NO782922L - NEW N-PHENYL-N`-METHYL-N`-METHOXY-URINARY DERIVATIVES AND HERBICIDES CONTAINING SUCH DERIVATIVES - Google Patents

NEW N-PHENYL-N`-METHYL-N`-METHOXY-URINARY DERIVATIVES AND HERBICIDES CONTAINING SUCH DERIVATIVES

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Publication number
NO782922L
NO782922L NO782922A NO782922A NO782922L NO 782922 L NO782922 L NO 782922L NO 782922 A NO782922 A NO 782922A NO 782922 A NO782922 A NO 782922A NO 782922 L NO782922 L NO 782922L
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parts
weight
derivatives
plants
methoxy
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NO782922A
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Norwegian (no)
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Friedrich Linhart
Bernd Zeeh
Peter Jacobs
Bruno Wuerzer
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Basf Ag
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Publication of NO782922L publication Critical patent/NO782922L/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/64—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups singly-bound to oxygen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, 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
    • A01N47/08—Biocides, 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
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products

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

Description

Den foreliggende oppfinnelse angår nye verdifulle N-fenyl-N'-metyl-N<1->metoksyurinstoff-derivater med god herbicidvirkning, og herbicider inneholdende disse forbindelser som aktive eller virksomme stoffer. The present invention relates to new valuable N-phenyl-N'-methyl-N<1->methoxyurea derivatives with good herbicidal activity, and herbicides containing these compounds as active or effective substances.

Det er kjent at N-(4-isopropyl-fenyl)-N<1>,N<1->dimety1-urinstoff (US patent 2 655 447, tysk offentliggjørelsesskrift nr. 2 107 774 og nr. 2 039 041) har en god forenlighet med vinterhvete. Samtidig eliminerer denne forbindelse uønskede grasplanter såsom Alopecurus myosuroides og noen bredbladede arter. Virkningen er imidlertid helt utilstrekkelig overfor Galium apårine og andre tofrøbladede arter. It is known that N-(4-isopropyl-phenyl)-N<1>,N<1->dimethylurea (US Patent 2,655,447, German Publication No. 2,107,774 and No. 2,039,041) has a good compatibility with winter wheat. At the same time, this compound eliminates unwanted grass plants such as Alopecurus myosuroides and some broad-leaved species. However, the effect is completely insufficient against Galium apårine and other dicotyledonous species.

Betrakter man parallelt med denne de tilsvarende kjente N-(4-isopropyl-fenyl)-N<1->metoksy-N<1->metyl-urinstoff (tysk patent nr. 1 062 059), så viser denne forbindelse en lignende herbicid-aktivitet. If one considers in parallel with this the correspondingly known N-(4-isopropyl-phenyl)-N<1->methoxy-N<1->methyl-urea (German patent no. 1 062 059), then this compound shows a similar herbicide -Activity.

Det kjente N-(3-tert.-butyl-fenyl)-N<1>,N<1->dimetyl-urinstoff (tysk offentliggjørelsesskrift nr. 2 436 108) er en forbindelse med intensiv herbicidvirkning. Forbindelsen viser imidlertid ikke en tilstrekkelig forenlighet med kornarter. En sammenligningsvis gjennomsnittlig noe svakere herbicidvirkning viser det kjente N-(3-metyl-fenyl)-N<1->metoksy-N'metyl-urinstoff (tysk offentliggjørelsesskrift 1 905 598), samtidig som det The known N-(3-tert-butyl-phenyl)-N<1>,N<1->dimethylurea (German publication no. 2 436 108) is a compound with intensive herbicidal activity. However, the compound does not show sufficient compatibility with grain species. The known N-(3-methyl-phenyl)-N<1->methoxy-N'methyl-urea (German Publication No. 1 905 598) shows a comparatively weaker herbicidal effect, while the

viser en noe gunstigere, men likevel høyst marginal selektivitet overfor kornarter. shows a somewhat more favorable, but still highly marginal selectivity towards grain species.

Overraskende ble det nå funnet at metoksymetylurinstoff-derivater med den generelle formel Surprisingly, it was now found that methoxymethylurea derivatives of the general formula

hvor R betyr en forgrenet alkylrest med 3-5 karbonatomer (f. where R means a branched alkyl residue with 3-5 carbon atoms (e.g.

eks. isopropyl, isobutyl, sek.-butyl, tert.-butyl, 1,1-dimetylpropyl, 1-etylpropyl, 1-metylbutyl, 2,2-dimetylpropyl, 2-metylbutyl eller 3-metylbutyl), har en meget god herbicidvirkning mot uønskede enfrøbladede og tofrøbladede (gras- og bredbladede) planter, herunder Galium aparine, samtidig som de oppviser en høy grad av forenlighet med kornplanter, særlig vinterkorn (rug, hvete, bygg) ved anvendelse før eller etter plantenes oppkomst. e.g. isopropyl, isobutyl, sec.-butyl, tert.-butyl, 1,1-dimethylpropyl, 1-ethylpropyl, 1-methylbutyl, 2,2-dimethylpropyl, 2-methylbutyl or 3-methylbutyl), have a very good herbicidal effect against unwanted monocots and dicots (grass and broad-leaved) plants, including Galium aparine, while showing a high degree of compatibility with cereal plants, especially winter cereals (rye, wheat, barley) when used before or after the plants emerge.

Forbindelsene ifølge oppfinnelsen er nye og kan- fremstilles på følgende måter: 1. Et anilin med den generelle formel II, hvor R har den ovenfor angitte betydning, omdannes etter kjente metoder ved hjelp av.fosgen til det tilsvarende arylisocyanat med den generelle formel III, hvilket omsettes med hydroksylamin eller et salt derav i nærvær eller fravær av et oppløsnings- eller fortynningsmiddel, idet det ved anvendelse av et salt dessuten anvendes en organisk eller uorganisk hjelpebase. Det således fremstilte N-aryl-N<1->hydroksy-urinstoff med den generelle formel IV omsettes med et sterkt metyleringsmiddel, f.eks. dimetylsulfat, etter kjente metoder i nærvær av organiske eller uorganiske hjelpebaser i et oppløsnings- eller fortynningsmiddel, . hvorved forbindelsen I ifølge oppfinnelsen erholdes. The compounds according to the invention are new and can be prepared in the following ways: 1. An aniline with the general formula II, where R has the above meaning, is converted according to known methods with the help of phosgene to the corresponding aryl isocyanate with the general formula III, which is reacted with hydroxylamine or a salt thereof in the presence or absence of a solvent or diluent, with an organic or inorganic auxiliary base also being used when a salt is used. The thus produced N-aryl-N<1->hydroxy-urea with the general formula IV is reacted with a strong methylating agent, e.g. dimethyl sulfate, by known methods in the presence of organic or inorganic auxiliary bases in a solvent or diluent, . whereby the compound I according to the invention is obtained.

Istedenfor hydroksylamin eller et salt derav kan man også anvende N-metylhydroksylamin eller 0,N-dimetyl-hydroksylamin eller salter derav; ved anvendelse av dimetylhydroksylaminet bortfaller selvsagt den på-følgende metylering. Instead of hydroxylamine or a salt thereof, N-methylhydroxylamine or 0,N-dimethylhydroxylamine or salts thereof can also be used; when using the dimethylhydroxylamine, the subsequent methylation is of course omitted.

2. En annen vei som leder frem til urinstoffderivatene 2. Another pathway leading to the urea derivatives

med formelen I, går ut på at et anilin med den generelle formel II omsettes med N-metoksy-N-metylkarbamin-syreklorid med formelen V i nærvær av et oppløsnings-eller fortynningsmiddel under tilsetning av en organisk eller uorganisk hjelpebase: with the formula I, involves an aniline of the general formula II being reacted with N-methoxy-N-methylcarbamic acid chloride of the formula V in the presence of a solvent or diluent with the addition of an organic or inorganic auxiliary base:

De aniliner med den generelle formelen II som anvendes ved fremstillingen av urinstoffderivatene ifølge oppfinnelsen, kan eksempelvis fremstilles etter frem-gangsmåten til H. G. Gilman et al., J. Org. Chem. 19, 1071 (1954) . The anilines with the general formula II which are used in the preparation of the urea derivatives according to the invention can, for example, be prepared according to the method of H.G. Gilman et al., J. Org. Chem. 19, 1071 (1954).

Fremgangsmåte 1 foretrekkes.Method 1 is preferred.

Egnede aniliner er eksempelvis:Suitable anilines are, for example:

m-tert.-butylanilin KpQQ1= 73°Cm-tert-butylaniline KpQQ1= 73°C

m-iso-propylanilin Kp^ = 65°Cm-iso-propylaniline Kp^ = 65°C

Eksempel 1Example 1

Til en oppløsning av 14,9 deler (vektdeler). meta-tert.-butylanilin og 10,1 deler trietylamin i 100 deler toluen tilsettes dråpevis ved 20-40°C 12,4 deler N-metoksy-N-metylkarbamin-syreklorid. Etter en halv times omrøring vaskes reaksjons-blandingen med vann, og den organiske fase fraskilles og inn-dampes. To a resolution of 14.9 parts (parts by weight). meta-tert.-butylaniline and 10.1 parts of triethylamine in 100 parts of toluene are added dropwise at 20-40°C 12.4 parts of N-methoxy-N-methylcarbamic acid chloride. After stirring for half an hour, the reaction mixture is washed with water, and the organic phase is separated and evaporated.

Etter omkrystallisasjonen fra metylcykloheksan erholdes 17,2 deler N-meta-tert.-butylfenyl-N'-metoksy-N'-metyl-urinstoff med smeltepunkt 82-83°C. After the recrystallization from methylcyclohexane, 17.2 parts of N-meta-tert-butylphenyl-N'-methoxy-N'-methylurea with a melting point of 82-83°C are obtained.

Eksempel 2Example 2

Til en blanding av 287 deler hydroksylaminhydroklorid, 367 deler vann og 770 deler diklormetan tilsettes dråpevis under omrøring ved 0-5°C 330 deler 33% natronlut. Deretter til-dryppes 443 deler meta-isopropylfenylisocyanat oppløst i 400 deler diklormetan, og blandingen omrøres natten over ved rom-temperatur. Det utfelte bunnfall frafiltreres, vaskes med vann og tørkes. Det erholdes 505 deler N-meta-isopropylfenyl-N'-hydroksyurinstoff med smeltepunkt 120-123°C. Dette suspenderes i 1350 deler vann og oppløses ved tildrypping av 1000 deler av en 39% natronlut. Under omrøring tilsettes dråpevis ved 20-40°C 920 deler dimetylsulfat, blandingen omrøres i en time ved rom-temperatur, kjøles til 5°C, bunnfallet frafiltreres, vaskes med vann og tørkes. Det erholdes 480 deler N-meta-isopropylfenyl-N<1->metoksy-N<1->metylurinstoff, som etter omkrystallisasjonen fra metylcykloheksan smelter ved 78-79°C. To a mixture of 287 parts of hydroxylamine hydrochloride, 367 parts of water and 770 parts of dichloromethane, 330 parts of 33% caustic soda are added dropwise while stirring at 0-5°C. 443 parts of meta-isopropylphenyl isocyanate dissolved in 400 parts of dichloromethane are then added dropwise, and the mixture is stirred overnight at room temperature. The precipitate is filtered off, washed with water and dried. 505 parts of N-meta-isopropylphenyl-N'-hydroxyurea with melting point 120-123°C are obtained. This is suspended in 1,350 parts of water and dissolved by adding 1,000 parts of a 39% sodium hydroxide solution drop by drop. While stirring, 920 parts of dimethylsulphate are added dropwise at 20-40°C, the mixture is stirred for one hour at room temperature, cooled to 5°C, the precipitate is filtered off, washed with water and dried. 480 parts of N-meta-isopropylphenyl-N<1->methoxy-N<1->methylurea are obtained, which after recrystallization from methylcyclohexane melts at 78-79°C.

De nye virksomme stoffer kan anvendes ved innarbeidelse i jordsmonnet, overflatebehandling av jordsmonnet eller behandling av oppkomne planter. Også spesialanvendelser som underblad-sprøyting (post-directed, lay-by) kan benyttes. Man styrer da sprøytestrålen slik at bladene av oppkomne, ømfintlige kulturplanter såvidt mulig ikke treffes, mens midlene påsprøytes på den derunder liggende jordflate og på de uønskede planter som vokser der. The new active substances can be used for incorporation into the soil, surface treatment of the soil or treatment of emerging plants. Special applications such as underleaf spraying (post-directed, lay-by) can also be used. The spray jet is then directed so that the leaves of emerging, sensitive cultivated plants are not hit as far as possible, while the agents are sprayed on the underlying soil surface and on the unwanted plants growing there.

I betraktning av anvendelsesmetodens mangesidighet kan midlene ifølge oppfinnelsen eller blandinger inneholdende disse anvendes i forbindelse med et stort antall kulturplanter, i til-legg til de i tabellene anførte nytteplanter, til bekjempelse av uønsket plantevekst. De mengder som anvendes, kan variere mellom 0,1 og 15 kg/ha alt etter bekjempelsesobjektet. Considering the versatility of the application method, the agents according to the invention or mixtures containing them can be used in connection with a large number of cultivated plants, in addition to the useful plants listed in the tables, to combat unwanted plant growth. The amounts used can vary between 0.1 and 15 kg/ha, depending on the object to be controlled.

Bekjempelsen av gras- og bredbladede uønskede planterThe control of grass and broad-leaved unwanted plants

i vinterkorn.illustreres av de følgende eksempler, som også viser de virksomme stoffers gode forenlighet med kulturplantene. Forsøkene ble utført i drivhus og på friland. in winter grains. is illustrated by the following examples, which also show the good compatibility of the active substances with the cultivated plants. The experiments were carried out in a greenhouse and in the open field.

1. Drivhusforsøk1. Greenhouse experiment

Forsøkene ble utført i blomsterpotter av plast med et volum på.300 cm 3. Disse ble fylt med leirholdig sand inneholdende ca. 1,5% humus. Frøene av de i tabell 1 angitte forsøksplanter ble overflate-sådd adskilt etter art. Umiddelbart deretter fulgte, ved behandling før plantenes oppkomst, påføringen av de virksomme stoffer på jordoverflaten. Stoffene ble anvendt suspendert eller'emulgert i vann og ble utsprøytet ved hjelp av fint fordelende dyser. Etter påføringen av midlene ble pottene lett dusjet for at spiring og vekst skulle komme i gang, og for samtidig å aktivere, de kjemiske midler. Deretter ble pottene dekket med gjennomsiktige plasthetter inntil plantene hadde nådd en viss størrelse. Den overdekking bevirker en ens-artet oppskyting av forsøksplantene, for så vidt som dette ikke ble forstyrret av kjemikaliene, og hindrer fordampning av lett flyktige stoffer. The experiments were carried out in plastic flower pots with a volume of 300 cm 3. These were filled with clayey sand containing approx. 1.5% humus. The seeds of the test plants listed in Table 1 were surface-sown separately by species. This was immediately followed by the application of the active substances to the soil surface, in the case of treatment before the emergence of the plants. The substances were used suspended or emulsified in water and were sprayed using finely distributing nozzles. After the application of the agents, the pots were lightly showered in order to initiate germination and growth, and to simultaneously activate the chemical agents. The pots were then covered with transparent plastic caps until the plants had reached a certain size. The covering causes a uniform shoot-up of the experimental plants, insofar as this was not disturbed by the chemicals, and prevents evaporation of easily volatile substances.

Ved behandling etter plantenes oppkomst lot man plantene alt etter vekstformen vokse til en høyde på 3-10 cm i forsøkspottene før plantene ble behandlet. Over-dekkingen etter behandlingen ble sløyfet. Pottene ble deretter plassert i drivhus. Forsøksperioden strekte seg over 4-6 uker. I denne tiden ble plantene pleiet, og deres reaksjon på de enkelte behandlinger ble vurdert. Nedenstående tabeller viser prøvestoffene, doseringer When treating after the emergence of the plants, depending on the growth form, the plants were allowed to grow to a height of 3-10 cm in the test pots before the plants were treated. The over-covering after the treatment was looped. The pots were then placed in greenhouses. The trial period extended over 4-6 weeks. During this time, the plants were cared for, and their reaction to the individual treatments was assessed. The tables below show the test substances, dosages

i kg/ha aktivt stoff og forsøksplantene. Vurderingen ble foretatt etter en skala mellom 0 og 100. Her betyr 0 ingen beskadigelse eller normalt forløp, og 100 betyr at plantene ikke kom opp, eller at de ble fullstendig ødelagt - i det minste de overjordiske deler av skuddet eller stengelen. in kg/ha active substance and the experimental plants. The assessment was made on a scale between 0 and 100. Here 0 means no damage or a normal course, and 100 means that the plants did not come up, or that they were completely destroyed - at least the above-ground parts of the shoot or stem.

2. Frilandsforsøk2. Field trial

Det dreier seg her om forsøk på små parseller med leirholdig sand og leire med pH 5-6 og et humusinnhold på 1-1,5%. Det beskrives behandlinger før plantenes oppkomst, hvor behandlingen ble foretatt umiddelbart eller senest tre dager etter såingen av kulturplantene. Ved behandlingene etter plantenes oppkomst var plantene 1 et utviklingsstadium kjennetegnet ved kimblad og opp til flere ekte blad. Kornplantene eller de uønskede grasplanter hadde imidlertid enda ikke overskredet utviklingsstadiet. En ugrasflora omfattende de for-skjelligste arter var naturlig forekommende. Stoffene ble anvendt suspendert eller emulgert i vann som bærer-og spredningsmedium og ble påført ved hjelp av en motordrevet parsellsprøyte montert på en traktor. Naturlig nedbør var tilstrekkelig for nytteplantenes og ugrasplantenes spiring og vekst. Alle forsøk løp over flere måneder. I dette tidsrom ble vurderingen utført med visse mellomrom og innenfor skalaen fra 0 til 100. This concerns experiments on small plots of clayey sand and clay with a pH of 5-6 and a humus content of 1-1.5%. Treatments are described before the plants emerge, where the treatment was carried out immediately or at the latest three days after sowing the cultivated plants. In the treatments after the emergence of the plants, the plants were in a developmental stage characterized by cotyledons and up to several true leaves. However, the cereal plants or the unwanted grass plants had not yet exceeded the development stage. A weed flora comprising the most diverse species was naturally occurring. The substances were used suspended or emulsified in water as a carrier and spreading medium and were applied using a motor-driven parcel sprayer mounted on a tractor. Natural rainfall was sufficient for the germination and growth of beneficial plants and weeds. All trials ran over several months. During this period, the assessment was carried out at certain intervals and within the scale from 0 to 100.

ResultatResult

Tabellene 2-8 viser tallverdiene vedrørende resultatene: Forbindelsene ifølge oppfinnelsen utmerker seg ved en god..aktivi-tet mot et bredt spektrum av uønskede planter. Forenligheten med vinterkorn er også god.. I forhold til de kjente sammen-iigningsstoffer oppviser forbindelsene ifølge oppfinnelsen en betydelig bedre virkning når det gjelder bekjempelse av bredbladede planter. Dette gjelder i første rekke arter som man vanskelig har kunnet bekjempe med selektive urinstoffderivater i kornåkrer. En ytterligere fordel med de nye forbindelser er deres lavere phytotoksisitet sammenlignet med kjente virksomme stoffer. Tables 2-8 show the numerical values regarding the results: The compounds according to the invention are distinguished by good activity against a wide spectrum of unwanted plants. The compatibility with winter grains is also good. Compared to the known compounds, the compounds according to the invention show a significantly better effect when it comes to combating broad-leaved plants. This primarily applies to species that have been difficult to control with selective urea derivatives in cornfields. A further advantage of the new compounds is their lower phytotoxicity compared to known active substances.

De nye herbicide substituerte urinstoffderivater kan blandes med og anvendes sammen med tallrike representanter for andre herbicide eller vekstregulerende virksomme stoffer. Slike kombinasjoner tjener til å utvide virkningsspekteret, og under tiden oppnås synergiske virkninger. En rekke virksomme stoffer som sammen med de nye forbindelser gir hensiktsmessige blandinger, anføres nedenfor som eksempler: The new herbicidal substituted urea derivatives can be mixed with and used together with numerous representatives of other herbicidal or growth-regulating active substances. Such combinations serve to expand the spectrum of action, and in the meantime synergistic effects are achieved. A number of active substances which, together with the new compounds, provide suitable mixtures, are listed below as examples:

Det er også en fordel at de nye forbindelser ifølge oppfinnelsen, alene eller i kombinasjon med andre herbicider, It is also an advantage that the new compounds according to the invention, alone or in combination with other herbicides,

kan anvendes blandet med ytterligere plantevernmidler. Blant disse nevnes midler til bekjempelse av skadedyr, phytopatpgene sopper eller vekstregulatorer. Av interesse er videre blandbar-heten med mineralgjødningsløsninger som anvendes mot ernærings-eller sporelementmangel. can be used mixed with additional pesticides. These include agents for combating pests, phytopathogenic fungi or growth regulators. Also of interest is the miscibility with mineral fertilizer solutions that are used against nutritional or trace element deficiencies.

Anvendelsen skjer eksempelvis i form av direkte sprøyt-bare løsninger, pulvere, suspensjoner, også høyprosentige, vandige olje- eller andre suspensjoner eller dispersjoner, emulsjoner, oljedispersjoner, pastaer, støvformige midler, strømidler eller granulater, ved utsprøyting, forstøvning, utspredning eller ut-helling. Bruksformene retter seg helt etter anvendelsesformålet; de tar alltid sikte på en mest mulig fin fordeling av de virksomme stoffer ifølge oppfinnelsen. The application takes place, for example, in the form of directly sprayable solutions, powders, suspensions, also high-percentage, aqueous oil or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusty agents, flow agents or granules, by spraying, atomizing, spreading or slope. The forms of use depend entirely on the purpose of use; they always aim for the finest possible distribution of the active substances according to the invention.

Ved fremstilling av direkte sprøytbare løsninger, emulsjoner, pastaer og oljedispersjoner kan man anvende mineral-oljefraksjoner med midlere til høyt kokepunkt, såsom kerosin eller dieselolje, enn videre kulltjæreolje etc., samt oljer av vegeta-bilsk eller animalsk opprinnelse, alifatiske, sykliske og aromatiske hydrokarboner, f.eks. benzen, toluen, xylen, parafin, tetrahydronaftalin, alkylerte naftaliner eller derivater derav, f.eks. metanol, etanol, propanol, butanol, kloroform, karbon-tetraklorid, cykloheksanol, cykloheksanon, klorbenzen, isophoron etc., sterkt polare løsningsmidler, f.eks. dimetylformamid, dimetylsulfoksyd, N-metylpyrrolidon, vann etc. When producing directly sprayable solutions, emulsions, pastes and oil dispersions, you can use mineral oil fractions with high boiling points, such as kerosene or diesel oil, as well as coal tar oil etc., as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or derivatives thereof, e.g. methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, etc., strongly polar solvents, e.g. dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, water, etc.

Vandige bruksformer kan fremstilles av emulsjons-konsentrater, pastaer eller fuktbare pulvere (sprøytepulvere),'oljedispersjoner, ved tilsetning av vann. For fremstilling av emulsjoner, pastaer eller oljedispersjoner kan stoffene som så-danne eller oppløst i en olje eller et løsningsmiddel homogeni-seres i vann ved hjelp av fukt-, klebe-, dispergerings- eller emulgeringsmidler. Man kan imidlertid også fremstille konsentrater bestående av virksomt stoff, fukte-, klebe-, dispergerings-eller emulgeringsmiddel og eventuelt løsningsmiddel eller olje, hvilke konsentrater er egnet til å fortynnes med vann. Aqueous forms of use can be prepared from emulsion concentrates, pastes or wettable powders (spray powders), oil dispersions, by adding water. For the production of emulsions, pastes or oil dispersions, the substances as such or dissolved in an oil or a solvent can be homogenised in water using wetting agents, adhesives, dispersants or emulsifiers. However, it is also possible to prepare concentrates consisting of active substance, wetting, adhesive, dispersing or emulsifying agent and any solvent or oil, which concentrates are suitable for diluting with water.

Blant overflateaktive stoffer kan nevnes følgende: Alkali-, jordalkali-, ammoniumsalter av ligninsulfonsyre, naf talinsulf onsyrer, f enolsulf onsyre , alkylarylsulfpnater, alkylsulfater, alkylsulfonater, alkali- og jordalkalisalter av dibutylnaftalinsulfonsyre, fettalkoholsulfater, fettsure alkali-og jordalkalisalter, salter av sulfaterte heksadekanoler, hepta-dekanoler, oktadekanoler, salter av sulfatert fettalkohol-glykoleter, kondensasjonsprodukter av sulfonert naftalin og naftalinderivater med formaldehyd, kondensasjonsprodukter av naftalin eller naftalinsulfonsyrer med fenol og formaldehyd, polyoksyetylenoktylfenoleter, etoksylert isooktylfenol, oktyl-fenol, nonylfenol, alkylfenolpolyglykoleter, tributylfenylpoly-glykoleter, alkylarylpolyeteralkoholer, isotridecylalkohol, fettalkohol-etylenoksyd-kondensater, etoksylert ricinusolje, polyoksyetylenalkyleter, etoksylert polyoksypropylen, lauryl-alkohol-polyglykoleteracetal, sorbitolestere, lignin, sulfit-avluter og metylcellulose. Among surfactants, the following can be mentioned: Alkali, alkaline earth, ammonium salts of ligninsulfonic acid, naphthalene sulfonic acids, phenolsulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, alkali and alkaline earth salts of dibutylnaphthalene sulfonic acid, fatty alcohol sulfates, fatty acid alkali and alkaline earth salts, salts of sulfated hexadecanols , hepta-decanols, octadecanols, salts of sulfated fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalene sulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ether, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin, sulphite deluters and methyl cellulose.

Pulver-, strø- og støvformige midler kan fremstillesPowder, sprinkle and dust agents can be produced

ved blanding eller sammaling av de virksomme stoffer med et fast bærer materiale. by mixing or mixing the active substances with a solid carrier material.

Granulater, eksempelvis omhyllings-, impregnerings-Granulates, for example covering, impregnating

og homogengranulater, kan fremstilles ved binding av de virksomme stoffer til faste bærermaterialer. Faste bærermaterialer er f.eks. mineralske stoffer såsom silika-gel, kiselsyrer, kiselgeler, silikater, talkum, kaolin, attapulgitt, kalkstein, kalk, kritt, bolus, leire, dolomitt, diatoméenjord, kalsium- og magnesium-sulfat, magnesiumoksyd, malte harpikser, gjødningsstoffer, som f.eks. ammoniumsulfat, ammoniumfosfat, ammoniumnitrat, urin-stoffer og vegetabilske materialer såsom mel av korn, mel av and homogenous granules, can be produced by binding the active substances to solid carrier materials. Solid carrier materials are e.g. mineral substances such as silica gel, silicic acids, silica gels, silicates, talc, kaolin, attapulgite, limestone, lime, chalk, bolus, clay, dolomite, diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, ground resins, fertilizers, such as e.g. ammonium sulphate, ammonium phosphate, ammonium nitrate, urine substances and vegetable materials such as flour from cereals, flour from

bark, tre og nøtteskall, cellulosepulver og andre faste bærermaterialer . bark, wood and nut shells, cellulose powder and other solid carrier materials.

Preparatene inneholder mellom 0,1 og 95 vekt% virksomt stoff, fortrinnsvis mellom 0,5 og 90 vekt%. The preparations contain between 0.1 and 95% by weight of active substance, preferably between 0.5 and 90% by weight.

Til blandingene eller de enkelte virksomme stoffer kan det tilsettes olje av forskjellige typer, fukte eller klebemidler, nematocider, baktericider, antiskumningsmidler (f.eks. silikoner).Tilblandingen av disse midler til herbicidene ifølge oppfinnelsen kan skje i vektforholdet 1:10 til 10:1. Det samme gjelder olje, fukte- eller klebemidler, fungicider, nematocider, insekticider, baktericider og vekstregulatorer. Oil of different types, wetting agents or adhesives, nematocides, bactericides, anti-foaming agents (e.g. silicones) can be added to the mixtures or the individual active substances. The mixing of these agents to the herbicides according to the invention can take place in a weight ratio of 1:10 to 10: 1. The same applies to oil, wetting agents or adhesives, fungicides, nematocides, insecticides, bactericides and growth regulators.

Eksempel 3Example 3

90 vektdeler av forbindelsen i eksempel 1 blandes med 10 vektdeler N-metyl-a-pyrrolidon, hvorved det erholdes en løsning som er egnet til anvendelse i form av meget fine dråper. 90 parts by weight of the compound in example 1 are mixed with 10 parts by weight of N-methyl-α-pyrrolidone, whereby a solution is obtained which is suitable for use in the form of very fine droplets.

Eksempel 4Example 4

20 vektdeler av forbindelsen i eksempel 2 oppløses i en blanding bestående av 80 vektdeler xylen, 10 vektdeler av et addisjonsprodukt av 8-10 mol etylenoksyd og 1 mol ol jesyre-N-mono-etanolamid, 5 vektdeler av kalsiumsaltet av dodecylbenzen-sulfonsyre og•5 vektdeler av addisjonsproduktet av 40 mol etylenoksyd og 1 mol ricinusolje. Ved innblanding og finfor-deling av oppløsningen i 100 000 vektdeler vann erholdes en vandig dispersjon som inneholder 0,02 vekt% av det virksomme stoff. 20 parts by weight of the compound in example 2 are dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of an addition product of 8-10 mol of ethylene oxide and 1 mol of oleic acid-N-mono-ethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid and• 5 parts by weight of the addition product of 40 mol of ethylene oxide and 1 mol of castor oil. By mixing and finely distributing the solution in 100,000 parts by weight of water, an aqueous dispersion containing 0.02% by weight of the active substance is obtained.

Eksempel 5Example 5

20 vektdeler av forbindelsen i eksempel 2 oppløses i en blanding bestående av 40 vektdeler cykloheksanon, 30 vektdeler isobutanol, 20 vektdeler av addisjonsproduktet av 7 mol etylenoksyd og 1 mol isooktylfenol og 10 vektdeler av addisjonsproduktet av 40 mol etylenoksyd og 1 mol ricinusolje. Oppløsningen innblandes og finfordeles i 100 000 vektdeler vann, hvorved det erholdes en vandig dispersjon som inneholder 0,02 vekt% av det virksomme stoff. 20 parts by weight of the compound in example 2 are dissolved in a mixture consisting of 40 parts by weight cyclohexanone, 30 parts by weight isobutanol, 20 parts by weight of the addition product of 7 mol ethylene oxide and 1 mol isooctylphenol and 10 parts by weight of the addition product of 40 mol ethylene oxide and 1 mol castor oil. The solution is mixed and finely divided into 100,000 parts by weight of water, whereby an aqueous dispersion containing 0.02% by weight of the active substance is obtained.

Eksempel 6Example 6

20 vektdeler av forbindelsen i eksempel 2 oppløses i en blanding bestående av 25 vektdeler cykloheksanol, 65 vektdeler av en mineraloljefraksjon med kokepunkt 210-280°C og 20 parts by weight of the compound in example 2 are dissolved in a mixture consisting of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction with a boiling point of 210-280°C and

10 vektdeler av addisjonsproduktet av 40 mol etylenoksyd og10 parts by weight of the addition product of 40 moles of ethylene oxide and

1 mol ricinusolje. Oppløsningen innblandes og finfordeles i 100 000 vektdeler vann, hvorved det erholdes en vandig dispersjon som inneholder 0,02 vekt% av det virksomme stoff. 1 mole of castor oil. The solution is mixed and finely divided into 100,000 parts by weight of water, whereby an aqueous dispersion containing 0.02% by weight of the active substance is obtained.

Eksempel 7Example 7

20 vektdeler av det virksomme stoff ifølge eksempel 2 blandes godt med 3 vektdeler av natriumsaltet av diisobutyl-naftalin-a-sulfonsyre, 17 vektdeler av natriumsaltet av en ligninsulfonsyre fra en sulfittavlut og 60 vektdeler pulverformig kiselsyregel, og blandingen males i en hammer-mølle. Blandingen finfordeles i 20 000 vektdeler vann, hvorved det erholdes en sprøyteblanding som inneholder 0,1 vekt% av det virksomme stoff. 20 parts by weight of the active substance according to example 2 are mixed well with 3 parts by weight of the sodium salt of diisobutyl-naphthalene-a-sulfonic acid, 17 parts by weight of the sodium salt of a ligninsulfonic acid from a sulphite leachate and 60 parts by weight of powdered silica gel, and the mixture is ground in a hammer mill. The mixture is finely divided into 20,000 parts by weight of water, whereby a spray mixture containing 0.1% by weight of the active substance is obtained.

Eksempel 8 .Example 8.

3 vektdeler av forbindelsen i eksempel 1, blandes3 parts by weight of the compound in example 1 are mixed

godt med 97 vektdeler findelt kaolin. Det erholdes på denne måte et støvformig middel som inneholder 3 vekt% av det virksomme stoff. well with 97 parts by weight finely divided kaolin. In this way, a dust-like agent containing 3% by weight of the active substance is obtained.

Eksempel 9Example 9

30 vektdeler av forbindelsen i eksempel 2 blandes godt med en blanding av 92 vektdeler pulverformig kiselsyregel og 8 vektdeler parafinolje, idet denne sprøytes over overflaten av kiselsyregelen. Det erholdes på denne måte et preparat av det virksomme stoff med god klebeevne. 30 parts by weight of the compound in example 2 are mixed well with a mixture of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil, this being sprayed over the surface of the silica gel. In this way, a preparation of the active substance with good adhesiveness is obtained.

Eksempel 10Example 10

40 vektdeler av det virksomme stoff i eksempel 1 blandes godt med 10 deler av natriumsaltet av et fenolsulfonsyre-urinstoff-formaldehyd-kondensat, 2 deler kiselsyregel og 48 deler vann. 40 parts by weight of the active ingredient in example 1 are mixed well with 10 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts silicic acid regel and 48 parts water.

Det erholdes en stabil, vandig dispersjon. Ved fortynning medA stable, aqueous dispersion is obtained. By dilution with

100 000 vektdeler vann erholdes en vandig dispersjon som inneholder 0,04 vekt% virksomt stoff. 100,000 parts by weight of water, an aqueous dispersion containing 0.04% by weight of active substance is obtained.

Eksempel 11Example 11

20 deler av det virksomme stoff ifølge eksempel 2 blandes godt med 2 deler av kalsiumsaltet av dodecylbenzensulfon-syre, 8 deler fettalkohol-polyglykoleter, 2 deler av natriumsaltet av et fenol-urinstoff-formaldehyd-kondensat og 68 deler av en parafinisk mineralolje. Det erholdes en stabil olje-dispers jon . 20 parts of the active substance according to example 2 are mixed well with 2 parts of the calcium salt of dodecylbenzenesulfonic acid, 8 parts of fatty alcohol polyglycol ether, 2 parts of the sodium salt of a phenol-urea-formaldehyde condensate and 68 parts of a paraffinic mineral oil. A stable oil dispersion is obtained.

Claims (2)

1. Herbicid inneholdende et N-fenyl-N'-metyl-N'- . metoksyurinstoffderivat•med formelen 1. Herbicide containing an N-phenyl-N'-methyl-N'-. methoxyurea derivative•with the formula i hvilken R betyr en forgrenet alkylrest med 3-5 karbonatomer.in which R means a branched alkyl radical with 3-5 carbon atoms. 2. Herbicid middel inneholdende et N-fenyl-N'-metyl-N <1-> metoksyurinstoffderivat valgt fra gruppen bestående av N-(3-tert.-butylfenyl)-N'-metoksy-N'-metylurinstoff N-(3-isopropylfenyl)-N'-metoksy-N'-metylurinstoff N-(3-sek.-butylfenyl)-N'-metoksy-N <1-> metylurinstoff N-(3-isobutylfenyl)-N'-metoksy-N <1-> metylurinstoff2. Herbicidal agent containing an N-phenyl-N'-methyl-N <1-> methoxyurea derivative selected from the group consisting of N-(3-tert-butylphenyl)-N'-methoxy-N'-methylurea N-(3-isopropylphenyl)-N'-methoxy-N'-methylurea N-(3-sec-butylphenyl)-N' -methoxy-N <1-> methylurea N-(3-isobutylphenyl)-N'-methoxy-N <1-> methylurea
NO782922A 1977-09-01 1978-08-28 NEW N-PHENYL-N`-METHYL-N`-METHOXY-URINARY DERIVATIVES AND HERBICIDES CONTAINING SUCH DERIVATIVES NO782922L (en)

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US3288586A (en) * 1963-11-07 1966-11-29 Du Pont Herbicidal methods employing an addition compound of 3-(3, 4-dichlorophenyl)-1-methyl-1-methoxyurea and dodecylbenzenesulfonic acid
IL31574A0 (en) * 1968-02-13 1969-04-30 Ciba Ltd Use of certain ureas for combating weeds
DE1911610A1 (en) * 1969-03-07 1970-10-01 Hoechst Ag Urea derivatives, their manufacture and use as herbicides
CH537148A (en) * 1970-02-27 1973-05-31 Ciba Geigy Ag Use of phenylureas as selective herbicides
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