NO781931L - DIURETANE WITH HERBICID EFFECT - Google Patents

DIURETANE WITH HERBICID EFFECT

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Publication number
NO781931L
NO781931L NO781931A NO781931A NO781931L NO 781931 L NO781931 L NO 781931L NO 781931 A NO781931 A NO 781931A NO 781931 A NO781931 A NO 781931A NO 781931 L NO781931 L NO 781931L
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parts
weight
alkyl
halogen
substituted
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NO781931A
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Norwegian (no)
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Ulrich Schirmer
Bruno Wuerzer
Wolfgang Rohr
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Basf Ag
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    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L25/00—Assemblies consisting of a plurality of individual semiconductor or other solid state devices ; Multistep manufacturing processes thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/20—N-Aryl derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/22—O-Aryl or S-Aryl esters thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/32—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C271/38—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/58—Ring systems containing bridged rings containing three rings
    • C07C2603/60—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members
    • C07C2603/62—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing three- or four-membered rings
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/0001—Technical content checked by a classifier
    • H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Environmental Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Power Engineering (AREA)
  • Computer Hardware Design (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

" Diuretan med herbicid virkning""Diuretic with herbicidal effect"

Description

Foreliggende oppfinnelse angår nye verdifulle svovelholdige diuretaner med utmerket herbicid virkning, som kan anvendes for bekjempelse av uønsket plantevekst. The present invention relates to new valuable sulphur-containing diurethanes with excellent herbicidal action, which can be used to combat unwanted plant growth.

Det er kjent å anvende metyl-N- ( 3-(N1 - (3 ' -metylf enyl-karbamoyloksy ))fenyl) -karbamat, etyl-N- (3- (N1 -fenylkarbamoyloksy) fenyl) - karbamat, metyl-N-(3-(N'-metyl-N<1->fenylkarbamoyloksy)-fenyl)- It is known to use methyl N- (3-(N1 - (3 '-methylphenyl-carbamoyloxy))phenyl)-carbamate, ethyl-N-(3-(N1-phenylcarbamoyloxy)phenyl)-carbamate, methyl-N -(3-(N'-methyl-N<1->phenylcarbamoyloxy)-phenyl)-

karbamat (DT-AS 15 67 151) eller 3-isopropyl-2,1,3-benzotiadiazinon-(4)-2,2-dioksyd (DT-AS 15 42 836) som herbicider. carbamate (DT-AS 15 67 151) or 3-isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide (DT-AS 15 42 836) as herbicides.

Det er nu funnet at de nye diuretaner med denIt has now been found that the new diurethanes with it

generelle formelgeneral formula

hvor where

Z betyr resten Z means the rest

og Y betyr resten and Y means the rest

idet Z alltid er forskjellig fra Y, since Z is always different from Y,

ol c2 etc. c2

og R og R and R and R

er uavhengig av is independent of

hverandre hydrogen, alkyl (f.eks. metyl, etyl, isopropyl), alkoksyalkyl (f.eks. metoksymetyl, 2-metoksyetyl), alkoksykarbonylalkyl (f.eks. metoksykarbonylmetyl), halogenalkyl (f.eks. klor-metyl) eller eventuelt med alkyl eller halogen substituert benzyl, R 3 og R 4er uavhengig av hverandre usubstituert alkyl eller med each other hydrogen, alkyl (e.g. methyl, ethyl, isopropyl), alkoxyalkyl (e.g. methoxymethyl, 2-methoxyethyl), alkoxycarbonylalkyl (e.g. methoxycarbonylmethyl), haloalkyl (e.g. chloromethyl) or optionally with alkyl or halogen substituted benzyl, R 3 and R 4 are independently unsubstituted alkyl or med

halogen eller alkoksy eller alkoksykarbonyl eller substituert eller usubstituert aryl substituert alkyl (f.eks. metyl, etyl, 2-kloretyl, 2-metoksyetyl, metoksykarbonylmetyl, benzyl, isopropyl, n-propyl, 4-klorbenzyl, n-butyl, sek.butyl, tert.butyl, isobutyl, 2.4- diklorbenzyl, 2-etylheksy1, n-decyl, 2-fenyletyl), eller eventuelt med halogen substituert alkenyl (f.eks. allyl, 2-klor-propen(l)yl(3), buten (1) yl ( 3) , 2,3-diklorallyl, 3,3-diklor-2-metyl-allyl), eller eventuelt med halogen eller alkoksy substituert alkynyl (f.eks. propargyl, butyn(1)yl(3), 1-klorbutyn (2)yl (4)) halogen or alkoxy or alkoxycarbonyl or substituted or unsubstituted aryl substituted alkyl (e.g. methyl, ethyl, 2-chloroethyl, 2-methoxyethyl, methoxycarbonylmethyl, benzyl, isopropyl, n-propyl, 4-chlorobenzyl, n-butyl, sec.butyl , tert.butyl, isobutyl, 2,4-dichlorobenzyl, 2-ethylhexyl, n-decyl, 2-phenylethyl), or optionally with halogen-substituted alkenyl (e.g. allyl, 2-chloro-propen(l)yl(3), buten (1) yl ( 3 ), 2,3-dichloroallyl, 3,3-dichloro-2-methyl-allyl), or optionally with halogen or alkoxy substituted alkynyl (e.g. propargyl, butyn(1)yl (3 ), 1-chlorobutyn (2)yl (4))

eller eventuelt med alkyl substituert cykloalkyl (f.eks. cyklo-pentyl, cykloheksyl, 3-metylcykloheksyl, 2,6-dimetylcykloheksyl, cykloheptyl, 4-tert.butylcykloheksyl, cyklooktyl, cyklododecyl, 3.5- dimetylcykloheksyl) eller bicykloalkyl (f.eks. norbornyl) or optionally with alkyl substituted cycloalkyl (e.g. cyclopentyl, cyclohexyl, 3-methylcyclohexyl, 2,6-dimethylcyclohexyl, cycloheptyl, 4-tert.butylcyclohexyl, cyclooctyl, cyclododecyl, 3.5-dimethylcyclohexyl) or bicycloalkyl (e.g. norbornyl)

eller tricykloalkyl (f.eks. tricyklo(4,3,1, ' 0 ' )-decyl),or tricycloalkyl (e.g. tricyclo(4,3,1, ' 0 ' )-decyl),

en fenylrest med påkondensert ringsystem (f.eks. naftyl eller indyl), fenyl eller en enkelt- eller flersubstituert fenylrest med substituentene alkyl, halogenalky1, alkoksyalkyl, cykloalkyl, halogen, alkoksy, halogenalkoksy, alkoksykarbonyl-alkoksy, nitro, amino, aryl, aryloksy, tiocyanato, cyano, a phenyl radical with a condensed ring system (e.g. naphthyl or indyl), phenyl or a singly or polysubstituted phenyl radical with the substituents alkyl, haloalkyl, alkoxyalkyl, cycloalkyl, halogen, alkoxy, haloalkoxy, alkoxycarbonyl-alkoxy, nitro, amino, aryl, aryloxy , thiocyanato, cyano,

(f.eks. fenyl, 4-fluorfenyl, 2-metoksyfenyl, 3-metylfenyl, 2-fluorfenyl, 3-mety1-5-isopropylfenyl, 3-etylfenyl, 3- klorfenyl, 2,4,6-trimetylfenyl, 3-fluorfenyl, 3-klor-4-fluorfenyl, 3,4-dimetylfenyl, 3-trifluormetylfenyl, 4-metylfenyl, 3,4-difluorfenyl, 3-klor-4-metylfenyl, 3-bromfenyl, 4-jodfenyl, 4- klorfenyl, 2-klorfenyl, 3-N,N-dimetylaminofenyl, 2-klor-4-fluorfenyl, 3-isopropylfenyl, 4-etylfenyl, 3-metoksykarbonylaminofenyl, 4-etoksyfenyl, 2-metylfenyl, 3-metoksyfenyl, 4-cyanofenyl, 2,6-dimetylfenyl, 2,4-diklorfenyl, 3-metyl-4-klorfenyl, 2-trifluormetylfenyl, 2,4-dibromfeny1, 4-trifluormetylfenyl, 4-metoksyfenyl, 3-(l<1->etoksykarbonyletoksy)-fenyl), 2,3,6-trimetylfenyl, 3-tert.-butylfenyl, 3-trif luormetoksyf enyl, 3-cx , a, (3 , 3~tetraf luoretoksy-fenyl, 3,5-diklorfeny1, 2-metyl-6-etylfenyl, 2,3-dimetylfenyl, 2-metyl-4-klorfenyl, 2,4,5-triklorfenyl, 2,3,6-triklorfenyl, 5 6 . p-klorfenoksy-fenyl), hvor R og R uavhengig av hverandre betyr hydrogen eller en eventuelt enkelt- eller flersubstituert arylrest, (e.g. phenyl, 4-fluorophenyl, 2-methoxyphenyl, 3-methylphenyl, 2-fluorophenyl, 3-methyl-5-isopropylphenyl, 3-ethylphenyl, 3-chlorophenyl, 2,4,6-trimethylphenyl, 3-fluorophenyl , 3-chloro-4-fluorophenyl, 3,4-dimethylphenyl, 3-trifluoromethylphenyl, 4-methylphenyl, 3,4-difluorophenyl, 3-chloro-4-methylphenyl, 3-bromophenyl, 4-iodophenyl, 4-chlorophenyl, 2 -chlorophenyl, 3-N,N-dimethylaminophenyl, 2-chloro-4-fluorophenyl, 3-isopropylphenyl, 4-ethylphenyl, 3-methoxycarbonylaminophenyl, 4-ethoxyphenyl, 2-methylphenyl, 3-methoxyphenyl, 4-cyanophenyl, 2,6 -dimethylphenyl, 2,4-dichlorophenyl, 3-methyl-4-chlorophenyl, 2-trifluoromethylphenyl, 2,4-dibromophenyl1, 4-trifluoromethylphenyl, 4-methoxyphenyl, 3-(l<1->ethoxycarbonylethoxy)-phenyl), 2 . 2,3-dimethylphenyl, 2-methyl-4-chlorophenyl, 2,4,5-trichlorophenyl, 2,3,6-trichlorophenyl, 5 6 . p-chlorophenoxy-phenyl), where R and R independently of each other mean hydrogen or a possibly single or polysubstituted aryl radical,

eller en av de to substituentene har de for R angitte betydninger, X betyr hydrogen, alkyl (f.eks. metyl), halogenalkyl (f.eks. tri-fluormetyl), alkoksy (f.eks. metoksy), halogen (f.eks. fluor, klor, brom eller jod), nitro eller amino, n betyr tallene 1 til 4, og A, B, D og E betyr uavhengig av hverandre oksygen eller svovel, idet ikke alle restene A, B, D og E samtidig kan bety oksygen, or one of the two substituents has the meanings given for R, X means hydrogen, alkyl (e.g. methyl), haloalkyl (e.g. trifluoromethyl), alkoxy (e.g. methoxy), halogen (e.g. e.g. fluorine, chlorine, bromine or iodine), nitro or amino, n means the numbers 1 to 4, and A, B, D and E independently mean oxygen or sulphur, not all the residues A, B, D and E at the same time can mean oxygen,

og minst én av disse rester betyr alltid svovel,and at least one of these residues always means sulphur,

har en god herbicid virkning mot tallrike viktige uønskede planter og samtidig en god forlikelighet overfor mange kulturplanter. Disse virkninger er bedre enn virkningene for de kjente aktive stoffer. has a good herbicidal effect against numerous important unwanted plants and at the same time a good compatibility with many cultivated plants. These effects are better than the effects of the known active substances.

De nye forbindelser kan f.eks. fremstilles ved de følgende fremgangsmåter, hvor restene A, B, D, E, R, R 1 , R , R , R 4, X og n har de ovenfor angitte betydninger. Når det i det følgende henvises til uretaner og klormaursyreestere, skal disse to samlebegreper også forstås å omfatte tiono-, tio- og ditio-uretaner foruten klormaursyretionoestere, klormaursyretioestere og klormaursyreditioestere. The new connections can e.g. are prepared by the following methods, where the residues A, B, D, E, R, R 1 , R , R , R 4 , X and n have the meanings given above. When in the following reference is made to urethanes and chloroformic acid esters, these two collective terms shall also be understood to include thiono-, thio- and dithio-urethanes in addition to chloroformic acid thioesters, chloroformic acid thioesters and chloroformic acid redithioesters.

Fra reaksjonsskjemaet fremgår klart den gjensidige avhengighet mellom utgangsstoffene. Videre fremgår tydelig at alt efter naturen av substituentene A, B, D, E, R , R , R 3 , R The reaction scheme clearly shows the mutual dependence between the starting substances. Furthermore, it is clear that depending on the nature of the substituents A, B, D, E, R , R , R 3 , R

og X og tilgjengeligheten av de aktuelle reaksjonskomponenter,and X and the availability of the relevant reaction components,

kan den ene eller annen vei være fordelaktig. Omsetningen fra F til H foretrekkes. can be beneficial one way or the other. The turnover from F to H is preferred.

Ved å gå ut fra kjente meta-nitraniliner (A) kan man fremstille meta-nitrofenyliso(tio)cyanater (1) (W. Siefken, Starting from known meta-nitranilines (A), meta-nitrophenyliso(thio)cyanates (1) can be prepared (W. Siefken,

J. Liebigs Annalen der Chemie, 562, 75 ff, (1949)), som på sin side reagerer glatt med komponentene R 3-BH til nitro(tio)uretanene ( Q) J. Liebigs Annalen der Chemie, 562, 75 ff, (1949)), which in turn react smoothly with the components R 3-BH to the nitro(thio)urethanes ( Q)

(S. Petersen i Methoden der Organ. Chemie, bind VIII, side 131, Georg, Thieme-Verlag, Stuttgart, 4. utgave (1952)), som riktignok også kan fremstilles direkte fra meta-nitranilinene (A) med klormaursyreestere (R 3 B-CA-C1) (DT-OS 16 4 3 763) eller me_d karbondisulfid resp. karbonoksysulfid, base og alkyleringsmiddel (S. Petersen in Methoden der Organ. Chemie, volume VIII, page 131, Georg, Thieme-Verlag, Stuttgart, 4th edition (1952)), which can of course also be prepared directly from the meta-nitranilines (A) with chloroformate esters (R 3 B-CA-C1) (DT-OS 16 4 3 763) or with carbon disulfide or carbonoxysulfide, base and alkylating agent

(Methoden der Organischen Chemie, bind IX, side 831 ff, Georg Thieme-Verlag, Stuttgart, 4. utgave, 1955). Påfølgende reduksjon fører til aminoforbindelsene (F, R 2=H) (S. Schroter i Methoden (Methoden der Organischen Chemie, volume IX, page 831 ff, Georg Thieme-Verlag, Stuttgart, 4th edition, 1955). Subsequent reduction leads to the amino compounds (F, R 2=H) (S. Schroter in Methoden

der Organischen Chemie, bind XI/1, side 360 ff., Georg Thieme-Verlag, Stuttgart, 4. utgave, 1957), som enten direkte eller der Organischen Chemie, volume XI/1, page 360 ff., Georg Thieme-Verlag, Stuttgart, 4th edition, 1957), as either directly or

efter påfølgende omvandling til produktet som er monosubstituertafter subsequent conversion to the product which is monosubstituted

på amino-nitrogenet (F, R 2=H) (Methoden der Organischen Chemie,on the amino nitrogen (F, R 2=H) (Methoden der Organischen Chemie,

bind XI/1, side 24 ff., Georg, Thieme-Verlag, Stuttgart, 4. utgave 1957), omsettes med klormaursyreestere (R<4>D-CE-C1) (DT-OS 16 43 763) eller med karbondisulfid resp. karbonoksysulfid, base og alkyleringsmiddel; (Methoden der Organischen Chemie, bind IX, side 831 ff, Georg-Thieme-Verlag, Stuttgart, 4. utgave, 1955) til de ønskede diuretaner (g) . Aminouretanene F_ kan imidlertid også fremstilles ved omsetning av meta-fenylendiaminer (p) med klormaursyreestere. volume XI/1, page 24 ff., Georg, Thieme-Verlag, Stuttgart, 4th edition 1957), react with chloroformic acid esters (R<4>D-CE-C1) (DT-OS 16 43 763) or with carbon disulphide resp. . carbonoxysulfide, base and alkylating agent; (Methoden der Organischen Chemie, volume IX, page 831 ff, Georg-Thieme-Verlag, Stuttgart, 4th edition, 1955) to the desired diuretans (g) . However, the aminourethanes F_ can also be prepared by reacting meta-phenylenediamines (p) with chloroformate esters.

