DE3007556A1 - Tetrahydrobenzothiazolylimidazolidinone und ihre verwendung als herbizide - Google Patents
Tetrahydrobenzothiazolylimidazolidinone und ihre verwendung als herbizideInfo
- Publication number
- DE3007556A1 DE3007556A1 DE19803007556 DE3007556A DE3007556A1 DE 3007556 A1 DE3007556 A1 DE 3007556A1 DE 19803007556 DE19803007556 DE 19803007556 DE 3007556 A DE3007556 A DE 3007556A DE 3007556 A1 DE3007556 A1 DE 3007556A1
- Authority
- DE
- Germany
- Prior art keywords
- tetrahydrobenzothiazol
- hydroxy
- imidazolidin
- reaction mixture
- compound according
- 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.)
- Withdrawn
Links
- 239000004009 herbicide Substances 0.000 title claims description 28
- FNLMKLJJRWRDRY-UHFFFAOYSA-N 1-(2,3,3a,4-tetrahydro-1,3-benzothiazol-2-yl)imidazolidin-2-one Chemical compound O=C1NCCN1C1SC2=CC=CCC2N1 FNLMKLJJRWRDRY-UHFFFAOYSA-N 0.000 title description 2
- 238000002360 preparation method Methods 0.000 claims description 45
- -1 5,5,7,7-tetramethyl-4,5,6,7-tetrahydrobenzothiazol-2-yl Chemical group 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 43
- 241000196324 Embryophyta Species 0.000 claims description 41
- 230000002363 herbicidal effect Effects 0.000 claims description 18
- 239000004480 active ingredient Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
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- 230000002588 toxic effect Effects 0.000 claims description 5
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- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- DOETVZCFKJCYJV-UHFFFAOYSA-N 6-(4,5-dihydro-1h-imidazol-2-yl)-2-[4-(4,5-dihydro-1h-imidazol-2-yl)phenyl]-1h-indole Chemical compound N1CCN=C1C1=CC=C(C=2NC3=CC(=CC=C3C=2)C=2NCCN=2)C=C1 DOETVZCFKJCYJV-UHFFFAOYSA-N 0.000 claims 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
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- 239000003279 phenylacetic acid Substances 0.000 description 1
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 description 1
- TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- ISEUFVQQFVOBCY-UHFFFAOYSA-N prometon Chemical compound COC1=NC(NC(C)C)=NC(NC(C)C)=N1 ISEUFVQQFVOBCY-UHFFFAOYSA-N 0.000 description 1
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
- WJNRPILHGGKWCK-UHFFFAOYSA-N propazine Chemical compound CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 WJNRPILHGGKWCK-UHFFFAOYSA-N 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- HKAMKLBXTLTVCN-UHFFFAOYSA-N simeton Chemical compound CCNC1=NC(NCC)=NC(OC)=N1 HKAMKLBXTLTVCN-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 235000005765 wild carrot Nutrition 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- 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)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1685479A | 1979-03-02 | 1979-03-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3007556A1 true DE3007556A1 (de) | 1980-09-11 |
Family
ID=21779343
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803007556 Withdrawn DE3007556A1 (de) | 1979-03-02 | 1980-02-28 | Tetrahydrobenzothiazolylimidazolidinone und ihre verwendung als herbizide |
Country Status (18)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0155523A1 (en) * | 1984-03-01 | 1985-09-25 | A. Nattermann & Cie. GmbH | 3-Amino-1-(4,5,6,7-Tetrahydro-benzothiazolyl)-2-Pyrazolines,a process for their preparation and pharmaceutical products containing these compounds |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57175189A (en) * | 1981-04-21 | 1982-10-28 | Kyowa Hakko Kogyo Co Ltd | Benzothiazole derivative and its preparation |
| JPS58110582A (ja) * | 1981-12-24 | 1983-07-01 | Kureha Chem Ind Co Ltd | テトラヒドロベンゾチアゾリルイミダゾリジノン誘導体及び該誘導体を有効成分とする除草剤 |
| DE3246705C2 (de) * | 1981-12-24 | 1986-07-10 | Kureha Kagaku Kogyo K.K., Tokio/Tokyo | Tetrahydrobenzthiazolderivate und diese Verbindungen als wirksamen Bestandteil enthaltende herbizide Mittel |
| US4577029A (en) * | 1982-05-10 | 1986-03-18 | Kureha Kagaku Kogyo Kabushiki Kaisha | Derivative of tetrahydrobenzothiazole and herbicidal composition containing the same as active ingredient |
| JPS59186979A (ja) * | 1983-04-08 | 1984-10-23 | Kureha Chem Ind Co Ltd | テトラヒドロベンゾチアゾ−ル誘導体及び該誘導体を含有する除草剤 |
| JPS6317880A (ja) * | 1986-07-09 | 1988-01-25 | Nippon Tokushu Noyaku Seizo Kk | 新規ｎ−ベンゾチアゾリル−２，５−ジヒドロピロ−ル類及び除草剤 |
| ES2245604B1 (es) * | 2004-06-25 | 2006-12-01 | Ragactives, S. L. | Procedimiento para la obtencion de 2-amino-6-alquil-amino-4,5,6,7-tetrahidrobenzotiazoles. |
| CN105873918A (zh) * | 2013-12-23 | 2016-08-17 | 先正达参股股份有限公司 | 具有除草活性的二氢-乙内酰脲衍生物 |
| GB201419827D0 (en) | 2014-11-07 | 2014-12-24 | Syngenta Participations Ag | Herbicidal compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ184082A (en) * | 1976-05-20 | 1980-05-27 | Velsicol Chemical Corp | 1-benzothiazol-2yl-1,3-imidazolidin-2-ones |
-
1980
- 1980-02-07 IL IL59334A patent/IL59334A/xx unknown
- 1980-02-08 AU AU55376/80A patent/AU531808B2/en not_active Ceased
- 1980-02-19 CA CA345,912A patent/CA1126734A/en not_active Expired
- 1980-02-20 NZ NZ192923A patent/NZ192923A/xx unknown
- 1980-02-20 ZA ZA00800978A patent/ZA80978B/xx unknown
- 1980-02-26 IT IT48013/80A patent/IT1127362B/it active
- 1980-02-27 BR BR8001161A patent/BR8001161A/pt unknown
- 1980-02-28 FR FR8004430A patent/FR2450257A1/fr active Granted
- 1980-02-28 DE DE19803007556 patent/DE3007556A1/de not_active Withdrawn
- 1980-02-28 SE SE8001556A patent/SE8001556L/xx not_active Application Discontinuation
- 1980-02-28 AR AR280125A patent/AR222375A1/es active
- 1980-02-29 BE BE0/199617A patent/BE882010A/fr not_active IP Right Cessation
- 1980-02-29 DK DK88880A patent/DK88880A/da not_active Application Discontinuation
- 1980-02-29 CH CH164080A patent/CH645109A5/de not_active IP Right Cessation
- 1980-02-29 AT AT0113780A patent/AT365409B/de not_active IP Right Cessation
- 1980-02-29 NL NL8001243A patent/NL8001243A/nl not_active Application Discontinuation
- 1980-02-29 GB GB8006873A patent/GB2045754B/en not_active Expired
- 1980-03-03 JP JP2649880A patent/JPS55133381A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0155523A1 (en) * | 1984-03-01 | 1985-09-25 | A. Nattermann & Cie. GmbH | 3-Amino-1-(4,5,6,7-Tetrahydro-benzothiazolyl)-2-Pyrazolines,a process for their preparation and pharmaceutical products containing these compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1127362B (it) | 1986-05-21 |
| GB2045754B (en) | 1983-03-30 |
| NZ192923A (en) | 1981-11-19 |
| GB2045754A (en) | 1980-11-05 |
| IT8048013A0 (it) | 1980-02-26 |
| CA1126734A (en) | 1982-06-29 |
| AR222375A1 (es) | 1981-05-15 |
| IL59334A (en) | 1984-01-31 |
| NL8001243A (nl) | 1980-09-04 |
| AT365409B (de) | 1982-01-11 |
| BE882010A (fr) | 1980-06-16 |
| FR2450257A1 (fr) | 1980-09-26 |
| ZA80978B (en) | 1981-02-25 |
| CH645109A5 (de) | 1984-09-14 |
| FR2450257B1 (enrdf_load_stackoverflow) | 1983-06-10 |
| DK88880A (da) | 1980-09-03 |
| BR8001161A (pt) | 1980-11-04 |
| ATA113780A (de) | 1981-06-15 |
| SE8001556L (sv) | 1980-09-03 |
| AU5537680A (en) | 1980-09-04 |
| AU531808B2 (en) | 1983-09-08 |
| JPS55133381A (en) | 1980-10-17 |
| IL59334A0 (en) | 1980-05-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8128 | New person/name/address of the agent |
Representative=s name: SCHWABE, H., DIPL.-ING. SANDMAIR, K., DIPL.-CHEM. |
|
| 8141 | Disposal/no request for examination |