GB1473224A - Substituted -3h- benzo 2,1,3-thiadiazine compounds and their use as active ingredients in herbicidal compositions - Google Patents
Substituted -3h- benzo 2,1,3-thiadiazine compounds and their use as active ingredients in herbicidal compositionsInfo
- Publication number
- GB1473224A GB1473224A GB4027174A GB4027174A GB1473224A GB 1473224 A GB1473224 A GB 1473224A GB 4027174 A GB4027174 A GB 4027174A GB 4027174 A GB4027174 A GB 4027174A GB 1473224 A GB1473224 A GB 1473224A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- hydrogen
- benzo
- halo
- sept
- 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
- -1 Substituted -3h- benzo 2,1,3-thiadiazine compounds Chemical class 0.000 title abstract 2
- 230000002363 herbicidal effect Effects 0.000 title abstract 2
- 239000004480 active ingredient Substances 0.000 title 1
- 239000000203 mixture Substances 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- GMCRNNWINPJXJN-UHFFFAOYSA-N 1h-2,1,3-benzothiadiazine Chemical class C1=CC=C2NSN=CC2=C1 GMCRNNWINPJXJN-UHFFFAOYSA-N 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 239000012670 alkaline solution Substances 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 125000000262 haloalkenyl group Chemical group 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000000232 haloalkynyl group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/15—Six-membered rings
- C07D285/16—Thiadiazines; Hydrogenated thiadiazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
1473224 Benzo - 2,1,3 - thiadiazine derivatives DOW CHEMICAL CO 16 Sept 1974 [17 Sept 1973] 40271/74 Heading C2C Novel benzo-2,1,3-thiadiazine derivatives of the general formula wherein each X is halo, Y<SP>1</SP>R<SP>2</SP>, Y<SP>11</SP>CF 2 CZ 3 , CF 3 , nitro or (C 1 -C 6 ) alkyl, provided that at least one X is always halo or nitro; n is 2, 3 or 4; m is 1 or 2; R and R<SP>1</SP> are each hydrogen, (C 1 -C 6 ) alkyl, haloalkyl, cycloalkyl, aryl, benzyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, -Y<SP>1</SP>R<SP>2</SP>, -SCCl 3 , -CONHR<SP>2</SP>, -NH 2 , -SO 2 aryl, -SO 2 alkyl, -COOR<SP>3</SP>, -C(CH 3 ) 2 C#CH or -C(CH 3 ) 2 -C#N; R<SP>2</SP> is hydrogen or (C 1 -C 4 ) alkyl; R<SP>3</SP> is (C 1 -C 6 ) alkyl; Y, Y<SP>1</SP> and Y<SP>11</SP> are oxygen or sulphur; Z is chloro, bromo, fluoro or hydrogen; and, where at least one of R and R<SP>1</SP> is hydrogen, a salt thereof with an organic or inorganic base, are prepared by cyclizing a sulphamide compound of the formula wherein T is a hydroxy, alkoxy, aryloxy, or halo group, by contact with a condensing agent, e.g. phosphorus oxychloride, thionyl chloride, or an aqueous or alcoholic alkaline solution. The cyclization reaction is suitably carried out in the presence of an inert organic solvent at a temperature of from 0‹ to 150‹ C. The novel compounds possess herbicidal properties.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39813973A | 1973-09-17 | 1973-09-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1473224A true GB1473224A (en) | 1977-05-11 |
Family
ID=23574146
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4027174A Expired GB1473224A (en) | 1973-09-17 | 1974-09-16 | Substituted -3h- benzo 2,1,3-thiadiazine compounds and their use as active ingredients in herbicidal compositions |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS6044281B2 (en) |
| AR (1) | AR210247A1 (en) |
| BE (1) | BE819949A (en) |
| BR (1) | BR7407705D0 (en) |
| CA (1) | CA1031339A (en) |
| DE (1) | DE2444383C2 (en) |
| FR (1) | FR2243945B1 (en) |
| GB (1) | GB1473224A (en) |
| HU (1) | HU170554B (en) |
| IT (1) | IT1048199B (en) |
| MY (1) | MY7800021A (en) |
| NL (1) | NL184363C (en) |
| PH (1) | PH11345A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2144919C1 (en) * | 1995-06-27 | 2000-01-27 | Акционерное общество "Химпром" | Method of preparing 3-isopropyl (1h)benz-2,1,3- thiadiazinone-4-dioxide-2,2 |
| CN114163430A (en) * | 2020-09-11 | 2022-03-11 | 东莞市东阳光农药研发有限公司 | Benzothiadiazine derivative and application thereof in agriculture |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2553209C2 (en) * | 1975-11-27 | 1986-01-02 | Basf Ag, 6700 Ludwigshafen | 1-methoxymethyl-3-isopropyl-2,1,3-benzothiadiazin (4) one-2,2-dioxide and herbicides containing them |
| DE2656290A1 (en) * | 1976-12-11 | 1978-06-15 | Basf Ag | BENZOTHIADIAZINE COMPOUNDS |
| DE2656289C2 (en) * | 1976-12-11 | 1982-08-12 | Basf Ag, 6700 Ludwigshafen | 1-cyano-3-isopropyl-2,1,3-benzothiadiazin-4-one-2,2-dioxide compounds |
| DE19700061A1 (en) * | 1997-01-03 | 1998-07-09 | Hoechst Schering Agrevo Gmbh | Production of new or known cyclic amino:sulphonamide derivatives |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3041336A (en) * | 1958-10-01 | 1962-06-26 | Norwich Pharma Co | 3-oxo-1.2.6-thiadiazine-1.1-dioxides |
| FR1354761A (en) * | 1959-09-30 | 1964-03-13 | Geigy Ag J R | Novel 3-oxo-1.2.6-thiadiazine 1.1-dioxides and their preparation |
| US3217001A (en) * | 1963-08-19 | 1965-11-09 | American Home Prod | Derivatives of 1h-2, 1, 3-benzothiadiazin-4(3h)-one 2-oxide and intermediates therefor |
| BE702877A (en) * | 1966-08-30 | 1968-02-21 | ||
| DE1670275B1 (en) * | 1967-09-30 | 1972-05-31 | Basf Ag | Salts of benzo-2,1,3-thiadiazinon- (4) -2,2-dioxyden and growth-regulating agents containing them and having simultaneous herbicidal action |
-
1974
- 1974-08-09 CA CA206,703A patent/CA1031339A/en not_active Expired
- 1974-09-11 PH PH16266A patent/PH11345A/en unknown
- 1974-09-13 IT IT2726274A patent/IT1048199B/en active
- 1974-09-13 NL NL7412188A patent/NL184363C/en not_active IP Right Cessation
- 1974-09-13 HU HUDO000385 patent/HU170554B/hu not_active IP Right Cessation
- 1974-09-16 BE BE148557A patent/BE819949A/en not_active IP Right Cessation
- 1974-09-16 BR BR770574A patent/BR7407705D0/en unknown
- 1974-09-16 GB GB4027174A patent/GB1473224A/en not_active Expired
- 1974-09-16 FR FR7431236A patent/FR2243945B1/fr not_active Expired
- 1974-09-17 JP JP49107082A patent/JPS6044281B2/en not_active Expired
- 1974-09-17 AR AR25562874A patent/AR210247A1/en active
- 1974-09-17 DE DE19742444383 patent/DE2444383C2/en not_active Expired
-
1978
- 1978-12-30 MY MY7800021A patent/MY7800021A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2144919C1 (en) * | 1995-06-27 | 2000-01-27 | Акционерное общество "Химпром" | Method of preparing 3-isopropyl (1h)benz-2,1,3- thiadiazinone-4-dioxide-2,2 |
| CN114163430A (en) * | 2020-09-11 | 2022-03-11 | 东莞市东阳光农药研发有限公司 | Benzothiadiazine derivative and application thereof in agriculture |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7412188A (en) | 1975-03-19 |
| MY7800021A (en) | 1978-12-31 |
| FR2243945A1 (en) | 1975-04-11 |
| IT1048199B (en) | 1980-11-20 |
| JPS5053530A (en) | 1975-05-12 |
| AR210247A1 (en) | 1977-07-15 |
| DE2444383A1 (en) | 1975-03-20 |
| JPS6044281B2 (en) | 1985-10-02 |
| NL184363C (en) | 1989-07-03 |
| DE2444383C2 (en) | 1983-12-08 |
| NL184363B (en) | 1989-02-01 |
| FR2243945B1 (en) | 1978-10-13 |
| HU170554B (en) | 1977-07-28 |
| CA1031339A (en) | 1978-05-16 |
| BE819949A (en) | 1975-03-17 |
| PH11345A (en) | 1977-11-02 |
| BR7407705D0 (en) | 1975-07-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |