CN1320855C - Fungicidal mixtures on the basis of oxime ether derivatives and guanidine derivatives - Google Patents

Fungicidal mixtures on the basis of oxime ether derivatives and guanidine derivatives Download PDF

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Publication number
CN1320855C
CN1320855C CNB038022710A CN03802271A CN1320855C CN 1320855 C CN1320855 C CN 1320855C CN B038022710 A CNB038022710 A CN B038022710A CN 03802271 A CN03802271 A CN 03802271A CN 1320855 C CN1320855 C CN 1320855C
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compound
plant
mixture
formula
harmful fungoid
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CN1615079A (en
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T·格罗特
E·安莫曼
R·施蒂尔勒
G·洛伦兹
G·斯坦穆勒
K·谢尔伯格
E·哈登
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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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
    • A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
    • A01N47/44—Guanidine; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3

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

Abstract

Disclosed are mixtures for controlling harmful fungi and insects, containing oxime ether derivatives of formula (I) as an active component (A), in which the substituents have the following meaning: X NH or oxygen; R1 and R3 independently of each other hydrogen, cyano, alkyl, cyclopropyl, or haloalkyl; R2 and R4 independently of each other hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, or haloalkynyl; and (B) the compound of formula (II) in a synergistically active quantity. Also disclosed are methods for controlling harmful fungi with mixtures of compounds I and II.

Description

Fungicidal mixture based on oxime ether derivatives and guanidine derivatives
The present invention relates to be used to prevent and treat the mixture of harmful fungoid and insect, the following component that this mixture comprises cooperative effective quantity is as active component:
A) oxime ether derivatives of formula I:
Wherein each substituting group is following defines:
X is NH or oxygen;
R 1, R 3Be hydrogen, cyano group, C independently of each other 1-C 4Alkyl, cyclopropyl or C 1-C 4Haloalkyl;
R 2, R 4Be hydrogen, C independently of each other 1-C 4Alkyl, C 3-C 6Alkenyl, C 3-C 6Alkynyl, C 1-C 4Haloalkyl, C 3-C 6Halogenated alkenyl or C 3-C 6The halo alkynyl;
With
B) formula II compound:
The purpose of this invention is to provide especially the fungal disease in the rice is had good fungicidal action and has good insecticidal action simultaneously, and the mixture (Synergistic mixture) that reduces of total amount of application of reactive compound.Because in the climatic province of rice growth, harmful insect also exists usually in a large number, has therefore both needed fungicidal action also to need insecticidal action.
We find that this purpose realizes by claim 1 mixture required for protection according to the present invention.We are surprisingly found out that the Compound I I that itself does not have fungicidal action has improved the Fungicidally active of the oxime ether derivatives of formula I.Therefore, Compound I I is as auxiliary agent.
Formula I compound and preparation thereof itself are known and are described in (WO-A 97/15552) in the document.
The insecticide of formula II is known (common name: Ma Niding (clothianidin)) and be described in (EP-A 376 279) in the document equally.
Because the biologically active of formula I compound, preferred R wherein 1And R 3Be hydrogen, cyano group, cyclopropyl, methyl, ethyl, 1-Methylethyl or CF 3Formula I compound.
Especially preferred R wherein 1And R 3Be C 1-C 4The Compound I of alkyl.
In addition, especially preferred R wherein also 1Compound I for methyl.
In addition, preferred R wherein also 1Be CF 3Compound I.
In addition, preferred R wherein also 2And R 4Compound I for hydrogen, cyclopropyl, methyl, ethyl, isopropyl.
In addition, preferred R wherein also 4Compound I for methyl.
In addition, preferred R wherein also 4Compound I for ethyl or isopropyl.
Preferred especially wherein X is the formula I oxime ether derivatives of NH.
Especially consider that they mix use with Compound I I in the present invention, preferably be summarised in the Compound I in the following table 1.
Table 1
The oxime ether derivatives of formula I:
Sequence number R 1 R 2 R 3 R 4 X
I-1 H H H H NH
I-2 H CH 3 H CH 3 NH
I-3 CH 3 H CH 3 H NH
I-4 CH 3 CH 3 CH 3 CH 3 NH
I-5 CH 3 Ring-C 3H 5 CH 3 Ring-C 3H 5 NH
I-6 CH 3 CH 2CH 3 CH 3 CH 2CH 3 NH
I-7 CH 3 CH(CH 3) 2 CH 3 CH(CH 3) 2 NH
I-8 CH 3 CH 2CH＝CH 2 CH 3 CH 2CH＝CH 2 NH
I-9 CF 3 H CF 3 H NH
I-10 CF 3 CH 3 CF 3 CH 3 NH
I-11 CF 3 CH(CH 3) 2 CF 3 CH(CH 3) 2 NH
I-12 CN H CH 3 H NH
I-13 CN CH 3 CH 3 CH 3 NH
I-14 H H H H O
I-15 H CH 3 H CH 3 O
I-16 CH 3 H CH 3 H O
I-17 CH 3 CH 3 CH 3 CH 3 O
I-18 CH 3 Ring-C 3H 5 CH 3 Ring-C 3H 5 O
I-19 CH 3 CH 2CH 3 CH 3 CH 2CH 3 O
I-20 CH 3 CH(CH 3) 2 CH 3 CH(CH 3) 2 O
I-21 CH 3 CH 2CH＝CH 2 CH 3 CH 2CH＝CH 2 O
I-22 CF 3 H CF 3 H O
I-23 CF 3 CH 3 CF 3 CH 3 O
I-24 CN H CH 3 H O
I-25 CN CH 3 CH 3 CH 3 O
The Compound I that is present in the mixture of the present invention has significant activity to the plant pathogenic fungi of wide region, and described fungi especially is selected from Ascomycetes (Ascomycetes), deuteromycetes (Deuteromycetes), Phycomycetes (Phycomycetes) and Basidiomycetes (Basidiomycetes) fungi.
They are even more important to a large amount of fungies of control in various crops such as cotton, vegetable variety (as cucumber, beans, tomato, potato and cucurbitaceous plant), barley, dogstail, oat, banana, coffee, corn, fruit variety, rice, rye, soybean, grape vine, wheat, ornamental plants, sugarcane and various seed.
They are particularly suitable for preventing and treating the following plants pathogenic epiphyte: the Blumeriagraminis on the cereal class (powdery mildew), two spore powdery mildews (Erysiphe cichoracearum) on the cucurbitaceous plant and monofilament shell (Sphaerotheca fuliginea), apple mildew bacterium (Podosphaeraleucotricha) on the apple, grape snag shell (Uncinula necator) on the grape vine, handle rest fungus (Puccinia) on the cereal class belongs to, cotton, rhizoctonia on rice and the lawn (Rhizoctonia) belongs to, smut on cereal class and the sugarcane (Ustilago) belongs to, venturia inaequalis on the apple (Venturia inaequalis) (scab), length on cereal class and the rice spore (Helminthosporium) of wriggling belongs to, clever withered septoria musiva on the wheat (Septoria nodorum), strawberry, vegetables, Botrytis cinerea on ornamental plants and the grape vine (Botrytiscinerea) (gray mold), peanut tail spore (Cercospora arachidicola) on the peanut, eye spot bacterium on wheat and the barley (Pseudocercosporella herpotrichoides), Pyricularia oryzae on rice and the lawn (Pyricularia oryzae), phytophthora infestans on potato and the tomato (Phytophthorainfestans), grape on the grape vine is given birth to single shaft mould (Plasmopara viticola), false downy mildew (Pseudoperonospora) on lupulus and the cucumber belongs to, chain lattice spore (Alternaria) on vegetables and the fruit belongs to, and the ball chamber bacterium (Mycosphaerella) on the banana belongs to and fusarium (Fusarium) and wheel branch spore (Verticillium) genus.
Formula II compound is used to prevent and treat the animal pest that is selected from insect, spider and nematode.It can and be used to prevent and treat animal pest in crop protection, in the protection field of health field and stored prod in veterinary applications.Described compound is particularly suitable for preventing and treating following animal pest:
Lepidopterous insects (Lepidoptera); black cutworm (Agrotis ypsilon) for example; white line dart moth of turnip (Agrotissegetum); Alabama argillacea; Anticarsia (Anticarsia gemmatalis); Argyresthia conjugella; Autographa gamma; tree looper (Bupalus piniarius); Cacoecia murinana; Capua reticulana; Cheimatobia brumata; dragon spruce Choristoneura spp (Choristoneura fumiferana); Choristoneura occidentalis; Cirphisunipuncta; codling moth (Cydia pomonella); Dendrolimus pini; Diaphanianitidalis; southwest corn straw crambid (Diatraea grandiosella); Egyptian brill noctuid (Eariasinsulana); South America maize seedling phycitid (Elasmopalpus lignosellus); ligustrum fine tortricidae (Eupoecilia ambiguella); Evetria bouliana; Feltia subterranea; galleria mellonella waxmoth (Galleria mellonella); Lee's Grapholita spp (Grapholitha funebrana); oriental fruit moth (Grapholitha molesta); cotton bollworm (Heliothis armigera); tobacco budworm (Heliothisvirescens); corn earworm (Heliothis zea); Oeobia undalis (Hellula undalis); Hiberniadefoliaria; fall webworm (Hyphantria cunea); Hyponomeuta malinellus; tomato worm moth (Keiferia lycopersicella); Lambdina fiscellaria; beet armyworm (Laphygmaexigua); coffee leafminer (Leucoptera coffeella); pear leaf blister moth (Leucoptera scitella); Lithotis blancardella; grape berry steinernema (Lobesia botrana); beet webworm (Loxostege sticticalis); gypsymoth (Lymantria dispar); lymantria monacha (Lymantriamonacha); peach leaf miner (Lyonetia clerkella); malacosoma neustria (Malacosomaneustria); tomato moth (Mamestra brassicae); Orgyia pseudotsugata; corn borer (Ostrinia nubilalis); small noctuid (Panolis flammea); cotton pink bollworm (Pectinophoragossypiella); boundary noctuid (Peridroma saucia); circle palm boat moth (Phalera bucephala); tobacco split worm (Phthorimaea operculella); citrus leaf-miner (Phyllocnistis citrella); Pieris brassicae (Pieris brassicae); the green noctuid of clover (Plathypena scabra); diamond-back moth (Plutellaxylostella); soybean noctuid (Pseudoplusia includens); Rhyacionia frustrana; Scrobipalpula absoluta; gelechiid (Sitotroga cerealella); grape berry moth (Sparganothis pilleriana); fall army worm (Spodoptera frugiperda); sea spodoptera (Spodoptera littoralis); prodenia litura (Spodoptera litura); Thaumatopoeapityocampa; Tortrix viridana; cabbage looper (Trichoplusia ni) and Zeirapheracanadensis
Beetle (coleoptera), the narrow lucky fourth of pears (Agrilus sinuatus) for example, vertical bar click beetle (Agrioteslineatus), dark-coloured click beetle (Agriotes obscurus), Amphimallus solstitialis, Anisandrus dispar, Mexico's cotton boll resembles (Anthonomus grandis), the apple flower resembles (Anthonomus pomorum), Atomaria linearis (Atomaria linearis), vertical pit cutting pin small moth (Blastophagus piniperda), Blitophaga undata, broad bean weevil (Bruchusrufimanus), pea weevil (Bruchus pisorum), Lens culinaris resembles (Bruchus lentis) in Europe, the apple volume resembles (Byctiscus betulae), the big tortoise plastron of beet (Cassida nebulosa), Cerotomatrifurcata, Chinese cabbage seed tortoise resembles (Ceuthorrhynchus assimilis), the blister beetle tortoise resembles (Ceuthorrhynchus napi), beet shin flea beetle (Chaetocnema tibialis), Conoderusvespertinus, asparagus scotellaris (Crioceris asparagi), Diabrotica longicornis, Diabrotica 12-punctata, corn root leaf A (Diabrotica virgifera), mexican bean ladybird (Epilachna varivestis), tobacco flea beetle (Epitrix hirtipennis), cotton ash covers and resembles mutation (Eutinobothrus brasiliensis), hylobius abietis (Hylobius abietis), Egyptian cloverleaf resembles (Hypera brunneipennis), alfalfa leaf resembles (Hypera postica), ips typographus (Ipstypographus), tobacco scotellaris (Lema bilineata), black angle scotellaris (Lemamelanopus), colorado potato beetles (Leptinotarsa decemlineata), Limoniuscalifornicus, rice water weevil (Lissorhoptrus oryzophilus), Melanotus communis, rape nitidulid (Meligethes aeneus), Da Li gill cockchafer (Melolontha hippocastani), gill cockchafer in May (Melolontha melolontha), Oulema oryzae (Oulema oryzae), vine black ear beak resembles (Ortiorrhynchus sulcatus), Otiorhynchus spp (Otiorrhynchus ovatus), horseradish ape chrysomelid (Phaedon cochleariae), Phyllotreta chrysocephala, food phyllobranchia cockchafer (Phyllophaga) belongs to, rutelian (Phyllopertha horticola) is sent out in the flower garden, the light sufficient flea beetle of soybean (Phyllotreta nemorum), Phyllotreta striolata (Phyllotreta striolata), Japanese beetle (Popillia japonica), the pea leaf resembles (Sitona lineatus) and grain weevil (Sitophilus granaria)
Dipteral insect (diptera), Aedes aegypti (Aedes aegypti) for example, perversely disturb yellow-fever mosquito (Aedesvexans), Mexico fruit bat (Anastrepha ludens), anopheles maculipennis (Anophelesmaculipennis), Mediterranean fruitfly (Ceratitis capitata), maggot disease gold fly (Chrysomyabezziana), Chrysomya hominivorax, Chrysomya macellaria, Chinese sorghum cecidomyiia (Contarinia sorghicola), Cordylobia anthropophaga, northern house (Culexpipiens), the melon fly, dacus oleae (Dacus oleae), the rape leave cecidomyiia, little Mao latrine fly (Fanniacanicularis), horse botfly (Gasterophilus intestinalis), glossina morsitans (Glossina morsitans), Haematobia irritans, Haplodiplosis equestris, peanut field delia platura (Hylemyiaplatura), heel fly (Hypoderma lineata), vegetables liriomyza bryoniae (Liriomyza sativae), U.S. Liriomyza (Liriomyza trifolii), Lucilia caprina, lucilia cuprina (Lucilia cuprina), lucilia sericata (Lucilia sericata), Lycoria pectoralis, wheat cecidomyiia (Mayetioladestructor), housefly (Musca domestica), false stable fly (Muscina stabulans), oestrosis of sheep (Oestrus ovis), Europe wheat stem maggot (Oscinella frit), henbane seed spring fly (Pegomyahysocyami), Phorbia antiqua, radish fly (Phorbia brassicae), Phorbiacoarctata, cherry fruit fly (Rhagoletis cerasi), Rhagoletis pomonella (Rhagoletis pomonella), Tabanus bovinus, Tipula oleracea and European daddy-longlegs (Tipula paludosa)
Thrips (thrips); for example cigarette brown thrip (Frankliniella fusca), honeysuckle thrips (Frankliniella occidentalis), east flower thrips (Frankliniella tritici), the hard thrips of tangerine (Scirtothrips citri), rice thrips (Thrips oryzae), palm thrips (Thrips palmi) and onion thrips (Thrips tabaci)
Hymenopteran (Hymenoptera), for example Xinjiang cabbage sawfly (Athalia rosae), Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, monomorium pharaonis (Monomorium pharaonis), Solenopsis geminata and red fire ant (Solenopsis invicta)
Heteroptera insect (Heteroptera), for example intend green stinkbug (Acrosternum hilare), corn chinch bug (Blissus leucopterus), blackspot cigarette fleahopper (Cyrtopeltis notatus), red cotton bug (Dysdercus cingulatus), Dysdercus intermedius, wheat Eurygasterspp (Eurygasterintegriceps), Euschistus impictiventris, cotton red bell beak coried (Leptoglossusphyllopus), America tarnished plant bug (Lygus lineolaris), tarnished plant bug (Lygus pratensis), green rice bug (Nezara viridula), beet is intended lace bug (Piesma quadrata), Solubea insularis and Thyanta perditor
Homoptera insect (Homoptera), Acyrthosiphon onobrychis for example, adelge laricis (Adelges laricis), Aphidula nasturtii, aphis fabae (Aphis fabae), apple aphid (Aphispomi), elder aphid (Aphis sambuci), welted thistle short-tail aphid (Brachycaudus cardui), cabbage aphid (Brevicoryne brassicae), Cerosipha gossypii, abies nordmanniana vertebra adelgid (Dreyfusia nordmannianae), dragon spruce vertebra adelgid (Dreyfusia piceae), Ju Genxi rounded tail aphid (Dysaphis radicola), Dysaulacorthum pseudosolani, broad bean Empoasca spp (Empoascafabae), English grain aphid (Macrosiphum avenae), root of Beijing euphorbia Macrosiphus spp (Macrosiphumeuphorbiae), rose pipe aphid (Macrosiphon rosae), the nest Lay is repaiied tail aphid (Megoura viciae), wheat does not have net aphid (Metopolophium dirhodum), Myzodes persicae, Lee's knurl aphid (Myzuscerasi), rice fulgorid (Nilaparvata lugens), suspensor goitre woolly aphid (Pemphigus bursarius), sugarcane plant hopper (Perkinsiella saccharicida), phorodon aphid (Phorodon humuli), apple leaf sucker (Psylla mali), pear sucker (Psylla piri), shallot knurl moth aphid (Rhopalomyzus ascalonicus), corn leaf aphids (Rhopalosiphum maidis), Sappaphis mala, Sappaphis mali, greenbug (Schizaphis graminum), elm woolly aphid (Schizoneura lanuginosa), trialeurodes vaporariorum (Trialeurodes vaporariorum) and grape phylloxera (Viteus vitifolii)
Termite (Isoptera), for example Calotermes flavicollis, Leucotermes flavipes, European reticulitermes flavipe (Reticulitermes lucifugus) and Termes natalensis,
Orthopteran (orthoptera), residential house Chinese mugwort Xi (Acheta domestica) for example, oriental cockroach (Blatta orientalis), Groton bug (Blattella germanica), European earwig (Forficulaauricularia), mole cricket (Gryllotalpa gryllotalpa), migratory locusts (Locusta migratoria), double cut is deceived locust (Melanoplus bivittatus), red foot is deceived locust (Melanoplus femur-rubrum), Mexico deceives locust (Melanoplus mexicanus), black locust (Melanoplus sanguinipes) migrates, stone is dwelt and is deceived locust (Melanoplus spretus), the red locust of striped (Nomadacris septemfasciata), american cockroach (Periplaneta americana), America desert locust (Schistocerca americana), Schistocerca peregrina, Stauronotus maroccanus and front yard disease kitchen range Zhong (Tachycinesasynamorus)
Spider guiding principle (Arachnoidea), as spider (Acarina), for example long star tick (Amblyommaamericanum), torrid zone flower tick (Amblyomma variegatum), adobe tick (Argaspersicus), ox tick (Boophilus annulatus), Boophilus decoloratus, boophilus microplus (Boophilus microplus), purplish red short hairs mite (Brevipalpus phoenicis), Bryobia praetiosa (Bryobia praetiosa), Dermacentor silvarum, carpinus turczaninowii beginning tetranychid (Eotetranychus carpini), tangerine bud goitre mite (Eriophyes sheldoni), Hyalommatruncatum, castor bean tick (Ixodes ricinus), Ixodes rubicundus, Ornithodorusmoubata, Otobius megnini, Paratetranychus pilosus, Dermanyssus gallinae (Dermanyssus gallinae), tangerine wrinkle leaf Aculus (Phyllocoptruta oleivora), Polyphagotarsonemus latus Banks (Polyphagotarsonemus latus), sheep scabies disease (Psoroptes ovis), Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei hominis (Sarcoptesscabiei), Tetranychus cinnabarinus (Tetranychus cinnabarinus), kamisawa tetranychus (Tetranychuskanzawai, Pacific Ocean tetranychid (Tetranychus pacificus), cotton spider mites (Tetranychustelarius) and T.urticae Koch (Tetranychus urticae)
Nematode, as root-knot nematode, for example northern root-knot nematode (Meloidogyne hapla), Meloidogyne incognita (Meloidogyne incognita), javanese root knot nematode (Meloidogyne javanica); Cyst roundworm, for example globodera rostochiensis (Globodera rostochiensis), oat Cyst nematode (Heterodera avenae), soybean Cyst nematode (Heterodera glycines), beet Cyst nematode (Heterodera schachtii), clover Cyst nematode (Heterodera trifolii); And stem eelworm and leaf nematode, for example long-tail thorn nematode (Belonolaimus longicaudatus), the potato nematode (Ditylenchus destructor) of rotting, fuller's teasel stem eelworm (Ditylenchus dipsaci), many band helicotylenchus (Heliocotylenchus multicinctus), stretch minute hand nematode (Longidoruselongatus), radopholus similes thorne (Radopholus similis), the strong nematode that spirals (Rotylenchusrobustus), original burr nematode (Trichodorus primitivus), Ke Laidun downgrades nematode (Tylenchorhynchus claytoni), indefinite dwarfing nematode (Tylenchorhynchus dubius), carelessness Pratylenchidae (Pratylenchus neglectus), Cobb root (Pratylenchuspenetrans), Pratylenchus curvitatus and Gu Di Pratylenchidae (Pratylenchusgoodeyi).
Compound I and II are usually with 20: 1 to 1: 200, and especially 10: 1 to 1: 180, preferred 2: 1 to 1: 160 weight ratio was used.
Under outdoor conditions, in order to prevent and treat animal pest, the rate of application of reactive compound is generally 0.01-2.0kg/ha, preferred 0.02-1.0kg/ha.
Mixture of the present invention especially preferably can be used for rice controlling plant diseases and harmful insect.
Compound I and Compound I I can use simultaneously, promptly use together or separately, or use successively, under situation about using separately, order of administration usually to the effect of prophylactico-therapeutic measures without any influence.
The kind that depends on required effect, the rate of application of mixture of the present invention are 0.01-8kg/ha in the crops zone especially, and preferred 0.1-5kg/ha especially is 0.5-3.0kg/ha.
The rate of application of Compound I is 0.01-2.5kg/ha, and preferred 0.05-2.5kg/ha especially is 0.1-1.0kg/ha.
For seed treatment, the rate of application of mixture is generally the 0.001-250g/kg seed, is preferably 0.01-100g/kg, especially is 0.01-50g/kg.
If need control plant-pathogenic harmful fungoid, by before or after the sowing plant or before or after plant emerges to seed, plant or soil spraying or dusting and the mixture of independent or co-administered Compound I and Compound I I or Compound I and Compound I I.
Mixture of the present invention can be mixed with and for example promptly spray solution, pulvis and form of suspension or water-based, oiliness or other suspension, dispersion, emulsion, oil dispersion, paste, the powder that highly concentrate, broadcasts sowing with the form of material or particle and by spraying, atomizing, dusting, broadcasts sowing or water and use.Type of service depends on desired purpose; Under any circumstance all should guarantee the meticulous as far as possible and distribution equably of mixture of the present invention.
Preparaton prepares in a known way, for example prepares by reactive compound is mixed with solvent and/or carrier, and the words that need are used emulsifier and dispersant, if make water as thinner, then can also use other organic solvent as secondary solvent.The auxiliary agent that is suitable for this purpose mainly is solvent such as arsol (as dimethylbenzene), chloro arsol (as chlorobenzene), alkane (as mineral oil fractions), alcohol (as methyl alcohol, butanols), ketone (as cyclohexanone), amine (as monoethanolamine, dimethyl formamide) and water; Carrier is as natural minerals (as kaolin, clay, talcum, chalk) that grinds and the synthetic mineral (as silica in small, broken bits, silicate) that grinds; Emulsifier such as nonionic and anion emulsifier (as polyoxyethylene aliphatic alcohol ether, alkylsulfonate and arylsulphonate) and dispersant such as lignin sulfite waste liquor and methylcellulose.
Suitable surfactant is aromatic sulfonic acid such as lignin sulfonic acid, phenolsulfonic acid, the alkali metal salt of naphthalene sulfonic acids and dibutyl naphthalene sulfonic acids and fatty acid, alkali salt and ammonium salt, alkyl-and alkylaryl sulfonates, alkyl sulfate, lauryl ether sulfate and aliphatic alcohol sulfate and sulphation 16-, 17-and the salt of octadecanol, or the salt of 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 octylphenol ether, the isooctylphenol of ethoxylation, octyl phenol or nonyl phenol, the alkyl phenyl polyglycol ether, tributyl phenyl polyglycol ether, alkyl aryl polyether alcohol, different tridecanol, fatty alcohol/ethylene oxide condensation product, ethoxylated castor oil, polyoxyethylene alkyl ether or polyoxypropylene alkyl ether, laruyl alcohol polyglycol ether acetic acid esters, sorbitol ester, lignin sulfite waste liquor and methylcellulose.
Powder, broadcast sowing with material and pulvis and can prepare by Compound I and Compound I I or Compound I are mixed or ground with solid carrier with the mixture of Compound I I.
Granula (as coating granula, dipping granula or homogeneous phase granula) is usually by preparing one or more reactive compounds and solid carrier adhesion.
Filler or solid carrier for example are that ore deposit soil is as silica, silica gel, silicate, talcum, kaolin, lime stone, lime, chalk, bole, loess, clay, dolomite, diatomite, calcium sulphate, magnesium sulfate, magnesia; The synthetic material that grinds; Fertilizer such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea; The product of plant origin such as flour, bark powder, wood powder and shuck powder; Cellulose powder or other solid carrier.
Preparaton comprises 0.1-95 weight % usually, the Compound I of preferred 0.5-90 weight % and the mixture of Compound I I or Compound I and Compound I I.Reactive compound is with 90-100%, and the purity (according to NMR spectrum or HPLC) of preferred 95-100% is used.
