CH480786A - Verwendung von Pyridinverbindungen zur Bekämpfung unerwünschter Vegetation - Google Patents
Verwendung von Pyridinverbindungen zur Bekämpfung unerwünschter VegetationInfo
- Publication number
- CH480786A CH480786A CH349469A CH349469A CH480786A CH 480786 A CH480786 A CH 480786A CH 349469 A CH349469 A CH 349469A CH 349469 A CH349469 A CH 349469A CH 480786 A CH480786 A CH 480786A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- use according
- active ingredient
- pyridine compounds
- post
- Prior art date
Links
- 150000003222 pyridines Chemical class 0.000 title claims description 6
- 239000000203 mixture Substances 0.000 claims description 27
- 239000004480 active ingredient Substances 0.000 claims description 22
- 239000004094 surface-active agent Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 10
- 241000196324 Embryophyta Species 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 8
- 239000012141 concentrate Substances 0.000 claims description 7
- 239000000375 suspending agent Substances 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 239000006185 dispersion Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 5
- 230000008029 eradication Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 240000005979 Hordeum vulgare Species 0.000 description 5
- 235000007340 Hordeum vulgare Nutrition 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 240000008415 Lactuca sativa Species 0.000 description 4
- 235000003228 Lactuca sativa Nutrition 0.000 description 4
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 4
- 240000003768 Solanum lycopersicum Species 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 235000005822 corn Nutrition 0.000 description 4
- 230000002363 herbicidal effect Effects 0.000 description 4
- 239000004009 herbicide Substances 0.000 description 4
- 150000003568 thioethers Chemical class 0.000 description 4
- WMEXKTFKTRANOS-UHFFFAOYSA-N 2,3,5-trichloro-6-fluoro-1H-pyridine-4-thione Chemical class ClC=1C(=NC(=C(C1S)Cl)Cl)F WMEXKTFKTRANOS-UHFFFAOYSA-N 0.000 description 3
- -1 alkaline earth metal salts Chemical class 0.000 description 3
- 239000002361 compost Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000885 phytotoxic effect Effects 0.000 description 3
- LVUQDNJRAHUUSB-UHFFFAOYSA-N 2,3,5,6-tetrachloro-1h-pyridine-4-thione Chemical compound SC1=C(Cl)C(Cl)=NC(Cl)=C1Cl LVUQDNJRAHUUSB-UHFFFAOYSA-N 0.000 description 2
- NMISIPLEABYZPI-UHFFFAOYSA-N 3,5-dichloro-2,6-difluoro-1H-pyridine-4-thione Chemical compound ClC=1C(=NC(=C(C1S)Cl)F)F NMISIPLEABYZPI-UHFFFAOYSA-N 0.000 description 2
- CSMWBJGJHGWFOH-UHFFFAOYSA-N 3-chloro-2,5,6-trifluoro-1h-pyridine-4-thione Chemical compound FC=1NC(F)=C(Cl)C(=S)C=1F CSMWBJGJHGWFOH-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 230000007775 late Effects 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- FHTDDANQIMVWKZ-UHFFFAOYSA-N 1h-pyridine-4-thione Chemical class SC1=CC=NC=C1 FHTDDANQIMVWKZ-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 1
- 241000766754 Agra Species 0.000 description 1
- 241001621841 Alopecurus myosuroides Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 244000192528 Chrysanthemum parthenium Species 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- MYWUWCRYMQZMIT-UHFFFAOYSA-N FC(C(F)=NC(Cl)=C1F)=C1S Chemical class FC(C(F)=NC(Cl)=C1F)=C1S MYWUWCRYMQZMIT-UHFFFAOYSA-N 0.000 description 1
- 235000017945 Matricaria Nutrition 0.000 description 1
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 244000292693 Poa annua Species 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 244000110797 Polygonum persicaria Species 0.000 description 1
- 235000004442 Polygonum persicaria Nutrition 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229920005550 ammonium lignosulfonate Polymers 0.000 description 1
- 125000003118 aryl group Chemical group 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229920005551 calcium lignosulfonate Polymers 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- VNSBYDPZHCQWNB-UHFFFAOYSA-N calcium;aluminum;dioxido(oxo)silane;sodium;hydrate Chemical compound O.[Na].[Al].[Ca+2].[O-][Si]([O-])=O VNSBYDPZHCQWNB-UHFFFAOYSA-N 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 229910000271 hectorite Inorganic materials 0.000 description 1
- KWLMIXQRALPRBC-UHFFFAOYSA-L hectorite Chemical compound [Li+].[OH-].[OH-].[Na+].[Mg+2].O1[Si]2([O-])O[Si]1([O-])O[Si]([O-])(O1)O[Si]1([O-])O2 KWLMIXQRALPRBC-UHFFFAOYSA-L 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 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
- 239000004571 lime Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 229910000273 nontronite Inorganic materials 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000012254 powdered material Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 229910000275 saponite Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 239000003799 water insoluble solvent Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/132—Heterocyclic compounds containing only one nitrogen as hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/68—One oxygen atom attached in position 4
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
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- C—CHEMISTRY; METALLURGY
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Description
Verwendung von Pyridinverbindungen zur Bekämpfung unerwünschter Vegetation Die vorliegende Erfindung bezieht sich auf die Verwendung von Pyridin-4-thiolen der Formel zur Bekämp- fung von unerwünschter Vegetation, insbesondere von Unkraut. Auch die entsprechenden Salze sowie Thioät- her zeigen diese phytotoxische Wirkung. Das Verfahren zur Herstellung der genannten Thiole sowie deren Salze von Aether, welche die Formel EMI1.1 worin X2, X3, Xó und X6 gleich oder verschieden sein können und Fluor oder Chlor und Y Wasserstoff, den Rest eines Salzes oder den Rest einer Aethergruppe bedeuten, ist im schweizerischen Patent Nr. 472 354 beschrieben. Das Produkt bildet mit einer grossen Zahl von organischen und anorganischen Basen Salze. Ferner kann es in entsprechende Thioäther übergeführt werden. Geeignete Salze sind insbesondere die wasserlöslichen Salze, z. B. die Alkali-und Erdalkalimetallsalze. Geeignete Thioäther sind die Alkyl- (z. B. Methyl), Alkenyl (z. B. Allyl), Aryl- (z. B. Benzyl) oder heterocyclischen (z. B. Pyridyl) Thioäther. Unkrautvertilgende Gemische Die bevorzugten Verbindungen zur Verwendung in unkrautvertilgenden Gemischen sind diejenigen Thiole, worin mindestens einer der Substituenten X2, X3, X5 5 und Xe ein Fluoratom ist. Solche Verbindungen sind z. B. Chlor-trifluorpyridin-4-thiole, dessen Salze und Aether, z. B. 3-Chlor-2, 5, 6-trifluor-pyridin-4-thiol, Dichlor-difluorpyridin-4-thiole, deren Salze und Aether, z. B. 3, 5-Dichlor-2, 6-difluor-pyridin-4-thiol, und Trichlor-fluorpyridin-4-thiole deren S alze und Aether, z. B. 3, 5, 6-Trichlor-2-fluor-pyridin-4-thiol. Die erwähnten unkrautvertilgenden Gemische kön- nen entweder fest oder flüssig sein. Feste unkrautvertil- gende Gemische können in Form eines Pulvers vorlie gen, in welchem eine geringe Menge des Wirkstoffes mit einer grösseren Menge eines festen Verdünnungsmittels vermischt ist. Geeignete feste Verdünner sind z. B. pulverförmiges Kaolin, Bleicherden, Gips, Kalk, Hewitt sche Erde oder Tonerde. Im allgemeinen werden flüssige unkrautvertilgende Gemische bevorzugt, da sie zweckmässiger verwendet werden können. Flüssige unkrautvertilgende Gemische bestehen im allgemeinen aus einer wässrigen Dispersion des Wirkstoffes in ein oberflächenaktives Mittel enthaltendem Wasser. Der Wirkstoff kann als feste Teilchen oder als Tröpfchen einer Lösung des Wirkstoffes in einem in Wasser unlöslichen Lösungsmittel im Gemisch vorliegen. Mitverwendbare oberflächenaktive Mittel sind z. B. Kondensationsprodukte von Aethylenoxyd mit verschiedenen Substanzen, z. B. mit alkylierten Phenolen, z. B. Octylphenol oder Nonylphenol ; Sorbitanmonolau- rat, Oleylalkohol, Cetylalkohol oder Propylenoxyd-polymer. Andere ebenfalls befriedigende oberflächenaktive Mittel sind ferner Calciumdedecylbenzolsulfonat, Cal ciumlignosulfonat, Natriumlignosulfonat oder Ammoniumlignosulfonat. Solche Gemische können hergestellt werden, indem man den Wirkstoff in einem organischen Lösungsmittel löst und die Lösung hierauf mit dem das oberflächenaktive Mittel enthaltenden Wasser schüttelt. Vorzugsweise werden zuerst sowohl das oberflächenakti- ve Mittel als auch der Wirkstoff im Lösungsmittel gelöst, worauf die Lösung mit Wasser geschüttelt wird. Die Mengen Wirkstoff, die im Gemisch verwendet werden können, können innerhalb weiter Grenzen variieren, je nach dem zu verwendenden Wirkstoff und dem zu vertilgenden Unkraut bzw. dessen Samen. Im allgemeinen werden mit 0, 1 bis 2, 0 Gew.- /o enthaltenden Gemischen gute Ergebnisse erzielt, doch können manchmal grössere oder geringere Mengen erwünscht sein. Die Gemische werden zweckmässig in Form eines Konzentrates geliefert, das eine grössere Konzentration an Wirkstoff enthält und deshalb im allgemeinen vor seiner Verwendung verdünnt werden muss, normalerwei- se mit Wasser. Die Konzentrate können 10 bis 80, vorzugsweise 25 bis 70 Gew.- /o Wirkstoff enthalten. Besonders vorteilhaft ist ein Konzentrat, das den Wirkstoff zusammen mit einem oberflächenaktiven Mittel und einem Suspensionsmittel enthält, das in Wasser fein dispergiert worden ist. Bevorzugt werden Suspensionsmittel, die dem Konzentrat thixotrope Eigenschaft verleihen und seine Viskosität erhöhen, wie z. B. wasserlösliche, wasserhaltige, kolloidale Mineralsilikate und organische Substanzen mit einem hohen Molekulargewicht. Bevorzugte Suspensionsmittel sind Montmorillo- nit, Beidellit, Nontronit, Hectorit, Saponit, Saucorit, Cellulose-Derivate und Polyvinylalkohol. Besonders bevor zugte Konzentrate enthalten Bentonit als Suspensionsmittel. Eine weitere Form des Konzentrates besteht aus einem benetzbaren Pulver, d. h. einem Gemisch des feinverteilten Wirkstoffes mit einem festen oberflächen- aktiven Mittel, entweder mit oder ohne zusätzlichen festen Verdünner. Wenn es mit Wasser geschüttelt wird, löst sich das oberflächenaktive Mittel auf und fördert die Streuung des feinverteilten Wirkstoffes. Das Gemisch kann zur Bekämpfung einer grossen Zahl breit-und schmalblättriger Gräser, wie z. B. Poa annua, Alopecurus myosuroides, Polygonum persicaria oder Matricaria inodurata, verwendet werden. Die Gemische können als unkrautvertilgende Mittel mit Frühwirkung verwendet werden. Zu diesem Zweck werden sie auf den Unkrautsamen enthaltenden Boden aufgetragen und verbleiben lange genug darin, um entweder die Samen zu töten oder die Sämlinge, die sie bilden, zu vernichten oder zu beschädigen. Die Gemische können auch in herkömmlicher Weise als Unkrautvertilger mit Spätwirkung verwendet werden. Sie werden dann gegen das bereits stehende Unkraut angesetzt. Ein Gemisch, das mit gutem Erfolg für den einen Zweck verwendet werden kann, ist nicht immer für den anderen Zweck wirksam genug, weshalb gewisse einfache Versuche erforderlich sein können, um zu bestimmen, welches Gemisch gegen das zu vertilgende Unkraut verwendet werden soll, damit die besten Ergebnisse erzielt werden. Versuch 1 Dieses und die folgenden Versuche beschreiben die Herstellung von die neuen Verbindungen enthaltenden unkrautvertilgenden Gemischen sowie Versuche zur Veranschaulichung der phytotoxischen Eigenschaften derselben. Bei gewissen Versuchen wurden Pflanzen verwendet, die normalerweise nicht als Unkraut betrach- tet werden, die jedoch zur Bestimmung der phytotoxischen Wirkung nützlich sind. Die Gemische wurden hergestellt, indem der Wirkstoff feingemahlen wurde und dann 1 Gewichts- /o des pulverförmigen Materials in Wasser dispergiert wurde, das 1 Gew.- /o eines unter der Bezeichnung AGRA 90 (eingetragenes Warenzeichen) erhältlichen oberflächen- aktiven Mittels enthielt. Um das Mahlen der Wirkstoffe zu erleichtern, wurde ein geringer Anteil des in den erzielten Gemischen vorhandenen oberflächenaktiven Mittel während des Mahlvorganges zugefügt. Die vorher und die nachher eintretende unkrautvertilgende Wirkung der Gemische wurde wie folgt geprüft : In den Versuchen zur Prüfung der Frühwirkung des Gemisches wurden Blumentöpfe mit Kompost gefüllt und darin Furchen gemacht. Der Kompost wurde mit der zu prüfenden Lösung behandelt und Samen in die Furchen gesät, die dann zugedeckt wurden, so dass der Samen mit Kompost überdeckt war. Nach Ablauf von 21 Tagen wurde die Anzahl gesunder Setzlinge, die sich zu entwickeln vermochten, mit der Anzahl derjenigen verglichen, die in Töpfen wuchsen, deren Inhalt nicht mit einem zu prüfenden Gemisch behandelt worden war. In den Versuchen zur Bestimmung der unkrautvertilgenden Spätwirkung wurde Samen in Blumentöpfe gesät. Man liess ihn sich bis zu Setzlingen der Zweiblatt-Stufe entwickeln. Diese Setzlinge wurden dann mit einem zu prüfenden Gemisch besprüht und nach 14 Tagen die Anzahl beschädigter oder zerstörter Setzlinge bestimmt. Die Ergebnisse der Versuche, bei denen der Wirkstoff 2, 6-Difluor-3, 5-dichlorpyridin-4-thiol war, sind in Tabelle I angegeben. Die Zahlen in der ersten Kolonne unter dem Namen der jeweiligen Prüflingspflanze gibt den Prozentsatz der Pflanzen an, die sich bei der Bestimmung der Frühwirkung (Pre) nicht zu unbeschädigten Setzlingen entwickelten, während die zweite Kolonne den Prozentsatz der Setzlinge angibt, die bei der Bestimmung der Spätwirkung (Post) beschädigt oder zerstört wurden. Tabelle I EMI2.1 <SEP> Gerste <SEP> Weizen <SEP> Wildhaf <SEP> er <SEP> <tb> Pre <SEP> Post <SEP> Pre <SEP> Post <SEP> Pre <SEP> Post <tb> <SEP> 60 <SEP> 4080 <SEP> 4080 <SEP> 60 <SEP> <tb> Versuch 2 Ein ähnlicher Versuch wurde unter Verwendung von 2-Fluor-3, 5, 6-trichlorpyridin-4-thiol als Wirkstoff ausgeführt. Die Ergebnisse sind in Tabelle II angegeben. Tabelle II EMI3.1 <SEP> Gerste <SEP> Lattich <SEP> Mais <SEP> Tomate <SEP> <tb> Pre <SEP> Post <SEP> Pre <SEP> Post <SEP> Pre <SEP> Post <SEP> Pre <SEP> Post <tb> <SEP> 100 <SEP> 0 <SEP> 100 <SEP> 10 <SEP> 50 <SEP> 20 <SEP> 100 <tb> Versuch 3 Ein ähnlicher Versuch wurde unter Verwendung von 3-Chlor-2, 5, 6-trifluorpyridin-4-thiol als Wirkstoff ausgeführt. Die Ergebnisse sind in Tabelle III zusammengefasst. Tabelle III EMI3.2 <SEP> Gerste <SEP> Lattich <SEP> Mais <SEP> Tomate <tb> Pre <SEP> Post <SEP> Pre <SEP> Post <SEP> Pre <SEP> Post <SEP> Pre <SEP> Post <tb> <SEP> 0 <SEP> 60 <SEP> 0 <SEP> 100 <SEP> 0 <SEP> 80 <SEP> 0 <SEP> 100 <tb> Versuch 4 Ein ahnlicher Versuch wurde unter Verwendung vor 2, 3, 5, 6-Tetrachlorpyridin-4-thiol als Wirkstoff ausge fiihrt. Die Ergebnisse sind in Tabelle IV angegeben. Tabelle IV EMI3.3 <SEP> Gerste <SEP> Lattich <SEP> Mais <SEP> Tomate <tb> Pre <SEP> Post <SEP> Pre <SEP> Post <SEP> Pre <SEP> Post <SEP> Pre <SEP> Post <tb> <SEP> 0 <SEP> 200 <SEP> 500 <SEP> 400 <SEP> 100 <SEP> <tb> Versuch 5 Ein ähnlicher Versuch wurde unter Verwendung des Allyl-äthers von 2, 3, 5, 6-Tetrachlorpyridin-4-thiol als Wirkstoff ausgeführt. Die Ergebnisse sind in Tabelle V zusammengefasst. Tabelle V EMI3.4 <SEP> Gerste <SEP> Lattich <SEP> Mais <SEP> Tomate <tb> Pre <SEP> Post <SEP> Pre <SEP> Post <SEP> Pre <SEP> Post <SEP> Pre <SEP> Post <tb> <SEP> 0 <SEP> 200 <SEP> 400 <SEP> 0 <SEP> 10 <SEP> 0 <SEP> 50 <tb>
Claims (1)
- PATENTANSPRUCH Verwendung von Pyridinverbindungen der Formel : EMI4.1 worin X2, X3, X5 und X6 gleich oder verschieden sein können und Fluor oder Chlor und Y Wasserstoff, den Rest eines Salzes oder den Rest einer Aethergruppe bedeuten, zur Bekämpfung unerwünschter Vegetation.UNTERANSPRtJCHE 1. Verwendung nach Patentanspruch zur Vertilgung von Unkraut.2. Verwendung nach Unteranspruch 1, dadurch gekennzeichnet, dass die Pyridinverbindungen zusammen mit einem festen Verdünnungsmittel verwendet werden.3. Verwendung nach Unteranspruch 1, dadurch gekennzeichnet, dass ein Gemisch der Pyridinverbindungen mit einem flüssigen Verdünnungsmittel und einem oberflächenaktiven Mittel verwendet wird.4. Verwendung nach Unteranspruch 3, dadurch gekennzeichnet, dass das Gemisch 3, eine wässrige Dispersion darstellt.5. Verwendung nach den Unteransprüchen 2 bis 4, dadurch gekennzeichnet, dass das Gemisch 0, 1 bis 2, 0 Gew.- /o Wirkstoff enthält.6. Verwendung nach Patentanspruch, dadurch gekennzeichnet, dass die Pyridinverbindungen, in Form eines Konzentrates, das 10 bis 80 Gew : /o Wirkstoff enthält, verwendet werden.7. Verwendung nach Unteranspruch 4, dadurch gekennzeichnet, dass die wässrige Dispersion ein oberflä- chenaktives Mittel und ein Suspensionsmittel in feiner Verteilung enthält.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB51579/64A GB1059990A (en) | 1964-12-18 | 1964-12-18 | Substituted pyridines |
| GB33064/66A GB1161492A (en) | 1964-12-18 | 1965-08-19 | Fluoropyridines useful inter alia as Herbicides |
| GB35596/65A GB1161491A (en) | 1964-12-18 | 1965-08-19 | Fluoropyridine Herbicides |
| GB4890465 | 1965-08-19 | ||
| CH1751165A CH472353A (de) | 1964-12-18 | 1965-12-20 | Verfahren zur Herstellung von Pyridin-4-thiolen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH480786A true CH480786A (de) | 1969-11-15 |
Family
ID=27509548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH349469A CH480786A (de) | 1964-12-18 | 1965-12-20 | Verwendung von Pyridinverbindungen zur Bekämpfung unerwünschter Vegetation |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH480786A (de) |
-
1965
- 1965-12-20 CH CH349469A patent/CH480786A/de not_active IP Right Cessation
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