CH340372A - Preparations for influencing plant growth, in particular for combating weeds - Google Patents
Preparations for influencing plant growth, in particular for combating weedsInfo
- Publication number
- CH340372A CH340372A CH340372DA CH340372A CH 340372 A CH340372 A CH 340372A CH 340372D A CH340372D A CH 340372DA CH 340372 A CH340372 A CH 340372A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- plant growth
- preparations
- combating weeds
- influencing plant
- Prior art date
Links
- 241000196324 Embryophyta Species 0.000 title claims description 13
- 230000008635 plant growth Effects 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000004094 surface-active agent Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000013543 active substance Substances 0.000 description 5
- -1 polyethylene Polymers 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 241000219198 Brassica Species 0.000 description 4
- 240000004658 Medicago sativa Species 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 230000002147 killing effect Effects 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 235000003351 Brassica cretica Nutrition 0.000 description 3
- 235000003343 Brassica rupestris Nutrition 0.000 description 3
- 244000000626 Daucus carota Species 0.000 description 3
- 235000002767 Daucus carota Nutrition 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 235000010460 mustard Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- NJYZCEFQAIUHSD-UHFFFAOYSA-N acetoguanamine Chemical compound CC1=NC(N)=NC(N)=N1 NJYZCEFQAIUHSD-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000035613 defoliation Effects 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 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 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 230000002028 premature Effects 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- DBJVBSDHJCGSRI-UHFFFAOYSA-N 6-ethoxy-2-n,2-n,4-n,4-n-tetraethyl-1,3,5-triazine-2,4-diamine Chemical compound CCOC1=NC(N(CC)CC)=NC(N(CC)CC)=N1 DBJVBSDHJCGSRI-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 235000010624 Medicago sativa Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 235000012216 bentonite Nutrition 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 235000010338 boric acid Nutrition 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 230000005094 fruit set Effects 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000009422 growth inhibiting effect Effects 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- ISEUFVQQFVOBCY-UHFFFAOYSA-N prometon Chemical compound COC1=NC(NC(C)C)=NC(NC(C)C)=N1 ISEUFVQQFVOBCY-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- HKAMKLBXTLTVCN-UHFFFAOYSA-N simeton Chemical compound CCNC1=NC(NCC)=NC(OC)=N1 HKAMKLBXTLTVCN-UHFFFAOYSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/48—Two nitrogen atoms
- C07D251/52—Two nitrogen atoms with an oxygen or sulfur atom attached to the third ring carbon atom
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Mittel zur Beeinflussung des Pflanzenwachstums, insbesondere zur Bekämpfung von Unkraut Es wurde die überraschende Beobachtung ge iacht, dass Triazine der Formel
EMI0001.0002
worin X Sauerstoff oder Schwefel n 0 oder 1 R, R1, R2, R3 und R4 Wasserstoff oder Kohlen wasserstoffreste bedeuten, bereits in sehr niedriger Konzentration auf Pflanzen wachstumshemmend und abtötend wirken. Verbindungen der oben definierten Formel 1 sind z.
B. durch Umsetzung von Cyanurchlorid mit ge eigneten Alkoholen oder Mercaptanen und Aminen, gegebenenfalls gefolgt von reduktiver Entfernung eines noch verbliebenen Chloratoms herstellbar, ferner durch Umsetzung von 2-Alkyl-4,6-dichlor-s- triazinen mit Aminen. Sie eignen sich vorzüglich als Wirkstoffe für Unkrautbekämpfungsmittel, sowohl zur selektiven Abtötung von Unkräutern unter Kul turpflanzen wie auch zur totalen Abtötung und Verhinderung unerwünschten Pflanzenwuchses. Unter Unkräutern werden hierbei auch unerwünschte, z.
B. vorher oder in der Nähe angebaute Kultur pflanzen verstanden. Die oben definierten Verbin dungen eignen sich weiterhin auch als Wirkstoffe für andere hemmende Beeinflussungen des Pflanzen wachstums, insbesondere Entblätterung, -Reifebe schleunigung durch vorzeitiges Austrocknen, z. B. von Kartoffelstauden, ferner Verminderung des Fruchtansatzes, Verzögerung der Blüte.
