GB1056235A - Quaternary ammonium derivatives of benzonitriles and herbicidal compositions containing them - Google Patents
Quaternary ammonium derivatives of benzonitriles and herbicidal compositions containing themInfo
- Publication number
- GB1056235A GB1056235A GB2178364A GB2178364A GB1056235A GB 1056235 A GB1056235 A GB 1056235A GB 2178364 A GB2178364 A GB 2178364A GB 2178364 A GB2178364 A GB 2178364A GB 1056235 A GB1056235 A GB 1056235A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- quaternary ammonium
- different
- formula
- same
- 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
- 125000001453 quaternary ammonium group Chemical group 0.000 title abstract 4
- 150000008359 benzonitriles Chemical class 0.000 title abstract 2
- 230000002363 herbicidal effect Effects 0.000 title abstract 2
- 239000000203 mixture Substances 0.000 title abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 4
- CHZCERSEMVWNHL-UHFFFAOYSA-N 2-hydroxybenzonitrile Chemical compound OC1=CC=CC=C1C#N CHZCERSEMVWNHL-UHFFFAOYSA-N 0.000 abstract 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 239000004480 active ingredient Substances 0.000 abstract 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000003085 diluting agent Substances 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 229910052740 iodine Inorganic materials 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 235000019260 propionic acid Nutrition 0.000 abstract 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 abstract 2
- 239000004094 surface-active agent Substances 0.000 abstract 2
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 abstract 2
- SMYMJHWAQXWPDB-UHFFFAOYSA-N (2,4,5-trichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl SMYMJHWAQXWPDB-UHFFFAOYSA-N 0.000 abstract 1
- 239000003559 2,4,5-trichlorophenoxyacetic acid Substances 0.000 abstract 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 abstract 1
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 abstract 1
- 239000000908 ammonium hydroxide Substances 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 229940006460 bromide ion Drugs 0.000 abstract 1
- 239000004009 herbicide Substances 0.000 abstract 1
- -1 hydroxy benzonitriles Chemical class 0.000 abstract 1
- NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention comprises quaternary ammonium derivatives of benzonitriles of the general formula <FORM:1056235/C2/1> in which X1 and X2 are the same or different and each represents a bromine or iodine atom, and R1, R2, R3 and R4 are the same or different and each represents a methyl or ethyl group. Compounds claimed per se are the tetramethyl-ammonium salts of 3,5-dibromo and 3,5-diiodo - 4 - hydroxybenzonitrile. The compounds may be prepared by reacting a soluble salt of a hydroxybenzonitrile of the general formula <FORM:1056235/C2/2> with a quaternary ammonium salt of formula <FORM:1056235/C2/3> wherein Y represents a suitable anion such as a chloride or bromide ion or by reacting a hydroxy benzonitrile of Formula 2 with a quaternary ammonium hydroxide of the formula <FORM:1056235/C2/4>ALSO:A herbicidal composition comprises as active ingredient at least one quaternary ammonium derivative of benzonitrile of the general formula: <FORM:1056235/A5-A6/1> in which X1 and X2 are the same or different and each represents a bromine or iodine atom and R1R2R3R4 are the same or different and each represents a methyl or ethyl group in association with at least one compatible diluent and/or suitable surface active agent. Many diluents and surface active agents are specified. There may also be included a quaternary ammonium salt of known phenoxy alkanoic acid herbicides, e.g. a -(4-chloro-2-methylphenoxy)propionic acid; a ,a -dichloropropionic butyric acid; 4-chloro-2-methylphenoxy-acetic acid; 2,4-dichlorophenoxyacetic acid; a -(4-chloro-2-methylphenoxy)-propionic acid; a -(2, 4-dichlorophenoxy)propionic acid; 2,4,5-trichlorophenoxyacetic acid; a -(2,4,5-trichlorophenoxy)propionic acid; a ,a -dichloropropionic acid or trichloroacetic acid. Specified active ingredients are the tetramethyl ammonium salts of 3,5-dibromo and 3,5-diiodo-4, hydroxy benzonitriles.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2178364A GB1056235A (en) | 1964-05-26 | 1964-05-26 | Quaternary ammonium derivatives of benzonitriles and herbicidal compositions containing them |
| NL6506449A NL6506449A (en) | 1964-05-26 | 1965-05-20 | |
| BE664317A BE664317A (en) | 1964-05-26 | 1965-05-21 | |
| CH732065A CH434869A (en) | 1964-05-26 | 1965-05-25 | Use of quaternary ammonium salts as herbicides |
| FR18351A FR1434786A (en) | 1964-05-26 | 1965-05-25 | New herbicide products |
| DE1965M0062830 DE1542963A1 (en) | 1964-05-26 | 1965-05-26 | New herbicide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2178364A GB1056235A (en) | 1964-05-26 | 1964-05-26 | Quaternary ammonium derivatives of benzonitriles and herbicidal compositions containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1056235A true GB1056235A (en) | 1967-01-25 |
Family
ID=10168732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2178364A Expired GB1056235A (en) | 1964-05-26 | 1964-05-26 | Quaternary ammonium derivatives of benzonitriles and herbicidal compositions containing them |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE664317A (en) |
| CH (1) | CH434869A (en) |
| DE (1) | DE1542963A1 (en) |
| FR (1) | FR1434786A (en) |
| GB (1) | GB1056235A (en) |
| NL (1) | NL6506449A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010519302A (en) * | 2007-02-26 | 2010-06-03 | ダウ アグロサイエンシィズ エルエルシー | Compounds derived from herbicidal carboxylic acids and tetraalkylammonium hydroxide or (arylalkyl) trialkylammonium hydroxide |
| AU2019253885B2 (en) * | 2007-02-26 | 2021-03-25 | Corteva Agriscience Llc | Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl) trialkylammonium hydroxides |
-
1964
- 1964-05-26 GB GB2178364A patent/GB1056235A/en not_active Expired
-
1965
- 1965-05-20 NL NL6506449A patent/NL6506449A/xx unknown
- 1965-05-21 BE BE664317A patent/BE664317A/xx unknown
- 1965-05-25 CH CH732065A patent/CH434869A/en unknown
- 1965-05-25 FR FR18351A patent/FR1434786A/en not_active Expired
- 1965-05-26 DE DE1965M0062830 patent/DE1542963A1/en active Pending
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010519302A (en) * | 2007-02-26 | 2010-06-03 | ダウ アグロサイエンシィズ エルエルシー | Compounds derived from herbicidal carboxylic acids and tetraalkylammonium hydroxide or (arylalkyl) trialkylammonium hydroxide |
| JP2015044813A (en) * | 2007-02-26 | 2015-03-12 | ダウ アグロサイエンシィズ エルエルシー | Compounds derived from herbicidal carboxylic acids and tetraalkylammonium hydroxide or (arylalkyl) trialkylammonium hydroxide |
| US9167810B2 (en) | 2007-02-26 | 2015-10-27 | Dow Agrosciences Llc | Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl) trialkylammonium hydroxides |
| JP2017002066A (en) * | 2007-02-26 | 2017-01-05 | ダウ アグロサイエンシィズ エルエルシー | Compounds derived from herbicidal carboxylic acids and tetraalkylammonium hydroxide or (arylalkyl) trialkylammonium hydroxide |
| JP2017125012A (en) * | 2007-02-26 | 2017-07-20 | ダウ アグロサイエンシィズ エルエルシー | Compounds derived from herbicidal carboxylic acids and tetraalkylammonium hydroxide or (arylalkyl) trialkylammonium hydroxide |
| US9839217B2 (en) | 2007-02-26 | 2017-12-12 | Dow Agrosciences Llc | Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl)trialkylammonium hydroxides |
| AU2019253885B2 (en) * | 2007-02-26 | 2021-03-25 | Corteva Agriscience Llc | Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl) trialkylammonium hydroxides |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6506449A (en) | 1965-11-29 |
| DE1542963A1 (en) | 1970-05-14 |
| BE664317A (en) | 1965-11-22 |
| FR1434786A (en) | 1966-04-08 |
| CH434869A (en) | 1967-04-30 |
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