GB1592043A - Tetrahydro-1,3,5-thiadiazin-4-one derivatives - Google Patents
Tetrahydro-1,3,5-thiadiazin-4-one derivatives Download PDFInfo
- Publication number
- GB1592043A GB1592043A GB26091/78A GB2609178A GB1592043A GB 1592043 A GB1592043 A GB 1592043A GB 26091/78 A GB26091/78 A GB 26091/78A GB 2609178 A GB2609178 A GB 2609178A GB 1592043 A GB1592043 A GB 1592043A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tetrahydro
- thiadiazin
- compound
- mole
- 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 abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 225
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 15
- 241000238631 Hexapoda Species 0.000 claims abstract description 14
- 125000001424 substituent group Chemical group 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 9
- 241000238876 Acari Species 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 126
- -1 p-hydroxyphenyl group Chemical group 0.000 claims description 49
- 239000002253 acid Substances 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 25
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 20
- 230000000749 insecticidal effect Effects 0.000 claims description 16
- 150000003840 hydrochlorides Chemical class 0.000 claims description 13
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 12
- 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 5
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 5
- 230000000266 injurious effect Effects 0.000 claims description 4
- 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 3
- 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
- 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 description 2
- 241001414720 Cicadellidae Species 0.000 claims description 2
- 241001466042 Fulgoromorpha Species 0.000 claims description 2
- 125000002425 furfuryl group Chemical group C(C1=CC=CO1)* 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 230000003129 miticidal effect Effects 0.000 claims description 2
- 239000002689 soil Substances 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 1
- 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
- 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 1
- YTLMBKFXWASSEX-UHFFFAOYSA-N 3-butan-2-yl-2-tert-butylimino-5-(2,4-dimethylphenyl)-1,3,5-thiadiazinan-4-one Chemical compound C1SC(=NC(C)(C)C)N(C(C)CC)C(=O)N1C1=CC=C(C)C=C1C YTLMBKFXWASSEX-UHFFFAOYSA-N 0.000 claims 1
- 239000003701 inert diluent Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 504
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 179
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 156
- 239000000243 solution Substances 0.000 description 105
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 100
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 91
- 239000013078 crystal Substances 0.000 description 91
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 86
- 125000001309 chloro group Chemical group Cl* 0.000 description 80
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 77
- 238000003756 stirring Methods 0.000 description 55
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 46
- 238000002844 melting Methods 0.000 description 46
- 230000008018 melting Effects 0.000 description 46
- 239000000126 substance Substances 0.000 description 45
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 37
- 238000012360 testing method Methods 0.000 description 37
- 239000011541 reaction mixture Substances 0.000 description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 29
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 28
- 238000004821 distillation Methods 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 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 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 239000004615 ingredient Substances 0.000 description 17
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 17