Als Wirkstoffe kommen z. B. die nachstehenden, zum Teil bekannten, zum Teil neuen Triazinderivate in Frage:
EMI0001.0021
EMI0001.0022
<U>X' <SEP> Y <SEP> Z</U>
<tb> OCH. <SEP> NH2 <SEP> NH-C2H5 <SEP> F: <SEP> 172-174
<tb> OCHS <SEP> NH-CH3 <SEP> NH-i-C3H7 <SEP> F: <SEP> 105-107
<tb> OCHS <SEP> NH-C2H5 <SEP> NH-C2H5 <SEP> F: <SEP> 92-94
<tb> OCHS <SEP> NH-C.H. <SEP> NH-i-C3H7 <SEP> F: <SEP> 94-95
<tb> OCHS <SEP> NH-i-C3'-17 <SEP> NH-i-C.H7 <SEP> F: <SEP> 91-92
<tb> OCH. <SEP> NH-n-C,H<B>7</B> <SEP> NH-i-C<B>3</B>H<B>7</B> <SEP> F: <SEP> 92-94
<tb> OCH. <SEP> NH-C2H5 <SEP> N-(C2H5)2 <SEP> F: <SEP> 106-108
<tb> OCHS <SEP> NH-i-C3H7 <SEP> N-(C2H5)2 <SEP> F:
<SEP> 75-77
<tb> OCH. <SEP> <B>N-(C2H5)2</B> <SEP> N-(C2H5)2 <SEP> Kpo.o5 <SEP> 97-100
EMI0002.0001
<U>X' <SEP> Y <SEP> Z</U>
<tb> OCHS <SEP> NH-#H <SEP> NH-<B>-- <SEP> < #</B> <SEP> F: <SEP> 126-127
<tb> O-C2H5 <SEP> NI-12 <SEP> NH2 <SEP> F: <SEP> 175-177
<tb> O-C1H5 <SEP> NH2 <SEP> NH-C2H5 <SEP> F: <SEP> 137-138
<tb> <B>O-C2H5</B> <SEP> NI-12 <SEP> N-(C@H5).2 <SEP> F: <SEP> 137-140
<tb> O-C2H5 <SEP> NH-C2H5 <SEP> NH-C2H5 <SEP> F: <SEP> 112-114
<tb> O-C2H5 <SEP> NH-i-C,1, <SEP> NH-i <SEP> C3H7 <SEP> F: <SEP> 96-98
<tb> O-C2H5 <SEP> N-(C<B><U>,></U></B>H5)2 <SEP> <B>N <SEP> -(C2".-)2</B> <SEP> Kpo,27 <SEP> 108-110
<tb> O <SEP> i.-C3H7 <SEP> NH2 <SEP> NH-C,H5 <SEP> F: <SEP> 131-133
<tb> O <SEP> i-C3H7 <SEP> NH-C2H5 <SEP> NH-C2H5 <SEP> F: <SEP> 92-94
<tb> O-i-C3H7 <SEP> NH-i-C3H7 <SEP> NH-i-C3H7 <SEP> F:
<SEP> 107-109
<tb> O-i-C3H7 <SEP> <B>N</B> <SEP> (C2"5)2 <SEP> N <SEP> (C2"5)2 <SEP> Kpo.2116-117
<tb> O-CH2 <SEP> CH=CH2 <SEP> NH-C2H5 <SEP> NH-C2H5 <SEP> F: <SEP> 96-97
<tb> O-CH2 <SEP> CH=CH2 <SEP> N-(C2H5)2 <SEP> N-(C2H5)2 <SEP> Kpo,o3104-106
<tb> O <SEP> n <SEP> C3"7 <SEP> NH-C2H5 <SEP> NH-C2H5 <SEP> F: <SEP> 81-83
<tb> O-n-C3H7 <SEP> N-(C@H5)" <SEP> N-(C2Hs),a <SEP> Kpo>o,2 <SEP> 112-113
<tb> O-n-CA <SEP> NH-C2H5 <SEP> NH-C2H5 <SEP> F: <SEP> 50
<tb> O-n-CSH17 <SEP> NH-C<B>.,</B>H- <SEP> NH-C2H5 <SEP> Kpo.oooi <SEP> 140-150
<tb> OH <SEP> NH-C2H5 <SEP> NH-C.H. <SEP> F: <SEP> > <SEP> 250
