AP65A - Pestcidal compounds. - Google Patents

Pestcidal compounds. Download PDF

Info

Publication number: AP65A
Authority: AP; ARIPO
Prior art keywords: phenyl; octane; group; alkyl; trioxabicyclo
Prior art date: 1985-09-23

Application number

APAP/P/1986/000045A

Other languages

English (en)

Other versions

AP8600045A0 (en

Inventor

John Edward Casida

Christopher John Palmer

John Patrick Larkin

Ian Harold Smith

Original Assignee

The Wellcome Foundation Ltd

Univ California

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.)

1985-09-23

Filing date

1986-09-22

Publication date

1989-12-12

1986-08-01 Publication of AP8600045A0 publication Critical patent/AP8600045A0/xx

1986-09-22 Application filed by The Wellcome Foundation Ltd, Univ California filed Critical The Wellcome Foundation Ltd

1989-12-12 Application granted granted Critical

1989-12-12 Publication of AP65A publication Critical patent/AP65A/en

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 153
-1 4-dibromomethylphenyl Chemical group 0.000 claims abstract description 38
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 135
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 125
239000000203 mixture Substances 0.000 claims description 111
125000000217 alkyl group Chemical group 0.000 claims description 96
229910052739 hydrogen Inorganic materials 0.000 claims description 67
239000001257 hydrogen Substances 0.000 claims description 65
125000004093 cyano group Chemical group *C#N 0.000 claims description 43
125000005843 halogen group Chemical group 0.000 claims description 38
125000003545 alkoxy group Chemical group 0.000 claims description 37
238000000034 method Methods 0.000 claims description 37
125000000304 alkynyl group Chemical group 0.000 claims description 28
125000003342 alkenyl group Chemical group 0.000 claims description 27
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
238000009472 formulation Methods 0.000 claims description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
229910052760 oxygen Inorganic materials 0.000 claims description 19
239000001301 oxygen Substances 0.000 claims description 19
125000004432 carbon atom Chemical group C* 0.000 claims description 17
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
241000607479 Yersinia pestis Species 0.000 claims description 13
125000001153 fluoro group Chemical group F* 0.000 claims description 13
125000001424 substituent group Chemical group 0.000 claims description 11
125000001246 bromo group Chemical group Br* 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
239000005864 Sulphur Chemical group 0.000 claims description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
125000001309 chloro group Chemical group Cl* 0.000 claims description 8
125000001183 hydrocarbyl group Chemical group 0.000 claims description 8
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 8
230000000361 pesticidal effect Effects 0.000 claims description 8
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 8
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
125000003277 amino group Chemical group 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 7
239000000460 chlorine Substances 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical group 0.000 claims description 7
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
125000001931 aliphatic group Chemical group 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
239000011630 iodine Chemical group 0.000 claims description 6
229910052740 iodine Chemical group 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
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
206010061217 Infestation Diseases 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 5
125000002837 carbocyclic group Chemical group 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
125000002346 iodo group Chemical group I* 0.000 claims description 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
WZWNCSJQQMWTMS-UHFFFAOYSA-N 1-ethyl-4-(4-ethynylphenyl)-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound O1CC(CC)(CO2)COC12C1=CC=C(C#C)C=C1 WZWNCSJQQMWTMS-UHFFFAOYSA-N 0.000 claims description 3
230000000895 acaricidal effect Effects 0.000 claims description 3
125000005103 alkyl silyl group Chemical group 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 3
125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
238000007269 dehydrobromination reaction Methods 0.000 claims description 3
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
230000000749 insecticidal effect Effects 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
RIZZXCJMFIGMON-UHFFFAOYSA-N prop-2-ynyl acetate Chemical compound CC(=O)OCC#C RIZZXCJMFIGMON-UHFFFAOYSA-N 0.000 claims description 3
QVCOXWYMPCBIMH-UHFFFAOYSA-N prop-2-ynyl carbamate Chemical compound NC(=O)OCC#C QVCOXWYMPCBIMH-UHFFFAOYSA-N 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
VXQAPGCBJDOBGN-UHFFFAOYSA-N 1-(2,2-dimethylpropyl)-4-(4-ethynylphenyl)-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound O1CC(CC(C)(C)C)(CO2)COC12C1=CC=C(C#C)C=C1 VXQAPGCBJDOBGN-UHFFFAOYSA-N 0.000 claims description 2
PEMCJTGVXDHHGC-UHFFFAOYSA-N 1-propyl-4-(4-prop-1-ynylphenyl)-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound O1CC(CCC)(CO2)COC12C1=CC=C(C#CC)C=C1 PEMCJTGVXDHHGC-UHFFFAOYSA-N 0.000 claims description 2
VTUKKVHSZDBIPA-UHFFFAOYSA-N 3,5,8-trioxabicyclo[2.2.2]octane Chemical compound O1CC2COC1OC2 VTUKKVHSZDBIPA-UHFFFAOYSA-N 0.000 claims description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims description 2
125000004043 oxo group Chemical group O=* 0.000 claims description 2
FMLJQWIMQVSUMF-UHFFFAOYSA-N trimethyl-[2-[4-(1-propyl-3,5,8-trioxabicyclo[2.2.2]octan-4-yl)phenyl]ethynyl]silane Chemical compound O1CC(CCC)(CO2)COC12C1=CC=C(C#C[Si](C)(C)C)C=C1 FMLJQWIMQVSUMF-UHFFFAOYSA-N 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 19
AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
WUJXRLUSCOFFIK-UHFFFAOYSA-N 1-tert-butyl-4-[4-(3-methoxyprop-1-ynyl)phenyl]-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound C1=CC(C#CCOC)=CC=C1C1(OC2)OCC2(C(C)(C)C)CO1 WUJXRLUSCOFFIK-UHFFFAOYSA-N 0.000 claims 1
VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 claims 1
YJVVJOQVKMBUMF-UHFFFAOYSA-N 2-[4-(1-cyclohexyl-3,5,8-trioxabicyclo[2.2.2]octan-4-yl)phenyl]ethynyl-trimethylsilane Chemical compound C1=CC(C#C[Si](C)(C)C)=CC=C1C1(OC2)OCC2(C2CCCCC2)CO1 YJVVJOQVKMBUMF-UHFFFAOYSA-N 0.000 claims 1
MDAICTYEICDMCR-UHFFFAOYSA-N 4-[4-(3-ethoxyprop-1-ynyl)phenyl]-1-propyl-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound O1CC(CCC)(CO2)COC12C1=CC=C(C#CCOCC)C=C1 MDAICTYEICDMCR-UHFFFAOYSA-N 0.000 claims 1
OPVIBLCKPJHWAK-UHFFFAOYSA-N 4-[4-(4-methoxybut-1-ynyl)phenyl]-1-propyl-3,5,8-trioxabicyclo[2.2.2]octane Chemical compound O1CC(CCC)(CO2)COC12C1=CC=C(C#CCCOC)C=C1 OPVIBLCKPJHWAK-UHFFFAOYSA-N 0.000 claims 1
125000004122 cyclic group Chemical group 0.000 claims 1
125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
150000002500 ions Chemical class 0.000 claims 1
PTMCQFYJMIDACW-UHFFFAOYSA-N methyl 3-[4-(1-propyl-3,5,8-trioxabicyclo[2.2.2]octan-4-yl)phenyl]prop-2-ynoate Chemical compound O1CC(CCC)(CO2)COC12C1=CC=C(C#CC(=O)OC)C=C1 PTMCQFYJMIDACW-UHFFFAOYSA-N 0.000 claims 1
WUVLAIKRGCITRH-UHFFFAOYSA-N n-[3-[4-(1-propyl-3,5,8-trioxabicyclo[2.2.2]octan-4-yl)phenyl]prop-2-ynyl]acetamide Chemical compound O1CC(CCC)(CO2)COC12C1=CC=C(C#CCNC(C)=O)C=C1 WUVLAIKRGCITRH-UHFFFAOYSA-N 0.000 claims 1
HCJTYESURSHXNB-UHFFFAOYSA-N propynamide Chemical compound NC(=O)C#C HCJTYESURSHXNB-UHFFFAOYSA-N 0.000 claims 1
125000005842 heteroatom Chemical group 0.000 abstract description 2
125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 abstract 1
150000001345 alkine derivatives Chemical class 0.000 abstract 1
238000007256 debromination reaction Methods 0.000 abstract 1
239000002917 insecticide Substances 0.000 abstract 1
239000000575 pesticide Substances 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 142
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 111
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 96
239000000243 solution Substances 0.000 description 81
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 51
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 50
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 48
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 44
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 40
229960004132 diethyl ether Drugs 0.000 description 37
238000006243 chemical reaction Methods 0.000 description 34
239000007787 solid Substances 0.000 description 32
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
229910052757 nitrogen Inorganic materials 0.000 description 25
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 24
229910052943 magnesium sulfate Inorganic materials 0.000 description 24
235000019341 magnesium sulphate Nutrition 0.000 description 24
239000003921 oil Substances 0.000 description 24
235000019198 oils Nutrition 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
229910021529 ammonia Inorganic materials 0.000 description 18
229920006395 saturated elastomer Polymers 0.000 description 17
239000002904 solvent Substances 0.000 description 17
239000011541 reaction mixture Substances 0.000 description 16
238000003756 stirring Methods 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
238000004587 chromatography analysis Methods 0.000 description 15
239000000284 extract Substances 0.000 description 15
238000001819 mass spectrum Methods 0.000 description 15
238000001030 gas--liquid chromatography Methods 0.000 description 14
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
241001465754 Metazoa Species 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
239000012442 inert solvent Substances 0.000 description 12
230000000694 effects Effects 0.000 description 11
YACFFSVYSPMSGS-UHFFFAOYSA-N 3-methoxyprop-1-yne Chemical compound COCC#C YACFFSVYSPMSGS-UHFFFAOYSA-N 0.000 description 10
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 10
241000238631 Hexapoda Species 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
239000007788 liquid Substances 0.000 description 10
239000007921 spray Substances 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
238000000451 chemical ionisation Methods 0.000 description 9
239000013078 crystal Substances 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
239000011734 sodium Substances 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
229910052708 sodium Inorganic materials 0.000 description 8
239000000725 suspension Substances 0.000 description 8
FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 7
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 7
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
239000012267 brine Substances 0.000 description 7
238000004821 distillation Methods 0.000 description 7
239000004495 emulsifiable concentrate Substances 0.000 description 7
229960005235 piperonyl butoxide Drugs 0.000 description 7
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
241000238421 Arthropoda Species 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
239000012259 ether extract Substances 0.000 description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
239000000843 powder Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
238000004440 column chromatography Methods 0.000 description 5
239000003350 kerosene Substances 0.000 description 5
239000012280 lithium aluminium hydride Substances 0.000 description 5
238000000746 purification Methods 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
239000008096 xylene Substances 0.000 description 5
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 4
241000196324 Embryophyta Species 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
239000000443 aerosol Substances 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
239000007900 aqueous suspension Substances 0.000 description 4
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 4
239000006185 dispersion Substances 0.000 description 4
239000003995 emulsifying agent Substances 0.000 description 4
150000008282 halocarbons Chemical class 0.000 description 4
238000002329 infrared spectrum Methods 0.000 description 4
230000001665 lethal effect Effects 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 4
239000004540 pour-on Substances 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
239000002453 shampoo Substances 0.000 description 4
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241000255626 Tabanus <genus> Species 0.000 description 1
241001454293 Tetranychus urticae Species 0.000 description 1
241000333689 Tineola Species 0.000 description 1
241000254086 Tribolium <beetle> Species 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
244000098338 Triticum aestivum Species 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
241001414985 Zygentoma Species 0.000 description 1
GLYOPNLBKCBTMI-UHFFFAOYSA-N [2-chloro-2-(1-chloro-2-phenylethoxy)ethyl]benzene Chemical compound C=1C=CC=CC=1CC(Cl)OC(Cl)CC1=CC=CC=C1 GLYOPNLBKCBTMI-UHFFFAOYSA-N 0.000 description 1
AOIYANWKFZQWRQ-UHFFFAOYSA-N [Na].[Na].CC(C)OS(=O)(=O)C1=CC=CC=C1 Chemical compound [Na].[Na].CC(C)OS(=O)(=O)C1=CC=CC=C1 AOIYANWKFZQWRQ-UHFFFAOYSA-N 0.000 description 1
YSVDXOJUVQMPCX-UHFFFAOYSA-N [propoxy(prop-2-ynoxy)phosphoryl]benzene Chemical compound CCCOP(=O)(OCC#C)C1=CC=CC=C1 YSVDXOJUVQMPCX-UHFFFAOYSA-N 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
GFFGJBXGBJISGV-UHFFFAOYSA-N adenyl group Chemical group N1=CN=C2N=CNC2=C1N GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
125000005257 alkyl acyl group Chemical group 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
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150000001503 aryl iodides Chemical class 0.000 description 1
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239000005667 attractant Substances 0.000 description 1
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230000004071 biological effect Effects 0.000 description 1
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YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
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235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
229940095259 butylated hydroxytoluene Drugs 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
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 1
238000002144 chemical decomposition reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
125000005112 cycloalkylalkoxy group Chemical group 0.000 description 1
238000005828 desilylation reaction Methods 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
FXORZKOZOQWVMQ-UHFFFAOYSA-L dichloropalladium;triphenylphosphane Chemical compound Cl[Pd]Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 FXORZKOZOQWVMQ-UHFFFAOYSA-L 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
LPTRPYKRNYNINY-UHFFFAOYSA-N diethyl 2-(2,2-dimethylpropyl)propanedioate Chemical compound CCOC(=O)C(CC(C)(C)C)C(=O)OCC LPTRPYKRNYNINY-UHFFFAOYSA-N 0.000 description 1
RPNFNBGRHCUORR-UHFFFAOYSA-N diethyl 2-butylpropanedioate Chemical compound CCCCC(C(=O)OCC)C(=O)OCC RPNFNBGRHCUORR-UHFFFAOYSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
235000019797 dipotassium phosphate Nutrition 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
244000078703 ectoparasite Species 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
230000008029 eradication Effects 0.000 description 1
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 1
NSNYHHADKMKJJE-UHFFFAOYSA-N ethyl 3-[4-(1-ethyl-3,5,8-trioxabicyclo[2.2.2]octan-4-yl)phenyl]prop-2-ynoate Chemical compound C1=CC(C#CC(=O)OCC)=CC=C1C1(OC2)OCC2(CC)CO1 NSNYHHADKMKJJE-UHFFFAOYSA-N 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000006260 foam Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
239000004519 grease Substances 0.000 description 1
239000010440 gypsum Substances 0.000 description 1
229910052602 gypsum Inorganic materials 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
239000010410 layer Substances 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
231100001225 mammalian toxicity Toxicity 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
201000002266 mite infestation Diseases 0.000 description 1
PHWISQNXPLXQRU-UHFFFAOYSA-N n,n-dimethylcarbamothioyl chloride Chemical compound CN(C)C(Cl)=S PHWISQNXPLXQRU-UHFFFAOYSA-N 0.000 description 1
KKQCXOPSDOZLQK-UHFFFAOYSA-N n-methyl-3-[4-(1-propyl-3,5,8-trioxabicyclo[2.2.2]octan-4-yl)phenyl]prop-2-ynamide Chemical compound O1CC(CCC)(CO2)COC12C1=CC=C(C#CC(=O)NC)C=C1 KKQCXOPSDOZLQK-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
239000012053 oil suspension Substances 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000003883 ointment base Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
125000001979 organolithium group Chemical group 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
239000006072 paste Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
239000003380 propellant Substances 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
230000005180 public health Effects 0.000 description 1
239000002728 pyrethroid Substances 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
125000003003 spiro group Chemical group 0.000 description 1
238000005507 spraying Methods 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
239000000126 substance Substances 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
150000003568 thioethers 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
125000003944 tolyl group Chemical group 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
GQOYBAHZFVZDEM-UHFFFAOYSA-N trimethyl-[2-[4-(1-pentyl-3,5,8-trioxabicyclo[2.2.2]octan-4-yl)phenyl]ethynyl]silane Chemical compound O1CC(CCCCC)(CO2)COC12C1=CC=C(C#C[Si](C)(C)C)C=C1 GQOYBAHZFVZDEM-UHFFFAOYSA-N 0.000 description 1
150000004072 triols Chemical class 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
150000003738 xylenes Chemical class 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
- 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
- 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
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
- C09K2019/3425—Six-membered ring with oxygen(s) in fused, bridged or spiro ring systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
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)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

APAP/P/1986/000045A 1985-09-23 1986-09-22 Pestcidal compounds. AP65A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/779,167 US4772624A (en)	1985-01-23	1985-09-23	1,4-bis-substituted-2,6,7-trioxabicyclo(2.2.2)-octanes having ethynyl substituted phenyl group

Publications (2)

Publication Number	Publication Date
AP8600045A0 AP8600045A0 (en)	1986-08-01
AP65A true AP65A (en)	1989-12-12

Family

ID=25115548

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
APAP/P/1986/000045A AP65A (en)	1985-09-23	1986-09-22	Pestcidal compounds.

Country Status (4)

Country	Link
US (1)	US4772624A (de)
AP (1)	AP65A (de)
DD (2)	DD275604A5 (de)
ZA (1)	ZA867208B (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5098929A (en) *	1985-07-30	1992-03-24	The Wellcome Foundation Limited	Pesticidal compounds
GB8606130D0 (en) *	1986-03-12	1986-04-16	Wellcome Found	Pesticidal compounds
US5116862A (en) *	1985-09-24	1992-05-26	The Wellcome Foundation Limited	Pesticidal compounds
US5466710A (en) *	1988-03-21	1995-11-14	Roussel Uclaf	Heterobicycloalkanes as pesticidal compounds
EP0380312A1 (de) *	1989-01-24	1990-08-01	Roussel-Uclaf	Pestizide Verbindungen
TWI550071B (zh)	2011-03-25	2016-09-21	捷恩智股份有限公司	原酸酯化合物、液晶組成物及液晶顯示元件

Citations (2)

* 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
EP0052229A1 (de) *	1980-11-14	1982-05-26	Societe Des Produits Nestle S.A.	Verfahren und Vorrichtung zum Füllen von Konservendosen

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3113068A (en) *	1960-09-19	1963-12-03	Diamond Alkali Co	Aromatic ethynyl pesticides
JPS59985A (ja) *	1982-06-25	1984-01-06	Nec Corp	半導体レ−ザ駆動回路
IL79532A0 (en) *	1985-07-30	1986-10-31	Wellcome Found	Substituted trioxabicyclooctanes,their preparation and their use as pesticides

1985
- 1985-09-23 US US06/779,167 patent/US4772624A/en not_active Expired - Lifetime
1986
- 1986-09-22 ZA ZA867208A patent/ZA867208B/xx unknown
- 1986-09-22 AP APAP/P/1986/000045A patent/AP65A/en active
- 1986-09-22 DD DD86321060A patent/DD275604A5/de not_active IP Right Cessation
- 1986-09-22 DD DD86294595A patent/DD260497A5/de not_active IP Right Cessation

Patent Citations (2)

* 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
EP0052229A1 (de) *	1980-11-14	1982-05-26	Societe Des Produits Nestle S.A.	Verfahren und Vorrichtung zum Füllen von Konservendosen

Also Published As

Publication number	Publication date
DD275604A5 (de)	1990-01-31
AP8600045A0 (en)	1986-08-01
DD260497A5 (de)	1988-09-28
US4772624A (en)	1988-09-20
ZA867208B (en)	1988-05-25

Publication	Publication Date	Title
AU604212B2 (en)	1990-12-13	Pesticidal compounds
EP0216624B1 (de)	1995-02-22	Pestizidverbindungen
AP65A (en)	1989-12-12	Pestcidal compounds.
EP0216625A2 (de)	1987-04-01	Pestizidverbindungen
US4942173A (en)	1990-07-17	Pesticidal compounds
NZ224894A (en)	1990-12-21	5-tert-butyldithiane derivatives and pesticidal compositions
US5057508A (en)	1991-10-15	Pesticidal compounds
JP2667916B2 (ja)	1997-10-27	有害生物防除剤
AP75A (en)	1990-03-05	Pesticidal compounds.
US4965257A (en)	1990-10-23	Pesticidal compounds
US5371075A (en)	1994-12-06	Trithiabicyclo[2,2,2]octanes
US4985582A (en)	1991-01-15	Pesticidal compounds
AP66A (en)	1989-12-12	Pestcidal compounds.
US5057504A (en)	1991-10-15	1-heterocyclic bicyclo-octanes
EP0279698A2 (de)	1988-08-24	Pestizide Verbindungen
US5098929A (en)	1992-03-24	Pesticidal compounds
US5116862A (en)	1992-05-26	Pesticidal compounds
US5466710A (en)	1995-11-14	Heterobicycloalkanes as pesticidal compounds
AP47A (en)	1989-08-20	Pesticidal compounds
EP0285342A2 (de)	1988-10-05	Peptizide
CA2008348A1 (en)	1990-07-24	Pesticidal compounds
EP0209289B1 (de)	1991-01-16	Ungesättigte Thiocarbonsäureamide als Pestizide
US5091420A (en)	1992-02-25	Method of combatting pests using N-(cyclo)alkyl-5-substituted-2,4-thiopentadienamide compounds
AP59A (en)	1989-10-30	Novel heterocyclic pesticidal compounds.
EP0225011A1 (de)	1987-06-10	Pestizide (1'-Naphthyloxy)-alken(oder -alkadien)-carbonsäureamide