GB1561050A - Substituted 2,1,3-benzothiadiazine compounds having herbicidal action - Google Patents
Substituted 2,1,3-benzothiadiazine compounds having herbicidal action Download PDFInfo
- Publication number
- GB1561050A GB1561050A GB49368/76A GB4936876A GB1561050A GB 1561050 A GB1561050 A GB 1561050A GB 49368/76 A GB49368/76 A GB 49368/76A GB 4936876 A GB4936876 A GB 4936876A GB 1561050 A GB1561050 A GB 1561050A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- substituted
- denotes
- benzothiadiazin
- dioxide
- 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
- 230000002363 herbicidal effect Effects 0.000 title claims description 22
- GMCRNNWINPJXJN-UHFFFAOYSA-N 1h-2,1,3-benzothiadiazine Chemical class C1=CC=C2NSN=CC2=C1 GMCRNNWINPJXJN-UHFFFAOYSA-N 0.000 title claims description 4
- -1 2,1,3-benzothiadiazine compound Chemical class 0.000 claims description 121
- 150000001875 compounds Chemical class 0.000 claims description 69
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- 239000001257 hydrogen Substances 0.000 claims description 19
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- 150000002431 hydrogen Chemical class 0.000 claims description 10
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 239000012442 inert solvent Substances 0.000 claims description 9
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- KEWVPTYTRMQFBW-UHFFFAOYSA-N 4-propyl-1H-2,1,3-benzothiadiazine Chemical compound C(CC)C1=NSNC2=C1C=CC=C2 KEWVPTYTRMQFBW-UHFFFAOYSA-N 0.000 claims 1
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- 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- 125000001196 nonadecyl 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])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])[H] 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- QNMLMAVEXUCXRG-UHFFFAOYSA-N oxadiazinane-4,5-dione Chemical group O=C1CONNC1=O QNMLMAVEXUCXRG-UHFFFAOYSA-N 0.000 description 1
- SDRLFDJOSQLRPB-UHFFFAOYSA-N oxadiazine-4,5-dione Chemical group O=C1CON=NC1=O SDRLFDJOSQLRPB-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical group 0.000 description 1
- YDCVQGAUCOROHB-UHFFFAOYSA-N oxadiazolidine-4,5-dione Chemical group O=C1NNOC1=O YDCVQGAUCOROHB-UHFFFAOYSA-N 0.000 description 1
- 150000002917 oxazolidines Chemical group 0.000 description 1
- 125000000913 palmityl 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])C([H])([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
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000002958 pentadecyl 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])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
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- REJGOFYVRVIODZ-UHFFFAOYSA-N phosphanium;chloride Chemical group 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
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical group 0.000 description 1
- 150000004892 pyridazines Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000005299 pyridinones Chemical group 0.000 description 1
- 150000003230 pyrimidines Chemical group 0.000 description 1
- 150000008318 pyrimidones Chemical group 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 group 0.000 description 1
- 150000004040 pyrrolidinones Chemical group 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- 150000003248 quinolines Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000004079 stearyl 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])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])[H] 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical group NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical group [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- OLPRIZQBWZMBAS-UHFFFAOYSA-N thiadiazolidine 1,1-dioxide Chemical group O=S1(=O)CCNN1 OLPRIZQBWZMBAS-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 150000003582 thiophosphoric acids Chemical class 0.000 description 1
- 150000003585 thioureas Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 150000003918 triazines Chemical group 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2553209A DE2553209C2 (de) | 1975-11-27 | 1975-11-27 | 1-Methoxymethyl-3-isopropyl-2,1,3-benzothiadiazin(4)on-2,2-dioxid und diese enthaltende Herbizide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1561050A true GB1561050A (en) | 1980-02-13 |
Family
ID=5962736
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB49368/76A Expired GB1561050A (en) | 1975-11-27 | 1976-11-26 | Substituted 2,1,3-benzothiadiazine compounds having herbicidal action |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4075004A (en, 2012) |
| JP (1) | JPS5268192A (en, 2012) |
| AR (1) | AR223802A1 (en, 2012) |
| AT (1) | AT350837B (en, 2012) |
| AU (1) | AU502268B2 (en, 2012) |
| BE (1) | BE848694A (en, 2012) |
| BR (1) | BR7607937A (en, 2012) |
| CA (1) | CA1074794A (en, 2012) |
| CH (1) | CH625395A5 (en, 2012) |
| DE (1) | DE2553209C2 (en, 2012) |
| DK (1) | DK145496C (en, 2012) |
| FR (1) | FR2332986A1 (en, 2012) |
| GB (1) | GB1561050A (en, 2012) |
| IL (1) | IL50702A (en, 2012) |
| IT (1) | IT1066622B (en, 2012) |
| NL (1) | NL7613158A (en, 2012) |
| NZ (1) | NZ182537A (en, 2012) |
| SE (1) | SE7613038L (en, 2012) |
| SU (1) | SU648047A3 (en, 2012) |
| ZA (1) | ZA766301B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2458343A1 (de) * | 1974-12-10 | 1976-06-16 | Basf Ag | N-n'-disubstituierte 2,1,3-benzothiadiazin(4)on-2.2-dioxide |
| DE2656290A1 (de) * | 1976-12-11 | 1978-06-15 | Basf Ag | Benzothiadiazinverbindungen |
| JPH0239520A (ja) * | 1988-07-29 | 1990-02-08 | Tokyo Electron Ltd | レジスト膜厚の測定方法 |
| DE19814805A1 (de) | 1998-04-02 | 1999-10-07 | Bosch Gmbh Robert | Beschichtungsverfahren eines Wischergummis |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1354761A (fr) * | 1959-09-30 | 1964-03-13 | Geigy Ag J R | Nouveaux 1.1-dioxydes de 3-oxo-1.2.6-thiadiazines et leur préparation |
| DE2105687C2 (de) * | 1971-02-08 | 1981-09-24 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von 3-substituierten 2,1,3-Benzothiadiazin-4-on-2,2-dioxiden |
| CA1031339A (en) * | 1973-09-17 | 1978-05-16 | Lennon H. Mckendry | Substituted 4(3h)-oxobenzo-2,1,3-thiadiazine-2,2-dioxides and their use as herbicides |
| CA1024144A (en) * | 1973-09-17 | 1978-01-10 | The Dow Chemical Company | 4(3h)-oxobenzo-2,1,3-thiadiazine-2,2-dioxides |
| DE2349114C2 (de) * | 1973-09-29 | 1985-11-14 | Basf Ag, 6700 Ludwigshafen | 3-sek.-Butyl-2,1,3-benzothiadiazin-(4)-on-2,2-dioxid |
| DE2355113A1 (de) * | 1973-11-03 | 1975-05-15 | Basf Ag | N,n'-disubstituierte 2,1,3-benzothiadiazin-(4)-on-2,2-dioxide |
| US3920641A (en) * | 1973-11-05 | 1975-11-18 | Dow Chemical Co | 1H-pyrido(2,3-c or 4,3-c) (1,2,6)thiadiazin-4(3H)-one-2,2-dioxides |
| DE2458343A1 (de) * | 1974-12-10 | 1976-06-16 | Basf Ag | N-n'-disubstituierte 2,1,3-benzothiadiazin(4)on-2.2-dioxide |
-
1975
- 1975-11-27 DE DE2553209A patent/DE2553209C2/de not_active Expired
-
1976
- 1976-10-18 US US05/733,524 patent/US4075004A/en not_active Expired - Lifetime
- 1976-10-18 IL IL50702A patent/IL50702A/xx unknown
- 1976-10-20 AU AU18855/76A patent/AU502268B2/en not_active Expired
- 1976-10-22 ZA ZA766301A patent/ZA766301B/xx unknown
- 1976-10-29 CA CA264,746A patent/CA1074794A/en not_active Expired
- 1976-11-02 AR AR265314A patent/AR223802A1/es active
- 1976-11-05 NZ NZ182537A patent/NZ182537A/xx unknown
- 1976-11-22 SE SE7613038A patent/SE7613038L/xx not_active Application Discontinuation
- 1976-11-24 BE BE172651A patent/BE848694A/xx not_active IP Right Cessation
- 1976-11-25 IT IT52348/76A patent/IT1066622B/it active
- 1976-11-25 CH CH1486776A patent/CH625395A5/de not_active IP Right Cessation
- 1976-11-25 SU SU762422654A patent/SU648047A3/ru active
- 1976-11-25 JP JP51140827A patent/JPS5268192A/ja active Granted
- 1976-11-25 NL NL7613158A patent/NL7613158A/xx not_active Application Discontinuation
- 1976-11-26 BR BR7607937A patent/BR7607937A/pt unknown
- 1976-11-26 FR FR7635800A patent/FR2332986A1/fr active Granted
- 1976-11-26 GB GB49368/76A patent/GB1561050A/en not_active Expired
- 1976-11-26 DK DK534976A patent/DK145496C/da not_active IP Right Cessation
- 1976-11-26 AT AT877776A patent/AT350837B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6115072B2 (en, 2012) | 1986-04-22 |
| SE7613038L (sv) | 1977-05-28 |
| FR2332986B1 (en, 2012) | 1980-03-28 |
| BE848694A (fr) | 1977-05-24 |
| NZ182537A (en) | 1978-04-03 |
| AU502268B2 (en) | 1979-07-19 |
| NL7613158A (nl) | 1977-06-01 |
| AR223802A1 (es) | 1981-09-30 |
| CA1074794A (en) | 1980-04-01 |
| ATA877776A (de) | 1978-11-15 |
| DE2553209C2 (de) | 1986-01-02 |
| JPS5268192A (en) | 1977-06-06 |
| CH625395A5 (en, 2012) | 1981-09-30 |
| DE2553209A1 (de) | 1977-06-16 |
| IT1066622B (it) | 1985-03-12 |
| DK145496B (da) | 1982-11-29 |
| AU1885576A (en) | 1978-04-27 |
| FR2332986A1 (fr) | 1977-06-24 |
| AT350837B (de) | 1979-06-25 |
| DK534976A (da) | 1977-05-28 |
| IL50702A (en) | 1979-10-31 |
| DK145496C (da) | 1983-05-09 |
| SU648047A3 (ru) | 1979-02-15 |
| IL50702A0 (en) | 1976-12-31 |
| US4075004A (en) | 1978-02-21 |
| ZA766301B (en) | 1977-10-26 |
| BR7607937A (pt) | 1977-11-08 |
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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 |