CA1084921A - Derivatives of 2-cyclopropylamino-4,6-diamino-s- triazine as insecticides - Google Patents
Derivatives of 2-cyclopropylamino-4,6-diamino-s- triazine as insecticidesInfo
- Publication number
- CA1084921A CA1084921A CA284,903A CA284903A CA1084921A CA 1084921 A CA1084921 A CA 1084921A CA 284903 A CA284903 A CA 284903A CA 1084921 A CA1084921 A CA 1084921A
- Authority
- CA
- Canada
- Prior art keywords
- represents hydrogen
- cyclopropylamino
- methyl
- triazine
- cyclopropyl
- 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.)
- Expired
Links
- LVQDKIWDGQRHTE-UHFFFAOYSA-N cyromazine Chemical class NC1=NC(N)=NC(NC2CC2)=N1 LVQDKIWDGQRHTE-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 239000002917 insecticide Substances 0.000 title description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 47
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 47
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 28
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 18
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 11
- 241000238631 Hexapoda Species 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 6
- -1 1-imidazolyl Chemical group 0.000 claims description 46
- 150000001875 compounds Chemical class 0.000 claims description 31
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 10
- 241000255925 Diptera Species 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
- 150000003335 secondary amines Chemical class 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 241000257226 Muscidae Species 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- SRDNQMPCQFDOJE-UHFFFAOYSA-N 2-n,4-n-dicyclopropyl-1,3,5-triazine-2,4,6-triamine Chemical compound N=1C(NC2CC2)=NC(N)=NC=1NC1CC1 SRDNQMPCQFDOJE-UHFFFAOYSA-N 0.000 claims description 3
- PDEAKEHGTLHCBC-UHFFFAOYSA-N 4-n-cyclopropyl-2-n,2-n-dimethyl-1,3,5-triazine-2,4,6-triamine Chemical compound CN(C)C1=NC(N)=NC(NC2CC2)=N1 PDEAKEHGTLHCBC-UHFFFAOYSA-N 0.000 claims description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
- 150000003840 hydrochlorides Chemical class 0.000 claims description 3
- 230000029052 metamorphosis Effects 0.000 claims description 3
- GGDSREHMWWSRBZ-UHFFFAOYSA-N 2-N-cyclopropyl-4-N-methyl-1,3,5-triazine-2,4,6-triamine dihydrochloride Chemical compound Cl.Cl.C1(CC1)NC1=NC(=NC(=N1)N)NC GGDSREHMWWSRBZ-UHFFFAOYSA-N 0.000 claims description 2
- ISULFBJTXXCURV-UHFFFAOYSA-N 4-n-cyclopropyl-2-n-ethyl-2-n-methyl-1,3,5-triazine-2,4,6-triamine Chemical compound CCN(C)C1=NC(N)=NC(NC2CC2)=N1 ISULFBJTXXCURV-UHFFFAOYSA-N 0.000 claims description 2
- 241000257161 Calliphoridae Species 0.000 claims description 2
- GCUXLQJDOSGYOL-UHFFFAOYSA-N Cl.Cl.C1(CC1)NC1=NC(=NC(=N1)NCC)NCC Chemical compound Cl.Cl.C1(CC1)NC1=NC(=NC(=N1)NCC)NCC GCUXLQJDOSGYOL-UHFFFAOYSA-N 0.000 claims description 2
- 241000256113 Culicidae Species 0.000 claims description 2
- 241000256103 Simuliidae Species 0.000 claims description 2
- 241000131339 Tipulidae Species 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 230000001418 larval effect Effects 0.000 claims 1
- 239000013543 active substance Substances 0.000 description 41
- 239000000203 mixture Substances 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 239000000969 carrier Substances 0.000 description 9
- 239000008187 granular material Substances 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 239000002270 dispersing agent Substances 0.000 description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
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- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
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- 238000009472 formulation Methods 0.000 description 4
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 4
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- 239000003960 organic solvent Substances 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- GJVAYPWJOBBCKD-UHFFFAOYSA-N 2-n-cyclopropyl-6-morpholin-4-yl-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2CCOCC2)=NC(N)=NC=1NC1CC1 GJVAYPWJOBBCKD-UHFFFAOYSA-N 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000003559 chemosterilizing effect Effects 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 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 3
- 239000000463 material Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
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- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 2
- JCRNSBKSAQHNIN-UHFFFAOYSA-N 2,4-dibutylnaphthalene-1-sulfonic acid Chemical class C1=CC=CC2=C(S(O)(=O)=O)C(CCCC)=CC(CCCC)=C21 JCRNSBKSAQHNIN-UHFFFAOYSA-N 0.000 description 2
- VAVHFSLANKKYFJ-UHFFFAOYSA-N 2-n-cyclopropyl-4-n-ethyl-6-morpholin-4-yl-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N2CCOCC2)=NC(NCC)=NC=1NC1CC1 VAVHFSLANKKYFJ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
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- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 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
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 235000001465 calcium Nutrition 0.000 description 1
- 229960005069 calcium Drugs 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000007931 coated granule Substances 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 239000004491 dispersible concentrate Substances 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 244000078703 ectoparasite Species 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000010433 feldspar Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical class CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002949 juvenile hormone Substances 0.000 description 1
- 229930014550 juvenile hormone Natural products 0.000 description 1
- 150000003633 juvenile hormone derivatives Chemical class 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 230000000974 larvacidal effect Effects 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000012219 potassium aluminium silicate Nutrition 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000019617 pupation Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- 238000002336 sorption--desorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C07D251/70—Other substituted melamines
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C07D251/66—Derivatives of melamine in which a hetero atom is directly attached to a nitrogen atom of melamine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1055876A CH604517A5 (enrdf_load_stackoverflow) | 1976-08-19 | 1976-08-19 | |
| CH10558/76 | 1976-08-19 | ||
| CH2718/77 | 1977-03-04 | ||
| CH271877A CH609835A5 (en) | 1976-08-19 | 1977-03-04 | Pesticide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1084921A true CA1084921A (en) | 1980-09-02 |
Family
ID=25691226
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA284,903A Expired CA1084921A (en) | 1976-08-19 | 1977-08-17 | Derivatives of 2-cyclopropylamino-4,6-diamino-s- triazine as insecticides |
Country Status (19)
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4187304A (en) * | 1978-02-17 | 1980-02-05 | Ciba-Geigy Corporation | Procedure for treating mammals to control parasitic diptera larvae |
| US4187305A (en) * | 1978-02-17 | 1980-02-05 | Ciba-Geigy Corporation | Procedure for treating mammals to control parasitic diptera larvae |
| JPS5622731A (en) * | 1979-08-03 | 1981-03-03 | Ciba Geigy Ag | Method of treating mammals to repel parasites |
| JPS5626883A (en) * | 1979-08-11 | 1981-03-16 | Ciba Geigy Ag | Compound and composition for treating mammal to expel parasite |
| US4402954A (en) * | 1980-11-24 | 1983-09-06 | Ciba-Geigy Corporation | Synergistic pesticidal compositions comprising N-(2-methyl-4-chlorophenyl)-N',N'-dimethylthiourea and 2,4-diamino-6-cyclopropylamino-2-triazine or 2,4-diamino-6-isopropylamino-2-triazine |
| EP0053100B1 (de) * | 1980-11-25 | 1984-09-19 | Ciba-Geigy Ag | Schädlingsbekämpfungsmittel |
| ATE9428T1 (de) * | 1980-11-25 | 1984-10-15 | Ciba-Geigy Ag | Schaedlingsbekaempfungsmittel. |
| JPS5840314A (ja) * | 1981-09-04 | 1983-03-09 | Mitsui Toatsu Chem Inc | プロピレンブロツク共重合体組成物 |
| JPS5941317A (ja) * | 1982-08-31 | 1984-03-07 | Mitsui Toatsu Chem Inc | プロピレン―エチレンブロック共重合体の製造法 |
| CH660110A5 (de) * | 1984-12-06 | 1987-03-31 | Ciba Geigy Ag | Triazine als schaedlingsbekaempfungsmittel. |
| NZ221262A (en) * | 1986-08-06 | 1990-08-28 | Ciba Geigy Ag | Preventing the reinfestation of dogs and cats by fleas by administering to the host a flea growth inhibiting substance orally, parenterally or by implant |
| JPS6415408U (enrdf_load_stackoverflow) * | 1987-07-15 | 1989-01-26 | ||
| US4967158A (en) * | 1989-03-31 | 1990-10-30 | Hydro-Quebec | Portable detector device for detecting partial electrical discharge in live voltage distribution cables and/or equipment |
| DE19825379A1 (de) * | 1998-06-06 | 1999-12-09 | Bayer Ag | Verwendung von substituierten 2,4-Diamino-1,3,5-triazinen zur Bekämpfung tierischer Schädlinge |
| PT1941798E (pt) | 2004-12-17 | 2012-08-22 | Devgen Nv | Composições nematodicidas |
| DE102007045922A1 (de) | 2007-09-26 | 2009-04-02 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| DE102007045957A1 (de) | 2007-09-26 | 2009-04-09 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akarziden Eigenschaften |
| EP2127522A1 (de) | 2008-05-29 | 2009-12-02 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| EP2410849A1 (de) | 2009-03-25 | 2012-02-01 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden eigenschaften |
| EP2382865A1 (de) | 2010-04-28 | 2011-11-02 | Bayer CropScience AG | Synergistische Wirkstoffkombinationen |
| CN108276351A (zh) * | 2018-02-11 | 2018-07-13 | 天津大学 | 具有潜在抗癌效果化合物及其测定方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2567847A (en) * | 1951-09-11 | Preparation of substituted | ||
| US3189521A (en) * | 1964-12-24 | 1965-06-15 | Alexej B Borkovec | Diamino- and triamino-s-triazines as chemosterilants for insects |
| IL39385A (en) * | 1971-06-01 | 1974-12-31 | Ciba Geigy Ag | A method for combating insects by the use of 4-azido-2,6-diamino triazine derivatives,certain such novel derivatives and their manufacture |
-
1977
- 1977-03-04 CH CH271877A patent/CH609835A5/xx active Protection Beyond IP Right Term
- 1977-08-16 DE DE19772736876 patent/DE2736876A1/de active Granted
- 1977-08-17 IL IL52765A patent/IL52765A/xx unknown
- 1977-08-17 NL NLAANVRAGE7709096,A patent/NL184894B/xx active Protection Beyond IP Right Term
- 1977-08-17 CA CA284,903A patent/CA1084921A/en not_active Expired
- 1977-08-17 SU SU772511554A patent/SU727104A3/ru active
- 1977-08-17 YU YU1988/77A patent/YU41077B/xx unknown
- 1977-08-18 GB GB34793/77A patent/GB1587573A/en not_active Expired
- 1977-08-18 NZ NZ184953A patent/NZ184953A/xx unknown
- 1977-08-18 BE BE180257A patent/BE857896A/xx not_active IP Right Cessation
- 1977-08-18 CY CY1248A patent/CY1248A/xx unknown
- 1977-08-18 AT AT598677A patent/AT361249B/de not_active IP Right Cessation
- 1977-08-18 ES ES461715A patent/ES461715A1/es not_active Expired
- 1977-08-18 FR FR7725247A patent/FR2362134A1/fr active Granted
- 1977-08-19 JP JP52099398A patent/JPS6052705B2/ja not_active Expired
- 1977-08-19 AU AU28041/77A patent/AU518896B2/en not_active Expired
-
1982
- 1982-05-31 KE KE3216A patent/KE3216A/xx unknown
- 1982-06-04 YU YU1191/82A patent/YU41270B/xx unknown
- 1982-06-10 HK HK253/82A patent/HK25382A/en not_active IP Right Cessation
-
1983
- 1983-12-30 MY MY55/83A patent/MY8300055A/xx unknown
-
1993
- 1993-06-22 NL NL930086C patent/NL930086I2/nl unknown
-
1997
- 1997-08-08 NL NL971032C patent/NL971032I2/nl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL184894B (nl) | 1989-07-03 |
| FR2362134A1 (fr) | 1978-03-17 |
| IL52765A0 (en) | 1977-10-31 |
| AT361249B (de) | 1981-02-25 |
| MY8300055A (en) | 1983-12-31 |
| YU119182A (en) | 1984-06-30 |
| FR2362134B1 (enrdf_load_stackoverflow) | 1980-02-01 |
| AU518896B2 (en) | 1981-10-29 |
| DE2736876A1 (de) | 1978-02-23 |
| DE2736876C2 (enrdf_load_stackoverflow) | 1989-01-19 |
| AU2804177A (en) | 1979-02-22 |
| BE857896A (fr) | 1978-02-20 |
| JPS6052705B2 (ja) | 1985-11-20 |
| NL930086I2 (nl) | 1995-03-01 |
| NL7709096A (nl) | 1978-02-21 |
| KE3216A (en) | 1982-07-09 |
| SU727104A3 (ru) | 1980-04-05 |
| NL971032I2 (nl) | 1998-03-02 |
| JPS5325585A (en) | 1978-03-09 |
| HK25382A (en) | 1982-06-18 |
| NL971032I1 (nl) | 1997-10-01 |
| ATA598677A (de) | 1980-07-15 |
| NL930086I1 (nl) | 1993-09-16 |
| GB1587573A (en) | 1981-04-08 |
| IL52765A (en) | 1981-12-31 |
| CH609835A5 (en) | 1979-03-30 |
| ES461715A1 (es) | 1978-10-01 |
| YU41270B (en) | 1986-12-31 |
| NZ184953A (en) | 1980-08-26 |
| YU198877A (en) | 1982-10-31 |
| YU41077B (en) | 1986-12-31 |
| CY1248A (en) | 1984-08-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |