EP0593438A1 - Compositions fongicides, composes fongicides, ainsi que leur production et utilisation - Google Patents

Compositions fongicides, composes fongicides, ainsi que leur production et utilisation

Info

Publication number
EP0593438A1
EP0593438A1 EP90915139A EP90915139A EP0593438A1 EP 0593438 A1 EP0593438 A1 EP 0593438A1 EP 90915139 A EP90915139 A EP 90915139A EP 90915139 A EP90915139 A EP 90915139A EP 0593438 A1 EP0593438 A1 EP 0593438A1
Authority
EP
European Patent Office
Prior art keywords
formula
group
compound
composition
hydrogen
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.)
Withdrawn
Application number
EP90915139A
Other languages
German (de)
English (en)
Inventor
John Walter Liebeshuetz
Michel Jean Jung
Thomas Alexander Kendrick Smith
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.)
Corteva Agriscience LLC
Original Assignee
DowElanco LLC
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 DowElanco LLC filed Critical DowElanco LLC
Publication of EP0593438A1 publication Critical patent/EP0593438A1/fr
Withdrawn legal-status Critical Current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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/62—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms three- or four-membered rings or rings with more than six members
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/44—Nitrogen atoms not forming part of a nitro radical
    • C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
    • C07D239/12—Nitrogen atoms not forming part of a nitro radical
    • C07D239/14—Nitrogen atoms not forming part of a nitro radical with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to said nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/04—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring

Definitions

  • This invention relates to novel chemical compounds having fungicidal activity, and in particular to such compounds containing a guanidine group and to the use of these and other compounds as fungicides.
  • Fungicidally active compounds containing a guanidine- type grouping compounds are also disclosed, for example in U.S. Patent No. 2988478.
  • the present invention provides the use as a fungicide of compounds of the formula
  • R 1 and R 7 are each independently
  • R 2 is hydrogen or C 1 -C 6 alkyl
  • R 5 independently and each R 5 independently are hydrogen or C 1 -C 4 alkyl
  • R 6 is a cyclohexyl group or a monocyclic or bicyclic aromatic group (for example phenyl or
  • naphthalenyl substituted with from 1 to 5 groups of the formula R 8 ,
  • R 8 is halogen, a C 1 -C 10 alkyl
  • Y is a group of the formula -(CR 9 R 9 ) n -,
  • n 2, 3, or 4
  • each R 9 independently is hydrogen or C 1 -C 4 alkyl, and X- is a suitable counter-ion.
  • the invention also provides fungicidal compositions which contain such compounds, particularly together with an
  • a number of compounds of formula I-A, I-B and I-C are novel, particularly those wherein p is 1 or 2 and n is 3 or 4. Accordingly, the invention also provides such novel compounds.
  • the compounds of the invention contain three basic nitrogen atoms, and thus can exist either in the form of the free base (formulae I-B and I-C), or a salt (formula I-A), for example a quaternary salt or an acid addition salt.
  • the compound can thus exist in tautomeric forms, all of which are within the scope of the present invention.
  • R 1 and R 7 are preferably each hydrogen, methyl or ethyl more preferably hydrogen, and R 2 is
  • Y is preferably a group of the formula
  • Each of groups R 4 and R 5 are preferably
  • group R 3 is preferably methyl, and p is preferably 1.
  • the group R 6 is preferably a substituted phenyl group, more preferably a 4-t- butylphenyl group or 4-trimethylsilylphenyl.
  • the ring containing the guanidine group is preferably six membered, i.e. n in the definition of Y is preferably 3.
  • alkyl, alkoxy, alkylene, alkenylene and the like are intended to include within their scope both straight and branched groups
  • alkenyl, alkenylene and the like are intended to include groups containing one or more than one double bonds.
  • halogen and halo as used herein include chlorine, bromine, fluorine and iodine. It will be appreciated that certain combinations of substituent groups for compounds which fall within the definition of formula I-A, I-B and I-C given above will be impossible to prepare for steric and other chemical reasons. Such compounds are not included within the scope of the invention.
  • the anion X" in formula I-A may be any anion addition salt capable of forming an acid, for example chloride, bromide, acetate, stearate, benzoate or dodecylbenzenesulphonate, the chloride being
  • the compounds of formula I-A, I-B and I-C may be prepared by reacting a compound of the formula
  • R 1 to R 6 , Y, x and p are as defined above, and L is a suitable leaving group, for example an alkylthio group, preferably at a temperature of from 50 to 200oC.
  • the reaction may be carried out in a suitable organic solvent for example an alkanol such as
  • L is preferably an alkylthio gooup.
  • the compounds of formula I-A, I-B and I-C may also be prepared by reducing a compound of formula
  • the reaction may be carried out at atmospheric
  • the compound of formula V may be prepared by reacting a compound of the formula
  • R 2 to R 6 and each R 9 independently, is as defined above, and L is a suitable leaving group.
  • the reaction between compound II and compound III is preferably carried out in a polar solvent at a temperature of from 50 to 200oC, in the presence of a base.
  • Compounds of the formula II may generally be prepared by the reaction of a compound of the formula
  • Compound VI may be prepared according to Katrizky, de Ville and Patel (J.C.S. Chem. Comm. 1979, 602) from a compound of formula
  • compounds of formula I-B wherein certain of the R 5 groups are restricted to hydrogen, may be prepared by the reaction of a compound of the formula
  • the reduction may be carried out, for example using a metal hydride such as LiA1E 4 , at a temperature of from -80 to
  • the compounds of formula I-A, I-B and I-C may be used as fungicides in particular for agricultural use, against a wide range of pathogens, for example
  • the compounds in accordance with the invention may be applied to the roots, seeds, or foliage of barley and other plants, for the control of various fungi, without damaging their commercial value.
  • the compounds of the present invention effectively control a variety of undesirable fungi which infest useful plant crops.
  • Deuteromycotina such as Septoria nodorum (glume blotch of cereals), Pyricularia oryzae (rice-blast), Botrytis cinerea (grey mould of grapes and Fusarium Oxysporum (various wilt diseases), ii) Ascomycotina such as Pyrenophora teres (net-blotch) and Erysiphe graminis (powdery mildew), and iii)
  • Deuteromycotina such as Septoria nodorum (glume blotch of cereals), Pyricularia oryzae (rice-blast), Botrytis cinerea (grey mould of grapes and Fusarium Oxysporum (various wilt diseases)
  • Ascomycotina such as Pyrenophora teres (net-blotch) and Erysiphe graminis (powdery mildew)
  • Basidiomycotina such as Puccinia recondita (leaf rust).
  • the compounds can be applied to the seeds, roots or foliage of cereals or other plants and will kill or control the growth of various fungi without damaging the commercial value of the said plants.
  • the improved water solubility also allows the preparation of solutions (in water or organic solvents) in which, at use rate, the addition salt is completely soluble in the spray dilution.
  • a single application of the compounds can provide a residual control of powdery mildew diseases over an extended period. Also, the compounds can be effective in eliminating established barley powdery mildew infestation. Furthermore, many
  • the compounds of the invention may also find application as non-agricultural fungicides for example in medicine as antimycotics against organisms such as Candida albicans, Candida spp, Trichophyton spp,
  • Aspergillus spp, Microsporum spp and Sporothrix spp, and also as agents against parasites such as
  • the invention includes within its scope fungicidal compositions comprising a
  • compositions may be in the form of a liquid, powder, dust or granular composition containing one or more of the active compounds in and one or more inert, non-phytotoxic materials, known in the art as agricultural adjuvants and/or carriers, in solid or liquid form.
  • the active compound (s) can be admixed with one or more additives including water or other liquid carriers such as organic
  • solvents and petroleum distillates, surface active dispersing agents, and finely divided inert solids.
  • the active ingredients are generally present in a concentration of from 2 per cent to about 95 per cent by weight preferably from 10 per cent to 95 per cent by weight and most advantageously 10 per cent to 75 per cent by weight.
  • the compound can be employed in the form of a solution, a diluted flowable compositions or a wettable powder composition containing 2 to 10 , 000 ppm of active ingredient .
  • the carrier contains a surface active agent, from about 0.1 to about 20 per cent by weight of the active ingredient is advantageously employed.
  • compositions are adapted to be employed for the control of the undesirable fungi or employed as concentrates and subsequently diluted with additional inert carrier, e.g. water, to produce the ultimate treating compositions.
  • additional inert carrier e.g. water
  • liquid compositions containing from about 0.0001 to about 2.0 per cent by weight of the active compound in the final diluted form can usually be obtained with compositions containing from about 0.1 to about 2.0 per cent or more by weight of active compound.
  • the toxicant be present in an amount not to exceed about 0.8 per cent in liquid compositions and about 1.0 per cent in dusts.
  • the toxicant products can be compounded with any of the finely divided solids, such as
  • the finely divided carrier is ground or mixed with the toxicant or wet with a solution of the toxicant in a volatile organic solvent.
  • compositions when employed as concentrates can be dispersed in water, with or without the aid of dispersing agents to form spray mixtures. Dust
  • compositions are advantageously employed when treating seeds.
  • Granular formulations are usually prepared by impregnating a solution of the toxicant in a volatile organic solvent onto a bed of coarsely divided
  • Attapulgite attapulgite, bentonite, diatomite, or the like.
  • the toxicant products can be compounded with a suitable water-immiscible inert organic liquid and a surface active dispersing agent to produce an emulsifiable concentrate which can be further diluted with water and oil to form spray mixtures in the form of oil-in-water emulsions which may optionally contain water miscible organic co-solvents to improve the physical properties of the formulation.
  • the carrier comprises an aqueous
  • emulsion i.e., a mixture of inert water-immiscible solvent and optional water miscible organic co-solvent, emulsifying agent, and water.
  • Emulsifiers which can be advantageously employed herein can be readily determined by those skilled in the art and include various nonionic, anionic, cationic and amphoteric emulsifiers, or a blend of two or more emulsifiers.
  • nonionic emulsifiers useful in preparing the emulsifiable concentrates include the polyalkylene glycol ethers and condensation products of alkyl and aryl phenols, aliphatic alcohols, aliphatic amines or fatty acids with ethylene oxide, propylene oxide or mixtures of ethylene and propylene oxides such as the ethoxylated alkyl phenols and carboxylic esters solubilized with the polyol or polyoxyalkylene.
  • Cationic emulsifiers include quaternary ammonium compounds and fatty amines.
  • Anionic emulsifiers include the oil-soluble salts (e.g., calcium) of alkylaryl sulphonic acids, oil soluble salts or
  • the preferred organic liquids are xylene, and propyl benzene fractions, with xylene being most preferred .
  • the surface active dispersing agents are usually employed in liquid compositions and in the amount of from 0.1 to 20 per cent by weight of the combined weight of the dispersing
  • the active compositions can also contain other compatible additives, for example, plant growth regulators and other biologically active compounds used in agriculture.
  • the active compositions may contain adjuvant surfactants to enhance the deposition, wetting and penetration of the composition onto the target crop and organism.
  • adjuvant surfactants may be included in particular, the active compositions.
  • adjuvant surfactant will vary from 0.01 per cent to 1.0 per cent v/v based on a spray-volume of water, preferably 0.05 to 0.5 per cent.
  • Suitable adjuvant surfactants include ethoxylated nonyl phenols, ethoxylated synthetic or natural alcohols, salts of the esters or sulphosuccinic acids, ethoxylated organosilicones, ethoxylated fatty amines and blends of surfactants with mineral or vegetable oils.
  • the compounds of the present invention or compositions containing the same can be advantageously employed in combination with one or more additional pesticidal compounds.
  • additional pesticidal compounds may be insecticides, nematocides, miticides, arthropodicides, or bactericides that are compatible with the compounds of the present invention in the medium selected for application and not
  • the pesticidal compound is employed as a supplemental toxicant for the same or for a different pesticidal use or as an
  • the compounds in combination can generally be present in a ratio of from 1:100 to 100:1.
  • the exact amount of the active material to be applied is dependent not only on the specific active material being applied, but also on the particular action desired, the fungal species to be controlled and the stage of growth thereof as well as the part of the plant to be contacted with the toxic active ingredient. Thus, all of the active ingredients of the present invention and compositions containing the same may not be equally effective at similar concentrations or against the same fungal species.
  • the compounds in accordance with the invention may be applied in the form of any of the generally used formulation types, for example as solutions, dusts, wettable powders, flowable concentrates, or
  • the invention includes within its scope a method for the control or prevention of fungal attack, which method comprises applying to the locus of the fungus, or to a locus in which the infestation is to prevented, (for example applying to cereal grain plants), a fungicidal amount of one or more of the compounds.
  • nitroethane and 2.9g of ammonium acetate were refluxed together under nitrogen for 4 hours.
  • the nitroethane was distilled off and the residue taken up in
  • 4-t butylphenethylamine was prepared in a manner analogous to that used in steps (a) and (b) in Example 1, except that nitromethane was used in place of nitroethane in step (a).
  • Example 3 N-(1-(4-t-butylphenyl)prop-2-yl)-N',N"-pent-2,4 diyl guanidinium acetate (Example 3) and chloride (Example 4) were prepared by methods analogous with those used in Example 1, except that 2-chloro, 4,6 dimethyl pyrimidine was used in place of 2-chloro pyrimidine in step (c), and in Example 5, acetic acid was used in place of hydrochloric acid. NMR and IR spectra were consistent with the expected structure.
  • Test compounds are generally dissolved in acetone and made up with distilled water to give a solution with a final concentration of compound of 400 ppm and 10 per cent acetone. 2 ml aliquots of the latter solutions are pipetted into sterile petri dishes, and 18 ml of agar is then added to each dish using an automatic agar plate pourer to give a final
  • discs of pathogens are cut from stock agar plates using a cork borer, and placed (pathogen face down) onto the test agar surface.
  • Pathogens used in the primary screen include:- 1. Alternaria brassicola
  • the pathogens on plate 1 are assessed after 5 days and those on plate 2 after 8 days.
  • the diameters of the fungal colonies are measured after the incubation period and compared to the control measurements. Allowing for the diameter of the original disc,
  • Seeds are sown 1 cm deep in 4 rows per plastic tray 60 cm x 30 cm. Seedlings are inoculated at 1-2 leaf stage. 0.05 g of uredospores are put into 100 ml distilled water with a melting agent. This solution is sprayed onto seedlings leaving a fine coverage on the leaves. The plants are then incubated with 100% relative humidity at 15-20oC for 4 days.
  • % infection is scored from 3 replicate plants and expressed as a % of acetone/water control plants. % control is then recorded.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Compositions fongicides agricoles comprenant des composés de la formule (I-A), (I-B) ou (I-C), où R1 et R7 sont chacun indépendamment hydrogène ou C1-C3 alkyle R2 est hydrogène ou C1-C6 alkyle, R3 et R4 indépendamment et chaque R5 indépendamment sont hydrogène ou C1-C4 alkyle, R6 est un groupe cyclohexyle ou un groupe aromatique monocyclique ou bicyclique, substitué par 1 à 5 groupes de la formule R8, où R8 est halogène, un groupe alhyle C1-C10, un groupe alkoxy C1-C10, un groupe tri-C1-C4-alkylsilyle, ou un groupe phénoxy, phényle, phényle-C1-C2-alkylène ou phényle-C2-alkenylène, chacun optionnellement substituté sur le groupe phényle ou phénoxy par un atome d'hydrogène ou davantage, des groupes alkyle C1-C6 ou alkyle C1-C6, ou alkoxy C1-C6, des groupes trihalométhyle, phényle ou phénoxy. p est 0, 1 ou 2, Y est un groupe de la formule -(CR9R9)n-, où n est 2, 3 ou 4, chaque R9 indépendamment est hydrogène ou C1-C4 alkyle et X est un contre-ion approprié, l'ensemble avec un diluant ou un transporteur acceptable pour l'agriculture, et de nouveaux composés fongicides de la formule (I-A), (I-B) ou (I-C) où p est 1 ou 2 et n est 3 ou 4.
EP90915139A 1989-10-10 1990-10-09 Compositions fongicides, composes fongicides, ainsi que leur production et utilisation Withdrawn EP0593438A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB898922750A GB8922750D0 (en) 1989-10-10 1989-10-10 Fungicidal compounds,their production and use
GB8922750 1989-10-10
PCT/GB1990/001555 WO1991005473A1 (fr) 1989-10-10 1990-10-09 Compositions fongicides, composes fongicides, ainsi que leur production et utilisation

Publications (1)

Publication Number Publication Date
EP0593438A1 true EP0593438A1 (fr) 1994-04-27

Family

ID=10664306

Family Applications (1)

Application Number Title Priority Date Filing Date
EP90915139A Withdrawn EP0593438A1 (fr) 1989-10-10 1990-10-09 Compositions fongicides, composes fongicides, ainsi que leur production et utilisation

Country Status (8)

Country Link
EP (1) EP0593438A1 (fr)
JP (1) JPH05504946A (fr)
AU (1) AU647416B2 (fr)
BR (1) BR9007740A (fr)
CA (1) CA2066164A1 (fr)
GB (1) GB8922750D0 (fr)
NZ (1) NZ235608A (fr)
WO (1) WO1991005473A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101287366A (zh) 2005-05-19 2008-10-15 拜尔农作物科学股份公司 杀虫的取代的苄基氨基杂环及杂芳基衍生物

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2988478A (en) * 1958-12-22 1961-06-13 Pfizer & Co C Agricultural compositions and use
CH630507A5 (en) * 1977-10-11 1982-06-30 Ciba Geigy Ag Pesticides
NL7711390A (nl) * 1977-10-18 1979-04-20 Philips Nv Nieuwe 2-arylimino-hexahydopyrimidinen en - imi- dazolidinen, zouten en complexen daarvan, werk- wijze ter bereiding van de nieuwe verbindingen, alsmede fungicide preparaten op basis van de nieuwe verbindingen.
NL7810350A (nl) * 1978-10-16 1980-04-18 Duphar Int Res Preparaat met groeiregulerende werking en gebruik van dit preparaat in land- en tuinbouw.
US4931455A (en) * 1988-01-07 1990-06-05 Ube Industries, Ltd. Alkylaminopyrimidine derivative and insecticide, acaricide and fungicide containing the same as active ingredient

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9105473A1 *

Also Published As

Publication number Publication date
WO1991005473A1 (fr) 1991-05-02
AU6507590A (en) 1991-05-16
CA2066164A1 (fr) 1991-04-11
NZ235608A (en) 1991-08-27
BR9007740A (pt) 1992-09-15
GB8922750D0 (en) 1989-11-22
JPH05504946A (ja) 1993-07-29
AU647416B2 (en) 1994-03-24

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