- 238000002156 mixing Methods 0.000 description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
- 238000001914 filtration Methods 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 238000010992 reflux Methods 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000004927 clay Substances 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 11
- 239000000376 reactant Substances 0.000 description 11
- RFONJRMUUALMBA-UHFFFAOYSA-N 2-methanidylpropane Chemical compound CC(C)[CH2-] RFONJRMUUALMBA-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 239000007983 Tris buffer Substances 0.000 description 10
- 241000607479 Yersinia pestis Species 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 10
- NUJIXNWAWRCFKV-UHFFFAOYSA-N n-(chloromethyl)-n-phenylcarbamoyl chloride Chemical compound ClCN(C(Cl)=O)C1=CC=CC=C1 NUJIXNWAWRCFKV-UHFFFAOYSA-N 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- 239000007921 spray Substances 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 239000012752 auxiliary agent Substances 0.000 description 8
- 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 8
- 239000000725 suspension Substances 0.000 description 8
- 239000008096 xylene Substances 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 239000011575 calcium Substances 0.000 description 7
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
- 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 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- VLCDUOXHFNUCKK-UHFFFAOYSA-N N,N'-Dimethylthiourea Chemical compound CNC(=S)NC VLCDUOXHFNUCKK-UHFFFAOYSA-N 0.000 description 6
- 241001556089 Nilaparvata lugens Species 0.000 description 6
- 241000209094 Oryza Species 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229910052791 calcium Inorganic materials 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000000428 dust Substances 0.000 description 6
- 239000004495 emulsifiable concentrate Substances 0.000 description 6
- 235000013312 flour Nutrition 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 239000008202 granule composition Substances 0.000 description 6
- 239000002917 insecticide Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 241000358422 Nephotettix cincticeps Species 0.000 description 5
- 235000007164 Oryza sativa Nutrition 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 241000176086 Sogatella furcifera Species 0.000 description 5
- 241001454293 Tetranychus urticae Species 0.000 description 5
- 238000007605 air drying Methods 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000000440 bentonite Substances 0.000 description 5
- 229910000278 bentonite Inorganic materials 0.000 description 5
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000123 paper Substances 0.000 description 5
- 235000009566 rice Nutrition 0.000 description 5
- 239000004563 wettable powder Substances 0.000 description 5
- 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 4
- 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 4
- 101150041968 CDC13 gene Proteins 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000005909 Kieselgur Substances 0.000 description 4
- 241000488581 Panonychus citri Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 235000013339 cereals Nutrition 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 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 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
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 4
- 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 3
- FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical compound COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 3
- LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
- 241000254113 Tribolium castaneum Species 0.000 description 3
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 239000003350 kerosene Substances 0.000 description 3
- 238000004898 kneading Methods 0.000 description 3
- 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 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- 230000001766 physiological effect Effects 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 3
- 239000002023 wood Substances 0.000 description 3
- FSJYRLHKLVGCNH-UHFFFAOYSA-N (3-tert-butylphenyl) n-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC(C(C)(C)C)=C1 FSJYRLHKLVGCNH-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
- 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 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- FOQGRRCSZSDSPW-UHFFFAOYSA-N 1-methyl-3-propan-2-ylthiourea Chemical compound CNC(=S)NC(C)C FOQGRRCSZSDSPW-UHFFFAOYSA-N 0.000 description 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 2
- 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 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- FBEHFRAORPEGFH-UHFFFAOYSA-N Allyxycarb Chemical compound CNC(=O)OC1=CC(C)=C(N(CC=C)CC=C)C(C)=C1 FBEHFRAORPEGFH-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 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
- 240000000560 Citrus x paradisi Species 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 241000256059 Culex pipiens Species 0.000 description 2
- SDKQRNRRDYRQKY-UHFFFAOYSA-N Dioxacarb Chemical compound CNC(=O)OC1=CC=CC=C1C1OCCO1 SDKQRNRRDYRQKY-UHFFFAOYSA-N 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- 241001299253 Henosepilachna vigintioctopunctata Species 0.000 description 2
- 241001470017 Laodelphax striatella Species 0.000 description 2
- 229920001732 Lignosulfonate Polymers 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 241000699670 Mus sp. Species 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
- 241000500437 Plutella xylostella Species 0.000 description 2
- ISRUGXGCCGIOQO-UHFFFAOYSA-N Rhoden Chemical compound CNC(=O)OC1=CC=CC=C1OC(C)C ISRUGXGCCGIOQO-UHFFFAOYSA-N 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
- CVQODEWAPZVVBU-UHFFFAOYSA-N XMC Chemical compound CNC(=O)OC1=CC(C)=CC(C)=C1 CVQODEWAPZVVBU-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 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 2
- 239000000969 carrier Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 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
- 230000007613 environmental effect Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 235000019256 formaldehyde Nutrition 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 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 2
- 150000002576 ketones Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- VOEYXMAFNDNNED-UHFFFAOYSA-N metolcarb Chemical compound CNC(=O)OC1=CC=CC(C)=C1 VOEYXMAFNDNNED-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
- 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 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
- 230000000704 physical effect Effects 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000047 product Substances 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
- 229920001059 synthetic polymer Polymers 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 2
- XUNYDVLIZWUPAW-UHFFFAOYSA-N (4-chlorophenyl) n-(4-methylphenyl)sulfonylcarbamate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)OC1=CC=C(Cl)C=C1 XUNYDVLIZWUPAW-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- HUTLODTYVWHFRI-UHFFFAOYSA-N 1,3,5-thiadiazin-4-one Chemical compound O=C1N=CSC=N1 HUTLODTYVWHFRI-UHFFFAOYSA-N 0.000 description 1
- LKLLNYWECKEQIB-UHFFFAOYSA-N 1,3,5-triazinane Chemical compound C1NCNCN1 LKLLNYWECKEQIB-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
- 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
- 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 1
- 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 1
- KAJICSGLHKRDLN-UHFFFAOYSA-N 1,3-dicyclohexylthiourea Chemical compound C1CCCCC1NC(=S)NC1CCCCC1 KAJICSGLHKRDLN-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
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-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
- WWIODCQAOPIKHL-UHFFFAOYSA-N 1-butan-2-yl-3-phenylthiourea Chemical compound CCC(C)NC(=S)NC1=CC=CC=C1 WWIODCQAOPIKHL-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
- QAHPQPNUAZUXFL-UHFFFAOYSA-N 1-methyl-3-(2-methylphenyl)thiourea Chemical compound CNC(=S)NC1=CC=CC=C1C QAHPQPNUAZUXFL-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
- 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
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-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
- KDAXBHLKHKJTNO-UHFFFAOYSA-N 2-butan-2-ylimino-3,5-diphenyl-1,3,5-thiadiazinan-4-one Chemical compound CCC(C)N=C1SCN(C=2C=CC=CC=2)C(=O)N1C1=CC=CC=C1 KDAXBHLKHKJTNO-UHFFFAOYSA-N 0.000 description 1
- UJFZUBNVQYHFIS-UHFFFAOYSA-N 2-butan-2-ylimino-5-(4-fluorophenyl)-3-propan-2-yl-1,3,5-thiadiazinan-4-one Chemical compound O=C1N(C(C)C)C(=NC(C)CC)SCN1C1=CC=C(F)C=C1 UJFZUBNVQYHFIS-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- LBZOCIPSMSMQBN-UHFFFAOYSA-N 2-cyclohexylimino-5-(2,3-dimethylphenyl)-3-ethyl-1,3,5-thiadiazinan-4-one Chemical compound CCN1C(=O)N(C=2C(=C(C)C=CC=2)C)CSC1=NC1CCCCC1 LBZOCIPSMSMQBN-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
- YYFSUBWPSVQAKC-UHFFFAOYSA-N 2-tert-butylimino-5-(2,3-dimethylphenyl)-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)=C1C YYFSUBWPSVQAKC-UHFFFAOYSA-N 0.000 description 1
- QDNQJFXUQXDEDB-UHFFFAOYSA-N 2-tert-butylimino-5-(2,4-dimethylphenyl)-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=C1C QDNQJFXUQXDEDB-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
- LNHUWTMGWZELTI-UHFFFAOYSA-N 2-tert-butylimino-5-(3,4-dichlorophenyl)-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(Cl)=C1 LNHUWTMGWZELTI-UHFFFAOYSA-N 0.000 description 1
- VKXBPGSOZBOWIH-UHFFFAOYSA-N 2-tert-butylimino-5-(3-chlorophenyl)-3-ethyl-1,3,5-thiadiazinan-4-one Chemical compound C1SC(=NC(C)(C)C)N(CC)C(=O)N1C1=CC=CC(Cl)=C1 VKXBPGSOZBOWIH-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
- 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
- VYVOTZQPTJMCBY-UHFFFAOYSA-N 3-benzyl-2-benzylimino-5-(4-methylphenyl)-1,3,5-thiadiazinan-4-one Chemical compound C1=CC(C)=CC=C1N(CS1)C(=O)N(CC=2C=CC=CC=2)C1=NCC1=CC=CC=C1 VYVOTZQPTJMCBY-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
- OPROYKCGKAMRTI-UHFFFAOYSA-N 3-benzyl-2-tert-butylimino-5-(2,3-dimethylphenyl)-1,3,5-thiadiazinan-4-one Chemical compound CC1=CC=CC(N2C(N(CC=3C=CC=CC=3)C(=NC(C)(C)C)SC2)=O)=C1C OPROYKCGKAMRTI-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
- IVETUOFIKGZGTO-UHFFFAOYSA-N 3-benzyl-5-(3,5-dichlorophenyl)-2-propan-2-ylimino-1,3,5-thiadiazinan-4-one Chemical compound CC(C)N=C1SCN(C=2C=C(Cl)C=C(Cl)C=2)C(=O)N1CC1=CC=CC=C1 IVETUOFIKGZGTO-UHFFFAOYSA-N 0.000 description 1
- SVOQTCQOICABEE-UHFFFAOYSA-N 3-benzyl-5-(4-methoxyphenyl)-2-propan-2-ylimino-1,3,5-thiadiazinan-4-one Chemical compound C1=CC(OC)=CC=C1N1C(=O)N(CC=2C=CC=CC=2)C(=NC(C)C)SC1 SVOQTCQOICABEE-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
- JPUWMQKEPFVTQM-UHFFFAOYSA-N 3-butan-2-yl-2-tert-butylimino-5-(2-ethylphenyl)-1,3,5-thiadiazinan-4-one Chemical compound C1SC(=NC(C)(C)C)N(C(C)CC)C(=O)N1C1=CC=CC=C1CC JPUWMQKEPFVTQM-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
- 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
- IZYJJNNBULXTMK-UHFFFAOYSA-N 3-cyclohexyl-2-cyclohexylimino-5-(2-methylphenyl)-1,3,5-thiadiazinan-4-one Chemical compound CC1=CC=CC=C1N(CS1)C(=O)N(C2CCCCC2)C1=NC1CCCCC1 IZYJJNNBULXTMK-UHFFFAOYSA-N 0.000 description 1
- NLWFOGRGBNCQEZ-UHFFFAOYSA-N 3-methyl-2-methylimino-5-phenyl-1,3,5-thiadiazinan-4-one Chemical compound O=C1N(C)C(=NC)SCN1C1=CC=CC=C1 NLWFOGRGBNCQEZ-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
- IROKIESUZZKUHR-UHFFFAOYSA-N 3-methyl-2-phenylimino-5-propan-2-yl-1,3,5-thiadiazinan-4-one Chemical compound C1(=CC=CC=C1)N=C1SCN(C(N1C)=O)C(C)C IROKIESUZZKUHR-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
- ZGOHCJXAEGQJOU-UHFFFAOYSA-N 3-methyl-5-phenyl-2-phenylimino-1,3,5-thiadiazinan-4-one Chemical compound C1(=CC=CC=C1)N=C1SCN(C(N1C)=O)C1=CC=CC=C1 ZGOHCJXAEGQJOU-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
- ANCAEIZILMBKEP-UHFFFAOYSA-N 3-methyl-5-propan-2-yl-2-propan-2-ylimino-1,3,5-thiadiazinan-4-one Chemical compound CC(C)N=C1SCN(C(C)C)C(=O)N1C ANCAEIZILMBKEP-UHFFFAOYSA-N 0.000 description 1
- RYXVIROPOSSDSJ-UHFFFAOYSA-N 3-propan-2-yl-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)C)C(=NC(C)C)SC1 RYXVIROPOSSDSJ-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
- 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
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 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
- 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
- HHGPZCBNAXJVIR-UHFFFAOYSA-N 5-(2-chlorophenyl)-2-ethylimino-3-phenyl-1,3,5-thiadiazinan-4-one Chemical compound CCN=C1SCN(C=2C(=CC=CC=2)Cl)C(=O)N1C1=CC=CC=C1 HHGPZCBNAXJVIR-UHFFFAOYSA-N 0.000 description 1
- OUGFZEKADJXSKD-UHFFFAOYSA-N 5-(2-chlorophenyl)-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=C1Cl OUGFZEKADJXSKD-UHFFFAOYSA-N 0.000 description 1
- UGTNFQRBWDUYRY-UHFFFAOYSA-N 5-(4-bromophenyl)-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(Br)C=C1 UGTNFQRBWDUYRY-UHFFFAOYSA-N 0.000 description 1
- YBHPGDZUGBVOJS-UHFFFAOYSA-N 5-(4-chlorophenyl)-3-methyl-2-methylimino-1,3,5-thiadiazinan-4-one Chemical compound O=C1N(C)C(=NC)SCN1C1=CC=C(Cl)C=C1 YBHPGDZUGBVOJS-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
- SUPXZOQQOVANRP-UHFFFAOYSA-N 5-benzyl-3-methyl-2-methylimino-1,3,5-thiadiazinan-4-one Chemical compound O=C1N(C)C(=NC)SCN1CC1=CC=CC=C1 SUPXZOQQOVANRP-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
- VTIUXLLGSFXBDM-UHFFFAOYSA-N 5-tert-butyl-2-tert-butylimino-3-phenyl-1,3,5-thiadiazinan-4-one Chemical compound CC(C)(C)N=C1SCN(C(C)(C)C)C(=O)N1C1=CC=CC=C1 VTIUXLLGSFXBDM-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
- GZODLKMDUFIKKR-UHFFFAOYSA-N 5-tert-butyl-3-methyl-2-methylimino-1,3,5-thiadiazinan-4-one Chemical compound CN=C1SCN(C(C)(C)C)C(=O)N1C GZODLKMDUFIKKR-UHFFFAOYSA-N 0.000 description 1
- PPXINQKLBMBOJU-UHFFFAOYSA-N 5-tert-butyl-3-phenyl-2-phenylimino-1,3,5-thiadiazinan-4-one Chemical compound C=1C=CC=CC=1N1C(=O)N(C(C)(C)C)CSC1=NC1=CC=CC=C1 PPXINQKLBMBOJU-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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 125000006519 CCH3 Chemical group 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- STUSTWKEFDQFFZ-UHFFFAOYSA-N Chlordimeform Chemical compound CN(C)C=NC1=CC=C(Cl)C=C1C STUSTWKEFDQFFZ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 241000144210 Culex pipiens pallens Species 0.000 description 1
- 241000256113 Culicidae Species 0.000 description 1
- LRNJHZNPJSPMGK-UHFFFAOYSA-N Cyanofenphos Chemical compound C=1C=CC=CC=1P(=S)(OCC)OC1=CC=C(C#N)C=C1 LRNJHZNPJSPMGK-UHFFFAOYSA-N 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
- 239000005893 Diflubenzuron Substances 0.000 description 1
- 239000005947 Dimethoate Substances 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
- 229920000084 Gum arabic Polymers 0.000 description 1
- 229910003944 H3 PO4 Inorganic materials 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
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- POXAIQSXNOEQGM-UHFFFAOYSA-N Isopropylthioharnstoff Natural products CC(C)NC(N)=S POXAIQSXNOEQGM-UHFFFAOYSA-N 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- FLVIGYVXZHLUHP-UHFFFAOYSA-N N,N'-diethylthiourea Chemical compound CCNC(=S)NCC FLVIGYVXZHLUHP-UHFFFAOYSA-N 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
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000238814 Orthoptera Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 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
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 235000019774 Rice Bran oil Nutrition 0.000 description 1
- 101150059476 SLC44A3 gene Proteins 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 241000779819 Syncarpia glomulifera Species 0.000 description 1
- 241000843170 Togo hemipterus Species 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 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
- 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
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 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
- 150000008431 aliphatic amides Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 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
- 125000003118 aryl group Chemical group 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
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 239000011230 binding agent Substances 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
- 125000006226 butoxyethyl group Chemical group 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
- 239000000073 carbamate insecticide Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- DUEPRVBVGDRKAG-UHFFFAOYSA-N carbofuran Chemical compound CNC(=O)OC1=CC=CC2=C1OC(C)(C)C2 DUEPRVBVGDRKAG-UHFFFAOYSA-N 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
- IRUJZVNXZWPBMU-UHFFFAOYSA-N cartap Chemical compound NC(=O)SCC(N(C)C)CSC(N)=O IRUJZVNXZWPBMU-UHFFFAOYSA-N 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
- 239000003795 chemical substances by application 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
- 239000002361 compost Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000011096 corrugated fiberboard Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000010908 decantation 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
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- OMYMWKVYKBYCBS-UHFFFAOYSA-N diethoxy-(6-methyl-2-propan-2-ylpyrimidin-4-yl)oxy-sulfanylidene-$l^{5}-phosphane;trihydroxy(sulfanylidene)-$l^{5}-phosphane Chemical compound OP(O)(O)=S.CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 OMYMWKVYKBYCBS-UHFFFAOYSA-N 0.000 description 1
- RXQHCVMGXZLBBZ-UHFFFAOYSA-N diethyl 2-dihydroxyphosphinothioylsulfanylbutanedioate Chemical compound CCOC(=O)CC(SP(O)(O)=S)C(=O)OCC RXQHCVMGXZLBBZ-UHFFFAOYSA-N 0.000 description 1
- 229940019503 diflubenzuron Drugs 0.000 description 1
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
- SPCNPOWOBZQWJK-UHFFFAOYSA-N dimethoxy-(2-propan-2-ylsulfanylethylsulfanyl)-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)SCCSC(C)C SPCNPOWOBZQWJK-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- DOFZAZXDOSGAJZ-UHFFFAOYSA-N disulfoton Chemical compound CCOP(=S)(OCC)SCCSCC DOFZAZXDOSGAJZ-UHFFFAOYSA-N 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 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
- 239000004744 fabric Substances 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
- 239000002657 fibrous material Substances 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
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 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
- 229910052736 halogen Inorganic materials 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
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-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
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine 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
- QBSJMKIUCUGGNG-UHFFFAOYSA-N isoprocarb Chemical compound CNC(=O)OC1=CC=CC=C1C(C)C QBSJMKIUCUGGNG-UHFFFAOYSA-N 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- KLGMSAOQDHLCOS-UHFFFAOYSA-N mecarbam Chemical compound CCOC(=O)N(C)C(=O)CSP(=S)(OCC)OCC KLGMSAOQDHLCOS-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
- 230000001459 mortal effect Effects 0.000 description 1
- PTPFCDUAUCDTRW-UHFFFAOYSA-N n-(3-chlorophenyl)carbamoyl chloride Chemical compound ClC(=O)NC1=CC=CC(Cl)=C1 PTPFCDUAUCDTRW-UHFFFAOYSA-N 0.000 description 1
- ZOCYRJKGMXEYTN-UHFFFAOYSA-N n-(4-chlorophenyl)carbamoyl chloride Chemical compound ClC(=O)NC1=CC=C(Cl)C=C1 ZOCYRJKGMXEYTN-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 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
- 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 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
- 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
- YSBUANSGDLZTKV-UHFFFAOYSA-N n-phenylcarbamoyl chloride Chemical compound ClC(=O)NC1=CC=CC=C1 YSBUANSGDLZTKV-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 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
- 235000015097 nutrients Nutrition 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
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 235000021317 phosphate Nutrition 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
- 239000005648 plant growth regulator 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
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 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
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- PWYIUEFFPNVCMW-UHFFFAOYSA-N propaphos Chemical compound CCCOP(=O)(OCCC)OC1=CC=C(SC)C=C1 PWYIUEFFPNVCMW-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 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
- 239000008262 pumice Substances 0.000 description 1
- 239000008165 rice bran oil Substances 0.000 description 1
- MSHXTAQSSIEBQS-UHFFFAOYSA-N s-[3-carbamoylsulfanyl-2-(dimethylamino)propyl] carbamothioate;hydron;chloride Chemical compound [Cl-].NC(=O)SCC([NH+](C)C)CSC(N)=O MSHXTAQSSIEBQS-UHFFFAOYSA-N 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
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 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
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 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
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- RYOCWONLFFPYMN-UHFFFAOYSA-N tert-butylthiourea Chemical compound CC(C)(C)NC(N)=S RYOCWONLFFPYMN-UHFFFAOYSA-N 0.000 description 1
- PTOSZROYCHWBJI-UHFFFAOYSA-N thiadiazin-4-one Chemical compound O=C1C=CSN=N1 PTOSZROYCHWBJI-UHFFFAOYSA-N 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
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 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
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 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)
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 (1)
| Publication Number | Publication Date |
|---|---|
| GB1592043A true GB1592043A (en) | 1981-07-01 |
Family
ID=27457792
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB26091/78A Expired GB1592043A (en) | 1977-06-09 | 1978-05-31 | Tetrahydro-1,3,5-thiadiazin-4-one derivatives |
Country Status (11)
| Country | Link |
|---|---|
| BR (1) | BR7803606A (nl) |
| CH (1) | CH633546A5 (nl) |
| CU (1) | CU34933A (nl) |
| DE (1) | DE2824126C2 (nl) |
| FR (1) | FR2393798A1 (nl) |
| GB (1) | GB1592043A (nl) |
| IT (1) | IT1109653B (nl) |
| MX (1) | MX6009E (nl) |
| MY (1) | MY8400338A (nl) |
| NL (2) | NL175694C (nl) |
| SU (1) | SU876057A3 (nl) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2172804A (en) * | 1985-02-25 | 1986-10-01 | Nihon Nohyaku Co Ltd | Thiadiazin pesticidal composition |
Families Citing this family (6)
| 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 |
| ES2051911T3 (es) * | 1988-07-08 | 1994-07-01 | Mitsui Toatsu Chemicals | Tiadiacinas, procedimiento para su produccion, y agentes insecticidas y acaricidas que comprenden las tiadiacinas. |
| 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 |
| WO2022238576A1 (en) | 2021-05-14 | 2022-11-17 | Syngenta Crop Protection Ag | Seed treatment compositions |
-
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 FR FR787817145A patent/FR2393798A1/fr active Granted
- 1978-06-08 IT IT68334/78A patent/IT1109653B/it active Protection Beyond IP Right Term
- 1978-06-08 MX MX787132U patent/MX6009E/es unknown
- 1978-06-09 NL NLAANVRAGE7806296,A patent/NL175694C/nl 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
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2172804A (en) * | 1985-02-25 | 1986-10-01 | Nihon Nohyaku Co Ltd | Thiadiazin pesticidal composition |
Also Published As
| Publication number | Publication date |
|---|---|
| SU876057A3 (ru) | 1981-10-23 |
| NL175694B (nl) | 1984-07-16 |
| NL7806296A (nl) | 1978-12-12 |
| NL971006I1 (nl) | 1997-08-01 |
| NL175694C (nl) | 1984-12-17 |
| FR2393798A1 (fr) | 1979-01-05 |
| IT1109653B (it) | 1985-12-23 |
| IT7868334A0 (it) | 1978-06-08 |
| MX6009E (es) | 1984-09-24 |
| DE2824126A1 (de) | 1978-12-14 |
| FR2393798B1 (nl) | 1982-01-08 |
| MY8400338A (en) | 1984-12-31 |
| BR7803606A (pt) | 1979-02-20 |
| DE2824126C2 (de) | 1984-06-20 |
| NL971006I2 (nl) | 1997-10-01 |
| CU34933A (en) | 1981-12-04 |
| CH633546A5 (en) | 1982-12-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1077048A (en) | Pyrazole derivatives | |
| ES2231805T3 (es) | Agente de lucha contra las enfermedades en los ambitos de la agricultura y de la horticultura y procedimiento de lucha contra estas enfermedades. | |
| JPS6115877A (ja) | Ｎ‐（２‐ニトロフエニル）‐２‐アミノピリミジン誘導体、その製造方法及び該化合物を含有する組成物 | |
| EP0171768A1 (en) | Substituted propargyloxyacetonitrile derivatives, process for production thereof, and herbicide and agricultural-horticultural fungicide comprising said derivatives as active ingredients | |
| WO1991007392A1 (en) | Pesticidal pyrimidinyl benzoic acids and esters | |
| KR900001196B1 (ko) | 피라졸 유도체의 제조방법 | |
| FR2460936A1 (fr) | Derives de pyridazines et leur application comme fongicides | |
| US4159328A (en) | Tetrahydro-1,3,5-thiadiazin-4-one derivative | |
| GB2194233A (en) | Herbicidal triazolinone derivatives compounds of formula | |
| GB1592043A (en) | Tetrahydro-1,3,5-thiadiazin-4-one derivatives | |
| JPS6036467A (ja) | 置換フエニルスルホニルグアニジン誘導体、その中間体、それらの製法及び雑草防除剤 | |
| KR100254147B1 (ko) | 치환된 아미노퀴나졸리논(티온) 유도체 또는 이의 염, 이의 중간체, 및 해충 구제제 및 이를 이용한 해충 구제방법 | |
| EA000109B1 (ru) | Производные триазина | |
| JPH035454A (ja) | 新規のｎ―フェニルピロリジン類 | |
| IE44486B1 (en) | Propane-1,2-dione-dioximes,a process for their manufacture and their use as pest-combating agents | |
| KR810001411B1 (ko) | 테트라하이드로-1, 3, 5-티아디아진-4-온 유도체의 제조방법 | |
| DE69823191T2 (de) | 1,2,3-thiadiazol-derivate, mittel zur kontrolle von pflanzenkrankheiten und methode zu seiner anwendung | |
| JPH04211065A (ja) | ３−置換フェニルピラゾール誘導体又はその塩類及びその用途 | |
| JPS6231715B2 (nl) | ||
| EP0414511A1 (en) | Thiadiazole derivatives and herbicide compositions containing the same | |
| EP0194562B1 (en) | Fungicidal composition | |
| JPS63122671A (ja) | １−カルバモイル−２−ピラゾリン誘導体、その製造方法およびこの化合物を含有する除草剤 | |
| IL44428A (en) | 3-alkyl-1-(5-substituted-1,3,4-thiadiazol-2-yl)-5-hydroxy-2-imidazolidinones | |
| PL242496B1 (pl) | Nowe pochodne izoselenocyjanianów, selenomoczników i selenokarbaminianów oraz ich zastosowanie | |
| CA1155135A (en) | Herbicide compositions |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 704A | Declaration that licence is not available as of right for an excepted use (par. 4a/1977) | ||
| CTFF | Supplementary protection certificate filed |
Free format text: SPC/GB97/030, 19970721 |
|
| CTFG | Supplementary protection certificate granted |
Free format text: SPC/GB97/030, 19980519, EXPIRES: 20021117 |
|
| PE20 | Patent expired after termination of 20 years |
Effective date: 19980530 |
|
| CTFE | Supplementary protection certificate entered into force |
Free format text: SPC/GB97/030, 980531, EXPIRES: 20021117 |
|
| SPCE | Supplementary protection certificate expired |
Spc suppl protection certif: SPC/GB97/030: Expiry date: 20021117 |