DE2754238A1 - Neue 3-phenyl-tetrahydro-1,3,5-oxadiazin-4-on-derivate, verfahren zu deren herstellung und diese enthaltende herbizide zusammensetzungen - Google Patents
Neue 3-phenyl-tetrahydro-1,3,5-oxadiazin-4-on-derivate, verfahren zu deren herstellung und diese enthaltende herbizide zusammensetzungenInfo
- Publication number
- DE2754238A1 DE2754238A1 DE19772754238 DE2754238A DE2754238A1 DE 2754238 A1 DE2754238 A1 DE 2754238A1 DE 19772754238 DE19772754238 DE 19772754238 DE 2754238 A DE2754238 A DE 2754238A DE 2754238 A1 DE2754238 A1 DE 2754238A1
- Authority
- DE
- Germany
- Prior art keywords
- active material
- tetrahydro
- phenyl
- acid
- oxadiazin
- 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- Withdrawn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
- 238000000034 method Methods 0.000 title claims description 20
- 239000000203 mixture Substances 0.000 title claims description 20
- 230000002363 herbicidal effect Effects 0.000 title claims description 14
- NOJINLLSGYWYMM-UHFFFAOYSA-N 3-phenyl-1,3,5-oxadiazinan-4-one Chemical class O=C1NCOCN1C1=CC=CC=C1 NOJINLLSGYWYMM-UHFFFAOYSA-N 0.000 title claims 2
- 239000004009 herbicide Substances 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- 239000011149 active material Substances 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 25
- 241000196324 Embryophyta Species 0.000 claims description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- 240000008042 Zea mays Species 0.000 claims description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
- -1 N, N'-disubstituted phenylurea Chemical class 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 12
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 10
- 235000013339 cereals Nutrition 0.000 claims description 9
- 229920000742 Cotton Polymers 0.000 claims description 8
- 240000007594 Oryza sativa Species 0.000 claims description 8
- 235000007164 Oryza sativa Nutrition 0.000 claims description 8
- 244000105624 Arachis hypogaea Species 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 235000020232 peanut Nutrition 0.000 claims description 6
- 235000009566 rice Nutrition 0.000 claims description 6
- 235000010777 Arachis hypogaea Nutrition 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
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- 235000018262 Arachis monticola Nutrition 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 4
- ILIKVSYOPGBFMA-UHFFFAOYSA-N 3-(3-chloro-4-propan-2-ylphenyl)-5-methyl-1,3,5-oxadiazinan-4-one Chemical compound C1=C(Cl)C(C(C)C)=CC=C1N1C(=O)N(C)COC1 ILIKVSYOPGBFMA-UHFFFAOYSA-N 0.000 claims description 3
- BPGIYOHXHVPOFG-UHFFFAOYSA-N 3-(3-fluoro-4-propan-2-ylphenyl)-5-methyl-1,3,5-oxadiazinan-4-one Chemical compound C1=C(F)C(C(C)C)=CC=C1N1C(=O)N(C)COC1 BPGIYOHXHVPOFG-UHFFFAOYSA-N 0.000 claims description 3
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- 239000002798 polar solvent Substances 0.000 claims description 3
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- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000003377 acid catalyst Substances 0.000 claims 2
- 125000005489 p-toluenesulfonic acid group Chemical group 0.000 claims 2
- 241000219146 Gossypium Species 0.000 claims 1
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
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- 244000098338 Triticum aestivum Species 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 235000007244 Zea mays Nutrition 0.000 description 3
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- ZHFNUPJVYVQVLI-UHFFFAOYSA-N 2,3-dihydrooxadiazin-4-one Chemical compound O=C1NNOC=C1 ZHFNUPJVYVQVLI-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 244000144786 Chrysanthemum segetum Species 0.000 description 2
- 235000005470 Chrysanthemum segetum Nutrition 0.000 description 2
- 244000152970 Digitaria sanguinalis Species 0.000 description 2
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000192043 Echinochloa Species 0.000 description 2
- 241000287828 Gallus gallus Species 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 241001355178 Setaria faberi Species 0.000 description 2
- 235000002594 Solanum nigrum Nutrition 0.000 description 2
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- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
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- 238000005260 corrosion Methods 0.000 description 2
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- 238000002474 experimental method Methods 0.000 description 2
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- 238000011835 investigation Methods 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
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- 239000012429 reaction media Substances 0.000 description 2
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- WNLWIJRZMFZDNR-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-5-methyl-1,3,5-oxadiazinan-4-one Chemical compound O=C1N(C)COCN1C1=CC=C(Cl)C(Cl)=C1 WNLWIJRZMFZDNR-UHFFFAOYSA-N 0.000 description 1
- GXEGGKVAMCWENR-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-methyl-1,3,5-oxadiazinan-4-one Chemical compound O=C1N(C)COCN1C1=CC=C(Cl)C=C1 GXEGGKVAMCWENR-UHFFFAOYSA-N 0.000 description 1
- 235000006760 Acer pensylvanicum Nutrition 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
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- 240000006122 Chenopodium album Species 0.000 description 1
- 235000009344 Chenopodium album Nutrition 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 235000017896 Digitaria Nutrition 0.000 description 1
- 241001303487 Digitaria <clam> Species 0.000 description 1
- 239000001692 EU approved anti-caking agent Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 240000000047 Gossypium barbadense Species 0.000 description 1
- 235000009429 Gossypium barbadense Nutrition 0.000 description 1
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- 241000209082 Lolium Species 0.000 description 1
- 244000100545 Lolium multiflorum Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
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- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
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- 239000006184 cosolvent Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
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- 239000002270 dispersing agent Substances 0.000 description 1
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- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
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- 239000011368 organic material Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
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- 235000011152 sodium sulphate Nutrition 0.000 description 1
- FGDMJJQHQDFUCP-UHFFFAOYSA-M sodium;2-propan-2-ylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=CC2=C(S([O-])(=O)=O)C(C(C)C)=CC=C21 FGDMJJQHQDFUCP-UHFFFAOYSA-M 0.000 description 1
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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
- A01N43/88—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 six-membered rings with three ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
- C07D273/04—Six-membered rings
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7637543A FR2372815A1 (fr) | 1976-12-06 | 1976-12-06 | Nouveaux derives de la tetrahydro oxadiazine-1,3,5 one-4 et compositions herbicides les contenant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2754238A1 true DE2754238A1 (de) | 1978-06-15 |
Family
ID=9181005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772754238 Withdrawn DE2754238A1 (de) | 1976-12-06 | 1977-12-06 | Neue 3-phenyl-tetrahydro-1,3,5-oxadiazin-4-on-derivate, verfahren zu deren herstellung und diese enthaltende herbizide zusammensetzungen |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4155747A (enExample) |
| JP (1) | JPS5371090A (enExample) |
| AR (1) | AR216929A1 (enExample) |
| AU (1) | AU3118777A (enExample) |
| BE (1) | BE861546A (enExample) |
| BG (1) | BG28553A3 (enExample) |
| BR (1) | BR7708107A (enExample) |
| CA (1) | CA1088532A (enExample) |
| CS (1) | CS196225B2 (enExample) |
| DD (1) | DD136794A5 (enExample) |
| DE (1) | DE2754238A1 (enExample) |
| DK (1) | DK541577A (enExample) |
| EG (1) | EG12860A (enExample) |
| ES (1) | ES464423A1 (enExample) |
| FR (1) | FR2372815A1 (enExample) |
| GB (1) | GB1545715A (enExample) |
| GR (1) | GR61618B (enExample) |
| IE (1) | IE46176B1 (enExample) |
| LU (1) | LU78633A1 (enExample) |
| NL (1) | NL7713439A (enExample) |
| OA (1) | OA05812A (enExample) |
| PL (1) | PL107652B1 (enExample) |
| SE (1) | SE7713849L (enExample) |
| SU (1) | SU659067A3 (enExample) |
| TR (1) | TR19486A (enExample) |
| ZA (1) | ZA777214B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0549645U (ja) * | 1991-11-30 | 1993-06-29 | 須田産業株式会社 | 手提げ付フィルムバッグ |
| TW240163B (en) * | 1992-07-22 | 1995-02-11 | Syngenta Participations Ag | Oxadiazine derivatives |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1450485A (fr) * | 1964-04-30 | 1966-06-24 | Rohm & Haas | Tétrahydro-1. 3. 5-oxa-4-diazinones |
-
1976
- 1976-12-06 FR FR7637543A patent/FR2372815A1/fr active Granted
-
1977
- 1977-11-15 US US05/851,795 patent/US4155747A/en not_active Expired - Lifetime
- 1977-11-24 ES ES464423A patent/ES464423A1/es not_active Expired
- 1977-11-30 OA OA56327A patent/OA05812A/xx unknown
- 1977-12-02 CA CA292,282A patent/CA1088532A/en not_active Expired
- 1977-12-02 AU AU31187/77A patent/AU3118777A/en active Pending
- 1977-12-02 GB GB50408/77A patent/GB1545715A/en not_active Expired
- 1977-12-02 IE IE2447/77A patent/IE46176B1/en unknown
- 1977-12-02 CS CS778042A patent/CS196225B2/cs unknown
- 1977-12-03 EG EG663/77A patent/EG12860A/xx active
- 1977-12-05 NL NL7713439A patent/NL7713439A/xx not_active Application Discontinuation
- 1977-12-05 JP JP14598077A patent/JPS5371090A/ja active Pending
- 1977-12-05 AR AR270241A patent/AR216929A1/es active
- 1977-12-05 BG BG037952A patent/BG28553A3/xx unknown
- 1977-12-05 SU SU772549602A patent/SU659067A3/ru active
- 1977-12-05 ZA ZA00777214A patent/ZA777214B/xx unknown
- 1977-12-05 GR GR54918A patent/GR61618B/el unknown
- 1977-12-05 LU LU78633A patent/LU78633A1/xx unknown
- 1977-12-05 DK DK541577A patent/DK541577A/da unknown
- 1977-12-05 PL PL1977202654A patent/PL107652B1/pl unknown
- 1977-12-06 TR TR19486A patent/TR19486A/xx unknown
- 1977-12-06 DE DE19772754238 patent/DE2754238A1/de not_active Withdrawn
- 1977-12-06 BE BE183203A patent/BE861546A/xx unknown
- 1977-12-06 DD DD77202435A patent/DD136794A5/xx unknown
- 1977-12-06 BR BR7708107A patent/BR7708107A/pt unknown
- 1977-12-06 SE SE7713849A patent/SE7713849L/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NL7713439A (nl) | 1978-06-08 |
| CS196225B2 (en) | 1980-03-31 |
| AU3118777A (en) | 1979-06-07 |
| DK541577A (da) | 1978-06-07 |
| BE861546A (fr) | 1978-06-06 |
| PL202654A1 (pl) | 1978-10-23 |
| GR61618B (en) | 1978-12-04 |
| FR2372815B1 (enExample) | 1979-04-06 |
| JPS5371090A (en) | 1978-06-24 |
| FR2372815A1 (fr) | 1978-06-30 |
| IE46176L (en) | 1978-06-06 |
| ES464423A1 (es) | 1978-08-01 |
| BR7708107A (pt) | 1978-08-08 |
| AR216929A1 (es) | 1980-02-15 |
| US4155747A (en) | 1979-05-22 |
| CA1088532A (en) | 1980-10-28 |
| OA05812A (fr) | 1981-05-31 |
| GB1545715A (en) | 1979-05-16 |
| SE7713849L (sv) | 1978-06-07 |
| SU659067A3 (ru) | 1979-04-25 |
| ZA777214B (en) | 1978-09-27 |
| TR19486A (tr) | 1979-04-17 |
| PL107652B1 (pl) | 1980-02-29 |
| BG28553A3 (bg) | 1980-05-15 |
| EG12860A (en) | 1981-03-31 |
| DD136794A5 (de) | 1979-08-01 |
| IE46176B1 (en) | 1983-03-23 |
| LU78633A1 (fr) | 1979-06-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |