DE2120862A1 - 3,5-Disubstituierte 2-Acyloxybenzoesäureanilide, Verfahren zu ihrer Herstellung und ihre insektizide und akarizide Verwendung - Google Patents
3,5-Disubstituierte 2-Acyloxybenzoesäureanilide, Verfahren zu ihrer Herstellung und ihre insektizide und akarizide VerwendungInfo
- Publication number
- DE2120862A1 DE2120862A1 DE19712120862 DE2120862A DE2120862A1 DE 2120862 A1 DE2120862 A1 DE 2120862A1 DE 19712120862 DE19712120862 DE 19712120862 DE 2120862 A DE2120862 A DE 2120862A DE 2120862 A1 DE2120862 A1 DE 2120862A1
- Authority
- DE
- Germany
- Prior art keywords
- stands
- alkyl
- acid
- acid anilides
- carbon atoms
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 239000002253 acid Substances 0.000 title claims description 27
- 150000003931 anilides Chemical class 0.000 title claims description 25
- 238000002360 preparation method Methods 0.000 title claims description 12
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 title claims description 11
- 230000000895 acaricidal effect Effects 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 9
- 230000000749 insecticidal effect Effects 0.000 title claims description 8
- 239000000460 chlorine Substances 0.000 claims description 80
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 241000238631 Hexapoda Species 0.000 claims description 12
- -1 3,5-disubstituted 2-hydroxybenzoic acid anilides Chemical class 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 241000238876 Acari Species 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 239000011230 binding agent Substances 0.000 claims description 6
- 241001454295 Tetranychidae Species 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001805 chlorine compounds Chemical class 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 claims 1
- 239000004744 fabric Substances 0.000 claims 1
- 239000002917 insecticide Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 39
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 230000006378 damage Effects 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 239000003995 emulsifying agent Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 241001454294 Tetranychus Species 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 240000007124 Brassica oleracea Species 0.000 description 5
- 210000003298 dental enamel Anatomy 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 241000258937 Hemiptera Species 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 244000046052 Phaseolus vulgaris Species 0.000 description 4
- 241000500439 Plutella Species 0.000 description 4
- 241001454293 Tetranychus urticae Species 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 3
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 3
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 3
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 3
- 241001608568 Phaedon Species 0.000 description 3
- 241000500437 Plutella xylostella Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical compound C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241001124076 Aphididae Species 0.000 description 2
- 206010004194 Bed bug infestation Diseases 0.000 description 2
- 235000011303 Brassica alboglabra Nutrition 0.000 description 2
- 235000011302 Brassica oleracea Nutrition 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241001414835 Cimicidae Species 0.000 description 2
- 241001465977 Coccoidea Species 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 241000721703 Lymantria dispar Species 0.000 description 2
- 241000721621 Myzus persicae Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ZZNADTCEUJQVLB-UHFFFAOYSA-N OC(C(Br)=CC(Cl)=C1)=C1C(NC1=CC=CC=C1)=O Chemical compound OC(C(Br)=CC(Cl)=C1)=C1C(NC1=CC=CC=C1)=O ZZNADTCEUJQVLB-UHFFFAOYSA-N 0.000 description 2
- 241000488583 Panonychus ulmi Species 0.000 description 2
- 241001608567 Phaedon cochleariae Species 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- 241001396980 Phytonemus pallidus Species 0.000 description 2
- 241000255969 Pieris brassicae Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 235000001537 Ribes X gardonianum Nutrition 0.000 description 2
- 235000001535 Ribes X utile Nutrition 0.000 description 2
- 235000016919 Ribes petraeum Nutrition 0.000 description 2
- 244000281247 Ribes rubrum Species 0.000 description 2
- 235000002355 Ribes spicatum Nutrition 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000013256 coordination polymer Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000008187 granular material Substances 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
- 239000006072 paste Substances 0.000 description 2
- 239000003495 polar organic solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000011435 rock Substances 0.000 description 2
- WKEDVNSFRWHDNR-UHFFFAOYSA-N salicylanilide Chemical class OC1=CC=CC=C1C(=O)NC1=CC=CC=C1 WKEDVNSFRWHDNR-UHFFFAOYSA-N 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 125000004953 trihalomethyl group Chemical group 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- CDIDGWDGQGVCIB-UHFFFAOYSA-N 3,5-bis(trifluoromethyl)aniline Chemical compound NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CDIDGWDGQGVCIB-UHFFFAOYSA-N 0.000 description 1
- DKKXHIJXVWEVGN-UHFFFAOYSA-N 3-bromo-5-chloro-2-hydroxybenzoyl chloride Chemical compound OC1=C(Br)C=C(Cl)C=C1C(Cl)=O DKKXHIJXVWEVGN-UHFFFAOYSA-N 0.000 description 1
- 241000218475 Agrotis segetum Species 0.000 description 1
- 241000489242 Amphitetranychus viennensis Species 0.000 description 1
- 241001425390 Aphis fabae Species 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- 241000387321 Aspidiotus nerii Species 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 241001107116 Castanospermum australe Species 0.000 description 1
- 241001221118 Cecidophyopsis ribis Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000254137 Cicadidae Species 0.000 description 1
- 241001327638 Cimex lectularius Species 0.000 description 1
- 241001479447 Coccus hesperidum Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241001094913 Cryptomyzus Species 0.000 description 1
- 241001581006 Dysaphis plantaginea Species 0.000 description 1
- 241001425477 Dysdercus Species 0.000 description 1
- 241000630736 Ephestia Species 0.000 description 1
- 241001221110 Eriophyidae Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000483001 Euproctis chrysorrhoea Species 0.000 description 1
- 241000239245 Euscelis Species 0.000 description 1
- 241000255896 Galleria mellonella Species 0.000 description 1
- 241001659688 Hercinothrips femoralis Species 0.000 description 1
- 241001251909 Hyalopterus pruni Species 0.000 description 1
- 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 1
- 241001631692 Lasiocampa quercus Species 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 241000721715 Macrosiphum Species 0.000 description 1
- 241000721714 Macrosiphum euphorbiae Species 0.000 description 1
- 241000255685 Malacosoma neustria Species 0.000 description 1
- 241000555303 Mamestra brassicae Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000237852 Mollusca Species 0.000 description 1
- 241000332345 Myzus cerasi Species 0.000 description 1
- 241000961933 Nephotettix virescens Species 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 241001491877 Operophtera brumata Species 0.000 description 1
- 241000690748 Piesma Species 0.000 description 1
- 241000952063 Polyphagotarsonemus latus Species 0.000 description 1
- 235000014441 Prunus serotina Nutrition 0.000 description 1
- 241000722238 Pseudococcus maritimus Species 0.000 description 1
- 241000722249 Rhodnius prolixus Species 0.000 description 1
- 241000125167 Rhopalosiphum padi Species 0.000 description 1
- 241001412173 Rubus canescens Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 241000256251 Spodoptera frugiperda Species 0.000 description 1
- 241000256250 Spodoptera littoralis Species 0.000 description 1
- 241000985245 Spodoptera litura Species 0.000 description 1
- 241001414989 Thysanoptera Species 0.000 description 1
- 241001238451 Tortrix viridana Species 0.000 description 1
- 241001414831 Triatoma infestans Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 241001466337 Yponomeuta Species 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical class [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- 238000009739 binding Methods 0.000 description 1
- 235000021279 black bean Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000002699 waste material Substances 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
- A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
Landscapes
- 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)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712120862 DE2120862A1 (de) | 1971-04-28 | 1971-04-28 | 3,5-Disubstituierte 2-Acyloxybenzoesäureanilide, Verfahren zu ihrer Herstellung und ihre insektizide und akarizide Verwendung |
| US246011A US3906023A (en) | 1971-04-28 | 1972-04-20 | Substituted-2-alkoxycarbonyloxy benzoic acid anilides |
| BE782677A BE782677A (fr) | 1971-04-28 | 1972-04-26 | Nouveaux anilides d'acides 2-acyloxybenzoiques disubstitues en positions 3,5, leur preparation et leurs applications comme insecticides et acaricides |
