DD143721A5 - Insektizides mittel - Google Patents
Insektizides mittel Download PDFInfo
- Publication number
- DD143721A5 DD143721A5 DD78213690A DD21369078A DD143721A5 DD 143721 A5 DD143721 A5 DD 143721A5 DD 78213690 A DD78213690 A DD 78213690A DD 21369078 A DD21369078 A DD 21369078A DD 143721 A5 DD143721 A5 DD 143721A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- amino
- methyl
- chlorobenzoyl
- urea
- pyrazinyl
- Prior art date
Links
- 239000002917 insecticide Substances 0.000 title description 10
- -1 C_-C g -cycloalky Chemical group 0.000 claims description 73
- 239000000203 mixture Substances 0.000 claims description 65
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 239000004480 active ingredient Substances 0.000 claims description 27
- 150000002367 halogens Chemical group 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 21
- 150000002431 hydrogen Chemical group 0.000 claims description 16
- 239000000460 chlorine Substances 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 230000000749 insecticidal effect Effects 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 79
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 47
- 239000007787 solid Substances 0.000 description 41
- 238000002844 melting Methods 0.000 description 37
- 230000008018 melting Effects 0.000 description 37
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 235000013877 carbamide Nutrition 0.000 description 30
- 239000000243 solution Substances 0.000 description 30
- 238000000034 method Methods 0.000 description 28
- ZTUIVBFRTPPWEZ-UHFFFAOYSA-N 2-chlorobenzoyl isocyanate Chemical compound ClC1=CC=CC=C1C(=O)N=C=O ZTUIVBFRTPPWEZ-UHFFFAOYSA-N 0.000 description 27
- 238000002360 preparation method Methods 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 26
- 239000004202 carbamide Substances 0.000 description 25
- 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 description 24
- 241000238631 Hexapoda Species 0.000 description 24
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 22
- 240000001307 Myosotis scorpioides Species 0.000 description 20
- 239000002904 solvent Substances 0.000 description 19
- 241000254173 Coleoptera Species 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 238000002329 infrared spectrum Methods 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 229920000742 Cotton Polymers 0.000 description 14
- 239000000543 intermediate Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- 241000196324 Embryophyta Species 0.000 description 13
- 241000219146 Gossypium Species 0.000 description 13
- 238000000921 elemental analysis Methods 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 235000021186 dishes Nutrition 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 10
- 239000000155 melt Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 150000002923 oximes Chemical class 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 8
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 7
- 244000068988 Glycine max Species 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 235000013601 eggs Nutrition 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 7
- SJYCYRJOUJAQFB-UHFFFAOYSA-N 5-(4-bromophenyl)-6-methylpyrazin-2-amine Chemical compound CC1=NC(N)=CN=C1C1=CC=C(Br)C=C1 SJYCYRJOUJAQFB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- NHUFIOMPICRXFX-UHFFFAOYSA-N 5,6-dichloropyrazin-2-amine Chemical compound NC1=CN=C(Cl)C(Cl)=N1 NHUFIOMPICRXFX-UHFFFAOYSA-N 0.000 description 5
- 241000255749 Coccinellidae Species 0.000 description 5
- 241000255925 Diptera Species 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000012085 test solution Substances 0.000 description 5
- RZMVHCYCUAKRMM-UHFFFAOYSA-N 2-methylbenzoyl isocyanate Chemical compound CC1=CC=CC=C1C(=O)N=C=O RZMVHCYCUAKRMM-UHFFFAOYSA-N 0.000 description 4
- ILDRNIDSVAZBMZ-UHFFFAOYSA-N 5-(trifluoromethyl)pyrazin-2-amine Chemical compound NC1=CN=C(C(F)(F)F)C=N1 ILDRNIDSVAZBMZ-UHFFFAOYSA-N 0.000 description 4
- HWCKAMAVEWVBDO-UHFFFAOYSA-N 5-chloropyrazin-2-amine Chemical compound NC1=CN=C(Cl)C=N1 HWCKAMAVEWVBDO-UHFFFAOYSA-N 0.000 description 4
- 241000256118 Aedes aegypti Species 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 4
- 241000255777 Lepidoptera Species 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
- 244000046052 Phaseolus vulgaris Species 0.000 description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 4
- 241001521235 Spodoptera eridania Species 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 150000003216 pyrazines Chemical class 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 150000003672 ureas Chemical class 0.000 description 4
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 description 3
- SSNIXANZPPREMK-UHFFFAOYSA-N 1-(4-bromophenyl)-2-hydroxyiminopropan-1-one Chemical compound ON=C(C)C(=O)C1=CC=C(Br)C=C1 SSNIXANZPPREMK-UHFFFAOYSA-N 0.000 description 3
- RUIZBQQGWNBRFH-UHFFFAOYSA-N 1-oxidopyrazin-1-ium Chemical class [O-][N+]1=CC=NC=C1 RUIZBQQGWNBRFH-UHFFFAOYSA-N 0.000 description 3
- 125000004098 2,6-dichlorobenzoyl group Chemical group O=C([*])C1=C(Cl)C([H])=C([H])C([H])=C1Cl 0.000 description 3
- JTPXVCKCLBROOJ-UHFFFAOYSA-N 2-amino-6-chloropyrazine Chemical compound NC1=CN=CC(Cl)=N1 JTPXVCKCLBROOJ-UHFFFAOYSA-N 0.000 description 3
- HEPPAPZASXFWTB-UHFFFAOYSA-N 3,3-dibromo-1,1,1-trifluoropropan-2-one Chemical compound FC(F)(F)C(=O)C(Br)Br HEPPAPZASXFWTB-UHFFFAOYSA-N 0.000 description 3
- TZEPSUWOCPVNMM-UHFFFAOYSA-N 3-amino-6-chloropyrazine-2-carboxylic acid Chemical compound NC1=NC=C(Cl)N=C1C(O)=O TZEPSUWOCPVNMM-UHFFFAOYSA-N 0.000 description 3
- LURGZVKKNLPCSQ-UHFFFAOYSA-N 3-amino-6-methylpyrazine-2-carbonitrile Chemical compound CC1=CN=C(N)C(C#N)=N1 LURGZVKKNLPCSQ-UHFFFAOYSA-N 0.000 description 3
- QYCWZGDAYYKQTL-UHFFFAOYSA-N 5-(4-bromophenyl)-6-ethylpyrazin-2-amine Chemical compound CCC1=NC(N)=CN=C1C1=CC=C(Br)C=C1 QYCWZGDAYYKQTL-UHFFFAOYSA-N 0.000 description 3
- CVJPYKAULVWKBH-UHFFFAOYSA-N 5-(4-methoxyphenyl)-6-methylpyrazin-2-amine Chemical compound C1=CC(OC)=CC=C1C1=NC=C(N)N=C1C CVJPYKAULVWKBH-UHFFFAOYSA-N 0.000 description 3
- FMBKXKZEXQCCFM-UHFFFAOYSA-N 6-(trifluoromethyl)pyrazin-2-amine Chemical compound NC1=CN=CC(C(F)(F)F)=N1 FMBKXKZEXQCCFM-UHFFFAOYSA-N 0.000 description 3
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- 241001465754 Metazoa Species 0.000 description 3
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- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 210000003608 fece Anatomy 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- JGAJCAJHSHUPGH-UHFFFAOYSA-N methyl 3-amino-6-chloropyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(Cl)=CN=C1N JGAJCAJHSHUPGH-UHFFFAOYSA-N 0.000 description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 3
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- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical class CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
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- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
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- 125000005999 2-bromoethyl group Chemical group 0.000 description 2
- PSKYXWMZYBYVDK-UHFFFAOYSA-N 3,3,3-trifluoro-1-phenylpropane-1,2-dione;hydrate Chemical compound O.FC(F)(F)C(=O)C(=O)C1=CC=CC=C1 PSKYXWMZYBYVDK-UHFFFAOYSA-N 0.000 description 2
- ASONUAQLGIPYMA-UHFFFAOYSA-N 3,3-dimethyl-2-oxobutanal Chemical compound CC(C)(C)C(=O)C=O ASONUAQLGIPYMA-UHFFFAOYSA-N 0.000 description 2
- NRDPLJROSGVEDO-UHFFFAOYSA-N 3,5,6-trichloropyrazin-2-amine Chemical compound NC1=NC(Cl)=C(Cl)N=C1Cl NRDPLJROSGVEDO-UHFFFAOYSA-N 0.000 description 2
- CJXBBQKTUJXSGF-UHFFFAOYSA-N 3,6-dichloropyrazin-2-amine Chemical compound NC1=NC(Cl)=CN=C1Cl CJXBBQKTUJXSGF-UHFFFAOYSA-N 0.000 description 2
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- JGNQFJDHMNVADD-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-methylpyrazin-2-amine Chemical compound CC1=NC(N)=CN=C1C1=CC=C(Cl)C=C1 JGNQFJDHMNVADD-UHFFFAOYSA-N 0.000 description 2
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- YWJPZSPKFLCFRU-UHFFFAOYSA-N 5-(4-ethylphenyl)-6-methylpyrazin-2-amine Chemical compound C1=CC(CC)=CC=C1C1=NC=C(N)N=C1C YWJPZSPKFLCFRU-UHFFFAOYSA-N 0.000 description 2
- BBGAQYOMHGXLGG-UHFFFAOYSA-N 5-cyclohexyl-6-methylpyrazin-2-amine Chemical compound CC1=NC(N)=CN=C1C1CCCCC1 BBGAQYOMHGXLGG-UHFFFAOYSA-N 0.000 description 2
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- UMKXTWMATLULJT-UHFFFAOYSA-N 5-phenyl-6-(trifluoromethyl)pyrazin-2-amine Chemical compound FC(F)(F)C1=NC(N)=CN=C1C1=CC=CC=C1 UMKXTWMATLULJT-UHFFFAOYSA-N 0.000 description 2
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- XBUOJHOOEZUBQU-UHFFFAOYSA-N 6-methyl-5-(4-methylphenyl)pyrazin-2-amine Chemical compound C1=CC(C)=CC=C1C1=NC=C(N)N=C1C XBUOJHOOEZUBQU-UHFFFAOYSA-N 0.000 description 2
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- JINBYESILADKFW-UHFFFAOYSA-N aminomalonic acid Chemical compound OC(=O)C(N)C(O)=O JINBYESILADKFW-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
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- 230000005540 biological transmission Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000005997 bromomethyl group Chemical group 0.000 description 2
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
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- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 241000256250 Spodoptera littoralis Species 0.000 description 1
- 241001494115 Stomoxys calcitrans Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- FDPGLXSGGNIGGP-UHFFFAOYSA-N [5-(trifluoromethyl)pyrazin-2-yl]urea Chemical compound FC(C=1N=CC(=NC1)NC(=O)N)(F)F FDPGLXSGGNIGGP-UHFFFAOYSA-N 0.000 description 1
- OZQAAFKBIANAMU-UHFFFAOYSA-N [O-][N+]1=C(N)C(C(=O)OCC)=NC(C=2C=CC(Br)=CC=2)=C1 Chemical compound [O-][N+]1=C(N)C(C(=O)OCC)=NC(C=2C=CC(Br)=CC=2)=C1 OZQAAFKBIANAMU-UHFFFAOYSA-N 0.000 description 1
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 150000003936 benzamides Chemical class 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical class O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 description 1
- 150000008047 benzoylureas Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000004148 curcumin Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000000911 decarboxylating effect Effects 0.000 description 1
- QQQYTWIFVNKMRW-UHFFFAOYSA-N diflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C1 QQQYTWIFVNKMRW-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000013057 ectoparasiticide Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- JYGRVMQGWVVHJE-UHFFFAOYSA-N ethyl 2-amino-2-cyanoacetate Chemical compound CCOC(=O)C(N)C#N JYGRVMQGWVVHJE-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 244000037666 field crops Species 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 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
- 239000004571 lime Substances 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- INCSQLZZXBPATR-UHFFFAOYSA-N methyl 3-aminopyrazine-2-carboxylate Chemical compound COC(=O)C1=NC=CN=C1N INCSQLZZXBPATR-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- UGJMSGSIDRFEEF-UHFFFAOYSA-N n-[(5-benzyl-6-chloropyrazin-2-yl)carbamoyl]-2-methylbenzamide Chemical compound CC1=CC=CC=C1C(=O)NC(=O)NC(N=C1Cl)=CN=C1CC1=CC=CC=C1 UGJMSGSIDRFEEF-UHFFFAOYSA-N 0.000 description 1
- ULVHFQQAAZLUGN-UHFFFAOYSA-N n-[(5-benzyl-6-methylpyrazin-2-yl)carbamoyl]-2-bromobenzamide Chemical compound C=1N=C(CC=2C=CC=CC=2)C(C)=NC=1NC(=O)NC(=O)C1=CC=CC=C1Br ULVHFQQAAZLUGN-UHFFFAOYSA-N 0.000 description 1
- WLGZBILSGUJQAI-UHFFFAOYSA-N n-[(5-bromo-6-ethylpyrazin-2-yl)carbamoyl]-2-methylbenzamide Chemical compound N1=C(Br)C(CC)=NC(NC(=O)NC(=O)C=2C(=CC=CC=2)C)=C1 WLGZBILSGUJQAI-UHFFFAOYSA-N 0.000 description 1
- BBWXIGVVKXICQF-UHFFFAOYSA-N n-[(6-bromo-5-cyanopyrazin-2-yl)carbamoyl]-2-chlorobenzamide Chemical compound ClC1=CC=CC=C1C(=O)NC(=O)NC1=CN=C(C#N)C(Br)=N1 BBWXIGVVKXICQF-UHFFFAOYSA-N 0.000 description 1
- ZGOLQMOPAHHQCC-UHFFFAOYSA-N n-carbamoyl-2-chlorobenzamide Chemical compound NC(=O)NC(=O)C1=CC=CC=C1Cl ZGOLQMOPAHHQCC-UHFFFAOYSA-N 0.000 description 1
- 125000006124 n-propyl sulfonyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000194 ovacidal Toxicity 0.000 description 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 1
- ZJVAWPKTWVFKHG-UHFFFAOYSA-N p-Methoxypropiophenone Chemical compound CCC(=O)C1=CC=C(OC)C=C1 ZJVAWPKTWVFKHG-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000013138 pruning Methods 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- XFTQRUTUGRCSGO-UHFFFAOYSA-N pyrazin-2-amine Chemical compound NC1=CN=CC=N1 XFTQRUTUGRCSGO-UHFFFAOYSA-N 0.000 description 1
- NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000002641 tar oil Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 230000036642 wellbeing Effects 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
- C07C275/48—Y being a hydrogen or a carbon atom
- C07C275/54—Y being a carbon atom of a six-membered aromatic ring, e.g. benzoylureas
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
- C07D241/20—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D241/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with nitrogen atoms directly attached to ring carbon atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2609377 | 1977-06-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD143721A5 true DD143721A5 (de) | 1980-09-10 |
Family
ID=10238257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD78213690A DD143721A5 (de) | 1977-06-22 | 1978-06-22 | Insektizides mittel |
Country Status (11)
| Country | Link |
|---|---|
| BE (1) | BE868228A (cs) |
| CA (1) | CA1129861A (cs) |
| CS (1) | CS198104B2 (cs) |
| DD (1) | DD143721A5 (cs) |
| ES (1) | ES471057A1 (cs) |
| FR (1) | FR2398739A1 (cs) |
| GB (1) | GB2066806B (cs) |
| HU (1) | HU185336B (cs) |
| IN (1) | IN149912B (cs) |
| SE (1) | SE8303206L (cs) |
| ZA (1) | ZA783553B (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2878198A1 (de) | 2013-11-29 | 2015-06-03 | Flügel GmbH | Verfahren zum Anlocken von kambiophagen, xylophagen und/oder myzetophagen Insekten |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4212870A (en) * | 1979-06-18 | 1980-07-15 | Gulf Oil Corporation | 1-(2,6-Dichlorobenzoyl)-3-(5-chloro-2-pyridinyl-N-oxide)urea and use as insecticide |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EG11837A (en) * | 1974-09-19 | 1977-12-31 | Lilly Co Eli | Novel 1-(substituted benzoyl)-3-(substituted pyrazinyl ureas used as insecticides |
-
1978
- 1978-06-16 IN IN666/CAL/78A patent/IN149912B/en unknown
- 1978-06-19 BE BE1008936A patent/BE868228A/xx not_active IP Right Cessation
- 1978-06-19 CA CA305,703A patent/CA1129861A/en not_active Expired
- 1978-06-19 GB GB8019107A patent/GB2066806B/en not_active Expired
- 1978-06-20 HU HU821470A patent/HU185336B/hu unknown
- 1978-06-21 ZA ZA783553A patent/ZA783553B/xx unknown
- 1978-06-21 CS CS784095A patent/CS198104B2/cs unknown
- 1978-06-22 DD DD78213690A patent/DD143721A5/de unknown
- 1978-06-22 ES ES471057A patent/ES471057A1/es not_active Expired
- 1978-11-17 FR FR7832550A patent/FR2398739A1/fr active Granted
-
1983
- 1983-06-07 SE SE8303206A patent/SE8303206L/sv not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2878198A1 (de) | 2013-11-29 | 2015-06-03 | Flügel GmbH | Verfahren zum Anlocken von kambiophagen, xylophagen und/oder myzetophagen Insekten |
Also Published As
| Publication number | Publication date |
|---|---|
| BE868228A (fr) | 1978-12-19 |
| ES471057A1 (es) | 1980-01-16 |
| GB2066806B (en) | 1982-08-18 |
| HU185336B (en) | 1985-01-28 |
| SE8303206D0 (sv) | 1983-06-07 |
| ZA783553B (en) | 1980-02-27 |
| IN149912B (cs) | 1982-05-29 |
| FR2398739A1 (fr) | 1979-02-23 |
| CS198104B2 (en) | 1980-05-30 |
| FR2398739B1 (cs) | 1982-11-05 |
| SE8303206L (sv) | 1983-06-07 |
| GB2066806A (en) | 1981-07-15 |
| CA1129861A (en) | 1982-08-17 |
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