AP75A - Pesticidal compounds. - Google Patents

Pesticidal compounds. Download PDF

Info

Publication number: AP75A
Authority: AP; ARIPO
Prior art keywords: octane; group; trioxabicyclo; ynyl; propyl
Prior art date: 1987-07-22

Application number

APAP/P/1988/000096A

Other languages

English (en)

Other versions

AP8800096A0 (en

Inventor

John Bernard Weston

John Patrick Larkin

Ian Harold Smith

Original Assignee

Roussel Uclaf

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

1988-07-22

Publication date

1990-03-05

1987-07-22 Priority claimed from GB878717274A external-priority patent/GB8717274D0/en

1987-10-07 Priority claimed from GB878723488A external-priority patent/GB8723488D0/en

1988-04-26 Priority claimed from GB888809851A external-priority patent/GB8809851D0/en

1988-05-01 Publication of AP8800096A0 publication Critical patent/AP8800096A0/xx

1988-07-22 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1990-03-05 Application granted granted Critical

1990-03-05 Publication of AP75A publication Critical patent/AP75A/en

Links

150000001875 compounds Chemical class 0.000 title claims description 204
230000000361 pesticidal effect Effects 0.000 title claims description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 338
239000000203 mixture Substances 0.000 claims description 219
238000000034 method Methods 0.000 claims description 106
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 85
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 80
125000005843 halogen group Chemical group 0.000 claims description 77
-1 C. Chemical group 0.000 claims description 67
238000006243 chemical reaction Methods 0.000 claims description 54
125000004093 cyano group Chemical group *C#N 0.000 claims description 54
125000000217 alkyl group Chemical group 0.000 claims description 45
239000001257 hydrogen Substances 0.000 claims description 41
229910052739 hydrogen Inorganic materials 0.000 claims description 41
229910052757 nitrogen Inorganic materials 0.000 claims description 40
125000003545 alkoxy group Chemical group 0.000 claims description 39
229910052727 yttrium Inorganic materials 0.000 claims description 29
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
238000009472 formulation Methods 0.000 claims description 24
125000004432 carbon atom Chemical group C* 0.000 claims description 23
LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 21
241001465754 Metazoa Species 0.000 claims description 17
125000000304 alkynyl group Chemical group 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
125000001931 aliphatic group Chemical group 0.000 claims description 15
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
125000001153 fluoro group Chemical group F* 0.000 claims description 15
229910052760 oxygen Inorganic materials 0.000 claims description 15
239000001301 oxygen Substances 0.000 claims description 15
125000001183 hydrocarbyl group Chemical group 0.000 claims description 13
125000004423 acyloxy group Chemical group 0.000 claims description 12
125000003342 alkenyl group Chemical group 0.000 claims description 12
239000002585 base Substances 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
125000003118 aryl group Chemical group 0.000 claims description 11
238000004519 manufacturing process Methods 0.000 claims description 11
241000238421 Arthropoda Species 0.000 claims description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
241000607479 Yersinia pestis Species 0.000 claims description 10
125000001246 bromo group Chemical group Br* 0.000 claims description 10
125000001309 chloro group Chemical group Cl* 0.000 claims description 10
239000005864 Sulphur Substances 0.000 claims description 9
239000004480 active ingredient Substances 0.000 claims description 9
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
239000000126 substance Substances 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 8
239000012634 fragment Substances 0.000 claims description 8
244000000013 helminth Species 0.000 claims description 8
125000005842 heteroatom Chemical group 0.000 claims description 8
206010061217 Infestation Diseases 0.000 claims description 7
125000002837 carbocyclic group Chemical group 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
125000001188 haloalkyl group Chemical group 0.000 claims description 6
108010034145 Helminth Proteins Proteins 0.000 claims description 5
239000004593 Epoxy Substances 0.000 claims description 4
239000003377 acid catalyst Substances 0.000 claims description 4
125000001118 alkylidene group Chemical group 0.000 claims description 4
239000000969 carrier Substances 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
150000002923 oximes Chemical class 0.000 claims description 4
125000004043 oxo group Chemical group O=* 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
241000282414 Homo sapiens Species 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
150000001721 carbon Chemical group 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
239000000417 fungicide Substances 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
OJHDPDDCXDBZOQ-UHFFFAOYSA-N 4-propyl-2,6,7-trioxabicyclo[2.2.2]octane Chemical compound C1OC2OCC1(CCC)CO2 OJHDPDDCXDBZOQ-UHFFFAOYSA-N 0.000 claims description 2
125000005103 alkyl silyl group Chemical group 0.000 claims description 2
239000005667 attractant Substances 0.000 claims description 2
239000003899 bactericide agent Substances 0.000 claims description 2
125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
108010069898 fibrinogen fragment X Proteins 0.000 claims description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
239000005871 repellent Substances 0.000 claims description 2
230000002940 repellent Effects 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 8
HLRXHMOZGARBHT-UHFFFAOYSA-N 4-(2-methylhex-5-ynyl)-1-propyl-3,5,8-trioxabicyclo[2.2.2]octane-2-carbonitrile Chemical compound C1OC2(CC(C)CCC#C)OCC1(CCC)C(C#N)O2 HLRXHMOZGARBHT-UHFFFAOYSA-N 0.000 claims 1
TVCDXZNFJLOHME-UHFFFAOYSA-N 4-(4-ethynylcyclohexyl)-1-propyl-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound O1CC(CCC)(CO2)COC12C1CCC(C#C)CC1 TVCDXZNFJLOHME-UHFFFAOYSA-N 0.000 claims 1
AHVUEKRGNHHGKT-UHFFFAOYSA-N 4-hex-5-ynyl-1-propyl-3,5,8-trithiabicyclo[2.2.2]octane Chemical compound C1SC2(CCCCC#C)SCC1(CCC)CS2 AHVUEKRGNHHGKT-UHFFFAOYSA-N 0.000 claims 1
PXUBJTOXYZIXRU-UHFFFAOYSA-N C(CCCC#C)C12OCC(CS1)(CS2)CC(C)C.C(CCCC#C)C21OCC(CO2)(CO1)C1=CC=CC=C1 Chemical compound C(CCCC#C)C12OCC(CS1)(CS2)CC(C)C.C(CCCC#C)C21OCC(CO2)(CO1)C1=CC=CC=C1 PXUBJTOXYZIXRU-UHFFFAOYSA-N 0.000 claims 1
101100260565 Dictyostelium discoideum thyA gene Proteins 0.000 claims 1
235000006679 Mentha X verticillata Nutrition 0.000 claims 1
235000002899 Mentha suaveolens Nutrition 0.000 claims 1
235000001636 Mentha x rotundifolia Nutrition 0.000 claims 1
230000031902 chemoattractant activity Effects 0.000 claims 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
229910052698 phosphorus Inorganic materials 0.000 claims 1
229910052717 sulfur Inorganic materials 0.000 claims 1
101150068774 thyX gene Proteins 0.000 claims 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 180
239000000243 solution Substances 0.000 description 180
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 164
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 138
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 117
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 90
229960004132 diethyl ether Drugs 0.000 description 89
239000003921 oil Substances 0.000 description 84
235000019198 oils Nutrition 0.000 description 84
229910052943 magnesium sulfate Inorganic materials 0.000 description 82
235000019341 magnesium sulphate Nutrition 0.000 description 82
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 68
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 68
239000000284 extract Substances 0.000 description 61
239000002904 solvent Substances 0.000 description 61
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 60
239000007787 solid Substances 0.000 description 42
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 41
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 40
239000012267 brine Substances 0.000 description 40
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 40
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
238000001819 mass spectrum Methods 0.000 description 33
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 33
238000002329 infrared spectrum Methods 0.000 description 32
239000011541 reaction mixture Substances 0.000 description 31
238000003756 stirring Methods 0.000 description 30
238000001030 gas--liquid chromatography Methods 0.000 description 29
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 25
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
238000001035 drying Methods 0.000 description 24
239000007788 liquid Substances 0.000 description 24
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 23
238000000451 chemical ionisation Methods 0.000 description 23
238000001704 evaporation Methods 0.000 description 23
229920006395 saturated elastomer Polymers 0.000 description 23
230000008020 evaporation Effects 0.000 description 22
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 19
229910021529 ammonia Inorganic materials 0.000 description 18
238000010992 reflux Methods 0.000 description 18
239000000377 silicon dioxide Substances 0.000 description 18
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 17
239000012074 organic phase Substances 0.000 description 17
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
238000004587 chromatography analysis Methods 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
239000002253 acid Substances 0.000 description 15
238000004821 distillation Methods 0.000 description 15
238000000746 purification Methods 0.000 description 15
239000007921 spray Substances 0.000 description 15
239000012442 inert solvent Substances 0.000 description 13
239000011734 sodium Substances 0.000 description 12
CUBVDBSVGQEYCB-UHFFFAOYSA-N (3-propyloxetan-3-yl)methanol Chemical compound CCCC1(CO)COC1 CUBVDBSVGQEYCB-UHFFFAOYSA-N 0.000 description 11
SMHORIXQSMDYEY-UHFFFAOYSA-N 2-ethylheptanenitrile Chemical compound CCCCCC(CC)C#N SMHORIXQSMDYEY-UHFFFAOYSA-N 0.000 description 11
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 11
230000015572 biosynthetic process Effects 0.000 description 11
230000000694 effects Effects 0.000 description 11
229910052708 sodium Inorganic materials 0.000 description 11
239000000725 suspension Substances 0.000 description 11
238000003786 synthesis reaction Methods 0.000 description 11
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
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 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
CSCYIHSLRZZOIB-UHFFFAOYSA-N 2-but-3-ynoxyacetic acid Chemical compound OC(=O)COCCC#C CSCYIHSLRZZOIB-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 9
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
241000196324 Embryophyta Species 0.000 description 8
241000238631 Hexapoda Species 0.000 description 8
239000006185 dispersion Substances 0.000 description 8
VPFMEXRVUOPYRG-UHFFFAOYSA-N hex-5-ynoic acid Chemical compound OC(=O)CCCC#C VPFMEXRVUOPYRG-UHFFFAOYSA-N 0.000 description 8
239000000843 powder Substances 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
235000017557 sodium bicarbonate Nutrition 0.000 description 8
229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
YPRJMIHDDZMEJB-UHFFFAOYSA-N 3-propyloxetane-3-carbaldehyde Chemical compound CCCC1(C=O)COC1 YPRJMIHDDZMEJB-UHFFFAOYSA-N 0.000 description 7
OFCPMJGTZUVUSM-UHFFFAOYSA-N 6-heptynoic acid Chemical compound OC(=O)CCCCC#C OFCPMJGTZUVUSM-UHFFFAOYSA-N 0.000 description 7
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 7
238000004440 column chromatography Methods 0.000 description 7
239000004495 emulsifiable concentrate Substances 0.000 description 7
239000010410 layer Substances 0.000 description 7
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
239000012312 sodium hydride Substances 0.000 description 7
229910000104 sodium hydride Inorganic materials 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
239000004255 Butylated hydroxyanisole Substances 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
229940022663 acetate Drugs 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
235000019282 butylated hydroxyanisole Nutrition 0.000 description 6
229940043253 butylated hydroxyanisole Drugs 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
239000013078 crystal Substances 0.000 description 6
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 6
239000003995 emulsifying agent Substances 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
241000254173 Coleoptera Species 0.000 description 5
101150052863 THY1 gene Proteins 0.000 description 5
235000011054 acetic acid Nutrition 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
OTJZCIYGRUNXTP-UHFFFAOYSA-N but-3-yn-1-ol Chemical compound OCCC#C OTJZCIYGRUNXTP-UHFFFAOYSA-N 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
238000001816 cooling Methods 0.000 description 5
238000010828 elution Methods 0.000 description 5
239000012259 ether extract Substances 0.000 description 5
150000004820 halides Chemical class 0.000 description 5
239000003350 kerosene Substances 0.000 description 5
239000012280 lithium aluminium hydride Substances 0.000 description 5
239000012299 nitrogen atmosphere Substances 0.000 description 5
GHLZUHZBBNDWHW-UHFFFAOYSA-N nonanamide Chemical compound CCCCCCCCC(N)=O GHLZUHZBBNDWHW-UHFFFAOYSA-N 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 4
GMFDYXLFHSFUHE-UHFFFAOYSA-N 3-prop-2-ynoxypropanoic acid Chemical compound OC(=O)CCOCC#C GMFDYXLFHSFUHE-UHFFFAOYSA-N 0.000 description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
241000238876 Acari Species 0.000 description 4
FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 4
241000257229 Musca <genus> Species 0.000 description 4
241000500439 Plutella Species 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
235000019270 ammonium chloride Nutrition 0.000 description 4
239000007900 aqueous suspension Substances 0.000 description 4
229910002092 carbon dioxide Inorganic materials 0.000 description 4
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 4
NZNMSOFKMUBTKW-UHFFFAOYSA-M cyclohexanecarboxylate Chemical compound [O-]C(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-M 0.000 description 4
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
238000000605 extraction Methods 0.000 description 4
239000007789 gas Substances 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
239000000463 material Substances 0.000 description 4
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 4
PYRGQXMUCOQROF-UHFFFAOYSA-N methyl 4-(2,2-dibromoethenyl)cyclohexane-1-carboxylate Chemical class COC(=O)C1CCC(C=C(Br)Br)CC1 PYRGQXMUCOQROF-UHFFFAOYSA-N 0.000 description 4
AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 4
229960005235 piperonyl butoxide Drugs 0.000 description 4
239000004540 pour-on Substances 0.000 description 4
239000002453 shampoo Substances 0.000 description 4
239000004094 surface-active agent Substances 0.000 description 4
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
230000000699 topical effect Effects 0.000 description 4
239000008096 xylene Substances 0.000 description 4
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125000004433 nitrogen atom Chemical group N* 0.000 description 1
GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 1
231100001143 noxa Toxicity 0.000 description 1
229920002113 octoxynol Polymers 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000003883 ointment base Substances 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000002905 orthoesters Chemical class 0.000 description 1
125000003544 oxime group Chemical group 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000000123 paper Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
239000006072 paste Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
LQAVWYMTUMSFBE-UHFFFAOYSA-N pent-4-en-1-ol Chemical compound OCCCC=C LQAVWYMTUMSFBE-UHFFFAOYSA-N 0.000 description 1
CRWVOXFUXPYTRK-UHFFFAOYSA-N pent-4-yn-1-ol Chemical compound OCCCC#C CRWVOXFUXPYTRK-UHFFFAOYSA-N 0.000 description 1
VWYVHZFRBJJWSM-UHFFFAOYSA-N pent-4-ynal Chemical compound O=CCCC#C VWYVHZFRBJJWSM-UHFFFAOYSA-N 0.000 description 1
ZKCDAGCMMFDKFX-UHFFFAOYSA-N pent-4-ynyl methanesulfonate Chemical compound CS(=O)(=O)OCCCC#C ZKCDAGCMMFDKFX-UHFFFAOYSA-N 0.000 description 1
239000002304 perfume Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 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
IQWMWCXBJXUPIX-UHFFFAOYSA-N prop-2-ynyl 2-(1-propyl-3,5,8-trioxabicyclo[2.2.2]octan-4-yl)acetate Chemical compound C1OC2(CC(=O)OCC#C)OCC1(CCC)CO2 IQWMWCXBJXUPIX-UHFFFAOYSA-N 0.000 description 1
PVKOJYHDOXEPJY-UHFFFAOYSA-N prop-2-ynyl 3-prop-2-ynylsulfanylpropanoate Chemical compound C#CCOC(=O)CCSCC#C PVKOJYHDOXEPJY-UHFFFAOYSA-N 0.000 description 1
UNKYWUDQUIRKKG-UHFFFAOYSA-N propan-2-yl benzenesulfonate;sodium Chemical compound [Na].CC(C)OS(=O)(=O)C1=CC=CC=C1 UNKYWUDQUIRKKG-UHFFFAOYSA-N 0.000 description 1
239000003380 propellant Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
229940095574 propionic acid Drugs 0.000 description 1
MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical compound CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 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
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
235000012045 salad Nutrition 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000000523 sample Substances 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
235000009518 sodium iodide 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
239000002689 soil Substances 0.000 description 1
238000001228 spectrum Methods 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
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
235000013616 tea Nutrition 0.000 description 1
239000012085 test solution Substances 0.000 description 1
239000004753 textile Substances 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
229930003799 tocopherol Natural products 0.000 description 1
239000011732 tocopherol Substances 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
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-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
238000001665 trituration Methods 0.000 description 1
239000004532 vaporising mat Substances 0.000 description 1
239000013598 vector Substances 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
235000020234 walnut Nutrition 0.000 description 1
238000010792 warming Methods 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

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/02—Thiols having mercapto groups bound to acyclic carbon atoms
- C07C321/04—Thiols having mercapto groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D305/06—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D305/08—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms 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 atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/08—Bridged systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D497/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D497/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D497/08—Bridged systems

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Dentistry (AREA)
Plant Pathology (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Tropical Medicine & Parasitology (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

APAP/P/1988/000096A 1987-07-22 1988-07-22 Pesticidal compounds. AP75A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB878717274A GB8717274D0 (en)	1987-07-22	1987-07-22	Pesticidal compounds
GB878723488A GB8723488D0 (en)	1987-10-07	1987-10-07	Pesticidal compounds
GB888809851A GB8809851D0 (en)	1988-04-26	1988-04-26	Pesticidal compounds

Publications (2)

Publication Number	Publication Date
AP8800096A0 AP8800096A0 (en)	1988-05-01
AP75A true AP75A (en)	1990-03-05

Family

ID=27263521

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
APAP/P/1988/000096A AP75A (en)	1987-07-22	1988-07-22	Pesticidal compounds.

Country Status (22)

Country	Link
EP (3)	EP0622370A3 (pl)
JP (1)	JPS6447787A (pl)
KR (1)	KR890002086A (pl)
CN (1)	CN1030759A (pl)
AP (1)	AP75A (pl)
AT (1)	ATE128711T1 (pl)
AU (1)	AU611702B2 (pl)
BR (1)	BR8803652A (pl)
DE (1)	DE3854544D1 (pl)
DK (1)	DK167188B1 (pl)
EG (1)	EG18921A (pl)
FI (1)	FI883453A7 (pl)
GR (1)	GR3018584T3 (pl)
HU (1)	HU209128B (pl)
IL (1)	IL87183A (pl)
MC (1)	MC1956A1 (pl)
MY (1)	MY103751A (pl)
NZ (1)	NZ225508A (pl)
PL (2)	PL159875B1 (pl)
PT (1)	PT88053B (pl)
RU (2)	RU2034847C1 (pl)
TR (1)	TR25921A (pl)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9027246D0 (en) *	1990-12-17	1991-02-06	Wellcome Found	Pesticidal compounds
NO328803B1 (no)	2000-03-03	2010-05-18	Thia Medica	Nye fettsyreanaloger
NZ537762A (en)	2002-06-20	2007-02-23	Thia Medica As	Sulfur-containing phospholipid derivatives
RU2318385C2 (ru) *	2006-03-16	2008-03-10	Общество с ограниченной ответственностью "Медицинская компания "Пери"	Способ инсектицидной обработки и инсектицидная композиция "пешка" для его осуществления
FR2953369B1 (fr) *	2009-12-07	2016-02-05	Total Raffinage Marketing	Concentre emulsionnable pour composition phytosanitaire, concentre emulsionnable et film phytosanitaire

Citations (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0152229A2 (en) *	1984-01-30	1985-08-21	The Regents Of The University Of California	A class of pesticides comprising 1,4-bis-substituted-2,6,7-trioxabicyclo(2.2.2)octanes
EP0211598A2 (en) *	1985-07-30	1987-02-25	Roussel-Uclaf	Pesticidal compounds
EP0216624A2 (en) *	1985-09-23	1987-04-01	Roussel-Uclaf	Pesticidal compounds
EP0235979A1 (en) *	1986-02-11	1987-09-09	The Wellcome Foundation Limited	Pesticidal formulations

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3686224A (en)	1970-02-24	1972-08-22	Gulf Research Development Co	2,6,7-trioxabicyclo(2.2.2)octane compounds
ES2003872A6 (es) *	1985-09-24	1988-12-01	Wellcome Found	Un procedimiento para la preparacion de derivados de heterobicicloalcanos
EP0216625A3 (en) *	1985-09-24	1988-08-17	The Wellcome Foundation Limited	Pesticidal compounds

1988
- 1988-07-21 CN CN88106390A patent/CN1030759A/zh active Pending
- 1988-07-21 EP EP94111438A patent/EP0622370A3/en not_active Withdrawn
- 1988-07-21 DE DE3854544T patent/DE3854544D1/de not_active Expired - Lifetime
- 1988-07-21 JP JP63180441A patent/JPS6447787A/ja active Pending
- 1988-07-21 MY MYPI88000824A patent/MY103751A/en unknown
- 1988-07-21 PT PT88053A patent/PT88053B/pt not_active IP Right Cessation
- 1988-07-21 EP EP88306718A patent/EP0300797B1/en not_active Expired - Lifetime
- 1988-07-21 DK DK407188A patent/DK167188B1/da active
- 1988-07-21 AU AU19776/88A patent/AU611702B2/en not_active Ceased
- 1988-07-21 PL PL1988273850A patent/PL159875B1/pl unknown
- 1988-07-21 EG EG40388A patent/EG18921A/xx active
- 1988-07-21 EP EP93100641A patent/EP0545892A1/en not_active Withdrawn
- 1988-07-21 MC MC881993A patent/MC1956A1/fr unknown
- 1988-07-21 PL PL1988278571A patent/PL158212B1/pl unknown
- 1988-07-21 AT AT88306718T patent/ATE128711T1/de not_active IP Right Cessation
- 1988-07-21 BR BR8803652A patent/BR8803652A/pt not_active Application Discontinuation
- 1988-07-21 IL IL8718388A patent/IL87183A/en not_active IP Right Cessation
- 1988-07-21 KR KR1019880009205A patent/KR890002086A/ko not_active Ceased
- 1988-07-21 HU HU883799A patent/HU209128B/hu not_active IP Right Cessation
- 1988-07-21 NZ NZ225508A patent/NZ225508A/en unknown
- 1988-07-21 FI FI883453A patent/FI883453A7/fi not_active Application Discontinuation
- 1988-07-22 AP APAP/P/1988/000096A patent/AP75A/en active
- 1988-07-22 TR TR88/0532A patent/TR25921A/xx unknown
1991
- 1991-03-22 RU SU914894846A patent/RU2034847C1/ru active
1992
- 1992-05-05 RU SU925011568A patent/RU2063972C1/ru active
1995
- 1995-10-05 GR GR950400760T patent/GR3018584T3/el unknown

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0152229A2 (en) *	1984-01-30	1985-08-21	The Regents Of The University Of California	A class of pesticides comprising 1,4-bis-substituted-2,6,7-trioxabicyclo(2.2.2)octanes
EP0211598A2 (en) *	1985-07-30	1987-02-25	Roussel-Uclaf	Pesticidal compounds
EP0216624A2 (en) *	1985-09-23	1987-04-01	Roussel-Uclaf	Pesticidal compounds
EP0235979A1 (en) *	1986-02-11	1987-09-09	The Wellcome Foundation Limited	Pesticidal formulations

Also Published As

Publication number	Publication date
ATE128711T1 (de)	1995-10-15
FI883453A0 (fi)	1988-07-21
RU2063972C1 (ru)	1996-07-20
EP0622370A2 (en)	1994-11-02
DK407188A (da)	1989-01-23
DK167188B1 (da)	1993-09-13
AP8800096A0 (en)	1988-05-01
TR25921A (tr)	1993-09-17
EP0300797A1 (en)	1989-01-25
PL159875B1 (pl)	1993-01-29
DE3854544D1 (de)	1995-11-09
PL278571A1 (en)	1989-10-30
HUT47584A (en)	1989-03-28
RU2034847C1 (ru)	1995-05-10
MY103751A (en)	1993-09-30
MC1956A1 (fr)	1989-06-30
CN1030759A (zh)	1989-02-01
HU209128B (en)	1994-03-28
JPS6447787A (en)	1989-02-22
EG18921A (en)	1994-10-30
PT88053A (pt)	1989-06-30
EP0300797B1 (en)	1995-10-04
KR890002086A (ko)	1989-04-08
EP0622370A3 (en)	1995-03-08
FI883453A7 (fi)	1989-01-23
PL158212B1 (pl)	1992-08-31
NZ225508A (en)	1992-04-28
IL87183A (en)	1995-05-26
GR3018584T3 (en)	1996-04-30
AU1977688A (en)	1989-01-27
PL273850A1 (en)	1990-01-22
AU611702B2 (en)	1991-06-20
DK407188D0 (da)	1988-07-21
BR8803652A (pt)	1989-02-14
PT88053B (pt)	1995-03-01
IL87183A0 (en)	1988-12-30
EP0545892A1 (en)	1993-06-09

Publication	Publication Date	Title
AU604212B2 (en)	1990-12-13	Pesticidal compounds
AU626525B2 (en)	1992-08-06	5-t-butyl-1,3-dithiane derivatives
AP75A (en)	1990-03-05	Pesticidal compounds.
EP0216624B1 (en)	1995-02-22	Pesticidal compounds
AP65A (en)	1989-12-12	Pestcidal compounds.
JP2667916B2 (ja)	1997-10-27	有害生物防除剤
US4942173A (en)	1990-07-17	Pesticidal compounds
US5116862A (en)	1992-05-26	Pesticidal compounds
US5466710A (en)	1995-11-14	Heterobicycloalkanes as pesticidal compounds
US5204333A (en)	1993-04-20	Pesticidal compounds
US5026874A (en)	1991-06-25	Pesticidal compounds
EP0380312A1 (en)	1990-08-01	Pesticidal compounds
WO1990006304A1 (en)	1990-06-14	Novel heterocyclic pesticidal compounds
US5502073A (en)	1996-03-26	Heterocyclic pesticidal compounds
US5057508A (en)	1991-10-15	Pesticidal compounds
US5157029A (en)	1992-10-20	Pesticidal compounds
AU663691B2 (en)	1995-10-19	Tri thiabicyclo {2.2.2.}octane derivatives as pesticides
US4965257A (en)	1990-10-23	Pesticidal compounds
AP59A (en)	1989-10-30	Novel heterocyclic pesticidal compounds.
EP0285342A2 (en)	1988-10-05	Improvements relating to pesticides
EP0372817B1 (en)	1992-05-13	Novel heterocyclic pesticidal compounds
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
EP0372870A2 (en)	1990-06-13	Novel heterocyclic pesticidal compounds