GB1337269A - Phosphorus and thiophosphorus acid ester derivatives of substituted hydantoins - Google Patents
Phosphorus and thiophosphorus acid ester derivatives of substituted hydantoinsInfo
- Publication number
- GB1337269A GB1337269A GB5534270A GB5534270A GB1337269A GB 1337269 A GB1337269 A GB 1337269A GB 5534270 A GB5534270 A GB 5534270A GB 5534270 A GB5534270 A GB 5534270A GB 1337269 A GB1337269 A GB 1337269A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- reacting
- compound
- halogen
- hydantoin
- 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
- 150000001469 hydantoins Chemical class 0.000 title abstract 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title 1
- 239000002253 acid Substances 0.000 title 1
- 150000002148 esters Chemical class 0.000 title 1
- 229910052698 phosphorus Inorganic materials 0.000 title 1
- 239000011574 phosphorus Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- 230000000895 acaricidal effect Effects 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 229940053195 antiepileptics hydantoin derivative Drugs 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [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
- 150000001768 cations Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 230000000361 pesticidal effect Effects 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 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 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34
- A01N57/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34 containing heterocyclic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1337269 Hydantoin derivatives ESSO RESEARCH & ENG CO 20 Nov 1970 [5 Jan 1970] 55342/70 Headings C2P and C2C Novel compounds of Formula I where R 1 is C 1-4 alkyl optionally substituted by halogen or alkoxy, C 2-4 alkenyl, C 3-6 cycloalkyl, phenyl or benzyl optionally substituted by one or more halogen atoms, C 2-5 alkylcarbonyl or C 3-6 alkoxycarbonylalkyl, R 2 and R 3 are hydrogen, C 1-4 alkyl or phenyl, or R 2 and R 1 together form a tri- or tetra-methylene bridge, R 4 and R 5 are C 1-4 alkoxy or alkylthio and X is oxygen or sulphur, with the proviso that when R 1 is methyl or alkylcarbonyl, R 4 and R 5 may not both represent simultaneously methoxy or ethoxy, may be prepared by reacting a compound of Formula II with a compound of Formula III where Hal is halogen and M<SP>+n</SP> is an n-valent cation. The starting materials of Formula II may be prepared by reacting a corresponding 1- substituted or 1,5-disubstituted hydantoin with formaldehyde to form a 3-hydroxymethyl hydantoin derivative and reacting this compound with a halogenating agent. The compounds of Formula I have insecticidal and acaricidal properties and may be used as the active ingredients in conventional pesticidal compositions.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80270A | 1970-01-05 | 1970-01-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1337269A true GB1337269A (en) | 1973-11-14 |
Family
ID=21693087
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5534270A Expired GB1337269A (en) | 1970-01-05 | 1970-11-20 | Phosphorus and thiophosphorus acid ester derivatives of substituted hydantoins |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE761209A (en) |
| CA (1) | CA930366A (en) |
| DE (1) | DE2064474A1 (en) |
| FR (1) | FR2090470A5 (en) |
| GB (1) | GB1337269A (en) |
| IL (1) | IL35731A (en) |
| NL (1) | NL7018205A (en) |
| ZA (1) | ZA708041B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001025216A1 (en) * | 1999-10-01 | 2001-04-12 | Basf Aktiengesellschaft | 1-aryl-1,3-dihydro-imidazol-2-(thi)one derivatives, production of said compound and use as a dessicating/defoliating agent for plants |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH573920A5 (en) * | 1972-12-12 | 1976-03-31 | Ciba Geigy Ag | |
| US4260769A (en) * | 1977-04-22 | 1981-04-07 | Interx Research Corporation | 5,5-Diphenylhydantoins |
-
1970
- 1970-11-20 GB GB5534270A patent/GB1337269A/en not_active Expired
- 1970-11-25 CA CA099112A patent/CA930366A/en not_active Expired
- 1970-11-26 IL IL35731A patent/IL35731A/en unknown
- 1970-11-27 ZA ZA708041A patent/ZA708041B/en unknown
- 1970-12-14 NL NL7018205A patent/NL7018205A/xx unknown
- 1970-12-30 DE DE19702064474 patent/DE2064474A1/en active Pending
-
1971
- 1971-01-04 FR FR7100052A patent/FR2090470A5/fr not_active Expired
- 1971-01-04 BE BE761209A patent/BE761209A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001025216A1 (en) * | 1999-10-01 | 2001-04-12 | Basf Aktiengesellschaft | 1-aryl-1,3-dihydro-imidazol-2-(thi)one derivatives, production of said compound and use as a dessicating/defoliating agent for plants |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA708041B (en) | 1971-09-29 |
| BE761209A (en) | 1971-07-05 |
| IL35731A0 (en) | 1971-01-28 |
| DE2064474A1 (en) | 1971-07-15 |
| NL7018205A (en) | 1971-07-07 |
| IL35731A (en) | 1974-05-16 |
| CA930366A (en) | 1973-07-17 |
| FR2090470A5 (en) | 1972-01-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |