SU649296A3 - Insecticide-acaricide - Google Patents
Insecticide-acaricideInfo
- Publication number
- SU649296A3 SU649296A3 SU741994402A SU1994402A SU649296A3 SU 649296 A3 SU649296 A3 SU 649296A3 SU 741994402 A SU741994402 A SU 741994402A SU 1994402 A SU1994402 A SU 1994402A SU 649296 A3 SU649296 A3 SU 649296A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- compound
- insecticide
- acaricide
- death
- hours
- Prior art date
Links
- 239000000642 acaricide Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000238631 Hexapoda Species 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- 241000256111 Aedes <genus> Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 241000238876 Acari Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- 241000257229 Musca <genus> 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
- QINBHWDDSDDTEG-UHFFFAOYSA-N [O-]P(O)(O)=[S+]C(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound [O-]P(O)(O)=[S+]C(C1=CC=CC=C1)C1=CC=CC=C1 QINBHWDDSDDTEG-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- -1 bromodiphenylmethyl Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 231100000862 numbness Toxicity 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1653—Esters of thiophosphoric acids with arylalkanols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
1one
Изобрегение огносигс к химическим средствам дл борьбы с насекомыми к клещами, а именно к инсектоакарицидным средствам на основе производного S -дифенилмегилтиофосфага .The ognosigs isobregnation of insect control agents against ticks, namely insecticide-acaricides based on the derivative S-diphenylmethylthiophosphate.
Известно средство на основе 0,О-ди- этил-5 -дифенилметилтиофосфата и обычных добавок, обладающее песгицидной активностью i. Однако активность его недостаточна.A means is known on the basis of 0, O-diethyl-5-diphenylmethylthiophosphate and the usual additives, which possess pesgicidal activity i. However, its activity is insufficient.
Целью изобрегени вл етс изыскание нового инсектоакарицидного средства,обладающего более высокой биологической активностью.The aim of the invention is to find a new insecticoacaricidal agent with a higher biological activity.
Предлагаетс в качестве инсектоака- рицидного средства использовать производное 5 -дифенилметилтиофосфата общей формулы и 2It is proposed to use a 5-diphenylmethylthiophosphate derivative of the general formula and 2 as an insecticoacaricidal agent.
Л/осгн ,L / Osgn,
FF
CDCD
где R, и ) каждый означает атом водорода ил|. хлор,where R, and) each means a hydrogen atom or |. chlorine,
в количестве 0,5-99,5 вес.%.in the amount of 0.5-99.5 wt.%.
Соединени общей формулы Т можно получать следующим известным методом;Compounds of general formula T can be prepared by the following known method;
СНХ SNH
Нй1Ny1
даYes
+ Me Hal (iv) + Me hal (iv)
2(f где f, Rjj и имеют указанное значение:2 (f where f, Rjj and have the specified value:
Наб означает атом галогена; Мб - щелочной мета;и1, в частносги натрий или калий.Nab means a halogen atom; Mb - alkaline meta; u1, in particular, sodium or potassium.
Спекзоб провод т при нормальном давлении , при температуре 0-150 С, пред почтительно при 20-80 0, и в инертных по отношению к реагентам рас твори гел х или разбавител х. f.lna этого пригодны, например, ароматические углеводороды, галогенуглеводороды, хлорированные алканы , имеющие атома углерода, прос тые эфиры, сложные зфиры, кегоны, ниг рилы. Формы применени препаратов обычные.The specimen is carried out at normal pressure, at a temperature of 0-150 ° C, preferably at 20-80 ° C, and in inert solutions with respect to reagents or diluent gels. f.lna of this are suitable, for example, aromatic hydrocarbons, halohydrocarbons, chlorinated alkanes having a carbon atom, a simple ester, ester, kegon, nigril. The form of use of drugs is normal.
Пример 1. Получение О-атил- «5 пропил-Б -дифенилметилового эфира дитиофосфорной кислоты.Example 1. Getting O-atil- "5 propyl-B-diphenylmethyl ester of dithiophosphoric acid.
к раствору 18,5 г бромдифенилмети ла в 100 мл абсолютного ацетонитрила при комнатной температуре порци ми добавл ют 19 г 0-етил- 6 Лропилдитиофос- форнокислого кали . Реакционную смесь затем перемешивают в течение 12 ч и фильтруют. После выпаривани фильтрата остаток обрабатывают эфиром, промывают полученный раствор 2 раза (по 1ОО мл) водой и органическую фазу сушат над сульфатом натри . В качестве продукта получают сырой О-этил«5-пропил- З-дифенилметиловый эфир дитиофосфорной кислот формулыto a solution of 18.5 g of bromodiphenylmethyl in 100 ml of absolute acetonitrile, at room temperature, 19 g of 0-ethyl-6 Lropyl dithiophosphoric acid potassium is added in portions. The reaction mixture is then stirred for 12 hours and filtered. After evaporation of the filtrate, the residue is treated with ether, the resulting solution is washed 2 times (1OO ml) with water and the organic phase is dried over sodium sulfate. Crude O-ethyl "5-propyl-3-diphenylmethyl ester of dithiophosphoric acid of the formula
..
С1C1
// //
// Ч// H
С1C1
Н IH I
ClCl
$ I О T-OOj-Hj$ I About T-OOj-Hj
$С1зН7 (соединение 4), П 1,5991,$ С1зН7 (compound 4), P 1,5991,
Пример 2. Инсектицидное дейст« вие на Миека domestka.Example 2. Insecticidal action on Myeka domestka.
1 мл ацетонового раствора, содержаще го 5 мг испытуемого соединени , вносзт пипеткой в чашку Петри. Спуст 1 час в чашку помешают Ю опытных насекомых (MusKO domestica ) в состо нии окоченени от холода и чашку снова закрывают. На одно испытуемое веш.ество примен ют по две чашки и оценку действи произво- д т спуст О,5, 1, 2, 4 и 8 ч. В качесг ве этапона испо ьзуют известное соедине ние, прин тое за прототип, формулы1 ml of an acetone solution containing 5 mg of the test compound is pipetted into a Petri dish. After 1 hour, Yu experienced insects (MusKO domestica) would be in a state of cold numbness and the cup was closed again. Two cups are used per test subject and the evaluation of the effect is made after 0, 5, 1, 2, 4 and 8 hours. As a stadium, a known compound, used as a prototype, is used
(V)(V)
0 F-OC2ir5S-C31I7-W0 F-OC2ir5S-C31I7-W
(соединение 1), который очищают путем хроматографировани: на колонке с силика« гелем, п 1,5878.(compound 1), which is purified by chromatography: on a silica gel column, p 1.5878.
Аналогичным образом получают следующие соединени :The following compounds are prepared in a similar manner:
/ /
// //
ОНHE
10 Р-ОСгК5 SC-jH -ff (соединение 2), п 1,5930;10 P-OSgK5 SC-jH -ff (compound 2), p 1.5930;
Оценивают инсектицидное пействие по п тибальной шкале:Insecticidal effect is evaluated according to the tibal scale:
5 гибель спустк 0,5 ч; 4 .- 100%- а гибель спуст 1 ч; 3 100%«на гибель спуст 2 ч; 2 . 95-10О%««а гибель спуст 8 ч; 1 неактивно в течение 8 ч. Результаты опыта приведены в табл. 1,5 death down 0.5 h; 4 .- 100% - and death after 1 h; 3 100% "for death after 2 hours; 2 95-10O% ““ and death after 8 h; 1 inactive for 8 hours. The results of the experiment are shown in Table. one,
Т а бT a b
л и ц аl and c
Соединение Оценка, баллCompound Score, score
33
1one
Q-P-OC HSQ-P-OC HS
$ СзН7 (соединение 3), nl 1,5974;$ CzN7 (compound 3), nl 1.5974;
П р и м е р . 3. Инсектицидное деист вие на Aedes .PRI me R. 3. Insecticidal effect on Aedes.
Использу насекомые вида AedeS аеgypti вместоMusca domesticQ и i мл ацетонового раствора, содержащего 1 мг испытуемого соединени , повтор ют опи санную в примере 2 методику. Результаты приведены в табл. 2.Using insects of the species AedeS aégypti instead of Musca domesticQ and i ml of an acetone solution containing 1 mg of the test compound, the procedure described in example 2 is repeated. The results are shown in Table. 2
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH175573A CH573710A5 (en) | 1973-02-07 | 1973-02-07 | S-diphenylmethyl phosphorodithioates - with insecticidal, acaricidal, bactericidal, fungicidal and nematocidal activity |
Publications (1)
Publication Number | Publication Date |
---|---|
SU649296A3 true SU649296A3 (en) | 1979-02-25 |
Family
ID=4217802
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SU741994402A SU649296A3 (en) | 1973-02-07 | 1974-02-05 | Insecticide-acaricide |
Country Status (5)
Country | Link |
---|---|
AT (1) | AT322277B (en) |
BE (1) | BE810668A (en) |
CH (1) | CH573710A5 (en) |
SU (1) | SU649296A3 (en) |
ZA (1) | ZA74762B (en) |
-
1973
- 1973-02-07 CH CH175573A patent/CH573710A5/en not_active IP Right Cessation
-
1974
- 1974-02-05 SU SU741994402A patent/SU649296A3/en active
- 1974-02-06 AT AT92574A patent/AT322277B/en active
- 1974-02-06 ZA ZA740762A patent/ZA74762B/en unknown
- 1974-02-06 BE BE140599A patent/BE810668A/en unknown
Also Published As
Publication number | Publication date |
---|---|
BE810668A (en) | 1974-08-06 |
ZA74762B (en) | 1974-12-24 |
AT322277B (en) | 1975-05-12 |
CH573710A5 (en) | 1976-03-31 |
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