CN1149924C - Fungicide mixtures based on triple oxime ether derivatives and other strobilurings - Google Patents

Fungicide mixtures based on triple oxime ether derivatives and other strobilurings Download PDF

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CN1149924C
CN1149924C CNB99804315XA CN99804315A CN1149924C CN 1149924 C CN1149924 C CN 1149924C CN B99804315X A CNB99804315X A CN B99804315XA CN 99804315 A CN99804315 A CN 99804315A CN 1149924 C CN1149924 C CN 1149924C
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alkyl
methyl
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CN1294487A (en
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K·斯克尔伯格
T·格尔特
H·索特
E·阿莫尔曼
G·罗恩兹
S·斯特瑞斯曼
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BASF SE
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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
    • 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
    • A01N37/50—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 the nitrogen atom being doubly bound to the carbon skeleton
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • A01N25/06—Aerosols
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/12—Powders or granules
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
    • C07C251/56—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by doubly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants

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

Abstract

The invention relates to fungicide mixtures comprised as active components a) phenylacetic acid derivatives of formula (I) in which the substituents and the index have the meanings cited in the description, and the salts thereof, and b) at least one compound of formulas (II) to (V) in a synergistically effective quantity.

Description

Fungicidal mixture based on three (oxime ether) derivative and other strobilurins
The present invention relates to be used to prevent and treat the Fungicidal mixture of harmful fungoid, it comprises:
A) formula I phenylacetic acid derivatives and salt thereof
Wherein each substituting group and subscript implication are as follows:
X is NOCH 3, CHOCH 3, CHCH 3
Y is O, NR;
R 1, R is hydrogen or C separately independently of one another 1-C 4-alkyl;
R 2Be cyano group, nitro, trifluoromethyl, halogen, C 1-C 4-alkyl or C 1-C 4-alkoxyl;
M is 0,1 or 2, when m is 2, and radicals R 2Can be different;
R 3Be hydrogen, cyano group, C 1-C 4-alkyl, C 1-C 4-haloalkyl, C 3-C 6-cycloalkyl;
R 4, R 6Be hydrogen separately independently of one another,
C 1-C 10-alkyl, C 3-C 6-cycloalkyl, C 2-C 10-alkenyl, C 2-C 10-alkynyl, C 1-C 10-alkyl-carbonyl, C 2-C 10-alkenyl carbonyl, C 3-C 10-alkynyl carbonyl or C 1-C 10-alkyl sulphonyl, these groups can be part or all of halos, perhaps are connected with 1-3 following radicals: cyano group, nitro, hydroxyl, sulfydryl, amino, carboxyl, amino carbonyl, amino thiocarbonyl, halogen, C 1-C 6-alkyl, C 1-C 6-haloalkyl, C 1-C 6-alkyl sulphonyl, C 1-C 6-alkyl sulphinyl (sulfoxyl), C 1-C 6-alkoxyl, C 1-C 6-halogenated alkoxy, C 1-C 6-alkoxy carbonyl, C 1-C 6-alkylthio group, C 1-C 6-alkyl amino, two-C 1-C 6-alkyl amino, C 1-C 6-alkyl amino-carbonyl, two-C 1-C 6-alkyl amino-carbonyl, C 1-C 6-thio-alkyl amino-carbonyl, two-C 1-C 6-thio-alkyl amino-carbonyl, C 2-C 6-alkenyl, C 2-C 6-alkenyloxy, C 3-C 6-cycloalkyl, C 3-C 6-cycloalkyl oxy, heterocyclic radical, heterocyclic oxy group, benzyl, benzyloxy, aryl, aryloxy group, arylthio, heteroaryl, heteroaryloxy and heteroarylthio, cyclic group wherein itself can be again part or all of halo, perhaps is connected with 1-3 following groups: cyano group, nitro, hydroxyl, sulfydryl, amino, carboxyl, amino carbonyl, amino thiocarbonyl, halogen, C 1-C 6-alkyl, C 1-C 6-haloalkyl, C 1-C 6-alkyl sulphonyl, C 1-C 6-alkyl sulphinyl, C 3-C 6-cycloalkyl, C 1-C 6-alkoxyl, C 1-C 6-halogenated alkoxy, C 1-C 6-alkoxy carbonyl, C 1-C 6-alkylthio group, C 1-C 6-alkyl amino, two-C 1-C 6-alkyl amino, C 1-C 6-alkyl amino-carbonyl, two-C 1-C 6-alkyl amino-carbonyl, C 1-C 6-thio-alkyl amino-carbonyl, two-C 1-C 6-thio-alkyl amino-carbonyl, C 2-C 6-alkenyl, C 2-C 6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy group, arylthio, heteroaryl, heteroaryloxy, heteroarylthio or C (=NOR 7)-A n-R 8
Aryl, aryl carbonyl, aryl sulfonyl, heteroaryl, heteroaryl carbonyl or heteroarylsulfonyl, these groups can be part or all of halos; perhaps can have 1-3 following groups: cyano group, nitro, hydroxyl, sulfydryl, amino; carboxyl, amino carbonyl, amino thiocarbonyl, halogen, C 1-C 6-alkyl, C 1-C 6-haloalkyl, C 1-C 6-alkyl-carbonyl, C 1-C 6-alkyl sulphonyl, C 1-C 6-alkyl sulphinyl, C 3-C 6-cycloalkyl, C 1-C 6-alkoxyl, C 1-C 6-halogenated alkoxy, C 1-C 6-alkoxy carbonyl, C 1-C 6-alkylthio group, C 1-C 6-alkyl amino, two-C 1-C 6-alkyl amino, C 1-C 6-alkyl amino-carbonyl, two-C 1-C 6-alkyl amino-carbonyl, C 1-C 6-thio-alkyl amino-carbonyl, two-C 1-C 6-thio-alkyl amino-carbonyl, C 2-C 6-alkenyl, C 2-C 6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy group, heteroaryl, heteroaryloxy or C (=NOR 7)-A n-R 8
R 5Be hydrogen;
C 1-C 6-alkyl, C 2-C 6-alkenyl, C 2-C 6-alkynyl, these alkyl can perhaps be connected with 1-3 following groups by part or all of halo: cyano group, nitro, hydroxyl, sulfydryl, amino, carboxyl, amino carbonyl, amino thiocarbonyl, halogen, C 1-C 6-alkyl amino-carbonyl, two-C 1-C 6-alkyl amino-carbonyl, C 1-C 6-thio-alkyl amino-carbonyl, two-C 1-C 6-thio-alkyl amino-carbonyl, C 1-C 6Alkyl sulphonyl, C 1-C 6-alkyl sulphinyl, C 1-C 6-alkoxyl, C 1-C 6-halogenated alkoxy, C 1-C 6-alkoxy carbonyl, C 1-C 6-alkylthio group, C 1-C 6-alkyl amino, two-C 1-C 6-alkyl amino, C 2-C 6-alkenyloxy, C 3-C 6-cycloalkyl, C 3-C 6-cycloalkyl oxy, heterocyclic radical, heterocyclic oxy group, aryl, aryloxy group, aryl-C 1-C 4-alkoxyl, arylthio, aryl-C 1-C 4-alkylthio group, heteroaryl, heteroaryloxy, heteroaryl-C 1-C 4-alkoxyl, heteroarylthio, heteroaryl-C 1-C 4-alkylthio group, and cyclic group wherein itself can be part or all of halo and/or be connected with 1-3 following groups: cyano group, nitro, hydroxyl, sulfydryl, amino, carboxyl, amino carbonyl, amino thiocarbonyl, C 1-C 6-alkyl, C 1-C 6-haloalkyl, C 1-C 6-alkyl sulphonyl, C 1-C 6-alkyl sulphinyl, C 3-C 6-cycloalkyl, C 1-C 6-alkoxyl, C 1-C 6-halogenated alkoxy, C 1-C 6-alkoxy carbonyl, C 1-C 6-alkylthio group, C 1-C 6-alkyl amino, two-C 1-C 6-alkyl amino, C 1-C 6-alkyl amino-carbonyl, two-C 1-C 6-alkyl amino-carbonyl, C 1-C 6-thio-alkyl amino-carbonyl, two-C 1-C 6-thio-alkyl amino-carbonyl, C 2-C 6-alkenyl, C 2-C 6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy group, arylthio, heteroaryl, heteroaryloxy, heteroarylthio and C (=NOR 7)-A n-R 8
C 3-C 6-cycloalkyl, C 3-C 6-cycloalkenyl group, heterocyclic radical, aryl, heteroaryl, these cyclic groups can or be connected with 1-3 following groups by part or all of halo: cyano group, nitro, hydroxyl, sulfydryl, amino, carboxyl, amino carbonyl, amino thiocarbonyl, halogen, C 1-C 6-alkyl, C 1-C 6-haloalkyl, C 1-C 6-alkyl sulphonyl, C 1-C 6-alkyl sulphinyl, C 3-C 6-cycloalkyl, C 1-C 6-alkoxyl, C 1-C 6-halogenated alkoxy, C 1-C 6-alkoxy carbonyl, C 1-C 6-alkylthio group, C 1-C 6-alkyl amino, two-C 1-C 6-alkyl amino, C 1-C 6-alkyl amino-carbonyl, two-C 1-C 6-alkyl amino-carbonyl, C 1-C 6-thio-alkyl amino-carbonyl, two-C 1-C 6-thio-alkyl amino-carbonyl, C 2-C 6-alkenyl, C 2-C 6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy group, heteroaryl and heteroaryloxy;
Wherein A is an oxygen, sulphur or nitrogen, and wherein nitrogen is connected with hydrogen or C 1-C 6Alkyl;
N is 0 or 1;
R 7Be hydrogen or C 1-C 6Alkyl; With
R 8Be hydrogen or C 1-C 6Alkyl,
With
B) at least a fungicide that is selected from formula II-V:
The purpose of this invention is to provide and have good Fungicidally active (particularly to the rice fungal disease) and its effectiveness surmount the Fungicidal mixture that each component of mixture is renderd a service separately.
We find that this purpose of the present invention can be realized by the described mixture of claim 1.
Formula I compound itself is known, and is recorded in the document (WO 97/15552).
Formula II-V fungicide also is known, and is recorded in the document.In addition, if suitable, they can be buied from the market with the trade name that provides in the following bracket:
II: common name: azoxystrobin (trade name: Amistar , Zeneca)
III:EP-A 253,313, common name: kresoxim-methyl (trade name: Brio , BASF)
IV:EP 398,692, recommend common name: metominostrobin (to develop code: SSF-126, Shionogi);
V:EP 398,692, CAS RN 162535-21-9, SSF 129, the development of Shionogi Co., Ltd).
In view of its C=C and the two keys of C=N, may produce the E/Z isomer mixture during preparation Compound I, their available subsequently conventional methods (for example crystallization and chromatography) are separated into the unification compound.
Yet, if the synthetic isomer mixture that produced, because in preparing the process of using preparation or the process of using preparation, in some cases, individual isomer can transform (for example under light, acid or alkali effect) mutually, so do not need usually necessarily they to be separated.Similarly conversion also can take place after use, for example when handling plant, betides in the plant corpus that is subject to processing or in the harmful fungoid that will prevent and treat or animal pest body.
With regard to the two keys of C=X, in view of its activity, the preferred E-isomer of Compound I (based on-OCH 3Or-CH 3Group is with respect to-CO 2R 1The configuration of group).
Right-C (R 3)=NOCH 2-two keys are considered their activity, and the cis-isomer of preferred compound I is (based on radicals R 3With respect to-OCH 2The configuration of-group).
