PL108414B1 - Method of producing thiocarbamic acid esters - Google Patents

Method of producing thiocarbamic acid esters Download PDF

Info

Publication number: PL108414B1
Authority: PL; Poland
Prior art keywords: mercaptan; chloride; transfer catalyst; carbon atoms; formula
Prior art date: 1976-09-03

Application number

PL1977200632A

Other languages

English (en)

Polish (pl)

Other versions

PL200632A1 (pl

Inventor

Harold M Pitt

Original Assignee

Stauffer Chemical Co

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.)

1976-09-03

Filing date

1977-09-02

Publication date

1980-04-30

1977-09-02 Application filed by Stauffer Chemical Co filed Critical Stauffer Chemical Co

1978-05-22 Publication of PL200632A1 publication Critical patent/PL200632A1/xx

1980-04-30 Publication of PL108414B1 publication Critical patent/PL108414B1/pl

Links

238000000034 method Methods 0.000 title claims description 94
150000003560 thiocarbamic acids Chemical class 0.000 title claims description 8
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 64
125000004432 carbon atom Chemical group C* 0.000 claims description 60
239000003054 catalyst Substances 0.000 claims description 50
230000008569 process Effects 0.000 claims description 46
238000006243 chemical reaction Methods 0.000 claims description 44
-1 thiocarbamic acid ester Chemical class 0.000 claims description 42
CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 40
239000000203 mixture Chemical group 0.000 claims description 35
125000000217 alkyl group Chemical group 0.000 claims description 34
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
230000003197 catalytic effect Effects 0.000 claims description 20
239000012670 alkaline solution Substances 0.000 claims description 19
239000007864 aqueous solution Substances 0.000 claims description 19
239000003795 chemical substances by application Substances 0.000 claims description 18
230000016507 interphase Effects 0.000 claims description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
229910052757 nitrogen Inorganic materials 0.000 claims description 15
229910052801 chlorine Inorganic materials 0.000 claims description 14
239000000460 chlorine Substances 0.000 claims description 13
150000003839 salts Chemical group 0.000 claims description 13
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 11
239000003444 phase transfer catalyst Substances 0.000 claims description 11
125000003118 aryl group Chemical group 0.000 claims description 10
229910052794 bromium Inorganic materials 0.000 claims description 10
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 claims description 10
239000012074 organic phase Substances 0.000 claims description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
125000003342 alkenyl group Chemical group 0.000 claims description 9
125000002877 alkyl aryl group Chemical group 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 8
125000003710 aryl alkyl group Chemical group 0.000 claims description 8
238000002474 experimental method Methods 0.000 claims description 8
229910052731 fluorine Inorganic materials 0.000 claims description 8
229910052698 phosphorus Inorganic materials 0.000 claims description 8
239000011574 phosphorus Chemical group 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
239000003513 alkali Substances 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
125000000262 haloalkenyl group Chemical group 0.000 claims description 6
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
VUYCBBHNGBWOJM-UHFFFAOYSA-N NCOCl Chemical compound NCOCl VUYCBBHNGBWOJM-UHFFFAOYSA-N 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 5
239000011630 iodine Substances 0.000 claims description 5
230000035484 reaction time Effects 0.000 claims description 5
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
239000008346 aqueous phase Substances 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 4
CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 0.000 claims description 4
150000001805 chlorine compounds Chemical group 0.000 claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 4
OWRABTHGOKNUDV-UHFFFAOYSA-N n,n-dipropylcarbamoyl chloride Chemical compound CCCN(C(Cl)=O)CCC OWRABTHGOKNUDV-UHFFFAOYSA-N 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
150000001450 anions Chemical group 0.000 claims description 3
229910052787 antimony Inorganic materials 0.000 claims description 3
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 3
229910052785 arsenic Inorganic materials 0.000 claims description 3
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 3
229910052797 bismuth Chemical group 0.000 claims description 3
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical group [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 3
150000001768 cations Chemical class 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 3
GZNVFRIHZRYMFK-UHFFFAOYSA-N n-butyl-n-ethylcarbamoyl chloride Chemical compound CCCCN(CC)C(Cl)=O GZNVFRIHZRYMFK-UHFFFAOYSA-N 0.000 claims description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
229940079593 drug Drugs 0.000 claims description 2
150000004820 halides Chemical group 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 claims description 2
RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 claims description 2
239000004215 Carbon black (E152) Substances 0.000 claims 1
229930195733 hydrocarbon Natural products 0.000 claims 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 18
239000000047 product Substances 0.000 description 14
241000196324 Embryophyta Species 0.000 description 8
150000001875 compounds Chemical class 0.000 description 8
239000000243 solution Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
238000002156 mixing Methods 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
238000005507 spraying Methods 0.000 description 6
230000006378 damage Effects 0.000 description 5
230000008901 benefit Effects 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
238000010924 continuous production Methods 0.000 description 4
239000007789 gas Substances 0.000 description 4
230000002363 herbicidal effect Effects 0.000 description 4
239000007791 liquid phase Substances 0.000 description 4
125000001624 naphthyl group Chemical group 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
241000894007 species Species 0.000 description 4
239000000126 substance Substances 0.000 description 4
244000075850 Avena orientalis Species 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000002689 soil Substances 0.000 description 3
239000007921 spray Substances 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
235000007319 Avena orientalis Nutrition 0.000 description 2
241000219198 Brassica Species 0.000 description 2
229920000298 Cellophane Polymers 0.000 description 2
244000046052 Phaseolus vulgaris Species 0.000 description 2
235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
240000007001 Rumex acetosella Species 0.000 description 2
235000015761 Rumex acetosella Nutrition 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
125000000304 alkynyl group Chemical group 0.000 description 2
238000010923 batch production Methods 0.000 description 2
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 2
229940006460 bromide ion Drugs 0.000 description 2
125000004965 chloroalkyl group Chemical group 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
125000002704 decyl 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])* 0.000 description 2
150000008050 dialkyl sulfates Chemical class 0.000 description 2
125000002541 furyl group Chemical group 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000004009 herbicide Substances 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
125000001041 indolyl group Chemical group 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
239000002917 insecticide Substances 0.000 description 2
239000010410 layer Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
125000002757 morpholinyl group Chemical group 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
229920000136 polysorbate Polymers 0.000 description 2
125000004076 pyridyl group Chemical group 0.000 description 2
125000000714 pyrimidinyl group Chemical group 0.000 description 2
125000005493 quinolyl group Chemical group 0.000 description 2
239000000376 reactant Substances 0.000 description 2
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
238000005303 weighing Methods 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 1
XOFNHZHCGBPVGJ-UHFFFAOYSA-N 5-ethyl-2-methylpiperidine Chemical compound CCC1CCC(C)NC1 XOFNHZHCGBPVGJ-UHFFFAOYSA-N 0.000 description 1
244000237956 Amaranthus retroflexus Species 0.000 description 1
235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
235000005781 Avena Nutrition 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
235000003351 Brassica cretica Nutrition 0.000 description 1
244000178993 Brassica juncea Species 0.000 description 1
235000011332 Brassica juncea Nutrition 0.000 description 1
235000014700 Brassica juncea var napiformis Nutrition 0.000 description 1
235000010570 Brassica rapa var. rapa Nutrition 0.000 description 1
235000003343 Brassica rupestris Nutrition 0.000 description 1
239000005745 Captan Substances 0.000 description 1
244000152970 Digitaria sanguinalis Species 0.000 description 1
235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
235000001018 Hibiscus sabdariffa 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
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
229910001209 Low-carbon steel Inorganic materials 0.000 description 1
244000115721 Pennisetum typhoides Species 0.000 description 1
235000007195 Pennisetum typhoides Nutrition 0.000 description 1
229920001213 Polysorbate 20 Polymers 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
235000005291 Rumex acetosa Nutrition 0.000 description 1
235000021501 Rumex crispus Nutrition 0.000 description 1
244000207667 Rumex vesicarius Species 0.000 description 1
235000008515 Setaria glauca Nutrition 0.000 description 1
GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 1
229910052776 Thorium Inorganic materials 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
238000013019 agitation Methods 0.000 description 1
125000003302 alkenyloxy group Chemical group 0.000 description 1
125000006383 alkylpyridyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
GCGYREODZIZPLJ-UHFFFAOYSA-N azepan-1-ium;chloride Chemical compound Cl.C1CCCNCC1 GCGYREODZIZPLJ-UHFFFAOYSA-N 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
239000002585 base Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
CXUFAAUKTHVLAL-UHFFFAOYSA-N butylphosphanium;chloride Chemical compound [Cl-].CCCC[PH3+] CXUFAAUKTHVLAL-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229940117949 captan Drugs 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
GNVMUORYQLCPJZ-UHFFFAOYSA-N carbamothioic s-acid Chemical compound NC(S)=O GNVMUORYQLCPJZ-UHFFFAOYSA-N 0.000 description 1
125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
DXHPZXWIPWDXHJ-UHFFFAOYSA-N carbon monosulfide Chemical compound [S+]#[C-] DXHPZXWIPWDXHJ-UHFFFAOYSA-N 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
230000008859 change Effects 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
125000004966 cyanoalkyl group Chemical group 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 1
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 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
239000003995 emulsifying agent Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000003292 glue Substances 0.000 description 1
125000004438 haloalkoxy group Chemical group 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000006178 methyl benzyl group Chemical group 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
244000005700 microbiome Species 0.000 description 1
235000010460 mustard Nutrition 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
HVZWVEKIQMJYIK-UHFFFAOYSA-N nitryl chloride Chemical compound [O-][N+](Cl)=O HVZWVEKIQMJYIK-UHFFFAOYSA-N 0.000 description 1
230000009972 noncorrosive effect Effects 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 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
239000003960 organic solvent Substances 0.000 description 1
150000004028 organic sulfates Chemical class 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
125000005359 phenoxyalkyl group Chemical group 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
125000005936 piperidyl group Chemical group 0.000 description 1
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000010926 purge Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
125000002755 pyrazolinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
WPLQGUQIRXKRFR-UHFFFAOYSA-N s-ethyl n-butyl-n-ethylcarbamothioate Chemical compound CCCCN(CC)C(=O)SCC WPLQGUQIRXKRFR-UHFFFAOYSA-N 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000013049 sediment Substances 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
238000009331 sowing Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
230000009466 transformation Effects 0.000 description 1
125000004417 unsaturated alkyl group Chemical group 0.000 description 1
125000005023 xylyl group Chemical group 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/21—Radicals derived from sulfur analogues of carbonic acid
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring

Landscapes

Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Furan Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

PL1977200632A 1976-09-03 1977-09-02 Method of producing thiocarbamic acid esters PL108414B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US72028476A	1976-09-03	1976-09-03

Publications (2)

Publication Number	Publication Date
PL200632A1 PL200632A1 (pl)	1978-05-22
PL108414B1 true PL108414B1 (en)	1980-04-30

Family

ID=24893423

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PL1977200632A PL108414B1 (en)	1976-09-03	1977-09-02	Method of producing thiocarbamic acid esters

Country Status (22)

Country	Link
JP (1)	JPS6058748B2 (cs)
AR (1)	AR219718A1 (cs)
AU (1)	AU508898B2 (cs)
BE (1)	BE858348A (cs)
BR (1)	BR7705777A (cs)
CA (1)	CA1103665A (cs)
CH (1)	CH636605A5 (cs)
CS (1)	CS207480B1 (cs)
DD (1)	DD132432A5 (cs)
DE (1)	DE2738628A1 (cs)
DK (1)	DK390277A (cs)
ES (1)	ES462081A1 (cs)
FR (1)	FR2363551A1 (cs)
GB (1)	GB1538643A (cs)
HU (1)	HU175829B (cs)
IL (1)	IL52868A (cs)
IN (1)	IN145874B (cs)
IT (1)	IT1091119B (cs)
NL (1)	NL7709711A (cs)
PL (1)	PL108414B1 (cs)
SU (1)	SU921464A3 (cs)
ZA (1)	ZA775331B (cs)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4147715A (en) *	1978-03-23	1979-04-03	Stauffer Chemical Company	Thiocarbamate preparation utilizing quaternary ammonium salt catalysts
ZA849423B (en) *	1983-12-05	1985-10-30	Stauffer Chemical Co	Herbicidal compositions and method of controlling weeds
JP7016454B2 (ja) *	2019-11-20	2022-02-04	三菱電機株式会社	判定装置、判定方法及び判定プログラム

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2983747A (en) *	1958-07-28	1961-05-09	Stauffer Chemical Co	Process for making thiolcarbamates

1977
- 1977-08-26 DE DE19772738628 patent/DE2738628A1/de not_active Withdrawn
- 1977-08-26 CA CA285,552A patent/CA1103665A/en not_active Expired
- 1977-08-29 FR FR7726182A patent/FR2363551A1/fr active Granted
- 1977-08-30 BR BR7705777A patent/BR7705777A/pt unknown
- 1977-08-31 CH CH1062077A patent/CH636605A5/de not_active IP Right Cessation
- 1977-09-01 DD DD7700200853A patent/DD132432A5/xx unknown
- 1977-09-01 IL IL52868A patent/IL52868A/xx unknown
- 1977-09-01 DK DK390277A patent/DK390277A/da not_active Application Discontinuation
- 1977-09-01 CS CS570777A patent/CS207480B1/cs unknown
- 1977-09-02 AR AR269075A patent/AR219718A1/es active
- 1977-09-02 SU SU772517657A patent/SU921464A3/ru active
- 1977-09-02 NL NL7709711A patent/NL7709711A/xx not_active Application Discontinuation
- 1977-09-02 AU AU28508/77A patent/AU508898B2/en not_active Expired
- 1977-09-02 ZA ZA00775331A patent/ZA775331B/xx unknown
- 1977-09-02 PL PL1977200632A patent/PL108414B1/pl unknown
- 1977-09-02 GB GB36761/77A patent/GB1538643A/en not_active Expired
- 1977-09-02 BE BE2056207A patent/BE858348A/xx not_active IP Right Cessation
- 1977-09-02 IT IT50870/77A patent/IT1091119B/it active
- 1977-09-02 ES ES462081A patent/ES462081A1/es not_active Expired
- 1977-09-02 HU HU77SA3059A patent/HU175829B/hu unknown
- 1977-09-02 IN IN1360/CAL/77A patent/IN145874B/en unknown
- 1977-09-03 JP JP52105400A patent/JPS6058748B2/ja not_active Expired

Also Published As

Publication number	Publication date
HU175829B (hu)	1980-10-28
IT1091119B (it)	1985-06-26
CH636605A5 (en)	1983-06-15
ES462081A1 (es)	1978-12-01
IL52868A0 (en)	1977-11-30
BR7705777A (pt)	1978-06-06
DD132432A5 (de)	1978-09-27
JPS6058748B2 (ja)	1985-12-21
ZA775331B (en)	1978-07-26
JPS5334722A (en)	1978-03-31
FR2363551A1 (fr)	1978-03-31
IL52868A (en)	1980-06-30
AU2850877A (en)	1979-03-08
NL7709711A (nl)	1978-03-07
GB1538643A (en)	1979-01-24
DE2738628A1 (de)	1978-03-09
FR2363551B1 (cs)	1983-09-23
CA1103665A (en)	1981-06-23
DK390277A (da)	1978-03-04
SU921464A3 (ru)	1982-04-15
PL200632A1 (pl)	1978-05-22
AR219718A1 (es)	1980-09-15
CS207480B1 (en)	1981-07-31
IN145874B (cs)	1979-01-13
BE858348A (nl)	1978-03-02
AU508898B2 (en)	1980-04-03

Publication	Publication Date	Title
JPH026465A (ja)	1990-01-10	有機ジスルフィド及びポリスルフィドの製造方法
SU656462A3 (ru)	1979-04-05	Инсектицидно-овицидное средство
Heydari et al.	2009	Trifluoroethanol as a metal-free, homogeneous and recyclable medium for the efficient one-pot synthesis of α-amino nitriles and α-amino phosphonates
PL91624B1 (cs)	1977-03-31
US4435575A (en)	1984-03-06	Process for preparing carboxylated organic compounds
EP0004377B1 (en)	1982-03-17	Thiocarbamate preparation utilizing quaternary ammonium salt catalysts
US3093537A (en)	1963-06-11	Chlorothiolformate pesticide
US2805257A (en)	1957-09-03	1-ethynyl-cyclohexylthiols
CS207480B1 (en)	1981-07-31	method of preparation of esters of the thiocarbame acids
RU2725878C1 (ru)	2020-07-07	Хиральные миртанилсульфонамиды
US3412117A (en)	1968-11-19	Preparation of heavy metal complex salts of ethylenebisdithiocarbamic acid and dimethyldithiocarbamic acid
US4613461A (en)	1986-09-23	Process for preparing esters of thiolcarbamic acids
KR810000377B1 (ko)	1981-04-24	상전이(相轉移)촉매를 사용한 티오카르 바민산 에스테르의 제조방법
US3737457A (en)	1973-06-05	Process for making compounds containing the sulfonyl cyanide group
CA1080240A (en)	1980-06-24	Preparation of esters of thiocarbamic acids
US3266882A (en)	1966-08-16	Herbicidal compositions and their use
US3308132A (en)	1967-03-07	6, 8-dithiooctanoyl amides and intermediates
EP0156728B1 (en)	1988-11-02	Process for the preparation of thiocarbamates
US3206491A (en)	1965-09-14	Compounds for combatting plantparasitic nematodes
US4929268A (en)	1990-05-29	Substituted oxirane compounds
US3354157A (en)	1967-11-21	Trichlorofuramides
US3162689A (en)	1964-12-22	Polychalkogen ethers
US3984481A (en)	1976-10-05	Bis-2-substituted-thiovinyl sulfones
US3899318A (en)	1975-08-12	Herbicidal 1,5-dithia-2,4,6,8-tetrazacyclooctane-3,7-dione
JPH0253764A (ja)	1990-02-22	ジチオビスフェノールの製造方法