CH616653A5 - Herbicidal composition containing aniline derivatives - Google Patents
Herbicidal composition containing aniline derivatives Download PDFInfo
- Publication number
- CH616653A5 CH616653A5 CH375175A CH375175A CH616653A5 CH 616653 A5 CH616653 A5 CH 616653A5 CH 375175 A CH375175 A CH 375175A CH 375175 A CH375175 A CH 375175A CH 616653 A5 CH616653 A5 CH 616653A5
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- fluorine
- chlorine
- wind
- compounds
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title claims description 11
- 239000000203 mixture Substances 0.000 title claims description 8
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 title 1
- 239000000460 chlorine Substances 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 26
- 235000007319 Avena orientalis Nutrition 0.000 claims description 16
- 244000075850 Avena orientalis Species 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 235000007340 Hordeum vulgare Nutrition 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 235000013339 cereals Nutrition 0.000 claims description 7
- 239000004009 herbicide Substances 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 230000000885 phytotoxic effect Effects 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 240000005979 Hordeum vulgare Species 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 241000209140 Triticum Species 0.000 claims 1
- 235000021307 Triticum Nutrition 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 231100000208 phytotoxic Toxicity 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 241000209219 Hordeum Species 0.000 description 8
- -1 sulfuric acid Chemical class 0.000 description 6
- 241000209761 Avena Species 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 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
- 230000035515 penetration Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 230000000052 comparative effect Effects 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
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000004546 suspension concentrate Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- 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 description 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 description 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 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 235000007320 Avena fatua Nutrition 0.000 description 1
- 241000209764 Avena fatua Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241001176357 Imber Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide 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
- 238000006480 benzoylation reaction Methods 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 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
- 239000002917 insecticide Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 239000004563 wettable powder 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 |
|---|---|
| CH616653A5 true CH616653A5 (en) | 1980-04-15 |
Family
ID=10016622
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH375175A CH616653A5 (en) | 1974-03-25 | 1975-03-24 | Herbicidal composition containing aniline derivatives |
Country Status (13)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63172770U (enrdf_load_stackoverflow) * | 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 CH CH375175A patent/CH616653A5/de not_active IP Right Cessation
- 1975-03-24 NL NLAANVRAGE7503464,A patent/NL181163C/xx not_active IP Right Cessation
- 1975-03-24 DE DE2512940A patent/DE2512940C2/de not_active Expired
- 1975-03-24 HU HU75SE00001774A patent/HU172883B/hu not_active IP Right Cessation
- 1975-03-24 IL IL46907A patent/IL46907A/xx unknown
- 1975-03-24 BE BE1006552A patent/BE827046A/xx not_active IP Right Cessation
- 1975-03-24 FR FR7509085A patent/FR2265728B1/fr not_active Expired
- 1975-03-24 DD DD184991A patent/DD117333A5/xx unknown
- 1975-03-24 ES ES435952A patent/ES435952A1/es not_active Expired
- 1975-03-24 JP JP50034586A patent/JPS6124361B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2512940A1 (de) | 1975-10-09 |
| CA1052386A (en) | 1979-04-10 |
| NL181163C (nl) | 1987-07-01 |
| HU172883B (hu) | 1978-12-28 |
| FR2265728B1 (enrdf_load_stackoverflow) | 1977-04-15 |
| JPS6124361B2 (enrdf_load_stackoverflow) | 1986-06-10 |
| FR2265728A1 (enrdf_load_stackoverflow) | 1975-10-24 |
| IT1049376B (it) | 1981-01-20 |
| IL46907A0 (en) | 1975-05-22 |
| GB1498411A (en) | 1978-01-18 |
| JPS50160234A (enrdf_load_stackoverflow) | 1975-12-25 |
| BE827046A (nl) | 1975-09-24 |
| ES435952A1 (es) | 1976-12-16 |
| DD117333A5 (enrdf_load_stackoverflow) | 1976-01-12 |
| AU7943175A (en) | 1976-09-30 |
| IL46907A (en) | 1978-03-10 |
| NL181163B (nl) | 1987-02-02 |
| DE2512940C2 (de) | 1984-04-19 |
| NL7503464A (nl) | 1975-09-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |