NO135470B - - Google Patents
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- Publication number
- NO135470B NO135470B NO572/73A NO57273A NO135470B NO 135470 B NO135470 B NO 135470B NO 572/73 A NO572/73 A NO 572/73A NO 57273 A NO57273 A NO 57273A NO 135470 B NO135470 B NO 135470B
- Authority
- NO
- Norway
- Prior art keywords
- compound
- ether
- propylthio
- compounds
- propylsulfinyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 60
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 230000000895 acaricidal effect Effects 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- 229910052757 nitrogen Inorganic materials 0.000 description 28
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000013078 crystal Substances 0.000 description 14
- 238000000921 elemental analysis Methods 0.000 description 14
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- -1 3- amylthio-4-chlorophenol Chemical compound 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 241000238876 Acari Species 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 235000013601 eggs Nutrition 0.000 description 9
- WWGMCNVDBQVYIG-UHFFFAOYSA-N 4-methyl-3-propylsulfanylphenol Chemical compound CCCSC1=CC(O)=CC=C1C WWGMCNVDBQVYIG-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 241001454293 Tetranychus urticae Species 0.000 description 5
- 239000000642 acaricide Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- 241000488581 Panonychus citri Species 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- BGDCQZFFNFXYQC-UHFFFAOYSA-N 1-chloro-2-methyl-4-nitrobenzene Chemical compound CC1=CC([N+]([O-])=O)=CC=C1Cl BGDCQZFFNFXYQC-UHFFFAOYSA-N 0.000 description 3
- JDTMUJBWSGNMGR-UHFFFAOYSA-N 1-nitro-4-phenoxybenzene Chemical class C1=CC([N+](=O)[O-])=CC=C1OC1=CC=CC=C1 JDTMUJBWSGNMGR-UHFFFAOYSA-N 0.000 description 3
- CFPIGEXZPWTNOR-UHFFFAOYSA-N 4-chloro-1-nitro-2-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1C(F)(F)F CFPIGEXZPWTNOR-UHFFFAOYSA-N 0.000 description 3
- FLNUAZNTVKRTPO-UHFFFAOYSA-N 4-chloro-3-propylsulfanylphenol Chemical compound CCCSC1=CC(O)=CC=C1Cl FLNUAZNTVKRTPO-UHFFFAOYSA-N 0.000 description 3
- GOZHYHNLGPCNPO-UHFFFAOYSA-N 4-chloro-3-propylsulfinylphenol Chemical compound CCCS(=O)C1=CC(O)=CC=C1Cl GOZHYHNLGPCNPO-UHFFFAOYSA-N 0.000 description 3
- KCNSCDOKYZTNGP-UHFFFAOYSA-N 4-methyl-3-propylsulfonylphenol Chemical compound CCCS(=O)(=O)C1=CC(O)=CC=C1C KCNSCDOKYZTNGP-UHFFFAOYSA-N 0.000 description 3
- JTAWVCZUHBOEPM-UHFFFAOYSA-N C(CC)S(=O)C=1C=C(C=CC1OC)O Chemical compound C(CC)S(=O)C=1C=C(C=CC1OC)O JTAWVCZUHBOEPM-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- ZULNPOUURDISTK-UHFFFAOYSA-N 4-bromo-3-propylsulfanylphenol Chemical compound C(CC)SC=1C=C(C=CC1Br)O ZULNPOUURDISTK-UHFFFAOYSA-N 0.000 description 2
- ABEUJUYEUCCZQF-UHFFFAOYSA-N 4-chloro-2-methoxy-1-nitrobenzene Chemical compound COC1=CC(Cl)=CC=C1[N+]([O-])=O ABEUJUYEUCCZQF-UHFFFAOYSA-N 0.000 description 2
- KOSDSVOGPOBPHW-UHFFFAOYSA-N 4-chloro-3-ethylsulfanylphenol Chemical compound CCSC1=CC(O)=CC=C1Cl KOSDSVOGPOBPHW-UHFFFAOYSA-N 0.000 description 2
- VDEOSERJRRJBQX-UHFFFAOYSA-N 4-methyl-3-propylsulfinylphenol Chemical compound CCCS(=O)C1=CC(O)=CC=C1C VDEOSERJRRJBQX-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 244000144730 Amygdalus persica Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KCFGAHJSBKQGPI-UHFFFAOYSA-N C(CC)S(=O)C=1C=C(C=CC1Br)O Chemical compound C(CC)S(=O)C=1C=C(C=CC1Br)O KCFGAHJSBKQGPI-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RAPBNVDSDCTNRC-UHFFFAOYSA-N Chlorobenzilate Chemical compound C=1C=C(Cl)C=CC=1C(O)(C(=O)OCC)C1=CC=C(Cl)C=C1 RAPBNVDSDCTNRC-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 244000141359 Malus pumila Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000218231 Moraceae Species 0.000 description 2
- 235000008708 Morus alba Nutrition 0.000 description 2
- 235000006040 Prunus persica var persica Nutrition 0.000 description 2
- 241000220324 Pyrus Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 235000021016 apples Nutrition 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 235000021017 pears Nutrition 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- NTBYINQTYWZXLH-UHFFFAOYSA-N 1,2-dichloro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(Cl)=C1 NTBYINQTYWZXLH-UHFFFAOYSA-N 0.000 description 1
- JXIJUAWSDBACEB-UHFFFAOYSA-N 1-chloro-2-methoxy-4-nitrobenzene Chemical compound COC1=CC([N+]([O-])=O)=CC=C1Cl JXIJUAWSDBACEB-UHFFFAOYSA-N 0.000 description 1
- XQCLSNIGOKBZRS-UHFFFAOYSA-N 1-chloro-2-methylsulfanyl-4-nitrobenzene Chemical compound CSC1=CC([N+]([O-])=O)=CC=C1Cl XQCLSNIGOKBZRS-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
- DURYCUGTJCWVAW-UHFFFAOYSA-N 3-ethylsulfonyl-4-methoxyphenol Chemical compound CCS(=O)(=O)C1=CC(O)=CC=C1OC DURYCUGTJCWVAW-UHFFFAOYSA-N 0.000 description 1
- AKHBCQPGESWQFN-UHFFFAOYSA-N 4-bromo-3-propylsulfonylphenol Chemical compound CCCS(=O)(=O)C1=CC(O)=CC=C1Br AKHBCQPGESWQFN-UHFFFAOYSA-N 0.000 description 1
- NSMZCUAVEOTJDS-UHFFFAOYSA-N 4-chloro-2-methyl-1-nitrobenzene Chemical compound CC1=CC(Cl)=CC=C1[N+]([O-])=O NSMZCUAVEOTJDS-UHFFFAOYSA-N 0.000 description 1
- XMEYYAFJTIZCEJ-UHFFFAOYSA-N 4-chloro-3-propylsulfonylphenol Chemical compound CCCS(=O)(=O)C1=CC(O)=CC=C1Cl XMEYYAFJTIZCEJ-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- PAZGAXGUXHDVDL-UHFFFAOYSA-N C(CC)SC=1C=C(C=CC1[N+](=O)[O-])O Chemical compound C(CC)SC=1C=C(C=CC1[N+](=O)[O-])O PAZGAXGUXHDVDL-UHFFFAOYSA-N 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 235000008694 Humulus lupulus Nutrition 0.000 description 1
- 244000025221 Humulus lupulus Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 239000005909 Kieselgur Substances 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000488583 Panonychus ulmi Species 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 244000061458 Solanum melongena Species 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- 244000223014 Syzygium aromaticum Species 0.000 description 1
- 235000016639 Syzygium aromaticum Nutrition 0.000 description 1
- 241000488589 Tetranychus kanzawai Species 0.000 description 1
- 241000488533 Tetranychus viennensis Species 0.000 description 1
- 240000006677 Vicia faba Species 0.000 description 1
- 235000010749 Vicia faba Nutrition 0.000 description 1
- 235000002098 Vicia faba var. major Nutrition 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 238000004458 analytical method Methods 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
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 229960004132 diethyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 235000005489 dwarf bean Nutrition 0.000 description 1
- 244000013123 dwarf bean Species 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 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 1
- 239000003350 kerosene Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 231100000194 ovacidal Toxicity 0.000 description 1
- 230000003151 ovacidal effect Effects 0.000 description 1
- 230000017448 oviposition Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-OUBTZVSYSA-N potassium-40 Chemical compound [40K] ZLMJMSJWJFRBEC-OUBTZVSYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000020095 red wine Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP47014865A JPS529732B2 (cs) | 1972-02-14 | 1972-02-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO135470B true NO135470B (cs) | 1977-01-03 |
| NO135470C NO135470C (cs) | 1977-04-13 |
Family
ID=11872904
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO572/73A NO135470C (cs) | 1972-02-14 | 1973-02-13 |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US3857954A (cs) |
| JP (1) | JPS529732B2 (cs) |
| AR (1) | AR196905A1 (cs) |
| AT (1) | AT322906B (cs) |
| AU (1) | AU470132B2 (cs) |
| BE (1) | BE795355A (cs) |
| BG (1) | BG22777A3 (cs) |
| BR (1) | BR7301076D0 (cs) |
| CA (1) | CA1017360A (cs) |
| CH (2) | CH592618A5 (cs) |
| CS (1) | CS172966B2 (cs) |
| DD (1) | DD108030A5 (cs) |
| DK (1) | DK137720B (cs) |
| EG (1) | EG11645A (cs) |
| FR (1) | FR2172199B1 (cs) |
| GB (1) | GB1395451A (cs) |
| HU (1) | HU166282B (cs) |
| IL (1) | IL41222A (cs) |
| IT (1) | IT979065B (cs) |
| LU (1) | LU67018A1 (cs) |
| NL (1) | NL7301634A (cs) |
| NO (1) | NO135470C (cs) |
| RO (1) | RO71876A (cs) |
| SE (1) | SE403476B (cs) |
| SU (1) | SU540564A3 (cs) |
| ZA (1) | ZA73490B (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4091109A (en) * | 1976-06-18 | 1978-05-23 | Nippon Kayaku Kabushiki Kaisha | Diphenylether derivatives and use thereof as an acaricide |
| JPS6341451A (ja) * | 1986-08-06 | 1988-02-22 | Nippon Kayaku Co Ltd | エ−テル誘導体およびそれを有効成分とする殺ダニ、殺虫組成物 |
| MXPA05012669A (es) * | 2003-05-20 | 2007-06-14 | Flexitral Inc | Alcoxi alquilosulfanil feniles. |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3506720A (en) * | 1963-02-22 | 1970-04-14 | Geigy Chem Corp | Halogenated hydroxy-diphenyl ethers |
| CH480012A (de) * | 1966-11-11 | 1969-10-31 | Ciba Geigy | Schädlingsbekämpfungsmittel |
| CA956974A (en) * | 1970-06-22 | 1974-10-29 | Yasunori Abe | Compounds having the herbicidal effect and the process for the manufacture thereof |
-
0
- BE BE795355D patent/BE795355A/xx unknown
-
1972
- 1972-02-14 JP JP47014865A patent/JPS529732B2/ja not_active Expired
-
1973
- 1973-01-02 IL IL41222A patent/IL41222A/en unknown
- 1973-01-23 ZA ZA730490A patent/ZA73490B/xx unknown
- 1973-02-02 GB GB534073A patent/GB1395451A/en not_active Expired
- 1973-02-06 AU AU51869/73A patent/AU470132B2/en not_active Expired
- 1973-02-06 NL NL7301634A patent/NL7301634A/xx not_active Application Discontinuation
- 1973-02-11 EG EG53/73A patent/EG11645A/xx active
- 1973-02-12 AR AR246531A patent/AR196905A1/es active
- 1973-02-12 CH CH197973A patent/CH592618A5/xx not_active IP Right Cessation
- 1973-02-12 DD DD169164A patent/DD108030A5/xx unknown
- 1973-02-12 CH CH318476A patent/CH590604A5/xx not_active IP Right Cessation
- 1973-02-13 LU LU67018A patent/LU67018A1/xx unknown
- 1973-02-13 HU HUNI160A patent/HU166282B/hu unknown
- 1973-02-13 RO RO7373824A patent/RO71876A/ro unknown
- 1973-02-13 DK DK76973AA patent/DK137720B/da unknown
- 1973-02-13 SE SE7301992A patent/SE403476B/xx unknown
- 1973-02-13 NO NO572/73A patent/NO135470C/no unknown
- 1973-02-13 BG BG022713A patent/BG22777A3/xx unknown
- 1973-02-13 IT IT20334/73A patent/IT979065B/it active
- 1973-02-13 CA CA163,601A patent/CA1017360A/en not_active Expired
- 1973-02-13 SU SU1886152A patent/SU540564A3/ru active
- 1973-02-13 AT AT128073A patent/AT322906B/de not_active IP Right Cessation
- 1973-02-13 US US00332181A patent/US3857954A/en not_active Expired - Lifetime
- 1973-02-14 FR FR7305134A patent/FR2172199B1/fr not_active Expired
- 1973-02-14 CS CS1083A patent/CS172966B2/cs unknown
- 1973-02-14 BR BR731076A patent/BR7301076D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK137720B (da) | 1978-04-24 |
| DD108030A5 (cs) | 1974-09-05 |
| CA1017360A (en) | 1977-09-13 |
| AU470132B2 (en) | 1976-03-04 |
| IL41222A0 (en) | 1973-03-30 |
| NL7301634A (cs) | 1973-08-16 |
| FR2172199A1 (cs) | 1973-09-28 |
| US3857954A (en) | 1974-12-31 |
| NO135470C (cs) | 1977-04-13 |
| SU540564A3 (ru) | 1976-12-25 |
| CH592618A5 (cs) | 1977-10-31 |
| BG22777A3 (bg) | 1977-04-20 |
| IL41222A (en) | 1976-01-30 |
| DE2307248B2 (de) | 1976-09-23 |
| CH590604A5 (cs) | 1977-08-15 |
| CS172966B2 (cs) | 1977-01-28 |
| FR2172199B1 (cs) | 1977-08-19 |
| SE403476B (sv) | 1978-08-21 |
| DK137720C (cs) | 1978-10-02 |
| GB1395451A (en) | 1975-05-29 |
| AR196905A1 (es) | 1974-02-28 |
| JPS529732B2 (cs) | 1977-03-18 |
| LU67018A1 (cs) | 1973-05-15 |
| EG11645A (en) | 1977-10-31 |
| ZA73490B (en) | 1973-10-31 |
| IT979065B (it) | 1974-09-30 |
| BR7301076D0 (pt) | 1973-09-20 |
| BE795355A (fr) | 1973-05-29 |
| JPS4885731A (cs) | 1973-11-13 |
| DE2307248A1 (de) | 1973-08-23 |
| AU5186973A (en) | 1974-08-08 |
| RO71876A (ro) | 1982-02-26 |
| HU166282B (cs) | 1975-02-28 |
| AT322906B (de) | 1975-06-10 |
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