NO126292B - - Google Patents

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Publication number
NO126292B
NO126292B NO02754/69A NO275469A NO126292B NO 126292 B NO126292 B NO 126292B NO 02754/69 A NO02754/69 A NO 02754/69A NO 275469 A NO275469 A NO 275469A NO 126292 B NO126292 B NO 126292B
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Norway
Prior art keywords
active substance
comparison
beetles
triazole
emulsion
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NO02754/69A
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Norwegian (no)
Inventor
Walter Finkenbrink
Ludwig Friedrich Emmel
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Hoechst Ag
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    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals
    • 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
    • C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Molecular Biology (AREA)
  • Agronomy & Crop Science (AREA)
  • Biochemistry (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

Insekticid og akaricid middel. Insecticide and acaricide agent.

Oppfinnelsens gjenstand er et insekticid og akaricid The object of the invention is an insecticide and acaricide

middel som er karakterisert ved at det består av eller inneholder en blanding av 1-10 vektdeler av 1,2,3,^,7,7-heksaklorbicyklo-- £~ 2 >2, l/-hepten- (2 )-bis-/~~hydroksymetylen- (5 ,6 y/-sulf it med formelen agent which is characterized in that it consists of or contains a mixture of 1-10 parts by weight of 1,2,3,^,7,7-hexachlorobicyclo-- £~ 2 >2, l/-heptene-(2 )-bis -/~~hydroxymethylene- (5 .6 y/-sulphite with the formula

og 1 vektdel l-fenyl-3(0,0-dietyltionofosforyl)-l,2,4-triazol med formelen and 1 part by weight of 1-phenyl-3(0,0-diethylthionophosphoryl)-1,2,4-triazole with the formula

Den førstnevnte heksaklorbicykloheptenforbindelse er kjent fra tysk patent nr. 1.015-797 og US-patent nr. 2.799-685. The former hexachlorobicycloheptene compound is known from German Patent No. 1,015-797 and US Patent No. 2,799-685.

Den anvendes som insekticid og akaricid, spesielt i frukt-, grønnsak-og akerbruk overfor bitende og sugende insekter og i forstvesenet mot biller, insektlarver og trelus. It is used as an insecticide and acaricide, especially in fruit, vegetable and arable farming against biting and sucking insects and in forestry against beetles, insect larvae and woodlice.

Det har imidlertid vist seg at virkningen av nevnte heksaklorbicykloheptenforbindelse i mange tilfeller ikke er til-strekkelig til å oppnå en fullstendig utryddelse av skadedyrene. However, it has been shown that the effect of said hexachlorobicycloheptene compound is in many cases not sufficient to achieve a complete eradication of the pests.

Det har nå blitt funnet at blandinger av heksdklorbi-cyklo-/-2,2 , iy-hepten- (2 ) -bis-/~hydroksymetylen- (5 , 6_)/-sulfit med 1-fenyl-3-(0,0-dietyltionofosforyl)-l,2,4-triazol har en fremragende virkning nettopp i slike tilfeller hvor førstnevnte forbindelse er utilstrekkelig. Anvendelig er da slike skadedyrsbekjempelses-midler som er karakterisert ved et innhold av 1-10 vektdeler heksa-klorbicyklo-^~2 ,2 ,1/-he pt en- (2)-bis - £~ hy droksymetylen- (5 ,6 _)/-sulf it i blanding med 1 vektdel 1-feny1-3-(0,0-dietyltionofos fory1)-l,2,4-triazol. It has now been found that mixtures of hexdchlorobi-cyclo-/-2,2 , iy-heptene-(2)-bis-/~hydroxymethylene-(5 , 6_)/-sulphite with 1-phenyl-3-(0, O-diethylthionophosphoryl)-1,2,4-triazole has an outstanding effect precisely in such cases where the first-mentioned compound is insufficient. Such pest control agents which are characterized by a content of 1-10 parts by weight of hexa-chlorobicyclo-^~2 ,2 ,1/-he pt en-(2)-bis -£~ hydroxymethylene-(5 ,6 _)/-sulphite in a mixture with 1 part by weight of 1-phenyl-3-(0,0-diethylthiophos phoryl)-1,2,4-triazole.

Med disse virksomme stoffblandinger ifølge oppfinnelsen kan det meget bedre bekjempes et større antall av skadedyr enn det er mulig med den kjente heksaklorbicykloheptenforbindelse alene. Dette er spesielt tilfelle ved spinnemidd (Tetranychidae), skjoldlus (Pseudococcusarter), ved insektlarver av familien viklere (Tortrici-dae) og ved vanskelig bekjempbare skadedyr som den egyptiske bomulls-larven (Prodenia litura). Spesielt bemerkelsesverdig er en synergisk With these effective substance mixtures according to the invention, a greater number of pests can be combated much better than is possible with the known hexachlorobicycloheptene compound alone. This is especially the case with spider mites (Tetranychidae), scale lice (Pseudococcus species), with insect larvae of the family of spinners (Tortrici-dae) and with difficult-to-control pests such as the Egyptian cotton caterpillar (Prodenia litura). Particularly noteworthy is a synergistic

effekt mellom de to virksomme stoffer slik den f.eks. opptrer ved bekjempelse av meksikansk bønnebille (Epilachna varivestis). De virksomme stoffblandinger ifølge oppfinnelsen viser ved. siden av overfor enkeltkomponentene vesentlig forsterkede insekticid virkning også ovicid og akaricid virkning. effect between the two active substances as it e.g. occurs when fighting the Mexican bean beetle (Epilachna varivestis). The active substance mixtures according to the invention show wood. since compared to the individual components, the insecticidal effect also significantly increased the ovicidal and acaricidal effect.

De virksomme stoffblandinger ifølge oppfinnelsen kan til-beredes i kombinasjon med faste og flytende inerte bærestoffer med The active substance mixtures according to the invention can be prepared in combination with solid and liquid inert carriers with

klebemidler, fuktemidler, dispergeringsmidler og malehjelpemidler som sprøytepulvere, emulsjoner, suspensjoner, støv, granulater, fluebånd, strømidler og vaskemidler. De lar seg også blande med andre insekti- adhesives, wetting agents, dispersants and painting aids such as spray powders, emulsions, suspensions, dust, granules, fly tapes, streamers and detergents. They can also be mixed with other insecticides

cider, fungicider, nematocider og herbicider. cider, fungicides, nematocides and herbicides.

Som faste bærestoffer kan det anvendes mineralske stoffer som aluminiumsilikat, lerjord, kaolin, kritt, kiselgur eller hydratisert kiselgur eller tilberedninger av disse mineralske stoffer med spesielle tilsetninger, f.eks. kritt fettet med natriumstearat. Mineral substances such as aluminum silicate, clay soil, kaolin, chalk, diatomaceous earth or hydrated diatomaceous earth or preparations of these mineral substances with special additives, e.g. chalk greased with sodium stearate.

Som flytende bærestoffer kan det anvendes organiske opp-løsningsmidler som ketoner, f.eks. metyletyIketon, metylisobutyl- Organic solvents such as ketones can be used as liquid carriers, e.g. methyl ethyl ketone, methyl isobutyl-

keton og isoforon, videre estere som butylacetat bg glykoldiacetat, etere som dietylenglykol-dimetyleter, dietylenglykol-dietyleter og dietylenglykol-dibutyleter og videre høyere kokende aromater som xylen, anisol, decalin og tetralin. ketone and isophorone, further esters such as butyl acetate bg glycol diacetate, ethers such as diethylene glycol dimethyl ether, diethylene glycol diethyl ether and diethylene glycol dibutyl ether and further higher boiling aromatics such as xylene, anisole, decalin and tetralin.

Som klebestoffer kan det anvendes limaktige cellulose-produkter eller polyvinylalkoholer. Glue-like cellulose products or polyvinyl alcohols can be used as adhesives.

Som fuktestoffer kan det anvendes alle egnede emulgatorer som oksetylerte alkylfenoler, fettalkoholpolyglykoletere, fettsyre-polyglykolestere, salter av aryl- eller alkylarylsulfonsyrer, salter av metyltaurin, salter av fenylkogasinsulfonsyrer eller såper. All suitable emulsifiers such as oxytylated alkylphenols, fatty alcohol polyglycol ethers, fatty acid polyglycol esters, salts of aryl or alkylaryl sulphonic acids, salts of methyl taurine, salts of phenylcogasine sulphonic acids or soaps can be used as wetting agents.

Som dispergeringsstoffer kan det anvendes porebek (salter av sulfitavlut), salter av naftalinsulfonsyre såvel som undertiden hydratiserte kiselsyrer eller også kiselgur. As dispersants, pore pitch (salts of sulphite liquor), salts of naphthalene sulphonic acid as well as sometimes hydrated silicic acids or also diatomaceous earth can be used.

Som malehjelpemidler kan det anvendes egnede uorganiske eller organiske salter som natriumsulfat, ammoniumsulfat, natrium-karbonat, natriumbikarbonat, natriumtiosulfat, natriumstearat, natriumacetat. Suitable inorganic or organic salts such as sodium sulphate, ammonium sulphate, sodium carbonate, sodium bicarbonate, sodium thiosulphate, sodium stearate, sodium acetate can be used as grinding aids.

De insekticide og akaricide midler ifølge oppfinnelsen kan med fordel anvendes i form av et emulsjonskonsentrat som inneholder 10-70 vekt% av en virksom stoffblanding og 5-15 vekt% av et fuktemiddel, mens resten inntil 100 vekt% utgjøres av et organisk oppløsningsmiddel. The insecticidal and acaricidal agents according to the invention can advantageously be used in the form of an emulsion concentrate which contains 10-70% by weight of an active substance mixture and 5-15% by weight of a wetting agent, while the rest up to 100% by weight is made up of an organic solvent.

For den såkalte ultra-low-volum-fremgangsmåten hvor det fra flyvemaskiner sprøytes ut høykonsentrerte blandinger.ved hjelp av dyser, kan det anvendes midler som inneholder 70 - 95 vekt# av en virksom stoffblanding ifølge oppfinnelsen og 30 - 5 vekt$ av alifa-tiske og/eller aromatiske mineraloljer og/eller ketoner, hver med kokepunkt over 120°C, og/eller planteoljer som bomullsfrøolje eller ricinusolje og/eller flytende emulgatorer som eboksylerte alkylfenoler, f.eks. nonylfenol med 5-15 etylenoksydenheter pr. molekyl. For the so-called ultra-low-volume method, where highly concentrated mixtures are sprayed from airplanes using nozzles, means can be used which contain 70-95 wt% of an active substance mixture according to the invention and 30-5 wt% of aliphatic tic and/or aromatic mineral oils and/or ketones, each with a boiling point above 120°C, and/or vegetable oils such as cottonseed oil or castor oil and/or liquid emulsifiers such as eboxylated alkylphenols, e.g. nonylphenol with 5-15 ethylene oxide units per molecule.

Eksempel 1. Example 1.

En xylenoppløsrfng som inneholdt 35$ 1,2,3,4,7,7-heksa-klorbicyklo-/~2,2 ,l/-hepten- (2 )-bis-/T"hydroksymetylen- (5,6_)/-sulf it A xylene solvent containing 35$ 1,2,3,4,7,7-hexa-chlorobicyclo-/~2,2,1/-heptene-(2)-bis-/T"hydroxymethylene-(5,6_)/ -sulphite

(A) og 6% av en emulgatorblanding av alkylarylsulfonater og etoksylert alkylfenoler, ble emulgert i vann med en ytterligere xylenoppløsning (A) and 6% of an emulsifier mixture of alkylarylsulfonates and ethoxylated alkylphenols, was emulsified in water with a further xylene solution

som inneholdt 40% 1-feny1-3-(0,0-dietyltionofosforyl)-l,2,4-triazol which contained 40% 1-phenyl-3-(0,0-diethylthionophosphoryl)-1,2,4-triazole

(B) og 10% av en emulgatorblanding av alkylarylsulfonater med etoksy-lerte alkylfenoler som 2% f ettsyrepolyglykolester, således at den (B) and 10% of an emulsifier mixture of alkylaryl sulphonates with ethoxylated alkylphenols as 2% fatty acid polyglycol ester, so that the

virksomme stoffkonsentrasjon av bicykloheptenderivat (A) utgjorde 0. 007% resp. 0,0035% og den virksomme stoffkonsentrasjon av triazol-derivatet (B) utgjorde 0,001% resp. 0,0005%. active substance concentration of bicycloheptene derivative (A) amounted to 0.007% resp. 0.0035% and the active substance concentration of the triazole derivative (B) amounted to 0.001% resp. 0.0005%.

Denne virksomme stoffblanding ifølge oppfinnelsen ble sprøytet på meksikanske bønnebiller (Epilachna varivestis) i larve-resp. imago-stadiene likeledes som på deres for som besté av Phaseolus-blad, i maskinelt doserte, like mengder, dvs. like virksomme stoff-mengder pr. flateenhet. De behandlede insekter ble deretter satt på This effective substance mixture according to the invention was sprayed on Mexican bean beetles (Epilachna varivestis) in larvae or. the imago stages as well as on their lining which consisted of Phaseolus leaves, in mechanically dosed, equal amounts, i.e. equal amounts of active substance per surface unit. The treated insects were then put on

de tørkede blader. Det virksomme stoffs effekt ble vurdert etter 1, 2, 3 og 5 dager og angitt i følgende tabell 1. the dried leaves. The effect of the active substance was assessed after 1, 2, 3 and 5 days and is indicated in the following table 1.

Til sammenligning ble meksikanske bønnebiller behandlet under de samme betingelser med det ovennevnte bicykloheptenderivat For comparison, Mexican bean beetles were treated under the same conditions with the above-mentioned bicycloheptene derivative

(A) emulgert i den likeledes ovennevnte xylenoppløsning med vann til et virksomt stoffinnhold på 0,007% resp. 0,0035%. Denne sammenligningsemulsjon er i tabell 1 betegnet med sammenligning I. Til ytterligere sammenligning ble meksikansk bønnebille under de samme betingelser behandlet med den ovennevnte triazolderivat (B) i den ovenfor angitte xylenoppløsning, emulgert med vann til et virksomt stoffinnhold på 0,001% resp. 0,0005%. Denne sammenligningsemulsjon er i tabell I betegnet som sammenligning II. (A) emulsified in the likewise above-mentioned xylene solution with water to an active substance content of 0.007% resp. 0.0035%. This comparison emulsion is designated in Table 1 as comparison I. For further comparison, the Mexican bean beetle was treated under the same conditions with the above-mentioned triazole derivative (B) in the above-mentioned xylene solution, emulsified with water to an active substance content of 0.001% resp. 0.0005%. This comparison emulsion is designated in Table I as comparison II.

De i tabell I oppførte data viser at ved den virksomme stoffblanding ifølge oppfinnelsen i den angitte konsentrasjon ut-ryddes billene allerede etter 1 dag fullstendig, mens sammenligningsemulsjon I heller ikke etter 5 dager viser noen virkning og sammenligningsemulsjon II formår etter 2 dager og senere bare å utrydde 40% av billene. The data listed in Table I show that with the active substance mixture according to the invention in the specified concentration, the beetles are completely eradicated already after 1 day, while comparison emulsion I does not show any effect after 5 days either and comparison emulsion II manages after 2 days and later only to eradicate 40% of the beetles.

Ved anvendelse av blandingen ifølge oppfinnelsen i en konsentrasjon som er halvparten så stor som den som ble anvendt på billene var allerede etter 1 dag 100% av larvene beskadiget og etter 5 dager var de fullstendig utryddet, mens sammenligningsemulsjon I heller ikke viste noen virkning og sammenligningsemulsjon II etter When using the mixture according to the invention in a concentration that is half as great as that used on the beetles, 100% of the larvae were already damaged after 1 day and after 5 days they were completely eradicated, while comparison emulsion I also showed no effect and comparison emulsion II after

5 dager bare formådde å utrydde 30% av larvene. 5 days only managed to eradicate 30% of the larvae.

Dessuten har det ved gjennomføring av disse forsøk vist seg at ved anvendelse av den virksomme stoffblanding ifølge oppfinnelsen spiser billene bladene bare sporvis således at plantene prak-tisk talt ikke beskadiges. Derimot ødelegges ved anvendelse av sammenligningsemulsjonene bladene ved sterke spiseangrep til fullstendig oppspising. Furthermore, when carrying out these experiments, it has been shown that when using the active substance mixture according to the invention, the beetles eat the leaves only in traces, so that the plants are practically not damaged. In contrast, when using the comparison emulsions, the leaves are destroyed by strong feeding attacks until they are completely eaten.

Eksempel 2. Example 2.

Epler av valnøttstørrelse ble på- alle sider sprøytet med en virksom stoffblanding ifølge oppfinnelsen som var sammensatt tilsvarende den i eksempel 1 omtalte og inneholdt 0,2% 1,2,3,4,7,7-heksaklorbicyklo-/~2,2 jl^-hepten-(2)-bis-/ hydroksymetylen-(5, 6) J-sulfit (A) sammen med 0,025% l-fenyl-3-(0,0-dietyltionofosforyl)-1,2,4-triazol (B) i vandig emulsjon. Apples the size of walnuts were sprayed on all sides with an effective substance mixture according to the invention, which was composed similarly to that described in example 1 and contained 0.2% 1,2,3,4,7,7-hexachlorobicyclo-/~2.2 jl ^-heptene-(2)-bis-/hydroxymethylene-(5, 6) J-sulphite (A) together with 0.025% 1-phenyl-3-(0,0-diethylthionophosphoryl)-1,2,4-triazole ( B) in aqueous emulsion.

Eplene ble tørket .hengende på stilken og deretter belagt med egg av eplevikler (Carpocapsa pomonella). Vurderingen av virkningen etter 7 dager viser at 100% av billene var utryddet. The apples were dried hanging on the stem and then coated with eggs of the apple borer (Carpocapsa pomonella). The assessment of the effect after 7 days shows that 100% of the beetles were eradicated.

Til sammenligning ble ved en behandling med en emulsjon som inneholder 0,2% (A) under ellers like betingelser bare 52% av billene utryddet. In comparison, when treated with an emulsion containing 0.2% (A) under otherwise similar conditions, only 52% of the beetles were eradicated.

En ytterligere sammenligning med' en emulsjon som inneholder 0,025% (B) under ellers like betingelser ga som resultat at bare 88% av billene ble utryddet. A further comparison with an emulsion containing 0.025% (B) under otherwise identical conditions resulted in only 88% of the beetles being eradicated.

Eksempel 3- Example 3-

Små epletrær i potter som var sterkt befengt med frukt-trespinnemidd (Metatetranychus ulmi) ble sprøytet med en virksom stoffblanding ifølge oppfinnelsen som var sammensatt tilsvarende det i eksempel 1 nevnte og inneholdt 0,04% 1,2,3,4,7,7-heksaklorbicyklo-_/~2,2 ,l7-hepten-( 2 )-bis-/~hydroksymetylen-(5 56_)7-sulfit (A) sammen med 0,01% 1-fenyl-3-(0,0-dietyltionofosforyl)-1,2,4-triazol (B). Den mikroskopiske undersøkelse på akaricide og ovicide virkninger etter 8 dager viser en 100%-ig utryddelse av spinnemidden og eggene. Eksempel 4. Small apple trees in pots that were heavily infested with fruit wood spider mite (Metatetranychus ulmi) were sprayed with an effective substance mixture according to the invention which was composed similarly to that mentioned in example 1 and contained 0.04% 1,2,3,4,7,7 -hexachlorobicyclo-_/~2,2 ,17-heptene-( 2 )-bis-/~hydroxymethylene-(5 56_)7-sulphite (A) together with 0.01% 1-phenyl-3-(0.0 -diethylthionophosphoryl)-1,2,4-triazole (B). The microscopic examination of the acaricidal and ovicidal effects after 8 days shows a 100% eradication of the spider mite and the eggs. Example 4.

Små mandarintrær i potter som var sterkt befengt med skjoldlus (Pseudococcus citri) ble sprøytet med en virksom stoffblanding ifølge oppfinnelsen som var sammensatt tilsvarende det i eksempel 1 nevnte og inneholdt 0,04% 1,2,3}4,7,7-heksaklorbicyklo-£~ 2 ,2 ,iy-hepten- ( 2 )-bis-/J~hydroksymetylen- (5 ,6_)7-sulfit (A) sammen med 0,02% 1- f enyl-3- (0 ,.0-diety ltionof os f ory 1)-1,2 , 4-triazol (B). Skjoldlusene, ble fullstendig utryddet i løpet av 4 dager. Small mandarin trees in pots that were heavily infested with scale lice (Pseudococcus citri) were sprayed with an effective substance mixture according to the invention which was composed similarly to that mentioned in example 1 and contained 0.04% 1,2,3}4,7,7-hexachlorobicyclo -£~ 2 ,2 ,iy-heptene- ( 2 )-bis-/J~hydroxymethylene- (5 ,6_)7-sulphite (A) together with 0.02% 1- f enyl-3- (0 ,. 0-diety ltionof os f ory 1)-1,2 , 4-triazole (B). The scale insects were completely eradicated within 4 days.

Eksempel 5- Example 5-

Ved siden av de i eksempel 1 nevnte virksomme stoffblandinger ifølge oppfinnelsen kan eksempelvis følgende med fordel anvendes. Emulsjonskonsentratene emulgeres i tilsvarende mengde vann for å gi den ønskede virksomme stoffkonsentrasjon. In addition to the active substance mixtures according to the invention mentioned in example 1, for example the following can be advantageously used. The emulsion concentrates are emulsified in a corresponding amount of water to give the desired active substance concentration.

Claims (1)

Insekticid og akaricid middel, karakterisert ved at det består av eller inneholder en blanding av 1-10 vektdeler av 1,2,3,4,7,7-heksaklorbicyklo-/<->2,2,l7-hepten-(2)-bis-/_ hy droksymetylen-( 5 ,6_)7-sulfit med formelenInsecticide and acaricidal agent, characterized in that it consists of or contains a mixture of 1-10 parts by weight of 1,2,3,4,7,7-hexachlorobicyclo-/<->2,2,17-heptene-(2) -bis-/_ hydroxymethylene-(5,6_)7-sulphite with the formula og 1 vektdel 1-fenyl-3(0,0-dietyltionofosfory1)-1,2,4-triazol med formelenand 1 part by weight of 1-phenyl-3(0,0-diethylthionophosphory1)-1,2,4-triazole with the formula
NO02754/69A 1968-07-06 1969-07-01 NO126292B (en)

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DE19681767970 DE1767970B1 (en) 1968-07-06 1968-07-06 Pest repellants

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NO126292B true NO126292B (en) 1973-01-22

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DK (1) DK121479B (en)
ES (1) ES369183A1 (en)
FR (1) FR2012453A1 (en)
GB (1) GB1252679A (en)
IE (1) IE33463B1 (en)
IL (1) IL32533A (en)
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NO (1) NO126292B (en)
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DE2364892C2 (en) * 1973-12-28 1984-10-04 Hoechst Ag, 6230 Frankfurt Insecticidal agent for ULV application
DE2364894C2 (en) * 1973-12-28 1984-11-22 Hoechst Ag, 6230 Frankfurt Insecticidal agent for ULV application

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DK121479B (en) 1971-10-18
IL32533A (en) 1972-10-29
AT298151B (en) 1972-04-25
BE735744A (en) 1970-01-07
OA03328A (en) 1970-12-15
LU59014A1 (en) 1971-06-21
FR2012453A1 (en) 1970-03-20
DE1767970B1 (en) 1971-02-04
NL142314B (en) 1974-06-17
RO55859A (en) 1974-02-01
SE343461B (en) 1972-03-13
ES369183A1 (en) 1971-10-16
PL80200B1 (en) 1975-08-30
NL6909726A (en) 1970-01-08
IE33463L (en) 1970-01-06
IE33463B1 (en) 1974-07-10
CS154631B2 (en) 1974-04-30

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