| IL39311A IL39311A (en) | 1971-04-28 | 1972-04-26 | 3,5-disubstituted 2-acyloxybenzoic acid anilides,process for their preparation and their insecticidal and acaricidal use |
| IT23531/72A IT961154B (it) | 1971-04-28 | 1972-04-26 | 2 acilossibenzanilidi 3 5 diso stituite procedimento per la loro preparazione e loro impiego inset ticida ed acaricida |
| CH627972A CH564522A5 (enExample) | 1971-04-28 | 1972-04-27 | |
| GB1957772A GB1363597A (en) | 1971-04-28 | 1972-04-27 | 2-acyloxy-benzoic acid anilides process for their preparation and their insecticidal and acaricidal use |
| FR7215311A FR2136794A5 (enExample) | 1971-04-28 | 1972-04-28 | |
| NL7205828A NL7205828A (enExample) | 1971-04-28 | 1972-04-28 | |
| US05/836,989 US4159342A (en) | 1971-04-28 | 1977-09-27 | Substituted 2-acyloxybenzoic acid anilides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712120862 DE2120862A1 (de) | 1971-04-28 | 1971-04-28 | 3,5-Disubstituierte 2-Acyloxybenzoesäureanilide, Verfahren zu ihrer Herstellung und ihre insektizide und akarizide Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2120862A1 true DE2120862A1 (de) | 1972-11-09 |
Family
ID=5806230
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712120862 Pending DE2120862A1 (de) | 1971-04-28 | 1971-04-28 | 3,5-Disubstituierte 2-Acyloxybenzoesäureanilide, Verfahren zu ihrer Herstellung und ihre insektizide und akarizide Verwendung |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3906023A (enExample) |
| BE (1) | BE782677A (enExample) |
| CH (1) | CH564522A5 (enExample) |
| DE (1) | DE2120862A1 (enExample) |
| FR (1) | FR2136794A5 (enExample) |
| GB (1) | GB1363597A (enExample) |
| IL (1) | IL39311A (enExample) |
| IT (1) | IT961154B (enExample) |
| NL (1) | NL7205828A (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55129256A (en) * | 1979-02-28 | 1980-10-06 | Isao Ozawa | Antifungal compound |
| UA82827C2 (en) * | 2000-12-18 | 2008-05-26 | Inhibitors against the production and release of inflammatory cytokines | |
| DE10222895A1 (de) * | 2002-05-23 | 2003-12-11 | Bosch Gmbh Robert | Hochdruckspeicher für Kraftstoffeinspritzsysteme mit integriertem Druckregelventil |
| TW200410671A (en) * | 2002-06-05 | 2004-07-01 | Inst Med Molecular Design Inc | Medicines for inhibiting the activation of AP-1 |
| CN101103977A (zh) * | 2002-06-05 | 2008-01-16 | 株式会社医药分子设计研究所 | 糖尿病治疗药 |
| AU2003242131A1 (en) * | 2002-06-05 | 2003-12-22 | Institute Of Medicinal Molecular Design, Inc. | Immunity-related protein kinase inhibitors |
| CN1658872B (zh) * | 2002-06-06 | 2010-09-22 | 株式会社医药分子设计研究所 | 抗过敏药 |
| CN1658855B (zh) * | 2002-06-06 | 2010-04-28 | 株式会社医药分子设计研究所 | O-取代羟基芳基衍生物 |
| EP1535610A4 (en) * | 2002-06-10 | 2008-12-31 | Inst Med Molecular Design Inc | THERAPEUTIC CANCER |
| EA010470B1 (ru) * | 2002-06-10 | 2008-08-29 | Инститьют Оф Медисинал Молекьюлар Дизайн. Инк. | ИНГИБИТОРЫ АКТИВАЦИИ NF-kB |
| EA011707B1 (ru) * | 2002-06-11 | 2009-04-28 | Инститьют Оф Медисинал Молекьюлар Дизайн. Инк. | Лекарственное средство для лечения нейродегенеративных заболеваний |
| AU2003244325A1 (en) * | 2002-11-12 | 2004-06-03 | Nok Corporation | Rubber-like elastic part |
| US7671058B2 (en) * | 2006-06-21 | 2010-03-02 | Institute Of Medicinal Molecular Design, Inc. | N-(3,4-disubstituted phenyl) salicylamide derivatives |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2476559A (en) * | 1946-10-01 | 1949-07-19 | Gen Aniline & Film Corp | Oxazine diones |
| US3147300A (en) * | 1955-09-26 | 1964-09-01 | Bayer Ag | Gastropod combating salicylanilides |
| DE1543416A1 (de) * | 1965-04-01 | 1969-09-11 | Parke Davis & Co | Verfahren zur Herstellung von halogenhaltigen 2-Acyloxybenzanilinverbindungen |
-
1971
- 1971-04-28 DE DE19712120862 patent/DE2120862A1/de active Pending
-
1972
- 1972-04-20 US US246011A patent/US3906023A/en not_active Expired - Lifetime
- 1972-04-26 BE BE782677A patent/BE782677A/xx unknown
- 1972-04-26 IL IL39311A patent/IL39311A/xx unknown
- 1972-04-26 IT IT23531/72A patent/IT961154B/it active
- 1972-04-27 CH CH627972A patent/CH564522A5/xx not_active IP Right Cessation
- 1972-04-27 GB GB1957772A patent/GB1363597A/en not_active Expired
- 1972-04-28 FR FR7215311A patent/FR2136794A5/fr not_active Expired
- 1972-04-28 NL NL7205828A patent/NL7205828A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IT961154B (it) | 1973-12-10 |
| GB1363597A (en) | 1974-08-14 |
| FR2136794A5 (enExample) | 1972-12-22 |
| BE782677A (fr) | 1972-10-26 |
| IL39311A0 (en) | 1972-06-28 |
| CH564522A5 (enExample) | 1975-07-31 |
| NL7205828A (enExample) | 1972-10-31 |
| IL39311A (en) | 1975-11-25 |
| US3906023A (en) | 1975-09-16 |
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