CA1052386A - Selective herbicides - Google Patents
Selective herbicidesInfo
- Publication number
- CA1052386A CA1052386A CA221,216A CA221216A CA1052386A CA 1052386 A CA1052386 A CA 1052386A CA 221216 A CA221216 A CA 221216A CA 1052386 A CA1052386 A CA 1052386A
- Authority
- CA
- Canada
- Prior art keywords
- compounds
- chlorine
- fluorine
- aminopropionate
- chloroethyl
- 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
- 239000004009 herbicide Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 235000007320 Avena fatua Nutrition 0.000 claims abstract description 15
- 244000075850 Avena orientalis Species 0.000 claims abstract description 15
- 235000005373 Uvularia sessilifolia Nutrition 0.000 claims abstract description 14
- 239000000460 chlorine Substances 0.000 claims abstract description 12
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 10
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052731 fluorine Chemical group 0.000 claims abstract description 8
- 239000011737 fluorine Chemical group 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 235000013339 cereals Nutrition 0.000 claims abstract description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 2
- QRANPOAGRHSSMN-UHFFFAOYSA-N 2-chloroethyl 2-(N-benzoyl-3,4-dichloroanilino)propanoate Chemical compound C(C1=CC=CC=C1)(=O)N(C(C(=O)OCCCl)C)C1=CC(=C(C=C1)Cl)Cl QRANPOAGRHSSMN-UHFFFAOYSA-N 0.000 claims 1
- FYTQLMHHVHDTRJ-UHFFFAOYSA-N 2-chloroethyl 2-(N-benzoyl-3-chloro-4-fluoroanilino)propanoate Chemical compound C(C1=CC=CC=C1)(=O)N(C(C(=O)OCCCl)C)C1=CC(=C(C=C1)F)Cl FYTQLMHHVHDTRJ-UHFFFAOYSA-N 0.000 claims 1
- UKDPYBMPYKTMND-UHFFFAOYSA-N 2-chloroethyl 2-(N-benzoyl-4-fluoroanilino)propanoate Chemical compound C(C1=CC=CC=C1)(=O)N(C(C(=O)OCCCl)C)C1=CC=C(C=C1)F UKDPYBMPYKTMND-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 10
- 241000209219 Hordeum Species 0.000 description 9
- 235000007340 Hordeum vulgare Nutrition 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 231100000167 toxic agent Toxicity 0.000 description 6
- 239000003440 toxic substance Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- -1 amino-acid ester Chemical class 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000000885 phytotoxic effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000004546 suspension concentrate Substances 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- SUWRMAZHFSUJCB-UHFFFAOYSA-N 2-(3,4-dichloroanilino)propanoic acid Chemical compound OC(=O)C(C)NC1=CC=C(Cl)C(Cl)=C1 SUWRMAZHFSUJCB-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001176357 Imber Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000007798 antifreeze agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000006480 benzoylation reaction Methods 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000008268 mayonnaise Substances 0.000 description 1
- 235000010746 mayonnaise Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB13088/74A GB1498411A (en) | 1974-03-25 | 1974-03-25 | 2-haloalkyl-aminopropionates and their use as selective herbicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1052386A true CA1052386A (en) | 1979-04-10 |
Family
ID=10016622
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA221,216A Expired CA1052386A (en) | 1974-03-25 | 1975-03-04 | Selective herbicides |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS6124361B2 (en, 2012) |
| BE (1) | BE827046A (en, 2012) |
| CA (1) | CA1052386A (en, 2012) |
| CH (1) | CH616653A5 (en, 2012) |
| DD (1) | DD117333A5 (en, 2012) |
| DE (1) | DE2512940C2 (en, 2012) |
| ES (1) | ES435952A1 (en, 2012) |
| FR (1) | FR2265728B1 (en, 2012) |
| GB (1) | GB1498411A (en, 2012) |
| HU (1) | HU172883B (en, 2012) |
| IL (1) | IL46907A (en, 2012) |
| IT (1) | IT1049376B (en, 2012) |
| NL (1) | NL181163C (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63172770U (en, 2012) * | 1987-04-30 | 1988-11-09 |
-
1974
- 1974-03-25 GB GB13088/74A patent/GB1498411A/en not_active Expired
-
1975
- 1975-03-04 CA CA221,216A patent/CA1052386A/en not_active Expired
- 1975-03-21 IT IT21527/75A patent/IT1049376B/it active
- 1975-03-24 IL IL46907A patent/IL46907A/xx unknown
- 1975-03-24 DD DD184991A patent/DD117333A5/xx unknown
- 1975-03-24 BE BE1006552A patent/BE827046A/xx not_active IP Right Cessation
- 1975-03-24 ES ES435952A patent/ES435952A1/es not_active Expired
- 1975-03-24 JP JP50034586A patent/JPS6124361B2/ja not_active Expired
- 1975-03-24 FR FR7509085A patent/FR2265728B1/fr not_active Expired
- 1975-03-24 CH CH375175A patent/CH616653A5/de not_active IP Right Cessation
- 1975-03-24 DE DE2512940A patent/DE2512940C2/de not_active Expired
- 1975-03-24 NL NLAANVRAGE7503464,A patent/NL181163C/xx not_active IP Right Cessation
- 1975-03-24 HU HU75SE00001774A patent/HU172883B/hu not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| HU172883B (hu) | 1978-12-28 |
| DD117333A5 (en, 2012) | 1976-01-12 |
| JPS6124361B2 (en, 2012) | 1986-06-10 |
| DE2512940A1 (de) | 1975-10-09 |
| NL181163C (nl) | 1987-07-01 |
| FR2265728A1 (en, 2012) | 1975-10-24 |
| IL46907A (en) | 1978-03-10 |
| IL46907A0 (en) | 1975-05-22 |
| FR2265728B1 (en, 2012) | 1977-04-15 |
| GB1498411A (en) | 1978-01-18 |
| DE2512940C2 (de) | 1984-04-19 |
| CH616653A5 (en) | 1980-04-15 |
| IT1049376B (it) | 1981-01-20 |
| ES435952A1 (es) | 1976-12-16 |
| AU7943175A (en) | 1976-09-30 |
| NL7503464A (nl) | 1975-09-29 |
| JPS50160234A (en, 2012) | 1975-12-25 |
| BE827046A (nl) | 1975-09-24 |
| NL181163B (nl) | 1987-02-02 |
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