DE3029280A1 - Additionsverbindungen von 4-hydroxycumarin- bzw. 1-hydroxy-3-oxoind-1-enderivaten, verfahren zu ihrer herstellung und solche enthaltende rodenticide - Google Patents
Additionsverbindungen von 4-hydroxycumarin- bzw. 1-hydroxy-3-oxoind-1-enderivaten, verfahren zu ihrer herstellung und solche enthaltende rodenticideInfo
- Publication number
- DE3029280A1 DE3029280A1 DE19803029280 DE3029280A DE3029280A1 DE 3029280 A1 DE3029280 A1 DE 3029280A1 DE 19803029280 DE19803029280 DE 19803029280 DE 3029280 A DE3029280 A DE 3029280A DE 3029280 A1 DE3029280 A1 DE 3029280A1
- Authority
- DE
- Germany
- Prior art keywords
- radical
- hydroxy
- general formula
- oxoind
- phenylacetyl
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims description 62
- 239000003128 rodenticide Substances 0.000 title claims description 49
- 238000000034 method Methods 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title description 10
- 239000012141 concentrate Substances 0.000 claims description 65
- -1 Isobutyl- Chemical group 0.000 claims description 63
- 239000004480 active ingredient Substances 0.000 claims description 44
- 150000001412 amines Chemical class 0.000 claims description 44
- VXIXUWQIVKSKSA-UHFFFAOYSA-N 4-hydroxycoumarin Chemical compound C1=CC=CC2=C1OC(=O)C=C2O VXIXUWQIVKSKSA-UHFFFAOYSA-N 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 30
- 239000003921 oil Substances 0.000 claims description 30
- 235000019198 oils Nutrition 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 239000007788 liquid Substances 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 15
- 239000007787 solid Substances 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000001298 alcohols Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 231100001184 nonphytotoxic Toxicity 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 230000002195 synergetic effect Effects 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 230000002708 enhancing effect Effects 0.000 claims description 2
- 239000005871 repellent Substances 0.000 claims description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 2
- 239000008158 vegetable oil Substances 0.000 claims description 2
- 230000002940 repellent Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 24
- UHKAJLSKXBADFT-UHFFFAOYSA-N 1,3-indandione Chemical class C1=CC=C2C(=O)CC(=O)C2=C1 UHKAJLSKXBADFT-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- 239000007983 Tris buffer Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 230000001119 rodenticidal effect Effects 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 241000283984 Rodentia Species 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 229940099259 vaseline Drugs 0.000 description 8
- MFNHXHPEFJPDKK-UHFFFAOYSA-N 2-(2,2-diphenylacetyl)-3-hydroxyinden-1-one Chemical compound O=C1C2=CC=CC=C2C(O)=C1C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 MFNHXHPEFJPDKK-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- UDHXJZHVNHGCEC-UHFFFAOYSA-N Chlorophacinone Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)C(=O)C1C(=O)C2=CC=CC=C2C1=O UDHXJZHVNHGCEC-UHFFFAOYSA-N 0.000 description 7
- 239000004464 cereal grain Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- JYGLAHSAISAEAL-UHFFFAOYSA-N Diphenadione Chemical compound O=C1C2=CC=CC=C2C(=O)C1C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 JYGLAHSAISAEAL-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 150000002085 enols Chemical group 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- DTFNUCZNYWVBRK-UHFFFAOYSA-N O=C1C2=CC=CC=C2C(O)=C1C(=O)C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 Chemical compound O=C1C2=CC=CC=C2C(O)=C1C(=O)C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 DTFNUCZNYWVBRK-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 235000019486 Sunflower oil Nutrition 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 239000004495 emulsifiable concentrate Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000011833 salt mixture Substances 0.000 description 4
- 239000002600 sunflower oil Substances 0.000 description 4
- 235000013311 vegetables Nutrition 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 description 3
- ULSLJYXHZDTLQK-UHFFFAOYSA-N Coumatetralyl Chemical group C1=CC=CC2=C1OC(=O)C(C1C3=CC=CC=C3CCC1)=C2O ULSLJYXHZDTLQK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000699705 Ondatra Species 0.000 description 2
- 239000005662 Paraffin oil Substances 0.000 description 2
- RZKYEQDPDZUERB-UHFFFAOYSA-N Pindone Chemical compound C1=CC=C2C(=O)C(C(=O)C(C)(C)C)C(=O)C2=C1 RZKYEQDPDZUERB-UHFFFAOYSA-N 0.000 description 2
- BAECOWNUKCLBPZ-HIUWNOOHSA-N Triolein Natural products O([C@H](OCC(=O)CCCCCCC/C=C\CCCCCCCC)COC(=O)CCCCCCC/C=C\CCCCCCCC)C(=O)CCCCCCC/C=C\CCCCCCCC BAECOWNUKCLBPZ-HIUWNOOHSA-N 0.000 description 2
- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 239000003146 anticoagulant agent Substances 0.000 description 2
- 229940127219 anticoagulant drug Drugs 0.000 description 2
- 235000019568 aromas Nutrition 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- AFYCEAFSNDLKSX-UHFFFAOYSA-N coumarin 460 Chemical class CC1=CC(=O)OC2=CC(N(CC)CC)=CC=C21 AFYCEAFSNDLKSX-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 235000011869 dried fruits Nutrition 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000012261 resinous substance Substances 0.000 description 2
- 230000035943 smell Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 2
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 2
- 229960005080 warfarin Drugs 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- PJLHSJWRNNCCEA-UHFFFAOYSA-N 2-(2,2-dimethylpropanoyl)-3-hydroxyinden-1-one Chemical compound C1=CC=C2C(=O)C(C(=O)C(C)(C)C)=C(O)C2=C1 PJLHSJWRNNCCEA-UHFFFAOYSA-N 0.000 description 1
- WNNMZEZFZJIRNB-UHFFFAOYSA-N 2-[2-(4-bromophenyl)-2-phenylacetyl]indene-1,3-dione Chemical compound Brc1ccc(cc1)C(C(=O)C1C(=O)c2ccccc2C1=O)c1ccccc1 WNNMZEZFZJIRNB-UHFFFAOYSA-N 0.000 description 1
- DJQWSIGATNDGBR-UHFFFAOYSA-N 2-[2-(4-methylphenyl)-2-phenylacetyl]indene-1,3-dione Chemical compound C1=CC(C)=CC=C1C(C=1C=CC=CC=1)C(=O)C1C(=O)C2=CC=CC=C2C1=O DJQWSIGATNDGBR-UHFFFAOYSA-N 0.000 description 1
- NESQNDMXYPJEQS-UHFFFAOYSA-N 2-methylbutan-1-one Chemical compound CCC(C)[C]=O NESQNDMXYPJEQS-UHFFFAOYSA-N 0.000 description 1
- KTOQRRDVVIDEAA-UHFFFAOYSA-N 2-methylpropane Chemical compound [CH2]C(C)C KTOQRRDVVIDEAA-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- DEKWZWCFHUABHE-UHFFFAOYSA-N Coumachlor Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=C(Cl)C=C1 DEKWZWCFHUABHE-UHFFFAOYSA-N 0.000 description 1
- JFIXKFSJCQNGEK-UHFFFAOYSA-N Coumafuryl Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CO1 JFIXKFSJCQNGEK-UHFFFAOYSA-N 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 239000004129 EU approved improving agent Substances 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 244000141359 Malus pumila Species 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
- YQUDZELTQBBBQI-UHFFFAOYSA-N OC1=C(C(=O)C(C2=CC=CC=C2)C2=CC=C(Br)C=C2)C(=O)C2=C1C=CC=C2 Chemical compound OC1=C(C(=O)C(C2=CC=CC=C2)C2=CC=C(Br)C=C2)C(=O)C2=C1C=CC=C2 YQUDZELTQBBBQI-UHFFFAOYSA-N 0.000 description 1
- 241000699700 Ondatra zibethicus Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- VKWNTWQXVLKCSG-ZDXBJJIESA-N Sudan Red 7B Chemical compound CCNC1=CC=C2C=CC=CC2=C1\N=N\C(C=C1)=CC=C1\N=N\C1=CC=CC=C1 VKWNTWQXVLKCSG-ZDXBJJIESA-N 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 241001464837 Viridiplantae Species 0.000 description 1
- MECHNRXZTMCUDQ-UHFFFAOYSA-N Vitamin D2 Natural products C1CCC2(C)C(C(C)C=CC(C)C(C)C)CCC2C1=CC=C1CC(O)CCC1=C MECHNRXZTMCUDQ-UHFFFAOYSA-N 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 229960002061 ergocalciferol Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229940013317 fish oils Drugs 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 239000012052 hydrophilic carrier Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003993 interaction Effects 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
- 231100001231 less toxic Toxicity 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- NHLUVTZJQOJKCC-UHFFFAOYSA-N n,n-dimethylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCN(C)C NHLUVTZJQOJKCC-UHFFFAOYSA-N 0.000 description 1
- MJCJUDJQDGGKOX-UHFFFAOYSA-N n-dodecyldodecan-1-amine Chemical compound CCCCCCCCCCCCNCCCCCCCCCCCC MJCJUDJQDGGKOX-UHFFFAOYSA-N 0.000 description 1
- HKUFIYBZNQSHQS-UHFFFAOYSA-N n-octadecyloctadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCNCCCCCCCCCCCCCCCCCC HKUFIYBZNQSHQS-UHFFFAOYSA-N 0.000 description 1
- PZFYOFFTIYJCEW-UHFFFAOYSA-N n-tridecyltridecan-1-amine Chemical compound CCCCCCCCCCCCCNCCCCCCCCCCCCC PZFYOFFTIYJCEW-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- GPTFURBXHJWNHR-UHFFFAOYSA-N protopine acetate Natural products C1=C2C(=O)CC3=CC=C4OCOC4=C3CN(C)CCC2=CC2=C1OCO2 GPTFURBXHJWNHR-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000012262 resinous product Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 description 1
- 235000001892 vitamin D2 Nutrition 0.000 description 1
- 239000011653 vitamin D2 Substances 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 101150061972 zur gene Proteins 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/42—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4
- C07D311/56—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 without hydrogen atoms in position 3
-
- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/42—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4
- C07D311/44—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3
- C07D311/46—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 with one hydrogen atom in position 3 unsubstituted in the carbocyclic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (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)
- Pest Control & Pesticides (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU77RE654A HU177497B (en) | 1979-08-01 | 1979-08-01 | Acaricide preparation further process for preparing the active materials |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3029280A1 true DE3029280A1 (de) | 1981-02-26 |
Family
ID=11000780
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803029280 Withdrawn DE3029280A1 (de) | 1979-08-01 | 1980-08-01 | Additionsverbindungen von 4-hydroxycumarin- bzw. 1-hydroxy-3-oxoind-1-enderivaten, verfahren zu ihrer herstellung und solche enthaltende rodenticide |
Country Status (15)
| Country | Link |
|---|---|
| AT (1) | AT368680B (fr) |
| BG (2) | BG46302A3 (fr) |
| CH (1) | CH650258A5 (fr) |
| CS (1) | CS244658B2 (fr) |
| CU (1) | CU35299A (fr) |
| DD (1) | DD279370A7 (fr) |
| DE (1) | DE3029280A1 (fr) |
| FR (1) | FR2462435B1 (fr) |
| GB (1) | GB2055831B (fr) |
| HU (1) | HU177497B (fr) |
| IT (1) | IT1132274B (fr) |
| MN (1) | MN330A8 (fr) |
| PL (1) | PL129076B1 (fr) |
| SU (2) | SU1584736A3 (fr) |
| YU (1) | YU48445B (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2048090B1 (es) * | 1992-01-31 | 1994-10-01 | Rovi Lab Farmaceut Sa | Procedimiento para la obtencion de nuevos antitromboticos derivados de la cumarina. |
| RU2732014C1 (ru) * | 2019-12-17 | 2020-09-10 | Федеральное государственное бюджетное образовательное учреждение высшего образования "МИРЭА - Российский технологический университет" | Полиморфная модификация 3,4-дигидро-2-метокси-2-метил-4-фенил-2Н,5Н-пирано[3,2-c]бензопиран-5-она, способ ее получения и применение в качестве родентицидного средства |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2687365A (en) * | 1951-07-18 | 1954-08-24 | D Con Company Inc | Warfarin rodenticide bait composition and process of making same |
| US2900302A (en) * | 1956-02-27 | 1959-08-18 | Upjohn Co | Rodenticide |
| FR1601076A (en) * | 1968-02-09 | 1970-08-10 | Coumafene-contg compsns as rodenticides | |
| FR95858E (fr) * | 1968-02-28 | 1971-11-12 | Trehet Alexander Francois | Produit commercialisable pour la destruction des rats musqués. |
| DE2218893A1 (fr) * | 1971-04-21 | 1972-11-09 | ||
| DE2227843A1 (de) * | 1971-06-10 | 1972-12-14 | Lipha, Lyormaise IndustneUe Pharmaceutique, Lyone, Rhone (Frankreich) | Kodergifte |
| DE2341853A1 (de) * | 1972-08-21 | 1974-03-14 | Lipha | Rodentizidverbindungen |
| DE2753183A1 (de) * | 1977-01-21 | 1978-07-27 | Reanal Finomvegyszergyar | Rodenticide mittel und verfahren zur herstellung derselben |
-
1979
- 1979-08-01 HU HU77RE654A patent/HU177497B/hu unknown
-
1980
- 1980-05-10 MN MN80588A patent/MN330A8/xx unknown
- 1980-07-30 FR FR8016803A patent/FR2462435B1/fr not_active Expired
- 1980-07-31 AT AT0396580A patent/AT368680B/de not_active IP Right Cessation
- 1980-07-31 SU SU802957251A patent/SU1584736A3/ru active
- 1980-07-31 BG BG48692A patent/BG46302A3/xx unknown
- 1980-07-31 CS CS805365A patent/CS244658B2/cs unknown
- 1980-07-31 CH CH5865/80A patent/CH650258A5/de not_active IP Right Cessation
- 1980-07-31 IT IT23850/80A patent/IT1132274B/it active
- 1980-07-31 PL PL1980225992A patent/PL129076B1/pl unknown
- 1980-08-01 DE DE19803029280 patent/DE3029280A1/de not_active Withdrawn
- 1980-08-01 DD DD80223065A patent/DD279370A7/de unknown
- 1980-08-01 YU YU195380A patent/YU48445B/sh unknown
- 1980-08-01 GB GB8025214A patent/GB2055831B/en not_active Expired
- 1980-08-01 CU CU8035299A patent/CU35299A/es unknown
- 1980-12-26 BG BG50178A patent/BG45854A3/xx unknown
-
1981
- 1981-03-27 SU SU813262401A patent/SU1181537A3/ru active
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2687365A (en) * | 1951-07-18 | 1954-08-24 | D Con Company Inc | Warfarin rodenticide bait composition and process of making same |
| US2900302A (en) * | 1956-02-27 | 1959-08-18 | Upjohn Co | Rodenticide |
| FR1601076A (en) * | 1968-02-09 | 1970-08-10 | Coumafene-contg compsns as rodenticides | |
| FR95858E (fr) * | 1968-02-28 | 1971-11-12 | Trehet Alexander Francois | Produit commercialisable pour la destruction des rats musqués. |
| DE2218893A1 (fr) * | 1971-04-21 | 1972-11-09 | ||
| DE2227843A1 (de) * | 1971-06-10 | 1972-12-14 | Lipha, Lyormaise IndustneUe Pharmaceutique, Lyone, Rhone (Frankreich) | Kodergifte |
| DE2341853A1 (de) * | 1972-08-21 | 1974-03-14 | Lipha | Rodentizidverbindungen |
| DE2753183A1 (de) * | 1977-01-21 | 1978-07-27 | Reanal Finomvegyszergyar | Rodenticide mittel und verfahren zur herstellung derselben |
Non-Patent Citations (1)
| Title |
|---|
| WEGLER, R.: Chemie der Pflanzenschutz- und Schädlingsbekämpfungsmittel, Springer Verlag, 1970, Bd. I, S. 614-627 * |
Also Published As
| Publication number | Publication date |
|---|---|
| MN330A8 (en) | 1985-06-15 |
| GB2055831B (en) | 1983-03-23 |
| YU195380A (en) | 1983-02-28 |
| YU48445B (sh) | 1998-07-10 |
| BG46302A3 (en) | 1989-11-15 |
| CH650258A5 (de) | 1985-07-15 |
| PL129076B1 (en) | 1984-03-31 |
| FR2462435A1 (fr) | 1981-02-13 |
| SU1181537A3 (ru) | 1985-09-23 |
| AT368680B (de) | 1982-10-25 |
| SU1584736A3 (ru) | 1990-08-07 |
| IT8023850A0 (it) | 1980-07-31 |
| BG45854A3 (en) | 1989-08-15 |
| GB2055831A (en) | 1981-03-11 |
| FR2462435B1 (fr) | 1987-07-17 |
| DD279370A7 (de) | 1990-06-06 |
| ATA396580A (de) | 1981-11-15 |
| PL225992A1 (fr) | 1981-04-24 |
| HU177497B (en) | 1981-10-28 |
| IT1132274B (it) | 1986-07-02 |
| CS244658B2 (en) | 1986-08-14 |
| CU35299A (en) | 1982-03-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2603877C2 (de) | Oxadiazolinonverbindungen, ihre Herstellung und sie enthaltendes Mittel | |
| DE2461513A1 (de) | Morpholinderivate | |
| DE2524577C3 (de) | Substituierte Tetrahydropyran-3,5dione und 13-Dioxan-4,6-dione, Verfahren zu ihrer Herstellung und ihre Verwendung als selektive Herbicide | |
| DE1051847B (de) | Verfahren zur Herstellung von als Pflanzenwachstumsregler wirkenden ª‡-Cyan-ª‰-(polychlorphenyl)-acrylsaeuren, deren Salzen und Estern | |
| DE3029280A1 (de) | Additionsverbindungen von 4-hydroxycumarin- bzw. 1-hydroxy-3-oxoind-1-enderivaten, verfahren zu ihrer herstellung und solche enthaltende rodenticide | |
| CH657847A5 (de) | 2-(1-oximino-butyl)-5-(2-aethylthiopropyl)-3-oxy-2-cyclohexenone, herbizide zusammensetzungen, welche diese enthalten und verfahren zur bekaempfung von unkraeutern. | |
| DD160270A5 (de) | Zusammensetzung zur bekaempfung von warmbluetigem ungeziefer | |
| DE1016058B (de) | Unkrautvertilgungsmittel | |
| DE956549C (de) | Schaedlings- und Pflanzenvernichtungsmittel | |
| DE2601447B2 (de) | Cyclohexenon-derivate, verfahren zu deren herstellung und diese enthaltende herbizide mittel | |
| DE2753183C2 (de) | Rodenticides Mittel und Verfahren zu dessen Herstellung | |
| DE1913688A1 (de) | Abscisin II-Derivate und Verfahren zu ihrer Herstellung | |
| DE2349474A1 (de) | Triorganozinnverbindungen | |
| DD149891A5 (de) | Mittel zur bekaempfung von pilzerkrankungen bei pflanzen | |
| DE2457599A1 (de) | Pyran-derivate und ihre verwendung als herbicide | |
| DE1301175B (de) | Totalherbizid mit insektizider Wirkung | |
| DE1098281B (de) | Fungicides Mittel | |
| DD236868A5 (de) | Mittel zum protahieren der wirkungsdauer und zur erhoehung der selektivitaet von herbiziden zusammensetzungen | |
| AT331563B (de) | Mittel zur bekampfung von pilzen und milben | |
| AT267964B (de) | Schädlingsbekämpfungsmittel | |
| DE2551257A1 (de) | Phosphonsaeureester und insektizide mittel | |
| DD155131A5 (de) | Wachstumsregulierende zsammensetzung | |
| DE3345453C2 (fr) | ||
| DD142277A5 (de) | Herbizide zusammensetzungen | |
| DE1567217C3 (de) | Tetrachlorterephthalsäurederivate, Verfahren zu deren Herstellung und ihre Verwendung als Herbicide |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8130 | Withdrawal |