<tb> OH <SEP> NH-C2H5 <SEP> NH-i-C3H7 <SEP> F: <SEP> > <SEP> 250
<tb> OH <SEP> N-(C2H5)2 <SEP> N-(C2H5)2 <SEP> F: <SEP> 177-179
<tb> S-CH3 <SEP> NH-CH3 <SEP> NI-i <SEP> C3H7 <SEP> F: <SEP> 83-85
<tb> S-CH3 <SEP> NH-C2H. <SEP> NH-C2H5 <SEP> F:
<SEP> 82-83
<tb> S--CH. <SEP> NH-C2H5 <SEP> NH-i-C.H. <SEP> F: <SEP> 88-89
<tb> S-CH3 <SEP> NH-i-C.H7 <SEP> NH-i-C3H7 <SEP> F: <SEP> 118-120
<tb> SH <SEP> NH-CZHS <SEP> NH-C2H5 <SEP> F: <SEP> etwa <SEP> 260
<tb> SH <SEP> <B>N-(C2H5)2</B> <SEP> N-(C2H5)2 <SEP> F: <SEP> 155-156
<tb> CH3 <SEP> NH-C2H5 <SEP> NH-C2H5 <SEP> F: <SEP> 165-167
<tb> CH3 <SEP> NH-i-C3H7 <SEP> NH-i-C3,7 <SEP> F: <SEP> 167-168
<tb> CH3 <SEP> NH-n-C.H. <SEP> NH-n-C,H, <SEP> F: <SEP> 164-165
<tb> CH3 <SEP> N-(C2H5)2 <SEP> N-(C2H5)2 <SEP> Kpo,o2 <SEP> 80
<tb> C2H5 <SEP> NH-C2H5 <SEP> NH-C2H5 <SEP> F: <SEP> 151-153
<tb> C2"5 <SEP> NH-i-C.H@ <SEP> NH-i-C3H7 <SEP> F: <SEP> 97-99
<tb> 02H5 <SEP> N <SEP> (C2"5)2 <SEP> N-(C-H5)2 <SEP> Kpo,le <SEP> 96
<tb> i-C3H7 <SEP> NH-C2H5 <SEP> NH-C2H5 <SEP> F:
<SEP> 89
<tb> i-C3H7 <SEP> NH-i-C3H7 <SEP> NH-i-C3H7 <SEP> Kpo,o1109
<tb> n-C.H7 <SEP> NH-C2H5 <SEP> NH-C2H. <SEP> F: <SEP> 151-153
<tb> n-C.H7 <SEP> NH-i <SEP> C3H7 <SEP> NH-i-C.H7 <SEP> F: <SEP> 94
<tb> n-C4H. <SEP> NH-C2H<B>,i</B> <SEP> NH-C2H5 <SEP> F: <SEP> 131-132 Gegenstand des vorliegenden Patentes ist ein Mittel zur Beeinflussung des Pflanzenwachstums, insbesondere zur Bekämpfung von Unkraut, dadurch gekennzeichnet, dass es eine Verbindung der Formel
EMI0002.0004
worin X, n, R, R1, R2, R3 und R4 die oben angege bene Bedeutung haben, und einen oberflächenaktiven Stoff enthält.
Die erfindungsgemässen Mittel können Emul sionen oder Suspensionen darstellen. Die Anwen dungsformen richten sich ganz nach den Verwen dungszwecken, lediglich müssen alle Applikations- formen eine feine Verteilbarkeit der Wirksubstanz gewährleisten. Zur Herstellung erfindungsgemässer Mittel werden die Substanzen z. B. als solche oder in einem der weiter unten genannten Lösungsmittel mittels oberflächenaktiven Stoffen, wie Netz- oder Dispergiermitteln, in Wasser homogenisiert.
An kationaktiven Emulgier- oder Dispergiermit- teln seien als Beispiele quaternäre Ammoniumver- bindungen genannt, an anionaktiven Emulgiermitteln Seife, Schmierseife, aliphatische langkettige Schwe- felsäuremonoester, aliphatische oder aromatische Sulfosäuren, langkettige Alkoxyessigsäuren,
an nicht- ionogenen Emulgiermitteln Polyäthylenäther von Fettalkoholen und Polyäthylenkondensationspro- dukte. Anderseits können auch aus Wirkstoff, Emul- gator oder Dispergator und eventuell Lösungsmittel bestehende Konzentrate hergestellt werden, die sich zur Verdünnung mit Wasser eignen.
Zur Herstellung von Lösungen der Wirkstoffe mit oberflächenaktiven Stoffen kommen Lösungs mittel, wie insbesondere Alkohole, z. B. Äthyl- oder Isopropylalkohol, Ketone, wie Aceton oder Cyclo- hexanon, aliphatische Kohlenwasserstoffe, wie Kerosen und cyclische Kohlenwasserstoffe, wie Benzol, Toluol, Xylol, Tetrahydronaphthalin,
alky- lierte Naphthaline, ferner chlorierte Kohlenwasser stoffe, wie Tetrachloräthan, Äthylenchlorid und end lich auch mineralische und pflanzliche Öle oder Ge mische der obengenannten Stoffe in Frage.
Insbesondere bei der totalen Abtötung von Pflanzenwuchs, bei der vorzeitigen Austrocknung so wie der Entblätterung kann die Wirkung durch die Verwendung von an sich phytotoxischen organischen Flüssigkeiten, wie z. B. hochsiedenden Mineralöl fraktionen oder Chlorkohlenwasserstoffe, verstärkt werden; anderseits kommt die Selektivität der Wachs tumshemmung bei der Verwendung von gegenüber Pflanzen indifferenten Trägerstoffen, z. B. in der selektiven Unkrautbekämpfung, unter Umständen deutlicher zur Geltung.
Zur Bereitung von Konzentraten für Suspen sionen kann man auch zunächst pulverförmige Prä parate durch Mischen oder gemeinsames Vermahlen von Wirksubstanz mit einem festen Trägerstoff her gestellt werden. Als solche kommen in Frage: Talkum, Diatomeenerde, Kaolin, Bentonit, Calcium- karbonat, Borsäure, Tricalciumphosphat, aber auch Holzmehl, Korkmehl, Kohle und andere Materia lien pflanzlicher Herkunft. Anderseits können die Substanzen auch mittels eines flüchtigen Lösungs mittels auf die Trägerstoffe aufgezogen werden.
Durch Kombination mit Netzmitteln und gegebenen falls Schutzkolloiden werden hierauf die pulverförmi gen Präparate in Wasser suspendierbar und als Spritzmittel verwendbar gemacht. Zu ähnlichen Mit teln gelangt man auch durch Zusatz von Netzmitteln zu Pasten, das heisst Gemischen von festen Wirk stoffen mit nichtlösenden Flüssigkeiten.
Die verschiedenen Anwendungsformen können in üblicher Weise durch Zusatz von Stoffen, welche die Verteilung, die Haftfestigkeit, die Regenbestän digkeit und evtl. das Eindringungsvermögen verbes sern, wie von z. B. Fettsäuren, Harzen, Leim, Casein oder Alginaten, den Verwendungszwecken näher an- gepasst werden. Ebenso lässt sich ihre biologische Wirkung verbreitern durch Zusatz von Stoffen mit bakteriziden, fungiziden oder ebenfalls das Pflanzen wachstum beeinflussenden Eigenschaften sowie von Düngemitteln.
Des weiteren werden folgende Beispiele für ty pische Applikationsmittel und -formen angeführt. <I>Beispiel 1</I> 20 Teile 2-Methoxy-4,6-bis-äthylamino-s-triazin werden mit 70 Teilen fester inerter Trägersubstanz, z. B. Talk, Kaolin, Bentonit oder Kieselgur, 7 Teilen. eines nichtionogenen Netzmittels, z. B. eines Schwe- felsäureesters eines Alkyl-polyglykoläthers und 3 Teilen Schutzkolloid, z.
