DD236445A5

DD236445A5 - Insektizide mittel

Insektizide mittel Download PDF

Info

Publication number: DD236445A5
Authority: DD; German Democratic Republic
Prior art keywords: pyridylmethyl; ethylenediamine; group; chloro; trimethylenediamine
Prior art date: 1984-04-13

Application number

DD85275098A

Other languages

German (de)

English (en)

Inventor

Kozo Shiokawa

Shinichi Tsuboi

Shinzo Kagabu

Koichi Moriya

Original Assignee

Nihon Tokushu Noyaku Seizo K. K.,Jp

Priority date

1984-04-13

Filing date

1985-04-11

Publication date

1986-06-11

1985-04-11 Application filed by Nihon Tokushu Noyaku Seizo K. K.,Jp filed Critical Nihon Tokushu Noyaku Seizo K. K.,Jp

1986-06-11 Publication of DD236445A5 publication Critical patent/DD236445A5/de

Links

239000002917 insecticide Substances 0.000 title claims description 12
-1 nitromethylene Chemical class 0.000 claims abstract description 133
125000005843 halogen group Chemical group 0.000 claims abstract description 18
125000000217 alkyl group Chemical group 0.000 claims abstract description 16
125000003118 aryl group Chemical group 0.000 claims abstract description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 6
125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 5
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 5
125000000304 alkynyl group Chemical group 0.000 claims abstract description 5
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 5
125000005110 aryl thio group Chemical group 0.000 claims abstract description 5
125000004104 aryloxy group Chemical group 0.000 claims abstract description 5
238000000034 method Methods 0.000 claims description 49
241000238631 Hexapoda Species 0.000 claims description 29
238000002360 preparation method Methods 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 11
239000004094 surface-active agent Substances 0.000 claims description 6
239000004606 Fillers/Extenders Substances 0.000 claims description 5
238000002156 mixing Methods 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 95
230000000749 insecticidal effect Effects 0.000 abstract description 5
125000001309 chloro group Chemical group Cl* 0.000 description 36
SCZVXVGZMZRGRU-UHFFFAOYSA-N n'-ethylethane-1,2-diamine Chemical compound CCNCCN SCZVXVGZMZRGRU-UHFFFAOYSA-N 0.000 description 31
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 25
239000000203 mixture Substances 0.000 description 23
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 15
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 14
125000004432 carbon atom Chemical group C* 0.000 description 12
239000000126 substance Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000000460 chlorine Substances 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
239000000843 powder Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
239000008187 granular material Substances 0.000 description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
238000003756 stirring Methods 0.000 description 9
239000004480 active ingredient Substances 0.000 description 8
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
239000003085 diluting agent Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
239000000243 solution Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000000853 adhesive Substances 0.000 description 6
230000001070 adhesive effect Effects 0.000 description 6
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MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
241000196324 Embryophyta Species 0.000 description 5
KIDHWZJUCRJVML-UHFFFAOYSA-N Putrescine Natural products NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 5
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241000607479 Yersinia pestis Species 0.000 description 5
239000002253 acid Substances 0.000 description 5
239000000463 material Substances 0.000 description 5
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
239000003921 oil Substances 0.000 description 5
238000005507 spraying Methods 0.000 description 5
239000003381 stabilizer Substances 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
241000721621 Myzus persicae Species 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
240000007594 Oryza sativa Species 0.000 description 4
239000003905 agrochemical Substances 0.000 description 4
125000002947 alkylene group Chemical group 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000010790 dilution Methods 0.000 description 4
239000012895 dilution Substances 0.000 description 4
239000004495 emulsifiable concentrate Substances 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
238000001914 filtration Methods 0.000 description 4
238000009472 formulation Methods 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
239000002245 particle Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
239000012747 synergistic agent Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
239000008096 xylene Substances 0.000 description 4
NXGHEDHQXXXTTP-UHFFFAOYSA-N 1,1-bis(methylsulfanyl)-2-nitroethene Chemical group CSC(SC)=C[N+]([O-])=O NXGHEDHQXXXTTP-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
241000358422 Nephotettix cincticeps Species 0.000 description 3
241001556089 Nilaparvata lugens Species 0.000 description 3
239000004372 Polyvinyl alcohol Substances 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000013543 active substance Substances 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
230000001276 controlling effect Effects 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000004744 fabric Substances 0.000 description 3
230000002363 herbicidal effect Effects 0.000 description 3
YRPFXWFBVGRDGO-UHFFFAOYSA-N n'-[(6-methylpyridin-2-yl)methyl]ethane-1,2-diamine Chemical compound CC1=CC=CC(CNCCN)=N1 YRPFXWFBVGRDGO-UHFFFAOYSA-N 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
229920002451 polyvinyl alcohol Polymers 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
238000010998 test method Methods 0.000 description 3
OCHXITZDNXMPAU-UHFFFAOYSA-N (1-benzylsulfanyl-2-nitroethenyl)sulfanylmethylbenzene Chemical group C=1C=CC=CC=1CSC(=C[N+](=O)[O-])SCC1=CC=CC=C1 OCHXITZDNXMPAU-UHFFFAOYSA-N 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
XMZJJLHHTJLEMK-UHFFFAOYSA-N 2-(nitromethylidene)-1,3-dithiolane Chemical compound [O-][N+](=O)C=C1SCCS1 XMZJJLHHTJLEMK-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
DUZJSFHGFDSUQM-UHFFFAOYSA-N 6-methylpyridine-3-carbothioic s-acid Chemical compound CC1=CC=C(C(S)=O)C=N1 DUZJSFHGFDSUQM-UHFFFAOYSA-N 0.000 description 2
QGKIRTLPMZFMDB-UHFFFAOYSA-N 6-methylpyridine-3-carbothioyl chloride Chemical compound CC1=CC=C(C(Cl)=S)C=N1 QGKIRTLPMZFMDB-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
241000258937 Hemiptera Species 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
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FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
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241000176086 Sogatella furcifera Species 0.000 description 2
244000061458 Solanum melongena Species 0.000 description 2
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
229940072049 amyl acetate Drugs 0.000 description 2
PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 2
244000000054 animal parasite Species 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
150000004657 carbamic acid derivatives Chemical class 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
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239000000969 carrier Substances 0.000 description 2
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235000013339 cereals Nutrition 0.000 description 2
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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 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
239000003814 drug Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
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MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
239000011630 iodine Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
239000003350 kerosene Substances 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000003949 liquefied natural gas Substances 0.000 description 2
229910052901 montmorillonite Inorganic materials 0.000 description 2
UXTKHOGVMWLKIK-UHFFFAOYSA-N n'-[(2,3,5,6-tetrafluoropyridin-4-yl)methyl]ethane-1,2-diamine Chemical compound NCCNCC1=C(F)C(F)=NC(F)=C1F UXTKHOGVMWLKIK-UHFFFAOYSA-N 0.000 description 2
IMRJRHPGWPFQCV-UHFFFAOYSA-N n'-[(2,3,5,6-tetrafluoropyridin-4-yl)methyl]propane-1,3-diamine Chemical compound NCCCNCC1=C(F)C(F)=NC(F)=C1F IMRJRHPGWPFQCV-UHFFFAOYSA-N 0.000 description 2
XGBLLSJHNVETLS-UHFFFAOYSA-N n'-[(2,6-dibromopyridin-4-yl)methyl]ethane-1,2-diamine Chemical compound NCCNCC1=CC(Br)=NC(Br)=C1 XGBLLSJHNVETLS-UHFFFAOYSA-N 0.000 description 2
ANOHFARTQVMMHC-UHFFFAOYSA-N n'-[(2,6-dichloropyridin-4-yl)methyl]ethane-1,2-diamine Chemical compound NCCNCC1=CC(Cl)=NC(Cl)=C1 ANOHFARTQVMMHC-UHFFFAOYSA-N 0.000 description 2
ROEONOHHVUPASG-UHFFFAOYSA-N n'-[(2,6-dichloropyridin-4-yl)methyl]propane-1,3-diamine Chemical compound NCCCNCC1=CC(Cl)=NC(Cl)=C1 ROEONOHHVUPASG-UHFFFAOYSA-N 0.000 description 2
PMZNWPGFMGFDSR-UHFFFAOYSA-N n'-[(2,6-difluoropyridin-4-yl)methyl]propane-1,3-diamine Chemical compound NCCCNCC1=CC(F)=NC(F)=C1 PMZNWPGFMGFDSR-UHFFFAOYSA-N 0.000 description 2
MIMIMQIGASWMCZ-UHFFFAOYSA-N n'-[(2,6-dimethylpyridin-4-yl)methyl]ethane-1,2-diamine Chemical compound CC1=CC(CNCCN)=CC(C)=N1 MIMIMQIGASWMCZ-UHFFFAOYSA-N 0.000 description 2
SIWMOXLQAFEUMY-UHFFFAOYSA-N n'-[(2-bromopyridin-4-yl)methyl]ethane-1,2-diamine Chemical compound NCCNCC1=CC=NC(Br)=C1 SIWMOXLQAFEUMY-UHFFFAOYSA-N 0.000 description 2
YRXSNDZLFUOGEI-UHFFFAOYSA-N n'-[(2-chloropyridin-4-yl)methyl]ethane-1,2-diamine Chemical compound NCCNCC1=CC=NC(Cl)=C1 YRXSNDZLFUOGEI-UHFFFAOYSA-N 0.000 description 2
MNSXMTVFPULMDS-UHFFFAOYSA-N n'-[(2-chloropyridin-4-yl)methyl]propane-1,3-diamine Chemical compound NCCCNCC1=CC=NC(Cl)=C1 MNSXMTVFPULMDS-UHFFFAOYSA-N 0.000 description 2
QZFXQMUBVLUSIE-UHFFFAOYSA-N n'-[(2-fluoropyridin-4-yl)methyl]ethane-1,2-diamine Chemical compound NCCNCC1=CC=NC(F)=C1 QZFXQMUBVLUSIE-UHFFFAOYSA-N 0.000 description 2
RYGDGRBHCPTMPE-UHFFFAOYSA-N n'-[(2-fluoropyridin-4-yl)methyl]propane-1,3-diamine Chemical compound NCCCNCC1=CC=NC(F)=C1 RYGDGRBHCPTMPE-UHFFFAOYSA-N 0.000 description 2
UVSZZLLROVQCTG-UHFFFAOYSA-N n'-[(2-methylpyridin-4-yl)methyl]ethane-1,2-diamine Chemical compound CC1=CC(CNCCN)=CC=N1 UVSZZLLROVQCTG-UHFFFAOYSA-N 0.000 description 2
BRWOPEJDGXXNAX-UHFFFAOYSA-N n'-[(3,5-dichloropyridin-2-yl)methyl]ethane-1,2-diamine Chemical compound NCCNCC1=NC=C(Cl)C=C1Cl BRWOPEJDGXXNAX-UHFFFAOYSA-N 0.000 description 2
GZZCBPSOLPINOG-UHFFFAOYSA-N n'-[(4,5,6-trichloropyridin-3-yl)methyl]ethane-1,2-diamine Chemical compound NCCNCC1=CN=C(Cl)C(Cl)=C1Cl GZZCBPSOLPINOG-UHFFFAOYSA-N 0.000 description 2
JSZABKJLNQZBSX-UHFFFAOYSA-N n'-[(4-methylpyridin-2-yl)methyl]propane-1,3-diamine Chemical compound CC1=CC=NC(CNCCCN)=C1 JSZABKJLNQZBSX-UHFFFAOYSA-N 0.000 description 2
ZNLGNIJKKBFKAY-UHFFFAOYSA-N n'-[(5,6-dichloropyridin-3-yl)methyl]ethane-1,2-diamine Chemical compound NCCNCC1=CN=C(Cl)C(Cl)=C1 ZNLGNIJKKBFKAY-UHFFFAOYSA-N 0.000 description 2
YYIBJISPVAMQEE-UHFFFAOYSA-N n'-[(5-bromo-6-fluoropyridin-3-yl)methyl]ethane-1,2-diamine Chemical compound NCCNCC1=CN=C(F)C(Br)=C1 YYIBJISPVAMQEE-UHFFFAOYSA-N 0.000 description 2
CCBDOWHKCSTLCG-UHFFFAOYSA-N n'-[(5-bromopyridin-3-yl)methyl]ethane-1,2-diamine Chemical compound NCCNCC1=CN=CC(Br)=C1 CCBDOWHKCSTLCG-UHFFFAOYSA-N 0.000 description 2
LJQUNIXGVRZLIG-UHFFFAOYSA-N n'-[(5-butylpyridin-2-yl)methyl]ethane-1,2-diamine Chemical compound CCCCC1=CC=C(CNCCN)N=C1 LJQUNIXGVRZLIG-UHFFFAOYSA-N 0.000 description 2
BCUNNLJOBULFSF-UHFFFAOYSA-N n'-[(5-ethylpyridin-2-yl)methyl]ethane-1,2-diamine Chemical compound CCC1=CC=C(CNCCN)N=C1 BCUNNLJOBULFSF-UHFFFAOYSA-N 0.000 description 2
WVKUBIFRCLJLQJ-UHFFFAOYSA-N n'-[(5-fluoropyridin-3-yl)methyl]ethane-1,2-diamine Chemical compound NCCNCC1=CN=CC(F)=C1 WVKUBIFRCLJLQJ-UHFFFAOYSA-N 0.000 description 2
PQSQSQCWPWLQPX-UHFFFAOYSA-N n'-[(5-methylpyridin-3-yl)methyl]ethane-1,2-diamine Chemical compound CC1=CN=CC(CNCCN)=C1 PQSQSQCWPWLQPX-UHFFFAOYSA-N 0.000 description 2
ICJUXOSURLWJLR-UHFFFAOYSA-N n'-[(6-bromopyridin-2-yl)methyl]ethane-1,2-diamine Chemical compound NCCNCC1=CC=CC(Br)=N1 ICJUXOSURLWJLR-UHFFFAOYSA-N 0.000 description 2
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