DD250043B3 - Schaedlingsbekaempfungsmittel - Google Patents
Schaedlingsbekaempfungsmittel Download PDFInfo
- Publication number
- DD250043B3 DD250043B3 DD86295576A DD29557686A DD250043B3 DD 250043 B3 DD250043 B3 DD 250043B3 DD 86295576 A DD86295576 A DD 86295576A DD 29557686 A DD29557686 A DD 29557686A DD 250043 B3 DD250043 B3 DD 250043B3
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- phenyl
- alkoxy
- formula
- halogen
- alkyl
- Prior art date
Links
- -1 (substituted) phenyl Chemical group 0.000 claims abstract description 258
- 150000001875 compounds Chemical class 0.000 claims abstract description 56
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 29
- 150000002367 halogens Chemical class 0.000 claims abstract description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 29
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 6
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 125000005545 phthalimidyl group Chemical group 0.000 claims abstract description 4
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 4
- MNLVCBKWEVXHGE-UHFFFAOYSA-N [CH]1[CH]CC[CH]1 Chemical compound [CH]1[CH]CC[CH]1 MNLVCBKWEVXHGE-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000001721 carbon Chemical group 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000002541 furyl group Chemical group 0.000 claims abstract description 3
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 21
- 150000003254 radicals Chemical class 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 238000009472 formulation Methods 0.000 claims description 10
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 229910052710 silicon Inorganic materials 0.000 claims description 7
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000002917 insecticide Substances 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- 125000003302 alkenyloxy group Chemical group 0.000 claims 1
- 125000005103 alkyl silyl group Chemical group 0.000 claims 1
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 1
- 125000004995 haloalkylthio group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 8
- 230000000895 acaricidal effect Effects 0.000 abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 abstract description 4
- 230000000749 insecticidal effect Effects 0.000 abstract description 4
- 230000001069 nematicidal effect Effects 0.000 abstract description 4
- 238000000034 method Methods 0.000 description 32
- 239000004480 active ingredient Substances 0.000 description 21
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 16
- 229910000077 silane Inorganic materials 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- 239000003153 chemical reaction reagent Substances 0.000 description 11
- 125000002524 organometallic group Chemical group 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 241000238631 Hexapoda Species 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- 244000046052 Phaseolus vulgaris Species 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- 150000004756 silanes Chemical class 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 241000244206 Nematoda Species 0.000 description 5
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 4
- 241000258937 Hemiptera Species 0.000 description 4
- 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 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 150000001342 alkaline earth metals Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 125000001188 haloalkyl group Chemical group 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000238657 Blattella germanica Species 0.000 description 3
- 241000462639 Epilachna varivestis Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229910008326 Si-Y Inorganic materials 0.000 description 3
- 229910006773 Si—Y Inorganic materials 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 229940100198 alkylating agent Drugs 0.000 description 3
- 239000002168 alkylating agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 244000079386 endoparasite Species 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 230000001473 noxious effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 241001143309 Acanthoscelides obtectus Species 0.000 description 2
- 241000952611 Aphis craccivora Species 0.000 description 2
- 241000239223 Arachnida Species 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical class NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 241000257303 Hymenoptera Species 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241001481703 Rhipicephalus <genus> Species 0.000 description 2
- 241000985245 Spodoptera litura Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 241000018137 Trialeurodes vaporariorum Species 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 239000000642 acaricide Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 210000003608 fece Anatomy 0.000 description 2
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 2
- NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical class 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000005645 nematicide Substances 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 2
- 230000000737 periodic effect Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 150000003606 tin compounds Chemical class 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- ZCVAOQKBXKSDMS-PVAVHDDUSA-N (+)-trans-(S)-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-PVAVHDDUSA-N 0.000 description 1
- ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 description 1
- YATDSXRLIUJOQN-SVRRBLITSA-N (2,3,4,5,6-pentafluorophenyl)methyl (1r,3s)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=C(F)C(F)=C(F)C(F)=C1F YATDSXRLIUJOQN-SVRRBLITSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- IXGNGGPNRHNMJF-UHFFFAOYSA-N (4-ethoxyphenyl)-dimethyl-[3-(2,3,4,5,6-pentafluorophenyl)propyl]silane Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=C(F)C(F)=C(F)C(F)=C1F IXGNGGPNRHNMJF-UHFFFAOYSA-N 0.000 description 1
- DECGNXVVNBDTQK-UHFFFAOYSA-N (4-ethoxyphenyl)-dimethylsilane Chemical compound CCOC1=CC=C([SiH](C)C)C=C1 DECGNXVVNBDTQK-UHFFFAOYSA-N 0.000 description 1
- XGWIJUOSCAQSSV-XHDPSFHLSA-N (S,S)-hexythiazox Chemical compound S([C@H]([C@@H]1C)C=2C=CC(Cl)=CC=2)C(=O)N1C(=O)NC1CCCCC1 XGWIJUOSCAQSSV-XHDPSFHLSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- TVVRDLJSUQVKGY-UHFFFAOYSA-N 1-(3-chloropropyl)-3-phenoxybenzene Chemical compound ClCCCC1=CC=CC(OC=2C=CC=CC=2)=C1 TVVRDLJSUQVKGY-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- FMTFEIJHMMQUJI-NJAFHUGGSA-N 102130-98-3 Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C FMTFEIJHMMQUJI-NJAFHUGGSA-N 0.000 description 1
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- BOTNFCTYKJBUMU-UHFFFAOYSA-N 2-[4-(2-methylpropyl)piperazin-4-ium-1-yl]-2-oxoacetate Chemical compound CC(C)C[NH+]1CCN(C(=O)C([O-])=O)CC1 BOTNFCTYKJBUMU-UHFFFAOYSA-N 0.000 description 1
- GXJQMKFJQFGQKV-KHPPLWFESA-N 2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS(O)(=O)=O GXJQMKFJQFGQKV-KHPPLWFESA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- ZRDUSMYWDRPZRM-UHFFFAOYSA-N 2-sec-butyl-4,6-dinitrophenyl 3-methylbut-2-enoate Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)C=C(C)C ZRDUSMYWDRPZRM-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- SPVZAYWHHVLPBN-UHFFFAOYSA-N 3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylic acid Chemical compound CC1(C)C(C=C(Cl)C(F)(F)F)C1C(O)=O SPVZAYWHHVLPBN-UHFFFAOYSA-N 0.000 description 1
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- 238000000746 purification Methods 0.000 description 1
- QHGVXILFMXYDRS-UHFFFAOYSA-N pyraclofos Chemical compound C1=C(OP(=O)(OCC)SCCC)C=NN1C1=CC=C(Cl)C=C1 QHGVXILFMXYDRS-UHFFFAOYSA-N 0.000 description 1
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- 239000004576 sand Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004544 spot-on Substances 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- YWSCPYYRJXKUDB-KAKFPZCNSA-N tralomethrin Chemical compound CC1(C)[C@@H](C(Br)C(Br)(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 YWSCPYYRJXKUDB-KAKFPZCNSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/12—Organo silicon halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicines Containing Plant Substances (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3538139 | 1985-10-26 | ||
| DE3618354 | 1986-05-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DD250043A5 DD250043A5 (de) | 1987-09-30 |
| DD250043B3 true DD250043B3 (de) | 1993-02-25 |
Family
ID=25837330
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD86295576A DD250043B3 (de) | 1985-10-26 | 1986-10-24 | Schaedlingsbekaempfungsmittel |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US4864027A (pt) |
| EP (1) | EP0224024B1 (pt) |
| JP (1) | JP2688588B2 (pt) |
| KR (1) | KR940009030B1 (pt) |
| CN (3) | CN1032005C (pt) |
| AT (1) | ATE53998T1 (pt) |
| AU (2) | AU599932B2 (pt) |
| BR (1) | BR8605220A (pt) |
| CA (1) | CA1340979C (pt) |
| CS (2) | CS268683B2 (pt) |
| DD (1) | DD250043B3 (pt) |
| DE (1) | DE3672135D1 (pt) |
| DK (1) | DK510186A (pt) |
| EG (1) | EG17914A (pt) |
| ES (1) | ES2016793B3 (pt) |
| GR (1) | GR3000632T3 (pt) |
| HU (1) | HU202368B (pt) |
| IL (3) | IL80409A (pt) |
| MA (1) | MA20800A1 (pt) |
| MY (1) | MY101121A (pt) |
| NZ (1) | NZ218058A (pt) |
| PH (1) | PH25134A (pt) |
| PT (1) | PT83625B (pt) |
| TR (1) | TR22800A (pt) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61263988A (ja) * | 1985-05-16 | 1986-11-21 | Shionogi & Co Ltd | シリル置換エ−テル類および殺虫・殺ダニ剤 |
| US4883789A (en) * | 1986-06-02 | 1989-11-28 | Fmc Corporation | Substituted phenyltrialkylsilane insecticides |
| DE3731609A1 (de) * | 1987-09-19 | 1989-03-30 | Hoechst Ag | Verfahren zur herstellung von (aryl)-(dimethyl)-(3-(4-fluoro-3-aryloxyphenyl)propyl)silanen |
| DE3731608A1 (de) * | 1987-09-19 | 1989-03-30 | Hoechst Ag | Verfahren zur herstellung von 2-fluoro-5-allyl-diphenylethern |
| DE3810378A1 (de) * | 1988-03-26 | 1989-10-05 | Hoechst Ag | Schaedlingsbekaempfungsmittel |
| US5139785A (en) * | 1988-03-26 | 1992-08-18 | Hoechst Aktiengesellschaft | Pesticides |
| DE3810379A1 (de) * | 1988-03-26 | 1989-10-12 | Hoechst Ag | Azaneophyl- und silazaneophylsulfide, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung als schaedlingsbekaempfungsmittel |
| DE3823979A1 (de) * | 1988-07-15 | 1990-01-18 | Hoechst Ag | Verfahren zur herstellung von halosilanen |
| DE3828926A1 (de) * | 1988-08-26 | 1990-03-01 | Hoechst Ag | Verfahren zur herstellung von (aryl)-(dimethyl)-(3-arylpropyl)-silanen |
| DE3836675A1 (de) * | 1988-10-28 | 1990-05-03 | Hoechst Ag | Glykosidase-inhibitor salbostatin, verfahren zu seiner herstellung und seine verwendung |
| JPH02124893A (ja) * | 1988-11-01 | 1990-05-14 | Hitachi Chem Co Ltd | １，３−ビス（ジカルボキシフエニル）−１，１，３，３−テトラフエニルジシロキサン誘導体，その製造法及びそれを用いたポリイミドの製造法 |
| US4997944A (en) * | 1990-01-18 | 1991-03-05 | Indiana University Foundation | Aminopyridyl silanes |
| DE4005155A1 (de) * | 1990-02-17 | 1991-08-22 | Hoechst Ag | Konzentrierte waessrige emulsionen von neophanen und azaneophanen zur anwendung im pflanzenschutz |
| DE4005153A1 (de) * | 1990-02-17 | 1991-08-22 | Hoechst Ag | Hochkonzentrierte emulgierbare konzentrate von neophanen und azaneophanen zur anwendung im pflanzenschutz |
| DE4005154A1 (de) * | 1990-02-17 | 1991-08-22 | Hoechst Ag | Wasserdispergierbare granulate von neophanen und azaneophanen zur anwendung im pflanzenschutz |
| DE4023288A1 (de) * | 1990-07-21 | 1992-01-23 | Hoechst Ag | Verfahren zur herstellung von aryl-alkylmethylsilanen |
| HU206625B (en) * | 1990-07-27 | 1992-12-28 | Richter Gedeon Vegyeszet | Process for producing pharmaceutical composition containing pharmaceutically active organosilane derivatives |
| DE4031001A1 (de) * | 1990-10-01 | 1992-04-02 | Hoechst Ag | Verfahren zur herstellung von 4-ethoxyphenyl-3-arylpropyl-(dimethyl)silanen |
| TR24937A (tr) * | 1991-02-15 | 1992-07-01 | Hoechst Ag | BITKILERIN KORUNMASINDA KULLANILMAGA MAHSUS NEOFANLARIN VE AZANEOFANLARIN SUDA DISPERSIYONLAS GRANüLLERI |
| US5162560A (en) * | 1991-02-15 | 1992-11-10 | Dow Corning Corporation | Olefinic and acetylenic azasilacyclopentanes |
| KR0141464B1 (ko) * | 1993-12-01 | 1998-07-01 | 김은영 | 알릴알킬실란 화합물 및 그의 제조방법 |
| US5506269A (en) * | 1993-12-27 | 1996-04-09 | Mitsui Toatsu Chemicals, Inc. | Parasiticide employing pyrethroid type compounds |
| DE4403062A1 (de) * | 1994-02-02 | 1995-08-10 | Hoechst Schering Agrevo Gmbh | Formulierung und Verfahren zur Bekämpfung von sozialen Insekten |
| TW328044B (en) * | 1994-12-01 | 1998-03-11 | Mitsui Toatsu Chemicals | An insecticidal and acaricidal composition |
| EP0796860A3 (en) * | 1996-03-18 | 1998-08-19 | American Cyanamid Company | Difluorvinylsilane insecticidal and acaridal agents |
| US5710102A (en) * | 1996-03-18 | 1998-01-20 | American Cyanamid Company | Difluorovinylsilane insecticidal and acaricidal agents |
| MX2007006534A (es) * | 2004-12-17 | 2007-07-25 | Devgen Nv | Composiciones nematicidas. |
| US7759511B2 (en) * | 2005-01-13 | 2010-07-20 | Lg Chem, Ltd. | Liquid crystal composition comprising novel silicon containing compounds and liquid crystal display device using the same |
| US7919008B2 (en) * | 2005-01-13 | 2011-04-05 | Lg Chem, Ltd. | Liquid crystal composition comprising novel silicon containing compounds and liquid crystal display device using the same |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3334123A (en) * | 1963-10-09 | 1967-08-01 | Dow Corning | Haloethersilanes |
| US3362933A (en) * | 1963-10-09 | 1968-01-09 | Dow Corning | Polymers of haloethersilanes and their quaternary salts |
| US3925434A (en) * | 1975-01-22 | 1975-12-09 | Union Carbide Corp | The reaction of chlorosilanes with unsaturated organic compounds |
| AU553808B2 (en) * | 1981-06-24 | 1986-07-31 | E.I. Du Pont De Nemours And Company | Organosilicon derivatives of imidazolc and 1,2,4- triazole |
| DE3141860A1 (de) * | 1981-10-22 | 1983-05-05 | Bayer Ag, 5090 Leverkusen | Trifluormethyl-phenoxy-phenyl-silicium-derivate, verfahren zu ihrer herstellung und ihre verwendung als herbizide und pflanzenwuchsregulatoren |
| JPS60123491A (ja) | 1983-12-08 | 1985-07-02 | Sumitomo Chem Co Ltd | 有機ケイ素化合物、その製造法およびその化合物を有効成分とする殺虫剤 |
| JPS6153291A (ja) * | 1984-08-23 | 1986-03-17 | Sumitomo Chem Co Ltd | 有機ケイ素化合物およびそれを有効成分とする殺虫剤 |
| JPS6187687A (ja) * | 1984-10-05 | 1986-05-06 | Yoshio Katsuta | 有機ケイ素系芳香族アルカン誘導体を含有する殺虫、殺ダニ剤及びその製法 |
| JPS61229883A (ja) * | 1985-04-04 | 1986-10-14 | Sumitomo Chem Co Ltd | 有機ケイ素化合物、その製造法およびその化合物を有効成分とする殺虫剤 |
| JPS61263988A (ja) * | 1985-05-16 | 1986-11-21 | Shionogi & Co Ltd | シリル置換エ−テル類および殺虫・殺ダニ剤 |
| US4806608A (en) * | 1987-03-16 | 1989-02-21 | Loctite Corporation | Curable siloxane maleimide composition |
-
1986
- 1986-10-21 DE DE8686114578T patent/DE3672135D1/de not_active Expired - Lifetime
- 1986-10-21 ES ES86114578T patent/ES2016793B3/es not_active Expired - Lifetime
- 1986-10-21 AT AT86114578T patent/ATE53998T1/de active
- 1986-10-21 EP EP86114578A patent/EP0224024B1/de not_active Expired - Lifetime
- 1986-10-23 EG EG664/86A patent/EG17914A/xx active
- 1986-10-23 MA MA21030A patent/MA20800A1/fr unknown
- 1986-10-24 TR TR590/86A patent/TR22800A/xx unknown
- 1986-10-24 IL IL8040986A patent/IL80409A/en not_active IP Right Cessation
- 1986-10-24 DK DK510186A patent/DK510186A/da not_active Application Discontinuation
- 1986-10-24 HU HU864478A patent/HU202368B/hu not_active IP Right Cessation
- 1986-10-24 BR BR8605220A patent/BR8605220A/pt not_active IP Right Cessation
- 1986-10-24 AU AU64376/86A patent/AU599932B2/en not_active Ceased
- 1986-10-24 CS CS867727A patent/CS268683B2/cs not_active IP Right Cessation
- 1986-10-24 DD DD86295576A patent/DD250043B3/de not_active IP Right Cessation
- 1986-10-24 CA CA000521290A patent/CA1340979C/en not_active Expired - Fee Related
- 1986-10-24 JP JP61252120A patent/JP2688588B2/ja not_active Expired - Lifetime
- 1986-10-24 PH PH34413A patent/PH25134A/en unknown
- 1986-10-24 IL IL9691386A patent/IL96913A/en not_active IP Right Cessation
- 1986-10-24 NZ NZ218058A patent/NZ218058A/xx unknown
- 1986-10-25 CN CN90108829A patent/CN1032005C/zh not_active Expired - Lifetime
- 1986-10-25 CN CN86107292A patent/CN1025501C/zh not_active Expired - Lifetime
- 1986-10-25 KR KR1019860008960A patent/KR940009030B1/ko not_active IP Right Cessation
- 1986-10-27 PT PT83625A patent/PT83625B/pt not_active IP Right Cessation
- 1986-11-18 MY MYPI86000103A patent/MY101121A/en unknown
-
1988
- 1988-06-22 US US07/211,155 patent/US4864027A/en not_active Expired - Lifetime
-
1989
- 1989-05-30 US US07/359,098 patent/US4990621A/en not_active Expired - Lifetime
-
1990
- 1990-07-06 GR GR90400430T patent/GR3000632T3/el unknown
- 1990-07-18 AU AU59077/90A patent/AU636156B2/en not_active Ceased
-
1991
- 1991-01-09 IL IL96913A patent/IL96913A0/xx unknown
- 1991-12-30 CS CS914167A patent/CS416791A3/cs unknown
-
1993
- 1993-04-28 CN CN93105241A patent/CN1044661C/zh not_active Expired - Lifetime
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B3 | Exclusive patent (sect. 18(1)) | ||
| ENJ | Ceased due to non-payment of renewal fee |