NL8204109A - 1,2,4-Triazoline-5-one herbicides for galium species - give good control of resistant weeds in cereal and sugar beet e.g. the 3-benzyl-4-para methoxyphenyl cpd. - Google Patents

1,2,4-Triazoline-5-one herbicides for galium species - give good control of resistant weeds in cereal and sugar beet e.g. the 3-benzyl-4-para methoxyphenyl cpd. Download PDF

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NL8204109A
NL8204109A NL8204109A NL8204109A NL8204109A NL 8204109 A NL8204109 A NL 8204109A NL 8204109 A NL8204109 A NL 8204109A NL 8204109 A NL8204109 A NL 8204109A NL 8204109 A NL8204109 A NL 8204109A
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herbicides
aryl
galium
herbicidal
triazoline
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Fahlberg List Veb
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D249/00Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/081,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647Triazoles; Hydrogenated triazoles
    • A01N43/6531,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N47/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20N-Aryl derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D231/00Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D249/00Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/081,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/101,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/12Oxygen or sulfur atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
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  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Herbicide compsn. for control of weeds, esp. Galium ssp., contains 3-R1-4-R2-1,2,4- triazoline-5-one of formula (I) as active cpd., with diluents, supports, vehicles and/or classical formulation additives (where R1, R2 independently are H or alkyl, aryl, aralkyl or cycloalkyl all opt. substd. by gp(s) such as halo, hydroxy, alkoxy, aryloxy, alkylthio, arylthio or amino (opt. substd. by alkyl and/or aryl gps.)). Pref. the individual ingredients of the compsn. are mixed immediately prior to use ("tank mix") and opt. diluted with water. Herbicide compsn. which is effective for control of Galium ssp. (catchweed) and is partic. useful for control in cereal and sugar beet crops. The selectivity and/or synergistic activity of (I) may be increased by use in combination with other herbicides.

Description

S 3072-17 Ned. * - -*S 3072-17 Ned. * - - *

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Korte aanduiding: Herbicide_J&iddalen,die 1.2.4-triazolinon- (5) -verbindingen bevatten.Short designation: Herbicides, containing 1,2,4-triazolinone (5) compounds.

De uitvinding heeft betrekking op nieuwe herbicide middelen ter bestrijding van ongewenste plantengroei in de landbouw, tuinbouw en bosbouw, op zichzelf of in kombinatie met andere landbouwchemicaliën.The invention relates to new herbicidal agents for controlling undesired plant growth in agriculture, horticulture and forestry, alone or in combination with other agricultural chemicals.

De bestrijding van ongewenste grassoorten en onkruidsoorten met land-5 bouwchemicaliën in landbouwcultures wordt vaak bemoeilijkt, doordat problemen opleverende onkruidsoorten door de meeste middelen niet aangetast worden. Deze leemtes in de werking leiden er vaak toe, dat speciale onkruidsoorten door de uitschakeling van de natuurlijke concurenten bijzonder goede ontwikkelingscanstandigheden aantreffen en zich sterk vermeerderen. Het wordt 10 dan onvermijdelijk preparaten toe te passen, die deze onkruidsoorten, die zich eenzijdig sterk vermeerderd hebben, bestrijden. Bijzonder moeilijk te bestrijden onkruidsoorten zijn Galium ssp.The control of unwanted grasses and weeds with agricultural chemicals in agricultural cultures is often complicated, because problematic weeds are not affected by most means. These gaps in operation often lead to special weeds encountering particularly good development conditions and multiplication by eliminating natural competitors. It then becomes inevitable to use preparations which control these weeds which have multiplied strongly on one side. Galium ssp. Are particularly difficult to control weeds.

De uitvinding heeft derhalve betrekking op de toepassing van nieuwe herbicida_Mddélen die in het bijzonder een voldoende werking vertonen 15 tegenover problemen gevende onkruidsoorten, bijvoorbeeld Galium ssp.The invention therefore relates to the use of new herbicides which are in particular sufficiently effective against problematic weeds, for example Galium ssp.

Verrassenderwijs werd gevonden, dat 3.4-digesubstitueerde 1.2.4-tri-azolinonen-(5) met de op het formuleblad weergegeven formule een goede werking vertonen tegenover enige onkruidsoorten, in het bijzonder tegen Galium ssp., waarbij in de genoemde formule en onafhankelijk van el-20 kaar waterstof of eventueel gesubstitueerde alkyl-, aryl-, aralkyl- of cyclo-alkyIresten voorstellen. Daarbij is het beslist ook mogelijk, dat alkyl-, aryl-, aralkyl- en cycloalkylresten enkelvoudig of meervoudig gesubstitueerd kunnen zijn door halogeenatomen, hydroxylgroepen, eventueel door alkyl- en/ of arylresten gesubstitueerde aminogroepen, benevens door alkoxy-, aryloxy-, 25 alkylthio- en arylthioresten.Surprisingly, it has been found that 3,4-disubstituted 1,2,4-triazolinones- (5) with the formula shown on the formula sheet show good activity against some weeds, in particular against Galium ssp., Wherein in said formula and independently of each other represents hydrogen or optionally substituted alkyl, aryl, aralkyl or cycloalkyl radicals. It is certainly also possible that alkyl, aryl, aralkyl and cycloalkyl radicals can be singly or multiply substituted by halogen atoms, hydroxyl groups, optionally substituted amino groups by alkyl and / or aryl radicals, in addition to alkoxy, aryloxy, alkylthio and arylthio residues.

De aktieve stoffen volgens de uitvinding kunnen als zodanig toegepast worden, maar doelmatigerwijze geschiedt hun toepassing echter in de voor herbiciden gebruikelijke preparaat- respectievelijk aanbrengingsvormen, zoals oplos.Ji£3délen emulsies, suspensies, concentraten, stuifpoeders, 30 strooimiddelen, respectievelijk granulaten. Deze formuleringen worden bereid onder toepassing van de gebruikelijke hulpstoffen, zoals oplosmiddelen, dragerstoffen, emulgeer- en dispergeermiddelen.The active substances according to the invention can be used as such, but advantageously, however, they are used in the preparation or application forms customary for herbicides, such as solvents, three-part emulsions, suspensions, concentrates, dusting powders, dispersing agents or granulates. These formulations are prepared using the usual auxiliaries, such as solvents, carriers, emulsifying and dispersing agents.

De herbicide_middelen volgens de uitvinding zijn geschikt voor de selectieve bestrijding van onkruidsoorten en ongewenste grassoorten in landbouw-, 35 tuinbouw- en bosbouwcultures, bij voorkeur in graansoorten en beta-bieten.The herbicides according to the invention are suitable for the selective control of weeds and undesirable grasses in agricultural, horticultural and forestry cultures, preferably in cereals and beta beets.

Ter bereiding van synergistische, respectievelijk selectieve effekten kunnen zij met andere geschikte herbiciden, respectievelijk landbouwchemicaliën gekombineerd worden. Een doelmatige toepassingsvorm is ook het tankmengsel, 8204109 - 2 -For the preparation of synergistic or selective effects, they can be combined with other suitable herbicides or agricultural chemicals. An effective application form is also the tank mixture, 8204109 - 2 -

Daarbij worden de geformuleerde afzonderlijke komponenten kort vóór het aanbrengen verenigd, respectievelijk gemeenschappelijk met de benodigde hoeveelheid water verdund.The formulated individual components are then combined shortly before application or diluted together with the required amount of water.

Enige verbindingen van de uitvinding, met inbegrip van hun fysische 5 gegevens, zijn in tabel k opgegeven, waarbij de synthese van afzonderlijke vertegenwoordigers uit de literatuur bekend is (H. Gehlen en W Schade, Liebigs Ann. Chem. 675 (1964), 180.Some compounds of the invention, including their physical data, are listed in Table k, where the synthesis of individual representatives is known from the literature (H. Gehlen and W Schade, Liebigs Ann. Chem. 675 (1964), 180 .

De volgende, niet-beperkende voorbeelden lichten de uitvinding toe.The following non-limiting examples illustrate the invention.

Voorbeeld 1 10 Bij proeven in potten werd de herbicide·,/werking van de bovengenoemde stof bij proeven vóór en na het uitkomen onderzocht onder toepassing van een bodem met een middelmatige sorptiecapaciteit (sL) bij een watercapa-citeit van 60%. Het aanbrengen van de nieuwe chemische verbinding geschiedde als aktieve stof in oplossing in aceton (1000 1/ha) met behulp 15 van een injektiespuit direkt na het uitzaaien van de onkruiden (VA), respectievelijk op de na 14 dagen groeiende planten (NA).Example 1 In pot tests, the herbicidal activity of the above substance was tested in pre and hatch tests using a soil of medium sorption capacity (sL) at a water capacity of 60%. The application of the new chemical compound was carried out as an active substance in solution in acetone (1000 l / ha) by means of a syringe immediately after the seeding of the weeds (VA) and the plants growing after 14 days (NA).

De waardering van de herbicide /werking geschiedde volgens de onderstaande schaal:The herbicide / effect was assessed on the scale below:

Nummer op schaal_Ernst van de schade_% Bezetting met onkruid 20 1 vernietigd 0 2 5 3 15 4 30 5 50 25 6 70 7 85 8 95 9 onbeschadigd 100Number on scale_ Serious damage_% Weed cover 20 1 destroyed 0 2 5 3 15 4 30 5 50 25 6 70 7 85 8 95 9 undamaged 100

De chemische verbindingen van de uitvinding onderscheiden zich door 30 de vernietiging van de moeilijk bestrijdbare onkruidsoorten Galium ssp., waarbij behandeling vóór het uitlopen van de onkruidplanten werkzamer is dan de behandeling na het uitlopen.The chemical compounds of the invention are distinguished by the destruction of the hard-to-control weed species Galium ssp., Where pre-weed treatment is more effective than post-weed treatment.

Als representatief voor de verbindingen van de uitvinding zijn in tabel B de proefresultaten weergegeven onder toepassing van de boven aange-35 geven waarderingsschaal.As representative of the compounds of the invention, Table B shows the test results using the rating scale noted above.

Voorbeeld ÏIExample II

Verbinding 4(zie tabel 1) werd als 20-%'s spuitpoeder in een concen-tratietrajekt van 0,5 - 2,0 kg aktieve stof per ha bij een proef vóór het opkomen onderzocht op zijn werking tegen Galium aparine en enige gekozen 8204109 - 3 - ' · < cultuurplanten. Hierbij bleek bij· een dosis van 1,5 kg aktieve stof per ha de herbicide werking tegen galium aparine zeer goed te zijn en selectiviteit op te treden. De resultaten zijn weergegeven in tabel C.Compound 4 (see Table 1) was tested for its activity against Galium aparine and some selected 8204109 as 20% by weight spray powder in a concentration range of 0.5 - 2.0 kg of active substance per ha in a pre-emergence test. - 3 - '· <cultivated plants. At a dose of 1.5 kg of active substance per ha, the herbicidal action against galium aparine was found to be very good and selectivity to occur. The results are shown in Table C.

Voorbeeld IIIExample III

5 Bij veldproeven werd verbinding 4 als 50-%'s spuitpoeder vóór het op komen onderzocht in suikerbieten in doses van 0,8, 1,2 en 1,8 kg aktieve stof per ha. Galium aparine behoorde tot de onkruiksoorten, die het onkruid-bestand pp het proefveld vormden, en het werd bij toepassing van 1,8 kg aktieve stof per ha zeer goed bestreden. De ontwikkeling van de bieten 10 onderging geen enkele, door het preparaat veroorzaakte beïnvloeding. De resultaten zijn weergegeven in tabel D.In field trials, Compound 4 was tested as a 50% pre-emergence spray powder in sugar beet at doses of 0.8, 1.2 and 1.8 kg of active substance per hectare. Galium aparine was one of the cultivars that made up the weed stock in the test field, and it was very well controlled when using 1.8 kg of active substance per hectare. The development of the beets 10 did not undergo any influence caused by the preparation. The results are shown in Table D.

Tabel A Verbindings- no. _h_^2_Smeltpunt (°C) 15 1 H C.H -0CH_-p 195 - 197 6 4 3 2 CH, C-.H -OCH.--p 201 - 203 3 6 4 3 3 CH20H C6H4-OCH3-p 215 - 217 4 C.H.CH. CJH -OCH.-p 172 - 174 6 5 2 6 4 3 * 20 5 C-H_CH0 C.H_ 224 - 225 6 5 2 6 5 6 C.H-CH- C.H -Cl-p 170 - 172 6 5 2 6 4 7 C.H-CH,, CJH,-3.4-Cl0 164 - 166 6 5 2 6 3 2 2S 8 ^Λΐ C6H4~OCH3-J> 210 9 tert-C.H„ C.ö-CCH-p 198 4 9 6 4 3 10 C^H-CH- C.H.-OH—p 241 - 242 6 5 2- 6 4 * 11 C.H CH„ CcH-OCHc-p 174 - 176 6 5 2 6 4 6 5 30 12 CgHgC^ C6H4-N(CH3)2-p 191 - 192 13 C H..NHCB- CcH -OCH.-p 165 - 168 o j 6 b 4 <3 14 C-H- CJB,-0CH--p 230 - 231 6 5 6 4 3 15 C H.CH.CH. C.H OCH -p 174 - 176 6 5 2 2 6 4 3 35 16 C.H.NHCOOCH. C.H.OCH.-p 92 - 97 6 5 2 6 4 3 17 C1CH2 CgH4OCH3-p 143 - 145 18 CrH_CH(OH) C^H -OCH.-p 198 - 200 6 5 6 4 3 1 8204109 C.H-CH C,H CH„ 139 - 140 6 5 2 6 5 2 T 'V- ι 9 - 4 -Table A Connection No. _h_ ^ 2_ Melting point (° C) 15 1 H CH -0CH_-p 195 - 197 6 4 3 2 CH, C-.H -OCH .-- p 201 - 203 3 6 4 3 3 CH20H C6H4 -OCH3 -p 215-217 4 CHCH. CJH -OCH.-p 172 - 174 6 5 2 6 4 3 * 20 5 C-H_CH0 C.H_ 224 - 225 6 5 2 6 5 6 CH-CH- CH -Cl-p 170 - 172 6 5 2 6 4 7 CH-CH ,, CJH, -3.4-Cl0 164 - 166 6 5 2 6 3 2 2S 8 ^ Λΐ C6H4 ~ OCH3-J> 210 9 tert-CH „C.ö-CCH-p 198 4 9 6 4 3 10 C ^ H-CH-CH-OH — p 241 - 242 6 5 2- 6 4 * 11 CH CH · CcH-OCHc-p 174 - 176 6 5 2 6 4 6 5 30 12 CgHgC ^ C6H4-N (CH3 ) 2-p 191 - 192 13 C H..NHCB- CcH -OCH.-p 165 - 168 oj 6 b 4 <3 14 CH- CJB, -0CH - p 230 - 231 6 5 6 4 3 15 C H .CH.CH. C.H OCH -p 174 - 176 6 5 2 2 6 4 3 35 16 C.H.NHCOOCH. CHOCH.-p 92 - 97 6 5 2 6 4 3 17 C1CH2 CgH4OCH3-p 143 - 145 18 CrH_CH (OH) C ^ H -OCH.-p 198 - 200 6 5 6 4 3 1 8204109 CH-CH C, H CH „139 - 140 6 5 2 6 5 2 T 'V- ι 9 - 4 -

Verbindings- R. R„ Smeltpunt (°C) no._1_2___'_ 20 C-H CH„ n-C.H. 95 - 97 5 5 2 4 9 21 C,HeCH_ cyclo-C H 195 - 197 5 5 2 * 6 11Compound R. R „Melting point (° C) no._1_2 ___'_ 20 C-H CH„ n-C.H. 95 - 97 5 5 2 4 9 21 C, HeCH_ cyclo-C H 195 - 197 5 5 2 * 6 11

5 Tabel B5 Table B

; 1,0 1,0 3,0 6,0 kg ASb)/ha; 1.0 1.0 3.0 6.0 kg ASb) / ha

Onkruidsoort Prometryn Verbinding 4a^ _VA NA VA_NA VA NA VA_NA_Weed species Prometryn Compound 4a ^ _VA NA VA_NA VA NA VA_NA_

Stellaria 10 media 111 1111 1Stellaria 10 media 111 1111 1

Agrostemma githago 211 1111 1Agrostemma githago 211 1111 1

Lamium purpureum 2 11 4141 1Lamium purpureum 2 11 4141 1

Thlaspi 15 arvense 211 1111 1Thlaspi 15 arvense 211 1111 1

Spergula arvensis 111 1111 1 . Galium aparine 993 3111 1Spergula arvensis 111 1111 1. Galium aparine 993 3111 1

a) zie tabel Aa) see table A.

b) aktieve stof Tabel Cb) Active Substance Table C

Herbicide werkingen verdraagbaarheid voor cultuurplanten van 3-benzyl 4-p.methoxyfenyl 1.2,4-triazoli.non-(5) bij toepassing vóór het opkomen. Onderzochte plant 0,5 0,75 1,1 1,5 2,0 kg AS/ha _(waarderingscij fer^_Herbicidal actions tolerance for cultivated plants of 3-benzyl 4-p-methoxyphenyl 1,2,4-triazoli.non- (5) when used before emergence. Investigated plant 0.5 0.75 1.1 1.5 2.0 kg AS / ha _ (rating ^ _

Galium aparine 5 5 3 1 1Galium aparine 5 5 3 1 1

Mais 9 9 9 9 9Maize 9 9 9 9 9

Haver 9 9 9 8 7Oats 9 9 9 8 7

Tarwe 9 9 9 9 8 30 Bieten 99 986Wheat 9 9 9 9 8 30 Beets 99 986

Tabel DTable D

Herbicide werking van 3-benzyl 4-p.methoxyfenyl 1.2.4-triazolinon-(5) tegenHerbicidal action of 3-benzyl 4-p-methoxyphenyl 1,2,4-triazolinone- (5) against

Galium aparine bij toepassing vóór het opkomen in suikerbieten (7 weken na de behandeling) 35Galium aparine when used before emergence in sugar beet (7 weeks after treatment) 35

Toegepaste hoeveelheid Bedekkingsgraad Bestrijdingsresultaat _kg AS/ha %_% _ onbeh. controle 38 0,8 35 8 1,2 20 49 1,8 4 90 8204109 40Amount applied Coverage rate Control result _kg AS / ha% _% _ untreated. control 38 0.8 35 8 1.2 20 49 1.8 4 90 8 204 109 40

Claims (4)

1, Herbicide miflctelen ter bestrijding van onkruidsoorten en ongewenste grassoorten, in het bijzonder van Salium ssp., welke middelen 1.2.4-tria-zolinon-(5)-verbindingen bevatten, met het kenmerk, dat als aktieve stof-5 fen verbindingen met de op het formuleblad aangegeven algemene formule, waarin en R£ onafhankelijk van elkaar waterstof of eventueel gesubstitueerde alkyl-, aryl-, aralkyl- of cycloalkylresten voorstellen, aanwezig zijn in kombinatie met gebruikelijke verdunnings-, drager- en/of andere hulpstoffen voor de formulering.1, Herbicidal insecticides to control weeds and undesirable grasses, in particular of Salium ssp., Which contain agents 1.2.4-tria-zolinone (5) compounds, characterized in that as active substances 5 the general formula indicated on the formula sheet, in which and R 1 independently represents hydrogen or optionally substituted alkyl, aryl, aralkyl or cycloalkyl radicals, are present in combination with conventional diluents, carriers and / or other auxiliary substances for the formulation . 2. Herbicide^ffliaaelen volgens conclusie 1, met het kenmerk, dat de alley1-, aryl-, aralkyl- of cycloalkylresten enkelvoudig of meervoudig gesubstitueerd kunnen zijn door halogeenatomen, hydroxylgroepen, eventueel door alkyl- en/of arylresten gesubstitueerde aminogroepen, alkoxygroepen, aryloxygroepen, alkylthiogroepen en arylthiogroepen.2. Herbicidal compounds according to claim 1, characterized in that the alleyl, aryl, aralkyl or cycloalkyl radicals can be singly or multiply substituted by halogen atoms, hydroxyl groups, optionally substituted alkyl and / or aryl radicals, alkoxy groups, aryloxy groups , alkylthio groups and arylthio groups. 3. Herbicidermiddelen volgens conclusie 1 of 2, met het kenmerk, dat de aktieve stoffen aanwezig zijn in kombinatie met andere herbiciden en/of landbouwchemicaliën, waarbij het middel ook de vorm kan hebben van een tankmengsel.Herbicidal agents according to claim 1 or 2, characterized in that the active substances are present in combination with other herbicides and / or agricultural chemicals, the agent also being in the form of a tank mixture. 4. Werkwijze voor het bestrijden van -ongewenste plantengroei, met het 20 kenmerk, dat men hiertoe.een herbicide_jmiddël volgens conclusies 1-3 toepast. 82041094. A method for controlling undesired plant growth, characterized in that a herbicidal agent according to claims 1-3 is used for this purpose. 8204109
NL8204109A 1982-10-25 1982-10-25 1,2,4-Triazoline-5-one herbicides for galium species - give good control of resistant weeds in cereal and sugar beet e.g. the 3-benzyl-4-para methoxyphenyl cpd. NL8204109A (en)

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NL8204109A NL8204109A (en) 1982-10-25 1982-10-25 1,2,4-Triazoline-5-one herbicides for galium species - give good control of resistant weeds in cereal and sugar beet e.g. the 3-benzyl-4-para methoxyphenyl cpd.

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NL8204109 1982-10-25
NL8204109A NL8204109A (en) 1982-10-25 1982-10-25 1,2,4-Triazoline-5-one herbicides for galium species - give good control of resistant weeds in cereal and sugar beet e.g. the 3-benzyl-4-para methoxyphenyl cpd.

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US9505728B2 (en) 2012-03-09 2016-11-29 Inception 2, Inc. Triazolone compounds and uses thereof
US9676754B2 (en) 2012-12-20 2017-06-13 Inception 2, Inc. Triazolone compounds and uses thereof
US9776976B2 (en) 2013-09-06 2017-10-03 Inception 2, Inc. Triazolone compounds and uses thereof

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9505728B2 (en) 2012-03-09 2016-11-29 Inception 2, Inc. Triazolone compounds and uses thereof
US9676754B2 (en) 2012-12-20 2017-06-13 Inception 2, Inc. Triazolone compounds and uses thereof
US10568871B2 (en) 2012-12-20 2020-02-25 Tempest Therapeutics, Inc. Triazolone compounds and uses thereof
US11666557B2 (en) 2012-12-20 2023-06-06 Tempest Therapeutics, Inc. Triazolone compounds and uses thereof
US9776976B2 (en) 2013-09-06 2017-10-03 Inception 2, Inc. Triazolone compounds and uses thereof

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