JPS5826724B2 - １− チアジアゾリル −６− アシロキシテトラヒドロピリミジノンルイ - Google Patents
１− チアジアゾリル −６− アシロキシテトラヒドロピリミジノンルイInfo
- Publication number
- JPS5826724B2 JPS5826724B2 JP50110439A JP11043975A JPS5826724B2 JP S5826724 B2 JPS5826724 B2 JP S5826724B2 JP 50110439 A JP50110439 A JP 50110439A JP 11043975 A JP11043975 A JP 11043975A JP S5826724 B2 JPS5826724 B2 JP S5826724B2
- Authority
- JP
- Japan
- Prior art keywords
- thiadiazol
- reaction mixture
- methyl
- tetrahydro
- pyrimidinone
- 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
- 239000000203 mixture Substances 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 42
- 241000196324 Embryophyta Species 0.000 claims description 31
- 239000004009 herbicide Substances 0.000 claims description 10
- 231100000331 toxic Toxicity 0.000 claims description 5
- 230000002588 toxic effect Effects 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 description 78
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 70
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 60
- 238000006243 chemical reaction Methods 0.000 description 53
- 238000010992 reflux Methods 0.000 description 50
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- 239000000047 product Substances 0.000 description 47
- 239000011521 glass Substances 0.000 description 38
- 239000002244 precipitate Substances 0.000 description 37
- NBBJYMSMWIIQGU-UHFFFAOYSA-N propionic aldehyde Natural products CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 29
- 238000004519 manufacturing process Methods 0.000 description 23
- 238000003756 stirring Methods 0.000 description 20
- -1 η-butylamine Chemical compound 0.000 description 20
- 238000002360 preparation method Methods 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 230000002363 herbicidal effect Effects 0.000 description 18
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 16
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000539 dimer Substances 0.000 description 10
- 238000001914 filtration Methods 0.000 description 9
- 239000012948 isocyanate Substances 0.000 description 9
- 150000002513 isocyanates Chemical class 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 229910001873 dinitrogen Inorganic materials 0.000 description 8
- 239000012047 saturated solution Substances 0.000 description 8
- 239000002002 slurry Substances 0.000 description 8
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 7
- 239000007810 chemical reaction solvent Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000012265 solid product Substances 0.000 description 6
- WGKZCFPJVPNRAV-UHFFFAOYSA-N 3-bromopropanal Chemical compound BrCCC=O WGKZCFPJVPNRAV-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- AAOIVJJZEDSKPA-UHFFFAOYSA-N 3-(methylamino)propanal Chemical compound CNCCC=O AAOIVJJZEDSKPA-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 150000001241 acetals Chemical class 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000006053 organic reaction Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- YCIPQJTZJGUXND-UHFFFAOYSA-N Aglaia odorata Alkaloid Natural products C1=CC(OC)=CC=C1C1(C(C=2C(=O)N3CCCC3=NC=22)C=3C=CC=CC=3)C2(O)C2=C(OC)C=C(OC)C=C2O1 YCIPQJTZJGUXND-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- MZGRODPRIKETFE-UHFFFAOYSA-N 1-hydroxypyrimidin-2-one Chemical compound ON1C=CC=NC1=O MZGRODPRIKETFE-UHFFFAOYSA-N 0.000 description 2
- JUPUBWHBHDEZIX-UHFFFAOYSA-N 2-cyclopropyl-5-isocyanato-1,3,4-thiadiazole Chemical class S1C(N=C=O)=NN=C1C1CC1 JUPUBWHBHDEZIX-UHFFFAOYSA-N 0.000 description 2
- RRLBNHGOAVKNNB-UHFFFAOYSA-N 2-isocyanato-5-methyl-1,3,4-thiadiazole Chemical class CC1=NN=C(N=C=O)S1 RRLBNHGOAVKNNB-UHFFFAOYSA-N 0.000 description 2
- DAURFRNOXYUHFB-UHFFFAOYSA-N 2-isocyanato-5-methylsulfanyl-1,3,4-thiadiazole Chemical class CSC1=NN=C(N=C=O)S1 DAURFRNOXYUHFB-UHFFFAOYSA-N 0.000 description 2
- WMIBZKNFYVSASG-UHFFFAOYSA-N 3-(ethylamino)propanal Chemical compound CCNCCC=O WMIBZKNFYVSASG-UHFFFAOYSA-N 0.000 description 2
- OAKKGTKCSDUIDC-UHFFFAOYSA-N 3-(prop-2-ynylamino)propanal Chemical compound O=CCCNCC#C OAKKGTKCSDUIDC-UHFFFAOYSA-N 0.000 description 2
- RWWDBUYAKHYTLT-UHFFFAOYSA-N 3-(propylamino)propanal Chemical compound CCCNCCC=O RWWDBUYAKHYTLT-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 2
- 230000006735 deficit Effects 0.000 description 2
- 239000002837 defoliant Substances 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 244000144972 livestock Species 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 150000004867 thiadiazoles Chemical class 0.000 description 2
- 244000045561 useful plants Species 0.000 description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- GMSKHXBAHLYELG-UHFFFAOYSA-N 1-oxopropan-2-ylurea Chemical compound O=CC(C)NC(N)=O GMSKHXBAHLYELG-UHFFFAOYSA-N 0.000 description 1
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- WZIOQSFJDVWWSM-UHFFFAOYSA-N 2-isocyanato-3H-thiadiazole Chemical class S1N(NC=C1)N=C=O WZIOQSFJDVWWSM-UHFFFAOYSA-N 0.000 description 1
- LJGUQVJJWFWIBA-UHFFFAOYSA-N 2-isocyanato-5-(trifluoromethyl)-1,3,4-thiadiazole Chemical class FC(F)(F)C1=NN=C(N=C=O)S1 LJGUQVJJWFWIBA-UHFFFAOYSA-N 0.000 description 1
- FJFTXFLFJQICLP-UHFFFAOYSA-N 3-(5-methylsulfanyl-1,3,4-thiadiazol-2-yl)-1-(3-oxopropyl)-1-propylurea Chemical compound O=CCCN(CCC)C(=O)NC1=NN=C(SC)S1 FJFTXFLFJQICLP-UHFFFAOYSA-N 0.000 description 1
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
- 244000055702 Amaranthus viridis Species 0.000 description 1
- 235000004135 Amaranthus viridis Nutrition 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 235000009344 Chenopodium album Nutrition 0.000 description 1
- 235000005484 Chenopodium berlandieri Nutrition 0.000 description 1
- 235000009332 Chenopodium rubrum Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 1
- YCDMJWFYAXJVRR-UHFFFAOYSA-N [1-ethyl-3-(5-methoxy-1,3,4-thiadiazol-2-yl)-2-oxo-1,3-diazinan-4-yl] propanoate Chemical compound O=C1N(CC)CCC(OC(=O)CC)N1C1=NN=C(OC)S1 YCDMJWFYAXJVRR-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- JOHUAELJNSBTGS-UHFFFAOYSA-N cyclohexanecarbonyl cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OC(=O)C1CCCCC1 JOHUAELJNSBTGS-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000003966 growth inhibitor Substances 0.000 description 1
- PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000000937 inactivator Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/505,118 US3979388A (en) | 1974-09-11 | 1974-09-11 | Thiadiazolyltetrahydropyrimidinones |
| US05/580,636 US4006009A (en) | 1975-05-27 | 1975-05-27 | 1-Thiadiazolyl-6-acyloxytetrahydropyrimidinone herbicides |
| US05/594,932 US4004912A (en) | 1975-07-10 | 1975-07-10 | 1-Thiadiazolyl-6-acyloxytetrahydropyrimidinone herbicides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5154926A JPS5154926A (en) | 1976-05-14 |
| JPS5826724B2 true JPS5826724B2 (ja) | 1983-06-04 |
Family
ID=27414276
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50110439A Expired JPS5826724B2 (ja) | 1974-09-11 | 1975-09-11 | １− チアジアゾリル −６− アシロキシテトラヒドロピリミジノンルイ |
Country Status (17)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111727185A (zh) | 2017-12-19 | 2020-09-29 | 拜耳公司 | 取代的n-杂环基-和n-杂芳基四氢嘧啶酮及其盐，以及其作为除草活性物质的用途 |
-
1975
- 1975-08-20 IL IL47960A patent/IL47960A/xx unknown
- 1975-09-04 AR AR260261A patent/AR219690A1/es active
- 1975-09-05 CH CH1152175A patent/CH614443A5/xx not_active IP Right Cessation
- 1975-09-09 BR BR7505773A patent/BR7505773A/pt unknown
- 1975-09-09 CA CA235,106A patent/CA1049522A/en not_active Expired
- 1975-09-10 IT IT51281/75A patent/IT1046966B/it active
- 1975-09-10 SE SE7510083A patent/SE7510083L/xx unknown
- 1975-09-10 YU YU2282/75A patent/YU39948B/xx unknown
- 1975-09-10 AT AT699375A patent/AT344700B/de not_active IP Right Cessation
- 1975-09-10 NL NL7510653A patent/NL7510653A/xx not_active Application Discontinuation
- 1975-09-10 DK DK404275A patent/DK404275A/da unknown
- 1975-09-10 GB GB37193/75A patent/GB1510133A/en not_active Expired
- 1975-09-10 NO NO753099A patent/NO753099L/no unknown
- 1975-09-10 DE DE19752540366 patent/DE2540366A1/de not_active Ceased
- 1975-09-10 ES ES440841A patent/ES440841A1/es not_active Expired
- 1975-09-11 JP JP50110439A patent/JPS5826724B2/ja not_active Expired
- 1975-09-11 FR FR7527937A patent/FR2284605A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| AT344700B (de) | 1978-08-10 |
| SE7510083L (sv) | 1976-03-12 |
| FR2284605A1 (fr) | 1976-04-09 |
| CA1049522A (en) | 1979-02-27 |
| JPS5154926A (en) | 1976-05-14 |
| IL47960A (en) | 1978-09-29 |
| YU228275A (en) | 1982-05-31 |
| FR2284605B1 (enrdf_load_stackoverflow) | 1980-04-04 |
| IT1046966B (it) | 1980-09-10 |
| BR7505773A (pt) | 1976-08-31 |
| AU8395775A (en) | 1977-02-17 |
| NL7510653A (nl) | 1976-03-15 |
| ATA699375A (de) | 1977-12-15 |
| CH614443A5 (en) | 1979-11-30 |
| YU39948B (en) | 1985-06-30 |
| AR219690A1 (es) | 1980-09-15 |
| DK404275A (da) | 1976-03-12 |
| NO753099L (enrdf_load_stackoverflow) | 1976-03-12 |
| DE2540366A1 (de) | 1976-03-25 |
| IL47960A0 (en) | 1975-11-25 |
| GB1510133A (en) | 1978-05-10 |
| ES440841A1 (es) | 1977-07-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR950001960B1 (ko) | 이소티아졸카르복실산 유도체, 이것을 유효성분으로 한 벼 도열병 방제제, 및 상기 방제제를 사용한 벼 도열병 방제방법 | |
| US4979982A (en) | Herbicidal cinnamic ester uracils | |
| JPH0660176B2 (ja) | ピラゾールスルホニルウレア誘導体、製法および選択性除草剤 | |
| WO1991007392A1 (en) | Pesticidal pyrimidinyl benzoic acids and esters | |
| KR800000505B1 (ko) | 1-티아디아 졸리이미다 졸리딘온의 제조방법 | |
| JPH05140126A (ja) | トリアゾール誘導体および除草剤 | |
| JP2788044B2 (ja) | マレイミド誘導体およびそれを有効成分として含有する農園芸用殺菌剤 | |
| US4237302A (en) | Dichloroacetylimino herbicide antagonists as plant protection agents | |
| JPS5826724B2 (ja) | １− チアジアゾリル −６− アシロキシテトラヒドロピリミジノンルイ | |
| US4346225A (en) | Herbicidal 2-methylamino thiadiazolines | |
| US4298375A (en) | 2-Substituted-5-phenyl-4-thiazolecarboxylic acids and their derivatives as safening agents | |
| CA1297873C (en) | Thiadiazines, process for production thereof, and insecticide | |
| US4059433A (en) | 3-Alkoxyisothiazole derivatives as herbicides | |
| JPS585161B2 (ja) | ジヨソウヨウソセイブツ | |
| CA1223594A (en) | Herbicidal novel 2-alkoxyaminosulfonylbenzene- sulfonylureas | |
| KR830001039B1 (ko) | 2-이미노-1, 3-디티오 및 1, 3-옥사티오 복소환 화합물 함유 제초제 조성물 | |
| KR970010173B1 (ko) | 함헤테로 시클로헥산디온 유도체, 그의 제조방법 및 제초제 | |
| GB1592043A (en) | Tetrahydro-1,3,5-thiadiazin-4-one derivatives | |
| US4057416A (en) | 3-Alkylthio-, 3-alkylsulfinyl-, and 3-alkylsulfonylisothiazole derivatives as herbicides | |
| JPS5810386B2 (ja) | 新規なチアジアゾリルイミダゾリジノン類の製造方法 | |
| KR800000506B1 (ko) | 1-티아디아졸일-5-아실이미다졸리딘온의 제조방법 | |
| IL44428A (en) | 3-alkyl-1-(5-substituted-1,3,4-thiadiazol-2-yl)-5-hydroxy-2-imidazolidinones | |
| KR810000003B1 (ko) | 1-티아디아졸릴-6-아씰록시 테트라 하이드로 피리미딘온의 제조방법 | |
| JPH0655705B2 (ja) | アシルアミノバレロニトリル誘導体、その製造法およびそれらを含有する除草剤および農園芸用殺菌剤 | |
| FR2519000A1 (enrdf_load_stackoverflow) |