NO116277B - - Google Patents
Info
- Publication number
- NO116277B NO116277B NO170854A NO17085467A NO116277B NO 116277 B NO116277 B NO 116277B NO 170854 A NO170854 A NO 170854A NO 17085467 A NO17085467 A NO 17085467A NO 116277 B NO116277 B NO 116277B
- Authority
- NO
- Norway
- Prior art keywords
- substituted
- phenyl radical
- bromine
- chlorine
- active substance
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 claims description 17
- 239000013543 active substance Substances 0.000 claims description 16
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 12
- -1 benzyl halide Chemical class 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 125000001246 bromo group Chemical group Br* 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 230000000895 acaricidal effect Effects 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000006185 dispersion Substances 0.000 description 11
- 239000000839 emulsion Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000443 aerosol Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 4
- JGFXSYYZFNHIFP-UHFFFAOYSA-N 1-benzyl-2-(2-benzyl-4-bromo-4-chlorocyclohexa-1,5-dien-1-yl)sulfanyl-5-bromo-5-chlorocyclohexa-1,3-diene Chemical compound BrC1(CC(=C(C=C1)SC1=C(CC(C=C1)(Br)Cl)CC1=CC=CC=C1)CC1=CC=CC=C1)Cl JGFXSYYZFNHIFP-UHFFFAOYSA-N 0.000 description 3
- 241000238876 Acari Species 0.000 description 3
- PVLLPWQZXRORLP-UHFFFAOYSA-N BrC1(C=CC(SC(C=C2)=C(CC3=CC=CC=C3)CC2(Br)Br)=C(CC2=CC=CC=C2)C1)Br Chemical compound BrC1(C=CC(SC(C=C2)=C(CC3=CC=CC=C3)CC2(Br)Br)=C(CC2=CC=CC=C2)C1)Br PVLLPWQZXRORLP-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000003517 fume Substances 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 229940057995 liquid paraffin Drugs 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000012875 nonionic emulsifier Substances 0.000 description 2
- 239000000346 nonvolatile oil Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- BSIIGUGKOPPTPZ-UHFFFAOYSA-N 1-bromo-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Br)C=C1 BSIIGUGKOPPTPZ-UHFFFAOYSA-N 0.000 description 1
- IFCHZSXOKYVTJT-UHFFFAOYSA-N 1-bromo-4-[(4-fluorophenyl)methylsulfanyl]benzene Chemical compound C1=CC(F)=CC=C1CSC1=CC=C(Br)C=C1 IFCHZSXOKYVTJT-UHFFFAOYSA-N 0.000 description 1
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 1
- HHDLNNQTGRYNKC-UHFFFAOYSA-N 1-chloro-4-[(4-iodophenyl)methylsulfanyl]benzene Chemical compound C1=CC(Cl)=CC=C1SCC1=CC=C(I)C=C1 HHDLNNQTGRYNKC-UHFFFAOYSA-N 0.000 description 1
- FTBCOQFMQSTCQQ-UHFFFAOYSA-N 4-bromobenzenethiol Chemical compound SC1=CC=C(Br)C=C1 FTBCOQFMQSTCQQ-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- LKMCJXXOBRCATQ-UHFFFAOYSA-N benzylsulfanylbenzene Chemical class C=1C=CC=CC=1CSC1=CC=CC=C1 LKMCJXXOBRCATQ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- YYJNOYZRYGDPNH-MFKUBSTISA-N fenpyroximate Chemical compound C=1C=C(C(=O)OC(C)(C)C)C=CC=1CO/N=C/C=1C(C)=NN(C)C=1OC1=CC=CC=C1 YYJNOYZRYGDPNH-MFKUBSTISA-N 0.000 description 1
- 238000010413 gardening Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F42—AMMUNITION; BLASTING
- F42C—AMMUNITION FUZES; ARMING OR SAFETY MEANS THEREFOR
- F42C15/00—Arming-means in fuzes; Safety means for preventing premature detonation of fuzes or charges
- F42C15/18—Arming-means in fuzes; Safety means for preventing premature detonation of fuzes or charges wherein a carrier for an element of the pyrotechnic or explosive train is moved
- F42C15/184—Arming-means in fuzes; Safety means for preventing premature detonation of fuzes or charges wherein a carrier for an element of the pyrotechnic or explosive train is moved using a slidable carrier
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F42—AMMUNITION; BLASTING
- F42C—AMMUNITION FUZES; ARMING OR SAFETY MEANS THEREFOR
- F42C15/00—Arming-means in fuzes; Safety means for preventing premature detonation of fuzes or charges
- F42C15/18—Arming-means in fuzes; Safety means for preventing premature detonation of fuzes or charges wherein a carrier for an element of the pyrotechnic or explosive train is moved
- F42C15/188—Arming-means in fuzes; Safety means for preventing premature detonation of fuzes or charges wherein a carrier for an element of the pyrotechnic or explosive train is moved using a rotatable carrier
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F42—AMMUNITION; BLASTING
- F42C—AMMUNITION FUZES; ARMING OR SAFETY MEANS THEREFOR
- F42C15/00—Arming-means in fuzes; Safety means for preventing premature detonation of fuzes or charges
- F42C15/34—Arming-means in fuzes; Safety means for preventing premature detonation of fuzes or charges wherein the safety or arming action is effected by a blocking-member in the pyrotechnic or explosive train between primer and main charge
Landscapes
- Engineering & Computer Science (AREA)
- General Engineering & Computer Science (AREA)
- Air Bags (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Description
Akaricid preparat. Acaricidal preparation.
