GB1018308A - Novel dichlorophenyl-substituted amides,thioamides,imidates and amidines,and herbicidal compositions containing them - Google Patents
Novel dichlorophenyl-substituted amides,thioamides,imidates and amidines,and herbicidal compositions containing themInfo
- Publication number
- GB1018308A GB1018308A GB1211963A GB1211963A GB1018308A GB 1018308 A GB1018308 A GB 1018308A GB 1211963 A GB1211963 A GB 1211963A GB 1211963 A GB1211963 A GB 1211963A GB 1018308 A GB1018308 A GB 1018308A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dichlorophenyl
- alkyl
- csnr1r2
- conr1r2
- alkenyl
- 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
- 150000001408 amides Chemical class 0.000 title abstract 3
- 150000002463 imidates Chemical class 0.000 title abstract 3
- 150000001409 amidines Chemical class 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 title abstract 2
- 150000003556 thioamides Chemical class 0.000 title abstract 2
- 230000002363 herbicidal effect Effects 0.000 title 1
- -1 2,6-dichlorophenyl Chemical group 0.000 abstract 4
- 125000003342 alkenyl group Chemical group 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000003118 aryl group Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 239000002585 base Substances 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- HDTAUMIOSWQZRW-UHFFFAOYSA-N 2,2-dichloro-2-phenylacetonitrile Chemical compound N#CC(Cl)(Cl)C1=CC=CC=C1 HDTAUMIOSWQZRW-UHFFFAOYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- 241000196324 Embryophyta Species 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 239000000428 dust Substances 0.000 abstract 1
- 239000004495 emulsifiable concentrate Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 239000008187 granular material Substances 0.000 abstract 1
- 150000004677 hydrates Chemical class 0.000 abstract 1
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 1
- 239000012433 hydrogen halide Substances 0.000 abstract 1
- 230000020477 pH reduction Effects 0.000 abstract 1
- 239000008188 pellet Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000004563 wettable powder Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds of formula Y-CH2-(CHR)n-Z and hydrohalides and hydrates thereof, wherein n is 0 or 1; when n is O, Y is 2,4- or 2,6-dichlorophenyl and Z is -CONR1R2, -CSNR1R2, -C(=NH)OR3 or -C(=NH)NR3R4, while when n is 1, Y is 2,6-dichlorophenyl and Z is -CONR1R2 or -CSNR1R2, R1 is alkyl, alkenyl, aryl or -CH2CO2H, R2 is H, alkyl, alkenyl or aryl, or R1 and R4 with the N form a heterocyclic ring; R3 and R4 are C1-3 alkyl or R4 may be H, and R is H, phenyl or -CONR3R4. The amides are prepared by reacting the appropriate amine and dichlorophenyl-substituted acid chloride under anyydrous conditions except where R1 is CH2CO2H, when the reaction with amido-acid is conducted in presence of aqueous alkali followed by acidification; an alternative method where R is phenyl and n is 1 is to react an alkali metal derivative of RCH2CONR1R2 with YCH2Cl. The thioamides are prepared by reacting the amides with P2S5 in presence of an inert organic solvent. The imidates are prepared by reacting the dichlorobenzyl cyanide with the alkanol in presence of hydrogen halide under anhydrous conditions and optionally treating the hydrohalide with a base. The amidines are prepared by reacting the imidates with the appropriate amine and optionally treating the hydrohalide with a base.ALSO:A method of eradicating weeds from crop areas comprises applying thereto a compound of formula Y-CH2-(CHR)n-Z (or a hydrohalide or hydrate thereof), n being 0 or 1, when n is 0, Y is 2, 4-or 2, 6-dichlorophenyl and Z is -CONR1R2, -CSNR1R2,-C(=NH)OR3 or-C(=NH)NR3R4, while when n is 1, Y is 2, 6-dichlorophenyl and Z is -CONR1R2 or -CSNR1R2, R1 is alkyl, alkenyl, aryl or -CH2CO2H, R2 is H, alkyl, alkenyl or aryl, or R1 and R2 with the N form a heterocyclic ring; R3 and R4 are C1-3 alkyl or R4 may be H, and R is H, phenyl or -CONR3R4. The compound may be applied as a composition, e.g. a dust, wettable powder, solution in an organic solvent, emulsifiable concentrate, aqueous emulsion or dispersion or one in the form of granules or pellets.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1211963A GB1018308A (en) | 1963-03-27 | 1963-03-27 | Novel dichlorophenyl-substituted amides,thioamides,imidates and amidines,and herbicidal compositions containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1211963A GB1018308A (en) | 1963-03-27 | 1963-03-27 | Novel dichlorophenyl-substituted amides,thioamides,imidates and amidines,and herbicidal compositions containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1018308A true GB1018308A (en) | 1966-01-26 |
Family
ID=9998718
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1211963A Expired GB1018308A (en) | 1963-03-27 | 1963-03-27 | Novel dichlorophenyl-substituted amides,thioamides,imidates and amidines,and herbicidal compositions containing them |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1018308A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USD299080S (en) | 1985-03-28 | 1988-12-27 | Thomas J. Lipton, Inc. | Confection |
| GB2209943A (en) * | 1987-12-14 | 1989-06-01 | Nat Res Dev | Benzene compounds useful for avian control |
| GB2229633A (en) * | 1988-12-14 | 1990-10-03 | Nat Res Dev | Amide rodent repellents |
-
1963
- 1963-03-27 GB GB1211963A patent/GB1018308A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USD299080S (en) | 1985-03-28 | 1988-12-27 | Thomas J. Lipton, Inc. | Confection |
| GB2209943A (en) * | 1987-12-14 | 1989-06-01 | Nat Res Dev | Benzene compounds useful for avian control |
| GB2209943B (en) * | 1987-12-14 | 1991-12-11 | Nat Res Dev | Improvements in or relating to avian control |
| GB2229633A (en) * | 1988-12-14 | 1990-10-03 | Nat Res Dev | Amide rodent repellents |
| GB2229633B (en) * | 1988-12-14 | 1992-08-12 | Nat Res Dev | Improvements in or relating to rodent control |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1039442A (en) | Imino-thiadiazolines and their use as agents for combating pests | |
| EP0001647B1 (en) | Imidazoline derivatives and salts thereof, their synthesis, pesticidal formulations containing the imidazolines, preparation thereof and their use as pesticides | |
| GB869169A (en) | New n-aryl-alkanamides, their preparation and use as herbicides | |
| GB1018308A (en) | Novel dichlorophenyl-substituted amides,thioamides,imidates and amidines,and herbicidal compositions containing them | |
| GB1067032A (en) | 4-hydroxybenzonitrile derivatives | |
| GB1129797A (en) | Phosphorus-containing pyrimidine derivatives and biologically active compositions containing them | |
| GB1019120A (en) | Novel hydrazine compounds and compositions containing them | |
| GB1398201A (en) | N-sulphenylated carbamidoximes a process for their preparation and their fungicidal and bactericidal use | |
| GB1476333A (en) | Urea and hydantoin derivatives and plant-growth regulating compositions | |
| GB947485A (en) | Improvements in or relating to heterocyclic amidophosphate compounds and combating noxious organisms thereby | |
| GB1256530A (en) | ||
| IL43299A (en) | Tetrasubstituted ureas,their preparation and their use as herbicides | |
| GB875828A (en) | Heterocyclic thiophosphoric acid esters and pesticidal compositions containing them | |
| GB947921A (en) | 2-thio-(pyridine-n-oxide)-molybdate complexes and fungicidal compositions containing them | |
| ES320727A1 (en) | Phosphorus carbonyl compounds | |
| CA1149392A (en) | Heterocyclic phenoxyalkanoic acid derivatives | |
| GB972008A (en) | Halogenated methylthiohydantoins | |
| GB887701A (en) | Processes for the preparation of benzo-1:3-thiazinediones-(2:4) | |
| GB1122043A (en) | Anilinoalkylcarboxamides and herbicidal compositions containing them | |
| GB955985A (en) | Chlorinated cyanocarboxylic esters | |
| GB1021014A (en) | Novel herbicidal compounds and compositions | |
| GB1506092A (en) | Diphenyl ether amides and the use thereof as herbicides | |
| GB1008266A (en) | 3-substituted benzoxazine-(1,4)-one-(2) derivatives | |
| GB1104414A (en) | N-formyl ª‡-haloacetanilides and herbicidal compositions containing them | |
| GB924657A (en) | Substituted thiophosphoric esters and insecticidal compositions containing them |