CA1108046A - Fungicidal combinations - Google Patents
Fungicidal combinationsInfo
- Publication number
- CA1108046A CA1108046A CA299,331A CA299331A CA1108046A CA 1108046 A CA1108046 A CA 1108046A CA 299331 A CA299331 A CA 299331A CA 1108046 A CA1108046 A CA 1108046A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- formulation
- fungicidal
- treating
- 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.)
- Expired
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
- 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
- A01N47/08—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 one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
ABSTRACT
A fungicidal formulation comprising as one fungicidally active ingredient a triazole or pyrimidine compound of the formula :- or I(a) I(b) where X is chlorine or fluorine, and as a second fungicidally active ingredient a benzimidazole or aluminium salt of the formula :- or
A fungicidal formulation comprising as one fungicidally active ingredient a triazole or pyrimidine compound of the formula :- or I(a) I(b) where X is chlorine or fluorine, and as a second fungicidally active ingredient a benzimidazole or aluminium salt of the formula :- or
Description
q~ ~
1 The present invention relates to a method of treating funga~ lnfections of cultivated plants with novel combinations of chemicals and also provides fungicidal formulations containing said novel combinationsO
According to one aspect of the present inventlon therefore, there is provided a fungicidal formulation comprlsing as o~e fungicidally active ingredient a triazole or pyrimidine compound of the formula :-~ ~ ~ N ~ ~ Cl ~ 3--o l co C(CH3~3 ~N ~
~ I(b) where X is chlorine or fluorine9 and as a second fungicidally active ingredient a benzimidazole or aluminium salt of the formula :-~ C - NH-C-OCH3 ~ [C2H50-¦-O( ~ AL
~ H
i II(a~ II(b) I - 2 ~
.~, . .
1 associated with one or more inert~ non-phytotoxic carriers therefor.
All of the aorementioned compounds are known compounds and may be prepared by methods well-defined in the literature. The combinations of active ingredients defined in the above formulation are novel and have been found to be surprisingly effective in controlling or combatting fungal infections of cultivated plants, the combination of a compound of formula I(a) or I(b) and II(b) being particularly useful in controlling mildew infections of grapes whilst the combination of a formula I(a) or I(b) and for~ula II(a) compound has been found to be especially valuable in the treatment of cereal diseases such as powdery mlldew9 foot rot, and other foliar or ear diseases affecting cereals at the ripening 3tage.
According to a second aspect of the invention thereforeg there is provided a method of treating fungal infections of plants especially cereals and grapes which comprises applying to said plants a fungicidally effective amount of a fungicidal formulation as defined above~ In the aforesaid method, the formulatlon is preferably applied by foliar application at any time after crop emergence until harvesting takes place, the amount and frequency of application being de~ermined by the severity or expected severity of the fungal disease. However it is a feature of the invention and a particular advantage obtained from the use of the above-defined combinations that a reduced frequency of treatment7 for example only once every 2 to 3 weeks to control grape mildew infectionsg may be effectively employed thus achieving a valuable reduction in labour co~ts.
The preferred pyrimidine for use in grape treatment is that in which I ~ is chlorine whereas the formula I(b) compound in which X is fluorlne is preferred for use in connection with fungal infections of cereals~
I
I
Il ~
, . `~ ' -~ ~';, ll~ I' t' ~ `4~ ~
The components of the formulations of this invention may be applied sequentially or simultaneously to the plant being treated, the latter being preferred in accordance with the invention. The compound of formula I(a) is preferably applied in an amount of from 10 to 500g. per hectare and the compo~lnds of formula I(b) are preferably applied in sn amount of from 10 to lOOg~ ost preferably 1to 30g per hectare in the treatment of grapes~
whereas the compounds of formula II(a) or II(b) are preferably applied in amounts of from 100 to 3000g. per hectare. Thùs the ratio of compounds of formula I to compounds of fo~mula II in the combinations of the invention may range from 5:1 to 1:300 by weight~ Preferably the ratio of formula I(a) to formula II(a~ compound lies between 2:1 and 1:~5 with from 20 to 200g. per hectare of formula I(a) compound being applied, and the ratio ;
of formula I(b) to formula II(a) compound lies between 1:1 and 1-25 with from 20 to lOOg. per hectare of formula I(b) compound being applied, whilst from 100 to SOOg. per hectare of formula LI(a) compound may be used. Preferably the ratio of formula I(a) to formula II(b) compound ls in the range of 1:5 to 1:100 with again 20 to 200g. per hectare of the formula I(a) compound being used, and the ratio of formula I(b) to Eormula II(b) compound is in the range of 1:10 to 1:100 with 20 to lOOg. per hectare of formula I(b) compound being used~ with from 1000 to 2000g. per hectare of the compound of formula II(b) being employed. ~
The formula II(b) compound,aluminium sslt of ethylphosphite (AEP)~ is ! preferably used in comblnation with a further fungicide for example 1 ~ancozeb or- possibly folpet, 2-[(trichloromethyl)-thio~-lH-isolndole-1,3~2H)-i dio~e (see Phvtiarie Phytoe~armacie 1 (1977)). When used in con~unction with I` the further fungicide the ratio of AEP to said fun~icide will lie in the li range 3:1 to 1:2 by weight.
,., ~ . .
~ 6 l In order to simplify manufacture~ storage and transport~ the combinations of the formulae I and II compounds will be normally produced in concentrate form intended for dilution in wa~er to the degree necessary to enable the abovementioned application rates to be easily achieved. Such concentrated formulations may contain from 0.5 to 90%, preferably 5 to 90%, by weight of active ingredients associated with one or more inert non ph~totoxic ca~rier(s) therefor. Such formulations will usually be in the form o a wettable powder or dust~ or aqueous suspension, although it should be noted that aqueous suspensions of AEP tend to be unstable because of the relatively short half-life (approximately 100 da~s) of AEP in aqueous media. The concentrate formulations are intended for appropriate dilution with water prior to use. This formation of an aqueous dispersion can be carried out in conventional spray tanks suitable for the purpose.
Wettable powders or dusts comprlse an intimate mixture of ~he active ingredients, one or more inert carriers and appropriate surfactants~ The inert carrier may be chosen from the attapulgite clays, the montmorillonite clays, the diatomaceous earths, kaolins7 micas7 talcs and purified silicates.
Effective surfactants may be found among the sulfonated lignins, the naphthslene sulfonates and condensed naphthalene sulfonates, the alkyl succinates, the alkylbenzene sulfonates, the alkyl sulfates and nonionic surfactants such as ethylene oxide adducts of phenolO Illustrative of wettable powders falling within the scope of the in~ention are those having the following composition :
Wettable Pouders ~!~
Formula I compound0.25 to 10 Formula II compound 10 to 80 ¦ Surfactant~s) 0 to 10 ¦ Dispersing Agent 0 to 10 Anticaking agent 0 to 10 I~ert carrier~s) to 100 1 Aqueous suspensions and solutions comprise the active lngredients suspended or dissolved in water or suitable soLvents respectively together with any desired surfactants, thickening agents, antifreezing agents or preservatives. Suitable surfactants may be chosen from those mentioned above in connection with wettable powders Thickenin~
agents~ if used~ are normally chosen from appropriate cellulose materials and natural gums whilst glycols will generally be used when an antifreezing agent is required. Preservatives may be chosen from a wide range of materials such as the various paraben antibacterials, phenol, o chlorocresol9 phenyl mercuric nitrate and formaldehyde. Typical examplas of aqueous suspensions 9 falling within the scope of the inventions are :
~) Formula I compound 0.1 to 8 Formula II(a) compound 20 to 52 Surfactant(s~ 0 to 15 Thickening agent 0 to 3 Antifreezing agent 0 to 20 Preservative 0 to Antifoaming agent 0 to 0.5 Water to 100 ¦ Whilst the foregoing general examples will adequately demonstrate to those skilled in the art the types of concentrate compositions of use in the present invention, the following non-limitative Examples will serve to ~urther illustrate the formulation aspects of the present invention.
1 In these Examples~ the term "CCPM" represents the ormula I(b) compound in which X is chlorine whilst the re ated compound in which X is fluorine is representea by the latters "CFPM". Similarly~ the formula I(a) compound is denoted by the symboL "CTDB", the formula II(a) compound "MBC" and the fonmula II(b) compound "AF,P", EXAMPLES 1 to 8 The following wettable powders were prepared ~-(1) ~ ~ weight . CCPM 0-5 A~P 50,0 Sodium dioctylsulphosuccinate2.0 Ethox~lated nonylphenol 2.0 Sodium lignin sulphonate 3,0 Silica 6.0 Kaolin clay to 100.0
1 The present invention relates to a method of treating funga~ lnfections of cultivated plants with novel combinations of chemicals and also provides fungicidal formulations containing said novel combinationsO
According to one aspect of the present inventlon therefore, there is provided a fungicidal formulation comprlsing as o~e fungicidally active ingredient a triazole or pyrimidine compound of the formula :-~ ~ ~ N ~ ~ Cl ~ 3--o l co C(CH3~3 ~N ~
~ I(b) where X is chlorine or fluorine9 and as a second fungicidally active ingredient a benzimidazole or aluminium salt of the formula :-~ C - NH-C-OCH3 ~ [C2H50-¦-O( ~ AL
~ H
i II(a~ II(b) I - 2 ~
.~, . .
1 associated with one or more inert~ non-phytotoxic carriers therefor.
All of the aorementioned compounds are known compounds and may be prepared by methods well-defined in the literature. The combinations of active ingredients defined in the above formulation are novel and have been found to be surprisingly effective in controlling or combatting fungal infections of cultivated plants, the combination of a compound of formula I(a) or I(b) and II(b) being particularly useful in controlling mildew infections of grapes whilst the combination of a formula I(a) or I(b) and for~ula II(a) compound has been found to be especially valuable in the treatment of cereal diseases such as powdery mlldew9 foot rot, and other foliar or ear diseases affecting cereals at the ripening 3tage.
According to a second aspect of the invention thereforeg there is provided a method of treating fungal infections of plants especially cereals and grapes which comprises applying to said plants a fungicidally effective amount of a fungicidal formulation as defined above~ In the aforesaid method, the formulatlon is preferably applied by foliar application at any time after crop emergence until harvesting takes place, the amount and frequency of application being de~ermined by the severity or expected severity of the fungal disease. However it is a feature of the invention and a particular advantage obtained from the use of the above-defined combinations that a reduced frequency of treatment7 for example only once every 2 to 3 weeks to control grape mildew infectionsg may be effectively employed thus achieving a valuable reduction in labour co~ts.
The preferred pyrimidine for use in grape treatment is that in which I ~ is chlorine whereas the formula I(b) compound in which X is fluorlne is preferred for use in connection with fungal infections of cereals~
I
I
Il ~
, . `~ ' -~ ~';, ll~ I' t' ~ `4~ ~
The components of the formulations of this invention may be applied sequentially or simultaneously to the plant being treated, the latter being preferred in accordance with the invention. The compound of formula I(a) is preferably applied in an amount of from 10 to 500g. per hectare and the compo~lnds of formula I(b) are preferably applied in sn amount of from 10 to lOOg~ ost preferably 1to 30g per hectare in the treatment of grapes~
whereas the compounds of formula II(a) or II(b) are preferably applied in amounts of from 100 to 3000g. per hectare. Thùs the ratio of compounds of formula I to compounds of fo~mula II in the combinations of the invention may range from 5:1 to 1:300 by weight~ Preferably the ratio of formula I(a) to formula II(a~ compound lies between 2:1 and 1:~5 with from 20 to 200g. per hectare of formula I(a) compound being applied, and the ratio ;
of formula I(b) to formula II(a) compound lies between 1:1 and 1-25 with from 20 to lOOg. per hectare of formula I(b) compound being applied, whilst from 100 to SOOg. per hectare of formula LI(a) compound may be used. Preferably the ratio of formula I(a) to formula II(b) compound ls in the range of 1:5 to 1:100 with again 20 to 200g. per hectare of the formula I(a) compound being used, and the ratio of formula I(b) to Eormula II(b) compound is in the range of 1:10 to 1:100 with 20 to lOOg. per hectare of formula I(b) compound being used~ with from 1000 to 2000g. per hectare of the compound of formula II(b) being employed. ~
The formula II(b) compound,aluminium sslt of ethylphosphite (AEP)~ is ! preferably used in comblnation with a further fungicide for example 1 ~ancozeb or- possibly folpet, 2-[(trichloromethyl)-thio~-lH-isolndole-1,3~2H)-i dio~e (see Phvtiarie Phytoe~armacie 1 (1977)). When used in con~unction with I` the further fungicide the ratio of AEP to said fun~icide will lie in the li range 3:1 to 1:2 by weight.
,., ~ . .
~ 6 l In order to simplify manufacture~ storage and transport~ the combinations of the formulae I and II compounds will be normally produced in concentrate form intended for dilution in wa~er to the degree necessary to enable the abovementioned application rates to be easily achieved. Such concentrated formulations may contain from 0.5 to 90%, preferably 5 to 90%, by weight of active ingredients associated with one or more inert non ph~totoxic ca~rier(s) therefor. Such formulations will usually be in the form o a wettable powder or dust~ or aqueous suspension, although it should be noted that aqueous suspensions of AEP tend to be unstable because of the relatively short half-life (approximately 100 da~s) of AEP in aqueous media. The concentrate formulations are intended for appropriate dilution with water prior to use. This formation of an aqueous dispersion can be carried out in conventional spray tanks suitable for the purpose.
Wettable powders or dusts comprlse an intimate mixture of ~he active ingredients, one or more inert carriers and appropriate surfactants~ The inert carrier may be chosen from the attapulgite clays, the montmorillonite clays, the diatomaceous earths, kaolins7 micas7 talcs and purified silicates.
Effective surfactants may be found among the sulfonated lignins, the naphthslene sulfonates and condensed naphthalene sulfonates, the alkyl succinates, the alkylbenzene sulfonates, the alkyl sulfates and nonionic surfactants such as ethylene oxide adducts of phenolO Illustrative of wettable powders falling within the scope of the in~ention are those having the following composition :
Wettable Pouders ~!~
Formula I compound0.25 to 10 Formula II compound 10 to 80 ¦ Surfactant~s) 0 to 10 ¦ Dispersing Agent 0 to 10 Anticaking agent 0 to 10 I~ert carrier~s) to 100 1 Aqueous suspensions and solutions comprise the active lngredients suspended or dissolved in water or suitable soLvents respectively together with any desired surfactants, thickening agents, antifreezing agents or preservatives. Suitable surfactants may be chosen from those mentioned above in connection with wettable powders Thickenin~
agents~ if used~ are normally chosen from appropriate cellulose materials and natural gums whilst glycols will generally be used when an antifreezing agent is required. Preservatives may be chosen from a wide range of materials such as the various paraben antibacterials, phenol, o chlorocresol9 phenyl mercuric nitrate and formaldehyde. Typical examplas of aqueous suspensions 9 falling within the scope of the inventions are :
~) Formula I compound 0.1 to 8 Formula II(a) compound 20 to 52 Surfactant(s~ 0 to 15 Thickening agent 0 to 3 Antifreezing agent 0 to 20 Preservative 0 to Antifoaming agent 0 to 0.5 Water to 100 ¦ Whilst the foregoing general examples will adequately demonstrate to those skilled in the art the types of concentrate compositions of use in the present invention, the following non-limitative Examples will serve to ~urther illustrate the formulation aspects of the present invention.
1 In these Examples~ the term "CCPM" represents the ormula I(b) compound in which X is chlorine whilst the re ated compound in which X is fluorine is representea by the latters "CFPM". Similarly~ the formula I(a) compound is denoted by the symboL "CTDB", the formula II(a) compound "MBC" and the fonmula II(b) compound "AF,P", EXAMPLES 1 to 8 The following wettable powders were prepared ~-(1) ~ ~ weight . CCPM 0-5 A~P 50,0 Sodium dioctylsulphosuccinate2.0 Ethox~lated nonylphenol 2.0 Sodium lignin sulphonate 3,0 Silica 6.0 Kaolin clay to 100.0
(2) CFPM loO
AEP 50.0 Sodium lauryl sulphate 3.0 Sulphonated lignin 2.0 Diatomaceous earth to 100.0
AEP 50.0 Sodium lauryl sulphate 3.0 Sulphonated lignin 2.0 Diatomaceous earth to 100.0
(3) CTDB 0.5 ¦ Sodium alkyl ether sulphate5.0 Sulphite lye powder 3.0 Silica 4~0 Talc to 100.0 1 t4) ZL~
MBC 50.0 Sodium dioctyl sulphosuccinate 4.0 Sodium lignin sulphonate 1.5 Precîpitated silica 2.5 Attapulgi~e to 100.0 ~5) % b~ weight CFPM 3.0 Sodium allcylnaphthalene sulphonate 8.0 Diatomaceous earth 6.0 Montmorillonite to 100.0 (6) CTDB 12.0 Sodium salt o condensed napthalene sulphonic acids 5.0 Sodium tridecyl sulphate 2.0 ~0 Silica 5.0 Kaolin to 100.0 ~7) ~L~~L
CCPM L~0 ~ .~EP 30OO
Folpet 15.0 j Sodium lauryl sulphate 2,5 ¦ Sodium lignin sulphonate 4~0 Precipitated silica 8.0 l Kaolin to 100.0 - B -1 ~8) % bv wei~
CTDs 2.0 AEP 40~0 Mancozeb 20.0 S Ethoxylated nonyl phenol 2~0 Sodium dioctyl sulphosuccinate 2.0 Sodlum.lignin sulphonate 300 Hydrated sodium silicoaluminate 7.5 Talc to 100.0 In each Example, the active ingredients were carefully blended ~ith the specified exclpients in con~entional mixi~g equipment. The blend was then further milled in a fluid enargy mill to a size range of from 1 to 10 microns and finally the mixture was reblended and deaerated prior to being packaged.
EX MPLES 9 to.ll The following aqueous suspensions were prepared :-(9) ~L~2 CFPM 40~
Polyoxyethylene polyoxypropylene block copolymer 2,0 Xanthan gum 004 Silicone antifoam 0.1 Water to 100.0 ~0 _ 9 _ ( 10) ~
CTDB 2.5 MBC 50.0 Sodium lauryl sulphate 3.0 Bentonite 3.0 Ethylene glycol 5.0 Formaldehyde 0.2 Water to 100~0 (11) ~
CCPM 5~0 ~sC 40.0 Ethoxylated nonyl phenol 4~0 Hydroxymethyl cellulose 2.0 Silicone antifoam 0.15 Propylene glycol 6 0 Water to ~~
Both active ingredients, size rèduced by conventional means~ where appropriate, were dispersed in water containing the surfactant system, preservative and part of the thickening agent. The particle si~e of both actives was further reduced by liquid millingl the balance of the thickeni~g agent added, allowed to hydrate and the product diluted to Yolume with water.
~ 10
MBC 50.0 Sodium dioctyl sulphosuccinate 4.0 Sodium lignin sulphonate 1.5 Precîpitated silica 2.5 Attapulgi~e to 100.0 ~5) % b~ weight CFPM 3.0 Sodium allcylnaphthalene sulphonate 8.0 Diatomaceous earth 6.0 Montmorillonite to 100.0 (6) CTDB 12.0 Sodium salt o condensed napthalene sulphonic acids 5.0 Sodium tridecyl sulphate 2.0 ~0 Silica 5.0 Kaolin to 100.0 ~7) ~L~~L
CCPM L~0 ~ .~EP 30OO
Folpet 15.0 j Sodium lauryl sulphate 2,5 ¦ Sodium lignin sulphonate 4~0 Precipitated silica 8.0 l Kaolin to 100.0 - B -1 ~8) % bv wei~
CTDs 2.0 AEP 40~0 Mancozeb 20.0 S Ethoxylated nonyl phenol 2~0 Sodium dioctyl sulphosuccinate 2.0 Sodlum.lignin sulphonate 300 Hydrated sodium silicoaluminate 7.5 Talc to 100.0 In each Example, the active ingredients were carefully blended ~ith the specified exclpients in con~entional mixi~g equipment. The blend was then further milled in a fluid enargy mill to a size range of from 1 to 10 microns and finally the mixture was reblended and deaerated prior to being packaged.
EX MPLES 9 to.ll The following aqueous suspensions were prepared :-(9) ~L~2 CFPM 40~
Polyoxyethylene polyoxypropylene block copolymer 2,0 Xanthan gum 004 Silicone antifoam 0.1 Water to 100.0 ~0 _ 9 _ ( 10) ~
CTDB 2.5 MBC 50.0 Sodium lauryl sulphate 3.0 Bentonite 3.0 Ethylene glycol 5.0 Formaldehyde 0.2 Water to 100~0 (11) ~
CCPM 5~0 ~sC 40.0 Ethoxylated nonyl phenol 4~0 Hydroxymethyl cellulose 2.0 Silicone antifoam 0.15 Propylene glycol 6 0 Water to ~~
Both active ingredients, size rèduced by conventional means~ where appropriate, were dispersed in water containing the surfactant system, preservative and part of the thickening agent. The particle si~e of both actives was further reduced by liquid millingl the balance of the thickeni~g agent added, allowed to hydrate and the product diluted to Yolume with water.
~ 10
Claims (8)
1. A fungicidal formulation comprising as one fungicidally active ingredient a triazole or pyrimidine compound of the formula :- or I(a) I(b) where X is chlorine or fluorine, and as a second fungicidally active ingredient a benzimidazole or aluminium salt of the formula :- or II(a) II(b) associated with one or more inert, non-phytotoxic carrier(s) therefor, said compounds of formula I and formula II being present in said fungicidal formulation in a ratio of the formula I compound to the formula II compound which ranges from 5:1 to 1:300 by weight.
2. A fungicidal formulation as claimed in claim 1, which comprises from 0.5 to 90% by weight of active ingredients, the remainder consisting of one or more inert, non-phytotoxio carrier(s) therefor.
3. A fungicidal formulation as claimed in claim 2, which comprises a compound of formula I(b) in which X is chlorine.
4. A fungicidal formulation as claimed in Claim 1 which comprises a compound of formula II(b) and additionally 2-[(trichloromethyl)-thio]-lH-isoindole-1,3(2H)-dione in a ratio by weight of from 3:1 to 1:1 of said compound of formula II(b) to said dione.
5. A method of preparing a fungicidal formulation as claimed in claim 1 or claim 2 which comprises admixing a Formula I compound and a Formula II compound, in a ratio of said formula I compound to said formula II compound which ranges from 5:1 to 1:300, with one or more inert, non phlytotoxic carriers) therefor.
6. A method of treating or preventing fungal infections in plants which comprises treating said plants with a formulation as claimed in claim 1 or claim 3 or with a formulation as claimed in claim 4 diluted with water.
7. A method for treating or preventing downy mildew in grapes which comprises spraying said grapes with an aqueous dispersion of a formulation as claimed in claim 1 or 2 which comprises a pyrimidine of formula I(b) in which X is chlorine and the aluminium salt of formula II(b).
8. A method for treating or preventing fungal infections in cereals which comprises spraying said cereals with an aqueous dispersion of a formulation according to claim 1 which comprises a pyrimidine of formula I(b) in which X is fluorine and the benzimidazole of formula II(a).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB12972/77A GB1596380A (en) | 1977-03-28 | 1977-03-28 | Fungicidal combinations |
| GB12972/77 | 1977-03-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1108046A true CA1108046A (en) | 1981-09-01 |
Family
ID=10014480
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA299,331A Expired CA1108046A (en) | 1977-03-28 | 1978-03-20 | Fungicidal combinations |
Country Status (34)
| Country | Link |
|---|---|
| JP (1) | JPS53121932A (en) |
| AR (2) | AR227124A1 (en) |
| AT (1) | AT362195B (en) |
| AU (1) | AU515204B2 (en) |
| BE (1) | BE865215A (en) |
| BG (4) | BG30167A4 (en) |
| BR (1) | BR7801746A (en) |
| CA (1) | CA1108046A (en) |
| CH (1) | CH629363A5 (en) |
| CS (4) | CS198292B2 (en) |
| DD (1) | DD135031A5 (en) |
| DE (2) | DE2858350C2 (en) |
| DK (1) | DK149442C (en) |
| ES (1) | ES468098A1 (en) |
| FR (4) | FR2390096A1 (en) |
| GB (1) | GB1596380A (en) |
| GR (1) | GR64791B (en) |
| HU (2) | HU179506B (en) |
| IE (1) | IE46690B1 (en) |
| IL (1) | IL54318A (en) |
| IN (1) | IN147690B (en) |
| IT (1) | IT1105157B (en) |
| LU (1) | LU79285A1 (en) |
| MX (1) | MX5640E (en) |
| NL (1) | NL7803064A (en) |
| NO (4) | NO147260C (en) |
| NZ (1) | NZ186757A (en) |
| PL (4) | PL112622B1 (en) |
| PT (1) | PT67801A (en) |
| RO (4) | RO78273A (en) |
| SE (5) | SE447783B (en) |
| SU (1) | SU1409119A3 (en) |
| TR (1) | TR20072A (en) |
| ZA (1) | ZA781700B (en) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2560510C2 (en) * | 1975-11-26 | 1989-02-16 | Bayer Ag, 5090 Leverkusen, De | |
| IT1143721B (en) * | 1977-12-01 | 1986-10-22 | Sipcam Spa | FUNGICIDAL COMPOSITION FOR THE FIGHT AGAINST PLANT DISEASES |
| DE2846038A1 (en) * | 1978-10-23 | 1980-05-08 | Basf Ag | 1,2,4-TRIAZOLE DERIVATIVES, THEIR PRODUCTION AND USE |
| DE3208142A1 (en) * | 1982-03-06 | 1983-09-08 | Bayer Ag, 5090 Leverkusen | FUNGICIDAL AGENT |
| FR2524261A1 (en) * | 1982-04-01 | 1983-10-07 | Rhone Poulenc Agrochimie | FENARIMOL FUNGICIDE POWDER COMPOSITION |
| GB8629360D0 (en) * | 1986-12-09 | 1987-01-21 | Sandoz Ltd | Fungicides |
| JPH01167287U (en) * | 1988-05-16 | 1989-11-24 | ||
| DE3818903A1 (en) * | 1988-06-03 | 1989-12-14 | Stama Maschinenfabrik Gmbh | DRILLING AND MILLING PLANT |
| JPH0274094U (en) * | 1988-11-28 | 1990-06-06 | ||
| JPH071190Y2 (en) * | 1989-03-01 | 1995-01-18 | 狭山精密工業株式会社 | Spiral control mechanism in pachinko ball lifting device |
| NZ260462A (en) * | 1994-05-05 | 1996-04-26 | Horticulture & Food Res Inst | Tree treatment and composition comprising phosphorous acid, a bioprecursor or a salt thereof and a triazole |
| FR2732191B1 (en) * | 1995-03-30 | 2000-12-29 | Rhone Poulenc Agrochimie | ANTIFUNGAL TREATMENT OF BANANA TREES |
| GB0811079D0 (en) * | 2008-06-17 | 2008-07-23 | Syngenta Participations Ag | Herbicide formulation |
| CN103583541B (en) * | 2012-08-17 | 2015-11-11 | 陕西美邦农药有限公司 | A kind of bactericidal composition containing Fenarimol |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1569940A (en) * | 1967-04-27 | 1969-06-06 | ||
| FR2140205B1 (en) | 1971-06-04 | 1977-12-23 | Oreal | |
| US3912752A (en) * | 1972-01-11 | 1975-10-14 | Bayer Ag | 1-Substituted-1,2,4-triazoles |
| US3869456A (en) * | 1972-03-13 | 1975-03-04 | Lilly Co Eli | Synthesis of 5-pyrimidinecarbinols |
| US3868244A (en) | 1972-03-13 | 1975-02-25 | Lilly Co Eli | Plant growth regulation |
| DE2303757A1 (en) * | 1973-01-26 | 1974-08-15 | Hoechst Ag | Fungicidal wettable powders contg. benzimidazole carbamates - mixed with powdered carrier, penetrating agent, but without emulsifying agents |
| DE2354467C3 (en) * | 1973-10-31 | 1981-07-30 | Hoechst Ag, 6000 Frankfurt | Fungicidal dispersions based on benzimidazole methyl carbamate |
| DE2456627C2 (en) * | 1973-12-14 | 1984-05-10 | PEPRO - Société pour le Développement et la Vente de Spécialités Chimiques, Lyon | Fungicidal agents based on phosphonic acid esters |
| FR2254276B1 (en) * | 1973-12-14 | 1977-03-04 | Philagro Sa | |
| FR2279331A1 (en) * | 1974-07-24 | 1976-02-20 | Hoechst Ag | Fungicidal wettable powders contg. benzimidazole carbamates - mixed with powdered carrier, penetrating agent, but without emulsifying agents |
| DE2560510C2 (en) * | 1975-11-26 | 1989-02-16 | Bayer Ag, 5090 Leverkusen, De |
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1977
- 1977-03-28 GB GB12972/77A patent/GB1596380A/en not_active Expired
-
1978
- 1978-03-15 IT IT48444/78A patent/IT1105157B/en active
- 1978-03-20 CA CA299,331A patent/CA1108046A/en not_active Expired
- 1978-03-20 IN IN295/CAL/78A patent/IN147690B/en unknown
- 1978-03-20 PT PT67801A patent/PT67801A/en unknown
- 1978-03-20 SE SE7803184A patent/SE447783B/en not_active IP Right Cessation
- 1978-03-20 FR FR7807978A patent/FR2390096A1/en active Granted
- 1978-03-20 MX MX786944U patent/MX5640E/en unknown
- 1978-03-21 CH CH306178A patent/CH629363A5/en not_active IP Right Cessation
- 1978-03-21 RO RO7899323A patent/RO78273A/en unknown
- 1978-03-21 DE DE2858350A patent/DE2858350C2/de not_active Expired
- 1978-03-21 IL IL54318A patent/IL54318A/en unknown
- 1978-03-21 AR AR271494A patent/AR227124A1/en active
- 1978-03-21 GR GR55758A patent/GR64791B/en unknown
- 1978-03-21 RO RO7899324A patent/RO78274A/en unknown
- 1978-03-21 DK DK127978A patent/DK149442C/en not_active IP Right Cessation
- 1978-03-21 DE DE2812287A patent/DE2812287C2/en not_active Expired
- 1978-03-21 RO RO7899325A patent/RO78260A/en unknown
- 1978-03-21 RO RO7893574A patent/RO73042A/en unknown
- 1978-03-21 ES ES468098A patent/ES468098A1/en not_active Expired
- 1978-03-21 BR BR7801746A patent/BR7801746A/en unknown
- 1978-03-22 NO NO781040A patent/NO147260C/en unknown
- 1978-03-22 BG BG7841508A patent/BG30167A4/en unknown
- 1978-03-22 NL NL7803064A patent/NL7803064A/en not_active Application Discontinuation
- 1978-03-22 LU LU79285A patent/LU79285A1/en unknown
- 1978-03-22 NZ NZ186757A patent/NZ186757A/en unknown
- 1978-03-22 BG BG7839128A patent/BG29863A3/en unknown
- 1978-03-22 AT AT203678A patent/AT362195B/en not_active IP Right Cessation
- 1978-03-22 BG BG7841507A patent/BG30166A4/en unknown
- 1978-03-22 BG BG7841506A patent/BG30165A4/en unknown
- 1978-03-22 DD DD78204345A patent/DD135031A5/en unknown
- 1978-03-22 AU AU34430/78A patent/AU515204B2/en not_active Expired
- 1978-03-22 BE BE6046404A patent/BE865215A/en not_active IP Right Cessation
- 1978-03-23 TR TR20072A patent/TR20072A/en unknown
- 1978-03-23 ZA ZA00781700A patent/ZA781700B/en unknown
- 1978-03-23 HU HU78LI322A patent/HU179506B/en unknown
- 1978-03-23 IE IE588/78A patent/IE46690B1/en unknown
- 1978-03-23 HU HU812978A patent/HU188701B/en unknown
- 1978-03-24 CS CS789185A patent/CS198292B2/en unknown
- 1978-03-24 PL PL1978216611A patent/PL112622B1/en unknown
- 1978-03-24 JP JP3402678A patent/JPS53121932A/en active Granted
- 1978-03-24 CS CS789183A patent/CS198290B2/en unknown
- 1978-03-24 SU SU782594402A patent/SU1409119A3/en active
- 1978-03-24 PL PL1978216612A patent/PL112286B1/en unknown
- 1978-03-24 PL PL1978205555A patent/PL108903B1/en unknown
- 1978-03-24 CS CS789184A patent/CS198291B2/en unknown
- 1978-03-24 PL PL1978216610A patent/PL112146B1/en unknown
- 1978-03-24 CS CS781922A patent/CS198289B2/en unknown
- 1978-09-08 FR FR7825893A patent/FR2390097A1/en active Granted
- 1978-09-08 FR FR7825894A patent/FR2390098A1/en active Granted
- 1978-09-08 FR FR7825895A patent/FR2390099B1/fr not_active Expired
-
1981
- 1981-02-02 AR AR284171A patent/AR225793A1/en active
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1982
- 1982-05-07 NO NO821513A patent/NO148241C/en unknown
- 1982-05-07 NO NO821512A patent/NO148622C/en unknown
- 1982-05-07 NO NO821514A patent/NO148621C/en unknown
-
1983
- 1983-03-23 SE SE8301606A patent/SE454398B/en not_active IP Right Cessation
-
1986
- 1986-05-30 SE SE8602470A patent/SE8602470D0/en not_active Application Discontinuation
-
1987
- 1987-08-19 SE SE8703223A patent/SE8703223L/en not_active Application Discontinuation
- 1987-08-19 SE SE8703224A patent/SE8703224D0/en not_active Application Discontinuation
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