Foreliggende oppfinnelse angår benzyl-fenylsulfider som er blitt funnet å ha verdi-fulle egenskaper som akaricider. The present invention relates to benzyl phenyl sulphides which have been found to have valuable properties as acaricides.
Oppfinnelsen består i forbindelse med den generelle formel The invention consists in connection with the general formula
hvori fenylradikalet X er usubstituert eller i p-stilling er substituert med brom, klor eller fluor og fenylradikalet Y i p-stilling er substituert med brom, klor eller jod, forutsatt at når fenylradikalet Y er substituert med brom er fenylradikalet X substituert med brom eller klor og forutsatt at når fenylradikalet Y er substituert med klor er fenylradikalet X substituert med brom. in which the phenyl radical X is unsubstituted or substituted in the p-position with bromine, chlorine or fluorine and the phenyl radical Y in the p-position is substituted with bromine, chlorine or iodine, provided that when the phenyl radical Y is substituted with bromine, the phenyl radical X is substituted with bromine or chlorine and provided that when the phenyl radical Y is substituted by chlorine, the phenyl radical X is substituted by bromine.
Det er blit funnet at støv, dispersjoner, emulsjoner, røk, tåke og aerosoler av forbindelsene med den ovenstående .generelle formel har egenskaper som gjør dem verdi-fulle ved kontroll av egg og aktive trinn av midd (Acari), særlig den planteetende te-tranychidae eller rødt midd, f. eks. tetra-nuchus telarius L og metatetranuchus ulmi Koch. Foreliggende oppfinnelse består der-for i forbindelsene med den ovenstående generelle formel og i støv, dispers joner, emulsjoner, tåker, røk og aerosoler av disse forbindelser som kan anvendes for have-bruksformål. It has been found that dusts, dispersions, emulsions, fumes, mists and aerosols of the compounds of the above general formula have properties which make them valuable in the control of eggs and active stages of mites (Acari), especially the herbivorous tea- tranychidae or red mite, e.g. tetra-nuchus telarius L and metatetranuchus ulmi Koch. The present invention therefore consists in the compounds with the above general formula and in dust, dispersion ions, emulsions, mists, smoke and aerosols of these compounds which can be used for gardening purposes.
Forbindelsene ifølge oppfinnelsen fåes ved reaksjon mellom det substituerte benzylhalogenid av den generelle formel The compounds according to the invention are obtained by reaction between the substituted benzyl halide of the general formula
hvor hal er et halogenatom og den tilsvarende tiol med den generelle formel where hal is a halogen atom and the corresponding thiol of the general formula
i nævær av et alkalisk kondensasjonsmiddel slik som natriumetoksyd, idet fenylradikalene X og Y er definert i det ovenstående. Kondensasjonen utføres fortrinsvis idet det anvendes natriumhydroksyd i et alkoholisk eller natriumetoksyd i et vannfritt medium. in the presence of an alkaline condensing agent such as sodium ethoxide, the phenyl radicals X and Y being defined above. The condensation is preferably carried out using sodium hydroxide in an alcoholic or sodium ethoxide in an anhydrous medium.
Dispersj onene som har en fast disper-gert fase ifølge oppfinnelsen kan omfatte det aktive stoff i kombinasjon med et dispersj onsmiddel og/eller et suspensjonsmid-del i vandig medium. Det er hensiktsmessig at preparatet består av aktivt stoff blandet med et dispersj onsmiddel og/eller et sus-pensj onsmiddel slik at det dannes en dispersj on når blandingen settes til vann. For å lette dannelsen av en dispersj on på denne måte kan preparatet som skal fortynnes også inneholde et vannblandbart organisk oppløsningsmiddel, f. eks. aceton. Dispersj onene ifølge oppfinnelsen omfatter også suspensjoner hvori den faste dispergerte fase er blandet med en vandig oljeemulsjon, idet det aktive stoff er vesentlig uoppløse-lig i oljen og oljen fortrinsvis er en ikke-flyktig olje, f. eks. flytende parafin. The dispersions which have a solid dispersed phase according to the invention may comprise the active substance in combination with a dispersing agent and/or a suspending agent in an aqueous medium. It is appropriate that the preparation consists of active substance mixed with a dispersing agent and/or a suspending agent so that a dispersion is formed when the mixture is added to water. To facilitate the formation of a dispersion in this way, the preparation to be diluted can also contain a water-miscible organic solvent, e.g. acetone. The dispersions according to the invention also include suspensions in which the solid dispersed phase is mixed with an aqueous oil emulsion, the active substance being essentially insoluble in the oil and the oil preferably being a non-volatile oil, e.g. liquid paraffin.
Emulsjonene fremstilt ifølge oppfinnelsen kan omfatte aktivt stoff i kombinasjon med et emulsj onsmiddel ,og et organisk oppløsningsmiddel, f. eks. xylol eller et aro-matisk oppløsningsmiddel som koker innenfor området 80—300° C. Det kan være for-delaktig å tilsette en ikke-flyktig vegetabilsk eller mineralsk olje slik som flytende parafin for å virke som aktivator og/eller som klebemiddel. Emulsjonspreparatet ifølge oppfinnelsen kan også inneholde et fuktningsmiddel. Preparatet kan hensiktsmessig bestå av aktivt stoff blandet med eller i oppløsning i et organisk oppløsnings-middel som beskrevet ovenfor sammen med et emulsj onsmiddel og hvis ønskes et fuktningsmiddel slik at det dannes en emulsjon ved blanding av preparatet med vann. Slik preparater utgjør også en del av foreliggende oppfinnelse. De vandige dispersjoner og emulsjoner som er beskrevet i det ovenstående, kan være fortynnet med vann før anvendelsen for å oppnå en endelig konsentrasjon av aktivt stoff innenfor området av 0,001—10 pst. beregnet som vekt pr. volum, men oppfinnelsen er ikke be-grenset til preparater som inneholder denne konsentrasjon av aktivt stoff. Konsentra-sjonen i oppløsningene som anvendes av-henger av de krav som stilles for det spe-sielle sprøytemaskiner som anvendes. . Dispersjoner av aktivt stoff hvor basen er et pulverformet fast fortynningsmiddel utgjør også en del av foreliggende oppfinnelse. Slike dispersjoner kan inneholde opp til 50 pst. beregnet som vekt pr. volum av det aktive stoff. The emulsions produced according to the invention can comprise active substance in combination with an emulsifier and an organic solvent, e.g. xylol or an aromatic solvent boiling in the range 80-300° C. It may be advantageous to add a non-volatile vegetable or mineral oil such as liquid paraffin to act as an activator and/or as an adhesive. The emulsion preparation according to the invention can also contain a wetting agent. The preparation can suitably consist of active substance mixed with or in solution in an organic solvent as described above together with an emulsifying agent and, if desired, a wetting agent so that an emulsion is formed by mixing the preparation with water. Such preparations also form part of the present invention. The aqueous dispersions and emulsions described in the above can be diluted with water before use to achieve a final concentration of active substance within the range of 0.001-10 percent calculated as weight per volume, but the invention is not limited to preparations containing this concentration of active substance. The concentration in the solutions used depends on the requirements for the special spraying machines used. . Dispersions of active substance where the base is a powdered solid diluent also form part of the present invention. Such dispersions can contain up to 50 percent calculated as weight per volume of the active substance.
Det er nå blitt funnet at det er mulig å anvende forbindelsene med den ovenstående generelle formel i form av røk, tåker og aerosoler. Denne anvendelsesmåte er meget hensiktsmessig når de planter som det er ønskelig å behandle for å kon-trollere midd, er anbrakt i lukkede områder, f. eks. i drivhus. It has now been found that it is possible to use the compounds of the above general formula in the form of fumes, mists and aerosols. This method of application is very appropriate when the plants which it is desirable to treat to control mites are placed in closed areas, e.g. in a greenhouse.
Foreliggende oppfinnelse omfatter der-for også preparater for fremstilling av aka-ricide tåker og aerosoler som inneholder som aktivt stoff en forbindelse med den ovenstående generelle formel. The present invention therefore also includes preparations for the production of acaricidal mists and aerosols which contain as active substance a compound with the above general formula.
Ved fremstilling av tåker og aerosoler som inneholder som aktivt stoff forbindelser med den ovenstående generelle formel, kan det aktive stoff oppløses i en blanding av en ikke-flyktig olje, slik som vegetabilsk olje og et ekstra blandbart oppløsnings-middel, slik som cykloheksanon eller aceton. Den således erholdte oppløsning kan dispergeres ved mekaniske midler eller ved å innføre i oppløsningen et flyktig drivmid-del, slik som Freon (en blanding av kloro-fluorderivater av metan og etan). Følgende eksempler illustrerer oppfinnelsen. In the production of mists and aerosols containing as active substance compounds with the above general formula, the active substance can be dissolved in a mixture of a non-volatile oil, such as vegetable oil, and an additional miscible solvent, such as cyclohexanone or acetone . The solution thus obtained can be dispersed by mechanical means or by introducing into the solution a volatile propellant, such as Freon (a mixture of chlorofluoroderivatives of methane and ethane). The following examples illustrate the invention.
Eksempel 1: Example 1:
Ved fremstilling av p-bromobenzyl-p- bromofenylsulfid oppløses 1,0 g natrium i In the preparation of p-bromobenzyl-p- bromophenyl sulphide dissolve 1.0 g sodium in
en blanding av 6,3 g p-bromof enyltioi og 100 cm<3> vannfri etanol. Oppløsningen til-settes 6,9 g p-bromobenzylklorid og blandingen opphetes med tilbakeløpskjøler i 1,5 time. Produktet tillates å avkjøle og hel-les i 150 cm<3> vann. Det faste stoff som skil-les ut, isoleres ved filtrering og omkrystal-liseres fra vandig alkohol. Det fåes således p-brombenzyl-p-bromfenylsulfid i form av et krystallinsk fast stoff som har et smeltepunkt på 106-107° C (funnet C, 43,9; H, 2,7; a mixture of 6.3 g of p-bromofenylthio and 100 cm<3> of anhydrous ethanol. 6.9 g of p-bromobenzyl chloride are added to the solution and the mixture is heated with a reflux condenser for 1.5 hours. The product is allowed to cool and poured into 150 cm<3> of water. The solid substance that separates is isolated by filtration and recrystallized from aqueous alcohol. p-Bromobenzyl-p-bromophenyl sulphide is thus obtained in the form of a crystalline solid which has a melting point of 106-107° C (found C, 43.9; H, 2.7;
C13HioBr2S krever C, 34,6; H, 2,8). C13HioBr2S requires C, 34.6; H, 2.8).
På liknende måte fremstilles det føl-gende forbindelse av den tilsvarende fenyltiol og det tilsvarende benzylhalogenid. In a similar way, the following compound is prepared from the corresponding phenylthiol and the corresponding benzyl halide.
p-brombenzyl-p-klorfenylsulfid sm.p. p-bromobenzyl-p-chlorophenyl sulfide m.p.
87-88° C. 87-88°C.
Funnet: C, 49,6: H, 3,05: CmHioBr C1S krever C, 49,8; H, 3,2. Found: C, 49.6: H, 3.05: CmHioBr C1S requires C, 49.8; H, 3.2.
Eksempel 2: Example 2:
Ved fremstilling av p-klorbenzyl-p-bromfenylsulfid settes en oppløsning av 3,2 g natriumhydroksyd i 50 cm<3> vannfri metanol til en varm oppløsning av 10,9 g p-klor-benzylklorid og 13,5 g p-bromfenyltiol i 50 cm:! vannfri metanol. Etter tilsetning opphetes blandingen med tilbakeløpskjøler i 30 minutter. Det meste av oppløsningsmidlet fjernes ved destillasjon, og overskudd av koldt vann settes til residuet. Det utfelte faste stoff isoleres ved filtrering og omkry-stalliseres to ganger fra etanol. Det fåes således p-bromfenyl-p-klorbenzylsulfid i form av et krystallinsk fast stoff som har et smeltepunkt på 87-88° C. In the preparation of p-chlorobenzyl-p-bromophenyl sulfide, a solution of 3.2 g of sodium hydroxide in 50 cm<3> of anhydrous methanol is added to a hot solution of 10.9 g of p-chlorobenzyl chloride and 13.5 g of p-bromophenylthiol in 50 cm:! anhydrous methanol. After addition, the mixture is heated with a reflux condenser for 30 minutes. Most of the solvent is removed by distillation, and an excess of cold water is added to the residue. The precipitated solid is isolated by filtration and recrystallized twice from ethanol. Thus p-bromophenyl-p-chlorobenzyl sulphide is obtained in the form of a crystalline solid which has a melting point of 87-88°C.
Funnet: C, 49,6; H, 3,2: CsHmBr C1S Found: C, 49.6; H, 3.2: CsHmBrC1S
krever C, 49,8; H, 3,2). requires C, 49.8; H, 3.2).
På liknende måte fremstilles det fra den tilsvarende fenyltiol og den tilsvarende benzylhalogenid p-fluorbenzyl p-bromfenylsulfid med sm.p. 65,5—57,5° C. In a similar way, it is prepared from the corresponding phenylthiol and the corresponding benzyl halide p-fluorobenzyl p-bromophenyl sulfide with m.p. 65.5—57.5° C.
(Funnet: C, 52,9; H, 3,4: CnHioBr FS (Found: C, 52.9; H, 3.4: CnHioBr FS
krever C, 52,5; H, 3,4). requires C, 52.5; H, 3,4).
p-klorfenyl p-jodbenzylsulfid sm.p. p-chlorophenyl p-iodobenzyl sulfide m.p.
101° C. 101°C.
(Funnet: C, 43,5; H, 2,8: CjsHmCl JS krever C, 43,3; H, 2,8). p-fluorfenyl-p-jodbenzylsulfid sm.p. 54,5-56° C. (Found: C, 43.5; H, 2.8: CjsHmCl JS requires C, 43.3; H, 2.8). p-fluorophenyl-p-iodobenzyl sulfide m.p. 54.5-56°C.
(Funnet: C, 45,3; H, 3,0: CisHioFJS krever C, 45,3; H, 2,9). (Found: C, 45.3; H, 3.0: CisHioFJS requires C, 45.3; H, 2.9).
p-jodbenzylfenylsulfid sm.p. 87-88,5° C. p-iodobenzylphenylsulfide m.p. 87-88.5°C.
(Funnet: C 48,0; H, 3,3: CisHnJS krever C, 47,9; H, 3,4). p-bromfenyl-p-jodbenzylsulfid sm.p. 117-118° C. (Found: C 48.0; H, 3.3: CisHnJS requires C, 47.9; H, 3.4). p-bromophenyl-p-iodobenzyl sulfide m.p. 117-118°C.
Funnet: C, 38,8; H, 2,4: CjsHioBr JS krever C, 38,5; H, 2,5). Found: C, 38.8; H, 2.4: CjsHioBr JS requires C, 38.5; H, 2.5).
Eksempel 3: Ved fremstilling av et dispergerbart pulver blandes 20 vektsdeler p-brombenzyl-p-bromfenylsulfid grundig med 8 vektsdeler Belloid T.D. (et kondensat av formaldehyd og et alkyl-arylsulfonat) og 72 vektsdeler kaolin. Dette preparat kan settes til vann slik at det dannes en stabil dispersj on eg-net for hagebruksformål. Example 3: When preparing a dispersible powder, 20 parts by weight of p-bromobenzyl-p-bromophenyl sulphide are thoroughly mixed with 8 parts by weight of Belloid T.D. (a condensate of formaldehyde and an alkyl aryl sulfonate) and 72 parts by weight of kaolin. This preparation can be added to water so that a stable dispersion suitable for horticultural purposes is formed.
Eksempel 4: Ved fremstilling av et preparat som egner seg for fortynning med vann for å oppnå en stabil emulsjon oppløses det tilstrek-kelig p-klorbenzyl-p-bromfenylsulfid i en blanding av 10 volumdeler Insem 108 (et ikke-jonisk emulsj onsmiddel som antas å være en oleinsyreester av en glykol) og 90 volumdeler benzol for å oppnå en oppløs-ning som inneholder 5 pst. beregnet som vekt pr. volum aktivt stoff. Example 4: When preparing a preparation that is suitable for dilution with water to obtain a stable emulsion, the sufficient amount of p-chlorobenzyl-p-bromophenyl sulfide is dissolved in a mixture of 10 parts by volume of Insem 108 (a non-ionic emulsifier which is assumed to be an oleic acid ester of a glycol) and 90 parts by volume of benzene to obtain a solution containing 5 percent calculated as weight per volume of active substance.
Eksempel 5: Ved fremstilling av et preparat som egner seg for fortynning med vann for å oppnå en stabil emulsjon oppløses tilstrek-kelig p-jodbenzylfenylsulfid i en blanding av 10 volumdeler Insem 108 (et ikke-jonisk emulsj onsmiddel som antas å være en oleinsyreester av en glykol) og 90 volumdeler benzol for å oppnå en oppløsning som inneholder 10 pst. beregnet som vekt pr. volum aktivt stoff. Example 5: When preparing a preparation suitable for dilution with water to obtain a stable emulsion, sufficient p-iodobenzylphenylsulfide is dissolved in a mixture of 10 parts by volume of Insem 108 (a non-ionic emulsifier which is believed to be an oleic acid ester of a glycol) and 90 parts by volume of benzene to obtain a solution containing 10 per cent calculated as weight per volume of active substance.
Liknende dispersjoner og preparater som beskrevet i eksemplene 3, 4 og 5 kan fremstilles hvori det aktive stoff som spesi-elt er nevnt er erstattet med en hvilken som helst av de forbindelser som er opp-ført i eksemplene 1 og 2. Similar dispersions and preparations as described in examples 3, 4 and 5 can be prepared in which the active substance that is specifically mentioned is replaced by any of the compounds listed in examples 1 and 2.
Claims (3)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DED0052301 | 1967-02-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
NO116277B true NO116277B (en) | 1969-02-24 |
Family
ID=7054060
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO170854A NO116277B (en) | 1967-02-17 | 1967-12-05 |
Country Status (9)
Country | Link |
---|---|
US (1) | US3547033A (en) |
BE (1) | BE710176A (en) |
DE (1) | DE1646334C3 (en) |
FI (1) | FI50280C (en) |
FR (1) | FR1554361A (en) |
GB (1) | GB1204927A (en) |
NL (1) | NL6801715A (en) |
NO (1) | NO116277B (en) |
SE (1) | SE343390B (en) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE407286B (en) * | 1975-11-07 | 1979-03-19 | Bofors Ab | FUSE DEVICE |
US4172421A (en) * | 1978-03-30 | 1979-10-30 | Jet Research Center, Inc. | Fluid desensitized safe/arm detonator assembly |
FR2428233A1 (en) * | 1978-06-08 | 1980-01-04 | Ruggieri Ets | Delayed action primer for hand grenade - has percussion mechanism and delay type primer with safety screen at explosive side |
AU514818B2 (en) * | 1979-06-25 | 1981-02-26 | Jet Research Center Inc. | Fluid-desensitized safe/arm detonator assembly |
US4319526A (en) * | 1979-12-17 | 1982-03-16 | Schlumberger Technology Corp. | Explosive safe-arming system for perforating guns |
FR2560984B1 (en) * | 1984-03-09 | 1987-12-11 | Maury Louis | ELECTRIC DEVICE FOR PYROTECHNIC INITIATION OF THE DETONATOR AND FUSE TYPE INCORPORATING SUCH A DEVICE |
CN112780204A (en) * | 2019-11-07 | 2021-05-11 | 中国石油天然气股份有限公司 | Releasing device and releasing method |
-
1967
- 1967-02-17 DE DE1646334A patent/DE1646334C3/en not_active Expired
- 1967-12-05 NO NO170854A patent/NO116277B/no unknown
-
1968
- 1968-01-24 FI FI680186A patent/FI50280C/en active
- 1968-01-31 BE BE710176D patent/BE710176A/xx unknown
- 1968-02-07 NL NL6801715A patent/NL6801715A/xx unknown
- 1968-02-13 FR FR1554361D patent/FR1554361A/fr not_active Expired
- 1968-02-14 SE SE1924/68A patent/SE343390B/xx unknown
- 1968-02-15 GB GB7565/68A patent/GB1204927A/en not_active Expired
- 1968-02-19 US US706570A patent/US3547033A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
US3547033A (en) | 1970-12-15 |
FI50280C (en) | 1976-01-12 |
DE1646334A1 (en) | 1971-07-08 |
FR1554361A (en) | 1969-01-17 |
DE1646334C3 (en) | 1973-11-22 |
DE1646334B2 (en) | 1973-04-26 |
GB1204927A (en) | 1970-09-09 |
NL6801715A (en) | 1968-08-19 |
BE710176A (en) | 1968-05-30 |
FI50280B (en) | 1975-09-30 |
SE343390B (en) | 1972-03-06 |
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