SU259891A1 - METHOD OF OBTAINING 2-OXO-3-HRIZANTEMOILOXY- - Google Patents
METHOD OF OBTAINING 2-OXO-3-HRIZANTEMOILOXY-Info
- Publication number
- SU259891A1 SU259891A1 SU1261749A SU1261749A SU259891A1 SU 259891 A1 SU259891 A1 SU 259891A1 SU 1261749 A SU1261749 A SU 1261749A SU 1261749 A SU1261749 A SU 1261749A SU 259891 A1 SU259891 A1 SU 259891A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- oxo
- thio
- acid
- hrizantemoiloxy
- obtaining
- Prior art date
Links
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- FOHRCMUANUUOIL-UHFFFAOYSA-N 3-(hydroxymethyl)-1,3-benzoxazol-2-one Chemical compound C1=CC=C2OC(=O)N(CO)C2=C1 FOHRCMUANUUOIL-UHFFFAOYSA-N 0.000 claims description 2
- 206010008415 Chediak-Higashi syndrome Diseases 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N n-heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- VNTCVNLNEOVBEE-UHFFFAOYSA-N 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carbonyl chloride Chemical compound CC(C)=CC1C(C(Cl)=O)C1(C)C VNTCVNLNEOVBEE-UHFFFAOYSA-N 0.000 description 2
- 101700087259 CISH Proteins 0.000 description 2
- 241000723353 Chrysanthemum Species 0.000 description 2
- 235000007516 Chrysanthemum Nutrition 0.000 description 2
- 235000005986 Chrysanthemum x morifolium Nutrition 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 210000003165 Abomasum Anatomy 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- 230000000855 fungicidal Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 230000000749 insecticidal Effects 0.000 description 1
- 125000001810 isothiocyanato group Chemical group *N=C=S 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Description
Изобретение относитс к способу получени новых Соединений, обладающих высокой фунгицидной активностью.This invention relates to a process for the preparation of novel Compounds with high fungicidal activity.
Известна реакци 2,4-диоксо- или 2-тио-4оксо-3-оксиметилтиазолидина с хризантемкарбоновой кислотой или ее реакпиониоспособным производным. Полученные три этом соединени про вл ют инсектицидную активность .The reaction of 2,4-dioxo-or 2-thio-4oxo-3-hydroxymethylthiazolidine with chrysanthemocarboxylic acid or its reagion-derived derivative is known. The three compounds obtained exhibit insecticidal activity.
Предлагаетс способ получени 2-оксо-Зхризантемоилоксиметилбензоксазолина или 2тио -3 - хризантемоилоксиметилбензоксазолина общей формулыA method is proposed for the preparation of 2-oxo-Zhrizantemoyloxymethylbenzoxazoline or 2thio-3-chrysanthemoyloxymethylbenzoxazoline of the general formula
СНз SNS
CHnOCQCH- СН-СН С НзCHnOCQCH-CH-CH C Nz
0(8)0 (8)
//
НзС СНзNCS CHS
где X - водород, галоид, заключающийс в том, что 2-оксо-З-оксиметилбепзоксазолин или 2-тио-З-оксиметилбепзоксазолии .подвергают взаимодействию с хлорангидридом хризанчемовой кислоты в присутствии акцептора хлористого водорода, например пиридина. Процесс ведут лреимущественно при температуре О-9°С в среде органического растворител where X is hydrogen, halogen, which consists in the fact that 2-oxo-3-hydroxymethyl-benzoxazoline or 2-thio-3-hydroxymethyl-benzoxazolium is reacted with chrysanthemum chloride in the presence of a hydrogen chloride acceptor, for example pyridine. The process is carried out mainly at a temperature of about -9 ° C in an environment of an organic solvent
или без лего. Целевые продукты выдел ют известным способом, выход 90-93%.or without lego. The desired products are isolated in a known manner, yield 90-93%.
1. К суспензии 1,8 г (0.01 люль 2-тио-З-оксиметилбензоксазолина в 10 мл сухого толуола добавл ют при перемещиванпи 3,16 г fO,04 моль) сухого пиридина, затем прикапывают при температуре 5-9°С раствор 1.9 г (0,01 моль) хлорангидрида хризантемовой кислоты в 10 мл сухого толуола. Реакционную смесь пере мешивают в течение 5 час при комнатной тем111ературе, после чего отфильтровывают сол нокислую соль пиридина. Раствор последовательно экстрагируют 5%-ной сол ной кислотой, раствором бикарбоната натри , 1. To a suspension of 1.8 g (0.01 a lul of 2-thio-3-hydroxymethylbenzoxazoline in 10 ml of dry toluene is added, while transferring 3.16 g of fO, 04 mol) of dry pyridine, then a solution of 1.9 is added dropwise at a temperature of 5-9 ° C. g (0.01 mol) of chrysanthemic acid chloride in 10 ml of dry toluene. The reaction mixture is stirred for 5 hours at room temperature, after which the hydrochloric acid salt of pyridine is filtered off. The solution is successively extracted with 5% hydrochloric acid, sodium bicarbonate solution,
раствором поваренной соли и сушат сернокислым натрием.solution of sodium chloride and dried with sodium sulfate.
Растворитель отгон ют в вакууме, а остаток перекристаллизовывают из гептана. Получают 2,9 г (90%) 2-тио-З-хризантемоилоксиметилоензоксазолина с т. пл. 91-92°С.The solvent is distilled off in vacuo, and the residue is recrystallized from heptane. 2.9 g (90%) of 2-thio-3-chrysanthemoyloxymethyl-benzoxazoline are obtained with an mp. 91-92 ° C.
Найдено, %: С 65,08: 65,15; Н 6,69; 6,37; N 4,30; 4,25; S 9,89; 9,73.Found,%: C 65.08: 65.15; H 6.69; 6.37; N 4.30; 4.25; S 9.89; 9.73.
CisH,iNO,S.CisH, iNO, S.
Вычислено, %: С 65,23; П 6,38; N 4,22; S 9,67.Calculated,%: C 65.23; P 6.38; N 4.22; S 9.67.
Пример 2. Аналогично .примеру 1 из 2оксо-3-оксиметилбензоксазолина и хлоранпп,рида хризантемсвой кислоты получают 2-оксо3-хризантемоилоксиметилбензоксазолина . Выход 90%; т. пл. 85-86°С из гептана.Example 2. Analogously to Example 1 of 2oxo-3-hydroxymethylbenzoxazoline and hloranpp, reed chrysanthemoux acid get 2-oxo3-chrysanthemoyloxymethylbenzoxazoline. Yield 90%; m.p. 85-86 ° C from heptane.
Найдено, %: С 68,78; 68,70; Н 6,80; 6,71; N 4,50; 4,68. CisHaiNOi. Вычислено, %: С 68,55; Н 6,71; N 4,44.Found,%: C 68.78; 68.70; H 6.80; 6.71; N 4.50; 4.68. CisHaiNOi. Calculated,%: C 68.55; H 6.71; N 4.44.
Пример 3. Из 2-оксо-3-0:КСиметил-6-хлорбензоксазолина и хлорангидрида хриэантем.овой .кислоты получают 2-о1ксо-3-хриза1Нтемоилоксиметилен-6-хлорббнзоксазолин в .виде светлого масла. Выход 93%.Example 3. From 2-oxo-3-0: Xymethyl-6-chlorobenzoxazoline and chloroanthamboxylic acid chloride, 2-o1 xo-3-hryza1Ntemoxyloxymethylene-6-chlorobbnzoxazoline is obtained in the form of a light oil. Yield 93%.
Найдено, %: С 61,60; 61,48; Н 5,42; 5,55; С1 9,94; 9,93; N 4,07; 4,00.Found,%: C 61.60; 61.48; H 5.42; 5.55; C1 9.94; 9.93; N 4.07; 4.00.
Ci8H,oClN04.Ci8H, oClN04.
Вычислено, %: С 61,80; Н 5,76; С1 10,13; N 4,00.Calculated,%: C, 61.80; H 5.76; C1 10.13; N 4.00.
НрИМер 4. Из 2-аксо-3-окси.метил-6-бромбензоксазолина и хлорангидрида хризантемовой 1КИСЛОТЫ получают 2-оксо-3-хризантемоилоксиметилен-6-бромбензоксазолин в услови х Примера 1. Выход 91%; т. пл. 78-79°С из гептана .HpIMER 4. From 2-axo-3-hydroxy.methyl-6-bromobenzoxazoline and chrysanthemum 1-ACID chlorohydride, 2-oxo-3-chrysanthemoyloxy-oxymethylene-6-bromobenzoxazoline is obtained under the conditions of Example 1. Yield 91%; m.p. 78-79 ° C from heptane.
Найдено, %: С 55,60; 56,40; Н 5,20; 5,17; Вг 20,30; 20,37.Found,%: C 55.60; 56.60; H 5.20; 5.17; Br 20.30; 20.37.
CisHaoBrNOi.CisHaoBrNOi.
Вычислено, %: С 55,34; Н 5,11; Вг 20,26.Calculated,%: C 55.34; H 5.11; Вг 20,26.
Н р и м е р 5. Аналогично юр меру 1 из 2тио-3-оксиэтил-6-бромбензоксазолина и хлорангидрида хризантемовой .кислоты .получают 2-тио-3-хризантемоилоксиметилен-6 - бромбензоксазолин в виде светлого масла. Выход 95%.Notice 5. Similarly to the legal measure 1 of 2-3-hydroxyethyl-6-bromobenzoxazoline and chrysanthemic acid chloride, 2-thio-3-chrysanthemoyloxyloxymethylene-6 - bromobenzoxazoline is obtained in the form of a light oil. Yield 95%.
Найдено, %: С 52,80; 52,62; Н 4,80; 4,85; Вг 19,30; 19,37. CisH oBrNOaS.Found,%: C 52.80; 52.62; H 4.80; 4.85; Br 19.30; 19.37. CisH oBrNOaS.
Вычислено, %; С 52,68; Н 4,91; Вг 19,22; S 7.81.Calculated,%; C 52.68; H 4.91; Br 19.22; S 7.81.
Нредмет изобретени Nredmet of the invention
Claims (3)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU259891A1 true SU259891A1 (en) |
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