CS246094B2 - Herbicide - Google Patents
Herbicide Download PDFInfo
- Publication number
- CS246094B2 CS246094B2 CS849999A CS999984A CS246094B2 CS 246094 B2 CS246094 B2 CS 246094B2 CS 849999 A CS849999 A CS 849999A CS 999984 A CS999984 A CS 999984A CS 246094 B2 CS246094 B2 CS 246094B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- bromoxynil
- octanoate
- heptanoate
- mixture
- molar ratio
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 24
- 239000004009 herbicide Substances 0.000 title abstract description 9
- 239000000203 mixture Substances 0.000 claims abstract description 62
- DQKWXTIYGWPGOO-UHFFFAOYSA-N (2,6-dibromo-4-cyanophenyl) octanoate Chemical compound CCCCCCCC(=O)OC1=C(Br)C=C(C#N)C=C1Br DQKWXTIYGWPGOO-UHFFFAOYSA-N 0.000 claims description 60
- BHZWBQPHPLFZSV-UHFFFAOYSA-N (2,6-dibromo-4-cyanophenyl) heptanoate Chemical compound CCCCCCC(=O)OC1=C(Br)C=C(C#N)C=C1Br BHZWBQPHPLFZSV-UHFFFAOYSA-N 0.000 claims description 37
- 239000004480 active ingredient Substances 0.000 claims description 6
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 abstract description 25
- 239000005489 Bromoxynil Substances 0.000 abstract description 20
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 13
- 229930195733 hydrocarbon Natural products 0.000 abstract description 13
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 13
- 239000003921 oil Substances 0.000 abstract description 13
- 241000196324 Embryophyta Species 0.000 abstract description 11
- 150000002148 esters Chemical class 0.000 abstract description 11
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical class CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 abstract description 11
- 238000002844 melting Methods 0.000 abstract description 7
- 230000008018 melting Effects 0.000 abstract description 7
- 239000002253 acid Substances 0.000 abstract description 4
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 abstract description 4
- 238000000034 method Methods 0.000 abstract description 3
- 150000008064 anhydrides Chemical class 0.000 abstract description 2
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 abstract 3
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 29
- 239000002480 mineral oil Substances 0.000 description 25
- 125000003118 aryl group Chemical group 0.000 description 15
- 239000007788 liquid Substances 0.000 description 15
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
- 235000008504 concentrate Nutrition 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 8
- 235000014666 liquid concentrate Nutrition 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 7
- 235000010446 mineral oil Nutrition 0.000 description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 5
- -1 bromoxynil ester Chemical class 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 150000004996 alkyl benzenes Chemical class 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QFMDFTQOJHFVNR-UHFFFAOYSA-N 1-[2,2-dichloro-1-(4-ethylphenyl)ethyl]-4-ethylbenzene Chemical compound C1=CC(CC)=CC=C1C(C(Cl)Cl)C1=CC=C(CC)C=C1 QFMDFTQOJHFVNR-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 239000002178 crystalline material Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical class CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- DAPZDAPTZFJZTO-UHFFFAOYSA-N heptanoyl heptanoate Chemical compound CCCCCCC(=O)OC(=O)CCCCCC DAPZDAPTZFJZTO-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- HVEDSLSAMRVHBR-UHFFFAOYSA-N (2-cyanophenyl) heptanoate Chemical compound CCCCCCC(=O)OC1=CC=CC=C1C#N HVEDSLSAMRVHBR-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- YWFBBSXJAWFZBC-UHFFFAOYSA-N ClC1=CC(=C(OC(C(=O)O)C)C=C1)OC Chemical compound ClC1=CC(=C(OC(C(=O)O)C)C=C1)OC YWFBBSXJAWFZBC-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- KDPAWGWELVVRCH-UHFFFAOYSA-M bromoacetate Chemical compound [O-]C(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-M 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- UCVODTZQZHMTPN-UHFFFAOYSA-N heptanoyl chloride Chemical compound CCCCCCC(Cl)=O UCVODTZQZHMTPN-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000005499 meniscus Effects 0.000 description 1
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
- RAFYDKXYXRZODZ-UHFFFAOYSA-N octanoyl octanoate Chemical compound CCCCCCCC(=O)OC(=O)CCCCCCC RAFYDKXYXRZODZ-UHFFFAOYSA-N 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
- A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (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 |
|---|---|---|---|
| GB838334005A GB8334005D0 (en) | 1983-12-21 | 1983-12-21 | Compositions of matter |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS246094B2 true CS246094B2 (en) | 1986-10-16 |
Family
ID=10553620
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS849999A CS246094B2 (en) | 1983-12-21 | 1984-12-19 | Herbicide |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6255252B1 (de) |
| AT (1) | AT397452B (de) |
| AU (1) | AU580573B2 (de) |
| BE (1) | BE901335A (de) |
| CA (1) | CA1233041A (de) |
| CH (1) | CH660729A5 (de) |
| CS (1) | CS246094B2 (de) |
| DD (1) | DD233066A5 (de) |
| DE (1) | DE3446351C2 (de) |
| FR (1) | FR2556933B1 (de) |
| GB (2) | GB8334005D0 (de) |
| HU (1) | HUT36661A (de) |
| IE (1) | IE57912B1 (de) |
| NL (1) | NL8403807A (de) |
| ZA (1) | ZA849904B (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2591069B1 (fr) * | 1985-12-09 | 1988-03-18 | Produits Ind Cie Fse | Produits herbicides a base d'esters de bromoxynil et/ou d'ioxynil |
| FR2591068B1 (fr) * | 1985-12-09 | 1988-03-18 | Produits Ind Cie Fse | Produits herbicides a base d'esters d'oxynil |
| FR2685996B1 (fr) * | 1992-01-13 | 2002-03-22 | Francais Prod Ind Cfpi | Compositions phytosanitaires comprenant en combinaison un oxynil et au moins une substance liquide a temperature ambiante et procede pour leur mise en óoeuvre. |
| WO2017153221A1 (en) | 2016-03-08 | 2017-09-14 | Bayer Cropscience Aktiengesellschaft | Herbicidal compositions comprising carfentrazone-ethyl and bromoxynil |
| AU2021221815A1 (en) * | 2021-08-25 | 2023-03-16 | Adama Australia Pty Limited | Highly Loaded Bromoxynil Formulations |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1067033A (en) * | 1962-09-24 | 1967-04-26 | May & Baker Ltd | 4-hydroxybenzonitrile derivatives |
| EP0008061B1 (de) * | 1978-08-08 | 1981-07-29 | Ciba-Geigy Ag | Neue halogenierte Phenolester, diese enthaltende antimikrobielle Mittel und deren Verwendung |
| US4332613A (en) * | 1979-12-26 | 1982-06-01 | Union Carbide Corporation | Solutions of bromoxynil and ioxynil |
| EP0064478B1 (de) * | 1981-04-24 | 1985-11-27 | Ciba-Geigy Ag | Herbizide Mittel |
-
1983
- 1983-12-21 GB GB838334005A patent/GB8334005D0/en active Pending
-
1984
- 1984-12-14 NL NL8403807A patent/NL8403807A/nl active Search and Examination
- 1984-12-17 FR FR8419489A patent/FR2556933B1/fr not_active Expired
- 1984-12-19 CA CA000470541A patent/CA1233041A/en not_active Expired
- 1984-12-19 CH CH6040/84A patent/CH660729A5/fr not_active IP Right Cessation
- 1984-12-19 AU AU36905/84A patent/AU580573B2/en not_active Expired
- 1984-12-19 DE DE3446351A patent/DE3446351C2/de not_active Expired - Lifetime
- 1984-12-19 ZA ZA849904A patent/ZA849904B/xx unknown
- 1984-12-19 IE IE3258/84A patent/IE57912B1/en not_active IP Right Cessation
- 1984-12-19 CS CS849999A patent/CS246094B2/cs unknown
- 1984-12-20 GB GB08432203A patent/GB2152376B/en not_active Expired
- 1984-12-20 HU HU844759A patent/HUT36661A/hu unknown
- 1984-12-20 BE BE0/214207A patent/BE901335A/fr not_active IP Right Cessation
- 1984-12-21 DD DD84233066A patent/DD233066A5/de unknown
- 1984-12-21 AT AT0407184A patent/AT397452B/de not_active IP Right Cessation
-
1994
- 1994-04-18 US US08/229,118 patent/US6255252B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CH660729A5 (fr) | 1987-06-15 |
| US6255252B1 (en) | 2001-07-03 |
| BE901335A (fr) | 1985-06-20 |
| AT397452B (de) | 1994-04-25 |
| DD233066A5 (de) | 1986-02-19 |
| AU3690584A (en) | 1985-07-04 |
| FR2556933A1 (fr) | 1985-06-28 |
| IE57912B1 (en) | 1993-05-19 |
| AU580573B2 (en) | 1989-01-19 |
| DE3446351A1 (de) | 1985-07-11 |
| GB8432203D0 (en) | 1985-01-30 |
| IE843258L (en) | 1985-06-21 |
| GB2152376B (en) | 1987-08-19 |
| NL8403807A (nl) | 1985-07-16 |
| GB8334005D0 (en) | 1984-02-01 |
| ATA407184A (de) | 1993-09-15 |
| CA1233041A (en) | 1988-02-23 |
| DE3446351C2 (de) | 1994-07-07 |
| HUT36661A (en) | 1985-10-28 |
| FR2556933B1 (fr) | 1987-09-11 |
| ZA849904B (en) | 1985-08-28 |
| GB2152376A (en) | 1985-08-07 |
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