DK172805B1 - Anvendelse af heterocycliske forbindelser til bekæmpelse af skadelige insekter, insekticide midler indeholdende de heterocy - Google Patents
Anvendelse af heterocycliske forbindelser til bekæmpelse af skadelige insekter, insekticide midler indeholdende de heterocy Download PDFInfo
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- DK172805B1 DK172805B1 DK198600519A DK51986A DK172805B1 DK 172805 B1 DK172805 B1 DK 172805B1 DK 198600519 A DK198600519 A DK 198600519A DK 51986 A DK51986 A DK 51986A DK 172805 B1 DK172805 B1 DK 172805B1
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- atom
- methyl
- pyridylmethyl
- optionally
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- 239000002917 insecticide Substances 0.000 title claims abstract description 11
- 241000238631 Hexapoda Species 0.000 title claims description 24
- 150000002391 heterocyclic compounds Chemical class 0.000 title claims description 21
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- -1 benzylcarbonyl group Chemical group 0.000 claims description 260
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 187
- 229910052801 chlorine Inorganic materials 0.000 claims description 104
- 239000000203 mixture Substances 0.000 claims description 85
- 229910052731 fluorine Inorganic materials 0.000 claims description 79
- 125000001153 fluoro group Chemical group F* 0.000 claims description 77
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 77
- 238000000034 method Methods 0.000 claims description 75
- 230000008569 process Effects 0.000 claims description 57
- 125000004432 carbon atom Chemical group C* 0.000 claims description 55
- 125000001424 substituent group Chemical group 0.000 claims description 54
- 239000000460 chlorine Chemical group 0.000 claims description 51
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 50
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 30
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
- 125000004434 sulfur atom Chemical group 0.000 claims description 14
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 11
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 9
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 8
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 8
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 8
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 8
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 7
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 7
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 6
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 5
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 4
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical compound [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 claims description 4
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 4
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- XZODFQRTNMIPJZ-UHFFFAOYSA-N n-[1-[(6-chloropyridin-3-yl)methyl]-5,6-dihydro-4h-pyrimidin-2-yl]nitramide Chemical compound [O-][N+](=O)N=C1NCCCN1CC1=CC=C(Cl)N=C1 XZODFQRTNMIPJZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- GROQTGWKUWLQBQ-UHFFFAOYSA-N 2-[[2-(nitromethylidene)imidazolidin-1-yl]methyl]pyrazine Chemical compound [O-][N+](=O)C=C1NCCN1CC1=CN=CC=N1 GROQTGWKUWLQBQ-UHFFFAOYSA-N 0.000 claims description 2
- XKVCBURYVNLQRB-FNORWQNLSA-N 2-chloro-5-[[(2e)-2-(nitromethylidene)imidazolidin-1-yl]methyl]-1,3-thiazole Chemical compound [O-][N+](=O)\C=C1/NCCN1CC1=CN=C(Cl)S1 XKVCBURYVNLQRB-FNORWQNLSA-N 0.000 claims description 2
- CIJFOPHRPXJWDL-UHFFFAOYSA-N 2-chloro-5-[[2-(nitromethylidene)-1,3-diazinan-1-yl]methyl]-1,3-thiazole Chemical compound [O-][N+](=O)C=C1NCCCN1CC1=CN=C(Cl)S1 CIJFOPHRPXJWDL-UHFFFAOYSA-N 0.000 claims description 2
- GUENHXVYSLGOHB-UHFFFAOYSA-N 2-chloro-5-[[2-(nitromethylidene)-1,3-diazinan-1-yl]methyl]pyrimidine Chemical compound [O-][N+](=O)C=C1NCCCN1CC1=CN=C(Cl)N=C1 GUENHXVYSLGOHB-UHFFFAOYSA-N 0.000 claims description 2
- PMJVPSDDURPMHB-UHFFFAOYSA-N 2-methyl-5-[[2-(nitromethylidene)imidazolidin-1-yl]methyl]-1,3-thiazole Chemical compound S1C(C)=NC=C1CN1C(=C[N+]([O-])=O)NCC1 PMJVPSDDURPMHB-UHFFFAOYSA-N 0.000 claims description 2
- PSSQOQHTEFTBCY-UHFFFAOYSA-N 3-[(6-ethylpyridin-3-yl)methyl]-2-(nitromethylidene)-1,3-thiazolidine Chemical compound C1=NC(CC)=CC=C1CN1C(=C[N+]([O-])=O)SCC1 PSSQOQHTEFTBCY-UHFFFAOYSA-N 0.000 claims description 2
- QHAUAXJMSGBAOI-UHFFFAOYSA-N 3-[(6-fluoropyridin-3-yl)methyl]-2-(nitromethylidene)-1,3-thiazinane Chemical compound [O-][N+](=O)C=C1SCCCN1CC1=CC=C(F)N=C1 QHAUAXJMSGBAOI-UHFFFAOYSA-N 0.000 claims description 2
- WWPITHYQYHNEEJ-UHFFFAOYSA-N 3-[[2-(nitromethylidene)-1,3-diazinan-1-yl]methyl]-1,2,5-thiadiazole Chemical compound [O-][N+](=O)C=C1NCCCN1CC1=NSN=C1 WWPITHYQYHNEEJ-UHFFFAOYSA-N 0.000 claims description 2
- FTAMBTJBGQBTOO-UHFFFAOYSA-N 3-methyl-5-[[2-(nitromethylidene)-1,3-diazinan-1-yl]methyl]-1,2-oxazole Chemical compound O1N=C(C)C=C1CN1C(=C[N+]([O-])=O)NCCC1 FTAMBTJBGQBTOO-UHFFFAOYSA-N 0.000 claims description 2
- ORYOBGZJWMHZKR-UHFFFAOYSA-N 5-[[2-(nitromethylidene)imidazolidin-1-yl]methyl]-1,2-oxazole Chemical compound [O-][N+](=O)C=C1NCCN1CC1=CC=NO1 ORYOBGZJWMHZKR-UHFFFAOYSA-N 0.000 claims description 2
- AFCKSKZYJPAKBU-UHFFFAOYSA-N 5-[[2-(nitromethylidene)imidazolidin-1-yl]methyl]-1h-pyrazole Chemical compound [O-][N+](=O)C=C1NCCN1CC1=CC=NN1 AFCKSKZYJPAKBU-UHFFFAOYSA-N 0.000 claims description 2
- ZGAUPFNHLNYGSP-UHFFFAOYSA-N 5-[[2-(nitromethylidene)imidazolidin-1-yl]methyl]-2-(trifluoromethyl)-1,3-thiazole Chemical compound [O-][N+](=O)C=C1NCCN1CC1=CN=C(C(F)(F)F)S1 ZGAUPFNHLNYGSP-UHFFFAOYSA-N 0.000 claims description 2
- YPIYSOFZUVFMSN-UHFFFAOYSA-N 5-[[2-(nitromethylidene)imidazolidin-1-yl]methyl]pyrimidine Chemical compound [O-][N+](=O)C=C1NCCN1CC1=CN=CN=C1 YPIYSOFZUVFMSN-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 2
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 claims description 2
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 2
- LHAUOPZSWKIXSW-UHFFFAOYSA-N 1-methyl-4-[[2-(nitromethylidene)imidazolidin-1-yl]methyl]pyrazole Chemical compound C1=NN(C)C=C1CN1C(=C[N+]([O-])=O)NCC1 LHAUOPZSWKIXSW-UHFFFAOYSA-N 0.000 claims 1
- ULPODHWNXKGNNU-UHFFFAOYSA-N 2-chloro-5-[[2-(nitromethylidene)pyrrolidin-1-yl]methyl]pyridine Chemical compound [O-][N+](=O)C=C1CCCN1CC1=CC=C(Cl)N=C1 ULPODHWNXKGNNU-UHFFFAOYSA-N 0.000 claims 1
- SNAYJEGWUMEKAV-UHFFFAOYSA-N 3-[(6-bromopyridin-3-yl)methyl]-2-(nitromethylidene)-1,3-thiazinane Chemical compound [O-][N+](=O)C=C1SCCCN1CC1=CC=C(Br)N=C1 SNAYJEGWUMEKAV-UHFFFAOYSA-N 0.000 claims 1
- ZTLMFNYACJYRIS-UHFFFAOYSA-N 3-[(6-chloropyridin-3-yl)methyl]-2-(nitromethylidene)-1,3-thiazolidine Chemical compound [O-][N+](=O)C=C1SCCN1CC1=CC=C(Cl)N=C1 ZTLMFNYACJYRIS-UHFFFAOYSA-N 0.000 claims 1
- FVFSTVFUGPUFSR-UHFFFAOYSA-N 3-[(6-fluoropyridin-3-yl)methyl]-2-(nitromethylidene)-1,3-thiazolidine Chemical compound [O-][N+](=O)C=C1SCCN1CC1=CC=C(F)N=C1 FVFSTVFUGPUFSR-UHFFFAOYSA-N 0.000 claims 1
- OOHLVHUZMFQDQQ-UHFFFAOYSA-N 3-[(6-methylpyridin-3-yl)methyl]-2-(nitromethylidene)-1,3-thiazolidine Chemical compound C1=NC(C)=CC=C1CN1C(=C[N+]([O-])=O)SCC1 OOHLVHUZMFQDQQ-UHFFFAOYSA-N 0.000 claims 1
- VIHOWHRUDVRVPR-UHFFFAOYSA-N 3-[1-(6-chloropyridin-3-yl)ethyl]-2-(nitromethylidene)-1,3-thiazolidine Chemical compound C=1C=C(Cl)N=CC=1C(C)N1CCSC1=C[N+]([O-])=O VIHOWHRUDVRVPR-UHFFFAOYSA-N 0.000 claims 1
- IUAHUQGKIBEWCQ-UHFFFAOYSA-N 5-chloro-1-methyl-3-[[2-(nitromethylidene)imidazolidin-1-yl]methyl]pyrazole Chemical compound C1=C(Cl)N(C)N=C1CN1C(=C[N+]([O-])=O)NCC1 IUAHUQGKIBEWCQ-UHFFFAOYSA-N 0.000 claims 1
- QUTWBCIHMIKAJY-UHFFFAOYSA-N C1CN(C(N1CC2=CN=CC=C2)C[N+](=O)[O-])CC3=CN=C(C=C3)Cl Chemical compound C1CN(C(N1CC2=CN=CC=C2)C[N+](=O)[O-])CC3=CN=C(C=C3)Cl QUTWBCIHMIKAJY-UHFFFAOYSA-N 0.000 claims 1
- 125000005108 alkenylthio group Chemical group 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- ZMVSOXBOHGLVSJ-UHFFFAOYSA-N n-[1-[(2-chloro-1,3-thiazol-5-yl)methyl]-5,6-dihydro-4h-pyrimidin-2-yl]nitramide Chemical compound [O-][N+](=O)N=C1NCCCN1CC1=CN=C(Cl)S1 ZMVSOXBOHGLVSJ-UHFFFAOYSA-N 0.000 claims 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 1
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 9
- 239000001257 hydrogen Substances 0.000 abstract description 7
- 229910052727 yttrium Inorganic materials 0.000 abstract description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 150000004985 diamines Chemical class 0.000 description 316
- 150000001875 compounds Chemical class 0.000 description 219
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 165
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- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 119
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
- 239000000047 product Substances 0.000 description 31
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- 150000003462 sulfoxides Chemical class 0.000 description 1
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 1
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical class O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical class N1(CCCC=C1)* 0.000 description 1
- JJIHENIPUIXQDM-UHFFFAOYSA-N thiadiazole-5-carbaldehyde Chemical compound O=CC1=CN=NS1 JJIHENIPUIXQDM-UHFFFAOYSA-N 0.000 description 1
- AJZGFFKDLABHDD-UHFFFAOYSA-N thiazinane Chemical class C1CCSNC1 AJZGFFKDLABHDD-UHFFFAOYSA-N 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229940029273 trichloroacetaldehyde Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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- C—CHEMISTRY; METALLURGY
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- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/10—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyridine Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Ultra Sonic Daignosis Equipment (AREA)
- Slide Fasteners, Snap Fasteners, And Hook Fasteners (AREA)
- Valve Device For Special Equipments (AREA)
- Control Of Throttle Valves Provided In The Intake System Or In The Exhaust System (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1862885 | 1985-02-04 | ||
JP60018628A JPH0649699B2 (ja) | 1985-02-04 | 1985-02-04 | ニトロメチレン誘導体、その製法及び殺虫剤 |
JP60018627A JPH066585B2 (ja) | 1985-02-04 | 1985-02-04 | ニトロメチレン誘導体、その製法及び殺虫剤 |
JP1862785 | 1985-02-04 | ||
JP60023683A JPH07613B2 (ja) | 1985-02-12 | 1985-02-12 | ニトロメチレン誘導体、その製法及び殺虫剤 |
JP2368385 | 1985-02-12 | ||
JP10685385 | 1985-05-21 | ||
JP10685485 | 1985-05-21 | ||
JP10685385A JPH0629258B2 (ja) | 1985-05-21 | 1985-05-21 | 殺虫性ニトロメチレン誘導体 |
JP60106854A JPS61267575A (ja) | 1985-05-21 | 1985-05-21 | ニトロイミノ誘導体、その製法及び殺虫剤 |
JP60219082A JPH0730070B2 (ja) | 1985-10-03 | 1985-10-03 | 新規複素環式化合物 |
JP21908285 | 1985-10-03 |
Publications (3)
Publication Number | Publication Date |
---|---|
DK51986D0 DK51986D0 (da) | 1986-02-03 |
DK51986A DK51986A (da) | 1986-08-05 |
DK172805B1 true DK172805B1 (da) | 1999-08-02 |
Family
ID=27548804
