NO137547B - 3,7,11-TRIMETHYL DODECAENOATS FOR USE AS INSECTICIDES - Google Patents
3,7,11-TRIMETHYL DODECAENOATS FOR USE AS INSECTICIDES Download PDFInfo
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- NO137547B NO137547B NO4260/72A NO426072A NO137547B NO 137547 B NO137547 B NO 137547B NO 4260/72 A NO4260/72 A NO 4260/72A NO 426072 A NO426072 A NO 426072A NO 137547 B NO137547 B NO 137547B
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- 239000002917 insecticide Substances 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 7
- BFAKENXZKHGIGE-UHFFFAOYSA-N bis(2,3,5,6-tetrafluoro-4-iodophenyl)diazene Chemical compound FC1=C(C(=C(C(=C1F)I)F)F)N=NC1=C(C(=C(C(=C1F)F)I)F)F BFAKENXZKHGIGE-UHFFFAOYSA-N 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- FZRBKIRIBLNOAM-UHFFFAOYSA-N (E,E)-2-propynyl 3,7,11-trimethyl-2,4-dodecadienoate Chemical group CC(C)CCCC(C)CC=CC(C)=CC(=O)OCC#C FZRBKIRIBLNOAM-UHFFFAOYSA-N 0.000 claims 1
- IMCPOQXXXJCLRK-UHFFFAOYSA-N 3,7,11-trimethyldodec-2-enoic acid Chemical class CC(C)CCCC(C)CCCC(C)=CC(O)=O IMCPOQXXXJCLRK-UHFFFAOYSA-N 0.000 claims 1
- 241000238631 Hexapoda Species 0.000 description 13
- 241001124076 Aphididae Species 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 229920001213 Polysorbate 20 Polymers 0.000 description 5
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241001674048 Phthiraptera Species 0.000 description 4
- 241000219843 Pisum Species 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- 230000018109 developmental process Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 4
- 244000061456 Solanum tuberosum Species 0.000 description 3
- 235000002595 Solanum tuberosum Nutrition 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- -1 3-pentynyl Chemical group 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000258937 Hemiptera Species 0.000 description 2
- 241000691880 Planococcus citri Species 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 230000029052 metamorphosis Effects 0.000 description 2
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000001850 reproductive effect Effects 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- QMVSVDPAWIVPNR-UHFFFAOYSA-N 3,7,11-trimethyldodeca-2,4-dienoic acid Chemical compound CC(C)CCCC(C)CC=CC(C)=CC(O)=O QMVSVDPAWIVPNR-UHFFFAOYSA-N 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- 241000253994 Acyrthosiphon pisum Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003163 gonadal steroid hormone Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- 230000007653 larval development Effects 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000001161 mammalian embryo Anatomy 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 239000000025 natural resin Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/587—Monocarboxylic acid esters having at least two carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Foreliggende oppfinnelse vedrorer 3-7-11-trimetyldodekaenoater The present invention relates to 3-7-11-trimethyldodecaenoates
med formelen A, for anvendelse som insekticid. with the formula A, for use as an insecticide.
hvor R betegner lavere alkynylmed 3-6 karbonatomer, where R denotes lower alkynyl with 3-6 carbon atoms,
hvilke forbindelser foreligger som en blanding av trans-2, which compounds exist as a mixture of trans-2,
trans-4 og cis-2,trans-4-isomerer. trans-4 and cis-2,trans-4 isomers.
Fra tysk off.skrift 2.115.673 er kjent nær beslektede for- From German official document 2,115,673 are known closely related
bindelser med insekticid virkning. compounds with insecticidal action.
I det etterfolgende sammenligningseksempel er de nær beslektede forbindelser 2-8 sammenlignet, med hensyn til insekticid akti- In the following comparison example, the closely related compounds 2-8 are compared, with regard to insecticidal activity
vitet med en foretrukket forbindelse ifolge oppfinnelsen. with a preferred compound according to the invention.
