DK146337B - Benzothiadiazinforbindelser med herbicid virkning - Google Patents
Benzothiadiazinforbindelser med herbicid virkning Download PDFInfo
- Publication number
- DK146337B DK146337B DK549077AA DK549077A DK146337B DK 146337 B DK146337 B DK 146337B DK 549077A A DK549077A A DK 549077AA DK 549077 A DK549077 A DK 549077A DK 146337 B DK146337 B DK 146337B
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- DK
- Denmark
- Prior art keywords
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- weight
- compounds
- methyl
- benzothiadiazine
- Prior art date
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- 230000002363 herbicidal effect Effects 0.000 title description 6
- 150000007658 benzothiadiazines Chemical class 0.000 title description 4
- 239000004009 herbicide Substances 0.000 title description 4
- 230000000694 effects Effects 0.000 title description 3
- -1 sulfone ester Chemical class 0.000 description 55
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/88—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with three ring hetero atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—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 no bond to a nitrogen atom
- A01N47/06—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 no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues 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
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
- A01N57/32—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing heterocyclic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
- C07F9/6544—Six-membered rings
- C07F9/6547—Six-membered rings condensed with carbocyclic rings or carbocyclic ring systems
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Description
(is) DANMARK (Φ|
(12) FREMLÆGGELSESSKRIFT (11) 146337 B
DIREKTORATET FOR PATENT- OG VAREMÆRKEVÆSENET
(21) Patentansøgning nr.: 5490/77 (51) lnt.CI.3: C 07 D 285/16 (22) Indleveringsdag: 09 dec 1977 C 07 D 417/12 C07F 9/65 (41) Aim. tilgængelig: 12 jun 1970 A 01 N 43/88 (44) Fremlagt: 12 sep 1983 A 01 N 47/10 (86) International ansøgning nr.:- A01 N 47/06 A 01 N 57/32 (30) Prioritet: 11 dec 1976 DE2656290 (71) Ansøger: *BASF AKTIENGESELLSCHAFT; 6700 Ludwlgshafen, DE.
(72) Opfinder: Gerhard ‘Hamprecht; DE, Gerd "Stubenrauch; DE, Hans ‘Urbach; DE, Bruno 'Wuerzer; DE
(74) Fuldmægtig: Patentbureauet Hofman-Bang & Boutard (54) Benzothiadiazinforbindelser med herbicid virk· ning
Opfindelsen angår hidtil ukendte, substituerede 2,1,3-benzothia-diazinforbindelser med herbicid virkning.
Det er kendt, at 3-isopropyl-2,l,3-benzothiadiazon-(4)-on-2,2- ' dioxid har en selektiv herbicid virkning (tysk patentskrift nr.
Q 1 542 836). Desuden kender man yderligere herbicider af denne n. stofkategori, der skal anvendes til fjernelse af uønsket plante- 9 vækst i en række af kulturplanter (tysk offentliggørelsesskrifter J nr. 2 444 383, 2 443 901 og 2 458 343).
^ Det har nu ifølge opfindelsen vist sig, at forbindelser, med den i kravets kendetegnende del angivne formel VIII, muliggør, at man kan 2 146337 fjerne uønskede, bredbladede planter og cyperaceae udover det kendte område for denne stofkategori i yderligere kulturplanter og med væsentligt ringere risiko, end det hidtil har været muligt.
Forbindelserne ifølge opfindelsen udviser en bedre opløseliglied i upolære carbonhydrider, f.eks. vegetabilske eller animalske olier, og udviser derfor også anvendelsestekniske fordele ved fremstillingen og påføringen af stofferne i form af herbicide midler. Forbindelserne ifølge opfindelsen frembyder derfor en betydelig berigelse af teknikken.
De omhandlede benzothiadiazinforbindelser kan fremstilles ved omsætning af 2,1,3-benzothiadiazinforbindelser med formlen: H /n .KCA^ Λ ti
Y
p hvor R , Y, Σ og m har de i kravet angivne betydninger, (a) med en halogenforbindelse med formlen
Hal - R1 II, i hvor R har den i kravet angivne betydning, og Hal betyder et halogenatom, eller (b) med et sulfat med formlen:
so2(or1)2 III
eller (c) med en sulfonester med formlen:
ArS020R1 IV, hvori R har den i kravet angivne betydning og Ar betyder aryl, even- 5 146337 tuelt i nærværelse af et syrebindende middel og eventuelt i nærværelse af et opløsningsmiddel, eller ved omsætning af salte af forbindelser med formel I med en halogenforbindelse med formel II eller et sulfat med formel III eller en sulfonester med formel IV i nærværelse af et opløsningsmiddel, eller ved omsætning af benzothiadiazinforbindelser med formlen:
?H2Hal 7L
Y
2 hvor R , Y, X og m har den i kravet angivne betydning,'og Hal betyder et halogenatom, med et salt af hydrogencyanid, hydrogen-rhodanid, azoimid, eventuelt substitueret carbamin- eller thiocarbaminsyre, O-alkyl-N-alkylaminothiophosphorsyre eller et 0,0,O-trialkylphosphit. I sidstanførte tilfælde, når reaktanten er et 0,0,O-trialkylphosphit, foregår der ved sub-stituenten R* først en omsætning med natriumazid til methyl-azid, hvorefter methylazidet omsættes med 0,0,O-trialkylphosphit til dannelse af den tilsvarende phosphinylimino-forbindelse.
Man foretrækker omsætningen mellem udgangsforbindelseme I og II.
R1 kan blandt andet betyde: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert.-butyl, n-pentyl, 2-pentyl, 3-pentyl, tert.-amyl, neopentyl, 2-methylbutyl, 3-methylbutyl, 3-methyl-2-butyl, n-hexyl, 4-methyl-2-pentyl, 2,3-dimethylbutyl, 2-methyl-l-pentyl, 2-hexyl, 3-methyl-2-pentyl, 3-methylpentyl, 4-methylpenty1, 3-methyl -3-pentyl, 4,4-dimethylbutyl, chlortert.-butyl, 1,1-dichlor- 2-methyl-2-propyl, 1,3-dichlor-2-methyl-2-propyl, 1-chlorethyl, 2-chlorethyl, 1-chlorpropyl, 2-chlorpropyl, 3-chlorpropyl, 1-chlor- 2-propyl, 2-chlorbutyl, 2-chlor-2-methylpropyl, 1-fluorethyl, 2-fluorethyl, 2-fluorpropyl, 3-fluorpropyl, 1-fluor-2-propyl, 2-fluorbutyl, 2-fluor-2-methylpropyl, 2-bromethyl, 3-brompropyl, 4-chlorbutyl, 1,1,1-trifluorisopropyl, hexafluor-2-methyl-isopropyl, 4 146337 hexafluorisopropyl, hexachlorisopropyl, 2,2,2-trifluorethyl, 1-chlor-butyn-2-yl-4, 3-chlorbutyn-l-yl~4, 2,2,2-trichlorethyl, 2,2,2-tri-bromethyl, l-brom-2-propyl, 1,3-dibrom-2-propyl, benzyl, ethynyl, propen-l-yl, propyn-l-yl, allyl, propargyl, crotyl, butyn-2-yl-l, methallyl, buten-l-yl-3, butyn-l-yl-3, buten-l-yl-4, butyn-l-yl-4, β-methyl-mercapto-ethyl, β-e thy liner capto-e thyl, 3-methylmercapto-propyl, 3-methyl-mercaptobutyl, l-methylmercaptobutyl-2, methyl-mercapto-tert.-butyl, 2-methylmercaptobutyl, 4-methylmercapto-butyl, 2-methyl-butanon-3-yl-2, 2-methyl-pentanon-4-yl-2, 3-butanon- 1-yl, 3-butanon-2-yl, 2-propanon-l-yl, 2-pentanon-l-yl, carbamoyl-methyl, carbamoylethyl, Λ-cyanethyl, β-cyanethyl, tf-cyanethyl, 0,0,0, -triethylphosphinyl-iminomethyl og β, ψ, jg-trichlor-ethy 1.
Betegnelsen "halogen” betyder fluor, chlor, brom og iod.
Hvis man anvender 3-ethyl-2,l,3-benzothiadiazon(4)on-2,2-dioxid-natriumsalt og butynylchlorid som udgangsmaterialer, kan reaktionsforløbet repræsenteres ved følgende formelskema: (a)
CH«-CH_-C=CH
Na i 2 2 °CO + 01-0VCH2-c;ra =1«I* °;ζΧ) °2η5Χ S c2<
Hvis man anvender 3-ethyl-2,1,3-benzothiadiazin(4)on-2,2-dioxid og dimethylsulfat (b) eller p-toluensulfonsyremethylester (c) som udgangsmaterialer, repræsenteres reaktionsforløbet ved følgende formelskemaer b og c: 5 146337 (¾) ch3 °€0 · “Λ”> °$0 C2Hf 1 C2H5 g (c) H ?H3 \0Q* ch3-o-s°=och3 ^ °*co C2H5 » °2n5 0 I tilfælde af, at man anvender 1-chlormethyl-3-ethyl-2,1,3-benzo-thiadiazin(4)on-2,2-dioxid og dimethyl-dithiocarbaminsyre-dimethyl-ammoniumsalt som udgangssubstanser, repræsenteres reaktionsforløbet ved følgende formelskema:
(d) S ✓CH
II /Cii- CH2C1 ch2-s-c-n -5 °€0* (ch3)2i,-5-|Sh2{ch3,2 °200
C2H5" O C2< S
Ved en foretrukken udførelsesform omsætter man ved fremgangsmådevarianterne a, b, c et 2,1,3-benzothiadiazin(4)-on-2,2-dioxid eller dettes salt med en halogenforbindelse, et al-kylsulfat eller en sulfonester, eventuelt i nærværelse af et indifferent opløsningsmiddel og eventuelt i nærværelse af et syrebindende middel ved en temperatur på -30 til 150°C, fortrinsvis 10 - 90°C, i 10 minutter til 6 timer, trykløst eller under tryk, kontinuerligt eller diskontinuerligt.
Ved udøvelsen af fremgangsmåden i henhold til variant d omsætter man for eksempel en forbindelse med formel 6 146337 V med et salt af O-alkyl-N-alkylaminothiophosphorsyre, hydrogencyanid, hydrogenrhodanid, azoimid, eventuelt substitueret carbamin- eller thiocarbaminsyre eller et 0,0,0-trialkylphosphit, eventuelt i nærværelse af et opløsningsmiddel og eventuelt i nærværelse af et syrebindende middel ved en temperatur på -30 til 150 °C, fortrinsvis 10-90 °C, i 10 minutter til 6 timer, trykløst eller under tryk, kontinuerligt eller diskontinuerligt.
Hvis reaktanten er et 0,0,0-trialkylphosphit, foregår der en forudgående reaktion med natriumazid til methylazid ved substi-1 tuenten R .
Til de foretrukne indifferente opløsningsmidler hører carbon-hydrider, såsom ligroin, benzinfraktioner, f.eks. med et kogepunktsinterval på 70-140 °C, cyclohexan, pentan, hexan, petroleumsether, o,m,p-xylenj nitrocarbonhydrider, såsom nitrobenzen, nitroethan? nitriler, såsom acetonitril, butyronitril, isobutyronitril; ethere, såsom diethylether, di-n-propylether, tetrahydrofuran, dioxan, ani-sol; estere, såsom aceteddikesyreester, ethylacetat, isobutylace-tat, benzoesyremethylester, phenylacetat; amider, såsom formamid, methylformamid eller dimethylformamid, eller ketoner, såsom acetone, methylethylketon, cyclohexanon, acetophenon.
Hvis man i stedet for saltene deraf direkte anvender forbindelserne med formel I , hører også halogencarbonhydrider som methylenchlorid, chloroform, tetrachlorkulstof, 1,1- og 1,2-di-ehlorethan, 1,1,1- og 1,1,2-trichlorethan, chlorbenzen, o,m,p-dichlorbenzen eller o,m,p-chlortoluen til de foretrukne opløsningsmidler. Hvis saltene af forbindelserne med formel I anvendes, henregnes ved fremgangsmådevarianterne a, b, c også vand til de foretrukne opløsningsmidler. Som syrebindende midler kan man anvende alle sædvanlige syrebindende midler. Hertil hører fortrinsvis alkalimetalhydroxider, alkalimetalcarbonater og tertiære organiske baser. Som særligt velegnede eksempler skal anføres: natriumhydroxid, natriumcarbonat, natriumhydrogencarbonat, triethyl-amin, pyridin, trimethylamin^^^-picolin, lutidin, N,N-dimethyl-anilin, Ν,Ν-dimethylcyclohexylamin, quinolin, tri-n-propylamin, n-propyl-diisopropylamin og tri-n-butylamin.
7 146337
Foruden udgangsmaterialerne I lader disses tilsvarende alkalimetal-, jordalkalimetal- eller ammoniumsalte sig med fordel anvende som udgangsmaterialer. De som udgangsmateriale anvendte forbindelser med formel I og V anvendes fortrinsvis i en mængde på mellem 0,3 og 1, fortrinsvis mellem 0,8 og 1 mol pr. mol udgangsstof.
Tilsætningen af udgangsmaterialerne kan gennemføres i vilkårlig rækkefølge. Følgende fremgangsmåde er særlig fordelagtig: man lader en opløsning af udgangsmaterialerne II, III eller IV i et af de før angivne indifferente opløsningsmidler løbe til en opløsning eller suspension af udgangsmaterialet I eller dettes salt i et af de før angivne indifferente opløsningsmidler, eller man lader en opløsning eller suspension af et salt af O-alkyl-N-alkylamino-thiophosphorsyre, hydrogencyanid, hyclrogenrhodanid, . azoimid, eventuelt substitueret carbamin- eller thiocarbaminsyre eller et 0,0,0-trialkylphosphit i et af de før angivne indifferente opløsningsmidler løbe til en opløsning af udgangsmaterialet V og gennemfører derpå omsætningen i det før angivne temperaturområde. Hvis reaktanten er en af de før angivne forbindelser af 0,0,O~trialkylphosphit, foregår omsætningen ikke med halogenforbindelsen V, men med den til V svarende azidomethylforbindelse.
For at accelerere reaktionen mellem udgangsmaterialerne I og halogenforbindelserne II kan man ved anvendelse af fluor— eller chlorforbindelser med formel II tilføre et alkalime— tal- eller ø ordalkal ime t al salt af et tungt halogenatom, f.eks. natriumeller calciumiodid, som katalysator. Yed anvendelse af et tofaset opløsningsmiddelsystem er også kvaternære forbindelser velegnede som katalysatorer. Mængden af den katalysator, der skal anvendes ifølge opfindelsen, ligger mellem 0,1 og 10 vægtprocent, beregnet i forhold til udgangsstoffet II. Med henblik på isolering af forbindelserne med formel VIII fra reaktionsblandingen svarende til varianterne a til d indrører man reaktionsblandingen i en fortyndet, vandig alkaliopløsning i tilfælde af anvendelse af med vand blandbare opløsningsmidler. Den udskilte olie bliver ligeledes ekstraheret, vasket med vand og tørret.
Hvis man har udvalgt kun lidet polære, med vand ikke blandbare 8 146337 opløsningsmidler, kan man også ekstrahere reaktionsopløsningen direkte med fortyndet vandig alkaliopløsning og vand. Eventuelt kan man også først koncentrere reaktionsblandingen, optage den i et med vand ikke blandbart opløsningsmiddel og rense, som anført. Efter tørringen og koncentreringen af den organiske fase opnår man de ønskede slutprodukter. Eventuelt kan de renses yderligere på sædvanlig måde, f.eks. ved omkrystallisation eller kromatografi.
er-rempel 1
Til en opløsning af 1 del natriumiodid og 80 dele 3-isopropyl- 2,1,3-benzothiadiazin(4)-2,2-dioxid-1-kaliumsalt i 630 dele aceto-nitril tildryppedes 25,3 dele l-chiorbutyn-3 inden for 10 minutter under omrøring ved 24°C. Efter 10 timers omrøring ved 82°C blev reaktionsblandingen koncentreret i vakuum, optaget i 300 dele methylenehlorid, ekstraheret 4 gange, i hvert tilfælde med 100 ml 0,5 n natronlud, og ekstraheret med vand. Efter tørringen over magnesiumsulfat, chromatografering over neutralt aluminiumoxid og koncentrering i vakuum isoleredes l-butyn(3')yl-3-iso-propyl-2,1,3-benzothiadiazin(4)on-2,2-dioxidet i form af farveløse krystaller med smeltepunkt 66-70°C.