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DK198600519A DK172805B1 (da) | 1985-02-04 | 1986-02-03 | Anvendelse af heterocycliske forbindelser til bekæmpelse af skadelige insekter, insekticide midler indeholdende de heterocy |
DK199201042A DK172809B1 (da) | 1985-02-04 | 1992-08-21 | Heterocycliske forbindelser og fremgangsmåde til deres fremstilling |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DK199201042A DK172809B1 (da) | 1985-02-04 | 1992-08-21 | Heterocycliske forbindelser og fremgangsmåde til deres fremstilling |
Country Status (19)
Country | Link |
---|---|
US (9) | US4742060A (uk) |
EP (1) | EP0192060B1 (uk) |
KR (1) | KR930006348B1 (uk) |
AT (1) | ATE67493T1 (uk) |
AU (1) | AU584388B2 (uk) |
BR (1) | BR8600428A (uk) |
CA (1) | CA1276018C (uk) |
CS (1) | CS255867B2 (uk) |
DE (1) | DE3681465D1 (uk) |
DK (2) | DK172805B1 (uk) |
GR (1) | GR860308B (uk) |
HK (1) | HK34294A (uk) |
HU (2) | HU202365B (uk) |
IL (1) | IL77750A (uk) |
NL (1) | NL971014I2 (uk) |
NZ (1) | NZ215008A (uk) |
PH (1) | PH30435A (uk) |
PL (1) | PL149199B1 (uk) |
SG (1) | SG138493G (uk) |
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DE3818163A1 (de) * | 1988-05-28 | 1989-12-07 | Bayer Ag | 3-heterocyclylalkyl-1-nitro-2-imino-1,3-diazacycloalkane, verfahren zu ihrer herstellung und ihre verwendung in schaedlingsbekaempfungsmitteln |
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1986
- 1986-01-17 EP EP86100708A patent/EP0192060B1/de not_active Expired - Lifetime
- 1986-01-17 DE DE86100708T patent/DE3681465D1/de not_active Expired - Lifetime
- 1986-01-17 AT AT86100708T patent/ATE67493T1/de active
- 1986-01-21 US US06/821,621 patent/US4742060A/en not_active Expired - Lifetime
- 1986-01-30 AU AU52866/86A patent/AU584388B2/en not_active Expired
- 1986-01-31 IL IL77750A patent/IL77750A/xx not_active IP Right Cessation
- 1986-01-31 PH PH33363A patent/PH30435A/en unknown
- 1986-01-31 CA CA000500793A patent/CA1276018C/en not_active Expired - Lifetime
- 1986-02-03 CS CS86754A patent/CS255867B2/cs not_active IP Right Cessation
- 1986-02-03 BR BR8600428A patent/BR8600428A/pt not_active IP Right Cessation
- 1986-02-03 NZ NZ215008A patent/NZ215008A/xx unknown
- 1986-02-03 PL PL1986257774A patent/PL149199B1/pl unknown
- 1986-02-03 HU HU895815A patent/HU202365B/hu unknown
- 1986-02-03 GR GR860308A patent/GR860308B/el unknown
- 1986-02-03 HU HU86466A patent/HU200651B/hu unknown
- 1986-02-03 DK DK198600519A patent/DK172805B1/da not_active IP Right Cessation
- 1986-02-04 KR KR1019860000740A patent/KR930006348B1/ko not_active IP Right Cessation
-
1987
- 1987-07-01 US US07/068,991 patent/US4845106A/en not_active Expired - Lifetime
-
1992
- 1992-02-06 US US07/832,174 patent/US5298507A/en not_active Expired - Lifetime
- 1992-08-21 DK DK199201042A patent/DK172809B1/da not_active IP Right Cessation
-
1993
- 1993-05-25 US US08/067,642 patent/US5461167A/en not_active Expired - Lifetime
- 1993-12-20 US US08/169,902 patent/US5428032A/en not_active Expired - Lifetime
- 1993-12-22 SG SG138493A patent/SG138493G/en unknown
-
1994
- 1994-04-14 HK HK34294A patent/HK34294A/xx not_active IP Right Cessation
-
1995
- 1995-03-15 US US08/404,849 patent/US5580889A/en not_active Expired - Lifetime
-
1996
- 1996-06-12 US US08/662,096 patent/US5750704A/en not_active Expired - Fee Related
-
1997
- 1997-07-17 NL NL971014C patent/NL971014I2/nl unknown
-
1998
- 1998-01-23 US US09/012,620 patent/US6022967A/en not_active Expired - Fee Related
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1999
- 1999-05-11 US US09/309,988 patent/US6297374B1/en not_active Expired - Fee Related
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B1 | Patent granted (law 1993) | ||
PUP | Patent expired |