Compound I and Compound I I, mixture or corresponding preparaton are by with the mixture of antifungal effective dose or using separately under the situation, and Compound I and Compound I I processing harmful fungoid, its habitat maybe need to prevent and treat plant, seed, soil, zone, material or the space of harmful fungoid and use.
Use and before or after harmful fungoid infects, to carry out.
This class examples of formulations that comprises reactive compound is:
I.90 the solution of weight portion reactive compound and 10 weight portion N-Methyl pyrrolidone; This solution is suitable for using with droplet;
The mixture of the adduct of adduct, 5 weight portion calcium dodecyl benzene sulfonates, 5 weight portion 40mol ethylene oxides and the 1mol castor oil of II.20 weight portion reactive compound, 80 weight portion dimethylbenzene, 10 weight portion 8-10mol ethylene oxides and 1mol oleic acid N-single ethanol amide; By being distributed in subtly, this solution obtains dispersion in the water;
The aqueous dispersion of the adduct of III.20 weight portion reactive compound, 40 weight portion cyclohexanone, 30 weight portion isobutanols, 20 weight portion 40mol ethylene oxides and 1mol castor oil;
IV.20 weight portion reactive compound, 25 weight portion cyclohexanol, 65 weight portion boiling points are the aqueous dispersion of the adduct of 210-280 ℃ mineral oil fractions and 10 weight portion 40mol ethylene oxides and 1mol castor oil;
V.80 the mixture that in hammer-mill, grinds from the sodium lignosulfonate and the 7 weight portion granular colloidal silicas of sulfite waste liquor of weight portion reactive compound, 3 weight portion diisobutyl naphthalene 1-sodium sulfonates, 10 weight portions; By being distributed in subtly, this mixture obtains the Spray Mixing thing in the water;
VI.3 weight portion reactive compound and 97 weight portions kaolinic homogeneous mixture in small, broken bits; This powder comprises 3 weight % reactive compounds;
VII.30 weight portion reactive compound, 92 weight portion granular colloidal silicas and 8 weight portions sparge the homogeneous mixture of the lip-deep paraffin oil of this silica gel; This preparaton is given reactive compound with good adhesiveness;
The stable aqueous dispersions of the sodium salt of VIII.40 weight portion reactive compound, 10 weight portion phenolsulfonic acid/urea/formaldehyde condensation products, 2 weight portion silica gel and 48 weight parts waters; This dispersion can further be diluted;
The sodium salt of IX.20 weight portion reactive compound, 2 weight portion calcium dodecyl benzene sulfonates, 8 weight portion fatty alcohol polyglycol ethers, 20 weight portion phenolsulfonic acid/urea/formaldehyde condensation products and the stabilize oil dispersion of 88 weight portion alkane mineral oil.
Application Example
The Synergistic active of mixture of the present invention can be confirmed by following test:
Reactive compound is mixed with 10% emulsion and is diluted with water to required concentration in the mixture of 63 weight % cyclohexanone and 27 weight % emulsifier separately or together.
Estimate by the leaf area (%) that mensuration infects.These percentages are changed into effectiveness.Use the Abbot formula to render a service (W) by following calculating:
W＝(1-α/β)·100
A corresponding to the fungal infection of handling plant (%) and
B is corresponding to the fungal infection (%) of (contrast) plant of being untreated.
Effectiveness is 0 to be meant the degree that infects of the handling plant degree that infects corresponding to the untreated control plant; Effectiveness is 100 to be meant that handling plant is infected.
The expection of the mixture of reactive compound is renderd a service and is used the Colby formula to determine [R.S.Colby, Weeds (weeds) 15, 20-22 (1967)] and with observed effectiveness relatively.
Colby formula: E=x+y-xy/100
E is that the expection when using the mixture of reactive compound A and B with concentration a and b is renderd a service, represents with % with respect to untreated control,
X is the effectiveness when using reactive compound A with concentration a, represents with the % with respect to untreated control, and y is the effectiveness when using reactive compound B with concentration b, represents with the % with respect to untreated control.
Application Example: to the protection activity of the rice blast that causes by Pyricularia oryzae (Pyricularia oryzae)
The leaf that cultivar is carried rice sprouts for the basin of " Tai-Nong67 " is sprayed to drip with the aqueous compositions of reactive compound, and described preparation is prepared by the stock solution that comprises 10% reactive compound, 85% cyclohexanone and 5% emulsifier.Second day with the moisture spore suspension inoculation of plant with Pyricularia oryzae.Then test plant was placed 6 days in the climate regulation chamber under 22-24 ℃ of relative atmospheric humidity with 95-99%.The naked eyes evaluation is infected development degree on leaf then.
The percentage measured value that will infect leaf area changes into the effectiveness with respect to the % of untreated control.The expection of reactive compound combination is renderd a service and is used the Colby formula to determine that [weeds (Weeds, 15, the 20-22 pages or leaves (1967)) are also compared with the effectiveness that observes for R.S.Colby, " calculating the Synergistic and the antagonism reaction of combinations of herbicides ".
Table 1: comparative trial
Reactive compound The concentration [ppm] of reactive compound in spray liquid Phase time is in the effectiveness of the % of untreated control
Contrast (being untreated) (89% infects) 0
I-4 8 2 0.5 77 66 10
II 80 20 5 0 0 0
Table 2: mixture of the present invention
Mixture of the present invention The effectiveness that observes The effectiveness of calculating *)
I-4+II 8+5ppm mixing ratio 1.6: 1 97 77
I-4+II 8+20ppm mixing ratio 1: 2.5 94 77
I-4+II 8+80ppm mixing ratio 1: 10 97 77
I-4+II 2+20ppm mixing ratio 1: 10 83 66
I-4+II 0.5+5ppm mixing ratio 1: 10 21 10
I-4+II 0.5+20ppm mixing ratio 1: 40 32 10
I-4+II 0.5+80ppm mixing ratio 1: 160 21 10
*) effectiveness of using the Colby formula to calculate
Result of the test shows that the effectiveness that observes is higher than the effectiveness that prior use Colby formula calculates under all mixing ratios.

Claims (6)

1. mixture that is used for crop protection, the following component that comprises cooperative effective quantity are as active component:
A) oxime ether derivatives of formula I:
Wherein each substituting group is following defines:
X is NH or oxygen;
R 1, R 3Be hydrogen, C independently of each other 1-C 4Alkyl, cyclopropyl or C 1-C 4Haloalkyl;
R 2, R 4Be hydrogen, C independently of each other 1-C 4Alkyl, C 3-C 6Alkenyl, C 3-C 6Alkynyl, C 1-C 4Haloalkyl, C 3-C 6Halogenated alkenyl or C 3-C 6The halo alkynyl;
With
B) formula II compound:
Figure C038022710002C2
2. as the desired mixture of claim 1, inclusion compound I-4 is as component A:
Figure C038022710002C3
3. as claim 1 or 2 desired mixtures, wherein component A and B exist with 20: 1 to 1: 200 mixing ratio.
4. method of preventing and treating the plant-pathogenic harmful fungoid, comprise the material, plant, seed, soil, zone or the space that maybe need to prevent and treat fungal infection with each desired Fungicidal mixture processing fungi, its habitat among the claim 1-3, wherein using of Compound I and Compound I I can simultaneously or be carried out successively.
5. as the desired method of claim 4, handle with the Compound I as claimed in claim 1 or 2 of 0.005-1kg/ha in the plant, seed, soil, zone, material or the space that wherein harmful fungoid, its habitat are maybe needed to prevent and treat harmful fungoid.
6. as the desired method of claim 4, wherein harmful fungoid, its habitat are maybe needed to prevent and treat the Compound I I processing as claimed in claim 1 of plant, seed, soil, zone, material or the space of harmful fungoid with 0.01-1kg/ha.
CNB038022710A 2002-01-17 2003-01-03 Fungicidal mixtures on the basis of oxime ether derivatives and guanidine derivatives Expired - Fee Related CN1320855C (en)

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WO1997015552A1 (en) * 1995-10-23 1997-05-01 Basf Aktiengesellschaft Phenylacetic acid derivatives, process and intermediate products for use in producing them and agents containing them
WO1999063826A2 (en) * 1998-06-10 1999-12-16 Bayer Aktiengesellschaft Agents for combating plant pests

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EP0376279A2 (en) * 1988-12-27 1990-07-04 Takeda Chemical Industries, Ltd. Guanidine derivatives, their production and insecticides
WO1997015552A1 (en) * 1995-10-23 1997-05-01 Basf Aktiengesellschaft Phenylacetic acid derivatives, process and intermediate products for use in producing them and agents containing them
WO1999063826A2 (en) * 1998-06-10 1999-12-16 Bayer Aktiengesellschaft Agents for combating plant pests

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