JPS61267575A - ニトロイミノ誘導体、その製法及び殺虫剤 - Google Patents
ニトロイミノ誘導体、その製法及び殺虫剤Info
- Publication number
- JPS61267575A JPS61267575A JP60106854A JP10685485A JPS61267575A JP S61267575 A JPS61267575 A JP S61267575A JP 60106854 A JP60106854 A JP 60106854A JP 10685485 A JP10685485 A JP 10685485A JP S61267575 A JPS61267575 A JP S61267575A
- Authority
- JP
- Japan
- Prior art keywords
- group
- pyridylmethyl
- formula
- carbon atoms
- general formula
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- -1 Nitroimino Chemical class 0.000 title claims abstract description 52
- 239000002917 insecticide Substances 0.000 title claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 39
- 150000001875 compounds Chemical class 0.000 claims abstract description 95
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 16
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 10
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 9
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 9
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 9
- 125000004995 haloalkylthio group Chemical group 0.000 claims abstract description 9
- 125000005843 halogen group Chemical group 0.000 claims abstract description 9
- 125000002252 acyl group Chemical group 0.000 claims abstract description 7
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 7
- 125000000262 haloalkenyl group Chemical group 0.000 claims abstract description 7
- DJZWNSRUEJSEEB-UHFFFAOYSA-N n-(4,5-dihydro-1h-imidazol-2-yl)nitramide Chemical compound [O-][N+](=O)NC1=NCCN1 DJZWNSRUEJSEEB-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 239000000126 substance Substances 0.000 claims description 17
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Chemical group 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 239000000460 chlorine Chemical group 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 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
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 230000001276 controlling effect Effects 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 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 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 19
- 238000000034 method Methods 0.000 description 17
- 239000003795 chemical substances by application Substances 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 241000238631 Hexapoda Species 0.000 description 12
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 12
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical class NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 241000607479 Yersinia pestis Species 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 230000000749 insecticidal effect Effects 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 239000003085 diluting agent Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- 238000009472 formulation Methods 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 5
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
- 241001556089 Nilaparvata lugens Species 0.000 description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- CNQCWYFDIQSALX-UHFFFAOYSA-N 3-(chloromethyl)pyridine Chemical compound ClCC1=CC=CN=C1 CNQCWYFDIQSALX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- 150000001204 N-oxides Chemical class 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QHMQWEPBXSHHLH-UHFFFAOYSA-N sulfur tetrafluoride Chemical compound FS(F)(F)F QHMQWEPBXSHHLH-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical compound C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- UEQZFAGVRGWPDK-UHFFFAOYSA-N 1-[(6-chloropyridin-3-yl)methyl]-4,5-dihydroimidazol-2-amine Chemical compound C1=NC(Cl)=CC=C1CN1C(=N)NCC1 UEQZFAGVRGWPDK-UHFFFAOYSA-N 0.000 description 2
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 2
- IDCPFAYURAQKDZ-UHFFFAOYSA-N 1-nitroguanidine Chemical compound NC(=N)N[N+]([O-])=O IDCPFAYURAQKDZ-UHFFFAOYSA-N 0.000 description 2
- SKCNYHLTRZIINA-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)pyridine Chemical compound ClCC1=CC=C(Cl)N=C1 SKCNYHLTRZIINA-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- FHMVOYGAZCZVOX-UHFFFAOYSA-N 5-(chloromethyl)pyridine-2-carbonitrile Chemical compound ClCC1=CC=C(C#N)N=C1 FHMVOYGAZCZVOX-UHFFFAOYSA-N 0.000 description 2
- HALCBPJUGWBVBU-UHFFFAOYSA-N 5-methyl-2-(trifluoromethyl)pyridine Chemical compound CC1=CC=C(C(F)(F)F)N=C1 HALCBPJUGWBVBU-UHFFFAOYSA-N 0.000 description 2
- 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
- 241000254173 Coleoptera Species 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 241000256602 Isoptera Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 244000061458 Solanum melongena Species 0.000 description 2
- 235000002597 Solanum melongena Nutrition 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 244000000054 animal parasite Species 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000003595 mist Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- DEUJSGDXBNTQMY-UHFFFAOYSA-N 1,2,2-trifluoroethanol Chemical compound OC(F)C(F)F DEUJSGDXBNTQMY-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZCDGHEWSWOTSGZ-UHFFFAOYSA-N 1-(pyridin-3-ylmethyl)-4,5-dihydroimidazol-2-amine Chemical compound N=C1NCCN1CC1=CC=CN=C1 ZCDGHEWSWOTSGZ-UHFFFAOYSA-N 0.000 description 1
- WBRCNPDMGLACAV-UHFFFAOYSA-N 1-[(6-bromopyridin-3-yl)methyl]-4,5-dihydroimidazol-2-amine Chemical compound C1=NC(Br)=CC=C1CN1C(=N)NCC1 WBRCNPDMGLACAV-UHFFFAOYSA-N 0.000 description 1
- DBYCTPQLPKSOCZ-UHFFFAOYSA-N 1-[(6-chloropyridin-3-yl)methyl]-5,6-dihydro-4h-pyrimidin-2-amine Chemical compound C1=NC(Cl)=CC=C1CN1C(=N)NCCC1 DBYCTPQLPKSOCZ-UHFFFAOYSA-N 0.000 description 1
- UZPXOJCKCHEASG-UHFFFAOYSA-N 1-[(6-fluoropyridin-3-yl)methyl]-4,5-dihydroimidazol-2-amine Chemical compound C1=NC(F)=CC=C1CN1C(=N)NCC1 UZPXOJCKCHEASG-UHFFFAOYSA-N 0.000 description 1
- FCDOKMMAGJZWBL-UHFFFAOYSA-N 1-[(6-methylpyridin-3-yl)methyl]-4,5-dihydroimidazol-2-amine Chemical compound C1=NC(C)=CC=C1CN1C(=N)NCC1 FCDOKMMAGJZWBL-UHFFFAOYSA-N 0.000 description 1
- UFWFXHURCRRZPQ-UHFFFAOYSA-N 1-[[6-(trifluoromethyl)pyridin-3-yl]methyl]-4,5-dihydroimidazol-2-amine Chemical compound C1=NC(C(F)(F)F)=CC=C1CN1C(=N)NCC1 UFWFXHURCRRZPQ-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- URNADWHGTCBJFK-UHFFFAOYSA-N 2-(2-chloroethyl)-5-(chloromethyl)pyridine Chemical compound ClCCC1=CC=C(CCl)C=N1 URNADWHGTCBJFK-UHFFFAOYSA-N 0.000 description 1
- VYEFLSRYAXMVDI-UHFFFAOYSA-N 2-(chloromethyl)-4,6-dimethylpyridine Chemical compound CC1=CC(C)=NC(CCl)=C1 VYEFLSRYAXMVDI-UHFFFAOYSA-N 0.000 description 1
- MHMJNRKGRRCAFE-UHFFFAOYSA-N 2-(chloromethyl)-4-methylpyridine Chemical compound CC1=CC=NC(CCl)=C1 MHMJNRKGRRCAFE-UHFFFAOYSA-N 0.000 description 1
- XOVKMILMYFEUMK-UHFFFAOYSA-N 2-(chloromethyl)-5-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=C(CCl)N=C1 XOVKMILMYFEUMK-UHFFFAOYSA-N 0.000 description 1
- RFQANNQGIYHMHO-UHFFFAOYSA-N 2-(chloromethyl)-5-ethylpyridine Chemical compound CCC1=CC=C(CCl)N=C1 RFQANNQGIYHMHO-UHFFFAOYSA-N 0.000 description 1
- YHIOCGXGAXHMDQ-UHFFFAOYSA-N 2-(chloromethyl)-5-fluoropyridine Chemical compound FC1=CC=C(CCl)N=C1 YHIOCGXGAXHMDQ-UHFFFAOYSA-N 0.000 description 1
- MXOPKPMEGUYUCV-UHFFFAOYSA-N 2-(chloromethyl)-5-methylpyridine Chemical compound CC1=CC=C(CCl)N=C1 MXOPKPMEGUYUCV-UHFFFAOYSA-N 0.000 description 1
- PFQYGHGKTNHYRQ-UHFFFAOYSA-N 2-(chloromethyl)-6-methylpyridine Chemical compound CC1=CC=CC(CCl)=N1 PFQYGHGKTNHYRQ-UHFFFAOYSA-N 0.000 description 1
- WRCMVKYFKWKRIG-UHFFFAOYSA-N 2-bromo-4-(chloromethyl)pyridine Chemical compound ClCC1=CC=NC(Br)=C1 WRCMVKYFKWKRIG-UHFFFAOYSA-N 0.000 description 1
- BFJMOUIKUSEUQF-UHFFFAOYSA-N 2-bromo-5-(1-chloro-2,2-difluoroethyl)pyridine Chemical compound FC(F)C(Cl)C1=CC=C(Br)N=C1 BFJMOUIKUSEUQF-UHFFFAOYSA-N 0.000 description 1
- RAUCGVCCODJPPW-UHFFFAOYSA-N 2-chloro-3-(chloromethyl)-6-methylpyridine Chemical compound CC1=CC=C(CCl)C(Cl)=N1 RAUCGVCCODJPPW-UHFFFAOYSA-N 0.000 description 1
- QWIIJVGEBIQHSW-UHFFFAOYSA-N 2-chloro-3-(chloromethyl)pyridine Chemical compound ClCC1=CC=CN=C1Cl QWIIJVGEBIQHSW-UHFFFAOYSA-N 0.000 description 1
- VDOWAYUAAQUDNR-UHFFFAOYSA-N 2-chloro-4-(1-chloroethyl)pyridine Chemical compound CC(Cl)C1=CC=NC(Cl)=C1 VDOWAYUAAQUDNR-UHFFFAOYSA-N 0.000 description 1
- QELZCGMVHLQNSO-UHFFFAOYSA-N 2-chloro-4-(chloromethyl)pyridine Chemical compound ClCC1=CC=NC(Cl)=C1 QELZCGMVHLQNSO-UHFFFAOYSA-N 0.000 description 1
- UEOCLBUKKVLGJR-UHFFFAOYSA-N 2-chloro-5-(1-chloroethyl)pyridine Chemical compound CC(Cl)C1=CC=C(Cl)N=C1 UEOCLBUKKVLGJR-UHFFFAOYSA-N 0.000 description 1
- DGKPTNFDTFHUFN-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)-3-fluoropyridine Chemical compound FC1=CC(CCl)=CN=C1Cl DGKPTNFDTFHUFN-UHFFFAOYSA-N 0.000 description 1
- VUOXMMUURWOTAY-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)-3-methylpyridine Chemical compound CC1=CC(CCl)=CN=C1Cl VUOXMMUURWOTAY-UHFFFAOYSA-N 0.000 description 1
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- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N hydrofluoric acid Substances F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
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- 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
- 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
- 210000003127 knee Anatomy 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [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
- 239000004579 marble Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- PXWBWOCRWUOMGY-UHFFFAOYSA-N n'-[(2-chloropyrimidin-5-yl)methyl]ethane-1,2-diamine Chemical compound NCCNCC1=CN=C(Cl)N=C1 PXWBWOCRWUOMGY-UHFFFAOYSA-N 0.000 description 1
- HTFHALGFLUWNGS-UHFFFAOYSA-N n'-[(6-chloropyridin-3-yl)methyl]propane-1,3-diamine Chemical compound NCCCNCC1=CC=C(Cl)N=C1 HTFHALGFLUWNGS-UHFFFAOYSA-N 0.000 description 1
- MLUIYAYLWDNVSO-UHFFFAOYSA-N n-(1-benzyl-4,5-dihydroimidazol-2-yl)nitramide Chemical compound [O-][N+](=O)N=C1NCCN1CC1=CC=CC=C1 MLUIYAYLWDNVSO-UHFFFAOYSA-N 0.000 description 1
- CKUGESARMUZQGU-UHFFFAOYSA-N n-[5-(chloromethyl)pyridin-2-yl]acetamide Chemical compound CC(=O)NC1=CC=C(CCl)C=N1 CKUGESARMUZQGU-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
- 229920005615 natural polymer Polymers 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol 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
- 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
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 239000012488 sample solution Substances 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
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000012257 stirred material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000008054 sulfonate salts Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 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
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000003039 volatile agent Substances 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
Landscapes
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (32)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
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 |
AT86100708T ATE67493T1 (de) | 1985-02-04 | 1986-01-17 | Heterocyclische verbindungen. |
DE86100708T DE3681465D1 (enrdf_load_stackoverflow) | 1985-02-04 | 1986-01-17 | |
EP86100708A EP0192060B1 (de) | 1985-02-04 | 1986-01-17 | Heterocyclische Verbindungen |
US06/821,621 US4742060A (en) | 1985-02-04 | 1986-01-21 | Heterocyclic compounds |
AU52866/86A AU584388B2 (en) | 1985-02-04 | 1986-01-30 | Novel heterocyclic compounds |
CA000500793A CA1276018C (en) | 1985-02-04 | 1986-01-31 | 2-nitromethylene and 2-nitroimine derivatives of triazolidine, thiazine, oxazolidine, oxazine, imidazolidine, tetrahydropyrimidine, pyrrolidine and piperidine as insecticides |
IL77750A IL77750A (en) | 1985-02-04 | 1986-01-31 | Insecticidal compositions containing oxazines and/or thiazines,some such novel compounds and process for their preparation |
PH33363A PH30435A (en) | 1985-02-04 | 1986-01-31 | Heterocyclic compounds |
HU895815A HU202365B (en) | 1985-02-04 | 1986-02-03 | Insecticide compositions containing nitro-methylene derivative and process for producing the active component |
BR8600428A BR8600428A (pt) | 1985-02-04 | 1986-02-03 | Compostos heterociclicos,processo para sua preparacao,composicoes inseticidas,processo para combate a insetos daninhos,utilizacao e processo para a preparacao de composicoes |
NZ215008A NZ215008A (en) | 1985-02-04 | 1986-02-03 | Heterocyclic compounds and herbicidal compositions |
CS86754A CS255867B2 (en) | 1985-02-04 | 1986-02-03 | Insecticide and process for preparing active component |
GR860308A GR860308B (en) | 1985-02-04 | 1986-02-03 | Novel heterocyclic compounds |
DK198600519A DK172805B1 (da) | 1985-02-04 | 1986-02-03 | Anvendelse af heterocycliske forbindelser til bekæmpelse af skadelige insekter, insekticide midler indeholdende de heterocy |
PL1986257774A PL149199B1 (en) | 1985-02-04 | 1986-02-03 | Insecticide |
HU86466A HU200651B (en) | 1985-02-04 | 1986-02-03 | Insecticide comprising nitromethylene or nitroimino derivative and process for producing such compounds |
KR1019860000740A KR930006348B1 (ko) | 1985-02-04 | 1986-02-04 | 헤테로사이클릭 화합물의 제조방법 |
US07/068,991 US4845106A (en) | 1985-02-04 | 1987-07-01 | Heterocyclic thiazole compounds |
US07347836 US5001138B1 (en) | 1985-02-04 | 1989-05-04 | Heterocyclic compounds |
US07/557,292 US5204360A (en) | 1985-02-04 | 1990-07-24 | Heterocyclic compounds |
US07/832,174 US5298507A (en) | 1985-02-04 | 1992-02-06 | Heterocyclic compounds |
DK199201042A DK172809B1 (da) | 1985-02-04 | 1992-08-21 | Heterocycliske forbindelser og fremgangsmåde til deres fremstilling |
US08/067,642 US5461167A (en) | 1985-02-04 | 1993-05-25 | Heterocyclic compounds |
US08/169,902 US5428032A (en) | 1985-02-04 | 1993-12-20 | Heterocyclic compounds |
SG138493A SG138493G (en) | 1985-02-04 | 1993-12-22 | Heterocyclic compounds. |
HK34294A HK34294A (en) | 1985-02-04 | 1994-04-14 | Heterocyclic compounds |
US08/404,849 US5580889A (en) | 1985-02-04 | 1995-03-15 | Insecticidal nitromethyl or niteoimino-heteromethyl-heterocyclics |
US08/662,096 US5750704A (en) | 1985-02-04 | 1996-06-12 | 1-heterocyclylmethyl-2-halonitromethyl-imidazolines and-tetrahydropyrimidines |
NL971014C NL971014I2 (nl) | 1985-02-04 | 1997-07-17 | Heterocyclische verbindingen. |
US09/012,620 US6022967A (en) | 1985-02-04 | 1998-01-23 | Heterocyclic compounds |
US09/309,988 US6297374B1 (en) | 1985-02-04 | 1999-05-11 | Nitroimino-nitromethylene—azole or-azine heterocyclic compounds, insecticidal compositions containing them, and insecticidal methods of using them |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
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 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP23515292A Division JPH0720953B2 (ja) | 1992-08-12 | 1992-08-12 | 殺虫性ニトロイミノ誘導体 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS61267575A true JPS61267575A (ja) | 1986-11-27 |
JPH0514716B2 JPH0514716B2 (enrdf_load_stackoverflow) | 1993-02-25 |
Family
ID=14444185
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP60106854A Granted JPS61267575A (ja) | 1985-02-04 | 1985-05-21 | ニトロイミノ誘導体、その製法及び殺虫剤 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS61267575A (enrdf_load_stackoverflow) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63150204A (ja) * | 1986-12-16 | 1988-06-22 | Nippon Tokushu Noyaku Seizo Kk | 農業用の殺虫殺菌組成物 |
JPS63154602A (ja) * | 1986-12-18 | 1988-06-27 | Nippon Tokushu Noyaku Seizo Kk | 農園芸用の殺虫殺菌組成物 |
JPS63156705A (ja) * | 1986-12-19 | 1988-06-29 | Nippon Tokushu Noyaku Seizo Kk | 農業用殺虫殺菌剤組成物 |
JPS646203A (en) * | 1986-12-17 | 1989-01-10 | Nihon Tokushu Noyaku Seizo Kk | Agricultural and horticultural insecticidal and germicidal composition |
JPH05345760A (ja) * | 1987-08-01 | 1993-12-27 | Takeda Chem Ind Ltd | ピリジルメチルアミン類 |
EP0685477A1 (en) | 1994-06-03 | 1995-12-06 | MITSUI TOATSU CHEMICALS, Inc. | Insecticidal tetrahydrofuran-compound |
JP2011153145A (ja) * | 2003-10-13 | 2011-08-11 | Bayer Cropscience Ag | 相乗作用性殺虫剤混合物 |
-
1985
- 1985-05-21 JP JP60106854A patent/JPS61267575A/ja active Granted
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63150204A (ja) * | 1986-12-16 | 1988-06-22 | Nippon Tokushu Noyaku Seizo Kk | 農業用の殺虫殺菌組成物 |
JPS646203A (en) * | 1986-12-17 | 1989-01-10 | Nihon Tokushu Noyaku Seizo Kk | Agricultural and horticultural insecticidal and germicidal composition |
JPS63154602A (ja) * | 1986-12-18 | 1988-06-27 | Nippon Tokushu Noyaku Seizo Kk | 農園芸用の殺虫殺菌組成物 |
JPS63156705A (ja) * | 1986-12-19 | 1988-06-29 | Nippon Tokushu Noyaku Seizo Kk | 農業用殺虫殺菌剤組成物 |
JPH05345760A (ja) * | 1987-08-01 | 1993-12-27 | Takeda Chem Ind Ltd | ピリジルメチルアミン類 |
EP0685477A1 (en) | 1994-06-03 | 1995-12-06 | MITSUI TOATSU CHEMICALS, Inc. | Insecticidal tetrahydrofuran-compound |
US5614527A (en) * | 1994-06-03 | 1997-03-25 | Mitsui Toatsu Chemicals, Inc. | Insecticidal tetrahydrofuran-compound |
JP2011153145A (ja) * | 2003-10-13 | 2011-08-11 | Bayer Cropscience Ag | 相乗作用性殺虫剤混合物 |
Also Published As
Publication number | Publication date |
---|---|
JPH0514716B2 (enrdf_load_stackoverflow) | 1993-02-25 |
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