WO1999025187A2 - Pesticidal compositions of emamectin - Google Patents

Pesticidal compositions of emamectin Download PDF

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Publication number
WO1999025187A2
WO1999025187A2 PCT/EP1998/006953 EP9806953W WO9925187A2 WO 1999025187 A2 WO1999025187 A2 WO 1999025187A2 EP 9806953 W EP9806953 W EP 9806953W WO 9925187 A2 WO9925187 A2 WO 9925187A2
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WO
WIPO (PCT)
Prior art keywords
composition
emamectin
propagation material
xxxiv
london
Prior art date
Application number
PCT/EP1998/006953
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French (fr)
Other versions
WO1999025187A3 (en
Inventor
Martine Arslan-Bir
Original Assignee
Novartis Ag
Novartis-Erfindungen Verwaltungsgesellschaft Mbh
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from CH264797A external-priority patent/CH692595A5/en
Application filed by Novartis Ag, Novartis-Erfindungen Verwaltungsgesellschaft Mbh filed Critical Novartis Ag
Priority to AU16659/99A priority Critical patent/AU1665999A/en
Publication of WO1999025187A2 publication Critical patent/WO1999025187A2/en
Publication of WO1999025187A3 publication Critical patent/WO1999025187A3/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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N29/00—Biocides, pest repellants or attractants, or plant growth regulators containing halogenated hydrocarbons
    • A01N29/04—Halogen directly attached to a carbocyclic ring system
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
    • A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/32—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
    • 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
    • A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
    • 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
    • A01N49/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
    • A01N57/28—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing acyclic or cycloaliphatic radicals
    • 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
    • A01N63/00—Biocides, pest repellants or attractants, or plant growth regulators containing microorganisms, viruses, microbial fungi, animals or substances produced by, or obtained from, microorganisms, viruses, microbial fungi or animals, e.g. enzymes or fermentates
    • A01N63/20—Bacteria; Substances produced thereby or obtained therefrom
    • A01N63/22—Bacillus
    • A01N63/23—B. thuringiensis

Definitions

  • the present invention relates to a composition comprising a pesticidal combination of active ingredients, to a method for controlling pests with this composition, to a method for preparing the composition, to its use and to plant propagation material treated with the composition, as well as to the use of emamectin and compounds of the following formulae (I) to (XXXIV) for preparing the composition.
  • the object of the invention is accordingly a composition for the control of insects and/or members of the order Acarina, which comprises a combination in variable proportions of emamectin (A), in free form or in the form of a salt, and one or more of the compounds:
  • (XXXIV) a product which can be isolated from a strain of Bacillus thuringiensis; in each case in free form or in the form of a salt, and at least one adjuvant.
  • Emamectin is a mixture of 4"-deoxy-4"-N-methylamino avermectin B ⁇ a /B i and is described in US-P-4,4874,749 and as MK-244 in Journal of Organic Chemistry, Vol. 59 (1994), 7704- 7708. Salts of emamectin which are of particular agrochemicat value are described in US-P- 5,288,710.
  • (XXI) 0-4-bromo-2-chlorophenyl O-ethyl S-propyl phosphorothioate (profenofos), from The Pesticide Manual, 9 th Ed. (1991 ), The British Crop Protection Council, London, page 705;
  • (XXII) a mixture of 50 to 80% (2RS,4SR)-4-(2-ethyl-1 ,3-dioxolan-4-ylmethoxy)phenyl phenyl ether and 50 to 20% (2RS,4RS)-4-(2-ethyl-1 ,3-dioxolan-4-ylmethoxy)phenyl phenyl ether (diofenolan), from The Pesticide Manual, 10 th Ed. (1994), The British Crop Protection Council, London, page 363;
  • mineral acids e.g. sulfuric acid, perchloric acid, nitric acid, nitrous acid, a phosphoric acid or a hydrogen halide acid
  • strong organic carbonic acids typically d-C 4 alkanecarbonic acids substituted where appropriate for example by halogen, e.g.
  • acetic acid such as dicarbonic acids that are unsaturated where appropriate, e.g. oxalic, malonic, succinic, maleic, fumaric or phthalic acid, typically hydroxycarbonic acids, e.g. ascorbic, lactic, malic, tartaric or citric acid, or benzoic acid, or with organic sulfonic acids, typically C ⁇ -C 4 alkanesulfonic or arylsulfonic acids substituted where appropriate for example by halogen, e.g. methanesulfonic or p- toluenesulfonic acid.
  • compounds of formula (I) to (XXXIV) with at least one acid group can form salts with bases.
  • Suitable salts with bases are for example metal salts, typically alkali or alkaline earth metal salts, e.g. sodium, potassium or magnesium salts, or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower alkylamine, e.g. ethyl, diethyl, triethyl or dimethylpropylamine, or a mono-, di- or trihydroxy-lower alkylamine, e.g. mono-, di- or triethanolamine.
  • Corresponding internal salts where appropriate may also be formed.
  • Preferred compounds within the scope of this invention are agrochemically useful salts.
  • composition comprising emamectin as agrochemically acceptable salt, especially as benzoate, substituted benzoate, benzenesulfonate, citrate, phosphate, tartrate or maleate; preferably as benzoate or benzenesulfonate; especially benzoate.
  • mixtures comprising emamectin (MK-244) in a ratio of B 1a > 80 wt-%, B 1b ⁇ 20 wt-%, especially B 1a > 90 wt-%, B ib ⁇ 10 wt-%.
  • compositions which comprises in addition to emamectin only one further pesticidally active compound (I) to (XXXIV).
  • Further preferred compositions are those comprising in addition to emamectin also azamethiphos, or fenoxycarb, or cypermethrin high-cis, or profenofos, or lufenuron, or pymetrozine.
  • compositions comprising a compound which is obtainable from a strain of Bacillus thuringiensis.
  • Thuricide®, Vault® CGA237218 (M200, Able®), H14, GC91 (Agree®, Turex®), DSM3435, known from US-P-4,996,156; DSM3440, known from US-P-4,996,156; HD541 , HD571 and
  • HD73 particularly H7 (B401 ), H14, H3a,3b, CGA237218 (M200), H14, GC91 , DSM3435;
  • the combination of active ingredients according to the invention comprises active ingredient (A) and one of the active ingredients (I) to (XXXIV) preferably in a ratio of 100:1 to 1 :6000, especially 1 :50 to 50:1 , in particular in a ratio of between 1 :20 and 20:1 , especially between 10:1 and 1 :10, very especially between 5:1 and 1 :5, especially preferably between 2:1 and 1 :2, also preferably between 4:1 and 2:1 , very particularly in the ratio 1 :1 , or 5:1 , or 5:2, or 5:3, or 5:4, or 4:1 , or 4:2, or 4:3, or 3:1 , or 3:2, or 2:1 , or 1 :5, or 2:5, or 3:5, or 4:5, or 1 :4, or 2:4, or 3:4, or 1 :3, or 2:3, or 1 :2, or, 1 :600, or 1 :300, or 1 :150, or 1 :35, or 2:35, or 4:35, or 1 :75
  • the concentrations of emamectin and the individual compounds (I) to (XXXIV) are reduced, while efficacy remains unchanged.
  • the combined mixture also achieves a high degree of pest control where the two individual substances have become completely ineffective when applied at unduly low concentrations. This allows a considerable widening of the spectrum of pests which can be controlled and increased safety of use.
  • composition of the invention also shows further surprising advantages, which can likewise be described as synergistic in a broader sense: for example, they allow the control of pests which are not sufficiently, or not at all, susceptible to treatment with emamectin or a compound (I) to (XXXIV) when applied separately, and the compositions of the invention are better tolerated by plants, i.e. they are less phytotoxic, for example, than emamectin and (I) to (XXXIV).
  • insects can also be controlled in their different development stages, which is not always the case with emamectin or the individual compounds (I) to (XXXIV), because these compounds for example can be used only as adulticides or only as larvicides against very specific instars.
  • combinations of emamectin with certain compounds (I) to (XXXIV) show more favourable behaviour during grinding, mixing, storage, and also spraying.
  • compositions of the invention are of preventive and/or curative merit for use in pest control among warm-blooded animals, fish, and plants even at low concentrations and show a very favourable spectrum of biocidal activity.
  • the active ingredients according to the invention are active against all or individual development stages of animal pests showing normal sensitivity, and also of those showing resistance, for example insects or members of the order acarina.
  • the insecticidal or acaricidal effect of the compositions of the invention can manifest itself directly, i.e. killing the pests either immediately or after some time has elapsed, for example when moulting occurs, or indirectly, e.g. reducing the number of eggs laid and/or the hatching rate, good efficacy corresponding to a destruction rate (mortality) of at least 50 to 60%.
  • the said animal pests include, for example, those which are mentioned in the European Patent application EP-A-736'252 .
  • the pests mentioned in EP-A-736'252 are thus included by reference in the object of the present invention.
  • Pests of said type which occur on plants, especially on crops and ornamentals in agriculture, horticulture and forestry, or on parts of such plants, such as fruits, blooms, leaves, stems, tubers or roots, can be controlled, i.e. kept in check or eradicated, using the active ingredient mixtures of the invention, this protection remaining for parts of some plants whose growth does not occur until later.
  • the pesticide mixture according to the invention can be used to advantage for pest control especially in cereals, such as corn or sorghum; in fruit, e.g. pomes, drupes and soft fruit, such as apples, pears, plums, peaches, almonds, cherries or berries, e.g.
  • strawberries, raspberries or blackberries in leguminous plants, such as beans, lentils, peas or soybean; in oil crops, such as rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans or groundnuts; in cucumber plants, such as pumpkins, cucumbers or melons; in fibrous plants, such as cotton, flax, hemp or jute; in citrus fruits, such as oranges, lemons, grapefruit or mandarins; in vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes or paprika; in lauraceae, such as avocado, cinnamon or camphor; and in tobacco, nuts, coffee, aubergines, sugar cane, tea, pepper, grapevines, hops, banana plants, natural rubber plants and ornamentals, most especially in corn, sorghum, pomes and drupes, leguminous plants, cucumber plants, cotton, citrus fruits, vegetables, aubergines, vines, hops, or ornamentals, especially in corn, sorghum, apples
  • the pesticides of the invention are, depending on the intended objectives and prevailing circumstances, emulsifiable concentrates, suspension concentrates, directly sprayable or dilutable solutions, coatable pastes, dilute emulsions, spray powders, soluble powders, dispersible powders, wettable powders, dusts, granulates or encapsulations in polymeric substances, comprising emamectin and one of the other active ingredients (I) to (XXXIV) according to the invention.
  • the active ingredients are employed in pure form, the solid active ingredients in a specific particle size, or preferably together with - at least - one of the adjuvants conventionally used in the art of formulation, such as extenders, e.g. solvents or solid carriers, or surface-active compounds (surfactants).
  • the adjuvants which can be used for formulation are, for example, solid carriers, solvents, stabilizers, "slow-release” agents, dyes, and where appropriate surfactants.
  • Carriers and adjuvants can be any substance conventionally used in crop protection agents.
  • Adjuvants such as solvents, solid carriers, surface-active compounds, non-ionic surfactants, cationic surfactants, anionic surfactants, and other adjuvants in the compositions of the invention can, for example, be the same as those described in EP-A-736'252 .
  • the compositions comprise 0.01 to 99.99%, in particular 0.1 to 95%, of a mixture of active ingredient (A) with one of the active ingredients (I) to (XXXIV), and 1 to 99.9%, in particular 5 to 99.9%, of - at least - one solid or liquid adjuvant, it being possible as a rule for 0 to 25%, in particular 0.1 to 20%, of the compositions to be surfactants (% in each case meaning percent by weight).
  • surfactants % in each case meaning percent by weight
  • the end consumer as a rule uses dilute compositions which have substantially lower concentrations of active ingredient.
  • Preferred compositions are composed in particular as mentiond in EP-A-736'252.
  • compositions of the invention can also comprise other solid or liquid adjuvants, such as stabilizers, e.g. vegetable oils, epoxidized where appropriate (e.g. epoxidized coconut oil, rapeseed oil or soya oil), antifoams, e.g. silicone oil, preservatives, viscosity modulators, binders and/or tackifiers, and also fertilizers or other active ingredients to achieve specific effects, e.g. acaricides, bactericides, fungicides, nematocides, molluscicides or selective herbicides.
  • stabilizers e.g. vegetable oils, epoxidized where appropriate (e.g. epoxidized coconut oil, rapeseed oil or soya oil), antifoams, e.g. silicone oil, preservatives, viscosity modulators, binders and/or tackifiers, and also fertilizers or other active ingredients to achieve specific effects, e.g
  • compositions of the invention are prepared in a known manner, e.g. in the absence of adjuvants by grinding, sieving, and/or compressing a solid active ingredient or active ingredient mixture, e.g. to a specific particle size, and in the presence of at least one adjuvant, e.g. by intimately mixing and/or grinding the active ingredient or the mixture of active ingredients with the adjuvant(s).
  • the method for preparing the compositions is therefore a further object of the invention.
  • the mixtures of emamectin with one or more of the compounds (I) to (XXXIV) are preferably employed with the adjuvants conventionally used in the art of formulation and are therefore processed in a known manner to give, for example, emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules or microencapsulations in for example polymeric substances.
  • the methods of application such as spraying, atomizing, dusting, wetting, scattering or pouring, are selected in accordance with the intended objectives and the prevailing circumstances.
  • compositions i.e. the methods of controlling pests of said type, such as spraying, atomizing, dusting, coating, dressing, scattering or pouring (chosen in accordance with the intended objectives and prevailing circumstances), and the use of the compositions for controlling pests of said type are further objects of the invention.
  • Typical concentrations of active ingredient are between 0.1 and 1000 ppm, preferably between 0.1 and 500 ppm.
  • the rate of application can vary within wide limits and depends on the nature of the soil, the type of application (leaf application, seed dressing, application to the seed furrow), the cultivated plant, the pest to be controlled, the prevailing climatic conditions, and on other factors governed by the type and time of application and the target crop.
  • the rates of application are generally 1 to 2000 g of active ingredient (a.i.) per hectare, especially 10 to 1000 g a.i./ha, and preferably 20 to 600 g a.i./ha.
  • a preferred method of application for crop protection is to apply the active ingredient to the foliage of the plants (leaf application), the number of applications and the rate of application depending on the intensity of infestation by the pest in question.
  • the active ingredients can also penetrate the plant through the roots via the soil (systemic action) by drenching the locus of the plants with a liquid composition, or by applying the compounds in solid form to the locus of the plants, e.g. to the soil, for example in granular form (soil application). With paddy rice cultures, granules may be metered into the flooded paddy field.
  • compositions of the invention are also suitable for protecting plant propagation material, e.g. seeds, such as fruits, tubers or grains, or plant seedlings, from animal pests.
  • the propagation material can be treated with the composition before the start of cultivation, seeds for example being dressed before they are sown.
  • the active ingredients of the invention can also be applied to seeds (coating) by either soaking the seeds in a liquid composition or coating them with a solid composition.
  • the composition can also be given when the propagation material is introduced to the place of cultivation, e.g. when the seeds are sown in the seed furrow.
  • the treatment procedures for plant propagation material and the propagation material thus treated are further objects of the invention.
  • the invention is illustrated by the following examples. They do not impose any limitation on the invention.
  • Example F1 Emulsion concentrates a) b) c)
  • Tributyl phenol polyethylene glycol ether (30 mol EO) 12 % 4 %
  • EO means the degree of ethoxylation of castor oil or tributyl phenol.
  • Emulsions of any desired concentration can be prepared from such concentrates by dilution with water.
  • Example F2 Solutions a) b) c) d)
  • Epoxidized coconut oil 1 1 %% 5 %
  • the solutions are suitable for use in the form of microdrops.
  • Example F3 Granulates a) b) c) d)
  • Attapulgite 90 % 18 % Th e active ingredients are dissolved in dichloromethane, the solution sprayed onto the carrier, and the solvent subsequently evaporated in vacuo.
  • a synergistic effect is present whenever the action Ae of the combination of an active ingredient of formula (A) with one of the compounds (I) to (XXXIV) is greater than the sum of the actionss of the active ingredients applied individually:
  • the expected pesticidal action Ae for a given combination of two pesticides can be calculated as follows (q.v. COLBY, S.R., "Calculating synergistic and antagonistic response of herbicide combinations", Weeds 15, pages 20-22, 1967):
  • Y percent mortality after treatment with compound (I) to (XXXIV) at a rate of application of q kg / ha versus untreated controls.
  • Ae expected pesticidal action (percent mortality versus the untreated controls) after treatment with emamectin and a compound (I) to (XXXIV) at a rate of application of p + q kg / ha.
  • Example B1 Effect on Bemisia tabaci
  • Dwarf bean plants are placed into gauze cages and populated with adults of Bemisia tabaci. Following oviposition, all adults are removed. Ten days later, the plants and the nymphs thereon are sprayed with an aqueous suspension spray mixture comprising 50 ppm of the mixture of active ingredients. After a further 14 days, the percentage hatching rate of the eggs is compared with that for untreated controls.
  • Example B2 Effect on Spodoptera littoralis caterpillars
  • Young soya plants are sprayed with an aqueous emulsion spray mixture comprising 360 ppm of the mixture of active ingredients. After the spray deposit has dried, the soya plants are populated with 10 third-instar caterpillars of Spodoptera littoralis and placed in a plastic container. Three days later they are evaluated. The percentage reduction of the population and percentage reduction in feeding damage (% response) is determined by comparing the number of dead caterpillars and the extent of feeding damage on the treated plants with those on the untreated plants.
  • Example B3 Ovicidal effect on Lobesia botrana
  • Eggs of Lobesia botrana deposited on filter paper are immersed briefly in a test solution comprising 400 ppm of the mixture of active ingredients to be tested in acetone / water. After the test solution has dried, the eggs are incubated in Petri dishes. After 6 days, the percentage hatching rate of the eggs is compared with that for untreated controls (% reduction in hatching rate).
  • Example B4 Ovicidal effect on Heliothis virescens
  • Example B5 Effect on Plutella xylostella caterpillars
  • Young cabbage plants are sprayed with an aqueous emulsion spray mixture comprising the mixture of active ingredients. After the spray deposit has dried, the cabbage plants are populated with 10 third-instar caterpillars of Plutella xylostella and placed in a plastic container. Three days later they are evaluated. The percentage reduction of the population and percentage reduction in feeding damage (% response) is determined by comparing the number of dead caterpillars and the extent of feeding damage on the treated plants with those on the untreated plants.

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Abstract

The object of the invention is accordingly a composition for the control of insects and/or members of the order acarina, which comprises a combination in variable proportions of emamectin, in free form or in the form of a salt, and one or more of the compounds: azamethiphos; chlorfenvinphos; cypermethrin; cypermethrin high-cis; cyromazine; diafenthiuron; diazinon; dichlorvos; dicrotophos; dicyclanil; fenoxycarb; fluazuron; furathiocarb; isazofos; jodfenphos; kinoprene; lufenuron; methacriphos; methidathion; monocrotophos; phosphamidon; profenofos; diofenolan; pymetrozine; bromopropylate; methoprene; disulfoton; quinalphos; tau-fluvalinate; thiocyclam; thiometon; propetamphos; formothion; dienochlor, or a product which can be isolated from a strain of si(Bacillus thuringiensis); in free form or in the form of a salt, and at least one adjuvant; a method for controlling pests, a method for preparing the composition, the use thereof, and plant propagation material treated with the composition, as well as the use of emamectin to prepare the composition.

Description

Pesticidal composition
The present invention relates to a composition comprising a pesticidal combination of active ingredients, to a method for controlling pests with this composition, to a method for preparing the composition, to its use and to plant propagation material treated with the composition, as well as to the use of emamectin and compounds of the following formulae (I) to (XXXIV) for preparing the composition.
In the literature, certain mixtures of active ingredients are proposed for pest control. The biological properties of these mixtures of known compounds, however, are not fully satisfactory in the field of pest control, which is why there is a need to produce further mixtures with synergistic pesticidal properties, especially for the control of insects and members of the order acarina. This problem is solved according to the invention with the development of the present composition.
The object of the invention is accordingly a composition for the control of insects and/or members of the order Acarina, which comprises a combination in variable proportions of emamectin (A), in free form or in the form of a salt, and one or more of the compounds:
(I) azamethiphos; (XVI) lufenuron;
(II) chlorfenvinphos; (XVII) methacriphos;
(III) cypermethrin, cypermethrin high-cis; (XVIII) methidathion;
(IV) cyromazine; (XIX) monocrotophos;
(V) diafenthiuron; (XX) phosphamidon;
(VI) diazinon; (XXI) profenofos;
(VII) dichlorvos; (XXII) diofenolan;
(VIII) dicrotophos; (XXIII) pymetrozine;
(IX) dicyclanil; (XXIV) bromopropylate;
(X) fenoxycarb; (XXV) methoprene;
(XI) fluazuron; (XXVI) disulfoton;
(XII) furathiocarb; (XXVII) quinalphos;
(XIII) isazofos; (XXVIII) tau-fluvalinate;
(XIV) jodfenphos; (XXIX) thiocyclam;
(XV) kinoprene; (XXX) thiometon; (XXXI) propetamphos, (XXXIII) dienochlor; or
(XXXII) formothion,
(XXXIV) a product which can be isolated from a strain of Bacillus thuringiensis; in each case in free form or in the form of a salt, and at least one adjuvant.
Emamectin is a mixture of 4"-deoxy-4"-N-methylamino avermectin Bιa/Bi and is described in US-P-4,4874,749 and as MK-244 in Journal of Organic Chemistry, Vol. 59 (1994), 7704- 7708. Salts of emamectin which are of particular agrochemicat value are described in US-P- 5,288,710.
(I) S-6-chloro-2,3-dihydro-2-oxo-1 ,3-oxazolo[4,5-b]pyridin-3-ylmethyl 0,0-dimethyl phosphorothioate (azamethiphos), The Pesticide Manual, 9thEd. (1991 ), is known from The British Crop Protection Council, London, page 44;
(II) 2-chloro-1 -(2,4-dichlorophenyl)vinyl diethyl phosphate (chlorfenvinphos), from The Pesticide Manual, 10th Ed. (1994), is from The British Crop Protection Council, London, page 174;
(III) (RS)-α-cyano-3-phenoxybenzyl (1 RS)-cis-trans-3-(2,2-dichlorovinyl)-1 ,1 -dimethylcyclo- propanecarboxylate (cypermethrin, cypermethrin high-cis), from The Pesticide Manual, 9th Ed. (1991 ), The British Crop Protection Council, London, page 208;
(IV) N-cyclopropyl-1 ,3,5-triazine-2,4,6-triamine (cyromazine), from The Pesticide Manual, 9th Ed. (1991 ), The British Crop Protection Council, London, page 217;
(V) 1 -tert-butyl-3-(2,6-di-isopropyl-4-phenoxyphenyl)thiourea (diafenthiuron), from The Pesticide Manual, 10th Ed. (1994), The British Crop Protection Council, London, page 294;
(VI) 0,0-Diethyl 0-2-lsopropyl-6-methylpyrimidin-4-yl-phosphorothioate (diazinon), from The Pesticide Manual, 9th Ed. (1991 ), The British Crop Protection Council, London, page 243;
(VII) 2,2-dichlorovinyl dimethyl phosphate (dichlorvos), from The Pesticide Manual, 9th Ed. (1991 ), The British Crop Protection Council, London, page 259;
(VIII) (E)-2-dimethylcarbamoyl-1 -methylvinyl dimethyl phosphate (dicrotophos), from The Pesticide Manual, 10th Ed. (1994), The British Crop Protection Council, London, page 322;
(IX) 5-cyano-2-cyclopropylamino-4,6-diaminopyrimidine (dicyclanil), known from EP-A- 244360; (X) ethyl 2-(4-phenoxyphenoxy)ethylcarbamate (fenoxycarb), from The Pesticide Manual, 9th Ed. (1991 ), The British Crop Protection Council, London, page 375;
(XI) 1 -[4-chloro-3-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenyl]-3-(2,6-difluorobenzoyl)urea (fluazuron), from The Pesticide Manual, 10th Ed. (1994), The British Crop Protection Council, London, page 475;
(XII) butyl 2,3-dihydro-2,2-dimethylbenzofuran-7-yl N,N'-dimethyl-N,N'-thiodicarbamate (furathiocarb), from The Pesticide Manual, 9th Ed. (1991 ), The British Crop Protection Council, London, page 448;
(XIII) 0-5-chloro-1 -isopropyl-1 H-1 ,2,4-triazol-3-yl O,0-diethylphosphorothioate (isazofos), aus The Pesticide Manual, 9th Ed. (1991 ), The British Crop Protection Council, London, page 502;
(XIV) 0-2,5-dichloro-4-iodophenyl O,0-dimethylphosphorothioate (jodfenphos), from The Pesticide Manual, 10th Ed. (1994), The British Crop Protection Council, London, page 1102;
(XV) prop-2-ynyl (±) (E,E)-3,7,11 -trimethyldodeca-2,4-dienoate (kinoprene) from The Pesticide Manual, 10th Ed. (1994), The British Crop Protection Council, London, page 1102;
(XVI) (R,S)-1-[2,5-dichloro-4-(1 ,1 ,2,3,3,3-hexafluoropropoxy)phenyl]-3-(2,6- difluorobenzoyl)urea (lufenuron), from The Pesticide Manual, 10lh Ed. (1994), The British Crop Protection Council, London, page 628;
(XVII) methyl (E)-3-(dimethoxyphosphinothioyloxy)-2-methylacrylate (methacriphos) from The Pesticide Manual, 9th Ed. (1991 ), The British Crop Protection Council, London, page 562;
(XVIII) S-2,3-dihydro-5-methoxy-2-oxo-1 ,3,4-thiadiazol-3-ylmethyl 0,0-dimethyl phosphorodithioate (methidathion), from The Pesticide Manual, 10th Ed. (1994), The British Crop Protection Council, London, page 674;
(XIX) dimethyl (E)-1 -methyl-2-(methylcarbamoyl)vinyl phosphate (monocrotophos), from The Pesticide Manual, 9th Ed. (1991 ), The British Crop Protection Council, London, page 597;
(XX) 2-chloro-2-diethylcarbamoyl-1 -methylvinyl dimethyl phosphate (phosphamidon), known from The Pesticide Manual, 9th Ed. (1991 ), The British Crop Protection Council, London, page 679;
(XXI) 0-4-bromo-2-chlorophenyl O-ethyl S-propyl phosphorothioate (profenofos), from The Pesticide Manual, 9th Ed. (1991 ), The British Crop Protection Council, London, page 705; (XXII) a mixture of 50 to 80% (2RS,4SR)-4-(2-ethyl-1 ,3-dioxolan-4-ylmethoxy)phenyl phenyl ether and 50 to 20% (2RS,4RS)-4-(2-ethyl-1 ,3-dioxolan-4-ylmethoxy)phenyl phenyl ether (diofenolan), from The Pesticide Manual, 10th Ed. (1994), The British Crop Protection Council, London, page 363;
(XXIII) 2,3,4,5-tetrahydro-3-oxo-4-[(pyridin-3-yl)methyleneamino]-6-methyl-1 ,2,4-triazine (pymetrozine), from The Pesticide Manual, 10th Ed. (1994), The British Crop Protection Council, London, page 868; and
(XXIV) isopropyl 4,4'-dibromobenzilate (bromopropylate), from The Pesticide Manual, 9th Ed. (1991 ), The British Crop Protection Council, London, page 99,
(XXV) Isopropyl (E,E)-(R,S)-1 1 -methoxy-3J,1 1-trimethyl-dodeca-2,4-dienoat (Methoprene), aus The Pesticide Manual, 10th Ed. (1994), The British Crop Protection Council, London, Seite 680;isopropyl (E,E)-(R,S)-1 1 -methoxy-3J,1 1-trimethyl-dodeca-2,4-dienoate (methoprene) from The Pesticide Manual, 10th Ed. (1994), The British Crop Protection Council, London, page 680;
(XXVI) 0,0-diethyl S-2-ethylthioethyl phosphorodithioate (disulfoton), from The Pesticide Manual, 10thEd. (1994), The British Crop Protection Council, London, page 372;
(XXVII) O.O-diethyl O-quinoxalin-2-yl phosphorothioate (quinalphos), from The Pesticide Manual, 10thEd. (1994), The British Crop Protection Council, London, page 890, and
(XXVIII) (RS)-α-cyano-3-phenoxybenzyl N-(2-Chloro-α,α,α-trifluoro-p-tolyl)-D-valinate (tau- fluvalinate), known from The Pesticide Manual, 9,hEd. (1991 ), The British Crop Protection Council, London, page 428;
(XXIX) N,N-dimethyl-1 ,2,3-trithian-5-yl-amine (thiocyclam) from The Pesticide Manual, 9thEd. (1991 ), The British Crop Protection Council, London, page 816;
(XXX) S-2-ethylthioethyl 0,0-dimethyl phosphorodithioate (thiometon) from The Pesticide Manual, 9,hEd. (1991 ), The British Crop Protection Council, London, page 819, and
(XXXI) propetamphos from The Pesticide Manual, 10thEd. (1994), from The British Crop Protection Council, London, page 852;
(XXXII) formothion from The Pesticide Manual, 10,hEd. (1994), from The British Crop Protection Council, London, page 527;
(XXXIII) dienochlor from The Pesticide Manual, 10,hEd. (1994), The British Crop Protection Council, London, page 523, and
(XXXIV) products obtainable from a strain of Bacillus thuringiensis, known from The Pesticide Manual, 10thEd. (1994), The British Crop Protection Council, London, page 62; Compounds (I) to (XXXIV) showing at least one basic centre may form acid addition salts. These are formed for example with strong inorganic acids, such as mineral acids, e.g. sulfuric acid, perchloric acid, nitric acid, nitrous acid, a phosphoric acid or a hydrogen halide acid, with strong organic carbonic acids, typically d-C4alkanecarbonic acids substituted where appropriate for example by halogen, e.g. acetic acid, such as dicarbonic acids that are unsaturated where appropriate, e.g. oxalic, malonic, succinic, maleic, fumaric or phthalic acid, typically hydroxycarbonic acids, e.g. ascorbic, lactic, malic, tartaric or citric acid, or benzoic acid, or with organic sulfonic acids, typically Cι-C4alkanesulfonic or arylsulfonic acids substituted where appropriate for example by halogen, e.g. methanesulfonic or p- toluenesulfonic acid. In a broader sense, compounds of formula (I) to (XXXIV) with at least one acid group can form salts with bases. Suitable salts with bases are for example metal salts, typically alkali or alkaline earth metal salts, e.g. sodium, potassium or magnesium salts, or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower alkylamine, e.g. ethyl, diethyl, triethyl or dimethylpropylamine, or a mono-, di- or trihydroxy-lower alkylamine, e.g. mono-, di- or triethanolamine. Corresponding internal salts where appropriate may also be formed. Preferred compounds within the scope of this invention are agrochemically useful salts. The term compounds (I) to (XXXIV) in free form used hereinbefore and hereinafter refers also to the corresponding salts, and the term salts is taken to refers by the same token also to the free compounds (I) to (XXXIV). The same applies also to tautomers of compounds (I) to (XXXIV) and their salts. In each case, the free form is generally preferred. Thiocyclam is preferred as a hydrogen oxalate salt.
Preferred within the scope of the present invention is a composition comprising emamectin as agrochemically acceptable salt, especially as benzoate, substituted benzoate, benzenesulfonate, citrate, phosphate, tartrate or maleate; preferably as benzoate or benzenesulfonate; especially benzoate.
Also preferred are mixtures comprising emamectin (MK-244) in a ratio of B1a > 80 wt-%, B1b < 20 wt-%, especially B1a > 90 wt-%, Bib < 10 wt-%.
A composition is preferred which comprises in addition to emamectin only one further pesticidally active compound (I) to (XXXIV). Further preferred compositions are those comprising in addition to emamectin also azamethiphos, or fenoxycarb, or cypermethrin high-cis, or profenofos, or lufenuron, or pymetrozine. Likewise preferred are compositions comprising a compound which is obtainable from a strain of Bacillus thuringiensis. Especially preferred are the following insecticidally active compounds or strains from which these compounds are obtainable:
SAN 4151, San 2391, SAN 4011, H7 (B401 ), H14, EG2348 (Condor OF®), EG2349
(Bollgard®), EG2371 (Cutlass®), EG2424 (Foil®, Jackpot®); H3a,3b (Javelin®, Steward®,
Thuricide®, Vault®); CGA237218 (M200, Able®), H14, GC91 (Agree®, Turex®), DSM3435, known from US-P-4,996,156; DSM3440, known from US-P-4,996,156; HD541 , HD571 and
HD73; particularly H7 (B401 ), H14, H3a,3b, CGA237218 (M200), H14, GC91 , DSM3435;
DSM3440, HD541 , HD571 and HD73; especially GC91 ; H3a,3b; and M200; most especially GC91.
The combination of active ingredients according to the invention comprises active ingredient (A) and one of the active ingredients (I) to (XXXIV) preferably in a ratio of 100:1 to 1 :6000, especially 1 :50 to 50:1 , in particular in a ratio of between 1 :20 and 20:1 , especially between 10:1 and 1 :10, very especially between 5:1 and 1 :5, especially preferably between 2:1 and 1 :2, also preferably between 4:1 and 2:1 , very particularly in the ratio 1 :1 , or 5:1 , or 5:2, or 5:3, or 5:4, or 4:1 , or 4:2, or 4:3, or 3:1 , or 3:2, or 2:1 , or 1 :5, or 2:5, or 3:5, or 4:5, or 1 :4, or 2:4, or 3:4, or 1 :3, or 2:3, or 1 :2, or, 1 :600, or 1 :300, or 1 :150, or 1 :35, or 2:35, or 4:35, or 1 :75, or 2:75, or 4:75, or 1 :6000, or 1 :3000, or 1 :1500, or 1 :350, or 2:350, or 4:350, or 1 :750, or 2:750, or 4:750. These ratios refer both to weight ratios and to molar ratios.
It has now been surprisingly found that the combination of emamectin or one of its salts with one of the active ingredients (I) to (XXXIV) not only has an additive effect with regard to the spectrum of activity against the pests to be controlled, which in principle was to be expected, but also exerts a synergistic effect, extending the spectrum of activity of each composition in two respects:
Firstly, the concentrations of emamectin and the individual compounds (I) to (XXXIV) are reduced, while efficacy remains unchanged. Secondly, the combined mixture also achieves a high degree of pest control where the two individual substances have become completely ineffective when applied at unduly low concentrations. This allows a considerable widening of the spectrum of pests which can be controlled and increased safety of use. In addition to the actual synergistic effect with regard to the pesticidal activity, however, the composition of the invention also shows further surprising advantages, which can likewise be described as synergistic in a broader sense: for example, they allow the control of pests which are not sufficiently, or not at all, susceptible to treatment with emamectin or a compound (I) to (XXXIV) when applied separately, and the compositions of the invention are better tolerated by plants, i.e. they are less phytotoxic, for example, than emamectin and (I) to (XXXIV). The insects can also be controlled in their different development stages, which is not always the case with emamectin or the individual compounds (I) to (XXXIV), because these compounds for example can be used only as adulticides or only as larvicides against very specific instars. In addition, combinations of emamectin with certain compounds (I) to (XXXIV) show more favourable behaviour during grinding, mixing, storage, and also spraying.
The compositions of the invention are of preventive and/or curative merit for use in pest control among warm-blooded animals, fish, and plants even at low concentrations and show a very favourable spectrum of biocidal activity. The active ingredients according to the invention are active against all or individual development stages of animal pests showing normal sensitivity, and also of those showing resistance, for example insects or members of the order acarina. The insecticidal or acaricidal effect of the compositions of the invention can manifest itself directly, i.e. killing the pests either immediately or after some time has elapsed, for example when moulting occurs, or indirectly, e.g. reducing the number of eggs laid and/or the hatching rate, good efficacy corresponding to a destruction rate (mortality) of at least 50 to 60%.
The said animal pests include, for example, those which are mentioned in the European Patent application EP-A-736'252 . The pests mentioned in EP-A-736'252 are thus included by reference in the object of the present invention.
Pests of said type which occur on plants, especially on crops and ornamentals in agriculture, horticulture and forestry, or on parts of such plants, such as fruits, blooms, leaves, stems, tubers or roots, can be controlled, i.e. kept in check or eradicated, using the active ingredient mixtures of the invention, this protection remaining for parts of some plants whose growth does not occur until later. The pesticide mixture according to the invention can be used to advantage for pest control especially in cereals, such as corn or sorghum; in fruit, e.g. pomes, drupes and soft fruit, such as apples, pears, plums, peaches, almonds, cherries or berries, e.g. strawberries, raspberries or blackberries; in leguminous plants, such as beans, lentils, peas or soybean; in oil crops, such as rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans or groundnuts; in cucumber plants, such as pumpkins, cucumbers or melons; in fibrous plants, such as cotton, flax, hemp or jute; in citrus fruits, such as oranges, lemons, grapefruit or mandarins; in vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes or paprika; in lauraceae, such as avocado, cinnamon or camphor; and in tobacco, nuts, coffee, aubergines, sugar cane, tea, pepper, grapevines, hops, banana plants, natural rubber plants and ornamentals, most especially in corn, sorghum, pomes and drupes, leguminous plants, cucumber plants, cotton, citrus fruits, vegetables, aubergines, vines, hops, or ornamentals, especially in corn, sorghum, apples, pears, plums, peaches, beans, peas, soybeans, olives, sunflowers, coconut, cocoa, peanuts, cucumbers, pumpkins, citrus fruits, cabbages, tomatoes, potatoes, vines, or cotton, with special preference in vines, citrus fruits, apples, pears, tomatoes and cotton.
Other indication areas for the active ingredient mixtures of the invention are the protection of stored products and stores and of material and, in the hygiene sector, in particular the protection of domestic animals and livestock against pests of said type.
The pesticides of the invention are, depending on the intended objectives and prevailing circumstances, emulsifiable concentrates, suspension concentrates, directly sprayable or dilutable solutions, coatable pastes, dilute emulsions, spray powders, soluble powders, dispersible powders, wettable powders, dusts, granulates or encapsulations in polymeric substances, comprising emamectin and one of the other active ingredients (I) to (XXXIV) according to the invention.
In these compositions, the active ingredients are employed in pure form, the solid active ingredients in a specific particle size, or preferably together with - at least - one of the adjuvants conventionally used in the art of formulation, such as extenders, e.g. solvents or solid carriers, or surface-active compounds (surfactants). The adjuvants which can be used for formulation are, for example, solid carriers, solvents, stabilizers, "slow-release" agents, dyes, and where appropriate surfactants. Carriers and adjuvants can be any substance conventionally used in crop protection agents. Adjuvants such as solvents, solid carriers, surface-active compounds, non-ionic surfactants, cationic surfactants, anionic surfactants, and other adjuvants in the compositions of the invention can, for example, be the same as those described in EP-A-736'252 .
As a rule, the compositions comprise 0.01 to 99.99%, in particular 0.1 to 95%, of a mixture of active ingredient (A) with one of the active ingredients (I) to (XXXIV), and 1 to 99.9%, in particular 5 to 99.9%, of - at least - one solid or liquid adjuvant, it being possible as a rule for 0 to 25%, in particular 0.1 to 20%, of the compositions to be surfactants (% in each case meaning percent by weight). Whereas concentrated compositions tend to be preferred for commercial goods, the end consumer as a rule uses dilute compositions which have substantially lower concentrations of active ingredient. Preferred compositions are composed in particular as mentiond in EP-A-736'252.
The compositions of the invention can also comprise other solid or liquid adjuvants, such as stabilizers, e.g. vegetable oils, epoxidized where appropriate (e.g. epoxidized coconut oil, rapeseed oil or soya oil), antifoams, e.g. silicone oil, preservatives, viscosity modulators, binders and/or tackifiers, and also fertilizers or other active ingredients to achieve specific effects, e.g. acaricides, bactericides, fungicides, nematocides, molluscicides or selective herbicides.
The compositions of the invention are prepared in a known manner, e.g. in the absence of adjuvants by grinding, sieving, and/or compressing a solid active ingredient or active ingredient mixture, e.g. to a specific particle size, and in the presence of at least one adjuvant, e.g. by intimately mixing and/or grinding the active ingredient or the mixture of active ingredients with the adjuvant(s). The method for preparing the compositions is therefore a further object of the invention.
The mixtures of emamectin with one or more of the compounds (I) to (XXXIV) are preferably employed with the adjuvants conventionally used in the art of formulation and are therefore processed in a known manner to give, for example, emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules or microencapsulations in for example polymeric substances. As with the type of compositions, the methods of application, such as spraying, atomizing, dusting, wetting, scattering or pouring, are selected in accordance with the intended objectives and the prevailing circumstances.
The methods of application for the compositions, i.e. the methods of controlling pests of said type, such as spraying, atomizing, dusting, coating, dressing, scattering or pouring (chosen in accordance with the intended objectives and prevailing circumstances), and the use of the compositions for controlling pests of said type are further objects of the invention. Typical concentrations of active ingredient are between 0.1 and 1000 ppm, preferably between 0.1 and 500 ppm. The rate of application can vary within wide limits and depends on the nature of the soil, the type of application (leaf application, seed dressing, application to the seed furrow), the cultivated plant, the pest to be controlled, the prevailing climatic conditions, and on other factors governed by the type and time of application and the target crop. The rates of application are generally 1 to 2000 g of active ingredient (a.i.) per hectare, especially 10 to 1000 g a.i./ha, and preferably 20 to 600 g a.i./ha.
A preferred method of application for crop protection is to apply the active ingredient to the foliage of the plants (leaf application), the number of applications and the rate of application depending on the intensity of infestation by the pest in question. However, the active ingredients can also penetrate the plant through the roots via the soil (systemic action) by drenching the locus of the plants with a liquid composition, or by applying the compounds in solid form to the locus of the plants, e.g. to the soil, for example in granular form (soil application). With paddy rice cultures, granules may be metered into the flooded paddy field.
The compositions of the invention are also suitable for protecting plant propagation material, e.g. seeds, such as fruits, tubers or grains, or plant seedlings, from animal pests. The propagation material can be treated with the composition before the start of cultivation, seeds for example being dressed before they are sown. The active ingredients of the invention can also be applied to seeds (coating) by either soaking the seeds in a liquid composition or coating them with a solid composition. The composition can also be given when the propagation material is introduced to the place of cultivation, e.g. when the seeds are sown in the seed furrow. The treatment procedures for plant propagation material and the propagation material thus treated are further objects of the invention. The invention is illustrated by the following examples. They do not impose any limitation on the invention.
Formulation examples (% = percent by weight, ratios of active ingredients = weight ratios)
Example F1 : Emulsion concentrates a) b) c)
Active ingredient mixture [emamectin benzoate: compound (I) to (XXXIV) = 1 : 30] 25 % 40 % 50 %
Calcium dodecylbenzenesulfonate 5 % 8 % 6 %
Castor oil polyethylene glycol ether (36 mol EO) 5 %
Tributyl phenol polyethylene glycol ether (30 mol EO) 12 % 4 %
Cyclohexanone 15 % 20 %
Xylene mixture 65 % 25 % 20 %
EO means the degree of ethoxylation of castor oil or tributyl phenol.
Emulsions of any desired concentration can be prepared from such concentrates by dilution with water.
Example F2: Solutions a) b) c) d)
Active ingredient mixture [emamectin benzoate: compound (I) to (XXXIV) = 1 : 10] 8 800 %% 1 100 %% 5 5 %% 95 %
Ethylene glycol monomethyl ether 20 %
Polyethylene glycol MW 400 - 70 %
N-Methyl-2-pyrrolidone 20 %
Epoxidized coconut oil 1 1 %% 5 %
Petroleum ether (boiling limits 160-190°C) 94 %
The solutions are suitable for use in the form of microdrops.
Example F3: Granulates a) b) c) d)
Active ingredient mixture [emamectin benzoate: compound (I) to (XXXIV) = 1 : 5] 5 % 10 % 8 % 21 %
Kaolin 94 % 79 % 54 %
Highly dispersed silicic acid 1 % 13 % 7 %
Attapulgite 90 % 18 % Th e active ingredients are dissolved in dichloromethane, the solution sprayed onto the carrier, and the solvent subsequently evaporated in vacuo.
It is often more convenient to formulate the active ingredient of formula (A) and one of the compounds (I) to (XXXIV) separately and not to combine them until shortly before application in the applicator in the desired mixing ratio in the form of a "tank mix" in water.
Biological examples (% = percent by weight, unless otherwise indicated)
A synergistic effect is present whenever the action Ae of the combination of an active ingredient of formula (A) with one of the compounds (I) to (XXXIV) is greater than the sum of the actionss of the active ingredients applied individually:
Ae > X + Y (B)
The expected pesticidal action Ae for a given combination of two pesticides can be calculated as follows (q.v. COLBY, S.R., "Calculating synergistic and antagonistic response of herbicide combinations", Weeds 15, pages 20-22, 1967):
100 In this formula:
X = percent mortality after treatment with emamectin at a rate of application of p kg / hectare (ha = approximately 2.471 acres) versus untreated controls (= 0 %).
Y = percent mortality after treatment with compound (I) to (XXXIV) at a rate of application of q kg / ha versus untreated controls.
Ae = expected pesticidal action (percent mortality versus the untreated controls) after treatment with emamectin and a compound (I) to (XXXIV) at a rate of application of p + q kg / ha.
If the effect actually observed is greater than the expected Ae value, then synergism is present. Example B1 : Effect on Bemisia tabaci
Dwarf bean plants are placed into gauze cages and populated with adults of Bemisia tabaci. Following oviposition, all adults are removed. Ten days later, the plants and the nymphs thereon are sprayed with an aqueous suspension spray mixture comprising 50 ppm of the mixture of active ingredients. After a further 14 days, the percentage hatching rate of the eggs is compared with that for untreated controls.
In this experiment, the combinations of emamectin with one of the compounds (I) to (XXXIV) show a synergistic effect. In particular, a suspension spray mixture comprising 40 ppm emamectin and 10 ppm of compound (II) is very effective.
Example B2: Effect on Spodoptera littoralis caterpillars
Young soya plants are sprayed with an aqueous emulsion spray mixture comprising 360 ppm of the mixture of active ingredients. After the spray deposit has dried, the soya plants are populated with 10 third-instar caterpillars of Spodoptera littoralis and placed in a plastic container. Three days later they are evaluated. The percentage reduction of the population and percentage reduction in feeding damage (% response) is determined by comparing the number of dead caterpillars and the extent of feeding damage on the treated plants with those on the untreated plants.
In this experiment, the combinations of emamectin with one of the compounds (I) to (XXXIV) show a synergistic effect. In particular, a suspension spray mixture comprising 20 ppm emamectin and 160 ppm of compound (II) and a suspension spray mixture comprising 180 ppm emamectin and 180 ppm of compound (XV) are very effective.
Example B3: Ovicidal effect on Lobesia botrana
Eggs of Lobesia botrana deposited on filter paper are immersed briefly in a test solution comprising 400 ppm of the mixture of active ingredients to be tested in acetone / water. After the test solution has dried, the eggs are incubated in Petri dishes. After 6 days, the percentage hatching rate of the eggs is compared with that for untreated controls (% reduction in hatching rate).
In this experiment, the combinations of emamectin with one of the compounds (I) to (XXXIV) show a synergistic effect. In particular, a suspension spray mixture comprising 300 ppm emamectin and 100 ppm of compound (III) and a suspension spray mixture comprising 200 ppm emamectin and 200 ppm of compound (XVI) are very effective.
Example B4: Ovicidal effect on Heliothis virescens
Eggs of Heliothis virescens deposited on filter paper are immersed briefly in a test solution comprising 400 ppm of the mixture of active ingredients to be tested in acetone / water. After the test solution has dried, the eggs are incubated in Petri dishes. After 6 days, the percentage hatching rate of the eggs is compared with that for untreated controls (% reduction in hatching rate).
In this experiment, the combinations of emamectin with one of the compounds (I) to (XXXIV) show a synergistic effect. In particular, a suspension spray mixture comprising 240 ppm emamectin and 160 ppm of compound (XII) and a suspension spray mixture comprising 300 ppm emamectin and 100 ppm of compound (V) are very effective.
Example B5: Effect on Plutella xylostella caterpillars
Young cabbage plants are sprayed with an aqueous emulsion spray mixture comprising the mixture of active ingredients. After the spray deposit has dried, the cabbage plants are populated with 10 third-instar caterpillars of Plutella xylostella and placed in a plastic container. Three days later they are evaluated. The percentage reduction of the population and percentage reduction in feeding damage (% response) is determined by comparing the number of dead caterpillars and the extent of feeding damage on the treated plants with those on the untreated plants.
In this study, the combinations of emamectin with one of the compounds (I) to (XXXIV) show a synergistic effect. In particular, a suspension spray mixture comprising 400 ppm emamectin and 40 ppm of compound (VII) and a suspension spray mixture comprising 220 ppm emamectin and 220 ppm of compound (IV) are very effective.

Claims

What is claimed is:
1. A composition for the control of insects and/or members of the order acarina which comprises a combination in variable proportions of emamectin (A), in free form or in the form of a salt, and one or more of the compounds:
(I) azamethiphos; (XVIII) methidathion;
(II) chlorfenvinphos; (XIX) monocrotophos;
(III) cypermethrin, cypermethrin high-cis; (XX) phosphamidon;
(IV) cyromazine; (XXI) profenofos;
(V) diafenthiuron; (XXII) diofenolan;
(VI) diazinon; (XXIII) pymetrozine;
(VII) dichlorvos; (XXIV) bromopropylate;
(VIII) dicrotophos; (XXV) methoprene;
(IX) dicyclanil; (XXVI) disulfoton;
(X) fenoxycarb; (XXVII) quinalphos;
(XI) fluazuron; (XXVIII) tau-fluvalinate;
(XII) furathiocarb; (XXIX) thiocyclam;
(XIII) isazofos; (XXX) thiometon;
(XIV) jodfenphos; (XXXI) propetamphos,
(XV) kinoprene; (XXXII) formothion;
(XVI) lufenuron; (XXXIII) dienochlor; or
(XVII) methacriphos;
(XXXIV) a product obtainable from a strain of Bacillus thuringiensis; in each case in free form or in the form of a salt, and at least one adjuvant.
2. A composition of claim 1 comprising azamethiphos.
3. A composition of claim 1 comprising cypermethrin high-cis.
4. A composition of claim 1 comprising fenoxycarb.
5. A method for the control of pests comprising the application of a composition, such as described in one of the claims 1 to 4, to pests or their habitat.
6. A method of claim 5 for protecting plant propagation material, comprising treatment of said propagation material or of the locus for cultivation of said propagation material.
7. A method for preparing a composition such as described in one of the claims 1 to 4, comprising the intimate mixing of the active ingredients with the adjuvant(s).
8. Plant propagation material which is treated according to the method described in claim 6.
9. Use of a composition according to one of the claims 1 to 4 in a method as described in one of the claims 5 or 6.
10. Use of emamectin for the preparation a composition according to one of the claims 1 to 4.
PCT/EP1998/006953 1997-11-14 1998-11-03 Pesticidal compositions of emamectin WO1999025187A2 (en)

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CN101416635A (en) * 2008-11-06 2009-04-29 张少武 Insecticidal composition containing cyromazine with synergistic action
CN102258014A (en) * 2011-05-17 2011-11-30 广西田园生化股份有限公司 Quinalphos emulsion in water and preparation method thereof
CN103583552A (en) * 2013-11-21 2014-02-19 济南凯因生物科技有限公司 Composition for preventing and controlling rice planthoppers
CN103651555A (en) * 2013-12-06 2014-03-26 济南凯因生物科技有限公司 Emulsion in water containing isazofos and applications thereof
CN104255726A (en) * 2014-08-29 2015-01-07 广东省农业科学院植物保护研究所 Emulsion in water containing methoprene and preparation method thereof
CN105432665A (en) * 2014-08-07 2016-03-30 江苏龙灯化学有限公司 Cyhalodiamide and bacillus thuringiensis-containing pesticidal composition
CN105851073A (en) * 2016-04-29 2016-08-17 山东胜伟园林科技有限公司 Saline-alkali soil Chinese cabbage special vegetable insecticide containing derris extracts and preparation method of vegetable insecticide
US9643991B2 (en) * 2015-06-08 2017-05-09 Rotam Agrochem International Company Limited Process for preparing a novel crystalline form of emamectin benzoate and use the same
WO2019005700A1 (en) * 2017-06-26 2019-01-03 Merial, Inc. Dual active parasiticidal granule compositions, methods and uses thereof
CN109169688A (en) * 2018-09-28 2019-01-11 华南农业大学 A kind of Pesticidal combination and application thereof containing thiocyclam and emamectin-benzoate
CN113973833A (en) * 2021-10-18 2022-01-28 河南好年景生物发展有限公司 Sustained-release granule containing lufenuron and emamectin benzoate and applied to corn carpopodium for preventing and treating spodoptera frugiperda
WO2022238576A1 (en) 2021-05-14 2022-11-17 Syngenta Crop Protection Ag Seed treatment compositions
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WO2000002453A1 (en) * 1998-07-07 2000-01-20 Novartis Ag Pesticidal composition comprising emamectin
GR990100222A (en) * 1998-07-07 2000-03-31 Novartis Ag Pesticidal composition comprising emamectin
CN101416635A (en) * 2008-11-06 2009-04-29 张少武 Insecticidal composition containing cyromazine with synergistic action
CN102258014A (en) * 2011-05-17 2011-11-30 广西田园生化股份有限公司 Quinalphos emulsion in water and preparation method thereof
CN103583552A (en) * 2013-11-21 2014-02-19 济南凯因生物科技有限公司 Composition for preventing and controlling rice planthoppers
CN103651555B (en) * 2013-12-06 2015-04-29 济南凯因生物科技有限公司 Emulsion in water containing isazofos and applications thereof
CN103651555A (en) * 2013-12-06 2014-03-26 济南凯因生物科技有限公司 Emulsion in water containing isazofos and applications thereof
CN105432665A (en) * 2014-08-07 2016-03-30 江苏龙灯化学有限公司 Cyhalodiamide and bacillus thuringiensis-containing pesticidal composition
CN105432665B (en) * 2014-08-07 2018-04-17 江苏龙灯化学有限公司 A kind of Pesticidal combination containing chlorine fluorine cyanogen insect amide and Dipel
CN104255726A (en) * 2014-08-29 2015-01-07 广东省农业科学院植物保护研究所 Emulsion in water containing methoprene and preparation method thereof
US9643991B2 (en) * 2015-06-08 2017-05-09 Rotam Agrochem International Company Limited Process for preparing a novel crystalline form of emamectin benzoate and use the same
CN105851073A (en) * 2016-04-29 2016-08-17 山东胜伟园林科技有限公司 Saline-alkali soil Chinese cabbage special vegetable insecticide containing derris extracts and preparation method of vegetable insecticide
WO2019005700A1 (en) * 2017-06-26 2019-01-03 Merial, Inc. Dual active parasiticidal granule compositions, methods and uses thereof
US11147273B2 (en) 2017-06-26 2021-10-19 Boehringer Ingelheim Animal Health USA Inc. Dual active parasiticidal granule compositions, methods and uses thereof
CN109169688A (en) * 2018-09-28 2019-01-11 华南农业大学 A kind of Pesticidal combination and application thereof containing thiocyclam and emamectin-benzoate
WO2022238576A1 (en) 2021-05-14 2022-11-17 Syngenta Crop Protection Ag Seed treatment compositions
WO2022268813A1 (en) 2021-06-24 2022-12-29 Syngenta Crop Protection Ag Insect, acarina and nematode pest control
CN113973833A (en) * 2021-10-18 2022-01-28 河南好年景生物发展有限公司 Sustained-release granule containing lufenuron and emamectin benzoate and applied to corn carpopodium for preventing and treating spodoptera frugiperda

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