CH633546A5 - Tetrahydro-1,3,5-thiadiazin-4-one compounds - Google Patents

Tetrahydro-1,3,5-thiadiazin-4-one compounds Download PDF

Info

Publication number: CH633546A5
Authority: CH; Switzerland
Prior art keywords: carbon atoms; thiadiazin; group; groups; tetrahydro
Prior art date: 1977-06-09

Application number

CH621178A

Other languages

German (de)

English (en)

Inventor

Kenichi Ikeda

Hideo Kanno

Michihiro Yasui

Tatsuo Harada

Original Assignee

Nihon Nohyaku Co Ltd

Priority date (The priority date 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 date listed.)

1977-06-09

Filing date

1978-06-07

Publication date

1982-12-15

1977-06-09 Priority claimed from JP6813877A external-priority patent/JPS543083A/ja

1977-06-29 Priority claimed from JP7759477A external-priority patent/JPS5412390A/ja

1977-07-30 Priority claimed from JP9157077A external-priority patent/JPS5427590A/ja

1978-02-28 Priority claimed from JP2255078A external-priority patent/JPS54115387A/ja

1978-06-07 Application filed by Nihon Nohyaku Co Ltd filed Critical Nihon Nohyaku Co Ltd

1982-12-15 Publication of CH633546A5 publication Critical patent/CH633546A5/de

Links

PAMXRTQIJNZQPB-UHFFFAOYSA-N 1,3,5-thiadiazinan-4-one Chemical class O=C1NCSCN1 PAMXRTQIJNZQPB-UHFFFAOYSA-N 0.000 title claims description 10
150000001875 compounds Chemical class 0.000 claims description 154
239000000203 mixture Substances 0.000 claims description 115
-1 substituted-5-substituted phenyl groups Chemical group 0.000 claims description 72
125000004432 carbon atom Chemical group C* 0.000 claims description 39
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 35
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
239000002253 acid Substances 0.000 claims description 27
125000000217 alkyl group Chemical group 0.000 claims description 27
238000006243 chemical reaction Methods 0.000 claims description 25
238000000034 method Methods 0.000 claims description 25
238000002360 preparation method Methods 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 25
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 22
125000001424 substituent group Chemical group 0.000 claims description 20
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 20
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 18
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
230000000749 insecticidal effect Effects 0.000 claims description 16
241000238631 Hexapoda Species 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 10
241000238876 Acari Species 0.000 claims description 9
239000004480 active ingredient Substances 0.000 claims description 8
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 5
CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 5
239000002917 insecticide Substances 0.000 claims description 5
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
241001414720 Cicadellidae Species 0.000 claims description 2
150000007522 mineralic acids Chemical class 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 7
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 6
244000045561 useful plants Species 0.000 claims 4
HUTLODTYVWHFRI-UHFFFAOYSA-N 1,3,5-thiadiazin-4-one Chemical compound O=C1N=CSC=N1 HUTLODTYVWHFRI-UHFFFAOYSA-N 0.000 claims 2
239000003139 biocide Substances 0.000 claims 2
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
241001466042 Fulgoromorpha Species 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
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239000001257 hydrogen Substances 0.000 claims 1
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239000003701 inert diluent Substances 0.000 claims 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 1
239000002689 soil Substances 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 510
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125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 141
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239000013078 crystal Substances 0.000 description 94
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 91
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238000002844 melting Methods 0.000 description 19
230000008018 melting Effects 0.000 description 19
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 19
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125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 18
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
150000003840 hydrochlorides Chemical class 0.000 description 14
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230000000704 physical effect Effects 0.000 description 13
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
229910052799 carbon Inorganic materials 0.000 description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
238000010438 heat treatment Methods 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
WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 10
241000196324 Embryophyta Species 0.000 description 10
241000209094 Oryza Species 0.000 description 10
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 10
235000019441 ethanol Nutrition 0.000 description 10
239000008187 granular material Substances 0.000 description 10
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IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
229910000041 hydrogen chloride Inorganic materials 0.000 description 9
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 9
235000009566 rice Nutrition 0.000 description 9
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
238000001914 filtration Methods 0.000 description 8
239000000725 suspension Substances 0.000 description 8
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 7
241001465754 Metazoa Species 0.000 description 7
239000002585 base Substances 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 7
239000008096 xylene Substances 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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VLCDUOXHFNUCKK-UHFFFAOYSA-N N,N'-Dimethylthiourea Chemical compound CNC(=S)NC VLCDUOXHFNUCKK-UHFFFAOYSA-N 0.000 description 6
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CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
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125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000004495 emulsifiable concentrate Substances 0.000 description 6
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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 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
LKLLNYWECKEQIB-UHFFFAOYSA-N 1,3,5-triazinane Chemical compound C1NCNCN1 LKLLNYWECKEQIB-UHFFFAOYSA-N 0.000 description 5
RFONJRMUUALMBA-UHFFFAOYSA-N 2-methanidylpropane Chemical compound CC(C)[CH2-] RFONJRMUUALMBA-UHFFFAOYSA-N 0.000 description 5
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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
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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 4
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VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
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 3
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 3
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 3
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 3
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
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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
239000002361 compost 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
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
FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-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
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
229940019503 diflubenzuron Drugs 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
NAGJZTKCGNOGPW-UHFFFAOYSA-K dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [O-]P([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-K 0.000 description 1
CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical group C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
150000002170 ethers Chemical class 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
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 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
238000009472 formulation Methods 0.000 description 1
239000007789 gas Substances 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
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
238000011835 investigation Methods 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
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
230000002147 killing effect Effects 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
229920000609 methyl cellulose Polymers 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 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
239000003595 mist Substances 0.000 description 1
ZMBSRNHDTFKMLI-UHFFFAOYSA-N n-(2,6-diethylphenyl)methanimine Chemical compound CCC1=CC=CC(CC)=C1N=C ZMBSRNHDTFKMLI-UHFFFAOYSA-N 0.000 description 1
LMLUKXSZGTUNLD-UHFFFAOYSA-N n-(4-bromophenyl)-n-(chloromethyl)carbamoyl chloride Chemical compound ClCN(C(Cl)=O)C1=CC=C(Br)C=C1 LMLUKXSZGTUNLD-UHFFFAOYSA-N 0.000 description 1
WBJUPEKXYABYPT-UHFFFAOYSA-N n-(chloromethyl)-n-[3-(trifluoromethyl)phenyl]carbamoyl chloride Chemical compound FC(F)(F)C1=CC=CC(N(CCl)C(Cl)=O)=C1 WBJUPEKXYABYPT-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
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
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
239000006072 paste Substances 0.000 description 1
239000008188 pellet Substances 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
239000001739 pinus spp. Substances 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
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 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
108090000623 proteins and genes Proteins 0.000 description 1
239000008262 pumice Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin 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
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
239000004455 soybean meal Substances 0.000 description 1
241000894007 species Species 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
239000004575 stone Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
229920001059 synthetic polymer Polymers 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
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
239000008170 walnut oil Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 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)

CH621178A 1977-06-09 1978-06-07 Tetrahydro-1,3,5-thiadiazin-4-one compounds CH633546A5 (en)

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
CH633546A5 true CH633546A5 (en)	1982-12-15

Family

ID=27457792

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH621178A CH633546A5 (en)	1977-06-09	1978-06-07	Tetrahydro-1,3,5-thiadiazin-4-one compounds

Country Status (11)

Country	Link
BR (1)	BR7803606A (it)
CH (1)	CH633546A5 (it)
CU (1)	CU34933A (it)
DE (1)	DE2824126C2 (it)
FR (1)	FR2393798A1 (it)
GB (1)	GB1592043A (it)
IT (1)	IT1109653B (it)
MX (1)	MX6009E (it)
MY (1)	MY8400338A (it)
NL (2)	NL175694C (it)
SU (1)	SU876057A3 (it)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
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
EP0354297B1 (en) *	1988-07-08	1992-08-05	MITSUI TOATSU CHEMICALS, Inc.	Thiadiazines, process for production thereof, and insecticidal and acaricidal agents comprising the thiadiazines
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
JP2024517342A (ja)	2021-05-14	2024-04-19	シンジェンタクロッププロテクションアクチェンゲゼルシャフト	種子処理組成物

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 CU CU7834933A patent/CU34933A/es unknown
- 1978-06-09 NL NLAANVRAGE7806296,A patent/NL175694C/xx not_active IP Right Cessation
- 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
DE2824126A1 (de)	1978-12-14
BR7803606A (pt)	1979-02-20
CU34933A (en)	1981-12-04
IT7868334A0 (it)	1978-06-08
FR2393798B1 (it)	1982-01-08
NL971006I2 (nl)	1997-10-01
GB1592043A (en)	1981-07-01
NL175694C (nl)	1984-12-17
NL175694B (nl)	1984-07-16
IT1109653B (it)	1985-12-23
MY8400338A (en)	1984-12-31
SU876057A3 (ru)	1981-10-23
MX6009E (es)	1984-09-24
NL7806296A (nl)	1978-12-12
NL971006I1 (nl)	1997-08-01
FR2393798A1 (fr)	1979-01-05
DE2824126C2 (de)	1984-06-20

Legal Events

Date	Code	Title	Description
1998-06-30	PL	Patent ceased
1999-07-15	SPCF	Supplementary protection certificate filed	Free format text: BLW-NR. W 4156/19881118, 19990617
1999-08-31	SPCG	Supplementary protection certificate granted	Free format text: BLW-NR. W 4156/19881118, 19990617, EXPIRES: 20030606

Publication	Publication Date	Title
DE2648008B2 (de)	1979-11-29	Acetanilide
DD144498A5 (de)	1980-10-22	Verfahren zur verringerung von herbizidschaeden
DD283760A5 (de)	1990-10-24	Herbizide und pflanzenwachstumregulierende mittel und deren verwendung sowie verfahren zur herstellung des in ihnen enthaltenen wirkstoffes
DE3713774C2 (de)	1993-10-07	Pyrazol-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende Fungizide
DE3810080A1 (de)	1989-10-05	Trisubstituierte 1,3,5-triazin-2,4,6-trione
DE3883695T2 (de)	1994-02-17	Amid-Derivate, Verfahren zu deren Herstellung sowie diese enthaltende Fungizide in der Agrikultur und im Gartenbau.
DE3618662A1 (de)	1987-12-10	Trisubstituierte 1,3,5-triazin-2,4,6-trione
EP0037971B1 (de)	1983-12-21	Trisubstituierte Cyanguanidine, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide
DE1695989A1 (de)	1971-05-19	Verfahren zur Herstellung von neuen Aryl-1,2,4-oxadiazolidinverbindungen mit herbicider Aktivitaet und Verwendung der neuen Verbindungen als Herbicide
DE2824126C2 (de)	1984-06-20	Tetrahydro-1,3,5-thiadiazin-4-on-Verbindungen
DE3780011T2 (de)	1993-01-14	3-perfluoroalkyl-isoxazol-5-yl-oxycarbonsaeure-derivate, verfahren zu ihrer herstellung und ihre verwendung als herbizide.
EP0117482B1 (de)	1986-09-17	Substituierte Maleinsäureimide und deren Verwendung als Schädlingsbekämpfungsmittel
CA1180334A (en)	1985-01-02	N-sulphenylated biurets, processes for their preparation and their use as fungicides
DE2919825C2 (it)	1988-09-01
DE69823191T2 (de)	2004-08-19	1,2,3-thiadiazol-derivate, mittel zur kontrolle von pflanzenkrankheiten und methode zu seiner anwendung
DE2451899A1 (de)	1975-05-07	Triazindionverbindungen
EP0144052A2 (de)	1985-06-12	Chinolinoxyphenylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchhses
DD262359A5 (de)	1988-11-30	Gyanoacetamidderivate mit fungizider wirksamkeit
CH617571A5 (it)	1980-06-13
DD144354A5 (de)	1980-10-15	Insektizides mittel
KR810001411B1 (ko)	1981-10-20	테트라하이드로-1, 3, 5-티아디아진-4-온 유도체의 제조방법
DE2408234A1 (de)	1975-09-04	Isothiazolylharnstoffe
DE1643039C3 (de)	1976-02-19	Bromacetylharnstoffe, Verfahren zu deren Herstellung und diese enthaltende biocide Mittel
DE1810581C3 (de)	1977-12-29	N-Acyl-p-dialkylamino-phenylhydrazone, Verfahren zu ihrer Herstellung und deren Verwendung zur Bekämpfung von phytopathogene Pilzen
DE3032327A1 (de)	1982-04-01	N-sulfenylierte harnstoffe, verfahren zu ihrer herstellung, diese enthaltende fungizide mittel und ihre verwendung