IL31333A - 1,3,4-thiadiazolyl urea compounds,their preparation,and herbicidal compositions containing them - Google Patents
1,3,4-thiadiazolyl urea compounds,their preparation,and herbicidal compositions containing themInfo
- Publication number
- IL31333A IL31333A IL31333A IL3133368A IL31333A IL 31333 A IL31333 A IL 31333A IL 31333 A IL31333 A IL 31333A IL 3133368 A IL3133368 A IL 3133368A IL 31333 A IL31333 A IL 31333A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- radical
- ureas
- compound
- urea
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 23
- 230000002363 herbicidal effect Effects 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title description 4
- CMQJDYXIZIONAP-UHFFFAOYSA-N 1,3,4-thiadiazol-2-ylurea Chemical class NC(=O)NC1=NN=CS1 CMQJDYXIZIONAP-UHFFFAOYSA-N 0.000 title description 2
- 239000013543 active substance Substances 0.000 claims description 30
- -1 compound compound Chemical class 0.000 claims description 26
- 235000013877 carbamide Nutrition 0.000 claims description 25
- 241000196324 Embryophyta Species 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- 150000003672 ureas Chemical class 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 239000000969 carrier Substances 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Chemical group 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000002270 dispersing agent Substances 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 2
- 230000003115 biocidal effect Effects 0.000 claims 1
- 150000004651 carbonic acid esters Chemical class 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- 239000006072 paste Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 239000005995 Aluminium silicate Substances 0.000 description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 7
- 235000012211 aluminium silicate Nutrition 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 7
- 239000008187 granular material Substances 0.000 description 7
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000003513 alkali Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 244000056139 Brassica cretica Species 0.000 description 4
- 235000003351 Brassica cretica Nutrition 0.000 description 4
- 235000003343 Brassica rupestris Nutrition 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 235000010460 mustard Nutrition 0.000 description 4
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 235000007319 Avena orientalis Nutrition 0.000 description 3
- 244000075850 Avena orientalis Species 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 239000004009 herbicide Substances 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 229920000137 polyphosphoric acid Polymers 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 150000003583 thiosemicarbazides Chemical class 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 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 241000209504 Poaceae Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 125000003118 aryl group Chemical class 0.000 description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 230000035784 germination Effects 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 2
- 235000012219 potassium aluminium silicate Nutrition 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 150000004867 thiadiazoles Chemical group 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 150000003738 xylenes Chemical class 0.000 description 2
- QFZFLTTWZPPFSM-UHFFFAOYSA-N (2,2,3,3,3-pentafluoropropanoylamino)thiourea Chemical compound NC(=S)NNC(=O)C(F)(F)C(F)(F)F QFZFLTTWZPPFSM-UHFFFAOYSA-N 0.000 description 1
- SMYMJHWAQXWPDB-UHFFFAOYSA-N (2,4,5-trichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl SMYMJHWAQXWPDB-UHFFFAOYSA-N 0.000 description 1
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 description 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
- PHMQAUXMGFUICG-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-1,3,3-trimethylurea Chemical compound CN(C)C(=O)N(C)C1=CC=C(Cl)C(Cl)=C1 PHMQAUXMGFUICG-UHFFFAOYSA-N 0.000 description 1
- ZRRCPKLWTBJUHI-UHFFFAOYSA-N 1-[(2,3,6-trichlorophenyl)methoxy]propan-1-ol Chemical compound CCC(O)OCC1=C(Cl)C=CC(Cl)=C1Cl ZRRCPKLWTBJUHI-UHFFFAOYSA-N 0.000 description 1
- AXLDYWDVWIIVJD-UHFFFAOYSA-N 1-methyl-3-[(2,2,2-trifluoroacetyl)amino]thiourea Chemical compound CNC(=S)NNC(=O)C(F)(F)F AXLDYWDVWIIVJD-UHFFFAOYSA-N 0.000 description 1
- PYLXUTHKBUVGOP-UHFFFAOYSA-N 2,2-dichloro-5-(2,4,5-trichlorophenoxy)pentanoic acid Chemical class OC(=O)C(Cl)(Cl)CCCOC1=CC(Cl)=C(Cl)C=C1Cl PYLXUTHKBUVGOP-UHFFFAOYSA-N 0.000 description 1
- UYGUFXUBSNDUFA-UHFFFAOYSA-N 2,3,5,6-tetrachlorobenzoic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl UYGUFXUBSNDUFA-UHFFFAOYSA-N 0.000 description 1
- XZIDTOHMJBOSOX-UHFFFAOYSA-N 2,3,6-TBA Chemical compound OC(=O)C1=C(Cl)C=CC(Cl)=C1Cl XZIDTOHMJBOSOX-UHFFFAOYSA-N 0.000 description 1
- 239000003559 2,4,5-trichlorophenoxyacetic acid Substances 0.000 description 1
- YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 description 1
- 239000002794 2,4-DB Substances 0.000 description 1
- JCRNSBKSAQHNIN-UHFFFAOYSA-N 2,4-dibutylnaphthalene-1-sulfonic acid Chemical class C1=CC=CC2=C(S(O)(=O)=O)C(CCCC)=CC(CCCC)=C21 JCRNSBKSAQHNIN-UHFFFAOYSA-N 0.000 description 1
- AUAXYMOBWXOEQD-UHFFFAOYSA-N 2,5-dichloro-3-nitrobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC([N+]([O-])=O)=C1Cl AUAXYMOBWXOEQD-UHFFFAOYSA-N 0.000 description 1
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 1
- FUJSJWRORKKPAI-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)acetyl chloride Chemical compound ClC(=O)COC1=CC=C(Cl)C=C1Cl FUJSJWRORKKPAI-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- IZQAUUVBKYXMET-UHFFFAOYSA-N 2-bromoethanamine Chemical compound NCCBr IZQAUUVBKYXMET-UHFFFAOYSA-N 0.000 description 1
- IULJSGIJJZZUMF-UHFFFAOYSA-N 2-hydroxybenzenesulfonic acid Chemical compound OC1=CC=CC=C1S(O)(=O)=O IULJSGIJJZZUMF-UHFFFAOYSA-N 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- LLWADFLAOKUBDR-UHFFFAOYSA-N 2-methyl-4-chlorophenoxybutyric acid Chemical compound CC1=CC(Cl)=CC=C1OCCCC(O)=O LLWADFLAOKUBDR-UHFFFAOYSA-N 0.000 description 1
- CYWGSFFHHMQKET-UHFFFAOYSA-N 2-methylsulfanylethanamine Chemical compound CSCCN CYWGSFFHHMQKET-UHFFFAOYSA-N 0.000 description 1
- PYSWMLOJSZEZCM-UHFFFAOYSA-N 3,6-dichloro-2-methylbenzoic acid Chemical compound CC1=C(Cl)C=CC(Cl)=C1C(O)=O PYSWMLOJSZEZCM-UHFFFAOYSA-N 0.000 description 1
- XENORHLEQQVHAP-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-1,1-diethylurea Chemical compound CCN(CC)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XENORHLEQQVHAP-UHFFFAOYSA-N 0.000 description 1
- IUJKVTWTCTYOQX-UHFFFAOYSA-N 3-[2-(4-chlorophenoxy)phenyl]-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CC=CC=C1OC1=CC=C(Cl)C=C1 IUJKVTWTCTYOQX-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- KCEKCKYZZHREFI-UHFFFAOYSA-N 3h-thiadiazol-2-amine Chemical class NN1NC=CS1 KCEKCKYZZHREFI-UHFFFAOYSA-N 0.000 description 1
- PTVZQOAHCSKAAS-UHFFFAOYSA-N 4-methyl-3-thiosemicarbazide Chemical compound CNC(=S)NN PTVZQOAHCSKAAS-UHFFFAOYSA-N 0.000 description 1
- NBYBUGOZPWDCPX-UHFFFAOYSA-N 5-(trifluoromethyl)-3h-thiadiazol-2-amine Chemical compound NN1NC=C(C(F)(F)F)S1 NBYBUGOZPWDCPX-UHFFFAOYSA-N 0.000 description 1
- TYMRJKKKYZIDFH-UHFFFAOYSA-N 6-chloro-2-n,4-n-bis(3-methoxypropyl)-1,3,5-triazine-2,4-diamine Chemical compound COCCCNC1=NC(Cl)=NC(NCCCOC)=N1 TYMRJKKKYZIDFH-UHFFFAOYSA-N 0.000 description 1
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 235000003276 Apios tuberosa Nutrition 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000010744 Arachis villosulicarpa Nutrition 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- HSSBORCLYSCBJR-UHFFFAOYSA-N Chloramben Chemical compound NC1=CC(Cl)=CC(C(O)=O)=C1Cl HSSBORCLYSCBJR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- RYECOJGRJDOGPP-UHFFFAOYSA-N Ethylurea Chemical compound CCNC(N)=O RYECOJGRJDOGPP-UHFFFAOYSA-N 0.000 description 1
- 241000220485 Fabaceae Species 0.000 description 1
- ZLSWBLPERHFHIS-UHFFFAOYSA-N Fenoprop Chemical compound OC(=O)C(C)OC1=CC(Cl)=C(Cl)C=C1Cl ZLSWBLPERHFHIS-UHFFFAOYSA-N 0.000 description 1
- 241000910494 Heth Species 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical class [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 239000005983 Maleic hydrazide Substances 0.000 description 1
- BGRDGMRNKXEXQD-UHFFFAOYSA-N Maleic hydrazide Chemical compound OC1=CC=C(O)N=N1 BGRDGMRNKXEXQD-UHFFFAOYSA-N 0.000 description 1
- 244000182930 Matricaria sp Species 0.000 description 1
- 235000008885 Matricaria sp Nutrition 0.000 description 1
- LKJPSUCKSLORMF-UHFFFAOYSA-N Monolinuron Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C=C1 LKJPSUCKSLORMF-UHFFFAOYSA-N 0.000 description 1
- CCGPUGMWYLICGL-UHFFFAOYSA-N Neburon Chemical compound CCCCN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 CCGPUGMWYLICGL-UHFFFAOYSA-N 0.000 description 1
- 244000133018 Panax trifolius Species 0.000 description 1
- 241000071358 Panicum philadelphicum subsp. gattingeri Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000220261 Sinapis Species 0.000 description 1
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 241000219873 Vicia Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- YOKAYYZWWYJPBC-UHFFFAOYSA-N [(2,2,2-trifluoroacetyl)amino]thiourea Chemical compound NC(=S)NNC(=O)C(F)(F)F YOKAYYZWWYJPBC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229940115440 aluminum sodium silicate Drugs 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- PXWUKZGIHQRDHL-UHFFFAOYSA-N atraton Chemical compound CCNC1=NC(NC(C)C)=NC(OC)=N1 PXWUKZGIHQRDHL-UHFFFAOYSA-N 0.000 description 1
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000000022 bacteriostatic agent Substances 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 235000019993 champagne Nutrition 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000007931 coated granule Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- LMKPHJYTFHAGHK-UHFFFAOYSA-N cyclodrine Chemical compound C1CCCC1(O)C(C(=O)OCCN(CC)CC)C1=CC=CC=C1 LMKPHJYTFHAGHK-UHFFFAOYSA-N 0.000 description 1
- CLMGCKCDSPUQEE-UHFFFAOYSA-N cyclopropylurea Chemical compound NC(=O)NC1CC1 CLMGCKCDSPUQEE-UHFFFAOYSA-N 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
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 1
- SWWQNNDPJXYCNJ-UHFFFAOYSA-N didodecylazanium;chloride Chemical compound Cl.CCCCCCCCCCCCNCCCCCCCCCCCC SWWQNNDPJXYCNJ-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000010459 dolomite Substances 0.000 description 1
- 229910000514 dolomite Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 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
- 239000010433 feldspar Substances 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 235000012245 magnesium oxide Nutrition 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229940032007 methylethyl ketone Drugs 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- BMLIZLVNXIYGCK-UHFFFAOYSA-N monuron Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C=C1 BMLIZLVNXIYGCK-UHFFFAOYSA-N 0.000 description 1
- BRWGXKIBQUPVKC-UHFFFAOYSA-N n-[4-(diethylamino)-6-methoxy-1,3,5-triazin-2-yl]-3-methylbutanamide Chemical compound CCN(CC)C1=NC(NC(=O)CC(C)C)=NC(OC)=N1 BRWGXKIBQUPVKC-UHFFFAOYSA-N 0.000 description 1
- ARAFQFMXQDBEPU-UHFFFAOYSA-N n-methyl-5-(trifluoromethyl)-1,3,4-thiadiazol-2-amine Chemical compound CNC1=NN=C(C(F)(F)F)S1 ARAFQFMXQDBEPU-UHFFFAOYSA-N 0.000 description 1
- IOXXVNYDGIXMIP-UHFFFAOYSA-N n-methylprop-2-en-1-amine Chemical compound CNCC=C IOXXVNYDGIXMIP-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000000441 potassium aluminium silicate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- ISEUFVQQFVOBCY-UHFFFAOYSA-N prometon Chemical compound COC1=NC(NC(C)C)=NC(NC(C)C)=N1 ISEUFVQQFVOBCY-UHFFFAOYSA-N 0.000 description 1
- WJNRPILHGGKWCK-UHFFFAOYSA-N propazine Chemical compound CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 WJNRPILHGGKWCK-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- JVXFWBQTVKQAOE-UHFFFAOYSA-N s-phenyl carbamothioate Chemical compound NC(=O)SC1=CC=CC=C1 JVXFWBQTVKQAOE-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- HKAMKLBXTLTVCN-UHFFFAOYSA-N simeton Chemical compound CCNC1=NC(NCC)=NC(OC)=N1 HKAMKLBXTLTVCN-UHFFFAOYSA-N 0.000 description 1
- 239000000429 sodium aluminium silicate Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- WCLDITPGPXSPGV-UHFFFAOYSA-N tricamba Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1C(O)=O WCLDITPGPXSPGV-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1820667A CH488723A (de) | 1967-12-27 | 1967-12-27 | Verfahren zur Herstellung von Thiadiazolyl-harnstoffen |
| CH1520568A CH503757A (de) | 1967-12-27 | 1968-10-11 | Verfahren zur Herstellung von Thiadiazolyl-harnstoffen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL31333A0 IL31333A0 (en) | 1969-02-27 |
| IL31333A true IL31333A (en) | 1972-07-26 |
Family
ID=25715932
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL31333A IL31333A (en) | 1967-12-27 | 1968-12-26 | 1,3,4-thiadiazolyl urea compounds,their preparation,and herbicidal compositions containing them |
Country Status (13)
| Country | Link |
|---|---|
| AT (3) | AT291276B (de) |
| BE (1) | BE725984A (de) |
| BG (3) | BG15579A3 (de) |
| CH (2) | CH488723A (de) |
| CS (1) | CS157650B2 (de) |
| DE (1) | DE1816696C2 (de) |
| DK (1) | DK122728B (de) |
| ES (3) | ES361839A1 (de) |
| FR (1) | FR1601517A (de) |
| GB (1) | GB1254468A (de) |
| IL (1) | IL31333A (de) |
| MY (1) | MY7500074A (de) |
| NL (1) | NL139172B (de) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE757655A (fr) * | 1969-10-17 | 1971-04-16 | Air Prod & Chem | Pesticides pour l'usage agricole |
| CA931961A (en) * | 1970-04-17 | 1973-08-14 | Gulf Research And Development Company | Combating unwanted vegetation with 1,3,4-thiadiazolylureas |
| DE2059328C2 (de) * | 1970-11-24 | 1984-02-23 | Schering AG, 1000 Berlin und 4709 Bergkamen | 1,1,3-Trimethyl-3-(5-äthylsulfinyl-1,3,4-thiadiazol-2-YL)-harnstoff |
| DE2330453A1 (de) * | 1973-06-15 | 1975-01-09 | Velsicol Chemical Corp | Dialkylacetale von heterocyclischem ureidoacetaldehyd und deren wasserloesliche salze |
| US3990881A (en) * | 1975-08-25 | 1976-11-09 | Eli Lilly And Company | 5-(Hetero-ring sulfamoyl)-1,3,4-thiadiazol-2-ylureas |
| GB1561636A (en) * | 1975-11-07 | 1980-02-27 | Lilly Industries Ltd | Herbicidal combinations |
| US4271166A (en) * | 1977-08-15 | 1981-06-02 | Eli Lilly And Company | N-(1,3,4-Thiadiazol-2-yl)benzamides |
| ZA775225B (en) * | 1977-08-29 | 1978-03-29 | Lilly Co Eli | Herbicidal combinations |
| US4987233A (en) * | 1988-06-15 | 1991-01-22 | Eli Lilly And Company | Process for preparing herbicidal ureas and insecticidal carbamates and carbamate derivatives |
| JP5527923B2 (ja) * | 2007-03-28 | 2014-06-25 | 公益財団法人相模中央化学研究所 | パーフルオロアルキル基を有する複素環化合物およびその製造方法 |
| CN109053634A (zh) * | 2018-09-26 | 2018-12-21 | 河北工业大学 | 一种噻氟隆原药的制备方法 |
| CN111218200B (zh) * | 2020-01-17 | 2022-03-01 | 北京信为兢创科技有限公司 | 一种高耐磨性防潮涂覆组合物及其制备方法和应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2655445A (en) * | 1949-12-06 | 1953-10-13 | Du Pont | 3-(halophenyl)-1-methyl-1-(methyl or ethyl) ureas and herbicidal compositions and methods employing same |
| DE964548C (de) * | 1955-06-03 | 1957-05-23 | Bayer Ag | Unkrautvertilgungsmittel |
| DE1028986B (de) * | 1956-01-17 | 1958-04-30 | Hoechst Ag | Verfahren zur Herstellung von neuen Harnstoffderivaten |
| BE594227A (de) * | 1959-08-21 | |||
| CH403391A (de) * | 1960-11-22 | 1965-11-30 | Ciba Geigy | Herbicides Mittel, enthaltend neue Harnstoffe |
| CH398543A (de) * | 1961-05-06 | 1966-03-15 | Ciba Geigy | Verfahren zur Herstellung von Harnstoffderivaten |
| NL293262A (de) * | 1962-05-28 | |||
| OA01933A (fr) * | 1965-04-06 | 1970-02-04 | Pechiney Saint Gobain | Dérivés du thiazole. |
| DE1542789C3 (de) * | 1965-09-18 | 1978-05-18 | Bayer Ag, 5090 Leverkusen | Selektive Unkrautbekämpfung |
-
1967
- 1967-12-27 CH CH1820667A patent/CH488723A/de not_active IP Right Cessation
-
1968
- 1968-10-11 CH CH1520568A patent/CH503757A/de not_active IP Right Cessation
- 1968-12-20 DK DK628068AA patent/DK122728B/da not_active IP Right Cessation
- 1968-12-23 DE DE1816696A patent/DE1816696C2/de not_active Expired
- 1968-12-23 GB GB60940/68A patent/GB1254468A/en not_active Expired
- 1968-12-23 AT AT1249468A patent/AT291276B/de active
- 1968-12-23 AT AT305170A patent/AT291670B/de not_active IP Right Cessation
- 1968-12-23 AT AT305070A patent/AT291282B/de not_active IP Right Cessation
- 1968-12-23 ES ES361839A patent/ES361839A1/es not_active Expired
- 1968-12-24 NL NL686818641A patent/NL139172B/xx not_active IP Right Cessation
- 1968-12-24 ES ES361837A patent/ES361837A1/es not_active Expired
- 1968-12-24 BE BE725984D patent/BE725984A/xx not_active IP Right Cessation
- 1968-12-24 ES ES361838A patent/ES361838A1/es not_active Expired
- 1968-12-26 BG BG013638A patent/BG15579A3/bg unknown
- 1968-12-26 BG BG011317A patent/BG15577A3/bg unknown
- 1968-12-26 FR FR1601517D patent/FR1601517A/fr not_active Expired
- 1968-12-26 IL IL31333A patent/IL31333A/en unknown
- 1968-12-27 CS CS882468A patent/CS157650B2/cs unknown
-
1969
- 1969-04-16 BG BG012072A patent/BG15522A3/bg unknown
-
1975
- 1975-12-30 MY MY74/75A patent/MY7500074A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR1601517A (de) | 1970-08-24 |
| BG15579A3 (bg) | 1972-05-20 |
| GB1254468A (en) | 1971-11-24 |
| CH503757A (de) | 1971-02-28 |
| ES361839A1 (es) | 1971-01-01 |
| CH488723A (de) | 1970-04-15 |
| BG15522A3 (bg) | 1976-06-21 |
| DE1816696A1 (de) | 1969-08-21 |
| ES361837A1 (es) | 1970-11-16 |
| NL6818641A (de) | 1969-07-01 |
| AT291282B (de) | 1971-07-12 |
| DK122728B (da) | 1972-04-04 |
| CS157650B2 (de) | 1974-09-16 |
| AT291276B (de) | 1971-07-12 |
| MY7500074A (en) | 1975-12-31 |
| DE1816696C2 (de) | 1983-05-19 |
| NL139172B (nl) | 1973-06-15 |
| AT291670B (de) | 1971-07-26 |
| IL31333A0 (en) | 1969-02-27 |
| BG15577A3 (bg) | 1972-05-20 |
| ES361838A1 (es) | 1970-11-01 |
| BE725984A (de) | 1969-06-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3326663A (en) | Herbicidal phenylureas | |
| IL31333A (en) | 1,3,4-thiadiazolyl urea compounds,their preparation,and herbicidal compositions containing them | |
| EP0171768A1 (de) | Substituierte Propargyloxyacetonitrilderivate, Verfahren zu ihrer Herstellung sowie diese Derivate als Wirkstoffe enthaltende Herbizide und Fungizide für Landwirtschaft und Gartenbau | |
| IL32632A (en) | 1,3,4-thiadiazolyl ureas,their preparation and use as herbicides | |
| GB1572573A (en) | Organophosphorus herbicidal agents | |
| PL76443B1 (pl) | Środek chwastobójczy | |
| US3917478A (en) | Herbicidal compositions and methods utilizing thiadiazolis ureas | |
| US3564607A (en) | Halogenated aryloxyacetyl cyanamides | |
| US3629275A (en) | Carboxylic acid (1 2 4-thiadiazol-5-yl)-amides | |
| US4686294A (en) | 1,3,4-thiadiazolyl ureas and processes for controlling weeds and wild grasses therewith | |
| US4144049A (en) | N-(4-Benzyloxyphenyl)-N-methyl-N-methoxyurea | |
| US3756803A (en) | Herbicidal pyrido(1,2-delta)-s-triazinediones | |
| EP0026034B1 (de) | 5-Amino-4-cyano-1-(2,4,6-trichlorphenyl)pyrazol, Verfahren zu seiner Herstellung, es enthaltende herbizide Zusammensetzungen und deren Verwendung | |
| US3962306A (en) | Sulfonyloxyphenylurea compounds and herbicidal compositions | |
| US4169721A (en) | N-(ortho-substituted benzyl)-dinitro-trifluoromethyl-anilines as plant growth regulants | |
| US3646136A (en) | 2-ureido-benzamides their production and use | |
| US4412855A (en) | 2-Chloro-N-(2'-methoxypropyl)- and 2-chloro-N-(2'-ethoxypropyl)-2",6"-dimethyl-acetanilide as long term weed killers | |
| US3981714A (en) | Cyclic N-thiadiazolyl-(2)-carboxylic acid compounds and herbicidal compositions | |
| US4501605A (en) | Herbicidal heterocyclic compounds and compositions | |
| PL79493B1 (de) | ||
| USRE29439E (en) | Certain 1,2,4-Oxa- and -thiadiazol-5-ylthioalkanoic acid derivatives | |
| US4405791A (en) | Arylthioureido pyridinecarbamino compounds and use as plant growth regulants | |
| US4854965A (en) | Herbicidal compositions | |
| US3763209A (en) | 2,4-dicyano-6-nitro-benzene amines | |
| US4482737A (en) | Preparation of N-substituted N-isocyanatocarbonyl-carbamates |