En ytterligere syntesemulighet består i omsetning av aryl-1,3-diiso(tio)cyanater (E) med bare ett mol av komponenten R 3-BH, A further synthesis option consists in reacting aryl-1,3-diiso(thio)cyanates (E) with only one mole of the component R 3-BH,

som fører til iso (tio)cyanatouretanene ( Q) (J.A. Parker, J.J. Thomas og CL. Zeise, J. Org. Chem. 22y 594 til 596 (1957)), som også leading to the iso (thio)cyanatoureethanes ( Q) (J.A. Parker, J.J. Thomas and CL. Zeise, J. Org. Chem. 22y 594 to 596 (1957)), which also

kan fremstilles ved (tio) fosgenering av.aminouretanene (F_)can be prepared by (thio)phosgenation of the aminourethanes (F_)

(DT-OS 19 14 270, side 5, eksempel 8). Påfølgende omsetning med komponentene R 4DH fører til de ønskede sluttprodukter. Prinsipielt skal det bemerkes at rekkefølgen av -CABR<3>resp. -CEDR<4->grupperingene er vilkårlig. (DT-OS 19 14 270, page 5, example 8). Subsequent turnover with the components R 4DH leads to the desired end products. In principle, it should be noted that the order of -CABR<3>resp. -CEDR<4->groupings are arbitrary.

I det følgende skal de foretrukne synteseveier beskrives nærmere: In the following, the preferred synthesis routes will be described in more detail:

a) Omsetningen av 3-nitrofenyliso(tio)cyanatené (B)a) The turnover of 3-nitrophenyliso(thio)cyanatene (B)

skjer med eller uten en katalysator som er egnet for iso(tio)cyanat-reaksjoner, f.eks. tertiære aminer (trietylamin, 1,4-diaza-bicyklo[2.2.2]oktan), nitrogenholdige heterocykliske forbindelser (pyridin, 1,2-dimetylimidazol) eller organiske tinnforbindelser (dibutyltinndiacetat, dimetyltinndiklorid), eventuelt i et opp-løsningsmiddel som er inert under reaksjonsbetingelsene, f.eks. hydrokarboner (ligroin, bensin, toluen, pentan, cykloheksan), halogenhydrokarboner (metylenklorid, kloroform, dikloretan, klorbenzen, o-, m- eller p-diklorbenzen), nitrohydrokarboher (nitrobenzen, nitrometan), nitriler (acetonitril, butyronitril, benzonitril), etere (dietyleter, tetrahydrofuran, dioksan), occurs with or without a catalyst suitable for iso(thio)cyanate reactions, e.g. tertiary amines (triethylamine, 1,4-diaza-bicyclo[2.2.2]octane), nitrogen-containing heterocyclic compounds (pyridine, 1,2-dimethylimidazole) or organic tin compounds (dibutyltin diacetate, dimethyltin dichloride), optionally in a solvent that is inert under the reaction conditions, e.g. hydrocarbons (naphtha, petrol, toluene, pentane, cyclohexane), halogenated hydrocarbons (methylene chloride, chloroform, dichloroethane, chlorobenzene, o-, m- or p-dichlorobenzene), nitrohydrocarbons (nitrobenzene, nitromethane), nitriles (acetonitrile, butyronitrile, benzonitrile), ethers (diethyl ether, tetrahydrofuran, dioxane),

estere (eddiksyreetylester, propionsyremetylester), ketoner (aceton, metyletylketon) eller amider (dimetylformamid, formamid) esters (acetic acid ethyl ester, propionic acid methyl ester), ketones (acetone, methyl ethyl ketone) or amides (dimethylformamide, formamide)

(DT-OS 15 68 138) ved temperaturer i området fra 0 til 150°C, fortrinnsvis i området fra 40 til l00°C. (DT-OS 15 68 138) at temperatures in the range from 0 to 150°C, preferably in the range from 40 to 100°C.

b) 3-nitraniliner (A) omsettes med klormaursyreestere i et egnet oppløsningsmiddel, f.eks. vann, alkoholer (metanol, etanol, isopropanol) eller som angitt under a), under tilsetning av et vanlig syrebindende middel, f.eks. alkalihydroksyder, -karbonater, -hydrogenkarbonater, jordalkalioksyder, -hydroksyder, b) 3-nitranilines (A) are reacted with chloroformate esters in a suitable solvent, e.g. water, alcohols (methanol, ethanol, isopropanol) or as stated under a), with the addition of a common acid-binding agent, e.g. alkali hydroxides, carbonates, hydrogen carbonates, alkaline earth oxides, hydroxides,

-karbonater, -hydrogenkarbonater, tertiære organiske baser-carbonates, -hydrogen carbonates, tertiary organic bases

(f.eks. trietylamin, pyridin, N,N-dimetylanilin, N,N-dimetyl-cykloheksylamin, kinolin, tributylamin) eller utgangsproduktet 3-nitranilin, ved temperaturer fra -20 til 150°C, fortrinnsvis i området fra 20 til 80°C. (e.g. triethylamine, pyridine, N,N-dimethylaniline, N,N-dimethylcyclohexylamine, quinoline, tributylamine) or the starting product 3-nitraniline, at temperatures from -20 to 150°C, preferably in the range from 20 to 80 °C.

c) Reduksjonen av nitrouretanene (C) kan foretas i henhold til en kjent fremgangsmåte, f.eks. ved katalytisk c) The reduction of the nitrourethanes (C) can be carried out according to a known method, e.g. by catalytic

hydrogenering, ved hjelp av en metall-syre-kombinasjon, f.eks. en kombinasjon jern-syre, ved hjelp av en metall-alkohol-kombinasjon, f.eks. sinkstøv-vandig alkohol, jern-vandig alkohol. hydrogenation, using a metal-acid combination, e.g. an iron-acid combination, using a metal-alcohol combination, e.g. zinc dust-aqueous alcohol, iron-aqueous alcohol.

d) For omsetningen av m-fenylendiaminer (D) gjelder tilsvarende betingelser som for b), idet det imidlertid kan være d) For the turnover of m-phenylenediamines (D) similar conditions apply as for b), although it may, however, be

fordelaktig å arbeide med et overskudd av m-fenylendiaminer.advantageous to work with an excess of m-phenylenediamines.

e) Omsetningen av, aminouretanene F med klormaursyre-es trene foretas analogt med b), idet man også kan anvende direkte den oppløsning som erholdes f.eks. ved katalytisk hydrogenering av nitrouretanene C uten ytterligere rensning. e) The reaction of the aminourethanes F with chloroformate esters is carried out analogously to b), as one can also use directly the solution obtained, e.g. by catalytic hydrogenation of the nitrourethanes C without further purification.

De følgende eksempler skal illustrere fremstillingenThe following examples shall illustrate the preparation

av de nye diuretaner og deres forprodukter:of the new diurethanes and their precursors:

I. NitrouretanerI. Nitrourethanes

Eksempel AExample A

En oppløsning av. 64,3 vektdeler 4-klorfenol og 3 vektdeler trietylamin i 4 30 vektdeler toluen (absolutt) ble under omrøring ved 20 til 25°C satt til en blanding av 85 vektdeler 3-nitrofenylisocyanat og 43 vektdeler toluen (absolutt). A resolution of. 64.3 parts by weight of 4-chlorophenol and 3 parts by weight of triethylamine in 4 30 parts by weight of toluene (absolute) were added with stirring at 20 to 25°C to a mixture of 85 parts by weight of 3-nitrophenyl isocyanate and 43 parts by weight of toluene (absolute).

For å fullføre omsetningen rørte man videre i 1 time ved romtemperatur. Efter avkjøling til 0°C ble reaksjonsproduktet ' avsuget: Sm.p. 137-138°C. To complete the reaction, stirring was continued for 1 hour at room temperature. After cooling to 0°C, the reaction product was filtered off: mp. 137-138°C.

Forbindelsen har følgende strukturformel:The compound has the following structural formula:

Eksempel B Example B

Til 138 vektdeler m-nitranilin i 500 vektdeler tetrahydrofuran (THF) settes 87 vektdeler natriumhydrogenkarbonat. Under omrøring tilsetter man dråpevis ved romtemperatur 120 vektdeler klormaursyretiometylester, omrører videre i 16 timer ved romtemperatur, filtrerer, avdestillerer oppløsningsmidlet på en rotasjonsfordamper og rører den erholdte olje inn i toluen. De utskilte krystaller avsuges og tørres: Sm.p. 137-138°C. 87 parts by weight of sodium bicarbonate are added to 138 parts by weight of m-nitraniline in 500 parts by weight of tetrahydrofuran (THF). While stirring, 120 parts by weight of chloroformic acid thiomethyl ester are added dropwise at room temperature, stirred for 16 hours at room temperature, filtered, the solvent is distilled off on a rotary evaporator and the resulting oil is stirred into toluene. The separated crystals are suctioned off and dried: mp. 137-138°C.

Forbindelsen har følgende strukturformel:The compound has the following structural formula:

Eksempel C Example C

Til 26 vektdeler 3-nitro-N-metylanilin i 320 vektdeler eddiksyreetylester settes 17,4 vektdeler natriumhydrogenkarbonat. Under omrøring tilsetter man langsomt 3 3 vektdeler klormaursyre-m-tolylester, omrører i 20 timer ved romtemperatur, filtrerer, avdriver oppløsningsmidlet i vakuum og omkrystalliserer det gjenværende residuum fra toluen/cykloheksan. 17.4 parts by weight of sodium bicarbonate are added to 26 parts by weight of 3-nitro-N-methylaniline in 320 parts by weight of acetic acid ethyl ester. While stirring, 3 parts by weight of chloroformic acid-m-tolyl ester are slowly added, stirred for 20 hours at room temperature, filtered, the solvent is evaporated in vacuo and the remaining residue is recrystallized from toluene/cyclohexane.

Sm.p..114-116°C. M.p..114-116°C.

Forbindelsen har følgende strukturformel: The compound has the following structural formula:

Ved tilsvarende fremgangsmåter kan følgende nitrouretaner (C) fremstilles: By similar methods, the following nitrourethanes (C) can be produced:

II. Aminouretaner II. Aminourethanes

Eksempel DExample D

En oppløsning av 135 vektdeler N-(3-nitrofenyl)karbamin-syre-4-klorfenylester i 900 vektdeler tetrahydrofuran (absolutt) ble tilsatt 3 deler hydrogeneringskatalysator (palladium-på-benkull, 10%) og hydrogenert ved romtemperatur og 0,02 bar t^-trykk til konstant trykk. For opparbeidelse ble oppløsningen som var befridd for katalysator og tørret med MgSO^, befridd for så mye oppløsningsmiddel at det krystallinske reaksjonsprodukt lot seg godt avsuge: 186-187°C. A solution of 135 parts by weight of N-(3-nitrophenyl)carbamic acid-4-chlorophenyl ester in 900 parts by weight of tetrahydrofuran (absolute) was added with 3 parts of hydrogenation catalyst (palladium-on-bone charcoal, 10%) and hydrogenated at room temperature and 0.02 bar t^ pressure to constant pressure. For work-up, the solution, which had been freed of catalyst and dried with MgSO 4 , was freed of so much solvent that the crystalline reaction product could be well filtered off: 186-187°C.

Struktur:Structure:

Eksempel E Example E

Til en oppløsning av 108 vektdeler m-fenylendiaminTo a solution of 108 parts by weight of m-phenylenediamine

i 1000 vektdeler vann ble under intens omrøring satt dråpevis meget langsomt 25,2 vektdeler klormaursyrefenylester. Efter av-sluttet omsetning ble reaksjonsblandingen underkastet avsugning, det faste stoff ble vasket flere ganger med fortynnet saltsyre, de samlede, sure oppløsninger ble nøytralisert med ammoniakk og avsugd. Det således erholdte, tørrede produkt smelter ved 178 til 180°C under spaltning. in 1000 parts by weight of water, 25.2 parts by weight of chloroformic acid phenyl ester were added drop by drop very slowly under intense stirring. After completion of the reaction, the reaction mixture was subjected to suction, the solid was washed several times with dilute hydrochloric acid, the combined acidic solutions were neutralized with ammonia and suctioned off. The dried product thus obtained melts at 178 to 180°C during decomposition.

Struktur:Structure:

Eksempel F Example F

Til 51 vektdeler 2,4-diaminonitrobenzen og 43 vektdeler natriumhydrogenkarbonat i 600 vektdeler tetrahydrofuran setter man langsomt dråpevis under intens omrøring 52,1 vektdeler klormaursyrefenylester. Efter 14 timers omrøring foretas filtrering og efter-vasking med tetrahydrofuran. Man befrir oppløsningen for så mye oppløsningsmiddel at det krystallinske råprodukt lett kan avsuges, og efter vasking med dietyleter og tørring smelter produktet ved 223-225°C. I henhold til NMR-spektrum og elementæranalyse har det følgende struktur: To 51 parts by weight of 2,4-diaminonitrobenzene and 43 parts by weight of sodium hydrogen carbonate in 600 parts by weight of tetrahydrofuran, 52.1 parts by weight of chloroformic acid phenyl ester are slowly added dropwise under intense stirring. After 14 hours of stirring, filtration and post-washing with tetrahydrofuran is carried out. The solution is freed from so much solvent that the crystalline crude product can be easily suctioned off, and after washing with diethyl ether and drying, the product melts at 223-225°C. According to the NMR spectrum and elemental analysis, it has the following structure:

Eksempel G Example G

Til en til 80°C oppvarmet blanding av 33 vektdeler jern-pulver, 75 vektdeler alkohol, 60 vektdeler vann og 3 vektdeler konsentrert saltsyre setter man under intens omrøring 40 vektdeler 3-(S-metyltiokarbamoyl)-nitrobenzen i slike porsjoner at temperaturen uten ytterligere oppvarmning holdes ved 80°C. Derefter koker man i ytterligere 1 time under tilbakéløpskjøling, avsuger reaksjonsblandingen i varm tilstand, oppslutter residuet og filtratet med ca. 1000 vektdeler metylenklorid, tørrer over natriumsulfat, inndamper og omkrystalliserer fra toluen, sm.p. 101-103°C. Struktur: To a mixture heated to 80°C of 33 parts by weight of iron powder, 75 parts by weight of alcohol, 60 parts by weight of water and 3 parts by weight of concentrated hydrochloric acid, 40 parts by weight of 3-(S-methylthiocarbamoyl)-nitrobenzene are added under intense stirring in such portions that the temperature without further heating is maintained at 80°C. It is then boiled for a further 1 hour under reflux, the reaction mixture is filtered off while still hot, the residue and the filtrate are washed with approx. 1000 parts by weight of methylene chloride, dry over sodium sulphate, evaporate and recrystallize from toluene, m.p. 101-103°C. Structure:

I henhold til tilsvarende fremgangsmåter kan følgende aminouretaner (g) fremstilles: According to corresponding methods, the following aminourethanes (g) can be prepared:

III. Diuretaner III. Diurethans

Eksempel 1Example 1

En oppløsning av 22,8 vektdeler N-(3-aminofenyl)karbaminsyre-fenylester i 200 vektdeler tetrahydrofuran (absolutt) ble tilsatt 11 vektdeler natriumbikarbonat og derefter ved 20 til 25°C under avkjøling tilsatt 13,3 vektdeler klormaursyretiometylester. To a solution of 22.8 parts by weight of N-(3-aminophenyl)carbamic acid phenyl ester in 200 parts by weight of tetrahydrofuran (absolute) was added 11 parts by weight of sodium bicarbonate and then at 20 to 25°C under cooling added 13.3 parts by weight of chloroformate thiomethyl ester.

For fullføring av omsetningen ble omrøring foretatt i 1 time ved romtemperatur. Derefter ble reaksjonsblandingen filtrert, og filtratet inndampes i vakuum. Det oljeaktige residuum ble bragt til krystallisasjon ved tilsetning av toluen. To complete the reaction, stirring was carried out for 1 hour at room temperature. The reaction mixture was then filtered, and the filtrate evaporated in vacuo. The oily residue was brought to crystallisation by the addition of toluene.

Sm.p. 155-157°C (nr. 1). Forbindelsen har følgende struktur: Sm.p. 155-157°C (No. 1). The connection has the following structure:

Eksempel 2 Example 2

En blanding av 20 vektdeler N-(3-isotiocyanatofenyl)-O-metylkarbamat (som kan fremstilles fra N-(3-aminofenyl)-O-metyl-karbamat og tiofosgeh, sm.p. 99-lOO°C), 20 vektdeler metanol, 3 vektdeler trietylamin og 150 vektdeler toluen oppvarmes i 6 timer til kokning. Efter inndampning omkrystalliserer man fra toluen: Sm.p. 147-149°C (nr. 2). A mixture of 20 parts by weight of N-(3-isothiocyanatophenyl)-O-methylcarbamate (which can be prepared from N-(3-aminophenyl)-O-methyl-carbamate and thiophosgeh, m.p. 99-100°C), 20 parts by weight methanol, 3 parts by weight of triethylamine and 150 parts by weight of toluene are heated for 6 hours to boiling. After evaporation, it is recrystallized from toluene: mp. 147-149°C (No. 2).

Forbindelsen har følgende strukturformel: The compound has the following structural formula:

Eksempel 3 Example 3

Til en oppløsning av 16,6 vektdeler N-(3-aminofenyl)-0-metyluretan og 10,1 vektdeler trietylamin i 300 vektdeler dietyleter setter man dråpevis ved romtemperatur 10 vektdeler karbondisulfid. Efter 20 timers omrøring foretas avsugning, residuet suspenderes i 120 vektdeler vann og tilsettes 9,1 volumdeler dietylsulfat under omrøring. Efter 20 timers omrøring foretas avsugning, vasking med vann og tørring i luft: Smp. 122-124°C (nr. 3) . To a solution of 16.6 parts by weight of N-(3-aminophenyl)-0-methylurethane and 10.1 parts by weight of triethylamine in 300 parts by weight of diethyl ether, 10 parts by weight of carbon disulfide are added dropwise at room temperature. After stirring for 20 hours, suction is carried out, the residue is suspended in 120 parts by weight of water and 9.1 parts by volume of diethyl sulphate are added while stirring. After stirring for 20 hours, suction is carried out, washing with water and drying in air: mp. 122-124°C (No. 3) .

Forbindelsen har følgende strukturformel: The compound has the following structural formula:

For de følgende forsøk ble kjente herbicide stoffer anvendt som sammenligning. Metyl-N-(3-(N<1->(3<1->metylfenyl-karbamoyloksy ))-f enyl ) -karbamat og etyl-N-(3-(N'-fenylkarbamoyloksy)-fenyl)-karbamat (DT-AS 15 67 151) utmerker seg ved sin, riktignok forskjellige, virkning mot bredbladete uønskede planter ved en betydelig grad av forlikelighet overfor sukkerroer. Her forekommer som kjent imidlertid forskjeller, da metyl-N-(3-(N1 - (3 '-metylfenylkarbamoyloksy)fenyl)-karbamat oppviser en gunstigere selektivitet i denne kultur enn den annen ovennevnte forbindelse av denne type. Et helt annet anvendelsesområde har 3-isopropyl-2,1,3-benzotiadiazinon-(4)-2,2-dioksyd (DT-AS 15 42 836). For the following experiments, known herbicidal substances were used as a comparison. Methyl N-(3-(N<1->(3<1->methylphenyl-carbamoyloxy)-phenyl)-carbamate and ethyl-N-(3-(N'-phenylcarbamoyloxy)-phenyl)-carbamate ( DT-AS 15 67 151) is distinguished by its, albeit different, action against broad-leaved unwanted plants with a significant degree of compatibility with sugar beet. Here, however, there are, as is known, differences, as methyl-N-(3-(N1 - (3 '-methylphenylcarbamoyloxy)phenyl)-carbamate exhibits a more favorable selectivity in this culture than the other above-mentioned compound of this type. A completely different area of application has 3 -isopropyl-2,1,3-benzothiadiazinone-(4)-2,2-dioxide (DT-AS 15 42 836).

Med denne forbindelse bekjempes forskjellige bredbladete ugressWith this compound, various broad-leaved weeds are combated

i soyabønner, jordnøtter, korn, mais og noen grønnsakarter.in soybeans, peanuts, grains, corn and some vegetables.

Her forekommer imidlertid også manglende virkninger. Metyl-N-(3-(N'— metyl-N'-fenyl-karbamoyloksy)-fenyl)-karbamat viser ved en for sin klasse god herbicid virkning knapt noen kulturplanteselektivitet, hvorfor forbindelsen f.eks. for soya bare er anbefalt for underblads-sprøytning (Arndt, F. og G. Boroschewsky: New Selective Herbicides VIII International Plant Protection Congress, Reports. and Information, Section III Chemical Control, Part I, Moskva 19 75, Here, however, there are also missing effects. Methyl-N-(3-(N'— methyl-N'-phenyl-carbamoyloxy)-phenyl)-carbamate, with a good herbicidal effect for its class, shows hardly any crop plant selectivity, which is why the compound e.g. for soy is only recommended for underleaf spraying (Arndt, F. and G. Boroschewsky: New Selective Herbicides VIII International Plant Protection Congress, Reports. and Information, Section III Chemical Control, Part I, Moscow 19 75,

s. 42-49). Herunder skal de unge skudd og bladene hos kultur-plantene ikke treffes av sprøytevæsken, men bare uønskede planter som befinner seg under disse. pp. 42-49). Below this, the young shoots and leaves of the cultivated plants must not be hit by the spray liquid, but only unwanted plants that are located below them.

Eksempler på herbicid virkning av nye svovelholdige diuretaner Examples of herbicidal action of new sulphur-containing diurethans

Tallrike forsøksresultater beviser de gode herbicide egenskaper hos de nye forbindelser. De klassifiseres med hensyn til sin herbicide aktivitet og sin selektivitet overfor kulturplanter på grunnlag av den biologiske virkning ved følgende forsøk: Numerous experimental results prove the good herbicidal properties of the new compounds. They are classified with regard to their herbicidal activity and their selectivity towards cultivated plants on the basis of the biological effect in the following tests:

VeksthusforsøkGreenhouse experiment

Plast-blomsterpotter med innhold 300 cm 3ble fylt med leiraktig sand, og forsøksplantene ble anbragt i disse adskilt efter art. Det er her overveiende tale om såing av frø eller også om planting når det gjelder arter som formerer seg vegetativt. Plastic flowerpots with a content of 300 cm 3 were filled with clayey sand, and the experimental plants were placed in these separated by species. This is mainly about sowing seeds or also about planting in the case of species that reproduce vegetatively.

De aktive stoffer ble suspendert eller emulgert i vann som for-delingsmiddel og ble sprøytet ved hjelp av finfordelende dyser i økende mengder på prøveplantenes blad eller bare på den nakne jordoverflate. For bladbehandlingen anvendte man plantene alt efter The active substances were suspended or emulsified in water as a distribution agent and were sprayed with the aid of fine-distributing nozzles in increasing amounts on the leaves of the test plants or only on the bare soil surface. For the leaf treatment, the plants were used as appropriate

vekstform i forsøksbeholderne først når de hadde nådd en høydegrowth form in the experimental containers only when they had reached a height

på 3-10 cm, og behandlet dem derefter. Prøveplantenes temperatur-krav imøtekom man forsåvidt som at man stilte dem opp i kaldere eller varmere deler av veksthusanleggene. Forsøksperioden varte of 3-10 cm, and then treated them. The temperature requirements of the trial plants were naturally met by placing them in colder or warmer parts of the greenhouse facilities. The trial period lasted

2- 4 uker. I løpet av denne tid ble plantene pleiet, og deres reaksjon på de enkelte behandlinger ble bedømt. De anvendte mengder av prøveforbindelsene er angitt som kg/ha aktivt stoff. For bedømmelsen tjente en graderingsskala fra 0 til 100. Her betyr 0: ingen beskadigelse, 100: plantene døde. 2-4 weeks. During this time, the plants were cared for, and their reaction to the individual treatments was assessed. The amounts of the test compounds used are indicated as kg/ha of active substance. For the assessment, a grading scale from 0 to 100 was used. Here 0 means: no damage, 100: the plants died.

ResultaterResults

Tallmaterialet i de følgende tabeller illustrerer virkningen av de aktive stoffer ved bladbehandling efter spiring av kulturplanter og uønskede planter (tabell 2 til 12). Det skal her legges merke til at de nye forbindelser med hensyn til herbicid aktivitet The figures in the following tables illustrate the effect of the active substances in foliar treatment after germination of cultivated plants and unwanted plants (tables 2 to 12). It should be noted here that the new compounds with regard to herbicidal activity

og virkningsspektrum nærmer seg diuretanene som er anvendt som sammenligningsmidler. Tyngdepunktene i selektiviteten for kulturplanter er imidlertid andre. Det lar seg f.eks. godt illustrere på soyabønner og korn. På disse kulturer får man forlikelighetsgrader som er jevnbyrdige med hva man får med det for samme formål kjente 3- isopropyl-2,1,3-benzotiadiazinon(4)-2,2-dioksyd (tabell 5, 6). Dessuten eksisterer en rekke kulturplanter som har en utmerket toleranse overfor de nye forbindelser, mens de undersøkte sammenligningsmidler er uegnet (tabell 2, 4, 5). and spectrum of action approaches the diurethanes used as comparators. However, the focal points in the selectivity for cultivated plants are different. It is possible, e.g. well illustrated on soybeans and cereals. On these cultures, degrees of compatibility are obtained which are equivalent to what is obtained with the 3-isopropyl-2,1,3-benzothiadiazinone(4)-2,2-dioxide known for the same purpose (tables 5, 6). In addition, a number of cultivated plants exist which have an excellent tolerance towards the new compounds, while the investigated comparative agents are unsuitable (tables 2, 4, 5).

Som anvendelsesmetode kan man benytte seg av innføringIntroduction can be used as an application method

i jorden eller behandling av jordoverflaten, men behandling av planter som er kommet opp, foretrekkes. Også spesialanvendelser så som underbladsprøyting (post directed, lay-by) kommer på tale. Herunder rettes sprøytestrålen slik at bladene på ømfindtlige kulturplanter som er kommet opp, såvidt mulig ikke treffes, mens midlet derimot treffer den underliggende jordflate og de uønskede planter som vokser der. in the soil or treatment of the soil surface, but treatment of plants that have emerged is preferred. Special applications such as underleaf spraying (post directed, lay-by) are also considered. Below this, the spray jet is directed so that the leaves of sensitive cultivated plants that have come up are not hit as far as possible, while the agent, on the other hand, hits the underlying soil surface and the unwanted plants that grow there.

I betraktning av alle de mulige anvendelsesmetoder kanConsidering all the possible application methods can

de nye forbindelser og blandinger inneholdene disse, foruten påthe new compounds and mixtures containing these, besides on

de i tabellen angitte nytteplanter, også anvendes på en rekke andre kulturer til bekjempelse av uønsket plantevekst. Anvendelses-konsentrasjonene kan være fra 0,1 til 15 kg/ha og mer, alt efter det objekt som bekjempes. the useful plants indicated in the table are also used on a number of other cultures to combat unwanted plant growth. The application concentrations can be from 0.1 to 15 kg/ha and more, depending on the object being combated.

Særskilt skal de følgende nytteplanter nevnes: The following beneficial plants must be mentioned separately:

For ytterligere utvidelse av virkningsspekteret for de nye enkeltforbindelser, for å oppnå en synergistisk virkning eller for å forbedre den gjenværende virkning på jorden, kan de nye forbindelser blandes med hverandre, eller tallrike andre herbicider eller vekstregulerende forbindelser kan anvendes som blandings-og kombinasjonspartnere. Alt efter anvendelsesområde- og bekjempningsplan kan de nedenfor angitte forbindelser eller kjemisk lignende derivater anvendes som partnere: To further expand the spectrum of action of the new individual compounds, to achieve a synergistic effect or to improve the remaining effect on the soil, the new compounds can be mixed with each other, or numerous other herbicides or growth-regulating compounds can be used as mixing and combination partners. Depending on the area of application and control plan, the following compounds or chemically similar derivatives can be used as partners:

Dessuten er det mulig å anvende de nye forbindelser alene eller i kombinasjon med andre.herbicider og dessuten også med andre plantebeskyttelsesmidler. Det er her aktuelt med midler for bekjempelse av skadelige organismer eller fytopatogene sopper eller bakterier. Av interesse er dessuten blandbarheten med mineral-saltoppløsninger, som kan anvendes for avhjelpning av ernærings- og sporelementmangel. Moreover, it is possible to use the new compounds alone or in combination with other herbicides and also with other plant protection agents. It is relevant here to use agents for combating harmful organisms or phytopathogenic fungi or bacteria. Also of interest is the mixability with mineral salt solutions, which can be used to remedy nutritional and trace element deficiencies.

For aktivering av den herbicide virkning kan fukte- og heftemidler såvel som ikke-fytotoksiske oljer anvendes. To activate the herbicidal effect, wetting agents and adhesives as well as non-phytotoxic oils can be used.

Anvendelsen skjer f.eks. i form av direkte sprøytbare oppløsninger, pulvere, suspensjoner eller dispersjoner, emulsjoner, oljedispersjoner, pastaer, støvmidler, strømidler, granulater, ved utsprøytning, tåkedannelse, forstøvning, strøing eller helling. Anvendelsesformene retter seg helt efter formålet, men de bør ihvertfall medføre så fin fordeling av de nye forbindelser som mulig. The application takes place e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusting agents, streamers, granules, by spraying, fogging, atomizing, scattering or pouring. The forms of application depend entirely on the purpose, but they should in any case lead to as fine a distribution of the new compounds as possible.

