NO141650B - HETEROCYCLIC ANILIDES WITH HERBICIDE EFFECT - Google Patents

HETEROCYCLIC ANILIDES WITH HERBICIDE EFFECT Download PDF

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NO141650B
NO141650B NO740449A NO740449A NO141650B NO 141650 B NO141650 B NO 141650B NO 740449 A NO740449 A NO 740449A NO 740449 A NO740449 A NO 740449A NO 141650 B NO141650 B NO 141650B
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formula
dioxolan
chloroacetyl
ylmethyl
compound
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NO740449A
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NO141650C (en
NO740449L (en
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Sidney B Richter
John Krenzer
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Velsicol Chemical Corp
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Publication of NO141650C publication Critical patent/NO141650C/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
    • C07D327/04—Five-membered rings
    • 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
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/16—Radicals substituted by halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/28—Radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D321/00—Heterocyclic compounds containing rings having two oxygen atoms as the only ring hetero atoms, not provided for by groups C07D317/00 - C07D319/00
    • C07D321/02—Seven-membered rings
    • C07D321/04—Seven-membered rings not condensed with other rings
    • C07D321/06—1,3-Dioxepines; Hydrogenated 1,3-dioxepines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D325/00—Heterocyclic compounds containing rings having oxygen as the only ring hetero atom according to more than one of groups C07D303/00 - C07D323/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/10—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms two oxygen atoms and one sulfur atom, e.g. cyclic sulfates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
    • C07D339/02—Five-membered rings
    • C07D339/06—Five-membered rings having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
    • C07D339/08—Six-membered rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Furan Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Description

Foreliggende oppfinnelse gjelder nye, heterocykliske anilider med herbicid virkning og med den generelle formel: The present invention relates to new, heterocyclic anilides with herbicidal action and with the general formula:

hvor where

Y er hydrogen eller halogen, Y is hydrogen or halogen,

R^ er hydrogen eller lavere alkyl, R 1 is hydrogen or lower alkyl,

2 2

R er lavere alkyl, R is lower alkyl,

X er halogen, X is halogen,

Q er: Q is:

hvor where

1 2 1 2

Z og Z hver er oksygen eller svovel, Z and Z are each oxygen or sulfur,

, , R^ og R^ er hver hydrogen eller lavere alkyl, og m er et tall fra 0 til 2. , , R^ and R^ are each hydrogen or lower alkyl, and m is a number from 0 to 2.

Uttrykket lavere slik det brukes her skal betegne en lineær eller forgrenet karbonkjede med opp til 4 karbonatomer.... The term lower as used herein shall denote a linear or branched carbon chain of up to 4 carbon atoms....

Forbindelsene ifølge oppfinnelsen er uventet nyttige som herbicider og er spesielt nyttige ved bekjempelse av gress-aktige ugress. The compounds of the invention are unexpectedly useful as herbicides and are particularly useful in controlling grass-like weeds.

I en foretrukket utførelsesform av oppfinnelsen er In a preferred embodiment of the invention is

Y hydrogen, X klor eller brom og minst to av R3, R4, R~* eller R^ er hydrogen. Y hydrogen, X chlorine or bromine and at least two of R3, R4, R~* or R^ are hydrogen.

Forbindelsene ifølge oppfinnelsen kan fremstilles ved The compounds according to the invention can be prepared by

å omsette en forbindelse med formelen: to react a compound with the formula:

1 2 hvor Y, R , R , n og Q er som foran beskrevet, med et a-halogenace,tylklorid med formelen: 1 2 where Y, R , R , n and Q are as described above, with an α-halogenacetyl chloride of the formula:

hvor X er som angitt ovenfor.. Denne reaksjon kan utføres ved å kombinere en forbindelse med formel II med en forbindelse med formel III i et inert organisk reaksjonsmedium, som f.eks. dioksan, i nærvær av en syreakseptor, som f.eks. et alkalimetallkarbonat eller -bikarbonat ved en temperatur fra -10 til 25°C og omrøring av den erholdte blanding i et tidsrom på 15 til 120 minutter. Derefter kan reaksjonsblandingen vaskes med vann for å fjerne uorganiske salter og løsningsmidlet kan avdestilleres slik at det ønskede produkt erholdes. Dette produkt kan anvendes som sådant eller kan renses ytterligere ved omkrystallisasjon eller ved andre vanlige midler. where X is as indicated above. This reaction can be carried out by combining a compound of formula II with a compound of formula III in an inert organic reaction medium, such as e.g. dioxane, in the presence of an acid acceptor, such as e.g. an alkali metal carbonate or bicarbonate at a temperature of -10 to 25°C and stirring the resulting mixture for a period of 15 to 120 minutes. The reaction mixture can then be washed with water to remove inorganic salts and the solvent can be distilled off so that the desired product is obtained. This product can be used as such or can be further purified by recrystallization or by other usual means.

Forbindelsene med formel II hvor Q er: The compounds of formula II where Q is:

kan fremstilles ved å omsette et substituert anilin med formelen: hvor Y, R 1 og R 2 er som foran beskrevet, med en forbindelse med formelen can be prepared by reacting a substituted aniline of the formula: where Y, R 1 and R 2 are as described above, with a compound of the formula

hvor Hal betegner halogen, som f.eks. klor eller brom og 7?~, 7?", R3, R4, R^, R^ og m er som foran beskrevet. Denne reaksjon kan utføres ved å kombinere en forbindelse med formel IV med en forbindelse med formel V i et inert organisk reaksjonsmedium som f.eks. dimetylformamid i nærvær av en syreakseptor som f.eks. et alkalimetallkarbonat eller -bikarbonat og å oppvarme den erholdte blanding under tilbakeløp i et tidsrom av fra 4 til 4 8 timer. Efter denne tid kan reaksjonsblandingen filtreres og destilleres slik at det ønskede produkt erholdes. where Hal denotes halogen, such as e.g. chlorine or bromine and 7?~, 7", R3, R4, R^, R^ and m are as described above. This reaction can be carried out by combining a compound of formula IV with a compound of formula V in an inert organic reaction medium such as dimethylformamide in the presence of an acid acceptor such as an alkali metal carbonate or bicarbonate and heating the resulting mixture under reflux for a period of from 4 to 48 hours. After this time the reaction mixture can be filtered and distilled as follows that the desired product is obtained.

Forbindelsene med formel V kan fremstilles ved å omsette et acetal med formelen: med en diol eller ditiol med formelen: The compounds of formula V can be prepared by reacting an acetal of the formula: with a diol or dithiol of the formula:

hvor R<3>, R<4>, R^,. R^, Z"<1>", 7? og m er som foran beskrevet . where R<3>, R<4>, R^,. R^, Z"<1>", 7? and m is as described above.

Denne reaksjon kan utføres ved å kombinere forbindelsen med formel VI med forbindelsen med formel VII i omtrent ekvimolare mengder og i nærvær av en sur katalysator, som f.eks. svovelsyre eller toluensulfonsyre, under vannfrie betingelser. This reaction can be carried out by combining the compound of formula VI with the compound of formula VII in approximately equimolar amounts and in the presence of an acid catalyst, such as e.g. sulfuric acid or toluenesulfonic acid, under anhydrous conditions.

Blandingen kan oppvarmes under tilbakeløp i et tidsrom av fra The mixture can be heated under reflux for a period of from

1 til 4 timer. Efter denne tid kan reaksjonsblandingen destilleres under redusert trykk for å gi det ønskede produkt. 1 to 4 hours. After this time, the reaction mixture can be distilled under reduced pressure to give the desired product.

Fytotoksiske 2-substituerte a-halogenacetanilider er beskrevet i US-patent 3.442.945, og i britisk patent 781.702 Phytotoxic 2-substituted α-haloacetanilides are described in US patent 3,442,945, and in British patent 781,702

beskrives N-substituerte halogenacetamider med herbicid virkning. N-substituted haloacetamides with herbicidal action are described.

Ugress er uvelkomne planter som vokser der de er uønsket, de har ingen økonomisk verdi, de forstyrrer produksjonen av kulturplan-ter, forstyrrer veksten av prydplanter og påvirker husdyrenes helse. De nye forbindelsene ifølge oppfinnelsen er spesielt verdifulle for ugressbekjempelse fordi de er toksiske overfor mange arter og grupper av ugress, mens de er relativt ikke-toksiske overfor mange nytte-planter. Den nøyaktige mengde av forbindelsen som behøves vil av-henge av mange faktorer, omfattende de spesielle ugressarters mot-standskraft, været, jordarten, applikasjonsmetoden, typer av nytte-planter i samme område og lignende. Således vil anvendelse av bare opp til ca. 0,007 g/m 2 til 0,014 g/m 2 av aktivt stoff være tilstrek-kelig for god bekjempelse av lette angrep av ugress som vokser under vanskelige betingelser, mens anvendelse av 0,07 g/m eller mer av aktiv forbindelse kan behøves for god bekjempelse av tette infestasjo-ner av motstandskraftige flerårige ugress som vokser under fordel-aktige betingelser. Weeds are unwelcome plants that grow where they are not wanted, they have no economic value, they interfere with the production of cultivated plants, interfere with the growth of ornamental plants and affect the health of livestock. The new compounds according to the invention are particularly valuable for weed control because they are toxic to many species and groups of weeds, while they are relatively non-toxic to many useful plants. The exact amount of compound needed will depend on many factors, including the resistance of the particular weed species, the weather, the type of soil, the method of application, types of beneficial plants in the same area and the like. Thus, the application of only up to approx. 0.007 g/m 2 to 0.014 g/m 2 of active substance may be sufficient for good control of light infestations of weeds growing under difficult conditions, while the use of 0.07 g/m or more of active compound may be needed for good control of dense infestations of resistant perennial weeds growing under favorable conditions.

Den herbicide toksisitet for de nye forbindelsene ifølge oppfinnelsen ble demonstrert ved forsøk som ble utført for før-spiringsbekjempelse av forskjellige ugress. I disse forsøk ble det sådd ugressfrø i små plastblomsterpotter fylt med tørr jord. Tjue-fire timer eller mindre etter at det var sådd ble pottene vannet inntil jorden var våt og forsøksforbindelsene i form av vandige emulsjoner av acetonløsninger inneholdende emulgeringsmidler ble påsprøytet i de angitte konsentrasjoner på jordoverflaten . The herbicidal toxicity of the new compounds according to the invention was demonstrated in experiments carried out for pre-emergence control of various weeds. In these experiments, weed seeds were sown in small plastic flower pots filled with dry soil. Twenty-four hours or less after sowing, the pots were watered until the soil was wet and the test compounds in the form of aqueous emulsions of acetone solutions containing emulsifiers were sprayed in the specified concentrations on the soil surface.

Etter påsprøyting ble jordbeholderne plassert i drivhus og tilført varme etter behov og ble vannet daglig eller oftere. Plantene ble holdt under disse betingelser i fra 25 til 35 dager, ved hvilket tidspunkt plantenes tilstand og graden av skade på plantene ble vurdert etter en skala på fra 0 til 10, som følgerr 0 = ingen skade, 1,2 = svak skade, 3,4 = moderat skade, 5,6 = moderat sterk skade, 7,8,9 = alvorlig skade og 10 = død. Effektiviteten for disse forbindelsene vises av de følgende data, hvor Tabell I illustrerer virkningen av tre forbindelser ifølge oppfinnelsen, og Tabell II illustrerer virkningen av de to forbindelser ifølge oppfinnelsen som er de mest aktive og derfor de mest foretrukne, sammenlignet med fire kjente forbindelser. After spraying, the soil containers were placed in greenhouses and heated as needed and watered daily or more often. The plants were kept under these conditions for from 25 to 35 days, at which time the condition of the plants and the degree of damage to the plants were assessed on a scale from 0 to 10, as follows 0 = no damage, 1.2 = slight damage, 3 ,4 = moderate damage, 5,6 = moderate severe damage, 7,8,9 = severe damage and 10 = death. The effectiveness of these compounds is shown by the following data, where Table I illustrates the effect of three compounds according to the invention, and Table II illustrates the effect of the two compounds according to the invention which are the most active and therefore the most preferred, compared to four known compounds.

Fremstillingen av forbindelsene ifølge foreliggende oppfinnelse er mer utførlig illustrert i de følgende eksempler. The production of the compounds according to the present invention is illustrated in more detail in the following examples.

Eksempel I Example I

Fremstilling av N- ot- kloracetyl- N-( 1, 3- dioksolan- 2- ylmetyl)- 2, 6-dimetylanilin. Preparation of N-o-chloroacetyl-N-(1,3-dioxolan-2-ylmethyl)-2,6-dimethylaniline.

