CN102905523B - 具有酰基吗啉和极性非质子助溶剂的农业配制剂 - Google Patents
具有酰基吗啉和极性非质子助溶剂的农业配制剂 Download PDFInfo
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- CN102905523B CN102905523B CN201180024941.3A CN201180024941A CN102905523B CN 102905523 B CN102905523 B CN 102905523B CN 201180024941 A CN201180024941 A CN 201180024941A CN 102905523 B CN102905523 B CN 102905523B
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- morpholine
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- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 title claims abstract description 108
- 125000002252 acyl group Chemical group 0.000 title claims abstract description 47
- 239000006184 cosolvent Substances 0.000 title claims abstract description 44
- 239000000203 mixture Substances 0.000 title claims description 27
- 239000003905 agrochemical Substances 0.000 claims abstract description 38
- 239000005648 plant growth regulator Substances 0.000 claims abstract description 34
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 claims description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 27
- -1 alkylene carbonates Chemical class 0.000 claims description 18
- 239000005906 Imidacloprid Substances 0.000 claims description 15
- 229940056881 imidacloprid Drugs 0.000 claims description 15
- YWTYJOPNNQFBPC-UHFFFAOYSA-N imidacloprid Chemical group [O-][N+](=O)\N=C1/NCCN1CC1=CC=C(Cl)N=C1 YWTYJOPNNQFBPC-UHFFFAOYSA-N 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 13
- MTXSIJUGVMTTMU-JTQLQIEISA-N (S)-anabasine Chemical class N1CCCC[C@H]1C1=CC=CN=C1 MTXSIJUGVMTTMU-JTQLQIEISA-N 0.000 claims description 10
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- QIIPQYDSKRYMFG-UHFFFAOYSA-N phenyl hydrogen carbonate Chemical class OC(=O)OC1=CC=CC=C1 QIIPQYDSKRYMFG-UHFFFAOYSA-N 0.000 claims description 4
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- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 3
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 11
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- PGOOBECODWQEAB-UHFFFAOYSA-N (E)-clothianidin Chemical compound [O-][N+](=O)\N=C(/NC)NCC1=CN=C(Cl)S1 PGOOBECODWQEAB-UHFFFAOYSA-N 0.000 description 2
- CFRPSFYHXJZSBI-DHZHZOJOSA-N (E)-nitenpyram Chemical compound [O-][N+](=O)/C=C(\NC)N(CC)CC1=CC=C(Cl)N=C1 CFRPSFYHXJZSBI-DHZHZOJOSA-N 0.000 description 2
- NWWZPOKUUAIXIW-DHZHZOJOSA-N (E)-thiamethoxam Chemical compound [O-][N+](=O)/N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-DHZHZOJOSA-N 0.000 description 2
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- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 2
- UFNOUKDBUJZYDE-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Chemical compound C1=NC=NN1CC(O)(C=1C=CC(Cl)=CC=1)C(C)C1CC1 UFNOUKDBUJZYDE-UHFFFAOYSA-N 0.000 description 2
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- 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
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 230000032823 cell division Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229940071118 cumenesulfonate Drugs 0.000 description 1
- 229960002483 decamethrin Drugs 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- BQYJATMQXGBDHF-UHFFFAOYSA-N difenoconazole Chemical compound O1C(C)COC1(C=1C(=CC(OC=2C=CC(Cl)=CC=2)=CC=1)Cl)CN1N=CN=C1 BQYJATMQXGBDHF-UHFFFAOYSA-N 0.000 description 1
- YKBZOVFACRVRJN-UHFFFAOYSA-N dinotefuran Chemical compound [O-][N+](=O)\N=C(/NC)NCC1CCOC1 YKBZOVFACRVRJN-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- AHXDSVSZEZHDLV-UHFFFAOYSA-N mesulfen Chemical compound CC1=CC=C2SC3=CC(C)=CC=C3SC2=C1 AHXDSVSZEZHDLV-UHFFFAOYSA-N 0.000 description 1
- XWPZUHJBOLQNMN-UHFFFAOYSA-N metconazole Chemical compound C1=NC=NN1CC1(O)C(C)(C)CCC1CC1=CC=C(Cl)C=C1 XWPZUHJBOLQNMN-UHFFFAOYSA-N 0.000 description 1
- OJQWZQBYOGZGSC-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1.O=CN1CCOCC1 OJQWZQBYOGZGSC-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
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- 150000002825 nitriles Chemical class 0.000 description 1
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- WUHLVXDDBHWHLQ-UHFFFAOYSA-N pentazole Chemical class N=1N=NNN=1 WUHLVXDDBHWHLQ-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
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- 239000007787 solid Substances 0.000 description 1
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- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- 239000003799 water insoluble solvent Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 229940071104 xylenesulfonate Drugs 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
Classifications
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- 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
- 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
-
- 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
- A01N39/04—Aryloxy-acetic acids; Derivatives thereof
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
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- 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
- A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
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Abstract
本发明提供了一种配制剂,其包含农药和/或植物生长调节剂、式(I)的酰基吗啉和不同于式(I)的酰基吗啉的极性非质子助溶剂,其中R为H、CH3或C2H5。所述配制剂可用于植物处理中,尤其适于用作可溶液体配制剂。
Description
技术领域
本发明涉及包含农药和/或植物生长调节剂和溶剂体系的配制剂,所述配制剂的制备方法,使用所述配制剂处理植物的方法,以及溶剂体系作为农药和/或植物生长调节剂的溶剂的用途。
背景技术
农业活性物质如农药和植物生长调节剂通常以不同浓缩程度的形式提供给最终用户,从而由最终用户稀释于水或其他合适介质中以获得稀即用型配制剂。这类浓缩形式包括固体配制剂如粉末,和液体配制剂。在许多应用场合中,优选液体配制剂,这是因为可避免撒粉有毒粉末和在稀释剂中溶解缓慢的问题。
液体浓缩配制剂包括所谓的乳液浓缩物和可溶液体浓缩物。乳液浓缩物包含农业活性物质、水不溶性溶剂和乳化剂,且当添加至水中时,其自发或者在混合后形成水包油型乳液,农业活性物质主要存在于乳液液滴中。该种浓缩乳液尤其适于水不溶性/具有低水溶性的农业活性物质,以及适用于在即用型配制剂中的推荐浓度超过该农业活性物质的溶解度的场合。
可溶液体浓缩物包含水溶性溶剂和农业活性物质,且当添加至水中时,所述溶剂和农业活性物质二者均自发或者在混合后溶于水中。该种浓缩配制剂尤其适于在超过于即用型配制剂中的推荐浓度的浓度下也可溶于水中的农业活性物质。
当将可溶液体浓缩物与含水介质混合时,首先,在所得配制剂达到平衡之前,所述活性物质会存在局部高浓度。因此,当将可溶液体浓缩物稀释于含水介质中时,所述农业活性物质存在发生沉淀的风险。由于沉淀物的缓慢溶解,该沉淀可能导致问题。在一些情况下,沉淀物甚至基本上为水不溶性的。
WO2007/028518公开了一种吡虫啉(imidacloprid,一种新烟碱类(neonicotinide)杀虫剂)可溶液体配制剂,其中使用N-甲基吡咯烷酮(NMP)作为溶剂。
然而,已显示NMP是一种生殖毒剂(Merlet,S.等,“GreenSolventsforAgrochemicals”,AdjuvantNewsletter,第7卷第2期,2010年2月,第1-3页)。
WO2008/101620描述了一种解决与在农业配制剂中使用NMP有关的问题的方法,其中提出将包含羟基取代的酰基的二烷基酰胺用作生物杀伤剂的溶剂。
然而,正如Merlet,S.等(参见上文)所报道的那样,某些引人关注的市售生物杀伤剂(如吡虫啉)在该含羟基取代的酰基的二烷基酰胺中不具有很高的溶解度。
因此,本领域需要寻找可取代农业活性物质的可溶液体配制剂中的NMP,同时保持所述农业活性物质的高溶解度的溶剂。
发明简述
本发明的一个目的在于至少部分克服现有技术的缺点,并提供一种可用于可溶液体配制剂中且至少部分可取代NMP的使用的溶剂体系。
本发明的另一目的在于提供一种用于农业活性物质的溶剂体系,其允许溶剂和农业活性物质与含水介质混合而不导致所述活性物质沉淀或者仅少部分沉淀的浓缩配制剂。
本发明人令人惊讶地发现,某些短链酰基吗啉,如N-甲酰基、N-乙酰基和N-丙酰基吗啉可用于实现该目的。
特别地发现一种包含该短链酰基吗啉和极性非质子助溶剂的溶剂体系可用于实现该目的。
因此,在第一方面中,本发明涉及一种配制剂,其包含农药和/或植物生长调节剂、式(I)的酰基吗啉和优选的不同于式(I)的酰基吗啉的极性非质子助溶剂:
其中R为H、CH3或C2H5。
在第二方面中,本发明涉及一种制备包含至少90%水的上述配制剂的方法,包括将包含至多10%水的上述配制剂与含水介质混合。
在第三方面中,本发明涉及一种处理植物的方法,包括使所述植物与上述配制剂接触。
在第四方面中,本发明涉及本发明的配制剂在处理植物中的用途。
在第五方面中,本发明涉及式(I)的酰基吗啉或者包含式(I)的酰基吗啉和不同于式(I)的酰基吗啉的极性非质子助溶剂的溶剂体系作为农药和/或植物生长调节剂的用途:
其中R为H、CH3或C2H5。
应注意的是,本发明涉及所附权利要求书的所有可能的组合。
发明详述
本发明的配制剂包含:
a)一种或多种农药和/或一种或多种植物生长调节剂;
b)一种或多种式(I)的酰基吗啉:
其中R为H、CH3或C2H5;和优选的
c)一种或多种不同于式(I)的酰基吗啉的极性非质子助溶剂。
本文所用的术语“农药”是指防止、破坏、趋避或减少任何害物的有机化合物。
本文所用的术语“植物生长调节剂”是指通过生理学作用促进或延缓观赏植物或作物或其产品的生长速度或成熟速度或改变其行为的有机化合物。
可用于本发明中的农药包括但不限于杀真菌剂、除草剂、杀昆虫剂、灭疥药、杀线虫剂、杀螨剂和杀软体动物剂。
可用于本发明中的优选农业活性物质包括但不限于如下类别的农药和植物生长调节剂:三唑类、嗜球果伞素类、亚烷基双(二硫代氨基甲酸酯)化合物、苯并咪唑类、苯氧基羧酸类、苯甲酸类、氨基酸类、磺酰脲类、三嗪类、三唑啉酮类、吡啶羧酸类、新烟碱类、脒类、有机磷酸酯类和拟除虫菊酯类。
可用于本发明中的杀真菌剂实例包括但不限于如下类别的杀真菌剂:三唑类(例如戊唑醇(tebuconazole)、氟醚唑(tetraconazole)、环唑醇(cyproconazole)、氧唑菌(epoxiconazole)、醚唑(difenconazole)、丙环唑(propiconazole)、丙硫菌唑(prothioconazole)、环戊唑菌(metconazole)),嗜球果伞素类(例如肟菌酯(trifloxystrobin)、腈嘧菌酯(azoxystrobin)、氟嘧菌酯(fluoxastrobin)、唑菌胺酯(pyraclostrobin)),亚烷基双(二硫代氨基甲酸酯)化合物(例如代森锰锌(mancozeb))和苯并咪唑类(例如多菌灵(carbendazim))。
可用于本发明中的除草剂实例包括但不限于苯氧基羧酸(例如2,4-滴(2,4-D)酸、2甲4氯(MCPA)),苯甲酸类(例如麦草畏(dicamba)酸),氨基酸类(例如草铵膦(glufosinate))、磺酰脲类(例如精甲磺胺黄隆(methylsulfuron-methyl)、玉嘧黄隆(rimsulfuron)),三嗪类(例如莠去津(atrazine)和西玛津(simazine)),三唑啉酮类(例如氨唑草酮(amicarbazone))和吡啶羧酸类(例如定草酯(triclopyr))。
可用于本发明中的杀虫剂实例包括但不限于新烟碱类(例如噻虫嗪(thiamethoxam)、噻虫胺(clothianidin)、噻虫啉(thiacloprid)、呋虫胺(dinotefuran)、吡虫清(acetamiprid)、硝胺烯啶(nitenpyram)、吡虫啉(imidacloprid)),脒类(例如虫螨脒(amitraz)),有机磷酸酯类(例如毒死蜱(chlorpyrifos))和拟除虫菊酯类(例如氯菊酯(permethrin)、氟氯菊酯(bifenthrin)、溴氰菊酯(deltamethrin))。
可用于本发明中的植物生长调节剂实例包括但不限于膦酸类(例如乙烯利(ethephon)),赤霉素,细胞分裂素(例如6-苄基氨基嘌呤)和植物生长素(例如1-萘基乙酸)。
本发明的配制剂优选包含新烟碱类、苯氧基羧酸类、苯甲酸类和三唑类,更优选包含吡虫啉。
上述各种农药和植物生长调节剂的详细描述参见各种手册,如“Thee-PesticideManualv4.0”,BCPCPublicationsLtd,Alton,Hampshire(ISBN1901396428)。
尤其可用于本发明配制剂中的农药和植物生长调节剂包括在即用型配制剂中于推荐浓度下为水溶性的那些,即所述农药或植物生长调节剂优选呈即用型配制剂溶液的形式。
在本发明的上下文中,水溶解度应解释为根据ASTME1148-87“StandardTestMethodforMeasurementsofAqueousSolubility”测定。
本发明配制剂可包含单一农药或植物生长调节剂,或者可包含两种或更多种不同农药或两种或更多种植物生长调节剂的混合物或至少一种农药与至少一种植物生长调节剂的混合物。
可用于本发明配制剂中的酰基吗啉为4-甲酰基吗啉(R=H,也称为N-甲酰基吗啉或NFM)、4-乙酰基吗啉(R=CH3,也称为N-乙酰基吗啉或NAM)、4-丙酰基吗啉(R=C2H5,也称为N-丙酰基吗啉或NPM)及其两种或更多种的任意混合物。优选地,当所述配制剂中包含不同于通式(I)的酰基吗啉的极性非质子助溶剂时,本发明配制剂包含4-甲酰基吗啉,更优选4-甲酰基吗啉占该配制剂中的式(I)的酰基吗啉的至少50重量%,最优选占100重量%。
然而,对不包含任何不同于通式(I)的酰基吗啉的极性非质子助溶剂的配制剂而言,尤其是对其中农药为N,N’-双[(1-甲酰胺基-2,2,2-三氯)乙基]哌嗪的这类配制剂而言,优选所述酰基吗啉选自4-乙酰基吗啉和4-丙酰基吗啉。
所述酰基吗啉本身是公知的化合物,且可由标准化学品供应商市售。
除式(I)的酰基吗啉之外,本发明配制剂优选进一步包含一种或多种不同于式(I)的酰基吗啉的极性非质子溶剂(本文称为“极性非质子助溶剂”)。
所述极性非质子助溶剂优选选自闪点为至少65°C的那些,根据DIN51758“FlashandFirePointsbyClevelandOpenCupTester”测定。
所述极性非质子助溶剂优选选自如下组:亚砜、酰胺、碳酸烃基酯和碳酸亚烃基酯,及其两种或更多种的混合物。优选的亚砜包括二甲亚砜。优选的碳酸烃基酯包括碳酸二烷基酯,如具有C1-C8烷基链的那些。优选的碳酸亚烃基酯包括碳酸亚烷基酯,更优选为碳酸C2-C4亚烷基酯,最优选为碳酸亚丙酯。更优选所述极性非质子助溶剂选自二甲亚砜、碳酸亚丙酯及其混合物,最优选为碳酸亚丙酯。
不包含不同于通式(I)的酰基吗啉的极性非质子助溶剂的本发明配制剂优选包含从约10重量%,更优选从约20重量%,最优选从约25重量%,至约70重量%,更优选至约60重量%,最优选至约50重量%的a)农药和/或植物生长调节剂;和从约10重量%,更优选从约20重量%,最优选从约25重量%,至约90重量%,更优选至约80重量%,最优选至约70重量%的b)式(I)的酰基吗啉。
进一步包含不同于通式(I)的酰基吗啉的极性非质子助溶剂的本发明配制剂优选包含从约10重量%,更优选从约20重量%,最优选从约25重量%,至约70重量%,更优选至约60重量%,最优选至约50重量%的a)农药和/或植物生长调节剂;从约10重量%,更优选从约20重量%,最优选从约25重量%,至约89重量%,更优选至约80重量%,最优选至约70重量%的b)通式(I)的酰基吗啉;和从约1重量%,更优选从约5重量%,最优选从约10重量%,至约50重量%,更优选至约40重量%,最优选至约30重量%的c)不同于式(I)的酰基吗啉的极性非质子助溶剂,基于该组合物中的a)、b)和c)总重量计算,即在该计算中不计入水和其他组分。
当存在不同于式(I)的酰基吗啉的极性非质子助溶剂时,b)式(I)的酰基吗啉与c)不同于式(I)的酰基吗啉的极性非质子助溶剂的重量比从5:95,优选从30:70,更优选从50:50,甚至更优选从70:30,甚至更优选从75:25,最优选从78:22,至95:5,优选至90:10,更优选至85:15,最优选至82:18,例如约80:20。
特别地,当式(I)的酰基吗啉为4-甲酰基吗啉(N-甲酰基吗啉)且所述极性非质子助溶剂为碳酸亚丙酯时,b)与c)的重量比从70:30,更优选从75:25,最优选从78:22,至90:10,更优选至85:15,最优选至82:18,如约80:20。
在目前优选的实施方案中,a)为新烟碱类,优选为吡虫啉;b)为4-甲酰基吗啉且c)为碳酸亚丙酯。
优选a)、b)和存在时的c)占本发明配制剂的非水组分总重的从约60重量%,更优选从约70重量%,最优选从约80重量%,至100重量%。
本发明配制剂通常以使得各组分以所需比例和所需浓度混合的方式制备。所述配制剂通常在10-50°C的温度下制备。用于制备农业配制的合适的装置适于作为用于制备本发明配制剂的装置。
在一个实施方案中,本发明配制剂包含少于10重量%,优选少于5重量%,甚至更优选少于2重量%,最优选少于1重量%的水,基于所述配制剂的总重量,该配制剂在下文中称为“浓缩配制剂”。
在本发明的该浓缩配制剂中,农药或植物生长调节剂的浓度优选为所述农药或植物生长调节剂在所述溶剂中(即,在式(I)的酰基吗啉与极性非质子助溶剂的组合中)的溶解度或更低。因此,所述浓缩配制剂优选为澄清的均质配制剂。
在另一实施方案中,本发明配制剂包含至少90重量%,优选至少95重量%,更优选至少99重量%的水,基于所述配制剂的总重,其在下文中称为“稀配制剂”。
在该稀配制剂中,农药或植物生长调节剂的浓度优选为所述农药或植物生长调节剂在该稀配制剂中的溶解度或更低。因此,所述稀配制剂优选为澄清的均质配制剂。
本发明的稀配制剂的农药或植物生长调节剂的浓度通常与所述农药或植物生长调节剂的最终应用(例如植物处理)推荐浓度相匹配。
本发明的稀配制剂可通过将本发明的浓缩配制剂与含水介质混合而获得。所述含水介质通常为自来水。
可将所述浓缩配制剂添加至含水介质中,或者可将所述含水介质添加至所述浓缩配制剂中。通常使用前一方法。
式(I)的酰基吗啉和不同于式(I)的酰基吗啉的极性非质子助溶剂一起形成其中农药和/或植物生长调节剂高度可溶的溶剂体系。
可用于本发明中的酰基吗啉的熔点高于室温,因此,显而易见其不能立即用于农药配制剂的溶剂体系中,其优选应在通常为室温或稍低于室温的温度下为液态。然而,当与农药和/或植物生长调节剂混合时,通常形成在室温下为液态的组合物。
所述农药和植物生长调节剂在式(I)的酰基吗啉中显示出高溶解度。然而,当将农药/植物生长调节剂和所述酰基吗啉(但不含任何极性非质子助溶剂)的浓缩配制剂添加至含水介质中时,在一些情况下,所述农药/植物生长调节剂沉淀。通过将所述极性非质子助溶剂添加至所述浓缩配制剂中,沉淀倾向得以降低,且如果形成一些沉淀,则其可容易地溶于所得稀配制剂中。
4-甲酰基吗啉和碳酸亚丙酯和/或二甲亚砜是目前优选用于本发明中的溶剂体系。
在优选实施方案中,本发明配制剂基本不含或者包含小于约5重量%,优选小于约2重量%的质子酰胺溶剂。
本领域技术人员知晓除所述农药和/或植物生长调节剂、式(I)的酰基吗啉和极性非质子助溶剂之外,本发明的配制剂可任选包含d)其他组分。该类其他组分的实例包括例如一种或多种助剂,如农业活性物质的生物学效价提高剂、保湿剂、润湿剂、流变调节剂、表面活性剂、粘着剂、漂移降低剂和/或通常用于农化组合物中的其他额外组分。
本发明配制剂优选包含从0重量%,更优选从约5重量%,最优选从约10重量%,至约40重量%,更优选至约30重量%,最优选至约20重量%的其他组分d),基于所述组合物中的a)、b)、c)和d)的总重量计算,即在该计算中不计入任何水。
在优选实施方案中,本发明配制剂包含至少一种表面活性剂。将表面活性剂添加至所述配制剂中可防止本发明的浓缩组合物在将含水介质添加至其中时处于其表面上,且可额外起助剂和/或润湿剂的作用。
用于本发明中的表面活性剂实例包括非离子、阴离子、两性、两性离子表面活性剂及其两种或更多种的混合物。
所述非离子表面活性剂包括但不限于烷氧基化的,优选乙氧基化的和/或丙氧基化的醇,优选包含8-22个碳原子;烷基(聚)苷,如直链或支化的C4-C10烷基(聚)苷;以及烷氧基化的,优选乙氧基化的脱水山梨糖醇或山梨糖醇酯。优选的乙氧基化醇具有1-50,更优选2-20,最优选3-10的乙氧基化度。可用于本发明中的一些烷氧基化醇包括基于支化醇的那些,所述醇如Guerbet醇,例如2-丙基庚醇和2-乙基己醇,和C10-C13羰基合成醇,即主要组分由至少一种支化C10-C13醇构成的醇混合物,且所述醇可以以Exxal醇由ExxonMobileChemicals商购获得,且以Neodol由ShellChemicals商购获得。
阴离子表面活性剂包括但不限于磺基琥珀酸盐;烷基苯磺酸盐如十二烷基苯磺酸钙或钠;烷基磺酸盐;烷基醚硫酸盐;任选烷氧基化的,优选乙氧基化的和/或丙氧基化的醇的磷酸酯;二甲苯磺酸盐和异丙苯磺酸盐;萘磺酸盐或烷基萘磺酸盐,其可为缩合的。
阳离子表面活性剂包括但不限于烷氧基化的,优选乙氧基化的和/或丙氧基化的脂肪胺或醚胺;烷氧基化的,优选乙氧基化的和/或丙氧基化的季铵化合物,如以Berol556和BerolR648市售的那些(获自瑞典AkzoNobelSurfaceChemistryAB)。
两性离子/两性表面活性剂包括但不限于甜菜碱表面活性剂,如烷基甜菜碱、烷基酰胺基亚烷基甜菜碱和磺基甜菜碱;氧化胺表面活性剂,如烷基氧化胺和烷基酰胺基亚烷基氧化胺;脂肪族亚氨基二丙酸盐和脂肪族亚氨基甘氨酸盐。
表面活性剂可占从0重量%,优选从约0.5重量%,更优选从约1重量%,至约20重量%,优选至约15重量%,更优选至约10重量%,基于所述组合物中的a)、b)、c)(当存在时)和d)的总重量,即在该计算中不计入水。
本发明的一个独立方面为一种处理植物的方法。所述方法包括使所述植物与本发明配制剂接触的步骤。本发明的配制剂可通过喷雾、浇灌、雾化、喷射或刷涂施用。优选与植物的接触通过喷雾上述稀配制剂进行。
本发明配制剂的施用率可在很宽范围内变化。施用率可取决于所述配制剂中的农药和/或植物生长调节剂及其在配制剂中的浓度。当然希望与植物接触的配制剂的量为包含有效实现该配制剂的目的的农药和/或植物生长调节剂的量。
本发明配制剂可用于处理所有植物和植物部分。在本发明的上下文中,植物应理解为意指所有植物和植物种群,如所希望的和不希望的野生植物或作物以及任何植物部分。
植物部分应理解为意指植物的所有地上和地下部分和器官,包括嫩枝、叶、针叶、秆、茎、花、结果体、果实、种子、根、块茎和根茎。植物部分也包括收获的材料以及无性和有性繁殖材料如插条、块茎、根茎、插枝和种子。
实施例
实施例1在酰基吗啉中的溶解度
将不同农业活性成分溶解于N-甲酰基吗啉、N-乙酰基吗啉和N-丙酰基吗啉中,以评价所述活性成分在所述溶剂中的溶解度。这通过将所述活性成分添加至烧杯中,其后添加所述溶剂直至获得澄清溶液而进行。在试验过程中,继续在23°C的温度下搅拌该溶液。当所有物质均溶解时,使烧杯处于未搅动状态达24小时,以观察该溶液是否稳定(即,不结晶)。表1:将活性成分溶于N-甲酰基吗啉(NFM)、N-乙酰基吗啉(NAM)和N-丙酰基吗啉(NPM)中,以每100g溶剂中的活性成分克数测定。
*获自AdjuvantNewsletter的文献值(参见上文)。
实施例2吡虫啉配制剂在水中的稀释
将包含200g/l吡虫啉的配制剂与40g/l醇乙氧基化物(基于每摩尔醇用8摩尔EO乙氧基化的2-丙基庚醇)配制在一起,并用溶剂N-甲酰基吗啉、N-乙酰基吗啉和N-丙酰基吗啉中的各自一种与助溶剂一起稀释至1升的最终体积。所用助溶剂为二甲亚砜(DMSO)、碳酸亚丙酯(PC)、二甲基甲酰胺(DMF)和乳酸乙酯(EL)。乳酸乙酯为质子溶剂且用于该试验中以进行对比。各助溶剂的用量(以所述吗啉类和助溶剂总重量的重量%计)参见表2。用水将所述溶液稀释至0.4g/l的吡虫啉最终浓度,该稀释通过用肉眼视觉观察判断,在下表中,使用如下符号:
+易于溶解,
-永久晶体,
NS不溶解
表2:在将吡虫啉溶于与助溶剂(即二甲亚砜(DMSO)、碳酸亚丙酯(PC)、二甲基甲酰胺(DMF)或乳酸乙酯(EL))一起的N-甲酰基吗啉(NFM)、N-乙酰基吗啉(NAM)和N-丙酰基吗啉(NPM)中的浓缩溶液(200g/l)稀释于水中时吡虫啉的结晶。
实施例3:氨唑草酮配制剂在水中的稀释
在类似于上述实施例2的试验中,将包含100g/l氨唑草酮的配制剂与40g/l的醇乙氧基化物(基于每摩尔醇用8摩尔EO乙氧基化的2-丙基庚醇)配制在一起,并用溶剂N-甲酰基吗啉和N-乙酰基吗啉各自与助溶剂一起稀释至1升的最终体积。所用助溶剂为碳酸亚丙酯(PC)、二甲基甲酰胺(DMF)和乳酸乙酯(EL)。各助溶剂的用量(以所述吗啉类和助溶剂总重量的重量%计)可参见表2。在现场将所述溶液稀释于自来水中至7g/l的最终浓度,该稀释通过用肉眼视觉观察判断,在下表中,使用如下符号:
+无晶体
-永久晶体
表3:在将氨唑草酮分别溶于与助溶剂(即碳酸亚丙酯(PC)、二甲基甲酰胺(DMF)或乳酸乙酯(EL))一起的N-甲酰基吗啉(NFM)和N-乙酰基吗啉(NAM)中的浓缩溶液(100g/l)稀释于水中时氨唑草酮的结晶。
实施例4:差示扫描量热法(DSC)
为了监测蒸发焓,使用差示扫描量热法。进行这些测量的原因在于确定N-甲酰基吗啉与碳酸亚丙酯之间的内聚力。所述混合物(不同比例的N-甲酰基吗啉/碳酸亚丙酯)在20-300°C范围内以5°C/分钟的温升,使用获自MettlerToledo且具有STARe软件的DSC1量热仪扫描。DSC测量的结果可参见表4。从该结果可以清楚看出,80/20的N-甲酰基吗啉/碳酸亚丙酯(w/w)混合物显示出显著下降的蒸发焓,即在该比值下或者接近该比值时,混合物具有最低蒸发焓。
表4:在N-甲酰基吗啉(NFM)和碳酸亚丙酯(PC)的不同重量比下的蒸发焓
NFM:PC重量比 | 蒸发焓(J/g) |
100:0 | 382 |
95:5 | 421 |
90:10 | 433 |
85:15 | 405 |
80:20 | 331 |
75:25 | 369 |
50:50 | 366 |
0:100 | 392 |
Claims (28)
1.一种配制剂,其包含:
a)农药;
b)式(I)的酰基吗啉:
其中R为H或CH3;和
c)不同于式(I)的酰基吗啉的极性非质子助溶剂,其选自亚砜、酰胺、碳酸亚烃基酯及其两种或更多种的混合物。
2.根据权利要求1的配制剂,其中R为H。
3.根据权利要求1的配制剂,其中所述极性非质子助溶剂具有至少为65℃的闪点。
4.根据权利要求1的配制剂,其中所述极性非质子助溶剂选自二甲亚砜、碳酸亚丙酯及其混合物。
5.根据权利要求1的配制剂,其中所述式(I)的酰基吗啉为4-甲酰基吗啉且所述极性非质子助溶剂为碳酸亚丙酯。
6.根据权利要求5的配制剂,其中4-甲酰基吗啉与碳酸亚丙酯的重量比为70:30-90:10。
7.根据权利要求1的配制剂,其中所述农药选自如下组:三唑类、嗜球果伞素类、亚烷基双(二硫代氨基甲酸酯)化合物、苯并咪唑类、苯氧基羧酸类、苯甲酸类、氨基酸类、磺酰脲类、三嗪类、三唑啉酮类、吡啶羧酸类、新烟碱类、脒类、有机磷酸酯类、拟除虫菊酯类、膦酸类、赤霉素类、细胞分裂素类、植物生长素及其两种或更多种的混合物。
8.根据权利要求1的配制剂,其中所述农药为植物生长调节剂。
9.根据权利要求7的配制剂,其中所述农药为新烟碱类。
10.根据权利要求9的配制剂,其中所述新烟碱类为吡虫啉(imidacloprid)。
11.根据权利要求1的配制剂,其包含:
10-70重量%的a);
10-89重量%的b);和
1-50重量%的c);
基于该配制剂中a)、b)和c)的总重量。
12.根据权利要求1的配制剂,进一步包含d)至少一种选自如下组的其他组分:助剂。
13.根据权利要求12的配制剂,其中所述助剂选自表面活性剂、润湿剂、流变调节剂及其两种或更多种的混合物。
14.根据权利要求12的配制剂,包含5-40重量%的d),基于该配制剂中a)、b)、c)和d)的总重量。
15.根据权利要求1的配制剂,其包含至多10重量%的水。
16.根据权利要求1的配制剂,其包含至少90重量%的水。
17.一种制备根据权利要求16的配制剂的方法,包括将根据权利要求11的配制剂与含水介质混合。
18.一种处理植物的方法,包括使所述植物与根据权利要求1-16中任一项的配制剂接触。
19.根据权利要求1-16中任一项的配制剂在处理植物中的用途。
20.包含式(I)的酰基吗啉和不同于式(I)的酰基吗啉的极性非质子助溶剂的配制剂作为农药的溶剂的用途,
其中R为H或CH3;
其中所述极性非质子助溶剂选自亚砜、酰胺、碳酸亚烃基酯及其两种或更多种的混合物。
21.根据权利要求20的用途,其中所述式(I)的酰基吗啉为4-甲酰基吗啉且所述极性非质子助溶剂为碳酸亚丙酯。
22.根据权利要求20的用途,其中4-甲酰基吗啉与碳酸亚丙酯的重量比为70:30-90:10。
23.根据权利要求20的用途,其中所述农药为植物生长调节剂。
24.根据权利要求20-22中任一项的用途,其中所述农药为新烟碱类。
25.根据权利要求24的用途,其中所述新烟碱类为吡虫啉。
26.一种配制剂,其包含式(I)的酰基吗啉和不同于式(I)的酰基吗啉的极性非质子助溶剂,
其中R为H或CH3;
其中所述极性非质子助溶剂选自亚砜、酰胺、碳酸亚烃基酯及其两种或更多种的混合物。
27.根据权利要求26的配制剂,其中所述式(I)的酰基吗啉为4-甲酰基吗啉且所述极性非质子助溶剂为碳酸亚丙酯。
28.根据权利要求27的配制剂,其中4-甲酰基吗啉与碳酸亚丙酯的重量比为70:30-90:10。
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EP10164079.5 | 2010-05-27 | ||
PCT/EP2011/058460 WO2011147822A2 (en) | 2010-05-27 | 2011-05-24 | Agricultural formulations with acyl morpholines and polar aprotic co-solvents |
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AU2012342490B2 (en) * | 2011-11-24 | 2015-08-06 | Akzo Nobel Chemicals International B.V. | Agricultural formulations with aromatic solvents and acyl morpholines |
RU2606800C2 (ru) * | 2011-11-24 | 2017-01-10 | Акцо Нобель Кемикалз Интернэшнл Б.В. | Сельскохозяйственные составы с амидами и ацилморфолинами |
WO2013087430A1 (de) * | 2011-12-14 | 2013-06-20 | Basf Se | Emulgierbares konzentrat enthaltend pestizid, amid und carbonat |
US9622478B2 (en) * | 2012-10-16 | 2017-04-18 | Solano S.P. Ltd. | Topical formulations for treating parasitic infestations |
KR102148891B1 (ko) * | 2012-12-15 | 2020-08-28 | 비와이케이-케미 게엠베하 | 유동성 조절용 조성물 |
CN104955331A (zh) * | 2013-01-29 | 2015-09-30 | 日产化学工业株式会社 | 乳化稳定性优异的农药乳化性组合物 |
JP2017520661A (ja) * | 2014-06-24 | 2017-07-27 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | N−ホルミルモルホリン又はn−アセチルモルホリン中におけるポリフッ化ビニリデン溶液 |
CN107105642A (zh) | 2015-01-14 | 2017-08-29 | 斯托尔勒企业公司 | 植物生长调节剂与极性和/或半极性有机溶剂的非水溶液 |
WO2017187435A1 (en) | 2016-04-24 | 2017-11-02 | Solano S.P. Ltd. | Dinotefuran liquid flea and tick treatment |
WO2024018453A1 (en) * | 2022-07-21 | 2024-01-25 | Adama Makhteshim Ltd. | Compositions of triazole fungicides |
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PL2575446T3 (pl) | 2016-10-31 |
WO2011147822A2 (en) | 2011-12-01 |
AU2011257348A1 (en) | 2012-11-22 |
WO2011147822A3 (en) | 2012-04-12 |
ES2581805T3 (es) | 2016-09-07 |
EA201291293A1 (ru) | 2013-04-30 |
CA2798997C (en) | 2018-05-15 |
EP2575446B1 (en) | 2016-04-20 |
EA022368B1 (ru) | 2015-12-30 |
CN102905523A (zh) | 2013-01-30 |
JP2013527188A (ja) | 2013-06-27 |
EP2575446A2 (en) | 2013-04-10 |
NZ603409A (en) | 2014-01-31 |
US20130130908A1 (en) | 2013-05-23 |
BR112012029606A2 (pt) | 2015-10-13 |
AU2011257348B2 (en) | 2014-02-27 |
US8791145B2 (en) | 2014-07-29 |
JP5632536B2 (ja) | 2014-11-26 |
BR112012029606B1 (pt) | 2018-04-03 |
CA2798997A1 (en) | 2011-12-01 |
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