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CN107708421A - For the reagent and method of the E/Z isomerization for reducing dimethomorph - Google Patents

For the reagent and method of the E/Z isomerization for reducing dimethomorph Download PDF

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Publication number
CN107708421A
CN107708421A CN201680032793.2A CN201680032793A CN107708421A CN 107708421 A CN107708421 A CN 107708421A CN 201680032793 A CN201680032793 A CN 201680032793A CN 107708421 A CN107708421 A CN 107708421A
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dimethomorph
isomers
composition
weight
phosethyl
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Granted
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CN201680032793.2A
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CN107708421B (en
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詹姆斯·蒂莫西·布里斯托
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Jiangsu Rotam Chemical Co Ltd
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Jiangsu Rotam Chemical Co Ltd
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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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • 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
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The method for providing the E/Z isomerization for reducing dimethomorph, this method include applying dimethomorph together with phosethyl-Al.Additionally provide make dimethomorph in the presence of light Fungicidally active unstability reduce method, this method include dimethomorph is contacted with phosethyl-Al.The method for further providing the fungal infection for preventing or reducing plant in place, this method include applying dimethomorph and phosethyl-Al to the place.Composition includes dimethomorph and phosethyl-Al.

Description

For the reagent and method of the E/Z isomerization for reducing dimethomorph
The cross reference of related application
This application claims in the priority of the GB1515894.2 UK Patent Applications submitted on the 8th of September in 2015, its Content is incorporated herein by reference.
The invention provides the reagent of the E/Z isomerization for reducing dimethomorph.The invention further relates to composition, Said composition includes E the and/or Z isomers and conversion reagent of dimethomorph.The invention further relates to the E/Z for reducing dimethomorph The method of isomerization.
Agrochemically active compound such as agricultural chemicals is commonly exposed in shining upon after applying out of doors.For some Reactive compound, this causes the reduction of their pesticide activities.
(EZ) -4- [3- (4- chlorphenyls) -3- (3,4- Dimethoxyphenyl) acryloyl group] morpholine, popular name dimethomorph, It is known fungicide.Dimethomorph can be used as E and Z isomers to exist, as follows.
However, the only Z isomers of dimethomorph as fungicide is substantially active.By light irradiation, most Isomerization occurs for the Z isomers just applied, and turns into E isomer.
It has been found that after light irradiation, dimethomorph loses activity.More specifically, the effect of light irradiation dimethomorph is Z isomers is converted into E isomer, causes the loss of Fungicidally active.
Therefore, it is necessary to increase the technology of stability when dimethomorph is exposed to light.In particular it is required that reduce dimethomorph Isomerization after light is more particularly the technology of E/Z isomerization.
Unexpectedly, it has now been found that E/Z isomerization of the dimethomorph after light can be by using reagent (particularly phosethyl-Al) reduces.Specifically, it has been found that apply dimethomorph and triethylphosphine acid to pending place It is sudden and violent that aluminium (such as by way of composition comprising both dimethomorph and phosethyl-Al) significantly reduces dimethomorph It is exposed to the isomerization after light, particularly conversion of the Z isomers to E isomer.This so maintain dimethomorph active component Fungicidally active.
Therefore, in a first aspect, the invention provides the method for the E/Z isomerization for reducing dimethomorph, this method includes Using dimethomorph together with phosethyl-Al.
In second aspect, reduced the invention provides the unstability for making dimethomorph Fungicidally active in the presence of light Method, this method include making dimethomorph contact with phosethyl-Al.
In a further aspect, the invention provides the method in place prevention or the fungal infection for reducing plant, this method Including applying dimethomorph and phosethyl-Al to the place.
In another further aspect, the invention provides the composition for including dimethomorph and phosethyl-Al.
Still further, the purposes the invention provides phosethyl-Al in the E/Z isomerization for reducing dimethomorph.
The E/Z isomerization of dimethomorph is understood to refer to from E isomer to Z isomers or from Z isomers to E isomer Double bond conversion.It has been found that the Z isomers that the presence of phosethyl-Al significantly reduces dimethomorph turns to E isomer Change.Furthermore, it has been found that in the case of the mixture of the E and Z isomers of dimethomorph, the presence of phosethyl-Al can be with With the amount of the existing Z isomers of time increase.
If the weight ratio of the Z isomers of dimethomorph and E isomer is with being not present three in the presence of phosethyl-Al The change of the ratio, which is compared, during fosetyl-aluminium reduces slower, or the weight of Z isomers and E isomer ratio originates with it Value is identical compared to holding or increases, then the reduction of the E/Z isomerization of dimethomorph is achieved.
