NO115345B - - Google Patents
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- NO115345B NO115345B NO157521A NO15752165A NO115345B NO 115345 B NO115345 B NO 115345B NO 157521 A NO157521 A NO 157521A NO 15752165 A NO15752165 A NO 15752165A NO 115345 B NO115345 B NO 115345B
- Authority
- NO
- Norway
- Prior art keywords
- mites
- production
- trihalobenzene
- halogen
- hig
- Prior art date
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 241000238876 Acari Species 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 241001454295 Tetranychidae Species 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000000575 pesticide Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 9
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 5
- 235000013601 eggs Nutrition 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- OQBAIYJURBWUML-UHFFFAOYSA-N sulfurochloridic acid 1,2,4-trichlorobenzene Chemical compound S(=O)(=O)(O)Cl.ClC1=CC=C(C(=C1)Cl)Cl OQBAIYJURBWUML-UHFFFAOYSA-N 0.000 description 2
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 2
- CZNPEAXFCSYHTD-UHFFFAOYSA-N 1,2,3-trichloro-5-(4-chlorophenyl)sulfonylbenzene Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C(Cl)=C1 CZNPEAXFCSYHTD-UHFFFAOYSA-N 0.000 description 1
- MMYVDBHFYSHDSL-UHFFFAOYSA-N 1,2-dichloro-4-(3,4-dichlorophenyl)sulfonylbenzene Chemical compound C1=C(Cl)C(Cl)=CC=C1S(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 MMYVDBHFYSHDSL-UHFFFAOYSA-N 0.000 description 1
- GVOBBMKHUZFSHB-UHFFFAOYSA-N 2,4,5-trichlorobenzenesulfonamide Chemical class NS(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl GVOBBMKHUZFSHB-UHFFFAOYSA-N 0.000 description 1
- GPAPPPVRLPGFEQ-UHFFFAOYSA-N 4,4'-dichlorodiphenyl sulfone Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 GPAPPPVRLPGFEQ-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- 241000219122 Cucurbita Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 102000011782 Keratins Human genes 0.000 description 1
- 108010076876 Keratins Proteins 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 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
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000013014 purified material Substances 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
- H01J23/00—Details of transit-time tubes of the types covered by group H01J25/00
- H01J23/02—Electrodes; Magnetic control means; Screens
- H01J23/06—Electron or ion guns
- H01J23/065—Electron or ion guns producing a solid cylindrical beam
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
- H01J3/00—Details of electron-optical or ion-optical arrangements or of ion traps common to two or more basic types of discharge tubes or lamps
- H01J3/02—Electron guns
- H01J3/027—Construction of the gun or parts thereof
Landscapes
- Microwave Tubes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Particle Accelerators (AREA)
Description
Fremgangsmåte til fremstilling av polyhalogendifenylsulfoner og midler innehol-dende disse forbindelser til å bekjempe utviklingsfasene av midder. Process for the production of polyhalogendiphenylsulfones and agents containing these compounds to combat the developmental phases of mites.
For å beskytte tekstilvarer mot angrep To protect textile goods from attack
fra møll er det blitt foreslått å behandle from moths it has been proposed to treat
slike varer med forbindelser av den almindelige formel such goods with compounds of the general formula
hvor B og X bl. a. kan bety halogensubsti-tuerte bensolradikaler. Som sådanne kun-ne f. eks. også 4,4' diklorfenylsulfon, 3.4-diklorfenylsulfon, 2, 4, 4'-triklordifenylsulfon, 3,4,4'-triklordifenylsulfon, 2,3'4,4' kom-me til anvendelse. where B and X among others a. can mean halogen-substituted benzene radicals. As such only, e.g. also 4,4'-dichlorophenylsulfone, 3,4-dichlorophenylsulfone, 2,4,4'-trichlorodiphenylsulfone, 3,4,4'-trichlorodiphenylsulfone, 2,3'4,4' can be used.
