CH632742A5 - Process for the preparation of thiocarbamates - Google Patents
Process for the preparation of thiocarbamates Download PDFInfo
- Publication number
- CH632742A5 CH632742A5 CH1192877A CH1192877A CH632742A5 CH 632742 A5 CH632742 A5 CH 632742A5 CH 1192877 A CH1192877 A CH 1192877A CH 1192877 A CH1192877 A CH 1192877A CH 632742 A5 CH632742 A5 CH 632742A5
- Authority
- CH
- Switzerland
- Prior art keywords
- reaction
- amine
- thiocarbamic acid
- alkyl
- chlorine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 22
- 238000002360 preparation method Methods 0.000 title claims description 8
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 title claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 34
- -1 thiocarbamic acid ester Chemical class 0.000 claims description 23
- JJWKPURADFRFRB-UHFFFAOYSA-N carbonyl sulfide Chemical compound O=C=S JJWKPURADFRFRB-UHFFFAOYSA-N 0.000 claims description 18
- 150000004820 halides Chemical class 0.000 claims description 18
- 150000001412 amines Chemical class 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 16
- 239000000047 product Substances 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 150000003560 thiocarbamic acids Chemical class 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 239000006227 byproduct Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 5
- 239000007788 liquid Substances 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
- 150000003335 secondary amines Chemical class 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 150000001348 alkyl chlorides Chemical class 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000012736 aqueous medium Substances 0.000 claims description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 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 claims description 2
- 239000004009 herbicide Substances 0.000 claims description 2
- 239000002917 insecticide Substances 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 6
- 150000001350 alkyl halides Chemical class 0.000 claims 4
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims 3
- 159000000000 sodium salts Chemical class 0.000 claims 3
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims 2
- 230000032683 aging Effects 0.000 claims 2
- GNVMUORYQLCPJZ-UHFFFAOYSA-N carbamothioic s-acid Chemical compound NC(S)=O GNVMUORYQLCPJZ-UHFFFAOYSA-N 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 238000012544 monitoring process Methods 0.000 claims 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims 2
- 241000894006 Bacteria Species 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 238000013019 agitation Methods 0.000 claims 1
- 239000012670 alkaline solution Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000008051 alkyl sulfates Chemical class 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000003849 aromatic solvent Substances 0.000 claims 1
- KVVXFPNTQJIKNH-UHFFFAOYSA-N bis(prop-2-enyl) sulfate Chemical compound C=CCOS(=O)(=O)OCC=C KVVXFPNTQJIKNH-UHFFFAOYSA-N 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 230000007812 deficiency Effects 0.000 claims 1
- 150000008050 dialkyl sulfates Chemical class 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 244000005700 microbiome Species 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 150000004028 organic sulfates Chemical class 0.000 claims 1
- 230000005501 phase interface Effects 0.000 claims 1
- 150000003141 primary amines Chemical class 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 235000005074 zinc chloride Nutrition 0.000 claims 1
- 239000011592 zinc chloride Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 7
- 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
- 230000006378 damage Effects 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 244000178993 Brassica juncea Species 0.000 description 4
- 244000046052 Phaseolus vulgaris Species 0.000 description 4
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 4
- 229960003750 ethyl chloride Drugs 0.000 description 4
- 230000002363 herbicidal effect Effects 0.000 description 4
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 4
- 235000005474 African couch grass Nutrition 0.000 description 3
- 244000075850 Avena orientalis Species 0.000 description 3
- 235000007319 Avena orientalis Nutrition 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 description 3
- 244000025254 Cannabis sativa Species 0.000 description 3
- 241001520106 Eustachys Species 0.000 description 3
- 241000287828 Gallus gallus Species 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- 229920001213 Polysorbate 20 Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 3
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 3
- 238000012216 screening Methods 0.000 description 3
- 244000237956 Amaranthus retroflexus Species 0.000 description 2
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- 235000019713 millet Nutrition 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 1
- 241000219318 Amaranthus Species 0.000 description 1
- 235000011332 Brassica juncea Nutrition 0.000 description 1
- 235000014700 Brassica juncea var napiformis Nutrition 0.000 description 1
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
- 125000006539 C12 alkyl 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
- DFCAFRGABIXSDS-UHFFFAOYSA-N Cycloate Chemical compound CCSC(=O)N(CC)C1CCCCC1 DFCAFRGABIXSDS-UHFFFAOYSA-N 0.000 description 1
- 244000152970 Digitaria sanguinalis Species 0.000 description 1
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 1
- GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 244000088461 Panicum crus-galli Species 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- SGEJQUSYQTVSIU-UHFFFAOYSA-N Pebulate Chemical compound CCCCN(CC)C(=O)SCCC SGEJQUSYQTVSIU-UHFFFAOYSA-N 0.000 description 1
- 235000021501 Rumex crispus Nutrition 0.000 description 1
- 244000207667 Rumex vesicarius Species 0.000 description 1
- OKUGPJPKMAEJOE-UHFFFAOYSA-N S-propyl dipropylcarbamothioate Chemical compound CCCSC(=O)N(CCC)CCC OKUGPJPKMAEJOE-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl 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
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011086 glassine Substances 0.000 description 1
- 239000003966 growth inhibitor Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 1
- AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical compound CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000021395 porridge Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72956976A | 1976-10-04 | 1976-10-04 | |
| US79022277A | 1977-04-25 | 1977-04-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH632742A5 true CH632742A5 (en) | 1982-10-29 |
Family
ID=27111912
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1192877A CH632742A5 (en) | 1976-10-04 | 1977-09-29 | Process for the preparation of thiocarbamates |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS596301B2 (ro) |
| AU (1) | AU510456B2 (ro) |
| CA (1) | CA1080240A (ro) |
| CH (1) | CH632742A5 (ro) |
| DD (1) | DD132787A5 (ro) |
| DE (1) | DE2743513C2 (ro) |
| DK (1) | DK419477A (ro) |
| FR (1) | FR2366274A1 (ro) |
| GB (1) | GB1540367A (ro) |
| IL (1) | IL53037A (ro) |
| IT (1) | IT1090309B (ro) |
| MX (1) | MX4768E (ro) |
| NL (1) | NL7710849A (ro) |
| PL (1) | PL108304B1 (ro) |
| PT (1) | PT67111B (ro) |
| RO (1) | RO75743A (ro) |
| YU (1) | YU41425B (ro) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4759647A (en) * | 1986-10-22 | 1988-07-26 | International Business Machines Corporation | Dual pitch impact printer |
| CN101704776B (zh) * | 2009-04-27 | 2012-12-05 | 南通泰禾化工有限公司 | 一种生产茵达灭的改进工艺 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5612880B2 (ro) * | 1973-07-16 | 1981-03-25 | ||
| JPS5088030A (ro) * | 1973-12-12 | 1975-07-15 | ||
| US3954729A (en) * | 1974-03-25 | 1976-05-04 | Ihara Chemical Industry Co., Ltd. | Process for preparing a thiolcarbamate |
-
1977
- 1977-09-22 YU YU2257/77A patent/YU41425B/xx unknown
- 1977-09-22 DK DK419477A patent/DK419477A/da not_active Application Discontinuation
- 1977-09-22 AU AU29029/77A patent/AU510456B2/en not_active Expired
- 1977-09-26 CA CA287,514A patent/CA1080240A/en not_active Expired
- 1977-09-26 FR FR7728884A patent/FR2366274A1/fr active Granted
- 1977-09-27 RO RO7791675A patent/RO75743A/ro unknown
- 1977-09-28 MX MX776440U patent/MX4768E/es unknown
- 1977-09-28 DE DE2743513A patent/DE2743513C2/de not_active Expired
- 1977-09-29 CH CH1192877A patent/CH632742A5/de not_active IP Right Cessation
- 1977-09-30 IL IL53037A patent/IL53037A/xx unknown
- 1977-09-30 JP JP52116984A patent/JPS596301B2/ja not_active Expired
- 1977-10-03 PL PL1977201267A patent/PL108304B1/pl unknown
- 1977-10-03 PT PT67111A patent/PT67111B/pt unknown
- 1977-10-04 DD DD7700201356A patent/DD132787A5/xx unknown
- 1977-10-04 NL NL7710849A patent/NL7710849A/xx not_active Application Discontinuation
- 1977-10-04 GB GB41175/77A patent/GB1540367A/en not_active Expired
- 1977-10-04 IT IT51253/77A patent/IT1090309B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| DK419477A (da) | 1978-04-05 |
| GB1540367A (en) | 1979-02-14 |
| DD132787A5 (ro) | 1978-11-01 |
| PT67111A (en) | 1977-11-01 |
| IL53037A0 (en) | 1977-11-30 |
| MX4768E (es) | 1982-09-08 |
| RO75743A (ro) | 1981-02-28 |
| DE2743513A1 (de) | 1978-04-06 |
| PT67111B (en) | 1979-03-14 |
| NL7710849A (nl) | 1978-04-06 |
| DE2743513C2 (de) | 1986-05-28 |
| FR2366274B1 (ro) | 1984-06-08 |
| PL108304B1 (en) | 1980-04-30 |
| AU510456B2 (en) | 1980-06-26 |
| CA1080240A (en) | 1980-06-24 |
| JPS596301B2 (ja) | 1984-02-10 |
| YU225777A (en) | 1982-08-31 |
| YU41425B (en) | 1987-06-30 |
| AU2902977A (en) | 1979-03-29 |
| FR2366274A1 (fr) | 1978-04-28 |
| JPS5344524A (en) | 1978-04-21 |
| IL53037A (en) | 1981-09-13 |
| IT1090309B (it) | 1985-06-26 |
| PL201267A1 (pl) | 1978-09-11 |
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