Dimethomorph can be adopted in the form of the combination of E isomer, Z isomers or both isomers in the present invention With or exist.E and Z isomers can be present in dimethomorph component with any relative quantity.Based on dimethomorph E and Z isomery The total amount of body, E the or Z isomers of dimethomorph can each with least 5wt.%, preferably at least 10wt.%, more preferably at least 20wt.%, still more preferably at least 30wt.%, even more preferably at least 40wt.%, particularly preferably at least 50wt.% amount exist In said composition.These values are related to alkene acyl existing for initial (i.e. when dimethomorph merges or contacted with phosethyl-Al) The amount of the isomers of morpholine.
In an aspect, the invention provides the composition for including dimethomorph and phosethyl-Al.Dimethomorph can It is present in the amount with Fungicidally active needed for any be adapted to provide in said composition.Dimethomorph can be with least 0.1wt.%, more preferably at least 1wt.%, still more preferably at least 2wt.%, more preferably at least 3wt.% amount are present in the combination In thing.Dimethomorph can with most 99wt.%, preferably up to 90wt.%, more preferably up to 80wt.%, still more preferably at most 75wt.% amount is present.The amount of dimethomorph can be the 0.1wt.% to 99wt.% of said composition, and preferably 1wt.% is extremely 70wt.%, more preferably 1wt.% are to 50wt.%, and still more preferably from 1wt.% to 30wt.%, still more preferably 1wt.% is extremely 10wt.%.In one embodiment, dimethomorph is present in said composition with the 7wt.% of said composition amount.
As discussed above, the presence of phosethyl-Al reduces or prevented the Z isomers of dimethomorph to E isomer Conversion, and conversion of the E isomer to Z isomers can be promoted.It is not intended to any particular theory, it is believed that triethylphosphine The group that sour aluminium can produce the double bond of attack dimethomorph E isomer and allow singly-bound to rotate.Phosethyl-Al can be with pure Form used as industrial grade mixture.
As it is indicated above, in one aspect of the invention, there is provided comprising dimethomorph and phosethyl-Al Composition.In the present compositions, phosethyl-Al can be with any phase for being suitable for maintaining dimethomorph fungicide The amount of Fungicidally active is hoped to exist.Phosethyl-Al can be with said composition from 0.1wt.%, preferably from 1wt.%, more preferably From 5wt.%, still more preferably from 10wt.%, still more preferably exist from 20wt.% amount.Phosethyl-Al can be with most 99wt.%, preferably up to 90wt.%, more preferably up to 80wt.%, still more preferably at most 75wt.%, still more preferably at most 70wt.% amount is present.Phosethyl-Al can in the composition with 0.1wt.% to 99wt.%, preferably from 1wt.% to To 70wt.%, still more preferably 50wt.% to 60wt.% amount is present by 80wt.%, more preferably 30wt.%.
As it is indicated above, in the present invention, the effect of phosethyl-Al is to reduce the Z isomers of dimethomorph to E Isomers converts and increases conversion of the E isomer to Z isomers.In the present invention, initial dimethomorph can be with Z isomeries The form of the mixture of body, E isomer or both isomers uses.It is present in initial alkene in the Z isomers of dimethomorph In the case of in morpholide material, the effect of phosethyl-Al is to maintain the presence of Z isomers.In the E isomer of dimethomorph In the case of being present in initial dimethomorph material, the effect of phosethyl-Al is that E isomer is converted into Z isomers, Thus maintain or increase the amount of existing Z isomers.
It is preferred that use dimethomorph in the form of including Z isomers at least in part.In this way, from beginning to use, alkene Morpholide just has Fungicidally active.
Preferably, the initial dimethomorph material includes at least 10wt.% Z isomers, more preferably at least 20wt.%, Still more preferably at least 30wt.%, at least still more preferably 40wt.%, at least particularly preferably 50wt.%.The initial dimethomorph material Material can include the Z isomers of higher amount, for example, at least 60wt.%, 70wt.%, 80wt.% or 90wt.%.The initial alkene acyl Morpholine material substantially can be made up of Z isomers.Alternately, the initial dimethomorph material can be substantially by E isomeries Body forms, although this is not preferred embodiment.
In the presence of phosethyl-Al, the amount of Z isomers generally changes, and more preferably increases.Preferably, triethylphosphine acid Aluminium is used with following amount so that after being contacted with dimethomorph, the Z isomers of dimethomorph with dimethomorph material at least 50wt.% amount is present, more preferably at least 60wt.% amount, still more preferably at least 70wt.% amount, still more preferably at least 80wt.% amount, wherein particularly preferably at least 85wt% and at least 90wt%.Z isomeries with higher pesticide activity Body is preferably what is be present in excess.
The present invention can use the composition comprising dimethomorph and phosethyl-Al.Alternately, or additionally, this hair It is bright to use with the dimethomorph and phosethyl-Al of separated composition offer.
Composition for the present invention can be configured to conventional any type for agrochemical formulations, such as Solution, emulsion, suspension, dirt agent, pulvis, paste and particle.The type of preparation depends on specific desired use and should carried For the fine and uniform distribution of active component phosethyl-Al and dimethomorph.The example of suitable types of compositions is solvable Liquor (water-soluble concentrates, SL), missible oil (emulsifiable concentrates, EC), aqueous emulsion (emulsions, EW), microemulsion (micro-emulsions, ME), suspending agent (suspension concentrates, SC), Oil-based suspension (oil-based suspension concentrates, OD), suspension seed-coating agent (flowable Suspensions, FS), water dispersible granules (water-dispersible granules, WG), soluble granule (water- Soluble granules, SG), wettable powder (wettable powders, WP), solvable pulvis (water-soluble Powders, SP), granule (granules, GR), microcapsulated granule (encapsulated granules, CG), granula subtilis (fine granules, FG), big granula (macrogranules, GG), suspension emulsion (aqueous suspo-emulsions, SE), microcapsule suspending agent (capsule suspensions, CS) and fine granule (microgranules, MG).Preferable preparation class Type is water dispersible granules (WG) and suspending agent (SC).
As it is indicated above, the alternative solution as the present composition, can be used separately phosethyl-Al and alkene Morpholide, such as place is applied to by being used as separated preparation, or by merge before the place is applied to (such as when During preparing bucket mixture (tank mix)).In such a case, it is possible to phosethyl-Al is each used with one of above-mentioned preparation type And dimethomorph.
Preparation can further include conventional auxiliary agent for plant protection composition as known in the art, auxiliary agent Selection depending on preparation type and its desired use.Typical auxiliary agent include extender, carrier, solvent, surfactant, Stabilizer, defoamer, antifreezing agent, preservative, antioxidant, colouring agent, thickener, solid sticks and inert filler.This Analog assistant is known in the art and is commercially available.Their uses in the preparation of the present composition are to this area It will be apparent for technical staff.
Composition can further include one or more inert fillers.Such inert filler is known in the art simultaneously And it is commercially available.Suitable filler includes for example natural ground mineral, as kaolin, aluminum oxide, talcum, chalk, quartz, Attapulgite, montmorillonite and diatomite；Or synthesis ground mineral, such as the silicic acid of high degree of dispersion, aluminum oxide, silicate and phosphorus Sour calcium and hydrophosphate.Suitable inert filler for granule includes the natural minerals for for example crushing and being classified, such as side's solution Stone, marble, float stone, sepiolite and dolomite；Or the synthesis particle of inorganic and organic earth material；And organic material is for example Wood sawdust, coconut husk, the particle of corncob and tobacco stem.
Composition optionally includes one or more of surfactants, is nonionic, cationic on preferred property And/or anionic；And surfactant mixture, it, which has, good emulsify, disperses and wet characteristic.Surfactant Selection depending on preparation type and desired use.Suitable surfactant be known in the art and be can business Purchase.
Suitable anion surfactant can be so-called water-soluble soap and water-soluble synthetic surface reactive compound Both.The soap that can be used is higher fatty acids (C10To C22) alkali metal salt, alkali salt or substituted or unsubstituted Ammonium salt, such as the sodium salt or sylvite of oleic acid or stearic acid or natural acid mixture.Surfactant can be ion or non- Emulsifying agent, dispersant or the wetting agent of ionic.The example that can be used is the salt of polyacrylic acid, the salt of lignosulphonic acid, benzene sulphur Acid or naphthalene sulfonic acids salt, oxirane and fatty alcohol with aliphatic acid or with the condensation polymer of fatty amine, fortified phenol (especially alkane Base phenol), sulfosuccinate ester salt, taurine derivatives (especially taurine Arrcostab) or the phosphoric acid of polyethoxylated phenol or alcohol Ester.When reactive compound and/or inert carrier and/or auxiliary agent/adjuvant is not soluble in water and the final of composition is using carrier Usually require at least one surfactant be present during water.
Composition optionally further includes one or more of polymer stabilizers.What can be used in the present invention is suitable The polymer stabilizer of conjunction includes but is not limited to the copolymerization of polypropylene, polyisobutene, polyisoprene, monoolefine and alkadienes Thing, polyacrylate, polystyrene, polyvinyl acetate, polyurethane or polyamide.Suitable stabilizer is known in the art And be commercially available.
It has been generally acknowledged that surfactant mentioned above and polymer stabilizer, which are composition, assigns stability, allow for Prepare, store, transport and using composition.
Suitable defoamer includes all substances that generally can be in agrochemical composition for this purpose.Suitable disappears Infusion is known in the art and is commercially available.Particularly preferred defoamer is dimethyl silicone polymer and perfluoroalkyl The mixture of phosphonic acids, such as the silicone antifoams agent that can be obtained from GE or Compton Co., Ltd (Compton).
Suitable organic solvent is selected from all usual organic solvents of fully reactive compound used in dissolving.Similarly, Suitable organic solvent for dimethomorph and phosethyl-Al is as known in the art.Mentioned below can be preferred 's：1-METHYLPYRROLIDONE, NOP, cyclohexyl -1- pyrrolidones；Or SOLVESSOTM200, paraffin hydrocarbon, different stone The mixture of wax hydrocarbon, ring paraffin hydrocarbon and aromatic hydrocarbon.Suitable solvent is commercially available.
Suitable preservative includes that the institute of this purpose can be generally used in such agrochemical composition There is material and be equally well-known in the art.It can be mentioned that suitable example include(come from and visit Ear company (Bayer AG)) and(coming from Beyer Co., Ltd).
Suitable antioxidant is all substances that can be generally used for this purpose in agrochemical composition, is such as existed It is known in the art.Preferably Butylated Hydroxytoluene.
Suitable thickener includes all substances that generally can be in agrochemical composition for this purpose.Such as xanthan Glue, polyvinyl alcohol (PVOH), cellulose and its derivates, clay hydration silicate, zeopan or their mixture.Together Sample, such thickener is as is generally known in the art and is commercially available.
Said composition can be applied with method as known in the art.These methods include spraying (misting), dusting, Spread, brush, perfusion, coating, spraying (spraying), dipping, immersion, injection and irrigate.
Phosethyl-Al can contact in any stage during the preparation and use of the present invention with dimethomorph.Example Such as, two kinds of components can be merged in single composition.Alternately, can be by two kinds of component separate administrations and in place Place merges.As another alternative solution, two kinds of component into contact can be made before use is faced, such as mix by being used as bucket The mode of agent.
In the present invention administration (use) rate of phosethyl-Al and dimethomorph can for example according to usage type, make species Type, used concrete activity compound, vegetation type and change, but should make it that the reactive compound in combination is with carrying Applied for the effective dose of hope effect (for example, disease or harmful organism control).It can be readily determined and be directed to by experiment The component amount of application of one group of specified criteria.
Dimethomorph and the respective appropriate rate of application of phosethyl-Al are in the range of 50 to 5000 grams/ha.Alkene The preferred compositions rate of application of both morpholide and phosethyl-Al is from 500 to 5000 grams/ha.
Generally, when using 100 to 400 grams/ha, such as 210 grams/ha of dimethomorph and 750 to 3000 grams/ Hectare, such as during 1500 or 1800 grams/ha of phosethyl-Al, gratifying result will be obtained.
The present invention can be used for preventing and/or treat the disease as caused by the fungal pathogens of wide scope, these nosomycosises Substance is such as, but not limited to：
Pseudoperonospora cubensis (Pseudoperonos pora cubensis) (downy mildew)；Phytophthora (Phytophthora)； Pseudoperonospora cubensis such as on muskmelon, watermelon, small cucumber, pumpkin and the Curcurbitaceae of cucumber；
Fruit such as apple, avocado, black raspberry, blackberry, blueberry, blueberry, citrus, Cranberry, grape, grapevine, peach, phoenix Phytophthora, grape branch-rot bacterium (Phomopsis viticola), vascular bundle on pears, raspberry, raspberry and strawberry is false Cup fungi (Pseudopeziza tracheiphila), blister spot (pseudomonas syringae bleb pvs oryzae and oryzicola (Pseudomonas Syringae pv.papulans)), phytophthora root rot (the strawberry epidemic disease certain kind of berries (Phytophthora fragariae)), phytophthora root-rot Sick (phytophthora species), red stele (the strawberry epidemic disease certain kind of berries), phytophthora root rot (camphor tree phytophthora (Phytophthora cinnamomi)), Anthracnose fruit rot (colletotrichum gloeosporioides Penz (Colletotrichum gloeosporioides)), Phomopsis canker are (more Tangerine Phomopsis (Phomopsis vaccini-i)), neck rot (Phytophthora cactorum (Phytophthora cactorum)), rotten worry (camphor tree phytophthora), root rot (mutation of Phytophthora nicotianae parasitism (Phytophthora nicotinanae var.parasitica)), frost Mildew (downy mildew (Plasmopara viticola)), crown rot (Phytophthora cactorum), root rot (phytophthora species)；
Phytophthora root rot on ginseng；
Pythium (Phythium), Phytophthora, crown rot and root rot (phytophthora species), phytophthora root on ornamental plant Maize ear rot (camphor tree phytophthora), air phytophthora (aerial phytophthora) (phytophthora species, including robur sudden death pathogen (Phytophthora ramorum), moral thunder phytophthora (Phytophthora drechsleri), Phytophthora nicotianae Breda (Phytophthora nicotinanae) and phytophthora parasitica (Phytophthora parasitica)), phytophthora root, hat and Stem rot (phytophthora species), downy mildew (Bremia (Bremia), Pseudoperonospora (Pseudoperonospora), Peronospora (Peronospora) and Plasmopara (Plasmopara) species), downy mildew (tree-shaped downy mildew (Peronospora Arborescens)), downy mildew (humulus grass vacation downy mildew (Pseudoperonospora humuli))；
Mould (Peronospora tabacina (Peronospora tabacina)) on tobacco；
Rotten mildew, blade face and basal rot anthracnose, bent grass dead point (bentgrass deadspot) on turf；
Black spot (Alternaria species (Alternaria spp.)) on vegetables, anthracnose (colletotrichum species (Colletotrichum spp.), potato anthrax bacteria (Colletotrichum coccodes), C. dematium (Colletotrichum dematium), colletotrichum gloeosporioides Penz (Colletotrichum gloeosporioides), GLOMERFLLA CINGULATA (Glomerella cingulata) [epigamous], the born of the same parents bacterium of lettuce disk two (Marssonina panattoniana)), gray mold (lettuce disk obstructs mould (Bremia for (botrytis bunch rot) (Botrytis cinerea (Botrytis cinerea)), downy mildew Lactucae), spinach powder downy mildew (Peronospora farinose f.sp.Spinaciae), parasitic transparent downy mildew (Hyaloperonospora parasitica), Peronospora parasitic (Peronospora parasitica), shallot downy mildew (Peronospora destructor), shallot downy mildew (Peronospora destructor), bacterium of downy mildew of cucumber (Pseudoperonospora cubensis), lettuce disk obstruct mould, downy mildew species), early blight (alternaria solani sorauer (Alternaria solani)), blight dis-ease (melon didymella bryoniae (Didymella bryoniae)), late blight (phytophthora infestans (Phytophthora infestans)), leaf blight (squamous grape spore (Botrytis squamosal)), leaf spot (peace enlightening Dagger-axe receives Phoma sp An Dina mutation (Phoma andigena var.andina)), phytophthora root rot (phytophthora species, hidden ground epidemic disease Mould (P.cryptogea)), purple blotch (green onion rod method (Alternaria porri)), septoria musiva leaf spot (septoria Leaf spot) (Septoria species (Septoria spp.)), white blister (west white rust (Albugo Occidentalis)), for example Chinese cucumber of the vegetables, balsam apple, balsam pear, Belgian endive, pakchoi, long calyx Cymbidium leaf The small cabbage of vegetables, broccoli, wild cabbage, cabbage, cabbage (Chinese (napa)), cabbage (Chinese leaf mustard), cantaloupe, flower It is cabbage, Franco Cavallo broccoli, Chinese wax gourd, citron watermelon, cucurbit, edible cucurbit, eggplant, garlic, garlic (major part), small Cucumber, ground-cheery, root-mustard, leek, lettuce, muskmelon, onion, onion (dry bulb), onion (green), onion (Wei Erqi (Welch)), eggplant melon, capsicum, potato, turnip, green onion, spinach, zucchini, green tomato, tomato and butternut squash.
In addition, the present invention can be used for preventing and/or treatment disease as caused by fungal pathogens, these fungal pathogen styles Such as but it is not limited to：
Downy mildew (downy mildew) of the fruit for example on grape；
Phytophthora infestans (late blight) of the vegetables for example on tomato, eggplant and capsicum；And
Bacterium of downy mildew of cucumber (downy mildew) of the Curcurbitaceae for example on muskmelon, watermelon, small cucumber, pumpkin and cucumber.
The present invention has series of advantages.First, the Z of dimethomorph to E isomerization rate significantly reduces.As knot Fruit, the dimethomorph material of administration keep sustained activity more long in the sun.As other result, the rate of application of dimethomorph It can reduce.
Dimethomorph and phosethyl-Al simultaneously or continuously can be applied on the same day with short time interval, for example Wish by plant, plant part and/or the surrounding controlled.Dimethomorph and phosethyl-Al can be administered in any order Plant, one or more part (such as leaf or seed) or surrounding.Every kind of compound can be using only once or repeatedly.It is preferred that Ground, dimethomorph and phosethyl-Al each apply repeatedly, particularly from 1 to 5 times, more preferably 2 times.
Dimethomorph and phosethyl-Al can sequentially or concurrently be applied by any desired order, any combinations. In the case of dimethomorph and phosethyl-Al are administered simultaneously in the present invention, they can be used as and include dimethomorph and three second The composition of phosphonic acids aluminium is applied, in this case dimethomorph and phosethyl-Al can each be obtained from single preparation source and Mix and (be referred to as mixed bucket, instant, spray liquid or slurry), optionally together with other agricultural chemicals；Or dimethomorph and Phosethyl-Al can be provided as unitary agent mix source (be referred to as premix, concentrate, prepare compound (or production Product)), and optionally together with other pestsides synthesis.
Following facts is distinguished by according to the composition of the present invention：They are particularly well resistant to by plant and are Environment-friendly.
The present invention will be further described by specific examples below, and these embodiments are presented and are for illustration purposes only.
In the examples below, indicated percentage is by weight, unless otherwise indicated.
Embodiment
The preparation of embodiment 1- compositions
It is prepared for following composition.Prepare composition 8 and 9 for comparative purposes, and not embodiments of the invention.
Composition 1：The phosethyl-Als of WDG 10%
Water-dispersible granular material (WDG) preparation is prepared as with consisting of：
7% dimethomorph；10% phosethyl-Al；5% lauryl sodium sulfate；5% poly alkyl alcohol glycol ethers；2% wood Quality sulfonic acid, sodium salt are sulfomethylated；8% ammonium sulfate；1% defoamer；25% sucrose and 37% lactose.
For forming the mixture that the dimethomorph of said composition includes E and Z isomers.
Composition 2：The phosethyl-Als of WDG 20%
Water-dispersible granular material (WDG) preparation is prepared as with consisting of：
7% dimethomorph；20% phosethyl-Al；5% lauryl sodium sulfate；5% poly alkyl alcohol glycol ethers；2% wood Quality sulfonic acid, sodium salt are sulfomethylated；8% ammonium sulfate；1% defoamer；20% sucrose and 32% lactose.
For forming the mixture that the dimethomorph of said composition includes E and Z isomers.
Composition 3：The phosethyl-Als of WDG 30%
Water-dispersible granular material (WDG) preparation is prepared as with consisting of：
7% dimethomorph；30% phosethyl-Al；5% lauryl sodium sulfate；5% poly alkyl alcohol glycol ethers；2% wood Quality sulfonic acid, sodium salt are sulfomethylated；8% ammonium sulfate；1% defoamer；17% sucrose and 25% lactose.
For forming the mixture that the dimethomorph of said composition includes E and Z isomers.
Composition 4：The phosethyl-Als of WDG 50%
Water-dispersible granular material (WDG) preparation is prepared as with consisting of：
7% dimethomorph；50% phosethyl-Al；5% lauryl sodium sulfate；5% poly alkyl alcohol glycol ethers；2% wood Quality sulfonic acid, sodium salt are sulfomethylated；8% ammonium sulfate；1% defoamer；9% sucrose and 13% lactose.
For forming the mixture that the dimethomorph of said composition includes E and Z isomers.
Composition 5：The phosethyl-Als of WDG 60%
Water-dispersible granular material (WDG) preparation is prepared as with consisting of：
7% dimethomorph；60% phosethyl-Al；5% lauryl sodium sulfate；5% poly alkyl alcohol glycol ethers；2% wood Quality sulfonic acid, sodium salt are sulfomethylated；8% ammonium sulfate；1% defoamer；6% sucrose and 16% lactose.
For forming the mixture that the dimethomorph of said composition includes E and Z isomers.
Composition 6：The phosethyl-Als of WDG 70%
Water-dispersible granular material (WDG) preparation is prepared as with consisting of：
7% dimethomorph；70% phosethyl-Al；5% lauryl sodium sulfate；5% poly alkyl alcohol glycol ethers；2% wood Quality sulfonic acid, sodium salt are sulfomethylated；8% ammonium sulfate；1% defoamer；1% sucrose and 1% lactose.
For forming the mixture that the dimethomorph of said composition includes E and Z isomers.
Composition 7：The phosethyl-Als of SC 50%
Suspending agent (SC) preparation is prepared as with consisting of：
7% dimethomorph；50% phosethyl-Al；10% propane diols；5% triphenylethylene base polyoxyether；1% sulfomethylated lignin Sour sodium；1% carboxymethyl cellulose；1% silicone oil (form in 75% emulsion in water)；Water (is balanced to 1L).
Such as include the mixture of E and Z isomers for forming the dimethomorph of said composition.
Composition 8：The phosethyl-Als of WDG 0%
Water-dispersible granular material (WDG) preparation is prepared as with consisting of：
7% dimethomorph；5% lauryl sodium sulfate；5% poly alkyl alcohol glycol ethers；2% lignin sulfonic acid, sodium salt, sulphur Methylate；8% ammonium sulfate；1% defoamer；30% sucrose and 42% lactose.
For forming the mixture that the dimethomorph of said composition includes E and Z isomers.
Composition 9：The phosethyl-Als of SC 0%
Suspending agent (SC) preparation is prepared as with consisting of：
7% dimethomorph；10% propane diols；5% tristyrylphenol polyoxyethylene ether；1% sodium lignin sulfonate； 1% carboxymethyl cellulose；1% silicone oil (form of 75% emulsion in water)；Water (is balanced to 1L).
For forming the mixture that the dimethomorph of said composition includes E and Z isomers.
Irradiation and the isomerization analysis of embodiment 2- dimethomorphs
The effect that light irradiation is used on composition in embodiment 1 is tested as follows：
The composition prepared in embodiment 1 is each diluted with water.Three samples of 20mg gained dilution are taken, and Drip on glass plate and be placed in and dry at room temperature.Then 0,25 and 100 minute is continued with three drying samples of UV light irradiations. After irradiation, pass through ultrasound application 4mL dimethyl sulfoxides (DMSO) washing sample from glass plate.Sample is separated by HPLC Into E the and Z isomers of dimethomorph.The amount of the E and Z isomers of dimethomorph is measured by peak area, and for each The percentage of the Z isomers of dimethomorph existing for sample measure.These results are shown in table 1 below.
Table 1
Can be seen that the presence of phosethyl-Al in the composition from the data being presented in table 1 reduces alkene acyl Conversion of the E isomer of quinoline to Z isomers, and cause the amount of Z isomers to increase with experimental period.
Example 3 is directed to field test viny (downy mildew)
Immature grape tree plant is given into suspension spray with the mitogenetic spore of downy mildew, and it is relatively large in 20 DEG C and 100% It is incubated 48 hours under air humidity degree.
Following compositions are prepared, is then each diluted with water and is sprayed on plant.
Composition A：
7% dimethomorph (Z isomers)；50% phosethyl-Al；5% lauryl sodium sulfate；5% poly alkyl alcohol glycol Ether；2% lignin sulfonic acid, sodium salt are sulfomethylated；8% ammonium sulfate；1% defoamer；9% sucrose and 13% lactose.
Composition B：
7% dimethomorph (Z isomers)；5% lauryl sodium sulfate；5% poly alkyl alcohol glycol ethers；2% sulfomethylated lignin Acid, sodium salt are sulfomethylated；8% ammonium sulfate；1% defoamer；30% sucrose and 42% lactose.
Composition C：
50% phosethyl-Al；5% lauryl sodium sulfate；5% poly alkyl alcohol glycol ethers；2% lignin sulfonic acid, sodium Salt, it is sulfomethylated；8% ammonium sulfate；1% defoamer；30% sucrose and 42% lactose.
Using composition B and C merely for omparison purpose, and not embodiment of the present invention.
The reference composition (but without dimethomorph and phosethyl-Al) prepared according to composition A is also prepared for, again For comparative purposes.
One group of plant is stored in dark, and another group of plant is stored in the sunlight.By two groups of plants all 15 DEG C and the greenhouse of 80% relative atmospheric humidity in kept for 7 days.
After this, the seriousness of the fungal infection of plant is checked.Seriousness is defined as to show visual fungal infection Plant percentage.As a result listed in table 2 below.
Table 2
It is can be seen that from the data in upper table 2 when with plant of the solar radiation through processing, composition B and C and control Show significantly reduced fungicidal action.By contrast, under dark condition and when with solar radiation in the case of two kinds, alkene The presence of both morpholide and phosethyl-Al in composition A provides the Fungicidally active of height.

Claims (51)

1. reducing the method for the E/Z isomerization of dimethomorph, methods described includes applying dimethomorph together with phosethyl-Al.
2. according to the method for claim 1, wherein dimethomorph is with E isomer, Z isomers or E isomer and Z isomeries The form of the combination of body is present.
3. according to the method described in any preceding claims, wherein the dimethomorph includes alkene existing by weight The E isomer or Z isomers of at least 5% amount of morpholide total amount.
4. according to the method for claim 3, wherein the dimethomorph includes dimethomorph existing by weight The E isomer or Z isomers of at least 10% amount of total amount.
5. according to the method for claim 4, wherein the dimethomorph includes dimethomorph existing by weight The E isomer or Z isomers of at least 40% amount of total amount.
6. according to the method described in any preceding claims, wherein dimethomorph initially includes by weight at least 10% Z Isomers.
7. according to the method for claim 6, wherein dimethomorph initially includes by weight at least 30% Z isomers.
8. according to the method described in any preceding claims, wherein methods described uses and includes dimethomorph and phosethyl-Al Composition.
9. method according to any one of claim 1 to 7, wherein dimethomorph and phosethyl-Al are dividually applied To pending place.
10. make dimethomorph in the presence of light Fungicidally active unstability reduce method, methods described include make alkene acyl Morpholine contacts with phosethyl-Al.
11. according to the method for claim 10, wherein dimethomorph is different with E isomer, Z isomers or E isomer and Z The form of the combination of structure body is present.
12. according to the method described in any one of claim 10 or 11, wherein the dimethomorph includes institute by weight The E isomer or Z isomers of at least 5% amount of existing dimethomorph total amount.
13. according to the method for claim 12, wherein the dimethomorph includes alkene acyl existing by weight The E isomer or Z isomers of at least 10% amount of quinoline total amount.
14. according to the method for claim 13, wherein the dimethomorph includes alkene acyl existing by weight The E isomer or Z isomers of at least 40% amount of quinoline total amount.
15. the method according to any one of claim 10 to 14, wherein dimethomorph are initially comprising by weight at least 10% Z isomers.
16. according to the method for claim 15, wherein dimethomorph initially includes by weight at least 30% Z isomeries Body.
17. the method according to any one of claim 10 to 16, wherein methods described use and include dimethomorph and three The composition of fosetyl-aluminium.
18. the method according to any one of claim 10 to 16, wherein by dimethomorph and phosethyl-Al dividually It is applied to pending place.
19. prevent in place or the method for the fungal infection of reduction plant, methods described include applying alkene acyl to the place Quinoline and phosethyl-Al.
20. according to the method for claim 19, wherein dimethomorph is different with E isomer, Z isomers or E isomer and Z The form of the combination of structure body is present.
21. according to the method described in any one of claim 19 or 20, wherein the dimethomorph includes institute by weight The E isomer or Z isomers of at least 5% amount of existing dimethomorph total amount.
22. according to the method for claim 21, wherein the dimethomorph includes alkene acyl existing by weight The E isomer or Z isomers of at least 10% amount of quinoline total amount.
23. according to the method for claim 22, wherein the dimethomorph includes alkene acyl existing by weight The E isomer or Z isomers of at least 40% amount of quinoline total amount.
24. the method according to any one of claim 19 to 23, wherein dimethomorph are initially comprising by weight at least 10% Z isomers.
25. according to the method for claim 24, wherein dimethomorph initially includes by weight at least 30% Z isomeries Body.
26. the method according to any one of claim 19 to 25, wherein methods described use and include dimethomorph and three The composition of fosetyl-aluminium.
27. the method according to any one of claim 19 to 26, wherein by dimethomorph and phosethyl-Al dividually It is applied to pending place.
28. the method according to any one of claim 19 to 27, wherein by dimethomorph with 100 grams/ha to 400 Gram/ha ratio be applied to the place.
29. the method according to any one of claim 19 to 28, wherein by phosethyl-Al with 750 grams/ha extremely 1000 grams/ha of ratio is applied to the place.
30. the method according to any one of claim 19 to 29, it is applied when handling or preventing following infect：
Downy mildew (downy mildew) on fruit；
Phytophthora infestans (late blight) on vegetables；Or
Bacterium of downy mildew of cucumber (downy mildew) on Curcurbitaceae.
31. composition, the composition includes dimethomorph and phosethyl-Al.
32. composition according to claim 31, wherein dimethomorph are present in described with least 1% amount by weight In composition.
33. composition according to claim 32, wherein dimethomorph are present in described with least 3% amount by weight In composition.
34. the composition according to any one of claim 31 to 33, wherein dimethomorph are by weight with most 90% Amount be present in the composition.
35. composition according to claim 34, wherein dimethomorph are present in institute with most 75% amount by weight State in composition.
36. the composition according to any one of claim 31 to 35, wherein phosethyl-Al are by weight with least 1% Amount be present in the composition.
37. composition according to claim 36, wherein phosethyl-Al are present in at least 10% amount by weight In the composition.
38. the composition according to any one of claim 31 to 37, wherein phosethyl-Al are by weight with most 90% amount is present in the composition.
39. the composition according to claim 38, wherein dimethomorph are present in institute with most 75% amount by weight State in composition.
40. the composition according to any one of claim 31 to 39, wherein dimethomorph with E isomer, Z isomers or The form of the combination of person's E isomer and Z isomers is present.
41. the composition according to any one of claim 31 to 40, wherein the dimethomorph includes by weight The E isomer or Z isomers of at least 5% amount of existing dimethomorph total amount.
42. composition according to claim 41, wherein the dimethomorph includes alkene acyl existing by weight The E isomer or Z isomers of at least 10% amount of morpholine total amount.
43. composition according to claim 42, wherein the dimethomorph includes alkene acyl existing by weight The E isomer or Z isomers of at least 40% amount of morpholine total amount.
44. the composition according to any one of claim 31 to 43, wherein the dimethomorph is initially comprising by weight The Z isomers of meter at least 10%.
45. composition according to claim 44, wherein dimethomorph initially include by weight at least 30% Z isomeries Body.
46. purposes of the phosethyl-Al in the E/Z isomerization for reducing dimethomorph.
47. substantially as described above, reduce dimethomorph E/Z isomerization method.
48. substantially as described above, make dimethomorph in the presence of light Fungicidally active unstability reduce method.
49. substantially as described above, place prevent or reduce plant fungal infection method.
50. substantially as described above, the composition that includes dimethomorph and phosethyl-Al.
51. substantially as described above, phosethyl-Al is reducing the purposes of the E/Z isomerization of dimethomorph.
CN201680032793.2A 2015-09-08 2016-08-30 Reagent and method for reducing E/Z isomerization of dimethomorph Expired - Fee Related CN107708421B (en)

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