NO117271B - - Google Patents
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- NO117271B NO117271B NO16984467A NO16984467A NO117271B NO 117271 B NO117271 B NO 117271B NO 16984467 A NO16984467 A NO 16984467A NO 16984467 A NO16984467 A NO 16984467A NO 117271 B NO117271 B NO 117271B
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- amino
- compounds
- triazine
- ethyl
- methyl
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 230000008635 plant growth Effects 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 42
- -1 alkyl mercaptan Chemical compound 0.000 description 20
- 241000196324 Embryophyta Species 0.000 description 17
- 239000002689 soil Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 13
- 230000002363 herbicidal effect Effects 0.000 description 12
- 239000004009 herbicide Substances 0.000 description 9
- 125000004093 cyano group Chemical group *C#N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000009331 sowing Methods 0.000 description 6
- 231100000674 Phytotoxicity Toxicity 0.000 description 5
- 240000008042 Zea mays Species 0.000 description 5
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 5
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 230000035784 germination Effects 0.000 description 5
- 235000009973 maize Nutrition 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 150000003918 triazines Chemical class 0.000 description 4
- RTNUTCOTGVKVBR-UHFFFAOYSA-N 4-chlorotriazine Chemical class ClC1=CC=NN=N1 RTNUTCOTGVKVBR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 2
- 235000005637 Brassica campestris Nutrition 0.000 description 2
- 235000014750 Brassica kaber Nutrition 0.000 description 2
- 240000008100 Brassica rapa Species 0.000 description 2
- 235000010149 Brassica rapa subsp chinensis Nutrition 0.000 description 2
- 235000010570 Brassica rapa var. rapa Nutrition 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 235000004431 Linum usitatissimum Nutrition 0.000 description 2
- 240000006240 Linum usitatissimum Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 235000021536 Sugar beet Nutrition 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical class 0.000 description 2
- 150000001540 azides 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
- 239000011230 binding agent Substances 0.000 description 2
- 239000005018 casein Substances 0.000 description 2
- 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 2
- 235000021240 caseins Nutrition 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 230000000885 phytotoxic effect Effects 0.000 description 2
- 238000002203 pretreatment Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- SKDGWNHUETZZCS-UHFFFAOYSA-N 2,3-ditert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(O)=C1C(C)(C)C SKDGWNHUETZZCS-UHFFFAOYSA-N 0.000 description 1
- SLYVQEOUGKXEAV-UHFFFAOYSA-N 4-azidotriazine Chemical class [N-]=[N+]=NC1=CC=NN=N1 SLYVQEOUGKXEAV-UHFFFAOYSA-N 0.000 description 1
- DILHXKUVSSSQPL-UHFFFAOYSA-N 6-chloro-2,4-diethyl-2h-1,3,5-triazin-1-amine Chemical compound CCC1N=C(CC)N=C(Cl)N1N DILHXKUVSSSQPL-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000508725 Elymus repens Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000209082 Lolium Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 1
- UAZDIGCOBKKMPU-UHFFFAOYSA-O azanium;azide Chemical compound [NH4+].[N-]=[N+]=[N-] UAZDIGCOBKKMPU-UHFFFAOYSA-O 0.000 description 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 125000001309 chloro group Chemical class Cl* 0.000 description 1
- 239000002361 compost 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
- 230000035613 defoliation Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000005094 fruit set Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000008040 ionic compounds Chemical class 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
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical class C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
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- 150000003839 salts Chemical class 0.000 description 1
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- 150000007949 saponins Chemical class 0.000 description 1
- 235000017709 saponins Nutrition 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
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- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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- 239000000080 wetting agent Substances 0.000 description 1
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Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Middel for plantevekstkontroll. Agent for plant growth control.
Foreliggende oppfinnelse angår midler for bekjempelse av plantevekst, og da spesielt som herbicider. The present invention relates to agents for combating plant growth, and in particular as herbicides.
Det er kjent herbicider som inneholder, som aktiv ingrediens, et s-triazin som i 2-stilling inneholder en azidogruppe, en alkylmercapto-gruppe eller et halogenatom, og som i 4-stilling inneholder en cyano-alkylaminogruppe (belgiske patenter 656 233 og 644 355). I disse forbindelser er imidlertid cyanogruppen bundet til et pri-mært C-atom, og forbindelser av denne type har ikke hatt samme herbicide virkning som de beste kommersielle produkter. Herbicides are known which contain, as active ingredient, an s-triazine which in the 2-position contains an azido group, an alkylmercapto group or a halogen atom, and which in the 4-position contains a cyano-alkylamino group (Belgian patents 656 233 and 644 355). In these compounds, however, the cyano group is bound to a primary C atom, and compounds of this type have not had the same herbicidal effect as the best commercial products.
Man har nå funnet at cyano-alkylamino-s-triaziner hvor cyano-gruppen er bundet til et tertiært C-atom, særmerker seg ved en spesielt høy og selektiv herbicid virkning foruten at de raskt dekomponeres i jorden. It has now been found that cyano-alkylamino-s-triazines where the cyano group is bound to a tertiary C atom are characterized by a particularly high and selective herbicidal effect, in addition to the fact that they quickly decompose in the soil.
Oppfinnelsen vedrører altså et middel til bekjempelse av plantevekst, idet midlet er ka- The invention therefore relates to an agent for combating plant growth, as the agent is ca-
rakterisert ved at det består av eller som aktiv komponent inneholder s-triaziner med den generelle formel: characterized in that it consists of or contains as an active component s-triazines with the general formula:
I hvor X er halogen, lavere alkoksy, lavere alkyl- In where X is halogen, lower alkoxy, lower alkyl-
R<1>og R<2>er like eller forskjellige og er hydrogen eller lavere alkyl- eller alkenylgrupper med rette eller forgrenede kjeder, enten usubstituert eller substituert med minst én —OH, —OR, —SR eller —CN-gruppe; R<1> and R<2> are the same or different and are hydrogen or lower straight or branched chain alkyl or alkenyl groups, either unsubstituted or substituted with at least one —OH, —OR, —SR or —CN group;
R er lavere alkyl, ogR is lower alkyl, and
R3 og R<4>er like eller forskjellige, og er enten alkyl eller alkenylgrupper med rette eller forgrenede kjeder og med fra 1 til 8 karbonatomer, eller de danner sammen en tetra-, penta- eller heksa-metylengruppe. R3 and R<4> are the same or different, and are either alkyl or alkenyl groups with straight or branched chains and with from 1 to 8 carbon atoms, or they together form a tetra-, penta- or hexa-methylene group.
Med «lavere grupper» forståes bare grupper med fra 1 til 4 karbonatomer. By "lower groups" is meant only groups with from 1 to 4 carbon atoms.
Fremstillingen av disse forbindelser kan skje ved hjelp av fremgangsmåter som er kjent i seg selv. For eksempel kan 1 mol triklor-s-triazin omsettes med 1 mol a-amino-nitril med den generelle formel The production of these compounds can take place using methods which are known per se. For example, 1 mol of trichloro-s-triazine can be reacted with 1 mol of α-amino-nitrile with the general formula
i nærvær av et mol med et hydrogen-halogenid-bindemiddel, f. eks. natriumhydroksyd, og der-etter med 1 mol ammoniakk eller et amin med den generelle formel NHR3R<*>, også i nærvær av 1 mol natriumhydroksyd. Nitriler som egner seg for dette formål, er f. eks.: in the presence of a mole with a hydrogen halide binder, e.g. sodium hydroxide, and then with 1 mol of ammonia or an amine of the general formula NHR3R<*>, also in the presence of 1 mol of sodium hydroxide. Nitriles that are suitable for this purpose are, for example:
Alkylmercaptoforbindelsene kan f. eks. fremstilles ved en reaksjon mellom de tilsvarende klor-triaziner og et alkylmercaptan i nærvær av et syrebindemiddel. The alkyl mercapto compounds can e.g. is produced by a reaction between the corresponding chlorotriazines and an alkyl mercaptan in the presence of an acid binder.
Alkoksyforbindelsene kan f. eks. fremstilles med høyt utbytte hvis de tilsvarende klorderi-vater omsettes med natriumalkolat i en alkohol med forhøyet temperatur og trykk. Alkoxy compounds can e.g. is produced in high yield if the corresponding chlorine derivatives are reacted with sodium alcoholate in an alcohol at elevated temperature and pressure.
Azidotriaziner av den type som er nevnt ovenfor, kan enten fremstilles ved en reaksjon mellom halogentriazinene og et alkaliazid eller et ammoniumazid i dimetylformamid eller di-metylsulfoksyd, eller enda bedre fra den tilsvarende kvaternære forbindelse ved en reaksjon med et av de nevnte azider i vann. Azidotriazines of the type mentioned above can either be prepared by a reaction between the halogenotriazines and an alkali azide or an ammonium azide in dimethylformamide or dimethylsulfoxide, or even better from the corresponding quaternary compound by a reaction with one of the azides mentioned in water.
De ovenfor angitte forbindelser har gode herbicide egenskaper og kan både brukes som forbehandlingsherbicider og som etterbehand-lingsherbicider. Selv ved lave konsentrasjoner er de i stand til å regulere plantevekst. Avhengig av substituentene R<1>til R* kan de brukes for total nedkjempelse eller selektiv inhibering av ugress blant kulturplanter foruten for full-stendig nedkjempelse og inhibering av uønskede planter. The above-mentioned compounds have good herbicidal properties and can be used both as pre-treatment herbicides and as post-treatment herbicides. Even at low concentrations, they are able to regulate plant growth. Depending on the substituents R<1> to R*, they can be used for total control or selective inhibition of weeds among cultivated plants in addition to complete control and inhibition of unwanted plants.
De nye forbindelser kan også brukes for defoliering, reduksjon av fruktsetning, forsin-kelse av blomstring etc. De kan brukes indivi-duelt eller i blanding med hverandre eller sammen med andre herbicider. De kan også brukes i blanding med insekticider, fungisider og gjød-ningsstoffer. The new compounds can also be used for defoliation, reduction of fruit set, delay of flowering, etc. They can be used individually or in a mixture with each other or together with other herbicides. They can also be used in a mixture with insecticides, fungicides and fertilisers.
Eksempler på forbindelser med den generelle formel (I) er følgende: Examples of compounds with the general formula (I) are the following:
Det er allerede kjent en rekke substituerte bisalkylamino-triaziner. Enkelte av disse har vist seg å være utmerkede herbicider i praksis, som f. eks. forbindelsene 2,4-bisetyl-amino-6-klor-triazin, 2-etyl-amino-4-isopropyl-amino-6-klor-triazin, 2-metyl-amino-4-isopropyl-amino-6-metyl-mercapto-triazin og 2,4-bis-i-propyl-amino-6-metyl-mercapto-triazin. A number of substituted bisalkylaminotriazines are already known. Some of these have proven to be excellent herbicides in practice, such as e.g. the compounds 2,4-bisethyl-amino-6-chloro-triazine, 2-ethyl-amino-4-isopropyl-amino-6-chloro-triazine, 2-methyl-amino-4-isopropyl-amino-6-methyl-mercapto -triazine and 2,4-bis-i-propyl-amino-6-methyl-mercapto-triazine.
Disse forbindelser inneholder to alkylsubsti-tuerte aminogrupper med 1 til 3 karbonatomer. Man kjenner imidlertid ikke til 2-amino-4-alkylamino triaziner med sterk herbicid virkning. These compounds contain two alkyl-substituted amino groups with 1 to 3 carbon atoms. However, 2-amino-4-alkylamino triazines with strong herbicidal action are not known.
Det var derfor overraskende og uventet at de angjeldende triaziner med en aminogruppe og en cyanogruppe direkte tilknyttet et tertiært C-atom er meget kraftige herbicider ettersom alle forbindelser med en karboksamid, karboksyl eller karboalkoksygruppe i stedet for cyanogruppen ikke viser noen fytotoksisk virkning i det hele tatt, noe som f .eks. er tilfellet med forbindelsene 2-klor-4-etyl-amino-6-(-metyl-l-carboamyl-etyl)-amino-s-triazin og 2-klor-4-etyl-amino-6-(l-metyl-l-carboksy-etyl)-amino-s-triazin. It was therefore surprising and unexpected that the triazines in question with an amino group and a cyano group directly attached to a tertiary C atom are very powerful herbicides, since all compounds with a carboxamide, carboxyl or carbo alkoxy group instead of the cyano group show no phytotoxic effect at all , something that e.g. is the case with the compounds 2-chloro-4-ethyl-amino-6-(-methyl-1-carboamyl-ethyl)-amino-s-triazine and 2-chloro-4-ethyl-amino-6-(1-methyl- 1-carboxyethyl)-amino-s-triazine.
Den herbicide virkning av forbindelsene er således avhengig av cyanogruppen, og denne må være bundet til et tærtiært C-atom. Cyano-alkylamino-triaziner med gruppen -NH-(CH„)n-CN, er langt mindre effektive. The herbicidal effect of the compounds is thus dependent on the cyano group, and this must be bound to a tertiary C atom. Cyano-alkylamino-triazines with the group -NH-(CH„)n-CN are far less effective.
De klor-triaziner som anvendes i praksis, er virksomme lenge i jorden, noe som ofte er uøns-ket. Sammenliknet med disse forbindelser dekomponeres triazinene i midlene ifølge foreliggende oppfinnelse etter et relativt kort tidsrom. The chlorotriazines used in practice are active for a long time in the soil, which is often undesirable. Compared to these compounds, the triazines in the agents according to the present invention decompose after a relatively short period of time.
De klor-triaziner som anvendes ifølge foreliggende oppfinnelse, er meget selektive, f. eks. for dyrking av mais. I dette henseende likner de f. eks. 2-4-bisetyl-amino-6-klor-triazin. Sammenliknet med denne forbindelse har de imidlertid den store fordel at de etter en dyrknings-periode dekomponeres i jorden til forbindelser uten herbicid virkning. Det er således ikke nød-vendig igjen å dyrke mais neste år på samme område. The chlorotriazines used according to the present invention are very selective, e.g. for the cultivation of maize. In this respect, they are similar to e.g. 2-4-bisethyl-amino-6-chloro-triazine. Compared to this compound, however, they have the great advantage that after a cultivation period they decompose in the soil into compounds without herbicidal action. It is therefore not necessary to grow maize again next year in the same area.
Forbindelsenes selektivitet er imidlertid ikke bare begrenset til mais. Man har oppnådd selek-tiviteter også for andre kulturvekster. Forbindelser som f. eks. har følgende substituenter, er også selektive i mais: However, the selectivity of the compounds is not only limited to maize. Selectivities have also been achieved for other crops. Connections such as have the following substituents, are also selective in maize:
De følgende forbindelser er selektive i hvete: The following compounds are selective in wheat:
Man oppnådde en selektivitet i ris med følgende forbindelser Forbindelser med substituentene A selectivity was achieved in rice with the following compounds Compounds with the substituents
er eksempler på forbindelser som er selektive i bomull. are examples of compounds that are selective in cotton.
Avhengig av substituentene har forbindelsene en utmerket aktivitet både med hensyn til forbehandling og etterbehandling. I de fleste tilfelle er forbindelsene krystallinske og de er meget godt løselig i de fleste organiske løsnings-midler. I dette henseende skiller de seg fra kjente klor-bis-alkylamino-triaziner, som er meget van-skelig løselig i alle vanlige løsningsmidler. De nye forbindelser kan følgelig oppløst i oppløs-ningsmidler meget lett sprøytes ut over jord-bruksområder fra fly. Depending on the substituents, the compounds have an excellent activity both with respect to pre-treatment and post-treatment. In most cases, the compounds are crystalline and they are very soluble in most organic solvents. In this respect, they differ from known chloro-bis-alkylamino-triazines, which are very difficult to dissolve in all common solvents. The new compounds can therefore be dissolved in solvents very easily sprayed over agricultural areas from aircraft.
Man kan f. eks. anvende følgende løsnings-midler, alkoholer, ketoner, hydrokarboner, halo-generte hydrokarboner som f. eks. klornaftalin, mineralolje som dieselolje, vegetabilske oljer eller blandinger av disse løsningsmidler. One can e.g. use the following solvents, alcohols, ketones, hydrocarbons, halo-generated hydrocarbons such as e.g. chloronaphthalene, mineral oil such as diesel oil, vegetable oils or mixtures of these solvents.
Triazinforbindelsene kan også pålegges et fast substrat. Alle kjente bærestoffer for dette formål kan brukes her, f. eks. leire, kaolin, kiselgur, bentonit, talkum, finmalt kalsiumkarbonat, trekull, sagflis og liknende. The triazine compounds can also be applied to a solid substrate. All known carriers for this purpose can be used here, e.g. clay, kaolin, diatomaceous earth, bentonite, talc, finely ground calcium carbonate, charcoal, sawdust and the like.
De aktive forbindelser kan også blandes med substrater i tørr form. Det er imidlertid også mu-lig å sprøyte løsninger eller emulsjoner på substratet, eller blande det med sistnevnte og der-etter tørke blandingen. The active compounds can also be mixed with substrates in dry form. However, it is also possible to spray solutions or emulsions on the substrate, or mix it with the latter and then dry the mixture.
For å oppnå bedre adhesjon mellom de aktive forbindelser og substratet kan man anvende kjente tilklebningsmidler som stivelse, kasein, alginater og liknende. In order to achieve better adhesion between the active compounds and the substrate, known adhesives such as starch, casein, alginates and the like can be used.
Endelig kan triazinforbindelsene (hvis nød-vendig, sammen med substratene) blandes med dispergerende og stabiliserende forbindelser, og de kan f. eks. opparbeides til en pasta eller et pulver som så kan utrøres i vann til en suspen-sjon. Finally, the triazine compounds (if necessary, together with the substrates) can be mixed with dispersing and stabilizing compounds, and they can e.g. processed into a paste or a powder which can then be stirred in water to form a suspension.
Anioniske, kationiske eller ikkeioniske forbindelser kan brukes som fuktemidler, emulge-rende og stabiliserende forbindelser. Eksempelvis kan nevnes salter av fettsyrer, alkylarylsulfo-nater, sekundære alkylsulfater, resinater, poly-etyleneter av fettalkoholer, fettsyrer eller fett-aminer, kvaternære ammoniumforbindelser, lig-ninsulfonsyre, saponin, gelatin, kasein, enten en-keltvis eller i blanding med hverandre. Anionic, cationic or non-ionic compounds can be used as wetting agents, emulsifying and stabilizing compounds. For example, mention may be made of salts of fatty acids, alkylarylsulfonates, secondary alkyl sulfates, resinates, polyethylene ethers of fatty alcohols, fatty acids or fatty amines, quaternary ammonium compounds, ligninsulfonic acid, saponin, gelatin, casein, either individually or in a mixture with each other .
Eksempel 1.Example 1.
10 deler 2-metyl-a<mino-4-(l-metyl-l-cyano-etyl)-amino-6-klor-s-triazin, 89 deler bentonitt og 1 del høydispergert, pyrogenisk fremstilt sili-siumsyre ble malt i en kule-mølle til støvfinhet. Denne blanding kan brukes som et forstøvnings-pulver. 10 parts of 2-methyl-amino-4-(1-methyl-1-cyano-ethyl)-amino-6-chloro-s-triazine, 89 parts of bentonite and 1 part of highly dispersed, pyrogenically produced silicic acid were ground in a ball mill for dust fineness. This mixture can be used as an atomizing powder.
Eksempel 2.Example 2.
En blanding av 2-etyl-amino-4-(l-cyano-l-metyl-n-propyl) -amino-6-metoksy-s-triazin og 98 deler kiselgur ble malt i en kulemølle til mak-simal finhet. Blandingen kan brukes som et for-støvningspulver. A mixture of 2-ethyl-amino-4-(1-cyano-1-methyl-n-propyl)-amino-6-methoxy-s-triazine and 98 parts diatomaceous earth was ground in a ball mill to maximum fineness. The mixture can be used as a pre-dusting powder.
Eksempel 3.Example 3.
En blanding av 20 deler 2-isopropyl-amino-4-(l-cyano-l-metyl-etyl)-amino-6-metyl-mercapto-s-triazin og 70 deler klorbenzen og 10 deler av en oktyl-fenyl-polyglykoleter av di-t-butylfenol og 10 til 12 mol etylenoksyd («Hosta-pal CV») ble fremstilt. Med vann danner denne blanding en stabil dispersjon. A mixture of 20 parts of 2-isopropyl-amino-4-(1-cyano-1-methyl-ethyl)-amino-6-methyl-mercapto-s-triazine and 70 parts of chlorobenzene and 10 parts of an octyl-phenyl-polyglycol ether of di-t-butylphenol and 10 to 12 moles of ethylene oxide ("Hosta-pal CV") was prepared. With water, this mixture forms a stable dispersion.
Eksempel 4.Example 4.
25 deler 2-isopropyl-amino-4-(l-cyano-l-mietyl-etyl)-amino-6-klor-triazin oppløses i 150 deler cycloheksanon, 15 deler xylen og 10 deler av en substituert naftalendisulfosyre, f. eks. «BX». Med vann danner denne blanding en stabil emulsjon. 25 parts of 2-isopropyl-amino-4-(1-cyano-1-methyl-ethyl)-amino-6-chloro-triazine are dissolved in 150 parts of cyclohexanone, 15 parts of xylene and 10 parts of a substituted naphthalenedisulfonic acid, e.g. "BX". With water, this mixture forms a stable emulsion.
Eksempel 5.Example 5.
50 deler 2-etyl-amino-4-(l-cyano-l-metyl-etyl)-amino-6-azido-triazin oppløses i 450 deler paraffin. Denne løsning kan anvendes for øye-blikkelig utsprøytning. 50 parts of 2-ethyl-amino-4-(1-cyano-1-methyl-ethyl)-amino-6-azido-triazine are dissolved in 450 parts of paraffin. This solution can be used for instant spraying.
Eksempel 6.Example 6.
De følgende prøver ble utført for å undersøke forbindelsenes herbicide aktivitet: The following tests were carried out to investigate the herbicidal activity of the compounds:
a) Behandling av jorden etter såingen:a) Treatment of the soil after sowing:
I et drivhus hvis temperatur var 21°C ble In a greenhouse whose temperature was 21°C was
forskjellige typer frø satt ned i jorden som igjen befant seg i små plastikkar. Om morgenen ble de vannet og om ettermiddagen ble de behandlet med en dispersjon som var fremstilt ved å helle en løsning av herbicidet over i like deler vann. Ved normale vanningsbetingelser undersøkte man så spiringen av frøene. To uker etter såingen undersøkte man i hvilken grad planteveksten var hemmet. different types of seeds were planted in the soil, which in turn were in small plastic containers. In the morning they were watered and in the afternoon they were treated with a dispersion made by pouring a solution of the herbicide into equal parts of water. The germination of the seeds was then examined under normal watering conditions. Two weeks after sowing, the extent to which plant growth was inhibited was examined.
b) Behandling av jorden etter spiring.b) Treatment of the soil after germination.
I et drivhus hvis temperatur var 21°C, ble In a greenhouse whose temperature was 21°C,
forskjellige typer frø satt ned i jorden.different types of seeds planted in the soil.
Etter spiringen ble jorden behandlet med samme vandige dispersjon som nevnt under avsnitt a). Etter to uker bestemte man i hvilken grad planteveksten var nedsatt. After germination, the soil was treated with the same aqueous dispersion as mentioned under section a). After two weeks, it was determined to what extent plant growth had been reduced.
c) Fremgangsmåten var den samme som beskrevet under avsnitt b), men med den forskjell at c) The procedure was the same as described under section b), but with the difference that
den vandige dispersjon av den aktive forbindelse ikke ble sprøytet på jorden, men på bladene. the aqueous dispersion of the active compound was not sprayed on the soil, but on the leaves.
Resultatene av prøvene er angitt i de føl-gende tabeller. Ved bedømmelsen av den herbicide aktivitet anvendte man en skala hvor 0 står for normal og 9 for total ødeleggelse av planten. The results of the tests are indicated in the following tables. When assessing the herbicidal activity, a scale was used where 0 stands for normal and 9 for total destruction of the plant.
Som den aktive forbindelse ble følgende forbindelser anvendt i en konsentrasjon på 20 kg/ ha i prøvene under avsnitt a) og i en konsentrasjon på 10 og 1 kg/ha i prøvene under avsnitt b) og c) henholdsvis. As the active compound, the following compounds were used in a concentration of 20 kg/ha in the samples under section a) and in a concentration of 10 and 1 kg/ha in the samples under sections b) and c) respectively.
I 2-amino-4-(l-metyl-l-cyano-etyl)-amino-6-klor-s-triazin I 2-amino-4-(1-methyl-1-cyano-ethyl)-amino-6-chloro-s-triazine
II 2-metyl-amino-4-(l-metyl-l-cyano-etyl-amino-6-klor-s-triazin II 2-methyl-amino-4-(1-methyl-1-cyano-ethyl-amino-6-chloro-s-triazine
III 2-etyl-amino-4- (1-metyl-lcyano-etyl)-amino-6-klor-s-triazin III 2-Ethyl-amino-4-(1-methyl-1-cyano-ethyl)-amino-6-chloro-s-triazine
IV 2-etyl-amino-4- (1-metyl-1-cyano-n-propyl)-amino-6-klor-s-triazin IV 2-ethyl-amino-4-(1-methyl-1-cyano-n-propyl)-amino-6-chloro-s-triazine
V 2-metyl-amino-4-(l-metyl-l-cyano-V 2-methyl-amino-4-(1-methyl-1-cyano-
etyl) -amino-6-azido-s-triazinethyl)-amino-6-azido-s-triazine
VI 2-etyl-amino-4-(l-metyl-l-cyano-etyl)-amino-6-azido-s-triazin VI 2-Ethyl-amino-4-(1-methyl-1-cyano-ethyl)-amino-6-azido-s-triazine
VII 2-etyl-amino-4-(l-metyl-l-cyano-etyl)-amino-6-metyl-mercapto-s-triazin VII 2-Ethyl-amino-4-(1-methyl-1-cyano-ethyl)-amino-6-methyl-mercapto-s-triazine
VIII 2,4-bisetyl-amino-6-klor-s-triazinVIII 2,4-bisethyl-amino-6-chloro-s-triazine
IX 2-etyl-amino-4-isopropyl-amino-6-klor-s-triazin IX 2-ethyl-amino-4-isopropyl-amino-6-chloro-s-triazine
X 2-etyl-amino-4-t-butyl-amino-6-metyl-mercapto-triazin X 2-ethyl-amino-4-t-butyl-amino-6-methyl-mercapto-triazine
Eksempel 7. Example 7.
Frø av havre, åkersennep og lin ble sådd i små kar fylt med jord. Etterat plantene hadde fått en høyde på ca. 8 cm, ble de behandlet med 0,5 pst. emulsjon av 2-etyl-amino-4-(l-metyl-l-cyano-etyl)-amino-6-metoksy-s-triazin. Etter 18 dager var alle plantene helt ødelagt. Seeds of oats, field mustard and flax were sown in small pots filled with soil. After the plants had reached a height of approx. 8 cm, they were treated with 0.5% emulsion of 2-ethyl-amino-4-(1-methyl-1-cyano-ethyl)-amino-6-methoxy-s-triazine. After 18 days, all the plants were completely destroyed.
Eksempel 8.Example 8.
For å bestemme den herbicide virkning ble følgende prøver utført: a) Behandling av jorden etter såing. To determine the herbicidal effect, the following tests were carried out: a) Treatment of the soil after sowing.
Prøveplanter ble sådd i smale striper i plastikkar (38 x 13 x 6 cm) fylt med John Innes pot-ing compost. Såing, vanning foruten sprøyting med selve herbicidet ble utført på samme dag. Man anvendte forskjellige konsentrasjoner av den aktive forbindelse, og etter ca. 14 dager ble den oppnådde fytotoksitet bestemt. Man anvendte en skala hvor 0 står for normal vekst og 9 for total ødeleggelse av planten. Pytotoksiteten for hver type plante ble omregnet til pst. og plot-tet mot konsentrasjonen av den aktive forbindelse, og ut fra dette kunne man bestemme PD50, dvs. den konsentrasjon av aktiv forbindelse i kg/ ha som resulterer i en 50 pst. reduksjon av veksten. Test plants were sown in narrow strips in plastic pots (38 x 13 x 6 cm) filled with John Innes potting compost. Sowing, watering in addition to spraying with the herbicide itself was carried out on the same day. Different concentrations of the active compound were used, and after approx. After 14 days, the phytotoxicity achieved was determined. A scale was used where 0 stands for normal growth and 9 for total destruction of the plant. The phytotoxicity for each type of plant was converted to percent and plotted against the concentration of the active compound, and from this the PD50 could be determined, i.e. the concentration of active compound in kg/ha that results in a 50 percent reduction of the growth.
b) Behandling etter spiring.b) Treatment after germination.
I dette tilfelle ble frøene satt i sirkulære In this case, the seeds were set in circulars
plastikkar (diameter 0,9 cm). Når plantene kom-mer opp av jorden, blir de sprøytet med forskjellige konsentrasjoner av den aktive forbindelse. Etter 10 dager ble fytotoksiteten og PD50bestemt slik det er beskrevet under avsnitt a). plastic tub (diameter 0.9 cm). When the plants emerge from the soil, they are sprayed with different concentrations of the active compound. After 10 days, the phytotoxicity and PD50 were determined as described under section a).
Hvis kveke (Agropyron repens) ble brukt som prøveplante, ble skuddene kuttet ved jordover- If quack (Agropyron repens) was used as a test plant, the shoots were cut at above-ground
flaten og den videre vekst ble så bestemt etter 3 uker. the area and further growth were then determined after 3 weeks.
PDg,, verdiene og de typer planter som ble prøvd er angitt i tabell I (for prøvene under avsnitt a) og i tabell II (for prøvene under avsnitt PDg,, the values and the types of plants tested are indicated in table I (for the samples under section a) and in table II (for the samples under section
b). I prøvene anvendte man aktive forbindelser med den generelle formel b). Active compounds with the general formula were used in the tests
hvilke grupper X, R], R<3>og R<*>representerer i hvert enkelt tilfelle, er angitt i tabellene. which groups X, R], R<3>and R<*> represent in each individual case are indicated in the tables.
Eksempel 9. Example 9.
For å prøve den herbicide virkning ble forbindelser ifølge foreliggende oppfinnelse anvendt i form av løsninger eller suspensjoner i en blanding av like deler vann og aceton som også inne-holdt 1 pst. av et kommersielt dispergeringsmid-del og 2 pst. glycerol. Følgende typer planter ble behandlet: Mais, hvete, rai-gress, erter, lin, åkersennep og sukkerroe. To test the herbicidal effect, compounds according to the present invention were used in the form of solutions or suspensions in a mixture of equal parts water and acetone which also contained 1 percent of a commercial dispersant and 2 percent of glycerol. The following types of plants were treated: maize, wheat, rye grass, peas, flax, field mustard and sugar beet.
Ved behandling ble bladene sprøytet med suspensjonen eller løsningene ved hjelp av en sprøyteanordning. Anordningen muliggjorde en utsprøytning på 1 eller 10 kg/ha aktiv forbindelse i et volum på 630 liter pr. time. In treatment, the leaves were sprayed with the suspension or solutions using a spray device. The device made it possible to spray 1 or 10 kg/ha of active compound in a volume of 630 liters per hour.
For behandling av jorden etter såing ble prø-veplantene sådd i jorden som igjen var plasert i For treatment of the soil after sowing, the test plants were sown in the soil which was again placed in
små plastikkar. Såingen og vanningen fant sted kort tid før behandlingen, dvs. samtidig med behandlingen av bladene, slik at man brukte de samme mengder aktiv forbindelse. small plastics. The sowing and watering took place shortly before the treatment, i.e. simultaneously with the treatment of the leaves, so that the same amounts of active compound were used.
Ved slutten av prøveperioden (7 dager for behandling av bladene og 11 dager for behandling av jorden før spiringen), ble resultatene bestemt ved undersøkelse. Den fytotoksiske virkning ble bedømt etter en skala fra 0 til 9, hvor 0 står for ingen effekt og 9 for total ødeleggelse av planten. Fytotokslteten for alle 7 typer planter ved en konsentrasjon av den aktive forbindelse på 1 kg/ha, er angitt i de følgende tabeller sammen med data vedrørende strukturen av de anvendte forbindelser. Tabell (VI) viser en sam-menlikning med tidligere kjente forbindelser. At the end of the trial period (7 days for the treatment of the leaves and 11 days for the treatment of the soil before germination), the results were determined by examination. The phytotoxic effect was judged on a scale from 0 to 9, where 0 stands for no effect and 9 for total destruction of the plant. The phytotoxicity for all 7 types of plants at a concentration of the active compound of 1 kg/ha is indicated in the following tables together with data concerning the structure of the compounds used. Table (VI) shows a comparison with previously known compounds.
Eksempel 10. Example 10.
For å undersøke dekomponerbarheten av forbindelser Ifølge foreliggende oppfinnelse i jorden ble følgende fremgangsmåte anvendt: Luft-tørket leire ble vannet til et fuktighets-innhold på 20 pst. Løsninger av den aktive forbindelse i 5 cm<2>aceton, dvs. en konsentrasjon . på 0,3 kgm/ha, ble tilsatt hvert 2 kg av dette materialet, som så ble lagret i lukkede plastikk-beholdere ved en konstant temperatur på 21°C. Ved gitte tidsintervaller ble det tatt ut prøver som ble plaser i potter og hvori man plantet frø-planter av sukkerroe. Pottene fikk vann neden-fra og ble holdt på 21 °C i et drivhus. Fytotoksiteten ble bestemt en uke etter inmplantningen. Ødeleggelsen av planten i pst. er angitt i den nedenstående tabell: To investigate the decomposability of compounds according to the present invention in the soil, the following procedure was used: Air-dried clay was watered to a moisture content of 20 percent. Solutions of the active compound in 5 cm<2>acetone, i.e. a concentration of . of 0.3 kgm/ha, was added every 2 kg of this material, which was then stored in closed plastic containers at a constant temperature of 21°C. At given time intervals, samples were taken which were placed in pots and in which sugar beet seedlings were planted. The pots received water from below and were kept at 21 °C in a greenhouse. Phytotoxicity was determined one week after implantation. The destruction of the plant in pst. is indicated in the table below:
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