NO753099L - - Google Patents
Info
- Publication number
- NO753099L NO753099L NO753099A NO753099A NO753099L NO 753099 L NO753099 L NO 753099L NO 753099 A NO753099 A NO 753099A NO 753099 A NO753099 A NO 753099A NO 753099 L NO753099 L NO 753099L
- Authority
- NO
- Norway
- Prior art keywords
- thiadiazol
- pyrimidinone
- tetrahydro
- alkyl
- methyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 56
- 238000002360 preparation method Methods 0.000 claims description 56
- 238000006243 chemical reaction Methods 0.000 claims description 51
- 238000010992 reflux Methods 0.000 claims description 47
- 241000196324 Embryophyta Species 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- -1 Thiadiazole compound Chemical class 0.000 claims description 24
- 230000002363 herbicidal effect Effects 0.000 claims description 21
- 125000001188 haloalkyl group Chemical group 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 8
- 150000008064 anhydrides Chemical class 0.000 claims description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 239000012429 reaction media Substances 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- OVAAROARWYHXPN-UHFFFAOYSA-N 4-hydroxy-1-methyl-3-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]-1,3-diazinan-2-one Chemical group O=C1N(C)CCC(O)N1C1=NN=C(C(F)(F)F)S1 OVAAROARWYHXPN-UHFFFAOYSA-N 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 239000012430 organic reaction media Substances 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 231100000331 toxic Toxicity 0.000 claims description 4
- 230000002588 toxic effect Effects 0.000 claims description 4
- KCHYNHBKOZBLQJ-UHFFFAOYSA-N 3-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-4-hydroxy-1-methyl-1,3-diazinan-2-one Chemical compound O=C1N(C)CCC(O)N1C1=NN=C(C(C)(C)C)S1 KCHYNHBKOZBLQJ-UHFFFAOYSA-N 0.000 claims description 3
- AWQGVMHYDKFROX-UHFFFAOYSA-N [1-methyl-2-oxo-3-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]-1,3-diazinan-4-yl] acetate Chemical group O=C1N(C)CCC(OC(C)=O)N1C1=NN=C(C(F)(F)F)S1 AWQGVMHYDKFROX-UHFFFAOYSA-N 0.000 claims description 3
- ISGNQTVYHROXAT-UHFFFAOYSA-N [1-methyl-2-oxo-3-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]-1,3-diazinan-4-yl] benzoate Chemical group FC(C1=NN=C(S1)N1C(N(CCC1OC(C1=CC=CC=C1)=O)C)=O)(F)F ISGNQTVYHROXAT-UHFFFAOYSA-N 0.000 claims description 3
- IIYLCOQNDYYSHI-UHFFFAOYSA-N [3-(5-methylsulfanyl-1,3,4-thiadiazol-2-yl)-2-oxo-1-propyl-1,3-diazinan-4-yl] butanoate Chemical group O=C1N(CCC)CCC(OC(=O)CCC)N1C1=NN=C(SC)S1 IIYLCOQNDYYSHI-UHFFFAOYSA-N 0.000 claims description 3
- ZDHDLIMIBWXQTB-UHFFFAOYSA-N [3-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-1-methyl-2-oxo-1,3-diazinan-4-yl] acetate Chemical group O=C1N(C)CCC(OC(C)=O)N1C1=NN=C(C(C)(C)C)S1 ZDHDLIMIBWXQTB-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 2
- IJZGFAHHROHFIF-UHFFFAOYSA-N [3-(5-methylsulfinyl-1,3,4-thiadiazol-2-yl)-2-oxo-1-prop-2-ynyl-1,3-diazinan-4-yl] benzoate Chemical group S1C(S(=O)C)=NN=C1N1C(=O)N(CC#C)CCC1OC(=O)C1=CC=CC=C1 IJZGFAHHROHFIF-UHFFFAOYSA-N 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 description 77
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 72
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- 239000000047 product Substances 0.000 description 42
- 239000011521 glass Substances 0.000 description 35
- 239000002244 precipitate Substances 0.000 description 35
- 239000000203 mixture Substances 0.000 description 33
- 238000003756 stirring Methods 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000706 filtrate Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 238000001914 filtration Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 8
- 229910001873 dinitrogen Inorganic materials 0.000 description 8
- 239000004009 herbicide Substances 0.000 description 8
- 239000012047 saturated solution Substances 0.000 description 8
- 239000002002 slurry Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- 241001290610 Abildgaardia Species 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
- 239000000243 solution Substances 0.000 description 6
- SWJVFAOGXDGTCX-UHFFFAOYSA-N 2-cyanoethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCC#N SWJVFAOGXDGTCX-UHFFFAOYSA-N 0.000 description 5
- 150000001241 acetals Chemical class 0.000 description 5
- 230000006378 damage Effects 0.000 description 5
- 239000000428 dust Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- UIOXNNAWANDJCZ-UHFFFAOYSA-N 1,1-dimethoxypropane Chemical compound CCC(OC)OC UIOXNNAWANDJCZ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 3
- LPTCOWQQRGJMNE-UHFFFAOYSA-N 2-isocyanato-5-methoxy-1,3,4-thiadiazole Chemical class COC1=NN=C(N=C=O)S1 LPTCOWQQRGJMNE-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 3
- QYOSQYFLNBXVKF-UHFFFAOYSA-N 2-isocyanato-5-methylsulfonyl-1,3,4-thiadiazole Chemical class CS(=O)(=O)C1=NN=C(N=C=O)S1 QYOSQYFLNBXVKF-UHFFFAOYSA-N 0.000 description 3
- TWAUUVMXSRYMPA-UHFFFAOYSA-N 2-tert-butyl-5-isocyanato-1,3,4-thiadiazole Chemical class CC(C)(C)C1=NN=C(N=C=O)S1 TWAUUVMXSRYMPA-UHFFFAOYSA-N 0.000 description 3
- FRNBQLDGXCGOTH-UHFFFAOYSA-N 3,3-dimethoxy-n-methylpropan-1-amine Chemical compound CNCCC(OC)OC FRNBQLDGXCGOTH-UHFFFAOYSA-N 0.000 description 3
- SIVRIOHWGDOMNB-UHFFFAOYSA-N 3-(5-cyclopropyl-1,3,4-thiadiazol-2-yl)-4-hydroxy-1-prop-2-ynyl-1,3-diazinan-2-one Chemical compound OC1CCN(CC#C)C(=O)N1C1=NN=C(C2CC2)S1 SIVRIOHWGDOMNB-UHFFFAOYSA-N 0.000 description 3
- QYNUDMYVEAVPQD-UHFFFAOYSA-N 4-hydroxy-3-(5-methylsulfanyl-1,3,4-thiadiazol-2-yl)-1-propyl-1,3-diazinan-2-one Chemical compound O=C1N(CCC)CCC(O)N1C1=NN=C(SC)S1 QYNUDMYVEAVPQD-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000004965 chloroalkyl group Chemical group 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- XOIYUDRMTQZUOZ-UHFFFAOYSA-N n-ethyl-3,3-dimethoxypropan-1-amine Chemical compound CCNCCC(OC)OC XOIYUDRMTQZUOZ-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 3
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 3
- 150000004867 thiadiazoles Chemical class 0.000 description 3
- 244000045561 useful plants Species 0.000 description 3
- LEIMMJJENBPWPK-UHFFFAOYSA-N 1-ethyl-4-hydroxy-3-(5-methoxy-1,3,4-thiadiazol-2-yl)-1,3-diazinan-2-one Chemical compound O=C1N(CC)CCC(O)N1C1=NN=C(OC)S1 LEIMMJJENBPWPK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- TUAFOYVYXNSXRH-UHFFFAOYSA-N 3,3-dimethoxy-n-prop-2-ynylpropan-1-amine Chemical compound COC(OC)CCNCC#C TUAFOYVYXNSXRH-UHFFFAOYSA-N 0.000 description 2
- IZTWTTYZZGKEKO-UHFFFAOYSA-N 4-hydroxy-1-methyl-3-(5-methyl-1,3,4-thiadiazol-2-yl)-1,3-diazinan-2-one Chemical compound O=C1N(C)CCC(O)N1C1=NN=C(C)S1 IZTWTTYZZGKEKO-UHFFFAOYSA-N 0.000 description 2
- LTEUXHSAYOSFGQ-UHFFFAOYSA-N 5-(trifluoromethyl)-1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=C(C(F)(F)F)S1 LTEUXHSAYOSFGQ-UHFFFAOYSA-N 0.000 description 2
- AVLUMBXGKFNNAS-UHFFFAOYSA-N 5-cyclopropyl-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1C1CC1 AVLUMBXGKFNNAS-UHFFFAOYSA-N 0.000 description 2
- DRHLSQJZTGPDMP-UHFFFAOYSA-N 5-methoxy-1,3,4-thiadiazol-2-amine Chemical compound COC1=NN=C(N)S1 DRHLSQJZTGPDMP-UHFFFAOYSA-N 0.000 description 2
- HMPUHXCGUHDVBI-UHFFFAOYSA-N 5-methyl-1,3,4-thiadiazol-2-amine Chemical compound CC1=NN=C(N)S1 HMPUHXCGUHDVBI-UHFFFAOYSA-N 0.000 description 2
- PCLAZAJARAIGGD-UHFFFAOYSA-N 5-methylsulfanyl-1,3,4-thiadiazol-2-amine Chemical compound CSC1=NN=C(N)S1 PCLAZAJARAIGGD-UHFFFAOYSA-N 0.000 description 2
- GXPKJOYKJDOUKX-UHFFFAOYSA-N 5-methylsulfonyl-1,3,4-thiadiazol-2-amine Chemical compound CS(=O)(=O)C1=NN=C(N)S1 GXPKJOYKJDOUKX-UHFFFAOYSA-N 0.000 description 2
- ICXDPEFCLDSXLI-UHFFFAOYSA-N 5-tert-butyl-1,3,4-thiadiazol-2-amine Chemical compound CC(C)(C)C1=NN=C(N)S1 ICXDPEFCLDSXLI-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 235000005637 Brassica campestris Nutrition 0.000 description 2
- 240000008100 Brassica rapa Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 241000132536 Cirsium Species 0.000 description 2
- 240000004153 Hibiscus sabdariffa Species 0.000 description 2
- 235000001018 Hibiscus sabdariffa Nutrition 0.000 description 2
- 241000209082 Lolium Species 0.000 description 2
- 244000236458 Panicum colonum Species 0.000 description 2
- 235000015225 Panicum colonum Nutrition 0.000 description 2
- 244000292697 Polygonum aviculare Species 0.000 description 2
- 235000006386 Polygonum aviculare Nutrition 0.000 description 2
- 235000002357 Ribes grossularia Nutrition 0.000 description 2
- 244000171263 Ribes grossularia Species 0.000 description 2
- 235000005291 Rumex acetosa Nutrition 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- YHXLMBAWSJESHD-UHFFFAOYSA-N [3-(5-cyclopropyl-1,3,4-thiadiazol-2-yl)-2-oxo-1-prop-2-ynyl-1,3-diazinan-4-yl] benzoate Chemical compound C=1C=CC=CC=1C(=O)OC1CCN(CC#C)C(=O)N1C(S1)=NN=C1C1CC1 YHXLMBAWSJESHD-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000000443 aerosol Substances 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
- 238000007796 conventional method Methods 0.000 description 2
- JOHUAELJNSBTGS-UHFFFAOYSA-N cyclohexanecarbonyl cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OC(=O)C1CCCCC1 JOHUAELJNSBTGS-UHFFFAOYSA-N 0.000 description 2
- 239000002274 desiccant Substances 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 244000144972 livestock Species 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
- 239000000843 powder Substances 0.000 description 2
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 208000037974 severe injury Diseases 0.000 description 2
- 230000009528 severe injury Effects 0.000 description 2
- 235000003513 sheep sorrel Nutrition 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FUKOTTQGWQVMQB-UHFFFAOYSA-N (2-bromoacetyl) 2-bromoacetate Chemical compound BrCC(=O)OC(=O)CBr FUKOTTQGWQVMQB-UHFFFAOYSA-N 0.000 description 1
- PNVPNXKRAUBJGW-UHFFFAOYSA-N (2-chloroacetyl) 2-chloroacetate Chemical compound ClCC(=O)OC(=O)CCl PNVPNXKRAUBJGW-UHFFFAOYSA-N 0.000 description 1
- PEHFQQWAINXOQG-UHFFFAOYSA-N (2-methoxyacetyl) 2-methoxyacetate Chemical compound COCC(=O)OC(=O)COC PEHFQQWAINXOQG-UHFFFAOYSA-N 0.000 description 1
- NLWILHIIFVRCSH-UHFFFAOYSA-N (3,4,5-trichlorobenzoyl) 3,4,5-trichlorobenzoate Chemical compound ClC1=C(Cl)C(Cl)=CC(C(=O)OC(=O)C=2C=C(Cl)C(Cl)=C(Cl)C=2)=C1 NLWILHIIFVRCSH-UHFFFAOYSA-N 0.000 description 1
- DZJZPASJHDOOQA-UHFFFAOYSA-N (3-bromobenzoyl) 3-bromobenzoate Chemical compound BrC1=CC=CC(C(=O)OC(=O)C=2C=C(Br)C=CC=2)=C1 DZJZPASJHDOOQA-UHFFFAOYSA-N 0.000 description 1
- MWUSAETYTBNPDG-UHFFFAOYSA-N (4-chlorobenzoyl) 4-chlorobenzoate Chemical compound C1=CC(Cl)=CC=C1C(=O)OC(=O)C1=CC=C(Cl)C=C1 MWUSAETYTBNPDG-UHFFFAOYSA-N 0.000 description 1
- GLPAOYCUUFPDQJ-UHFFFAOYSA-N (4-ethoxybenzoyl) 4-ethoxybenzoate Chemical compound C1=CC(OCC)=CC=C1C(=O)OC(=O)C1=CC=C(OCC)C=C1 GLPAOYCUUFPDQJ-UHFFFAOYSA-N 0.000 description 1
- BBLXFRIGTQYGOT-UHFFFAOYSA-N (4-fluorobenzoyl) 4-fluorobenzoate Chemical compound C1=CC(F)=CC=C1C(=O)OC(=O)C1=CC=C(F)C=C1 BBLXFRIGTQYGOT-UHFFFAOYSA-N 0.000 description 1
- YGMHIBLUWGDWKP-UHFFFAOYSA-N (4-methoxybenzoyl) 4-methoxybenzoate Chemical compound C1=CC(OC)=CC=C1C(=O)OC(=O)C1=CC=C(OC)C=C1 YGMHIBLUWGDWKP-UHFFFAOYSA-N 0.000 description 1
- QFUSOYKIDBRREL-NSCUHMNNSA-N (e)-but-2-en-1-amine Chemical compound C\C=C\CN QFUSOYKIDBRREL-NSCUHMNNSA-N 0.000 description 1
- VWJYDONMXDIHNY-NSCUHMNNSA-N (e)-pent-3-en-1-amine Chemical compound C\C=C\CCN VWJYDONMXDIHNY-NSCUHMNNSA-N 0.000 description 1
- GFUOIQFPJDKRCI-UHFFFAOYSA-N 1,1-dimethoxybutan-2-amine Chemical compound CCC(N)C(OC)OC GFUOIQFPJDKRCI-UHFFFAOYSA-N 0.000 description 1
- YCCAUCBGSSRGRJ-UHFFFAOYSA-N 1,1-dimethoxyhexan-2-amine Chemical compound CCCCC(N)C(OC)OC YCCAUCBGSSRGRJ-UHFFFAOYSA-N 0.000 description 1
- RLFIBHNMDAYLHJ-UHFFFAOYSA-N 1-ethyl-3-(5-methoxy-1,3,4-thiadiazol-2-yl)-1-(3-oxopropyl)urea Chemical compound O=CCCN(CC)C(=O)NC1=NN=C(OC)S1 RLFIBHNMDAYLHJ-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- KAIIYJPXPCAYEO-UHFFFAOYSA-N 1-methyl-3-(5-methyl-1,3,4-thiadiazol-2-yl)-1-(3-oxopropyl)urea Chemical compound O=CCCN(C)C(=O)NC1=NN=C(C)S1 KAIIYJPXPCAYEO-UHFFFAOYSA-N 0.000 description 1
- QXTRPGAMVIONMK-UHFFFAOYSA-N 2-amino-5-ethyl-1,3,4-thiadiazole Chemical compound CCC1=NN=C(N)S1 QXTRPGAMVIONMK-UHFFFAOYSA-N 0.000 description 1
- ZNLWSJYZRSCVEU-UHFFFAOYSA-N 3,3-dimethoxy-n-propylpropan-1-amine Chemical compound CCCNCCC(OC)OC ZNLWSJYZRSCVEU-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
- BPYRCLVDOPPPIY-UHFFFAOYSA-N 3-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-1-methyl-1-(3-oxopropyl)urea Chemical compound O=CCCN(C)C(=O)NC1=NN=C(C(C)(C)C)S1 BPYRCLVDOPPPIY-UHFFFAOYSA-N 0.000 description 1
- RWWDBUYAKHYTLT-UHFFFAOYSA-N 3-(propylamino)propanal Chemical compound CCCNCCC=O RWWDBUYAKHYTLT-UHFFFAOYSA-N 0.000 description 1
- ASVKKRLMJCWVQF-UHFFFAOYSA-N 3-buten-1-amine Chemical compound NCCC=C ASVKKRLMJCWVQF-UHFFFAOYSA-N 0.000 description 1
- DYUZZXXUVYQTQX-UHFFFAOYSA-N 4-chlorobut-2-en-1-amine Chemical compound NCC=CCCl DYUZZXXUVYQTQX-UHFFFAOYSA-N 0.000 description 1
- PDUVPBCMEMJQGB-UHFFFAOYSA-N 5-(chloromethyl)-1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=C(CCl)S1 PDUVPBCMEMJQGB-UHFFFAOYSA-N 0.000 description 1
- KMICNGJJXVPIQO-UHFFFAOYSA-N 5-(trichloromethyl)-1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=C(C(Cl)(Cl)Cl)S1 KMICNGJJXVPIQO-UHFFFAOYSA-N 0.000 description 1
- UDPUNVVGMBRZKE-UHFFFAOYSA-N 5-butoxy-1,3,4-thiadiazol-2-amine Chemical compound CCCCOC1=NN=C(N)S1 UDPUNVVGMBRZKE-UHFFFAOYSA-N 0.000 description 1
- QPLFNKQUAMIOGI-UHFFFAOYSA-N 5-butylsulfonyl-1,3,4-thiadiazol-2-amine Chemical compound CCCCS(=O)(=O)C1=NN=C(N)S1 QPLFNKQUAMIOGI-UHFFFAOYSA-N 0.000 description 1
- ROBHTWLKDVLHNY-UHFFFAOYSA-N 5-cyclobutyl-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1C1CCC1 ROBHTWLKDVLHNY-UHFFFAOYSA-N 0.000 description 1
- IKOPPSIEFDHKOR-UHFFFAOYSA-N 5-cycloheptyl-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1C1CCCCCC1 IKOPPSIEFDHKOR-UHFFFAOYSA-N 0.000 description 1
- BLBDGPFJLDEFFL-UHFFFAOYSA-N 5-cyclohexyl-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1C1CCCCC1 BLBDGPFJLDEFFL-UHFFFAOYSA-N 0.000 description 1
- MGSBORAJOCQFOK-UHFFFAOYSA-N 5-cyclopentyl-1,3,4-thiadiazol-2-amine Chemical compound S1C(N)=NN=C1C1CCCC1 MGSBORAJOCQFOK-UHFFFAOYSA-N 0.000 description 1
- UNWILELBTFFRJV-UHFFFAOYSA-N 5-ethoxy-1,3,4-thiadiazol-2-amine Chemical compound CCOC1=NN=C(N)S1 UNWILELBTFFRJV-UHFFFAOYSA-N 0.000 description 1
- VWRHSNKTSSIMGE-UHFFFAOYSA-N 5-ethylsulfanyl-1,3,4-thiadiazol-2-amine Chemical compound CCSC1=NN=C(N)S1 VWRHSNKTSSIMGE-UHFFFAOYSA-N 0.000 description 1
- NIMCWMVFUNIBEL-UHFFFAOYSA-N 5-ethylsulfinyl-1,3,4-thiadiazol-2-amine Chemical compound CCS(=O)C1=NN=C(N)S1 NIMCWMVFUNIBEL-UHFFFAOYSA-N 0.000 description 1
- UDPZHCABSWZTLM-UHFFFAOYSA-N 5-hexoxy-1,3,4-thiadiazol-2-amine Chemical compound CCCCCCOC1=NN=C(N)S1 UDPZHCABSWZTLM-UHFFFAOYSA-N 0.000 description 1
- HBDKAKQWNIAKPV-UHFFFAOYSA-N 5-methylsulfinyl-1,3,4-thiadiazol-2-amine Chemical compound CS(=O)C1=NN=C(N)S1 HBDKAKQWNIAKPV-UHFFFAOYSA-N 0.000 description 1
- DSSWCGPUVTWPPT-UHFFFAOYSA-N 5-pent-3-enyl-1,3,4-thiadiazol-2-amine Chemical compound CC=CCCC1=NN=C(N)S1 DSSWCGPUVTWPPT-UHFFFAOYSA-N 0.000 description 1
- ZQWRZVFWBDLVBP-UHFFFAOYSA-N 5-propoxy-1,3,4-thiadiazol-2-amine Chemical compound CCCOC1=NN=C(N)S1 ZQWRZVFWBDLVBP-UHFFFAOYSA-N 0.000 description 1
- NLQURINLKRAGIF-UHFFFAOYSA-N 5-propyl-1,3,4-thiadiazol-2-amine Chemical compound CCCC1=NN=C(N)S1 NLQURINLKRAGIF-UHFFFAOYSA-N 0.000 description 1
- UWXTXBIBHSFVCG-UHFFFAOYSA-N 5-propylsulfanyl-1,3,4-thiadiazol-2-amine Chemical compound CCCSC1=NN=C(N)S1 UWXTXBIBHSFVCG-UHFFFAOYSA-N 0.000 description 1
- AVISACKEXWPKOD-UHFFFAOYSA-N 6-chlorohex-4-en-1-amine Chemical compound NCCCC=CCCl AVISACKEXWPKOD-UHFFFAOYSA-N 0.000 description 1
- 240000000073 Achillea millefolium Species 0.000 description 1
- 235000016704 Achillea millefolium ssp. borealis Nutrition 0.000 description 1
- 235000014418 Achillea millefolium var alpicola Nutrition 0.000 description 1
- 235000013159 Achillea millefolium var arenicola Nutrition 0.000 description 1
- 235000013169 Achillea millefolium var millefolium Nutrition 0.000 description 1
- 235000013184 Achillea millefolium var puberula Nutrition 0.000 description 1
- 240000001592 Amaranthus caudatus Species 0.000 description 1
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 1
- 235000003129 Ambrosia artemisiifolia var elatior Nutrition 0.000 description 1
- 235000009051 Ambrosia paniculata var. peruviana Nutrition 0.000 description 1
- 241000272525 Anas platyrhynchos Species 0.000 description 1
- 240000000662 Anethum graveolens Species 0.000 description 1
- 241000272814 Anser sp. Species 0.000 description 1
- 241000218157 Aquilegia vulgaris Species 0.000 description 1
- 240000005528 Arctium lappa Species 0.000 description 1
- 235000003130 Arctium lappa Nutrition 0.000 description 1
- 235000008078 Arctium minus Nutrition 0.000 description 1
- 235000003097 Artemisia absinthium Nutrition 0.000 description 1
- 240000001851 Artemisia dracunculus Species 0.000 description 1
- 235000017731 Artemisia dracunculus ssp. dracunculus Nutrition 0.000 description 1
- 235000003261 Artemisia vulgaris Nutrition 0.000 description 1
- 241000132092 Aster Species 0.000 description 1
- 240000008399 Barbarea vulgaris Species 0.000 description 1
- 235000007563 Barbarea vulgaris Nutrition 0.000 description 1
- 241001645380 Bassia scoparia Species 0.000 description 1
- 240000004062 Batis maritima Species 0.000 description 1
- 235000014750 Brassica kaber Nutrition 0.000 description 1
- 235000010149 Brassica rapa subsp chinensis Nutrition 0.000 description 1
- 235000010570 Brassica rapa var. rapa Nutrition 0.000 description 1
- 240000009258 Camassia scilloides Species 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
- 241000973174 Carex alba Species 0.000 description 1
- 244000281762 Chenopodium ambrosioides Species 0.000 description 1
- 235000010523 Cicer arietinum Nutrition 0.000 description 1
- 244000045195 Cicer arietinum Species 0.000 description 1
- 244000168525 Croton tiglium Species 0.000 description 1
- 241000219992 Cuphea Species 0.000 description 1
- 244000301850 Cupressus sempervirens Species 0.000 description 1
- 244000052363 Cynodon dactylon Species 0.000 description 1
- 235000004266 Cynoglossum officinale Nutrition 0.000 description 1
- 240000004487 Cynoglossum officinale Species 0.000 description 1
- 235000005853 Cyperus esculentus Nutrition 0.000 description 1
- 244000075634 Cyperus rotundus Species 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 235000002206 Daucus carota subsp carota Nutrition 0.000 description 1
- 244000078127 Eleusine coracana Species 0.000 description 1
- 235000013499 Eleusine coracana subsp coracana Nutrition 0.000 description 1
- 244000294661 Emex spinosa Species 0.000 description 1
- 235000006369 Emex spinosa Nutrition 0.000 description 1
- 240000006212 Erythrina crista-galli Species 0.000 description 1
- 244000207543 Euphorbia heterophylla Species 0.000 description 1
- 244000248416 Fagopyrum cymosum Species 0.000 description 1
- 235000016622 Filipendula ulmaria Nutrition 0.000 description 1
- 244000061544 Filipendula vulgaris Species 0.000 description 1
- 241001488529 Fumaria vaillantii Species 0.000 description 1
- 241000237858 Gastropoda Species 0.000 description 1
- 235000017335 Hordeum vulgare subsp spontaneum Nutrition 0.000 description 1
- 241001299819 Hordeum vulgare subsp. spontaneum Species 0.000 description 1
- 241000320639 Leptochloa Species 0.000 description 1
- 241001071917 Lithospermum Species 0.000 description 1
- 240000004296 Lolium perenne Species 0.000 description 1
- 235000017945 Matricaria Nutrition 0.000 description 1
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 1
- 244000042664 Matricaria chamomilla Species 0.000 description 1
- 235000012629 Mentha aquatica Nutrition 0.000 description 1
- 235000009382 Mollugo verticillata Nutrition 0.000 description 1
- 235000014720 Myrica gale Nutrition 0.000 description 1
- 244000024215 Myrica gale Species 0.000 description 1
- 241000721619 Najas Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000001439 Opuntia Species 0.000 description 1
- 235000013389 Opuntia humifusa var. humifusa Nutrition 0.000 description 1
- 241001148659 Panicum dichotomiflorum Species 0.000 description 1
- 241001520808 Panicum virgatum Species 0.000 description 1
- 240000000275 Persicaria hydropiper Species 0.000 description 1
- 235000017337 Persicaria hydropiper Nutrition 0.000 description 1
- 240000005218 Phyla nodiflora Species 0.000 description 1
- 235000004442 Polygonum persicaria Nutrition 0.000 description 1
- 244000234609 Portulaca oleracea Species 0.000 description 1
- 235000001855 Portulaca oleracea Nutrition 0.000 description 1
- 235000016311 Primula vulgaris Nutrition 0.000 description 1
- 244000028344 Primula vulgaris Species 0.000 description 1
- 241000220286 Sedum Species 0.000 description 1
- 240000003705 Senecio vulgaris Species 0.000 description 1
- 235000002834 Sida rhombifolia Nutrition 0.000 description 1
- 240000003194 Sida rhombifolia Species 0.000 description 1
- 240000002439 Sorghum halepense Species 0.000 description 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 240000001949 Taraxacum officinale Species 0.000 description 1
- 235000005187 Taraxacum officinale ssp. officinale Nutrition 0.000 description 1
- 241000201404 Verbascum blattaria Species 0.000 description 1
- 244000145469 Vernonia anthelmintica Species 0.000 description 1
- 235000013018 Vernonia anthelmintica Nutrition 0.000 description 1
- 244000105017 Vicia sativa Species 0.000 description 1
- 208000000260 Warts Diseases 0.000 description 1
- GHZXBFJJTBWYTH-KQQUZDAGSA-N [(E)-pent-2-enoyl] (E)-pent-2-enoate Chemical compound CC\C=C\C(=O)OC(=O)\C=C\CC GHZXBFJJTBWYTH-KQQUZDAGSA-N 0.000 description 1
- AYNOVABBKQHYBX-UHFFFAOYSA-N [1-butyl-2-oxo-3-(5-propyl-1,3,4-thiadiazol-2-yl)-1,3-diazinan-4-yl] but-3-enoate Chemical compound O=C1N(CCCC)CCC(OC(=O)CC=C)N1C1=NN=C(CCC)S1 AYNOVABBKQHYBX-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
- NUNBGBODAFRTDV-UHFFFAOYSA-N [1-methyl-2-oxo-3-(5-pent-4-enyl-1,3,4-thiadiazol-2-yl)-1,3-diazinan-4-yl] cyclopentanecarboxylate Chemical compound N=1N=C(CCCC=C)SC=1N1C(=O)N(C)CCC1OC(=O)C1CCCC1 NUNBGBODAFRTDV-UHFFFAOYSA-N 0.000 description 1
- KOYGJCFIHJBGGJ-UHFFFAOYSA-N [1-methyl-2-oxo-3-(5-propoxy-1,3,4-thiadiazol-2-yl)-1,3-diazinan-4-yl] 4-propylbenzoate Chemical compound S1C(OCCC)=NN=C1N1C(=O)N(C)CCC1OC(=O)C1=CC=C(CCC)C=C1 KOYGJCFIHJBGGJ-UHFFFAOYSA-N 0.000 description 1
- WAQRVYFVHCQKRN-UHFFFAOYSA-N [1-methyl-2-oxo-3-(5-propylsulfanyl-1,3,4-thiadiazol-2-yl)-1,3-diazinan-4-yl] 4-iodobenzoate Chemical compound S1C(SCCC)=NN=C1N1C(=O)N(C)CCC1OC(=O)C1=CC=C(I)C=C1 WAQRVYFVHCQKRN-UHFFFAOYSA-N 0.000 description 1
- WCGYHXMSMKDFJY-UHFFFAOYSA-N [1-methyl-2-oxo-3-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]-1,3-diazinan-4-yl] 2-bromoacetate Chemical compound O=C1N(C)CCC(OC(=O)CBr)N1C1=NN=C(C(F)(F)F)S1 WCGYHXMSMKDFJY-UHFFFAOYSA-N 0.000 description 1
- XDJWDGQWLYEIJV-UHFFFAOYSA-N [1-methyl-3-(5-methyl-1,3,4-thiadiazol-2-yl)-2-oxo-1,3-diazinan-4-yl] acetate Chemical compound O=C1N(C)CCC(OC(C)=O)N1C1=NN=C(C)S1 XDJWDGQWLYEIJV-UHFFFAOYSA-N 0.000 description 1
- WDHUWLJOSSBKOQ-UHFFFAOYSA-N [2-(4-methylphenyl)acetyl] 2-(4-methylphenyl)acetate Chemical compound C1=CC(C)=CC=C1CC(=O)OC(=O)CC1=CC=C(C)C=C1 WDHUWLJOSSBKOQ-UHFFFAOYSA-N 0.000 description 1
- LXNCKMZKIUQDQH-UHFFFAOYSA-N [3-(5-cyclopentyl-1,3,4-thiadiazol-2-yl)-2-oxo-1-(trichloromethyl)-1,3-diazinan-4-yl] 2-chloroacetate Chemical compound ClCC(=O)OC1CCN(C(Cl)(Cl)Cl)C(=O)N1C1=NN=C(C2CCCC2)S1 LXNCKMZKIUQDQH-UHFFFAOYSA-N 0.000 description 1
- GXPDNZUEPBGAMR-UHFFFAOYSA-N [3-(5-cyclopropyl-1,3,4-thiadiazol-2-yl)-1-hex-4-enyl-2-oxo-1,3-diazinan-4-yl] hexanoate Chemical compound CCCCCC(=O)OC1CCN(CCCC=CC)C(=O)N1C1=NN=C(C2CC2)S1 GXPDNZUEPBGAMR-UHFFFAOYSA-N 0.000 description 1
- LAHVOZRFOFWURA-UHFFFAOYSA-N [3-(5-ethoxy-1,3,4-thiadiazol-2-yl)-1-methyl-2-oxo-1,3-diazinan-4-yl] 3-ethylbenzoate Chemical compound S1C(OCC)=NN=C1N1C(=O)N(C)CCC1OC(=O)C1=CC=CC(CC)=C1 LAHVOZRFOFWURA-UHFFFAOYSA-N 0.000 description 1
- PEJGISJZLQVLOP-UHFFFAOYSA-N [3-(5-ethyl-1,3,4-thiadiazol-2-yl)-1-methyl-2-oxo-1,3-diazinan-4-yl] prop-2-enoate Chemical compound S1C(CC)=NN=C1N1C(=O)N(C)CCC1OC(=O)C=C PEJGISJZLQVLOP-UHFFFAOYSA-N 0.000 description 1
- YIUNPUZXGQZAHN-UHFFFAOYSA-N [3-(5-ethylsulfinyl-1,3,4-thiadiazol-2-yl)-1-methyl-2-oxo-1,3-diazinan-4-yl] 4-(trifluoromethyl)benzoate Chemical compound S1C(S(=O)CC)=NN=C1N1C(=O)N(C)CCC1OC(=O)C1=CC=C(C(F)(F)F)C=C1 YIUNPUZXGQZAHN-UHFFFAOYSA-N 0.000 description 1
- SOCDBWQTIPBJMX-UHFFFAOYSA-N [3-(5-ethylsulfonyl-1,3,4-thiadiazol-2-yl)-1-methyl-2-oxo-1,3-diazinan-4-yl] 2-ethoxybenzoate Chemical compound CCOC1=CC=CC=C1C(=O)OC1N(C=2SC(=NN=2)S(=O)(=O)CC)C(=O)N(C)CC1 SOCDBWQTIPBJMX-UHFFFAOYSA-N 0.000 description 1
- XXXZREKCRJCZJZ-UHFFFAOYSA-N [3-(5-hex-4-enyl-1,3,4-thiadiazol-2-yl)-1-methyl-2-oxo-1,3-diazinan-4-yl] cyclohexanecarboxylate Chemical compound S1C(CCCC=CC)=NN=C1N1C(=O)N(C)CCC1OC(=O)C1CCCCC1 XXXZREKCRJCZJZ-UHFFFAOYSA-N 0.000 description 1
- VGTSNJCEGWWDEC-UHFFFAOYSA-N [3-(5-hexoxy-1,3,4-thiadiazol-2-yl)-1-methyl-2-oxo-1,3-diazinan-4-yl] 4-hexylbenzoate Chemical compound S1C(OCCCCCC)=NN=C1N1C(=O)N(C)CCC1OC(=O)C1=CC=C(CCCCCC)C=C1 VGTSNJCEGWWDEC-UHFFFAOYSA-N 0.000 description 1
- SJCXOWZZGYNYGD-UHFFFAOYSA-N [3-(5-hexyl-1,3,4-thiadiazol-2-yl)-2-oxo-1-pent-3-enyl-1,3-diazinan-4-yl] pentanoate Chemical compound S1C(CCCCCC)=NN=C1N1C(=O)N(CCC=CC)CCC1OC(=O)CCCC SJCXOWZZGYNYGD-UHFFFAOYSA-N 0.000 description 1
- YPSZPNDDSWVUQD-UHFFFAOYSA-N [3-(5-hexylsulfinyl-1,3,4-thiadiazol-2-yl)-1-methyl-2-oxo-1,3-diazinan-4-yl] acetate Chemical compound S1C(S(=O)CCCCCC)=NN=C1N1C(=O)N(C)CCC1OC(C)=O YPSZPNDDSWVUQD-UHFFFAOYSA-N 0.000 description 1
- PCFAXOZMIABJBP-UHFFFAOYSA-N [3-(5-hexylsulfonyl-1,3,4-thiadiazol-2-yl)-1-methyl-2-oxo-1,3-diazinan-4-yl] 3-(chloromethyl)benzoate Chemical compound S1C(S(=O)(=O)CCCCCC)=NN=C1N1C(=O)N(C)CCC1OC(=O)C1=CC=CC(CCl)=C1 PCFAXOZMIABJBP-UHFFFAOYSA-N 0.000 description 1
- MSUVTSYFEULEAC-UHFFFAOYSA-N [3-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-1-methyl-2-oxo-1,3-diazinan-4-yl] but-3-enoate Chemical compound O=C1N(C)CCC(OC(=O)CC=C)N1C1=NN=C(C(C)(C)C)S1 MSUVTSYFEULEAC-UHFFFAOYSA-N 0.000 description 1
- FLGQHDOJHONRLR-UHFFFAOYSA-N [3-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-1-methyl-2-oxo-1,3-diazinan-4-yl] hex-4-enoate Chemical compound CC=CCCC(=O)OC1CCN(C)C(=O)N1C1=NN=C(C(C)(C)C)S1 FLGQHDOJHONRLR-UHFFFAOYSA-N 0.000 description 1
- RAZJGZXTVSVASC-UHFFFAOYSA-N [3-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-1-methyl-2-oxo-1,3-diazinan-4-yl] pent-4-enoate Chemical compound O=C1N(C)CCC(OC(=O)CCC=C)N1C1=NN=C(C(C)(C)C)S1 RAZJGZXTVSVASC-UHFFFAOYSA-N 0.000 description 1
- UHVNRUQUUXYTFI-UHFFFAOYSA-N [3-[5-(chloromethyl)-1,3,4-thiadiazol-2-yl]-1-methyl-2-oxo-1,3-diazinan-4-yl] cycloheptanecarboxylate Chemical compound N=1N=C(CCl)SC=1N1C(=O)N(C)CCC1OC(=O)C1CCCCCC1 UHVNRUQUUXYTFI-UHFFFAOYSA-N 0.000 description 1
- UYTHXLPLGPBBTQ-UHFFFAOYSA-N [4-(chloromethyl)benzoyl] 4-(chloromethyl)benzoate Chemical compound C1=CC(CCl)=CC=C1C(=O)OC(=O)C1=CC=C(CCl)C=C1 UYTHXLPLGPBBTQ-UHFFFAOYSA-N 0.000 description 1
- FNAWJOBKLWLHTA-UHFFFAOYSA-N [4-(trifluoromethyl)benzoyl] 4-(trifluoromethyl)benzoate Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)OC(=O)C1=CC=C(C(F)(F)F)C=C1 FNAWJOBKLWLHTA-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 235000003484 annual ragweed Nutrition 0.000 description 1
- 239000001138 artemisia absinthium Substances 0.000 description 1
- 235000005770 birds nest Nutrition 0.000 description 1
- 235000006263 bur ragweed Nutrition 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 235000003488 common ragweed Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002837 defoliant Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 240000000971 garden vetch Species 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000003966 growth inhibitor Substances 0.000 description 1
- QCPOKUXLSVMAIW-UHFFFAOYSA-N hex-1-yn-3-amine Chemical compound CCCC(N)C#C QCPOKUXLSVMAIW-UHFFFAOYSA-N 0.000 description 1
- FICBXRYQMBKLJJ-UHFFFAOYSA-N hex-5-en-1-amine Chemical compound NCCCCC=C FICBXRYQMBKLJJ-UHFFFAOYSA-N 0.000 description 1
- PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 description 1
- 230000000937 inactivator Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000002500 ions Chemical class 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
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 230000009526 moderate injury Effects 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 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
- IRILZLKKSNFQHA-UHFFFAOYSA-N o-[3-[5-(bromomethyl)-1,3,4-thiadiazol-2-yl]-1-methyl-2-oxo-1,3-diazinan-4-yl] 4-methylbenzenecarbothioate Chemical compound N=1N=C(CBr)SC=1N1C(=O)N(C)CCC1OC(=S)C1=CC=C(C)C=C1 IRILZLKKSNFQHA-UHFFFAOYSA-N 0.000 description 1
- UVBBCQLPTZEDHT-UHFFFAOYSA-N pent-4-en-1-amine Chemical compound NCCCC=C UVBBCQLPTZEDHT-UHFFFAOYSA-N 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
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 235000009736 ragweed Nutrition 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 201000010153 skin papilloma Diseases 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 239000012747 synergistic agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- 235000005765 wild carrot Nutrition 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 (1)
| Publication Number | Publication Date |
|---|---|
| NO753099L true NO753099L (enrdf_load_stackoverflow) | 1976-03-12 |
Family
ID=27414276
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO753099A NO753099L (enrdf_load_stackoverflow) | 1974-09-11 | 1975-09-10 |
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 |
| DE2540366A1 (de) | 1976-03-25 |
| IL47960A0 (en) | 1975-11-25 |
| JPS5826724B2 (ja) | 1983-06-04 |
| GB1510133A (en) | 1978-05-10 |
| ES440841A1 (es) | 1977-07-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0143751B2 (enrdf_load_stackoverflow) | ||
| US4175081A (en) | 5-Substituted thiadiazole ureas | |
| US4979982A (en) | Herbicidal cinnamic ester uracils | |
| NO752680L (enrdf_load_stackoverflow) | ||
| KR920005414B1 (ko) | 5-할로게노알킬-1, 3, 4-티아디아졸-2-일옥시아세트 아미드의 제조방법 | |
| US4338449A (en) | Herbicidal thiadiazolines | |
| PL114534B1 (en) | Herbicide | |
| NO753099L (enrdf_load_stackoverflow) | ||
| US4182712A (en) | 5-Substituted thiadiazole ureas | |
| US4066436A (en) | Method of controlling sicklepod in soybeans | |
| NO753861L (enrdf_load_stackoverflow) | ||
| CA1057291A (en) | 5-cyanoalkyl-1,3,4-thiadiazole-2-ylureas | |
| US3981714A (en) | Cyclic N-thiadiazolyl-(2)-carboxylic acid compounds and herbicidal compositions | |
| KR810000003B1 (ko) | 1-티아디아졸릴-6-아씰록시 테트라 하이드로 피리미딘온의 제조방법 | |
| NO140382B (no) | Tiadiazolylimidazolidinoner med herbicid virkning | |
| GB2111996A (en) | Herbicidal derivatives of tetrahydrobenzothiazole | |
| US3959301A (en) | Algicidol 2-chloro-5-tolyl-1,3,4-thiadiazoles | |
| JPS6013772A (ja) | イソチアゾリルウレア誘導体 | |
| US3944409A (en) | Method of increasing the yield of plants having storage organs by treatment with thiadiazolylimidazolines | |
| US4217459A (en) | Benzylthio-1,3,4-thiadiazol-2-yl ureas | |
| CA1081701A (en) | 3-benzyl-2-methylimino-5-phenyl-.delta..sup.4-1,3,4- thiadiazolines and method of combating undesired plant growth | |
| 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 | |
| EP0093589A1 (en) | Thiadiazolylimidazolidinones, intermediates, formulations and herbicidal method | |
| NO141991B (no) | 1,2,4-triazolidin-3-on-derivater med herbicid virkning | |
| CH433351A (de) | Verfahren zur Herstellung von Isothioharnstoffderivaten |