GB1591511A - Herbicidally active 2-(dimethylcarbamoylimino)-benzthiazolin-3-carboxylic acid esters process for their manufacture and their use - Google Patents
Herbicidally active 2-(dimethylcarbamoylimino)-benzthiazolin-3-carboxylic acid esters process for their manufacture and their use Download PDFInfo
- Publication number
- GB1591511A GB1591511A GB39093/77A GB3909377A GB1591511A GB 1591511 A GB1591511 A GB 1591511A GB 39093/77 A GB39093/77 A GB 39093/77A GB 3909377 A GB3909377 A GB 3909377A GB 1591511 A GB1591511 A GB 1591511A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- general formula
- ester
- dimethylcarbamoylimino
- benzthiazolin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 28
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- NJUXASYUHPEHGA-UHFFFAOYSA-N 2-(dimethylcarbamoylimino)-1,3-benzothiazole-3-carboxylic acid Chemical class C1=CC=C2N(C(O)=O)C(=NC(=O)N(C)C)SC2=C1 NJUXASYUHPEHGA-UHFFFAOYSA-N 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 60
- 150000002148 esters Chemical class 0.000 claims description 28
- 241000196324 Embryophyta Species 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 18
- 230000002363 herbicidal effect Effects 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 5
- 239000004009 herbicide Substances 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000011230 binding agent Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 150000002736 metal compounds Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004803 chlorobenzyl group Chemical group 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- 125000006286 dichlorobenzyl group Chemical group 0.000 claims description 2
- 125000004188 dichlorophenyl group Chemical group 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 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 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 239000011734 sodium Chemical group 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- XVIGADSBHCKJLF-UHFFFAOYSA-N 2-methylpropyl 2-(dimethylcarbamoylimino)-1,3-benzothiazole-3-carboxylate Chemical compound C1=CC=C2SC(=NC(=O)N(C)C)N(C(=O)OCC(C)C)C2=C1 XVIGADSBHCKJLF-UHFFFAOYSA-N 0.000 claims 1
- IAIIXGSYWLKUFD-UHFFFAOYSA-N benzyl 2-(dimethylcarbamoylimino)-1,3-benzothiazole-3-carboxylate Chemical compound CN(C)C(=O)N=C1SC2=CC=CC=C2N1C(=O)OCC1=CC=CC=C1 IAIIXGSYWLKUFD-UHFFFAOYSA-N 0.000 claims 1
- BLPKFIXWOGHNTA-UHFFFAOYSA-N butyl 2-(dimethylcarbamoylimino)-1,3-benzothiazole-3-carboxylate Chemical compound C1=CC=C2SC(=NC(=O)N(C)C)N(C(=O)OCCCC)C2=C1 BLPKFIXWOGHNTA-UHFFFAOYSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- ZNVZAXZWNPXCHD-UHFFFAOYSA-N methyl 2-(dimethylcarbamoylimino)-1,3-benzothiazole-3-carboxylate Chemical compound C1=CC=C2SC(=NC(=O)N(C)C)N(C(=O)OC)C2=C1 ZNVZAXZWNPXCHD-UHFFFAOYSA-N 0.000 claims 1
- MFZGQJQLYPXYSG-UHFFFAOYSA-N pentyl 2-(dimethylcarbamoylimino)-1,3-benzothiazole-3-carboxylate Chemical compound C1=CC=C2SC(=NC(=O)N(C)C)N(C(=O)OCCCCC)C2=C1 MFZGQJQLYPXYSG-UHFFFAOYSA-N 0.000 claims 1
- MWMLZCSVPFBSMT-UHFFFAOYSA-N phenyl 2-(dimethylcarbamoylimino)-1,3-benzothiazole-3-carboxylate Chemical compound CN(C)C(=O)N=C1SC2=CC=CC=C2N1C(=O)OC1=CC=CC=C1 MWMLZCSVPFBSMT-UHFFFAOYSA-N 0.000 claims 1
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- NQQUAVOWFXERQR-UHFFFAOYSA-N propan-2-yl 2-(dimethylcarbamoylimino)-1,3-benzothiazole-3-carboxylate Chemical compound C1=CC=C2SC(=NC(=O)N(C)C)N(C(=O)OC(C)C)C2=C1 NQQUAVOWFXERQR-UHFFFAOYSA-N 0.000 claims 1
- DOXCBFUUHPURBJ-UHFFFAOYSA-N s-ethyl 2-(dimethylcarbamoylimino)-1,3-benzothiazole-3-carbothioate Chemical compound C1=CC=C2SC(=NC(=O)N(C)C)N(C(=O)SCC)C2=C1 DOXCBFUUHPURBJ-UHFFFAOYSA-N 0.000 claims 1
- -1 dimethylcarbamoylimino Chemical group 0.000 description 24
- 150000003839 salts Chemical class 0.000 description 21
- 150000001408 amides Chemical class 0.000 description 16
- 230000006378 damage Effects 0.000 description 11
- 239000013543 active substance Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- AMIJSEIHRANBNZ-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)-1,1-dimethylurea Chemical compound C1=CC=C2SC(NC(=O)N(C)C)=NC2=C1 AMIJSEIHRANBNZ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 241000220261 Sinapis Species 0.000 description 3
- 235000002634 Solanum Nutrition 0.000 description 3
- 241000207763 Solanum Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 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
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- 239000007900 aqueous suspension Substances 0.000 description 2
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
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- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
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- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 2
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- 150000003566 thiocarboxylic acids Chemical class 0.000 description 2
- FTDGDIFUDKDKAW-UHFFFAOYSA-N 1,1a,5,5a,6,6a-hexahydrocyclopropa[a]indene Chemical class C12C(CC3CC=CC=C13)C2 FTDGDIFUDKDKAW-UHFFFAOYSA-N 0.000 description 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical class C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- AYQVYEBEWIDXRO-UHFFFAOYSA-N 1,3-benzothiazol-2-ylurea Chemical class C1=CC=C2SC(NC(=O)N)=NC2=C1 AYQVYEBEWIDXRO-UHFFFAOYSA-N 0.000 description 1
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- 150000002989 phenols Chemical class 0.000 description 1
- REJGOFYVRVIODZ-UHFFFAOYSA-N phosphanium;chloride Chemical class P.Cl REJGOFYVRVIODZ-UHFFFAOYSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- ZUDYYFQERNHIOD-UHFFFAOYSA-N prop-2-enyl 2-(dimethylcarbamoylimino)-1,3-benzothiazole-3-carboxylate Chemical compound C1=CC=C2N(C(=O)OCC=C)C(=NC(=O)N(C)C)SC2=C1 ZUDYYFQERNHIOD-UHFFFAOYSA-N 0.000 description 1
- IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- BFZYLUGEHGYJKJ-UHFFFAOYSA-N pyrazolidine-3-thione Chemical class S=C1CCNN1 BFZYLUGEHGYJKJ-UHFFFAOYSA-N 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000005299 pyridinones Chemical class 0.000 description 1
- 150000008318 pyrimidones Chemical class 0.000 description 1
- NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical class OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- QCMHWZUFWLOOGI-UHFFFAOYSA-N s-ethyl chloromethanethioate Chemical compound CCSC(Cl)=O QCMHWZUFWLOOGI-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- KISXBSWDCSYUKO-UHFFFAOYSA-N thiadiazinane 1,1-dioxide Chemical class O=S1(=O)CCCNN1 KISXBSWDCSYUKO-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000003582 thiophosphoric acids Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/82—Nitrogen atoms
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762644425 DE2644425A1 (de) | 1976-09-30 | 1976-09-30 | 2-(dimethylcarbamoylimino)-benzthiazolin-3-carbonsaeureester, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1591511A true GB1591511A (en) | 1981-06-24 |
Family
ID=5989471
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB39093/77A Expired GB1591511A (en) | 1976-09-30 | 1977-09-20 | Herbicidally active 2-(dimethylcarbamoylimino)-benzthiazolin-3-carboxylic acid esters process for their manufacture and their use |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4183739A (enExample) |
| JP (1) | JPS5344561A (enExample) |
| BE (1) | BE859271A (enExample) |
| DE (1) | DE2644425A1 (enExample) |
| DK (1) | DK410277A (enExample) |
| FR (1) | FR2366287A1 (enExample) |
| GB (1) | GB1591511A (enExample) |
| IE (1) | IE45688B1 (enExample) |
| IT (1) | IT1084535B (enExample) |
| LU (1) | LU78199A1 (enExample) |
| NL (1) | NL7710193A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2790299B2 (ja) * | 1989-02-01 | 1998-08-27 | 保土谷化学工業株式会社 | ペンゾチアゾール誘導体 |
| US10287259B2 (en) | 2016-03-14 | 2019-05-14 | The Penn State Research Foundation | Selenazolidine and thiazolidine compounds for treating cancer and other diseases |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2756135A (en) * | 1955-07-13 | 1956-07-24 | Du Pont | 1-methyl-3-(2-benzothiazolyl)-ureas and their use as herbicides |
| BE569605A (enExample) * | 1957-07-19 | |||
| US3501285A (en) * | 1968-06-10 | 1970-03-17 | Shell Oil Co | 2,1,3-benzothiadiazole-dicarbonitriles as defoliants |
| US3654296A (en) * | 1969-01-10 | 1972-04-04 | Merck & Co Inc | 2-chlorobenzothiazolecarboxamides |
| BE754782A (fr) * | 1969-08-14 | 1971-02-12 | May & Baker Ltd | Derives du thiophene a action herbicide |
| US3671531A (en) * | 1970-12-10 | 1972-06-20 | Monsanto Co | Benzothiazolinylidene substituted ureas |
| JPS5614643B2 (enExample) * | 1973-07-02 | 1981-04-06 | ||
| US3989505A (en) * | 1975-06-23 | 1976-11-02 | Hawaiian Sugar Planters' Association | Use of polycyclic thiophene compounds as ripeners for sugarcane |
| US4013681A (en) * | 1975-06-23 | 1977-03-22 | Hawaiian Sugar Planters' Association | Derivatives of thiophene |
| DE2624823A1 (de) * | 1976-05-31 | 1977-12-15 | Schering Ag | 2-(dimethylcarbamoylimino)-benzthiazolin-3-id-salze, verfahren zur herstellung dieser verbindungen sowie diese enthaltende herbizide mittel |
-
1976
- 1976-09-30 DE DE19762644425 patent/DE2644425A1/de not_active Withdrawn
-
1977
- 1977-09-15 DK DK410277A patent/DK410277A/da not_active Application Discontinuation
- 1977-09-16 NL NL7710193A patent/NL7710193A/xx not_active Application Discontinuation
- 1977-09-20 GB GB39093/77A patent/GB1591511A/en not_active Expired
- 1977-09-21 IE IE1923/77A patent/IE45688B1/en unknown
- 1977-09-22 US US05/835,530 patent/US4183739A/en not_active Expired - Lifetime
- 1977-09-28 IT IT28010/77A patent/IT1084535B/it active
- 1977-09-28 LU LU78199A patent/LU78199A1/xx unknown
- 1977-09-29 FR FR7729284A patent/FR2366287A1/fr active Granted
- 1977-09-30 BE BE181369A patent/BE859271A/xx not_active IP Right Cessation
- 1977-09-30 JP JP11778877A patent/JPS5344561A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| LU78199A1 (enExample) | 1978-01-23 |
| BE859271A (fr) | 1978-03-30 |
| DE2644425A1 (de) | 1978-04-06 |
| IT1084535B (it) | 1985-05-25 |
| NL7710193A (nl) | 1978-04-03 |
| JPS5616791B2 (enExample) | 1981-04-18 |
| DK410277A (da) | 1978-03-31 |
| IE45688B1 (en) | 1982-10-20 |
| FR2366287A1 (fr) | 1978-04-28 |
| FR2366287B1 (enExample) | 1982-10-01 |
| JPS5344561A (en) | 1978-04-21 |
| IE45688L (en) | 1978-03-30 |
| US4183739A (en) | 1980-01-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |