GB2024015A - 1,2,4,-Triazolidin-3-ones and 1,2,4-triazolidin-3-thiones fungicides - Google Patents
1,2,4,-Triazolidin-3-ones and 1,2,4-triazolidin-3-thiones fungicides Download PDFInfo
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- GB2024015A GB2024015A GB7918106A GB7918106A GB2024015A GB 2024015 A GB2024015 A GB 2024015A GB 7918106 A GB7918106 A GB 7918106A GB 7918106 A GB7918106 A GB 7918106A GB 2024015 A GB2024015 A GB 2024015A
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- triazolidin
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- thione
- phenyl
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- TVGORZIXNONOIQ-UHFFFAOYSA-N 1,2,4-triazolidine-3-thione Chemical class S=C1NCNN1 TVGORZIXNONOIQ-UHFFFAOYSA-N 0.000 title claims description 6
- 239000000417 fungicide Substances 0.000 title description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 239000000203 mixture Substances 0.000 claims abstract description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- NXHDERLYZNBICI-UHFFFAOYSA-N 1,2,4-triazolidin-3-one Chemical compound O=C1NCNN1 NXHDERLYZNBICI-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 206010017533 Fungal infection Diseases 0.000 claims abstract description 5
- 208000031888 Mycoses Diseases 0.000 claims abstract description 5
- 241001061127 Thione Species 0.000 claims abstract description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 239000001301 oxygen Substances 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims abstract description 3
- 239000000843 powder Substances 0.000 claims description 7
- -1 2-(3,4 dichlorophenyl)-5,5-dimethyl-1,2,4-triazolidin-3-one Chemical compound 0.000 claims description 6
- 230000000855 fungicidal effect Effects 0.000 claims description 6
- ZQAJNJUOCBBHEO-UHFFFAOYSA-N 2-(4-chlorophenyl)-5,5-dimethyl-1,2,4-triazolidin-3-one Chemical compound O=C1NC(C)(C)NN1C1=CC=C(Cl)C=C1 ZQAJNJUOCBBHEO-UHFFFAOYSA-N 0.000 claims description 5
- 239000007900 aqueous suspension Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- QLKGDFIEQGUNML-UHFFFAOYSA-N 2-(3-chlorophenyl)-5,5-dimethyl-1,2,4-triazolidine-3-thione Chemical compound S=C1NC(C)(C)NN1C1=CC=CC(Cl)=C1 QLKGDFIEQGUNML-UHFFFAOYSA-N 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 239000000080 wetting agent Substances 0.000 claims description 2
- 241000575946 Ione Species 0.000 claims 1
- LTXREWYXXSTFRX-QGZVFWFLSA-N Linagliptin Chemical compound N=1C=2N(C)C(=O)N(CC=3N=C4C=CC=CC4=C(C)N=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 LTXREWYXXSTFRX-QGZVFWFLSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 description 25
- 230000000694 effects Effects 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 230000001143 conditioned effect Effects 0.000 description 10
- 208000015181 infectious disease Diseases 0.000 description 8
- 241000221577 Uromyces appendiculatus Species 0.000 description 6
- 238000011534 incubation Methods 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000000454 talc Substances 0.000 description 5
- 229910052623 talc Inorganic materials 0.000 description 5
- 241000233866 Fungi Species 0.000 description 4
- 241000233626 Plasmopara Species 0.000 description 4
- 241000221301 Puccinia graminis Species 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 230000003449 preventive effect Effects 0.000 description 4
- 241001120669 Colletotrichum lindemuthianum Species 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- ZUTUVZYGIDTWJP-UHFFFAOYSA-N 2-(3,5-dichlorophenyl)-5,5-dimethyl-1,2,4-triazolidine-3-thione Chemical compound CC1(C)NN(C(=S)N1)C1=CC(Cl)=CC(Cl)=C1 ZUTUVZYGIDTWJP-UHFFFAOYSA-N 0.000 description 2
- HTXUDEXIYYPGEV-UHFFFAOYSA-N 5-ethyl-5-methyl-2-phenyl-1,2,4-triazolidine-3-thione Chemical compound S=C1NC(CC)(C)NN1C1=CC=CC=C1 HTXUDEXIYYPGEV-UHFFFAOYSA-N 0.000 description 2
- 241000123650 Botrytis cinerea Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241001518836 Monilinia fructigena Species 0.000 description 2
- 229920001213 Polysorbate 20 Polymers 0.000 description 2
- 241001123668 Verticillium dahliae Species 0.000 description 2
- 230000000843 anti-fungal effect Effects 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- 230000003053 immunization Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- QRNATDQRFAUDKF-UHFFFAOYSA-N 2-carbamothioylsulfanylethyl carbamodithioate Chemical compound NC(=S)SCCSC(N)=S QRNATDQRFAUDKF-UHFFFAOYSA-N 0.000 description 1
- LIYDZGWOZZFIKI-UHFFFAOYSA-N 2-phenyl-5,5-dipropyl-1,2,4-triazolidin-3-one Chemical compound O=C1NC(CCC)(CCC)NN1C1=CC=CC=C1 LIYDZGWOZZFIKI-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241001450781 Bipolaris oryzae Species 0.000 description 1
- 241001465180 Botrytis Species 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 241001363490 Monilia Species 0.000 description 1
- 241000122123 Penicillium italicum Species 0.000 description 1
- 241000221300 Puccinia Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000082085 Verticillium <Phyllachorales> Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Natural products OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- GYSSRZJIHXQEHQ-UHFFFAOYSA-N carboxin Chemical compound S1CCOC(C)=C1C(=O)NC1=CC=CC=C1 GYSSRZJIHXQEHQ-UHFFFAOYSA-N 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 230000001473 noxious effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/12—Oxygen or sulfur atoms
Abstract
Compositions for, and a method of treating plants to prevent or combat fungal infections in which the plants are treated with a compound which is a 1,2,4-triazolidin- 3-one or thione of the general formula: <IMAGE> in which: R<2> represents a linear or branched C1 to 6 alkyl group having an optionally substituted phenyl group or a benzyl group, R<2> represents a linear or branched C1 to 6 alkyl group, a benzyl group, an optionally substituted phenyl group or R<1> and R<2> together form a spiranic ring optionally containing a heteroatom as part of the ring, R<3> represents an alkyl group, a phenyl group which is optionally substituted with one or more substituents which are alkyl or alkoxyl groups, halogen atoms or NO2 groups; R<4> represents a hydrogen atom or a phenyl group optionally substituted with one or more halogen atoms, and X represents an oxygen or sulphur atom.
Description
SPECIFICATION 1,2 ,4-Triazolidin-3-ones and 1,2 ,4-triazolidin-3-thiones fungicides
The present invention relates to the use of 1 ,2,3-triazolidin-3-ones and -thiones as fungicides and to compositions containing 1,2,4,triazolidin-3-one and -thiones useful for fighting fungal infections in plants of agricultural interest.
1,2,4-triazolidin-3-ones and 1,2,4-triazolidin-3-thiones are known and are disclosed for example in the following publications: H. Schildknecht and G. Renner: Liebig's Ann. der
Chemmie 724(1969), page 226; ibid. 761(1972) page 189; 1. Aroli: Bull. Chem. Soc. Japan 46(1973) page 2215: K. Pilgram, R.D. Skiles, G.E. Pollard: Jr. Heterocyclic Cem. 13(1976) page 1257; Iwas Yamamoto, Akio Mamba, Harno Gotoh; Jr Chem. Soc. Perkin 1 (1976) p.
1275.
United States Patent Specification No. 3,922,162 discloses the use of 4-phenyl-1 2,4- triazolidin-3-ones, not substituted in the 5 position, as herbicides and German Offenlegungsschrift No. 2440378 discloses the use of 1,2,4-triazolidin-3-thiones as drugs developing antiphlogistical and analgesic activities.
1,2,4-triazolidin-3-ones and -thiones substituted in the 2 and 5 positions in our Copending
Application No. 79/18107.
According to the present invention there is provided a method of treating plants to prevent or combat fungal infection, in which the plants are treated with a compound which is a 1,2,4triazolidin-3-one or thione of the general formula:
in which:
R1 represents a linear or branched alkyl group having 1 to 6 carbon atoms, a phenyl group, a substituted phenyl group or a benzyl group,
R2 represents a linear or branched alkyl group having 1 to 6 carbon atoms, a cycloalkyl group, a benzyl group, a phenyl group or a substituted phenyl group or
R1 and R2 together form a spiranic ring, optionally containing a heteroatom as part of the ring;
R3 represents an alkyl group, a phenyl groups which is optionally substituted with one or more substituents which are alkyl or alkoxyl groups, halogen atoms or NO2 groups;;
R4 represents a hydrogen atom or a phenyl group optionally substituted with one or more halogen atoms, and
X represents an oxygen or sulphur atom.
The compound may be applied to the plants as such or in the form of powders, wettable powders, emulsions or aqueous suspensions, solutions in solvents, etc. It has been found that the above compounds are suited for preventing and curing infections due for instance to
Colletotrichum lindemuthianum, Monilia fructigena, Botrytis cinerea, Penicillum italicum, Helminthosporium oryzae, Verticillum dahliae, Plasmopora viticola, Puccinia graminis, Uromyces appendiculatus and other fungi noxious for plants of agricultural or ornamental interest.
The fungicide 1,2,4-triazolidin-3-ones or -thiones may be used as such by sprinkling them on the plants to be protected or cured, or they may suitably be formulated with a carrier according to the conventional techniques known to the skilled in the art. The compounds may be admixed in quantities of from 0.1 % upwards, e.g., up to 50% with inert powders such as diatomite earth, talc and chalk, or they may be absorbed in the form of solutions by the powders optionally by additioning them with surfactants, wetting agents to assist absorption. The compounds may also be dissolved in solvents. The plants are simply treated by applying the compositions e.g. by sprinkling. The invention also extends to the above described compositions.
As reported in TABLES I and li (relating to the antifungal activity 'in vitro', and 'in vivo' of the triazolidin-3-ones and -thiones of this invention, tested according to the procedures in Examples 1 to 4 a wide range of fungicidal activity has been shown by the following compounds: 2-phenyl-5, 5-di-n-propyl-l, 2,4-triazolidin-3-one 2-(4-Chlorophenyl)-5,5-dimethyl-1,2,4-triazolidin-3-one 2-(3,4-dichloropheny1)-5, 5-dimethyl-l ,2,4-triazolidin-3-one.
2-phenyl-5-methyl-isobutyl- 1 , 2,4-triazolidin-3-one 2-phenyl-5, 5-dimethyl-1 , 2,4-triazolidin-3-thione 2-(p.chlorophenyl)-5,5-dimethyl-1,2,4-triazolidin-3-thione.
Other compounds, e.g. 2-(3, 5-dichlorophenyl)-5, 5-dimethyl-l ,2,4-triazoiidin-3-thione, display a high specificity against Pasmopora viticola, Colletotrichum lindemuthianum and Verticillium dahlia.
The fungicidal activity of the compounds causes the infection in progress to regress (curative activity), or preserves the plant from the infection itself (preventive activity), or hinders the infection also of untreated parts (immunological activity).
The anti-fungal activity tested according to the methods described in Examples 1 to 4, is reported in the following TABLES I and 11.
Table I
Fungicide activity 'in vitro' (applied dose = 100 ppm)
Helmintho
Colletotichum Monilia Botrytis Penicilium sporium Verticillium
Compound Lindemuthianum furctigen einerea italicum oryzae dahliae 2-(4-chlorophenyl)-5,5-dimethyl1,2,4-triazolidin-3-one 100 100 100 - 100 100 2-(3,4-dichlorophenyl)5,5dimethyl-1,2,4-triazolidine-3-one 100 100 - - 100 100 2-(4-chlorophenyl)1,2,4-triazospyro-4,5-decan-3-thione 100 100 - - 100 100 2-(3,5-dichlorophenyl)-5,5-dimethyl 1,2,4-triazolidine-3-thione 100 - - - - 100 2-phenyl-5-methyl-5-ethyl-1,2,4triazolidin-3-thione 100 100 100 - 100 100 2-(4-chlorpphenyl)-5,5-dimethyl1,2,4-triazolidin-3-thione 100 100 100 100 100 100 2-(3-chlorophenyl)-5,5-dimethyl1,2,4-triazolidin-3-thione 100 100 100 100 100 100 Table II
Fungicide activity on plams
Puocinia Graminis Uomices appendiculatus
Plasmopora Viticola Preventive Curative Curative Immunizing
Compound 1% 0.5% 1% 1% 1% 0.5% 1% 0.5% 2-phenyl-5,5-dipropyl-1,2,4-triazolidin-3-one 100 100 60 78 100 76 100 100 2-(4-chlorophenyl)-5,5-dimethyl-1,2,4triazolidin-3-one 100 100 77 80 100 100 100 100 2-(3,4-dichlorophenyl)-5,5-dimethyl1,2,4-triazolidin-3-one 100 100 - - - - 76 36 2-(4-chlorophenyl)-1,2,4-triaza-spyro [4,5]-decan-3-thione - 32 75 85 100 100 100 100 2-(3,5-dichlorophenyl)-5,5-dimethyl1,2,4-triazolidin-3-thione 100 100 - - - - - 2-phenyl-5-methyl-5-n-propyl-1,2,4triazolidin-3-one 100 100 - - - - - 2-phenyl-5-ethyl-5-i.butyl-1,2,4triazolidin-3-one 100 64 92 80 100 100 100 60 2-phenyl-5-methyl-5-ethyl-1,2,4triazolidin-3-thione 100 74 85 86 100 100 100 50 2-phenyl-5-methyl-5-n.propyl-1,2,4triazolidin-3-thione 100 100 - - - - - 2-phenyl-5,5-di-n.propyl-1,2,4triazolidin-3-thione 100 100 - - - - - 2-(4-chlorophenyl)-5,5-dimethyl- 100 100 100 100 1,2,4-triazolidin-3-thione 100 100 73 74 100 80 85 50 2-(3-chlorophenyl)-5,5-dimethyl1,2,4-triazolidin-3-thione 100 80 - - - - - 2-methyl-1,2,4-triaza-spyro-[4,5]decan-3-thione 100 100 -
Zineb (1) (reference product) 100 70
Vitavax (Registered Trade Mark) (2) (reference product) - - 84 89 100 100 100 100 (-) no activity; (1) zine ethylene-bis-dithiocarbamate by Montedison S.p.A.
(2) 2-3-dihydro-6-methyl-5-phenyl-carbamoyl-1,4-oxazyne.
The invention will now be illustrated by the following Examples.
Example 1
Activity 'in vitro'.
The activity was determined by evaluating the percentage inhibition of the growth of the fungi cultivated on a nutrient medium (PDA Difco (Registered Trade Mark)) containing growing concentrations of the compounds under examination. These latter were emulsified in the culture medium, formulating them with dimethylsulphoxide + Tween 20 (Registered Trade Mark), so that the final concentration was 0.5% dimethylsulphoxide and 0.01 % Tween 20.
For the species Colletotrichum lindemuthianum, Monilia fructigena, Botrytis cinerea and
Penicillium italicum, small agar discs of 5 mm zit with the mycelium of each fungus were placed in the centre of Petri dishes. For the species Hleminthosporium oryzae and Verticillium dahliae drops of a suspension of spores and mycelium were placed in the centre of the dishes, thereby obtaining a circular inoculum.
After a 4-day growth at 25"C the diameters of the colonies that developed were measured and the percentage of inhibition of the growth in comparison with the control was calculated.
The results are reported in TABLE I.
Example 2
Preventive activity on Peronospera of the vine.
(Plasmopora viticola (B. et C.) et de Toni)
Vine leaves cv. Dolcetto, grown in pots in an environment conditioned at 25"C and 60% relative humidity, were treated by besprinkling on both leaf faces with the products under examination, in hydroacetonic solution (20% of acetone vol/vol.). After one day from the treatment the leaves were besprinkled on the lower face with an aqueous suspension of
Plasmopora viticola conydia (200,000 conidya per cc) and were then kept in a moisture saturated environment at 21"C for 24 hours.
Subsequently, the plants were transferred into an environment with 70% relative humidity at 21"C, for an incubation period of 7 days. At the end of the treatment the intensity of the infestation was evaluated using the indexes of an evaluation scale ranging from 100 (heaithy plant) to 0 (for a completely infected plant). The results of the activity are reported in TABLE II.
Example 3 (a) Curative activity on wheat rust.
(Puccinia graminis Pers.)
Wheat leaves cv. Irnerio and Mentana, grown in pots in a conditioned environment, were besprinkled on both leaf faces with a mixture of Puccinia graminis spores in talc (100 mg of spores/5 g of talc). After 48 hours dwelling time in a moisture saturated environment at 21 C, the leaves were treated with the products under examination in a hydroacetonic solution (20% acetone vol./vol.) besprinkled on both leaf faces.
At the end of the incubation period (14 days), the extent of the infection was usually estimated on the basis of indexes of an evaluation scale ranging from 100 (healthy plant) to O (completely infected plant).
(b) Preventive activity on wheat rust.
(Puccinia graminis Pers.)
