NO751314L - - Google Patents
Info
- Publication number
- NO751314L NO751314L NO751314A NO751314A NO751314L NO 751314 L NO751314 L NO 751314L NO 751314 A NO751314 A NO 751314A NO 751314 A NO751314 A NO 751314A NO 751314 L NO751314 L NO 751314L
- Authority
- NO
- Norway
- Prior art keywords
- bis
- pyridine
- reaction
- trichloro
- mixture
- Prior art date
Links
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Chemical group 0.000 claims description 2
- DOJKHTWRFHKSFU-UHFFFAOYSA-N [2,3,5-trichloro-6-(thiocyanatomethylsulfanyl)-1H-pyridin-2-yl]sulfanylmethyl thiocyanate Chemical group ClC1=C(NC(C(=C1)Cl)(SCSC#N)Cl)SCSC#N DOJKHTWRFHKSFU-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 230000000361 pesticidal effect Effects 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000003440 toxic substance Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 231100000167 toxic agent Toxicity 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 2
- 239000010730 cutting oil Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- CXURGFRDGROIKG-UHFFFAOYSA-N 3,3-bis(chloromethyl)oxetane Chemical compound ClCC1(CCl)COC1 CXURGFRDGROIKG-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241001465318 Aspergillus terreus Species 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000208680 Hamamelis mollis Species 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241000187481 Mycobacterium phlei Species 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- -1 building boards Substances 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 229940055036 mycobacterium phlei Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229940118846 witch hazel Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Fats And Perfumes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
"Peoticide halogen-bi»(tio-cyanstometyltio)-pyridiner"
Foreliggende oppfinnelse gjelder pesticide h^logen-bis-(tiocy?>np?.tomatyltio) pyridiner som er særegne ved *t de h?r forme-lent
I denne og etterfølgende formler betyr X klor eller brom
og n betyr et tnll p5 ? eller 3.
Forbindelsene ifølge oppfinnelsen er krystalliske faste3toffer ellar oljar som hnr liten løselighet i v onn og moderat lø-selighet i vnlige orgnniake løsningsmidler. Disse forbindelser hsr lr.v fytotoksisitet og er egnet for anvendelse som baktericider og fungicider.
Forbindelsene ifølge oppfinnelsen kon fremstilles ved reaksjon mellom et p->«?sende halogensubstituert 2, 4-bis-[ (klorroetyl) -tiol-pyridin (fremstilt sons vist i US patent nr. 3.549.647) og et ælkrali-raetPlltiocy<p>n~t i na?rva»r nv et løsningsmiddel. Denne reaksjon kan representeres ora følger»
hvor X og n er som for*»n definert og Me betyr natrium, litium, kalium, cesium eller rubidium.
Ved utførelsen av denne reaksjon bringes reaktantene i kontakt med hverandre i nærvær av et løsningsmiddel som f.eks. dimetylformomid, heksametylfosfommid eller 4-formylmorfolin. Reaksjonen utføres ved temperaturer i området fra 105 til 150°C. Reaksjonen utføres vanligvis ved atmosfærisk trykk. Mens renksjo-neneforbruker reaktantene i forholdet 7 mol<p>lkalimetrlltiocyanat til en mol pyridinstartmateritile, er det foretrukket å anvende et overskudd<p>v opp til 3 ganger den støkiometriske mengde av tiocya-nrstet.
Rer>ks jonsdeltagerne holdes sammen under omrøring inntil reaksjonen er fullstendig. Den nødvendige reaksjonstid er vanligvis mellom 30 minutter og 4 timer. Når reaksjonen er ferdig, for-tynnes re«ksjon«sblandingen med knldt vann for å felle ut eventuelt fnst stoff. Det fuste produktet kan om ønsket renses ved ornkrystal-1 isn sjon fra bensren, hekssn. penton «Iler blandinger derav.
Forbindelsene ifølge oppfinnelsen kan anvendes for bekjem-pelse av mnnge bakterie- og sopporgr»nismer.Forbindelsene ifølge oppfinnelsen eller preparater som inneholder dem som toksiske be-standdeler kr*n innblandes i mørtel, trykksverte, bygningsplater, tekstiler, pnpir, lim, såper, syntetiske detergenter, skjæreoljer, polymere materialer, bnlsnmeringsvæsker, oljemalinger og lnteks-mrilinger for 5. hindre angrep ov forskjellige soppsykdéMKto r og det følgende Økonomiske tsp på grunn av nedbrytning av slike produfctar i?v mikroorganismer. Forbindelsene kan også fordeles i tekstiler eller cellulosematerialer for å konservere og beskytte slike materialer mot nngrep fræ råte-, mugg- og forfall3orgnnismer.
Den nøyaktige konsentrasjon av det toksiske stoff i be-hnndlingsprepnrnter er ikke kritisk og kan variere betydelig for-utsatt r>t den nødvendige dosering av det effektive middelet tilføres til trykksverten, limet, såpen, skjæreoljen, det polymere mcterialet, malingen, tekstilen, papiret eller vekstmediet. Konsentrasjonen av det toksiske stoffet i væskeprepamter er vanligvis fra 0.0001 til 50 vekt%. Konsentrasjoner opp til 95 vekt% cnvendes hensiktsmessig mrnge ganger og spesielt i konsentrerte preparater . I støv kan konsentrrsjonene av toksisk middel være frn 0,1 til 95 vekt%. I prep.imter som skal anvendes som konsentrater kan de toksiske stof-fene være tilstede i en konsentrasjon sv frp 5 til 98 vekt%. For anvendelse som sprny er det ofte hensiktsmessig å fremstille forbindelsene som fuktbore pulvere.
I et representativt forsøk ble det funnet at 3,5,6-triklor-?. 4-bis-(tiocyRnatometyltio)pyridin, når det bl©anvendt som det eneste toksiske stoff i etl næringsagar i en konsentrasjon av 10 vektdeler «v forbindelsen pr. million deler agar, bekjempet 100% 5V orgnnismane Stnphylococcus cmreus, Mycobacterium phlei, Bacillus subtilis, Trichophyton mentagrophytes, Cerotocystia ips
og Aspergillus terreus.
Det følgende eksempel illustrerer foreliggende oppfinnelse.
Eksempal 1
Tii on omrørt løsning<p>v 11,87 grnm (0,1? mol) koliumtio-cysnst i 35 ml diiietylformsmid ble det tilsatt 7,0 gram (0,0? mol) 3,5,6-triklo;-2,4-bis(klormetyltio)pyridin i 25 ml dimetylformnmid ved 60°C. Etter j»t tilsetningen var fullstendig ble temperaturen hevet til 100°C og blandingen holdt på denne temperatur med omrør-ing i on timer Deretter ble temperaturen hevet til 140°c og blen-dingen boldt der i 15 minutter. Temperaturen ble senket til 110°C og blandingen holdt vedodenne temperntur i on time. Ds reaksjonen v?r ferdig ble re?"ksjonsbl^ndingen avkjølt oghhelt i isvnnn. Det fm ste-stoff som fnit ut ble utvunnet ved filtrering og tørket. Det fnste stoffat ble tatt opp i varmt benzen, tørket over natriuia-sul£?t og filtrert varmt* Ben.ronet ble fjernet til det vor igjen 1/3 o.v. volumet og hek sn n ble tilsatt. Blandingen ble avkjølt og det ønskede 3,5.6-triklor-a,4-bis-(tiocyonatometyltio)pyridin som falt ut ble utvunnet ved filtrering. Produktet smeltet ved 96°C og ble oppnådd i utbytte på 2,2 gram (27%). Produktet ble funnet 3 ha karbon-, hydrogen-, klor-, nitrogen- og svovelinnhold på 77, 2. 1, 7, 28.2, 10.4. og 31.4% respektive, sammenlignet med de teoretiske innhold på 37,8, 1,0. 27,4, 10,3 og 33,0 respektive.
Følgende forbindelser ifølge oppfinnelsen er fremstilt ifølge den metodersom er angitt foran.
3, 5-diklor - 7-, 4-bis~(tiocyan^toraotyltio) pyridin. 3. 5-dibrorn-?. 4-bis-(tiocynnatom3tyltio) pyridin.
3, 5,6-tribrom-»?, 4-bis (tiocy.^natometyltio) pyridin.
3,5,6-triklor-?,4-bis~(tiocynn?tometyltio)pyridin.
Claims (2)
1. Pjesticide hrilogen-bis-(tiocypnstoirøtyltio) -pyridiner, karakterisert ved at de hnr formicieni
hvor x er klor eller brom og n er et helt tall på f rn 2 til 3.
2. Forbindelse ifølge krov 1, karakterisert ved? it den er 3,5,6-triklor-2, 6-bis (tiocyanatometyltio) pyridin.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US461063A US3894035A (en) | 1974-04-15 | 1974-04-15 | Bis-(thioalkylthio cyanato)halo pyridines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO751314L true NO751314L (no) | 1975-10-16 |
Family
ID=23831074
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO751314A NO751314L (no) | 1974-04-15 | 1975-04-14 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3894035A (no) |
| JP (1) | JPS50140461A (no) |
| CA (1) | CA1027569A (no) |
| DE (1) | DE2515773A1 (no) |
| ES (1) | ES436374A1 (no) |
| GB (1) | GB1472022A (no) |
| NL (1) | NL7504115A (no) |
| NO (1) | NO751314L (no) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4994252A (en) * | 1990-02-09 | 1991-02-19 | Dowelanco | Removal of potassium chloride from solvents |
| JP2587377Y2 (ja) * | 1992-02-17 | 1998-12-16 | 日本バイリーン株式会社 | 作業用ワイパー |
| WO1998054139A1 (de) * | 1997-05-30 | 1998-12-03 | Basf Aktiengesellschaft | Verfahren zur herstellung substituierter thiopyridine |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3758482A (en) * | 1971-06-30 | 1973-09-11 | Dow Chemical Co | Halopyridyl thiocyanates |
| US3787425A (en) * | 1973-02-09 | 1974-01-22 | Dow Chemical Co | Halopyridyl thiocyanates |
| US3787422A (en) * | 1973-02-09 | 1974-01-22 | Dow Chemical Co | Halopyridyl thiocyanates |
-
1974
- 1974-04-15 US US461063A patent/US3894035A/en not_active Expired - Lifetime
-
1975
- 1975-04-07 ES ES436374A patent/ES436374A1/es not_active Expired
- 1975-04-07 NL NL7504115A patent/NL7504115A/xx unknown
- 1975-04-08 CA CA224,021A patent/CA1027569A/en not_active Expired
- 1975-04-09 GB GB1460075A patent/GB1472022A/en not_active Expired
- 1975-04-10 DE DE19752515773 patent/DE2515773A1/de active Pending
- 1975-04-10 JP JP50043861A patent/JPS50140461A/ja active Pending
- 1975-04-14 NO NO751314A patent/NO751314L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3894035A (en) | 1975-07-08 |
| JPS50140461A (no) | 1975-11-11 |
| NL7504115A (nl) | 1975-10-17 |
| DE2515773A1 (de) | 1975-10-23 |
| ES436374A1 (es) | 1977-01-16 |
| GB1472022A (en) | 1977-04-27 |
| CA1027569A (en) | 1978-03-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1180708A (en) | Process for preparing organic sulphides | |
| NO751314L (no) | ||
| US3641004A (en) | Alkyl esters of 6-(benzenesulfonyl)-trihalo-2-picolinic acid | |
| US3888868A (en) | Preparation of chloropyridylsulfone-n-oxides | |
| US3758482A (en) | Halopyridyl thiocyanates | |
| US3197495A (en) | S-(10-phenoxarsinyl) 2-phenoxyethyl xanthate | |
| US3787422A (en) | Halopyridyl thiocyanates | |
| US3639413A (en) | (thio- sulfinyl- and sulfonyl) containing pyridine compounds | |
| US3787425A (en) | Halopyridyl thiocyanates | |
| US3850929A (en) | (1,2,5)thiadiazolo(3,4-b)pyrazines | |
| CN109206363A (zh) | 一种制备2-氯烟酸的绿色新工艺 | |
| US3393209A (en) | Furfuryl and tetrahydrofurfuryl phenyl ureas | |
| US3197494A (en) | S-(10-phenoxarsinyl) xanthates | |
| NO751315L (no) | ||
| US3591596A (en) | 1,2-dihydro - 6 -methyl-2-oxo-4-pyridyl esters of certain benzene sulfonic acids and derivatives thereof | |
| NO751311L (no) | ||
| US3117146A (en) | Organotin hydroxides | |
| NO751313L (no) | ||
| EP0018100B1 (en) | Substituted aromatic biologically active compound, a process for its preparation and its use as biocide | |
| US3674795A (en) | Pyridyl xanthates | |
| GB882541A (en) | New unsaturated thiophosphoric acid esters | |
| US3719682A (en) | (thio-,sulfinyl-and sulfonyl)containing pyridine compounds | |
| US3635994A (en) | Halopyridine sulfenyl- and sulfonylhalides | |
| US2922791A (en) | Certain pyridine-2-dithiophosphonate, n-oxides | |
| US3226427A (en) | Carbamate thiosulfonates |