US20210195901A1 - Herbicidal composition - Google Patents
Herbicidal composition Download PDFInfo
- Publication number
- US20210195901A1 US20210195901A1 US17/202,997 US202117202997A US2021195901A1 US 20210195901 A1 US20210195901 A1 US 20210195901A1 US 202117202997 A US202117202997 A US 202117202997A US 2021195901 A1 US2021195901 A1 US 2021195901A1
- Authority
- US
- United States
- Prior art keywords
- methyl
- composition according
- ester
- weight
- diethyl
- 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.)
- Pending
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- 239000000203 mixture Substances 0.000 title claims abstract description 51
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 21
- 239000004495 emulsifiable concentrate Substances 0.000 claims abstract description 31
- MGOHCFMYLBAPRN-UHFFFAOYSA-N pinoxaden Chemical compound CCC1=CC(C)=CC(CC)=C1C(C1=O)=C(OC(=O)C(C)(C)C)N2N1CCOCC2 MGOHCFMYLBAPRN-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000003799 water insoluble solvent Substances 0.000 claims abstract description 10
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 8
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 claims description 24
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 24
- 239000004009 herbicide Substances 0.000 claims description 16
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 8
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 8
- COYBRKAVBMYYSF-UHFFFAOYSA-N heptan-2-yl [(5-chloroquinolin-8-yl)oxy]acetate Chemical group C1=CN=C2C(OCC(=O)OC(C)CCCCC)=CC=C(Cl)C2=C1 COYBRKAVBMYYSF-UHFFFAOYSA-N 0.000 claims description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 5
- 239000000194 fatty acid Substances 0.000 claims description 5
- -1 fatty alcohol acetate Chemical class 0.000 claims description 5
- 150000004702 methyl esters Chemical class 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
- 125000005907 alkyl ester group Chemical group 0.000 claims description 4
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- 238000000034 method Methods 0.000 claims description 3
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- HCNBYBFTNHEQQJ-UHFFFAOYSA-N 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-6-(trifluoromethyl)pyridine-3-carboxylic acid Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=C(N=2)C(F)(F)F)C(O)=O)=N1 HCNBYBFTNHEQQJ-UHFFFAOYSA-N 0.000 claims description 2
- UWHURBUBIHUHSU-UHFFFAOYSA-N 2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]benzoic acid Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 UWHURBUBIHUHSU-UHFFFAOYSA-N 0.000 claims description 2
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- 239000005502 Cyhalofop-butyl Substances 0.000 claims description 2
- TYIYMOAHACZAMQ-CQSZACIVSA-N Cyhalofop-butyl Chemical group C1=CC(O[C@H](C)C(=O)OCCCC)=CC=C1OC1=CC=C(C#N)C=C1F TYIYMOAHACZAMQ-CQSZACIVSA-N 0.000 claims description 2
- 239000005504 Dicamba Substances 0.000 claims description 2
- 239000005505 Dichlorprop-P Substances 0.000 claims description 2
- 239000005507 Diflufenican Substances 0.000 claims description 2
- 239000005529 Florasulam Substances 0.000 claims description 2
- QZXATCCPQKOEIH-UHFFFAOYSA-N Florasulam Chemical compound N=1N2C(OC)=NC=C(F)C2=NC=1S(=O)(=O)NC1=C(F)C=CC=C1F QZXATCCPQKOEIH-UHFFFAOYSA-N 0.000 claims description 2
- RXCPQSJAVKGONC-UHFFFAOYSA-N Flumetsulam Chemical compound N1=C2N=C(C)C=CN2N=C1S(=O)(=O)NC1=C(F)C=CC=C1F RXCPQSJAVKGONC-UHFFFAOYSA-N 0.000 claims description 2
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- QBEXFUOWUYCXNI-UHFFFAOYSA-N Ioxynil octanoate Chemical compound CCCCCCCC(=O)OC1=C(I)C=C(C#N)C=C1I QBEXFUOWUYCXNI-UHFFFAOYSA-N 0.000 claims description 2
- KGEKLUUHTZCSIP-UHFFFAOYSA-N Isobornyl acetate Natural products C1CC2(C)C(OC(=O)C)CC1C2(C)C KGEKLUUHTZCSIP-UHFFFAOYSA-N 0.000 claims description 2
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- VGHPMIFEKOFHHQ-UHFFFAOYSA-N Metosulam Chemical compound N1=C2N=C(OC)C=C(OC)N2N=C1S(=O)(=O)NC1=C(Cl)C=CC(C)=C1Cl VGHPMIFEKOFHHQ-UHFFFAOYSA-N 0.000 claims description 2
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- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
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- 235000019438 castor oil Nutrition 0.000 description 2
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 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 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- 244000045561 useful plants Species 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CTTJWXVQRJUJQW-UHFFFAOYSA-N 2,2-dioctyl-3-sulfobutanedioic acid Chemical compound CCCCCCCCC(C(O)=O)(C(C(O)=O)S(O)(=O)=O)CCCCCCCC CTTJWXVQRJUJQW-UHFFFAOYSA-N 0.000 description 1
- 241000743985 Alopecurus Species 0.000 description 1
- 241001621841 Alopecurus myosuroides Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N Lactic Acid Natural products CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- 235000007238 Secale cereale Nutrition 0.000 description 1
- 244000082988 Secale cereale Species 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- CURLHBZYTFVCRG-UHFFFAOYSA-N butan-2-yl n-(3-chlorophenyl)carbamate Chemical compound CCC(C)OC(=O)NC1=CC=CC(Cl)=C1 CURLHBZYTFVCRG-UHFFFAOYSA-N 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
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 229960000878 docusate sodium Drugs 0.000 description 1
- 229940052296 esters of benzoic acid for local anesthesia Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 229940013317 fish oils Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 235000021281 monounsaturated fatty acids Nutrition 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000010499 rapseed oil Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- PZTAGFCBNDBBFZ-UHFFFAOYSA-N tert-butyl 2-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1CO PZTAGFCBNDBBFZ-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- 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
- 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
- A01N25/22—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 ingredients stabilising the active ingredients
Definitions
- the present invention relates to a herbicidal composition in the form of an emulsifiable concentrate which comprises 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester as herbicidally active compound, and to the use of such a composition in controlling weeds in crops of useful plants.
- 2,2-Dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester exhibits herbicidal action against weeds in cereals, especially against grasses in wheat, barley and rye crops.
- the compound is also known by the name pinoxaden and is described, for example, in EP-A-1 062 217.
- Emulsifiable concentrates of 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester are known from Example F1. of EP-A-1 062 217. It has been found, however, that those ECs do not have adequate stability and over the course of time the herbicide is decomposed or modified, for example by hydrolysis or transesterification reactions.
- the problem of the present invention is now to provide emulsifiable concentrates of 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester that are distinguished by improved storage stability.
- the present invention accordingly relates to a herbicidal composition in the form of an emulsifiable concentrate which comprises, in addition to emulsifiers and water-insoluble solvents,
- the alcohol is a C 1 -C 12 alkanol, propylene glycol, dipropylene glycol, 2-methyl-2,4-pentanediol, furfuryl alcohol, tetrahydrofurfuryl alcohol, benzyl alcohol, 4-hydroxy-4-methyl-2-pentanone, cyclopentanol, cyclohexanol, ethyl lactate or butyl lactate.
- the alcohols that come into consideration are preferably C 1 -C 12 alkanols such as methanol, ethanol, propanol, hexanol, octanol and dodecanol.
- the alcohols may be straight-chain or branched, for example 2-ethylhexanol; may be present in the form of diols or triols, specifically propylene glycol, dipropylene glycol or 2-methyl-2,4-pentanediol; and they may also be substituted, specifically furfuryl or tetrahydrofurfuryl alcohol, benzyl alcohol, or 4-hydroxy-4-methyl-2-pentanone; and may be present in the form of lactic acid alkyl esters, specifically ethyl lactate and butyl lactate.
- Cyclic alcohols, specifically cyclopentanol or cyclohexanol can likewise be used according to the invention.
- Preferred alcohols that may be mentioned are 2-ethylhexanol, n-octanol, benzyl alcohol, tetrahydrofurfuryl alcohol, 2-methyl-2,4-pentanediol, 4-hydroxy-4-methyl-2-pentanone and cyclohexanol as well as ethyl lactate and butyl lactate.
- Those alcohols can also be mixed with one another or used in admixture with customary water-insoluble solvents.
- water-insoluble solvents are aromatic hydrocarbons, such as toluene, xylene, cumene, mixtures of aromatic hydrocarbons having a boiling point of from 160 to 180° C. (Solvesso 100) or from 180 to 210° C. (Solvesso 150) or from 230 to 290° C.
- compositions according to the invention it is possible to use the emulsifiers customarily used in connection with ECs.
- emulsifiers customarily used in connection with ECs.
- examples that may be mentioned are castor oil ethoxylates, alcohol ethoxylates, tristyryl phenol ethoxylates, mixtures thereof and also mixtures with anionic surface-active compounds such as the calcium salt of dodecylbenzenesulfonic acid or the sodium salt of dioctylsulfosuccinic acid.
- emulsifier Preferably from 0.5 to 50% by weight of emulsifier are present in the emulsifiable concentrates according to the invention.
- compositions according to the invention may comprise, in addition to 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d]-[1,4,5]oxadiazepin-7-yl ester, one or more further herbicides that are compatible therewith.
- “Compatible” means in this context that the herbicide combination is chemically stable and exhibits neither antagonism nor increased phytotoxicity in respect of the useful plants.
- Such herbicides are preferably selected from the groups of the sulfonylureas, for example triasulfuron, tribenuron, metsulfuron, thifensulfuron, flupyrsulfuron, chlorsulfuron, prosulfuron, amidosulfuron, mesosulfuron, sulfosulfuron and tritosulfuron, aryloxyphenoxypropionates and heteroaryloxyphenoxypropionates such as clodinafop-propargyl, fenoxaprop-P-ethyl, diclofop-methyl and cyhalofop-butyl, triazolopyrimidines such as florasulam, metosulam and flumetsulam, arylcarboxylic acids, preferably dicamba and clopyralid, also aryloxycarboxylic acids, preferably esters of 2,4-D, 2,4-DP, mecoprop, meco
- herbicide 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester (alone or in admixture with one or more further herbicides) are present in the emulsifiable concentrates according to the invention.
- compositions according to the invention allow the simultaneous use of safeners, preference being given to cloquintocet-mexyl, mefenpyr-diethyl or isoxadifen-ethyl and derivatives thereof, such as the corresponding acid and salts.
- safeners are described, for example, in The Pesticide Manual, 12th Edition, BCPC, and in DE-A-43 31 448.
- Adjuvants may also be added to the compositions according to the invention, with the result that their activity can be increased.
- adjuvants can be, for example: non-ionic surfactants, mixtures of non-ionic surfactants, mixtures of anionic surfactants with non-ionic surfactants, organosilicon surfactants, mineral oil derivatives with and without surfactants, vegetable oil derivatives with and without added surfactant, fish oils and other oils of animal nature and alkyl derivatives thereof with and without surfactants, naturally occurring higher saturated and mono- or poly-unsaturated fatty acids, preferably having from 8 to 28 carbon atoms, and alkyl ester derivatives thereof, organic acids containing an aromatic ring system and one or more carboxylic acid radicals, as well as alkyl derivatives thereof. Mixtures of individual adjuvants with one another and in combination with organic solvents can result in a further enhancement of action.
- Adjuvants suitable for the present invention are described in EP-A-1 062 217.
- the preparation of the ECs according to the invention is carried out substantially in accordance with the known customary method of dissolving the herbicide in the alcohol and optionally in the water-insoluble solvent and then adding a customary emulsifier. The mixture so obtained is stirred until a clear solution has been formed.
- An emulsifiable concentrate of 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester is prepared by dissolving 10.5 g of that herbicide and 2.7 g of the safener cloquintocet-mexyl in a mixture of 1 g of Soprophor TS/10 (ethoxylated tristyryl phenol with 10 mol of ethylene oxide), 1 g of Atlas G-5000 (butanol EO/PO block copolymer), 1 g of Rhodacal 60/BE (calcium salt of dodecylbenzenesulfonic acid) and 86.7 g of Solvesso 200 ND (aromatic hydrocarbons). That corresponds substantially to the ECs according to Examples F1. a) and b) of EP-A-1 062
- An emulsifiable concentrate is prepared in the same way as EC 1 but instead of 86.7 g of Solvesso 200 ND there are used only 56.7 g and additionally 30.0 g of cyclohexanone. That corresponds substantially to the ECs according to Examples F1. c) and d) of EP-A-1 062 217.
- An emulsifiable concentrate is prepared in the same way as EC 1 but instead of 86.7 g of Solvesso 200 ND there are used only 56.7 g and additionally 30.0 g of tetrahydrofurfuryl alcohol. That corresponds to an EC according to the present invention.
- An emulsifiable concentrate containing 107 g of 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester and 26 g of cloquintocet-mexyl is prepared by dissolving those compounds in a mixture of 10 g of Soprophor TS/10 (ethoxylated tristyryl phenol with 10 mol of ethylene oxide), 10 g of Atlas G-5000 (butanol EO/PO block copolymer), 10 g of Rhodacal 60/BE (calcium salt of dodecylbenzenesulfonic acid), 524 g of Solvesso 200 ND (aromatic hydrocarbons) and 300 g of 2-methyl-2,4-pentanediol and stirring until a clear solution is obtained.
- the concentrate so prepared is stored for 4 weeks at a temperature of 50° C., after which only a 2% loss of 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester is observed.
- An emulsifiable concentrate is prepared as in Example 2 except that 300 g of diacetone alcohol are used instead of the 2-methyl-2,4-pentanediol.
- the concentrate so obtained is stored for 4 weeks at a temperature of 50° C., after which only a 2% loss of 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo-[1,2-d][1,4,5]oxadiazepin-7-yl ester is observed.
- An emulsifiable concentrate containing 129 g of 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester and 31 g of cloquintocet-mexyl is prepared by dissolving those compounds in a mixture of 10 g of Soprophor TS/10 (ethoxylated tristyryl phenol with 10 mol of ethylene oxide), 50 g of Atlas MBA 1307 (mono-branched fatty alcohol alkoxylate), 1320 g of Solvesso 200 ND (aromatic hydrocarbons) and 500 g of tetrahydrofurfuryl alcohol and stirring until a clear solution is obtained.
- Soprophor TS/10 ethoxylated tristyryl phenol with 10 mol of ethylene oxide
- Atlas MBA 1307 mono-branched
- the concentrate so prepared is stored for 4 weeks at a temperature of 50° C., after which only a 2% loss of 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester is observed.
- An emulsifiable concentrate containing 54 g of 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester and 13 g of cloquintocet-mexyl is prepared by dissolving those compounds in a mixture of 10 g of Soprophor TS/10 (ethoxylated tristyryl phenol with 10 mol of ethylene oxide), 10 g of Atlas G-5000 (butanol EO/PO block copolymer), 10 g of Rhodacal 60/BE (calcium salt of dodecylbenzenesulfonic acid), 158 g of Solvesso 200 ND (aromatic hydrocarbons), 450 g of rape oil methyl ester and 250 g of tetrahydrofurfuryl alcohol and stirring until a
- the concentrate so prepared is stored for 4 weeks at a temperature of 50° C., after which only a 3% loss of 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester is observed.
- An emulsifiable concentrate containing 60 g of 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester and 15 g of cloquintocet-mexyl is prepared by dissolving those compounds in a mixture of 20 g of NANSA EVM63/B (calcium dodecylbenzenesulfonate), 50 g of SERVIROX OEG 59 E (ethoxylated castor oil), 675 g of Solvesso 200 ND (aromatic hydrocarbon) and 200 g of benzyl alcohol and stirring until a clear solution is obtained.
- NANSA EVM63/B calcium dodecylbenzenesulfonate
- SERVIROX OEG 59 E ethoxylated castor oil
- the concentrate so prepared is stored for 4 weeks at a temperature of 50° C., after which only a 3% loss of 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d]-[1,4,5]oxadiazepin-7-yl ester is observed.
- 2,2-Dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester is generally applied to the plant or to the locus thereof at rates of application of from 5 to 200 g/ha, especially from 10 to 80 g/ha, more especially from 30 to 60 g/ha.
- the rates of application of safener are generally from 2 to 100 g/ha, preferably from 2 to 50 g/ha, especially from 7.5 to 15 g/ha.
- the concentration required to achieve the desired effect can be determined by experiment. It is dependent upon the nature of the action, the stage of development of the cultivated plant and of the weed and on the application (place, time, method) and may vary within wide limits as a function of those parameters.
- the rate of application of safener relative to herbicide is largely dependent upon the mode of application. Where a field treatment is carried out either by using a tank mixture with a combination of safener and herbicide or by separate application of safener and herbicide, the ratio of herbicide to safener will usually be from 1:1 to 10:1, preferably 4:1.
- Example B1 Herbicidal Action after Emergence of the Plants (Post-Emergence Action)
- Monocotyledonous and dicotyledonous weeds are raised under greenhouse conditions in standard soil in plastics pots.
- Application of the emulsifiable concentrate is effected at the 3- to 6-leaf stage of the test plants.
- the above-mentioned EC 3 is dissolved in 400 litres of water/ha.
- the results are given in Table 2 below:
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- Pest Control & Pesticides (AREA)
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Abstract
A herbicidal composition in the form of an emulsifiable concentrate which comprises, in addition to emulsifiers and water-insoluble solvents, 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester and an alcohol.
Description
- This application is a continuation of U.S. application Ser. No. 12/159,138, which is a 371 National Stage application, filed Jun. 25, 2008, of International Application No. PCT/EP2006/012539 filed Dec. 27, 2006, which claims priority to CH 2075/05 filed Dec. 27, 2005, the entire contents of these applications are hereby incorporated by reference.
- The present invention relates to a herbicidal composition in the form of an emulsifiable concentrate which comprises 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester as herbicidally active compound, and to the use of such a composition in controlling weeds in crops of useful plants.
- 2,2-Dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester exhibits herbicidal action against weeds in cereals, especially against grasses in wheat, barley and rye crops. The compound is also known by the name pinoxaden and is described, for example, in EP-A-1 062 217.
- Emulsifiable concentrates (ECs) of 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester are known from Example F1. of EP-A-1 062 217. It has been found, however, that those ECs do not have adequate stability and over the course of time the herbicide is decomposed or modified, for example by hydrolysis or transesterification reactions.
- The problem of the present invention is now to provide emulsifiable concentrates of 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester that are distinguished by improved storage stability.
- It has been found, surprisingly, that the problem can be solved by adding an alcohol as solvent to the ECs known from Example F1. of EP-A-1 062 217 or by replacing the ketone which may be present therein by the alcohol.
- The present invention accordingly relates to a herbicidal composition in the form of an emulsifiable concentrate which comprises, in addition to emulsifiers and water-insoluble solvents,
- a) 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester and
- b) an alcohol;
- wherein the alcohol is a C1-C12alkanol, propylene glycol, dipropylene glycol, 2-methyl-2,4-pentanediol, furfuryl alcohol, tetrahydrofurfuryl alcohol, benzyl alcohol, 4-hydroxy-4-methyl-2-pentanone, cyclopentanol, cyclohexanol, ethyl lactate or butyl lactate.
- The presence of the alcohol in the composition according to the invention surprisingly results in a marked stabilisation of the EC. Contrary to expectation, no transesterification reactions of the herbicide are observed.
- In the invention, the alcohols that come into consideration are preferably C1-C12alkanols such as methanol, ethanol, propanol, hexanol, octanol and dodecanol. The alcohols may be straight-chain or branched, for example 2-ethylhexanol; may be present in the form of diols or triols, specifically propylene glycol, dipropylene glycol or 2-methyl-2,4-pentanediol; and they may also be substituted, specifically furfuryl or tetrahydrofurfuryl alcohol, benzyl alcohol, or 4-hydroxy-4-methyl-2-pentanone; and may be present in the form of lactic acid alkyl esters, specifically ethyl lactate and butyl lactate. Cyclic alcohols, specifically cyclopentanol or cyclohexanol, can likewise be used according to the invention.
- Preferred alcohols that may be mentioned are 2-ethylhexanol, n-octanol, benzyl alcohol, tetrahydrofurfuryl alcohol, 2-methyl-2,4-pentanediol, 4-hydroxy-4-methyl-2-pentanone and cyclohexanol as well as ethyl lactate and butyl lactate.
- Special preference is given to tetrahydrofurfuryl alcohol, benzyl alcohol and 2-methyl-2,4-pentanediol.
- Preferably from 1 to 97% by weight of alcohol are present in the emulsifiable concentrates according to the invention. A content of from 5 to 50% by weight, especially from 10 to 30% by weight, is especially preferred.
- Those alcohols can also be mixed with one another or used in admixture with customary water-insoluble solvents. Examples of such water-insoluble solvents are aromatic hydrocarbons, such as toluene, xylene, cumene, mixtures of aromatic hydrocarbons having a boiling point of from 160 to 180° C. (Solvesso 100) or from 180 to 210° C. (Solvesso 150) or from 230 to 290° C. (Solvesso 200), aliphatic or cycloaliphatic hydrocarbons (Exxsol D80, Exxsol D100, Exxsol D120, Isobar H and Isobar V), fatty alcohol acetates (Exxate 700, Exxate 1000), isobornyl acetate, benzyl acetate, lower alkyl esters of dicarboxylic acids such as maleic, fumaric, succinic, glutaric and adipic acid (Solvent DBE), esters of benzoic acid such as benzyl benzoate, methyl benzoate and dipropylene glycol dibenzoate, as well as lower alkyl esters of higher fatty acids such as C8-C10fatty acid methyl esters and C16-C18fatty acid methyl esters, and ketones such as cyclohexanone, acetophenone, methyl-n-pentyl ketone.
- Preferably from 0 to 95% by weight of water-insoluble solvent are present in the emulsifiable concentrates according to the invention. A content of from 10 to 70% by weight, especially from 30 to 60% by weight, is especially preferred.
- For the compositions according to the invention it is possible to use the emulsifiers customarily used in connection with ECs. Examples that may be mentioned are castor oil ethoxylates, alcohol ethoxylates, tristyryl phenol ethoxylates, mixtures thereof and also mixtures with anionic surface-active compounds such as the calcium salt of dodecylbenzenesulfonic acid or the sodium salt of dioctylsulfosuccinic acid.
- Preferably from 0.5 to 50% by weight of emulsifier are present in the emulsifiable concentrates according to the invention. A content of from 2 to 30% by weight, especially from 2 to 10% by weight, is especially preferred.
- The compositions according to the invention may comprise, in addition to 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d]-[1,4,5]oxadiazepin-7-yl ester, one or more further herbicides that are compatible therewith. “Compatible” means in this context that the herbicide combination is chemically stable and exhibits neither antagonism nor increased phytotoxicity in respect of the useful plants. Such herbicides are preferably selected from the groups of the sulfonylureas, for example triasulfuron, tribenuron, metsulfuron, thifensulfuron, flupyrsulfuron, chlorsulfuron, prosulfuron, amidosulfuron, mesosulfuron, sulfosulfuron and tritosulfuron, aryloxyphenoxypropionates and heteroaryloxyphenoxypropionates such as clodinafop-propargyl, fenoxaprop-P-ethyl, diclofop-methyl and cyhalofop-butyl, triazolopyrimidines such as florasulam, metosulam and flumetsulam, arylcarboxylic acids, preferably dicamba and clopyralid, also aryloxycarboxylic acids, preferably esters of 2,4-D, 2,4-DP, mecoprop, mecoprop-P, MCPA, MCPB, dichlorprop-P and fluroxypyr, cyclohexanedione oximes such as tralkoxydim, thiocarbamates such as triallate and prosulfocarb, hydroxybenzonitriles such as bromoxynil, bromoxynil octanoate, ioxynil and ioxynil octanoate, dinitroanilines such as pendimethalin and trifluralin, and also pyridinecarboxamides such as diflufenican.
- Preferably from 1 to 50% by weight of herbicide (2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester (alone or in admixture with one or more further herbicides) are present in the emulsifiable concentrates according to the invention. A content of from 3 to 30% by weight, especially from 5 to 15% by weight, is especially preferred.
- The compositions according to the invention allow the simultaneous use of safeners, preference being given to cloquintocet-mexyl, mefenpyr-diethyl or isoxadifen-ethyl and derivatives thereof, such as the corresponding acid and salts. Such safeners are described, for example, in The Pesticide Manual, 12th Edition, BCPC, and in DE-A-43 31 448.
- Adjuvants may also be added to the compositions according to the invention, with the result that their activity can be increased. Such adjuvants can be, for example: non-ionic surfactants, mixtures of non-ionic surfactants, mixtures of anionic surfactants with non-ionic surfactants, organosilicon surfactants, mineral oil derivatives with and without surfactants, vegetable oil derivatives with and without added surfactant, fish oils and other oils of animal nature and alkyl derivatives thereof with and without surfactants, naturally occurring higher saturated and mono- or poly-unsaturated fatty acids, preferably having from 8 to 28 carbon atoms, and alkyl ester derivatives thereof, organic acids containing an aromatic ring system and one or more carboxylic acid radicals, as well as alkyl derivatives thereof. Mixtures of individual adjuvants with one another and in combination with organic solvents can result in a further enhancement of action. Adjuvants suitable for the present invention are described in EP-A-1 062 217.
- The preparation of the ECs according to the invention is carried out substantially in accordance with the known customary method of dissolving the herbicide in the alcohol and optionally in the water-insoluble solvent and then adding a customary emulsifier. The mixture so obtained is stirred until a clear solution has been formed.
- Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ formulations diluted with water.
- An emulsifiable concentrate of 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester is prepared by dissolving 10.5 g of that herbicide and 2.7 g of the safener cloquintocet-mexyl in a mixture of 1 g of Soprophor TS/10 (ethoxylated tristyryl phenol with 10 mol of ethylene oxide), 1 g of Atlas G-5000 (butanol EO/PO block copolymer), 1 g of Rhodacal 60/BE (calcium salt of dodecylbenzenesulfonic acid) and 86.7 g of Solvesso 200 ND (aromatic hydrocarbons). That corresponds substantially to the ECs according to Examples F1. a) and b) of EP-A-1 062 217.
- An emulsifiable concentrate is prepared in the same way as EC 1 but instead of 86.7 g of Solvesso 200 ND there are used only 56.7 g and additionally 30.0 g of cyclohexanone. That corresponds substantially to the ECs according to Examples F1. c) and d) of EP-A-1 062 217.
- An emulsifiable concentrate is prepared in the same way as EC 1 but instead of 86.7 g of Solvesso 200 ND there are used only 56.7 g and additionally 30.0 g of tetrahydrofurfuryl alcohol. That corresponds to an EC according to the present invention.
- The concentrates are stored for 2 weeks at a temperature of 70° C. The results obtained afterwards are given in Table 1 below.
-
TABLE 1 Comparison between EC 1, EC 2 and EC 3 in respect of the stability of the 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)- 9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d]-[1,4,5]oxadiazepin-7- yl ester contained therein. EC 1 EC 2 EC 3 [g] [g] [g] Pinoxaden 10.5 10.5 10.5 cloquintocet-mexyl 2.7 2.7 2.7 ATLAS G-5000 1.0 1.0 1.0 SOPROPHOR TS/10 1.0 1.0 1.0 RHODACAL 60/B-E 1.0 1.0 1.0 tetrahydrofurfuryl alcohol 30.0 Cyclohexanone 30.0 Solvesso 200 ND 86.7 56.7 56.7 Total 102.9 102.9 102.9 Test duration: 2 weeks at 70° C. Loss of pinoxaden in % by weight 25 39 13 - The Table shows that when tetrahydrofurfuryl alcohol (EC 3) is used it is possible to obtain a significantly more stable formulation than in the case of cyclohexanone (EC 2) and Solvesso 200D alone (EC 1).
- An emulsifiable concentrate containing 107 g of 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester and 26 g of cloquintocet-mexyl is prepared by dissolving those compounds in a mixture of 10 g of Soprophor TS/10 (ethoxylated tristyryl phenol with 10 mol of ethylene oxide), 10 g of Atlas G-5000 (butanol EO/PO block copolymer), 10 g of Rhodacal 60/BE (calcium salt of dodecylbenzenesulfonic acid), 524 g of Solvesso 200 ND (aromatic hydrocarbons) and 300 g of 2-methyl-2,4-pentanediol and stirring until a clear solution is obtained. The concentrate so prepared is stored for 4 weeks at a temperature of 50° C., after which only a 2% loss of 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester is observed.
- An emulsifiable concentrate is prepared as in Example 2 except that 300 g of diacetone alcohol are used instead of the 2-methyl-2,4-pentanediol. The concentrate so obtained is stored for 4 weeks at a temperature of 50° C., after which only a 2% loss of 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo-[1,2-d][1,4,5]oxadiazepin-7-yl ester is observed.
- An emulsifiable concentrate containing 129 g of 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester and 31 g of cloquintocet-mexyl is prepared by dissolving those compounds in a mixture of 10 g of Soprophor TS/10 (ethoxylated tristyryl phenol with 10 mol of ethylene oxide), 50 g of Atlas MBA 1307 (mono-branched fatty alcohol alkoxylate), 1320 g of Solvesso 200 ND (aromatic hydrocarbons) and 500 g of tetrahydrofurfuryl alcohol and stirring until a clear solution is obtained. The concentrate so prepared is stored for 4 weeks at a temperature of 50° C., after which only a 2% loss of 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester is observed.
- An emulsifiable concentrate containing 54 g of 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester and 13 g of cloquintocet-mexyl is prepared by dissolving those compounds in a mixture of 10 g of Soprophor TS/10 (ethoxylated tristyryl phenol with 10 mol of ethylene oxide), 10 g of Atlas G-5000 (butanol EO/PO block copolymer), 10 g of Rhodacal 60/BE (calcium salt of dodecylbenzenesulfonic acid), 158 g of Solvesso 200 ND (aromatic hydrocarbons), 450 g of rape oil methyl ester and 250 g of tetrahydrofurfuryl alcohol and stirring until a clear solution is obtained. The concentrate so prepared is stored for 4 weeks at a temperature of 50° C., after which only a 3% loss of 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester is observed.
- An emulsifiable concentrate containing 60 g of 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester and 15 g of cloquintocet-mexyl is prepared by dissolving those compounds in a mixture of 20 g of NANSA EVM63/B (calcium dodecylbenzenesulfonate), 50 g of SERVIROX OEG 59 E (ethoxylated castor oil), 675 g of Solvesso 200 ND (aromatic hydrocarbon) and 200 g of benzyl alcohol and stirring until a clear solution is obtained. The concentrate so prepared is stored for 4 weeks at a temperature of 50° C., after which only a 3% loss of 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d]-[1,4,5]oxadiazepin-7-yl ester is observed.
- 2,2-Dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester is generally applied to the plant or to the locus thereof at rates of application of from 5 to 200 g/ha, especially from 10 to 80 g/ha, more especially from 30 to 60 g/ha.
- The rates of application of safener are generally from 2 to 100 g/ha, preferably from 2 to 50 g/ha, especially from 7.5 to 15 g/ha.
- The concentration required to achieve the desired effect can be determined by experiment. It is dependent upon the nature of the action, the stage of development of the cultivated plant and of the weed and on the application (place, time, method) and may vary within wide limits as a function of those parameters.
- The rate of application of safener relative to herbicide is largely dependent upon the mode of application. Where a field treatment is carried out either by using a tank mixture with a combination of safener and herbicide or by separate application of safener and herbicide, the ratio of herbicide to safener will usually be from 1:1 to 10:1, preferably 4:1.
- The herbicidal activity of the emulsifiable concentrates according to the invention is demonstrated in the following Example:
- Monocotyledonous and dicotyledonous weeds are raised under greenhouse conditions in standard soil in plastics pots. Application of the emulsifiable concentrate is effected at the 3- to 6-leaf stage of the test plants. For that purpose, the above-mentioned EC 3 is dissolved in 400 litres of water/ha. The tests are evaluated after 20 days (% action, 100%=plant has died, 0%=no phytotoxic action); test plants: Alopecurus myrosuroides, Lolium rigidum, Avena fatua, Setaria viridis. The results are given in Table 2 below:
-
TABLE 2 Weed control (%) at a rate of application (g ai/ha) of Test plants 8 16 64 Alopecurus myosuroides 70 80 100 Avena fatua 95 98 100 Lolium rigidum 100 100 100 Setaria viridis 80 100 100
Claims (22)
1. A herbicidal composition in the form of an emulsifiable concentrate, comprising:
a) 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester;
b) benzyl alcohol or 2-methyl-2,4-pentanediol;
c) an emulsifier; and
d) a water-insoluble solvent.
2. The composition according to claim 1 , wherein the 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester is present from 1 to 50% by weight.
3. The composition according to claim 1 , wherein the (2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester is present from 3 to 30% by weight.
4. The composition according to claim 1 , wherein the benzyl alcohol or 2-methyl-2,4-pentanediol is present from 1 to 97% by weight.
5. The composition according to claim 1 , wherein the benzyl alcohol or 2-methyl-2,4-pentanediol is present from 5 to 50% by weight.
6. The composition according to claim 1 , wherein the benzyl alcohol or 2-methyl-2,4-pentanediol is present from 10 to 30% by weight.
7. The composition according to claim 1 , wherein the water-insoluble solvent comprises toluene; xylene; cumene; a mixture of aromatic hydrocarbons having a boiling point of from 160 to 180° C. or from 180 to 210° C. or from 230 to 290° C.; an aliphatic or cycloaliphatic hydrocarbon; a fatty alcohol acetate; isobornyl acetate; benzyl acetate; a lower alkyl ester of maleic, fumaric, succinic, glutaric or adipic acid; an ester of benzoic acid; a C8-C10fatty acid methyl ester; or a C16-C18fatty acid methyl ester.
8. The composition according to claim 7 , wherein the water-insoluble solvent is present from 10 to 70% by weight.
9. The composition according to 1, wherein the emulsifier is present from 2 to 30% by weight.
10. The composition according to claim 1 , further comprising one or more herbicides that are compatible with the 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester.
11. The composition according to claim 1 , further comprising a second herbicide member selected from the group of sulfonylureas, aryloxyphenoxypropionates, triazolopyrimidines, arylcarboxylic acids, aryloxycarboxylic acids, cyclohexanedione oximes, thiocarbamates, hydroxybenzonitriles, dinitroanilines and pyridinecarboxamides.
12. The composition according to claim 1 , further comprising a second herbicide member selected from the group of: triasulfuron, tribenuron, metsulfuron, thifensulfuron, flupyrsulfuron, chlorsulfuron, prosulfuron, amidosulfuron, mesosulfuron, sulfosulfuron, tritosulfuron, clodinafop-propargyl, fenoxaprop-P-ethyl, diclofop-methyl, cyhalofop-butyl, florasulam, metosulam, flumetsulam, dicamba, clopyralid, an ester of 2,4-D, 2,4-DP, mecoprop, mecoprop-P, MCPA, MCPB, dichlorprop-P, fluroxypyr, tralkoxydim, triallate, prosulfocarb, bromoxynil, bromoxynil octanoate, ioxynil, ioxynil octanoate, pendimethalin, trifluralin, and diflufenican.
13. The composition according to claim 1 , further comprising a safener.
14. The composition according to claim 1 , further comprising cloquintocet-mexyl, mefenpyr-diethyl or isoxadifen-ethyl.
15. The composition according to claim 1 , further comprising an adjuvant.
16. The composition according to claim 1 , wherein the composition has a storage stability characterized by a loss of no more than 13% by weight of the 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester, after storage of the emulsifiable concentrate for 2 weeks at a temperature of 70° C.
17. The composition according to claim 1 , wherein the composition has a storage stability characterized in that a loss of no more than 3% of the 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester is observed after storage of the emulsifiable concentrate for 4 weeks at a temperature of 50° C.
18. The composition according to claim 1 , wherein the composition has a storage stability characterized in that a loss of no more than 2% of the 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester is observed after storage of the emulsifiable concentrate for 4 weeks at a temperature of 50° C.
19. The composition according to claim 1 , comprising benzyl alcohol.
20. The composition according to claim 1 , comprising 2-methyl-2,4-pentanediol.
21. A method of controlling undesirable plant growth, comprising: applying a herbicidally effective amount of a composition according to claim 1 to the plants or to the locus thereof.
22. A herbicidal composition in the form of an emulsifiable concentrate, comprising:
a) 2,2-dimethyl-propionic acid 8-(2,6-diethyl-4-methyl-phenyl)-9-oxo-1,2,4,5-tetrahydro-9H-pyrazolo[1,2-d][1,4,5]oxadiazepin-7-yl ester from 3 to 30% by weight;
b) benzyl alcohol or 2-methyl-2,4-pentanediol from 10 to 30% by weight;
c) an emulsifier from 2 to 30% by weight; and
d) a water-insoluble solvent from 10 to 70% by weight.
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JP5086272B2 (en) | 2012-11-28 |
EP1965646B1 (en) | 2010-03-17 |
DK1965646T3 (en) | 2010-06-07 |
EA200801448A1 (en) | 2009-06-30 |
CA2632323A1 (en) | 2007-07-05 |
JP2009524597A (en) | 2009-07-02 |
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BRPI0621268A2 (en) | 2011-12-06 |
AU2006331031A1 (en) | 2007-07-05 |
WO2007073933A3 (en) | 2009-02-19 |
WO2007073933A8 (en) | 2008-07-17 |
AR058747A1 (en) | 2008-02-20 |
ZA200804764B (en) | 2009-10-28 |
US10952437B2 (en) | 2021-03-23 |
UA92512C2 (en) | 2010-11-10 |
PT1965646E (en) | 2010-05-20 |
SI1965646T1 (en) | 2010-07-30 |
EA018654B1 (en) | 2013-09-30 |
CN101453894A (en) | 2009-06-10 |
US20230263163A1 (en) | 2023-08-24 |
DE602006013038D1 (en) | 2010-04-29 |
CA2632323C (en) | 2015-03-17 |
EP1965646A2 (en) | 2008-09-10 |
WO2007073933A2 (en) | 2007-07-05 |
US20090005246A1 (en) | 2009-01-01 |
BRPI0621268B1 (en) | 2015-10-27 |
CN101453894B (en) | 2012-08-08 |
MA30087B1 (en) | 2008-12-01 |
AU2006331031B2 (en) | 2013-06-13 |
SA06270491B1 (en) | 2010-10-20 |
ATE460839T1 (en) | 2010-04-15 |
PL1965646T3 (en) | 2010-08-31 |
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