NO742937L - - Google Patents

Info

Publication number: NO742937L
Authority: NO; Norway
Prior art keywords: ester; acid; alkyl; dichloro; mercapto
Prior art date: 1973-09-01

Application number

NO742937A

Other languages

English (en)

Norwegian (no)

Inventor

K Sasse

G Beck

L Eue

Original Assignee

Bayer Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1973-09-01

Filing date

1974-08-15

Publication date

1974-04-01

1974-04-01 Publication of NO742937L publication Critical patent/NO742937L/no

1974-08-15 Application filed by Bayer Ag filed Critical Bayer Ag

Links

-1 aryl mercapto Chemical class 0.000 claims description 40
125000000217 alkyl group Chemical group 0.000 claims description 24
125000004432 carbon atom Chemical group C* 0.000 claims description 21
FLDIPKCTYWJMAW-UHFFFAOYSA-N 4,5-dichloro-3h-1,3-thiazole-2-thione Chemical compound SC1=NC(Cl)=C(Cl)S1 FLDIPKCTYWJMAW-UHFFFAOYSA-N 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 13
125000003118 aryl group Chemical group 0.000 claims description 13
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 13
125000003545 alkoxy group Chemical group 0.000 claims description 12
125000004414 alkyl thio group Chemical group 0.000 claims description 12
229910052736 halogen Inorganic materials 0.000 claims description 12
239000011230 binding agent Substances 0.000 claims description 11
150000002367 halogens Chemical group 0.000 claims description 11
238000000034 method Methods 0.000 claims description 11
125000001188 haloalkyl group Chemical group 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
239000003085 diluting agent Substances 0.000 claims description 7
239000004009 herbicide Substances 0.000 claims description 7
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 6
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
150000001298 alcohols Chemical class 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
125000004104 aryloxy group Chemical group 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000004663 dialkyl amino group Chemical group 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
229910052717 sulfur Chemical group 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 3
150000002989 phenols Chemical class 0.000 claims description 3
239000011593 sulfur Chemical group 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
150000002366 halogen compounds Chemical class 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
239000004094 surface-active agent Substances 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims 2
230000008635 plant growth Effects 0.000 claims 2
125000004966 cyanoalkyl group Chemical group 0.000 claims 1
239000000080 wetting agent Substances 0.000 claims 1
238000006243 chemical reaction Methods 0.000 description 28
239000013543 active substance Substances 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
238000002844 melting Methods 0.000 description 14
230000008018 melting Effects 0.000 description 14
239000002904 solvent Substances 0.000 description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
150000003566 thiocarboxylic acids Chemical class 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
241000196324 Embryophyta Species 0.000 description 11
150000002148 esters Chemical class 0.000 description 10
239000000203 mixture Substances 0.000 description 10
HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical compound OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
238000002360 preparation method Methods 0.000 description 8
150000003839 salts Chemical class 0.000 description 8
239000000243 solution Substances 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
239000007788 liquid Substances 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000003995 emulsifying agent Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
230000002363 herbicidal effect Effects 0.000 description 4
239000000047 product Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
FDEQQCOTLPPCAO-UHFFFAOYSA-N Cl.OC(O)=O Chemical compound Cl.OC(O)=O FDEQQCOTLPPCAO-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000003513 alkali Substances 0.000 description 3
239000004202 carbamide Substances 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
150000001733 carboxylic acid esters Chemical class 0.000 description 3
239000000969 carrier Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
230000000855 fungicidal effect Effects 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
WREDNSAXDZCLCP-UHFFFAOYSA-N methanedithioic acid Chemical compound SC=S WREDNSAXDZCLCP-UHFFFAOYSA-N 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
FDWSIACICRBLGW-UHFFFAOYSA-N 2,4,5-trichloro-1,3-thiazole Chemical compound ClC1=NC(Cl)=C(Cl)S1 FDWSIACICRBLGW-UHFFFAOYSA-N 0.000 description 2
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 2
244000075850 Avena orientalis Species 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
241000234642 Festuca Species 0.000 description 2
241000219146 Gossypium Species 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
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
241000209094 Oryza Species 0.000 description 2
235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
244000046052 Phaseolus vulgaris Species 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
244000062793 Sorghum vulgare Species 0.000 description 2
239000005864 Sulphur Chemical group 0.000 description 2
241000209140 Triticum Species 0.000 description 2
235000021307 Triticum Nutrition 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
150000001447 alkali salts Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
SKOLWUPSYHWYAM-UHFFFAOYSA-N carbonodithioic O,S-acid Chemical compound SC(S)=O SKOLWUPSYHWYAM-UHFFFAOYSA-N 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
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000004088 foaming agent Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
150000004679 hydroxides Chemical class 0.000 description 2
239000005457 ice water Substances 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 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
239000003380 propellant Substances 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000004434 sulfur atom Chemical group 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 2
150000003585 thioureas Chemical class 0.000 description 2
ZUHZJWIQLCSXQQ-UHFFFAOYSA-N (4,5-dichloro-1,3-thiazol-2-yl) chloromethanedithioate Chemical compound ClC(=S)SC1=NC(Cl)=C(Cl)S1 ZUHZJWIQLCSXQQ-UHFFFAOYSA-N 0.000 description 1
OMJDPDUHBKZMTA-UHFFFAOYSA-N 1,1,2-trichloro-2-isocyanoethene Chemical compound ClC(Cl)=C(Cl)[N+]#[C-] OMJDPDUHBKZMTA-UHFFFAOYSA-N 0.000 description 1
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical class C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 1
QRWVOJLTHSRPOA-UHFFFAOYSA-N 1,3-bis(prop-2-enyl)urea Chemical compound C=CCNC(=O)NCC=C QRWVOJLTHSRPOA-UHFFFAOYSA-N 0.000 description 1
YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical class C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
YFBUDXNMBTUSOC-UHFFFAOYSA-N 1,4-dihydroquinoxaline-2,3-dithione Chemical compound C1=CC=C2NC(=S)C(=S)NC2=C1 YFBUDXNMBTUSOC-UHFFFAOYSA-N 0.000 description 1
FLFWJIBUZQARMD-UHFFFAOYSA-N 2-mercapto-1,3-benzoxazole Chemical class C1=CC=C2OC(S)=NC2=C1 FLFWJIBUZQARMD-UHFFFAOYSA-N 0.000 description 1
PPHAQZXMDYFUTI-UHFFFAOYSA-N 3,4,4a,5-tetrahydro-2H-quinoline-1-carbothioic S-acid Chemical compound N1(CCCC2CC=CC=C12)C(O)=S PPHAQZXMDYFUTI-UHFFFAOYSA-N 0.000 description 1
TWFRMOJOOVEFCI-UHFFFAOYSA-N 4,5-dichloro-1,3-thiazole Chemical class ClC=1N=CSC=1Cl TWFRMOJOOVEFCI-UHFFFAOYSA-N 0.000 description 1
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
QCVGEOXPDFCNHA-UHFFFAOYSA-N 5,5-dimethyl-2,4-dioxo-1,3-oxazolidine-3-carboxamide Chemical compound CC1(C)OC(=O)N(C(N)=O)C1=O QCVGEOXPDFCNHA-UHFFFAOYSA-N 0.000 description 1
240000002245 Acer pensylvanicum Species 0.000 description 1
235000006760 Acer pensylvanicum Nutrition 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
235000005781 Avena Nutrition 0.000 description 1
235000007319 Avena orientalis Nutrition 0.000 description 1
235000007689 Borago officinalis Nutrition 0.000 description 1
244000056139 Brassica cretica Species 0.000 description 1
235000003351 Brassica cretica Nutrition 0.000 description 1
240000002791 Brassica napus Species 0.000 description 1
235000011293 Brassica napus Nutrition 0.000 description 1
235000000540 Brassica rapa subsp rapa Nutrition 0.000 description 1
235000003343 Brassica rupestris Nutrition 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
241000209200 Bromus Species 0.000 description 1
235000007866 Chamaemelum nobile Nutrition 0.000 description 1
241000219312 Chenopodium Species 0.000 description 1
241000723377 Coffea Species 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 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
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
241000192043 Echinochloa Species 0.000 description 1
102000002322 Egg Proteins Human genes 0.000 description 1
108010000912 Egg Proteins Proteins 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
240000004282 Grewia occidentalis Species 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
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241000257303 Hymenoptera Species 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
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
VLCDUOXHFNUCKK-UHFFFAOYSA-N N,N'-Dimethylthiourea Chemical compound CNC(=S)NC VLCDUOXHFNUCKK-UHFFFAOYSA-N 0.000 description 1
SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 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
241000209117 Panicum Species 0.000 description 1
235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 1
235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 1
241001520808 Panicum virgatum Species 0.000 description 1
241000219833 Phaseolus Species 0.000 description 1
241000746981 Phleum 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
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
240000006694 Stellaria media 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
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical group ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 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
230000000895 acaricidal effect Effects 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
150000008051 alkyl sulfates 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
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000002969 artificial stone Substances 0.000 description 1
238000000889 atomisation Methods 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
QOHQYMPGUOODJU-UHFFFAOYSA-N butoxymethanethioic s-acid Chemical compound CCCCOC(S)=O QOHQYMPGUOODJU-UHFFFAOYSA-N 0.000 description 1
HUVDYZVGBKYNMO-UHFFFAOYSA-N carbononitridic chloride hydrochloride Chemical compound Cl.N#CCl HUVDYZVGBKYNMO-UHFFFAOYSA-N 0.000 description 1
239000012159 carrier gas Substances 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
239000004927 clay Substances 0.000 description 1
230000009194 climbing Effects 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-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
238000004821 distillation Methods 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
235000014103 egg white Nutrition 0.000 description 1
210000000969 egg white Anatomy 0.000 description 1
IOGRQVWSROKHGE-UHFFFAOYSA-N ethyl 4-carboxyoxybenzoate hydrochloride Chemical compound Cl.CCOC(=O)C1=CC=C(OC(O)=O)C=C1 IOGRQVWSROKHGE-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
VUWPFWPXBJVSQO-UHFFFAOYSA-N ethyl hydrogen carbonate;hydrochloride Chemical compound Cl.CCOC(O)=O VUWPFWPXBJVSQO-UHFFFAOYSA-N 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
150000002191 fatty alcohols Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000005826 halohydrocarbons Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
IFKONDWPXROQGA-UHFFFAOYSA-N imidazole-1-carbothioic s-acid Chemical compound OC(=S)N1C=CN=C1 IFKONDWPXROQGA-UHFFFAOYSA-N 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
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 1
239000011133 lead Substances 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
GPPYYOFCUVXNNH-UHFFFAOYSA-N methyl hydrogen carbonate;hydrochloride Chemical compound Cl.COC(O)=O GPPYYOFCUVXNNH-UHFFFAOYSA-N 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
238000002156 mixing Methods 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
GLRRWFXFSXZSDZ-UHFFFAOYSA-N morpholine-4-carbothioic s-acid Chemical compound OC(=S)N1CCOCC1 GLRRWFXFSXZSDZ-UHFFFAOYSA-N 0.000 description 1
235000010460 mustard Nutrition 0.000 description 1
OYCNYAYYFWFXRF-UHFFFAOYSA-N n,n-dipropylcarbamothioyl chloride Chemical compound CCCN(C(Cl)=S)CCC OYCNYAYYFWFXRF-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
RECCURWJDVZHIH-UHFFFAOYSA-N para-chlorophenylurea Natural products NC(=O)NC1=CC=C(Cl)C=C1 RECCURWJDVZHIH-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
BIFDXOOJPDHKJH-UHFFFAOYSA-N piperidine-1-carbonyl chloride Chemical compound ClC(=O)N1CCCCC1 BIFDXOOJPDHKJH-UHFFFAOYSA-N 0.000 description 1
HFGGXBQZQRVOKM-UHFFFAOYSA-N piperidine-1-carbothioic s-acid Chemical compound SC(=O)N1CCCCC1 HFGGXBQZQRVOKM-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
235000012015 potatoes Nutrition 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
AGWHITDTBBVFAA-UHFFFAOYSA-N propyl hydrogen carbonate;hydrochloride Chemical compound Cl.CCCOC(O)=O AGWHITDTBBVFAA-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
URXNOJQCVQXMCT-UHFFFAOYSA-N pyrrolidine-1-carbothioic s-acid Chemical compound SC(=O)N1CCCC1 URXNOJQCVQXMCT-UHFFFAOYSA-N 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 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
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
UNHKSXOTUHOTAB-UHFFFAOYSA-N sodium;sulfane Chemical compound [Na].S UNHKSXOTUHOTAB-UHFFFAOYSA-N 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000003892 spreading Methods 0.000 description 1
239000004575 stone Substances 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
125000003396 thiol group Chemical group [H]S* 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000003799 water insoluble solvent Substances 0.000 description 1
239000003021 water soluble solvent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/36—Sulfur atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Thiazole And Isothizaole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO742937A 1973-09-01 1974-08-15 NO742937L (es)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19732344134 DE2344134A1 (de)	1973-09-01	1973-09-01	Kohlensaeurederivate des 2-mercapto-4,5dichlor-thiazols, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide

Publications (1)

Publication Number	Publication Date
NO742937L true NO742937L (es)	1974-04-01

Family

ID=5891354

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO742937A NO742937L (es)	1973-09-01	1974-08-15

Country Status (16)

Country	Link
US (1)	US3989710A (es)
JP (2)	JPS5050375A (es)
BE (1)	BE819319A (es)
BR (1)	BR7407275D0 (es)
DE (1)	DE2344134A1 (es)
DK (1)	DK461974A (es)
FI (1)	FI255174A (es)
FR (1)	FR2242386B1 (es)
GB (1)	GB1429457A (es)
IL (1)	IL45565A0 (es)
LU (1)	LU70823A1 (es)
NL (1)	NL7411531A (es)
NO (1)	NO742937L (es)
OA (1)	OA04770A (es)
SE (1)	SE7410958L (es)
ZA (1)	ZA745547B (es)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4308052A (en) *	1977-09-21	1981-12-29	Monsanto Company	N-Substituted benzothiazolines substituted with thiol esters useful as herbicides and plant growth regulants
DE3060330D1 (en) *	1979-04-06	1982-06-09	Bayer Ag	Azolyloxy-acetamides, process for their preparation and their use as herbicides
DE2946524A1 (de) *	1979-11-17	1981-06-11	Bayer Ag, 5090 Leverkusen	Azolyloxy-carbonsaeure-n-oxy-amide, verfahren zu ihrer herstellung und ihre verwendung als herbizide
DE4225024A1 (de) *	1992-07-29	1994-02-03	Bayer Ag	Chlorthiazolderivate
DE10034132A1 (de) *	2000-07-13	2002-01-24	Bayer Ag	Heterocyclische Fluoralkenylthioether (lll)
ES2258408B1 (es) *	2005-03-14	2007-11-16	Catalana D'innovacions Per La Construccio, S.L.	Procedimiento y dispositivo para la realizacion de excavaciones de forma general paralelepipedica.
EP3968772A4 (en) *	2019-05-13	2023-05-24	Agrematch Ltd.	COMPOSITIONS FOR CROP PROTECTION

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2697098A (en) *	1950-12-28	1954-12-14	Sharples Chemicals Inc	Process for preparing dithiocarbamic acid derivatives
US2766253A (en) *	1954-02-26	1956-10-09	Monsanto Chemicals	Thiazolyl mercapto alkyl thionocarbamates
US2721868A (en) *	1954-05-03	1955-10-25	Monsanto Chemicals	5-carboxy-2-thiazolyl dithiocarbamates
DE1595995A1 (de) *	1966-04-23	1970-02-12	Merck Ag E	Fungizides Mittel

1973
- 1973-09-01 DE DE19732344134 patent/DE2344134A1/de active Pending
1974
- 1974-08-14 US US05/497,356 patent/US3989710A/en not_active Expired - Lifetime
- 1974-08-15 NO NO742937A patent/NO742937L/no unknown
- 1974-08-29 NL NL7411531A patent/NL7411531A/xx unknown
- 1974-08-29 IL IL45565A patent/IL45565A0/xx unknown
- 1974-08-29 SE SE7410958A patent/SE7410958L/xx unknown
- 1974-08-29 BE BE148008A patent/BE819319A/xx unknown
- 1974-08-30 DK DK461974A patent/DK461974A/da unknown
- 1974-08-30 ZA ZA00745547A patent/ZA745547B/xx unknown
- 1974-08-30 FR FR7429678A patent/FR2242386B1/fr not_active Expired
- 1974-08-30 LU LU70823A patent/LU70823A1/xx unknown
- 1974-08-30 BR BR7275/74A patent/BR7407275D0/pt unknown
- 1974-08-30 GB GB3800674A patent/GB1429457A/en not_active Expired
- 1974-08-30 OA OA55285A patent/OA04770A/xx unknown
- 1974-08-30 FI FI2551/74A patent/FI255174A/fi unknown
- 1974-08-31 JP JP49099506A patent/JPS5050375A/ja active Pending
- 1974-08-31 JP JP49099507A patent/JPS5049428A/ja active Pending

Also Published As

Publication number	Publication date
IL45565A0 (en)	1974-11-29
DE2344134A1 (de)	1975-03-13
LU70823A1 (es)	1975-06-11
GB1429457A (en)	1976-03-24
JPS5049428A (es)	1975-05-02
BR7407275D0 (pt)	1975-06-24
SE7410958L (es)	1975-03-03
OA04770A (fr)	1980-08-31
ZA745547B (en)	1975-09-24
FR2242386A1 (es)	1975-03-28
DK461974A (es)	1975-04-28
US3989710A (en)	1976-11-02
NL7411531A (nl)	1975-03-04
FI255174A (es)	1975-03-02
FR2242386B1 (es)	1978-06-09
JPS5050375A (es)	1975-05-06
BE819319A (fr)	1975-02-28

Publication	Publication Date	Title
NO140061B (no)	1979-03-19	Tetrahydro-1,3,5-triazin-2,6-dioner med herbicide egenskaper
US3726892A (en)	1973-04-10	Certain 5-sulfamoyl-1,3,4-thiadiazol-2-ylureas
NO742937L (es)	1974-04-01
GB2164936A (en)	1986-04-03	Pesticidal substituted carbodiimides
US3879190A (en)	1975-04-22	Herbicidal allophanimidates
US4045209A (en)	1977-08-30	Substituted ureas as herbicides
US3824247A (en)	1974-07-16	2-(1,3,3-trimethylureido)-1,3,4-thiadiazole-5-n,n-dimethylsulfonamide
US3679726A (en)	1972-07-25	Substituted benzyl-thiolcarbamic acid esters
US3888879A (en)	1975-06-10	Fungicidal n-polyhaloalkylthiosulfonamidothiophenes
US3873299A (en)	1975-03-25	1,2,4-thiodiazolyl-urea herbicidal agents
US3127408A (en)	1964-03-31	4-thiocyanato-2-butynyl carbamates
US3895046A (en)	1975-07-15	Cyanophenyl esters of oxime-o-carbonic acid
US4067720A (en)	1978-01-10	Certain 2-carbamoyl-1,2,4-thiadiazole-3-one herbicides
DE1795037A1 (de)	1972-01-20	N-Acyl-2-amino-1,3,4-thiadiazole
CA1103665A (en)	1981-06-23	Preparation of esters of thiocarbamic acids involving use of phase transfer catalysts
US3856503A (en)	1974-12-24	Herbicidal method and compositions
US3981714A (en)	1976-09-21	Cyclic N-thiadiazolyl-(2)-carboxylic acid compounds and herbicidal compositions
US3242209A (en)	1966-03-22	Iminomethyleneureas
CA1148957A (en)	1983-06-28	Herbicidally active 1,3,4-thiadiazole derivatives
US3863474A (en)	1975-02-04	Substituted Benzyl-Thiolcarbamate Acid Esters as Herbicides
US3810890A (en)	1974-05-14	Aminecarbotrithioates and preparation
US4239524A (en)	1980-12-16	Thiadiazolyl ureas with herbicidal effect
US4051130A (en)	1977-09-27	4(3H)-oxobenzo-2,1,3-thiadiazine-2,2-dioxides and derivatives thereof
US3758481A (en)	1973-09-11	Ridine m-(2,4-dichloro - 5-(haloalkoxy)-phenylcarbomoyl)-pyrrolidine or pipe
US4119432A (en)	1978-10-10	Herbicidal N-(dialkylcarbamyl)-N-trifluoromethyl-phenylcarbamyl alkyl disulfides