GB904706A - Isourea derivatives - Google Patents
Isourea derivativesInfo
- Publication number
- GB904706A GB904706A GB1853760A GB1853760A GB904706A GB 904706 A GB904706 A GB 904706A GB 1853760 A GB1853760 A GB 1853760A GB 1853760 A GB1853760 A GB 1853760A GB 904706 A GB904706 A GB 904706A
- Authority
- GB
- United Kingdom
- Prior art keywords
- general formula
- methyl
- substituted
- alk
- ring
- 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
- 150000002542 isoureas Chemical class 0.000 title abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 3
- 230000002363 herbicidal effect Effects 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 239000004480 active ingredient Substances 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 229910021529 ammonia Inorganic materials 0.000 abstract 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 150000003335 secondary amines Chemical class 0.000 abstract 2
- ZFULXOGYCDBCHD-UHFFFAOYSA-N (4-chlorophenyl)-methylidyneazanium Chemical compound ClC1=CC=C([N+]#C)C=C1 ZFULXOGYCDBCHD-UHFFFAOYSA-N 0.000 abstract 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 abstract 1
- -1 2-chloro-4-methylphenyl Chemical group 0.000 abstract 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 235000013877 carbamide Nutrition 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 239000004009 herbicide Substances 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
- 150000003949 imides Chemical class 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 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 abstract 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- 229920000151 polyglycol Polymers 0.000 abstract 1
- 239000010695 polyglycol Substances 0.000 abstract 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 239000007858 starting material Substances 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
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
-
- 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
- C07C275/70—Compounds containing any of the groups, e.g. isoureas
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
The invention comprises aromatic oalkyl-or substituted alkyl-isoureas of the general formula <FORM:0904706/IV (b)/1> in which Ar stands for an unsubstituted or substituted phenyl radical, Alk stands for an aliphatic hydrocarbon radical which may be substituted and R and R1, which may be the same or different, are hydrogen atoms or alkyl, aryl or cycloalkyl radicals or R and R1, together with the nitrogen atom, may form a ring, which may be interrupted by hetero atoms, said ring being 5- or 6- membered and processes for the preparation thereof wherein (a) an arylimino-halocarbonic acid amide of the general formula <FORM:0904706/IV (b)/2> in which Ar, R and R1 have the same meanings as above and Hal is halogen atom is reacted with an alkanol (b) an arylimino-halocarbonic acid alkyl ester of the general formula <FORM:0904706/IV (b)/3> in which Ar, Alk and Hal have the meanings given above is reacted with ammonia or a primary or secondary amine or (c) an N-arylurea dihalide of the general formula <FORM:0904706/IV (b)/4> wherein Ar, R, R1 and Hal have the meanings given above is reacted with an alkali metal alcoholate. Representative of specific isoureas of which the preparation is described are those of the given general formula in which Ar is phenyl, 4-chlorophenyl, 4-bromophenyl, 2-chloro-4-methylphenyl and 2, 4-dichlorophenyl, Alk is methyl, ethyl, propyl, R is hydrogen, methyl, ethyl and butyl, R1 is methyl, ethyl, propyl and butyl, or the NRR1 group is hetero-cyclic and is piperidine, morpholine or pyrrolidine residue. The products are used as active ingredients in herbicidal compositions (see Group VI). Arylimino-halocarbonic acid imides for use as starting materials are obtained by reacting aryl-isocyanide-dihalides with ammonia or a primary or secondary amine e.g. p-chlorophenyl isocyanide dichloride with dimethylamine. Urea-dihalides for use in the process are obtained by reacting ureas with phosphorous pentachloride.ALSO:Herbicidal compositions comprise as active ingredient a compound of the general formula <FORM:0904706/VI/1> in which Ar stands for an unsubstituted or substituted phenyl radical, Alk stands for an aliphatic hydrocarbon radical which may be substituted and R and R1, which may be the same or different, are hydrogen atoms or alkyl, aryl or cycloalkyl radicals or R and R1, together with the nitrogen atom, may form a ring, which may be interrupted by hetero atoms, said ring being 5- or 6-membered (see Group IV (b)) and a solid or liquid carrier or diluent. A herbicide is described comprising an aqueous dispersion of a mixture of N-phenyl-N1N1-dimethyl - O - methyl - isourea, dimethyl formamide and nonyl phenol-polyglycol ether.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF28463A DE1211163B (en) | 1959-05-16 | 1959-05-16 | Process for the preparation of arylimino-halocarbon acid amides |
| DEF28608A DE1138039B (en) | 1959-05-16 | 1959-06-04 | Process for the preparation of isourea derivatives |
| DEF29580A DE1219020B (en) | 1959-10-10 | 1959-10-10 | Process for the preparation of isourea derivatives |
| DEF0034480 | 1961-07-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB904706A true GB904706A (en) | 1962-08-29 |
Family
ID=31192177
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1704860A Expired GB888646A (en) | 1959-05-16 | 1960-05-13 | Halo formamidines |
| GB1853760A Expired GB904706A (en) | 1959-05-16 | 1960-05-25 | Isourea derivatives |
| GB2710562A Expired GB963312A (en) | 1959-05-16 | 1962-07-13 | Process for the production of arylimino-halo-carbonic acid amides |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1704860A Expired GB888646A (en) | 1959-05-16 | 1960-05-13 | Halo formamidines |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2710562A Expired GB963312A (en) | 1959-05-16 | 1962-07-13 | Process for the production of arylimino-halo-carbonic acid amides |
Country Status (4)
| Country | Link |
|---|---|
| CH (2) | CH385822A (en) |
| DE (2) | DE1211163B (en) |
| GB (3) | GB888646A (en) |
| NL (2) | NL252298A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3517844A1 (en) | 1984-08-30 | 1986-03-13 | Bayer Ag, 5090 Leverkusen | SULFONYLISO (THIO) UREA DERIVATIVES |
| DE3504453A1 (en) * | 1985-02-09 | 1986-08-14 | Basf Ag, 6700 Ludwigshafen | ISO-UREAS, METHOD FOR THEIR PRODUCTION AND THEIR USE FOR CONTROLLING UNWANTED PLANT GROWTH |
-
0
- NL NL251673D patent/NL251673A/xx unknown
- NL NL252298D patent/NL252298A/xx unknown
-
1959
- 1959-05-16 DE DEF28463A patent/DE1211163B/en active Pending
- 1959-06-04 DE DEF28608A patent/DE1138039B/en active Pending
-
1960
- 1960-05-09 CH CH528760A patent/CH385822A/en unknown
- 1960-05-13 GB GB1704860A patent/GB888646A/en not_active Expired
- 1960-05-24 CH CH600660A patent/CH387612A/en unknown
- 1960-05-25 GB GB1853760A patent/GB904706A/en not_active Expired
-
1962
- 1962-07-13 GB GB2710562A patent/GB963312A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB963312A (en) | 1964-07-08 |
| NL251673A (en) | |
| DE1211163B (en) | 1966-02-24 |
| CH385822A (en) | 1964-12-31 |
| GB888646A (en) | 1962-01-31 |
| CH387612A (en) | 1965-02-15 |
| DE1138039B (en) | 1962-10-18 |
| NL252298A (en) |
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