DD143024A5 - Lockstoffpraeparat zum selektiven anlocken von maennlichen kohleulen - Google Patents

Lockstoffpraeparat zum selektiven anlocken von maennlichen kohleulen Download PDF

Info

Publication number: DD143024A5
Authority: DD; German Democratic Republic
Prior art keywords: male; charcoal; formula; acetate; active ingredient
Prior art date: 1978-04-21

Application number

DD79212337A

Other languages

German (de)

English (en)

Inventor

Csaba Szantay

Lajos Novak

Miklos Toth

Jozsef Balla

Bela Stefko

Attila Kis-Tamas

Original Assignee

Egyt Gyogyszervegyeszeti Gyar

Priority date (The priority date 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 date listed.)

1978-04-21

Filing date

1979-04-19

Publication date

1980-07-30

1979-04-19 Application filed by Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar

1980-07-30 Publication of DD143024A5 publication Critical patent/DD143024A5/de

Links

239000003610 charcoal Substances 0.000 claims abstract description 14
238000002360 preparation method Methods 0.000 claims abstract description 13
239000005667 attractant Substances 0.000 claims abstract description 8
BTKXLQSCEOHKTF-SREVYHEPSA-N [(z)-hexadec-11-enyl] acetate Chemical compound CCCC\C=C/CCCCCCCCCCOC(C)=O BTKXLQSCEOHKTF-SREVYHEPSA-N 0.000 claims abstract description 7
230000031902 chemoattractant activity Effects 0.000 claims abstract description 7
241000555303 Mamestra brassicae Species 0.000 claims abstract description 6
239000000203 mixture Substances 0.000 claims description 40
238000000034 method Methods 0.000 claims description 22
239000004480 active ingredient Substances 0.000 claims description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 11
239000000877 Sex Attractant Substances 0.000 claims description 11
FQWSRDQVIFNBQE-SREVYHEPSA-N (z)-nonadec-13-enoic acid Chemical compound CCCCC\C=C/CCCCCCCCCCCC(O)=O FQWSRDQVIFNBQE-SREVYHEPSA-N 0.000 claims description 6
239000003921 oil Substances 0.000 claims description 6
241000238631 Hexapoda Species 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
239000007788 liquid Substances 0.000 claims description 4
239000007787 solid Substances 0.000 claims description 4
230000013011 mating Effects 0.000 claims description 3
239000002775 capsule Substances 0.000 claims description 2
239000000341 volatile oil Substances 0.000 claims description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
239000002671 adjuvant Substances 0.000 claims 1
239000000890 drug combination Substances 0.000 claims 1
229910052740 iodine Inorganic materials 0.000 claims 1
239000011630 iodine Substances 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
YJINQJFQLQIYHX-UHFFFAOYSA-N trans-11-tetradecenyl acetate Natural products CCC=CCCCCCCCCCCOC(C)=O YJINQJFQLQIYHX-UHFFFAOYSA-N 0.000 abstract description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 58
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
238000006243 chemical reaction Methods 0.000 description 28
150000001875 compounds Chemical class 0.000 description 24
239000003016 pheromone Substances 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
230000000694 effects Effects 0.000 description 19
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
229910052739 hydrogen Inorganic materials 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
239000000047 product Substances 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 14
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
125000001412 tetrahydropyranyl group Chemical group 0.000 description 13
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
241001465754 Metazoa Species 0.000 description 10
239000011521 glass Substances 0.000 description 10
-1 lithium aluminum hydride Chemical compound 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 9
JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 8
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 7
241000607479 Yersinia pestis Species 0.000 description 7
238000004458 analytical method Methods 0.000 description 7
239000007789 gas Substances 0.000 description 7
241000255777 Lepidoptera Species 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
239000012071 phase Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
125000006239 protecting group Chemical group 0.000 description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
239000013543 active substance Substances 0.000 description 5
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
PMOIAJVKYNVHQE-UHFFFAOYSA-N phosphanium;bromide Chemical compound [PH4+].[Br-] PMOIAJVKYNVHQE-UHFFFAOYSA-N 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000012312 sodium hydride Substances 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
239000002904 solvent Substances 0.000 description 5
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
RTVWBTSCOISEJT-FPLPWBNLSA-N [(z)-heptadec-11-enyl] acetate Chemical compound CCCCC\C=C/CCCCCCCCCCOC(C)=O RTVWBTSCOISEJT-FPLPWBNLSA-N 0.000 description 4
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 4
239000012346 acetyl chloride Substances 0.000 description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
239000012300 argon atmosphere Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000003814 drug Substances 0.000 description 4
FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
210000004907 gland Anatomy 0.000 description 4
HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
XFGANBYCJWQYBI-UHFFFAOYSA-N 11-bromoundecan-1-ol Chemical compound OCCCCCCCCCCCBr XFGANBYCJWQYBI-UHFFFAOYSA-N 0.000 description 3
HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
240000007124 Brassica oleracea Species 0.000 description 3
235000003899 Brassica oleracea var acephala Nutrition 0.000 description 3
235000011301 Brassica oleracea var capitata Nutrition 0.000 description 3
235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
239000012345 acetylating agent Substances 0.000 description 3
239000002585 base Substances 0.000 description 3
230000008901 benefit Effects 0.000 description 3
230000006378 damage Effects 0.000 description 3
229940079593 drug Drugs 0.000 description 3
RTVWBTSCOISEJT-UHFFFAOYSA-N heptadec-cis-11-en-1-ol acetate Natural products CCCCCC=CCCCCCCCCCCOC(C)=O RTVWBTSCOISEJT-UHFFFAOYSA-N 0.000 description 3
239000002917 insecticide Substances 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
BDLLSHRIFPDGQB-WAYWQWQTSA-N (13Z)-octadecenoic acid Chemical compound CCCC\C=C/CCCCCCCCCCCC(O)=O BDLLSHRIFPDGQB-WAYWQWQTSA-N 0.000 description 2
HETJRPQPDQODIY-UHFFFAOYSA-N 11-bromoundecyl acetate Chemical compound CC(=O)OCCCCCCCCCCCBr HETJRPQPDQODIY-UHFFFAOYSA-N 0.000 description 2
RHVMNRHQWXIJIS-WAYWQWQTSA-N 11Z-hexadecen-1-ol Chemical compound CCCC\C=C/CCCCCCCCCCO RHVMNRHQWXIJIS-WAYWQWQTSA-N 0.000 description 2
FXKYBLZSWZPWLL-SREVYHEPSA-N 2-[(z)-heptadec-11-enoxy]oxane Chemical compound CCCCC\C=C/CCCCCCCCCCOC1CCCCO1 FXKYBLZSWZPWLL-SREVYHEPSA-N 0.000 description 2
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
241000510032 Ellipsaria lineolata Species 0.000 description 2
241000196324 Embryophyta Species 0.000 description 2
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
229910052804 chromium Inorganic materials 0.000 description 2
239000011651 chromium Substances 0.000 description 2
239000003245 coal Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
230000009931 harmful effect Effects 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
238000011835 investigation Methods 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
230000033001 locomotion Effects 0.000 description 2
238000001819 mass spectrum Methods 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
150000004714 phosphonium salts Chemical class 0.000 description 2
230000008569 process Effects 0.000 description 2
239000003223 protective agent Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
230000001568 sexual effect Effects 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
241000894007 species Species 0.000 description 2
239000007858 starting material Substances 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
NDVAKACWHYXYJX-UHFFFAOYSA-N 1-bromo-1-(1-ethoxyethoxy)undecane Chemical compound C(C)OC(C)OC(CCCCCCCCCC)Br NDVAKACWHYXYJX-UHFFFAOYSA-N 0.000 description 1
ZCJSUBNAWABAJW-UHFFFAOYSA-N 1-bromo-11-(1-ethoxyethoxy)undecane Chemical compound CCOC(C)OCCCCCCCCCCCBr ZCJSUBNAWABAJW-UHFFFAOYSA-N 0.000 description 1
IKPSIIAXIDAQLG-UHFFFAOYSA-N 1-bromoundecane Chemical compound CCCCCCCCCCCBr IKPSIIAXIDAQLG-UHFFFAOYSA-N 0.000 description 1
GWJIBEXHLZWCRJ-UHFFFAOYSA-N 2-(11-bromoundecoxy)oxane Chemical compound BrCCCCCCCCCCCOC1CCCCO1 GWJIBEXHLZWCRJ-UHFFFAOYSA-N 0.000 description 1
244000125300 Argania sideroxylon Species 0.000 description 1
235000011299 Brassica oleracea var botrytis Nutrition 0.000 description 1
240000003259 Brassica oleracea var. botrytis Species 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
206010022998 Irritability Diseases 0.000 description 1
102100026933 Myelin-associated neurite-outgrowth inhibitor Human genes 0.000 description 1
241000251539 Vertebrata <Metazoa> Species 0.000 description 1
RHVMNRHQWXIJIS-UHFFFAOYSA-N Z11-16:OH Natural products CCCCC=CCCCCCCCCCCO RHVMNRHQWXIJIS-UHFFFAOYSA-N 0.000 description 1
230000021736 acetylation Effects 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
238000004166 bioassay Methods 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910000085 borane Inorganic materials 0.000 description 1
238000009395 breeding Methods 0.000 description 1
230000001488 breeding effect Effects 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
238000001311 chemical methods and process Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
230000009193 crawling Effects 0.000 description 1
DMSZORWOGDLWGN-UHFFFAOYSA-N ctk1a3526 Chemical compound NP(N)(N)=O DMSZORWOGDLWGN-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
238000003912 environmental pollution Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002168 ethanoic acid esters Chemical class 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
230000002431 foraging effect Effects 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
230000012447 hatching Effects 0.000 description 1
BTKXLQSCEOHKTF-UHFFFAOYSA-N hexadec-11-enyl acetate Chemical compound CCCCC=CCCCCCCCCCCOC(C)=O BTKXLQSCEOHKTF-UHFFFAOYSA-N 0.000 description 1
239000002035 hexane extract Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
SZMRMIJZRCGDOS-UHFFFAOYSA-N hydrogen sulfite;methylazanium Chemical compound NC.OS(O)=O SZMRMIJZRCGDOS-UHFFFAOYSA-N 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000002085 irritant Substances 0.000 description 1
231100000021 irritant Toxicity 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000012417 linear regression Methods 0.000 description 1
AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
ARNWQMJQALNBBV-UHFFFAOYSA-N lithium carbide Chemical compound [Li+].[Li+].[C-]#[C-] ARNWQMJQALNBBV-UHFFFAOYSA-N 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000003094 microcapsule Substances 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000000306 recurrent effect Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000004289 sodium hydrogen sulphite Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
239000011885 synergistic combination Substances 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1

Classifications

- 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
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/09—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis
- C07C29/10—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrolysis of ethers, including cyclic ethers, e.g. oxiranes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/15—Unsaturated ethers containing only non-aromatic carbon-to-carbon double bonds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/17—Unsaturated ethers containing halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/293—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
- C07C69/145—Acetic acid esters of monohydroxylic compounds of unsaturated alcohols
- 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
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Health & Medical Sciences (AREA)
Agronomy & Crop Science (AREA)
Molecular Biology (AREA)
Chemical Kinetics & Catalysis (AREA)
Biochemistry (AREA)
Pest Control & Pesticides (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)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

DD79212337A 1978-04-21 1979-04-19 Lockstoffpraeparat zum selektiven anlocken von maennlichen kohleulen DD143024A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU78EE2558A HU176515B (en)	1978-04-21	1978-04-21	Composition for enticing male agrotis of cabbage

Publications (1)

Publication Number	Publication Date
DD143024A5 true DD143024A5 (de)	1980-07-30

Family

ID=10995764

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79212337A DD143024A5 (de)	1978-04-21	1979-04-19	Lockstoffpraeparat zum selektiven anlocken von maennlichen kohleulen

Country Status (20)

Country	Link
US (1)	US4243660A (fr)
JP (1)	JPS54140722A (fr)
AT (1)	AT362191B (fr)
BE (1)	BE875696A (fr)
BG (1)	BG34606A3 (fr)
CH (1)	CH642231A5 (fr)
CS (1)	CS220786B2 (fr)
DD (1)	DD143024A5 (fr)
DE (1)	DE2916068A1 (fr)
DK (1)	DK164279A (fr)
FI (1)	FI791288A7 (fr)
FR (1)	FR2423227A1 (fr)
GB (1)	GB2021565B (fr)
HU (1)	HU176515B (fr)
IT (1)	IT1113322B (fr)
NL (1)	NL7903109A (fr)
PL (1)	PL119710B1 (fr)
RO (1)	RO76406A (fr)
SE (1)	SE436165B (fr)
YU (1)	YU94379A (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4837358A (en) *	1986-02-26	1989-06-06	Phillips Petroleum Company	Preparation of 9-alkenyl ester compounds
JPS62223136A (ja) *	1986-03-19	1987-10-01	Shin Etsu Chem Co Ltd	１―ハロ―（ｅ，ｚ）―７，９―アルカジエン化合物
DE19802750A1 (de) *	1998-01-26	1999-07-29	Lohmann Therapie Syst Lts	Vorrichtung zum Anlocken und Fangen von Insekten
CN107279137A (zh) *	2016-11-07	2017-10-24	中国农业科学院植物保护研究所	甘蓝夜蛾性诱剂的制备方法及应用
CN107439544B (zh) *	2017-08-03	2020-04-24	中国农业科学院植物保护研究所	一种甘蓝夜蛾的性诱剂组合物及其应用

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2355534A1 (de) *	1973-11-07	1975-09-11	Hoechst Ag	Verfahren zur herstellung von cisolefinen
US4042681A (en) *	1975-12-22	1977-08-16	Canadian Patents And Development Limited	Composite attractant for Bertha Armyworm moth
CA1043256A (fr) *	1976-02-05	1978-11-28	Her Majesty The Queen, In Right Of Canada, As Represented By The Ministe R Of Agriculture	Attractif pour la tisseuse de la betterave
US4107293A (en) *	1977-03-25	1978-08-15	Canadian Patents And Development Limited	Attractant for darksided cutworm moth

1978
- 1978-04-21 HU HU78EE2558A patent/HU176515B/hu not_active IP Right Cessation
1979
- 1979-04-19 PL PL1979215009A patent/PL119710B1/pl unknown
- 1979-04-19 YU YU00943/79A patent/YU94379A/xx unknown
- 1979-04-19 BE BE1/9361A patent/BE875696A/fr not_active IP Right Cessation
- 1979-04-19 DD DD79212337A patent/DD143024A5/de unknown
- 1979-04-19 IT IT21958/79A patent/IT1113322B/it active
- 1979-04-19 FI FI791288A patent/FI791288A7/fi not_active Application Discontinuation
- 1979-04-19 BG BG043296A patent/BG34606A3/xx unknown
- 1979-04-19 SE SE7903449A patent/SE436165B/sv not_active IP Right Cessation
- 1979-04-19 AT AT293179A patent/AT362191B/de not_active IP Right Cessation
- 1979-04-19 CH CH367779A patent/CH642231A5/de not_active IP Right Cessation
- 1979-04-19 US US06/031,583 patent/US4243660A/en not_active Expired - Lifetime
- 1979-04-19 RO RO7997301A patent/RO76406A/fr unknown
- 1979-04-20 DK DK164279A patent/DK164279A/da not_active Application Discontinuation
- 1979-04-20 FR FR7909991A patent/FR2423227A1/fr active Pending
- 1979-04-20 DE DE19792916068 patent/DE2916068A1/de not_active Withdrawn
- 1979-04-20 CS CS792750A patent/CS220786B2/cs unknown
- 1979-04-20 NL NL7903109A patent/NL7903109A/xx not_active Application Discontinuation
- 1979-04-21 JP JP4855879A patent/JPS54140722A/ja active Pending
- 1979-04-23 GB GB7914071A patent/GB2021565B/en not_active Expired

Also Published As

Publication number	Publication date
PL215009A1 (fr)	1980-03-10
NL7903109A (nl)	1979-10-23
BG34606A3 (bg)	1983-10-15
ATA293179A (de)	1980-09-15
GB2021565B (en)	1982-06-09
GB2021565A (en)	1979-12-05
IT1113322B (it)	1986-01-20
FR2423227A1 (fr)	1979-11-16
RO76406A (fr)	1981-03-30
US4243660A (en)	1981-01-06
HU176515B (en)	1981-03-28
PL119710B1 (en)	1982-01-30
SE7903449L (sv)	1979-10-22
AT362191B (de)	1981-04-27
YU94379A (en)	1983-04-30
FI791288A7 (fi)	1981-01-01
DK164279A (da)	1979-10-22
BE875696A (fr)	1979-10-19
SE436165B (sv)	1984-11-19
JPS54140722A (en)	1979-11-01
CH642231A5 (de)	1984-04-13
IT7921958A0 (it)	1979-04-19
DE2916068A1 (de)	1979-10-31
CS220786B2 (en)	1983-04-29

Publication	Publication Date	Title
DE2365555C2 (fr)	1987-10-15
DE2653189C2 (de)	1985-02-14	Cyclopropanverbindungen, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Insektizide
DE2802962C2 (de)	1985-10-03	Cyclopropancarbonsäureesterderivate und sie enthaltende insektizide Zusammensetzungen
DE2231312B2 (fr)	1974-03-14
DE2436178A1 (de)	1975-02-20	Cyclopropancarbonsaeureester, verfahren zu ihrer herstellung und ihre verwendung als pestizide
DE2327660C3 (de)	1978-06-15	Cyclopropancarbonsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide
DE2348930B2 (de)	1979-04-12	Insektizide Mittel auf Basis von Chrysanthemumsäureestern
CH646034A5 (de)	1984-11-15	Lockstoffpraeparat und verfahren zur herstellung von dessen komponenten.
DD142281A5 (de)	1980-06-18	Verfahren zur bekaempfung von insekten und acaren
CH642231A5 (de)	1984-04-13	Lockstoffpraeparat zum selektiven anlocken von maennlichen kohleulen.
DE2432951A1 (de)	1975-01-30	(+)-cis-chrysanthemumsaeureester und insektizide und akarizide mittel
EP0053756B1 (fr)	1984-09-12	2,6-Diéthyl-3,5-diméthyl-2,3-dihydro-4H-pyranne, procédé de préparation et son utilisation dans le diagnostic précoce, la localisation et pour combattre le Lasioderma serricorne F
DE1593835C3 (de)	1974-02-28	Substituierte Furfurylester der Chrysanthemumsäure und Verfahren zu deren Herstellung sowie diese enthaltende Insekticide
DE1695763B2 (de)	1974-10-24	Cyclopropancarbonsäureester
DE2406259B2 (de)	1976-12-30	Verfahren zur herstellung von tetradeca-9,11-dienyl-acetat und dieses anhaltende mittel zum anlocken von insekten
DE2825197A1 (de)	1979-01-11	Alpha -cyan-m-phenoxybenzylester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und/oder acarizide
DE2810031A1 (de)	1978-09-21	Alpha- oder beta- substituierte isovaleriansaeureester enthaltendes schaedlingsbekaempfungsmittel
DE1960155A1 (de)	1970-06-11	Lockmittel fuer die rosa Baumwollmotten
DE1960155C (de)	1972-04-20	Cis 7 Hexadecen lol acetat
EP0609253B1 (fr)	1995-12-20	Procede de fabrication d'un melange compose d'isomeres de dodecadienol, produits intermediaires pour cette fabrication et application de ce melange
DE1567198C (de)	1973-02-22	Schwefligsaurephenyl phenoxyalkyl ester und ihre Verwendung A,5\m Uuwoyal Uic , New Yolk, N Y (V St A)
DE2554883A1 (de)	1976-06-16	Insektizide ester
DE2335347C3 (de)	1977-04-07	Substituierte Essigsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Pestizide
DE1567199C (fr)	1973-05-24
DE4439223A1 (de)	1996-05-09	Zur Bekämpfung von Hylotrupes bajulus und Pyrrhidium sanguineum geeignete Mischungen und Mittel