DD290195A5 - Verfahren zur herstellung von derivaten von 2,6,7-trioxabicydo[2.2.2]-octanen, pestizide zusammensetzung und verfahren zur schaedlingsbekaempfung - Google Patents

Verfahren zur herstellung von derivaten von 2,6,7-trioxabicydo[2.2.2]-octanen, pestizide zusammensetzung und verfahren zur schaedlingsbekaempfung Download PDF

Info

Publication number: DD290195A5
Authority: DD; German Democratic Republic
Prior art keywords: group; compound; formula; mixture; ynyl
Prior art date: 1987-07-22

Application number

DD88318186A

Other languages

German (de)

English (en)

Inventor

John B Weston

John P Larkin

Ian H Smith

Original Assignee

The Wellcome Foundation Limited,Gb

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.)

1987-07-22

Filing date

1988-07-21

Publication date

1991-05-23

1988-07-21 Application filed by The Wellcome Foundation Limited,Gb filed Critical The Wellcome Foundation Limited,Gb

1991-05-23 Publication of DD290195A5 publication Critical patent/DD290195A5/de

Links

239000000203 mixture Substances 0.000 title claims abstract description 228
238000000034 method Methods 0.000 title claims abstract description 111
238000002360 preparation method Methods 0.000 title claims abstract description 22
230000008569 process Effects 0.000 title claims abstract description 12
239000000575 pesticide Substances 0.000 title claims description 3
150000001875 compounds Chemical class 0.000 claims abstract description 179
241000607479 Yersinia pestis Species 0.000 claims abstract description 11
241000238421 Arthropoda Species 0.000 claims abstract description 10
230000000361 pesticidal effect Effects 0.000 claims abstract description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 228
-1 C 1 Chemical group 0.000 claims description 199
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 54
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 50
238000006243 chemical reaction Methods 0.000 claims description 50
229910052736 halogen Inorganic materials 0.000 claims description 46
150000002367 halogens Chemical group 0.000 claims description 36
229910052727 yttrium Inorganic materials 0.000 claims description 36
239000001257 hydrogen Substances 0.000 claims description 35
125000004093 cyano group Chemical group *C#N 0.000 claims description 32
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
229910052757 nitrogen Inorganic materials 0.000 claims description 25
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 25
125000000217 alkyl group Chemical group 0.000 claims description 24
125000005843 halogen group Chemical group 0.000 claims description 23
229910052760 oxygen Inorganic materials 0.000 claims description 20
125000003545 alkoxy group Chemical group 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 17
241001465754 Metazoa Species 0.000 claims description 16
125000001183 hydrocarbyl group Chemical group 0.000 claims description 15
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
239000000460 chlorine Substances 0.000 claims description 13
239000001301 oxygen Substances 0.000 claims description 13
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
229910052717 sulfur Inorganic materials 0.000 claims description 12
239000002585 base Substances 0.000 claims description 11
125000001153 fluoro group Chemical group F* 0.000 claims description 11
125000001931 aliphatic group Chemical group 0.000 claims description 10
125000000304 alkynyl group Chemical group 0.000 claims description 10
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
239000012634 fragment Substances 0.000 claims description 9
239000011593 sulfur Substances 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
125000004423 acyloxy group Chemical group 0.000 claims description 8
125000005842 heteroatom Chemical group 0.000 claims description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
238000007363 ring formation reaction Methods 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
239000004215 Carbon black (E152) Substances 0.000 claims description 5
206010061217 Infestation Diseases 0.000 claims description 5
239000000969 carrier Substances 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
229930195733 hydrocarbon Natural products 0.000 claims description 4
150000002430 hydrocarbons Chemical class 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
239000000417 fungicide Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 3
241000972349 Ocoa Species 0.000 claims description 2
239000003377 acid catalyst Substances 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
239000000921 anthelmintic agent Substances 0.000 claims description 2
229940124339 anthelmintic agent Drugs 0.000 claims description 2
239000005667 attractant Substances 0.000 claims description 2
239000003899 bactericide agent Substances 0.000 claims description 2
125000002837 carbocyclic group Chemical group 0.000 claims description 2
125000001188 haloalkyl group Chemical group 0.000 claims description 2
239000005871 repellent Substances 0.000 claims description 2
230000002940 repellent Effects 0.000 claims description 2
125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 331
239000000243 solution Substances 0.000 description 187
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 150
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 149
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 119
239000003921 oil Substances 0.000 description 97
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 96
235000019198 oils Nutrition 0.000 description 95
229960004132 diethyl ether Drugs 0.000 description 94
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 75
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 74
239000002904 solvent Substances 0.000 description 70
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 66
239000000284 extract Substances 0.000 description 62
238000001030 gas--liquid chromatography Methods 0.000 description 59
239000007787 solid Substances 0.000 description 43
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 40
239000012230 colorless oil Substances 0.000 description 40
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
239000012267 brine Substances 0.000 description 37
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 37
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
238000001819 mass spectrum Methods 0.000 description 36
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 36
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 29
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 28
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
238000000451 chemical ionisation Methods 0.000 description 27
239000007788 liquid Substances 0.000 description 26
239000011541 reaction mixture Substances 0.000 description 26
238000003756 stirring Methods 0.000 description 25
238000010992 reflux Methods 0.000 description 24
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
229920006395 saturated elastomer Polymers 0.000 description 21
239000000741 silica gel Substances 0.000 description 21
229910002027 silica gel Inorganic materials 0.000 description 21
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
238000001704 evaporation Methods 0.000 description 19
239000012299 nitrogen atmosphere Substances 0.000 description 19
SMHORIXQSMDYEY-UHFFFAOYSA-N 2-ethylheptanenitrile Chemical compound CCCCCC(CC)C#N SMHORIXQSMDYEY-UHFFFAOYSA-N 0.000 description 18
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
229910021529 ammonia Inorganic materials 0.000 description 18
230000008020 evaporation Effects 0.000 description 18
150000002431 hydrogen Chemical class 0.000 description 18
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 17
238000001035 drying Methods 0.000 description 17
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
238000004821 distillation Methods 0.000 description 15
239000012074 organic phase Substances 0.000 description 15
238000000746 purification Methods 0.000 description 15
238000004587 chromatography analysis Methods 0.000 description 14
239000007921 spray Substances 0.000 description 14
229910052943 magnesium sulfate Inorganic materials 0.000 description 13
235000019341 magnesium sulphate Nutrition 0.000 description 13
238000002844 melting Methods 0.000 description 13
CSCYIHSLRZZOIB-UHFFFAOYSA-N 2-but-3-ynoxyacetic acid Chemical compound OC(=O)COCCC#C CSCYIHSLRZZOIB-UHFFFAOYSA-N 0.000 description 12
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
235000019256 formaldehyde Nutrition 0.000 description 12
230000008018 melting Effects 0.000 description 12
230000000694 effects Effects 0.000 description 11
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239000011734 sodium Substances 0.000 description 11
239000000725 suspension Substances 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
238000010828 elution Methods 0.000 description 10
239000000843 powder Substances 0.000 description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
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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 9
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
230000015572 biosynthetic process Effects 0.000 description 9
229910052708 sodium Inorganic materials 0.000 description 9
238000003786 synthesis reaction Methods 0.000 description 9
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
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NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 8
241000238631 Hexapoda Species 0.000 description 8
239000004480 active ingredient Substances 0.000 description 8
239000006185 dispersion Substances 0.000 description 8
239000012442 inert solvent Substances 0.000 description 8
238000002329 infrared spectrum Methods 0.000 description 8
239000000047 product Substances 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
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239000000126 substance Substances 0.000 description 8
125000001424 substituent group Chemical group 0.000 description 8
YHTBJYLPKQOJAY-UHFFFAOYSA-N 2-ethoxybutan-1-ol Chemical compound CCOC(CC)CO YHTBJYLPKQOJAY-UHFFFAOYSA-N 0.000 description 7
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 7
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238000012360 testing method Methods 0.000 description 7
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238000005481 NMR spectroscopy Methods 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
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238000004440 column chromatography Methods 0.000 description 6
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244000000013 helminth Species 0.000 description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
229910000041 hydrogen chloride Inorganic materials 0.000 description 6
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235000017557 sodium bicarbonate Nutrition 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
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238000009835 boiling Methods 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
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239000012280 lithium aluminium hydride Substances 0.000 description 5
239000000463 material Substances 0.000 description 5
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
SZSSMFVYZRQGIM-UHFFFAOYSA-N 2-(hydroxymethyl)-2-propylpropane-1,3-diol Chemical compound CCCC(CO)(CO)CO SZSSMFVYZRQGIM-UHFFFAOYSA-N 0.000 description 4
VRUHMDNPHCTABF-UHFFFAOYSA-N 2-but-3-ynylsulfanylacetic acid Chemical compound OC(=O)CSCCC#C VRUHMDNPHCTABF-UHFFFAOYSA-N 0.000 description 4
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FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 4
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125000001309 chloro group Chemical group Cl* 0.000 description 4
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QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
239000006072 paste Substances 0.000 description 4
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LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 4
239000002453 shampoo Substances 0.000 description 4
238000001228 spectrum Methods 0.000 description 4
CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 4
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BNEQHTNDYHYJFK-UHFFFAOYSA-N 2-tert-butyl-2-(hydroxymethyl)propane-1,3-diol Chemical compound CC(C)(C)C(CO)(CO)CO BNEQHTNDYHYJFK-UHFFFAOYSA-N 0.000 description 3
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WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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LQAVWYMTUMSFBE-UHFFFAOYSA-N pent-4-en-1-ol Chemical compound OCCCC=C LQAVWYMTUMSFBE-UHFFFAOYSA-N 0.000 description 1
FSUXYWPILZJGCC-UHFFFAOYSA-N pent-4-en-1-ol Natural products CC=CCCO FSUXYWPILZJGCC-UHFFFAOYSA-N 0.000 description 1
239000002304 perfume Substances 0.000 description 1
DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920001983 poloxamer Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
235000021039 pomes Nutrition 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
239000003380 propellant Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
239000002728 pyrethroid Substances 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
235000012045 salad Nutrition 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
XDEXVHOAFVJKAI-UHFFFAOYSA-M sodium;2-(1-propyl-3,5,8-trioxabicyclo[2.2.2]octan-4-yl)acetate Chemical compound [Na+].C1OC2(CC([O-])=O)OCC1(CCC)CO2 XDEXVHOAFVJKAI-UHFFFAOYSA-M 0.000 description 1
GIPRGFRQMWSHAK-UHFFFAOYSA-M sodium;2-propan-2-ylbenzenesulfonate Chemical compound [Na+].CC(C)C1=CC=CC=C1S([O-])(=O)=O GIPRGFRQMWSHAK-UHFFFAOYSA-M 0.000 description 1
239000002689 soil Substances 0.000 description 1
238000003892 spreading Methods 0.000 description 1
230000007480 spreading Effects 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000004575 stone Substances 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
235000013616 tea Nutrition 0.000 description 1
WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
239000012085 test solution Substances 0.000 description 1
239000004753 textile Substances 0.000 description 1
239000011732 tocopherol Substances 0.000 description 1
229930003799 tocopherol Natural products 0.000 description 1
235000019149 tocopherols Nutrition 0.000 description 1
238000002627 tracheal intubation Methods 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
229940078499 tricalcium phosphate Drugs 0.000 description 1
229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
235000019731 tricalcium phosphate Nutrition 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
IIHPVYJPDKJYOU-UHFFFAOYSA-N triphenylcarbethoxymethylenephosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-UHFFFAOYSA-N 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1
239000002966 varnish Substances 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
235000020234 walnut Nutrition 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1

Classifications

- 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
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/48—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —S—C≡N groups
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
- 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
- A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
- A01N55/02—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur containing metal atoms
- A01N55/04—Tin

Landscapes

Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

DD88318186A 1987-07-22 1988-07-21 Verfahren zur herstellung von derivaten von 2,6,7-trioxabicydo[2.2.2]-octanen, pestizide zusammensetzung und verfahren zur schaedlingsbekaempfung DD290195A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB878717274A GB8717274D0 (en)	1987-07-22	1987-07-22	Pesticidal compounds

Publications (1)

Publication Number	Publication Date
DD290195A5 true DD290195A5 (de)	1991-05-23

Family

ID=10621065

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD88318186A DD290195A5 (de)	1987-07-22	1988-07-21	Verfahren zur herstellung von derivaten von 2,6,7-trioxabicydo[2.2.2]-octanen, pestizide zusammensetzung und verfahren zur schaedlingsbekaempfung

Country Status (5)

Country	Link
DD (1)	DD290195A5 (pl)
GB (1)	GB8717274D0 (pl)
PL (2)	PL160117B1 (pl)
RU (1)	RU2056107C1 (pl)
ZA (1)	ZA885306B (pl)

1987
- 1987-07-22 GB GB878717274A patent/GB8717274D0/en active Pending
1988
- 1988-07-21 PL PL1988281393A patent/PL160117B1/pl unknown
- 1988-07-21 PL PL1988281392A patent/PL159996B1/pl unknown
- 1988-07-21 DD DD88318186A patent/DD290195A5/de not_active IP Right Cessation
- 1988-07-21 ZA ZA885306A patent/ZA885306B/xx unknown
1990
- 1990-03-07 RU SU904743282A patent/RU2056107C1/ru active

Also Published As

Publication number	Publication date
RU2056107C1 (ru)	1996-03-20
PL160117B1 (en)	1993-02-26
GB8717274D0 (en)	1987-08-26
ZA885306B (en)	1990-03-28
PL281392A1 (en)	1990-05-14
PL159996B1 (pl)	1993-01-29
PL281393A1 (en)	1990-05-14

Legal Events

Date	Code	Title	Description
1998-12-17	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
CA1084943A (en)	1980-09-02	Pesticidal m-phenoxybenzyl esters of 2,2- dimethylspiro 2,4 heptane-1-carboxylic acid derivatives
DE3689392T2 (de)	1994-05-26	Pestizidverbindungen.
DE2738150A1 (de)	1978-03-02	3-styryl-2,2-dimethylcyclopropan-1carbonsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide
DE3004177A1 (de)	1980-08-14	Optisch aktive alpha -cyan-3-(4-halogenphenoxy)-benzyl-2-(4-chlorphenyl)-isovalerat-derivate, verfahren zu ihrer herstellung und ihre verwendung
DE3876298T2 (de)	1993-04-08	Heterozyklische pestizidverbindungen.
DD298782A5 (de)	1992-03-12	N-phenylpyrazol-derivate
DE1667979A1 (de)	1971-07-15	Schaedlingsbekaempfungsmittel,die bestimmte Benzodioxole enthalten,sowie Verfahren zu deren Herstellung
DE68911876T2 (de)	1994-05-05	Pestizide.
DE3126327C2 (pl)	1991-11-14
DE3784028T2 (de)	1993-08-12	Pestizide verbindungen.
DE69937771T2 (de)	2008-12-24	1-Aryl-4-cycloalk(en)ylpyrazole als antiparasitäre Mittel
DE68902306T2 (de)	1993-03-11	Heterozyklische pestizide verbindungen.
RU2063972C1 (ru)	1996-07-20	Производные гетеробициклоалканов
DD275604A5 (de)	1990-01-31	Insektizide oder akarizide zusammensetzung
DD290195A5 (de)	1991-05-23	Verfahren zur herstellung von derivaten von 2,6,7-trioxabicydo[2.2.2]-octanen, pestizide zusammensetzung und verfahren zur schaedlingsbekaempfung
US5116862A (en)	1992-05-26	Pesticidal compounds
US5466710A (en)	1995-11-14	Heterobicycloalkanes as pesticidal compounds
US5352822A (en)	1994-10-04	Pesticides
DE2605828A1 (de)	1976-08-26	Phenoxybenzylester von spirocarbonsaeuren
AU663691B2 (en)	1995-10-19	Tri thiabicyclo {2.2.2.}octane derivatives as pesticides
DE69201784T2 (de)	1995-09-07	Heterocyclische Amidderivate und ihre Verwendung als Schädlingsbekämpfungsmittel.
DE68924199T2 (de)	1996-02-08	Arylfluoralkenamide und ihre Verwendung als Schädlingsbekämpfungsmittel.
DE2335347C3 (de)	1977-04-07	Substituierte Essigsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung als Pestizide
DD282688A5 (de)	1990-09-19	Verfahren zur herstellung von neuen 2,5-disubstituierten dithianen, pestizide formulierung und methode fuer die bekaempfung von schaedlichen gliederfuessern
DE1922572A1 (de)	1969-11-13	Insekticide und acaricide Benzimidazolverbindungen enthaltende Mittel