SU681830A1 - Acyl derivatives of oxymethylphosphoric acid possessing acaricidic and fungicidic activity - Google Patents
Acyl derivatives of oxymethylphosphoric acid possessing acaricidic and fungicidic activity Download PDFInfo
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- SU681830A1 SU681830A1 SU782578802A SU2578802A SU681830A1 SU 681830 A1 SU681830 A1 SU 681830A1 SU 782578802 A SU782578802 A SU 782578802A SU 2578802 A SU2578802 A SU 2578802A SU 681830 A1 SU681830 A1 SU 681830A1
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- SU
- USSR - Soviet Union
- Prior art keywords
- activity
- oxymethylphosphoric
- acaricidic
- fungicidic
- acyl derivatives
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- 239000002253 acid Substances 0.000 title claims description 3
- 230000000694 effects Effects 0.000 title description 2
- 125000002252 acyl group Chemical group 0.000 title 1
- 230000000895 acaricidal effect Effects 0.000 claims description 9
- 230000002378 acidificating effect Effects 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 5
- 230000000855 fungicidal effect Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 3
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 3
- 229960002447 thiram Drugs 0.000 description 3
- 241000239290 Araneae Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229960000453 malathion Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel 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
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
(54) АЦИЛПРОИЗВОДНЫЕ ОКСИМЕТИЛФОСФОНОВОЙ КИСЛОТЫ, ОБЛАДАЮЩИЕ АКАРИЦИДНОЙ И ФУНГИЦИДНОЙ АКТ 1ВНОСТЬЮ(54) ACYL DERIVATIVES OF OXYMETHYLPHOSPHONE ACID OWNING ACARICIDAL AND FUNGICIDA ACT 1
блюдаютс полосы поглощени в области 1250cM (Vfco), 1760-1750 см (),995- 1030 см (Ур-оАек)- ПМР-спектрах соединений наблюдались следующие сигналы: мультиплет протонов СН ( ,3 м.д), мультиплет протонов СНг группы СН2РС(О) 3,68 м.д. и группы Р-GHz,S 3,79 м.д. , мультиплет протонов CHj группы снз CHiOC(O) и (CHj) §The absorption bands in the 1250cM (Vfco), 1760-1750 cm (), 995-1030 cm (Ur-Aac) regions are observed. The following signals were observed in the PMR spectra of the compounds: CH multiplet protons (3 ppm), SNG proton multiplet CH2PC (O) 3.68 ppm and groups P-GHz, S 3.79 ppm. , multiplet of protons CHj of group of hz CHiOC (O) and (CHj) §
1,2 М.Д.. 1.2 M.D.
Эти соединени при использовании на биологическую активность про вили заметную фунгицидную активность против мицелий грибов различных видов. Например, соелинени (изо-СзНтО)гР(0)СН2.0С(6)ОСз(Нт-изо и (Cff,b)iP(0)CU O OCtHs приближаютс поThese compounds, when used for biological activity, have shown a marked fungicidal activity against the mycelium of fungi of various species. For example, the compounds (iso-CzNtoO) rP (0) CH2.0C (6) CCP (Ht-iso and (Cff, b) iP (0) CU O OCtHs are approximated by
ОABOUT
своим фунгицидным свойствам к тетраметилтиурамдисульфиду (ТМТД), прин тому за эталон.its fungicidal properties to tetramethylthiuram disulfide (TMTD), taken as the standard.
Акарицидна активность новых веществ определ лась против обыкновенного паутинного клеща. Все испытанные соединени показали акарицидные свойства, некоторые из них про вили акарицидную активность на уровне эталона - карбофоса. Так соединение ()iP(0)CHiOC(b)OCH3 про вилоThe acaricidal activity of new substances was determined against an ordinary spider mite. All tested compounds showed acaricidal properties, some of which showed acaricidal activity at the level of the standard, karbofos. So the connection () iP (0) CHiOC (b) OCH3 developed
акарицидную активность, равную активности карбофоса, а по величине CKso соединение оказалось более токсичным, чем карбофос .acaricidal activity, equal to the activity of karbofos, and the compound proved to be more toxic than karbofos in terms of CKso.
Пример 1. Получение 0-алкил-О -(диалкоксифосфонометил ) карбонатов.Example 1. Getting 0-alkyl-O - (dialkoxyphosphonomethyl) carbonates.
Соединени об формулыCompounds of formula
К суспензии 0,1 г-а металлического натри в абсолютном бензоле при комнатной температуре по капл м прибавл ют 0,1 г-моль диалкилфосфита, :месь выдерживают до полного растворени натри (1020 час). При 5-6°С порци ми быстро прибавл ют 0,1 г-моль параформа и перемащивают 1 ч при 20-25°. Окраска раствора становитс желтой. При температуре 4-6° медленно по капл м прибавл ют 0,1 г-моль алкоксихлоркарбоната, выдерживают при этой температуре 30 мин, температуру медленно повыщают до комнатной , перемешивают 1 ч. Затем постепенно повыщают температуру и перемещивают смесь 2-3 ч при 40-45°С и 4-6 ч при 50-60°С. За ходом реакции след т по исчезновению п тен, соответствующих исходным веществам на хроматограмме на силуфоле в системе ацетон-гексан 1:4, про витель иод.To a suspension of 0.1 g metal sodium in absolute benzene, 0.1 g mol of dialkyl phosphite is added dropwise at room temperature: the mixture is kept until the sodium is completely dissolved (1020 hours). At 5-6 ° C, 0.1 g-mol of paraform is quickly added in portions and re-coated for 1 hour at 20-25 °. The color of the solution turns yellow. At a temperature of 4-6 ° C, 0.1 g-mol of alkoxychlorocarbonate is slowly added dropwise, kept at this temperature for 30 minutes, the temperature slowly rises to room temperature, stirred for 1 hour. Then gradually increase the temperature and transfer the mixture for 2-3 hours at 40 -45 ° С and 4-6 h at 50-60 ° С. The progress of the reaction is followed by the disappearance of the spots corresponding to the starting materials on the chromatogram on a silufol in the acetone-hexane system 1: 4, the developer is iodine.
в конце реакции смесь охлаждают, осадок хлорнистого натри отфильтровывают, фильтрат дважды промывают водой, сущат сульфатом натри . После удалени растворител в вакууме остаток перегон ют, либо очищают хроматографически на пластинках с силикагелем. Выходы целевых продуктов составл ют 38-81/о.at the end of the reaction, the mixture is cooled, the precipitate of sodium chloride is filtered off, the filtrate is washed twice with water, and sodium sulfate. After removal of the solvent in vacuo, the residue is distilled, or purified by chromatography on silica gel plates. The outputs of the desired products are 38-81 / o.
Константы, выход, данные элементного анализа полученных соединений представлены в табл. 1.Constants, output, data of elemental analysis of the compounds obtained are presented in table. one.
О IIAbout II
ТаблицаTable
с-оГs-oG
Н К qHs- 41 изо CgHj- Н Н СгНу 51,3 Н ,7 изо СгН5- Н Н С,,5 -изо С,Н(| СН, СНд CjHj 62 Cj,Hj CHj CHj 38 119-122 1,42ОЗ 1,092О 61,92 62,15 44,90 7,ОЗ11,20 €,„ Hj, ОеР 44,77 7,89 11,55 0,15268,253 102-105 1,4191 1,1439 52,94 53,02 39,48 7,Об12,54 CjH,,OjP 4О,00 7,14 12,89 0 8240,199 120-121 1,4234 1,0777 66,64 66,52 46,52 8,1010,71 C jHjjOeP 46,81 8,21 10,97 0,3282,280 163-164 1,4274 1,1277 57,41 57,71 42,57 7,2112,35 CgR-pOeP 42,52 7,53 12,19 : 254,226 и хо Х:Г:А 1,4241 1,О891 75,88 76,ОО 51,90 9,119,23 С, 51,84 9,02 9,55 3:3:1324,361 130-13 2 1,4218 1,0555 62,02 62,57 47,30 7,3511,11 С,, Нг, OgP 7,89 11,55 0,3 -268,253 Х:Г:А 3:3:1 QHj, Н Н 55 С Н, НН С2%42 CjHy Н Н СНз 53,2 CHj Н Н CHj 66,7 H K qHs- 41 from CgHj-H H CrHu 51.3 H, 7 from CrH5-H H C ,, 5 -iso C, H (| CH, CHd CjHj 62 Cj, Hj CHj CHj 38 119-122 1,42ОЗ 1,092О 61,92 62,15 44,90 7, OZ11,20 €, „Hj, ОРР 44,77 7,89 11,55 0,15268,253 102-105 1,4191 1,1439 52,94 53, 02 39.48 7, Ob12.54 CjH ,, OjP 4O, 00 7.14 12.89 0 8240.199 120-121 1.4234 1.0777 66.64 66.52 46.52 8.1010.71 C jHjjOeP 46.81 8.21 10.97 0.3282,280 163-164 1.4274 1.1277 57.41 57.71 42.57 7.2112.35 CgR-pOeP 42.52 7.53 12.19 : 254.226 and ho X: G: A 1.4241 1, O891 75.88 76, GS 51.90 9.119.23 C, 51.84 9.02 9.55 3: 3: 1324.361 130-13 2 1 , 4218 1.0555 62.02 62.57 47.30 7.3511.11 С, Нg, OgP 7.89 11.55 0.3 -268.253 X: G: A 3: 3: 1 QHj, H N 55 С Н, НН С2% 42 CjHy Н Н СНз 53.2 CHj Н Н CHj 66.7
ЧН, Н Н CjH 57 тех1,4136CHN, N N CjH 57 technical1,4136
А:Г:Х 1:3:3A: D: X 1: 3: 3
e-Hj egHy Н 48 техe-Hj egHy H 48 tech
92-94 Примечание: А- ацетон, Б - бензол, Г - гексан, X Пример 2. Акарицидна активность сое- динений определена дл обыкновенного паутинного клеща Tetranychus urticae Koeh методом погружени растений, зараженных92-94 Note: A - acetone, B - benzene, G - hexane, X Example 2. The acaricidal activity of the compounds was determined for the common spider mite Tetranychus urticae Koeh by immersing plants infected
Проаопжение табл. 1Tables one
5О,40 8,50 10,ЗО 50,318,77 9,98 310,3345O, 40 8.50 10, AO 50.318.77 9.98 310.334
54,49 6,68 9,83 e,Hg|OjP 54,88 6,44 9,43 316,297 157-160 1,42311,052371,2671,7149,098,8711.20 48,64 8,51 10,45 0,3296,307 127-130 1,4302 1,1119 62,03 62,31 44,41 7,79 13,12 С,(, Н, OjP 44,77 7,89 11,55 0,2268,25 115-1161,4286 1,1896 48,17 48,99 37,37 6,9О 12,83 С Н Cfe Р 37,17 6,69 13,69 0,2226,172 тех1,4032 1,6452 38,93 39,25 30,58 5,73 15,12 30,31 5,60 15,63 А:Г 1:4198,118 хлороформ, ТеХ - тонкоспойна хроматографи клещами, в водоацетоновые растворы (с добавкой эмульгатора) этих соединений, Акарицидна активность соединений показана в табл. 2. Таблица 254.49 6.68 9.83 e, Hg | OjP 54.88 6.44 9.43 316.297 157-160 1.42311.052371.2671.7149.098.8711.20 48.64 8.51 10.45 0 , 3296.307 127-130 1.4302 1.1119 62.03 62.31 44.41 7.79 13.12 C, (, H, OjP 44.77 7.89 11.55 0.2268.25 115 -1161.4286 1.1896 48.77 48.99 37.37 6.9O 12.83 C H Cfe P 37.17 6.69 13.69 0.2226.172 Tah1,44032 1.6452 38.93 39 , 25 30.58 5.73 15.12 30.31 5.60 15.63 A: G 1: 4198.118 chloroform, TeX - finely chromatographed with mites, into water-acetone solutions (with the addition of an emulsifier) of these compounds, Acaricidal activity of the compounds shown in Table 2. Table 2
Эталон-карбофос Учет гибели клещей проводили через 48 ч В концентрации 0,06% высокую акарицидную активность про вили соединени №№ 2, 3, 4, 5, 6. По СК уо % (CjrHj О)г P(O)CHzOC(O)OCHs более токсичен, чем вз тый за эталонный препарат инсектоакарицид карбофос. Фунгицидна активность соединений фор мулы I против мицелий грибов рпредел етПродолжение табл. 2Reference karbofos Accounting for tick death was done after 48 hours. At a concentration of 0.06%, high acaricidal activity was reported by compounds Nos. 2, 3, 4, 5, 6. According to SC,% (CjrHj O) g P (O) CHzOC (O The OCHs are more toxic than the carbofos taken for the reference insecticacaricide drug. The fungicidal activity of the compounds of the formula I against fungal mycelium is distributed. Continuation of the table. 2
100100
0,0045 с в концентрации 0,003% по действующему веществу. Эталоном служит ТМТД. В та.бл. 3 представлена фунгицидна активность соединений. Результаты испытаний показывают, что некоторые соединени про вл ют заметные фунгицидные свойства, например, соединени 2 и 6 (табл. 3). Таблица 30.0045 s at a concentration of 0.003% for the active substance. The standard is TMTD. In ta.bl. 3 shows the fungicidal activity of the compounds. The test results show that some compounds exhibit noticeable fungicidal properties, for example, compounds 2 and 6 (Table 3). Table 3
681830 910681830 910
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU782578802A SU681830A1 (en) | 1978-02-13 | 1978-02-13 | Acyl derivatives of oxymethylphosphoric acid possessing acaricidic and fungicidic activity |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU782578802A SU681830A1 (en) | 1978-02-13 | 1978-02-13 | Acyl derivatives of oxymethylphosphoric acid possessing acaricidic and fungicidic activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU681830A1 true SU681830A1 (en) | 1981-05-23 |
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ID=20748497
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782578802A SU681830A1 (en) | 1978-02-13 | 1978-02-13 | Acyl derivatives of oxymethylphosphoric acid possessing acaricidic and fungicidic activity |
Country Status (1)
| Country | Link |
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| SU (1) | SU681830A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4608207A (en) * | 1983-05-07 | 1986-08-26 | Bayer Aktiengesellschaft | Dialkyl 2-alkylcarbonatoethanephosphonates |
-
1978
- 1978-02-13 SU SU782578802A patent/SU681830A1/en active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4608207A (en) * | 1983-05-07 | 1986-08-26 | Bayer Aktiengesellschaft | Dialkyl 2-alkylcarbonatoethanephosphonates |
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