NO750140L - - Google Patents

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Publication number
NO750140L
NO750140L NO750140A NO750140A NO750140L NO 750140 L NO750140 L NO 750140L NO 750140 A NO750140 A NO 750140A NO 750140 A NO750140 A NO 750140A NO 750140 L NO750140 L NO 750140L
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Prior art keywords
dimethyl
dihydro
substituted
methylaminosulfonate
parts
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NO750140A
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Norwegian (no)
Inventor
A Fischer
W Rohr
C Reitel
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Basf Ag
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
    • C07D307/83—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/80—Radicals substituted by oxygen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Furan Compounds (AREA)

Description

Den foreliggende oppfinnelse angår nye 4-benzofuranylestere, fremstillingen av disse forbindelser, deres anvendelse som herbicider, samt herbicider inneholdende disse forbindelser som virksomme stoffer. The present invention relates to new 4-benzofuranyl esters, the production of these compounds, their use as herbicides, and herbicides containing these compounds as active substances.

Anvendelsen av 2,3-dihydro-3,3-dimetyl-2-etoksybenzofuran-5-yl-metan-sulfonat (DT-OS 1 926 139) som herbicid er kjent? dets virkning er imidlertid bare liten. The use of 2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-methane-sulfonate (DT-OS 1 926 139) as a herbicide is known? however, its effect is only small.

Det ble nå funnet at benzofuran-5-yl-estere med den generelle formel It was now found that benzofuran-5-yl esters of the general formula

hvor R"<*>" betyr hydrogen eller en eventuelt med halogen (klor) eller alkoksy (metoksy) substituert alkyl^- (metyl, etyl, propyl, iso-propyl, butyl), alkenyl- (allyl, metallyl) eller alkynylrest (propargyl, butynyl), og R<2>betyr en alkenyl- (allyl, metallyl) eller alkynyl-rest (propargyl, butynyl), et metallatom (alkali- og jord-alkaliatom, natrium, kalium, magnesium, litium), en alkylsulfonyl-rest (metylsulfonyl), en aminosulfonylrest eller en acylrest med den generelle formel 4 hvor R er en eventuelt med halogen (klor), alkoksy (metoksy) eller alkyltio (tiometyl) substituert alkyl-, alkenyl- eller alkynyl-rest, en alkylamino- eller dialkylamino-rest, eller en eventuelt med halogen substituert alkoksyrest, og R 3 er hydrogen, en eventuelt med halogen (klor) eller alkoksy (metoksy) substituert alkyl-, alkenyl- eller alkynyl-rest eller en acylrest med den generelle formel where R"<*>" means hydrogen or an alkyl (methyl, ethyl, propyl, iso-propyl, butyl), alkenyl (allyl, metallyl) or alkynyl radical ( propargyl, butynyl), and R<2>means an alkenyl (allyl, metallyl) or alkynyl residue (propargyl, butynyl), a metal atom (alkali and alkaline earth atom, sodium, potassium, magnesium, lithium), an alkylsulfonyl -residue (methylsulfonyl), an aminosulfonyl residue or an acyl residue of the general formula 4 where R is an alkyl, alkenyl or alkynyl residue optionally substituted with halogen (chloro), alkoxy (methoxy) or alkylthio (thiomethyl), an alkylamino- or dialkylamino residue, or an optionally halogen-substituted alkoxy acid residue, and R 3 is hydrogen, an optionally halogen (chloro) or methoxy (methoxy) substituted alkyl, alkenyl or alkynyl residue or an acyl residue of the general formula

hvor R 5 er en eventuelt med halogen (klor), alkoksy (metoksy) eller alkyltio (tiometyl) substituert alkyl-, alkenyl- eller alkynyl-rest, en alkylamino- eller dialkylamino-rest, eller en eventuelt med halogen substituert alkoksyrest, where R 5 is an alkyl, alkenyl or alkynyl residue optionally substituted with halogen (chloro), alkoxy (methoxy) or alkylthio (thiomethyl), an alkylamino or dialkylamino residue, or an alkoxy acid residue optionally substituted with halogen,

har en god herbicid virkning som er bedre enn virkningen av kjente herbicider, videre har de nye forbindelser en bedre selektivitet has a good herbicidal effect which is better than the effect of known herbicides, furthermore the new compounds have a better selectivity

i forbindelse med nytteplanter, for eksempel Gossypium hirsutum,Zea mays, Beta spp., enn 2,3-dihydro-3,3-dimetyl-2-etoksybenzo-furan-5-yl-metan-sulfonat. in connection with useful plants, for example Gossypium hirsutum, Zea mays, Beta spp., than 2,3-dihydro-3,3-dimethyl-2-ethoxybenzo-furan-5-yl-methane-sulfonate.

Fremstillingen av forbindelsene ifølge oppfinnelsen kan eksempelvis skje ved den følgende fremgangsmåte: a) ved acylering av benzofuran-5-yl-aminosulfonater etter den føl-~;' 7 gende generelle reaksjonsligning 13 4 hvor substituentene R , R og R har samme betydning som ovenfor, og X eksempelvis betyr et halogenatom (klor, brom) eller resten The production of the compounds according to the invention can, for example, take place by the following method: a) by acylation of benzofuran-5-yl-aminosulfonates according to the following procedure. 7 general reaction equation 13 4 where the substituents R , R and R have the same meaning as above, and X, for example, means a halogen atom (chlorine, bromine) or the residue

De som utgangsmaterialer anvendte benzofuran-5-yl-aminosulfo-nater er beskrevet, b) Ved acylering av 2-hydroksybenzofuran-5-yl-amino-sulfonater som følger: The benzofuran-5-yl-aminosulfonates used as starting materials are described, b) In the acylation of 2-hydroxybenzofuran-5-yl-amino-sulfonates as follows:

hvor R1, R2 ogR<5>har samme betydning som ovenfor og X eksempelvis betyr et halogenatom (klor, brom) eller resten where R1, R2 and R<5> have the same meaning as above and X, for example, means a halogen atom (chlorine, bromine) or the residue

De benzofuranderivater som anvendes som utgangsmaterialer, kan fremstilles på følgende måte: The benzofuran derivatives used as starting materials can be prepared in the following way:

De under 1) angitte reaksjon er kjent fra det hollandske offent-\ ~lTgg j øre Ise s skr ijffe 6 512 311, fra Journal f Ur praktische Chemie, The reactions indicated under 1) are known from the Dutch public- \ ~lTgg j øre Ise s skr ijffe 6 512 311, from Journal f Ur praktische Chemie,

4. serie, bind 32, side 144 (1966) og fra US-PS 3 184 457.4th Series, Volume 32, Page 144 (1966) and from US-PS 3,184,457.

De under 2) til 4) angitte reaksjoner belyses ved de følgende forsøksbeskrivelser♦ The reactions indicated under 2) to 4) are elucidated by the following experimental descriptions♦

Forsøk A Try A

2,3-dihydro-3,3-dimetyl-2-morfolinobenzofuran-5-yl-metylaminosulfonat 2,3-dihydro-3,3-dimethyl-2-morpholinobenzofuran-5-yl-methylaminosulfonate

En oppløsning av 48,8 vektdeler 2,3-dihydro-3,3-dime-tyl-2-morfolino-5-hydroksybenzofuran og 27,3 vektdeler trietylamin i 130 vektdeler tetrahydrofuran ble under omrøring blandet med 36 vektdeler metylaminosulfonylklorid ved 0-5°C. Etter en times omrøring ved romtemperatur ble reaksjonsblandingen filtrert. Filtratet ble inndampet i vakuum, og residuet ble oppløst i 250 deler metanol. Etter tilsetning av 100 deler vann og behandling av løsningen med aktivkull ble krystallisa-sjonen innledet ved kjøling. Krystallgrøten ble avsuget, vasket med 50%'s (vekt%) metanol og tørret i vakuum. Råproduktet hadde et smeltepunkt på 125-128°C. Ved krystallisasjon av en prøve fia 80%'s metanol erholdtes rent 2,3-dihydro-3,3-dimetyl- 2"morfolinobenzofuran-5-yl~metylaminosulfonat, sm.p. 129-131°C. A solution of 48.8 parts by weight of 2,3-dihydro-3,3-dimethyl-2-morpholino-5-hydroxybenzofuran and 27.3 parts by weight of triethylamine in 130 parts by weight of tetrahydrofuran was mixed with stirring with 36 parts by weight of methylaminosulfonyl chloride at 0-5 °C. After stirring for one hour at room temperature, the reaction mixture was filtered. The filtrate was evaporated in vacuo, and the residue was dissolved in 250 parts of methanol. After adding 100 parts of water and treating the solution with activated charcoal, crystallization was initiated by cooling. The crystal slurry was suctioned off, washed with 50% (wt%) methanol and dried in vacuum. The crude product had a melting point of 125-128°C. By crystallization of a sample from 80% methanol, pure 2,3-dihydro-3,3-dimethyl-2"morpholinobenzofuran-5-yl-methylaminosulfonate was obtained, m.p. 129-131°C.

Forsøk B Attempt B

2,3-dihydro«3, 3-dimetyl-2-hydroksybenzof uran-5-yl-metylaminosulfonat 2,3-dihydro«3,3-dimethyl-2-hydroxybenzofuran-5-yl-methylaminosulfonate

Til en blanding av 133 deler vann og 68 deler konsentrert saltsyre ble det ved 80°C og under omrøring på én gang tilsatt 68 deler 2,3~dihydro«3, 3~dimetyl-2-morfolinobenzofuran-5-yl~metylaminosulfonat. Den erholdte blanding ble hurtig opp-varmet til 90-95°C og holdt ve å denne temperatur i 2 minutter. Deretter ble reaksjonsløsningen straks avkjølt ved tilsetning av is. For opparbeidelse ekstrahertes med eter, eterløsningen ble vasket to gangar med vann, tørret med magnesiumsulfat og inndampet i vakuum. To a mixture of 133 parts of water and 68 parts of concentrated hydrochloric acid, 68 parts of 2,3-dihydro«3,3-dimethyl-2-morpholinobenzofuran-5-yl-methylaminosulphonate were added at once at 80°C and with stirring. The resulting mixture was quickly heated to 90-95°C and held at this temperature for 2 minutes. The reaction solution was then immediately cooled by adding ice. For work-up it was extracted with ether, the ether solution was washed twice with water, dried with magnesium sulphate and evaporated in vacuo.

Den tyktflytende rest ble oppløst i 100 deler eter, og etter tilsetning av 60 deler n-heksan erholdtes ved kjøling 2,3~dihydro-3,3-dimetyl-2-hydroksybenzofuran-5-yl-metyl-aminosulfonat som krystallisat, sm.p. 111-112°C. The viscous residue was dissolved in 100 parts of ether, and after the addition of 60 parts of n-hexane, 2,3-dihydro-3,3-dimethyl-2-hydroxybenzofuran-5-yl-methylaminosulphonate was obtained as a crystallisate, sm. p. 111-112°C.

Forbindelsen har følgende strukturforme1:The compound has the following structural form1:

Forsøk C Attempt C

2, 3-dihydro-3, 3-dimetyl-2-metoksybenzof uran-5-yl-metylaminosulfonat 2, 3-dihydro-3, 3-dimethyl-2-methoxybenzofuran-5-yl-methylaminosulfonate

En oppløsning av 22,5 deler 2,3-dihydro-3,3-dimetyl-2-hydroksybenzofuran-5-yl-metylaminosulfonat i 200 deler metanol ble tilsatt 4 dråper konsentrert svovelsyre og deretter kokt i 30 minutter under tilbakeløp. For opparbeidelse ble reaksjons— blandingen etter kjøling nøytralisert med trietylamin og deretter inndampet til tørrhet i vakuum. Ved behandling av det seigtfly-tende residuum med eter/n-heksan-bl!anding erholdtes 2,3-dihydro-3 , 3-dimetyl-2-metoksyberizof uran-5-yl-metylaminosulfonat som krysital/lisat, sm.p. 89-91°C. To a solution of 22.5 parts of 2,3-dihydro-3,3-dimethyl-2-hydroxybenzofuran-5-yl-methylaminosulfonate in 200 parts of methanol was added 4 drops of concentrated sulfuric acid and then refluxed for 30 minutes. For work-up, the reaction mixture was neutralized with triethylamine after cooling and then evaporated to dryness in vacuo. By treating the viscous residue with an ether/n-hexane mixture, 2,3-dihydro-3,3-dimethyl-2-methoxyberizofuran-5-yl-methylaminosulfonate was obtained as crystals/lysate, m.p. 89-91°C.

Forbindelsen har følgende strukturforme1:The compound has the following structural form1:

I det tilfelle at R<4.>betyr en alkylamino-rest i de under In the event that R<4.> denotes an alkylamino residue in the below

a) eller b) beskrevne fremgangsmåter, er det acyleringsmiddel som anvendes, et isocyanat, som illustrert ved den følgende a) or b) described methods, the acylating agent used is an isocyanate, as illustrated by the following

reaksjonsligning med metylisocyanat som eksempel:reaction equation with methyl isocyanate as an example:

c) ved reaksjon av benzofuran-5-yl-am'inosulfonater med et alkylsulfonyl- eller amino-sulfonylhalogenid, som eksempelvis vist ved deh følgende reaks jonsligning, hvor metylsulfonylklorid anvendes: c) by reaction of benzofuran-5-yl-aminosulfonates with an alkylsulfonyl or aminosulfonyl halide, as shown for example by the following reaction equation, where methylsulfonyl chloride is used:

1 3 1 3

hvor R og R har samme betydning som ovenfor.where R and R have the same meaning as above.

d) ved innvirkning av metallhydroksyder, fortrinnsvis alkali- eller jordalkalihydroksyder, på benzofuran-5-yl-aminosulfonater som d) by the action of metal hydroxides, preferably alkali or alkaline earth hydroxides, on benzofuran-5-yl-aminosulfonates which

eksempelvis vist ved den følgende reaksjonsligning, hvor det anvendes natriumhydroksyd: for example shown by the following reaction equation, where sodium hydroxide is used:

1 3 1 3

hvor R og R har samme betydning som ovenfor.where R and R have the same meaning as above.

e) ved alkylering av benzofuran-5-yl-aminosulfonater med alkenyl-eller alkynyl-halogenider, idet man eksempelvis anvender de e) by alkylation of benzofuran-5-yl aminosulfonates with alkenyl or alkynyl halides, using for example the

ifølge d) fremstilte salter som reaksjonskomponenter, som illustrert ved anvendelse av allylbromid i den følgende reaksjonsligning: according to d) prepared salts as reaction components, as illustrated using allyl bromide in the following reaction equation:

1 3 1 3

hvor R og R har samme betydning som ovenfor.where R and R have the same meaning as above.

De følgende eksempler vil ytterligere belyse fremstillingen av de nye forbindelser. The following examples will further illustrate the preparation of the new compounds.

Eksempel 1Example 1

Til en oppløsning av ,30|, 1 vektdeler 2, 3-dihydro-3,3-dime-tyl-2-etoksy-benzofuran-5-yl-metylaminosulfonat og 12 vektdeler trietylamin i 90 vektdeler eter ble det ved 15-20°C og under om-røring tilsatt 9 vektdeler ajcetylklorid. Etter en time ble reaksjonsblandingen tre ganger ristet med vann. Eteroppløsningen ble tørret med magnesiumsulfat og Iinndampet i vakuum, hvorved man fikk forbindelsen 2,3-dihydro-3,3-dimetyl-2-etoksybenzofuran-5-yl-metyl-karbonyl-metylamino-sulfonat, nD 25 1,5042, som en oljeaktig rest som selv etter lengre tids henstand ikke krystalliserte. To a solution of .30|, 1 parts by weight of 2, 3-dihydro-3,3-dimethyl-2-ethoxy-benzofuran-5-yl-methylaminosulfonate and 12 parts by weight of triethylamine in 90 parts by weight of ether, at 15-20° C and, with stirring, added 9 parts by weight of ajcetyl chloride. After one hour, the reaction mixture was shaken three times with water. The ether solution was dried with magnesium sulfate and evaporated in vacuo to give the compound 2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-methyl-carbonyl-methylamino-sulfonate, nD 25 1.5042, as a oily residue which did not crystallize even after a long period of delay.

Analyse, infrarødt og NMR-spektra viser god overensstemmelse med den følgende strukturformel: Analysis, infrared and NMR spectra show good agreement with the following structural formula:

På tilsvarende måte ble de følgende forbindelser fremstilt: 2,3-dihydro-3,3-dimetyl-2-metoksybenzofuran-5-yl-N-metyl-karbonyl-25 metylammosulfonat, n£| 1,5085, 2,3-dihydro-3,3-dimetyl-2-metoksybenzofuran-S-yl-N-metyl-karbonyl-etylaminosulf onat, 2,3-dihydro-3,3-dimetyl-2-metoksybenzofuran-5-yl-N-etyl-karbonyl-metylaminosulfonat, 2,3-dihydro-3,3-dimetyl-2-etoksybenzofuran-5-yl-N-etyl-karbonyl-metylaminosulfonat, 2,3-dihydro-3,3-dimetyl-2-metoksybenzofuran-5-yl-N-klor-metylkar-25 bonyl-metylaminosulfonat, n£| 1,5195, 2,3-dihydro-3,3-dimetyl-2«etoksybenzofuran-5-yl-N-klor-metylkar-25 bonyl-metylaminosulfonat, n^ 1,5140, 2,3-dihydro-3,3-dimetyl-2-etoksybenzofuran-5-yl-N-diklor-metylkar-bonyl-metylaminosulfonat, n^ 25 1,5165, 2 , 3-dihydrc—3, 3-dimetyl-2-'metoksybenzof uran-S-yl-N-klor-metylkar-bonyl-etylaminosulfonat, In a similar manner, the following compounds were prepared: 2,3-dihydro-3,3-dimethyl-2-methoxybenzofuran-5-yl-N-methyl-carbonyl-25 methylammonosulfonate, n£| 1.5085, 2,3-dihydro-3,3-dimethyl-2-methoxybenzofuran-S-yl-N-methyl-carbonyl-ethylaminosulfonate, 2,3-dihydro-3,3-dimethyl-2-methoxybenzofuran-5 -yl-N-ethyl-carbonyl-methylaminosulfonate, 2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-N-ethyl-carbonyl-methylaminosulfonate, 2,3-dihydro-3,3-dimethyl -2-Methoxybenzofuran-5-yl-N-chloro-methylcarbonyl-25-bonyl-methylaminosulfonate, n£| 1.5195, 2,3-dihydro-3,3-dimethyl-2«ethoxybenzofuran-5-yl-N-chloro-methylcarbonyl-25-bonyl-methylaminosulfonate, n^ 1.5140, 2,3-dihydro-3,3 -dimethyl-2-ethoxybenzofuran-5-yl-N-dichloro-methylcarbonyl-methylaminosulfonate, n^ 25 1.5165, 2 , 3-dihydrc-3, 3-dimethyl-2-'methoxybenzofuran-S-yl- N-Chloro-methylcarbonyl-Ethylaminosulfonate,

2,3-dihydro-3,3«dimetyl-2-metoksybenzofuran-5-yl-N-metoksy-karbonyl-metylaminosulfonat, 2,3-dihydro-3,3'-dimethyl-2-methoxybenzofuran-5-yl-N-methoxy-carbonyl-methylaminosulfonate,

2, 3-dihydro-3, 3~dimetyl-2-metoksybenzof uran-5-yl-N-etoksykarbonyl-metylaminosulfonat, 2, 3-dihydro-3, 3-dimethyl-2-methoxybenzofuran-5-yl-N-ethoxycarbonyl-methylaminosulfonate,

2, 3-dihydro-3 / 3-dimetyl-2-metoksybenzof uran-5-yl-N-isopropoksy-karbonyl-metylaminosulfonat, 2, 3-dihydro-3/3-dimethyl-2-methoxybenzofuran-5-yl-N-isopropoxy-carbonyl-methylaminosulfonate,

2,3-dihydro—3,3-dimetyl-2-etoksybenzofuran-5-yl-N-metoksykarbonyl-25 2,3-dihydro—3,3-dimethyl-2-ethoxybenzofuran-5-yl-N-methoxycarbonyl-25

inetylamxnosulfonat/ 1,5000, inethylamine xnosulfonate/ 1.5000,

2, 3-dihydro-3, 3-dimetyl-2-etoksybenzof uran-5-yl-N-etoksykarbonyl-25 metylaminosulfonat, nD 1,4945, 2, 3-dihydro-3, 3-dimethyl-2-ethoxybenzofuran-5-yl-N-ethoxycarbonyl-25 methylaminosulfonate, nD 1.4945,

2,3-dihydro-3,3-dimetyl-2-etoksybenzofuran-5-yl-N-isopropoksykar-' 2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-N-isopropoxycar-'

rr-\25 bonyl-metylaminosulfonat, nD1,4880. rr-\25 bonyl methylaminosulfonate, nD 1.4880.

Eksempel 2Example 2

Til en oppløsning av 28,7 vektdeler 2,3-dihydro-3,3-dimetyl-2-hydroksybenzofuran-5-yl-dimetylaminosulfonat og 14,1 vektdeler trietylamin i 110 vektdeler eter ble det under omrøring ved -8 til To a solution of 28.7 parts by weight of 2,3-dihydro-3,3-dimethyl-2-hydroxybenzofuran-5-yl-dimethylaminosulfonate and 14.1 parts by weight of triethylamine in 110 parts by weight of ether, while stirring at -8 to

-12°Ctilsatt 10,3 vektdeler acetylklorid. Etter opparbeidelsen av reaksjonsblandingen som beskrevet i Eksempel 1 erholdtes forbindelsen 2,3-dihydro-3,3-dimetyl-2-metylkarbonyloksybenzofuran-5-yl-dimetylaminolulfonat som krystallisat, sm.p. 67-68°C; den har føl-gende strukturformel: -12°C with 10.3 parts by weight of acetyl chloride added. After working up the reaction mixture as described in Example 1, the compound 2,3-dihydro-3,3-dimethyl-2-methylcarbonyloxybenzofuran-5-yl-dimethylaminosulfonate was obtained as a crystallisate, m.p. 67-68°C; it has the following structural formula:

På tilsvarende måte ble de følgende forbindelser fremstilt: 2,3-dihydro-3,3-dimetyl-2-etylkarbonyloksybenzofuran-5-yl-dimetylaminosulfonat, sm.p. 53-54°C/ 2 , 3-dihydro-3 , 3-dimetyl-*2-klormetylkarbonyloksybenzof uran-5-yl-dimetylarainosulfonat, sm.p. 87-88°C, In a similar manner, the following compounds were prepared: 2,3-dihydro-3,3-dimethyl-2-ethylcarbonyloxybenzofuran-5-yl-dimethylaminosulfonate, m.p. 53-54°C/ 2 , 3-dihydro-3 , 3-dimethyl-*2-chloromethylcarbonyloxybenzofuran-5-yl-dimethylarainosulfonate, m.p. 87-88°C,

2,3-dihydro-3,3-dimetyl-2>=klormetylkarbonyloksybenzof uran~5-yl~2,3-dihydro-3,3-dimethyl-2>=chloromethylcarbonyloxybenzofuran~5-yl~

25 25

dietylaminosulfonat, nD 1,5078, diethylaminosulfonate, nD 1.5078,

2, 3~dihydro-3, 3-dimety l--2-<liklormetylkarbonyloksybenzofuran«=5«yl« dimetylaminosulfonat, 2 , 3-dihydro-3 , 3—dimetyl-2-diklormetylkarbonyloksy—benzofuran-5-yl-dietylam£lnosulfonat, 2, 3~dihydro-3, 3-dimethyl--2-<lichloromethylcarbonyloxybenzofuran«=5«yl« dimethylaminosulfonate, 2 , 3-dihydro-3 , 3-dimethyl-2-dichloromethylcarbonyloxy—benzofuran-5-yl-diethylam£ linosulfonate,

2, 3-dihydro-3, 3-dimetyl-2-metoksykarbonyloksybenzof ur'ah-5-yl-dimety laminosulf onat, sm.p. 101-102°C, 2,3-dihydro-3,3-dimethyl-2-methoxycarbonyloxybenzofuran-5-yl-dimethyl laminosulfonate, m.p. 101-102°C,

2,3-dihydro-3,3-dimetyl-2-etoksykarbonyloksybenzofuran-5-yl-dimetylamiSosulfonat, sm.p. 84-85°C, 2,3-dihydro-3,3-dimethyl-2-ethoxycarbonyloxybenzofuran-5-yl-dimethylamisulfonate, m.p. 84-85°C,

2,3-dihydro-3,3-dimetyl-2=isopropoksykarbonyloksybenzof uran-5-yl-dimetylaminosulfonat, 2,3-dihydro-3,3-dimethyl-2=isopropoxycarbonyloxybenzofuran-5-yl-dimethylaminosulfonate,

2,3-dihydro-3,3~dimetyl-2-metoksykarbonyloksybenzofuran-5-yl-dietylaminosulfonat, sm.p. 95-96°C, 2,3-dihydro-3,3-dimethyl-2-methoxycarbonyloxybenzofuran-5-yl-diethylaminosulfonate, m.p. 95-96°C,

2,3-dihydro-3,3-dimetyl-2-etoksykarbonyloksybenzofuran-5-yl-dietylaminosulfonat, 2,3-dihydro-3,3-dimethyl-2-ethoxycarbonyloxybenzofuran-5-yl-diethylaminosulfonate,

2,3-dihydro-3,3=dimetyl-2~isopropoksykarbonyloksybenzofuran-5-yl-dietylaminosulfonat.2,3-dihydro-3,3=dimethyl-2-isopropoxycarbonyloxybenzofuran-5-yl-diethylaminosulfonate.

Eksempel 3Example 3

Til en oppløsning av 28,7 vektdeler 2,3-dihydro-3,3-dimetyl-2-hydroksybenzofuran«5«»yl-dimetylaminosulfonat i 90 vektdeler tetrahydrofuran ble det ettes tilsetning av 1 vektdel trietylamin tilsatt 6,9 vektdeler metylisocyanat ved romtemperatur (20°C). Etter en svak temperaturstigning ble reaksjonsblandingen hensatt i 24 timer. For opparbeidelse ble løsningsmiddelet fjernet i vakuum og residuet omkrystallisert fra eter: sm.p. 101-103°C. To a solution of 28.7 parts by weight of 2,3-dihydro-3,3-dimethyl-2-hydroxybenzofuran«5«»yl-dimethylaminosulfonate in 90 parts by weight of tetrahydrofuran, 1 part by weight of triethylamine was added to 6.9 parts by weight of methyl isocyanate at room temperature (20°C). After a slight rise in temperature, the reaction mixture was allowed to stand for 24 hours. For work-up, the solvent was removed in vacuo and the residue recrystallized from ether: m.p. 101-103°C.

