CN1294488A - Fungicide mixtures based on triple oxime ether derivatives and insecticides - Google Patents

Fungicide mixtures based on triple oxime ether derivatives and insecticides Download PDF

Info

Publication number
CN1294488A
CN1294488A CN99804316A CN99804316A CN1294488A CN 1294488 A CN1294488 A CN 1294488A CN 99804316 A CN99804316 A CN 99804316A CN 99804316 A CN99804316 A CN 99804316A CN 1294488 A CN1294488 A CN 1294488A
Authority
CN
China
Prior art keywords
carbonyl
alkyl
amino
base
alkyl amino
Prior art date
Legal status (The legal status 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 status listed.)
Granted
Application number
CN99804316A
Other languages
Chinese (zh)
Other versions
CN1139323C (en
Inventor
K·谢尔伯格
T·格罗特
H·索特
E·阿默曼
G·洛伦兹
S·斯特拉思曼
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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
Application filed by BASF SE filed Critical BASF SE
Publication of CN1294488A publication Critical patent/CN1294488A/en
Application granted granted Critical
Publication of CN1139323C publication Critical patent/CN1139323C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • 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

Landscapes

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

Abstract

The invention relates to mixture for protecting the crop: a) phenylacetic acid derivatives of formula (I) in which the substituents and the index have the meanings cited in the description, and to the salts thereof, and to b) at least one compound of formulas (II) to (XI) in a synergistically effective quantity.

Description

Fungicidal mixture based on three (oxime ether) derivatives and insecticide
The present invention relates to prevent and treat the Fungicidal mixture of harmful fungoid and insect, it comprises a) phenyl acetic acid derivatives and the salt thereof of formula (I)
Figure 9980431600081
Wherein to have following connotation: X be NOCH for substituting group and symbol 3, CHOCH 3Or CHCH 3Y is oxygen or NR; R 1, R is hydrogen or C independently of each other 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, if wherein m is 2, and radicals R then 2Can be identical or different; R 3Be hydrogen, cyano group, C 1-C 4-alkyl, C 1-C 4-haloalkyl or C 3-C 6-cycloalkyl; R 4, R 6Be hydrogen independently of each other,
Be C 1-C 10-alkyl, C 3-C 6-cycloalkyl, C 2-C 10-thiazolinyl, 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 sulfonyl
Base, wherein these groups can part-or whole halos, maybe can have one to three
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
Sulfonyl, C 1-C 6-alkylsulfonyloxy, 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-alkane
Base is 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-thiazolinyl,
C 2-C 6-alkene oxygen base, C 3-C 6-cycloalkyl, C 3-C 6-cycloalkyl oxy, heterocyclic radical, heterocycle
Base oxygen base, benzyl, benzyloxy, aryl, aryloxy group, arylthio, heteroaryl, assorted virtue
Oxygen base and heteroarylthio, wherein cyclic group part can part-or whole halos, or
Can have one to three following groups: cyano group, nitro, hydroxyl, sulfydryl, amino,
Carboxyl, amino carbonyl, amino thiocarbonyl, halogen, C 1-C 6-alkyl, C 1-C 6-halo
Alkyl, C 1-C 6-alkyl sulphonyl, C 1-C 6-alkylsulfonyloxy, 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-alkane
Base is amino, two-C 1-C 6-alkyl amino, C 1-C 6-alkyl amino-carbonyl, two-C 1-C 6-alkane
Base amino carbonyl, C 1-C 6-thio-alkyl amino-carbonyl, two-C 1-C 6-alkyl amino sulfo-
Carbonyl, C 2-C 6-thiazolinyl, C 2-C 6-alkene oxygen base, C 3-C 6-cycloalkyl, C 3-C 6-cycloalkyl
Oxygen base, heterocyclic radical, heterocyclyloxy base, benzyl, benzyloxy, aryl, aryloxy group, virtue
Sulfenyl, heteroaryl, heteroaryloxy, heteroarylthio and C (=NOR 7)-A n-R 8
Be aryl, aryl carbonyl, aryl sulfonyl, heteroaryl, heteroaryl carbonyl or heteroaryl
Sulfonyl, wherein these groups can part-or whole halo, maybe can have one to
Three following groups: cyano group, nitro, hydroxyl, sulfydryl, amino, carboxyl, amino carbonyl
Basic, amino thiocarbonyl, halogen, C 1-C 6-alkyl, C 1-C 6-haloalkyl, C 1-C 6-
Alkyl sulphonyl, C 1-C 6-alkylsulfonyloxy, C 1-C 6-alkoxyl, C 1-C 6-alkyl halide
Oxygen base, 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-thiazolinyl,
C 2-C 6-alkene oxygen base, C 3-C 6-cycloalkyl, C 3-C 6-cycloalkyl oxy, benzyl, benzyloxy,
Aryl, aryloxy group, arylthio, heteroaryl, heteroaryloxy, heteroarylthio and
C (=NOR 7)-A n-R 8R 5Be hydrogen,
Be C 1-C 6-alkyl, C 2-C 6-thiazolinyl, C 2-C 6-alkynyl, wherein these groups can part
-or whole halo maybe can have one to three following groups: 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 6-alkyl sulphonyl, C 1-C 6-alkylsulfonyloxy group
Base, 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-alkene oxygen base, C 3-C 6-
Cycloalkyl, C 3-C 6-cycloalkyl oxy, heterocyclic radical, heterocyclyloxy base, aryl, fragrant oxygen
Base, 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-alkane sulphur
Base, wherein cyclic group part can part-or whole halo, maybe can have one to
Three following groups: cyano group, nitro, hydroxyl, sulfydryl, amino, carboxyl, amino carbonyl
Basic, amino thiocarbonyl, C 1-C 6-alkyl, C 1-C 6-haloalkyl, C 1-C 6-alkyl sulphur
Acyl group, C 1-C 6-alkylsulfonyloxy, 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
Base, C 1-C 6-thio-alkyl amino-carbonyl, two-C 1-C 6-thio-alkyl amino-carbonyl, C 2-
C 6-thiazolinyl, C 2-C 6-alkene oxygen base, benzyl, benzyloxy, aryl, aryloxy group, arylthio,
Heteroaryl, heteroaryloxy, heteroarylthio and C (=NOR 7)-A n-R 8
Be C 3-C 6-cycloalkyl, C 3-C 6-cycloalkenyl group, heterocyclic radical, aryl, heteroaryl, wherein
Cyclic group part can part-or whole halos, maybe can have one to three following base
Group: cyano group, nitro, hydroxyl, sulfydryl, amino, carboxyl, amino carbonyl, amino sulphur
For carbonyl, C 1-C 6-alkyl, C 1-C 6-haloalkyl, C 1-C 6-alkyl sulphonyl, C 1-C 6-
Alkylsulfonyloxy, 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-alkane
Base is 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-thiazolinyl,
C 2-C 6-alkene oxygen base, benzyl, benzyloxy, aryl, aryloxy group, heteroaryl and assorted fragrant oxygen
Base;
Wherein
A is oxygen, sulphur or nitrogen, and wherein nitrogen has hydrogen or C 1-C 6-alkyl;
N is 0 or 1;
R 7Be hydrogen or C 1-C 6-alkyl and
R 8Be hydrogen or C 1-C 6-alkyl, and b) at least a insecticide that is selected from following formula II to XI
Figure 9980431600111
Figure 9980431600112
Figure 9980431600113
Figure 9980431600114
Figure 9980431600121
Figure 9980431600122
Figure 9980431600124
Figure 9980431600125
The purpose of this invention is to provide on the one hand particularly preventing and treating and have good Fungicidally active on the rice crops fungal disease, the mixture that has good insecticidal activity on the other hand again.Because the climatic province of rice crops cultivation also can meet with many harmful insects usually, therefore, it is desired that antifungal and insecticidal activity are combined.
We find that this purpose realizes by the mixture that requires in the claim 1.
Formula I compound and preparation thereof are that itself is known, and are described in (WO 97/15552) in the document.
Formula II to the insecticide of IX is known equally and is described in the document.In addition, they are sold with the trade (brand) name of being mentioned in the bracket hereinafter: II: EP-A 192,060, common name: Imidacloprid (trade (brand) name: Admire , Gaucho , Beyer Co., Ltd produces); III: common name: pyridine worm miaow (trade (brand) name: Mospilan , Cao Da company produces); IV: CAS RN 120738-89-8, common name: Nitenpyram (trade (brand) name: Bestgard  Takeda Chemicals produces); V: Colloit etc., Proc.Br.Conf.Dis.1, (1992), and 29, common name: fluorine worm nitrile (trade (brand) name: the special  of sharp strength, Rhone-Poulenc produces); VI: US 3474170, US 3474171 and DE-C 1493646; Common name: (trade (brand) name: Curaterr  Beyer Co., Ltd produces carbofuran; The red  of furans, FMC produces); VII: crop protection conference meeting newspaper (Proc.Br.Crop.Prot.Conf.) 2 (1979), 557 all over Britain, common name: carbosulfan (trade (brand) name: Marshall , FMC produces); VIII: FR-A 2489329; The 10th international crop protection conference meeting newspaper (Proc.Int.Congr.Plant Prot.10 Th), 2 (1983), 360, common name: Benfuracard micro (trade (brand) name: Oncol , Otsuka produces; Furacon , Siapa produces); IX: CAS RN 111 988-49-9, common name: thiacloprid (Beyer Co., Ltd's development product); X: about " insect and disease " Brighton conference meeting newspaper (Proc.Of the BrightonConference on " Pests and Diseases "), volume 1,21-26 page or leaf (MTI 446, and Mitsui produces); XI: about " insect and disease " Brighton conference meeting newspaper (Proc.Of the BrightonConference on " Pests and Diseases "), volume 1,21-26 page or leaf (CGA 293343, and Novartis Co.,Ltd produces).
Because the two keys of C=C and C=N, the preparation of chemical compounds I can produce the E/Z isomer mixture, and they can for example crystallisation or chromatography be separated into independent compound with usual manner.
Yet, if synthetic produce isomer mixture since in some cases (for example under light or acid or alkali effect), preparing to use or in use, independent isomer can be changed mutually, therefore do not need usually to separate.Similarly conversion can also in use take place, for example when handling plant or on the plant of handling or be intended to take place on the harmful fungoid prevented and treated or the animal pest.
For it was active, because the two keys of C=X, preferably the Z isomer of chemical compounds I was (with-OCH 3Or-CH 3Group is with respect to-CO 2R 1The configuration of group).
For it is active, because-C (R 3)=NOCH 2-two keys, preferably the cis-isomer of chemical compounds I is (with R 3Group is with respect to-OCH 2The configuration of group).
In the definition of the compound I that beginning provides, the following group of upperseat concept ordinary representation of use: halogen: fluorine, chlorine, bromine and iodine; Alkyl: have the straight or branched alkyl of 1 to 4,6 or 10 carbon atom, for example, C1-C 6-alkyl such as methyl, ethyl, propyl group, the 1-Methylethyl, butyl, 1-methyl propyl group, 2-methyl propyl group, 1, 1-dimethyl ethyl, amyl group, 1-methyl butyl, 2-methyl butyl, 3-methyl butyl, 1, 1-dimethyl propyl group, 1, 2-dimethyl propyl group, 2, 2-dimethyl propyl group, 1-ethyl propyl group, hexyl, 1-methyl amyl group, 2-methyl amyl group, 3-methyl amyl group, 4-methyl amyl group, 1, the 1-dimethylbutyl, 1, the 2-dimethylbutyl, 1, the 3-dimethylbutyl, 2, the 2-dimethylbutyl, 2, the 3-dimethylbutyl, 3, the 3-dimethylbutyl, 1-ethyl butyl, 1, 1, 2-trimethyl propyl group, 1, 2, 2-trimethyl propyl group, 1-ethyl-1-methyl propyl group or 1-Ethyl-2-Methyl propyl group, haloalkyl: have the straight or branched alkyl of 1 to 6 carbon atom, its part-or all by the above-mentioned halogen atom replacement of mentioning, for example C1-C 2-haloalkyl, as chloromethyl, dichloromethyl, trichloromethyl, methyl fluoride, difluoromethyl, trifluoromethyl, chlorine methyl fluoride, dichloro methyl fluoride, chlorine difluoromethyl, 1-fluorine ethyl, 2-fluorine ethyl, 2,2-difluoro ethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluorine ethyl, 2-chloro-2,2-difluoro ethyl, 2,2-two chloro-2-fluorine ethyls, 2,2,2-, three chloroethyls and pentafluoroethyl group; Cycloalkyl: have the monocycle shape alkyl of 3 to 6 ring memberses, for example cyclopropyl, cyclobutyl, cyclopenta and cyclohexyl; Thiazolinyl: have 2 to 6 or 10 carbon atoms and the straight or branched thiazolinyl of a pair of key is arranged on arbitrary position, for example, C2-C 6-thiazolinyl such as 1-acrylic, the 2-acrylic, 1-ethylene methacrylic base, the 1-cyclobutenyl, the 2-cyclobutenyl, the 3-cyclobutenyl, 1-methyl-1-propylene base, 2-methyl-1-propylene base, 1-methyl-2-acrylic, 2-methyl-2-acrylic, the 1-pentenyl, the 2-pentenyl, the 3-pentenyl, the 4-pentenyl, 1-methyl isophthalic acid-cyclobutenyl, the 2-methyl-1-butene thiazolinyl, the 3-methyl-1-butene base, 1-methyl-2-cyclobutenyl, 2-methyl-2-cyclobutenyl, 3-methyl-2-cyclobutenyl, 1-methyl-3-cyclobutenyl, 2-methyl-3-cyclobutenyl, 3-methyl-3-cyclobutenyl, 1,1-dimethyl-2-acrylic, 1,2-dimethyl-2-acrylic, 1,2-dimethyl-2-acrylic, 1-ethyl-1-acrylic, 1-ethyl-2-acrylic, the 1-hexenyl, the 2-hexenyl, the 3-hexenyl, the 4-hexenyl, the 5-hexenyl, 1-methyl isophthalic acid-pentenyl, 2-methyl isophthalic acid-pentenyl, 3-methyl isophthalic acid-pentenyl, the 4-methyl-1-pentene base, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, the 1-methyl-3-pentenyl, the 2-methyl-3-pentenyl, the 3-methyl-3-pentenyl, the 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-1-acrylic or 1-Ethyl-2-Methyl-2-acrylic, alkynyl: have 2 to 10 carbon atoms and have the straight or branched alkynyl of three key on arbitrary position, for example C2-C 6-alkynyl, as acetenyl, 2-propynyl, 2-butine base, 3-butine base, 1-methyl-2-propynyl, the valerylene base, 3-pentyne base, 4-pentyne base, 1-methyl-2-butine base, 1-methyl-3-butine base, 2-methyl-3-butine base, 1, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-hexin base, 3-hexin base, 4-hexin base, 5-hexin base, 1-methyl-2-pentyne base, 1-methyl-3-pentyne base, 1-methyl-4-pentyne base, 2-methyl-3-pentyne base, 2-methyl-4-pentyne base, 3-methyl-4-pentyne base, 4-methyl-valerylene base, 1, 1-dimethyl-2-butine base, 1, 1-dimethyl-3-butine base, 1, 2-dimethyl-3-butine base, 2, 2-dimethyl-3-butine base, 1-ethyl-2-butine base, 1-ethyl-3-butine base, 2-ethyl-3-butine base and 1-ethyl-1-methyl-2-propynyl, heterocyclic radical or heterocyclic radical oxygen base, heterocyclic radical sulfenyl and heterocyclic radical are amino: three to the hexa-atomic saturated or unsaturated list of part-or polycyclic heterocycle, and they contain one to three and are selected from oxygen, the hetero atom of sulphur and nitrogen and they are directly connected in or through oxygen atom (heterocyclic radical oxygen base) or through sulphur atom (heterocyclic radical sulfenyl) or through amino (heterocyclic radical is amino), are connected on main structure, for example the 2-tetrahydrofuran base, the cyclohexane base, the 3-tetrahydrofuran base, the 2-tetrahydro-thienyl, the 3-tetrahydro-thienyl, the 2-pyrrolidinyl, the 3-pyrrolidinyl, the 3-isoxazole alkyl, the 4-isoxazole alkyl, the 5-isoxazole alkyl, 3-isothiazole alkyl, 4-isothiazole alkyl, 5-isothiazole alkyl, the 3-pyrazolidinyl, the 4-pyrazolidinyl, the 5-pyrazolidinyl, 2-oxazole alkyl, 4-oxazole alkyl, 5-oxazole alkyl, the 2-thiazolidinyl, the 4-thiazolidinyl, the 5-thiazolidinyl, the 2-imidazolidinyl, the 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-thiatriazole alkane-2-base, 1,3,4-triazolidine-2-base, 2,3-dihydrofuran-2-base, 2,3-dihydrofuran-3-base, 2,3-dihydrofuran-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-pyrazoline-3-base, 2,3-dihydro isothiazole-4-base, 2,3-pyrazoline-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, 4,5-dihydro-oxazole-4-base, 4,5-dihydro-oxazole-5-base, 2,3-thiazoline-3-base, 2,3-thiazoline-4-base, 2,3-thiazoline-5-base, 4,5-thiazoline-3-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, the 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, the 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, the 2-THP trtrahydropyranyl, 1,3-dihydro pentane-2-base, 3,4,5,6-tetrahydropyridine-2-base, 4H-1,3-thiazine-2-base, 4H-3,1-benzo thiazine-2-base, 1,1-dioxa-2,3,4,5-thiophane-2-base, 2H-1,4-benzo thiazine-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 arylsulfonyl base: aromatics list-or polycyclic alkyl, they are directly connected in or through oxygen atom (O-) (aryloxy group) or through sulphur atom (O-) (arylthio) or through carbonyl (CO-) (aryl carbonyl) or sulfonyl (SO2-) be connected on main structure for example phenyl, naphthyl and anthryl or phenoxy group, naphthoxy and anthracene oxygen base and carbonyl and sulfonyl accordingly; Assorted virtue itself or assorted aryloxy group, assorted arylthio, assorted aromatic carbonyl and heteroaryl sulfonyl: aromatics list or polycyclic group; they except the carbocyclic ring member, can contain in addition one to four nitrogen-atoms or one to three nitrogen-atoms and oxygen atom or sulphur atom or oxygen atom or sulphur atom and they directly or (assorted aryloxy group) through oxygen atom (O-) or (assorted sulfenyl) through sulphur atom (S-), (heteroaryl carbonyl) through carbonyl (CO-) or (heteroaryl sulfonyl) through sulfonyl (SO2-) be connected on main structure, for example-5-unit heteroaryl, contain one to three nitrogen-atoms: 5-unit heteroaryl, and they are former except carbon
Outside the son, can contain one to three nitrogen-atoms as ring members, for example, 2-pyrrole radicals, 3-
Pyrrole radicals, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazole radicals, 4-imidazole radicals,
1,2,4-triazole-3-base and 1,3,4-triazole-2-base;-5-unit heteroaryl, contain one to four nitrogen-atoms or one to three nitrogen-atoms and sulphur or
Oxygen atom or an oxygen atom or sulphur atom: a 5-unit heteroaryl, they are former except carbon
Outside the son, can contain one to four nitrogen-atoms or one to three nitrogen-atoms or sulphur atom or
Oxygen atom is as ring members, for example, and 2-furyl, 3-furyl, 2-thienyl, 3-
Thienyl, 2-pyrrole radicals, 3-pyrrole radicals, 3-isoxazolyl, 4-isoxazolyl, 5-are different
Oxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrazolyl, 4-
Pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl,
4-thiazolyl, 5-thiazolyl, 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-3-base,
1,2,4-triazole-3-base, 1,3,4-triazole-2-base, 1,3,4-thiadiazoles-2-base, 1,3,4-
Triazole-2-base;-benzo-fused 5-unit heteroaryl, contain one to three nitrogen-atoms or nitrogen-atoms and/
Or oxygen or sulphur atom: 5-unit heteroaryl, they except carbon atom, can contain one to
Four nitrogen-atoms or one to three nitrogen-atoms and sulphur or oxygen atom or oxygen or sulphur are former
Son is as ring members, and wherein two adjacent carbon atoms or nitrogen-atoms with one mutually
Adjacent carbocyclic ring member can pass through fourth-1,3-diene-1,4-two basic bridge joints;-5-unit heteroaryl, through nitrogen atom bonding and contain one to four nitrogen-atoms, or benzo-fused
5-unit heteroaryl, through nitrogen atom bonding and contain one to three assorted virtue of nitrogen-atoms: 5-unit
Base, they can contain one to four nitrogen-atoms and one to three respectively except carbon atom
Individual nitrogen-atoms is as ring members, and adjacent two carbocyclic ring members or nitrogen-atoms and one
Individual adjacent carbocyclic ring member can pass through fourth-1,3-diene-1, and 4-two basic bridge joints, these
Group is connected in main structure with the azo-cycle member;-6-unit heteroaryl contains one to three nitrogen-atoms and one to four nitrogen-atoms respectively: 6-unit
Heteroaryl, they can contain one to three nitrogen-atoms or respectively except carbon atom
To four nitrogen-atoms as ring members, for example, 2-pyridine radicals, 3-pyridine radicals, 4-pyridine
Base, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidine radicals, 4-pyrimidine radicals, 5-pyrimidine radicals, 2-
Pyrazinyl, 1,3,4-triazine-2-base, 1,2,4-triazine-3-base and 1,2,4,5-four
Piperazine-3-base;-benzo-fused 6-unit heteroaryl contains one to four nitrogen-atoms: 6-unit heteroaryl, its
In two adjacent carbocyclic ring members can pass through fourth-1,3-diene-1,4-two basic bridge joints,
For example quinoline, isoquinolin, quinazoline and quinoxaline and oxygen, sulphur, carbonyl or sulfonyl accordingly.Heteroaryl amino: aromatics list-or polycyclic group, they can also contain one to four nitrogen-atoms or one to three nitrogen-atoms and oxygen or sulphur atom and they are connected on the main structure through nitrogen-atoms except the carbocyclic ring member.
" partly-or all halo " definition be intended to be expressed in part on the group of indication-or whole hydrogen atoms all may be substituted by the identical or different halogen atom of as above mentioning.
For it was active, preferably wherein m was 0 formula I compound.
R wherein equally, preferably 1It is the formula I compound of methyl.
In addition, R wherein preferably 3It is the chemical compounds I of hydrogen, cyano group, cyclopropyl, methyl, ethyl, 1-Methylethyl or trifluoromethyl.
And, R wherein preferably 3It is the chemical compounds I of methyl.
In addition, R wherein preferably 3It is the chemical compounds I of cyano group.
Also have, preferably R wherein 3It is the chemical compounds I of cyclopropyl.
In addition, R wherein preferably 2It is the chemical compounds I of trifluoromethyl.
In addition, R wherein preferably 5Be hydrogen, cyclopropyl, methyl, ethyl, isopropyl, the aryl that does not replace or replace or the chemical compounds I of heteroaryl.
And, R wherein preferably 5It is the chemical compounds I of methyl.
In addition, R wherein preferably 5It is the chemical compounds I of ethyl.
In addition, R wherein preferably 5It is the chemical compounds I of isopropyl.
Also have, preferably R wherein 5It is the chemical compounds I of cyclopropyl.
And, R wherein preferably 5It is the chemical compounds I of trifluoromethyl.
In addition, R wherein preferably 5Be the aryl that do not replace or replace or the compound of heteroaryl.
In addition, R wherein preferably 5It is the chemical compounds I of the pyridine radicals, pyrimidine radicals, pyrazinyl, pyridazinyl or the triazinyl that do not replace or replace.
In addition, R wherein preferably 5It is the chemical compounds I of the furyl, thienyl or the pyrrole radicals that do not replace or replace.
In addition, R wherein preferably 5It is the chemical compounds I that does not replace or replace De oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, pyrazolyl or imidazole radicals.
In addition, R wherein preferably 5Be not replace or replace De oxadiazole base, thiadiazolyl group or triazolyl chemical compounds I.
And, preferably also have such chemical compounds I, wherein R 5Be the phenyl that does not replace or have one or two following groups: nitro, cyano group, hydroxyl, amino, 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.
And, preferably also have such chemical compounds I, wherein R 4Be hydrogen, C 1-C 6-alkyl, C 2-C 6-thiazolinyl, C 1-C 6-alkynyl, pi-allyl, aralkyl, heteroarylalkyl, aryloxy alkyl, heteroaryloxy alkyl, aryl or heteroaryl.
In addition, R wherein preferably 4Be C 1-C 6The chemical compounds I of-alkyl.
Also preferred chemical compounds I is disclosed among the WO 97/15,552.
The formula I compound that is contained in the mixture of the present invention has excellent activity to the plant pathogenic fungi of wide spectrum, particularly to the fungi of Ascomycetes, Fungi Imperfecti, Phycomycetes and Basidiomycetes.
Their many plant pathogenic fungis aspect particular importances on control various crops such as cotton, vegetables (for example, cucumber, beans, tomato, potato and cucumber), barley, dogstail, oat, banana, coffee, corn, fruit, rice, rye, soybean, grape, wheat, ornamental plants, sugarcane and many seed.
They are particularly suitable for preventing and treating the following plants disease fungus: the standing grain powdery mildew on the cereal class (Erysiphe graminia), two spore powdery mildews (Erysiphe cichoracearum) on the cucumber and Siberian cocklebur monofilament shell bacterium (Sphaerotheca fuliginea), apple mildew handle coccus (Podosphaera leucotricha) on the apple, grape powdery mildew snag shell on the grape mould (Uncinula necator), 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 (Venturia Inaequalis), length on the cereal class spore bacterium (Helminthosporium) that wriggles, glume blight bacterium on the wheat (Septoria nodorum), strawberry, vegetables, botrytis cinerea on ornamental plants and the grape (Botrytis cinera), peanut tail spore bacterium (Cercospora arachidicola) on the peanut, eye spot bacterium on wheat and the barley (Pseudocercospora herpotophthora), Magnaporthe grisea on rice and the lawn (Pyricularia oryzae), phytophthora infestan on potato and the tomato (Phytophthorainfestans), grape on the grape is given birth to single shaft mould (Plasmopara viticola), alternaric bacteria on vegetables and the fruit (Alternaria) is with the ball chamber bacterium (Mycosphaerella) on the banana and sickle-like bacteria (Fusarium) and verticillium sp (Verticillum).
The formula II is suitable for preventing and treating the animal pest that belongs to insect, mite and Nematoda to the IX compound.They can be used in crop protection and health, preservation material protection and animal doctor aspect.Particularly they are suitable for preventing and treating following animal pest: the following purpose harmful insect, Lepidoptera, for example, black cutworm (Agrotis ypsilon), turnip noctuid (Agrotis segetum), cotton leaf ripple noctuid (Alabamaargillacea), Anticarsia (Anticarsia gemmatalis), apple silver moth (Argyresthia conjugella), Chinese horse noctuid (Autographa gamma), pine sphinx moth (Bupalus piniarius), Cacoecia murinana, Capua reticulana, winter geometrid moth (Cheimatobia brumata), spruce bunworm (Choristoneurafumiferana), west choristoneura fumiferana (Choristoneura occidentalis), some mythimna separatas (Cirphis unipuncta), the moth-eaten moth (Cydia pomonella) of apple, dendrolimus pini (Dendrolimus pini), the wild snout moth's larva (Diaphania nitidalis) of melon, southwestern corn borer (Diatraea grandiosella), the real moth (Earias insulana) of cotton spot, Africa sugarcane borer (Elasmopalpus lignosellus), Eupoecilia ambiguella, european pine shoot moth (Evetria bouliana), grain skin ground tiger (Feltia subterranea), galleria mellonella waxmoth (Galletia mellonella), Lee's Grapholita spp (Grapholithafunebrana), oriental fruit moth (Grapholitha molesta), cotton bollworm (Heliothisarmigera), tobacco budworm (Heliothis virescens), cotton bollworm (Heliothiszea), Hellula undalis (Hellula undalis), Hibernia defoliaria, fall webworm (Hyphantria cunea), Hyponomeuta malinellus, the moth-eaten moth (Keiferia lycopersicella) of tomato, Chinese hemlock spruce geometrid moth (Lambdina fiscellaria), beet armyworm (Laphygma exigua), some lyonetids of coffee (Leucopteracoffeella), lira noctuid (Leucoptera scitella), Lithocolletisblancardella, Lobesia botrana, beet webworm (Loxostegesticticalis), gypsymoth (Lymantria dispar), lymantria monacha (Lymantriamonacha), peach leaf miner (Lyonetia clerkella), tent caterpillar (Malacosomaneustria), tomato moth (Mamestra brassicae), star-spangled banner gypsymoth (Orgyiapseudotsugata), corn borer (Ostrinia nubilalis), small noctuid (Panolisflammea), pink bollworm (Pectinophora gossypiella), the variegated noctuid of beans (Peridroma saucia), circle palm boat moth (Phalera bucephala), potato poison moth (Phthorimaea operculella), tangerine leaf lyonetid (Phyllocnistiscitrella), large white butterfly (Pieris brassicae), the green noctuid of clover (Plathypenascabra), diamond-back moth (Plutella xylostella), soybean noctuid (Pseudoplusiaincludens), two or three pins pine steinernema (Rhyacionia frustrana), Scrobipalpula absoluta, gelechiid (Sitotroga cerealella), pilleriana (Sparganothis pilleriana), noctuid (Spodopterafrugiperda) is coveted on the meadow, Egyptian lap worm (Spodoptera littoralis), twill leaf moth (Spodoptera litura), Thaumatopoea pityocampa, the green volume of oak moth (Tortrix viridana), cabbage looper (Trichoplusia ni) and Canadian rouleau snout moth's larva (Zeiraphera canadensis);
Coleoptera, for example, the long lucky fourth (Agrilus sinuatus) of pears, vertical bar click beetle (Agrioteslineatus), dark and gloomy click beetle (Agriotes obscurus), Amphimallussolstitialis, Li Limu bark beetle (Anisandrus dispar), wild cotton resembles (Anthonomusgrandis), pear flower resembles (Anthonomus pomorum), Atomaria linearis (Atomarialinearis), Da Song, moth-eaten (Blastophagus piniperda), Blitophagaundata, broad bean weevil (Bruchus rufimanus), pea weevil (Bruchus pisorum), Bruchus lentis, the birch leaf roll resembles (Byctiscus betulae), the big tortoise plastron of beet (Cassida nebulosa), beans chrysomelid (Cerotoma trifurcata), wild cabbage pod weevil (Ceuthorhynchus assimilis), Ceuthorhynchus napi, beet shin flea beetle (Chaetocnema tibialis), cigarette wireworm (Conoderus vespertinus), the gate winter chrysomelid (Crioceris asparagi), northern corn root-worm (Diabroticalongicornis), 12 variegated leaf first (Diabrotica 12-punctata), corn bud root chrysomelid (Diabrotica virgifera), Mexico's beans first (Epilachna varivestis), tobacco flea beetle (Epitix hiripennis), cottonseed ash weevil (Eutinibothrusbrasiliensis), the big weevil (Hylobius abietis) of pine, Egyptian alfalfa snout beetle (Hyperabrunneipennis), alfalfa weevil (Hypera postica), ips typographus (Ipstypographus), cigarette scotellaris (Lema bilineata), cereal leaf beetle (Lemamelanopus), colorado potato beetle (Leptinotarsa decamlineata), California wireworm (Limonius californicus), american rice weevil (Lissorhoptrusoryzophilus), corn click beetle (Melanotus communis), pollen beetle (Meligethes aeneus), Melolontha hippocastani, the west melolonthid in May (Melolontha melolontha), rice leaf beetles (Oulema oryzae), vine black ear beak resembles (Otiorrhynchus sulcatus), strawberry ear beak resembles (Otiorrhynchusovatus), horseradish daikon leaf beetle (Phaedon cochleariae), Phyllotretachrysocephala, the melolonthid (Phyllophaga sp.), garden chafer (Phyllopertha horticola), the light sufficient flea beetle of turnip (Phyllotretanemorum), cabbage flea beetle (Phyllotreta striolata), Japanese beetle (Popilliajaponica) and grain weevil (Sitophilus granaria);
Diptera, for example, Aedes aegypti (Aedes aegypti), aedes vexans (Aedesvexans), Mexico oriental fruit fly (Anastrepha ludens), anopheles maculipennis (Anophelesmaculipennis), Mediterranean fruitfly (Ceratitis capitata), chrysomyia bezziana (Chrysomya bezziana), Chrysomya hominivorax, chrysomyia macellaria (Chrysomya macellaria), sorghum gall midge (Contarinia sorghicola), cordylobia anthropophaga (Cordylobia anthropophaga), northern house (Culex pipiens), melon trypetid (Dacus cucurbitae), oil olive trypetid (Dacus oleae), wild cabbage cecidomyiia (Dasineura brassicae), anthomyia canicularis (Fannia canicularis), Gasterophilus intestinalis (Gasterophilus intestinalis), Glossina morsitans, Deliacoarctata, Haematobia irritans (Haematobia irritans), Haplodiplosisequestris, plant fly (Hylemyia platura), Hypoderma lineata, Liriomyza sativae, Americal rice leaf miner (Liriomyza trifolii), Luciliacaprina, lucilia cuprina (Lucilia cuprina), lucilia sericata (Lucilia sericata), Lycoria pectoralis, hessian fly (Mayetiola destructor), housefly (Muscadomestica), nonbiting stable fly (Muscina stabulans), oestrosis of sheep (Oestrus ovis), Sweden's wheat stem chloropid fly (Oscinella frit), the leaf of spinach flowerfly (Pegomya hyoscyami), Phorbia antiqua, wild cabbage flowerfly (Phorbia brassicae), Phorbiacoarctata, cherry fruit fly (Rhagoletis cerasi), dish trypetid (Rhagoletispomonella), the gadfly (Tabanus boyinus), Tipula oleracea, marsh daddy-longlegs (Tipula paludosa)
Thrips, for example, cigarette brown thrip (Frankliniella fusca), west thrips (Frankliniella occidentalis), wheat thrips (Frankliniellatritici), wheat pipe thrips (Haplothrips tritici), the real thrips (Scirtothrips citri) of tangerine, rice thrips (Thrips oryzae), pale brown thrips (Thripspalmi), cotton thrips (Thrips tabaci);
Hymenoptera, for example, cabbage sawfly (Athalia rosae), tropical leaf cutting ant (Attacephalotes), leaf cutting ant (Atta sexdens), Texas leaf cutting ant (Atta texana), sawfly (Hoplocampa minuta), apple sawfly (Hoplocampa testudinea), MonomoriumMayr (Monomorium pharaonis), fiery ant (Solenopsis geminata) and the infrared ant of flaring up (Solenopsis invicta);
Semiptera, for example, like green stinkbug (Acrosternum hilare), hairy chinch bug (Blissusleucoperus), tobacco blackspot fleahopper (Cyrtopetis notatus), red cotton bug (Dysdercus cingulatus), in red stinkbug (Dysdercus intermedius), Eurygaster integriceps, cotton brown stinkbug (Euschistus imipictiventris), leaf beak coried (Leptoglossus phyllopus), tarnished plant bug (Lyguslineolaris), tarnished plant bug (Lygus pratensis), yellow shoulder green stinkbug (Nezaraviridula), beet is intended lace bug (Piesma quadrata), Solubea insularis and Thyanta perditor;
Homoptera, for example, Acyrthosiphon onobrychis, adelge laricis (Adelgeslaricis), Aphidula nasturtii, aphis fabae (Aphis fabae), apple aphid (Aphis pomi), Aphis sambuci, Ji short-tail aphid (Brachycaudus cardui), cabbage aphid (Brevicoryne brassicae), Cerosipha gossypii, Dreyfusianordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, egg beans Empoasca spp (Empoasca fabae), English grain aphid (Macrosiphum avenae), potato aphid (Macrosiphumeuphorbiae), rose aphid (Macrosiphon rosae), broad bean is repaiied tail aphid (Megouraviciae), rose wheat aphid (Metopolophium dirhodum), black peach aphid (Myzodespersicae), cherry knurl aphid (Myzus cerasi), brown plant-hopper (Nilaparvatalugens), handle goitre woolly aphid (Pemphigus bursarius), sugarcane plant hopper (Perkinsiellasaccharicida), hops wart volume aphid (Phorodon humuli), apple leaf sucker (Psyllamali), pear sucker (Psylla piri), Rhopalomyzus ascalonicus, corn Rhopalosiphum spp (Rhopalosiphum maidis), Sappaphis mala, Sappaphis mali, split aphid (Schizaphis graminum) between grass, Schizoneura lanuginosa, greenhouse whitefly (Trialeurodes vaporariorum) and grape phylloxera (Viteusvitifolii);
Isoptera, for example, Calotermes flavicollis, Leucotermesflavipes, Reticulitermes lucifugus and Termes natalensis;
Orthoptera, for example, acheta domestica (Acheta domestica), oriental cockroach (Blattaorientalis), Groton bug (Blattella germanica), Forficulaauricularia, Europe mole cricket (Gryllotalpa gryllotalpa), migratory locusts (Locustamigratoria), two-striped grasshopper (Melanoplus bivittatus), red leg grasshopper (Melanoplus femurrubrum), Mexico grasshopper (Melanoplus mexicanus), migrate grasshopper (Melanoplus sanguinipes), Luo Ji mountain grasshopper (Melanoplusspretus), red wing locust (Nomadacris septemfasciata), American cockroach (Periplaneta americana), America locust (Schistocerca americana), Schistocerca peregrina, Stauronotus maroccanus and desert locust (Schistocerca gregaria);
Arachnids, for example, the tick order such as the U.S. spend tick (Amblyomma americanum), Amblyomma variegatum, adobe tick (Argas persicus), annular ox tick (Boophilus annulatus), ox tick (Boophilus decoloratus) fades, boophilus microplus (Boophilus microplus), purplish red short hairs mite (Brevipalpusphoenicis), Bryobia praetiosa (Bryobia praetiosa), dermacentor silvarum (Dermacentorsilvarum), carpinus turczaninowii beginning tetranychid (Eotetranychus carpini), tangerine goitre mite (Eriophyes sheldoni), tack glass eye tick (Hyalomma truncatum), castor bean tick (Ixodes ricinus), Ixodes rubicundus, tampan tick (Ornithodorus moubata), ear stings residual beak beer (Otobius megnini), Paratetranychus pilosus, chicken peronium mite (Dermanyssus gallinae), citrus rust mite (Phyllocoptruta oleivora), Polyphagotarsonemus latus Banks (Polyphagotarsonemus latus), sheep sore mite (Psoroptes ovis), rhipicephalus appendiculatus (Rhipicephalus appendiculatus), Rhipicephalusevertsi, itch mite (Sarcoptes scabibei), Tetranychus cinnabarinus (Tetranychuscinnabarinus), kamisawa tetranychus (Tetranychus kanzawai), Pacific Ocean tetranychid (Tetranychus pacificus), cotton spider mites (Tetranychus telarius) and T.urticae Koch (Tetranychus urticae)
Nematode, for example, root-knot nematode, for example northern root-knot nematode (Meloidogyne hapla), jute root-knot nematode (Meloidogyne incognita), javanese root knot nematode (Meloidogynejavanica), the capsule nematode, globodera rostochiensis (Globodera rostochiensis) for example, oat golden nematode (Heterodera avenae), soybean cyst nematode (Heteroderaglycines), Shi Shi golden nematode (Heterodera schachtii), clover golden nematode (Heterodera trifolii), stem eelworm and leaf nematode, for example, long-tail thorn nematode (Belonolaimus longicaudatus), potato haulm nematode (Ditylenchusdestructor), fuller's teasel stem eelworm (Ditylenchus dipsaci), many band helicotylenchus (Heliocotylenchus multicinctus), ease is gone minute hand nematode (Longidoruselongatus), similar similes thorne (Radopholus similis), the strong nematode that spirals (Rotylenchus robustus), original burr nematode (Trichodorus primitivus), the Clayton downgrades nematode (Tylenchorhynchus claytoni), indefinite dwarfing nematode (Tylenchorhynchus dubius), unelected Pratylenchidae (Pratylenchusneglectus), Cobb root (Pratylenchus penetrans), cultivate Pratylenchidae (Pratylenchus curvitatus) and Gooch Pratylenchidae (Pratylenchusgoodeyi).
The active component application dosage normally 0.01 to 2.0 of control noxious animal is preferably 0.02 to 1.0kg/ hectare under field condition.
Mixture of the present invention is particularly suitable for preventing and treating plant disease and the harmful insect in the rice crops.
Chemical compounds I and at least a compound ii to XI can simultaneously, together or respectively or be used successively or successively under the situation of separate administration and not influence and prevent and treat the result.
The character that depends on required effect, the application dosage of mixture of the present invention on crops, is 0.01 to 8kg/ hectare particularly, preferred 0.1 to 5kg/ hectare, particularly 0.5 to 3.0kg/ hectare.
For chemical compounds I, application dosage is 0.01 to 2.5kg/ hectare, preferred 0.05g to 2.5kg/ hectare, particularly 0.1 to 1.kg/ hectare.
For seed treatment, the application dosage of mixture is 0.001 to 250g/kg seed normally, and preferred 0.01 to 100g/kg, and particularly 0.01 to 50g/kg.
If control plant pathogenic fungi, can be by to seed, plant or before and after the plant seeding or the spraying of the soil before and after the plant germination or dust, come the mixture of administered compound I and at least a compound ii separately or together to XI or chemical compounds I and at least a compound ii to IX.
The form that mixture of the present invention for example can be processed into directly spray solution, powder and suspension or high concentration water-based, oiliness or other suspension, dispersion liquid, emulsion, oily dispersion liquid, paste, pulvis, spread fertilizer over the fields composition or granule, and by spraying, atomizing, dust, spread fertilizer over the fields or pour use.Administration form depends on the purpose of use; Under each situation, should guarantee that the dispersion of mixture of the present invention is trickle as much as possible and even.
These preparations can prepare in a known manner, for example by with reactive compound solvent and/or carrier, if desired, adopt emulsifier and dispersant to fill, if use water as thinner, also can make cosolvent with other organic solvent.The cosolvent that is suitable for this purpose mainly is: solvent such 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 silicic acid of high dispersive, 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.
The surfactant that is fit to is a for example lignosulphonic acid of aromatic sulfonic acid, phenolsulfonic acid, the alkali metal of naphthalene sulfonic acids and dibutyl naphthalene sulfonic acids, alkali salt, and fatty acid, alkyl sulfonic acid and alkyl aryl sulphonic acid, alkylsurfuric acid, the alkali metal of lauryl ether sulfuric acid and fatty alcohol sulphuric acid, alkali salt, and Sulfated 16-, 17-and the salt of octadecanol or fatty alcohol ether, the condensation product of the derivative of sulfonated naphthalene and itself and formaldehyde, the condensation product of naphthalene or naphthalene sulfonic acids and phenol and formaldehyde, polyoxyethylene octylphenol ether, the iso-octyl of ethyoxyl alkanisation-, octyl group-or nonyl phenol, alkylphenol or tributyl phenyl polyglycol ether, alkyl aryl polyether alcohol, different three decyl alcohol, the fatty alcohol ethylene oxide condensate, ethoxylated castor oil, polyoxyethylene alkyl ether or polyoxypropylene, laruyl alcohol polyglycol ether acetic acid esters, sorbitan ester, lignin sulfite waste liquor or methylcellulose.
Powder, spreading fertilizer over the fields material and pulvis can be by mixing with at least a compound ii to the mixture of XI chemical compounds I and at least a compound ii to XI or chemical compounds I or grinding and produce with solid carrier.
Granule (for example, coating, dipping or homogeneous particle agent) can prepare by one or more reactive compounds are adhered on the solid carrier.
Solid carrier is that ore soil is as silica gel, silicic acid, silicate, talcum, kaolin, lime stone, lime, chalk, bole, loess, potter's clay, dolomite, diatomite, calcium sulphate and magnesium sulfate, magnesia, the synthetic material, the chemical fertilizer that grind are as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea and plant product such as flour, bark powder, wood powder and shuck powder, cellulose powder and other solid carrier.Activity compound concentration in direct useful formulations can change in wide relatively scope.
Usually, preparation contain by weight 0.1 to 95%, preferred a kind of chemical compounds I of 0.5 to 90% by weight and at least a compound ii mixture to XI or chemical compounds I and at least a compound ii to XI.The general employing 90 to 100% of reactive compound, preferred 95 to 100% purity (according to NMR or HPLC spectrum).
Chemical compounds I and at least a compound ii to XI, its mixture or corresponding preparation passed through the mixture with the antifungal effective dose, or under situation about using respectively, administered compound I and at least a compound ii be to XI, handles harmful fungoid, its dried rhizome of rehmannia or make it plant, seed, soil, zone, material or the space avoiding infecting of dwelling.
Use and to carry out before or after infecting at harmful fungoid.
These examples that comprise formulations of active ingredients have: the solution of the active component of I .90 weight portion and 10 weight portion N-Methyl pyrrolidone.This is molten
Liquid is suitable for using with the form of droplet.8 to 10 of the dimethylbenzene of the active component of II .20 weight portion, 80 weight portions, 10 weight portions
The adduct of moles of ethylene oxide and 1 mole of oleic acid N-single ethanol amide, 5 weight portions
Calcium salt of dodecylbenzene sulfonate and 40 moles of ethylene oxide and the l mole of 5 weight portions
The mixture of the adduct of castor oil.In this solution segmentation aproll, obtain dispersion liquid.The isobutanol of the cyclohexanone of the active component of III .20 weight portion, 40 weight portions, 30 weight portions
Moisture with the adduct of 40 moles of ethylene oxide of 20 weight portions and 1 mole of castor oil
Liquid looses.The cyclohexanol of the active component of IV .20 weight portion, 25 weight portions, 65 weight portion boiling points are 210
To the mineral oil fraction of 280C and 40 moles of ethylene oxide and the l mole of 10 weight portions
The aqueous dispersions of the addition product of castor oil.Diisobutyl naphthalene-1-the sulfonate sodium, 10 of the active component of V .80 weight portion, 3 weight portions
The lignin sodium sulfate salt that derives from sulfite waste liquor of weight portion and the powdery silicon of 7 weight portions
The mixture that glue grinds in sledge mill.This mixture is finely divided in water, obtain spraying
Liquid.The kaolinic intimate mixture that the active component of VI .3 weight portion and 97 weight portions are finely divided.
This agent of dusting contains 3% (weight) reactive compound by weight.The granular colloidal silica of the active component of VII .30 weight portion, 92 weight portions and 8 weight portions are sprayed
Intimate mixture to the paraffin on the surface of silica gel.This preparation is given reactive compound with very
Good viscosity.Phenolsulfonic acid/the urea of the active component of VIII .40 weight portion, 10 weight portions/formaldehyde condensation products
The silica gel of sodium salt, 2 weight portions and the stabilize water dispersion liquid of the water of 48 weight portions.This
Dispersion liquid can further dilute.The calcium salt of dodecylbenzene sulfonate of the active component of IX .20 weight portion, 2 weight portions, 8 weight
The sodium salt and 88 of the fatty alcohol glycol ether of part, the phenol/urea/formaldehyde condensation products of 20 weight portions
The stable oil dispersant of the paraffin sample mineral oil of weight portion.
The synergistic activity of mixture of the present invention can confirm by following experiment:
Active component process separately or together be formed in 63% cyclohexanone by weight and by weight the concentration in the mixture of 27% emulsifier be 10% emulsion, and be diluted with water to desired concn.
Estimate by definite susceptible leaf area percentage, and these fraction values are changed into effectiveness.Rendeing a service (W) uses the Abbot formula to calculate
W=(1-α)100／β
The fungal infection % of the treated plant of α
β is the fungal infection % of (in the same old way) plant of being untreated
Effectiveness is 0 o'clock, refers to that gradient of infection is suitable with the untreated control sample; Effectiveness is 100 o'clock, refers to that treated plant does not infect.
It is to calculate [R.S.Colby, " weeds " [Weeds] 15,20-22 (1967)] with the Colby formula that the expection of mixture of active principles is renderd a service, and makes comparisons with actual measurement effectiveness.
The Colby formula:
E=x+y-xy／100
Desired value when E uses the mixture of active components A and B with concentration a and b is to represent with respect to untreated % in the same old way
Effectiveness when x uses active components A with concentration a is to represent with respect to untreated % in the same old way
Effectiveness when y uses active component B with concentration b is to represent with respect to untreated % in the same old way.
Application Example 1-is to the activity of rice blast (Pyricularia oryzae)
With rice seedlings (kind: Tai Nong 67) use by the aqueous compositions spraying that comprises the active component that mother liquor prepares in 10% active component, 63% cyclohexanone and 27% emulsifier until downward drip.Second day,, and under 22-24 ℃, relative moisture 95-99%, kept 6 days the aqueous spore suspension spraying of plant with the fungi Magnaporthe grisea.Disease development degree on the visual assessment blade afterwards.
The incidence of leaf zone percentage that range estimation is definite changes into the effectiveness with respect to untreated control.Effectiveness 0 is meant identical with the occurring degree of untreated control sample, renders a service 100% and refers to that morbidity is 0%.The expection of active component combination render a service be with the Colby formula calculate [R.S.Colby, " synergy of calculating the weeding combination and antagonism reaction ", " weeds " [Weeds] 15,20-22 (1967)], and with survey effectiveness and make comparisons.
As component a), use the following compounds I ':
Result of the test is listed in hereinafter in the table 1 and 2:
Table 1
Embodiment Active component Concentration (in ppm) Effectiveness (%) with respect to the untreated control sample
????1C Do not have (infection rate 100%) ????0
????2C Chemical compounds I, ????2．0 ????0．5 ????20 ????0
????3C Compound ii ????2．0 ????0．5 ????0 ????0
????4C The compound V ????2．0 ????0．5 ????0 ????0
Table 2
Embodiment Mixture of the present invention (concentration is in ppm) Observed effectiveness The effectiveness * that calculates)
????5 ????2ppm?Ⅰ’+2ppm?Ⅱ ????50％ ????20％
????6 ?0．5ppm?Ⅰ’+0．5ppm?Ⅱ ????30％ ????10％
????7 ?2ppm?Ⅰ’+2ppm?Ⅴ ????40％ ????20％
????8 ?0．5ppm?Ⅰ’+0．5ppm?Ⅴ ????25％ ????10％
*) calculate with the Colby formula
Result of the test shows, observes to render a service to surpass and uses the effectiveness of calculating with the Colby formula in advance.

Claims (4)

1. the mixture that is used for crop protection, it comprises the following active component of synergistic activity amount: a) phenyl acetic acid derivatives and the salt thereof of formula (I) Wherein to have following connotation: X be NOCH for substituting group and symbol 3, CHOCH 3Or CHCH 3Y is oxygen or NR; R 1, R is hydrogen or C independently of each other 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, if wherein m is 2, and radicals R then 2Can be identical or different; R 3Be hydrogen, cyano group, C 1-C 4-alkyl, C 1-C 4-haloalkyl or C 3-C 6-cycloalkyl; R 4, R 6Be hydrogen independently of each other,
Be C 1-C 10-alkyl, C 3-C 6-cycloalkyl, C 2-C 10-thiazolinyl, 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 sulfonyl
Base, wherein these groups can part-or whole halos, maybe can have one to three
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
Sulfonyl, C 1-C 6-alkylsulfonyloxy, 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-alkane
Base is 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-thiazolinyl,
C 2-C 6-alkene oxygen base, C 3-C 6-cycloalkyl, C 3-C 6-cycloalkyl oxy, heterocyclic radical, heterocycle
Base oxygen base, benzyl, benzyloxy, aryl, aryloxy group, arylthio, heteroaryl, assorted virtue
Oxygen base and heteroarylthio, wherein cyclic group part can part-or whole halos, or
Can have one to three following groups: cyano group, nitro, hydroxyl, sulfydryl, amino,
Carboxyl, amino carbonyl, amino thiocarbonyl, halogen, C 1-C 6-alkyl, C 1-C 6-halo
Alkyl, C 1-C 6-alkyl sulphonyl, C 1-C 6-alkylsulfonyloxy, 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-alkane
Base is amino, two-C 1-C 6-alkyl amino, C 1-C 6-alkyl amino-carbonyl, two-C 1-C 6-alkane
Base amino carbonyl, C 1-C 6-thio-alkyl amino-carbonyl, two-C 1-C 6-alkyl amino sulfo-
Carbonyl, C 2-C 6-thiazolinyl, C 2-C 6-alkene oxygen base, C 3-C 6-cycloalkyl, C 3-C 6-cycloalkyl
Oxygen base, heterocyclic radical, heterocyclyloxy base, benzyl, benzyloxy, aryl, aryloxy group, virtue
Sulfenyl, heteroaryl, heteroaryloxy, heteroarylthio and C (=NOR 7)-A n-R 8
Be aryl, aryl carbonyl, aryl sulfonyl, heteroaryl, heteroaryl carbonyl or heteroaryl
Sulfonyl, wherein these groups can part-or whole halo, maybe can have one to
Three following groups: cyano group, nitro, hydroxyl, sulfydryl, amino, carboxyl, amino carbonyl
Basic, amino thiocarbonyl, halogen, C 1-C 6-alkyl, C 1-C 6-haloalkyl, C 1-C 6-
Alkyl sulphonyl, C 1-C 6-alkylsulfonyloxy, C 1-C 6-alkoxyl, C 1-C 6-alkyl halide
Oxygen base, 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-thiazolinyl,
C 2-C 6-alkene oxygen base, C 3-C 6-cycloalkyl, C 3-C 6-cycloalkyl oxy, benzyl, benzyloxy,
Aryl, aryloxy group, arylthio, heteroaryl, heteroaryloxy or C (=NOR 7)-A n-R 8R 5Be hydrogen,
Be C 1-C 6-alkyl, C 2-C 6-thiazolinyl, C 2-C 6-alkynyl, wherein these groups can part
-or whole halo, maybe can have one to three following groups: cyano group, nitro, hydroxyl
Base, 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-alkyl amino sulfo-carbonyl
Base, two-C 1-C 6-thio-alkyl amino-carbonyl, C 1-C 6-alkyl sulphonyl, C 1-C 6-alkane
Base sulfonyloxy, C 1-C 6-alkoxyl, C 1-C 6-halogenated alkoxy, C 1-C 6-alkoxyl carbonyl
Base, C 1-C 6-alkylthio group, C 1-C 6-alkyl amino, two-C 1-C 6-alkyl amino, C 2-C 6-
Alkene oxygen base, C 3-C 6-cycloalkyl, C 3-C 6-cycloalkyl oxy, heterocyclic radical, heterocyclyloxy base,
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, wherein cyclic group part can part-or whole halos, maybe can have
One to three following groups: cyano group, nitro, hydroxyl, sulfydryl, amino, carboxyl, ammonia
Base carbonyl, amino thiocarbonyl, C 1-C 6-alkyl, C 1-C 6-haloalkyl, C 1-C 6-alkane
Base sulfonyl, C 1-C 6-alkylsulfonyloxy, 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-alkane
Base is amino, two-C 1-C 6-alkyl amino, C 1-C 6-alkyl amino-carbonyl, two-C 1-C 6-alkane
Base amino carbonyl, C 1-C 6-thio-alkyl amino-carbonyl, two-C 1-C 6-alkyl amino sulfo-
Carbonyl, C 2-C 6-thiazolinyl, C 2-C 6-alkene oxygen base, benzyl, benzyloxy, aryl, aryloxy group,
Arylthio, heteroaryl, heteroaryloxy, heteroarylthio and C (=NOR 7)-A n-R 8
Be C 3-C 6-cycloalkyl, C 3-C 6-cycloalkenyl group, heterocyclic radical, aryl, heteroaryl, wherein
Cyclic group part can part-or whole halo, maybe can have one to three following
Group: 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-alkylsulfonyloxy, C 3-C 6-cycloalkyl, C 1-C 6-alkoxyl, C 1-C 6-haloalkoxy
Base, 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-thiazolinyl,
C 2-C 6-alkene oxygen base, benzyl, benzyloxy, aryl, aryloxy group, heteroaryl and assorted fragrant oxygen
Base;
Wherein
A is oxygen, sulphur or nitrogen, and wherein nitrogen has hydrogen or C 1-C 6-alkyl;
N is 0 or 1;
R 7Be hydrogen or C 1-C 6-alkyl and
R 8Be hydrogen or C 1-C 6-alkyl, and b) at least a compound that is selected from following formula II to XI
Figure 9980431600051
Figure 9980431600052
Figure 9980431600053
Figure 9980431600055
Figure 9980431600061
Figure 9980431600062
Figure 9980431600063
Figure 9980431600065
2. the mixture of claim 1, it is made up of two parts, and a part is included in the chemical compounds I in solid or the liquid-carrier, and another part is included at least a compound ii in solid or the liquid-carrier to XI.
3. methods for fighting harmful mushrooms, it comprises that mixture process fungi with claim 1 or 2, its dwell dried rhizome of rehmannia or processing are intended to prevent and kill off material, plant, seed, soil, surface or the space that harmful fungoid infects, and wherein chemical compounds I and at least a compound ii to using of XI can promptly be carried out simultaneously together or respectively or successively.
4. according to the method for claim 3, wherein, fungi, its dwell dried rhizome of rehmannia or processing are intended to prevent and kill off plant, seed, soil, surface or the space that harmful fungoid infects and handle with the chemical compounds I of 0.005 to 1kg/ hectare.
CNB998043168A 1998-03-24 1999-03-22 Fungicide mixtures based on triple oxime ether derivatives and insecticides Expired - Fee Related CN1139323C (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE19812762 1998-03-24
DE19812762.6 1998-03-24
DE19855331.5 1998-12-01
DE19855331 1998-12-01

Publications (2)

Publication Number Publication Date
CN1294488A true CN1294488A (en) 2001-05-09
CN1139323C CN1139323C (en) 2004-02-25

Family

ID=26044900

Family Applications (1)

Application Number Title Priority Date Filing Date
CNB998043168A Expired - Fee Related CN1139323C (en) 1998-03-24 1999-03-22 Fungicide mixtures based on triple oxime ether derivatives and insecticides

Country Status (14)

Country Link
EP (1) EP1082009A1 (en)
JP (1) JP4458666B2 (en)
KR (1) KR100557365B1 (en)
CN (1) CN1139323C (en)
AR (1) AR018809A1 (en)
AU (1) AU735903B2 (en)
BR (1) BR9909048A (en)
CA (1) CA2324460A1 (en)
CO (1) CO5060421A1 (en)
ID (1) ID26839A (en)
IL (1) IL138295A0 (en)
MX (1) MXPA00008747A (en)
TW (1) TW520274B (en)
WO (1) WO1999048366A1 (en)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19956098A1 (en) * 1999-11-22 2001-05-23 Bayer Ag Synergistic plant fungicide composition containing spiroxamine, quinoxyfen and imidacloprid, thiacloprid and/or thiamethoxam, especially effective against cereal diseases
CN100345482C (en) * 2000-12-18 2007-10-31 巴斯福股份公司 Fangicide mixtures based on oxime ether derivatives
DE10140108A1 (en) * 2001-08-16 2003-03-06 Bayer Cropscience Ag Fungicidal active ingredient combinations
CA2478587C (en) * 2002-03-08 2011-05-17 Basf Aktiengesellschaft Fungicidal mixtures based on prothioconazole and containing an insecticide
DE602004021026D1 (en) 2003-12-18 2009-06-18 Basf Se FUNGICIDAL MIXTURES BASED ON CARBAMATE DERIVATIVES AND INSECTICIDES
JP2008524150A (en) * 2004-12-20 2008-07-10 ビーエーエスエフ ソシエタス・ヨーロピア Methods for controlling fungal diseases in legumes
DE102004062513A1 (en) * 2004-12-24 2006-07-06 Bayer Cropscience Ag Insecticides based on neonicotinoids and selected strobilurins
US9326509B2 (en) 2005-02-22 2016-05-03 Basf Se Composition and method for improving plant health
WO2008095913A2 (en) 2007-02-06 2008-08-14 Basf Se Pesticidal mixtures
US8288315B2 (en) 2007-04-25 2012-10-16 Basf Se Fungicide mixtures
WO2009098210A2 (en) * 2008-02-05 2009-08-13 Basf Se Pesticidal mixtures
WO2009098228A2 (en) * 2008-02-05 2009-08-13 Basf Se Pesticidal mixtures
EA020599B1 (en) 2008-07-04 2014-12-30 Басф Се Fungicidal mixtures comprising substituted 1-methylpyrazol-4-ylcarboxanilides and abamectin
US8748341B2 (en) 2009-09-29 2014-06-10 Basf Se Pesticidal mixtures
KR20120105434A (en) 2009-09-29 2012-09-25 바스프 에스이 Pesticidal mixtures
US20120283095A1 (en) * 2009-12-02 2012-11-08 Basf Se Pesticidal mixtures
JP2012102075A (en) * 2010-10-14 2012-05-31 Sumitomo Chemical Co Ltd Noxious organism-preventing/eliminating composition and noxious organism-preventing/eliminating method

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19539324A1 (en) * 1995-10-23 1997-04-24 Basf Ag Phenylacetic acid derivatives, processes and intermediates for their preparation and compositions containing them

Also Published As

Publication number Publication date
JP2002507551A (en) 2002-03-12
EP1082009A1 (en) 2001-03-14
AU735903B2 (en) 2001-07-19
CA2324460A1 (en) 1999-09-30
CN1139323C (en) 2004-02-25
KR20010034646A (en) 2001-04-25
ID26839A (en) 2001-02-15
AR018809A1 (en) 2001-12-12
IL138295A0 (en) 2001-10-31
JP4458666B2 (en) 2010-04-28
BR9909048A (en) 2000-12-05
WO1999048366A1 (en) 1999-09-30
MXPA00008747A (en) 2001-03-01
AU2934899A (en) 1999-10-18
TW520274B (en) 2003-02-11
CO5060421A1 (en) 2001-07-30
KR100557365B1 (en) 2006-03-10

Similar Documents

Publication Publication Date Title
JP3388765B2 (en) Ortho-substituted phenylacetamide
EP0669319B1 (en) O-Benzyloxime ethers and plant-protecting agents containing them
CN1139323C (en) Fungicide mixtures based on triple oxime ether derivatives and insecticides
JP3325343B2 (en) Substituted oxime ethers and fungicides containing them
HU206326B (en) Process for killing harmful insects and acares with compositions containing pyrimidine derivatives and process for producing the active components
HU214153B (en) Azine substituted phenylacetic acid derivatives, fungicides and insecticides containing them and process for preparation of active ingredients and for use of the compositions
CN1066137C (en) Alpha-phenylbutenic acid methyl esters
CN1320855C (en) Fungicidal mixtures on the basis of oxime ether derivatives and guanidine derivatives
KR100221506B1 (en) Alpha-arylacrylic acid and the derivatives, their preparation and the composition containing them
EP0474042A1 (en) Alpha-arylacrylic acid derivatives, their production and use for the control of pests and fungi
EP0459285B1 (en) Ortho-substituted benzyl esters of cyclopropane carboxylic acids
EP1140926B1 (en) Azadioxacycloalkenes and their use for combating harmful fungi and animal pests
EP0372330B1 (en) Special substituted cyclopropane carboxamides, process for their preparation and their use for combatting pests
US5066673A (en) Substituted benzyl 2-phenyl-1-alk(en)ylcyclopropane-carboxylates and the use thereof for controlling pests
US5132326A (en) Cyclopropanethiocarboxamides
JP2003509415A (en) Unsaturated oxime ethers and their use for controlling harmful fungi and livestock pests
US6372766B1 (en) Substituted 2-(2′-pyridyloxy)phenylacetamides, as fungicides and pesticides
CN1199392A (en) Phenylacetic acid derivs, process for their preparation and their use as pesticides and fungicides
EP1121348B1 (en) Azadioxacycloalkene derivatives, methods for the production thereof and their use as fungicides and pest control agents
KR0156913B1 (en) Special substituted cyclopropane carboxamide process for their preparation and their use for combating pests
CN1199393A (en) Oxyamino oxime ethers, methods and intermediate products for their production, and composition contg. them and used for controlling harmful fungi and pests
MXPA00003550A (en) Substituted 2-(2'-pyridyloxy)phenyl acetamides as fungicides and pesticides
DE4024094A1 (en) New 2-substd. benzyl cyclopropane carboxylate ester derivs.

Legal Events

Date Code Title Description
BB1A Publication of application
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
C17 Cessation of patent right
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20040225

Termination date: 20100322