SU670198A3 - Insecticide - Google Patents

Insecticide

Info

Publication number
SU670198A3
SU670198A3 SU731879889A SU1879889A SU670198A3 SU 670198 A3 SU670198 A3 SU 670198A3 SU 731879889 A SU731879889 A SU 731879889A SU 1879889 A SU1879889 A SU 1879889A SU 670198 A3 SU670198 A3 SU 670198A3
Authority
SU
USSR - Soviet Union
Prior art keywords
hydrogen
methyl
group
ethyl
chlorine
Prior art date
Application number
SU731879889A
Other languages
Russian (ru)
Inventor
Каррер Фридрих
Original Assignee
Циба-Гейги Аг (Фирма)
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from CH187072A external-priority patent/CH571305A5/en
Priority claimed from CH43873A external-priority patent/CH584005A5/en
Application filed by Циба-Гейги Аг (Фирма) filed Critical Циба-Гейги Аг (Фирма)
Application granted granted Critical
Publication of SU670198A3 publication Critical patent/SU670198A3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/54—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/14—Unsaturated ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)

Description

(54) ИНСЕКТИЦИДНОЕ СРЕДСТВО MOC-CaC -Til Пэ 5 где Rj, R, Rj, Hi,, R, Y и Z им указанные значени ; М-означает катион, преимущес но металл, в частности металл 1 II главной группы периодической мы, или водород; X - галоген, преимущественно хлор, бром, или йод, П р и м е р. Получёние 4-прбпаргилоксидифениловоро эфира (1), Смесь 18,6 г 4-оксидифенилового эфира, 13,1 г пропаргилбромида и 16,6 г безводного карбоната кали  в 150 мл ацетона перемешивают 16 ч при температуре дефлегмации. Затем реакционную смесь отфильтровывают от осадка, ацетон отгон ют в вакууме, масл нистый остаток раствор ют в 200 мл эфира/гексана (1:1), этот раствор 4 раза промывают 10%-ным раствором едкого кали  и затем водой до нейтральной реакции. Органическую фазу высушивают над сульфатом натри  и отфильтровывают. После удалени  из фильтрата растворител  и летучих в вакууме получают чистый дл  анализа 4 -пропаргилоксилифенил6вь й эфир. Таким образом получают соединени , приведенные в табл. 1. Таблица 1(54) INSECTICIDE MEANS MOC-CaC -Til Peh 5 where Rj, R, Rj, Hi, R, Y, and Z have the indicated values; M-means cation, mainly metal, in particular metal 1 II of the main group of the periodic, or hydrogen; X - halogen, mainly chlorine, bromine, or iodine. Example: Preparation of 4-prbpargiloxydiphenyl ether (1), a mixture of 18.6 g of 4-oxydiphenyl ether, 13.1 g of propargyl bromide and 16.6 g of anhydrous potassium carbonate in 150 ml of acetone is stirred for 16 hours at reflux temperature. The reaction mixture is then filtered off from the precipitate, the acetone is distilled off in vacuo, the oily residue is dissolved in 200 ml of ether / hexane (1: 1), this solution is washed 4 times with 10% potassium hydroxide solution and then with water until neutral. The organic phase is dried over sodium sulfate and filtered. After removal of the solvent and volatiles from the filtrate in vacuo, 4-propargyloxyphenyl ester ether, pure for analysis, is obtained. In this way, the compounds shown in Table 1 are obtained. 1. Table 1

Т.пл. 77-79 СM.p. 77-79 С

Т.пл. 82-84 сM.p. 82-84 seconds

Т.пл. 83-85°СM.p. 83-85 ° C

Т.пл. 51-52 0M.p. 51-52 0

Т.пл. 78-80СM.p. 78-80С

Т.пл. 108-109 0M.p. 108-109 0

СоедиСтруктурна  формула нениеCompound Formula

67019866701986

Продолжение табл. 1Continued table. one

Физические константыPhysical constants

10ten

гоgo

njj 1,5769njj 1,5769

гII ;Г II ( .пл. 59-60 С Т.пл. 60-61 С 1,5632gII; GII (.p. 59-60 C; mp. 60-61 C 1.5632

ii

1414

Т.пл. 77-78 СM.p. 77-78 С

ГNr ГNr

1515

16sixteen

1717

1818

19nineteen

2020

2121

2222

2323

2424

Т.пл. 112-113 сM.p. 112-113 seconds

.снго.sngo

20 п 1,680520 p 1,6805

п 1,5185p 1,5185

Т.пл. 73-74СM.p. 73-74С

Т.пл. 38-39 СM.p. 38-39 С

Т.пл. 82-84 0M.p. 82-84 0

Т.пл. 71°СM.p. 71 ° C

Т.пл. 131-132СM.p. 131-132С

Структурна  формулаStructural formula

СоединениеCompound

2525

2626

2727

2828

2929

30thirty

3131

Физические константыPhysical constants

хТ .пл, 42-44°СxT.pl, 42-44 ° C

Т.пл. 61-62 сM.p. 61-62 seconds

96701989670198

Продолжение табл.2 Continuation of table 2

0-CHj-C CH0-CHj-C CH

0-ОН2-С ОН tB0-OH2-C OH tB

CHj-c-/ у-о-снг-с снCHj-c- / u-o-sng-sn

оabout

jj-CHz-O-CHj-0 s CHjj-CHz-O-CHj-0 s CH

Таким образом, предлагаемые соединени  обладают хорошей инсектицидной активностью.55Thus, the proposed compounds have good insecticidal activity.55

Claims (1)

Формула изобретени  Инсектицидное средство, содержащее производные фенилалкинилового эфира как активное вещество и добавку, вы- Q бранную из группы твердый или жидкий носитель, отличают е.е с п .тем, что, с целью усилени  инсектицид«ной активности, оно содержит в качестве производного фенилалкинилоЕОГо эфира соединение общей формулыInvention An insecticidal agent containing phenylalkynyl ether derivatives as an active substance and an additive that is selected from the group of solid or liquid carriers is distinguished from the fact that, in order to enhance insecticide activity, it contains as a derivative phenylalkynyl ester compound of the general formula 10 Продолжение табл.210 Continuation of table 2 Дл  сравнени  используют уже известные инсектицидыFor comparison, already known insecticides are used. 22 iC iC ww Выложенна  за вкаPosted for (E)(E) ФРГ № 2114257,Germany No. 2114257, кл, 120 19/03, 1971Cl 120/1903, 1971 R-,--YR -, - Y Z-C-C C-B.Z-C-C-B. где Rf водород, метил, йод;.where Rf is hydrogen, methyl, iodine; R - водород, метил, этил; Rj - водород, метил; R ц - циклогексил или группаR is hydrogen, methyl, ethyl; Rj is hydrogen, methyl; R C - cyclohexyl or group RTRT j „,„хгУ„j „,„ hgU „ / / п/ 1Ь где Rg - водород, фтор, хлор, метчп этил,- этокси; Rf - водород, н-пропил; RS - водород, хлор; У - кислород, группы , CH-CHj, -СНдО-, ил пр ма  св зь; кислород, группа -СН2О-,при чем -СНд-группа св зана с фенилом, в количестве 0,1- 95 вес.%, а остальное - добавка . Приоритет по признакам: 09.02.72 при Rf - водород, метил R - водород, метил, этил, RJ - водо род, метил, R - циклогексил или гру / 6 водород,фтор, хлор. 8 метил, этил, этокси, У - кислород, группы СгО, CH-CHj, , -СН.О-, Z - кислород или группа , причем СНд-группа св зана с фенилом; 12.01.73 при R - йод, Rf - группа о-сиг RJ - водород, хлор, R - водород , н-пропил, у - пр ма  св зь. Источники информации, прин тые во внимание при экспертизе 1.Выложенна  за вка ФРГ 2100325, кл. 30 h 2/36, 1971. 2,Патент Франции № 1510861, кл., С 07 С, 1968.n / 1b where Rg is hydrogen, fluorine, chlorine, ethyl ethyl is ethoxy; Rf is hydrogen, n-propyl; RS is hydrogen, chlorine; Y is oxygen, groups, CH — CH j, —CHDO—, or a direct bond; oxygen, the -CH2O- group, wherein the -CHD group is bound to phenyl, in an amount of 0.1-95 wt.%, and the rest is an additive. Priority on the following signs: 09.02.72 with Rf - hydrogen, methyl R - hydrogen, methyl, ethyl, RJ - hydrogen, methyl, R - cyclohexyl or gru / 6 hydrogen, fluorine, chlorine. 8 methyl, ethyl, ethoxy, Y - oxygen, CrO, CH-CHj, -CHNO-, Z-oxygen or a group, and the SND group is bound to phenyl; 01/12/73 with R — iodine, Rf — o-cig group, RJ — hydrogen, chlorine, R — hydrogen, n-propyl, y — direct bond. Sources of information taken into account in the examination 1. Published for Germany 2100325, cl. 30 h 2/36, 1971. 2, Patent of France No. 1510861, class, C 07 C, 1968.
SU731879889A 1972-02-09 1973-02-08 Insecticide SU670198A3 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH187072A CH571305A5 (en) 1972-02-09 1972-02-09 Phenyl-or benzyl-alkynyl ethers - prepd from phenol and alkinylhalides used as insecticides, nematocides
CH43873A CH584005A5 (en) 1973-01-12 1973-01-12 Phenyl-or benzyl-alkynyl ethers - prepd from phenol and alkinylhalides used as insecticides, nematocides

Publications (1)

Publication Number Publication Date
SU670198A3 true SU670198A3 (en) 1979-06-25

Family

ID=25684580

Family Applications (1)

Application Number Title Priority Date Filing Date
SU731879889A SU670198A3 (en) 1972-02-09 1973-02-08 Insecticide

Country Status (13)

Country Link
JP (1) JPS4887018A (en)
AT (1) AT324043B (en)
BE (1) BE795129A (en)
CA (1) CA996553A (en)
DD (1) DD107849A5 (en)
DE (1) DE2305698A1 (en)
FR (1) FR2171303B1 (en)
GB (1) GB1418824A (en)
HU (1) HU165798B (en)
IL (1) IL41437A (en)
IT (1) IT987010B (en)
NL (1) NL7301604A (en)
SU (1) SU670198A3 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4141921A (en) 1972-02-09 1979-02-27 Ciba-Geigy Corporation Phenoxyphenyl- and phenoxybenzyl-alkynyl ethers
DE2404951A1 (en) * 1973-02-05 1974-08-08 Ciba Geigy Ag 1-PHENYL-1-P-PROPARGYLOXYPHENYL-2NITRO-AETHANE DERIVATIVES, THE METHOD FOR THEIR PRODUCTION AND THEIR USE
DE58907763D1 (en) * 1988-09-15 1994-07-07 Ciba Geigy New ether.
EP1770089A1 (en) * 2005-10-03 2007-04-04 Institut Pasteur Pyranodibenzofuran derivatives with antifungal and antibacterial activity
WO2018135498A1 (en) * 2017-01-18 2018-07-26 三菱瓦斯化学株式会社 Compound, resin, composition, and method for forming pattern

Also Published As

Publication number Publication date
GB1418824A (en) 1975-12-24
IL41437A (en) 1977-01-31
IT987010B (en) 1975-02-20
JPS4887018A (en) 1973-11-16
NL7301604A (en) 1973-08-13
DD107849A5 (en) 1974-08-20
AT324043B (en) 1975-08-11
CA996553A (en) 1976-09-07
DE2305698A1 (en) 1973-08-16
FR2171303A1 (en) 1973-09-21
FR2171303B1 (en) 1979-10-12
HU165798B (en) 1974-11-28
BE795129A (en) 1973-08-08
IL41437A0 (en) 1973-03-30

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