CS209201B1 - Insecticide and its semisynthetic method of manufacture - Google Patents
Insecticide and its semisynthetic method of manufacture Download PDFInfo
- Publication number
- CS209201B1 CS209201B1 CS792571A CS257179A CS209201B1 CS 209201 B1 CS209201 B1 CS 209201B1 CS 792571 A CS792571 A CS 792571A CS 257179 A CS257179 A CS 257179A CS 209201 B1 CS209201 B1 CS 209201B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- hydroxy
- acetyloxy
- hydroxymethylpyrone
- insecticide
- supernatant
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 title abstract description 7
- 239000002917 insecticide Substances 0.000 title description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims abstract description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- 230000000749 insecticidal effect Effects 0.000 claims abstract description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000007788 liquid Substances 0.000 claims abstract description 5
- 239000006228 supernatant Substances 0.000 claims abstract description 4
- 241000228168 Penicillium sp. Species 0.000 claims abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 5
- FTWYBBBWGWWCAZ-UHFFFAOYSA-N (5-acetyloxy-4-oxopyran-2-yl)methyl acetate Chemical compound CC(=O)OCC1=CC(=O)C(OC(C)=O)=CO1 FTWYBBBWGWWCAZ-UHFFFAOYSA-N 0.000 abstract 1
- 230000000397 acetylating effect Effects 0.000 abstract 1
- 238000009472 formulation Methods 0.000 abstract 1
- BEJNERDRQOWKJM-UHFFFAOYSA-N kojic acid Chemical compound OCC1=CC(=O)C(O)=CO1 BEJNERDRQOWKJM-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241000238631 Hexapoda Species 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 241000607479 Yersinia pestis Species 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 235000013399 edible fruits Nutrition 0.000 description 3
- 238000000855 fermentation Methods 0.000 description 3
- 230000004151 fermentation Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000002211 ultraviolet spectrum Methods 0.000 description 3
- 241000218475 Agrotis segetum Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000004896 high resolution mass spectrometry Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 229930195730 Aflatoxin Natural products 0.000 description 1
- XWIYFDMXXLINPU-UHFFFAOYSA-N Aflatoxin G Chemical compound O=C1OCCC2=C1C(=O)OC1=C2C(OC)=CC2=C1C1C=COC1O2 XWIYFDMXXLINPU-UHFFFAOYSA-N 0.000 description 1
- 241000193388 Bacillus thuringiensis Species 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 102000015439 Phospholipases Human genes 0.000 description 1
- 108010064785 Phospholipases Proteins 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000005409 aflatoxin Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 238000009360 aquaculture Methods 0.000 description 1
- 244000144974 aquaculture Species 0.000 description 1
- 229940097012 bacillus thuringiensis Drugs 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000000688 bacterial toxin Substances 0.000 description 1
- 230000000035 biogenic effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000002158 endotoxin Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000009313 farming Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000002636 mycotoxin Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000005868 ontogenesis Effects 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 231100000654 protein toxin Toxicity 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
- C12P17/06—Oxygen as only ring hetero atoms containing a six-membered hetero ring, e.g. fluorescein
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/40—Oxygen atoms attached in positions 3 and 4, e.g. maltol
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/14—Fungi; Culture media therefor
- C12N1/145—Fungal isolates
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/645—Fungi ; Processes using fungi
- C12R2001/80—Penicillium
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Medicinal Chemistry (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- General Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Environmental Sciences (AREA)
- Botany (AREA)
- Mycology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- Virology (AREA)
- Biomedical Technology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pyrane Compounds (AREA)
Description
ČESKOSLOVENSKASOCIALISTICKÁREPUBLIKA( 10 ) POPIS VYNALEZU K AUTORSKÉMU OSVEDČENIU 209201 (11) (Bl) s (22) Přihlášené 17 04 79(21) (PV 2571-79) (51) Int. Cl.3 A 01 N 43/16 ÚŘAD PRO VYNÁLEZY A OBJEVY [......... (40) Zverejnené 15 09 80 (45) Vydané 01 05 83 (75)
Autor vynálezu BRTKO JÚLIUS ing., DOBIÁŠ JOSEF mg., CSc. a
NEMEC PAVEL člen korespondent, BRATISLAVA (54) Insektíddiiý prostriedok a jeho semisyntetický spósob výroby
Vynález sa týká insekticidného prostriedku na jochranu polnohospodárskych a ovodnárskych kul- jtůr voči škodcom širokého spektra, ktorý obsahuje Iako účinnú látku [5-acetyloxy-2-acetyloxymetyl- jpyron-(4)] vzorca: 1
a jeho semisyntetického spósobu výroby.
Boj so škodlivými druhmi hmyzu je v dnešnej době jednou z najvážnejších úloh světového (pol-nohospodárstva. Stúpajúci počet obyvatelstva', ne-ustále sa zvyšujúce nároky na kvantitu produkova-ných potravin na jednej straně, toxicita, maláSpecifičnost, nebezpečie znečisťovania biosféry re-ziduami syntetických chlórovaných insekticídovtypu DDT, organofosforových zlúčenín, ich kumu-latívny a tým i toxický účinok vo vyšších organiz-moch, ďalej vzrastajúca rezistencia hmyzu vočitýmto látkám, na druhej straně, aktualizujú hlada-nie nových spósobov ochrany polnohospodárskych rastlinných kultúr před hmyzími škodcami. Alar-mujúce zjavy univerzálneho rozšírenia chlórova-ných preparátov v telách organizmov, v dósledkupostupnej kontaminácie potravinového reťazca,posúvajú do popredia spósob ochrany rastlín,s novými, pre člověka netoxickými a v biosféřeZeme rozkladajúcimi sa preparátmi. Potvrdzuje toi doteraz urobený výskům s bakteriálnymi a hubo-vými toxínmi v praxi. Dnes sú podrobné popísanépřírodně protihmyzové látky typu aflatoxínov a de-struxínov. Známy je toxín producenta Badllusthuringiensis, ktorý produkuje endotoxín - krys-talické útvary, tzv. parasporálne telieska s obsa-hom velmi jedovatého toxínu bielkovinového cha-rakteru. Zaujímavé sa ukázali byť rožne lecitinázy,proteázy a iné enzýmy.
Uvedené nevýhody odstraňuje insekticidný pro-striedok, ktorý ako účinnú látku obsahuje [5-ace-tyloxy-2-acetyloxymetyl-pyron-(4)] vzorca: 0 0 II 11 JL/0-c-ch3
XT CHs-C-0-CHf^O^ 3 II * 0 209201 ..........'......-.........— ..............~.....'......
Podía výfíélezu sa insektiddný prostriedok vyrobísemisyntctickým spósobom, ktorého podstata spo-čívá v tom, že stadonámou alebo submerznoukultivádou Penidlium sp. pri teploto 27 °C naCzapek-Doxoviom tekutom médiu a následnouextrakdou výhodné acetónom a dalSou purifiká-dou s metanolům a rekryštalizádou pri pH 1,8 sapřipraví [5-hydroxy-2-hydroxy-metylpyron-(4)],ktorý sa ďalej acetyluje s anhydridom kyselinyóctovéj v bezvodom prostředí pyridinu. Nezreago-vaný [5-hydroxy-2-hydroxymetylpyron-(4)] saacetyládou oddělí od balastných látok a po zahuš-tění sa vrátí do reakčného cyklu. Následujúce příklady uvádzajú spósob výrobyinsektiddného prostriedku podlá vynálezu a cha-rakterizujú a konfrontuji! jeho vlastnosti. Přikladl a) [5-hydroxy-2-hydroxymetylpyron-(4)]mentačný spósob přípravy — Fer-
Penicillium sp. (zb. č. 29, Zbierka mikroorganiz-mov oddelenia biológie nízkomolekulárnych látok,Ústavu molekulámej biológie SA V, Bratislava) sakultivovalo stadonáme pri teplote 27 °C, 14 dnív 2000 ml Rouxových fíašiach na 200 ml Czapek-Doxovho tekutého média, alebo submerzným spó-sobom v laboratómych tančíkoch o obsahu 141 navyššie uvedenej póde, 5 dní pri teplote 27 °C, priotáčkách miešadla 150 . min-1 a prevzdušňovaní10 litrov za minútu. Mycélium, spolu s fermentač-nou tekutinou v množstve 2800 ml sa zhomogeni-zovalo v mixéri, 2 min., zmes sa centrifugovala pri3000 otáčok. min-1,10 min. Ďalšie kroky izoláde [5-hydroxy-2-hydroxyme-tylpyron-(4)] podlá vynálezu uvádza nasledovnáschéma:
Ako identifikačně reakde sa použili okrem kvalita-tívnych analytických reakdí s FeCl3, resp. s Fehlin-govými roztokmi, stanovenie bodu topenia, zá-znam spektra zlúčeniny v ultrafialovej a infračerve-nej oblasti. Porovnáme získaných údajov, spolu sozáznamom spektra v infračervenej a v ultrafialovejoblasti, s literámymi údajmi boli zhodné (bodtopenia: 152 °C, absorpda v UV oblasti spektra: 217,269 nm). Sumárny vzorec (C^HgOJ a mole-kulová hmotnost (142,11) boli stanovené vysoko- rozlišovacou hmotnostnou spektrometriou. ) - b)
Druhá etapa výroby podlá vynálezu je acetyláda s anhydridom kyseliny octovej v bezvodnom pro- středí pyridinu podía reakde:
Claims (3)
1. Insekticidný prostriedok vyznačujúci sa tým, že ako účinnú látku obsahuje [5-acetyloxy-2-ace- tyloxymetylpyron-(4)] vzorca: [5-acetyloxy-2-acetyl- oxymetylpyron-(4)j ZlUCenina ED50 (ug. gkultivačnej pódy) 895 209201 I ϊ χ5γ° CHpC-O-CHf^O^ "L............Ο____________i.................... .....
2. Semisyntetický spdsob výroby insektiddnéhoprostriedku podlá bodu 1, vyznačujúci sa tým, žePenicilium sp. sa stacionárně alebo submerzne kultivuje pri teplote 27 °Č na Czapek-Doxovomtekutom médiu, supernatant sa extrahuje s výho-dou acetónom a ďálej purifikuje s metanolom, a poúpravě pH na 1,8 sa rekryštalizuje a připravený[5-hydroxy-2-hydroxymetylpyron-(4)] sa ácetylu-je s anhydridom kyseliny octovej v bezvodomprostředí pyridinu.
3. Spósob výroby podlá bodu 1 a 2 vyznačujúcisa tým, že nezreagovaný [5-hydroxy-2-hydroxy-metylpyron-(4)] sa acetyládou oddělí od balast-ných látok a po zahuštění sa vrátí do reakčnéhocyklu. Cena: 2,40 Kčs Vytiskly Moravské tiskařské závody, provoz 12, Leninova 21, Olomouc
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS792571A CS209201B1 (en) | 1979-04-17 | 1979-04-17 | Insecticide and its semisynthetic method of manufacture |
| GB8011838A GB2047699A (en) | 1979-04-17 | 1980-04-10 | Process for the production of 2- acetyloxymethyl-5-acetyloxypyr-4-one |
| JP4877280A JPS55160703A (en) | 1979-04-17 | 1980-04-15 | Insecticide and its semisynthesis |
| DE19803014618 DE3014618A1 (de) | 1979-04-17 | 1980-04-16 | 5-acetoxy-2-acetoxymethylpyron-4, seine herstellung und verwendung als insektizid |
| HU80933A HU182668B (en) | 1979-04-17 | 1980-04-17 | Insecticide composition and semisynthetic process for preparing the active substance |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS792571A CS209201B1 (en) | 1979-04-17 | 1979-04-17 | Insecticide and its semisynthetic method of manufacture |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS209201B1 true CS209201B1 (en) | 1981-11-30 |
Family
ID=5363208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS792571A CS209201B1 (en) | 1979-04-17 | 1979-04-17 | Insecticide and its semisynthetic method of manufacture |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS55160703A (cs) |
| CS (1) | CS209201B1 (cs) |
| DE (1) | DE3014618A1 (cs) |
| GB (1) | GB2047699A (cs) |
| HU (1) | HU182668B (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116234445A (zh) * | 2020-08-18 | 2023-06-06 | 西悉尼大学 | 杀虫剂 |
-
1979
- 1979-04-17 CS CS792571A patent/CS209201B1/cs unknown
-
1980
- 1980-04-10 GB GB8011838A patent/GB2047699A/en not_active Withdrawn
- 1980-04-15 JP JP4877280A patent/JPS55160703A/ja active Pending
- 1980-04-16 DE DE19803014618 patent/DE3014618A1/de not_active Ceased
- 1980-04-17 HU HU80933A patent/HU182668B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55160703A (en) | 1980-12-13 |
| HU182668B (en) | 1984-02-28 |
| DE3014618A1 (de) | 1980-10-30 |
| GB2047699A (en) | 1980-12-03 |
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| Shakirzyanova et al. | Pheromone Monitoring in the Granaries of Uzbekistan | |
| Gatterdam et al. | The Absorption, Metabolism, and Excretion of C14-labelled TDE in Certain Insects | |
| Kohn et al. | The agrochemical industry | |
| Whitehead | The development and mechanism of insecticide resistance in the blue tick, Boophilus decoloratus Koch |