DE2824126C2 - Tetrahydro-1,3,5-thiadiazin-4-on-Verbindungen - Google Patents
Tetrahydro-1,3,5-thiadiazin-4-on-VerbindungenInfo
- Publication number
- DE2824126C2 DE2824126C2 DE2824126A DE2824126A DE2824126C2 DE 2824126 C2 DE2824126 C2 DE 2824126C2 DE 2824126 A DE2824126 A DE 2824126A DE 2824126 A DE2824126 A DE 2824126A DE 2824126 C2 DE2824126 C2 DE 2824126C2
- Authority
- DE
- Germany
- Prior art keywords
- thiadiazin
- tetrahydro
- mol
- isopropyl
- benzene
- 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
- PAMXRTQIJNZQPB-UHFFFAOYSA-N 1,3,5-thiadiazinan-4-one Chemical class O=C1NCSCN1 PAMXRTQIJNZQPB-UHFFFAOYSA-N 0.000 title claims description 4
- 239000000203 mixture Substances 0.000 claims description 106
- -1 4-hydroxylphenyl group Chemical group 0.000 claims description 50
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 36
- 238000002360 preparation method Methods 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 14
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 13
- 230000000749 insecticidal effect Effects 0.000 claims description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 6
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- PRLVTUNWOQKEAI-UHFFFAOYSA-N 2-(tert-butylimino)-5-phenyl-3-(propan-2-yl)-1,3,5-thiadiazinan-4-one Chemical compound O=C1N(C(C)C)C(=NC(C)(C)C)SCN1C1=CC=CC=C1 PRLVTUNWOQKEAI-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- KFDRMWUDUZKPST-UHFFFAOYSA-N 2-tert-butylimino-5-(2-chlorophenyl)-3-propan-2-yl-1,3,5-thiadiazinan-4-one Chemical compound C1SC(=NC(C)(C)C)N(C(C)C)C(=O)N1C1=CC=CC=C1Cl KFDRMWUDUZKPST-UHFFFAOYSA-N 0.000 claims description 2
- GNSVRFOSRMNIFW-UHFFFAOYSA-N 2-tert-butylimino-5-(3-chlorophenyl)-3-propan-2-yl-1,3,5-thiadiazinan-4-one Chemical compound C1SC(=NC(C)(C)C)N(C(C)C)C(=O)N1C1=CC=CC(Cl)=C1 GNSVRFOSRMNIFW-UHFFFAOYSA-N 0.000 claims description 2
- RGAKQOLQRRKCGM-UHFFFAOYSA-N 2-tert-butylimino-5-(4-methoxyphenyl)-3-propan-2-yl-1,3,5-thiadiazinan-4-one Chemical compound C1=CC(OC)=CC=C1N1C(=O)N(C(C)C)C(=NC(C)(C)C)SC1 RGAKQOLQRRKCGM-UHFFFAOYSA-N 0.000 claims description 2
- QKVOIYOWIYFNON-UHFFFAOYSA-N 2-tert-butylimino-5-(4-methylphenyl)-3-propan-2-yl-1,3,5-thiadiazinan-4-one Chemical compound O=C1N(C(C)C)C(=NC(C)(C)C)SCN1C1=CC=C(C)C=C1 QKVOIYOWIYFNON-UHFFFAOYSA-N 0.000 claims description 2
- 125000002425 furfuryl group Chemical group C(C1=CC=CO1)* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000003129 miticidal effect Effects 0.000 claims description 2
- XAKHWLVZKZBVCW-UHFFFAOYSA-N 2-tert-butylimino-5-(3-methylphenyl)-3-propan-2-yl-1,3,5-thiadiazinan-4-one Chemical compound O=C1N(C(C)C)C(=NC(C)(C)C)SCN1C1=CC=CC(C)=C1 XAKHWLVZKZBVCW-UHFFFAOYSA-N 0.000 claims 1
- STEMCTHCYKAKPE-UHFFFAOYSA-N 3-butan-2-yl-2-tert-butylimino-5-(4-methoxyphenyl)-1,3,5-thiadiazinan-4-one Chemical compound C1SC(=NC(C)(C)C)N(C(C)CC)C(=O)N1C1=CC=C(OC)C=C1 STEMCTHCYKAKPE-UHFFFAOYSA-N 0.000 claims 1
- 239000003701 inert diluent Substances 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 492
- 150000001875 compounds Chemical class 0.000 description 155
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 150
- 125000001309 chloro group Chemical group Cl* 0.000 description 133
- 239000000243 solution Substances 0.000 description 102
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 101
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 92
- 239000013078 crystal Substances 0.000 description 91
- 238000003756 stirring Methods 0.000 description 48
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
- 239000000126 substance Substances 0.000 description 45
- 238000005481 NMR spectroscopy Methods 0.000 description 37
- 239000011541 reaction mixture Substances 0.000 description 37
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- 238000002844 melting Methods 0.000 description 28
- 230000008018 melting Effects 0.000 description 28
- 229910052739 hydrogen Inorganic materials 0.000 description 27
- 101150065749 Churc1 gene Proteins 0.000 description 25
- 102100038239 Protein Churchill Human genes 0.000 description 25
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 23
- 238000004821 distillation Methods 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 230000000704 physical effect Effects 0.000 description 17
- 238000002156 mixing Methods 0.000 description 16
- 239000004615 ingredient Substances 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 150000003840 hydrochlorides Chemical class 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 241000238631 Hexapoda Species 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 11
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
- NUJIXNWAWRCFKV-UHFFFAOYSA-N n-(chloromethyl)-n-phenylcarbamoyl chloride Chemical compound ClCN(C(Cl)=O)C1=CC=CC=C1 NUJIXNWAWRCFKV-UHFFFAOYSA-N 0.000 description 11
- 241000209094 Oryza Species 0.000 description 10
- 241000607479 Yersinia pestis Species 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000007921 spray Substances 0.000 description 10
- 238000010998 test method Methods 0.000 description 10
- KREOCUNMMFZOOS-UHFFFAOYSA-N 1,3-di(propan-2-yl)thiourea Chemical compound CC(C)NC(S)=NC(C)C KREOCUNMMFZOOS-UHFFFAOYSA-N 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 235000007164 Oryza sativa Nutrition 0.000 description 9
- 239000004927 clay Substances 0.000 description 9
- 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 9
- 235000019441 ethanol Nutrition 0.000 description 9
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 9
- 235000009566 rice Nutrition 0.000 description 9
- JKZGKJJRHXYLRI-UHFFFAOYSA-N 1-tert-butyl-3-propan-2-ylthiourea Chemical compound CC(C)NC(=S)NC(C)(C)C JKZGKJJRHXYLRI-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 239000002917 insecticide Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 239000008096 xylene Substances 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 241001556089 Nilaparvata lugens Species 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000004495 emulsifiable concentrate Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- FOQGRRCSZSDSPW-UHFFFAOYSA-N 1-methyl-3-propan-2-ylthiourea Chemical compound CNC(=S)NC(C)C FOQGRRCSZSDSPW-UHFFFAOYSA-N 0.000 description 5
- 241000238876 Acari Species 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 241000488581 Panonychus citri Species 0.000 description 5
- 238000007605 air drying Methods 0.000 description 5
- 239000011575 calcium Substances 0.000 description 5
- 229910052791 calcium Inorganic materials 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 235000012054 meals Nutrition 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 239000000123 paper Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 5
- 239000004563 wettable powder Substances 0.000 description 5
- GNIXDZXDJIHLHY-UHFFFAOYSA-N 1,3,5-tris(4-propan-2-yloxyphenyl)-1,3,5-triazinane Chemical compound C1=CC(OC(C)C)=CC=C1N1CN(C=2C=CC(OC(C)C)=CC=2)CN(C=2C=CC(OC(C)C)=CC=2)C1 GNIXDZXDJIHLHY-UHFFFAOYSA-N 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000005909 Kieselgur Substances 0.000 description 4
- VLCDUOXHFNUCKK-UHFFFAOYSA-N N,N'-Dimethylthiourea Chemical compound CNC(=S)NC VLCDUOXHFNUCKK-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 241001454293 Tetranychus urticae Species 0.000 description 4
- 239000000440 bentonite Substances 0.000 description 4
- 229910000278 bentonite Inorganic materials 0.000 description 4
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- LQZPSWMMTICWHD-UHFFFAOYSA-N 1,3-bis(benzyl)thiourea Natural products C=1C=CC=CC=1CNC(=S)NCC1=CC=CC=C1 LQZPSWMMTICWHD-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- 241000255925 Diptera Species 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000358422 Nephotettix cincticeps Species 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 241000176086 Sogatella furcifera Species 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 229920005551 calcium lignosulfonate Polymers 0.000 description 3