Som bekj empningsmiddel mot i hus og As a means of combating in houses and
på planter levende skadelige insekter som on plants living harmful insects which
ikke eter keratin, eller utviklingsfaser av not ether keratin, or developmental stages of
slike insekter, med unntak av møll-larver, such insects, with the exception of moth larvae,
er det videre blitt foreslått forbindelsene Furthermore, the connections have been suggested
av den almindelige formel of the general formula
hvor Ar betegner et bensolradikal som i hvert fall i parastilling fører en bestand-del som ikke gir foranledning til saltdan-nelse og enn videre ikke inneholder noe kullstoff, Q er en organisk rest, Y svovel eller en svovelholdig gruppe, hvor Ar og Q er direkte bundet til svovelet. Som sådanne er 3,4,4'-triklordifenylsulfon, 2,4,4'-triklordifenylsulfon, 3,4,5,4'-tetraklordife-nylsulfon, 4,4'-diklorfenylsulfon og videre ved kvelstoffet acylert 2,4,5-triklorfenylsul-fonamid blitt foreslått. Enn videre ble det offentliggjort at difenylsulfon dreper egg av spinnmidder. Selv om paraklordifenylsulfon likeledes skal ha denne virkning er dette ikke til-fellet med 4,4'-diklordifenylsulfon. Oppfinnelsen angår polyhalogensub-stituerte difenylsulfoner som er meget godt egnet til å bekjempe utviklingsfasene av midder. Oppfinnelsen består i en fremgangsmåte til fremstilling av polyhalogensubsti-tuerte difenylsulfoner av den almindelige formel where Ar denotes a benzene radical which, at least in the para position, leads to a component which does not give rise to salt formation and furthermore does not contain any carbon, Q is an organic residue, Y sulfur or a sulphur-containing group, where Ar and Q are directly bound to the sulfur. As such, 3,4,4'-trichlorodiphenylsulfone, 2,4,4'-trichlorodiphenylsulfone, 3,4,5,4'-tetrachlorodiphenylsulfone, 4,4'-dichlorophenylsulfone and further at the nitrogen are acylated 2,4,5 -trichlorophenylsulfonamide has been proposed. Furthermore, it was announced that diphenylsulfone kills spider mite eggs. Although parachlorodiphenylsulfone should also have this effect, this is not the case with 4,4'-dichlorodiphenylsulfone. The invention relates to polyhalogen-substituted diphenylsulfones which are very well suited to combating the development phases of mites. The invention consists in a method for producing polyhalogen-substituted diphenylsulfones of the general formula
hvor Hig betegner et halogenatom og X en fenylgruppe, hvor vannstoff på stedet 4 eller på stedene 2, 4 og 5 (i kombinasjon) kan være substituert med halogen. Hen-siktsmessig utgjøres halogenet av klor. where Hig denotes a halogen atom and X a phenyl group, where hydrogen at position 4 or at positions 2, 4 and 5 (in combination) may be substituted with halogen. Conveniently, the halogen is made up of chlorine.
Fremstillingen av forbindelsene i henhold til oppfinnelsen kan skje på for fremstilling av polyhalogendifenylsulfoner i og for seg kjent måte, f. eks. ved at man sulfonerer 1, 2,4-trihalogenbensol med klorsulfonsyre og kobler det således erholdte trihalogenbensolsulfoklorid, under innflytelse av et kondensasjonsmiddel, f. eks. aluminiumklorid, med bensol resp. med monohalogenbensol eller 1,3,4-trihalogenbensol. The production of the compounds according to the invention can take place in a manner known per se for the production of polyhalogendiphenylsulfones, e.g. by sulfonating 1,2,4-trihalobenzene with chlorosulfonic acid and coupling the trihalobenzene sulfochloride thus obtained, under the influence of a condensing agent, e.g. aluminum chloride, with benzol or with monohalobenzene or 1,3,4-trihalobenzene.
Forsøk har vist at egg og nymfer av midder drepes av forbindelser av den nevnte formel, spesielt klorforbindelsene, og at de voksne midders forplantningsdyk-tighet nedsettes av disse forbindelser. Experiments have shown that the eggs and nymphs of mites are killed by compounds of the aforementioned formula, especially the chlorine compounds, and that the reproductive capacity of the adult mites is reduced by these compounds.
De forhold under hvilke forsøkene ble foretatt blir i det følgende forklart nærmere. The conditions under which the experiments were carried out are explained in more detail below.
Oppfinnelsen omfatter enn videre en fremgangsmåte til fremstilling av et middel til å bekjempe utviklingsfasene av midder, særlig spinnmidder. I henhold til denne fremgangsmåte blir forbindelser av den nevnte almindelige formel, spesielt klorforbindelsene, fortynnet med et pulver som talkumpulver, dolomitmergel, kaolin eller tatt opp i et oppløsningsmiddel som f. eks. xylol, toluol. Fortrinsvis blir forbindelsene suspendert eller emulgert i vann eller de blir som sådanne enten løst opp i en med vann ikke blandbar væske, eller blandet med et i vann ikke oppløselig pulver. The invention further comprises a method for the production of an agent to combat the developmental stages of mites, in particular spider mites. According to this method, compounds of the aforementioned general formula, especially the chlorine compounds, are diluted with a powder such as talcum powder, dolomite marl, kaolin or taken up in a solvent such as e.g. xylol, toluene. Preferably, the compounds are suspended or emulsified in water or they are as such either dissolved in a water-immiscible liquid, or mixed with a water-insoluble powder.
For å undersøke forbindelsenes virk-somhet ble det foretatt forsøk på følgende måte: Bladet av en bønne (Phasaeolus) på hvilket det befant seg opp til tre dager gamle egg av spinnmidder (Tetranychus urticae Koch) ble dyppet i en emulsjon av et polyhalogendifenylsulfon i vann inntil det var fullstendig fuktet. Prøvene ble foretatt med tre polyklordifenylsulfoner In order to investigate the activity of the compounds, experiments were carried out in the following way: The leaf of a bean (Phasaeolus) on which there were up to three-day-old eggs of spider mites (Tetranychus urticae Koch) was dipped in an emulsion of a polyhalogendiphenyl sulfone in water until it was completely moistened. The tests were carried out with three polychlorodiphenylsulfones
(første spalte i den. nedenstående tabell) (first column in the table below)
og ved forskjellige konsentrasjoner av difenylsulfoner i vann (annen spalte). Den prosentvise mengde av de etter fire dager ikke utklekkede egg ble bestemt (tredje spalte) og likeledes dødsprosenten etter fire dager av de utklekkede nymfer (fjerde spalte). and at different concentrations of diphenylsulfones in water (second column). The percentage of eggs that did not hatch after four days was determined (third column) and likewise the death percentage after four days of the hatched nymphs (fourth column).
De foran nevnte forsøk viste enn videre at forbindelsen 2,4,5,4'-tetraklordife-nylsulfon ikke har noen bladbeskadigende virkning og har liten giftighet. Som for-søksgjenstand ble det bl. a. anvendt blader av agurker (Cucurbita) og bønner (Phasaeolus). Den lille giftighet viste seg derved at ved utlegning av 1100 mg av dette stoff pr. kg levendevekt av mus, var den toksiske grense ennå ikke nådd. The experiments mentioned above also showed that the compound 2,4,5,4'-tetrachlorodiphenyl sulfone has no leaf-damaging effect and has little toxicity. As a pre-trial object, it was, among other things, a. used leaves of cucumbers (Cucurbita) and beans (Phasaeolus). The low toxicity was thereby shown that when laying out 1100 mg of this substance per kg live weight of mice, the toxic limit had not yet been reached.
Oppfinnelsen skal bli nærmere forklart i forbindelse med eksempler på fremstilling av 2,4,5-triklorbensolsulfon og 2,4,5,4'-tetraklordifenylsulfon. The invention will be explained in more detail in connection with examples of the production of 2,4,5-trichlorobenzenesulfone and 2,4,5,4'-tetrachlorodiphenylsulfone.
Eksempel 1: Example 1:
Til tørr 1,2,4-triklorbensol (2,76 mol) ble det ved 90° og under omrøring dråpevis tilsatt 19 mol klorsulfonsyre, og deretter ble reaksjonsblandingen oppvarmet ca. 3 timer på dampbad. Etter avkjøling ble reaksjonsblandingen helt ut på is, og det rå 2,4,5-triklorbensolsulfoklorid ble omkry-stallisert fra petroleumseter (kokeområde 40—60° C). Det rensede stoff smeltet mel-lom 65 og 67° C. To dry 1,2,4-trichlorobenzene (2.76 mol) 19 mol of chlorosulfonic acid were added dropwise at 90° and with stirring, and then the reaction mixture was heated approx. 3 hours in a steam bath. After cooling, the reaction mixture was poured onto ice, and the crude 2,4,5-trichlorobenzene sulphochloride was recrystallized from petroleum ether (boiling range 40-60° C). The purified material melted between 65 and 67°C.
0,23 mol av den således fremstilte for- 0.23 mol of the product thus prepared
bindelse ble oppløst i 0,28 mol vann og tio-fenfri bensol, og til oppløsningen ble det ved romtemperatur og under omrøring tilsatt 0,23 mol aluminiumklorid. Reaksjonsblandingen ble i ca. iy2 time oppvarmet på et oljebad av 80 til 90° og deretter helt ut i isvann. Den erholdte utfelling ble renset ved at den ble oppløst i etylacetat og deretter utfelt igjen ved tilsetning av petroleumseter. Det erholdte 2,4,5-triklordifenylsulfon hadde et smelteområde fra 127 til 129° C. bond was dissolved in 0.28 mol of water and thiophene-free benzol, and 0.23 mol of aluminum chloride was added to the solution at room temperature and with stirring. The reaction mixture was for approx. iy2 hours heated in an oil bath of 80 to 90° and then poured into ice water. The precipitate obtained was purified by dissolving it in ethyl acetate and then reprecipitating by adding petroleum ether. The 2,4,5-trichlorodiphenylsulfone obtained had a melting range from 127 to 129°C.
Eksempel 2: Example 2:
En oppløsning av 0,2 mol 2,4,5-triklorbensolsulfoklorid, fremstilt i henhold til A solution of 0.2 mol of 2,4,5-trichlorobenzene sulfochloride, prepared according to
eksempel 1, i 0,22 mol klorbensol ble under omrøring og utelukkelse av fuktighet tilsatt 0,21 mol vannfritt aluminiumklorid ved en badtemperatur av ca. 60° C. Deretter ble reaksjonsblandingen ytterligere opphetet ca. 3 timer ved 90° og deretter example 1, 0.21 mol of anhydrous aluminum chloride was added to 0.22 mol of chlorobenzene while stirring and exclusion of moisture at a bath temperature of approx. 60° C. The reaction mixture was then further heated approx. 3 hours at 90° and then
helt ut i isvann. Utfellingen ble omkry-stallisert fra etanol og gav 2,4,5,4'-triklor-difenylsulfoklorid med et smelteområde av 146 til 148° C. completely in ice water. The precipitate was recrystallized from ethanol and gave 2,4,5,4'-trichlorodiphenylsulfochloride with a melting range of 146 to 148°C.
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DES90561A DE1297242B (en) | 1964-04-15 | 1964-04-15 | Electrode system for generating a magnetically focused full electron beam with a high current density |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO115345B true NO115345B (en) | 1968-09-23 |
Family
ID=7515913
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO157521A NO115345B (en) | 1964-04-15 | 1965-04-02 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3358173A (en) |
| DE (1) | DE1297242B (en) |
| GB (1) | GB1099873A (en) |
| NO (1) | NO115345B (en) |
| SE (1) | SE311957B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2251096B1 (en) * | 1973-11-13 | 1977-08-19 | Thomson Csf |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2567874A (en) * | 1948-08-28 | 1951-09-11 | Cage Projects Inc | Cathode-ray tube |
| GB762107A (en) * | 1953-03-26 | 1956-11-21 | Standard Telephones Cables Ltd | Improvements in or relating to electron guns |
| US2956192A (en) * | 1959-01-02 | 1960-10-11 | Eitel Mccullough Inc | Gettering electron gun |
-
1964
- 1964-04-15 DE DES90561A patent/DE1297242B/en not_active Withdrawn
-
1965
- 1965-04-02 NO NO157521A patent/NO115345B/no unknown
- 1965-04-12 US US447574A patent/US3358173A/en not_active Expired - Lifetime
- 1965-04-13 SE SE4870/65A patent/SE311957B/xx unknown
- 1965-04-14 GB GB15908/65A patent/GB1099873A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1297242B (en) | 1969-06-12 |
| US3358173A (en) | 1967-12-12 |
| SE311957B (en) | 1969-06-30 |
| GB1099873A (en) | 1968-01-17 |
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