Forbindelsene av formelen A er verdifulle for bekjempelse The compounds of formula A are valuable for combating
av insekter. Anvendbarheten av forbindelsene som insektbe-kjempelsesmidler antas å bero på deres kjonnshormon-aktivitet. Forbindelsene appliseres fortrinnsvis på ikke fullt utviklede insekter, nemlig når disse befinner seg i embryo-, larve- eller puppestadiet, og da med tanke på deres virkning på metamorfo- of insects. The utility of the compounds as insecticides is believed to be due to their sex hormone activity. The compounds are preferably applied to insects that are not fully developed, namely when these are in the embryo, larval or pupal stage, and then in view of their effect on metamorphosis
sen og med tanke på at de forårsaker en unormal utvikling, som leder til at insektene dor eller at de ikke blir i stand til å forplante seg. Forbindelsene er effektive bekjempelsesmidler late and considering that they cause an abnormal development, which leads to the insects dying or not being able to reproduce. The compounds are effective control agents
for Lepidoptera, Homoptera såsom bladlus eller andre insekter. for Lepidoptera, Homoptera such as aphids or other insects.
De er spesielt anvendbare for bekjempelse av bladlus. Forbindelsene kan appliseres i lave doseringsmengder av størrelses-ordenen 0,01 - 1,0 jug pr. insekt. Egnede bærematerialer omfat-ter væskeformige eller faste bærere, såsom vann, aceton, xylen, mineraloljer eller vegetabilske oljer, talkum, vermikulit, natur-harpikser og syntetiske "harpikser samt kisel. Behandlingen av insektene foretas ved påsproytning, pudring eller ved They are particularly useful for combating aphids. The compounds can be applied in low dosage quantities of the order of magnitude 0.01 - 1.0 jug per insect. Suitable carrier materials include liquid or solid carriers, such as water, acetone, xylene, mineral oils or vegetable oils, talc, vermiculite, natural resins and synthetic resins as well as silicon. The insects are treated by spraying, dusting or by
at insektene utsettes for damper av forbindelsene av that the insects are exposed to vapors of the compounds of
formelen A. Vanligvis anvendes en konsentrasjon på mindre enn 25 % av den aktive forbindelse. Formuleringene kan omfatte insekttUtrekkende midler, emulgeringsmidler eller fuktnings-midler for å lette appliseringen og for å forbedre effektivi-teten av den aktive bestanddel. Ved appliseringen av forbindelsene anvendes vanligvis en blanding av trans(2),trans(4)- og cis(2),trans(4)-isomerer. the formula A. Usually a concentration of less than 25% of the active compound is used. The formulations may include insect repellants, emulsifiers or wetting agents to facilitate application and to improve the effectiveness of the active ingredient. When applying the compounds, a mixture of trans(2),trans(4) and cis(2),trans(4) isomers is usually used.
De nye esterene av formel A kan fremstilles ved forestring på vanlig måte ved å gå ut fra en syre eller et syrehalogenid av formelen B The new esters of formula A can be prepared by esterification in the usual way starting from an acid or an acid halide of formula B
hvor R' betegner hydroksy, brom eller klor, where R' denotes hydroxy, bromine or chlorine,
under anvendelse av en alkylol (R 7-0H). using an alkylol (R 7-OH).
Utgangsmaterialene av formelen B kan fremstilles The starting materials of formula B can be prepared
ifolge tysk off.skrift nr. 2.202.016. according to German official document no. 2.202.016.
Uttrykket "lavere alkynyl", slik som det anvendes her, henforer seg til en acetylenisk umettet hydrokarbongruppe som kan være rettkjedet eller forgrenet, og som har en kjedelengde på fra 3-6 karbonatomer, f.eks. 3-butynyl, 2-propynyl og 3-penty-nyl. The term "lower alkynyl", as used herein, refers to an acetylenically unsaturated hydrocarbon group which may be straight chain or branched, and which has a chain length of from 3-6 carbon atoms, e.g. 3-butynyl, 2-propynyl and 3-pentynyl.
Folgende utforelseseksempler belyser oppfinnelsen. The following exemplary embodiments illustrate the invention.
EKSEMPEL 1 EXAMPLE 1
Til 0,6 g omkrystallisert trans,trans-3,7,11-trimetyldodeka-2,4-dienonsyre i 10 ml torr benzen ble 0,23 ml oksalylklorid tilsatt ved romtemperatur under omroring. Etter 2 timer ble 2 ml prop-2-yn-l-ol tilsatt, og blandingen fikk henstå ca. 2 timer ved romtemperatur. Eter og mettet natriumhydrogenkarbonat ble tilsatt og den organiske fase ble separert. Denne ble va-sket med vannholdig natriumhydrogenkarbonat og mettet natrium-klorid, torket over kalsiumsulfat og dampet inn, hvorved man fikk prop-2'-yn-1'-yl-3,7,11-trimetyldodeka-2,4-dienoat (en blanding av trans-2, trans-4- og cis-2,trans-4), kokepunkt 121 - 122°C/0,010 mm, hvilken forbindelse kunne ytterligere renses ved kromatografi eller destillasjon. To 0.6 g of recrystallized trans,trans-3,7,11-trimethyldodeca-2,4-dienonic acid in 10 ml of dry benzene, 0.23 ml of oxalyl chloride was added at room temperature with stirring. After 2 hours, 2 ml of prop-2-yn-l-ol was added, and the mixture was allowed to stand for approx. 2 hours at room temperature. Ether and saturated sodium bicarbonate were added and the organic phase was separated. This was washed with aqueous sodium bicarbonate and saturated sodium chloride, dried over calcium sulfate and evaporated, whereby prop-2'-yn-1'-yl-3,7,11-trimethyldodeca-2,4-dienoate was obtained ( a mixture of trans-2, trans-4- and cis-2,trans-4), boiling point 121 - 122°C/0.010 mm, which compound could be further purified by chromatography or distillation.
EKSEMPEL 2 EXAMPLE 2
3 g 3,7,11-trimetyldodeka-2,4-dienonsyre i 100 ml benzen ble behandlet i nitrogenatmosfære med 4 ml oksalylklorid. Etter 4 timer ved romtemperatur ble opplosningsmidlet fjernet ved redusert trykk. Man tilsatte 100 ml fersk benzen under nitrogen og deretter 2,8 g prop-2-yn-l-ol. Reaksjonsblandingen ble rort om over natten ved romtemperatur. Reaksjonsblandingen ble oppar-beidet ved at man helte denne i vann og ved fortynning med 50 ml eter, vasking med vann, mettet natriumhydrogenkarbonat og saltlosning samt torkhing over kalsiumsulfat og inndampning ved redusert trykk, hvorved man fikk prop-2'-yn-1'-yl-3,7,11-tr imetyldodeka- 2 , 4-dienoat (blanding av trans-2,trans-4- og cis-2,trans-4-isomerer), som kunne renses ved destillasjon (kokepunkt 120 - 122°C/0,010 mm). 3 g of 3,7,11-trimethyldodeca-2,4-dienoic acid in 100 ml of benzene was treated in a nitrogen atmosphere with 4 ml of oxalyl chloride. After 4 hours at room temperature, the solvent was removed under reduced pressure. 100 ml of fresh benzene were added under nitrogen and then 2.8 g of prop-2-yn-1-ol. The reaction mixture was stirred overnight at room temperature. The reaction mixture was prepared by pouring this into water and by diluting with 50 ml of ether, washing with water, saturated sodium bicarbonate and brine as well as drying over calcium sulfate and evaporation at reduced pressure, whereby prop-2'-yn-1' was obtained -yl-3,7,11-trimethyldodeca-2,4-dienoate (mixture of trans-2,trans-4 and cis-2,trans-4 isomers), which could be purified by distillation (boiling point 120 - 122 °C/0.010 mm).
Ved anvendelse av en finfordelingsanordning besproytet man to ertefroplanter som var 9-11 dager gamle inntil en avrenning var nær forestående. Ca. 5 ml spray-losning ble utspredd under denne operasjon.. Spray-losningen ble fremstilt ved at 1,0 ml Using a fine distribution device, two pea seedlings that were 9-11 days old were sprayed until a runoff was imminent. About. 5 ml of spray solution was spread during this operation. The spray solution was prepared by 1.0 ml
av en acetonlosning, som inneholdt en egnet, forutbestemt mengde av en forbindelse ifolge oppfinnelsen, ble tilsatt til 9,0 ml av en vannholdig 0,01-%'s emulsjon av det overflateak-tive middel "Tween 20" (polyoksyetylen-(20)-sorbitanmonolaurat). Et par erteplanter ble også sprayet med en 1:9-tilberedning av aceton i 0,01 %'s"Tween 20" for anvendelse som spray-fortyn- of an acetone solution containing a suitable, predetermined amount of a compound of the invention was added to 9.0 ml of an aqueous 0.01% emulsion of the surfactant "Tween 20" (polyoxyethylene-(20 )-sorbitan monolaurate). A pair of pea plants were also sprayed with a 1:9 preparation of acetone in 0.01% "Tween 20" for use as a spray-diluent
ningskontroll. De vannholdige spray-væsker på plantene fikk torke. Enkelte planter ble deretter infisert med 10 st larver av ertebladlusen "Acyrthosiphon pisum" (Harris), som befant seg i tredje utviklingsstadium, og som var 72 - 96 timer gamle. Bladlusene ble deretter innestengt ved at en flyttbar pappsy-1inder ble anbragt over potten i hvilken hver påsprayet og infisert erteplante befant seg. Sylinderen ble lukket på toppen ved hjelp av en finmasket nylonsikt for å holde igjen bladlusene som forlot planten. Innestengte planteenheter ble overfort til et miljodrivhus, som ble holdt under konstante betingelser ning control. The aqueous spray fluids on the plants were allowed to dry. Certain plants were then infected with 10 larvae of the pea aphid "Acyrthosiphon pisum" (Harris), which were in the third stage of development, and which were 72 - 96 hours old. The aphids were then confined by placing a removable cardboard screen over the pot in which each sprayed and infected pea plant was located. The cylinder was closed at the top using a fine-mesh nylon screen to retain the aphids that left the plant. Confined plant units were transferred to an environmental greenhouse, which was maintained under constant conditions
(25°C, 50 %'s relativ fuktighet, 16 timer belysning pr. dag) (25°C, 50% relative humidity, 16 hours of lighting per day)
og plantene oppholdt seg her i 6 dager. I lopet av denne tid ble substratet for hver erteplante vannet etter behov. Ved slutten av perioden bedomte man bladlusene på hver plante ved anvendelse av folgende system: 0 = en normal bladlus $ 1 = en noe påvirket bladlus, hvilken oppviser karakteristika som ligger mellom de for et normalt utviklet insekt og en larve i fjerde utviklingsstadium; 2 = en sterkt påvirket bladlus som oppviste ett eller flere av folgende kjennetegn: tegn på et ekstra larveutviklingsstadium, inhibert reproduksjon, forplantningsåpningen sklerotisert og bakdelen mere lik en larve enn et utviklet insekt. For hver plante dividerte man summen av de to produkter av antall indi-vider i hver kategori ganger kategoribedommelsen med 20 (maksimal bedommelse) for oppnåelse av prosentuell respons eller resultat. Resultatet fra dobbeltforsok ble anvendt for beregning av middelverdien som anga den prosentuelle respons for det spesielt anvendte doser ingsnivå'. To eller flere dose-ringsnivåer (angitt som prosentull konsentrasjon) ble anvendt for hver eksperimentforbindelse. IC,-0-nivået for hver eksperimentforbindelse ble bestemt ved hjelp av et halvlogaritmisk diagram av prosentuell respons mot logaritmen av prosentuell konsentrasjon. For prop-2'-yn-1•-yl-3,7,11-trimetyldodeka-2,4-dienoat oppnådde man en ic50-verdi på 0,00074%. Kontrollene oppviste en neglisjerbar.(2 % eller mindre) respons under lig-nende serier av forsok. and the plants stayed here for 6 days. During this time, the substrate for each pea plant was watered as needed. At the end of the period, the aphids on each plant were assessed using the following system: 0 = a normal aphid $ 1 = a somewhat affected aphid, which exhibits characteristics that lie between those of a normally developed insect and a larva in the fourth stage of development; 2 = a severely affected aphid that showed one or more of the following characteristics: signs of an additional larval development stage, inhibited reproduction, the reproductive opening sclerotized and the rear part more like a larva than a developed insect. For each plant, the sum of the two products of the number of individuals in each category times the category rating was divided by 20 (maximum rating) to obtain a percentage response or result. The result from duplicate experiments was used to calculate the mean value which indicated the percentage response for the particular dosage level used. Two or more dosage levels (expressed as percent zero concentration) were used for each experimental compound. The IC,-0 level for each test compound was determined using a semi-logarithmic plot of percent response versus the logarithm of percent concentration. For prop-2'-yn-1•-yl-3,7,11-trimethyldodeca-2,4-dienoate, an ic50 value of 0.00074% was obtained. The controls showed a negligible (2% or less) response during similar series of trials.
Fullt utvokste skjoldlus (Pseudococcus citri) ble anbragt på ubehandlet potet (10 st pr. potet). Etter 24 timer ble skjold lusene sprayet med 0,1 % og O,01 % av forbindelsen prop-2'-yn-1'-yl-3,7,11-trimetyldodeka-2,4-dienoat, fortynnet i 0,1 % "Tween 20". Man gjentok forsoket tre ganger. Kontrollene ble sprayet med bare 0,1 % "Tween 20". Etter 7 dager talte man de overlevende skjoldlus (som samtlige var av hunkjonn under hele forsoket) og avkommet ble undersokt. Kontrollgruppen overlevde og forplantede seg hovedsakelig 100 % normalt. Spraying med 0,1 % av den aktive forbindelse medforte at bare 20 % av skjoldlusene av hunkjonn overlevde og disse var hovedsakelig ikke-reproduktive. Spraying med 0,01 % av den aktive forbindelse medforte at 47 % av skjoldlusene overlevde og at reproduser-barheten hos de overlevende insekter var drastisk lavere enn for kontrollen. Fully grown scale lice (Pseudococcus citri) were placed on untreated potatoes (10 per potato). After 24 hours, the scale lice were sprayed with 0.1% and 0.01% of the compound prop-2'-yn-1'-yl-3,7,11-trimethyldodeca-2,4-dienoate, diluted in 0.1 % "Tween 20". The experiment was repeated three times. Controls were sprayed with only 0.1% "Tween 20". After 7 days, the surviving scale lice were counted (all of which were female throughout the experiment) and the offspring were examined. The control group survived and reproduced mainly 100% normally. Spraying with 0.1% of the active compound resulted in only 20% of the female scale lice surviving and these being mainly non-reproductive. Spraying with 0.01% of the active compound meant that 47% of the scale insects survived and that the reproducibility of the surviving insects was drastically lower than for the control.
Insekter i siste nymfeutviklingsstadium (Pseudococcus citri) med forskjellig alder ble behandlet lokalt med 0,2 mikrogram av forbindelsen prop-2'-yn-1'-yl-3,7,11-trimetyldodeka-2,4-dienoat pr. insekt og ble anbragt på potetspirer. Etter 27 timer hadde bare 10 % av insektene overlevet. Insects in the final nymphal development stage (Pseudococcus citri) of different ages were treated locally with 0.2 micrograms of the compound prop-2'-yn-1'-yl-3,7,11-trimethyldodeca-2,4-dienoate per insect and was placed on potato sprouts. After 27 hours, only 10% of the insects had survived.
Sammenligninqsforsok Comparison test
Sammenlignende forsok med hensyn til effekten mot gronn bladlus ble utfort med forbindelsen propargyl-3,7,11-trimetyl-dodeka-2,4-dienoat, ifolge oppfinnelsen (forbindelse nr. 1 i den etterfølgende tabell) og 7 nær beslektede forbindelser kjent fra tysk off.skrift nr. 2.115.673 (forbindelsene 2-8 Comparative experiments with regard to the effect against green aphids were carried out with the compound propargyl-3,7,11-trimethyl-dodeca-2,4-dienoate, according to the invention (compound no. 1 in the following table) and 7 closely related compounds known from German official publication no. 2,115,673 (compounds 2-8
i den etterfølgende tabell). in the following table).
De viste resultater er den prosentvise konsentrasjon av den aktive bestanddel som er nodvendig for å gi 50% inhibering av insekticidets metamorfose. The results shown are the percentage concentration of the active ingredient required to give 50% inhibition of the insecticide's metamorphosis.
Claims (2)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US20110271A | 1971-11-22 | 1971-11-22 |
Publications (2)
Publication Number | Publication Date |
---|---|
NO137547B true NO137547B (en) | 1977-12-05 |
NO137547C NO137547C (en) | 1978-03-15 |
Family
ID=22744502
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO4260/72A NO137547C (en) | 1971-11-22 | 1972-11-21 | 3,7,11-TRIMETHYL DODECAENOATS FOR USE AS INSECTICIDES |
Country Status (22)
Country | Link |
---|---|
JP (1) | JPS5249452B2 (en) |
AT (1) | AT322281B (en) |
AU (1) | AU443536B2 (en) |
BE (1) | BE791620R (en) |
BG (1) | BG20525A3 (en) |
BR (1) | BR7208187D0 (en) |
CA (1) | CA992555A (en) |
CH (1) | CH596134A5 (en) |
DD (1) | DD104692A5 (en) |
DK (1) | DK133973C (en) |
ES (1) | ES407358A1 (en) |
FR (1) | FR2160801B2 (en) |
GB (1) | GB1404203A (en) |
HU (1) | HU167077B (en) |
IE (1) | IE36735B1 (en) |
IL (1) | IL39939A (en) |
IT (1) | IT1012036B (en) |
NL (1) | NL148586B (en) |
NO (1) | NO137547C (en) |
RO (1) | RO63833A (en) |
SE (1) | SE398113B (en) |
ZA (1) | ZA724929B (en) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5737016U (en) * | 1980-08-11 | 1982-02-26 | ||
JPH0610021U (en) * | 1992-07-15 | 1994-02-08 | 林口工業株式会社 | Anti-freezing equipment for automobile glass |
JPH08118963A (en) * | 1994-10-25 | 1996-05-14 | Daiko Kk | Window mask for automobile |
-
0
- BE BE791620D patent/BE791620R/en active
-
1972
- 1972-02-16 DK DK409572A patent/DK133973C/en active
- 1972-07-18 AU AU44663/72A patent/AU443536B2/en not_active Expired
- 1972-07-18 ZA ZA724929A patent/ZA724929B/en unknown
- 1972-07-18 IL IL39939A patent/IL39939A/en unknown
- 1972-07-21 CA CA147,670A patent/CA992555A/en not_active Expired
- 1972-08-01 SE SE7210033A patent/SE398113B/en unknown
- 1972-08-02 IT IT27811/72A patent/IT1012036B/en active
- 1972-08-02 GB GB3617972A patent/GB1404203A/en not_active Expired
- 1972-08-04 CH CH1159372A patent/CH596134A5/xx unknown
- 1972-08-16 FR FR7229291A patent/FR2160801B2/fr not_active Expired
- 1972-08-21 NL NL727211392A patent/NL148586B/en unknown
- 1972-08-24 JP JP47084960A patent/JPS5249452B2/ja not_active Expired
- 1972-08-29 IE IE1178/72A patent/IE36735B1/en unknown
- 1972-09-27 AT AT831372A patent/AT322281B/en active
- 1972-10-06 ES ES407358A patent/ES407358A1/en not_active Expired
- 1972-11-14 BG BG21850A patent/BG20525A3/xx unknown
- 1972-11-15 DD DD166869A patent/DD104692A5/xx unknown
- 1972-11-21 BR BR8187/72A patent/BR7208187D0/en unknown
- 1972-11-21 NO NO4260/72A patent/NO137547C/en unknown
- 1972-11-22 RO RO7200072898A patent/RO63833A/en unknown
- 1972-11-22 HU HUZO133A patent/HU167077B/hu unknown
Also Published As
Publication number | Publication date |
---|---|
AU443536B2 (en) | 1974-01-03 |
BE791620R (en) | 1973-05-21 |
BR7208187D0 (en) | 1973-09-18 |
DD104692A5 (en) | 1974-03-20 |
ZA724929B (en) | 1974-02-27 |
FR2160801B2 (en) | 1978-03-17 |
RO63833A (en) | 1978-11-15 |
DE2246924A1 (en) | 1973-05-30 |
NL148586B (en) | 1976-02-16 |
JPS5249452B2 (en) | 1977-12-17 |
CA992555A (en) | 1976-07-06 |
JPS4858127A (en) | 1973-08-15 |
IE36735B1 (en) | 1977-02-16 |
SE398113B (en) | 1977-12-05 |
AU4466372A (en) | 1974-01-03 |
NL7211392A (en) | 1973-05-24 |
IT1012036B (en) | 1977-03-10 |
DK133973B (en) | 1976-08-23 |
FR2160801A2 (en) | 1973-07-06 |
IE36735L (en) | 1973-05-22 |
AT322281B (en) | 1975-05-12 |
NO137547C (en) | 1978-03-15 |
HU167077B (en) | 1975-07-28 |
DK133973C (en) | 1977-01-31 |
BG20525A3 (en) | 1975-12-05 |
GB1404203A (en) | 1975-08-28 |
CH596134A5 (en) | 1978-02-28 |
ES407358A1 (en) | 1975-10-16 |
DE2246924B2 (en) | 1976-12-23 |
IL39939A (en) | 1976-05-31 |
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