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 3
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 3
- 210000003608 fece Anatomy 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
- 239000003350 kerosene Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- FQAINYUMTUUOFC-UHFFFAOYSA-N n-(chloromethyl)-n-propan-2-ylcarbamoyl chloride Chemical compound CC(C)N(CCl)C(Cl)=O FQAINYUMTUUOFC-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- HUTLODTYVWHFRI-UHFFFAOYSA-N 1,3,5-thiadiazin-4-one Chemical compound O=C1N=CSC=N1 HUTLODTYVWHFRI-UHFFFAOYSA-N 0.000 description 2
- LKLLNYWECKEQIB-UHFFFAOYSA-N 1,3,5-triazinane Chemical compound C1NCNCN1 LKLLNYWECKEQIB-UHFFFAOYSA-N 0.000 description 2
- VASMRQAVWVVDPA-UHFFFAOYSA-N 1,3,5-triphenyl-1,3,5-triazinane Chemical compound C1N(C=2C=CC=CC=2)CN(C=2C=CC=CC=2)CN1C1=CC=CC=C1 VASMRQAVWVVDPA-UHFFFAOYSA-N 0.000 description 2
- NUFYYNZSNVIRJN-UHFFFAOYSA-N 1,3,5-tris(2,4-dimethylphenyl)-1,3,5-triazinane Chemical compound CC1=CC(C)=CC=C1N1CN(C=2C(=CC(C)=CC=2)C)CN(C=2C(=CC(C)=CC=2)C)C1 NUFYYNZSNVIRJN-UHFFFAOYSA-N 0.000 description 2
- IPJSUMKHBGDQMQ-UHFFFAOYSA-N 1,3,5-tris(4-ethoxyphenyl)-1,3,5-triazinane Chemical compound C1=CC(OCC)=CC=C1N1CN(C=2C=CC(OCC)=CC=2)CN(C=2C=CC(OCC)=CC=2)C1 IPJSUMKHBGDQMQ-UHFFFAOYSA-N 0.000 description 2
- SJPZRVSVJDQKSP-UHFFFAOYSA-N 1,3,5-tris(4-ethylphenyl)-1,3,5-triazinane Chemical compound C1=CC(CC)=CC=C1N1CN(C=2C=CC(CC)=CC=2)CN(C=2C=CC(CC)=CC=2)C1 SJPZRVSVJDQKSP-UHFFFAOYSA-N 0.000 description 2
- UAJWDYLSRSNGFH-UHFFFAOYSA-N 1,3,5-tris(4-methylphenyl)-1,3,5-triazinane Chemical compound C1=CC(C)=CC=C1N1CN(C=2C=CC(C)=CC=2)CN(C=2C=CC(C)=CC=2)C1 UAJWDYLSRSNGFH-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- RLTDXTUGGXRDEW-UHFFFAOYSA-N 1-benzyl-3-tert-butylthiourea Chemical compound CC(C)(C)NC(=S)NCC1=CC=CC=C1 RLTDXTUGGXRDEW-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 235000010149 Brassica rapa subsp chinensis Nutrition 0.000 description 2
- 235000000536 Brassica rapa subsp pekinensis Nutrition 0.000 description 2
- 241000499436 Brassica rapa subsp. pekinensis Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 240000000560 Citrus x paradisi Species 0.000 description 2
- 241000255749 Coccinellidae Species 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 241001470017 Laodelphax striatella Species 0.000 description 2
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- FLVIGYVXZHLUHP-UHFFFAOYSA-N N,N'-diethylthiourea Chemical compound CCNC(=S)NCC FLVIGYVXZHLUHP-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 229940113088 dimethylacetamide Drugs 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- ZMBSRNHDTFKMLI-UHFFFAOYSA-N n-(2,6-diethylphenyl)methanimine Chemical compound CCC1=CC=CC(CC)=C1N=C ZMBSRNHDTFKMLI-UHFFFAOYSA-N 0.000 description 2
- DVEJPRNXGSWVJV-UHFFFAOYSA-N n-(2,6-dimethylphenyl)methanimine Chemical compound CC1=CC=CC(C)=C1N=C DVEJPRNXGSWVJV-UHFFFAOYSA-N 0.000 description 2
- KZCHEKYZIZAEGG-UHFFFAOYSA-N n-(chloromethyl)-n-(2-chlorophenyl)carbamoyl chloride Chemical compound ClCN(C(Cl)=O)C1=CC=CC=C1Cl KZCHEKYZIZAEGG-UHFFFAOYSA-N 0.000 description 2
- JJZXFDWKGLVKAR-UHFFFAOYSA-N n-(chloromethyl)-n-(3,4-dichlorophenyl)carbamoyl chloride Chemical compound ClCN(C(Cl)=O)C1=CC=C(Cl)C(Cl)=C1 JJZXFDWKGLVKAR-UHFFFAOYSA-N 0.000 description 2
- JCVCRMUMWKQENZ-UHFFFAOYSA-N n-(chloromethyl)-n-(4-chlorophenyl)carbamoyl chloride Chemical compound ClCN(C(Cl)=O)C1=CC=C(Cl)C=C1 JCVCRMUMWKQENZ-UHFFFAOYSA-N 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 230000001766 physiological effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- QMJZSLUHROJGLM-UHFFFAOYSA-N 1,3,5-tris(2,3-dimethylphenyl)-1,3,5-triazinane Chemical compound CC1=CC=CC(N2CN(CN(C2)C=2C(=C(C)C=CC=2)C)C=2C(=C(C)C=CC=2)C)=C1C QMJZSLUHROJGLM-UHFFFAOYSA-N 0.000 description 1
- QJDMZRQPSLCTRT-UHFFFAOYSA-N 1,3,5-tris(2-ethylphenyl)-1,3,5-triazinane Chemical compound CCC1=CC=CC=C1N1CN(C=2C(=CC=CC=2)CC)CN(C=2C(=CC=CC=2)CC)C1 QJDMZRQPSLCTRT-UHFFFAOYSA-N 0.000 description 1
- JZNPIGWAHAEPOW-UHFFFAOYSA-N 1,3,5-tris(2-methylphenyl)-1,3,5-triazinane Chemical compound CC1=CC=CC=C1N1CN(C=2C(=CC=CC=2)C)CN(C=2C(=CC=CC=2)C)C1 JZNPIGWAHAEPOW-UHFFFAOYSA-N 0.000 description 1
- OXCFNKCIPUZDPZ-UHFFFAOYSA-N 1,3,5-tris(4-chloro-2-methylphenyl)-1,3,5-triazinane Chemical compound CC1=CC(Cl)=CC=C1N1CN(C=2C(=CC(Cl)=CC=2)C)CN(C=2C(=CC(Cl)=CC=2)C)C1 OXCFNKCIPUZDPZ-UHFFFAOYSA-N 0.000 description 1
- KCXDQGHUQVPUFS-UHFFFAOYSA-N 1,3,5-tris(4-methoxyphenyl)-1,3,5-triazinane Chemical compound C1=CC(OC)=CC=C1N1CN(C=2C=CC(OC)=CC=2)CN(C=2C=CC(OC)=CC=2)C1 KCXDQGHUQVPUFS-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical class C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- CGYOFRQSUNUTHU-UHFFFAOYSA-N 1-(2-methylpropyl)-3-propan-2-ylthiourea Chemical compound CC(C)CNC(=S)NC(C)C CGYOFRQSUNUTHU-UHFFFAOYSA-N 0.000 description 1
- GDUBTTXVKWIAKV-UHFFFAOYSA-N 1-benzyl-3-methylthiourea Chemical compound CNC(=S)NCC1=CC=CC=C1 GDUBTTXVKWIAKV-UHFFFAOYSA-N 0.000 description 1
- IFPFRGOIUODXNB-UHFFFAOYSA-N 1-benzyl-3-propan-2-ylthiourea Chemical compound CC(C)NC(=S)NCC1=CC=CC=C1 IFPFRGOIUODXNB-UHFFFAOYSA-N 0.000 description 1
- QFGONZUOOBRNMD-UHFFFAOYSA-N 1-butan-2-yl-3-propan-2-ylthiourea Chemical compound CCC(C)NC(=S)NC(C)C QFGONZUOOBRNMD-UHFFFAOYSA-N 0.000 description 1
- HNHAUTOYMGIGCQ-UHFFFAOYSA-N 1-butan-2-yl-3-tert-butylthiourea Chemical compound CCC(C)NC(=S)NC(C)(C)C HNHAUTOYMGIGCQ-UHFFFAOYSA-N 0.000 description 1
- OROCFDLTBPBLFS-UHFFFAOYSA-N 1-ethyl-3-phenylthiourea Chemical compound CCNC(=S)NC1=CC=CC=C1 OROCFDLTBPBLFS-UHFFFAOYSA-N 0.000 description 1
- IIMGWZIVKIMTGU-UHFFFAOYSA-N 1-methyl-3-(4-methylphenyl)thiourea Chemical compound CNC(=S)NC1=CC=C(C)C=C1 IIMGWZIVKIMTGU-UHFFFAOYSA-N 0.000 description 1
- OIIFYBCNDAMJFE-UHFFFAOYSA-N 1-methyl-3-octylthiourea Chemical compound CCCCCCCCNC(=S)NC OIIFYBCNDAMJFE-UHFFFAOYSA-N 0.000 description 1
- IGEQFPWPMCIYDF-UHFFFAOYSA-N 1-methyl-3-phenylthiourea Chemical compound CNC(=S)NC1=CC=CC=C1 IGEQFPWPMCIYDF-UHFFFAOYSA-N 0.000 description 1
- GUABXNOIRYHFOC-UHFFFAOYSA-N 1-tert-butyl-3-cyclohexylthiourea Chemical compound CC(C)(C)NC(=S)NC1CCCCC1 GUABXNOIRYHFOC-UHFFFAOYSA-N 0.000 description 1
- PQNUKVMRFKBOJD-UHFFFAOYSA-N 1-tert-butyl-3-ethylthiourea Chemical compound CCNC(=S)NC(C)(C)C PQNUKVMRFKBOJD-UHFFFAOYSA-N 0.000 description 1
- SWQHPNZHQSIPCQ-UHFFFAOYSA-N 1-tert-butyl-3-methylthiourea Chemical compound CNC(=S)NC(C)(C)C SWQHPNZHQSIPCQ-UHFFFAOYSA-N 0.000 description 1
- JHMCTNQTJNGVRX-UHFFFAOYSA-N 1-tert-butyl-3-phenylthiourea Chemical compound CC(C)(C)NC(=S)NC1=CC=CC=C1 JHMCTNQTJNGVRX-UHFFFAOYSA-N 0.000 description 1
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- MUZHOURERNKMFG-UHFFFAOYSA-N 2-benzylimino-3-methyl-5-phenyl-1,3,5-thiadiazinan-4-one Chemical compound CN1C(=O)N(C=2C=CC=CC=2)CSC1=NCC1=CC=CC=C1 MUZHOURERNKMFG-UHFFFAOYSA-N 0.000 description 1
- QJQBMFHTRPMMSG-UHFFFAOYSA-N 2-butan-2-ylimino-5-phenyl-3-propan-2-yl-1,3,5-thiadiazinan-4-one Chemical compound C(C)(CC)N=C1SCN(C(N1C(C)C)=O)C1=CC=CC=C1 QJQBMFHTRPMMSG-UHFFFAOYSA-N 0.000 description 1
- LSRIAZBRACZROG-UHFFFAOYSA-N 2-methylimino-3-phenyl-5-propan-2-yl-1,3,5-thiadiazinan-4-one Chemical compound CN=C1SCN(C(C)C)C(=O)N1C1=CC=CC=C1 LSRIAZBRACZROG-UHFFFAOYSA-N 0.000 description 1
- GHXQUAACXLNXCS-UHFFFAOYSA-N 2-tert-butylimino-3-cyclohexyl-5-phenyl-1,3,5-thiadiazinan-4-one Chemical compound CC(C)(C)N=C1SCN(C=2C=CC=CC=2)C(=O)N1C1CCCCC1 GHXQUAACXLNXCS-UHFFFAOYSA-N 0.000 description 1
- AKQZGOQILFJRCF-UHFFFAOYSA-N 2-tert-butylimino-3-ethyl-5-phenyl-1,3,5-thiadiazinan-4-one Chemical compound C1SC(=NC(C)(C)C)N(CC)C(=O)N1C1=CC=CC=C1 AKQZGOQILFJRCF-UHFFFAOYSA-N 0.000 description 1
- CCFIAIYHTFDUDR-UHFFFAOYSA-N 2-tert-butylimino-5-(2,6-dimethylphenyl)-3-propan-2-yl-1,3,5-thiadiazinan-4-one Chemical compound O=C1N(C(C)C)C(=NC(C)(C)C)SCN1C1=C(C)C=CC=C1C CCFIAIYHTFDUDR-UHFFFAOYSA-N 0.000 description 1
- YHFMJBSLRGWYLW-UHFFFAOYSA-N 2-tert-butylimino-5-(4-chloro-2-methylphenyl)-3-propan-2-yl-1,3,5-thiadiazinan-4-one Chemical compound C1SC(=NC(C)(C)C)N(C(C)C)C(=O)N1C1=CC=C(Cl)C=C1C YHFMJBSLRGWYLW-UHFFFAOYSA-N 0.000 description 1
- RUKPMDNZGHNLPD-UHFFFAOYSA-N 2-tert-butylimino-5-(4-chlorophenyl)-3-propan-2-yl-1,3,5-thiadiazinan-4-one Chemical compound C1SC(=NC(C)(C)C)N(C(C)C)C(=O)N1C1=CC=C(Cl)C=C1 RUKPMDNZGHNLPD-UHFFFAOYSA-N 0.000 description 1
- GSRHRLURZNAPIX-UHFFFAOYSA-N 2-tert-butylimino-5-(4-ethylphenyl)-3-propan-2-yl-1,3,5-thiadiazinan-4-one Chemical compound C1=CC(CC)=CC=C1N1C(=O)N(C(C)C)C(=NC(C)(C)C)SC1 GSRHRLURZNAPIX-UHFFFAOYSA-N 0.000 description 1
- UXXCNIGXXCIREG-UHFFFAOYSA-N 2-tert-butylimino-5-(4-fluorophenyl)-3-propan-2-yl-1,3,5-thiadiazinan-4-one Chemical compound C1SC(=NC(C)(C)C)N(C(C)C)C(=O)N1C1=CC=C(F)C=C1 UXXCNIGXXCIREG-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- BGSOVOFSGODCIQ-UHFFFAOYSA-N 3,5-diethyl-2-ethylimino-1,3,5-thiadiazinan-4-one Chemical compound CCN=C1SCN(CC)C(=O)N1CC BGSOVOFSGODCIQ-UHFFFAOYSA-N 0.000 description 1
- VLZGCKVNKLNAQI-UHFFFAOYSA-N 3-(2-methylpropyl)-5-phenyl-2-propan-2-ylimino-1,3,5-thiadiazinan-4-one Chemical compound C1SC(=NC(C)C)N(CC(C)C)C(=O)N1C1=CC=CC=C1 VLZGCKVNKLNAQI-UHFFFAOYSA-N 0.000 description 1
- VPKOISSWTISNHY-UHFFFAOYSA-N 3-benzyl-2-benzylimino-5-(4-propan-2-yloxyphenyl)-1,3,5-thiadiazinan-4-one Chemical compound C1=CC(OC(C)C)=CC=C1N(CS1)C(=O)N(CC=2C=CC=CC=2)C1=NCC1=CC=CC=C1 VPKOISSWTISNHY-UHFFFAOYSA-N 0.000 description 1
- GKPJTODGTWOBKF-UHFFFAOYSA-N 3-benzyl-2-tert-butylimino-5-(4-chlorophenyl)-1,3,5-thiadiazinan-4-one Chemical compound CC(C)(C)N=C1SCN(C=2C=CC(Cl)=CC=2)C(=O)N1CC1=CC=CC=C1 GKPJTODGTWOBKF-UHFFFAOYSA-N 0.000 description 1
- ARPYFOHKOFNOEB-UHFFFAOYSA-N 3-benzyl-5-tert-butyl-2-tert-butylimino-1,3,5-thiadiazinan-4-one Chemical compound CC(C)(C)N=C1SCN(C(C)(C)C)C(=O)N1CC1=CC=CC=C1 ARPYFOHKOFNOEB-UHFFFAOYSA-N 0.000 description 1
- WGHXZCUQJIGEGV-UHFFFAOYSA-N 3-butan-2-yl-2-tert-butylimino-5-(3-chlorophenyl)-1,3,5-thiadiazinan-4-one Chemical compound C1SC(=NC(C)(C)C)N(C(C)CC)C(=O)N1C1=CC=CC(Cl)=C1 WGHXZCUQJIGEGV-UHFFFAOYSA-N 0.000 description 1
- RBJBODKEJXHROV-UHFFFAOYSA-N 3-butan-2-yl-2-tert-butylimino-5-(4-ethoxyphenyl)-1,3,5-thiadiazinan-4-one Chemical compound C1=CC(OCC)=CC=C1N1C(=O)N(C(C)CC)C(=NC(C)(C)C)SC1 RBJBODKEJXHROV-UHFFFAOYSA-N 0.000 description 1
- ZVRIGMHRMUJWMM-UHFFFAOYSA-N 3-butan-2-yl-2-tert-butylimino-5-(4-propan-2-yloxyphenyl)-1,3,5-thiadiazinan-4-one Chemical compound C1SC(=NC(C)(C)C)N(C(C)CC)C(=O)N1C1=CC=C(OC(C)C)C=C1 ZVRIGMHRMUJWMM-UHFFFAOYSA-N 0.000 description 1
- ZTLCHLISBJAYAA-UHFFFAOYSA-N 3-methyl-2-octylimino-5-phenyl-1,3,5-thiadiazinan-4-one Chemical compound O=C1N(C)C(=NCCCCCCCC)SCN1C1=CC=CC=C1 ZTLCHLISBJAYAA-UHFFFAOYSA-N 0.000 description 1
- QWPGROFTVKBJIF-UHFFFAOYSA-N 3-methyl-2-propan-2-ylimino-5-(4-propan-2-yloxyphenyl)-1,3,5-thiadiazinan-4-one Chemical compound C1=CC(OC(C)C)=CC=C1N1C(=O)N(C)C(=NC(C)C)SC1 QWPGROFTVKBJIF-UHFFFAOYSA-N 0.000 description 1
- PTZALIPZJFXNLD-UHFFFAOYSA-N 3-methyl-5-phenyl-2-propan-2-ylimino-1,3,5-thiadiazinan-4-one Chemical compound O=C1N(C)C(=NC(C)C)SCN1C1=CC=CC=C1 PTZALIPZJFXNLD-UHFFFAOYSA-N 0.000 description 1
- HKUVIWPUODJGAE-UHFFFAOYSA-N 3-propan-2-yl-2-propan-2-ylimino-5-[3-(trifluoromethyl)phenyl]-1,3,5-thiadiazinan-4-one Chemical compound O=C1N(C(C)C)C(=NC(C)C)SCN1C1=CC=CC(C(F)(F)F)=C1 HKUVIWPUODJGAE-UHFFFAOYSA-N 0.000 description 1
- BNNTXAOQVWBBLH-UHFFFAOYSA-N 3-propan-2-yl-5-[3-(trifluoromethyl)phenyl]-2-(2,4,4-trimethylpentan-2-ylimino)-1,3,5-thiadiazinan-4-one Chemical compound C1SC(=NC(C)(C)CC(C)(C)C)N(C(C)C)C(=O)N1C1=CC=CC(C(F)(F)F)=C1 BNNTXAOQVWBBLH-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- UKDNLAWAQUHTNI-UHFFFAOYSA-N 5-(2,4-dimethylphenyl)-3-methyl-2-propan-2-ylimino-1,3,5-thiadiazinan-4-one Chemical compound O=C1N(C)C(=NC(C)C)SCN1C1=CC=C(C)C=C1C UKDNLAWAQUHTNI-UHFFFAOYSA-N 0.000 description 1
- NDVCQCURQZAOOI-UHFFFAOYSA-N 5-(2,4-dimethylphenyl)-3-propan-2-yl-2-propan-2-ylimino-1,3,5-thiadiazinan-4-one Chemical compound O=C1N(C(C)C)C(=NC(C)C)SCN1C1=CC=C(C)C=C1C NDVCQCURQZAOOI-UHFFFAOYSA-N 0.000 description 1
- CDWLZOWDRXQWNX-UHFFFAOYSA-N 5-(2,6-diethylphenyl)-3-methyl-2-propan-2-ylimino-1,3,5-thiadiazinan-4-one Chemical compound CCC1=CC=CC(CC)=C1N1C(=O)N(C)C(=NC(C)C)SC1 CDWLZOWDRXQWNX-UHFFFAOYSA-N 0.000 description 1
- PRZACNROSKVBND-UHFFFAOYSA-N 5-(2,6-diethylphenyl)-3-propan-2-yl-2-propan-2-ylimino-1,3,5-thiadiazinan-4-one Chemical compound CCC1=CC=CC(CC)=C1N1C(=O)N(C(C)C)C(=NC(C)C)SC1 PRZACNROSKVBND-UHFFFAOYSA-N 0.000 description 1
- WPQOLRQSTGHIKJ-UHFFFAOYSA-N 5-(2,6-dimethylphenyl)-3-methyl-2-methylimino-1,3,5-thiadiazinan-4-one Chemical compound O=C1N(C)C(=NC)SCN1C1=C(C)C=CC=C1C WPQOLRQSTGHIKJ-UHFFFAOYSA-N 0.000 description 1
- HCNSCJNFDUNXSA-UHFFFAOYSA-N 5-(2-chlorophenyl)-2-cyclohexylimino-3-propan-2-yl-1,3,5-thiadiazinan-4-one Chemical compound O=C1N(C(C)C)C(=NC2CCCCC2)SCN1C1=CC=CC=C1Cl HCNSCJNFDUNXSA-UHFFFAOYSA-N 0.000 description 1
- ZTSRNIPPABAXGU-UHFFFAOYSA-N 5-(2-methylphenyl)-3-propan-2-yl-2-propan-2-ylimino-1,3,5-thiadiazinan-4-one Chemical compound O=C1N(C(C)C)C(=NC(C)C)SCN1C1=CC=CC=C1C ZTSRNIPPABAXGU-UHFFFAOYSA-N 0.000 description 1
- BXDMJLZOXBWLKV-UHFFFAOYSA-N 5-(3,4-dichlorophenyl)-3-ethyl-2-ethylimino-1,3,5-thiadiazinan-4-one Chemical compound O=C1N(CC)C(=NCC)SCN1C1=CC=C(Cl)C(Cl)=C1 BXDMJLZOXBWLKV-UHFFFAOYSA-N 0.000 description 1
- XZULNOHICFDBQY-UHFFFAOYSA-N 5-(4-chlorophenyl)-3-methyl-2-propan-2-ylimino-1,3,5-thiadiazinan-4-one Chemical compound O=C1N(C)C(=NC(C)C)SCN1C1=CC=C(Cl)C=C1 XZULNOHICFDBQY-UHFFFAOYSA-N 0.000 description 1
- PXWVWXZDTCSMJS-UHFFFAOYSA-N 5-(4-fluorophenyl)-3-methyl-2-methylimino-1,3,5-thiadiazinan-4-one;hydrochloride Chemical compound Cl.O=C1N(C)C(=NC)SCN1C1=CC=C(F)C=C1 PXWVWXZDTCSMJS-UHFFFAOYSA-N 0.000 description 1
- DXOCLYUTOCJHRQ-UHFFFAOYSA-N 5-methyl-3-propan-2-yl-2-propan-2-ylimino-1,3,5-thiadiazinan-4-one Chemical compound CC(C)N=C1SCN(C)C(=O)N1C(C)C DXOCLYUTOCJHRQ-UHFFFAOYSA-N 0.000 description 1
- HSXMWAMNNUETHN-UHFFFAOYSA-N 5-phenyl-3-propan-2-yl-2-propan-2-ylimino-1,3,5-thiadiazinan-4-one Chemical compound O=C1N(C(C)C)C(=NC(C)C)SCN1C1=CC=CC=C1 HSXMWAMNNUETHN-UHFFFAOYSA-N 0.000 description 1
- LHIYUXMWIRLYAE-UHFFFAOYSA-N 5-tert-butyl-2-ethylimino-3-(2-methylphenyl)-1,3,5-thiadiazinan-4-one Chemical compound CCN=C1SCN(C(C)(C)C)C(=O)N1C1=CC=CC=C1C LHIYUXMWIRLYAE-UHFFFAOYSA-N 0.000 description 1
- IDWCWUANPPDVTG-UHFFFAOYSA-N 5-tert-butyl-3-methyl-2-(4-methylphenyl)imino-1,3,5-thiadiazinan-4-one Chemical compound CN1C(=O)N(C(C)(C)C)CSC1=NC1=CC=C(C)C=C1 IDWCWUANPPDVTG-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 206010004194 Bed bug infestation Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OWEAIUDWIDYSAR-UHFFFAOYSA-N CC(C)NC(=S)NC(C)(C)CC(C)(C)C Chemical compound CC(C)NC(=S)NC(C)(C)CC(C)(C)C OWEAIUDWIDYSAR-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000887125 Chaptalia nutans Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241001414835 Cimicidae Species 0.000 description 1
- 241001498622 Cixius wagneri Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000256059 Culex pipiens Species 0.000 description 1
- 241000328422 Culiseta annulata Species 0.000 description 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 1
- 241001301805 Epilachna Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 240000002024 Gossypium herbaceum Species 0.000 description 1
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 244000118681 Iresine herbstii Species 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 239000005949 Malathion Substances 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 description 1
- FCSHMCFRCYZTRQ-UHFFFAOYSA-N N,N'-diphenylthiourea Chemical compound C=1C=CC=CC=1NC(=S)NC1=CC=CC=C1 FCSHMCFRCYZTRQ-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- VUYCBBHNGBWOJM-UHFFFAOYSA-N NCOCl Chemical compound NCOCl VUYCBBHNGBWOJM-UHFFFAOYSA-N 0.000 description 1
- 241000359016 Nephotettix Species 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 235000019774 Rice Bran oil Nutrition 0.000 description 1
- 241000176085 Sogatella Species 0.000 description 1
- 235000019764 Soybean Meal Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241000779819 Syncarpia glomulifera Species 0.000 description 1
- 241000843170 Togo hemipterus Species 0.000 description 1
- 241000254086 Tribolium <beetle> Species 0.000 description 1
- 241000254113 Tribolium castaneum Species 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 235000019498 Walnut oil Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- BZMIHNKNQJJVRO-LVZFUZTISA-N [(e)-c-(3-chloro-2,6-dimethoxyphenyl)-n-ethoxycarbonimidoyl] benzoate Chemical compound COC=1C=CC(Cl)=C(OC)C=1C(=N/OCC)\OC(=O)C1=CC=CC=C1 BZMIHNKNQJJVRO-LVZFUZTISA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- WFDOLCYFWRFQEG-UHFFFAOYSA-N butan-2-ylthiourea Chemical compound CCC(C)NC(N)=S WFDOLCYFWRFQEG-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 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
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- DCTOHCCUXLBQMS-UHFFFAOYSA-N cis-undecene Natural products CCCCCCCCCC=C DCTOHCCUXLBQMS-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 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
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 230000009189 diving Effects 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000000763 evoking effect Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 239000010881 fly ash Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QKGYJVXSKCDGOK-UHFFFAOYSA-N hexane;propan-2-ol Chemical compound CC(C)O.CCCCCC QKGYJVXSKCDGOK-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- UWNADWZGEHDQAB-UHFFFAOYSA-N i-Pr2C2H4i-Pr2 Natural products CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000003621 irrigation water Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000017932 juta Nutrition 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 229960000453 malathion Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 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
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- AXPMKKGXYIYYOJ-UHFFFAOYSA-N n-(chloromethyl)-n-(3-chlorophenyl)carbamoyl chloride Chemical compound ClCN(C(Cl)=O)C1=CC=CC(Cl)=C1 AXPMKKGXYIYYOJ-UHFFFAOYSA-N 0.000 description 1
- QYDQDLJLCQBUMQ-UHFFFAOYSA-N n-(chloromethyl)-n-(4-fluorophenyl)carbamoyl chloride Chemical compound FC1=CC=C(N(CCl)C(Cl)=O)C=C1 QYDQDLJLCQBUMQ-UHFFFAOYSA-N 0.000 description 1
- NYHTWFZRTZQTNZ-UHFFFAOYSA-N n-(chloromethyl)-n-ethylcarbamoyl chloride Chemical compound CCN(CCl)C(Cl)=O NYHTWFZRTZQTNZ-UHFFFAOYSA-N 0.000 description 1
- FSBLIZXPIXHWML-UHFFFAOYSA-N n-(chloromethyl)-n-methylcarbamoyl chloride Chemical compound ClCN(C)C(Cl)=O FSBLIZXPIXHWML-UHFFFAOYSA-N 0.000 description 1
- ICXBWJZFEPUSSN-UHFFFAOYSA-N n-benzyl-n-(chloromethyl)carbamoyl chloride Chemical compound ClCN(C(Cl)=O)CC1=CC=CC=C1 ICXBWJZFEPUSSN-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- VQWLIRNLTYKJMV-UHFFFAOYSA-N n-tert-butyl-n-(chloromethyl)carbamoyl chloride Chemical compound CC(C)(C)N(CCl)C(Cl)=O VQWLIRNLTYKJMV-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229920003124 powdered cellulose Polymers 0.000 description 1
- 235000019814 powdered cellulose Nutrition 0.000 description 1
- 239000012254 powdered material Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Chemical class 0.000 description 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000008165 rice bran oil Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010898 silica gel chromatography Methods 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
- 229920002545 silicone oil Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- QPQBEKRULCQLKT-UHFFFAOYSA-M sodium;benzene;hydroxide Chemical compound [OH-].[Na+].C1=CC=CC=C1 QPQBEKRULCQLKT-UHFFFAOYSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000004455 soybean meal Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000008170 walnut oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 235000015099 wheat brans Nutrition 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/88—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with three ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
- C07D285/34—1,3,5-Thiadiazines; Hydrogenated 1,3,5-thiadiazines
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material 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)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
CH,
Verbin
dung Nr. |
Substituentengruppe
R1 |
R2 | R3 |
Physikalische
Eigenschaften |
1 | CH3 | C2H5 | C2H5 | Fp. 82-840C |
2 | CH3 | i-C3H7 | J-C3H7 | Fp. 76-77°C |
3 | CH3 | n-C3H7 | t-C4H, | Fp. 81-820C |
4 | CH3 | n-C6H13 | n-C6H13 | Fp. 63-65°C |
5 | CjHs |
6 | CjH5 |
7 | C2H5 |
8 | C2H5 |
9 | CH2CH = CH2 |
10 | CH2CH = CH2 |
11 | C H2C H ^= C H 2 |
12 | CH2CH = CH2 |
13 | n-C3H7 |
14 | 11-C3H7 |
15 | n-C3H7 |
16 | J-C3H7 |
17 | i-C3H7 |
18 | .-C3H7 |
19 | i-C3H7 |
20 | i-C3H7 |
21 | i-C3H7 |
22 | UC3H7 |
23 | 1-C3H5 |
24 | 1-C3H7 |
25 | 11-C4H, |
26 | 11-C4H9 |
27 | i-C«H, |
28 | J-C3H7 |
29 | S-C4H9 |
30 | S-C4H, |
31 | t-C4H, |
32 | t-C4H, |
33 | t-C/4119 |
34 | t-C4H, |
35 | t-C4H9 |
36 | t-C4H, |
37 | t-C4H, |
38 | t-C4H, |
39 | t-C4H, |
40 | t-C4H, |
41 | t-C4H, |
42 | t-C4H, |
CH3 | Fp. 43-44°C |
t-C4H» | Fp. 68-690C |
C2H5 | Fp. 68-70°C |
UC3H, | Fp. 61-62°C |
CH3 | n2g 1,5615 |
UC3H7 | njf 1,5380 |
C2H5 | ni° 1,5397 |
n-C3H7 | «b" 1,5285 |
UC3H7 | ni° 1,5310 |
UC3H7 | «!," 1,5166 |
UC3H7 | «£" 1,5185 |
CH3 | Fp. 92-930C |
C2H5 | Fp. 93-95°C |
UC3H7 | Fp. 87-88°C |
Benzyl | Fp. 106-108°C |
H-C6H13 | n2 p 0 1,5199 |
2-Äthylhexyl | nj? 1,5180 |
n-CisH|7 | n-o" 1,5167 |
C2H5 | 4" 1,5264 |
n-C3H? | ng' 1,5160 |
UC3H7 | Fp. 84-85°C |
S-C4H, | Fp. 81-82°C |
UC3H, | Fp. 93-94°C |
Cyclohexyl | Fp. 98-990C |
UC3H7 | Fp. 82-83°C |
UC3H7 | Fp. 89-900C |
CH3 | Fp. 51-52°C |
n-C3H7 | n$ 1,5273 |
UC3H7 | Fp. 62-63°C |
n-C4H, | «b° 1,5185 |
S-C4H9 | Fp. 83-84°C |
UC4H, | Fp. 77-78°C |
t-C4H, | Fp. 107-1080C |
Benzyl | Fp. 125-1270C |
n-CfcHu | nJ D° 1,5122 |
n-C|H(7 | Fp. 58-59°C |
C2H5 | «-ο" 1,5235 |
t-C4H, | ni° 1,5189 |
43 | t-C4H, | n-C3H7 |
44 | IC4H, | n-C3H7 |
45 | t-C4H, | n-C4H, |
46 | t-C4H, | IVC4H, |
47 | 1-C4H, | Benzyl |
48 | t-C4Hv | i-C3H7 |
49 | t-C4H, | n-C,H, |
50 | H-C6H13 | CH3 |
51 | n-C*HI3 | J-C3H7 |
52 | Cyclohexyl | J-C3H7 |
53 | Cyclohexyl | CH3 |
54 | Benzyl | CH3 |
55 | Benzyl | C2H5 |
56 | Benzyl | n-C3H7 |
57 | Benzyl | Benzyl |
58 | t-C,H17 | CH3 |
59 | t-C,H17 | CH3 |
60 | t-C,H„ | CH, |
61 | t-C,H17 | t-C4H, |
62 | t-C,HI7 | CH3 |
63 | t-C,HI7 | CH3 |
64 | n-C,HI7 | CH3 |
65 | Ji-CgH17 | CH, |
66 | i-C,H, | Phenyl |
68 | S-C3H7 |
69 | t-C4H, |
70 | t-C4H, |
71 | t-C4H, |
72 | t-C4H, |
73 | t-C4H, |
R-1 |
Physikalische
Eigenschaften |
J-C3H7 | ng 1,5160 |
n-C4H, | η? 1,5096 |
H-C4H9 | n$ 1,5065 |
t-C4H, | «b° 1,5085 |
IC4H, | Fp. 75-760C |
t-C,H,7 | Fp. 89-9I0C |
n-C»H17 | κ§ 1,5003 |
J-C3H7 | nb° 1,5195 |
i-C3H7 | ng" 1,5188 |
i-C3H7 | n2S 1,5205 |
t-C4H, | η? 1,5210 |
CH, | Fp. 93-950C |
C2H5 | n2S 1,5630 |
n-C,H7 | ng" 1,5653 |
i-C3H7 | n2g 1,5780 |
CH3 | Fp. 66-680C |
i-C,H7 | β? 1,5100 |
CHj=CHCH2 | ng 1,5210 |
n-C4H, | ng 1,5112 |
J-C4H, | n$ 1,5110 |
t-C4H, | Fp. 91-93°C |
CH3 | ng' 1,5190 |
i-C,H7 | ni° 1,5185 |
CH3 | Fp. 174-176°C |
CHj | |
-V~V-ci | Fp. 91-92°C |
74 | 1-C4H, |
75 | t-C4H, |
7(5 | 1-C4H, |
77 | t-C4H, |
718 | t-C4H, |
79 | t-C4H, |
83 | t-C4H, |
84 | t-C4H, |
85 | Benzyl |
86 | Benzyl |
Phenyl | n-C3H, | Fp. 109-UO0C |
Phenyl | J-C3H7 | Fp. 136-137°C |
Phenyl | n-C4H, | Fp. 115-116°C |
Phenyl | t-C4H, | Fp. 133-134°C |
Phenyl | Phenyl | Fp. 111-112°C |
Phenyl | n-CgHi7 | Fp. 59°C |
CH3
I |
||
CjH5 | Fp. 157-158°C |
(CHj)JCHCHjCHj | t-C4H, |
Cyclohexyl | Cyclohexyl |
CH, | CH3 |
n-C4H, | i-C3H7 |
i-C4H, | t-C4H, |
n-C,H13 | i-C3H7 |
C2H5 | C2H5 |
Verbindung
Nr. |
Rz |
114 | CH3 |
115 | CH3 |
116 | CH3 |
117 | CH3 |
118 | CH3 |
119 | CH3 |
(Fortsetzung) | R2 | 28 24 126 | CH3 | Physikalische Eigenschaften | |
Verbindung
Nr. |
CH3 | Fp. 90-920C | |||
120 | CH3 | R3 | n2 D 0 1,5551 | ||
121 | CH3 | Benzyl | Fp. IO1-1O3°C | ||
122 | D-CjH17 | ||||
10 | CH3 | H | Fp. 113-1140C | ||
123 | |||||
< 15 | |||||
124 | C2H5 | C2H5 | Fp. 55-580C |
125 | C2H5 | D-C3H7 | /iff 1,5800 |
126 | C2H5 | i-C3H7 | Fp. 69-71°C |
127 | C2H5 | n-C4H, | ni" 1,5709 |
128 | C2H5 | i-C4H, | Fp. 85-88°C |
129 | C2H5 | S-C4H9 | Fp. 88-89°C |
130 | C2H5 | UC4H, | Fp. 93-94°C |
131 | C2H5 | Cyclohexyl | Fp. 133-135°C |
132 | C2H5 | n-CjHI7 | n:o° 1,5468 |
133 | n-C3H7 | n-C3H7 | nj? 1.5090 |
134 | n-C3H, | 1-C3H7 | n'D° 1,5646 |
135 | n-CjH, | S-C4H, | ng' 1,5579 |
136 | n-C3H7 | t-C4H, | Fp. 65-67°C |
137 | n-C3H7 | Cyclohexyl | /ig* 1,5697 |
138 | CH2=CHCH2 | CH2=CHCH3 | «b" 1,5941 |
139 | CH2=CHCH2 | n-C3H7 | «7? 1,5753 |
140 | CHj = CHCHj | i-C3H7 | /ΐί,6 1,5722 |
141 | CH2=CHCH2 | S-C4H, | «j,ft 1,5719 |
142 | CH2=CHCH2 | t-C4H, | Fp. 46-47°C |
143 | i-C3H7 | i-C3H7 | Fp. 92-94°C |
144 | i-CjH, | t-C4H, | Fp. 104-106°C |
145 | n-C4H, | n-C4H, | n$ 1,5604 |
146 | n-C4H, | i-C3H7 | «/," 1,5580 |
147 | i-C4H, | i-C4H, | Fp. 82-83°C |
148 | i-C4H, | i-C3H7 | Fp. 80-820C |
149 | i-C4H.„ | 1-C4H, | Fp. IS-ITC |
150 | S-C4H, | S-C4H9 | n%> 1,5561 |
151 | S-C4H, | t-C4H, | n?,' 1,5544 |
152 | n-C6H13 | 1-C3H7 | η;? 1,5464 |
153 | n-C»HI3 | n-C6H,3 | nil1 1,5420 |
154 | Cyclohexyl | t-C4H, | Fp. 86-89°C |
155 | 1-C1H7 | 1-C8H17 | njV 1,5382 |
156 | s-CH, | 1-C8H17 | nj',' !,5461 |
172 | S-C4H, |
173 | S-C3H7 |
174 | CH3 |
175 | Phenyl |
179 | C2H5OCH2CH2 | UC3H7 |
180 | C2H5OCH2CH2 | LC4H, |
ίο 181 | Cyclopentyl | t-C4H, |
182 | t-C4H, | t-C4H, |
Fp. 74-75,50C Fp. 103-104°C Fp. 109-1150C
184 | 4-Cl | H | UC3H7 | Fp. 190-1970C (Zers.) |
185 | 4-Cl | H | t-C4H, | Fp. 210-214°C (Zers.) |
i5 186 | 4-Cl | CH3 | CH3 | Fp. 98-1000C |
187 | 4-Cl | CH3 | UC3H7 | Fp. 106-1080C |
188 | 4-Cl | C2H5 | C2H5 | Fp. 123-1250C |
M) 189 | 4-Cl | C2H5 | t-C4H, | Fp. 154-157°C |
190 | 4-Cl | n-C3H7 | n-C3H7 | Fp. 81-82°C |
191 | 4-Cl | n-C3H7 | UC3H7 | Fp. 61-630C |
45 192 | 4-Cl | UC3H7 | UC3H7 | Fp. 127-1290C |
193 | 4-Cl | n-C3H7 | t-C4H, | Fp. 68-69°C |
194 | 4-Cl | UC3H7 | t-C4H, | Fp. 123-1250C |
50 195 | 4-Cl | S-C4H, | S-C4H, | Fp. 1O2-1O3°C |
196 | 4-Cl | S-C4H, | t-C4H, | Fp. 99-1000C |
197 | 4-Cl | CH2=CHCH2 | CH2== CHCH2 | ns D° 1,6003 |
« 198 | 4-Cl | CH2=CHCH2 | UC3H7 | Up 1,5833 |
203
210 | 4-Cl |
211 | 3-Cl |
212 | 3-Cl |
213 | 3-Cl |
214 | 3-Cl |
215 | 3-Cl |
216 | 3-Cl |
217 | 3-Cl |
218 | 3-Cl |
219 | 3-Cl |
220 | 3-Cl |
221 | 3-Cl |
222 | 3-Cl |
223 | 3-Cl |
226 | 3-Cl |
227 | 3-Cl |
228 | 3-Cl |
229 | 3-Cl |
X | 28 | R2 | 3 | 24126 | I | |
C2H5 | ||||||
(Fortsetzung) | 3-Cl | U-C1H7 | CH3 C2H5 CH2=CHCH, CH2=CHCH2 i-C3H7 i-C3H7 |
K3 | Physikalische Eigenschaften I | |
Ver | 3-Cl | i-C3H7 i-C3H7 ^C4H, S-C4H, |
||||
bindung 5 Nr. |
3-Cl | N ι. —) n-CbH)3 CH3 |
-CH2-^(J) | 1-C4H, | n: D- 1,5740 | |
230 | 3-Cl 3-Cl |
-CH2CH2CHCH3 n-C4H, |
J-C3H7 | nji' 1,5750 | ||
ίο 231 | CH3 | i-C3H7 | "-C3H7 | n-Ji' 1,5635 | ||
232 | 3-Cl 2-Cl |
— ( CH |
i-C4H, n-C6H,3 |
S-C4H, t-C4H, |
ng' 1,5518 ni3 1,56 |
|
15 233 234 |
2-Cl | -CH2Jg | ||||
2-Cl 2-Cl 2-Cl 2-Cl 2-Cl 2-Cl |
J-C3H7 CH3 |
Fp. 158-159°C I Fp. 142-144°C I (HCl Salz: I Fp. 198-20O0C Zers.) I |
||||
20 235 236 |
2-Cl 2-Cl 2-Cl 2-Cl |
C2H5 | Fp. 90-920C I (HCl Salz: I 167-1700C Zers.) I |
|||
25 237 |
2-Cl | i-C3H7 LC4H, i-C3H7 t-C4H, i-C3H7 t-C4H, |
ni: 1,5725 I Fp. 94-96°C I n{/ 1,5831 I Fp. 1O5-1O7°C I Fp. 95-96°C I Fp. 88-89°C I (HCl Salz: Fp. 2010C Zers.) I |
|||
30 238 239 240 35 241 242 243 |
2-Cl | n-C6H13 t-C,H17 S-C4H, t-C4H, |
n'D s 1,5581 I n'J 1,5822 I Fp. 89-900C I Fp. 67-68°C I |
|||
40 ... 244 245 246 45 247 |
2-Cl | i-C3H7 | Fp. 95-97°C I | |||
248 | 2-Cl 2-Cl |
-CH,- | -<f\ (HCl Salz: I N=/ Fp. 127-1300C Zers.) I |
|||
50 249 | 2-Cl | —<^HN | ) Fp. 123-125°C | | |||
250 | 2-Cl | S-C4H, i-C,H7 |
Hd U5582 I ntf 1,5581 |
|||
55 251 ) 252 |
2-Cl | i-C3H7 | Fp. 75-77°C | |||
; 253 ·; 60 |
2-Cl | C2H5 | Fp. 77-79°C | |||
I 254 | CH3 | Fp. 167-168°C | ||||
) 65 255 | CHjOCH2CH2CH2 t-C4H, | Fp. 87-880C I | ||||
I 256 | ||||||
f." | ||||||
16 |
157 | 3-CF3 | CH3 |
258 | 3-CF, | C2H5 |
259 | 3-CF, | C2H5 |
260 | 3-CF3 | CH2=CHCH2 |
261 | 3-CF, | n-C,H7 |
262 | 3-CF3 | n-C,H7 |
263 | 3-CF, | J-C3H7 |
264 | 3-CF, | J-C3H7 |
265 | 3-CFj | CH2=CHCH2 |
266 | 3-CFj | CH2=CHCH2 |
267 | 3-CF3 | JC3H7 |
268 | 3-CFj | J-C3H7 |
269 | 3-CF, | J-C4H, |
270 | 3-CFj | S-C4H, |
271 | 3-CF3 | J-C4H, |
272 | 3-CFj | S-C4H, |
273 | 4-F | H |
274 | 4-F | H |
275 | 4-F | CH3 |
276 | 4-F | C2H5 |
277 | 4-F | CH, |
278 | 4-F | C2H5 |
279 | 4-F | n-C,H7 |
280 | 4-F | J-C3H7 |
281 | 4-F | S-C4H, |
282 | 4-F | S-C4H, |
283 | 4-F | J-C3H7 |
CH3 | ||
284 | 4-F | |
285 | 4-F | C2H5 |
286 | 4-F | —/h] |
287 | 4-F | CH1 |
J-C3H7 | Fp. 119-12O0C |
(HCl Salz: Fp. 2020C Zers.) | |
t-C4H, | Fp. 99-100°C |
n-C»H„ | ng1 1,5596 |
t-C4H, | Fp. 109-110°C |
S-C4H, | Fp. 55-56°C |
t-C4H, | Fp. 61-620C |
J-C3H7 | Fp. 119-12O0C |
J-C3H7 | Fp. 141-1420C |
H | Fp. 88-910C |
t-C4H, | Fp. 103-1040C |
CHjCH=CHj | Fp. 81-82°C |
322 | 3-CHj | CjH5 |
323 | 3-CHj | 1-C3H7 |
324 | 3-CHj | '-C3H7 |
325 | 3-CH1 | S-C4H, |
326 | 3-CH3 | S-C4H, |
328 | 3-CH3 | n-C6H,3 | i-C3H7 | nj? 1,5465 |
329 | 4-C2H, | CH3 | CH3 | /»? 1,5922 |
330 | 4-C2H5 | !-C3H7 | 1-C3H7 | Fp. 81-82,5°C |
331 | 4-CjH5 | J-C3H7 | t-C4H, | Fp. 70-720C |
332 | 4-C2H5 | S-C4H, | t-C4H, | Fp. 67,5°C |
333 | 2-C2H5 | CH3 | CH3 | Fp. 122.O0C |
334 | 2-CjH, | CH2=CHCH2 | J-C3H7 | /i£" 1,5601 |
335 | 2-C2H, | i-C3H7 | i-CjH, | ng 1,5510 |
336 | 2-CjH, | !-C3H7 | t-C4H, | n;?' 1,5463 |
337 | 2-CjH, | S-C4H, | t-C4H, | n$ 1,5401 |
338 | 2-C3H7-I | CH, | CH, | Fp. 101-1020C |
339 | 2-C1H7-I | C2H5 | t-C4H, | Fp. 84-85°C |
340 | 2-CjHri | i-CjH7 | i-CjH7 | Fp. 85-86°C |
341 | 2-CjH7-J | i-C3H7 | t-C4H, | Fp. 108-1090C |
342 | 2-C3H7-I | S-C4H, | t-C4H, | Fp. 74-760C |
343 | 2-C3H7-I | CH2=CHCH2 | CH2=CHCH2 | Fp. 93-95°C |
344 | 2-C3H7-I | CH2=CHCH2 | i-C3H7 | n2 D 0 1,5526 |
345 | 4-CH3O | CH3 | i-C3H, | Fp. 69,5°C |
346 | 4-CHjO | C2H, | C2H, | Fp. 1000C |
347 | 4-CHjO | C2H, | t-C4H, | η j," 1,5591 |
348 | 4-CH3O | CH2=CHCH2 | i-CjH7 | Fp. 80,10C |
349 | 4-CHjO | n-C3H7 | i-CjH7 | Fp. 96-970C |
350 | 4-CHjO | iC3H7 | J-C3H7 | Fp. 67-68°C |
351 | 4-CH3O | J-C3H7 | t-C4H, | Fp. 99-101,50C |
352 | 4-CH3O | n-C,H7 | —/ITS | Fp. 85,S°C |
353 | 4-CH3O | S-C4H, | t-C4H, | Fp. 63°C |
354 | 4-CH3O | -CH2-</~\ | UC3H7 | Fp. 114°C |
i-C3H7 | Fp. 159,1°C |
IC4H9 | Fp. 88,70C |
S-C3H7 | NMR Spektrum (wie nachstehend beschrieben) |
S-C4H9 | NMR-Spektrum (wie nachstehend beschrieben) |
40 | 361 | H | 4-NOj | 1-C3H7 | H | Fp. 160-1630C |
362 | H | 4-NO3 | i-C3H7 | IC4H9 | Fp. 130-1310C | |
363 | H | 4-OH | i-C3H7 | 1-C4H9 | Fp. 197-198°C | |
45 | 364 | 2-NO2 | 4-NOj | i-C3H, | J-C3H7 | Fp. 130-1330C |
365 | H | 4-C;HS0 | "-C3H7 | UC4H9 | Fp. 79-800C | |
366 | H | 4-C2H5O | S-C4H9 | 1-C4H9 | Fp. 66-67°C | |
367 | H | 4-C2H5 | n-C6H13 | J-C3H7 | Fp. 78-790C | |
368 | H | 4-i-C3H7O | CH3 | i-C3H7 | Fp. 112-1130C | |
369 | H | 4-1-C3H7O | C2H5 | CjH5 | nb" 1,5649 | |
370 | H | 4-1-C3H7O | i-C3H, | 1-C3H7 | Fp. 60-610C | |
55 | 371 | H | 4-1-C3H7O | i-C,H7 | UC4H, | Fp. 88-890C |
372 | H | 4-1-C3H7O | S-C4H, | UC4H9 | WL," 1,5402 | |
60 | 373 | H | 4-UC3H7O | -CHj-</^> | — CH2—/~\ | Fp. 141-142°C |
374 | 2-CH3 | 4-CH3 | CH3 | CH3 . | ηΐ," 1,5900 | |
375 | 2-CH3 | 4-CH3 | CH, | 1-C3H1 | «7," 1,5674 | |
65 | 376 | 2-CH, | 4-CH, | J-C3H7 | i-C,H7 | njl1 1,5589 |
377 | 2-CH3 | 4-CH, | i-C3H7 | UC4H, | Fp. 99-1000C | |
378 | 2-CH, | 4-CH3 | S-C4H9 | UC4H, | nf," 1,5478 |
379 | 2-CHj | 3-CH3 | CH; | CH, | Fp. 78-790C |
380 | 2-CH3 | 3-CH3 | CjH5 | -<V> | Fp. 151-152°C |
381 | 2-CH3 | 3-CH3 | i-C3H7 | i-C3H7 | Fp. 71-720C |
382 | 2-CH3 | 3-CH3 | 1-C3H7 | t-C4H, | Fp. 91-92°C |
383 | 2-CH3 | 3-CH3 | S-C4H9 | t-Ο,Η, | n: n° 1,5465 |
384 | 2-CH3 | 3-CH3 | -cH2~<3> | t-C4H, | «h° 1,5769 |
385 | 2-CH3 | 4-Cl | UC3H7 | t-C4H, | Fp. 122-123°C |
386 | 2-CH3 | 6-CHj | J-C3H7 | t-C4H, | Fp. 103-1040C |
387 | 2-CH3 | 6-CH3 | CH3 | CH3 | nj? 1.5967 |
388 | 2-CH3 | 6-CH3 | C2H5 | C2H5 | Fp. 77-78°C |
389 | 2-C2H5 | 6-C2H5 | CH3 | CH3 | Fp. 88-89°C |
390 | 2-C2H5 | 6-C2H, | C2H5 | C2H5 | nh0 1,5644 |
391 | 2-C2H5 | 6-C2H5 | CH3 | i-C.,H7 | Fp. 106-1070C |
392 | 2-C2H5 | 6-C2H5 | CH2 = CHCH2 | CH2=CHCH2 | ni0 1,5583 |
393 | 2-C3H5 | 6-C2H5 | i-C,H7 | i-C,H7 | Fp. 89-9O°C |
394 | 2-CI | 4-Cl | CH3 | i-C,H7 | Fp. 109-111°C |
395 | 2-CI | 4-Cl | C2H5 | t-C4H, | Fp. 110-1120C |
396 | 2-CI | 4-Cl | i-C3H7 | J-C3H7 | Fp. 121-123°C |
397 | 2-CI | 4-Cl | J-C3H7 | t-C4H, | Fp. 130-132°C |
398 | 2-CI | 4-Cl | S-C4H, | S-C4H, | njf 1,5634 |
399 | 2-CI | 4-Cl | S-C4H, | t-C4H, | nj? 1,5602 |
400 | 2-CI | 3-Cl | S-C3H7 | J-C3H7 | Fp. 93-94°C |
401 | 3-Cl | 5-Cl | CH3 | CH3 | Fp. 145-147°C |
402 | 3-Cl | 5-Cl | C2H5 | C2H5 | Fp. 100-1020C |
403 | 3-Cl | 5-Cl | n-C3H7 | S-C3H7 | Fp. 80-82°C |
404 | 3-Cl | 5-Cl | J-C3H7 | i-C3H, | Fp. 81-83°C |
inc | 3-C! | 5'Cl | i-C3H7 | t-CjH; | Fp. !13-115°C |
406 | 3-Cl | 5-Cl | -CH3-<Q> | J-C3H7 | Fp. 90-92°C |
407 | 3-Cl | 5-Cl | J-C3H7 | t-C,H„ | Fp. 78-81°C |
408 | 3-Cl | 5-Cl | n-CtHu | i-C3H7 | ni3 1,5699 |
409 | 3-Cl | 5-Cl | S-C4H, | S-C4H, | if 1? 1,5822 |
410 | 3-Cl | 5-Cl | CH2=CHCH2 | J-C3H7 | n'D 9J 1,5962 |
411 | 3-Cl | 4-Cl | C2H5 | C2H5 | Fp. 86-88°C |
412 | 3-Cl | 4-Cl | n-C3H7 | n-C3H7 | ni° 1,5848 |
413 | 3-Cl | 4-Cl | i-C3H7 | S-C3H7 | Fp. 104-107°C |
414 | 3-Cl | 4-Cl | J-C3H7 | t-C4H, | Fp. 114,5-117,50C |
Eigenschaften
415 | 3-Cl | 4-Cl | n-CjH, | S-C4H, |
416 | 3-Cl | 4-Cl | C2H5 | t-C4H, |
417 | 3-Cl | 4-Cl | C2H5 | i-C«H, |
418 | 3-Cl | 4-Cl | n-CjH, | i-C4H, |
419 | 3-Cl | 4-Cl | CH2=CHCH2 | i-C3H, |
420 | 3-Cl | 4-C! | _CH2-^\ | i-C3H7 |
421 | 3-Cl | 4-Cl | -CH2 | |
422 | 3-Cl | 4-Cl | CH3 | i-C3H7 |
423 | 3-Cl | 4-Cl | S-C3H7 | —<JH |
424 | 2-Cl | 5-Cl | C2H5 | t-C4H, |
425 | 2-Cl | 5-Cl | UC3H7 | t-C4H, |
426 | 2-Cl | 5-Cl | S-C4H, | 1-C4H9 |
427 | 2-Cl | 5-Cl | _CH2-<^> | -CH3 |
428 | 2-Cl | 3-Cl | C2H5 | t-C4H, |
429 | 3-CH3 | 4-CH3 | i-C3H7 | i-C3H7 |
430 | 3-CH3 | 4-CH3 | i-C,H7 | t-C4H, |
431 | 3-CHj | 4-CH3 | S-C4H, | 1-C4H9 |
Fp. 1O5-1O7°C h|; 1,5912
«{," 1,5769
n'J 1,5920
Fp. 145-146°C Fp. 111-1120C
Fp. 109-UO0C Fp. 92-930C
Im Vergleich zu herkömmlichen Insektiziden, z. B. Phosphorverbindungen und Carbamatverbindungen,
Die Erfindung wird in den Beispielen erläutert.
(Verbindung Nr. 66)
(Verbindung Nr. 72)
(Verbindung Nr. 7)
CH
NMR (CDCl3)* 0,97 (S. 9H), 1,20 (S. 9H), 1,50 (S. 6H), 1,90 (S. 2H), 3,18 (S. 3H), 4.54 (S. 2H).
(Verbindung Nr. 144)
O
(Verbindung Nr. 154)
O
CH3
2-t-Butylimino-3-isopropyl-5-(p-methoxyphenyl)-tetrahydro-l,3,5-thiadiazin-4-on
O
O
O
O
\
(Verbindung Nr. 130)
Ein befeuchtbares Pulver wurde durch gleichförmiges Vermischen der folgenden Bestandteile hergestellt:
Eine Ölsprühzubereitung wurde durch Vermischen der folgenden Bestandteile hergestellt:
Eine Staubzubereitung wurde durch gleichförmiges Vermengen der folgenden Bestandteile hergestellt:
Ein befeuchtbares Pulver wurde durch gleichförmiges Vermischen der folgenden Bestandteile hergestellt:
Verbindung
Nr. |
Mortalität
(%) |
Verbindung
Nr. |
Mortalität
(%) |
Verbindung
Nr. |
Mortalität
(%) |
Verbindung
Nr. |
Mortalität
(%) |
2 | 100 | 65 | 100 | 141 | 100 | 217 | 100 |
6 | 100 | 66 | 100 | 146 | 100 | 218 | 100 |
S | 100 | 68 | 100 | 147 | 100 | 219 | 100 |
9 | 100 | 69 | 100 | 148 | 100 | 220 | 100 |
10 | 100 | 71 | 80 | 149 | 100 | 221 | 100 |
14 | 80 | 72 | 80 | 150 | 100 | 222 | 100 |
16 | 100 | 75 | 100 | 151 | 100 | 223 | 100 |
18 | 100 | 80 | 100 | (154 | 50) | 226 | 100 |
23 | 100 | 82 | 100 | 155 | 100 | 227 | 100 |
25 | 100 | 83 | 100 | 156 | 100 | 230 | 70 |
27 | 100 | 87 | 100 | 158 | 80 | 231 | 100 |
29 | 100 | 88 | 100 | 161 | 100 | 232 | 100 |
31 | 80 | 122 | 100 | 166 | 70 | 234 | 80 |
32 | 100 | 125 | 100 | 177 | 90 | 235 | 100 |
33 | 100 | 126 | 100 | 180 | 70 | 239 | 100 |
35 | 100 | 128 | 80 | 186 | 100 | 240 | 100 |
37 | 100 | 130 | 100 | 192 | 100 | 241 | 100 |
42 | 100 | 133 | 100 | 194 | 100 | 242 | i00 |
48 | 100 | 134 | 100 | 195 | 100 | 243 | 100 |
51 | 100 | 135 | 80 | 196 | 100 | 245 | 90 |
53 | 80 | 13d | 80 | 2Ί | 100 | 246 | 100 |
56 | 80 | 138 | 100 | 214 | 100 | 247 | 100 |
59 | 100 | 139 | too | 215 | 100 | 250 | 100 |
M | 100 | 140 | 100 | 216 | 100 | 251 | 80 |
Verbindung Mortalität Nr. (%) |
100 | Verbindung Nr. |
Mortalität (%) |
Verbindung Nr. |
Mortalität Pi.) |
Behandlung,
der Behandlung. |
Verbindung Nr. |
Mortalität <%) |
253 | 100 | 303 | 95 | 341 | 100 | 386 | 100 | |
256 | 60 | 305 | 70 | 342 | 100 | 388 | 60 | |
257 | 60 | 306 | 60 | 348 | 100 | 392 | 70 | |
258 | 80 | 310 | 100 | 350 | 100 | 393 | 100 | |
267 | 60 | 312 | 100 | 351 | 100 | 396 | 100 | |
268 | 100 | 313 | 100 | 352 | 100 | 397 | 100 | |
272 | 100 | 314 | 100 | 353 | 100 | 398 | 100 | |
273 | 100 | 315 | 100 | 358 | 100 | 399 | 100 | |
274 | 100 | 316 | 100 | 362 | 100 | 400 | 80 | |
278 | 100 | 317 | 100 | 365 | 80 | 404 | 80 | |
280 | 100 | 318 | 100 | 366 | 80 | 405 | 100 | |
281 | 100 | 319 | 85 | 369 | 75 | 407 | 60 | |
282 | 100 | 322 | 100 | 370 | 60 | 409 | 60 | |
283 | 100 | 323 | 100 | 371 | 80 | 410 | 100 | |
287 | 100 | 324 | 100 | 372 | 80 | 413 | 100 | |
289 | 100 | 325 | 100 | 374 | 60 | 414 | 100 | |
291 | 100 | 326 | 90 | 375 | 100 | 416 | 60 | |
292 | 100 | 330 | 100 | 376 | 100 | 419 | 60 | |
293 | 80 | 331 | 100 | 377 | 100 | 420 | 60 | |
295 | 100 | 332 | 100 | 378 | 100 | 423 | 60 | |
297 | 100 | 333 | 80 | 379 | 60 | 424 | 70 | |
298 | 100 | 334 | 80 | 380 | 80 | 425 | 100 | |
299 | 100 | 335 | 100 | 381 | 100 | .426 | 100 | |
300 | 100 | 336 | 100 | 382 | 100 | |||
301 | 100 | 337 | 100 | 383 | 100 | |||
302 |
Verbindung Nr. 2 -
Verbindung Nr. 125 |
340 | 100 | 385 | 100 | |||
*) |
Nr. 88: Werte von
- Nr. 426: Werte |
7 Tagen nach der von 5 Tagen nach |
63 | 100 |
65 | 100 |
66 | 100 |
68 | 100 |
69 | 100 |
71 | 80 |
72 | 100 |
75 | 100 |
80 | 100 |
82 | 100 |
83 | 100 |
87 | 100 |
88 | 100 |
143 | 100 |
144 | 100 |
150 | 100 |
151 | 100 |
194 | 90 |
195 | 90 |
196 | 100 |
218 | 100 |
219 | 100 |
222 | 100 |
Testbeispiel 3 | |
t gegenüber zweifleckij (Tetranychus urticae |
|
Testmethode |
Verbindung Nr. |
Mortalität
(%) |
223 | 100 |
242 | 100 |
243 | 100 |
280 | 100 |
281 | 100 |
282 | 100 |
283 | 100 |
289 | 100 |
300 | 100 |
301 | 100 |
314 | 100 |
316 | 100 |
317 | 100 |
323 | 100 |
324 | 100 |
325 | 100 |
326 | 100 |
331 | 100 |
350 | 100 |
351 | 100 |
353 | 100 |
363 | 100 |
393 | 90 |
2 | 100 | 10 | 100 | 23 | 100 |
6 | 100 | 14 | 100 | 25 | 100 |
S | 100 | 16 | 100 | 27 | 80 |
9 | 80 | 18 | 80 | 29 | 100 |
W
ί |
) (Fortsetzung) | 28 24 | 126 |
Verbindung
Nr. |
Mortalität | I | 10 | I | 45 | ■ | 60 |
ϊ I |
Mortalitiit
("/„> |
314 | 100 | I | 55 I | ||||||
I Tabelle IH* | 100 |
Verbindung
Nr. |
Mortalität | 315 | HX) | 30 I | I | ||||
'■ft Vorbinduni!
if Nr |
100 | 231 | 100 | 316 | 100 | 15 | 1 | 50 | I | 65 | |
§ 31 | 100 | 235 | 100 | 317 | 100 | 1 | I | ||||
I 32 | 100 | 239 | 70 | 318 | 70 | 35 I | |||||
100 | 240 | 70 | 319 | 70 | 20 | I | |||||
I 35 | 100 | 242 | 70 | 325 | 100 | I | |||||
I 37 | 100 | 243 | 100 | 326 | 100 | 40 I | |||||
1 42 | 100 | 245 | 70 | 334 | 100 | I | |||||
I 48 | 100 | 246 | 100 | 335 | 100 | 25 | |||||
I 51 | 100 | 247 | 70 | 348 | 100 | ||||||
I 53 | 100 | 253 | 100 | 351 | 100 | ||||||
I 56 | 80 | 256 | 100 | 352 | 100 | ||||||
I 59 | 100 | 257 | 100 | 353 | 100 | ||||||
63 | 100 | 258 | 100 | 357 | 100 | ||||||
65 | 100 | 268 | 70 | 362 | 60 | ||||||
06 | 100 | 272 | 100 | 365 | 100 | ||||||
68 | 100 | 279 | 80 | 366 | 100 | ||||||
69 | 100 | 280 | 80 | 368 | 100 | ||||||
71 | 80 | 281 | 70 | 369 | 100 | ||||||
72 | 80 | 282 | 100 | 370 | 100 | ||||||
75 | 100 | 283 | 100 | 371 | 100 | ||||||
80 | 100 | 287 | 100 | 372 | 100 | ||||||
82 | 100 | 289 | 100 | 374 | 100 | ||||||
83 | ιόο | 291 | 100 | 375 | 100 | ||||||
87 | 90 | 292 | 100 | 376 | 100 | ||||||
88 | 100 | 293 | 100 | 377 | 100 | ||||||
186 | 80 | 295 | 100 | 378 | 100 | ||||||
192 | 80 | 296 | 100 | 379 | 70 | ||||||
194 | 100 | 297 | 100 | 380 | 100 | ||||||
195 | 100 | 298 | 100 | 381 | 100 | ||||||
196 | 70 | 299 | 100 | 382 | 100 | ||||||
211 | Ιύο | 300 | 70 | 383 | 100 | ||||||
214 | 100 | 301 | 80 | 385 | 100 | ||||||
215 | 70 | 302 | 100 | 386 | MX) | ||||||
216 | 100 | 303 | 70 | 388 | 80 | ||||||
217 | 80 | 305 | 70 | 392 | 80 | ||||||
219 | 70 | 306 | 100 | 393 | 80 | ||||||
220 | 1Ö0 | 310 | 100 | 396 | 80 | ||||||
221 | 100 | 312 | 100 | ||||||||
222 | 313 | 100 | |||||||||
223 | |||||||||||
397 | 80 | 40b | 100 | 417 | 100 |
398 | 70 | 407 | 100 | 419 | 7t) |
lü 399 | 70 | 409 | HX) | 420 | 100 |
400 | 100 | 410 | KK) | 423 | 100 |
402 | 100 | 413 | 100 | 424 | 100 |
.5 404 | 60 | 414 | 100 | 425 | KK) |
405 | 100 | 416 | 70 | 426 | 100 |
2 | 50 | 33 | 100 | 71 | 50 | 144 | 100 |
6 | 80 | 35 | 100 | 72 | 80 | 147 | 100 |
8 | 80 | 37 | 100 | 75 | 50 | 152 | 100 |
9 | 50 | 42 | HX) | 80 | KK) | 160 | 100 |
10 | 80 | 48 | 100 | 82 | 100 | 216 | 100 |
14 | 50 | 51 | 50 | 83 | 50 | 217 | 100 |
16 | 100 | 53 | 100 | 87 | ICK) | 247 | 100 |
18 | 100 | 56 | 100 | 88 | 100 | 279 | K)O |
23 | 80 | 59 | 100 | 114 | 100 | 307 | 100 |
25 | 80 | 63 | 50 | 117 | 100 | 308 | 100 |
27 | 100 | 65 | 100 | 122 | 100 | 314 | 100 |
29 | 100 | 66 | 50 | 123 | 100 | 317 | 100 |
31 | 100 | 68 | 50 | 130 | KK) | 366 | 100 |
32 | 100 | 69 | 80 | 134 | 100 |
2 | 50 | 68 | 50 | 218 | 100 |
6 | 80 | 69 | 100 | 219 | 100 |
8 | 80 | 71 | 50 | 222 | 100 |
9 | 100 | 72 | 80 | 223 | 90 |
10 | 100 | 75 | 50 | 242 | 100 |
14 | 100 | 80 | 50 | 243 | 100 |
16 | 100 | 82 | 80 | 246 | 100 |
18 | 100 | 83 | 80 | 247 | 100 |
23 | 80 | 87 | 80 | 280 | 100 |
25 | 100 | 88 | 80 | 281 | 90 |
27 | 80 | 129 | 100 | 282 | 100 |
29 | 80 | 130 | 100 | 283 | 100 |
31 | 50 | 139 | 100 | 289 | 100 |
32 | 50 | 140 | 100 | 300 | 100 |
33 | 100 | 141 | 100 | 301 | 100 |
35 | 50 | 142 | 100 | 316 | 100 |
37 | 50 | 143 | 100 | 317 | 100 |
42 | 80 | 144 | 100 | 323 | 100 |
48 | 80 | 149 | 90 | 324 | 100 |
51 | 50 | 150 | 100 | 325 | 100 |
53 | 50 | 151 | 100 | 326 | 100 |
56 | 50 | 152 | 100 | 331 | 100 |
59 | 100 | 155 | 100 | 350 | 100 |
63 | 80 | 186 | 100 | 351 | 100 |
65 | 50 | 192 | 100 | 353 | 100 |
66 | 80 | 196 | 100 | 393 | 100 |
124 | 80 | 149 | 100 | 243 | 100 | 308 | 100 | |
125 | 100 | 150 | 100 | 245 | 100 | 310 | 100 | |
25 | 126 | 100 | 151 | 100 | 246 | 90 | 312 | 100 |
128 | 100 | 154 | 100 | 247 | 100 | 313 | lOO | |
130 | 100 | 155 | 100 | 257 | 100 | 314 | 70 | |
30 | 133 | 80 | 156 | 100 | 263 | 100 | 315 | 100 |
134 | 100 | 161 | 100 | 267 | 100 | 316 | 90 | |
135 | 100 | 186 | 100 | 268 | 100 | 317 | 100 | |
136 | 100 | 192 | 80 | 272 | 100 | 318 | 70 | |
138 | 100 | 195 | 100 | 278 | 90 | 319 | 70 | |
139 | 100 | 196 | 100 | 280 | 90 | 323 | 100 | |
140 | 100 | 211 | 100 | 281 | 70 | 324 | 100 | |
40 | 141 | 100 | 216 | 100 | 282 | 100 | 325 | 90 |
142 | 80 | 218 | 80 | 283 | 100 | 326 | 100 | |
143 | 100 | 219 | 100 | 289 | 70 | 331 | 100 | |
45 | 144 | 100 | 221 | 100 | 299 | 90 | 350 | 100 |
145 | 100 | 222 | 100 | 300 | 100 | 351 | 100 | |
146 | 100 | 223 | 100 | 305 | 100 | 353 | 90 | |
50 | 148 | 100 | ?42 | 100 | 306 | 100 | 393 | 100 |
Insektizide Aktivität gegenüber dem ausgewachsenen rostroten Mehlkäfer
getrocknet In eine Petrischale, die am Boden mit einem Stück Filterpapier bedeckt worden war, wurden 1 ml 25 Wasser und drei behandelte Tomatenblättchen eingeführt. Nach dem Befall mit sieben Larven des zweiten
Zustands von 28fleckigen Marienkäfern wurde die Petrischale in einem Schrank mit konstanter Temperatur von
25°C stehengelassen. 5 Tage nach der Behandlung wurden die toten und überlebenden Larven bestimmt und
das Mortalitätsverhältnis wurde errechnet (Test mit zweifacher Wiederholung).
Verbindung
Nr. |
Mortalität
(%) |
151 | 100 |
154 | 100 |
155 | 90 |
156 | 100 |
161 | 50 |
162 | 60 |
196 | 100 |
218 | 100 |
219 | 90 |
242 | 90 |
243 | 90 |
247 | 100 |
281 | 90 |
282 | 100 |
283 | 80 |
289 | 100 |
300 | 80 |
301 | 100 |
312 | 100 |
314 | 100 |
Verbindung
Nr. |
Mortalität
(%) |
316 | 100 |
317 | 100 |
323 | 100 |
324 | 100 |
325 | 100 |
326 | 100 |
350 | 100 |
351 | 100 |
353 | 100 |
362 | 80 |
363 | 100 |
396 | 80 |
397 | 100 |
402 | 90 |
403 | 90 |
409 | 100 |
410 | 100 |
416 | 70 |
420 | 90 |
117 | 100 | 138 | 100 | 150 | 80 |
125 | 100 | 139 | 50 | 151 | 100 |
126 | 100 | 140 | 80 | 154 | 100 |
128 | 100 | 141 | 100 | 155 | 50 |
130 | 100 | 142 | 100 | 156 | 100 |
133 | 80 | 143 | 100 | 161 | 50 |
134 | 100 | 144 | 100 | 214 | 100 |
135 | 100 | 148 | 50 | 215 | 100 |
136 | 50 | 149 | 50 | 220 | 100 |
Testbeispiel 10 | |||||
Insektizide | Aktivität gegenüber Larven von Motten | mit Diamantrücken | |||
(Plutilla xylostella Linne) | |||||
Testmethode |
205 | 100 | 230 | 70 | 327 | 100 |
206 | 80 | 234 | 100 | 329 | 100 |
217 | 80 | 322 | 100 | 331 | 100 |
226 | 100 | 324 | 100 | 364 | 100 |
228 | 100 | 325 | 100 |
Claims (15)
- Patentansprüche:
1. Tetrahydro-l,3,5-thiadiaEin-4-on-Verbindungen der allgemeinen Formelin derR1, R2 und R3, die gleich oder verschieden sein können, je eine Alkylgruppe mit 1 bis 8 Kohlenstoffatomen, eine Allylgruppc, Cycloalkylgruppe mit 3 bis 6 Kohlenstoffatomen, Alkoxyalkylgruppe mit insgesamt 3 bis 6 Kohlenstoffatomen, Benzylgruppe, Phenylgruppe oder substituierte Phenylgruppe, die als Substituenten eine oder zwei Alkylgruppen mit 1 bis 4 Kohlenstoffatomen, Nitrogruppen, Halogenatome, Alkoxygruppen mit 1 bis 4 Kohlenstoffatomen oder Triiluormethylgruppen, aufweist, bedeuten und R: oder R auch Wasserstaffatome sein können, oderR1 eine 2-Chlorphenylgruppe, R2 einen Furfurylrest und R3 eine Isopropylgruppe oder R1 eine 4-Hydroxylphenylgruppe, R2 eine Isopropylgruppe und R3 eine tert.-Butylgruppe oder R1 eine 3-Chlorphenylgruppe, R2 einen a-Methylbenzylrest und R3 eine Isopropylgruppebedeuten, sowie ihre Säureadditionssalze. - 2. 2-t-Butylimino-3-isopropyl-5-phenyl-tetrahydro-l,3,5-thiadiazin-4-on und die Säureadditionssalze davon.
- 3. 2-t-Butylimino-3-isopropyl-5-(4-tolyl)-tetrahydro-1.3,5-thiadiazin-4-on und die Säureadditionssalze davon.
- 4. 2-t-Butylimino-3-isopropyl-5-(3-chlorphenyl)-tetrahydro-l,3,5-thiadiazin-4-on und die Säureadditionssalze davon.
- 5. 2-t-Butylimino-3-isopropyl-5-{3-tolyl)-tetrahydro-l,3,5-thiadiazin-4-on und die Säureadditionssalze davon.
- 6.2-t-Butylimino-3-sek.-butyl-5-<2,4-dimethylphenyl)-tetrahydro-1,3,5-thiadiazin-4-on und die Säureadditionssalze davon.
- 7. 2-t-Butylimino-3-isopropyl-5-(2-chlorphenyl)-tetrahydro-l,3,5-thiadiazin-4-on und die Säureadditionssalze davon.
- 8. 2-t-Butylimino-3-isopropyl-5-(4-methoxyphenyl)-tetrahydro-l,3,5-thiadiazin-4-on und die Säureadditionssalze davon.
- 9. 2-t-Butylimino-3-sek.-butyl-5-(4-methoxyphenyl)-tetrahydro-l,3,5-thiadiazin-4-on und die Säureadditionssalze davon.
- 10. Verfahren zur Herstellung von Tetrahydro-l,3,5-thiadia7.in-4-on-Verbindungen nach einem der Ansprüche 1 bis 9 sowie ihrer Säureadditionssalze, dadurch gekennzeichnet, daß man ein Carbamoylchlorid der allgemeinen FormelR'_N —CCI (H)CH2Clin der R' die oben gegebene Bedeutung besitzt, mit einem Thioharnstoff der allgemeinen Formel SR2NHCNHR3 (111)in der R2 und R3 die obigen Bedeutungen besitzen, umsetzt.
- 11. Verfahren nach Anspruch 10 zur Herstellung eines l,3,5-Thiadiazin-4-on, dadurch gekennzeichnet, daß man die Reaktion in Gegenwart einer Base durchführt.
- 12. Verfahren nach Anspruch 10 zur Herstellung des Hydrochlorids als Säureadditionssalz, dadurch gekennzeichnet, daß man die Reaktion in Abwesenheit einer Base durchführt.
- 13. Insektizides und milbentötendes Mittel, dadurch gekennzeichnet, daß es ein Tetrahydro-l,3,5-thiadiazin-4-on nach einem der Ansprüche 1 bis 9 oder ein Säureadditionssalz davon und ein inertes Verdünnungsmittel enthält.
- 14. Mittel nach Anspruch 3, dadurch gekennzeichnet, daB es 2-t-Butylimino-3-isopropyl-5-phenyl-tetrahydro-1.3.S-thiadiazin-4-on oder ein Säureadditionssalz davon enthält.
- 15. Mittel nach Anspruch 13, dadurch gekennzeichnet, daß es 2-t-Butylimino-3-isopropyl-S-(p-tolyl)-tetrahydco-l,3,5-thiadiazin-4-on oder ein Säureadditionssalz davon enthält.Gegenstand der Erfindung sind Tetrahydro-l,3,5-thiadiazin-4-on-Verbindungen der allgemeinen Formel (1) OR1—N N —R2(D
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP6813877A JPS543083A (en) | 1977-06-09 | 1977-06-09 | Tetrahydro-1,3,5-thiadiazin-4-ones and insecticide-miticide containing the same |
JP7759477A JPS5412390A (en) | 1977-06-29 | 1977-06-29 | Thiadiazine and insecticide or acaricide containing the same |
JP9157077A JPS5427590A (en) | 1977-07-30 | 1977-07-30 | Preparation of thiadiazines |
JP2255078A JPS54115387A (en) | 1978-02-28 | 1978-02-28 | Tetrahydro-1,3,5-thiadiazine-4-one, insecticides and acaricides containing it |
Publications (2)
Publication Number | Publication Date |
---|---|
DE2824126A1 DE2824126A1 (de) | 1978-12-14 |
DE2824126C2 true DE2824126C2 (de) | 1984-06-20 |
Family
ID=27457792
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2824126A Expired DE2824126C2 (de) | 1977-06-09 | 1978-06-01 | Tetrahydro-1,3,5-thiadiazin-4-on-Verbindungen |
Country Status (11)
Country | Link |
---|---|
BR (1) | BR7803606A (de) |
CH (1) | CH633546A5 (de) |
CU (1) | CU34933A (de) |
DE (1) | DE2824126C2 (de) |
FR (1) | FR2393798A1 (de) |
GB (1) | GB1592043A (de) |
IT (1) | IT1109653B (de) |
MX (1) | MX6009E (de) |
MY (1) | MY8400338A (de) |
NL (2) | NL175694C (de) |
SU (1) | SU876057A3 (de) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4452795A (en) * | 1981-09-03 | 1984-06-05 | Ciba-Geigy Corporation | 5-Phenoxyphenyl-tetrahydro-1,3,5-thiadiazin-4-ones |
US4443445A (en) * | 1981-09-10 | 1984-04-17 | Ciba-Geigy Corporation | Imidazo- and pyrimido-1,3,5-thiadiazin-4-ones |
JPS61197503A (ja) * | 1985-02-25 | 1986-09-01 | Nippon Nohyaku Co Ltd | 殺虫組成物 |
BR8901356A (pt) * | 1988-07-08 | 1990-10-23 | Mitsui Toatsu Chemicals | Processo para a producao de novas tiadiazinas,e agentes inseticidas e acaricidas compreendendo as tiadiazinas |
EP2127522A1 (de) | 2008-05-29 | 2009-12-02 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
EP2382865A1 (de) | 2010-04-28 | 2011-11-02 | Bayer CropScience AG | Synergistische Wirkstoffkombinationen |
EP4337016A1 (de) | 2021-05-14 | 2024-03-20 | Syngenta Crop Protection AG | Zusammensetzungen zur saatgutbehandlung |
-
1978
- 1978-05-31 GB GB26091/78A patent/GB1592043A/en not_active Expired
- 1978-06-01 DE DE2824126A patent/DE2824126C2/de not_active Expired
- 1978-06-05 BR BR787803606A patent/BR7803606A/pt unknown
- 1978-06-07 CH CH621178A patent/CH633546A5/de active Protection Beyond IP Right Term
- 1978-06-08 MX MX787132U patent/MX6009E/es unknown
- 1978-06-08 FR FR787817145A patent/FR2393798A1/fr active Granted
- 1978-06-08 IT IT68334/78A patent/IT1109653B/it active Protection Beyond IP Right Term
- 1978-06-09 NL NLAANVRAGE7806296,A patent/NL175694C/xx not_active IP Right Cessation
- 1978-06-09 CU CU7834933A patent/CU34933A/es unknown
- 1978-12-22 SU SU782701050A patent/SU876057A3/ru active
-
1984
- 1984-12-30 MY MY338/84A patent/MY8400338A/xx unknown
-
1997
- 1997-05-30 NL NL971006C patent/NL971006I2/nl unknown
Also Published As
Publication number | Publication date |
---|---|
CU34933A (en) | 1981-12-04 |
NL971006I2 (nl) | 1997-10-01 |
DE2824126A1 (de) | 1978-12-14 |
CH633546A5 (en) | 1982-12-15 |
MX6009E (es) | 1984-09-24 |
IT7868334A0 (it) | 1978-06-08 |
FR2393798A1 (fr) | 1979-01-05 |
NL175694B (nl) | 1984-07-16 |
MY8400338A (en) | 1984-12-31 |
BR7803606A (pt) | 1979-02-20 |
NL7806296A (nl) | 1978-12-12 |
SU876057A3 (ru) | 1981-10-23 |
NL175694C (nl) | 1984-12-17 |
NL971006I1 (nl) | 1997-08-01 |
FR2393798B1 (de) | 1982-01-08 |
GB1592043A (en) | 1981-07-01 |
IT1109653B (it) | 1985-12-23 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE69028461T2 (de) | Triazin-derivate und unkrautvertilgungsmittel daraus | |
DE2701091A1 (de) | Fungizide zusammensetzungen und verbindungen | |
DD144498A5 (de) | Verfahren zur verringerung von herbizidschaeden | |
DE3713774C2 (de) | Pyrazol-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende Fungizide | |
DE3883695T2 (de) | Amid-Derivate, Verfahren zu deren Herstellung sowie diese enthaltende Fungizide in der Agrikultur und im Gartenbau. | |
DE3618662A1 (de) | Trisubstituierte 1,3,5-triazin-2,4,6-trione | |
CH633678A5 (en) | Pesticide | |
DE2824126C2 (de) | Tetrahydro-1,3,5-thiadiazin-4-on-Verbindungen | |
EP0388873B1 (de) | Herbizide [[1,3,5-Triazin-2-yl) aminocarbonyl] aminsulfonyl] benzoesäureester, Verfahren zu ihrer Herstellung und ihre Verwendung | |
EP0037971B1 (de) | Trisubstituierte Cyanguanidine, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide | |
DE1695989A1 (de) | Verfahren zur Herstellung von neuen Aryl-1,2,4-oxadiazolidinverbindungen mit herbicider Aktivitaet und Verwendung der neuen Verbindungen als Herbicide | |
DE2131745A1 (de) | Zyklische Schwefelverbindungen und deren Verwendung | |
DE3780011T2 (de) | 3-perfluoroalkyl-isoxazol-5-yl-oxycarbonsaeure-derivate, verfahren zu ihrer herstellung und ihre verwendung als herbizide. | |
DE69823191T2 (de) | 1,2,3-thiadiazol-derivate, mittel zur kontrolle von pflanzenkrankheiten und methode zu seiner anwendung | |
DE2428070C2 (de) | Butyramide und Butyrate, ihre Herstellung und diese enthaltende aphizide Mittel | |
EP0062254A1 (de) | Substituierte Acetanilide, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide | |
EP0010692A1 (de) | Neue m-Anilidurethane, sie enthaltende Herbizide und Verfahren zu deren Herstellung, sowie Verfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs | |
DE2919825C2 (de) | ||
DE2434922A1 (de) | Isothiazolylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizide | |
DE3306697A1 (de) | Substituierte maleinsaeureimide | |
DD262359A5 (de) | Gyanoacetamidderivate mit fungizider wirksamkeit | |
EP0144052A2 (de) | Chinolinoxyphenylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchhses | |
DE2850902A1 (de) | Neue phenoxy-phenoxi-propionsaeureamide und ihre verwendung als herbizide | |
EP0040310A2 (de) | Fungizide, heterocyclisch substituierte Thioglykolsäureanilide, Verfahren zu ihrer Herstellung und diese enthaltende Schädlingsbekämpfungsmittel | |
DE2556938C2 (de) | N,N-disubstituierte Alaninderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als herbicide Mittel |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
OAP | Request for examination filed | ||
OD | Request for examination | ||
D2 | Grant after examination | ||
8364 | No opposition during term of opposition | ||
V448 | Application of spc |
Free format text: PRODUCT NAME: BUPROFEZIN; REGISTRATION NO/DATE: 04089-00, 19961128 Spc suppl protection certif: 197 75 023 Filing date: 19970711 |
|
V457 | Spc granted |
Free format text: PRODUCT NAME: BUPROFEZIN; REGISTRATION NO/DATE: 04089-00, 19961128 Spc suppl protection certif: 197 75 023 Filing date: 19970711 |
|
V464 | Spc expired |
Free format text: PRODUCT NAME: BUPROFEZIN; REGISTRATION NO/DATE: 04089-00, 19961128 Spc suppl protection certif: 197 75 023 Filing date: 19970711 |