CN1092022C - Microbicides - Google Patents

Microbicides Download PDF

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Publication number
CN1092022C
CN1092022C CN97102855A CN97102855A CN1092022C CN 1092022 C CN1092022 C CN 1092022C CN 97102855 A CN97102855 A CN 97102855A CN 97102855 A CN97102855 A CN 97102855A CN 1092022 C CN1092022 C CN 1092022C
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Prior art keywords
plant
seed
formula
composition
active component
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CN97102855A
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CN1196176A (en
Inventor
N·里德比特尔
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Syngenta Participations AG
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Novartis AG
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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/26Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
    • A01N43/28Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
    • A01N43/30Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01CPLANTING; SOWING; FERTILISING
    • A01C1/00Apparatus, or methods of use thereof, for testing or treating seed, roots, or the like, prior to sowing or planting
    • A01C1/06Coating or dressing seed
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01GHORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
    • A01G22/00Cultivation of specific crops or plants not otherwise provided for
    • A01G22/20Cereals
    • A01G22/22Rice
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/06Peri-condensed systems
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N2300/00Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Environmental Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Botany (AREA)
  • Soil Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pyrrole Compounds (AREA)
  • Pretreatment Of Seeds And Plants (AREA)

Abstract

To obtain a microbicide having effective microbicidal effect in small amounts of application, and suitable for dealing with e.g. rice, containing fludioxonil and pyroquilone together with an appropriate support material. This microbicide contains (A) 4-(2,2-difluoro-1,3-benzodioxol-7- yl)-1H-pyrrole-3-carbonitrile of formula I (fludioxonil) and (B) 12,5,6-tetrahydro-4 H-pyrrolo[3,2,1-ij]quinolin-4-one of formula II (pyroquilone) together with an appropriate support material such as talc. The weight ratio A/B is (10:1) to (1:100), pref. (5:1) to (1:60), more pref. (1:1) to (1:25).

Description

Microbicide
The present invention relates to the Synergistic microbicidal compositions that the active component consumption greatly reduces, this Synergistic microbicidal compositions to plant disease and in plant propagation material or the microbial infection in other vegetable material the effect of enhancing is arranged, and the method for using said composition, especially for the method for seed dressing (seed dressing).
In particular, the present invention relates to control or prevent disease in the cereal crop.
Have found that active ingredient components I), the 4-of formula I (2,2-two fluoro-1,3-benzo dioxole-7-yl)-1H-pyrroles-3-nitrile (being fludioxonil (fludioxonil))
Figure C9710285500031
With active ingredient components II), 1,2,5 of formula II, the combination of 6-tetrahydrochysene-4H-pyrrolo-[3,2,1-ij] quinoline-4-ketone (being pyroquilon)
Figure C9710285500032
Cause the long-effect active on control and prevention plant disease to increase surprisingly.
Formula I compound is described among the EP-A-206 999 as Fungicidal active ingredient.Described compound has special effect as tagging property fungicide.
Formula II compound is described in " in the 8th edition the 732nd page of the agricultural chemicals handbook (seeing GB-1 394 373 in addition) as Fungicidal active ingredient.
In plant protection, adopt the active component of low as far as possible amount and reach that damage by disease and insect is infected resisting of top is a kind of permanent demand.And the composition of being made up of two kinds of active components with different biological mechanism of action has and reduces resistance greatly and form dangerous advantage.Therefore, is important demand at above-mentioned two kinds for the user, if active ingredient compositions I+II can combine the higher safety of using with the total amount of using that reduces significantly thereupon, so this combination will be undoubtedly a kind of accident and very desirable solution.The present invention has obtained this solution.
The novel composition of being made up of component I and component I I is suitable for the foliage applying of the raise crop that lives, and particularly the seed dressing of propagulum is used.Described propagulum comprises all types of seeds (fruit, stem tuber, grain), transplants a cutting, transplants etc.Preferably the field of using is the processing of all types of seed treatment, particularly cereal seed.
The present invention can adopt than the much lower amount of amount of existing conventional biocide so far and carry out the seed seed dressing, has therefore greatly enriched the seed dressing technology.
Except two-component composition I+II, the invention still further relates to the method for control fungi, this method comprises with any required order or uses a) active component I and b simultaneously) the active component II of formula II handles by fungal infection or is subject to the site of fungal infection, plant for example.
Also can add other farming active component such as insecticide, miticide, nematocide, weed killer herbicide, plant growth regulator and chemical fertilizer and particularly other microbicide to this novel active ingredient compositions.
The superior mixing ratio of two kinds of active components is I: II=10: 1 to 1: 100, and preferred I: II=5: 1 to 1: 60, and I: II=1 most preferably: 1 to 1: 25.Other superior mixing ratio is I: II=5: 2 to 2: 5, or 3: 5,1: 10,1: 20 or 3: 40.
Combination according to active component I+II of the present invention has obtained useful action of contace poison and systemic action and the long-acting on control seed dispersal and soil propagation plant disease.Microorganism on the microorganism, particularly seed of combination elimination on preserved food products and propagulum of this novelty, and protection growing plants make it to avoid the infringement that soil is propagated microorganism.
Novel active ingredient compositions I+II has very superior being used to and protects the treatment of raise crop, prevention and interior suction fungicide performance.As above mentioned; described active ingredient compositions can be used for suppressing eliminate on the plant that appears at different useful crops or plant part (really, flower, leaf, stem, stem tuber or root) on microorganism; meanwhile; after the plant part that grows also be protected, make it to avoid the infringement of microorganism.
This novel composition has activity to the plant pathogenic fungi that belongs to following kind: Ascomycetes (for example various fungies of Erysiphe, Sclerotinia, chain sclerotinia sclerotiorum genus, Helminthosporium (=eye spot disease belongs to (Drechslera)), mycosphaerella, nuclear cavity Pseudomonas); Basidiomycetes (for example various fungies of Puccinia, Tilletia, Rhizoctonia); Fungi Imperfecti (for example, various fungies such as Gerlachia (=Fusarium), Septoria, Phoma, Alternaria, rice blast).This novel composition is effective especially in seed (fruit, stem tuber, grain) processing, and is outstanding especially to the effect of the Gerlachia nivalis on the wheat (=rice is avenged rotten sickle spore).To rice disease such as rice blast, Hemintho-sporum leaf spot of rice plants, rice sheath blight disease, damping off of colza and effective especially to rice bacteriosis such as bacterial blight of rice.Yet described composition also is suitable for directly handling the other parts of soil or plant.The present composition can well be tolerated by plant and to ecological safety.
This novel composition generally uses with the adjuvant that routine is used for preparation technique.But the active component of formula I and II is mixed with (for example) in a known manner emulsifiable concentrate, can applies paste, directly sprayable or dilute solution, dilution emulsion, wetting powder, soluble powder, pulvis, granule or use polymeric encapsulate.As the character of composition, can select different application processes, for example spraying, atomizing, dust, spread fertilizer over the fields, brush or pour, and the form of composition is to be fit to its purpose that is intended to and popular environment.The plant propagation material (for example seed rice) that the normally every 100Kg of the superior amount of application of active ingredient compositions is intended to protect is with 0.0001 to maximum 0.5Kg, the gross activity composition I+II of preferred 0.0001-0.01Kg.Yet application conditions depends on the condition (surface area, density, water content) of article and the influence of environment more basically.
Within the scope of the invention, the target body crop is a following plants for example: cereal class (wheat, barley, rye, oat, triticale, Chinese sorghum, corn and particularly various rice varieties); Beet (sugar beet and fodder beet); Legume (Kidney bean, French beans, soybean, pea); Oil crop (rape, mustard seed dish, opium poppy, sunflower); Melon (cucumber, pumpkin, muskmelon); Fiber crop (cotton, flax); Vegetables (lettuce, wild cabbage, spinach, carrot, onion, tomato, potato, capsicum); Ornamental plants (tulip, daffodil, dahlia, chrysanthemum and other flowers); And aromatic crop and seed thereof.
The preferred application process of this novel composition is the method with spraying of the liquid preparation of active component or wetting vegetable material, or the method for mixing with vegetable material with the solid pharmaceutical preparation of active component.These guard methods and all be a part of the present invention with the plant propagation material of the compositions-treated of I+II." plant propagation material " speech comprises that growth property vegetable material is as transplanting a cutting and stem tuber (for example bulb of potato, edibility onion and ornamental plants) and particularly comprise the cereal seed of rice and rice seedlings.
According to the present invention, the active component of formula I and II uses with the form of composition, and if desired, can be used for the adjuvant that the promotion of preparation technique uses with other conventional carrier, surfactant or other routine and use.
The carrier and the adjuvant that are fit to can be solid or liquid, and are the materials that routine is used for preparation technique, for example natural or regeneration mineral matter, solvent, dispersant, wetting agent, tackifier, thickener, adhesive or chemical fertilizer.
The method for optimizing of using the mixture of active principles of formula I and II or comprising (agricultural) chemical composition of these active components is a foliage applying.Application times and amount of application depend on the danger that infected by corresponding cause of disease (fungi).Yet by adopting the liquid preparation plant growing place of drenching, or by using solid active agent in soil, for example with particle form (soil application), active ingredient compositions also can be penetrated into (systemic action) on the plant corpus by root system through soil.In particularly preferred method; by applying seed with the liquid preparation dipping seed of this fungicide or with solid pharmaceutical preparation, the mixture of active principles of formula I and II also can be applied on seed, stem tuber, fruit or other vegetable material that is intended to protect (coating).Under special situation, using of other type also is possible, and for example plant is transplanted a cutting or as the specific processing of the branch of brood body.
The compound of formula I and II is with unmodified form, or the adjuvant that preferably is used for preparation technique with routine uses.For this purpose, in a known manner they are mixed with (for example) but emulsifiable concentrate, can apply paste, directly sprayable or dilute solution, diluting emulsion, wetting powder, soluble powder, pulvis, granule or use polymeric encapsulate.The same with the character of composition, can select different application processes for example spraying, atomizing, dust, spread fertilizer over the fields, brush or pour, to be fit to its purpose that is intended to and popular environment.The superior amount of application of active ingredient compositions gross activity composition (a.i.) of per hectare (ha) 1g to 2Kg formula I and II normally in handle in the land for growing field crops, preferred 2g to 600g a.i./ha.
Preparation, the composition that promptly comprises formula I and II active component and (if desired) solid or liquid auxiliary agent, can prepare in known manner, typically by active component closely being mixed with incremental agent such as solvent, solid carrier and (if suitable) surface active cpd (surfactant) and/or grinding.
The solvent that is fit to is: aromatic hydrocarbon, preferably contain the fraction of 8 to 12 carbon atoms, and be typically the naphthalene of xylene mixture or replacement, phthalic acid ester such as dibutyl phthalate or dioctyl phthalate, aliphatic hydrocarbon such as cyclohexane or alkane; Pure and mild dihydroxylic alcohols and ether thereof and ester such as monomethyl ether, ketone such as cyclohexanone, intensive polar solvent such as N-N-methyl-2-2-pyrrolidone N-, dimethyl sulfoxide (DMSO) or dimethyl formamide, and vegetable oil or epoxidized vegetable oil or soybean oil; Or water.
But the solid carrier that typically is used for pulvis and dispersion powder is the silicic acid or the absorbable polymer of calcite, talcum, kaolin, montmorillonite or Attagel, high degree of dispersion.The granular adsorption particulate vector that is fit to is that float stone, brickbat, sepiolite or bentonite and suitable non-adsorptive support are typically calcite or dolomite.
Different according to the active component character of formula I that is intended to prepare and II, suitable surface active cpd is nonionic, cation and/or the anion surfactant with good emulsifying, dispersion and wettability." surfactant " speech also is appreciated that and becomes to comprise surfactant mixture.
In addition, the natural or synthetic phospholipid that adjuvant is cephalin and lecithin series is used in superior especially promotion, for example, and phosphatidyl-ethanolamine, phosphatidylserine, phosphatidyl glycerol, lysolecithin.
The farmingization composition comprises 0.1 to 99% usually, preferred 0.1 to 95% formula I active component, 99.9 to 1%, preferred 99.9 to 5% solids or liquid auxiliary agent and 0 to 25%, preferred 0.1 to 25% surfactant.
Though commercial product more preferably is mixed with concentrate, final user generally uses the preparation of dilution.
These (agricultural) chemical compositions are parts of the present invention.
The present invention describes with the following example, and wherein " active component " expression is by the Compound I of 10:1 to 1:25 specific blend ratio and the mixture that Compound I I forms. wettable powder is b are a)) c) active component I:II=25% 50% 77% (3:2 (a); 1: 9 (b), 1: 10 (c)) sodium lignosulfonate 5% 5%-lauryl sodium sulfate 3%-5% diisobutyl sodium naphthalene sulfonate-6% 9% octyl phenol polyglycol ether-2%-(oxirane of 7-8 mole) high dispersive silicic acid 5% 10% 9% kaolin 62% 27%-
Active component is fully mixed with adjuvant; And this mixture is fully ground in the mill that is fit to; Provide wetting powder.It can be diluted with water to the suspension of any desired concn.This preparation can be used for the leaf surface treatment of raise crop, also can be used for the wet type or the wetting seed dressing of plant propagation material such as cereal seed or stem tuber. emulsifiable concentrate active component (I: II=1: 20) 10.5% octyl phenol polyglycol ether 3% (oxirane of 4-5 mole) calcium dodecyl benzene sulfonate 3% castor oil polyglycol ether 4% (35 moles oxirane) cyclohexanone, 29.5% xylene mixture 50%
But can water with the thing dilution of contracting of this emulsion, prepare the emulsion that can be used on any desired concn in the crop protection.Pulvis is b a)) active component (I: II=1: 4 and 1: 1) 5% 8% talcum 95%-kaolin-92%
Direct available pulvis is to obtain by active component and carrier are ground in the mill that is fit to.This pulvis can be used for the dry type seed dressing.Extrude granule active component (1: II=1: 25) 13% sodium lignosulfonate, 2% carboxymethyl cellulose, 1% kaolin 84%
Active component is mixed with adjuvant, and this mixture is ground, use water-wet.This mixture is extruded, dry in air flow subsequently.Coating particle agent active component (I: II=3: 5) 8% polyethylene glycol (MW200), 3% kaolin 89% (MW=molecular weight)
In mixer; Levigate active component is coated onto uses on the wetting kaolin of polyethylene glycol, obtain non-dusting coating particle agent. suspending concentrate active component (1: II=1: 5) 42% propane diols, 10% nonyl phenol polyglycol ether 6% (15 moles of ethylene oxide) sodium lignosulfonate, 10% carboxymethyl cellulose, 1% silicone oil 1% (75% aqueous emulsion form) water 30%
Levigate active component is closely mixed with adjuvant, obtain suspending concentrate, suspending concentrate can dilute with water be made the suspension of any desired concn thus.Can use these dilutions,, protect them to avoid infecting of microorganism by spraying, watering or impregnation process live plant and plant product.Biological Examples is to the fungicidal action of the rice blast on the seed rice (Pyricularia) (seed dressing test) test method: in Colombian field trial
In the going barrel of sealing, the upland rice seed is with comprising or the slurry treatment of fludioxonil (I) or pyroquilon (II) or two kinds of mixture of active principles.The seed of handling is thus sowed at 30m with the amount of 120Kg/ha 2The sub-district in.The seed that is untreated in same source is with comparing.With regular time intervals the fungal infection (rice blast) on the plant that occurs is made an appraisal.What especially note is the long-acting of used seed dressing.Test 1
Rice blast infection rate %
Contrast after 50 days after 43 days after 30 days, (being untreated) 5.6 25 39fludioxonil, (I) 3.6 18 27, (20g) pyroquilon, (II) 29 17, (400g) I+II, (1: 20) 3.3 11 20, (5+100g) I+II, (1: 10) 3.3 14 27, (7.5+75g) test 2
Rice blast infection rate %
Contrast (being untreated) 9.3 25 53fludioxonil (I) 5 after 55 days after 48 days after 34 days- *) 32 (20g) pyroquilon (II) 4.3 11 13 (400g) I+II (1: 20) 7.3 14 22 (5+100g) *) test failure
The above results shows, uses according to composition I+II of the present invention, has obtained consistent good long-acting with the total amount of using that greatly reduces.
It is 30g a.i. to 130g a.i./100kg seed and I+II=1 that total amount is used in employing: 50,1: 5,3: 5 and other mixing ratio also obtain same result.

Claims (7)

1. a plant species Synergistic microbicidal compositions, it comprises at least two kinds of active ingredient components with the suitable carriers material, wherein a kind of component I) be formula I 4-(2,2-two fluoro-1,3-benzo dioxole-7-yl)-1H-pyrroles-3-nitrile, i.e. fludioxonil With another component I I) be 1,2,5 of formula II, 6-tetrahydrochysene-4H-pyrrolo-[3,2,1-ij] quinoline-4-ketone, i.e. pyroquilon;
Figure C9710285500022
Wherein the weight ratio of I: II is 10: 1 to 1: 100.
2. according to the composition of claim 1, wherein the weight ratio of I: II is 5: 1 to 1: 60.
3. according to the composition of claim 2, wherein the weight ratio of I: II is 1: 1 to 1: 25.
4. the method for control or prevention plant disease, it comprises with the infection of the compositions-treated of claim 1 or plant part that is easy to infect or the growth place of plant.
5. according to the method for claim 4, it comprises treatment of plant propagation material.
6. according to the method for claim 5, wherein propagating materials is a seed.
7. according to the method for claim 6, seed wherein is a rice.
CN97102855A 1996-03-06 1997-03-05 Microbicides Expired - Lifetime CN1092022C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH588/96 1996-03-06
CH58896 1996-03-06

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CN1196176A CN1196176A (en) 1998-10-21
CN1092022C true CN1092022C (en) 2002-10-09

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JP (1) JP3988093B2 (en)
KR (1) KR100437066B1 (en)
CN (1) CN1092022C (en)
BR (1) BR9701198A (en)
CO (1) CO4750754A1 (en)
ID (1) ID16122A (en)
MY (1) MY128483A (en)
TW (1) TW361994B (en)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1394373A (en) * 1972-05-17 1975-05-14 Pfizer Ltd Control of plant diseases
EP0206999A2 (en) * 1985-06-21 1986-12-30 Ciba-Geigy Ag Microbiocide compounds

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR950010410B1 (en) * 1990-11-16 1995-09-16 가부시끼가이샤 도시바 Low-voltage detecting circuit
UA39100C2 (en) * 1993-06-28 2001-06-15 Новартіс Аг Bactericide agent for plants, a method to control fungal diseases of plants and a plant propagating material
DE4422881A1 (en) * 1993-10-25 1995-04-27 Bayer Ag Colloidally dispersible drug formulations
HU223083B1 (en) * 1994-06-28 2004-03-29 Bayer Ag. Fungicidal amino-acid-derivatives, process for their preparation and their use

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1394373A (en) * 1972-05-17 1975-05-14 Pfizer Ltd Control of plant diseases
EP0206999A2 (en) * 1985-06-21 1986-12-30 Ciba-Geigy Ag Microbiocide compounds

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JPH107508A (en) 1998-01-13
BR9701198A (en) 1998-08-18
CN1196176A (en) 1998-10-21
JP3988093B2 (en) 2007-10-10
TW361994B (en) 1999-06-21
ID16122A (en) 1997-09-04
MY128483A (en) 2007-02-28
KR100437066B1 (en) 2005-01-27
CO4750754A1 (en) 1999-03-31
KR970064374A (en) 1997-10-13

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