N-(l,3-dioksolan-2-ylmetyl)-2,6-dimetylanilin (7,8 g), natriumbikarbonat (7,0 g), dioksan (20 ml) og vann (4 ml) innføres N-(1,3-dioxolan-2-ylmethyl)-2,6-dimethylaniline (7.8 g), sodium bicarbonate (7.0 g), dioxane (20 ml) and water (4 ml) are introduced

i en glassreaksjonskolbe utstyrt med mekanisk omrører og termometer. Blandingen avkjøles til en temperatur av ca. 0°C og kloracetylklorid (5,0 g) tilsettes i løpet av ca. 15 minutter med omrøring. Etter at tilsetningen er avsluttet fortsettes omrøringen i ca. 1 time. Deretter tilsettes eter (100 ml) til blandingen og den resulterende løsning vaskes med vann. Den vaskede løsning tørkes så over vannfritt magnesiumsulfat og løsningsmidlet avdrives og etterlater en fast rest. Resten omkrystalliseres fra en eter-pentanblanding og gir det ønskede produkt N-c£-kloracetyl-N-(1,3-dioksolan-2-ylmetyl)-2,6-dimetylanilin med smeltepunkt på 58-60°C. in a glass reaction flask equipped with a mechanical stirrer and thermometer. The mixture is cooled to a temperature of approx. 0°C and chloroacetyl chloride (5.0 g) is added during approx. 15 minutes with stirring. After the addition has finished, the stirring is continued for approx. 1 hour. Ether (100 ml) is then added to the mixture and the resulting solution is washed with water. The washed solution is then dried over anhydrous magnesium sulfate and the solvent is evaporated leaving a solid residue. The residue is recrystallized from an ether-pentane mixture and gives the desired product N-c£-chloroacetyl-N-(1,3-dioxolan-2-ylmethyl)-2,6-dimethylaniline with a melting point of 58-60°C.

Eksempel 2 Example 2

Fremstilling av N- gl- kloracetyl- N-( 1, 3- dioksolan- 2- ylmetyj)- 2, 6-dietylanilin. Preparation of N-gl-chloroacetyl-N-(1,3-dioxolan-2-ylmethyl)-2,6-diethylaniline.

N-(1,3-dioksolan-2-ylmetyl)-2,6-dietylanilin (7,7 g), natriumbikarbonat (6,0 g), dioksan (20 ml) og vann (4 ml) innføres N-(1,3-dioxolan-2-ylmethyl)-2,6-diethylaniline (7.7 g), sodium bicarbonate (6.0 g), dioxane (20 ml) and water (4 ml) are introduced

i en glassreaksjonskolbe utstyrt med mekanisk omrører og termometer. Denne blanding avkjøles til en temperatur på ca. 0°C og kloracetylklorid (4,0 g) tilsettes i løpet av ca. 15 minutter under omrøring. Etter at tilsetningen er avsluttet fortsettes omrøringen i ca. en time. Deretter tilsettes eter (100 ml) til blandingen og den resulterende løsning vaskes med vann. Den vaskede løsning tørkes så over vannfritt magnesiumsulfat og løsningsmidlet avdrives og etterlater en fast rest. Resten omkrystalliseres fra en eter-pentan-blanding for å gi det ønskede produkt N-oC-kloracetyl-N-(1,3-dioksolan-2-ylmetyl)-2,6-dietylanilin med et smeltepunkt på 86-87°C. in a glass reaction flask equipped with a mechanical stirrer and thermometer. This mixture is cooled to a temperature of approx. 0°C and chloroacetyl chloride (4.0 g) is added over approx. 15 minutes while stirring. After the addition has finished, the stirring is continued for approx. one hour. Ether (100 ml) is then added to the mixture and the resulting solution is washed with water. The washed solution is then dried over anhydrous magnesium sulfate and the solvent is evaporated leaving a solid residue. The residue is recrystallized from an ether-pentane mixture to give the desired product N-oC-chloroacetyl-N-(1,3-dioxolan-2-ylmethyl)-2,6-diethylaniline with a melting point of 86-87°C.

Eksempel 3 Example 3

Fremstilling av N-( 1, 3- dioksolan- 2- ylmetyl)- 2- metyl- 5- kloranilin. Preparation of N-(1,3-dioxolan-2-ylmethyl)-2-methyl-5-chloroaniline.

2-metyl-5-kloranilin (75 g), 2-klormetyl-l,3-dioksolan 2-methyl-5-chloroaniline (75 g), 2-chloromethyl-1,3-dioxolane

(25 g), kaliumkarbonat (22 g) qg dimetylformamid (50 ml) innføres i et glassreaksjonskar utstyrt med en mekanisk omrører, et termometer og en tilbakeløpskjøler. Reaksjonsblandingen oppvarmes under omrøring i ca. 26 timer. Deretter filtreres reaksjonsblandingen og destilleres slik at det erholdes det ønskede produkt N-(1,3-dioksolan-2-metyl-5-kloranilin med et kokepunkt på 116-118°c ved 0,1 mm trykk Hg. (25 g), potassium carbonate (22 g) qg dimethylformamide (50 ml) are introduced into a glass reaction vessel equipped with a mechanical stirrer, a thermometer and a reflux condenser. The reaction mixture is heated with stirring for approx. 26 hours. The reaction mixture is then filtered and distilled so that the desired product N-(1,3-dioxolane-2-methyl-5-chloroaniline) is obtained with a boiling point of 116-118°c at 0.1 mm Hg pressure.

Fremstilling av N- oC- kloracetyl- N-( 1, 3- dioksolan- 2- ylmetyl)- 2- metyl-5- kloranilin. Preparation of N-oC-chloroacetyl-N-(1,3-dioxolan-2-ylmethyl)-2-methyl-5-chloroaniline.

N-(1,3-dioksolan-2-ylmetyl)-2-metyl-5-kloranilin (8 g), natriumbikarbonat (7 g), dioksan (50 ml) og vann (5 ml) innføres i et reaksjonskar av glass utstyrt med en mekanisk omrører og et termometer. Denne blanding avkjøles til en temperatur på ca. 0°C og kloracetylklorid (4,3 g) tilsettes i løpet av ca. 15 minutter under omrøring. Etter at tilsetningen er avsluttet fortsettes omrøringen i ca. en time. Deretter tilsettes eter (100 ml) til blandingen og den resulterende løsning vaskes med vann. Den vaskede løsning tørkes så over vannfritt magnesiumsulfat og løsningsmidlet avdrives hvor-ved det blir tilbake en fast rest. Resten omkrystalliseres fra heksan og det erholdes det ønskede produkt N-oC -kloracetyl-N-(1, 3-dioksolan-2-ylmetyl)-2-metyl-5-kloranilin med smeltepunkt på 88-89°c. N-(1,3-dioxolan-2-ylmethyl)-2-methyl-5-chloroaniline (8 g), sodium bicarbonate (7 g), dioxane (50 ml) and water (5 ml) are introduced into a glass reaction vessel equipped with with a mechanical stirrer and a thermometer. This mixture is cooled to a temperature of approx. 0°C and chloroacetyl chloride (4.3 g) is added over approx. 15 minutes while stirring. After the addition has finished, the stirring is continued for approx. one hour. Ether (100 ml) is then added to the mixture and the resulting solution is washed with water. The washed solution is then dried over anhydrous magnesium sulphate and the solvent is driven off leaving a solid residue. The residue is recrystallized from hexane and the desired product N-oC-chloroacetyl-N-(1,3-dioxolan-2-ylmethyl)-2-methyl-5-chloroaniline with a melting point of 88-89°c is obtained.

Eksempel 4 Example 4

2-kloracetaldehyd-dimetylacetal + etandiol-1,2 + metylanilin + kloracetylklorid = N-o£-kloracetyl-N-(1,3-dioksolan-2-ylmetyl)-2-metylanilin, sm.p. 5 8-60°C.. 2-chloroacetaldehyde-dimethyl acetal + ethanediol-1,2 + methylaniline + chloroacetyl chloride = N-o£-chloroacetyl-N-(1,3-dioxolan-2-ylmethyl)-2-methylaniline, m.p. 5 8-60°C..

Eksempel 5 Example 5

2-kloracetaldehyd-dimetylacetal + etandiol-1,2 + 2-etylanilin + kloracetylklorid = N-o6-kloracetyl-N-(1,3-dioksolan-2-ylmetyl)-2-etylanilin, sm.p. 54-56°C. 2-chloroacetaldehyde-dimethyl acetal + ethanediol-1,2 + 2-ethylaniline + chloroacetyl chloride = N-o6-chloroacetyl-N-(1,3-dioxolan-2-ylmethyl)-2-ethylaniline, m.p. 54-56°C.

For praktisk bruk som herbicider innblandes forbindelsene ifølge oppfinnelsen i herbicide preparater som omfatter en inert bærer og en herbicid toksisk mengde av en slik forbindelse. Slike herbicidpreparater, som også kan kalles sammensetninger, gjør det mulig å påføre den aktive forbindelsen på stedet for ugréssinfeksjonen i en ønsket mengde. Disse preparater kan være faste som f.eks. støv, granuler eller fuktbare pulvere, eller de kan være flytende som f.eks. løsninger, aerosoler eller emulgerbare konsentrater. For practical use as herbicides, the compounds according to the invention are mixed into herbicidal preparations comprising an inert carrier and a herbicidally toxic amount of such a compound. Such herbicide preparations, which can also be called compositions, make it possible to apply the active compound to the site of the weed infection in a desired quantity. These preparations can be solid such as e.g. dust, granules or wettable powders, or they can be liquid such as e.g. solutions, aerosols or emulsifiable concentrates.

Claims (3)

1. Heterocykliske anilider for anvendelse som herbicider, karakterisert ved at de har formelen: hvor Y er hydrogen eller halogen, R^" er hydrogen eller lavere alkyl,1. Heterocyclic anilides for use as herbicides, characterized in that they have the formula: where Y is hydrogen or halogen, R^" is hydrogen or lower alkyl, 2 R er lavere alkyl, X er halogen, Q er:. hvor2 R is lower alkyl, X is halogen, Q is: where 1 2 Z og Z hver for seg er oksygen eller svovel,1 2 Z and Z are each oxygen or sulfur, 3 4 5 6 R , R , R og R er hver hydrogen eller lavere alkyl og m er et tall fra 0 til 2.3 4 5 6 R, R, R and R are each hydrogen or lower alkyl and m is a number from 0 to 2. 2. Forbindelse ifølge krav 1, karakterisert ved at den er N-a-kloracetyl-N-(1,3-dioksolan-2-ylmetyl)-2,6-dimetylanilin.2. Compound according to claim 1, characterized in that it is N-α-chloroacetyl-N-(1,3-dioxolan-2-ylmethyl)-2,6-dimethylaniline. 3. Forbindelse ifølge krav 1, karakterisert ved at forbindelsen er N-a-kloracetyl-N-(1,3-dioksolan-2-yl-metyl)-2,6-dietylanilin.3. Compound according to claim 1, characterized in that the compound is N-α-chloroacetyl-N-(1,3-dioxolan-2-yl-methyl)-2,6-diethylaniline.
NO740449A 1973-02-12 1974-02-11 HETEROCYCLIC ANILIDES WITH HERBICIDE EFFECT NO141650C (en)

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DE2648008C3 (en) * 1976-10-23 1980-09-04 Basf Ag, 6700 Ludwigshafen Acetanilide
IL53938A0 (en) * 1977-02-02 1978-04-30 Bayer Ag Novel n-substituted halogenoacetanilides, their preparation and their use as herbicides
DE2744396A1 (en) * 1977-10-03 1979-04-12 Basf Ag ACETANILIDE
DE2802211A1 (en) * 1978-01-19 1979-07-26 Basf Ag N-SUBSTITUTED 2,6-DIALKYLANILINES AND METHOD FOR PREPARING N-SUBSTITUTED 2,6-DIALKYLANILINES
US4243408A (en) * 1978-05-11 1981-01-06 Chevron Research Company Herbicidal N-triazolylmethyl-substituted alpha-haloacetanilide
DE2835157A1 (en) * 1978-08-10 1980-02-21 Bayer Ag METHOD FOR PRODUCING N-SUBSTITUTED ALPHA -HALOGENACETANILIDES
DE2842280A1 (en) * 1978-09-28 1980-04-10 Bayer Ag N- (1,3-AZOLYL) -ALKYL-HALOGENACETANILIDE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS HERBICIDES
DE3025694A1 (en) * 1979-07-09 1981-01-29 Ciba Geigy Ag PHENYLAMINOAL CHANNELS AND PHENYLAMINOACETALS, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE IN MICROBICIDES

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