EKSEMPEL 2 16,5 dele diethylsulfat indførtes ved 10°C under omrøring inden for 15 minutter i en opløsning af 24 dele 3-isopropyl-2,1,3-benzo-thiadiazin(4)on-2,2-dioxid og 4,5 dele natriumhydroxid i 25 dele vand. Reaktionsblandingen blev derpå holdt under omrøring i 10 timer ved 20°C, blandet med 150 dele 1,2-dichlorethan, ekstraheret 2 gange med i hvert tilfælde 70 ml 0,5 n natronlud og ekstraheret med vand. Efter tørringen, koncentrering i vakuum og gnidning med cyclohexan isoleredes 1-ethyl-3-isopropyl-2,1,3-benzo-thiadiazin(4)on-2,2-dioxidet i form af farveløse krystaller med smeltepunkt 56-58°C.
9 146337 EKSEMPEL 3 16 dele O-ethyl-N-isopropylamino-thiophosphorsyre-dimethylammonium-salt, opløst i 60 dele acetonitril, tilsattes inden for 10 minutter under omrøring ved 10°C til en opløsning af 20,2 dele 1-chlor-methyl-3-isopropyl-2,1,3-benzothiadiazin(4)on-2,2-dioxid i 160 dele acetonitril. Reaktionsblandingen blev derpå holdt under omrøring i 2 timer ved 25°C, koncentreret i vakuum, optaget i 200 dele diethylether og ekstraheret 3 gange, hver gang med 100 dele 10$ natriumhydrogencarbonatopløsning og med vand. Efter tørringen over magnesiumsulfat, koncentrering i vakuum og gnidning med cyclo-hexan fremkom 1 -methyl- (0-ethyl-N-isopropyl-amino-thiophosphory 1.) - 3-isopropyl-2,1,3-benzothiadiazin(4)on-2,2-dioxid i form af farveløse krystaller med smeltepunkt 79-84°C.
EKSEMPEL 4 100 dele 1-chlormethyl-3-isopropyl-2,1,3-benzothiadiazin(4)on- 2,2-dioxid og 150 dele natriumazid holdtes under omrøring i 800 dele dimethylformamid i 6 timer ved 25°C. Derpå fortyndede man suspensionen med et fem gange så stort volumen vand. Efter en times forløb frasugedes og tørredes de udfældede krystaller, hvorved der fremkom 100 dele (98$ teoretisk) l-azidomethyl-3-isopropyl- 2,1,3-benzothiadiazin(4)on-2,2-dioxid med smeltepunkt, 83 °C.
ίο 146337
Andre aktive stoffer svarende til den almene formel fremstilledes i henhold til tilsvarende metoder. De er sammenstillet i tabel I, hvor m er 0 hvis intet er angivet.
TABEL I
Y Smp. (°C) n-C3H? CH3 0 39 CH3 i_C3H7 0 54-55 n-C3H? i-C3H? 0 n^5= 1,5359 i-C3H7 i~C3H7 0 44-45 sek.-C4Hg i-C3H7 0 nD5= 1'5316 -CH2-CH2-CH(CH3)2 i-C3H7 0 nD5= 1'5278 C2H5 sek.-C4H9 0 68-71 -CH2-CSCH CH3 0 122-126 -CH2-C=CH C2H5 0 71-75 -CH2-C=CH n~C3H7 0 53-57 -CH2-CH=CH2 i_C3H7 0 41-43 -CH2-C=CH i-C3H7 0 108-112 -CH2-CH=CH-CH3 i-C3H? 0 n^5= 1,5436 -CH2-CH2-CSCH i-C3H7 0 66-69 -CH2-C=CH sek.-C4Hg 0 55-59 -CH2-CH2Br i_C3H7 0 n^5= 1»5648 -CH2-C=C-CH2C1 i_C3H7 0 68-72 C13C-CH-NHCH i~C3H7 0 209-211 O 0 -CH2-C-CH3 i-C3H7 0 nD5= i'5464 'CH2^0 i-C3H7 0 82-86 0 -CH2-CH2-C-CH3 i_C3H7 ° 69-73 11 146337 Y Smp. (°C)
O
-CH2-C-NH2 i_C3H7 0 161-163 -CH2-SCN i_C3H7 0 124-126 -CH2-CN i"C3H7 0 119-121 -CH2-CH2CN i_C3H7 0 115-117 -CH2-CH^-C-NH2 i_C3H7 O 139-141 -CH2-S-C-N(CH3)2 i-C3H7 O 139-141 § -CH2-S-C-N(C2H5)2 i_C3H7 0 85-87 -CH2S-C-N(i-C3H7)2 i-C3H? O 139-141
S
’ -GH9tS-C-N^C2H5 i-C,H7 O 70 s x<ch2>3ch3 -CH2-S-C-iO i-C3H7 0 110-113
CH
3 -CH2-S-IA i-C3H7 o 73-76 " Λ -CH2S-C-N > i_C3H7 0 72-74 -CH2-N=P(OC2H5)3 i-C3H? O n^5= 1,5072 X Rinqstilling m R^ R^ Y Smp. (° C)
Cl 7 1 CH2-C=CH i-C3H7 O 97-103 J 6 1 CH2-C=CH i-C3H7 O 105-109
Cl 7 1 CH2-CH2OH i-C^ 0 93-96
Cl 7 1 CH2-C-CH3 i_C3H7 0 94-97
Br 6 1 CH3 i-C3H7 O 135-137
Br 6 1 CH2C6H5 i-C3H? O 110-111 12 146337 X Rinqstillinq in r£ X Smp. (°C)
Cl 8 1 CH2-C5CH i_C3H7 0 86-90
Cl 6 1 CH2-C=CH i-C3H7 0 92-94
Cl 6 1 CH2C6H5 C2H5 0 105-109
Cl 6 1 CH3 C2H5 O 96-98 O CH2N3 CH3 O 108 O CH2-S-C-QCH3 i-C3H7 0 68 ** Viskos O CH2-N=P(0CH3)3 i-C3H7 O olie 7Π O CH-S-C2H5 i-C3H7 0 nD = 1»5497 ch3 EKSEMPEL 5
De herbicide og selektive virkninger af de omhandlede 2,1,3-benzothiadiazinforbindelser undersøgtes ved drivhus- og frilandsforsøg.
I. Drivhusforsøg
Formstofurtepotter med et indhold på 300 cm^ blev fyldt med lerholdigt sandjord og blev forsynet med forsøgsplanterne adskilt efter art.
Herved drejede det sig om såning af frø, nedlægning af knolde, der var begyndt at spire (f.eks. Cyperus esculentus) eller om en udplantning.; af ad vegetativ vej formerede arter.
13 146337
Ved behandling før spiringen kom kun frø i betragtning. De aktive stoffer suspenderedes eller emulgeredes i vand som fordelingsmiddel og blev ved hjælp af fint fordelende dyser sprøjtet på jordoverfladen. Efter behandlingen blev beholderne udsat for let vanding og blev afdækket med gennemsigtige formstofhætter, indtil planterne var i god vækst. Ved behandlingen efter spiringen (bladbehandlingen) fremdrev man først planterne i forsøgsbeholderne til en højde af 3 - 10 cm, afhængigt af vækstformen, hvorpå behandlingen foretoges. Man udelod naturligvis en øjéblikkelig vanding og ligeledes afdækningen. Man tog hensyn til forsøgsplanternes temperaturkrav i den henseende, at de blev opstillet i koldere eller varmere sektioner af drivhusanlæggene. Forsøgsperioden varede mellem 2 og 4 uger. I dette tidsrum plejede man planterne, og deres reaktion på de enkelte behandlinger blev bedømt. Een anvendte mængde af de undersøgte stoffer anføres som kg aktivt stof/ha. Bedømmelsen foregik ved hjælp af skalaen fra 0 til 100. Derved betød 0 ingen beskadigelse eller normal vækst, mens 100 betød ingen opvoksning eller ødelæggelse af planterne.
II. Frilandsforsøg 1 dette område gennemførte man behandlinger efter spiringen på små parceller. Påføringen af stofferne foregik i vand som bære--og fordelingsmedium, emulgeret eller suspenderet ved hjælp af en motordrevet, på en stativbærer monteret parcelsprøjte. Alle forsøg iagttoges over flere uger og blev ligeledes bedømt i henhold til skalaen fra 0 til 100.
Resultat
De i tabellerne 2-6 anførte repræsentanter for de omhandlede forbindelser bekæmper uønskede planter bedre end sammenligningsforbin-delsen l-chlor-methyl-3-isopropyl-2,1,3-benzothiadiazin-(4)-on-2,2-dioxid og på lignende måde, ofte svagere end sammenligningsforbindelsen 3-isopropyl~2,1,3-benzothiadiazin-(4)-2,2-dioxid. Forligeligheden svarer til de anvendte sammenligningsforbindelser ved nogle kulturplanter. Ved kulturplanter, hvor kendte forbindelser af denne stofkategori ikke kan anvendes eller kun kan anvendes med betydelig 14 146337 risiko for skade, som f.eks. kartofler, køkkenløg eller solsikker, viste forbindelserne ifølge opfindelsen sig som væsentligt bedre forligelige, og heri skal den fordelagtige tekniske virkning ses.
Liste over., plantenavne
Botanisk navn Forkortelse i tabeller
Abutilo.i theophrastii Abut. theo.
Allium cepa
Amaranthus sop. Amar. spp.
Ammania coccinea Amman, cocc.
Chenopodium spp. Chenop. spp.
Chrysanthemum segetum Chrys. seget.
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Det er desuden også muligt, at man kan påføre forbindelserne ifølge-opfindelsen alene eller i kombination med andre herbicider og også blandet med yderligere plantebeskyttelsesmidler. Herved tænkes der f.eks. på midler til bekæmpelse af skadelige organismer eller phytopatogene svampe eller bakterier. Desuden er blandbarheden med mineralsaltopløsninger, der kan anvendes til ophævelse af mangler, hvad angår ernærings- eller sporgrundstoffer, af interesse.
Til aktivering af den herbicide virkning kan man tilsætte befugt-nings- og adhæsionsmidler samt ikke phytotoxiske olier.
Påføringen foregår for eksempel i form af direkte udsprøjtelige opløsninger, pulvere, suspensioner eller dispersioner, ud-strøningsmidler, granulater, ved udsprøjtning, tågedannelse, forstøvning, udstrøning eller udhældning. Påføringsformerne retter sig helt efter anvendelsesformålene. De skal i hvert tilfælde sikre den finest mulige fordeling af de aktive stoffer ifølge opfindelsen.
Til fremstilling af direkte udsprøjtelige opløsninger, emulsioner, pastaer og oliedispersioner kommer mineraloliefraktioner med middelhøjt til højt kogepunkt, såsom petroleum eller dieselolie, desuden kultjæreolier, samt olier af vegetabilsk eller animalsk oprindelse, alifatiske, cycliske og aromatiske carbonhydri-der, f.eks. benzen, toluen, xylen, paraffin, tetrahydronaphtha-len, alkylerede naphthalener eller disses derivater, f.eks. methanol, ethanol, propanol, butanol, chloroform, tetrachlorkulstof, cyclohexanol, cyclohexanon, chlorbenzen og isophoron, stærkt polære opløsningsmidler, f.eks. dimethylformamid, dimethylsulfoxid, N-methylpyrrolidon og vand i betragtning.
Vandige påføringsformer kan fremstilles af emulsionskoncentrater, faste eller befugtelige pulvere (sprøjtepulvere), oliedispersioner ved tilsætning af vand. Til fremstilling af emulsioner, pastaer eller oliedispersioner kan stofferne som sådanne eller opløst i en olie eller opløst i et opløsningsmiddel homogeniseres i vand ved hjælp af befugtnings-, adhæsions-, disperge- 25 146337 rings- eller emulgeringsmidier. Men man kan også fremstille koncentrater, der består af aktivt stof, befugtnings-, adhæsions-, dispergerings- eller emulgeringsmiddel og eventuelt opløsningsmiddel eller olie, og som er velegnet til fortynding med vand.
Som eksempler på overfladeaktive stoffer skal anføres: alkali metal-, jordalkalimetal-, ammoniumsalte af ligninsulfonsyre, naphthalensulfonsyrer, phenolsulfonsyrer, alkylarylsulfonater, alkylsulfater, alkylsulfonater, alkalimetal- og jordalkalimetal-salte af dibutylnaphthalensulfonsyre, laurylethersulfat, fedt-alkoholsulfater, fedtsure alkalimetal-, og jordalkalimetalsalte, salte af sulfaterede hexadecanoler, heptadecanoler, octadeca-noler, salte af sulfateret fedtalkoholglycolether, kondensationsprodukter af sulfoneret naphthalen og naphthalenderivater med formaldehyd, kondensationsprodukter af naphthalen eller naphthalensulfonsyrer med phenol og formaldehyd, polyoxyethylen-octylphenol-ether, ethoxyleret isooctylphenol-, octylphenol-, nonylphenol, alkylphenolpolyglycolether, tributylphenolpolyglycolether, alkyl-arylpolyetheralkoholer, isotridecylalkohol, fedtalkoholethylen-oxid-kondensater, ethoxyleret ricinusolie, polyoxyethylenalkyl-ether, ethoxyleret polyoxypropylen, laurylalkoholpolyglycolether-acetal, sorbitester, lignin, sulfitaffaldslud og methylcellulose.
Pulvere, udstrønings- og pudringsmidier kan fremstilles ved blanding eller fælles formaling af de aktive stoffer med et fast bærestof.
Granulater, f.eks. omhyllings-, imprægnerings- og homogengranulater, kan fremstilles ved binding af de aktive stoffer til faste bærestoffer. Paste bærestoffer er for eksempel mineral3order, såsom silicagel, kiselsyrer, kiselgeler, silicater, talkum, kaolin, attaler, kalksten, kalk, kridt, talkum, bolus, løss, ler, dolomit, diatomejord, calcium- og magnesiumsulfat, magnesiumoxid, findelte formstoffer, gødningsmidler, såsom for eksempel ammoniumsulfat, ammoniumphosphat, ammoniumnitrat, urinstoffer og vegetabilske produkter, såsom kornmel, træbark-, træ- og nøddeskallerne!, cellulosepulver og andre faste bærestoffer.
26 146337
Blandingerne indeholder mellem 0,1 og 95 vægtprocent aktivt stof, fortrinsvis mellem 0,5 og 90 vægtprocent. De anvendte mængder andrager mellem 0,1 og 10 kg aktivt stof/ha, især mellem 0,5 og 5 kg aktivt stof/ha.
I eksempel 6-14 refererer forbindelsesnumrene til numrene for aktivt stof i tabel 2 og 3.
EKSEMPEL· 6
Man blander 90 vægtdele af forbindelsen nr. 1 med 10 vægtdele N-methyl-a-pyrrolidon og opnår en opløsning, der er velegnet til anvendelse i form af meget små dråber.
EKSEMPEL· 7 20 vægt dele af forbindelsen nr. 2 opløses i en blanding, der består af 80 vægtdele xylen, 10 vægtdele af additionsproduktet af 8 til 10 mol ethylenoxid til 1 mol oliesyre-N-monoethanolamid, 5 vægtdele calciumsalt af dodecylbenzen-sulfonsyre og 5 vægtdele af tillejringsproduktet af 40 mol ethylenoxid til 1 mol ricinusolie. Yed udhældning og fin fordeling af opløsningen i 100 000 vægtdele vand opnår man en vandig dispersion, der indeholder 0,02 vægtprocent af det aktive stof.
EKSEMPEL· 8 20 vægtdele af forbindelsen nr. 5 opløses i en blanding, der består af 40 vægtdele cyclohexanon, 30 vægtdele isobutanol, 20 vægtdele af additionsproduktet af 7 mol ethylenoxid til 1 mol isooctyl-phenol og 10 vægtdele af tillejringsproduktet af 40 mol ethylenoxid til 1 mol ricinusolie. Yed udhældning og fin fordeling af opløsningen i 100 000 vægtdele vand opnår man en vandig dispersion, der indeholder 0,02 vægtprocent af det aktive stof.
27 146337 EKSEMPEL· 9 20 vægtdele af forbindelsen nr. 6 opløses i en blanding, der består af 25 vægtdele cyclohexanol, 65 vægtdele af en mineraloliefrak-tion med kogepunkt 210 til 280°C og 10 vægtdele af additionsproduktet af 40 mol ethylenoxid til 1 mol ricinusolie. Ved ud-hældning og fin fordeling af opløsningen i 100 000 vægtdele opnår man en vandig opløsning, der indeholder 0,02 vægtprocent af det aktive stof.
EKSEMPEL· 10 20 vægtdele af det aktive stof nr. 1 .blandes godt med 3 vægtdele af natriumsaltet af diisobutylnaphthalen-oc-sulfonsyre, 17 vægtdele af natriumsaltet af en ligninsulfonsyre fra en sulfitaffaidslud og 60 vægtdele pulverformig kiselsyregel og formales i en hammermølle. Ved fin fordeling af blandingen i 20 000 vægtdele vand opnår man en sprøjtevæske, der indeholder 0,1 vægtprocent af det aktive stof.
EKSEMPEL· 11 3 vægtdele af forbindelsen nr. 2 blandes grundigt med 97 vægtdele findelt kaolin. Man opnår på denne måde et pudringsmiddel, der indeholder 3 vægtprocent af det aktive stof.
EKSEMPEL· 12 30 vægtdele af forbindelsen nr. 5 blandes grundigt med en blanding af 92 vægtdele pulverformig kiselsyregel og 8 vægtdele paraffinolie, der var sprøjtet på overfladen af denne kiselsyregel. På denne måde opnår man et præparat af det aktive stof med god adhæsionsevne.
EKSEMPEL· 13 40 vægtdele af det aktive stof nr. 6 blandes grundigt med 10 dele na- 28 146337 triumsalt af phenolsulfonsyre-urinstof-formaldehyd-kondensat, 2 dele kiselgel og 48 dele vand. Man opnår en stabil, vandig dispersion. Yed fortynding med 100 000 vægtdele vand opnår man en vandig dispersion, der indeholder 0,04 vægtprocent aktivt stof.
EKSEMPEL 14 20 dele af det aktive stof nr. 1 blandes grundigt med 2 dele calciumsalt af dodecylbenzensulfonsyre, 8 dele fedtalkohol-polyglycol-ether, 2 dele natriumsalt af et phenolsulfonsyre-urinstof-form-aldehydkondensat og 68 dele af en paraffinisk mineralolie. Man opnår en stabil olieagtig dispersion.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762656290 DE2656290A1 (de) | 1976-12-11 | 1976-12-11 | Benzothiadiazinverbindungen |
| DE2656290 | 1976-12-11 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK549077A DK549077A (da) | 1978-06-12 |
| DK146337B true DK146337B (da) | 1983-09-12 |
| DK146337C DK146337C (da) | 1984-02-20 |
Family
ID=5995330
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK549077A DK146337C (da) | 1976-12-11 | 1977-12-09 | Benzothiadiazinforbindelser med herbicid virkning |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4298731A (da) |
| JP (1) | JPS5373575A (da) |
| AT (1) | AT356448B (da) |
| AU (1) | AU509795B2 (da) |
| BE (1) | BE861756A (da) |
| BR (1) | BR7708210A (da) |
| CA (1) | CA1106372A (da) |
| CH (1) | CH634721A5 (da) |
| CS (1) | CS196400B2 (da) |
| DD (1) | DD133290A5 (da) |
| DE (1) | DE2656290A1 (da) |
| DK (1) | DK146337C (da) |
| FR (1) | FR2373536A1 (da) |
| GB (1) | GB1596384A (da) |
| HU (1) | HU178174B (da) |
| IL (1) | IL53398A (da) |
| IT (1) | IT1090731B (da) |
| NL (1) | NL7713610A (da) |
| SU (1) | SU843696A3 (da) |
| ZA (1) | ZA777234B (da) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH645367A5 (de) * | 1980-11-24 | 1984-09-28 | Ciba Geigy Ag | Substituierte benzo-2-thia-1,3-diazin-4(3h)-on-2,2-dioxyde. |
| GB8820129D0 (en) * | 1988-08-24 | 1988-09-28 | Schering Agrochemicals Ltd | Fungicides |
| ES2156725B1 (es) * | 1999-05-07 | 2002-03-01 | Consejo Superior Investigacion | Derivados de dioxidos n,n- y n,x-disustituidos de 1,2,6-tiadiazina fusionadas y procedimiento de obtencion. |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1120456B (de) * | 1958-10-01 | 1961-12-28 | Geigy Ag J R | Verfahren zur Herstellung von neuen 4-Oxo-3, 4-dihydro-2, 1, 3-benzothiadiazin-2, 2-dioxyden |
| US3217001A (en) * | 1963-08-19 | 1965-11-09 | American Home Prod | Derivatives of 1h-2, 1, 3-benzothiadiazin-4(3h)-one 2-oxide and intermediates therefor |
| US3940389A (en) * | 1973-09-17 | 1976-02-24 | The Dow Chemical Company | 4 (3H)-Oxobenzo-2,1,3-thiadiazine-2,2-dioxides |
| CA1031339A (en) * | 1973-09-17 | 1978-05-16 | Lennon H. Mckendry | Substituted 4(3h)-oxobenzo-2,1,3-thiadiazine-2,2-dioxides and their use as herbicides |
| CA1024144A (en) * | 1973-09-17 | 1978-01-10 | The Dow Chemical Company | 4(3h)-oxobenzo-2,1,3-thiadiazine-2,2-dioxides |
| DE2349114C2 (de) * | 1973-09-29 | 1985-11-14 | Basf Ag, 6700 Ludwigshafen | 3-sek.-Butyl-2,1,3-benzothiadiazin-(4)-on-2,2-dioxid |
| DE2355113A1 (de) * | 1973-11-03 | 1975-05-15 | Basf Ag | N,n'-disubstituierte 2,1,3-benzothiadiazin-(4)-on-2,2-dioxide |
| US4051130A (en) * | 1974-08-15 | 1977-09-27 | The Dow Chemical Company | 4(3H)-oxobenzo-2,1,3-thiadiazine-2,2-dioxides and derivatives thereof |
| DE2444822A1 (de) * | 1974-09-19 | 1976-04-08 | Basf Ag | 2,1,3-benzothiadiazin(4)on-2,2dioxid-derivate |
| DE2458343A1 (de) * | 1974-12-10 | 1976-06-16 | Basf Ag | N-n'-disubstituierte 2,1,3-benzothiadiazin(4)on-2.2-dioxide |
| DE2553209C2 (de) * | 1975-11-27 | 1986-01-02 | Basf Ag, 6700 Ludwigshafen | 1-Methoxymethyl-3-isopropyl-2,1,3-benzothiadiazin(4)on-2,2-dioxid und diese enthaltende Herbizide |
| US4208514A (en) * | 1976-02-23 | 1980-06-17 | The Dow Chemical Company | 4(3H)-Oxobenzo-2,1,3-thiadiazine-2,2-dioxides |
| US4054440A (en) * | 1976-02-23 | 1977-10-18 | The Dow Chemical Company | 4(3H)-Oxobenzo-2,1,3-thiadiazine-2,2-dioxides |
| DE2656289C2 (de) * | 1976-12-11 | 1982-08-12 | Basf Ag, 6700 Ludwigshafen | 1-Cyano-3-isopropyl-2,1,3--benzothiadiazin-4-on-2,2-dioxid-Verbindungen |
| US4139700A (en) * | 1977-07-27 | 1979-02-13 | Monsanto Company | Process for the preparation of bicyclothiadiazinones |
-
1976
- 1976-12-11 DE DE19762656290 patent/DE2656290A1/de not_active Withdrawn
-
1977
- 1977-11-15 IL IL53398A patent/IL53398A/xx unknown
- 1977-11-16 US US05/851,826 patent/US4298731A/en not_active Expired - Lifetime
- 1977-11-17 CA CA291,107A patent/CA1106372A/en not_active Expired
- 1977-11-25 AU AU30966/77A patent/AU509795B2/en not_active Expired
- 1977-11-30 JP JP14286077A patent/JPS5373575A/ja active Pending
- 1977-12-05 ZA ZA00777234A patent/ZA777234B/xx unknown
- 1977-12-05 GB GB50507/77A patent/GB1596384A/en not_active Expired
- 1977-12-06 CS CS778127A patent/CS196400B2/cs unknown
- 1977-12-07 CH CH1501577A patent/CH634721A5/de not_active IP Right Cessation
- 1977-12-08 NL NL7713610A patent/NL7713610A/xx not_active Application Discontinuation
- 1977-12-09 HU HU77BA3604A patent/HU178174B/hu unknown
- 1977-12-09 DK DK549077A patent/DK146337C/da not_active IP Right Cessation
- 1977-12-09 DD DD7700202514A patent/DD133290A5/xx unknown
- 1977-12-09 IT IT52137/77A patent/IT1090731B/it active
- 1977-12-09 AT AT881377A patent/AT356448B/de not_active IP Right Cessation
- 1977-12-09 SU SU772551152A patent/SU843696A3/ru active
- 1977-12-09 BR BR7708210A patent/BR7708210A/pt unknown
- 1977-12-12 BE BE183369A patent/BE861756A/xx not_active IP Right Cessation
- 1977-12-12 FR FR7737381A patent/FR2373536A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DD133290A5 (de) | 1978-12-27 |
| DE2656290A1 (de) | 1978-06-15 |
| BE861756A (fr) | 1978-06-12 |
| BR7708210A (pt) | 1978-08-15 |
| DK146337C (da) | 1984-02-20 |
| GB1596384A (en) | 1981-08-26 |
| CH634721A5 (de) | 1983-02-28 |
| JPS5373575A (en) | 1978-06-30 |
| FR2373536A1 (fr) | 1978-07-07 |
| SU843696A3 (ru) | 1981-06-30 |
| US4298731A (en) | 1981-11-03 |
| IL53398A (en) | 1982-12-31 |
| ATA881377A (de) | 1979-09-15 |
| HU178174B (en) | 1982-03-28 |
| FR2373536B1 (da) | 1982-05-21 |
| CA1106372A (en) | 1981-08-04 |
| AU3096677A (en) | 1979-05-31 |
| IT1090731B (it) | 1985-06-26 |
| AT356448B (de) | 1980-04-25 |
| ZA777234B (en) | 1978-10-25 |
| CS196400B2 (en) | 1980-03-31 |
| IL53398A0 (en) | 1978-01-31 |
| DK549077A (da) | 1978-06-12 |
| AU509795B2 (en) | 1980-05-22 |
| NL7713610A (nl) | 1978-06-13 |
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| Date | Code | Title | Description |
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| PBP | Patent lapsed |