IL42401A - Antibiotic substances b-41,their production and their use as insecticides and acaricides - Google Patents
Antibiotic substances b-41,their production and their use as insecticides and acaricidesInfo
- Publication number
- IL42401A IL42401A IL42401A IL4240173A IL42401A IL 42401 A IL42401 A IL 42401A IL 42401 A IL42401 A IL 42401A IL 4240173 A IL4240173 A IL 4240173A IL 42401 A IL42401 A IL 42401A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- hydrogen atom
- methyl group
- group
- bond
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G11/00—Antibiotics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Environmental Sciences (AREA)
- Biotechnology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pharmacology & Pharmacy (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Dentistry (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Compounds Of Unknown Constitution (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Claims (11)
1. A compound having the formula wherein R, represents a hydrogen atom or a methyl group; R2 represents a methyl grou "or when 1 is hydrogen Rg may also represent a pyrroyloxymethyl group of the formula ; R_ represents a methyl group or an ethyl group? R^ and ^ are each a hydrogen atom, or, when Rg anc Rj are. each a methyl group, A may also represent a group of CH3 the formula -0C0CH-(CH2)j-CH-- in which case R^ is a hydroxy group; Rg and R^ together represent a C-0 bond, but when R^ , and R^ are each a. methyl group and R^ and R^.are each hydrogen, then Rg and R^ may also be each a hydrogen atom.
2. The compound of formula I in Claim 1, wherein R1 is a hydrogen atom, is a methyl group, R^ is a methyl group, R^ and R^ are each a hydrogen atom and Rg and R^ together represent a C-0 bond. - 20 » 42401/2
3. The compound of formula I in. Claim 1, wherein is a hydrogen atom, g is a methyl group, R.. is an ethyl group, R^ and Rpj are each a hydrogen atom and Rg and R^ together represent a 0-0 bond .
4. The compound of formula I in Claim 1 , wherein R^ is a methyl group, Rg is a methyl group, ^ is a methyl group, R^ and R,. are each a hydrogen atom and Rg and R^ together represent a C-0 bond.
5. The compound of formula I in Claim 1, wherein is a methyl group, Rg is a methyl group, R^ is an ethyl group, R^ and Rj are each a hydrogen atom and Rg and R^ together represent a C-0 bond.
6. The compound of formula I in Claim 1, wherein 1 is a hydrogen atom, 2 is the pyrroyloxymethyl group, R^ is a methyl group, R^ and Bp. are each a hydrogen atom and Rg and R^ together represent a C-0 bond.
7. The compound of formula I in Claim 1 , wherein R1 is a hydrogen atom, R2 is the pyrroyloxyme hyl group, R^ is an ethyl group, R^ and R-. are each a hydrogen atom and Rg and ^ together represent a C-0 bond.
8. A compound according to Claim 1 having the formula 42401/2 .,,
9. An antibiotic substance B-^l-Ag-. effective against harmful insects, said substance being a colorless amorphous powder form which is difficultly soluble in water and easily soluble in n-hexane, benzene, acetone, ethanol and chloroform and has the formula I in Claim 1 , in which R^ is a hydrogen atom, R5 is a methyl group, R., is a' methyl group, RA is a group of the formula _oco-CH-(C*i ) -CH » R5 iS ^^νοχ^ ' and Rg and R^ together represent a C-0 bond*; said substance . has a molecular -formula of C^gK^gO^ Q, a compositio of 71.75%Tcarbon and 8.26% hydrogen and the following ■ properties; molecular weights of 672.1 obtained by an osmometric method. in acetone and of 672 according 20 1 mass spectrum; a specific rotatory power of (° D ° · ' '\ +5*-° obtained with the concentration of a sample of 5 mg./2 ml. and the length of a layer of 10 cm. in acetone; no p a at a pK ranging from 2 to 12; absorption maximum in the ultraviolet region of the spectrum at 24-5 ιημ; characteristic absorption bands j in the infrared region shown in Fig. 11; nuclear . 1 magnetic resonance spectrum in (CD^^CO shown in I Fig. 20; main peaks of the mass spectrum 672, 181, j 153 and.151 obtained under the conditions of 75 eV j at ionization room temperature of 2o6eC. and a sample temperature of 120-190°C; and the following color reactions according to a thin layer chromatography, ■ yellow to iodine/chloroform, negative to ninhydrin, reddish purple to sulfuric acid and yellow to potassium permanganate.
10. An- antibiotic substance B-41-B^ effective against harmful insects, said substance bein a -29- 42401 / 3 ethanol and chloroform and has the formula I in Claim 1 , i ethyl is substance has a molecular formula of a composition of 68,006 carbon and 8·32# hydrogen and the following properties; a melting point of 176-178°C ; molecular weights of 629o5 obtained by an osmometric method in acetone and of 686 according to mass spectrum; a specific rotatory power of (° D = obtained with the concentration of a sample of 5 mg./2 ml. and. the length of a layer of 10 cm. in acetone; no pKa at a pH ranging from 2 to 12; absorption maximum in the ultraviolet region of the spectrum at 2 5 πιμ; characteristic absorption bands in the infrared region shown in Fig. 14; nuclear magnetic resonance spectrum in (CD^^CO shown in Fig. 23; main peaks of the mass spectrum .686, 414, 195, .167, 151 and 125 obtained under the conditions of 75 eV at ionization room temperature of · 200eC. and a sample temperature of 120-i90°C; and the following color reactions according to a thin layer chromatography", yellow to iodine/chloroform, negative to ninhydrin, reddish purple to sulfuric acid and yellow to potassium permanganate.
11. A process for producing antibiotic substances B-41-Aj, B-41-A2, B-41-Aj, B-41-A^, B-41-B- B-41-B2, B-41-B^, B-41-C^ and B-41-C2 which comprises cultur-ing a B-41-producing strain belongin to the genus Streptomyces-= and then recovering, either singly or ■ in the form of mixtures , said antibiotic .substances from the fermentation broth.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP47057058A JPS4914624A (en) | 1972-06-08 | 1972-06-08 |
Publications (2)
Publication Number | Publication Date |
---|---|
IL42401A0 IL42401A0 (en) | 1973-07-30 |
IL42401A true IL42401A (en) | 1976-02-29 |
Family
ID=13044830
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IL42401A IL42401A (en) | 1972-06-08 | 1973-05-30 | Antibiotic substances b-41,their production and their use as insecticides and acaricides |
Country Status (11)
Country | Link |
---|---|
JP (1) | JPS4914624A (en) |
BR (1) | BR7304308D0 (en) |
CH (2) | CH585514A5 (en) |
DE (1) | DE2329486C2 (en) |
ES (1) | ES415591A1 (en) |
FR (1) | FR2187778B1 (en) |
GB (1) | GB1390336A (en) |
IL (1) | IL42401A (en) |
IT (1) | IT986430B (en) |
SU (2) | SU588926A3 (en) |
ZA (1) | ZA733857B (en) |
Families Citing this family (77)
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JPS5858164B2 (en) * | 1975-09-06 | 1983-12-23 | イシカワジマハリマジユウコウギヨウ カブシキガイシヤ | Chisel Souchi |
SE434277B (en) * | 1976-04-19 | 1984-07-16 | Merck & Co Inc | SET TO MAKE NEW ANTIHELMINTICALLY EFFECTIVE ASSOCIATIONS BY CULTIVATING STREPTOMYCS AVERMITILIS |
US4093629A (en) * | 1977-04-11 | 1978-06-06 | Merck & Co., Inc. | Derivatives of antibiotic substance milbemycin and processes therefor |
NZ186851A (en) * | 1977-04-11 | 1984-12-14 | Merck & Co Inc | Glycosyloxy derivatives of milbemycin and parasiticidal compositions |
PH15982A (en) * | 1977-10-03 | 1983-05-18 | Merck & Co Inc | Selective hydrogenation producta of c-076 compounds and derivatives thereof |
NZ188459A (en) * | 1977-10-03 | 1982-09-07 | Merck & Co Inc | Derivatives of c-076 compounds and pesticidal compositions |
PH16612A (en) * | 1977-12-19 | 1983-11-28 | Merck & Co Inc | 13-halo and 13-deoxy derivatives of c-076 compounds |
JPS5632481A (en) * | 1979-08-23 | 1981-04-01 | Sankyo Co Ltd | Antibiotic b-41d, its preparation, and acaricide and anthelminthic agent and repellent containing the same as active constituent |
JPS57139012A (en) * | 1981-02-23 | 1982-08-27 | Sankyo Co Ltd | Anthelmintic composition |
EP0102702B1 (en) * | 1982-07-22 | 1987-07-29 | Imperial Chemical Industries Plc | Methods and compositions of combating pests |
JPS60141293A (en) * | 1983-12-28 | 1985-07-26 | Kitasato Inst:The | Novel carcinostatic antibiotic substance 81-484 and its production |
US5169956A (en) * | 1984-06-05 | 1992-12-08 | American Cyanamid Company | Macrolide antibiotic compounds |
IE59394B1 (en) * | 1984-09-14 | 1994-02-23 | American Cyanamid Co | Antibiotic compounds and their preparation |
GB8606120D0 (en) * | 1986-03-12 | 1986-04-16 | Glaxo Group Ltd | Process |
JP2587241B2 (en) * | 1986-07-24 | 1997-03-05 | ビ−チヤム・グル−プ・ピ−エルシ− | Novel compound, production method thereof and pharmaceutical composition containing the same |
US4831016A (en) * | 1986-10-31 | 1989-05-16 | Merck & Co., Inc. | Reduced avermectin derivatives |
DE3888936T2 (en) * | 1987-11-03 | 1994-07-21 | Beecham Group Plc | Intermediates for the production of macrolide antibiotics with an anthelmintic effect. |
GB8804440D0 (en) * | 1988-02-25 | 1988-03-23 | Pfizer Ltd | Antiparasitic agents |
GB8815967D0 (en) * | 1988-07-05 | 1988-08-10 | Pfizer Ltd | Antiparasitic agents |
GB8917064D0 (en) * | 1989-07-26 | 1989-09-13 | Pfizer Ltd | Antiparasitic agent |
US5290804A (en) * | 1991-05-01 | 1994-03-01 | Merck & Co., Inc. | Anthelmintic milbemycin analogs of novel microorganisms |
GB9205007D0 (en) * | 1992-03-07 | 1992-04-22 | Pfizer Ltd | Antiparasitic agents |
JP2952265B2 (en) * | 1993-11-29 | 1999-09-20 | 井筒屋化学産業株式会社 | Composition and method for preventing pine wilt |
DE19613972A1 (en) * | 1996-04-09 | 1997-10-16 | Bayer Ag | Injection formulations of avermectins and milbemycins based on castor oil |
US6733767B2 (en) | 1998-03-19 | 2004-05-11 | Merck & Co., Inc. | Liquid polymeric compositions for controlled release of bioactive substances |
GB9825402D0 (en) * | 1998-11-19 | 1999-01-13 | Pfizer Ltd | Antiparasitic formulations |
PT1435786E (en) | 2001-09-17 | 2011-07-20 | Lilly Co Eli | Pesticidal formulations |
US7671034B2 (en) | 2003-12-19 | 2010-03-02 | Merial Limited | Stabilized formulation of ivermectin feed premix with an extended shelf life |
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KR101472649B1 (en) | 2007-05-15 | 2014-12-16 | 메리얼 리미티드 | Aryloazol-2-yl cyanoethylamino compounds, method of making and method of using thereof |
WO2010056999A1 (en) | 2008-11-14 | 2010-05-20 | Merial Limited | Enantiomerically enriched aryloazol- 2 -yl cyanoethylamino paraciticidal compounds |
AP3359A (en) | 2008-11-19 | 2015-07-31 | Merial Ltd | Compositions comprising 1-arylpyrazole alone or incombination with formamidine for the treatment of parasitic infection |
EP2327410A1 (en) * | 2009-10-28 | 2011-06-01 | Consiglio Nazionale Delle Ricerche - Infm Istituto Nazionale Per La Fisica Della Materia | Avermectins and milbemycins for the treatment of flavivirus infections |
WO2011069143A1 (en) | 2009-12-04 | 2011-06-09 | Merial Limited | Pesticidal bis-organosulfur compounds |
ES2569486T3 (en) | 2009-12-17 | 2016-05-11 | Merial, Inc. | Antiparasitic dihydroazole compounds and compositions comprising the same |
UA108641C2 (en) | 2010-04-02 | 2015-05-25 | PARASITICID COMPOSITION CONTAINING FOUR ACTIVE AGENTS AND METHOD OF APPLICATION | |
MX2013005414A (en) | 2010-11-16 | 2013-08-29 | Centre Nat Rech Scient | Novel monensin derivatives for the treatment and prevention of protozoal infections. |
US20120329832A1 (en) | 2011-06-27 | 2012-12-27 | Jean Delaveau | Novel Insect-Repellent Coumarin Derivatives, Syntheses, and Methods of Use |
WO2013003505A1 (en) | 2011-06-27 | 2013-01-03 | Merial Limited | Amido-pyridyl ether compounds and compositions and their use against parasites |
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US20130079394A1 (en) | 2011-09-23 | 2013-03-28 | Cnrs (Centre National Recherche Scientifique) | Indirect modeling of new repellent molecules active against insects, acarids, and other arthropods |
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EP2886640A1 (en) | 2013-12-18 | 2015-06-24 | Riga Technical University | Process for isolation of milbemycins A3 and A4 |
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US20220323421A1 (en) | 2019-07-22 | 2022-10-13 | Intervet Inc. | Soft Chewable Veterinary Dosage Form |
BR112022024156A2 (en) | 2020-05-29 | 2023-02-14 | Boehringer Ingelheim Animal Health Usa Inc | ANTHELMINTIC HETEROCYLIC COMPOUNDS |
US20220201983A1 (en) | 2020-12-21 | 2022-06-30 | Boehringer Ingelheim Animal Health USA Inc. | Parasiticidal collar comprising isoxazoline compounds |
JP2024516912A (en) | 2021-05-14 | 2024-04-17 | シンジェンタ クロップ プロテクション アクチェンゲゼルシャフト | Control of insect, acarine and nematode pests |
WO2023203038A1 (en) | 2022-04-19 | 2023-10-26 | Syngenta Crop Protection Ag | Insect, acarina and nematode pest control |
-
1972
- 1972-06-08 JP JP47057058A patent/JPS4914624A/ja active Pending
-
1973
- 1973-05-30 IL IL42401A patent/IL42401A/en unknown
- 1973-06-06 IT IT68686/73A patent/IT986430B/en active
- 1973-06-06 ES ES415591A patent/ES415591A1/en not_active Expired
- 1973-06-07 CH CH930276A patent/CH585514A5/xx not_active IP Right Cessation
- 1973-06-07 ZA ZA00733857A patent/ZA733857B/en unknown
- 1973-06-07 FR FR7320831A patent/FR2187778B1/fr not_active Expired
- 1973-06-07 CH CH826473A patent/CH585789A5/xx not_active IP Right Cessation
- 1973-06-08 SU SU731931001A patent/SU588926A3/en active
- 1973-06-08 DE DE2329486A patent/DE2329486C2/en not_active Expired
- 1973-06-08 BR BR4308/73A patent/BR7304308D0/en not_active IP Right Cessation
- 1973-06-08 GB GB2743773A patent/GB1390336A/en not_active Expired
-
1975
- 1975-08-20 SU SU752167200A patent/SU1360574A3/en active
Also Published As
Publication number | Publication date |
---|---|
SU1360574A3 (en) | 1987-12-15 |
DE2329486A1 (en) | 1973-12-20 |
IT986430B (en) | 1975-01-30 |
CH585789A5 (en) | 1977-03-15 |
BR7304308D0 (en) | 1974-08-29 |
FR2187778B1 (en) | 1976-06-11 |
GB1390336A (en) | 1975-04-09 |
ZA733857B (en) | 1975-04-30 |
DE2329486C2 (en) | 1984-01-12 |
CH585514A5 (en) | 1977-03-15 |
ES415591A1 (en) | 1976-07-01 |
FR2187778A1 (en) | 1974-01-18 |
IL42401A0 (en) | 1973-07-30 |
SU588926A3 (en) | 1978-01-15 |
AU5663173A (en) | 1974-12-12 |
JPS4914624A (en) | 1974-02-08 |
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