CA1142771A - Herbicidal compositions - Google Patents
Herbicidal compositionsInfo
- Publication number
- CA1142771A CA1142771A CA000345307A CA345307A CA1142771A CA 1142771 A CA1142771 A CA 1142771A CA 000345307 A CA000345307 A CA 000345307A CA 345307 A CA345307 A CA 345307A CA 1142771 A CA1142771 A CA 1142771A
- Authority
- CA
- Canada
- Prior art keywords
- weight
- linuron
- phthalic acid
- crystallization
- herbicidal composition
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 36
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 15
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 claims abstract description 57
- 239000005573 Linuron Substances 0.000 claims abstract description 55
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims abstract description 37
- 239000000839 emulsion Substances 0.000 claims abstract description 31
- 229920000180 alkyd Polymers 0.000 claims abstract description 27
- 238000002425 crystallisation Methods 0.000 claims abstract description 22
- 230000008025 crystallization Effects 0.000 claims abstract description 22
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 16
- 239000012141 concentrate Substances 0.000 claims abstract description 13
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 13
- 239000003960 organic solvent Substances 0.000 claims abstract description 13
- 239000005011 phenolic resin Substances 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 150000002148 esters Chemical class 0.000 claims abstract description 11
- 239000004480 active ingredient Substances 0.000 claims abstract description 9
- 239000007788 liquid Substances 0.000 claims abstract description 6
- 150000003022 phthalic acids Chemical class 0.000 claims abstract 3
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims description 20
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 12
- 239000008096 xylene Substances 0.000 claims description 12
- 241000196324 Embryophyta Species 0.000 claims description 10
- 150000002576 ketones Chemical class 0.000 claims description 7
- 239000003849 aromatic solvent Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000013078 crystal Substances 0.000 description 18
- 239000004495 emulsifiable concentrate Substances 0.000 description 17
- 229920000151 polyglycol Polymers 0.000 description 15
- 239000010695 polyglycol Substances 0.000 description 15
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 235000008504 concentrate Nutrition 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 239000004563 wettable powder Substances 0.000 description 11
- 239000004359 castor oil Substances 0.000 description 9
- 235000019438 castor oil Nutrition 0.000 description 9
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 159000000007 calcium salts Chemical class 0.000 description 8
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 6
- 229940055577 oleyl alcohol Drugs 0.000 description 6
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 244000075850 Avena orientalis Species 0.000 description 5
- 241000219198 Brassica Species 0.000 description 5
- 235000003351 Brassica cretica Nutrition 0.000 description 5
- 235000003343 Brassica rupestris Nutrition 0.000 description 5
- 240000006677 Vicia faba Species 0.000 description 5
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 5
- 239000000306 component Substances 0.000 description 5
- 235000010460 mustard Nutrition 0.000 description 5
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 235000007319 Avena orientalis Nutrition 0.000 description 4
- 235000002096 Vicia faba var. equina Nutrition 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- TYDSIOSLHQWFOU-UHFFFAOYSA-N 2-cyclohexylidenecyclohexan-1-one Chemical compound O=C1CCCCC1=C1CCCCC1 TYDSIOSLHQWFOU-UHFFFAOYSA-N 0.000 description 3
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical class CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- IJFPVINAQGWBRJ-UHFFFAOYSA-N Diisooctyl phthalate Chemical compound CC(C)CCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCC(C)C IJFPVINAQGWBRJ-UHFFFAOYSA-N 0.000 description 2
- -1 aliphatic fatty acids Chemical class 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000003801 milling Methods 0.000 description 2
- 238000009740 moulding (composite fabrication) Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 230000004224 protection Effects 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XZOYHFBNQHPJRQ-UHFFFAOYSA-N 7-methyloctanoic acid Chemical compound CC(C)CCCCCC(O)=O XZOYHFBNQHPJRQ-UHFFFAOYSA-N 0.000 description 1
- 235000005781 Avena Nutrition 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241000220485 Fabaceae Species 0.000 description 1
- KEJFAGMNOBNFJR-QMTHXVAHSA-N Isophorene Natural products S=C(NC[C@]1(C)C[C@H](NC(=S)NC)CC(C)(C)C1)NC KEJFAGMNOBNFJR-QMTHXVAHSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000779819 Syncarpia glomulifera Species 0.000 description 1
- 235000010749 Vicia faba Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000006136 alcoholysis reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide 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
- 235000013339 cereals Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 229940036248 turpentine Drugs 0.000 description 1
- 238000005303 weighing Methods 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2905122.7 | 1979-02-10 | ||
| DE19792905122 DE2905122A1 (de) | 1979-02-10 | 1979-02-10 | Herbizide mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1142771A true CA1142771A (en) | 1983-03-15 |
Family
ID=6062647
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000345307A Expired CA1142771A (en) | 1979-02-10 | 1980-02-08 | Herbicidal compositions |
Country Status (8)
| Country | Link |
|---|---|
| AU (1) | AU529280B2 (enrdf_load_stackoverflow) |
| CA (1) | CA1142771A (enrdf_load_stackoverflow) |
| DE (1) | DE2905122A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2448293A1 (enrdf_load_stackoverflow) |
| HU (1) | HU185782B (enrdf_load_stackoverflow) |
| IT (1) | IT1147303B (enrdf_load_stackoverflow) |
| NZ (1) | NZ192834A (enrdf_load_stackoverflow) |
| SU (1) | SU1079159A3 (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20170118979A1 (en) * | 2012-07-12 | 2017-05-04 | Adjuvants Unlimited, LLC | Methods And Compositions For Reducing Or Inhibiting Spray Drift And Driftable Fines |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3203779A1 (de) * | 1982-02-04 | 1983-08-11 | Hoechst Ag, 6230 Frankfurt | Herbizide mittel |
| GB8308749D0 (en) * | 1983-03-30 | 1983-05-11 | Dow Chemical Co | Emulsifiable concentrate formulations of pesticides |
| RU2067831C1 (ru) * | 1987-06-24 | 1996-10-20 | Мицуи Тоацу Кемикалз Инк. | Жидкая пестицидная композиция |
| IL123895A (en) * | 1997-04-14 | 2003-04-10 | Rohm & Haas | Pesticide compositions and method for controlling pests using such compositions |
-
1979
- 1979-02-10 DE DE19792905122 patent/DE2905122A1/de not_active Withdrawn
-
1980
- 1980-02-08 NZ NZ192834A patent/NZ192834A/xx unknown
- 1980-02-08 SU SU802878002A patent/SU1079159A3/ru active
- 1980-02-08 IT IT19820/80A patent/IT1147303B/it active
- 1980-02-08 HU HU80288A patent/HU185782B/hu unknown
- 1980-02-08 AU AU55345/80A patent/AU529280B2/en not_active Ceased
- 1980-02-08 CA CA000345307A patent/CA1142771A/en not_active Expired
- 1980-02-11 FR FR8002933A patent/FR2448293A1/fr active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20170118979A1 (en) * | 2012-07-12 | 2017-05-04 | Adjuvants Unlimited, LLC | Methods And Compositions For Reducing Or Inhibiting Spray Drift And Driftable Fines |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2905122A1 (de) | 1980-08-14 |
| HU185782B (en) | 1985-03-28 |
| FR2448293B1 (enrdf_load_stackoverflow) | 1983-04-01 |
| AU5534580A (en) | 1980-08-14 |
| NZ192834A (en) | 1982-03-09 |
| IT1147303B (it) | 1986-11-19 |
| SU1079159A3 (ru) | 1984-03-07 |
| AU529280B2 (en) | 1983-06-02 |
| IT8019820A0 (it) | 1980-02-08 |
| FR2448293A1 (fr) | 1980-09-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |