IL44136A - Haloacetanilides,their manufacture and their use for influencing plant growth - Google Patents
Haloacetanilides,their manufacture and their use for influencing plant growthInfo
- Publication number
- IL44136A IL44136A IL44136A IL4413674A IL44136A IL 44136 A IL44136 A IL 44136A IL 44136 A IL44136 A IL 44136A IL 4413674 A IL4413674 A IL 4413674A IL 44136 A IL44136 A IL 44136A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- methyl
- active substance
- methoxy
- formula
- Prior art date
Links
- 230000008635 plant growth Effects 0.000 title claims 3
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims 14
- 239000013543 active substance Substances 0.000 claims 11
- 239000003795 chemical substances by application Substances 0.000 claims 11
- 238000000034 method Methods 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 239000000460 chlorine Substances 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
- 229920000742 Cotton Polymers 0.000 claims 2
- 241000196324 Embryophyta Species 0.000 claims 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 2
- 239000005977 Ethylene Substances 0.000 claims 2
- 244000068988 Glycine max Species 0.000 claims 2
- 235000010469 Glycine max Nutrition 0.000 claims 2
- 240000004658 Medicago sativa Species 0.000 claims 2
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 claims 2
- 230000001276 controlling effect Effects 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 claims 1
- 244000025254 Cannabis sativa Species 0.000 claims 1
- 241000501458 Cultus Species 0.000 claims 1
- 239000004606 Fillers/Extenders Substances 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 241000219146 Gossypium Species 0.000 claims 1
- 240000005979 Hordeum vulgare Species 0.000 claims 1
- 235000007340 Hordeum vulgare Nutrition 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 240000006394 Sorghum bicolor Species 0.000 claims 1
- 235000011684 Sorghum saccharatum Nutrition 0.000 claims 1
- 235000021536 Sugar beet Nutrition 0.000 claims 1
- 235000021307 Triticum Nutrition 0.000 claims 1
- 244000098338 Triticum aestivum Species 0.000 claims 1
- 240000008042 Zea mays Species 0.000 claims 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims 1
- 229940106681 chloroacetic acid Drugs 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 230000002363 herbicidal effect Effects 0.000 claims 1
- 239000004009 herbicide Substances 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 235000009973 maize Nutrition 0.000 claims 1
- -1 methoxy, ethoxy Chemical group 0.000 claims 1
- 230000001105 regulatory effect Effects 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Claims (17)
1. An agent for influencing plant growth, which contains as active substance a compound of the formula I wherein A represents an unsubs tituted ethylene chain or an ethylene chain which is monosubs tituted or disubstituted by methyl, represents fluorine, chlorine, methoxy, ethoxy, tr ifluoromethy 1, represents hydrogen, methyl, ethyl, iso-propyl, is one of the two possible meta-positions to the amino group. and represents hydrogen, chlorine, methyl, methoxy or trifluoromethy1, and R represents methyl or ethyl, with the proviso that at least one of the two substituents R2 and R^ has a meaning different from hydrogen, if R^ represents methoxy or ethoxy, together with suitable carriers and/ or extenders.
2. An agent according to claim 1, which contains as active substance a compound of the formula la, wherein represents hydrogen, chlorine or methoxy, and represents hydrogen or methyl.
3. An agent according to claim 2, which contains as active substance the compound 2-trifluoromethyl-N- (2 ' -methoxy-ethyl) -N-chloroacetanilide of the formula
4. An agent according to claim 1, which contains as active substance the compound of the formula lb wherein R, and A have the meanings given for the formula I, and R represents chlorine, methoxy or ethoxy, and R^ represents methyl or ethyl.
5. An agent according to claim 4, which contains as active substance the compound 2-methyl-6-methoxy-N- (21 -methoxy ethyl) -N-chloroacetanilide of the formula
6. An agent according to claim 4, which contains as active substance the compound 2-methoxy-5-trifluoromethyl-N- (21 -methoxyethyl) -N-chloroacetanilide .
7. An agent according to claim 4, which contains as active substance the compound 2-chloro-6-methyl-N- (21 -methoxyethyl) -N-chloroacetanilide. ,
8. An agent according to claim 4, which contains as active substance the compound 2-chloro-6-methyl-N- (2 ' -ethoxy-ethyl) -N-chloroacetanilide.
9. An agent according to claim 4, which contains as active substance the compound 2-ethoxy-6-methyl-N- ^'-methoxyethyl) -N-chloroacetanilide .
10. A process for the manufacture of compounds of the formula I wherein R^, Rg, ^ an^ ^ have the meanings given in claim 1, wherein a N-subs tituted aniline of the formula II is reacted with a chloroacetylating agent.
11. A process according to claim 10, wherein the anhydride or a halide of chloroacetic acid is used as chloroacetylating agent.
12. A method for regulating plant growth, which comprises the use of an active substance as claimed in any one of claims 1 to 9.
13. A method comprising the use of an active substance as claimed in any one of claims 1 to 9 as selective herbicide.
14. A method for controlling grass-like and broad-leafed weeds in cultures of soya, cotton, rape, and alfalfa, which comprises applying thereto the compound 2-methyl-6 -methoxy- N- (2 ' -me hoxyeth l) -N-chloroace tanilide .
15. A method for controlling grass Like weeds in cultu res of sorghum, barley, wheat, maize, soya, cotton, sugar beet, and alfalfa, which comprises applying thereto the compound 2-trifluoromethyl-N- (2 ' -methoxyethyl) -N-chloro-acetanilide.
16. The compounds of the formula I as defined in claim 1. I
17. A compound of the formula/as described in any one of cjaims 2 to 9.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH180073A CH579348A5 (en) | 1973-02-08 | 1973-02-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL44136A0 IL44136A0 (en) | 1974-05-16 |
| IL44136A true IL44136A (en) | 1976-12-31 |
Family
ID=4218891
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL44136A IL44136A (en) | 1973-02-08 | 1974-02-04 | Haloacetanilides,their manufacture and their use for influencing plant growth |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS5736881B2 (en) |
| AT (1) | AT335220B (en) |
| BE (1) | BE810763A (en) |
| BG (1) | BG20265A3 (en) |
| BR (1) | BR7400927D0 (en) |
| CA (1) | CA1049558A (en) |
| CH (1) | CH579348A5 (en) |
| CS (1) | CS177162B2 (en) |
| DD (1) | DD111277A5 (en) |
| DE (1) | DE2405479C2 (en) |
| FR (1) | FR2216916B1 (en) |
| GB (1) | GB1455474A (en) |
| HU (1) | HU169034B (en) |
| IL (1) | IL44136A (en) |
| NL (1) | NL7401655A (en) |
| PH (1) | PH10605A (en) |
| PL (1) | PL98124B1 (en) |
| RO (1) | RO72493A (en) |
| SU (1) | SU579847A3 (en) |
| ZA (1) | ZA74817B (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL103793B1 (en) * | 1976-03-19 | 1979-07-31 | Monsanto Co | A WORMHOUSE |
| DE2726253A1 (en) * | 1977-06-10 | 1978-12-21 | Bayer Ag | N-ACYLMETHYL CHLORACETANILIDE, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS HERBICIDES |
| DE2825543A1 (en) * | 1978-06-10 | 1979-12-13 | Bayer Ag | N-SUBSTITUTED HALOGEN ACETANILIDES, METHOD FOR THEIR PRODUCTION AND USE AS HERBICIDES |
| HU177876B (en) * | 1979-04-24 | 1982-01-28 | Nitrokemia Ipartelepek | Process for preparing 2,6-dialkyl-n-/alkoxy-methyl/-chloro-acetanilide derivatives |
| MW1181A1 (en) * | 1980-03-25 | 1983-02-09 | Monsanto Co | Herbicidal 2-haloacetanilides |
| US4731109A (en) * | 1980-03-25 | 1988-03-15 | Monsanto Company | Herbicidal 2-haloacetanilides |
| US4606759A (en) * | 1980-03-25 | 1986-08-19 | Monsanto Company | Herbicidal 2-haloacetanilides |
| US4818273A (en) * | 1983-11-14 | 1989-04-04 | The Dow Chemical Company | Substituted 1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonamides, compositions containing them, and their utility as herbicides |
-
1973
- 1973-02-08 CH CH180073A patent/CH579348A5/xx not_active IP Right Cessation
-
1974
- 1974-01-31 CA CA191,475A patent/CA1049558A/en not_active Expired
- 1974-02-04 IL IL44136A patent/IL44136A/en unknown
- 1974-02-05 DE DE19742405479 patent/DE2405479C2/en not_active Expired
- 1974-02-06 RO RO7477538A patent/RO72493A/en unknown
- 1974-02-06 PH PH15480A patent/PH10605A/en unknown
- 1974-02-06 NL NL7401655A patent/NL7401655A/xx not_active Application Discontinuation
- 1974-02-06 BG BG025713A patent/BG20265A3/en unknown
- 1974-02-06 HU HUCI001443 patent/HU169034B/hu unknown
- 1974-02-06 DD DD17641274A patent/DD111277A5/xx unknown
- 1974-02-07 SU SU7401992654A patent/SU579847A3/en active
- 1974-02-07 PL PL16863674A patent/PL98124B1/en unknown
- 1974-02-07 GB GB564074A patent/GB1455474A/en not_active Expired
- 1974-02-07 ZA ZA00740817A patent/ZA74817B/en unknown
- 1974-02-07 AT AT96374A patent/AT335220B/en not_active IP Right Cessation
- 1974-02-07 FR FR7404083A patent/FR2216916B1/fr not_active Expired
- 1974-02-08 CS CS91074A patent/CS177162B2/cs unknown
- 1974-02-08 BE BE140680A patent/BE810763A/en not_active IP Right Cessation
- 1974-02-08 BR BR92774A patent/BR7400927D0/en unknown
- 1974-02-08 JP JP1616274A patent/JPS5736881B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU6526374A (en) | 1975-08-07 |
| AT335220B (en) | 1977-02-25 |
| ATA96374A (en) | 1976-06-15 |
| PL98124B1 (en) | 1978-04-29 |
| DE2405479C2 (en) | 1982-12-30 |
| CA1049558A (en) | 1979-02-27 |
| ZA74817B (en) | 1975-01-29 |
| FR2216916B1 (en) | 1976-11-26 |
| FR2216916A1 (en) | 1974-09-06 |
| IL44136A0 (en) | 1974-05-16 |
| BE810763A (en) | 1974-08-08 |
| JPS49109531A (en) | 1974-10-18 |
| CS177162B2 (en) | 1977-07-29 |
| BR7400927D0 (en) | 1974-09-10 |
| RO72493A (en) | 1982-08-17 |
| SU579847A3 (en) | 1977-11-05 |
| HU169034B (en) | 1976-09-28 |
| JPS5736881B2 (en) | 1982-08-06 |
| DD111277A5 (en) | 1975-02-12 |
| DE2405479A1 (en) | 1974-08-15 |
| BG20265A3 (en) | 1975-11-05 |
| GB1455474A (en) | 1976-11-10 |
| CH579348A5 (en) | 1976-09-15 |
| PH10605A (en) | 1977-07-15 |
| NL7401655A (en) | 1974-08-12 |
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