GB2552694A - A Synergistic fungicidal composition and use thereof - Google Patents

A Synergistic fungicidal composition and use thereof Download PDF

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GB2552694A
GB2552694A GB1613454.6A GB201613454A GB2552694A GB 2552694 A GB2552694 A GB 2552694A GB 201613454 A GB201613454 A GB 201613454A GB 2552694 A GB2552694 A GB 2552694A
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crystalline modification
boscalid
pyraclostrobin
range
composition
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GB2552694B (en
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Timothy Bristow James
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Rotam Agrochem International Co Ltd
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Rotam Agrochem International Co Ltd
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Priority to GB1613454.6A priority Critical patent/GB2552694B/en
Priority to BR112017022487-9A priority patent/BR112017022487B1/en
Priority to CN201780047244.7A priority patent/CN109561686A/en
Priority to PCT/CN2017/094632 priority patent/WO2018024147A1/en
Priority to TW106126000A priority patent/TWI789356B/en
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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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5
    • C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
    • 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
    • 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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • 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)
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  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

A fungicidal composition comprising: (A) the crystalline modification II of 2-chloro-N (4'chloro[1,1'bipheny1]-2-y1)3-pyridinecarboxamide (boscalid); and (B) the crystalline modification IV of methyl N-{2-[1-(4-chloropheny1)-1H-pyrazol-3-yloxymethyl]phenyll(N­methoxy)carbamate (pyraclostrobin). A method of preventing and/or treating fungal infestations in plants and plant parts materials is also provided, as well as the use of the fungicidal composition in the prevention and/or treatment of fungal infections in plants and/or plant parts.

Description

(71) Applicant(s):
Rotam Agrochem International Company Limited Unit 6, 26/F, Trend Centre, 29 Cheung Lee Street, Chai Wan, Hong Kong (72) Inventor(s):
(51) INT CL:
A01N 43/40 (2006.01) A01P3/00 (2006.01) C07D 231/22 (2006.01) (56) Documents Cited:
US 7816392 B2
A01N 47/24 (2006.01) C07D 213/82 (2006.01)
US 7501384 B2 (58) Field of Search:
INT CLA01N, A01P, C07D
Other: WPI, EPODOC, TXTA, BIOSIS, CAS ONLINE
James Timothy Bristow (74) Agent and/or Address for Service:
N J AKERS & CO
Lemon Street, Truro, Cornwall, TR1 2PN, United Kingdom (54) Title of the Invention: A Synergistic fungicidal composition and use thereof
Abstract Title: Fungicidal composition comprising the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin (57) Afungicidal composition comprising: (A) the crystalline modification II of 2-chloro-N-(4'chloro[1,rbipheny1]-2-y1)3pyridinecarboxamide (boscalid); and (B) the crystalline modification IV of methyl N-{2-[1-(4-chloropheny1)-1Hpyrazol-3-yloxymethyl]phenyll(Nmethoxy)carbamate (pyraclostrobin). A method of preventing and/or treating fungal infestations in plants and plant parts materials is also provided, as well as the use of the fungicidal composition in the prevention and/or treatment of fungal infections in plants and/or plant parts.
A SYNERGISTIC FUNGICIDAL COMPOSITION AND USE THEREOF
The present invention relates to a synergistic fungicidal composition. The composition finds use in preventing and/or treating fungal infestations in plants and plant parts. The present invention also relates to a method of preventing and/or treating fungal infestations in plants and plant parts.
There is a continuing need to develop improved fungicidally active compounds, for the protection of crops. Moreover, experience with the single active straight formulation fungicides worldwide indicates there is a high risk of development of resistance. Resistance has been reported worldwide in an increasing number of pathogens of field crops, fruit, vegetable, and so on. The mixing of different fungicides may help to reduce selection pressure towards resistance in the target pathogens.
The compound 2-chloro-N-(4’chloro[1,1 ’biphenyl]-2-yl)-3-pyridinecarboxamide having the common name boscalid, was first described in US 5,330,995. The crystalline modification I of the anhydrate of boscalid, having a melting point from 144 °C to 145°C, is known. This modification is discussed in US 7,501,384. Boscalid is active as a fungicide and is now commercially available in a range of formulations for the treatment of fungal infestations.
We have found that it is hard to mill the crystalline modification I of the anhydrate of boscalid in water. As a consequence, it is not a straightforward task to directly formulate the crystalline modification I of the anhydrate of boscalid into formulations which require grinding and/or milling processes. Such formulations are, for example, granules, encapsulated granules, tablets, water-dispersible granules, water-dispersible tablets, water-dispersible powders or water dispersible powders for seed treatment, dust formulations, and formulations in which the active compound is present in dispersed form, such as, for example, suspension concentrates, oil-based suspension concentrates, suspoemulsions, or suspension concentrates for seed treatment. Hydration of the crystalline modification I of the anhydrate of boscalid is needed prior formulating into a suspension concentrate.
It is suggested in US 7,501,384 that the crystalline modification II of the anhydrate of boscalid is more suitable for making formulations which require grinding/milling processes.
The compound methyl /V-[2-[[[1-(4-chlorophenyl)-1/7-pyrazol-3-yl]oxy]methyl] phenyl]-/V-methoxycarbamate, having the common name pyraclostrobin, is a known fungicide. Formulations comprising pyraclostrobin for the treatment of fungal infestations in crops are known and are commercially available. US 7,816,392 discloses four different crystalline modifications, I to IV, of pyraclostrobin.
We have surprisingly found that combining the crystalline modification II of boscalid with the crystalline modification IV of pyraclostrobin provides a composition having a synergistic activity, that is an increased fungicidal activity, compared with the activity expected from the activity of the two components when applied individually.
Accordingly, in a first aspect, the present invention provides a fungicidal composition comprising:
(A) the crystalline modification II of 3-pyridinecarboxamide, 2-chloro-N(4’chloro[1,1’biphenyl]-2-yl) (boscalid); and (B) the crystalline modification IV of methyl N-{2-[1-(4-chlorophenyl)-1Hpyrazol-3-yloxymethyl]phenyl}(N-methoxy)carbamate (pyraclostrobin).
The composition of the present invention is of particular use for preventing and/or treating fungal infestations in plants and/or plant parts.
In a second aspect, the present invention provides a method of preventing and/or treating fungal infestations in plants and/or plant parts comprising applying to the plants and/or plant parts:
(A) the crystalline modification II of 3-pyridinecarboxamide, 2-chloro-N(4’chloro[1,1’biphenyl]-2-yl) (boscalid); and (B) the crystalline modification IV of methyl N-{2-[1-(4-chlorophenyl)-1Hpyrazol-3-yloxymethyl]phenyl}(N-methoxy)carbamate (pyraclostrobin).
In a further aspect, the present invention provides the use in the prevention and/or treatment of fungal infestations in plants and/or plant parts of:
(A) the crystalline modification II of 3-pyridinecarboxamide, 2-chloro-N(4’chloro[1,1’biphenyl]-2-yl) (boscalid); and (B) the crystalline modification IV of methyl N-{2-[1-(4-chlorophenyl)-1Hpyrazol-3-yloxymethyl]phenyl}(N-methoxy)carbamate (pyraclostrobin).
The references to the crystalline modification II of boscalid as used herein, refer to the crystalline modification of boscalid disclosed in US 7,501,384. The references to the crystalline modifications I to IV of pyraclostrobin as used herein, refer to the crystalline modifications of pyraclostrobin disclosed in US 7,816,392.
Plant as used herein, refers to all plant and plant populations such as desired and undesired wild plants or crop plants.
Plant parts as used herein, refers to all parts and organs of plants, such as shoot, leaves, needles, stalks, stems, fruit bodies, fruits, seeds, roots, tubers and rhizomes. Harvested materials, and vegetative and generative propagation materials, for example, cutting, tubers, meristem tissue, rhizomes, offsets, seeds, single and multiple plant cells and any other plant tissues, are also included.
The word “locus” refers to the place on which the plants are growing, the place on which the plant propagation materials of the plants are sown or the place on which the plant propagation materials of the plants will be sown.
“At least one” designates a number of the respective compounds or components of 1, 2, 3, 4, 5, 6, 7, 8, 9 or more, preferably 1, 2, or 3.
The synergistic fungicidal composition, the method and use of the present invention are suitable for the treatment of plants of a wide range of crops, including: cereals, for example wheat, barley, rye, oats, corn, rice, sorghum, triticale and related crops; fruit, such as pome fruit, stone fruit and soft fruit, such as apples, pears, plums, peaches, pistachio, almonds, cherries, and berries, for example grape, banana, strawberries, bushberry, caneberry, raspberries and blackberries; leguminous plants, for example beans, lentils, peas, and soybeans; oil plants, for example oilseed rape, mustard and sunflowers; cucurbitaceae, for example cantaloupe, marrows, cucumbers, melons, pumpkin, squash and watermelon; citrus fruit, such as oranges, lemons, grapefruit and mandarins; and vegetables, for example spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika, garlic and leeks; coffee; sugarcane; hops; tree nuts; as well as ornamentals, for example flowers, such as roses, shrubs, broad-leaved trees and evergreens, such as conifers.
The composition, method and use of the present invention are particularly advantageous when applied to cereals, fruit, leguminous plants, oil plants and vegetables.
The composition, method and use of the present invention are of advantage when applied to wheat, barley, oats, rice, grape, banana, soybean, oilseed rape and vegetables.
The composition, method and use of the present invention can be used in the agricultural sector and related fields of use for preventing and/or treating fungal infestations, including but not limited to:
Cereals:
Oat: Leaf rust (Puccinia coronate var. a venae);
Barley: Stain-brown; common root rot (Bipolaris sorokinianay spot-type net blotch, blotch (Drechslera/Pyrenophora teresy Leaf blotch (Rhynchosporium secalisy Ramularia leaf spot (Ramularia collo-cygniy Brown rust (Puccinia hordeiy powdery mildew (Blumeria graminisy
Wheat: tan spot, helminthosporiosis (Pyrenophora tritici-repentisy leaf/brown rust (Puccinia triticina, Puccinia tritici-duriy, Septoria tritici blotch, Septoria (Septoria triticiy glume blotch (stagonospora nodorumy Helminthosporiose; common root rot (Bipolaris sorokinianay powdery mildew (Blumeria graminisy, yellow rust (Puccinia strillformisy
Berries: Alternaria leaf spot and fruit rot (Alternaria spp.y Anthracnose (Colletotrichum spp., Elsinoe spp.y Botrytis gray mold (Botrytis cinereay Leaf spot and blotch (Mycosphaerella spp., Septoria spp., Mycosphaerella fijiensisy Monilinia blight and mummy berry (Monilinia spp.y Phomopsis leaf spot, twig blight, and fruit rot (Phomopsis spp.y Powdery mildew (Sphaerotheca spp., Microsphaera spp., Oidium spp.y Spur blight (Didymella spp., Phoma spp.y Mal-de-Sigatoka, Sigatoka (Musicola Mycosphaerellay
Banana: Mycosphaerella fijiensis·,
Grapes: Angular leaf spot (Mycosphaerella angulatay Anthracnose (Elsinoe ampelinay Black rot (Guignardia bidwelliiy Downy mildew (Plasmopara viticolay Leaf blight (Pseudocercospora vitisy Phomopsis cane and leaf spot (Phomopsis viticolay
Powdery mildew (Uncinula necatofy, Ripe rot (Colletotrichum gloeosporioidesy
Summer bunch rot (Sour rot) (Cladosporium spp. and Aspergillus spp.y Botrytis gray mold (Botrytis cinereay
Soybean: Phakopsora pachyrhizr,
Bulb Vegetables: Botrytis leaf blight (Botrytis spp.y Botrytis neck rot (Botrytis spp.y Purple blotch and leaf blight (Alternaria porriy Stemphylium leaf blight and stalk rot (Stemphylium vesicariumy Downy mildew (Peronospora destructory
Carrots: Alternaria leaf spot (Alternaria spp.y Cercospora leaf spot (Cercospora spp.y Powdery mildew (Erysiphe spp.y Southern root rot (Sclerotium rolfsiiy yiuch;
Cucurbit Vegetables: Downy mildew (Pseudoperonospora cubensisy Alternaria blight (Alternaria cucumerinay Cercospora leaf spot (Cercospora citrulinay Gummy stem blight (Didymella bryoniaey Powdery mildew (Sphaerotheca fuliginea, Erysiphe cichoracearumy Anthracnose (Colletotrichum orbicularey
Hops: Powdery mildew (Erysiphe cichoracearum, Sphaerotheca spp.y Downy mildew (Pseudoperonospora humuliy, Powdery mildew (Erysiphe cichoracearum, Sphaerotheca humuli, Sphaerotheca macularis, Sphaerotheca spp.y
Pistachio: Alternaria late blight (Alternaria spp.y Botrytis blossom and shoot blight (Botrytis cinereay Panicle and shoot blight (Botryosphaeria dothideay
Pome Fruits: Alternaria blotch (Alternaria maliy Apple scab (Venturia inaequalisy Bitter rot (Colletotrichum spp.y Black rot/Frogeye leaf spot (Botryosphaeria obtusay Blue mold (Penicillium spp.y Brooks spot (Mycosphaerella pomiy Flyspeck (Zygophiala jamaicensisy Gray mold (Botrytis spp.y Pear scab (Venturia pirinay Powdery mildew (Podosphaera leucotrichay Sooty blotch (disease complex); White rot (Botryosphaeria dothideay Cedar apple rust (Gymnosporangium juniperi- virginianaey Ouince rust (Gymnosporangium clavipesy
Oilseed rape: phoma (Leptosphaeria maculansy light leaf spot (Pyrenopeziza brassicaey Sclerotinia sclerotiorum·,
Fruit: Powdery mildew (Podospheara leucotricha; Sphaerotheca pannosa), scab (Venturia inaequalisy
Stone Fruits: Alternaria leaf spot (Alternaria spp.y Anthracnose (Colletotrichum spp.y Blossom blight (Monilinia spp.y Brown rot (Monilinia spp.y Leaf spot (Blumeriella jaapiiy Powdery mildew (Sphaerotheca spp., Podosphaera spp.y, Ripe fruit rot (Monilinia fructicola, Monilinia laxa, Botrytis cinerea, Rhizopus spp.y Rust (Tranzschelia discolor); Scab (Cladosporium carpophilumy Shothole (Wilsonomyces carpophilusy
Strawberries: Anthracnose (Colletotrichum spp.y Botrytis gray mold (Botrytis cinerea)·, Leaf spot (Mycosphaerella fragariaey Powdery mildew (Sphaerotheca macularisy
Tree Nuts: Alternaria leaf spot (Alternaria spp.y, Anthracnose (Colletotrichum spp.y Blossom blight (Monilinia spp.)·, Eastern filbert blight (Anisogramma anomala)·,
Leaf rust (Tranzschelia discolor); Scab (Cladosporium carpophilum, C. caryigenum); Green fruit rot (Botrytis cinerea)·, Shothole (Wilsonomyces carpophilusy,
Vegetables: Downy mildew (Plasmopara spp.y Powdery mildew (Oidium spp.y Botrytis gray mold (Botrytis cinerea).
The fungicidal composition, method and use of the present invention exhibit surprisingly high effectiveness in treating and/or preventing fungal diseases caused by fungal pathogens, including:
Barley: blotch (Drechslera/Pyrenophora teres)·, Leaf blotch (Rhynchosporium secalis); Ramularia leaf spot (Ramularia collo-cygni);
Wheat: leaf/brown rust (Puccinia triticina, Puccinia tritici-duri); Septoria tritici blotch, Septoria (Septoria tritici)·, glume blotch (stagonospora nodorumy yellow rust (Puccinia strillformis);
Banana: Mycosphaerella fijiensis;
Grapes: Downy mildew (Plasmopara viticola); Powdery mildew (Uncinula necator); Botrytis gray mold (Botrytis cinerea)·,
Soybean: Phakopsora pachyrhizi;
Oilseed rape: phoma (Leptosphaeria maculans); light leaf spot (Pyrenopeziza brassicae); Sclerotinia sclerotiorum;
Fruit: Powdery mildew (Podospheara leucotricha; Sphaerotheca pannosa), scab (Venturia inaequalis);
Vegetables: Downy mildew (Plasmopara sppf Powdery mildew (Oidium sppf
Botrytis gray mold (Botrytis cinereal
The composition of the present invention comprises (A) the crystalline modification II of 3-pyridinecarboxamide, 2-chloro-N-(4’chloro[1,Tbiphenyl]-2-yl) (boscalid); and (B) the crystalline modification IV of methyl N-{2-[1-(4-chlorophenyl)1 H-pyrazol-3-yloxymethyl]phenyl}(N-methoxy)carbamate (pyraclostrobin). The crystalline modification II of boscalid may be present in the synergistic fungicidal composition of the present invention in any suitable amount, and is preferably present in an amount of up to 80% by weight, more preferably up to 70% by weight, still more preferably up to 60% by weight. The crystalline modification II of boscalid may be present in an amount of from about 1% to about 80% by weight of the composition, preferably from about 1% to 70% by weight, more preferably from about 1% to about 60% by weight of the composition.
The crystalline modification IV of pyraclostrobin may be present in the synergistic fungicidal composition in any suitable amount, and is preferably present in an amount of up to 70% by weight, more preferably up to 60% by weight, still more preferably up to 50% by weight. The crystalline modification IV of pyraclostrobin may be present in an amount of from about 1% to about 70% by weight of the composition, preferably from about 1% to about 60% by weight, more preferably from about 1% to about 50% by weight of the composition.
The components (A) and (B) may be employed in the composition, method or use of the present invention in any suitable weight ratio. The weight ratio of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin in the composition may be in the range of from about 50:1 to about 1:50, preferably from about 25:1 to about 1:25, more preferably from about 20:1 to about 1:20, still more preferably from about 15:1 to about 1:15, more preferably still from about 10:1 to about 1:10. A preferred weight ratio for many embodiments is about 5:1 to about 1:5.
The compositions of the present invention may be produced in a conventional manner, for example by mixing the crystalline modification II of boscalid with the crystalline modification IV of pyraclostrobin, together with auxiliaries appropriate for the form of the formulation. Suitable auxiliaries which may be comprised in the composition according to the invention include all customary formulation adjuvants or components, such as extenders, carriers, solvents, surfactants, stabilizers, antifoaming agents, anti-freezing agents, preservatives, antioxidants, colorants, thickeners, solid adherents and inert fillers. Such auxiliaries are known in the art and are commercially available. Their use in the formulation of the compositions of the present invention will be apparent to the person skilled in the art.
The composition of the present invention may be provided in a wide range of formulation types. Suitable formulations includes a water-soluble concentrate (SL), an emulsifiable concentrate (EC), an emulsion (EW), a micro-emulsion (ME), suspension concentrates (SC), oil-based suspension concentrates (OD), a flowable suspension (FS), water-dispersible granules (WG), water-soluble granules (SG), a waterdispersible powder (WP), a water soluble powder (SP), granules (GR), encapsulated granules (CG), fine granules (FG), macrogranules (GG), a suspo-emulsion (SE), a capsule suspension (CS) and microgranules (MG). Preferably, the synergistic fungicidal composition is formulated as a suspension concentrate (SC), waterdispersible granules (WG), a suspo-emulsion (SE), a capsule suspension (CS), an oilbased suspension concentrate (OD), or water-soluble granules (SG).
The fungicidal composition may comprise one or more inert fillers. Such inert fillers are known in the art and available commercially. Suitable fillers include, for example, natural ground minerals, such as kaolins, aluminas, talc, chalk, quartz, attapulgite, montmorillonite, and diatomaceous earth, or synthetic ground minerals, such as highly dispersed silicic acid, aluminum oxide, silicates, and calcium phosphates and calcium hydrogen phosphates. Suitable inert fillers for granules include, for example, crushed and fractionated natural minerals, such as calcite, marble, pumice, sepiolite, and dolomite, or synthetic granules of inorganic and organic ground materials, as well as granules of organic material, such as sawdust, coconut husks, corn cobs, and tobacco stalks.
The fungicidal composition optionally includes one or more surfactants which are preferably non-ionic, cationic and/or anionic in nature and surfactant mixtures which have good emulsifying, dispersing and wetting properties, depending on the nature of the active compound to be formulated. Suitable surfactants are known in the art and are commercially available.
Suitable anionic surfactants can be both so-called water-soluble soaps and water-soluble synthetic surface-active compounds. Soaps which may be used are the alkali metal, alkaline earth metal or substituted or unsubstituted ammonium salts of higher fatty acids (Cw to C22), for example the sodium or potassium salt of oleic or stearic acid, or of natural fatty acid mixtures.
The surfactant can be an emulsifier, dispersant or wetting agent of ionic or nonionic type. Examples which may be used are salts of polyacrylic acids, salts of lignosulphonic acid, salts of phenylsulphonic or naphthalenesulphonic acids, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols, especially alkylphenols, sulphosuccinic ester salts, taurine derivatives, especially alkyltaurates, or phosphoric esters of polyethoxylated phenols or alcohols. The presence of at least one surfactant is generally required when the active compound and/or the inert carrier and/or auxiliary/adjuvant are insoluble in water and the vehicle for the final application of the composition to the plants or plant parts is water.
The fungicidal composition optionally further comprises one or more polymeric stabilizers. The suitable polymeric stabilizers that may be used in the present invention include, but are not limited to, polypropylene, polyisobutylene, polyisoprene, copolymers of monoolefins and diolefins, polyacrylates, polystyrene, polyvinyl acetate, polyurethanes or polyamides. Suitable stabilizers are known in the art and commercially available.
The surfactants and polymeric stabilizers mentioned above are generally believed to impart stability to the composition, in turn allowing the composition to be formulated, stored, transported and applied.
Suitable anti-foam agents include all substances which can normally be used for this purpose in agrochemical compositions. Suitable anti-foam agents are known in the art and are available commercially. Particularly preferred antifoam agents are mixtures of polydimethylsiloxanes and perfluroalkylphosphonic acids, such as the silicone anti-foam agents available from GE or Compton.
Suitable organic solvents may be selected from all customary organic solvents which thoroughly dissolve the active compounds employed. Again, suitable organic solvents for tebuconazole and chlorothalonil are known in the art. The following may be mentioned as being preferred: N-methyl pyrrolidone, N-octyl pyrrolidone, cyclohexyl-1-pyrrolidone; or SOLVESSO™200, a mixture of paraffinic, isoparaffinic, cycloparaffinic and aromatic hydrocarbons. Suitable solvents are commercially available.
Suitable preservatives include all substances which can normally be used for this purpose in agrochemical compositions of this type and again are well known in the art. Suitable examples that may be mentioned include PREVENTOL® (from Bayer AG) and PROXEL® (from Bayer AG).
Suitable antioxidants are all substances which can normally be used for this purpose in agrochemical compositions, as is known in the art. Preference is given to butylated hydroxytoluene.
Suitable thickeners include all substances which can normally be used for this purpose in agrochemical compositions. For example xanthan gum, PVOH, cellulose and its derivatives, clay hydrated silicates, magnesium aluminum silicates or a mixture thereof. Again, such thickeners are known in the art and available commercially.
The fungicidal composition may further comprise one or more solid adherents. Such adherents are known in the art and available commercially. They include organic adhesives, including tackifiers, such as celluloses of substituted celluloses, natural and synthetic polymers in the form of powders, granules, or lattices, and inorganic adhesives such as gypsum, silica, or cement.
In addition, depending upon the formulation, the composition according to the invention may also comprise water.
The formulated composition may for example be applied in spray form, for example employing appropriate dilutions using a diluent, such as water.
The rates of application (use) of the components (A) and (B) in the method and use of the present invention may vary, for example, according to type of use, soil type, season, climate, soil ecology, type of plants, but are such that the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin are both applied in an effective amount to provide the desired action. The application rate of the components (A) and (B) for a given set of conditions can readily be determined by routine trials.
Typically, the application rate of the synergistic fungicidal composition of the present invention lies in the range of from about 1 to 3 liters or kg per ha.
The application rate of the total amount of component (A), the crystalline modification II of boscalid, and component (B), the crystalline modification IV of pyraclostrobin, in the method and use of the invention preferably lies in the range of from about 50 to 2000 gram per hectare, more preferably from about 100 to about 1000 gram per hectare. In general, satisfactory results will be obtained when employing from about 25 to about 800 gram per hectare, preferably from about 20 to about 650 gram per hectare, more preferably from about 100 to about 500 gram per hectare of the crystalline modification II of boscalid; and from about 5 to about 400 gram per hectare, preferably from about 5 to about 350 gram per hectare, more preferably from about 50 to about 300 gram per hectare of the crystalline modification IV of pyraclostrobin.
Using such formulations, either straight (that is undiluted) or diluted with a suitable solvent, especially, water, plants, plant parts and/or the locus can be treated and protected against fungal infestations by techniques known in the art. Generally, the formulations containing the active ingredients can be diluted with water. The composition can be applied with the methods known in the art. These methods include coating, spraying, dipping, pouring, immersing, soaking, injection, irrigation and the like.
Components (A) and (B) can be applied to the plants, plant parts and/or locus where control is desired either simultaneously and/or in succession, preferably at short intervals, for example on the same day.
The components (A) and (B) may be applied to the plant, one or more parts thereof (such as leaves or seeds), or the locus thereof in any order. Each component may be applied just once or a plurality of times. Preferably, each of the components (A) and (B) is applied a plurality of times, in particular from 1 to 6 times.
Components (A) and (B) may be applied in any suitable form, as described above. Typically, the active components will be applied as formulations, that is compositions comprising one or more of the active components together with further carriers, surfactants or other application-promoting adjuvants customarily employed in formulation technology.
In the event, components (A) and (B) are applied simultaneously in the present invention, they may be applied as a composition containing components (A) and (B), in which case components (A) and (B) can be obtained from a separate formulation source and mixed together (known as a tank-mix, ready-to-apply, spray broth, or slurry), optionally with other pesticides, or components (A) and (B) can be obtained as a single formulation mixture source (known as a pre-mix, concentrate, formulated compound (or product)), and optionally mixed together with other pesticides.
In a preferred embodiment, the method and use of the present invention employ a composition according to the present invention.
The compositions according to the invention are distinguished by the fact that they are especially well tolerated by plants being treated and are environmentally friendly.
Embodiments of the present invention will be described, for illustrative purposes, by way of the following examples.
In the examples, percentages are weight percent, unless otherwise indicated.
EXAMPLES
Formulation Examples
Example 1 - Crystalline modification II boscalid suspension concentrate (SC)
A suspension concentrate (SC) comprising the crystalline II modification of boscalid was prepared from the components set out in the following table.
Crystalline modification II boscalid 25.2%
Propylene glycol 10%
Tristyryl phenol ethoxylates 5%
Sodium lignosulfonate 1%
Carboxymethylcellulose 1%
Silicone oil (in the form of a 75% emulsion in water) 1%
Water Balance to 1L
Example 2 - Crystalline modification IV pyraclostrobin suspension concentrate (SC)
A suspension concentrate (SC) comprising the crystalline IV modification of 5 pyraclostrobin was prepared from the components set out in the following table.
Crystalline modification IV pyraclostrobin 12.8%
Propylene glycol 10%
Tristyryl phenol ethoxylates 5%
Sodium lignosulfonate 1%
Carboxymethylcellulose 1%
Silicone oil (in the form of a 75% emulsion in water) 1%
Water Balance to 1L
Example 3 - Crystalline modification I boscalid + Crystalline modification I pyraclostrobin suspension concentrate (SC)
A suspension concentrate (SC) comprising the crystalline I modification of boscalid and the crystalline I modification of pyraclostrobin was prepared from the components set out in the following table.
Crystalline modification I boscalid 25.2%
Crystalline modification I pyraclostrobin 12.8%
Propylene glycol 10%
Tristyryl phenol ethoxylates 5%
Sodium lignosulfonate 1%
Carboxymethylcellulose 1%
Silicone oil (in the form of a 75% emulsion in water) 1%
Water Balance to 1L
Example 4 - Crystalline modification I boscalid + crystalline modification II pyraclostrobin suspension (SC)
A suspension concentrate (SC) comprising the crystalline I modification of 5 boscalid and the crystalline II modification of pyraclostrobin was prepared from the components set out in the following table.
Crystalline modification 1 boscalid 25.2%
Crystalline modification II pyraclostrobin 12.8%
Propylene glycol 10%
Tristyryl phenol ethoxylates 5%
Sodium lignosulfonate 1%
Carboxymethylcellulose 1%
Silicone oil (in the form of a 75% emulsion in water) 1%
Water Balance to 1L
Example 5 - Crystalline modification I boscalid + crystalline modification III pyraclostrobin suspension concentrate (SC)
A suspension concentrate (SC) comprising the crystalline I modification of boscalid and the crystalline III modification of pyraclostrobin was prepared from the components set out in the following table.
Crystalline modification I boscalid 25.2%
Crystalline modification III pyraclostrobin 12.8%
Propylene glycol 10%
Tristyryl phenol ethoxylates 5%
Sodium lignosulfonate 1%
Carboxymethylcellulose 1%
Silicone oil (in the form of a 75% emulsion in water) 1%
Water Balance to 1L
Example 6 - Crystalline modification I boscalid + crystalline modification IV pyraclostrobin suspension concentrate (SC)
A suspension concentrate (SC) comprising the crystalline I modification of 5 boscalid and the crystalline IV modification of pyraclostrobin was prepared from the components set out in the following table.
Crystalline modification 1 boscalid 25.2%
Crystalline modification IV pyraclostrobin 12.8%
Propylene glycol 10%
Tristyryl phenol ethoxylates 5%
Sodium lignosulfonate 1%
Carboxymethylcellulose 1%
Silicone oil (in the form of a 75% emulsion in water) 1%
Water Balance to 1L
Example 7 - Crystalline modification II boscalid + crystalline modification I pyraclostrobin suspension (SC)
A suspension concentrate (SC) comprising the crystalline II modification of boscalid and the crystalline I modification of pyraclostrobin was prepared from the components set out in the following table.
Crystalline modification II boscalid 25.2%
Crystalline modification I pyraclostrobin 12.8%
Propylene glycol 10%
Tristyryl phenol ethoxylates 5%
Sodium lignosulfonate 1%
Carboxymethylcellulose 1%
Silicone oil (in the form of a 75% emulsion in water) 1%
Water Balance to 1L
Example 8 - Crystalline modification II boscalid + crystalline modification II pyraclostrobin suspension concentrate (SC)
A suspension concentrate (SC) comprising the crystalline II modification of 5 boscalid and the crystalline II modification of pyraclostrobin was prepared from the components set out in the following table.
Crystalline modification II boscalid 25.2%
Crystalline modification II pyraclostrobin 12.8%
Propylene glycol 10%
Tristyryl phenol ethoxylates 5%
Sodium lignosulfonate 1%
Carboxymethylcellulose 1%
Silicone oil (in the form of a 75% emulsion in water) 1%
Water Balance to 1L
Example 9 - Crystalline modification II boscalid + crystalline modification III pyraclostrobin suspension concentrate (SC)
A suspension concentrate (SC) comprising the crystalline II modification of boscalid and the crystalline III modification of pyraclostrobin was prepared from the components set out in the following table.
Crystalline modification II boscalid 25.2%
Crystalline modification III pyraclostrobin 12.8%
Propylene glycol 10%
Tristyryl phenol ethoxylates 5%
Sodium lignosulfonate 1%
Carboxymethylcellulose 1%
Silicone oil (in the form of a 75% emulsion in water) 1%
Water Balance to 1L
Example 10 - Crystalline modification II boscalid + crystalline modification IV pyraclostrobin suspension concentrate (SC)
A suspension concentrate (SC) comprising the crystalline II modification of 5 boscalid and the crystalline IV modification of pyraclostrobin was prepared from the components set out in the following table.
Crystalline modification II boscalid 25.2%
Crystalline modification IV pyraclostrobin 12.8%
Propylene glycol 10%
Tristyryl phenol ethoxylates 5%
Sodium lignosulfonate 1%
Carboxymethylcellulose 1%
Silicone oil (in the form of a 75% emulsion in water) 1%
Water Balance to 1L
Example 11 - Crystalline modification II boscalid + crystalline modification IV pyraclostrobin suspension concentrate (SC)
A suspension concentrate (SC) comprising the crystalline II modification of boscalid and the crystalline IV modification of pyraclostrobin was prepared from the components set out in the following table.
Crystalline modification II boscalid 16.67%
Crystalline modification IV pyraclostrobin 10%
Propylene glycol 10%
Tristyryl phenol ethoxylates 5%
Sodium lignosulfonate 1%
Carboxymethylcellulose 1%
Silicone oil (in the form of a 75% emulsion in water) 1%
Water Balance to 1L
Example 12 - Crystalline modification II boscalid + crystalline modification IV pyraclostrobin water dispersible granules (WG)
A water dispersible granule (WG) composition comprising the crystalline II modification of boscalid and the crystalline IV modification of pyraclostrobin was prepared from the components set out in the following table.
Crystalline modification II boscalid 5%
Crystalline modification IV pyraclostrobin 30%
Poly vinyl alcohol 2%
DISPERSOGEN®1494 (sodium salt of a cresol-formaldehyde condensation) 5%
Kaolin balance to 100 g
io
Example 13 - Crystalline modification II boscalid + crystalline modification IV pyraclostrobin capsule suspension (CS)
A capsule suspension (SC) comprising the crystalline II modification of boscalid and the crystalline IV modification of pyraclostrobin was prepared from the components set out in the following table.
Crystalline modification II boscalid 10%
Crystalline modification IV pyraclostrobin 5%
SOLVESSO™100 (blend of aromatic hydrocarbon solvents) 15%
PVA (polyvinyl alcohol) 0.8%
Sodium lignosulfonate 0.6%
SUPRASEC®5005 (polymeric diphenylmethane diisocyanate) 3%
Diethylenetriamine 1.4%
Propylene glycol 4%
Xanthan 0.1%
NIPACIDE BIT 20 (biocide) 0.1%
Silicone oil (in the form of a 75% emulsion in water) 0.2%
Water Balance to 100%
Example 14 - Crystalline modification II boscalid + crystalline modification IV pyraclostrobin water dispersible granules (WG)
A water dispersible granule (WG) composition comprising the crystalline II modification of boscalid and the crystalline IV modification of pyraclostrobin was prepared from the components set out in the following table.
Crystalline modification II boscalid 50%
Crystalline modification IV pyraclostrobin 2.5%
Poly vinyl alcohol 2%
DISPERSOGEN®1494 (sodium salt of a cresol-formaldehyde condensation) 5%
Kaolin balance to 100 g
io
Example 15 - Crystalline modification II boscalid + crystalline modification IV pyraclostrobin water soluble granules (SG)
A water soluble granule (SG) composition comprising the crystalline II 15 modification of boscalid and the crystalline IV modification of pyraclostrobin was prepared from the components set out in the following table.
Crystalline modification II boscalid 25%
Crystalline modification IV pyraclostrobin 15%
Sodium lauryl sulfate 0.5%
Sodium lignosulfonate 4.5%
Lactose 55%
Example 16 - Crystalline modification II boscalid + crystalline modification IV pyraclostrobin flowable suspension (FS)
A flowable suspension (FS) comprising the crystalline II modification of boscalid and the crystalline IV modification of pyraclostrobin was prepared from the components set out in the following table.
Crystalline modification II boscalid 3%
Crystalline modification IV pyraclostrobin 1.67%
Propylene glycol 10%
Tristyryl phenol ethoxylates 5%
Sodium lignosulfonate 1%
Carboxymethylcellulose 1%
Silicone oil (in the form of a 75% emulsion in water) 1%
Water Balance to 1L
io
Example 17 - Crystalline modification II boscalid + crystalline modification IV pyraclostrobin suspo-emulsion (SE)
A suspo-emulsion (SE) composition comprising the crystalline II modification of 15 boscalid and the crystalline IV modification of pyraclostrobin was prepared from the components set out in the following table.
Crystalline modification II boscalid 30%
Crystalline modification IV pyraclostrobin 20%
N-methylpyrrolidone 15%
Alkamuls OR/36 (ethoxylated castor oil) 4.5%
Polyurethanes 3%
TERSPERSE®2500 (comb-graft copolymer) 3.75%
SOPROPHOR®FLK (ethoxylated tristyrylphenol phosphate potassium salt) 1.5%
Propylene glycol 10%
2% xanthan gum 11.25%
Silicone oil (in the form of a 75% emulsion in water) 1.5%
Water Balance to 1L
Example 18 - Crystalline modification II boscalid + crystalline modification IV pyraclostrobin oil-based suspension concentrate (OP)
An oil-based suspension concentrate (OD) composition comprising the crystalline II modification of boscalid and the crystalline IV modification of pyraclostrobin was prepared from the components set out in the following table.
Crystalline modification II boscalid 40%
Crystalline modification IV pyraclostrobin 20%
Tristyrylphenol ethoxylates 7.5%
Sodium lignosulfonate 1.5%
Silicon dioxide 1.5%
Silicone oil 1.5%
Vegetable oil Balance to 100%
Example 19 - Crystalline modification II boscalid water dispersible granules (WG)
A water dispersible granule (WG) composition comprising the crystalline II modification of boscalid was prepared from the components set out in the following table.
Crystalline modification II boscalid 50%
PVA (Polyvinyl alcohol) 2%
DISPERSOGEN®1494 (sodium salt of a cresol-formaldehyde condensation) 5%
Kaolin balance to 100 g
Example 20 - Crystalline modification IV pyraclostrobin suspension concentrate (SC)
A suspension concentrate (SC) composition comprising the crystalline IV modification of pyraclostrobin was prepared from the components set out in the following table.
Crystalline modification IV pyraclostrobin 30%
Propylene glycol 10%
Tristyryl phenol ethoxylates 5%
Sodium lignosulfonate 1%
Carboxymethylcellulose 1%
Silicone oil (in the form of a 75% emulsion in water) 1%
Water Balance to 1L
Biological Examples
A synergistic effect exists with a combination of two active compounds when the activity of a composition comprising both active compounds is greater than the sum of the activities of the two active compounds applied individually. The expected activity for a given combination of two active compounds can be calculated by the so called “Colby equation” (see S.R. Colby, “Calculating Synergistic and Antagonistic
Responses of Herbicide Combinations”, Weeds 1967,15, 20-22):
whereby:
A — the activity percentage of compound A when active compound A is empolyed at an application rate of m g/ha;
B — the activity percentage of compound B when active compound B is empolyed at an application rate of n g/ha;
E — the percentage of estimated activity when compounds A and B are empolyed together at an application rate of m g/ha and n g/ha;
then:
Ε-Α+Β-(ΑχΒ/100).
If the actual activity observed for the combination of compunds A and B is greater than that calculated, then the activity of the combination is superadditive. In other words, synergism is present.
The severity of the fungal infestation is indicated in the following examples in terms of the percentage of the plant observed to be infested with the indicated fungus.
Biological Example 1 - Grape (Plasmopara viticola)
Grape plants were sprayed with a conidial suspension of Plasmopara viticola and incubated at conditions of 20°C and 100% relative atmospheric humidity for 48 hours. The plants were then sprayed with compositions of Formulations Examples 1 to 20 set out above. The treated plants were held in a greenhouse at conditions of 15°C and 80% relative atmospheric humidity for 10 days, after which, the severity of the fungal infestation was assessed.
The results are set out in the following table.
Example Application rate of boscalid and pyraclostrobin (g Al/ha) % Severity
Boscalid Pyraclostrobin
Example 1 252 0 55
Example 2 0 128 65
Example 3 252 128 45
Example 4 252 128 45
Example 5 252 128 40
Example 6 252 128 35
Example 7 252 128 40
Example 8 252 128 45
Example 9 252 128 35
Example 10 252 128 5
Example 11 333.4 200 5
Example 12 50 300 5
Example 13 100 50 5
Example 14 500 25 10
Example 15 250 150 5
Example 16 90 50 10
Example 17 300 200 5
Example 18 400 200 5
Example 19 500 0 50
Example 20 0 300 55
Control 0 0 80
As can be seen from the data set out in the above table, the combination of boscalid and pyraclostrobin, in particular the combination of the crystalline modification
II of boscalid and the crystalline modification IV of pyraclostrobin, exhibited significantly increased activity in the control of the fungal infestation. The results demonstrate a synergistic effect.
Biological Example 2 - Grape (Uncinula necator}
Grape plants were sprayed with a conidial suspension of Uncinula necator and incubated at conditions of 20°C and 100% relative atmospheric humidity for 48 hours. Thereafter, the plants were sprayed with compositions of Formulations Examples 1 to 20 set out above. The treated plants were kept in a greenhouse at conditions of 15°C and 80% relative atmospheric humidity for 10 days, after which the severity of the fungal infestation was assessed.
The results are set out in the table below.
Example Application rate of boscalid and pyraclostrobin (g Al/ha) % Severity
Boscalid Pyraclostrobin
Example 1 252 0 65
Example 2 0 128 65
Example 3 252 128 50
Example 4 252 128 45
Example 5 252 128 50
Example 6 252 128 40
Example 7 252 128 40
Example 8 252 128 45
Example 9 252 128 40
Example 10 252 128 5
Example 11 333.4 200 10
Example 12 50 300 5
Example 13 100 50 10
Example 14 500 25 5
Example 15 250 150 5
Example 16 90 50 10
Example 17 300 200 5
Example 18 400 200 5
Example 19 500 0 60
Example 20 0 300 65
Control 0 0 90
As can be seen from the data set out in the above table, the combination of boscalid and pyraclostrobin, in particular the combination of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin, exhibited significantly increased activity in the control of the fungal infestation. The results demonstrate a synergistic effect.
Biological Example 3 - Grape (Botrytis cinerea}
Grape plants were sprayed with a conidial suspension of Botrytis cinerea and 10 incubated at conditions of 20°C and 100% relative atmospheric humidity for 48 hours. The plants were then were sprayed with compositions of the Formulations Examples 1 to 20 set out above. After treatment, the plants were held in a greenhouse at conditions of 15°C and 80% relative atmospheric humidity for 10 days, following which the severity of the fungal infestation was assessed. The results are set out in the following table.
Example Application rate of boscalid and pyraclostrobin (g Al/ha) % Severity
Boscalid Pyraclostrobin
Example 1 252 0 55
Example 2 0 128 55
Example 3 252 128 50
Example 4 252 128 50
Example 5 252 128 45
Example 6 252 128 40
ΊΊ
Example 7 252 128 35
Example 8 252 128 40
Example 9 252 128 40
Example 10 252 128 10
Example 11 333.4 200 5
Example 12 50 300 10
Example 13 100 50 5
Example 14 500 25 5
Example 15 250 150 0
Example 16 90 50 10
Example 17 300 200 5
Example 18 400 200 10
Example 19 500 0 50
Example 20 0 300 60
Control 0 0 90
As can be seen from the data set out in the above table, the combination of boscalid and pyraclostrobin, in particular the combination of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin, exhibited significantly increased activity in the control of the fungal infestation. The results demonstrate a synergistic effect.
Biological Example 4 - Bariev (Drechslera/Pyrenophora teres}
Barley plants were sprayed with a conidial suspension of
Drechslera/Pyrenophora teres and incubated at conditions of 20°C and 100% relative atmospheric humidity for 48 hours. The plants were then were sprayed with compositions of Formulations Examples 1 to 20 set out above. After treatment, the plants were held in a greenhouse at conditions of 15°C and 80% relative atmospheric humidity for 10 days. The severity of the fungal infestation was then assessed.
The results are set out in the following table.
Example Application rate of boscalid and pyraclostrobin (g Al/ha) % Severity
Boscalid Pyraclostrobin
Example 1 252 0 50
Example 2 0 128 55
Example 3 252 128 45
Example 4 252 128 50
Example 5 252 128 45
Example 6 252 128 35
Example 7 252 128 40
Example 8 252 128 40
Example 9 252 128 35
Example 10 252 128 5
Example 11 333.4 200 5
Example 12 50 300 5
Example 13 100 50 10
Example 14 500 25 5
Example 15 250 150 10
Example 16 90 50 10
Example 17 300 200 5
Example 18 400 200 5
Example 19 500 0 45
Example 20 0 300 55
Control 0 0 85
As can be seen from the data set out in the above table, the combination of boscalid and pyraclostrobin, in particular the combination of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin, exhibited significantly increased activity in the control of the fungal infestation. The results demonstrate a synergistic effect.
Biological Example 5 - Bariev (Rhynchosporium secalis)
Barley plants were sprayed with a conidial suspension of Rhynchosporium secalis and incubated at conditions of 20°C and 100% relative atmospheric humidity for 48 hours. The plants were then sprayed with compositions of Formulations
Examples 1 to 20 set out above. The treated plants were held in a greenhouse at conditions of 15°C and 80% relative atmospheric humidity for 10 days, after which the severity of the fungal infestation was assessed.
The results are set out in the following table.
Example Application rate of boscalid and pyraclostrobin (g Al/ha) % Severity
Boscalid Pyraclostrobin
Example 1 252 0 55
Example 2 0 128 60
Example 3 252 128 45
Example 4 252 128 45
Example 5 252 128 50
Example 6 252 128 35
Example 7 252 128 40
Example 8 252 128 40
Example 9 252 128 35
Example 10 252 128 5
Example 11 333.4 200 5
Example 12 50 300 5
Example 13 100 50 5
Example 14 500 25 5
Example 15 250 150 5
Example 16 90 50 10
Example 17 300 200 10
Example 18 400 200 10
Example 19 500 0 50
Example 20 0 300 55
Control 0 0 80
As can be seen from the data set out in the above table, the combination of boscalid and pyraclostrobin, in particular the combination of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin, exhibited significantly increased activity in the control of the fungal infestation. The results demonstrate a synergistic effect.
Biological Example 6 - Barley (Ramularia collo-cygni)
Barley plants were sprayed with a conidial suspension of Ramularia collo-cygni 10 and incubated at conditions of 20°C and 100% relative atmospheric humidity for 48 hours. The plants were then were sprayed with compositions of Formulations Examples 1 to 20 set out above. The treated plants were held in a greenhouse at conditions of 15°C and 80% relative atmospheric humidity for 10 days, after which the severity of the fungal infestation was assessed.
The results are set out in the following table.
Example Application rate of boscalid and pyraclostrobin (g Al/ha) % Severity
Boscalid Pyraclostrobin
Example 1 252 0 60
Example 2 0 128 60
Example 3 252 128 50
Example 4 252 128 50
Example 5 252 128 45
Example 6 252 128 40
Example 7 252 128 40
Example 8 252 128 40
Example 9 252 128 35
Example 10 252 128 5
Example 11 333.4 200 5
Example 12 50 300 10
Example 13 100 50 5
Example 14 500 25 5
Example 15 250 150 5
Example 16 90 50 10
Example 17 300 200 5
Example 18 400 200 10
Example 19 500 0 55
Example 20 0 300 55
Control 0 0 85
As can be seen from the data set out in the above table, the combination of boscalid and pyraclostrobin, in particular the combination of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin, exhibited significantly increased activity in the control of the fungal infestation. The results demonstrate a synergistic effect.
Biological Example 7 - Wheat (Puccinia triticina]
Wheat plants were sprayed with a conidial suspension of Puccinia triticina and 10 incubated at conditions of 20°C and 100% relative atmospheric humidity for 48 hours. The plants were then sprayed with compositions according to Formulations Examples 1 to 20 set out above. Thereafter, the treated plants were held in a greenhouse at conditions of 15°C and 80% relative atmospheric humidity for 10 days, after which the severity of the fungal infestation was assessed.
The results are set out in the table below.
Example Application rate of boscalid and pyraclostrobin (g Al/ha) % Severity
Boscalid Pyraclostrobin
Example 1 252 0 55
Example 2 0 128 60
Example 3 252 128 45
Example 4 252 128 45
Example 5 252 128 50
Example 6 252 128 35
Example 7 252 128 40
Example 8 252 128 40
Example 9 252 128 35
Example 10 252 128 5
Example 11 333.4 200 5
Example 12 50 300 5
Example 13 100 50 5
Example 14 500 25 5
Example 15 250 150 10
Example 16 90 50 10
Example 17 300 200 5
Example 18 400 200 5
Example 19 500 0 50
Example 20 0 300 55
Control 0 0 85
As can be seen from the data set out in the above table, the combination of boscalid and pyraclostrobin, in particular the combination of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin, exhibited significantly increased activity in the control of the fungal infestation. The results demonstrate a synergistic effect.
Biological Example 8 - Wheat (Septoria tritici)
Wheat plants were sprayed with a conidial suspension of Septoria tritici and incubated at conditions of 20°C and 100% relative atmospheric humidity for 48 hours.
The plants were then sprayed with compositions according to Formulations Examples 1 to 20 set out above. Thereafter, the treated plants were held in a greenhouse at conditions of 15°C and 80% relative atmospheric humidity for 10 days, after which the severity of the fungal infestation was assessed.
The results are set out in the table below.
Example Application rate of boscalid and pyraclostrobin (g Al/ha) % Severity
Boscalid Pyraclostrobin
Example 1 252 0 55
Example 2 0 128 60
Example 3 252 128 50
Example 4 252 128 45
Example 5 252 128 45
Example 6 252 128 40
Example 7 252 128 35
Example 8 252 128 40
Example 9 252 128 40
Example 10 252 128 5
Example 11 333.4 200 10
Example 12 50 300 5
Example 13 100 50 5
Example 14 500 25 5
Example 15 250 150 5
Example 16 90 50 10
Example 17 300 200 5
Example 18 400 200 10
Example 19 500 0 50
Example 20 0 300 55
Control 0 0 90
As can be seen from the data set out in the above table, the combination of boscalid and pyraclostrobin, in particular the combination of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin, exhibited significantly increased activity in the control of the fungal infestation. The results demonstrate a synergistic effect.
Biological Example 9 - Wheat (stagonospora nodorum)
Wheat plants were sprayed with a conidial suspension of stagonospora 10 nodorum and incubated at conditions of 20°C and 100% relative atmospheric humidity for 48 hours. The plants were then sprayed with compositions according to Formulations Examples 1 to 20 set out above. Thereafter, the treated plants were held in a greenhouse at conditions of 15°C and 80% relative atmospheric humidity for days, after which the severity of the fungal infestation was assessed.
The results are set out in the table below.
Example Application rate of boscalid and pyraclostrobin (g Al/ha) % Severity
Boscalid Pyraclostrobin
Example 1 252 0 55
Example 2 0 128 60
Example 3 252 128 40
Example 4 252 128 40
Example 5 252 128 45
Example 6 252 128 40
Example 7 252 128 40
Example 8 252 128 40
Example 9 252 128 35
Example 10 252 128 0
Example 11 333.4 200 5
Example 12 50 300 5
Example 13 100 50 5
Example 14 500 25 5
Example 15 250 150 5
Example 16 90 50 10
Example 17 300 200 5
Example 18 400 200 5
Example 19 500 0 50
Example 20 0 300 50
Control 0 0 80
As can be seen from the data set out in the above table, the combination of boscalid and pyraclostrobin, in particular the combination of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin, exhibited significantly increased activity in the control of the fungal infestation. The results demonstrate a synergistic effect.
Biological Example 10 - Wheat (Puccinia sthiformis)
Wheat plants were sprayed with a conidial suspension of Puccinia sthiformis 10 and incubated at conditions of 20°C and 100% relative atmospheric humidity for 48 hours. The plants were then sprayed with compositions according to Formulations Examples 1 to 20 set out above. Thereafter, the treated plants were held in a greenhouse at conditions of 15°C and 80% relative atmospheric humidity for 10 days, after which the severity of the fungal infestation was assessed.
The results are set out in the table below.
Example Application rate of boscalid and pyraclostrobin (g Al/ha) % Severity
Boscalid Pyraclostrobin
Example 1 252 0 60
Example 2 0 128 65
Example 3 252 128 55
Example 4 252 128 50
Example 5 252 128 50
Example 6 252 128 40
Example 7 252 128 40
Example 8 252 128 40
Example 9 252 128 45
Example 10 252 128 5
Example 11 333.4 200 5
Example 12 50 300 10
Example 13 100 50 5
Example 14 500 25 5
Example 15 250 150 10
Example 16 90 50 10
Example 17 300 200 5
Example 18 400 200 5
Example 19 500 0 55
Example 20 0 300 60
Control 0 0 95
As can be seen from the data set out in the above table, the combination of boscalid and pyraclostrobin, in particular the combination of the crystalline modification
II of boscalid and the crystalline modification IV of pyraclostrobin, exhibited significantly increased activity in the control of the fungal infestation. The results demonstrate a synergistic effect.
Biological Example 11 - Banana (Mycosphaerella fijiensis)
Banana plants were sprayed with a conidial suspension of Mycosphaerella fijiensis and incubated at conditions of 20°C and 100% relative atmospheric humidity for 48 hours. The plants were then sprayed with compositions according to Formulations Examples 1 to 20 set out above. Thereafter, the treated plants were held in a greenhouse at conditions of 15°C and 80% relative atmospheric humidity for
10 days, after which the severity of the fungal infestation was assessed.
The results are set out in the table below.
Example Application rate of boscalid and pyraclostrobin (g Al/ha) % Severity
Boscalid Pyraclostrobin
Example 1 252 0 50
Example 2 0 128 65
Example 3 252 128 45
Example 4 252 128 40
Example 5 252 128 40
Example 6 252 128 40
Example 7 252 128 35
Example 8 252 128 45
Example 9 252 128 35
Example 10 252 128 5
Example 11 333.4 200 5
Example 12 50 300 5
Example 13 100 50 5
Example 14 500 25 5
Example 15 250 150 10
Example 16 90 50 10
Example 17 300 200 5
Example 18 400 200 5
Example 19 500 0 50
Example 20 0 300 55
Control 0 0 80
As can be seen from the data set out in the above table, the combination of boscalid and pyraclostrobin, in particular the combination of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin, exhibited significantly increased activity in the control of the fungal infestation. The results demonstrate a synergistic effect.
Biological Example 12 - Soybean (Phakopsora pachyrhizi)
Soybean plants were sprayed with a conidial suspension of Phakopsora 10 pachyrhizi and incubated at conditions of 20°C and 100% relative atmospheric humidity for 48 hours. The plants were then sprayed with compositions according to Formulations Examples 1 to 20 set out above. Thereafter, the treated plants were held in a greenhouse at conditions of 15°C and 80% relative atmospheric humidity for days, after which the severity of the fungal infestation was assessed.
The results are set out in the table below.
Example Application rate of boscalid and pyraclostrobin (g Al/ha) % Severity
Boscalid Pyraclostrobin
Example 1 252 0 55
Example 2 0 128 65
Example 3 252 128 50
Example 4 252 128 50
Example 5 252 128 45
Example 6 252 128 40
Example 7 252 128 40
Example 8 252 128 40
Example 9 252 128 40
Example 10 252 128 5
Example 11 333.4 200 5
Example 12 50 300 10
Example 13 100 50 10
Example 14 500 25 5
Example 15 250 150 5
Example 16 90 50 10
Example 17 300 200 5
Example 18 400 200 10
Example 19 500 0 55
Example 20 0 300 60
Control 0 0 90
As can be seen from the data set out in the above table, the combination of boscalid and pyraclostrobin, in particular the combination of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin, exhibited significantly increased activity in the control of the fungal infestation. The results demonstrate a synergistic effect.
Biological Example 13 - Oilseed rape (Leptosphaeria maculans)
Oilseed rape plants were sprayed with a conidial suspension of Leptosphaeria io maculans and incubated at conditions of 20°C and 100% relative atmospheric humidity for 48 hours. The plants were then sprayed with compositions according to Formulations Examples 1 to 20 set out above. Thereafter, the treated plants were held in a greenhouse at conditions of 15°C and 80% relative atmospheric humidity for days, after which the severity of the fungal infestation was assessed.
The results are set out in the table below.
Example Application rate of boscalid and pyraclostrobin (g Al/ha) % Severity
Boscalid Pyraclostrobin
Example 1 252 0 55
Example 2 0 128 60
Example 3 252 128 50
Example 4 252 128 45
Example 5 252 128 45
Example 6 252 128 40
Example 7 252 128 40
Example 8 252 128 45
Example 9 252 128 40
Example 10 252 128 10
Example 11 333.4 200 5
Example 12 50 300 5
Example 13 100 50 10
Example 14 500 25 5
Example 15 250 150 5
Example 16 90 50 10
Example 17 300 200 5
Example 18 400 200 5
Example 19 500 0 50
Example 20 0 300 55
Control 0 0 85
As can be seen from the data set out in the above table, the combination of boscalid and pyraclostrobin, in particular the combination of the crystalline modification
II of boscalid and the crystalline modification IV of pyraclostrobin, exhibited significantly increased activity in the control of the fungal infestation. The results demonstrate a synergistic effect.
Biological Example 14 - Oilseed rape (Pyrenopeziza brassicae)
Oilseed rape plants were sprayed with a conidial suspension of Pyrenopeziza brassicae and incubated at conditions of 20°C and 100% relative atmospheric humidity for 48 hours. The plants were then sprayed with compositions according to Formulations Examples 1 to 20 set out above. Thereafter, the treated plants were held in a greenhouse at conditions of 15°C and 80% relative atmospheric humidity for 10 days, after which the severity of the fungal infestation was assessed.
The results are set out in the table below.
Example Application rate of boscalid and pyraclostrobin (g Al/ha) % Severity
Boscalid Pyraclostrobin
Example 1 252 0 55
Example 2 0 128 55
Example 3 252 128 45
Example 4 252 128 45
Example 5 252 128 45
Example 6 252 128 40
Example 7 252 128 40
Example 8 252 128 35
Example 9 252 128 35
Example 10 252 128 5
Example 11 333.4 200 5
Example 12 50 300 5
Example 13 100 50 5
Example 14 500 25 5
Example 15 250 150 5
Example 16 90 50 10
Example 17 300 200 5
Example 18 400 200 10
Example 19 500 0 50
Example 20 0 300 50
Control 0 0 85
As can be seen from the data set out in the above table, the combination of boscalid and pyraclostrobin, in particular the combination of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin, exhibited significantly increased activity in the control of the fungal infestation. The results demonstrate a synergistic effect.
Biological Example 15 - Oilseed rape (Sclerotinia sclerotiorum)
Oilseed rape plants were sprayed with a conidial suspension of Sclerotinia 10 sclerotiorum and incubated at conditions of 20°C and 100% relative atmospheric humidity for 48 hours. The plants were then sprayed with compositions according to Formulations Examples 1 to 20 set out above. Thereafter, the treated plants were held in a greenhouse at conditions of 15°C and 80% relative atmospheric humidity for days, after which the severity of the fungal infestation was assessed.
The results are set out in the table below.
Example Application rate of boscalid and pyraclostrobin (g Al/ha) % Severity
Boscalid Pyraclostrobin
Example 1 252 0 60
Example 2 0 128 65
Example 3 252 128 50
Example 4 252 128 50
Example 5 252 128 45
Example 6 252 128 40
Example 7 252 128 40
Example 8 252 128 45
Example 9 252 128 45
Example 10 252 128 5
Example 11 333.4 200 5
Example 12 50 300 10
Example 13 100 50 10
Example 14 500 25 5
Example 15 250 150 5
Example 16 90 50 10
Example 17 300 200 5
Example 18 400 200 10
Example 19 500 0 50
Example 20 0 300 55
Control 0 0 90
As can be seen from the data set out in the above table, the combination of boscalid and pyraclostrobin, in particular the combination of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin, exhibited significantly increased activity in the control of the fungal infestation. The results demonstrate a synergistic effect.
Biological Example 16 - Apple (Podosphaera leucotricha)
Apple plants were sprayed with a conidial suspension of Podosphaera 10 leucotricha and incubated at conditions of 20°C and 100% relative atmospheric humidity for 48 hours. The plants were then sprayed with compositions according to
Formulations Examples 1 to 20 set out above. Thereafter, the treated plants were held in a greenhouse at conditions of 15°C and 80% relative atmospheric humidity for days, after which the severity of the fungal infestation was assessed.
The results are set out in the table below.
Example Application rate of boscalid and pyraclostrobin (g Al/ha) % Severity
Boscalid Pyraclostrobin
Example 1 252 0 55
Example 2 0 128 55
Example 3 252 128 45
Example 4 252 128 45
Example 5 252 128 40
Example 6 252 128 40
Example 7 252 128 40
Example 8 252 128 40
Example 9 252 128 35
Example 10 252 128 5
Example 11 333.4 200 5
Example 12 50 300 5
Example 13 100 50 5
Example 14 500 25 5
Example 15 250 150 10
Example 16 90 50 10
Example 17 300 200 10
Example 18 400 200 5
Example 19 500 0 50
Example 20 0 300 50
Control 0 0 80
As can be seen from the data set out in the above table, the combination of boscalid and pyraclostrobin, in particular the combination of the crystalline modification
II of boscalid and the crystalline modification IV of pyraclostrobin, exhibited significantly increased activity in the control of the fungal infestation. The results demonstrate a synergistic effect.
Biological Example 17 - Peach (Sphaerotheca pannosa)
Peach plants were sprayed with a conidial suspension of Sphaerotheca pannosa and incubated at conditions of 20°C and 100% relative atmospheric humidity for 48 hours. The plants were then sprayed with compositions according to Formulations Examples 1 to 20 set out above. Thereafter, the treated plants were held in a greenhouse at conditions of 15°C and 80% relative atmospheric humidity for 10 days, after which the severity of the fungal infestation was assessed.
The results are set out in the table below.
Example Application rate of boscalid and pyraclostrobin (g Al/ha) % Severity
Boscalid Pyraclostrobin
Example 1 252 0 55
Example 2 0 128 60
Example 3 252 128 45
Example 4 252 128 40
Example 5 252 128 45
Example 6 252 128 35
Example 7 252 128 40
Example 8 252 128 35
Example 9 252 128 35
Example 10 252 128 5
Example 11 333.4 200 5
Example 12 50 300 5
Example 13 100 50 10
Example 14 500 25 5
Example 15 250 150 5
Example 16 90 50 10
Example 17 300 200 5
Example 18 400 200 10
Example 19 500 0 50
Example 20 0 300 55
Control 0 0 85
As can be seen from the data set out in the above table, the combination of boscalid and pyraclostrobin, in particular the combination of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin, exhibited significantly increased activity in the control of the fungal infestation. The results demonstrate a synergistic effect.
Biological Example 18 - Pear (Venturia inaequalis)
Pear plants were sprayed with a conidial suspension of Venturia inaequalis and 10 incubated at conditions of 20°C and 100% relative atmospheric humidity for 48 hours. The plants were then sprayed with compositions according to Formulations Examples 1 to 20 set out above. Thereafter, the treated plants were held in a greenhouse at conditions of 15°C and 80% relative atmospheric humidity for 10 days, after which the severity of the fungal infestation was assessed.
The results are set out in the table below.
Example Application rate of boscalid and pyraclostrobin (g Al/ha) % Severity
Boscalid Pyraclostrobin
Example 1 252 0 55
Example 2 0 128 60
Example 3 252 128 45
Example 4 252 128 45
Example 5 252 128 45
Example 6 252 128 40
Example 7 252 128 45
Example 8 252 128 40
Example 9 252 128 35
Example 10 252 128 5
Example 11 333.4 200 5
Example 12 50 300 10
Example 13 100 50 5
Example 14 500 25 5
Example 15 250 150 5
Example 16 90 50 10
Example 17 300 200 10
Example 18 400 200 5
Example 19 500 0 50
Example 20 0 300 50
Control 0 0 80
As can be seen from the data set out in the above table, the combination of boscalid and pyraclostrobin, in particular the combination of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin, exhibited significantly increased activity in the control of the fungal infestation. The results demonstrate a synergistic effect.
Biological Example 19 - Cabbage (Plasmopara spy.)
Cabbage plants were sprayed with a conidial suspension of Plasmopara spp. 10 and incubated at conditions of 20°C and 100% relative atmospheric humidity for 48 hours. The plants were then sprayed with compositions according to Formulations
Examples 1 to 20 set out above. Thereafter, the treated plants were held in a greenhouse at conditions of 15°C and 80% relative atmospheric humidity for 10 days, after which the severity of the fungal infestation was assessed.
The results are set out in the table below.
Example Application rate of boscalid and pyraclostrobin (g Al/ha) % Severity
Boscalid Pyraclostrobin
Example 1 252 0 55
Example 2 0 128 60
Example 3 252 128 50
Example 4 252 128 45
Example 5 252 128 45
Example 6 252 128 40
Example 7 252 128 40
Example 8 252 128 45
Example 9 252 128 45
Example 10 252 128 5
Example 11 333.4 200 5
Example 12 50 300 10
Example 13 100 50 5
Example 14 500 25 5
Example 15 250 150 5
Example 16 90 50 10
Example 17 300 200 5
Example 18 400 200 10
Example 19 500 0 50
Example 20 0 300 55
Control 0 0 80
As can be seen from the data set out in the above table, the combination of boscalid and pyraclostrobin, in particular the combination of the crystalline modification
II of boscalid and the crystalline modification IV of pyraclostrobin, exhibited significantly increased activity in the control of the fungal infestation. The results demonstrate a synergistic effect.
Biological Example 20 - Tomato (Oidium sop.)
Tomato plants were sprayed with a conidial suspension of Oidium spp. and incubated at conditions of 20°C and 100% relative atmospheric humidity for 48 hours.
The plants were then sprayed with compositions according to Formulations Examples 1 to 20 set out above. Thereafter, the treated plants were held in a greenhouse at conditions of 15°C and 80% relative atmospheric humidity for 10 days, after which the severity of the fungal infestation was assessed.
The results are set out in the table below.
Example Application rate of boscalid and pyraclostrobin (g Al/ha) % Severity
Boscalid Pyraclostrobin
Example 1 252 0 60
Example 2 0 128 60
Example 3 252 128 50
Example 4 252 128 50
Example 5 252 128 45
Example 6 252 128 40
Example 7 252 128 40
Example 8 252 128 40
Example 9 252 128 45
Example 10 252 128 5
Example 11 333.4 200 5
Example 12 50 300 5
Example 13 100 50 5
Example 14 500 25 5
Example 15 250 150 5
Example 16 90 50 10
Example 17 300 200 10
Example 18 400 200 10
Example 19 500 0 50
Example 20 0 300 55
Control 0 0 85
As can be seen from the data set out in the above table, the combination of boscalid and pyraclostrobin, in particular the combination of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin, exhibited significantly increased activity in the control of the fungal infestation. The results demonstrate a synergistic effect.
Biological Example 21 - Cucumber (Botrytis cinerea)
Cucumber plants were sprayed with a conidial suspension of Botrytis cinerea 10 and incubated at conditions of 20°C and 100% relative atmospheric humidity for 48 hours. The plants were then sprayed with compositions according to Formulations Examples 1 to 20 set out above. Thereafter, the treated plants were held in a greenhouse at conditions of 15°C and 80% relative atmospheric humidity for 10 days, after which the severity of the fungal infestation was assessed.
The results are set out in the table below.
Example Application rate of boscalid and pyraclostrobin (g Al/ha) % Severity
Boscalid Pyraclostrobin
Example 1 252 0 55
Example 2 0 128 60
Example 3 252 128 50
Example 4 252 128 45
Example 5 252 128 45
Example 6 252 128 40
Example 7 252 128 45
Example 8 252 128 40
Example 9 252 128 40
Example 10 252 128 5
Example 11 333.4 200 5
Example 12 50 300 5
Example 13 100 50 10
Example 14 500 25 5
Example 15 250 150 5
Example 16 90 50 10
Example 17 300 200 5
Example 18 400 200 5
Example 19 500 0 50
Example 20 0 300 55
Control 0 0 80
As can be seen from the data set out in the above table, the combination of boscalid and pyraclostrobin, in particular the combination of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin, exhibited significantly increased activity in the control of the fungal infestation. The results demonstrate a synergistic effect.

Claims (57)

1. A fungicidal composition comprising:
(A) the crystalline modification II of 3-pyridinecarboxamide, 2-chloro-N5 (4’chloro[1,Tbiphenyl]-2-yl) (boscalid); and (B) the crystalline modification IV of methyl N-{2-[1-(4-chlorophenyl)-1Hpyrazol-3-yloxymethyl]phenyl}(N-methoxy)carbamate (pyraclostrobin).
2. The composition according to claim 1, wherein the crystalline modification II of
10 boscalid is present in the synergistic fungicidal composition in an amount of from about
1 % to about 80% by weight of the composition.
3. The composition according to claim 2, wherein the crystalline modification II of boscalid is present in the synergistic fungicidal composition in an amount of from about
15 1 % to 70% by weight.
4. The composition according to claim 3, wherein the crystalline modification II of boscalid is present in the synergistic fungicidal composition in an amount of from about 1 % to 60% by weight.
5. The composition according to any preceding claim, wherein the crystalline modification IV of pyraclostrobin is present in the synergistic fungicidal composition in an amount of from about 1 % to 70% by weight.
25
6. The composition according to claim 5, wherein the crystalline modification IV of pyraclostrobin is present in the synergistic fungicidal composition in an amount of from about 1% to 60% by weight.
7. The composition according to claim 6, wherein the crystalline modification IV of pyraclostrobin is present in the synergistic fungicidal composition in an amount of from about 1% to 50% by weight.
5
8. The composition according to any preceding claim, wherein the weight ratio of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin in the composition is in the range of from about 50:1 to about 1:50.
9. The composition according to claim 8, wherein the weight ratio of the
10 crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin in the composition is in the range of from about 25:1 to about 1:25.
10. The composition according to claim 9, wherein the weight ratio of the crystalline modification II of boscalid and the crystalline modification IV of
15 pyraclostrobin in the composition is in the range of from about 20:1 to about 1:20.
11. The composition according to claim 10, wherein the weight ratio of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin in the composition is in the range of from about 15:1 to about 1:15.
12. The composition according to claim 11, wherein the weight ratio of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin in the composition is in the range of from about 10:1 to about 1:10.
25
13. The composition according to claim 12, wherein the weight ratio of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin in the composition is in the range of from about 5:1 to about 1:5.
14. The composition according to any preceding claim, wherein the composition comprises one or more auxiliaries selected from extenders, carriers, solvents, surfactants, stabilizers, anti-foaming agents, anti-freezing agents, preservatives, antioxidants, colorants, thickeners, solid adherents and inert fillers.
15. The composition according to any preceding claim, wherein the composition is a water-soluble concentrate (SL), an emulsifiable concentrate (EC), an emulsion (EW), a micro-emulsion (ME), suspension concentrates (SC), oil-based suspension concentrates (OD), a flowable suspension (FS), water-dispersible granules (WG),
10 water-soluble granules (SG), a water-dispersible powder (WP), a water soluble powder (SP), granules (GR), encapsulated granules (CG), fine granules (FG), macrogranules (GG), a suspo-emulsion (SE), a capsule suspensions (CS) or microgranules (MG).
16. The composition according to claim 15, wherein the composition is a
15 suspension concentrate (SC), water-dispersible granules (WG), a suspo-emulsion (SE), a capsule suspension (CS), an oil-based suspension concentrate (OD), or watersoluble granules (SG).
17. A method of preventing and/or treating fungal infestations in plants and/or plant
20 parts comprising applying to the plants and/or plant parts:
(A) the crystalline modification II of 3-pyridinecarboxamide, 2-chloro-N(4’chloro[1,Tbiphenyl]-2-yl) (boscalid); and (B) the crystalline modification IV of methyl N-{2-[1-(4-chlorophenyl)-1Hpyrazol-3-yloxymethyl]phenyl}(N-methoxy)carbamate (pyraclostrobin).
18. The method according to claim 17, wherein the plants being treated are selected from cereals, fruit, berries, leguminous plants, oil plants, cucurbitaceae, citrus fruit, vegetables, ornamentals, broad-leaved trees and evergreens.
19. The method according to claim 18, wherein the plants being treated are selected from wheat, barley, rye, oats, corn, rice, sorghum and triticale;
apples, pears, plums, peaches, pistachio, almonds, cherries, grape, banana, strawberries, bushberry, caneberry, raspberries and blackberries; beans, lentils, peas,
5 and soybeans; oilseed rape, mustard and sunflowers; cantaloupe, marrows, cucumbers, melons, pumpkin, squash and watermelon; oranges, lemons, grapefruit and mandarins; spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika, garlic and leeks; coffee; sugarcane; hops; tree nuts; roses, shrubs, and conifers.
io
20. The method according to claim 19, wherein the plants being treated are selected from wheat, barley, oats, rice, grape, banana, soybean, oilseed rape and vegetables.
15
21. The method according to any of claims 17 to 20, wherein the weight ratio of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin is in the range of from about 50:1 to about 1:50.
22. The method according to claim 21, wherein the weight ratio of the crystalline
20 modification II of boscalid and the crystalline modification IV of pyraclostrobin is in the range of from about 25:1 to about 1:25.
23. The method according to claim 22, wherein the weight ratio of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin is in the
25 range of from about 20:1 to about 1:20.
24. The method according to claim 23, wherein the weight ratio of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin is in the range of from about 15:1 to about 1:15.
25. The method according to claim 24, wherein the weight ratio of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin is in the range of from about 10:1 to about 1:10.
5
26. The method according to claim 25, wherein the weight ratio of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin is in the range of from about 5:1 to about 1:5.
27. The method according to any of claims 17 to 26, wherein the application rate of
10 the total amount of component (A), the crystalline modification II of boscalid, and component (B), the crystalline modification IV of pyraclostrobin, is in the range of from about 100 to about 1000 gram per hectare.
28. The method according to any of claims 17 to 27, wherein the application rate of
15 component (A), the crystalline modification II of boscalid, is in the range of from about
25 to about 800 gram per hectare.
29. The method according to claim 28, wherein the application rate of the crystalline modification II of boscalid is in the range of from about 20 to about 650
20 gram per hectare.
30. The method according to claim 29, wherein the application rate of the crystalline modification II of boscalid is in the range of from about 100 to about 500 gram per hectare.
31. The method according to any of claims 17 to 30, wherein the application rate of component (B), the crystalline modification IV of pyraclostrobin, is in the range of from about 5 to about 400 gram per hectare.
32. The method according to claim 31, wherein the application rate of the crystalline modification IV of pyraclostrobin, is in the range of from about 5 to about
350 gram per hectare.
5
33. The method according to claim 32, wherein the application rate of the crystalline modification IV of pyraclostrobin is in the range of from about 50 to about 300 gram per hectare.
34. The method according to any of claims 17 to 33, wherein the components (A)
10 and (B) are applied to the plants, plant parts and/or locus where control is desired simultaneously and/or in succession.
35. The method according to any of claims 17 to 34, wherein a composition of any of claims 1 to 16 is employed.
36. The use in the prevention and/or treatment of fungal infestations in plants and/or plant parts of:
(A) the crystalline modification II of 3-pyridinecarboxamide, 2-chloro-N(4’chloro[1,1’biphenyl]-2-yl) (boscalid); and
20 (B) the crystalline modification IV of methyl N-{2-[1-(4-chlorophenyl)-1Hpyrazol-3-yloxymethyl]phenyl}(N-methoxy)carbamate (pyraclostrobin).
37. The use according to claim 36, wherein the plants being treated are selected from cereals, fruit, berries, leguminous plants, oil plants, cucurbitaceae, citrus fruit,
25 vegetables, ornamentals, broad-leaved trees and evergreens.
38. The use according to claim 37, wherein the plants being treated are selected from wheat, barley, rye, oats, corn, rice, sorghum and triticale; apples, pears, plums, peaches, pistachio, almonds, cherries, grape, banana, strawberries, bushberry, caneberry, raspberries and blackberries; beans, lentils, peas, and soybeans; oilseed rape, mustard and sunflowers; cantaloupe, marrows, cucumbers, melons, pumpkin, squash and watermelon; oranges, lemons, grapefruit and mandarins; spinach, lettuce,
5 asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika, garlic and leeks; coffee; sugarcane; hops; tree nuts; roses, shrubs, and conifers.
39. The use according to claim 38, wherein the plants being treated are selected from wheat, barley, oats, rice, grape, banana, soybean, oilseed rape and vegetables.
io
40. The use according to any of claims 36 to 39, wherein the weight ratio of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin is in the range of from about 50:1 to about 1:50.
15
41. The use according to claim 40, wherein the weight ratio of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin is in the range of from about 25:1 to about 1:25.
42. The use according to claim 41, wherein the weight ratio of the crystalline
20 modification II of boscalid and the crystalline modification IV of pyraclostrobin is in the range of from about 20:1 to about 1:20.
43. The use according to claim 42, wherein the weight ratio of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin is in the
25 range of from about 15:1 to about 1:15.
44. The use according to claim 43, wherein the weight ratio of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin is in the range of from about 10:1 to about 1:10.
45. The use according to claim 44, wherein the weight ratio of the crystalline modification II of boscalid and the crystalline modification IV of pyraclostrobin is in the range of from about 5:1 to about 1:5.
46. The use according to any of claims 36 to 45, wherein the application rate of the total amount of component (A), the crystalline modification II of boscalid, and component (B), the crystalline modification IV of pyraclostrobin, is in the range of from about 100 to about 1000 gram per hectare.
io
47. The use according to any of claims 36 to 46, wherein the application rate of component (A), the crystalline modification II of boscalid, is in the range of from about 25 to about 800 gram per hectare.
15
48. The use according to claim 47, wherein the application rate of the crystalline modification II of boscalid is in the range of from about 20 to about 650 gram per hectare.
49. The use according to claim 48, wherein the application rate of the crystalline
20 modification II of boscalid is in the range of from about 100 to about 500 gram per hectare.
50. The use according to any of claims 36 to 49, wherein the application rate of component (B), the crystalline modification IV of pyraclostrobin, is in the range of from
25 about 5 to about 400 gram per hectare.
51. The use according to claim 50, wherein the application rate of the crystalline modification IV of pyraclostrobin, is in the range of from about 5 to about 350 gram per hectare.
52. The use according to claim 51, wherein the application rate of the crystalline modification IV of pyraclostrobin is in the range of from about 50 to about 300 gram per hectare.
53. The use according to any of claims 36 to 52, wherein the components (A) and (B) are applied to the plants, plant parts and/or locus where control is desired simultaneously and/or in succession.
10
54. The use according to any of claims 36 to 53, wherein a composition of any of claims 1 to 16 is employed.
55. A fungicidal composition substantially as hereinbefore described.
15
56. A method for treating and/or preventing fungal infestations in plants and/or plant materials substantially as hereinbefore described.
57. The use substantially as hereinbefore described.
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Application No: GB1613454.6 Examiner: Helen Yard
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CN201780047244.7A CN109561686A (en) 2016-08-04 2017-07-27 Synergistic fungicidal composition and application thereof
PCT/CN2017/094632 WO2018024147A1 (en) 2016-08-04 2017-07-27 A synergistic fungicidal composition and use thereof
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US7501384B2 (en) * 2003-02-14 2009-03-10 Basf Aktiengesellschaft Crystalline modification of the anhydrate of boscalid
US7816392B2 (en) * 2005-06-20 2010-10-19 Basf Aktiengesellschaft Crystalline modifications to pyraclostrobin

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CN1731026A (en) * 2005-08-02 2006-02-08 范顺岐 Solar energy heat pump heating apparatus
PT2453739E (en) * 2009-07-14 2013-10-03 Basf Se A process for preparing an aqueous suspension of an organic pesticide compound
JP2013510113A (en) * 2009-11-06 2013-03-21 ビーエーエスエフ ソシエタス・ヨーロピア Crystalline complex of 4-hydroxybenzoic acid and selected pesticide
CN103347389A (en) * 2010-12-09 2013-10-09 拜耳知识产权有限责任公司 Pesticidal mixtures with improved properties
CN103719120A (en) * 2012-10-15 2014-04-16 海利尔药业集团股份有限公司 Sterilization composition containing pyraclostrobin and boscalid
CN103355333A (en) * 2013-07-31 2013-10-23 海利尔药业集团股份有限公司 Sterilization composition containing pyraclostrobin and boscalid
CN103392706B (en) * 2013-08-21 2017-04-12 陕西康禾立丰生物科技药业有限公司 Pesticide for preventing and treating fungous and bacterial diseases of crop, and preparation of pesticide
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CN104430435A (en) * 2014-12-29 2015-03-25 河北野田农用化学有限公司 Water-dispersing granulated pesticide containing pyraclostrobin and boscalid, preparation method and application thereof

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US7816392B2 (en) * 2005-06-20 2010-10-19 Basf Aktiengesellschaft Crystalline modifications to pyraclostrobin

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TWI789356B (en) 2023-01-11
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