Forbindelsen 2,3-dihydro-3,3-dimetyl-2-metylaminokarbonyl« oksybenzofuran-5-yl-dimetylaminosulfonat har følgende strukturformel: The compound 2,3-dihydro-3,3-dimethyl-2-methylaminocarbonyl« oxybenzofuran-5-yl-dimethylaminosulfonate has the following structural formula:

På tilsvarende måte ble de følgende forbindelser fremstilt: 2, 3-dihydro-3, 3-dimetyl~2-etylaminokarbonyloksybenzof uran-5-yl-dimetylaminosulfonat, sm.p. 112-113 oC, In a similar manner, the following compounds were prepared: 2,3-dihydro-3,3-dimethyl~2-ethylaminocarbonyloxybenzofuran-5-yl-dimethylaminosulfonate, m.p. 112-113 oC,

2,3-dihydro-3,3-dimetyl-2-propylaminokårbonyloksybenzofuran-5-yl-dimetylaminosulfonat, 2,3-dihydro-3,3-dimethyl-2-propylaminocarbonyloxybenzofuran-5-yl-dimethylaminosulfonate,

2,3-dihydro-3,3-dimetyl-2-isopropylaminokarbonyloksybenzofuran-5-yl-dimety laminosulf onat, sm.p. 107-109°C, 2,3-dihydro-3,3-dimethyl-2-isopropylaminocarbonyloxybenzofuran-5-yl-dimethyl laminosulfonate, m.p. 107-109°C,

2,3-dihydro-3,3-dimety1-2-metylaminokarbonyloksybenzofuran-5-yl-dietylaminosulfonat, sm.p. 122-123°C, 2,3-dihydro-3,3-dimethyl-2-methylaminocarbonyloxybenzofuran-5-yl-diethylaminosulfonate, m.p. 122-123°C,

2,3-dihydro-3,3-dimetyl-2-etylaminokarbonyloksybenzofuran-5-yl-dietylaminosulfonat, sm.p. 124-125°C, 2,3-dihydro-3,3-dimethyl-2-ethylaminocarbonyloxybenzofuran-5-yl-diethylaminosulfonate, m.p. 124-125°C,

2,3-dihydro-3,3-dimetyl-2-metylaminokarbonyloksybenzofuran-5-yl-metylaminosulfonat, 2,3-dihydro-3,3-dimethyl-2-methylaminocarbonyloxybenzofuran-5-yl methylaminosulfonate,

2,3-dihydro-3,3-dimety1-2-etylaminokarbonyloksybenzofuran-5-yl-metylaminosulfonat, 2,3-dihydro-3,3-dimethyl-2-ethylaminocarbonyloxybenzofuran-5-yl methylaminosulfonate,

2,3-dihydro-3,3-dimety1-2-propylaminokarbonyloksybenzofuran-5-yl-metylaminosulfonat, 2,3-dihydro-3,3-dimethyl-2-propylaminocarbonyloxybenzofuran-5-yl methylaminosulfonate,

2,3-dihydro-3,3-dimetyl-2-isopropylaminokarbonyloksybenzofuran-5-y1-metylaminosulfonat. 2,3-dihydro-3,3-dimethyl-2-isopropylaminocarbonyloxybenzofuran-5-yl-1-methylaminosulfonate.

Eksempel 4Example 4

Til en oppløsning av 68 vektdeler 2,3-dihydro-3,3-dimetyl-2-hydroksybenzofuran-5-yl-metylaminosulfonat og'55,5 vektdeler trietylamin ble det ved 10°C tilsatt 56 vektdeler acetanhydr|i<_>d under omrøring. To a solution of 68 parts by weight of 2,3-dihydro-3,3-dimethyl-2-hydroxybenzofuran-5-yl-methylaminosulfonate and 55.5 parts by weight of triethylamine, 56 parts by weight of acetic anhydride were added at 10°C while stirring.

Etter henstand natten over ble det utfelte reaksjonsprodukt avsuget, deretter vasket med kold eter og vann og tørret i vakuum ved 60°C: sm.p. 103-104°C. After standing overnight, the precipitated reaction product was filtered off with suction, then washed with cold ether and water and dried in vacuum at 60°C: m.p. 103-104°C.

Forbindelsen 2,3-dihydro-3,3-dimetyl-2-metylkarbonyloksy-benzofuran-5-yl-N—metylkarbonyl-metylaminosulfonat har den følgende The compound 2,3-dihydro-3,3-dimethyl-2-methylcarbonyloxy-benzofuran-5-yl-N-methylcarbonyl-methylaminosulfonate has the following

strukturformel: structural formula:

1 3 På tilsvarende måte ble de følgende forbindelser fremstilt: 2, 3-dihydro-3,3-dimetyl-2-klormetylkarbonyloksybenzofuran-5-yl-N-klormetylkarbonyl-metylaminosulfonat, 1 3 In a similar manner, the following compounds were prepared: 2, 3-dihydro-3,3-dimethyl-2-chloromethylcarbonyloxybenzofuran-5-yl-N-chloromethylcarbonyl-methylaminosulfonate,

2,3-dihydro-3,3-dimetyl-2-etylkarbonyloksybenzofuran-5-yI-N-etylkarbonyl-metylaminosulfonat, 2,3-dihydro-3,3-dimethyl-2-ethylcarbonyloxybenzofuran-5-yl-N-ethylcarbonyl-methylaminosulfonate,

2,3-dihydro-3,3-dimety1-2-metkarbonyloksybenzofuran-5-yI-N-metylkarbonyl-etylaminosulfonat. 2,3-dihydro-3,3-dimethyl-2-methcarbonyloxybenzofuran-5-yl-N-methylcarbonyl-ethylaminosulfonate.

Eksempel 5Example 5

Til en oppløsning av 28,7 vektdeler 2,3-dihydro-3,3-dimetyl-2-metoksybenzofuran-5-yl-metylaminosulfonat og 13,3 vektdeler tirietylamin i 130 vektdeler diklormetan ble det ved -8 til '-l^C tilsatt en oppløsning av 13,8 vektdeler metylsulfonylklorid To a solution of 28.7 parts by weight of 2,3-dihydro-3,3-dimethyl-2-methoxybenzofuran-5-yl-methylaminosulfonate and 13.3 parts by weight of triethylamine in 130 parts by weight of dichloromethane, at -8 to '-1^C added a solution of 13.8 parts by weight of methylsulfonyl chloride

i 30 vektdeler diklormetan. 30 minutter etter fullført reaksjon ble blandingen rystet tre ganger med vann. Den organiske fase ble tørret med magnesiumsulfat og løsningsmiddelet fjernet i va-25 —- in 30 parts by weight of dichloromethane. 30 minutes after completion of the reaction, the mixture was shaken three times with water. The organic phase was dried with magnesium sulfate and the solvent removed in va-25 —-

kuum. Det sirupaktige residuum (nD 1,5150) krystalliserte ikke selv etter lengre tids henstand. kuum. The syrupy residue (nD 1.5150) did not crystallize even after standing for a long time.

IR- og KMR-spektra og elementaranalyse av residuet er i god overensstemmelse med forbindelsen 2,3-dihydro-3,3-dimetyl-2-metoksybenzofuran-5-yl-N-metyl-sulfonyl-metylaminosulfonat med følgende strukturformel: IR and NMR spectra and elemental analysis of the residue are in good agreement with the compound 2,3-dihydro-3,3-dimethyl-2-methoxybenzofuran-5-yl-N-methyl-sulfonyl-methylaminosulfonate with the following structural formula:

På tilsvarende måte ble de følgende forbindelser fremstilt: 2,3=dihydro~3,3-dimety1-2-etoksybenzofuran-5-yl-N-metyl-sulfonyl-metylaminosulfonat, In a similar manner, the following compounds were prepared: 2,3=dihydro~3,3-dimethyl-2-ethoxybenzofuran-5-yl-N-methyl-sulfonyl-methylaminosulfonate,

2,3-dihydro-3,3-dimetyl-2-metoksybenzofuran-5-yl-N-etyl-sulfonyl-metylaminosulfonat, 2,3-dihydro-3,3-dimethyl-2-methoxybenzofuran-5-yl-N-ethyl-sulfonyl-methylaminosulfonate,

2,3-dihydro~3,3-dimetyl-2-etoksybenzofuran-5-yl-etyl-sulfonyl» metylaminosulfonat. 2,3-dihydro~3,3-dimethyl-2-ethoxybenzofuran-5-yl-ethyl-sulfonyl» methylaminosulfonate.

Eksempel 6Example 6

Til en oppløsning av 20,5~vektdeler 2,3-dihydro-3,3-dimetyl-2-etoksybenzofuran—5-yl-metylaminosulfonat i 70 vektdeler tetrahydrofuran ble det etter tilsetning av 0,5 vektdel trietylamin tilsatt 5,15 vektdeler metylisocyanat, hvoretter blandingen ble hensatt i 48 timer. For opparbeidelse ble løsningen inndampet i vakuum, residuet opptatt i eter og behandlet tre ganger med vann. Den organiske fase ble tørret med magnesiumsulfat, behandlet med 25 <— To a solution of 20.5 parts by weight of 2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-methylaminosulfonate in 70 parts by weight of tetrahydrofuran, 5.15 parts by weight of methyl isocyanate were added after the addition of 0.5 parts by weight of triethylamine , after which the mixture was left for 48 hours. For work-up, the solution was evaporated in vacuo, the residue taken up in ether and treated three times with water. The organic phase was dried with magnesium sulfate, treated with 25 <—

aktivkull og inndampet i vakuum, nD 1,5085.activated carbon and evaporated in vacuo, nD 1.5085.

IR- og NMR-spektra og elementaranalyse av det sirupaktige residuum er i god overensstemmelse med forbindelsen 2,3-dihydro-3,3-dimety1-2-etoksybenzofuran-5-yl-N-metylaminokarbonyl-metyl— aminosulfonat med følgende strukturformel: IR and NMR spectra and elemental analysis of the syrupy residue are in good agreement with the compound 2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-N-methylaminocarbonyl-methyl- aminosulfonate with the following structural formula:

På tilsvarende måte ble de følgende forbindelser fremstilt: 2, 3-dihydro-=-3,3-dimety 1-2-metoksybenzof uran-5-yl-N-metyl-amino-karbonyl-metylaminosulfonat, In a similar manner, the following compounds were prepared: 2, 3-dihydro-=-3,3-dimethyl 1-2-methoxybenzofuran-5-yl-N-methyl-amino-carbonyl-methylaminosulfonate,

2,3-dihydro-3,3-dimetyl-2-etoksybenzofuran-5-yl-N-etyl-amino» karbonyl-metylaminosulfonat, 2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-N-ethyl-amino» carbonyl methylaminosulfonate,

2,3-dihydro-3,3-dimety1-2-metoksybenzofuran-5-yl-N-etyl-amino-karbonyl-metylaminosulfonat. 2,3-dihydro-3,3-dimethyl-2-methoxybenzofuran-5-yl-N-ethyl-amino-carbonyl-methylaminosulfonate.

Eksempel 7Example 7

Til en suspensjon av 30,1 vektdeler 2,3-dihydro-3,3-dimetyl-2-etoksybenzofuran-5-yl-metylaminosulfonat i 55 vektdeler vann ble det tilsatt en oppløsning av 4 vektdeler natriumhydroksyd i 20 vektdeler vann. Man fikk en oppløsning. Fra denne opp-løsning kunne saltet utvinnes ved avdamping av vannet i vakuum. IR- og KMR-spektra og elementaranalyse av saltet er i god overensstemmelse med natriumsaltet av 2,3-dihydro-3,3-dimetyl-2-etoksy-benzofuran-5-yl-metylaminosulfonat-natriumsalt med følgende struk-turf ormel: To a suspension of 30.1 parts by weight of 2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-methylaminosulfonate in 55 parts by weight of water was added a solution of 4 parts by weight of sodium hydroxide in 20 parts by weight of water. A resolution was obtained. The salt could be recovered from this solution by evaporating the water in a vacuum. IR and NMR spectra and elemental analysis of the salt are in good agreement with the sodium salt of 2,3-dihydro-3,3-dimethyl-2-ethoxy-benzofuran-5-yl-methylaminosulfonate sodium salt with the following structural formula:

På tilsvarende måte ble litium- henholdsvis natrium- henholdsvis kalium-saltet av de følgende forbindelser fremstilt: 2,3-dihydro-3,3-dimetyl-2-metoksybenzofuran-5-yl-mety1-aminosulfonat, In a similar manner, the lithium, sodium and potassium salts of the following compounds were prepared: 2,3-dihydro-3,3-dimethyl-2-methoxybenzofuran-5-yl-methyl-aminosulfonate,

2,3-dihydro-3 ,\3-dimetyl-2-etoksybenzof uran-5-yl-metyl-aminosulfonat, 2,3-dihydro-3,\3-dimethyl-2-ethoxybenzofuran-5-yl-methyl-aminosulfonate,

2,3-dihydro-3,3-dimetyl-2-metoksybenzofuran-5-yl-ety1-aminosulfonat, 2,3-dihydro-3,3-dimethyl-2-methoxybenzofuran-5-yl-ethyl-1-aminosulfonate,

2,3-dihydro-3,3-dimetyl-2-etoksybenzofuran-5-yl-etyl-aminosulfonat. 2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl ethyl aminosulfonate.

Eksempel 8Example 8

Til 46 vektdeler av en 50%'s (vekt%) vandig løsning av To 46 parts by weight of a 50%'s (wt%) aqueous solution of

. natriumsaltet av 2,3-dihydro-3, 3-d,imetyl-2-etoksybenzofuran-5-yl-metylaminosulfonat(fremstilt som beskrevet i det foregående eksempel) ble det ved 20-23°C tilsatt en oppløsning av 8,5 vektdeler propargylbromid i 20 vektdeler aceton under omrøring. Her-under ble en svak temperaturstigning til 29°C obserbert. Reak- . the sodium salt of 2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-methylaminosulfonate (prepared as described in the previous example) was added at 20-23°C to a solution of 8.5 parts by weight propargyl bromide in 20 parts by weight of acetone with stirring. Below, a slight rise in temperature to 29°C was observed. Reac-

sjonen ble fullstendiggjort ved omrøring i 6 timer ved 35°C. For opparbeidelse ble reaksjonsblandingen tilsatt eddiksyreetylester og deretter ekstrahert, tre ganger med vann. Den organiske fase ble tørret med magnesiumsulfat og deretter inndampet til tørrhet i vakuum: n<25>1,5085. The reaction was completed by stirring for 6 hours at 35°C. For work-up, the reaction mixture was added with acetic acid ethyl ester and then extracted three times with water. The organic phase was dried with magnesium sulfate and then evaporated to dryness in vacuo: n<25>1.5085.

IR- og NMR-spektra og elementaranalyse av det sirupaktige residuum er i god overensstemmelse med forbindelsen 2,3-dihydro-3,3-dimety1-2-etoksybenzofuran-5-yl-N-propargyl-metylaminosulfonat med følgende strukturformel: IR and NMR spectra and elemental analysis of the syrupy residue are in good agreement with the compound 2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-N-propargyl methylaminosulfonate with the following structural formula:

På tilsvarende måte ble de følgende forbindelser fremstilt: 2,3-dihydro-3,3-dimetyl-2-etoksybenzofuran-5-yl-N-allyl-metylami- In a similar manner, the following compounds were prepared: 2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-N-allyl-methylami-

r 0,01 rn ' D -r 0.01 rn ' D -

nosulfonat, k.p._ _.. 137-146°C, n25 1,506517" nosulfonate, b.p._ _.. 137-146°C, n25 1.506517"

2,3-dihydro-3,3-dimetyl-etoksybenzofuran-5-yl-propargyl-aminosulfonat, 2,3-dihydro-3,3-dimethyl-ethoxybenzofuran-5-yl-propargyl-aminosulfonate,

2,3-dihydro-3,3-dimetyl-2-etoksybenzofuran-5-yl-allyl-aminosulfonat, 2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-allyl aminosulfonate,

2,3-dihydro-3,3-dimetyl-2~metoksybenzofuran-5-yl-propargyl-amino-sulfonåt, 2,3-dihydro-3,3-dimethyl-2-methoxybenzofuran-5-yl-propargyl-amino-sulfonate,

2,3-dihydro-3,3-dimetyl-2-metoksybenzofuran-5-yl-allyl-aminosulfonat, 2,3-dihydro-3,3-dimethyl-2-methoxybenzofuran-5-yl-allyl aminosulfonate,

2,3-dihydro-3,3-dimetyl-2-etoksybenzofuran-5-yl-diallyl-aminosulfonat, 2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl diallyl aminosulfonate,

De virksomme stoffer oppviser en sterk herbicid virkning og kan derfor anvendes som ugrasdrepende midler eller til bekjem-pelse av uønsket plantevekst. Om midlene'virker som totale eller selektjive Inidler avhenger hovedsakelig av den mengde virksomt stoff som anvendes pr. flateenhet. The active substances exhibit a strong herbicidal effect and can therefore be used as weedkillers or to combat unwanted plant growth. Whether the agents act as total or selective agents depends mainly on the amount of active substance used per surface unit.

Med ugras henholdsvis uønsket plantevekst menes alle enfrø-bladede og tofrøbladede planter som vokser på steder hvor de ikke By weeds or unwanted plant growth is meant all monocotyledonous and dicotyledonous plants which grow in places where they are not

ønsket.wished.

Således kan man med midlene ifølge oppfinnelsen eksempelvis bek j empe Thus, with the means according to the invention, for example, you can fight

Den mengde som anvendes av herbicidene ifølge oppfinnelsen kan variere. Mengden avhenger hovedsakelig av arten av den ønskede virkning. The quantity used of the herbicides according to the invention can vary. The amount depends mainly on the nature of the desired effect.

Den mengde som anvendes ligger vanligvis mellom 0,1 og 15 kg virksomt stoff pr. hektar eller mer, fortrinnsvis mellom 0,2 og 6 kg virksomt stoff pr. hektar. The quantity used is usually between 0.1 and 15 kg of active substance per hectare or more, preferably between 0.2 and 6 kg of active substance per hectares.

Herbicidene ifølge oppfinnelsen kan anvendes i kbrhkulturer, så som The herbicides according to the invention can be used in vegetable crops, such as

Bromeliaceae, f.eks. Bromeliaceae, e.g.

Ananas sativu!s3Pineapple sativu!s3

Anvendelsen av herbicidene skjer eksempelvis i form av direkte sprøytbare løsninger, pulvere, suspensjoner eller disper-sjoner, emulsjoner, oljedispersjoner, pastaer, støvformige midler, strømidler, granulater, ved sprøyting, forstøvning, spredning eller uthelling. Anvendelsesformene retter seg helt etter anvendelses-formålet; man tar imidlertid alltid sikte på å oppnå en mest mulig fin fordeling av de virksomme stoffer. The herbicides are used, for example, in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusty agents, flow agents, granules, by spraying, atomisation, spreading or pouring. The forms of application depend entirely on the purpose of application; however, the aim is always to achieve the best possible distribution of the active substances.

Ved fremstilling av direkte sprøytbare løsninger, emulsjoner, pastaer og oljedispersjoner kan man bruke mineraloljefraksjoner med midlere til høyt kokepunkt, så som*1 kerosin eller dieselolje, enn-videre kulltjæreoljer etc, samt oljer av vegetabilsk eller ani-malsk opprinnelse, alifatiske, cykliske og aromatiske hydrokarboner, for eksempel benzen, toluen, xylen, paraffin, tetrahydronaftalin, alkylerte naftaliner eller derivater derav, for eksempel! metanol, etanol, propanol, butanol, kloroform, karbontetraklorid, cykloheksa-nol, cykloheksanon, klorbenzen, isoforon<r>etc., sterkt polare løs-ningsmidler, så som dimetylformamid, dimetylsulfoksyd, n-metyl-pyr-rolidon, vann etc. When producing directly sprayable solutions, emulsions, pastes and oil dispersions, you can use mineral oil fractions with high boiling points, such as*1 kerosene or diesel oil, also coal tar oils, etc., as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or derivatives thereof, for example! methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, etc., strongly polar solvents, such as dimethylformamide, dimethyl sulfoxide, n-methyl-pyrrolidone, water, etc.

Vandige bruksformer kan fremstilles av emulsjonskonsentra-ter, pastaer eller fuktbare pulvere (sprøytepulvere) eller oljedispersjoner ved tilsetning av vann. Ved fremstilling av emulsjoner, pastaer eller oljedispersjoner, kan stoffene som sådanne eller opp-løst i olje eller løsningsmiddel homogeniseres i vann ved hjelp av fukte-, klebe-, dispergerings- eller emulgeringsmiddel. Det kan imidlertid ogs'å~fremstilles 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) or oil dispersions by adding water. When producing emulsions, pastes or oil dispersions, the substances as such or dissolved in oil or solvent can be homogenised in water by means of wetting, adhesive, dispersing or emulsifying agents. 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: alkali-, jord-alkali-, ammoniumsalter av ligninsulfonsyre, naftalinsulfonsyrer, fenolsulfonsyrer, alkylarylsulfonater, alkylsulfater, alkylsulfo-nater, alkali- og jordalkalisalter av dibutylnaftalinsulfonsyre, lauryletersulfat, fettalkoholsulfater, fettsure alkali- og jordalkalisalter, salter av sulfaterte heksadekanoler, heptadekanoler, oktadekanoler, salter av sulfatert fettalkoholglykoleter, kondensasjonsprodukter av sulfonert naftalin og naftalinderivater med formaldehyd, kondensasjonsprodukter av naftalin eller naftalinsulfon syrer med fenol og formaldehyd, polyoksye^Eylen-oktylfenoleter, etoksylert isooktylfenol, -oktylfenol, -nonylfenol, alkylfenolpolygly-koleter, tributylfenylpolyglykoleter, alkylarylpolyeteralkoholer, isotridecylalkohol, fettalkoholetylenoksyd-kondensater, etoksylert ricinusolje, polyoksyetylenalkyleter, etoksylert polyoksypropylen, laurylalkoholpolyglykoleteracetal, sorbitolester, lignin, sulfitt-avluter og metylcellulose. Among surfactants can be mentioned: alkali, alkaline earth, ammonium salts of ligninsulfonic acid, naphthalene sulfonic acids, phenolsulfonic acids, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, alkali and alkaline earth salts of dibutyl naphthalene sulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, fatty acid alkali and alkaline earth salts, salts of sulfated hexadecanols, heptadecanols, octadecanols, salts of sulfated fatty alcohol glycol ether, condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalene sulfonic acids with phenol and formaldehyde, polyoxy^Eylene-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 ester, lignin, sulphite deluters and methyl cellulose solve.

Pulver, strø- og støvformige midler kan fremstilles ved blanding eller sammaling av de virksomme stoffer med et fast bære-materiale. Powders, sprinkles and dust-like agents can be prepared by mixing or grinding together the active substances with a solid carrier material.

Granulater, for eksempel omhyllings-, impregnerings- og homogengranulater kan fremstilles ved binding av de virksomme stoffer på faste bærematerialer. Faste bærematerialer er eksempelvis mineralmaterialer så som silikagel, kiselsyrer, kiselgeler, silika-ter, talkum, kaolin, attaclay, kalkstein, kalk, kritt, bolus, løss, leire, dolomitt, diatoméjord, kalsium- og magnesiumsulfat, magne-siumoksyd, malte harpikser, gjødningsstoffer som for eksempel ammo-niumsulfat, ammoniumfosfat, ammoniumnitrat, urinstoffer og vege-tabilske produkter så som mel av korn, bark, tre og nøtteskall, cel-lulo^sepulver og andre faste bærematerialer. Granules, for example encasing, impregnation and homogenous granules, can be produced by binding the active substances to solid carrier materials. Solid carrier materials are, for example, mineral materials such as silica gel, silicic acids, silica gels, silicates, talc, kaolin, attack clay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, ground resins , fertilizers such as ammonium sulphate, ammonium phosphate, ammonium nitrate, urea and vegetable products such as flour from grain, 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 man, eventuelt først umiddelbart før anvendelsen (tankblanding), til-sette oljer av forskjellige typer, herbicider, fungicider, nematocider, insekticider, baktericider, sporelementer, gjødningsstoffer, skumhindrende midler (for eksempel silikoner), vekstregulatorer, motgiftmidler eller andre herbicid virksomme forbindelser, som for eksempel). Oils of different types, herbicides, fungicides, nematocides, insecticides, bactericides, trace elements, fertilisers, anti-foaming agents (for example silicones), growth regulators can be added to the mixtures or the individual active substances, possibly only immediately before use (tank mixture). , antidotes or other herbicidally active compounds, such as for example).

substituerte anilinersubstituted anilines

substituerte aryloksykarboksylsyrer og deres salter, estere og amider substituted aryloxycarboxylic acids and their salts, esters and amides

substituerte eteresubstituted ethers

substituerte arsonsyrer og deres salter, estere og amider substituerte benzimidazoler substituted arsonic acids and their salts, esters and amides substituted benzimidazoles

substituerte benzisotiazolersubstituted benzisothiazoles

substituerte benztiadiazinondioksydersubstituted benzthiadiazine dioxides

substituerte benzoksazinersubstituted benzoxazines

substituerte benzoksazinonersubstituted benzoxazinones

substituerte benztiadiazolersubstituted benzthiadiazoles

substituerte biuretersubstituted biurets

substituerte kinolinersubstituted quinolines

substituerte karbamatersubstituted carbamates

substituerte alifatiske karboksylsyrer og deres salter, estere og amider substituted aliphatic carboxylic acids and their salts, esters and amides

substituerte aromatiske karboksylsyrer og deres salter, estere og amider substituted aromatic carboxylic acids and their salts, esters and amides

substituerte karbamoylalkyl-tiol- eller ditiofosfater substituerte kinazoliner substituted carbamoylalkyl thiol or dithiophosphates substituted quinazolines

substituerte cykloalkylamidokarbontiolsyrer og deres salter, estere og amider substituted cycloalkylamidocarbonthiolic acids and their salts, esters and amides

substituerte cykloalkylkarbonamido-tiazoler substituerte dikarboksylsyrer og deres salter, estere og amider substituerte dihydrobenzofuransulfonater substituted cycloalkylcarbonamido-thiazoles substituted dicarboxylic acids and their salts, esters and amides substituted dihydrobenzofuran sulphonates

substituerte disulfidersubstituted disulfides

substituerte dipyridyliumsaltersubstituted dipyridylium salts

substituerte ditiokarbamatersubstituted dithiocarbamates

substituerte ditiofosforsyrer og deres salter, estere og amider substituerte urinstoffer substituted dithiophosphoric acids and their salts, esters and amides substituted ureas

sub st itue rte hek sahydro-l-H-kar bot ioate rsub st itue rte hek sahydro-l-H-kar bot ioate r

substituerte hydahfoinersubstituted hydahphoins

substituerte hydrazidersubstituted hydrazides

substituerte hydrazoniumsaltersubstituted hydrazonium salts

substituerte isooksazolpyrimidonersubstituted isoxazolepyrimidones

substituerte imidazolersubstituted imidazoles

substituerte isotiazolpyrimidonersubstituted isothiazolepyrimidones

substituerte ketonersubstituted ketones

substituerte naftokinonersubstituted naphthoquinones

substituerte alifatiske nitrilersubstituted aliphatic nitriles

substituerte aromatiske nitrilersubstituted aromatic nitriles

substituerte oksadiazolersubstituted oxadiazoles

substituerte oksadiazinonersubstituted oxadiazinones

substituerte oksadiazolidindionersubstituted oxadiazolidinediones

substituerte oksadiazindionersubstituted oxadiazinediones

substituerte fenoler og deres salter og estere substituerte fosfonsyrer og deres salter, estere]og amider substituerte fosfoniumklorider substituted phenols and their salts and esters substituted phosphonic acids and their salts, esters and amides substituted phosphonium chlorides

substituerte fosfonalkylglycinersubstituted phosphonalkylglycines

substituerte fosfitersubstituted phosphites

fosfdr^ylrér og deres salter, estere og amider phosphhydryls and their salts, esters and amides

substituerte piperidinersubstituted piperidines

substituerte pyrazoler substituted pyrazoles

substituerte pyrazolalkylkarboksylsyrer og deres salter, estere og amider substituted pyrazolealkylcarboxylic acids and their salts, esters and amides

substituerte pyrazoliumsaltersubstituted pyrazolium salts

substituerte pyrazoliumalkylsulfatersubstituted pyrazolium alkyl sulfates

substituerte pyridazinersubstituted pyridazines

substituerte pyridazonersubstituted pyridazones

substituerte pyridinkarboksylsyrer og deres salter, estere og amider substituted pyridine carboxylic acids and their salts, esters and amides

substituerte pyridinersubstituted pyridines

substituerte pyridinkarboksylatersubstituted pyridine carboxylates

substituerte pyridinonersubstituted pyridinones

substituerte pyrimidinersubstituted pyrimidines

substituerte pyrimidinersubstituted pyrimidines

substituerte pyrimidoner substituted pyrimidones

substituert ^/pyrrolidinkarboksylsyre og dennes salter, estere og amider substituted ^/pyrrolidine carboxylic acid and its salts, esters and amides

substituerte pyrrolidinersubstituted pyrrolidines

substituerte pyrrolidonersubstituted pyrrolidones

substituerte arylsulfonsyrer og deres salter, estere og amider substituerte styréner substituted arylsulfonic acids and their salts, esters and amides substituted styrenes

substituerte tetrahydro-oksadiazindionersubstituted tetrahydro-oxadiazindiones

substituerte tetrahydro-oksadiazoldionersubstituted tetrahydro-oxadiazolediones

substituerte tetrahydrometanoindener substituted tetrahydromethanoindenes

substituerte tetrahydro-diazol-tionersubstituted tetrahydrodiazole ions

substituerte tetrahydro-tiadiazin-tionersubstituted tetrahydro-thiadiazine ions

substituerte tetrahydro-tiadiazoldionersubstituted tetrahydrothiadiazolediones

substituerte aromatiske tiokarboksylsyreamider substituerte tiokarboksylsyrer og deres salter, estere og amider substituerte tiolkarbamater substituted aromatic thiocarboxylic acid amides substituted thiocarboxylic acids and their salts, esters and amides substituted thiol carbamates

substituerte tiourinstoffersubstituted thioureas

substituerte tiofosforsyrer og deres salter, estere og amider substituerte triaziner substituted thiophosphoric acids and their salts, esters and amides substituted triazines

substituerte triazolersubstituted triazoles

substituerte uracilersubstituted uracils

substituerte uretidindioner.substituted uretidine diones.

De sistnevnte herbicide forbindelser kan etter ønske anvendes før eller etter de virksomme enkeltstoffer eller blandinger ifølge oppfinnelsen. The latter herbicidal compounds can, if desired, be used before or after the active single substances or mixtures according to the invention.

Tilblandingen av disse midler til herbicidene ifølge oppfinnelsen kan skje i vektforholdet 1:10 til 10:1. Det samme gjelder for olje, fungicider, nematocider, insekticider, baktericider, motgiftmidler og vekstregulatorer. The addition 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, fungicides, nematocides, insecticides, bactericides, antidotes and growth regulators.

Herbicidene ifølge oppfinnelsen kan blant annet anvendes før plantingen, etter plantingen, før såingen, før plantene kommer opp av jorden, etter at plantene er kommet opp av jorden eller mens kulturplantene eller de uønskede planter er i ferd med å komme opp av jorden, og midlene kan anvendes én eTier flere ganger. The herbicides according to the invention can be used, among other things, before planting, after planting, before sowing, before the plants emerge from the soil, after the plants have emerged from the soil or while the cultivated plants or the unwanted plants are in the process of emerging from the soil, and the agents can be used one eTier several times.

Eksempel 9Example 9

I et drivhus ble leirholdig sandjord fyllt i forsøkskasser, og frø av forskjellige planter ble sådd. Umiddelbart deretter fulgte behandling med 2,3-dihydro-3,3-dimetyl-2-etoksybenzofuran-5-yl-metylaminosulfonat-natrium-salt (I), In a greenhouse, clayey sandy soil was filled in test boxes, and seeds of various plants were sown. Treatment with 2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-methylaminosulphonate sodium salt (I) followed immediately thereafter,

2,3-dihydro-3,3-dimetyl-2-etoksybenzofuran-5-yl-metyl-karbonyl-metylaminosulfonat (II) 2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-methyl-carbonyl-methylaminosulfonate (II)

2,3-dihydro-3,3-dimetyl-2-etoksybenzofuran-5-yl-N-klor-metylkarbo-nyl-metylaminosulfonat (III) 2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-N-chloro-methylcarbonyl-methylaminosulfonate (III)

2,3-dihy^io-3,3-dimetyl-2~metoksybenzofuran-5-yl-N-mety1-karbonyl-metylaminosulfonat (IV) 2,3-Dihydroxy-3,3-dimethyl-2-methoxybenzofuran-5-yl-N-methyl-carbonyl-methylaminosulfonate (IV)

2,3-dihydro-3,3-dimetyl-2-metoksybenzofuran-5-yl-N-klor-metylkar-bonyl-metylaminosulfonat (V) 2,3-dihydro-3,3-dimethyl-2-methoxybenzofuran-5-yl-N-chloro-methylcarbonyl-methylaminosulfonate (V)

2,3-dihydro-3,3-dimetyl-2-metySkarbonyloksybenzofuran-5-y1-N-metylkarbonyl-metylaminosulfonat (VI) 2,3-dihydro-3,3-dimethyl-2-methylcarbonyloxybenzofuran-5-yl1-N-methylcarbonyl-methylaminosulfonate (VI)

2,3-dihydro-3,3-dimetyl-2-etoksybenzofuran-5-yl-metoksy-karbonyl-metylaminosulfonat (VII) 2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-methoxy-carbonyl-methylaminosulfonate (VII)

2,3-dihydro-3,3-dimetyl-2-etoksybenzofuran-5-yl-N-etoksy-karbonyl-metylaminosulfonat (VIII) 2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-N-ethoxy-carbonyl-methylaminosulfonate (VIII)

2,3-dihydro-3,3-dimetyl-2-etoksybenzofuran-5-yl-N-isopropoksykar-bonyl-metylaminosulfonat (IX) 2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-N-isopropoxycarbonyl-methylaminosulfonate (IX)

2,3-dihydro-3,3-dimetyl-2-metoksykarbonyloksybenzofuran-5-yl-dimetylaminosulfonat (X) 2,3-dihydro-3,3-dimethyl-2-methoxycarbonyloxybenzofuran-5-yl-dimethylaminosulfonate (X)

2,3-dihydro-3,3-dimetyl-2-etoksykarbonyloksybenzofuran-5-yl-dimetylaminosulfonat (XI) 2,3-dihydro-3,3-dimethyl-2-ethoxycarbonyloxybenzofuran-5-yl-dimethylaminosulfonate (XI)

2,3-dihydro-3,3-dimetyl-2-metoksykarbonyloksybenzofuran-5-yl-dietylaminosulfonat (XII) 2,3-dihydro-3,3-dimethyl-2-methoxycarbonyloxybenzofuran-5-yl-diethylaminosulfonate (XII)

i sammenligning med de virksomme stoffer in comparison with the active substances

2-etoksy-2,3-dihydro-3,3»dimetyl-5-benzofuranyl-metansulfonat (XIII) 2-ethoxy-2,3-dihydro-3,3»dimethyl-5-benzofuranyl-methanesulfonate (XIII)

2,3-dihydro-3,3-dimetyl-2-isopropoksybenzofuran-5-yl-etyl-aminosulfonat (XIV). 2,3-dihydro-3,3-dimethyl-2-isopropoxybenzofuran-5-yl-ethylaminosulfonate (XIV).

Den anvendte mengde var i hvert tilfelle 2 kg pr. hektar og ble i hvert tilfelle dispergert, emulgert eller oppløst i 500 1 vann pr. hektar. The quantity used was in each case 2 kg per hectare and was in each case dispersed, emulsified or dissolved in 500 1 water per hectares.

Etter 4-5 uker ble det slått fast at de virksomme stoffer I-XII viste en bedre herbicid virkning ved samme forenlighet med kulturplantene enn de virksomme stoffer XIII og XIV. After 4-5 weeks, it was established that the active substances I-XII showed a better herbicidal effect at the same compatibility with the cultivated plants than the active substances XIII and XIV.

Forsøksresultatet vil fremgå av den følgende tabell: The test result will appear in the following table:

Eksempel 10 Example 10

I et drivhus ble forskjellige planter ved en veksthøyde på 2-15 cm behandlet med de virksomme stoffer I-XIV (som angitt i det foregående eksempel). Den anvendte mengde var i hvert tilfelle 2 kg pr. hektar og ble i hvert tilfelle dispergert, emulgert eller oppløst i 500 1 vann pr. hektar. In a greenhouse, different plants at a growth height of 2-15 cm were treated with the active substances I-XIV (as indicated in the previous example). The quantity used was in each case 2 kg per hectare and was in each case dispersed, emulsified or dissolved in 500 1 water per hectares.

Etter 2-3 uker ble det slått fast at de virksomme stoffer I-XII viste en bedre herbicid virkning ved samme forenlighet med kulturplantene enn de virksomme stoffer XIII og XIV. After 2-3 weeks, it was established that the active substances I-XII showed a better herbicidal effect at the same compatibility with the cultivated plants than the active substances XIII and XIV.

Forsøksresultatet vil fremgå av den følgende tabell: The test result will appear in the following table:

De følgende forbindelser har en tilsvarende biologisk virkning som forbindelsene i de foregående eksempler:2,3-dihydro-3,3-dimetyl-2-metoksybenzofuran-5-yl-N-metyl-sulfonyl-metylaminosulfonat The following compounds have a similar biological effect to the compounds in the previous examples: 2,3-dihydro-3,3-dimethyl-2-methoxybenzofuran-5-yl-N-methyl-sulfonyl-methylaminosulfonate

2,3-dihydro-3,3-dimetyl-2-metoksykarbonyloksybenzofuran-5-yl-dietylaminosulfonat 2,3-dihydro-3,3-dimethyl-2-methoxycarbonyloxybenzofuran-5-yl-diethylaminosulfonate

2,3-dihydro-3,3-dimetyl-2-metoksykarbonyloksybenzofuran-5-yl-dimetylaminosulfonat 2,3-dihydro-3,3-dimethyl-2-methoxycarbonyloxybenzofuran-5-yl-dimethylaminosulfonate

2,3-dihydro-3,3-dimetyl-2-etoksykarbonyloksybenzofuran-5-yl-dimetylaminosulfonat. 2,3-dihydro-3,3-dimethyl-2-ethoxycarbonyloxybenzofuran-5-yl-dimethylaminosulfonate.

Eksempel 11Example 11

I et drivhus ble forsøkskasser fyllt med leirholdig sandjord; og forskjellige frø ble sådd. Umiddelbart deretter fulgte behandlingen med de virksomme stoffer In a greenhouse, experimental boxes were filled with loamy sandy soil; and different seeds were sown. Treatment with the active substances followed immediately afterwards

2,3-dihydro-3,3-dimetyl-2-etoksybenzofuran-5-yl-N-mety1-karbonyl-metylaminosulfonat (II) 2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-N-methyl-carbonyl-methylaminosulfonate (II)

2,3-dihydro-3,3-dimetyl-2«etoksybenzofurah-5-yl-klormetyl-karbonyl-metylaminosulfonat (III) 2,3-dihydro-3,3-dimethyl-2«ethoxybenzofurah-5-yl-chloromethyl-carbonyl-methylaminosulfonate (III)

2,3-dihydro-3,3-dimetyl-2-etoksybenzofuran-5-yl-N-metoksy-karbonyl-metylaminosulfonat (Vil) 2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-N-methoxy-carbonyl-methylaminosulfonate (Vil)

2,3-dihydro-3,3-dimetyl-2-etoksybenzofuran-5-yl-N-etoksy-karbonyl-metylamiifosulfonat (VIII) 2,3-dihydro-3,3-dimethyl-2-ethoxybenzofuran-5-yl-N-ethoxy-carbonyl-methylamiphosulfonate (VIII)

i sammenligning med de virksomme stoffer in comparison with the active substances

2-etoksy-2,3-dihydro-3,3-dimety1-5-benzofuranyl-metan-sulfonat 2-ethoxy-2,3-dihydro-3,3-dimethyl-5-benzofuranyl methanesulfonate

(XIII) (XIII)

i hvert tilfelle dispergert eller emulgert i 500 1 vann pr. hektar. Den anvendte mengde var i hvert tilfelle 3 kg aktivt stoff pr. hektar. Under forsøket ble plantene holdt meget fuktige. in each case dispersed or emulsified in 500 1 water per hectares. The amount used was in each case 3 kg of active substance per hectares. During the experiment, the plants were kept very moist.

Etter 3-4 uker ble det slått fast at de. virksomme stoffer II, III, VII og VIII viste en bedre forenlighet med kulturplantene ved samme herbicide virkning enn det virksomme éboff XIII. After 3-4 weeks it was established that they. active substances II, III, VII and VIII showed a better compatibility with the cultivated plants with the same herbicidal action than the active éboff XIII.

Forsøksresultatet vil fremgå av den følgende tabell. The test result will appear in the following table.

Claims (1)

Substituerte benzofuranylestere med den generelle formel Substituted benzofuranyl esters of the general formula hvor R"*" betyr hydrogen eller en eventuelt med halogen eller alkoksy substituert alkyl-, alkenyl- eller alkynyl-rest, og R 2 betyr en alkenyl- eller alkynyl-rest, et metallatom, en alkylsulforiyl-rest eller en acylrest med den generelle formel where R"*" means hydrogen or an alkyl, alkenyl or alkynyl radical optionally substituted by halogen or alkoxy, and R 2 means an alkenyl or alkynyl radical, a metal atom, an alkylsulforiyl radical or an acyl radical with the general formula i 4 hvor R betyr en eventuelt med halogen, alkoksy eller alkyltio substituert alkyl-, alkenyl- eller alkynyl-rest, en alkylamino-eller dialkylamino-rest eller en eventuelt med halogen substituert alkoksyrest, og R 3betyr hydrogen, en eventuelt med halogen eller alkoksy substituert alkyl-, alkenyl- eller alkynylrest eller en acylrest med den generelle formel in 4 where R means an alkyl, alkenyl or alkynyl residue optionally substituted with halogen, alkoxy or alkylthio, an alkylamino or dialkylamino residue or an optionally halogen substituted alkoxy acid residue, and R 3 means hydrogen, an optionally with halogen or alkoxy substituted alkyl, alkenyl or alkynyl radical or an acyl radical of the general formula hvor R 5 betyr en eventuelt med halogen, alkoksy eller alkyltio substituert alkyl-, alkenyl- eller alkynylrest,. en alkylamino-eller dialkylamino-rest eller en eventuelt med halogen substituert alkoksyrest.where R 5 means an alkyl, alkenyl or alkynyl radical optionally substituted with halogen, alkoxy or alkylthio. an alkylamino or dialkylamino residue or an optionally halogen-substituted alkoxy acid residue.
NO750140A 1974-01-18 1975-01-17 NO750140L (en)

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FR (1) FR2258385B1 (en)
GB (1) GB1488575A (en)
HU (1) HU171224B (en)
IL (1) IL46287A (en)
IT (1) IT1050270B (en)
LU (1) LU71663A1 (en)
NL (1) NL7500326A (en)
NO (1) NO750140L (en)
PL (1) PL91954B1 (en)
SE (1) SE7500519L (en)
SU (1) SU519108A3 (en)
ZA (1) ZA75335B (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6011024A (en) 1991-08-28 2000-01-04 Imperial College Of Science Technology & Medicine Steroid sulphatase inhibitors
US6476011B1 (en) 1991-08-28 2002-11-05 Sterix Limited Methods for introducing an estrogenic compound
US6903084B2 (en) 1991-08-29 2005-06-07 Sterix Limited Steroid sulphatase inhibitors
GB2331988B (en) * 1997-12-04 2003-04-16 Imperial College Polycyclic sulphamate inhibitors or oestrone sulphatase
US7335650B2 (en) 2000-01-14 2008-02-26 Sterix Limited Composition

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JPS50101533A (en) 1975-08-12
CA1049539A (en) 1979-02-27
DK632474A (en) 1975-10-13
CS181286B2 (en) 1978-03-31
ZA75335B (en) 1976-01-28
AT339659B (en) 1977-11-10
PL91954B1 (en) 1977-03-31
BG25979A3 (en) 1979-01-12
SU519108A3 (en) 1976-06-25
FR2258385B1 (en) 1978-11-03
NL7500326A (en) 1975-07-22
DE2402370A1 (en) 1975-07-31
DD115561A5 (en) 1975-10-12
AU7660074A (en) 1976-06-24
IL46287A0 (en) 1975-03-13
ES433918A1 (en) 1976-11-16
SE7500519L (en) 1975-07-21
GB1488575A (en) 1977-10-12
FR2258385A1 (en) 1975-08-18
IL46287A (en) 1978-03-10
LU71663A1 (en) 1975-06-24
ATA33675A (en) 1977-02-15
BE823879A (en) 1975-06-27
CH595754A5 (en) 1978-02-28
IT1050270B (en) 1981-03-10
HU171224B (en) 1977-12-28
BR7500273A (en) 1975-11-04

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