The wheat leaves cv. Irnerio and Mentana, grown in pots in a conditioned environment, were treated by besprinkling both leaf faces with the products under examination in a hydroacetonic solution (20% acetone vol./vol.). After a dwell time of 4 days in a conditioned environment, at 23"C and 70% relative humidity, the plants were besprinkled on both leaf faces with a mixture of Puccinia graminisspires in talc (100 mg of spores of talc). After dwelling 48 hours in a moisture saturated environment at 21"C, the plants were kept in an environment conditioned for the incubation of the fungus.
At the end of the period (14 days), the extent of the infection was evaluated by means of indexes ranging from 100 (for a healthy plant) to 0 (for a completely infected plant). The results of the activity tests (a) and (b) are reported in TABLE II.
Example 4 (a) Curative activity on Rust on the bean (Uromyces appendiculatus (Pers.) Link).
The bean leaves cv. Borlotto of Vigevano, grown in pots and in a conditioned environment, were besprinkled on the lower leaf face with an aqueous suspension of Uromyces appendiculatus (200,000 spores per cc). After dwelling 24 hours in a moisture saturated environment at 21"C, the plants were kept for 1 day in an environment conditioned at 23"C and with 70% relative humidity. After 48 hours from the start of the test, the leaves were treated with the products under examination in a hydroacetonic solution (20% acetone vol./vol.) by besprinkling both leaf faces.
At the end of the incubation period (14 days), the extent of the infection was usually evaluated on the basis of an evaluation scale ranging from 100 (healthy plant) to O (completely infected plant).
(b) Immunizing activity on bean rust (Uromyces appendiculatus (Pers.) Link).
Bean leavs c.v. Borlotto of Vigevano, grown in pots in a conditioned environment, were besprinkled on the upper leaf face with the products under examination in a hydroacetonic solution (20% acetone vol./vol.). The plants were then kept in a conditioned environment for 6 days. On the seventh day the plants were besprinkled on the lower face of their leaves with a suspension of Uromyces appendiculatus spores (200,000 spores/cc). After 24 hours in a moisture saturated environment at 21"C, the plants were placed back in a conditioned environment.
At the end of the incubation period (14 days), the extent of the infection was usually assessed on the basis of an index of an evaluation scale ranging from 100 (for a healthy plant) to O (for a completely infested plant). The results of the activity tests (a) and (b) are reported in TABLE II.
Claims (20)
1. A method of treating plants to prevent or combact fungal infection, in which the plants are treated with a compound which is a 1 ,2,4-triazolidin-3-one or thione of the general formula:
in which:
R' represents a linear or branched alkyl group having 1 to 6 carbon atoms, a phenyl group, a substituted phenyl group or a benzyl group,
R2 represents a linear or branched alkyl group having 1 to 6 carbon atoms, a cycloalkyl group, a benzyl group, a phenyl group or a substituted phenyl group or R' and R2 together form a spiranic ring, optionally containing a heteroatom as part of the ring,
R3 represents an alkyl group, a phenyl group which is optionally substituted with one or more substituents which are alkyl or alkoxyl groups, halogen atoms or NO2 groups;;
R4 represents a hydrogen atom or a phenyl group optionally substituted with one or more halogen atoms, and
X represents an oxygen or sulphur atom.
2. A method as claimed in Claim 1 in which the compound is applied as such or in the form of powders, wettable powders, solutions, aqueous suspensions or emulsions.
3. A method of treating plants as claimed in Claim 1 substantially as herein described with reference to any one of the Examples.
4. A fungicidal composition comprising a compound which is a 1 ,2,4-triazolidin-3-one or thione of the general formula:
in an amount of at least 0.1 % by weight and a carrier.
5. A composition as claimed in Claim 4 which includes an inert powder and/or water and/or solvent, optionally in the presence of a surfactant and/or wetting agent.
6. A composition as claimed in Claim 4 or Claim 5 in which the compound is 2-phenyl-5,5 di-n.propyl- 1 , 2,4-triazolidin-3-one.
7. A composition as claimed in Claim 4 or Claim 5 in which the compound is 2-(4 chlorophenyl)-5,5-dimethyl- 1,2,4-triazolidin-3-one.
8. A composition as claimed in Claim 4 or Claim 5 in which the compound is 2-(3,4 dichlorophenyl)-5,5-dimethyl-1,2,4-triazolidin-3-one.
9. A composition as claimed in Claim 4 or Claim 5 in which the compound is 2-(4 chlorophenyl) ,2,4-triazaspi ro[4,41-deca n-3-th ione.
10. A composition as claimed in Claim 4 or Claim 5 in which the compound is 2-(3-5 dichlorophenyl)-5,5-dimethyl-1,2,4-triazolidin-3-thione.
11. A composition as claimed in Claim 4 or Claim 5 in which the compound is 2-phenyl-5 methyl-5-n-propyl-1,2,4-triazolidin-3-one.
12. A composition as claimed in Claim 4 or Claim 5 in which the compound is 2-phenyl-5 methyl-5-i.butyl-1 ,2,4-triazolidin-3-one.
13. A composition as claimed in Claim 4 or Claim 5 in which the compound is 2-phenyl-5 methyl-5-ethyl-1 1,2,4-triazolidin-3-thione.
14. A composition as claimed in Claim 4 or Claim 5 in which the compound is 2-phenyl-5methyl-5-n.propyl-1,2,4-triazolidin-3-one.
15. Acomposition as claimed in Claim 4 or Claim 5 in which the compound is 2-phenyl5,5-di-n.propyl-1,2,4-triazolidine-3-thione.
16. A composition as claimed in Claim 4 or Claim 5 in which the compound is 2-(4 chlorophenyl)-5, 5-dimethyl-1 , 2,4-triazolidin-3-one.
17. A composition as claimed in Claim 4 or Claim 5 in which the compound is 2-(3chlorophenyl)-5,5-dimethyl-1,2,4-triazolidin-3-thione.
18. A composition as claimed in Claim 4 or Claim 5 in which the compound is 2-methyl1,2,4-triazo-spiro-[4,5]-decan-3-thione.
19. A cmposition as claimed in Claim 4 substantially as herein described with reference to any one of the Examples.
20. A method of treating plants to prevent or combat fungal infections comprising treating the plants with a composition as claimed in any one of Claims 4 to 1 9.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT23795/78A IT1096332B (en) | 1978-05-25 | 1978-05-25 | 1,2,4-TRIAZOLIDIN-3-ONI FUNGICIDAL E-TIONS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2024015A true GB2024015A (en) | 1980-01-09 |
| GB2024015B GB2024015B (en) | 1982-08-25 |
Family
ID=11210051
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7918106A Expired GB2024015B (en) | 1978-05-25 | 1979-05-24 | 1,2,4-triazolidin - 3 - ones and 1,2,4-triazolidin 3 - thiones fungicides |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS54154524A (en) |
| BE (1) | BE876555A (en) |
| DE (1) | DE2921308A1 (en) |
| ES (1) | ES480872A1 (en) |
| FR (1) | FR2426410A1 (en) |
| GB (1) | GB2024015B (en) |
| IT (1) | IT1096332B (en) |
| NL (1) | NL7903972A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007068422A1 (en) * | 2005-12-12 | 2007-06-21 | Phenion Gmbh & Co. Kg | Fungicidally or antimycotically active compounds |
-
1978
- 1978-05-25 IT IT23795/78A patent/IT1096332B/en active
-
1979
- 1979-05-21 NL NL7903972A patent/NL7903972A/en not_active Application Discontinuation
- 1979-05-22 JP JP6228079A patent/JPS54154524A/en active Pending
- 1979-05-22 FR FR7912958A patent/FR2426410A1/en active Granted
- 1979-05-24 GB GB7918106A patent/GB2024015B/en not_active Expired
- 1979-05-24 ES ES480872A patent/ES480872A1/en not_active Expired
- 1979-05-25 BE BE0/195398A patent/BE876555A/en unknown
- 1979-05-25 DE DE19792921308 patent/DE2921308A1/en not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007068422A1 (en) * | 2005-12-12 | 2007-06-21 | Phenion Gmbh & Co. Kg | Fungicidally or antimycotically active compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2426410B1 (en) | 1981-12-11 |
| IT7823795A0 (en) | 1978-05-25 |
| DE2921308A1 (en) | 1979-11-29 |
| IT1096332B (en) | 1985-08-26 |
| GB2024015B (en) | 1982-08-25 |
| JPS54154524A (en) | 1979-12-05 |
| FR2426410A1 (en) | 1979-12-21 |
| ES480872A1 (en) | 1980-08-16 |
| NL7903972A (en) | 1979-11-27 |
| BE876555A (en) | 1979-11-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |