DE1770467A1 - 1,3,4-thiadiazolyl ureas - Google Patents
1,3,4-thiadiazolyl ureasInfo
- Publication number
- DE1770467A1 DE1770467A1 DE19681770467 DE1770467A DE1770467A1 DE 1770467 A1 DE1770467 A1 DE 1770467A1 DE 19681770467 DE19681770467 DE 19681770467 DE 1770467 A DE1770467 A DE 1770467A DE 1770467 A1 DE1770467 A1 DE 1770467A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- alkyl
- ureas
- thiadiazoly
- meaning given
- 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.)
- Pending
Links
- 235000013877 carbamide Nutrition 0.000 title claims description 11
- -1 1,3,4-thiadiazolyl ureas Chemical class 0.000 title claims description 9
- 241000196324 Embryophyta Species 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- 150000003672 ureas Chemical class 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 239000004009 herbicide Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- QUKGLNCXGVWCJX-UHFFFAOYSA-N 1,3,4-thiadiazol-2-amine Chemical class NC1=NN=CS1 QUKGLNCXGVWCJX-UHFFFAOYSA-N 0.000 claims description 3
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000004965 chloroalkyl group Chemical group 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 150000001805 chlorine compounds Chemical class 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- 239000003995 emulsifying agent Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 230000006378 damage Effects 0.000 description 5
- 230000002363 herbicidal effect Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 244000075850 Avena orientalis Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000219146 Gossypium Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 240000006694 Stellaria media Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 241000209200 Bromus Species 0.000 description 2
- 241000723377 Coffea Species 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000234642 Festuca Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000209082 Lolium Species 0.000 description 2
- 244000042664 Matricaria chamomilla Species 0.000 description 2
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241000209094 Oryza Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011435 rock Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- 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 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- 240000002245 Acer pensylvanicum Species 0.000 description 1
- 235000006760 Acer pensylvanicum Nutrition 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
- 235000005781 Avena Nutrition 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 244000056139 Brassica cretica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241001049165 Caria Species 0.000 description 1
- 235000007866 Chamaemelum nobile Nutrition 0.000 description 1
- 241000219312 Chenopodium Species 0.000 description 1
- 241000208175 Daucus Species 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- 244000239348 Echinochloa crus galli var. praticola Species 0.000 description 1
- 235000007351 Eleusine Nutrition 0.000 description 1
- 241000209215 Eleusine Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241001101998 Galium Species 0.000 description 1
- 235000009438 Gossypium Nutrition 0.000 description 1
- 206010053759 Growth retardation Diseases 0.000 description 1
- 241000209219 Hordeum Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 241000801118 Lepidium Species 0.000 description 1
- 244000211187 Lepidium sativum Species 0.000 description 1
- 235000007849 Lepidium sativum Nutrition 0.000 description 1
- 241000209510 Liliopsida Species 0.000 description 1
- 235000017945 Matricaria Nutrition 0.000 description 1
- 101100310622 Mus musculus Soga1 gene Proteins 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000219833 Phaseolus Species 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241000746981 Phleum Species 0.000 description 1
- 241000746983 Phleum pratense Species 0.000 description 1
- 241001310793 Podium Species 0.000 description 1
- 241000209051 Saccharum Species 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 241000780602 Senecio Species 0.000 description 1
- 240000003705 Senecio vulgaris Species 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- 241000220261 Sinapis Species 0.000 description 1
- 235000002634 Solanum Nutrition 0.000 description 1
- 241000207763 Solanum Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 244000152045 Themeda triandra Species 0.000 description 1
- 241000219422 Urtica Species 0.000 description 1
- 244000274883 Urtica dioica Species 0.000 description 1
- 235000009108 Urtica dioica Nutrition 0.000 description 1
- 241000209149 Zea Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 241001233957 eudicotyledons Species 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 244000230030 foxtail bristlegrass Species 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 208000037824 growth disorder Diseases 0.000 description 1
- 231100000001 growth retardation Toxicity 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 235000009973 maize Nutrition 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
- 235000019713 millet Nutrition 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical class O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000036435 stunted growth Effects 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 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
- CUWHXIJMTMMRTI-UHFFFAOYSA-N thiadiazol-4-amine Chemical class NC1=CSN=N1 CUWHXIJMTMMRTI-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
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 210000002268 wool Anatomy 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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Description
FARBENFABRIKEN BAYER AGFARBENFABRIKEN BAYER AG
LEVERKUSEN-Bayerwerk 2 1. Mai* 1968LEVERKUSEN-Bayerwerk 2 May 1st * 1968
; ΛΤΕΝΤ-ΑίΤΕΙΚ'Νΐ; ST/HS; ΛΤΕΝΤ-ΑίΤΕΙΚ'Νΐ; ST / HS
1.3.4-Thiadlazolyl-harnstoffe1.3.4-thiadlazolyl ureas
Die vorliegende Erfindung betrifft neue 1,3,4-tDhiadiazolylharnstoffe, welche herbizide Eigenschaften haben, sowie mehrere Verfahren zu ihrer Herstellung.The present invention relates to new 1,3,4-thiadiazolylureas which have herbicidal properties, as well as several processes for their preparation.
Es ist bereits bekannt geworden, daS man ü?hlazolyl-harnstoffe, wie den H(4-Methyl-1,3-thiazolyl-2)-N'-methylharnetoff, als Herbizide verwenden kann (belgische Patentschrift 679 138).It has already become known that one can use azolyl ureas, such as the H (4-methyl-1,3-thiazolyl-2) -N'-methyl urea, as Can use herbicides (Belgian patent 679 138).
Es wurde nun gefunden, daß die neuen 1,3,4-Thiadiazolylharnstoffe der FormelIt has now been found that the new 1,3,4-thiadiazolylureas of the formula
a S R * -nil a S R * -nil
(D(D
in welcherin which
H für Ealogenalkyl oder Trif luor-alkoxy-alkyl steht, R' für Wasserstoff, Alkyl, Hydroxyalkyl oder Alkoxy steht, E" für Wasserstoff oder Alkyl steht und Rt« für Alkyl, Alkenyl, Alkinyl, Chloralkyl, AlkoxyalkylH is halogenoalkyl or trifluoroalkoxyalkyl, R 'represents hydrogen, alkyl, hydroxyalkyl or alkoxy, E "represents hydrogen or alkyl and Rt «for alkyl, alkenyl, alkynyl, chloroalkyl, alkoxyalkyl
oder ggf. substituiertes Aryl steht, starke herbizide Eigenschaften aufweisen«or optionally substituted aryl, have strong herbicidal properties «
1098451/T878109845 1 / T878
Weiterhin wurde gefunden, daß man die 1,3.4-Thiadiazolylhamstoffe der Formel (I) erhält, wenn manIt has also been found that the 1,3,4-thiadiazolylureas of the formula (I) are obtained if
a) 2-Amino-1,3,4-thiadiazole der Formela) 2-Amino-1,3,4-thiadiazoles of the formula
H R»MR"
HHHH
(II)(II)
in welcherin which
R und Rf die oben angegebene Bedeutung haben, mit Isocyanaten der FormelR and R f have the meaning given above, with isocyanates of the formula
(III)(III)
in welcherin which
R"'die angegebene Bedeutung hat, in Gegenwart eines Verdünnungsmittels umsetzt oderR "'has the meaning given, reacts in the presence of a diluent or
b) 2 Amino-1,3,4-thiadiazole der Formel (II) mit Säurechloriden der Formelb) 2 amino-1,3,4-thiadiazoles of the formula (II) with acid chlorides of the formula
(IV)(IV)
in welcherin which
in Gegenwart von Verdünnungsmitteln und Säurebindern umsetzt.in the presence of diluents and acid binders.
Bs ist als auegesprochen überraschend su bezeichnen, daß die erfindungegemäfien 1,3,4-Tliiadiaiolyl-harnstoffe eine stärkere herbizide Wirkung und eine bessere selektir-herbizide Wirkung aufweisen als die vorbekannten Ihiasolylharnstoffe.Bs can be described as extremely surprising that the erfindungegemäfien 1,3,4-Tliiadiaiolyl-ureas a stronger herbicidal effect and a better selective herbicidal effect have than the previously known Ihiasolylureas.
1098ί52/Ϊ878 1098ί5 2 / Ϊ87 8
In der oben angegebenen formel (I) steht R vorzugsweise für Trihalogenmethyl sowie Trifluoralkoxy-alkyl mit 1-3 C-Atomen in der Alkoxygruppe und 1 -3 C-Atomen in der Alkylgruppe. . R1 steht vorzugsweise für Wasserstoff, Alkyl mit 1-4 C-Atomen, Hydroxyalkyl mit 1-3 C-Atomen, Alkoxy mit 1-2 C-Atomen, R1' steht vorzugsweise für Wasserstoff und Alkyl mit 1-4 C-Atomen. R»« steht vorzugsweise für Alkyl mit 1-4 C-Atomen, Alkenyl und Alkinyl mit 2-4 C-Atomen, Chloralkyl mit 1-4 C-Atomen, Alkoxyalkyl mit 1-4 C-Atomen in dem Alkoxy- und Alkyl-Rest, ferner für gegebenenfalls durch Chlor, Brom, Trifluormethyl und/oder Methyl substituiertes Phenyl.In the above formula (I), R preferably represents trihalomethyl and trifluoroalkoxy-alkyl with 1-3 carbon atoms in the alkoxy group and 1-3 carbon atoms in the alkyl group. . R 1 preferably stands for hydrogen, alkyl with 1-4 C atoms, hydroxyalkyl with 1-3 C atoms, alkoxy with 1-2 C atoms, R 1 'preferably stands for hydrogen and alkyl with 1-4 C atoms . R "" preferably stands for alkyl with 1-4 carbon atoms, alkenyl and alkynyl with 2-4 carbon atoms, chloroalkyl with 1-4 carbon atoms, alkoxyalkyl with 1-4 carbon atoms in the alkoxy and alkyl The remainder, also for phenyl which is optionally substituted by chlorine, bromine, trifluoromethyl and / or methyl.
Verwendet man 5-Trifluormethyl-2-amino-1,3,4-thiadiazol und Methylisocyanat als Ausgangsstoffe, so Τη*ητι der Reaktionsablauf gemäß Verfahren a) durch das folgende Formelschema wiedergegeben werden:If 5-trifluoromethyl-2-amino-1,3,4-thiadiazole and methyl isocyanate are used as starting materials, the reaction sequence according to process a) can be represented by the following equation:
N- -N N NN- -N N N
lIH-CO-IiH-CElIH-CO-IiH-CE
+ O=C=F-CH3 Il Il+ O = C = F-CH 3 II II
Verwendet man Dirnethylcarbamidsäurechlorid zur Umsetzung mit Λ dem gleichen Thiadiazol, so kann der Reaktionsablauf des Verfahrens b) durch das folgende Formelschema wiedergegeben werden:If you use dirnethylcarbamic acid chloride to react with Λ the same thiadiazole, the course of the reaction in process b) can be represented by the following equation:
N- -N 2 ^CE ΏββΑ N NN- -N 2 ^ CE ΏββΑ NN
I ff Cl-S-N" 3 Base , ,,I ff Cl-SN " 3 base , ,,
ff -Hff -H
JUh2 JUh 2
_hci_hci
Die Ausgangsstoffe gemäß den Formeln (III) und (IV). sind bereits bekannt.The starting materials according to formulas (III) and (IV). are already known.
Le A 11 487 - 3 - Le A 11 487 - 3 -
109S4S/ 1878109S4S / 1878
Sie als Ausgangemateri*1 benötigten Aminothiadiazole der Formel (II) sind zum Teil bereits bekannt· Die noch neuen Thiadiazole können in gleicher Weise wie die bereits bekannten hergestellt werden, z. B. durch Umsetzen der entsprechenden 1-Acylthiosemicarbazide mit wasserabspaltenden Mitteln, wie Acetanhydrid (Chemische Berichte 29, 2511 (1896)).Some of the aminothiadiazoles of the formula (II) required as starting materials are already known. The still new thiadiazoles can be used in the same way as those already known be produced, e.g. B. by reacting the corresponding 1-acylthiosemicarbazide with dehydrating agents, such as Acetic anhydride (Chemical Reports 29, 2511 (1896)).
Als Verdünnungsmittel kommen für die genannten Verfahren a) und b) alle inerten organischen Lösungsmittel in Präge. Hierzu gehören vorzugsweise Kohlenwasserstoffe, wie Benzol und Toluol, Aether, wie Diäthylather, Tetrahydrofuran und Dioxan, Ketone, wie Aceton, Ester, wie Essigsäureäthylester und polare Lösungsmittel, wie Dimethylformamid und Acetonitril.All inert organic solvents are used as diluents for the processes a) and b) mentioned. These preferably include hydrocarbons such as benzene and Toluene, ethers such as diethyl ether, tetrahydrofuran and dioxane, Ketones such as acetone, esters such as ethyl acetate and polar solvents such as dimethylformamide and acetonitrile.
Als Säurebinder können alle üblichen Säurebindungsmittel verwendet werden. Hierzu gehören vorzugsweise die Alkalihydroxide, Alkalicarbonate und tertiären Amine. Als besonders geeignet seien im einzelnen genannt:All customary acid-binding agents can be used as acid-binding agents. These preferably include the alkali hydroxides, Alkali carbonates and tertiary amines. Particularly suitable are:
Natriumhydroxid, Natriumcarbonat, Triäthylamin, N,N-Dimethylanllin und Fyridin.Sodium hydroxide, sodium carbonate, triethylamine, N, N-dimethylanlline and fyridine.
Die Reaktionstemperaturen können bei den beiden Verfahren in einem größeren Bereich variiert werden. Im allgemeinen arbeitet man zwischen O0 und 1400C, vorzugsweise zwischen 10° und 1200C.The reaction temperatures can be varied over a wide range in the two processes. In general, preferably carried out between 0 ° and 140 0 C between 10 ° and 120 0 C.
Bei der Durchführung der erfindungsgemäßen Verfahren setzt man zweckmäSigerweise äquimolare Mengen an Ausgangsstoffen ein. Die Aufarbeitung des Reaktionsgemisches wird in üblicher Weise vorgenommen.When carrying out the process according to the invention, equimolar amounts of starting materials are expediently employed. the The reaction mixture is worked up in the customary manner.
τ.« a 11 AB7 - 4. -τ. « a 11 AB7 - 4. -
109845/ 1 878109845/1 878
Die Harnstoffe weisen eine starke herbizide Potenz auf um. können deshalb als Unkrautvernichtungsmittel verwendet werden. Unter Unkraut im wesentlichen Sinne sind alle Pflanzen zu verstehen, die an Orten aufwachsen, wo sie unerwünscht sind. Ob die erfindungsgemäßen Wirkstoffe als totale oder selektive herbizide Mittel wirken, hängt von der Höhe der aufgewendeten Menge ab.The ureas have a strong herbicidal potency. can therefore be used as weed killers. Weeds in the essential sense include all plants to understand who grow up in places where they are undesirable are. Whether the active compounds according to the invention act as total or selective herbicidal agents depends on the level of used amount.
Die erfindungsgemäßen Stoffe können z. B. bei den folgenden Pflanzen verwendet werden: Dikotyle, wie Senf (Sinapis), Kresse (Lepidium), Klettenlabkraut (Galium), Vogelmiere (Stellaria), Kamille (Matricaria), Franzosenkraut (Galin-* soga), Gänsefuß (Chenopodium), Brennessel (Urtica), Kreuzkraut (Senecio), Baumwolle (Gossypium), Rüben (Beta), Möhren (Daucus), Bohnen (Phaseolus), Kartoffeln (Solanum), Kaffee (Coffea); Monokotyle, wie Lieschgras (Phleum), Rispengras (Poa), Schwingel (Festuca), Sleusine (Eleusine), Fennich (Setaria), Raygras (Lolium), Trespe (Bromus), Hühnerhirse (Echonochloa), Mais (Zea), Reis (Oryza), Hafer (Avena), Gerste (Hordeum), Weizen (Triticum), Hirse (Panlcum), Zuckerrohr (Saccharum).The substances according to the invention can, for. B. in the following Plants used: dicots, such as mustard (Sinapis), Cress (Lepidium), burdock (Galium), chickweed (Stellaria), chamomile (Matricaria), French herb (Galin- * soga), goose foot (Chenopodium), nettle (Urtica), ragwort (Senecio), cotton (Gossypium), beet (Beta), carrots (Daucus), beans (Phaseolus), potatoes (Solanum), coffee (Coffea); Monocots, such as timothy grass (phleum), Bluegrass (Poa), fescue (Festuca), Sleusine (Eleusine), Fennich (Setaria), ryegrass (Lolium), bromus (bromus), barnyard millet (Echonochloa), maize (Zea), rice (Oryza), oats (Avena), barley (Hordeum), wheat (Triticum), millet (Panlcum), Sugar cane (Saccharum).
Die Harnstoffe werden vorzugsweise als selektive Herbizide eingesetzt· Sie weisen eine gute Selektivität bei der Anwendung vor und nach dem Ablaufen in Baumwolle und Getreide, wie Weizen und Hafer, auf« The ureas are preferably used as selective herbicides used · They have a good selectivity when used before and after draining in cotton and cereals, such as wheat and oats «
Die erfindungsgemäßen Wirkstoffe können in die üblichen Formulierungen übergeführt werden, wie Lösungen, Emulsionen* Suspensionen, Pulver, Pasten uad Granulate. Diese werden in bekannter Weise hergestellt, e. B. durch Ver-The active compounds according to the invention can be converted into the customary Formulations such as solutions, emulsions * Suspensions, powders, pastes and granulates. These are produced in a known manner, e. B. by
a 11 487 109 8A5U a 11 487 109 8A5 U
mischen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln und/oder Dispergiermitteln. Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösungsmittel »la Hllfslösungsmittel verwendet werden· Als flüssige Lösungsmittel kommen im wesentlichen infrage: Aromaten, wir Xylol und Benzol, chlorierte Aromaten, wie Chlorbenzole, Paraffine, wie Erdölfranktionen, Alkohole, wie Methanol und Butanol, stark polare Lösungsmittel, wie Dimethylformamid und Dime thy lsulf oxid, sowie Wasser; als feste Trägerstoffe: natürliche Gesteinemehle, wie Kaoline, fonerden, Talkum und Kreide, und synthetische Gesteinsmehle, wie hochdlsperse Kieselsäure und Silikate; als Emulgiermittel: nichtionogene und anionische Emulgatoren, wie Polyoxyäthylen-Fettsäure-Ester, Polyoxyäthylen-Fettalkohol-Äther, z. B. Alkylaryl-polyglykoläther, Alkylsulfonate und Arylsulfonate, als Dispergiermittel: z. B. Lignin, Sulfitablaugen und Methylcellulose.mixing the active ingredients with extenders, i.e. liquids Solvents and / or dispersants. In the case of using water as an extender, e.g. Organic solvents »auxiliary solvents are used · The main liquid solvents are: aromatics such as xylene and benzene, chlorinated aromatics such as chlorobenzenes, paraffins such as petroleum fractions, alcohols such as methanol and butanol, strongly polar ones Solvents such as dimethylformamide and dimethyl sulfoxide, as well as water; as solid carrier materials: natural ground rock, such as kaolins, fonerden, talc and chalk, and synthetic ground rock, such as highly dehydrated silicic acid and Silicates; as emulsifiers: nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. alkylaryl polyglycol ethers, alkyl sulfonates and aryl sulfonates, as dispersants: z. B. lignin, sulphite waste liquors and methyl cellulose.
Die erfindungsgemäßen Wirkstoffe können in den Formulierungen in Mischungen mit anderen bekannten Wirkstoffen vorliegen.The active compounds according to the invention can be used in the formulations in mixtures with other known active ingredients.
Die Wirkstoffe können als solche, in Fora ihrer Formulierungen oder der daraus bereiteten Anwendungsformen, wie gebrauchsfertige Lösungen, Emulsionen, Suspensionen, Pulver, Pasten und Granulate, angewendet werden· Die Anwendung geschieht in üblicher Weise, z, B. durch Verstäuben, Versprühen, Verspritzen, Gießen und Verstreuen.The active compounds can, as such, their formulations or prepared therefrom forms of application, such as ready solutions, emulsions, suspensions, powders, pastes and granules, are applied in Fora · are used in the customary manner, for, example, by dusting, spraying, squirting , Pouring and scattering.
Die angewandte Menge kann in größeren Bereichen schwanken. Sie hängt im wesentlichen von der Art des gewünschten Effekts ab.The amount used can vary over a wide range. It essentially depends on the type of effect you want.
109845/1878 Le A 11 487 ~ 6 -109845/1878 Le A 11 487 ~ 6 -
Im allgemeinen liegen die Aufwandmengen zwischen 0,25 und 15 kg Wirkstoff pro ha, vorzugsweise zwischen 0,2 und 10 kg pro ha.In general, the application rates are between 0.25 and 15 kg Active ingredient per ha, preferably between 0.2 and 10 kg per ha.
Die Wirkstoff-Konzentrat ion liegt bei den üblichen wäßrigen Zubereitungen und bei der Anwendung, nach dem Ablaufen im allgemeinen zwischen 0,005 und 0,5 Gewichtsprozent, vorzugsweise zwischen 0v008 und 0,1 Gewichtsprozent.The active ingredient concentration is in the customary aqueous preparations and in the application, after the runoff, generally between 0.005 and 0.5 percent by weight, preferably between 0 v 008 and 0.1 percent by weight.
10 9845/1878 Le A 11 487 - 7 - 10 9845/1878 Le A 11 487 - 7 -
Pre-emergence-TestPre-emergence test
Lösungsmittelt 5 Gewichtsteile Aceton Solvent 5 parts by weight acetone
Emulgator: 1 Gewichtsteile Alkylarylpolyglykoläther Emulsifier: 1 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Grewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel» gibt die angegebene Menge Emulgator zu und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.Mixed to produce an appropriate preparation of active ingredients 1 part by weight of active ingredient with the specified amount of solvent is added and the specified amount of emulsifier is diluted the concentrate with water to the desired concentration.
Samen der Testpflanzen werden in normalen Boden ausgesät und nach 24 Stunden mit der Wirkstoffzubereitung begosaen. Dabei hält man die Wassermenge pro Flächeneinheit zweckmäßigerweise konstant. Die Wirkstoffkonzentrat ion in der Zubereitung spielt keine Rolle, entscheidend ist nur die Aufwandmenge des Wirkstoffes pro Flächeneinheit. Nach drei Wochen wird der Schädigungsgrad der Testpflanzen bestimmt und mit den Kennziffern 0-5 bezeichnet, welche die folgende Bedeutung haben:Seeds of the test plants are sown in normal soil and after 24 hours with the preparation of active ingredient gum. Included Keeping the amount of water per unit area expediently constant. The concentration of active ingredients in the preparation plays a role Doesn't matter, only the amount of active ingredient applied per unit area is decisive. After three weeks, the degree of damage will be of the test plants and designated with the code numbers 0-5, which have the following meaning:
0 keine Wirkung0 no effect
1 leichte Schäden oder Wachstumsverzögerung1 slight damage or growth retardation
2 deutliche Schäden oder Wachstumshemmung2 significant damage or stunted growth
3 . schwere Schaden und nur mangelnde Entwicklung oder nur3. severe damage and only lack of development or only
50 # aufgelaufen50 # accrued
4 Pflanzen nach der Keimung teilweise vernichtet oder nur 25 % aufgelaufen4 plants partially destroyed after germination or only 25 % emerged
5 Pflanzen vollständig abgestorben oder nicht aufgelaufen5 plants completely dead or not emerged
Wirkstoffe, Aufwandmengen und Resultate gehen aus der nachfolgenden Tabelle hervortActive ingredients, application rates and results are based on the following Table stands out
10984 5/1878 La A 11 A87 - β - 10984 5/1878 La A 11 A87 - β -
T a t> β 1 1 e
Pre-emergenee-Test T a t> β 1 1 e
Pre-emergenee test
WirkstoffActive ingredient
Wirkstoff- Echino- Cheno- Sina- Galin- Stel- Matri- Batuaaufwand chloa poditua pis eoga laria caria wolle kg/haActive ingredient- Echino- Cheno- Sina- Galin- St- Matri- Batua expenditure chloa poditua pis eoga laria caria wool kg / ha
HC - S I I HC - S II
-C C- HH-CO-HH-CH,-C C- HH-CO-HH-CH,
CD OOCD OO -C-CJI-C-CJI
(bekannt)(known)
oooo
coco P3CP 3 C
H - NH - N
Il I -C C-HH-CO-HH-CH, II I -C C-HH-CO-HH-CH,
5
5
55
5
5
5
5
55
5
5
5
5
55
5
5
5 5 55 5 5
5 5 55 5 5
5 5 55 5 5
Le A 11 A87 Le A 11 A87
H-H il H CF5-CH2O-CH2-CH2 -C C- HH-CO-NH-CH5 HH il H CF 5 -CH 2 O-CH 2 -CH 2 -C C-HH-CO-NH-CH 5
N-NN-N
Il HIl H
CF- -C C-H- CO-NH-CH \ / ·CF- -C CH- CO-NH-CH \ / ·
La A 11 4.37 -9a- La A 11 4.37 -9a-
109845/1878109845/1878
-ti-ti
Post-emergence-Test Lösungsmittel: 5 Gewichtateile AcetonPost-emergence test Solvent: 5 parts by weight acetone
Emulgator» 1 Gewichtsteile AlkylarylpolyglykoätherEmulsifier »1 part by weight of alkylaryl polyglycoether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel, gibt die angegebene Menge Emulgator zu und verdünnt das Konzentrat anschließend mit Wasser auf die gewünschte Konzentration. To produce an appropriate preparation of active ingredient, 1 part by weight of active ingredient is mixed with the stated amount Solvent, add the specified amount of emulsifier and then dilute the concentrate with water to the desired concentration.
Mit der Wirkstoffzubereitung spritzt man Testpflanzen, welche eine Höhe von etwa 5-15 cm haben, gerade taufeucht. Naoh drei Wochen wird der Schädigungsgrad der Pflanzen bestimmt und mit den Kennziffern 0-5 bezeichnet, welche die folgende Bedeutung haben:Test plants, which have a height of about 5-15 cm, just dewy. Well three In weeks, the degree of damage to the plants is determined and denoted by the code numbers 0-5, which have the following meaning to have:
0 keine Wirkung '0 no effect '
1 einzelne leichte Verbrennungeflecken1 single light burn marks
2 deutliche Blattschäden2 distinct leaf damage
3 einzelne Blätter und Stengelteile z.T. abgestorben3 individual leaves and stem parts partly dead
4 Pflanze teilweise vernichtet4 plant partially destroyed
5 Pflanze total abgestorben5 plant totally dead
Wirkstoffe, Wirkstoffkonzentrationen und Resultate gehen aus der nachfolgenden Tabelle hervortActive ingredients, active ingredient concentrations and results run out the table below
Le A 11 487 - 10 - Le A 11 487 - 10 -
1 09 845/ 18781 09 845/1878
I
C- NH-CO-NH-CH»- S.
I.
C- NH-CO-NH-CH »
konz.
* Active ingredient
conc.
*
4
34-5
4th
3
sogaGael-
so
lariaStel
laria
CUB Permanent
CUB
OfO25
0,01250.05
O f O25
0.0125
3
24-5
3
2
2
13
2
1
0
01
0
0
0
01
0
0
0
01-2
0
0
Echino- Cheno- Sina-
chloa podium pisPost-emergenoe test
Echino- Cheno- Sina-
chloa podium pis
Il
CH3 -σHC
Il
CH 3 -σ
1 4
0 23 4-5
1 4
0 2
(bekannt)(known)
P-C 3P-C 3
N-NN-N
II MII M
-C C- NH-CO-NH-CH, \ / 3-C C- NH-CO-NH-CH, \ / 3
0,050.05
0,0250.025
0,01250.0125
IAlAlAIAlAlA
Ul UI UlUl UI Ul
IAlAlAIAlAlA
UlUlUlUlUlUl
5 5 45 5 4
4 2 04 2 0
Le A 11 487Le A 11 487
- 11 -- 11 -
17/046717/0467
N - NN - N
II 11II 11
0-O-CH0-CH0 -C C- NH-CO-NH-CHx 2 2 \s/ 0 -O-CH 0 -CH 0 -C C- NH-CO-NH-CH x 2 2 \ s /
N-NN-N
« II CP- -C C-N- CO-NH-CH «II CP- -C CN- CO-NH-CH
5V 5 V
A 11 487 - 11 * -. A 11 487 - 11 * -.
109845/1878109845/1878
Zu 16,9 g (0,1 Mol) 5-Trifluoraethyl-2-aminQ-1,3,4-thiadiaa5ol In 100 ml Tetrahydrofuran werden 5,7 g (0,1 Mol) Methylisocyanat bei 200C unter Rühren eingetropft» Nach Abklingen der Wärmetönung wird noch 2 Stunden bei 500C gerührt, danach wird das Lösungsmittel im Vakuum entfernt. Nach Umkristallisieren des festen Rückstands aus Alkohol erhält man den H-(Trifluormethyl-1,3,4-thiadiazolyl)-Hf-methyl-harnstoff in kristalliner Porm (1. Tabelle).To 16.9 g (0.1 mole) of 5-trifluoroethyl-2-aminQ-1,3,4-thiadiaa5ol In 100 ml of tetrahydrofuran, 5.7 g (0.1 mole) of methyl isocyanate are added dropwise at 20 0 C with stirring " After the heat dissipation has subsided, the mixture is stirred for a further 2 hours at 50 ° C., after which the solvent is removed in vacuo. After recrystallization of the solid residue from alcohol, H- (trifluoromethyl-1,3,4-thiadiazolyl) -H f -methyl urea is obtained in crystalline form (1. Table).
In analoger Weise werden auch die weiteren in der Tabelle genannten Harnstoffe hergestellt:The other ureas listed in the table are also produced in an analogous manner:
Tu t 11 A87 - 12 - Tu t 11 A87 - 12 -
|ΓΤ 7 109845/1878 | ΓΤ 7 109845/1878
Beispiel 2Example 2 JFJF
Zu 16,9 g (0,1 Mol) 5-Trifluormethyl-2-aniino-1,3,4-thiadiazol in 150 al Pyridin gelöst, werden 0,1 Hol Dimethylcarbamidsäurechlorid gegeben und 24 Stunden bei Raumtemperatur stehengelassen.To 16.9 g (0.1 mole) of 5-trifluoromethyl-2-aniino-1,3,4-thiadiazole Dissolved in 150 al of pyridine, 0.1 hol of dimethylcarbamic acid chloride given and left to stand at room temperature for 24 hours.
Danach wird vom Pyridiniumhydrochlorid abgesaugt, die Pyridinlösung im Vakuum eingedampft und der feste Rückstand mit 100 ml 5 #iger Salzsäure verrührt. Der rohe N-(5-Trifluormethyl-1.3,4-thiadiaaolyl)-K'-dimethyl-iiarnstoff wird abgesaugt und aus Benzol umkrlstallislert (Vergl. !Tabelle 2).The pyridine solution is then suctioned off from the pyridinium hydrochloride evaporated in vacuo and the solid residue with 100 ml 5 # hydrochloric acid stirred. The crude N- (5-trifluoromethyl-1,3,4-thiadiaolyl) -K'-dimethyl-iiarnstoff is suctioned off and recrystallized from benzene (see Table 2).
Jn analoger Weise werden die weiteren in üqi? Tabelle genannten Harnstoffe hergestellt: In an analogous manner, the others in üqi? Table mentioned ureas produced:
R R1 Rft R"8 RR 1 R ft R " 8 Pp. 0CPp. 0 C
H GE CH3 120°H GE CH 3 120 °
GH3 CH, CH5 112°GH 3 CH, CH 5 112 °
fre A 11 487 - 13 - Friday A 11 487 - 13 -
10984 5/187810984 5/1878
Claims (6)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681770467 DE1770467A1 (en) | 1968-05-22 | 1968-05-22 | 1,3,4-thiadiazolyl ureas |
| CH591369A CH512181A (en) | 1968-05-22 | 1969-04-17 | Herbicidal agent |
| IL32047A IL32047A0 (en) | 1968-05-22 | 1969-04-20 | 1,3,4-thiadiazolyl ureas,their preparation and use for destroying weeds |
| RO59913A RO55667A (en) | 1968-05-22 | 1969-05-07 | |
| NL6906983A NL6906983A (en) | 1968-05-22 | 1969-05-07 | |
| BG012219A BG16162A3 (en) | 1968-05-22 | 1969-05-09 | HERBICIDE |
| CS3328A CS151513B2 (en) | 1968-05-22 | 1969-05-12 | |
| GB24853/69A GB1276925A (en) | 1968-05-22 | 1969-05-15 | 0,3,4-thiadiazolyl ureas |
| YU01234/69A YU123469A (en) | 1968-05-22 | 1969-05-19 | Process for preparing novel 1,3,4-thiadiazolyl-carbamates |
| FI691538A FI52723C (en) | 1968-05-22 | 1969-05-21 | As herbicides active 1,3,4-thiadiazolylureas. |
| BE733367D BE733367A (en) | 1968-05-22 | 1969-05-21 | |
| AT482969A AT290199B (en) | 1968-05-22 | 1969-05-21 | Herbicidal agent |
| ES367478A ES367478A1 (en) | 1968-05-22 | 1969-05-21 | 0,3,4-thiadiazolyl ureas |
| FR6916781A FR2009152A1 (en) | 1968-05-22 | 1969-05-22 | |
| MY285/73A MY7300285A (en) | 1968-05-22 | 1973-12-30 | 1,3,4-thiadiazolyl ureas |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681770467 DE1770467A1 (en) | 1968-05-22 | 1968-05-22 | 1,3,4-thiadiazolyl ureas |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1770467A1 true DE1770467A1 (en) | 1971-11-04 |
Family
ID=5700523
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681770467 Pending DE1770467A1 (en) | 1968-05-22 | 1968-05-22 | 1,3,4-thiadiazolyl ureas |
Country Status (15)
| Country | Link |
|---|---|
| AT (1) | AT290199B (en) |
| BE (1) | BE733367A (en) |
| BG (1) | BG16162A3 (en) |
| CH (1) | CH512181A (en) |
| CS (1) | CS151513B2 (en) |
| DE (1) | DE1770467A1 (en) |
| ES (1) | ES367478A1 (en) |
| FI (1) | FI52723C (en) |
| FR (1) | FR2009152A1 (en) |
| GB (1) | GB1276925A (en) |
| IL (1) | IL32047A0 (en) |
| MY (1) | MY7300285A (en) |
| NL (1) | NL6906983A (en) |
| RO (1) | RO55667A (en) |
| YU (1) | YU123469A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2330453A1 (en) * | 1973-06-15 | 1975-01-09 | Velsicol Chemical Corp | Thidiazolyl ureidoacetaldehyde acetals - as herbicies |
| US4174398A (en) * | 1977-03-23 | 1979-11-13 | Bayer Aktiengesellschaft | Combating fungi with 1-alkyl-1-(1,3,4-thiadiazol-2-yl)-3-phenyl-ureas |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1427087A (en) * | 1972-08-14 | 1976-03-03 | ||
| GB1561636A (en) * | 1975-11-07 | 1980-02-27 | Lilly Industries Ltd | Herbicidal combinations |
| ZA775225B (en) * | 1977-08-29 | 1978-03-29 | Lilly Co Eli | Herbicidal combinations |
| US4338449A (en) | 1981-06-15 | 1982-07-06 | Eli Lilly And Company | Herbicidal thiadiazolines |
| US4346225A (en) | 1981-06-15 | 1982-08-24 | Eli Lilly And Company | Herbicidal 2-methylamino thiadiazolines |
-
1968
- 1968-05-22 DE DE19681770467 patent/DE1770467A1/en active Pending
-
1969
- 1969-04-17 CH CH591369A patent/CH512181A/en not_active IP Right Cessation
- 1969-04-20 IL IL32047A patent/IL32047A0/en unknown
- 1969-05-07 RO RO59913A patent/RO55667A/ro unknown
- 1969-05-07 NL NL6906983A patent/NL6906983A/xx unknown
- 1969-05-09 BG BG012219A patent/BG16162A3/en unknown
- 1969-05-12 CS CS3328A patent/CS151513B2/cs unknown
- 1969-05-15 GB GB24853/69A patent/GB1276925A/en not_active Expired
- 1969-05-19 YU YU01234/69A patent/YU123469A/en unknown
- 1969-05-21 AT AT482969A patent/AT290199B/en not_active IP Right Cessation
- 1969-05-21 FI FI691538A patent/FI52723C/en active
- 1969-05-21 ES ES367478A patent/ES367478A1/en not_active Expired
- 1969-05-21 BE BE733367D patent/BE733367A/xx unknown
- 1969-05-22 FR FR6916781A patent/FR2009152A1/fr not_active Withdrawn
-
1973
- 1973-12-30 MY MY285/73A patent/MY7300285A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2330453A1 (en) * | 1973-06-15 | 1975-01-09 | Velsicol Chemical Corp | Thidiazolyl ureidoacetaldehyde acetals - as herbicies |
| US4174398A (en) * | 1977-03-23 | 1979-11-13 | Bayer Aktiengesellschaft | Combating fungi with 1-alkyl-1-(1,3,4-thiadiazol-2-yl)-3-phenyl-ureas |
Also Published As
| Publication number | Publication date |
|---|---|
| BG16162A3 (en) | 1972-07-20 |
| BE733367A (en) | 1969-11-21 |
| IL32047A0 (en) | 1969-06-25 |
| GB1276925A (en) | 1972-06-07 |
| NL6906983A (en) | 1969-11-25 |
| FI52723C (en) | 1977-11-10 |
| ES367478A1 (en) | 1971-04-01 |
| RO55667A (en) | 1973-11-20 |
| AT290199B (en) | 1971-05-25 |
| MY7300285A (en) | 1973-12-31 |
| CH512181A (en) | 1971-09-15 |
| YU123469A (en) | 1978-12-31 |
| FI52723B (en) | 1977-08-01 |
| FR2009152A1 (en) | 1970-01-30 |
| CS151513B2 (en) | 1973-10-19 |
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