DE2247507C2 - Verfahren zur Stabilisierung von steroidalen Insektenhäutungshormonen gegenüber der Einwirkung von Licht und dadurch stabilisierte Insektizide - Google Patents
Verfahren zur Stabilisierung von steroidalen Insektenhäutungshormonen gegenüber der Einwirkung von Licht und dadurch stabilisierte InsektizideInfo
- Publication number
- DE2247507C2 DE2247507C2 DE2247507A DE2247507A DE2247507C2 DE 2247507 C2 DE2247507 C2 DE 2247507C2 DE 2247507 A DE2247507 A DE 2247507A DE 2247507 A DE2247507 A DE 2247507A DE 2247507 C2 DE2247507 C2 DE 2247507C2
- Authority
- DE
- Germany
- Prior art keywords
- light
- hormone
- stabilized
- insecticides
- insect molting
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 239000002428 insect molting hormone Substances 0.000 title claims description 14
- 239000002917 insecticide Substances 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 8
- 230000003637 steroidlike Effects 0.000 title claims description 5
- 230000006641 stabilisation Effects 0.000 title 1
- 238000011105 stabilization Methods 0.000 title 1
- 239000003381 stabilizer Substances 0.000 claims description 11
- 230000000087 stabilizing effect Effects 0.000 claims description 5
- 150000001565 benzotriazoles Chemical class 0.000 claims description 4
- FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical class OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 230000000176 photostabilization Effects 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 229940088597 hormone Drugs 0.000 description 29
- 239000005556 hormone Substances 0.000 description 28
- NKDFYOWSKOHCCO-YPVLXUMRSA-N 20-hydroxyecdysone Chemical compound C1[C@@H](O)[C@@H](O)C[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@@](C)(O)[C@H](O)CCC(C)(O)C)CC[C@]33O)C)C3=CC(=O)[C@@H]21 NKDFYOWSKOHCCO-YPVLXUMRSA-N 0.000 description 19
- NKDFYOWSKOHCCO-UHFFFAOYSA-N beta-ecdysone Natural products C1C(O)C(O)CC2(C)C(CCC3(C(C(C)(O)C(O)CCC(C)(O)C)CCC33O)C)C3=CC(=O)C21 NKDFYOWSKOHCCO-UHFFFAOYSA-N 0.000 description 19
- 239000000243 solution Substances 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 11
- 239000000126 substance Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- WSSJONWNBBTCMG-UHFFFAOYSA-N 2-hydroxybenzoic acid (3,3,5-trimethylcyclohexyl) ester Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C1=CC=CC=C1O WSSJONWNBBTCMG-UHFFFAOYSA-N 0.000 description 6
- UWSMKYBKUPAEJQ-UHFFFAOYSA-N 5-Chloro-2-(3,5-di-tert-butyl-2-hydroxyphenyl)-2H-benzotriazole Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O UWSMKYBKUPAEJQ-UHFFFAOYSA-N 0.000 description 6
- SGNLNHWVOICCOZ-UHFFFAOYSA-N Crustecdyson Natural products CC(O)C1(CCC2(O)C3=CC(=O)C4CC(O)C(O)CC4(C)C3CCC12C)C(O)CCC(C)(C)O SGNLNHWVOICCOZ-UHFFFAOYSA-N 0.000 description 6
- DCEFCUHVANGEOE-UHFFFAOYSA-N Ecdysterone Natural products CC(CC(C)(C)O)C(O)C(C)(O)C1CCC2(O)C3=CC(=O)C4CC(O)C(O)CC4(C)C3CCC12C DCEFCUHVANGEOE-UHFFFAOYSA-N 0.000 description 6
- UPEZCKBFRMILAV-UHFFFAOYSA-N alpha-Ecdysone Natural products C1C(O)C(O)CC2(C)C(CCC3(C(C(C(O)CCC(C)(C)O)C)CCC33O)C)C3=CC(=O)C21 UPEZCKBFRMILAV-UHFFFAOYSA-N 0.000 description 6
- HXWZQRICWSADMH-SEHXZECUSA-N 20-hydroxyecdysone Natural products CC(C)(C)CC[C@@H](O)[C@@](C)(O)[C@H]1CC[C@@]2(O)C3=CC(=O)[C@@H]4C[C@@H](O)[C@@H](O)C[C@]4(C)[C@H]3CC[C@]12C HXWZQRICWSADMH-SEHXZECUSA-N 0.000 description 5
- UPEZCKBFRMILAV-JNEQICEOSA-N Ecdysone Natural products O=C1[C@H]2[C@@](C)([C@@H]3C([C@@]4(O)[C@@](C)([C@H]([C@H]([C@@H](O)CCC(O)(C)C)C)CC4)CC3)=C1)C[C@H](O)[C@H](O)C2 UPEZCKBFRMILAV-JNEQICEOSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- UPEZCKBFRMILAV-JMZLNJERSA-N ecdysone Chemical compound C1[C@@H](O)[C@@H](O)C[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@@H]([C@H](O)CCC(C)(C)O)C)CC[C@]33O)C)C3=CC(=O)[C@@H]21 UPEZCKBFRMILAV-JMZLNJERSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 241000238631 Hexapoda Species 0.000 description 4
- YXPVYQIMXPYFSF-UHFFFAOYSA-N Makisterone A Natural products CC(C)C(C)(O)CC(O)C(C)(O)C1CCC2(O)C3=CC(=O)C4CC(O)C(O)CC4(C)C3CCC12C YXPVYQIMXPYFSF-UHFFFAOYSA-N 0.000 description 4
- IJRBORPEVKCEQD-JMQWOFAPSA-N Makisterone A Chemical compound C1[C@@H](O)[C@@H](O)C[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@@](C)(O)[C@H](O)C[C@@H](C)C(C)(C)O)CC[C@]33O)C)C3=CC(=O)[C@@H]21 IJRBORPEVKCEQD-JMQWOFAPSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- ZMWRRFHBXARRRT-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=CC=CC3=N2)=C1O ZMWRRFHBXARRRT-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229930187267 Muristeron Natural products 0.000 description 3
- LRJUYAVTHIEHAI-LHBNDURVSA-N Muristerone Chemical compound C1[C@@H](O)[C@@H](O)C[C@]2(C)[C@@H]([C@H](O)C[C@@]3([C@@H]([C@@](C)(O)[C@H](O)CCC(C)C)CC[C@]33O)C)C3=CC(=O)[C@@]21O LRJUYAVTHIEHAI-LHBNDURVSA-N 0.000 description 3
- 229930182558 Sterol Natural products 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000749 insecticidal effect Effects 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 150000003432 sterols Chemical class 0.000 description 3
- 235000003702 sterols Nutrition 0.000 description 3
- FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical class OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 description 2
- -1 2-hydroxyphenyl Chemical group 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000003912 environmental pollution Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003053 toxin Substances 0.000 description 2
- 231100000765 toxin Toxicity 0.000 description 2
- 108700012359 toxins Proteins 0.000 description 2
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- VROYHCMGMRXPPB-UHFFFAOYSA-N Ecdysteron Natural products CC(CC(C)(C)O)C(O)C(C)(O)C1CCC2(O)C3CC(=O)C4CC(O)C(O)CC4(C)C3CCC12C VROYHCMGMRXPPB-UHFFFAOYSA-N 0.000 description 1
- HHLFWLYXYJOTON-UHFFFAOYSA-N Glyoxylic acid Natural products OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
- C07J31/006—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring not covered by C07J31/003
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/22—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients stabilising the active ingredients
-
- 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
- A01N63/00—Biocides, pest repellants or attractants, or plant growth regulators containing microorganisms, viruses, microbial fungi, animals or substances produced by, or obtained from, microorganisms, viruses, microbial fungi or animals, e.g. enzymes or fermentates
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/12—Fertilization attaching inhibition
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Toxicology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Virology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT29276/71A IT945969B (it) | 1971-09-29 | 1971-09-29 | Procedimento per la stabilizzazio ne di steroli poliidrossilati e prodotto insetticida biologico sta bilizzato cosi ottenuto |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2247507A1 DE2247507A1 (de) | 1973-04-05 |
| DE2247507C2 true DE2247507C2 (de) | 1982-04-29 |
Family
ID=11226666
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2247507A Expired DE2247507C2 (de) | 1971-09-29 | 1972-09-28 | Verfahren zur Stabilisierung von steroidalen Insektenhäutungshormonen gegenüber der Einwirkung von Licht und dadurch stabilisierte Insektizide |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4045555A (enExample) |
| JP (1) | JPS4840928A (enExample) |
| AU (1) | AU467967B2 (enExample) |
| BR (1) | BR7206805D0 (enExample) |
| CA (1) | CA966776A (enExample) |
| DD (1) | DD101547A1 (enExample) |
| DE (1) | DE2247507C2 (enExample) |
| ES (1) | ES407144A1 (enExample) |
| FR (1) | FR2154656B1 (enExample) |
| GB (1) | GB1401645A (enExample) |
| IT (1) | IT945969B (enExample) |
| NL (1) | NL7213159A (enExample) |
| OA (1) | OA04185A (enExample) |
| SE (1) | SE7212543L (enExample) |
| ZA (1) | ZA726611B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57175109A (en) * | 1981-04-21 | 1982-10-28 | Hokko Chem Ind Co Ltd | Improved purified machine oil emulsion |
| US4552885A (en) * | 1981-12-24 | 1985-11-12 | Ciba Geigy Corporation | Stabilized fungicide compositions |
| US4622315A (en) * | 1983-02-10 | 1986-11-11 | The Regents Of The University Of California | Additives for improved pesticide photstability |
| JPS60182659A (ja) * | 1984-02-29 | 1985-09-18 | Shin Kobe Electric Mach Co Ltd | 極板自動練塗装置 |
| JPH05121068A (ja) * | 1991-10-29 | 1993-05-18 | Shin Kobe Electric Mach Co Ltd | 極板製造用自動ペースト充填装置及びその制御方法 |
| CN118077701B (zh) * | 2022-11-25 | 2025-07-18 | 沈阳中化农药化工研发有限公司 | 一种杀虫和杀螨制剂及其应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE563210A (enExample) * | 1956-12-14 | 1958-06-13 | ||
| GB1159137A (en) | 1966-01-19 | 1969-07-23 | Int Minerals & Chem Corp | Stabilized Microbial Insecticides |
| US3453362A (en) * | 1966-05-10 | 1969-07-01 | Fmc Corp | Insect control methods and compositions |
-
1971
- 1971-09-29 IT IT29276/71A patent/IT945969B/it active
-
1972
- 1972-09-26 CA CA152,553A patent/CA966776A/en not_active Expired
- 1972-09-26 US US05/292,295 patent/US4045555A/en not_active Expired - Lifetime
- 1972-09-27 GB GB4467872A patent/GB1401645A/en not_active Expired
- 1972-09-27 FR FR7234224A patent/FR2154656B1/fr not_active Expired
- 1972-09-27 ZA ZA726611A patent/ZA726611B/xx unknown
- 1972-09-27 AU AU47159/72A patent/AU467967B2/en not_active Expired
- 1972-09-28 DE DE2247507A patent/DE2247507C2/de not_active Expired
- 1972-09-28 NL NL7213159A patent/NL7213159A/xx not_active Application Discontinuation
- 1972-09-28 OA OA54703A patent/OA04185A/xx unknown
- 1972-09-28 SE SE7212543A patent/SE7212543L/xx unknown
- 1972-09-28 DD DD165924A patent/DD101547A1/xx unknown
- 1972-09-29 BR BR6805/72A patent/BR7206805D0/pt unknown
- 1972-09-29 JP JP47097254A patent/JPS4840928A/ja active Pending
- 1972-09-29 ES ES407144A patent/ES407144A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU4715972A (en) | 1974-04-04 |
| AU467967B2 (en) | 1975-12-18 |
| DD101547A1 (enExample) | 1973-11-12 |
| IT945969B (it) | 1973-05-10 |
| US4045555A (en) | 1977-08-30 |
| NL7213159A (enExample) | 1973-04-02 |
| JPS4840928A (enExample) | 1973-06-15 |
| SE7212543L (enExample) | 1973-03-30 |
| GB1401645A (en) | 1975-07-16 |
| OA04185A (fr) | 1979-12-31 |
| DE2247507A1 (de) | 1973-04-05 |
| ES407144A1 (es) | 1975-11-01 |
| ZA726611B (en) | 1973-07-25 |
| BR7206805D0 (pt) | 1973-09-18 |
| CA966776A (en) | 1975-04-29 |
| FR2154656A1 (enExample) | 1973-05-11 |
| FR2154656B1 (enExample) | 1976-05-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |