IE32624L - Trifluoromethyl-phenyl-ureas - Google Patents
Trifluoromethyl-phenyl-ureasInfo
- Publication number
- IE32624L IE32624L IE690080A IE8069A IE32624L IE 32624 L IE32624 L IE 32624L IE 690080 A IE690080 A IE 690080A IE 8069 A IE8069 A IE 8069A IE 32624 L IE32624 L IE 32624L
- Authority
- IE
- Ireland
- Prior art keywords
- group
- atom
- substituted
- oxygen
- ureas
- Prior art date
Links
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 3
- -1 Trifluoromethyl - phenyl Chemical group 0.000 abstract 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 3
- 235000013877 carbamide Nutrition 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 239000001301 oxygen Substances 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 125000001424 substituent group Chemical group 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000006193 alkinyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 239000002837 defoliant Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 230000026030 halogenation Effects 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- 230000002363 herbicidal effect Effects 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 150000003585 thioureas Chemical class 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- 150000003672 ureas Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/64—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups singly-bound to oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/43—Y being a hetero atom
- C07C323/44—X or Y being nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/18—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/16—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with acylated ring nitrogen atoms
- C07D203/20—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with acylated ring nitrogen atoms by carbonic acid, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/06—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,260,386. Trifluoromethyl - phenyl - ureas. CIBA-GEIGY A.G. 23 Jan., 1969 [23 Jan., 1968], No. 3873/69. Heading C2C. Trifluoromethylphenyl ureas of the general formula in which X and Y each represents an oxygen or sulphur atom; R 1 represents an alkyl, alkenyl, alkinyl or alkoxy group which may be substituted by a halogen atom, or an alkyl group whose chain contains 1 or 2 oxygen atoms, or a phenyl group which may be substituted by a single -CF 3 group, and/or by one or more substituents, which may be the same or different, selected from halogen atoms, -CH 3 or -OCH 3 groups; R 2 represents a hydrogen atom or a lower alkyl group, or R 1 and R 2 together with the nitrogen atom linked with them form a heterocycle, and R 3 represents a lower aliphatic group whose chain may be interrupted by an oxygen or sulphur atom, or a phenyl group which may be unsubstituted or substituted in at most 3 positions by halogen atoms, lower alkyl, alkoxy, alkylmercapto, cyano and/or trifluoromethyl groups with the proviso that when both X and Y represent an O atom, R 2 represents a hydrogen atom or a C 1 -C 4 alkyl group and R 1 represents a methyl group, R 3 does not represent a substituted or unsubstituted phenyl group may be prepared by reacting an aromatic residue of the general formula with a second reactant B, which together are capable of forming the thioureas or ureas corresponding to the final formula, in which X and R 3 have the above meanings, and one of the substituents A or B represents the grouping -N-CYYR<SP>1</SP>, -N-CY-halogen, -N-CY-NH 2 or -N=C-Y, in which Y represents oxygen or sulphur and R<SP>1</SP> represents any desired residue that contains carbon and is easy to eliminate, and the other substituent represents the basic group -NH, in which the free valencies are linked with hydrogen unless they form part of a primary or secondary, linear or cyclic amine, in each case, if desired, with additional alkylation and/or additional halogenation. Several compounds are claimed per se. The compounds are used as active ingredients in herbicidal compositions and some act as defoliants.
[GB1260386A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH102268A CH493195A (en) | 1968-01-23 | 1968-01-23 | Pesticides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE32624L true IE32624L (en) | 1969-07-23 |
| IE32624B1 IE32624B1 (en) | 1973-10-03 |
Family
ID=4200614
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE80/69A IE32624B1 (en) | 1968-01-23 | 1969-01-21 | Trifluoromethyl-phenyl-ureas and pesticidal preparations containing them |
Country Status (15)
| Country | Link |
|---|---|
| BE (1) | BE727286A (en) |
| BG (1) | BG17267A3 (en) |
| CH (1) | CH493195A (en) |
| CS (1) | CS158236B2 (en) |
| DE (1) | DE1901501C3 (en) |
| DK (1) | DK124443B (en) |
| FR (1) | FR2000570A1 (en) |
| GB (1) | GB1260386A (en) |
| IE (1) | IE32624B1 (en) |
| IL (1) | IL31444A (en) |
| NL (1) | NL159091B (en) |
| RO (1) | RO54785A (en) |
| SE (1) | SE375095B (en) |
| SU (1) | SU404191A3 (en) |
| YU (1) | YU34874B (en) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3222974A1 (en) * | 1982-06-19 | 1983-12-22 | Basf Ag, 6700 Ludwigshafen | NEW 5-PHENOXYBENZISOTHIAZOL-4'-UREA DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS HERBICIDES |
| EP0427963B1 (en) * | 1989-11-10 | 1994-03-30 | Agrolinz Agrarchemikalien Gesellschaft M.B.H. | Process for the preparation of pure asymmetric disubstituted urea |
| DE10029564A1 (en) | 2000-06-22 | 2002-01-03 | Continental Ag | elastomeric bearings |
| CA2744893A1 (en) | 2002-06-27 | 2004-01-08 | Novo Nordisk A/S | Aryl carbonyl derivatives as glucokinase activators |
| BRPI0506662B8 (en) | 2004-01-06 | 2021-05-25 | Novo Nordisk As | glucokinase activating compounds |
| JP2009500378A (en) | 2005-07-08 | 2009-01-08 | ノボ・ノルデイスク・エー／エス | Dicycloalkylcarbamoylureas as glucokinase activators |
| JP4960355B2 (en) | 2005-07-14 | 2012-06-27 | ノボ・ノルデイスク・エー／エス | Urea-type glucokinase activator |
| JP2010515701A (en) | 2007-01-09 | 2010-05-13 | ノボ・ノルデイスク・エー／エス | Urea glucokinase activator |
| AU2008204530B2 (en) | 2007-01-11 | 2013-08-01 | Vtv Therapeutics Llc | Urea glucokinase activators |
| CA3093025A1 (en) | 2018-06-12 | 2019-12-19 | Vtv Therapeutics Llc | Therapeutic uses of glucokinase activators in combination with insulin or insulin analogs |
| US12391658B2 (en) | 2020-02-18 | 2025-08-19 | Vtv Therapeutics Llc | Sulfoxide and sulfone glucokinase activators and methods of use thereof |
| US12479808B2 (en) | 2020-06-08 | 2025-11-25 | Vtv Therapeutics Llc | Salts or co-crystals of {2-[3-cyclohexyl-3-(trans-4-propoxy-cyclohexyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid and uses thereof |
-
1968
- 1968-01-23 CH CH102268A patent/CH493195A/en not_active IP Right Cessation
-
1969
- 1969-01-14 DE DE1901501A patent/DE1901501C3/en not_active Expired
- 1969-01-16 FR FR6900613A patent/FR2000570A1/fr not_active Withdrawn
- 1969-01-19 IL IL31444A patent/IL31444A/en unknown
- 1969-01-21 IE IE80/69A patent/IE32624B1/en unknown
- 1969-01-21 SE SE6900757A patent/SE375095B/xx unknown
- 1969-01-22 DK DK34469AA patent/DK124443B/en unknown
- 1969-01-22 NL NL6901066.A patent/NL159091B/en not_active IP Right Cessation
- 1969-01-22 YU YU154/69A patent/YU34874B/en unknown
- 1969-01-22 BE BE727286D patent/BE727286A/xx unknown
- 1969-01-23 SU SU1300475A patent/SU404191A3/ru active
- 1969-01-23 CS CS45669*#A patent/CS158236B2/cs unknown
- 1969-01-23 GB GB3873/69A patent/GB1260386A/en not_active Expired
- 1969-01-23 BG BG011505A patent/BG17267A3/en unknown
- 1969-01-23 RO RO58846A patent/RO54785A/ro unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1901501B2 (en) | 1977-09-22 |
| NL159091B (en) | 1979-01-15 |
| RO54785A (en) | 1973-05-17 |
| IE32624B1 (en) | 1973-10-03 |
| YU34874B (en) | 1980-04-30 |
| IL31444A0 (en) | 1969-03-27 |
| YU15469A (en) | 1979-10-31 |
| BG17267A3 (en) | 1973-07-25 |
| DE1901501A1 (en) | 1969-08-28 |
| DE1901501C3 (en) | 1978-05-03 |
| NL6901066A (en) | 1969-07-25 |
| GB1260386A (en) | 1972-01-19 |
| CS158236B2 (en) | 1974-10-15 |
| BE727286A (en) | 1969-07-22 |
| DK124443B (en) | 1972-10-23 |
| CH493195A (en) | 1970-07-15 |
| SU404191A3 (en) | 1973-10-26 |
| IL31444A (en) | 1973-03-30 |
| FR2000570A1 (en) | 1969-09-12 |
| SE375095B (en) | 1975-04-07 |
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