In the definition of the Compound I that this paper beginning provides, used the collective term of general expression following radicals:
Halogen: fluorine, chlorine, bromine and iodine;
Alkyl: have the straight or branched alkyl of 1 to 4,6 or 10 carbon atom, for example, C 1-C 6-alkyl, as methyl, ethyl, propyl group, the 1-Methylethyl, butyl, 1-methyl-propyl, 2-methyl-propyl, 1,1-dimethyl ethyl, amyl group, 1-methyl butyl, the 2-methyl butyl, 3-methyl butyl, 2,2-dimethyl propyl, the 1-ethyl propyl, hexyl, 1,1-dimethyl propyl, 1,2-dimethyl propyl, 1-methyl amyl, 2-methyl amyl, the 3-methyl amyl, 4-methyl amyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethyl-butyl, 2-ethyl-butyl, 1,1,2-trimethyl propyl group, 1,2,2-trimethyl propyl group, 1-ethyl-1-methyl-propyl and 1-ethyl-2-methyl-propyl;
Haloalkyl: have the straight or branched alkyl of 1-6 carbon atom, some or all hydrogen atoms in these groups may be replaced by top mentioned halogen atom, for example C 1-C 2-haloalkyl, as chloromethyl, dichloromethyl, trichloromethyl, methyl fluoride, difluoromethyl, trifluoromethyl, chlorine methyl fluoride, dichlorofluoromethyl, chlorodifluoramethyl-, 1-fluoro ethyl, 2-fluoro ethyl, 2,2-two fluoro ethyls, 2,2, the 2-trifluoroethyl, 2-chloro-2-fluoro ethyl, 2-chloro-2,2-two fluoro ethyls, 2,2-two chloro-2-fluoro ethyls, 2,2,2-three chloroethyls and pentafluoroethyl group;
Cycloalkyl: have the monocycle alkyl of 3-6 carboatomic ring atom, for example cyclopropyl, cyclobutyl, cyclopenta and cyclohexyl.
Alkenyl: have the straight or branched thiazolinyl that 2 to 6 or 10 carbon atoms also have a pair of key at an arbitrary position, for example C 2-C 6-alkenyl, as vinyl, the 1-acrylic, the 2-acrylic, 1-methyl ethylene, 1-cyclobutenyl, the 2-cyclobutenyl, 3-cyclobutenyl, 1-methyl isophthalic acid-acrylic, 2-methyl isophthalic acid-acrylic, 1-methyl-2-acrylic, 2-methyl-2-acrylic, the 1-pentenyl, 2-pentenyl, 3-pentenyl, the 4-pentenyl, 1-methyl isophthalic acid-cyclobutenyl, 2-methyl-1-butene thiazolinyl, the 3-methyl-1-butene base, 1-methyl-2-butene base, 2-methyl-2-butene base, 3-methyl-2-butene base, 1-methyl-3-cyclobutenyl, 2-methyl-3-cyclobutenyl, 3-methyl-3-cyclobutenyl, 1,1-dimethyl-2-acrylic, 1,2-dimethyl-1-acrylic, 1,2-dimethyl-2-acrylic, 1-ethyl-1-acrylic, 1-ethyl-2-acrylic, the 1-hexenyl, the 2-hexenyl, 3-hexenyl, 4-hexenyl, the 5-hexenyl, 1-methyl-1-pentene thiazolinyl, 2-methyl-1-pentene thiazolinyl, 3-methyl-1-pentene thiazolinyl, the 4-methyl-1-pentene base, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-cyclobutenyl, 1,1-dimethyl-3-cyclobutenyl, 1,2-dimethyl-1-cyclobutenyl, 1,2-dimethyl-2-cyclobutenyl, 1,2-dimethyl-3-cyclobutenyl, 1,3-dimethyl-1-cyclobutenyl, 1,3-dimethyl-2-cyclobutenyl, 1,3-dimethyl-3-cyclobutenyl, 2,2-dimethyl-3-cyclobutenyl, 2,3-dimethyl-1-cyclobutenyl, 2,3-dimethyl-2-cyclobutenyl, 2,3-dimethyl-3-cyclobutenyl, 3,3-dimethyl-1-cyclobutenyl, 3,3-dimethyl-2-cyclobutenyl, 1-ethyl-1-cyclobutenyl, 1-ethyl-2-cyclobutenyl, 1-ethyl-3-cyclobutenyl, 2-ethyl-1-cyclobutenyl, 2-ethyl-2-cyclobutenyl, 2-ethyl-3-cyclobutenyl, 1,1,2-trimethyl-2-acrylic, 1-ethyl-1-methyl-2-acrylic, 1-ethyl-2-methyl isophthalic acid-acrylic and 1-ethyl-2-methyl-2-acrylic;
Alkynyl: have the straight or branched alkynyl that 2-10 carbon atom also has a triple bond at an arbitrary position, for example, C 2-C 6-alkynyl, as acetenyl, 2-propynyl, 2-butynyl, the 3-butynyl, 1-methyl-2-propynyl, valerylene base, the 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-hexin base, 3-hexin base, 4-hexin base, 5-hexin base, 1-methyl-valerylene base, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-valerylene base, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;
Heterocyclic radical or heterocyclic oxy group, heterocycle sulfenyl and heterocyclic amino group: contain 1-3 and be selected from oxygen, nitrogen and sulfur heteroatom three to the hexa-atomic saturated or undersaturated monocycle of part or encircle heterocycle more, described heterocycle directly or through oxygen atom (heterocyclic oxy group) or through sulphur atom (heterocycle sulfenyl) or through nitrogen-atoms (heterocyclic amino group) is connected on the skeleton, for example the 2-tetrahydrofuran base, Oxyranyle, 3-tetrahydrofuran base, 2-tetrahydro-thienyl, the 3-tetrahydro-thienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, the 3-isoxazole alkyl, 4-isoxazole alkyl, 5-isoxazole alkyl, 3-isothiazole alkyl, 4-isothiazole alkyl, 5-isothiazole alkyl, the 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazole alkyl, 4-oxazole alkyl, 5-oxazole alkyl, the 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, the 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazole alkane-3-base, 1,2,4-oxadiazole alkane-5-base, 1,2,4-thiadiazolidine-3-base, 1,2,4-thiadiazolidine-5-base, 1,2,4-triazolidine-3-base, 1,3,4-oxadiazole alkane-2-base, 1,3,4-thiadiazolidine-2-base, 1,3,4-triazolidine-2-base, 2,3-dihydrofuran-2-base, 2,3 dihydro furan-3-base, 2,3 dihydro furan-4-base, 2,3-dihydrofuran-5-base, 2,5-dihydrofuran-2-base, 2,5-dihydrofuran-3-base, 2,3-dihydro-thiophene-2-base, 2,3-dihydro-thiophene-3-base, 2,3-dihydro-thiophene-4-base, 2,3-dihydro-thiophene-5-base, 2,5-dihydro-thiophene-2-base, 2,5-dihydro-thiophene-3-base, 2,3-pyrrolin-2-base, 2,3-pyrrolin-3-base, 2,3-pyrrolin-4-base, 2,3-pyrrolin-5-base, 2,5-pyrrolin-2-base, 2,5-pyrrolin-3-base, 2,3-dihydro-isoxazole-3-base, 2,3-dihydro-isoxazole-4-base, 2,3-dihydro-isoxazole-5-base, 4,5-dihydro-isoxazole-3-base, 4,5-dihydro-isoxazole-4-base, 4,5-dihydro-isoxazole-5-base, 2,5-dihydro isothiazole-3-base, 2,5-dihydro isothiazole-4-base, 2,5-dihydro isothiazole-5-base, 2,3-dihydro imidazole-3-base, 2,3-dihydro imidazole-4-base, 2,3-dihydro imidazole-5-base, 4,5-dihydro imidazole-3-base, 4,5-dihydro imidazole-4-base, 4,5-dihydro imidazole-5-base, 2,5-dihydro imidazole-3-base, 2,5-dihydro imidazole-4-base, 2,5-dihydro imidazole-5-base, 2,3-dihydro-oxazole-3-base, 2,3-dihydro-oxazole-4-base, 2,3-dihydro-oxazole-5-base, 4,5-dihydro-oxazole-3-base, 4,5-dihydro-oxazole-4-base, 4,5-dihydro-oxazole-5-base, 2,5-dihydro-oxazole-3-base, 2,5-dihydro-oxazole-4-base, 2,5-dihydro-oxazole-5-base, 2,3-thiazoline-2-base, 2,3-thiazoline-4-base, 2,3-thiazoline-5-base, 4,5-thiazoline-2-base, 4,5-thiazoline-4-base, 4,5-thiazoline-5-base, 2,5-thiazoline-2-base, 2,5-thiazoline-4-base, 2,5-thiazoline-5-base, 2,3-glyoxalidine-2-base, 2,3-glyoxalidine-4-base, 2,3-glyoxalidine-5-base, 4,5-glyoxalidine-2-base, 4,5-glyoxalidine-4-base, 4,5-glyoxalidine-5-base, 2,5-glyoxalidine-2-base, 2,5-glyoxalidine-4-base, 2,5-glyoxalidine-5-base, the 2-morpholinyl, morpholinyl, 2-piperidyl, the 3-piperidyl, the 4-piperidyl, 3-tetrahydro pyridazine base, 4-tetrahydro pyridazine base, the 2-tetrahydro-pyrimidine base, the 4-tetrahydro-pyrimidine base, 5-tetrahydro-pyrimidine base, 2-tetrahydrochysene pyrazinyl, 1,3,5-tetrahydrotriazine-2-base, 1,2,4-tetrahydrotriazine-3-base, 1,3-Er Qing oxazine-2-base, 1,3-dithiane-2-base, 2-THP trtrahydropyranyl, 1,3-dioxolanes-2-base, 3,4,5,6-tetrahydropyridine-2-base, 4H-1,3-thiazine-2-base, 4H-3,1-benzothiazine-2-base, 1,1-dioxo-2,3,4,5-thiophane-2-base, 2H-1,4-benzothiazine-3-base, 2H-1,4-benzoxazine-3-base, 1,3-Er Qing oxazine-2-base, 1,3-dithiane-2-base;
Aryl or aryloxy group, arylthio, aryl carbonyl and aryl sulfonyl: directly or through oxygen atom (O-) (aryloxy group) or through sulphur atom (S-) (arylthio) or through carbonyl (CO-) (aryl carbonyl) or through sulfonyl (SO 2-) (aryl sulfonyl) be bonded to aromaticity monocycle or the multi-ring alkyl on the skeleton, phenyl for example, naphthyl or phenanthryl or phenoxy group, naphthoxy and luxuriant and rich with fragrance oxygen base and corresponding carbonyl and sulphonyl base class group;
Heteroaryl or heteroaryloxy, heteroarylthio, heteroaryl carbonyl and heteroarylsulfonyl: except that carboatomic ring atom; can contain 1-4 nitrogen-atoms in addition or contain 1-3 nitrogen-atoms and an oxygen or a sulphur atom or contain aromaticity monocycle or many cyclic groups of an oxygen or a sulphur atom, they directly or through oxygen atom (O-) (heteroaryloxy) or through sulphur atom (S-) (heteroarylthio), through carbonyl (CO-) (heteroaryl carbonyl) or through sulfonyl (SO 2-) (heteroarylsulfonyl) link to each other with skeleton, for example
-contain the quinary heteroaryl of 1-3 nitrogen-atoms: except that carbon atom, can also contain the quinary heteroaryl of 1-3 nitrogen-atoms, for example the 2-pyrrole radicals as annular atoms, the 3-pyrrole radicals, 3-pyrazolyl, 4-pyrazolyl, the 5-pyrazolyl, the 2-imidazole radicals, 4-imidazole radicals, 1,2,4-triazole-3-base and 1,3,4-triazole-2-base.
-contain 1-4 nitrogen-atoms or contain 1-3 nitrogen-atoms and a sulphur or an oxygen atom or contain the 5-unit heteroaryl of an oxygen or a sulphur atom: quinary heteroaryl, except that carbon atom, it can also contain 1-4 nitrogen-atoms or contain 1-3 nitrogen-atoms and a sulphur or an oxygen atom or contain an oxygen or sulphur atom as annular atoms, 2-furyl for example, the 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrole radicals, the 3-pyrrole radicals, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, the 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, the 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, the 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, the 2-imidazole radicals, 4-imidazole radicals, 1,2,4-oxadiazole-3-base, 1,2,4-oxadiazole-5-base, 1,2,4-thiadiazoles-3-base, 1,2,4-thiadiazoles-5-base, 1,2,4-triazole-3-base, 1,3,4-oxadiazole-2-base, 1,3,4-thiadiazoles-2-base, 1,3,4-triazole-2-base;
-contain 1-3 nitrogen-atoms or contain a nitrogen-atoms and/or the benzo-fused quinary heteroaryl of oxygen or sulphur atom: quinary heteroaryl, except that carbon atom, it can also contain 1-4 nitrogen-atoms or contain 1-3 nitrogen-atoms and a sulphur or an oxygen atom or contain an oxygen or a sulphur atom as annular atoms, and wherein two adjacent carbons annular atomses or a nitrogen-atoms and an adjacent carbons annular atoms can be through fourths-1,3-diene-1, the bridging of 4-subunit group;
-the quinary heteroaryl that contains 1-4 nitrogen-atoms and connect through the nitrogen key, or the benzo-fused quinary heteroaryl that contains 1-3 nitrogen-atoms and connect: quinary heteroaryl through the nitrogen key, except that carbon atom, can also contain 1-4 nitrogen-atoms and 1-3 nitrogen-atoms respectively as annular atoms, and two adjacent carbons annular atomses wherein or a nitrogen and an adjacent carbons annular atoms can be through fourths-1,3-diene-1,4-subunit group bridging Cheng Huan, these rings one and skeleton key company in the azo-cycle atom;
-contain the six membered heteroaryl of 1-3 or 1-4 nitrogen-atoms respectively: six membered heteroaryl, except that carbon atom, can also contain individual or 1-4 the nitrogen-atoms of 1-3 respectively as annular atoms, for example: the 2-pyridine radicals, the 3-pyridine radicals, 4-pyridine radicals, 3-pyridazinyl, 4-pyridazinyl, the 2-pyrimidine radicals, 4-pyrimidine radicals, 5-pyrimidine radicals, 2-pyrazinyl, 1,3,5-triazines-2-base, 1,2,4-triazine-3-base and 1,2,4,5-tetrazine-3-base;
-contain the benzo-fused six membered heteroaryl of 1-4 nitrogen-atoms: wherein two adjacent carbons annular atomses can be through fourth-1,3-diene-1, the six membered heteroaryl of 4-subunit group bridging Cheng Huan; quinoline for example; isoquinolin, quinazoline and quinoxaline, and corresponding oxygen base, sulfenyl, carbonyl or sulfonyl group.Heteroaryl amino: except that carboatomic ring atom, can also contain 1-4 nitrogen-atoms or contain 1-3 nitrogen-atoms and aromaticity monocycle or many cyclic groups of an oxygen or a sulphur atom, they link to each other with skeleton via nitrogen-atoms.
Term " partly or entirely halo " is meant that the some or all of hydrogen atoms in the group of modifying with this term can be replaced by aforesaid identical or different halogen atom.
Consider their biologically active, preferred wherein m is 0 formula I compound.
Equally preferred R wherein 1Formula I compound for methyl.
In addition, preferred R wherein also 3Be hydrogen, cyano group, cyclopropyl, methyl, ethyl, 1-Methylethyl or CF 3Compound I.
Preferred R wherein in addition 3Compound I for methyl.
Preferred R wherein also 3Compound I for cyano group.
And preferred R wherein 3Compound I for cyclopropyl.
In addition, preferred R wherein 3Be CF 3Compound I.
In addition, preferred R wherein 5Be hydrogen, cyclopropyl, methyl, ethyl, isopropyl, the aryl that does not replace or replace or the Compound I of heteroaryl.
Preferred R wherein in addition 5Compound I for methyl.
In addition, preferred R wherein 5Compound I for ethyl.
Preferred R wherein in addition 5Compound I for isopropyl.
Preferred R wherein in addition 5Compound I for cyclopropyl.
Preferred R wherein in addition 5Be CF 3Compound I.
In addition, preferred R wherein 5For not replacing or the aryl of replacement or the Compound I of heteroaryl.
Preferred in addition Compound I is R wherein 5Be those of the pyridine radicals, pyrimidine radicals, pyrazinyl, pyridazinyl or the triazinyl that do not replace or replace.
In addition, preferred R wherein 5Compound I for the furyl, thienyl or the pyrrole radicals that do not replace or replace.
In addition, preferred Compound I is R wherein 5For not replacing or replace those of De oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, pyrazolyl or imidazole radicals.
In addition, preferred R wherein 5For not replacing or replace the Compound I of De oxadiazole base, thiadiazolyl group or triazolyl.
In addition, also preferred these Compound I, wherein R 5For unsubstituted or have a phenyl of one or two following radicals: nitro, cyano group, hydroxyl, amino, amino carbonyl, amino thiocarbonyl, halogen, C 1-C 4-alkyl, C 1-C 4-haloalkyl, C 1-C 4-alkoxyl, C 1-C 4-halogenated alkoxy, C 1-C 4-alkyl amino, two-C 1-C 4-alkyl amino, C 1-C 4-alkyl sulphonyl, C 1-C 4-alkoxy carbonyl, C 1-C 4-alkyl amino-carbonyl or two-C 1-C 4-alkyl amino-carbonyl.
In addition, also preferred these Compound I, wherein R 4Be hydrogen, C 1-C 6-alkyl, C 2-C 6-alkenyl, C 2-C 6-alkynyl, pi-allyl, aralkyl, heteroaryl alkyl, aryloxy alkyl, heteroaryloxy alkyl, aryl or heteroaryl.
In addition, preferred R wherein 4Be C 1-C 6The Compound I of-alkyl.
Further preferred Compound I is disclosed in the WO 97/15,552.
The Compound I that is included in the mixture of the present invention all has superior activity to the various plants pathogen, particularly for Ascomycetes, deuteromycetes, Phycomycetes and Basidiomycetes fungi.
They are for each plant species, as cotton, greengrocery (as cucumber, Kidney bean, tomato, potato and Curcurbitaceae), the control of the multiple fungal disease on barley, herbage, oat, banana, coffee, corn, fruits, rice, rye, soybean, grape, wheat, ornamental plants, sugarcane and all kinds of seed particular importance all.
They are particularly suitable for preventing and treating the following plants disease fungus: the standing grain powdery mildew on the cereal class (Erysiphe graminis) (cereal powdery mildew), two spore powdery mildews (Erysiphe cichoracearum) and Siberian cocklebur monofilament shell bacterium (Sphaerothecafuliginea) on the Curcurbitaceae, apple mildew bacterium on the apple (Podosphaera leucotricha) (apple mildew), grape snag shell (Uncinula necator) (grape powdery mildew) on the grape, handle rest fungus (Puccinia) on the cereal class, cotton, rhizoctonia on rice and the lawn (Rhizoctonia), smut on cereal class and the sugarcane (Ustilago), venturia inaequalis on the apple (apple scab) (Venturia inaequalis), length on the cereal class spore bacterium (Helminthosporium) that wriggles, glume blight bacterium on the wheat (wheat Ying rot) (Septoria nodorum), strawberry, vegetables, Botrytis cinerea on ornamental plants and the grape (Botrytis cinera) (gray mold), peanut tail spore bacterium (Cercospora arachidicola) on the peanut, eye spot bacterium on wheat and the barley (Pseudocercosporella herpotrichoides), Magnaporthe grisea on the rice (Pyricularia oryzae), phytophthora infestans on potato and the tomato (Phytophthora infestans), grape on the grape is given birth to single shaft mould (Plasmoparaviticola), false downy mildew (Pseudoperonospora) on lupulus and the cucumber, alternaric bacteria on vegetables and the fruit (Alternaria), ball chamber bacterium (Mycosphaerella) on the banana, and sickle-like bacteria (Fusarium) and verticillium sp (Verticillium).
Compound I I-V is commercially available fungicide.
When the preparation mixture, preferred pure active component I and the II-V of adopting, wherein can sneak in addition harmful fungoid or other insect (as insect, arachnid or nematode) are had other active composition, or have the composition or the fertilizer of activity of weeding or plant growth regulating activity.
The mixture of Compound I and at least a Compound I I to V can be simultaneously (promptly together or respectively) uses, and demonstrate the broad-spectrum plant disease fungus, the fungi that particularly belongs to Ascomycetes, Basidiomycetes, deuteromycetes and Phycomycetes has excellent activity.Some can interiorly work with inhaling in these compounds, thereby can be used as blade face and soil fungicide.
They are for the various crops of control, as cotton, greengrocery (as cucumber, Kidney bean, tomato, potato and Curcurbitaceae), the particular importance all of the many fungies on barley, herbage, oat, banana, coffee, corn, fruits, rice, rye, soybean, grape, wheat, ornamental plants, sugarcane and the various seed.
They are particularly suitable for preventing and treating the following plants disease fungus: the standing grain powdery mildew on the cereal class (Erysiphe graminis) (cereal powdery mildew), two spore powdery mildews (Erysiphe cichoracearum) and Siberian cocklebur monofilament shell bacterium (Sphaerothecafuliginea) on the Curcurbitaceae, apple mildew bacterium on the apple (Podosphaera leucotricha) (apple mildew), grape snag shell (Uncinula necator) (grape powdery mildew) on the grape, handle rest fungus (Puccinia) on the cereal class, cotton, rhizoctonia on rice and the lawn (Rhizoctonia), smut on cereal class and the sugarcane (Ustilago), venturia inaequalis on the apple (apple scab) (Venturia inaequalis), length on cereal class and the rice spore bacterium (Helminthosporium) that wriggles, glume blight bacterium on the wheat (wheat Ying rot) (Septoria nodorum), strawberry, vegetables, Botrytis cinerea on ornamental plants and the grape (Botrytis cinera) (gray mold), peanut tail spore bacterium (Cercospora arachidicola) on the peanut, eye spot bacterium on wheat and the barley (Pseudocercosporella herpotrichoides), Magnaporthe grisea on rice and the lawn (Pyricularia oryzae), phytophthora infestans on potato and the tomato (Phytophthora infestans), grape on the grape is given birth to single shaft mould (Plasmoparaviticola), false downy mildew (Pseudoperonospora) on lupulus and the cucumber, alternaric bacteria on vegetables and the fruit (Alternaria), ball chamber bacterium (Mycosphaerella) on the banana, and sickle-like bacteria (Fusarium) and verticillium sp (Verticillium).
Mixture of the present invention is particularly preferred for preventing and treating rice blast (Pyriculariaoryzae).
Compound I and at least a Compound I I-V be (promptly using) together or respectively simultaneously, or successively use, and under the situation of using respectively, it uses order generally to preventing and treating the result without any influence.
The amount of application of mixture of the present invention particularly under the situation of land for growing field crops crops, is generally 0.01-8kg/ha, preferred 0.1-5kg/ha, and 0.5-3.0kg/ha particularly, this depends on desirable effect.
For Compound I, its amount of application is 0.01-2.5kg/ha, preferred 0.05-2.5kg/ha, particularly 0.1-1.0kg/ha.
Correspondingly, with regard to Compound I I-V, amount of application is generally 0.001-5kg/ha, preferred 0.005-2kg/ha, particularly 0.01-1.0kg/ha.
For the processing of seed, the amount of application of this mixture is generally 0.001-250 gram/kg seed, preferred 0.01-100 gram/kg, particularly 0.01-50 gram/kg.
If control pathogenic harmful fungoid, the difference of Compound I and at least a Compound I I-V or co-administered can be before or after plant seeding, perhaps before or after plant sprouts, by seed, plant or soil being sprayed or dusting is carried out.
Antifungal Synergistic blend of the present invention can be mixed with, for example be sprayable solution, pulvis and form of suspension, or the water-based of high concentration, oiliness or other suspension, dispersion liquid, emulsion, oil dispersion, paste, the agent of dusting, the form of broadcasting sowing agent or granule, and by spraying, atomizing, dusting, broadcast sowing or pour and use.Administration form depends primarily on intended purpose; Under any circumstance, should guarantee the trickle as far as possible and dispersion equably of mixture of the present invention.