B. Sulfitablauge, in einer Stiften-Mühle fein vermahlen. Das erhaltene Pulver ist in Wasser suspendierbar und kann zu Spritz- mitteln verarbeitet werden.
<I>Beispiel 2</I> 5 Teile 2-Methoxy-4,6-bis-isopropylamino-s-tri- azin werden in 90 Teilen flüssigen Trägerstoffes, z. B. Diacetonalkohol, Xylol, gelöst und mit 5 Teilen eines nichtionogenen Emulgators, z. B. Polyäthylen äther von Fettalkoholen, versetzt. Die Lösung wird im gewünschten Verhältnis mit Wasser vermischt und bildet eine milchige Emulsion.
<I>Beispiel 3</I> In Saatschalen wurden je eine Reihe (10 Samen) Weizen, Senf, Luzerne und Karotten mit einer Saat tiefe von 3 cm, und je eine zweite Reihe derselben Samenarten mit einer Saattiefe von 1 cm gesät und leicht begossen. Anschliessend wurden die Saat schalen mit 0,1 Liter pro m2 von 2 o/oigen Emulsio nen oder Suspensionen der zu prüfenden Verbindun gen (je nach ihrem Aggregatzustand), welche als oberflächenaktiven Stoff Alkylpolyglykoläther ent halten, bespritzt, entsprechend 2 g Wirksubstanz pro m2.
Nach 21 Tagen waren in den mit 2-Methyl-4,6- diamino-s-triazin behandelten Saatschalen die Lu zerne abgestorben, die übrigen Pflanzen dagegen nicht geschädigt. In den mit 2-Äthoxy-4,6-bis-di- äthylamino-s-triazin behandelten Saatschalen waren Senf und Luzerne abgestorben, dagegen Weizen und Karotten unversehrt.
In der mit 2-Äthoxy-4,6-bis-äthylamino-s-triazin behandelten Schale waren Senf und Luzerne abge storben und Weizen und Karotten geschädigt. <I>Beispiel 4</I> 0,5 o/oige Emulsionen von 2-Methyl-4,6-diamino- s-triazin, die als oberflächenaktiven Stoff Polyäthy- lenäther von Fettalkoholen enthalten, bewirkten an Senfpflanzen Blattverbrennungen.
Agents for influencing plant growth, in particular for combating weeds The surprising observation was made that triazines of the formula
EMI0001.0002
where X is oxygen or sulfur n 0 or 1 R, R1, R2, R3 and R4 are hydrogen or hydrocarbon residues, have a growth-inhibiting and killing effect on plants even in very low concentrations. Compounds of the formula 1 defined above are, for.
B. can be prepared by reacting cyanuric chloride with suitable alcohols or mercaptans and amines, optionally followed by reductive removal of a remaining chlorine atom, and also by reacting 2-alkyl-4,6-dichloro-s- triazines with amines. They are particularly suitable as active ingredients for weed control agents, both for the selective killing of weeds under culture plants as well as for the total killing and prevention of undesirable vegetation. Weeds here are also undesirable, e.g.
B. understood plants previously grown or in the vicinity. The compounds defined above are also suitable as active ingredients for other inhibitory effects on plant growth, in particular defoliation, -Reifebe acceleration due to premature drying out, eg. B. of potato plants, further reduction in fruit set, delay in flowering.
As active ingredients come z. B. the following, partly known, partly new triazine derivatives in question:
EMI0001.0021
EMI0001.0022
<U> X '<SEP> Y <SEP> Z </U>
<tb> OCH. <SEP> NH2 <SEP> NH-C2H5 <SEP> F: <SEP> 172-174
<tb> OCHS <SEP> NH-CH3 <SEP> NH-i-C3H7 <SEP> F: <SEP> 105-107
<tb> OCHS <SEP> NH-C2H5 <SEP> NH-C2H5 <SEP> F: <SEP> 92-94
<tb> OCHS <SEP> NH-C.H. <SEP> NH-i-C3H7 <SEP> F: <SEP> 94-95
<tb> OCHS <SEP> NH-i-C3'-17 <SEP> NH-i-C.H7 <SEP> F: <SEP> 91-92
<tb> OCH. <SEP> NH-n-C, H <B> 7 </B> <SEP> NH-i-C <B> 3 </B> H <B> 7 </B> <SEP> F: <SEP> 92-94
<tb> OCH. <SEP> NH-C2H5 <SEP> N- (C2H5) 2 <SEP> F: <SEP> 106-108
<tb> OCHS <SEP> NH-i-C3H7 <SEP> N- (C2H5) 2 <SEP> F:
<SEP> 75-77
<tb> OCH. <SEP> <B> N- (C2H5) 2 </B> <SEP> N- (C2H5) 2 <SEP> Kpo.o5 <SEP> 97-100
EMI0002.0001
<U> X '<SEP> Y <SEP> Z </U>
<tb> OCHS <SEP> NH- # H <SEP> NH- <B> - <SEP> <# </B> <SEP> F: <SEP> 126-127
<tb> O-C2H5 <SEP> NI-12 <SEP> NH2 <SEP> F: <SEP> 175-177
<tb> O-C1H5 <SEP> NH2 <SEP> NH-C2H5 <SEP> F: <SEP> 137-138
<tb> <B> O-C2H5 </B> <SEP> NI-12 <SEP> N- (C @ H5) .2 <SEP> F: <SEP> 137-140
<tb> O-C2H5 <SEP> NH-C2H5 <SEP> NH-C2H5 <SEP> F: <SEP> 112-114
<tb> O-C2H5 <SEP> NH-i-C, 1, <SEP> NH-i <SEP> C3H7 <SEP> F: <SEP> 96-98
<tb> O-C2H5 <SEP> N- (C <B> <U>,> </U> </B> H5) 2 <SEP> <B> N <SEP> - (C2 ".-) 2 </B> <SEP> Kpo, 27 <SEP> 108-110
<tb> O <SEP> i.-C3H7 <SEP> NH2 <SEP> NH-C, H5 <SEP> F: <SEP> 131-133
<tb> O <SEP> i-C3H7 <SEP> NH-C2H5 <SEP> NH-C2H5 <SEP> F: <SEP> 92-94
<tb> O-i-C3H7 <SEP> NH-i-C3H7 <SEP> NH-i-C3H7 <SEP> F:
<SEP> 107-109
<tb> O-i-C3H7 <SEP> <B> N </B> <SEP> (C2 "5) 2 <SEP> N <SEP> (C2" 5) 2 <SEP> Kpo.2116-117
<tb> O-CH2 <SEP> CH = CH2 <SEP> NH-C2H5 <SEP> NH-C2H5 <SEP> F: <SEP> 96-97
<tb> O-CH2 <SEP> CH = CH2 <SEP> N- (C2H5) 2 <SEP> N- (C2H5) 2 <SEP> Kpo, o3104-106
<tb> O <SEP> n <SEP> C3 "7 <SEP> NH-C2H5 <SEP> NH-C2H5 <SEP> F: <SEP> 81-83
<tb> O-n-C3H7 <SEP> N- (C @ H5) "<SEP> N- (C2Hs), a <SEP> Kpo> o, 2 <SEP> 112-113
<tb> O-n-CA <SEP> NH-C2H5 <SEP> NH-C2H5 <SEP> F: <SEP> 50
<tb> O-n-CSH17 <SEP> NH-C <B>., </B> H- <SEP> NH-C2H5 <SEP> Kpo.oooi <SEP> 140-150
<tb> OH <SEP> NH-C2H5 <SEP> NH-C.H. <SEP> F: <SEP>> <SEP> 250
<tb> OH <SEP> NH-C2H5 <SEP> NH-i-C3H7 <SEP> F: <SEP>> <SEP> 250
<tb> OH <SEP> N- (C2H5) 2 <SEP> N- (C2H5) 2 <SEP> F: <SEP> 177-179
<tb> S-CH3 <SEP> NH-CH3 <SEP> NI-i <SEP> C3H7 <SEP> F: <SEP> 83-85
<tb> S-CH3 <SEP> NH-C2H. <SEP> NH-C2H5 <SEP> F:
<SEP> 82-83
<tb> S - CH. <SEP> NH-C2H5 <SEP> NH-i-C.H. <SEP> F: <SEP> 88-89
<tb> S-CH3 <SEP> NH-i-C.H7 <SEP> NH-i-C3H7 <SEP> F: <SEP> 118-120
<tb> SH <SEP> NH-CZHS <SEP> NH-C2H5 <SEP> F: <SEP> about <SEP> 260
<tb> SH <SEP> <B> N- (C2H5) 2 </B> <SEP> N- (C2H5) 2 <SEP> F: <SEP> 155-156
<tb> CH3 <SEP> NH-C2H5 <SEP> NH-C2H5 <SEP> F: <SEP> 165-167
<tb> CH3 <SEP> NH-i-C3H7 <SEP> NH-i-C3,7 <SEP> F: <SEP> 167-168
<tb> CH3 <SEP> NH-n-C.H. <SEP> NH-n-C, H, <SEP> F: <SEP> 164-165
<tb> CH3 <SEP> N- (C2H5) 2 <SEP> N- (C2H5) 2 <SEP> Kpo, o2 <SEP> 80
<tb> C2H5 <SEP> NH-C2H5 <SEP> NH-C2H5 <SEP> F: <SEP> 151-153
<tb> C2 "5 <SEP> NH-i-C.H @ <SEP> NH-i-C3H7 <SEP> F: <SEP> 97-99
<tb> 02H5 <SEP> N <SEP> (C2 "5) 2 <SEP> N- (C-H5) 2 <SEP> Kpo, le <SEP> 96
<tb> i-C3H7 <SEP> NH-C2H5 <SEP> NH-C2H5 <SEP> F:
<SEP> 89
<tb> i-C3H7 <SEP> NH-i-C3H7 <SEP> NH-i-C3H7 <SEP> Kpo, o1109
<tb> n-C.H7 <SEP> NH-C2H5 <SEP> NH-C2H. <SEP> F: <SEP> 151-153
<tb> n-C.H7 <SEP> NH-i <SEP> C3H7 <SEP> NH-i-C.H7 <SEP> F: <SEP> 94
<tb> n-C4H. <SEP> NH-C2H <B>, i </B> <SEP> NH-C2H5 <SEP> F: <SEP> 131-132 The subject of the present patent is an agent for influencing plant growth, in particular for controlling weeds, characterized in that it is a compound of the formula
EMI0002.0004
wherein X, n, R, R1, R2, R3 and R4 have the meaning given above, and contains a surfactant.
The agents according to the invention can be emulsions or suspensions. The forms of application depend entirely on the purposes of use, only all forms of application must ensure that the active substance can be distributed fine. For the preparation of the inventive agents, the substances are z. B. as such or in one of the solvents mentioned below by means of surface-active substances, such as wetting agents or dispersants, homogenized in water.
Examples of cationic emulsifiers or dispersants are quaternary ammonium compounds;
of non-ionic emulsifiers, polyethylene ethers from fatty alcohols and polyethylene condensation products. On the other hand, concentrates consisting of active ingredient, emulsifier or dispersant and possibly solvent can also be prepared which are suitable for dilution with water.
For the preparation of solutions of the active ingredients with surface-active substances, solvents, such as alcohols in particular, such. B. ethyl or isopropyl alcohol, ketones such as acetone or cyclohexanone, aliphatic hydrocarbons such as kerosene and cyclic hydrocarbons such as benzene, toluene, xylene, tetrahydronaphthalene,
alkylated naphthalenes, and also chlorinated hydrocarbons, such as tetrachloroethane, ethylene chloride and, finally, mineral and vegetable oils or mixtures of the abovementioned substances.
Especially in the case of the total killing of vegetation, in the case of premature drying out and defoliation, the effect can be achieved through the use of organic liquids that are inherently phytotoxic, such as. B. high-boiling mineral oil fractions or chlorinated hydrocarbons are reinforced; on the other hand, the selectivity of the growth inhibition comes when using carriers indifferent to plants, eg. B. in selective weed control, may be more evident.
For the preparation of concentrates for suspensions, powdery preparations can first be made by mixing or co-grinding the active ingredient with a solid carrier. These include: talc, diatomaceous earth, kaolin, bentonite, calcium carbonate, boric acid, tricalcium phosphate, but also wood flour, cork flour, coal and other materials of vegetable origin. On the other hand, the substances can also be absorbed onto the carrier materials by means of a volatile solvent.
By combining them with wetting agents and, if necessary, protective colloids, the pulveriform preparations can then be suspended in water and used as sprays. Similar means can also be obtained by adding wetting agents to pastes, i.e. mixtures of solid active substances with non-dissolving liquids.
The various forms of application can in the usual way by adding substances that improve the distribution, the adhesive strength, the rain resistance and possibly the penetration capacity, such as z. B. fatty acids, resins, glue, casein or alginates, can be adapted more closely to the intended use. Their biological effect can also be broadened by adding substances with bactericidal, fungicidal or properties that also affect plant growth, as well as fertilizers.
In addition, the following examples of typical application means and forms are given. <I> Example 1 </I> 20 parts of 2-methoxy-4,6-bis-ethylamino-s-triazine are mixed with 70 parts of a solid inert carrier, e.g. B. talc, kaolin, bentonite or kieselguhr, 7 parts. a nonionic wetting agent, e.g. B. a sulfuric acid ester of an alkyl polyglycol ether and 3 parts of protective colloid, z.
B. sulphite waste liquor, finely ground in a pin mill. The powder obtained can be suspended in water and processed into spraying agents.
<I> Example 2 </I> 5 parts of 2-methoxy-4,6-bis-isopropylamino-s-triazine are dissolved in 90 parts of a liquid carrier, e.g. B. diacetone alcohol, xylene, dissolved and with 5 parts of a nonionic emulsifier, for. B. polyethylene ether of fatty alcohols, added. The solution is mixed with water in the desired ratio and forms a milky emulsion.
<I> Example 3 </I> A row (10 seeds) of wheat, mustard, alfalfa and carrots each with a seed depth of 3 cm, and a second row of the same seed types each with a seed depth of 1 cm were sown lightly in seed trays doused. The seed trays were then sprayed with 0.1 liters per m2 of 2% emulsions or suspensions of the compounds to be tested (depending on their physical state), which contain alkyl polyglycol ether as a surface-active substance, corresponding to 2 g of active substance per m2.
After 21 days, the lucerne in the seed trays treated with 2-methyl-4,6-diamino-s-triazine had died, but the other plants were not damaged. In the seed trays treated with 2-ethoxy-4,6-bis-diethylamino-s-triazine, mustard and alfalfa had died, while wheat and carrots were intact.
In the shell treated with 2-ethoxy-4,6-bis-äthylamino-s-triazine, mustard and alfalfa died and wheat and carrots were damaged. Example 4 0.5% emulsions of 2-methyl-4,6-diamino-s-triazine, which contain polyethylene ethers of fatty alcohols as surface-active substance, caused leaf burns on mustard plants.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH340372T | 1955-01-14 | ||
| CH337019T | 1955-01-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH340372A true CH340372A (en) | 1959-08-15 |
Family
ID=25736788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH340372D CH340372A (en) | 1955-01-14 | 1955-01-14 | Preparations for influencing plant growth, in particular for combating weeds |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH340372A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1149197B (en) * | 1959-10-22 | 1963-05-22 | Norddeutsche Affinerie | Means for killing weeds in the pre-emergence method in beet crops |
-
1955
- 1955-01-14 CH CH340372D patent/CH340372A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1149197B (en) * | 1959-10-22 | 1963-05-22 | Norddeutsche Affinerie | Means for killing weeds in the pre-emergence method in beet crops |
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