ-UHFFFAOYSA-N hexyl carbonochloridate Chemical compound CCCCCCOC(Cl)=O KIWBRXCOTCXSSZ-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- AMIZCEOUBZLIPK-UHFFFAOYSA-N methyl N-(6,11-dihydro-5H-benzo[b][1]benzazepin-5-yl)carbamate Chemical compound COC(=O)NC1CC2=C(NC3=C1C=CC=C3)C=CC=C2 AMIZCEOUBZLIPK-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- XHRRYUDVWPPWIP-UHFFFAOYSA-N pentyl carbonochloridate Chemical compound CCCCCOC(Cl)=O XHRRYUDVWPPWIP-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- OXROJQDKDANXDO-UHFFFAOYSA-N propan-2-yl N-(11-methyl-5,6-dihydrobenzo[b][1]benzazepin-5-yl)carbamate Chemical compound CN1C2=C(CC(C3=C1C=CC=C3)NC(=O)OC(C)C)C=CC=C2 OXROJQDKDANXDO-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
-
- 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
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR6921176A FR2045705A1 (en) | 1969-06-24 | 1969-06-24 | Fungicidal dihydrodibenzaxepine derivs |
| FR7012838A FR2086796A6 (en) | 1970-04-09 | 1970-04-09 | Fungicidal dihydrodibenzaxepine derivs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL34788A0 IL34788A0 (en) | 1970-08-19 |
| IL34788A true IL34788A (en) | 1973-04-30 |
Family
ID=26215129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL34788A IL34788A (en) | 1969-06-24 | 1970-06-23 | History of 01, 11-dihydrodibenzoazepine, process for their preparation and fungicidal mixtures containing them |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3792042A (de) |
| JP (1) | JPS4837036B1 (de) |
| AT (1) | AT300464B (de) |
| BE (1) | BE752411A (de) |
| CH (1) | CH509758A (de) |
| DK (1) | DK133466B (de) |
| ES (1) | ES381090A1 (de) |
| GB (1) | GB1253486A (de) |
| IL (1) | IL34788A (de) |
| LU (1) | LU61186A1 (de) |
| NL (1) | NL144275B (de) |
| OA (1) | OA03297A (de) |
| SE (2) | SE370237B (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI75561C (fi) * | 1979-10-30 | 1988-07-11 | Ciba Geigy Ag | Foerfarande foer framstaellning av 5- karbamoyl-10-oxo-10,11-dihydro-5h-dibens/b,f/azepin och daertill noedvaendiga mellanprodukter. |
| US20050049146A1 (en) * | 2001-11-05 | 2005-03-03 | Chiarello John F. | Use of substituted dibenzothiepine derivatives as insecticidal, acaricidal and nematicidal agents |
-
1970
- 1970-06-16 NL NL707008793A patent/NL144275B/xx unknown
- 1970-06-18 OA OA53954A patent/OA03297A/xx unknown
- 1970-06-22 GB GB30074/70A patent/GB1253486A/en not_active Expired
- 1970-06-22 US US00048450A patent/US3792042A/en not_active Expired - Lifetime
- 1970-06-23 SE SE7008694A patent/SE370237B/xx unknown
- 1970-06-23 CH CH951470A patent/CH509758A/fr not_active IP Right Cessation
- 1970-06-23 DK DK324870AA patent/DK133466B/da unknown
- 1970-06-23 IL IL34788A patent/IL34788A/en unknown
- 1970-06-23 BE BE752411D patent/BE752411A/xx unknown
- 1970-06-23 SE SE7301346A patent/SE381162B/xx unknown
- 1970-06-24 LU LU61186D patent/LU61186A1/xx unknown
- 1970-06-24 AT AT568770A patent/AT300464B/de not_active IP Right Cessation
- 1970-06-24 ES ES381090A patent/ES381090A1/es not_active Expired
-
1971
- 1971-03-05 JP JP46011358A patent/JPS4837036B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| OA03297A (fr) | 1970-12-15 |
| NL7008793A (de) | 1970-12-29 |
| BE752411A (fr) | 1970-12-23 |
| DK133466C (de) | 1976-10-18 |
| IL34788A0 (en) | 1970-08-19 |
| LU61186A1 (de) | 1971-07-06 |
| DE2031236A1 (de) | 1971-01-07 |
| NL144275B (nl) | 1974-12-16 |
| SE381162B (sv) | 1975-12-01 |
| US3792042A (en) | 1974-02-12 |
| GB1253486A (en) | 1971-11-17 |
| SE370237B (de) | 1974-10-07 |
| AT300464B (de) | 1972-07-25 |
| CH509758A (fr) | 1971-07-15 |
| JPS4837036B1 (de) | 1973-11-08 |
| DK133466B (da) | 1976-05-24 |
| DE2031236B2 (de) | 1975-09-25 |
| ES381090A1 (es) | 1972-11-01 |
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