These preparations for example mix with solvent and/or carrier by active component in a manner known way, if desired, prepare by using emulsifier and dispersant.If employed thinner is a water, also can make cosolvent with other organic solvent.To this adjuvant that is fit to mainly is solvent, as aromatic compounds (for example dimethylbenzene), chloro aromatic compounds (for example chlorobenzene), paraffin (for example petroleum cuts), alcohols (for example methyl alcohol, butanols), ketone (for example cyclohexanone), amine (for example monoethanolamine, dimethyl formamide) and water; Carrier is as the natural mineral matter (for example kaolin, alumina, talcum, chalk) that grinds and the synthetic mineral matter (for example finely divided silicic acid, silicate) of grinding; Emulsifier such as nonionic and anion emulsifier (for example polyoxyethylene aliphatic alcohol ether, alkylsulfonate and arylsulphonate) and dispersant such as lignin sulfite waste liquor or methylcellulose.
Suitable surface reactive material is alkali metal salt, alkali salt and the ammonium salt of following acid: aromatic sulfonic acid, as lignin sulfonic acid, phenolsulfonic acid, naphthalene sulfonic acids and dibutyl naphthalene sulfonic acids, with fatty acid, alkyl-and alkarylsulphonic acid, alkyl-, lauryl ether-and fatty alcohol sulphuric acid; And sulphation cetyl alcohol, the salt of pure and mild stearyl alcohol of heptadecyl or fatty alcohol glycol ether, the condensation product of sulfonated naphthalene and derivative thereof and formaldehyde, the condensation product of naphthalene or naphthalene sulfonic acids and phenol and formaldehyde, polyoxyethylene octyl phenol ether, the ethoxylation isooctyl phenol, octyl phenol or nonyl phenol, alkyl phenol polyethylene glycol ethers or tributyl phenyl polyglycol ether, alkyl aryl polyether alcohol, isotrideyl alcohol, the fatty alcohol ethylene epoxide condensation product, ethoxylated castor oil, polyoxyethylene alkyl ether or polyoxypropylene, dodecyl alcohol polyglycol ether acetate, sorbitol ester, lignin sulfite waste liquor or methylcellulose.
Pulvis, broadcast sowing agent and the agent of dusting can be by mixing or together mixture and the solid carrier of polishing compounds I and at least a Compound I I-V or Compound I and at least a Compound I I-V prepare.
Granule (for example, coated granule, impregnated granules and homogeneous particle) prepares by active component is adhered on the solid carrier usually.
Filler or solid carrier are, mineral great soil group for example, synthetic and fertilizer as silica gel, silicic acid, silica, silicate, talcum, kaolin, lime stone, lime, chalk, bole, loess, potter's clay, dolomite, diatomite, calcium sulphate, magnesium sulfate, magnesia, grinding, as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, and plant resource product, as cereal powder, bark fines, timber powder and shuck powder, cellulose powder or other solid carrier.
Preparation comprises 0.1-95% weight usually, the mixture of one of the Compound I of preferred 0.5-90% weight and at least a Compound I I-V or Compound I and at least a Compound I I-V.The purity of used active component is 90%-100%, preferred 95%-100% (measuring according to NMR spectrum or HPLC).
Its corresponding preparations is by the mixture with the antifungal effective dose, or (using respectively under the situation) Compound I and at least a Compound I I-IV handle harmful fungoid, it is assembled ground or desires to avoid plant, seed, soil, the surface that they infect, and the mode in material or space is used.
Use and after harmful fungoid infects preceding or infects, to carry out.
This class examples of formulations that contains active component is:
I.90 the solution formed of the N-Methyl pyrrolidone of the active component of weight portion and 10 weight portions, this solution is fit to use with the form of mist droplet.
The mixture that the adduct of the calcium salt of dodecylbenzene sulfonate of 8 to 10 moles of ethylene oxide of the dimethylbenzene of the active component of II.20 weight portion, 80 weight portions, 10 weight portions and the adduct of 1 mole of oleic acid-N-single ethanol amide, 5 weight portions and 40 moles of ethylene oxide of 5 weight portions and 1 mole of castor oil is formed; This solution is finely dispersed in obtains dispersion liquid in the water.
The aqueous dispersions that 40 moles of ethylene oxide of the isobutanol of the cyclohexanone of the active component of III.20 weight portion, 40 weight portions, 30 weight portions, 20 weight portions and the adduct of 1 mole of castor oil are formed.
The cyclohexanol of the active component of IV.20 weight portion, 25 weight portions, 65 weight portion boiling points are aqueous dispersions that the adduct of 210 to 280 ℃ petroleum cuts and 10 weight portions, 40 moles of ethylene oxide and 1 mole of castor oil is formed.
V. the active component with 80 weight portions mixes with the diisobutyl naphthalene-1-sulfonate sodium of 3 weight portions, the lignosulphonic acid sodium salt that derives from sulfite waste liquor and the 7 weight portion granular colloidal silicas of 10 weight portions, and in sledge mill, grind mixture, obtain the Spray Mixing thing in the water by this mixture is finely dispersed in;
VI. the active component of 3 weight portions and the fine powder of 97 weight portions is broken kaolin evenly mixes, and obtains to dust agent thus, and it comprises the active component of 3 weight %.
The granular colloidal silica of the active component of VII.30 weight portion, 92 weight portions and 8 weight portions spray to the homogeneous mixture that the lip-deep paraffin oil of silica gel is formed in advance; Obtain having the formulations of active ingredients of excellent adhering.
The stable aqueous dispersions that the sodium salt of the phenolsulfonic acid/urea of the active component of VIII.40 weight portion, 10 weight portions/formaldehyde condensation products, 2 weight portion silica gel and 48 weight parts waters are formed, this dispersion liquid can further dilute;
The stable oily dispersion that the paraffin mineral oil of the sodium salt of the phenolsulfonic acid/urea of the fatty alcohol polyglycol ether of the calcium dodecyl benzene sulfonate of the active component of IX.20 weight portion, 2 weight portions, 8 weight portions, 20 weight portions/formaldehyde condensation products and 88 weight portions is formed.
The synergistic activity of mixture of the present invention can prove by following test:
Active component (separately or together) is mixed with 10% emulsion in the mixture that 63% weight ring hexanone and 27% the weight of emulsifier are formed, is diluted with water to desired concn then.
Estimate by measuring the percentage that infects the blade face area.The effect of being converted into of these percentages is renderd a service.Effect is renderd a service (W) and is adopted following A bbot formula to calculate:
W＝(1-α/β)·100
α is corresponding to the fungal infection of handling plant, in % and
β is corresponding to the fungal infection of (control group) plant of being untreated, in %
The gradient of infection of rendeing a service 0 expression processing plant is suitable with untreated control plant infection degree; It is not infected to render a service 100 expression processing plants.
Employing Colby formula [R.S.Colby, weeds (Weeds), 15, 20-22 (1967)] and the predictive role of calculated activity constituents mixt renders a service and renders a service with the effect that observes and compared.
Colby formula: E=x+y-xy/100
E represents that the predictive role that working concentration is respectively under the situation of mixture of the active components A of a and b and B renders a service, and represents with the % of untreated control group
X represents that working concentration is that effect under the situation of active components A of a is renderd a service, and represents with the % of untreated control group
Y represents that working concentration is that effect under the situation of active component B of b is renderd a service, and represents with the % of untreated control group.
The anti-Magnaporthe grisea of Application Example 1-(Pyricularia oryzae) active (protective effect)
Use is sprayed potted plant " TaiNong 67 " kind rice sprouts blade face to drip by the aqueous compositions of the stoste preparation that the emulsifier of 10% active component, 63% cyclohexanone and 27% is formed.Second day, contaminate these plants with the Magnaporthe grisea aqueous spore suspension.Then test plant was placed 6 days in the 22-24 ℃ of climatic chamber with the relative atmospheric humidity of 95-99%, estimate the foliage disease development degree then.
Leaf area % value is infected in range estimation be converted into the effectiveness that the % with the untreated control group represents.Render a service 0 expression and have identical gradient of infection, render a service 100 expressions 0% and infect with the untreated control group.The expection effectiveness employing Colby formula calculating of active component combination (Colby, S.R. " calculating of the collaborative and antagonistic effect of combinations of herbicides ", " (weeds " (Weeds), the 15th rolls up the 20-22 page or leaf; 1967), and with the effectiveness that is observed compared.
Adopt following compounds I ' a) as component:
Figure C9980431500231
Result of the test is shown in table 1 and 2:
Table 1:
Embodiment Active component Concentration (ppm) Render a service (% of untreated control group)
1V Do not have (100% infects) 0
2V Compound I ' 2.0 0.5 20 0
3V Compound I I (common name: azoxystrobine) 0.5 20
4V Compound III (common name: kresoxim-methyl) 2.0 0.5 0 0
Table 2:
Embodiment Mixture (concentration: ppm) of the present invention The effectiveness value that observes The effectiveness value of calculating *
5 0.5ppm I+0.5ppm II 40 20
6 2ppm I+2ppm III 80 20
7 0.5ppm I+0.5ppm III 20 0
* adopt the Colby formula to calculate
Result of the test shows that for all mixed proportions, observed effectiveness value all is higher than employing Colby formula and calculates the effectiveness value.

Claims (10)

1. the mixture that is used for plant protection, it comprises following active component:
A) formula I phenylacetic acid derivatives and salt thereof:
Wherein each substituting group and subscript implication are as follows:
X is NOCH 3, CHOCH 3, CHCH 3
Y is O, NR;
R 1, R is hydrogen or C separately independently of one another 1-C 4-alkyl;
R 2Be cyano group, nitro, trifluoromethyl, halogen, C 1-C 4-alkyl or C 1-C 4-alkoxyl;
M is 0,1 or 2, when m is 2, and radicals R 2Can be different;
R 3Be hydrogen, cyano group, C 1-C 4-alkyl, C 1-C 4-haloalkyl, C 3-C 6-cycloalkyl;
R 4, R 6Be hydrogen separately independently of one another, C 1-C 10-alkyl, C 3-C 6-cycloalkyl, C 2-C 10-alkenyl or C 2-C 10-alkynyl;
R 5Be hydrogen, C 1-C 6-alkyl, C 2-C 6-alkenyl, C 2-C 6-alkynyl, C 3-C 6-cycloalkyl or C 3-C 6-cycloalkenyl group;
With
B) at least a compound that is selected from formula II, III and V
Figure C9980431500022
Wherein component a) and components b) mixing ratio be 1: 500-2500: 1.
2. the described Fungicidal mixture of claim 1, this mixture is adjusted to two parts, and wherein a part is included in the Compound I in solid or the liquid-carrier, and another part then is included at least a Compound I I, III or the V in solid or the liquid-carrier.
3. claim 1 or 2 described Fungicidal mixtures, wherein component is following formula I ' compound a)
4. claim 1 or 2 described Fungicidal mixture, wherein components b) be formula II compound.
5. the described Fungicidal mixture of claim 4, its Chinese style I phenylacetic acid derivatives has formula I ':
Figure C9980431500033
6. claim 1 or 2 described Fungicidal mixture, wherein components b) be the formula III compound.
7. the described Fungicidal mixture of claim 6, its Chinese style I phenylacetic acid derivatives has formula I ':
8. methods for fighting harmful mushrooms; this method comprise with each described Fungicidal mixture of claim 1 to 7 handle harmful fungoid, they gathering ground or desire to be protected from material, plant, seed, soil, surface or the space of fungal infection, wherein Compound I and at least a Compound I I, III or V can use with simultaneously or use respectively simultaneously or successively use with the amount of application of 0.01-8kg/ha.
9. the described method of claim 8, wherein with the described Compound I of 0.01-2.5kg/ha amount claim 1 handle harmful fungoid, they gathering ground or desire to avoid material, plant, seed, soil, surface or the space that they infect.
10. the described method of claim 8, wherein with Compound I I, the III described in the 0.01-1kg/ha amount claim 1 and at least a processing harmful fungoid among the V, they gathering ground or desire to avoid material, plant, seed, soil, surface or the space that they infect.
CNB99804315XA 1998-03-24 1999-03-22 Fungicide mixtures based on triple oxime ether derivatives and other strobilurings Expired - Fee Related CN1149924C (en)

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