For fremstilling av direkte sprøytbare oppløsninger, emulsjoner, pastaer og oljedispersjoner kan f.eks. anvendes mineraloljefraks joner med midlere til høyt kokepunkt, så som kerosen eller dieselolje,. dessuten kulltjæreoljer osv., oljer av vegetabilsk eller animalsk opprinnelse, alifatiske, cykliske og aromatiske hydrokarboner, f.eks. benzen, toluen, xylen, paraffin, tetrahydro-naftalen, alkylerte naftalener eller derivater derav, f.eks. For the production of directly sprayable solutions, emulsions, pastes and oil dispersions, e.g. mineral oil fractions with medium to high boiling points, such as kerosene or diesel oil, are used. also coal tar oils, etc., oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. benzene, toluene, xylene, paraffin, tetrahydro-naphthalene, alkylated naphthalenes or derivatives thereof, e.g.

metanol, etanol, propanol, butanol, kloroform, karbontetraklorid, cykloheksanol, cykloheksanon, klorbenzen, isoforon osv., sterkt polare oppløsningsmidler, f.eks. dimetylformamid, dimetylsulfoksyd, N-metylpyrrolidon, vann osv. methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride, cyclohexanol, cyclohexanone, chlorobenzene, isophorone, etc., strongly polar solvents, e.g. dimethylformamide, dimethylsulfoxide, N-methylpyrrolidone, water, etc.

Vandige anvendelsesformer kan. tilberedes fra emulsjons-konsentrater, pastaer eller fuktbare pulvere (sprøytepulvere), Aqueous application forms can. prepared from emulsion concentrates, pastes or wettable powders (spray powders),

og oljedispersjoner ved tilsetning av vann. For fremstilling av emulsjoner, pastaer eller oljedispersjoner kan forbindelsene som sådanne eller oppløst i en olje eller et oppløsningsmiddel homogeniseres ved hjelp av fukte-, hefte-, dispergerings- eller emulgeringsmidler i vann. Man kan imidlertid også fremstille konsentrater.bestående av aktivt stoff, fukte-, hefte-, dispergerings-eller emulgeringsmidler og eventuelt oppløsningsmidler eller olje, som er egnet til fortynning med vann. and oil dispersions by adding water. For the production of emulsions, pastes or oil dispersions, the compounds as such or dissolved in an oil or a solvent can be homogenised with the aid of wetting, binding, dispersing or emulsifying agents in water. However, it is also possible to prepare concentrates consisting of active substance, wetting, binding, dispersing or emulsifying agents and possibly solvents or oil, which are suitable for dilution with water.

Som overflateaktive stoffer kan nevnes:The following can be mentioned as surfactants:

Alkali-, jordalkali-, ammoniumsalter av ligninsulfonsyre, naftalensulfonsyre, fenolsulfonsyrer, alkylarylsulfonater, alkyl-sulfater, alkylsulfonater, alkali- og jordalkalisalter av dibutyl-naftalensulfonsyre, lauryletersulfat, fettalkoholsulfater, fettsure alkali- og jordalkalisalter, salter av sulfaterte heksadekanoler, heptadekanoler, oktadekanoler, salter av sulfatert fettalkohol-glykoleter, kondensasjonsprodukter av sulfonert naftalen og naftalenderivater med formaldehyd, kondensasjonsprodukter av naftalen resp. naftalensulfonsyrer med fenol og formaldehyd, polyoksyetylen-oktylfenoleter, etoksylerte isooktylfenol-, oktylfenol-, nonylfenol-, alkylfenol-polyglykoleter, tributylfenyl-glykoleteralkoholer, isotridecylalkohol, fettalkoholetylenoksyd-kondensater, etoksylert ricinusolje, polyoksyetylenalkyleter, etoksylert polyoksypropylen, laurylalkoholpolyglykoleteracetal, sorbitolestere, lignin, sulfittavlut og metylcellulose. Alkali, alkaline earth, ammonium salts of ligninsulfonic acid, naphthalenesulfonic acid, phenolsulfonic acids, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, alkali and alkaline earth salts of dibutyl naphthalenesulfonic acid, lauryl ether sulfate, fatty alcohol sulfates, fatty acid alkali and alkaline earth salts, salts of sulfated hexadecanols, heptadecanols, octadecanols, salts of sulphated fatty alcohol-glycol ether, condensation products of sulphonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene resp. naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl glycol ether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignin, sulphite liquor and methyl cellulose.

Pulvere, strø- og støvmidler kan fremstilles ved blanding eller ved å male de aktive stoffer sammen med et fast bæremiddel. Powders, dusting and dusting agents can be produced by mixing or by grinding the active substances together with a solid carrier.

Granulater, f.eks. omhylnings-, impregnerings- og homogengranulater, kan fremstilles ved å binde de aktive stoffer til faste bærestoffer. Faste bærestoffer er f.eks. mineraljord så som silikagel, kiselsyre, kiselgeler, silikater, talkum, kaolin, attapulgittleire, kalksten, kalk, kritt, bolus, løss, leire, dolomitt, diatoméjord, kalsium- og magnesiumsulfat, magnesiumoksyd, malte kunstoffer, gjødningsmidler så som ammonium-sulfat, ammoniumfosfat, ammoniumnitrat, urinstoff og plante-produkter så som kornmel, bark-, tre- og nøtteskallmel, cellulose-pulver og andre faste bæremidler. Granules, e.g. coating, impregnation and homogeneous granules, can be produced by binding the active substances to solid carriers. Solid carriers are e.g. mineral soil such as silica gel, silicic acid, silica gels, silicates, talc, kaolin, attapulgite clay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, ground synthetic substances, fertilizers such as ammonium sulphate, ammonium phosphate, ammonium nitrate, urea and plant products such as grain flour, bark, tree and nut shell flour, cellulose powder and other solid carriers.

Preparatene inneholder mellom 0,1 og 95 vekt% aktivt 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.

Eksempel 4Example 4

Man blander 90 vektdeler av forbindelse 2 med 10 vektdeler N-metyl-a-pyrrolidon og får en oppløsning som er egnet til anvendelse i form av de minste dråper. 90 parts by weight of compound 2 are mixed with 10 parts by weight of N-methyl-α-pyrrolidone and a solution is obtained which is suitable for use in the form of the smallest droplets.

Eksempel 5Example 5

20 vektdeler av forbindelse 8 oppløses i en blanding som består av 80 vektdeler xylen, 10 vektdeler av tilleiringsproduktet av 8 til 10 mol etylenoksyd til 1 mol oljesyre-N-monoetanolamid, 5 vektdeler kalsiumsalt av dodecylbenzensulfonsyre og 5 vektdeler 20 parts by weight of compound 8 are dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of the addition product of 8 to 10 moles of ethylene oxide to 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight

av tilleiringsproduktet av 40 mol etylenoksyd til 1 mol ricinusolje. Ved å helle og finfordele oppløsningen i 100 000 vektdeler vann får man en vandig dispersjon som inneholder 0,02 vekt% av det aktive stoff. of the addition product of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring and finely distributing the solution in 100,000 parts by weight of water, an aqueous dispersion containing 0.02% by weight of the active substance is obtained.

Eksempel 6Example 6

20 vektdeler av forbindelse 13 oppløses i en blanding som består av 40 vektdeler cykloheksanon, 30 vektdeler isobutanol, 20 parts by weight of compound 13 are dissolved in a mixture consisting of 40 parts by weight cyclohexanone, 30 parts by weight isobutanol,

20 vektdeler av tilleiringsproduktet av 7 mol etylenoksyd til20 parts by weight of the addition product of 7 moles of ethylene oxide to

1 mol isooktylfenol, og 10 vektdeler av tilleiringsproduktet av1 mole of isooctylphenol, and 10 parts by weight of the addition product of

40 mol etylenoksyd til 1 mol ricinusolje. Ved å helle og finfordele oppløsningen i 100 000 vektdeler vann får man en vandig dispersjon som inneholder 0,02 vekt% av det aktive stoff. 40 mol ethylene oxide to 1 mol castor oil. By pouring and finely distributing the solution in 100,000 parts by weight of water, an aqueous dispersion containing 0.02% by weight of the active substance is obtained.

Eksempel 7Example 7

20 vektdeler av forbindelse 2 3 oppløses i en blanding20 parts by weight of compound 2 3 are dissolved in a mixture

som består av 25 vektdeler cykloheksanol, 65 vektdeler av en mineraloljefraksjon med kokepunkt 210 til 280°C, og 10 vektdeler which consists of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction with a boiling point of 210 to 280°C, and 10 parts by weight

av tilleiringsproduktet av 40 mol etylenoksyd til 1 mol ricinusolje. Ved å helle og finfordele oppløsningen i 100 000 vektdeler vann of the addition product of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring and finely distributing the solution in 100,000 parts by weight of water

får man en vandige dispersjon som inneholder 0,02 vekt% av det aktive stoff. an aqueous dispersion containing 0.02% by weight of the active substance is obtained.

Eksempel 8Example 8

20 vektdeler av forbindelse 7 blandes godt med 3 vektdeler av natriumsaltet av diisobutylnaftalen-a-sulfonsyre, 17 vektdeler av natriumsaltet av en ligninsulfonsyre fra en sulfittavlut, og 60 vektdeler pulverformig kiselsyregel, og det hele males i en hammermølle. Ved finfordeling av blandingen i 20 000 vektdeler vann får man en sprøytevæske som inneholder 0,1 vekt% av det aktive stoff. 20 parts by weight of compound 7 are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalene-a-sulfonic acid, 17 parts by weight of the sodium salt of a ligninsulfonic acid from a sulphite leachate, and 60 parts by weight of powdered silicic acid rule, and the whole is ground in a hammer mill. By finely distributing the mixture in 20,000 parts by weight of water, a spray liquid containing 0.1% by weight of the active substance is obtained.

Eksempel 9Example 9

3 vektdeler av forbindelse 46 blandes godt med 9 7 vektdeler findelt kaolin. Man får på denne måte et støvmiddel som inneholder 3 vekt% av det aktive stoff. 3 parts by weight of compound 46 are mixed well with 9 7 parts by weight of finely divided kaolin. In this way, a dusting agent is obtained which contains 3% by weight of the active substance.

Eksempel 10Example 10

30 vektdeler av forbindelse 2 blandes godt med en blanding av 92 vektdeler pulverformig kiselsyregel og 8 vektdeler paraffin-olje som er sprøytet på overflaten av denne kiselsyregel. Man får på denne måte et preparat av det aktive stoff med god hefteevne. 30 parts by weight of compound 2 are mixed well with a mixture of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel. In this way, a preparation of the active substance with good adhesion is obtained.

Eksempel 11Example 11

40 vektdeler av forbindelse 7 blandes godt med 10 deler natriumsalt av et fenolsulfonsyre-urinstoff-formaldehyd-kondensat, 2 deler silikagel og 48 deler vann. Man får en stabil, vandig dispersjon. Ved fortynning med 100 000 vektdeler vann får man en vandig dispersjon som inneholder 0,04 vekt% aktivt stoff. 40 parts by weight of compound 7 are mixed well with 10 parts sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts silica gel and 48 parts water. A stable, aqueous dispersion is obtained. When diluted with 100,000 parts by weight of water, an aqueous dispersion is obtained which contains 0.04% by weight of active substance.

Eksempel 12Example 12

20 deler av forbindelse 8 blandes godt med 2 deler kalsiumsalt av dodecylbenzensulfonsyre, 8 deler fettalkohol-polyglykoleter, 2 deler natriumsalt av et fenolsulfonsyre-urinstoff-formaldehyd-kondensat og 68 deler av en paraffinisk mineralolje. Man får en stabil, oljeaktig dispersjon. 20 parts of compound 8 are mixed well with 2 parts calcium salt of dodecylbenzenesulfonic acid, 8 parts fatty alcohol-polyglycol ether, 2 parts sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts of a paraffinic mineral oil. A stable, oily dispersion is obtained.

Claims (1)

Diuretan med herbicid virkning, karakterisert ved at det har formelen: Diurethane with herbicidal effect, characterized in that it has the formula: hvor Z betyr resten ■ where Z means the remainder ■ og Y betyr.resten hvor Z alltid er forskjellig fra Y, og R og R2 er uavhengig av hverandre hydrogen, alkyl, alkoksyalkyl, alkoksykarbonylalkyl, halogenalkyl, eventuelt med alkyl eller halogen substituert benzyl, 3 4 R og R er uavhengig av hverandre usubstituert alkyl eller med halogen eller alkoksy eller substituert eller usubstituert aryl substituert alkyl; eventuelt med halogen substituert alkenyl, eventuelt med halogen eller alkoksy substituert alkynyl; eventuelt med alkyl substituert cykloalkyl; bicykloalkyl; tricykloalkyl; en fenylring med påkondensert ringsystem, fenyl, enkelt- eller flersubstituert fenyl, med substituentene alkyl, halogenalkyl, alkoksyalkyl, alkoksykarbonylalkyl, alkoksykarbonylalkoksy, cykloalkyl, halogen, alkoksy, halogenalkoksy, nitro, amino, aryl, aryloksy, tiocyanato, cyano, NH-COR5, NHCOOR <5> , NHCONR5R6, COOR <5> , and Y means the residue where Z is always different from Y, and R and R2 are independently of each other hydrogen, alkyl, alkoxyalkyl, alkoxycarbonylalkyl, haloalkyl, optionally with alkyl or halogen substituted benzyl, 3 4 R and R are independently of one another unsubstituted alkyl or with halogen or alkoxy or substituted or unsubstituted aryl substituted alkyl; optionally halogen-substituted alkenyl, optionally halogen- or alkoxy-substituted alkynyl; optionally with alkyl substituted cycloalkyl; bicycloalkyl; tricycloalkyl; a phenyl ring with a fused ring system, phenyl, mono- or polysubstituted phenyl, with the substituents alkyl, haloalkyl, alkoxyalkyl, alkoxycarbonylalkyl, alkoxycarbonylalkyloxy, cycloalkyl, halogen, alkoxy, haloalkoxy, nitro, amino, aryl, aryloxy, thiocyanato, cyano, NH-COR5, NHCOOR <5> , NHCONR5R6, COOR <5> , CONR5R6, SR5, S02 R <5> , OSC^ R <5> , COR <5> , S02 NR <5> R <6> , hvor R5 og R6 uavhengig av hverandre betyr hydrogen eller en eventuelt enkelt-eller flersubstituert arylrest, eller en av de to substituentene har de for R" <*> " angitte betydninger; og X betyr hydrogen, alkyl, halogenalkyl, alkoksy, halogen, nitro eller amino, n betyr tallene 1 til 4, og A, B, D og E betyr uavhengig av hverandre oksygen eller svovel, idet ikke alle restene A, B, D og E samtidig betyr oksygen, og minst én av disse rester betyr alltid svovel,CONR5R6, SR5, S02 R <5> , OSC^ R <5> , COR <5> , S02 NR <5> R <6> , where R5 and R6 independently of each other means hydrogen or an optionally singly or polysubstituted aryl residue, or one of the two substituents has the meanings indicated for R" <*> "; and X means hydrogen, alkyl, haloalkyl, alkoxy, halogen, nitro or amino, n means the numbers 1 to 4, and A, B, D and E independently mean oxygen or sulphur, not all the residues A, B, D and E at the same time means oxygen, and at least one of these residues always means sulphur,
NO781931A 1977-06-03 1978-06-02 DIURETANE WITH HERBICID EFFECT NO781931L (en)

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JPS5951205A (en) * 1982-06-23 1984-03-24 Toyo Soda Mfg Co Ltd Herbicide containing carbamate derivative
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