DD247599A5 - Insektizide mittel - Google Patents
Insektizide mittel Download PDFInfo
- Publication number
- DD247599A5 DD247599A5 DD86288541A DD28854186A DD247599A5 DD 247599 A5 DD247599 A5 DD 247599A5 DD 86288541 A DD86288541 A DD 86288541A DD 28854186 A DD28854186 A DD 28854186A DD 247599 A5 DD247599 A5 DD 247599A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- group
- formula
- nitromethylene
- carbon atoms
- halogen
- Prior art date
Links
- 239000002917 insecticide Substances 0.000 title claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 20
- 125000005843 halogen group Chemical group 0.000 claims abstract description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 4
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 3
- 125000003277 amino group Chemical group 0.000 claims abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 68
- -1 methoxy, ethoxy, methylthio, ethylthio, nitro Chemical group 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 241000238631 Hexapoda Species 0.000 claims description 17
- DQHLXESBWCWKIY-UHFFFAOYSA-N 2-(nitromethylidene)-3,4-dihydro-1h-pyrimidine Chemical class [O-][N+](=O)C=C1NCC=CN1 DQHLXESBWCWKIY-UHFFFAOYSA-N 0.000 claims description 8
- 241000607479 Yersinia pestis Species 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 5
- IQXANBUFCHKFAF-UHFFFAOYSA-N 2-(nitromethylidene)-1-[[4-(trifluoromethyl)phenyl]methyl]-1,3-diazinane Chemical compound [O-][N+](=O)C=C1NCCCN1CC1=CC=C(C(F)(F)F)C=C1 IQXANBUFCHKFAF-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- CVPWCXWWPQXQKQ-UHFFFAOYSA-N 2-(nitromethylidene)-1-[(4-nitrophenyl)methyl]-1,3-diazinane Chemical compound [O-][N+](=O)C=C1NCCCN1CC1=CC=C([N+]([O-])=O)C=C1 CVPWCXWWPQXQKQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 230000001473 noxious effect Effects 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 230000000749 insecticidal effect Effects 0.000 abstract description 9
- 239000003795 chemical substances by application Substances 0.000 abstract description 4
- 239000004480 active ingredient Substances 0.000 abstract description 3
- 230000000361 pesticidal effect Effects 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 2
- 125000000547 substituted alkyl group Chemical group 0.000 abstract description 2
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- 238000009472 formulation Methods 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
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- 239000008187 granular material Substances 0.000 description 5
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- 230000000694 effects Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 4
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- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
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- 239000007787 solid Substances 0.000 description 3
- 239000012747 synergistic agent Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- NXGHEDHQXXXTTP-UHFFFAOYSA-N 1,1-bis(methylsulfanyl)-2-nitroethene Chemical group CSC(SC)=C[N+]([O-])=O NXGHEDHQXXXTTP-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
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- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
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- SIERTSRYNYSRSX-UHFFFAOYSA-N n'-[[4-(trifluoromethyl)phenyl]methyl]propane-1,3-diamine Chemical compound NCCCNCC1=CC=C(C(F)(F)F)C=C1 SIERTSRYNYSRSX-UHFFFAOYSA-N 0.000 description 2
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- SYYSBZOSEAUMEY-UHFFFAOYSA-N 1,1,1-trifluoro-2-$l^{1}-sulfanylethane Chemical group FC(F)(F)C[S] SYYSBZOSEAUMEY-UHFFFAOYSA-N 0.000 description 1
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- 241000907661 Pieris rapae Species 0.000 description 1
- 241000500437 Plutella xylostella Species 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 241000596535 Pseudococcus comstocki Species 0.000 description 1
- 241000526145 Psylla Species 0.000 description 1
- 241000722251 Rhodnius Species 0.000 description 1
- 239000004113 Sepiolite Substances 0.000 description 1
- 241000270295 Serpentes Species 0.000 description 1
- 241000254154 Sitophilus zeamais Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 241000985245 Spodoptera litura Species 0.000 description 1
- 241000283614 Stephanitis nashi Species 0.000 description 1
- 241001494139 Stomoxys Species 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 241000018137 Trialeurodes vaporariorum Species 0.000 description 1
- 241000254113 Tribolium castaneum Species 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 241001259047 Trichodectes Species 0.000 description 1
- 241001630065 Unaspis yanonensis Species 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical class ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
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- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
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- 239000000205 acacia gum Substances 0.000 description 1
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- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- DCYOBGZUOMKFPA-UHFFFAOYSA-N iron(2+);iron(3+);octadecacyanide Chemical compound [Fe+2].[Fe+2].[Fe+2].[Fe+3].[Fe+3].[Fe+3].[Fe+3].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] DCYOBGZUOMKFPA-UHFFFAOYSA-N 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- DEDIZNMVLNPCCV-UHFFFAOYSA-N methyl 4-[[2-(nitromethylidene)-1,3-diazinan-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(=C[N+]([O-])=O)NCCC1 DEDIZNMVLNPCCV-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- IRKRYKYYQONACD-UHFFFAOYSA-N n'-[(2-methoxyphenyl)methyl]propane-1,3-diamine Chemical compound COC1=CC=CC=C1CNCCCN IRKRYKYYQONACD-UHFFFAOYSA-N 0.000 description 1
- VZFQZLMHBJTQLK-UHFFFAOYSA-N n'-[(3,4-dichlorophenyl)methyl]propane-1,3-diamine Chemical compound NCCCNCC1=CC=C(Cl)C(Cl)=C1 VZFQZLMHBJTQLK-UHFFFAOYSA-N 0.000 description 1
- NXSZCPBBZUMDNI-UHFFFAOYSA-N n'-[(3-methylphenyl)methyl]propane-1,3-diamine Chemical compound CC1=CC=CC(CNCCCN)=C1 NXSZCPBBZUMDNI-UHFFFAOYSA-N 0.000 description 1
- FQKRJKLKICLAQV-UHFFFAOYSA-N n'-[(3-nitrophenyl)methyl]propane-1,3-diamine Chemical compound NCCCNCC1=CC=CC([N+]([O-])=O)=C1 FQKRJKLKICLAQV-UHFFFAOYSA-N 0.000 description 1
- SLZROWDFJYSNST-UHFFFAOYSA-N n'-[(4-aminophenyl)methyl]propane-1,3-diamine Chemical compound NCCCNCC1=CC=C(N)C=C1 SLZROWDFJYSNST-UHFFFAOYSA-N 0.000 description 1
- TZVSZCNNBFSCKI-UHFFFAOYSA-N n'-[(4-ethylphenyl)methyl]propane-1,3-diamine Chemical compound CCC1=CC=C(CNCCCN)C=C1 TZVSZCNNBFSCKI-UHFFFAOYSA-N 0.000 description 1
- GOPCLQUKFLLWCG-UHFFFAOYSA-N n'-[(4-methoxyphenyl)methyl]propane-1,3-diamine Chemical compound COC1=CC=C(CNCCCN)C=C1 GOPCLQUKFLLWCG-UHFFFAOYSA-N 0.000 description 1
- WUSFNOHQQLRSCV-UHFFFAOYSA-N n'-[(4-methylphenyl)methyl]propane-1,3-diamine Chemical compound CC1=CC=C(CNCCCN)C=C1 WUSFNOHQQLRSCV-UHFFFAOYSA-N 0.000 description 1
- LZZFLYYLSYNYHO-UHFFFAOYSA-N n'-[(4-methylsulfanylphenyl)methyl]propane-1,3-diamine Chemical compound CSC1=CC=C(CNCCCN)C=C1 LZZFLYYLSYNYHO-UHFFFAOYSA-N 0.000 description 1
- DTAYWASIRKMWDV-UHFFFAOYSA-N n'-[(4-nitrophenyl)methyl]propane-1,3-diamine Chemical compound NCCCNCC1=CC=C([N+]([O-])=O)C=C1 DTAYWASIRKMWDV-UHFFFAOYSA-N 0.000 description 1
- YICLHHALWQINHG-UHFFFAOYSA-N n'-[[3-(dimethylamino)phenyl]methyl]propane-1,3-diamine Chemical compound CN(C)C1=CC=CC(CNCCCN)=C1 YICLHHALWQINHG-UHFFFAOYSA-N 0.000 description 1
- UMAFAPIRMTYISO-UHFFFAOYSA-N n'-[[4-(dimethylamino)phenyl]methyl]propane-1,3-diamine Chemical compound CN(C)C1=CC=C(CNCCCN)C=C1 UMAFAPIRMTYISO-UHFFFAOYSA-N 0.000 description 1
- UIGVXDWNDIPEPN-UHFFFAOYSA-N n'-[[4-(fluoromethyl)phenyl]methyl]propane-1,3-diamine Chemical compound NCCCNCC1=CC=C(CF)C=C1 UIGVXDWNDIPEPN-UHFFFAOYSA-N 0.000 description 1
- IIFZFIIEOZDIOV-UHFFFAOYSA-N n-[3-[[2-(nitromethylidene)-1,3-diazinan-1-yl]methyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(CN2C(NCCC2)=C[N+]([O-])=O)=C1 IIFZFIIEOZDIOV-UHFFFAOYSA-N 0.000 description 1
- WDRXOROLIDMWKO-UHFFFAOYSA-N n-[4-[[2-(nitromethylidene)-1,3-diazinan-1-yl]methyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1CN1C(=C[N+]([O-])=O)NCCC1 WDRXOROLIDMWKO-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000725 suspension Substances 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
-
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60068551A JPS61227571A (ja) | 1985-04-02 | 1985-04-02 | ニトロメチレン−テトラヒドロピリミジン誘導体、その製法及び殺虫剤 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD247599A5 true DD247599A5 (de) | 1987-07-15 |
Family
ID=13377008
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD86288541A DD247599A5 (de) | 1985-04-02 | 1986-03-31 | Insektizide mittel |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0199974A3 (da) |
| JP (1) | JPS61227571A (da) |
| KR (1) | KR860008151A (da) |
| BR (1) | BR8601444A (da) |
| DD (1) | DD247599A5 (da) |
| DK (1) | DK146686A (da) |
| HU (1) | HU197495B (da) |
| IL (1) | IL78378A0 (da) |
| PH (1) | PH23304A (da) |
| ZA (1) | ZA862375B (da) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07121909B2 (ja) * | 1986-09-10 | 1995-12-25 | 日本バイエルアグロケム株式会社 | 新規複素環式化合物及び殺虫剤 |
| IL109422A0 (en) * | 1993-04-30 | 1994-07-31 | Shell Int Research | N-benzyl heterocyclic compounds, process for their preparation and pesticidal compositions containing them |
| EP0623601A1 (en) * | 1993-04-30 | 1994-11-09 | Shell Internationale Researchmaatschappij B.V. | N-(3-Fluorobenzyl)heterocyclic derivatives and their use as pesticides |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2514402A1 (de) * | 1975-04-02 | 1976-10-21 | Hoechst Ag | Insektizide mittel |
| JPH0629256B2 (ja) * | 1983-10-06 | 1994-04-20 | 日本バイエルアグロケム株式会社 | ニトロメチレン−テトラヒドロピリミジン誘導体,その製法及び殺虫,殺ダニ,殺センチユウ剤 |
-
1985
- 1985-04-02 JP JP60068551A patent/JPS61227571A/ja active Pending
-
1986
- 1986-03-21 EP EP86103881A patent/EP0199974A3/de not_active Withdrawn
- 1986-03-25 PH PH33584A patent/PH23304A/en unknown
- 1986-03-31 DD DD86288541A patent/DD247599A5/de unknown
- 1986-03-31 IL IL78378A patent/IL78378A0/xx unknown
- 1986-04-01 DK DK146686A patent/DK146686A/da not_active IP Right Cessation
- 1986-04-01 HU HU861336A patent/HU197495B/hu unknown
- 1986-04-01 ZA ZA862375A patent/ZA862375B/xx unknown
- 1986-04-01 BR BR8601444A patent/BR8601444A/pt unknown
- 1986-04-01 KR KR1019860002456A patent/KR860008151A/ko not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| PH23304A (en) | 1989-06-30 |
| IL78378A0 (en) | 1986-07-31 |
| EP0199974A3 (de) | 1987-08-12 |
| DK146686A (da) | 1986-10-03 |
| DK146686D0 (da) | 1986-04-01 |
| JPS61227571A (ja) | 1986-10-09 |
| HUT42273A (en) | 1987-07-28 |
| KR860008151A (ko) | 1986-11-12 |
| BR8601444A (pt) | 1986-12-09 |
| HU197495B (en) | 1989-04-28 |
| ZA862375B (en) | 1986-11-26 |
| EP0199974A2 (de) | 1986-11-05 |
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