US20110003011A1 - Fungicidal active compound combinations - Google Patents
Fungicidal active compound combinations Download PDFInfo
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- US20110003011A1 US20110003011A1 US12/832,460 US83246010A US2011003011A1 US 20110003011 A1 US20110003011 A1 US 20110003011A1 US 83246010 A US83246010 A US 83246010A US 2011003011 A1 US2011003011 A1 US 2011003011A1
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- GQNLTLIFCWNUJF-UHFFFAOYSA-N CCNSO(O)N(SC(F)(Cl)Cl)C1=CC=CC=C1 Chemical compound CCNSO(O)N(SC(F)(Cl)Cl)C1=CC=CC=C1 GQNLTLIFCWNUJF-UHFFFAOYSA-N 0.000 description 1
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- OTGOTUCHLNLTAY-UHFFFAOYSA-N COC(=O)NC1NC2=CC=CC=C2N1 Chemical compound COC(=O)NC1NC2=CC=CC=C2N1 OTGOTUCHLNLTAY-UHFFFAOYSA-N 0.000 description 1
- LDVVMCZRFWMZSG-UHFFFAOYSA-N O=C1C2CC=CCC2C(=O)N1SC(Cl)(Cl)Cl Chemical compound O=C1C2CC=CCC2C(=O)N1SC(Cl)(Cl)Cl LDVVMCZRFWMZSG-UHFFFAOYSA-N 0.000 description 1
- UZCGKGPEKUCDTF-UHFFFAOYSA-N O=[N+]([O-])C1=CC(C(F)(F)F)=C(Cl)C([N+](=O)[O-])=C1NC1=C(Cl)C=C(C(F)(F)F)C=N1 Chemical compound O=[N+]([O-])C1=CC(C(F)(F)F)=C(Cl)C([N+](=O)[O-])=C1NC1=C(Cl)C=C(C(F)(F)F)C=N1 UZCGKGPEKUCDTF-UHFFFAOYSA-N 0.000 description 1
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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
- A01N37/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides containing at least one oxygen or sulfur atom being directly attached to the same aromatic ring system
Definitions
- the present application relates to novel active compound combinations which consist of a compound of the formula I
- the active compound of the formula (I) is known (EP-A-339,418).
- the components additionally present in the combinations according to the invention are also known.
- the active compound combinations according to the invention contain at least one active compound from the compounds of the groups (A) to (II). They may also moreover contain further fungicidally active admixed components.
- the active compounds are present in the active compound combinations according to the invention in certain weight ratios, the synergistic effect is seen particularly distinct.
- the weight ratios of the active compounds in the active compound combinations can be varied with a relatively wide range. In general, the following are proportioned to 1 part by weight of active compound of the formula (I)
- 0.5 to 50 part by weight preferably 0.5 to 10 parts by weight of active compound propineb (D) 0.5 to 50 parts by weight, preferably 0.5 to 10 parts by weight of active compound mancozeb (F) 0.5 to 50 parts by weight, preferably 0.5 to 10 parts by weight of active compound TMTD (E) 0.5 to 50 parts by weight, preferably 0.5 to 10 parts by weight of active compound metiram (W) 0.5 to 50 parts by weight, preferably 0.5 to 20 parts by weight of active compound dichlofluanid (A) 0.5 to 50 parts by weight, preferably 0.5 to 20 parts by weight of active compound tolylfluanid (B) 0.5 to 50 parts by weight, preferably 0.5 to 20 parts by weight of active compound phaltan (M) 0.5 to 50 parts by weight, preferably 0.5 to 50 parts by weight of active compound captan (I)
- the active compound combinations according to the invention have very good fungicidal properties and can be employed in particular for the control of phytopathogenic fungi, such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes etc.
- the active compound combinations according to the invention are very particularly suitable for the control of cereal diseases, such as Erysiphe, Cochliobolus, Pyrenophora and Leptosphaeria , and against fungal attack on vegetables, grapes and fruit, for example against Venturia on apples, Botrytis on beans and Phytophthora on tomatoes.
- cereal diseases such as Erysiphe, Cochliobolus, Pyrenophora and Leptosphaeria
- fungal attack on vegetables, grapes and fruit for example against Venturia on apples, Botrytis on beans and Phytophthora on tomatoes.
- the good plant tolerability of the active compound combinations in the concentrations to necessary for the control of plant diseases enables a treatment of above-ground parts of plants, of plants and seeds, and of the soil.
- the active compound combinations according to the invention can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine capsules in polymeric substances and in coating compositions for seeds, as well as ULV formulations.
- customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine capsules in polymeric substances and in coating compositions for seeds, as well as ULV formulations.
- formulations are produced in a known manner, for example by mixing the active compounds or the active compound combinations with extenders, that is, liquid solvents, liquefied gases under pressure, and/or solid carriers, optionally with the use of surface-active agents, that is, emulsifying agents and/or dispersing agents, and/or foam-forming agents.
- extenders that is, liquid solvents, liquefied gases under pressure, and/or solid carriers
- surface-active agents that is, emulsifying agents and/or dispersing agents, and/or foam-forming agents.
- organic solvents can, for example, also be used as auxiliary solvents.
- liquid solvents there are suitable in the main: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example mineral oil fractions, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, as well as water.
- aromatics such as xylene, toluene or alkylnaphthalenes
- chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride
- liquefied gaseous extenders or carriers liquids which are gaseous at ambient temperature and under atmospheric pressure, for example aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
- aerosol propellants such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
- solid carriers there are suitable: for example ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly-disperse silica, alumina and silicates.
- solid carriers for granules there are suitable: for example crushed and fractionated natural minerals such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks.
- emulsifying- and/or foam-forming agents there are suitable: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates alkyl sulphates, arylsulphonates as well as albumen hydrolysis products.
- dispersing agents there are suitable: for example lignin-sulphite waste liquors and methylcellulose.
- Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or lattices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations.
- Other additives can be mineral and vegetable oils.
- colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
- organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs
- trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
- the formulations in general contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
- the active compound combinations according to the invention can be present in the formulations as a mixture with other known active compounds, such as fungicides, insecticides, acaricides and herbicides, as well as in mixtures with fertilizers or plant growth regulators.
- the active compound combinations can be used as such or in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions, suspensions wettable powders, soluble powders and granules.
- the active compound concentrations in the use forms can be varied within a substantial range. They are, in general, between 1 and 0.0001% by weight, preferably between 0.5 and 0.001%.
- active compound concentrations of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02% by weight, are required at the site of action.
- the good fungicidal action of the active compound combinations according to the invention can be seen from the following Examples. While the individual active compounds have weaknesses in their fungicidal action, the combinations exhibit an action which extends beyond a simple additive action.
- a synergistic effect is always present with fungicides if the fungicidal action of the active compound combinations is greater than the sum of the actions of the individually applied active compounds.
- the combination is superadditive in its action, i.e. a synergistic effect is present.
- the actually observed degree of efficacy must be greater than the value for the expected degree of efficacy (E) calculated from the abovementioned formula.
- active compound formulations (individual active compounds or active compound combinations) are diluted with water to the desired concentration in each case.
- the plants are placed in a greenhouse at a temperature of 15° C. and a relative atmospheric humidity of about 80%.
- Evaluation is effected 10 days after the inoculation.
- active compound 1 part by weight of active compound is mixed with the stated amount of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
- the plants are placed in a greenhouse at a temperature of about 20° C. and a relative atmospheric humidity of about 80%, in order to promote-the development of powdery mildew pustules.
- Evaluation is carried out 7 days after the inoculation.
- active compound 1 part by weight of active compound is mixed with the stated amount of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
- the plants are placed in a greenhouse at a temperature of about 20° C. and a relative atmospheric humidity of about 80%, in order to promote the development of powdery mildew pustules.
- Evaluation is carried out 7 days after the inoculation.
- active compound 1 part by weight of active compound is mixed with the stated amount of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
- the plants are placed in a greenhouse at a temperature of about 20° C. and a relative atmospheric humidity of about 80%, in order to promote the development of powdery mildew pustules.
- Evaluation is carried out 7 days after the inoculation.
- the plants are placed in a greenhouse at a temperature of 15° C. and a relative atmospheric humidity of about 80%.
- active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
- the plants are placed in a greenhouse at a temperature of 20° and a relative atmospheric humidity of about 80%.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Zoology (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
- This application is a divisional of U.S. Ser. No. 10/860,868 filed Jun. 3, 2004, now allowed, which is a division of Ser. No. 10/022,136, filed on Dec. 13, 2001, now U.S. Pat. No. 6,776,994, which is a division of Ser. No. 09/736,917, filed on Dec. 14, 2000, now U.S. Pat. No. 6,365,195, which is a division of Ser. No. 09/541,950, filed on Apr. 3, 2000, now U.S. Pat. No. 6,235,744, which is a division of Ser. No. 09/249,690, filed on Feb. 12, 1999, U.S. Pat. No. 6,071,940, now U.S. Pat. No. 6,071,940, which is a division of Ser. No. 08/846,872, filed on May 1, 1997, now U.S. Pat. No. 5,922,762, which is a division of Ser. No. 08/629,245, filed on Apr. 8, 1996, now U.S. Pat. No. 5,672,619, which is a divisional of Ser. No. 08/462,408, filed on Jun. 5, 1995, now U.S. Pat. No. 5,532,262, which is a continuation of Ser. No. 08/232,923, filed on Apr. 25, 1994, now abandoned.
- The present application relates to novel active compound combinations which consist of a compound of the formula I
- on the one hand and other known fungicidal active compounds on the other hand and are very highly suitable for the control of phytopathogenic fungi.
- It is already known that the compounds of the formula (I) has fungicidal properties (cf. EP-A 339,418). The activity of this substance is good; however, in some cases it leaves something to be desired at low application rates.
- It is also already known that numerous azole derivatives, aromatic carboxylic acid derivatives, morpholine compounds and other heterocycles can be employed for the control of fungi (cf. K. H. Büchel “Pflanzenschutz and Schädlingsbekämpfung” [Plant protection and pest control] pages 87, 136, 140, 141 and 146 to 153, Georg Thieme Verlag, Stuttgart 1977).
- The action of the substances concerned, however, is not always satisfactory at low application rates.
- It has now been found that the new active compound combinations of a compound of the formula I
- and
(A) dichlofluanid of the formula - and/or
(B) tolylfluanid of the formula - and/or
(C) tetrachloro-isophthalo-dinitrile of the formula - and/or
(D) propineb of the formula - and/or
(E) tetramethyl-thiuram disulphide of the formula - and/or
(F) mancozeb of the formula - and/or
(G) anilazine of the formula - and/or
(H) copper oxychloride
and/or
(I) captan of the formula - and/or
(K) a morpholine derivative of the formula - and/or
(L) dithianone of the formula - and/or
(M) phaltan of the formula - and/or
(N) cymoxanil of the formula - and/or
(O) methyl benzimidazole-2-carbamate of the formula - and/or
(P) fosetyl of the formula -
- or its aluminium adduct
and/or
(Q) metalaxyl of the formula
- or its aluminium adduct
- and/or
(R) oxadixyl of the formula - and/or
(S) fluazinam of the formula - and/or
(T) 1-(4-chlorophenyl)-4,4-dimethyl-3-(1,2,4-triazol-1-yl-ethyl)-pentan-3-ol of the formula - and/or
(U) an azole derivative of the formula - and/or
(V) an azole derivative from the group consisting of
a) difenconazole
b) penconazole
c) flusilazole
d) hexaconazole
e) myclobutanil
f) prochloraz
g) fluquinconazole
h) epoxiconazole
i) fenpropidin
j) perifenox
k) 8-t-butyl-2-(N-ethyl-N-n-propylamino)-methyl-1,4-dioxaspiro[4,5]decane
and/or
(W) metiram
and/or
(X) pyrimethanil
and/or
(Y) diethofencarb
and/or
(Z) mepanipyrim and/or cyprodinyl
and/or
(α) phenylpyrrole and/or
(β) iprodione
and/or
(Γ) vinclozolin
and/or
(δ) procymidone
and/or
(e) benomyl
and/or
(⊖) thiophanate and/or -
- thiophanate-methyl
and/or
(II) sulphur
and/or
(n) compounds of the formula
- thiophanate-methyl
- and/or
- have very good fungicidal properties.
- The active compound of the formula (I) is known (EP-A-339,418). The components additionally present in the combinations according to the invention are also known.
- In addition to the active compound of the formula (I), the active compound combinations according to the invention contain at least one active compound from the compounds of the groups (A) to (II). They may also moreover contain further fungicidally active admixed components.
- If the active compounds are present in the active compound combinations according to the invention in certain weight ratios, the synergistic effect is seen particularly distinct. However, the weight ratios of the active compounds in the active compound combinations can be varied with a relatively wide range. In general, the following are proportioned to 1 part by weight of active compound of the formula (I)
- 0.5 to 50 part by weight, preferably
0.5 to 10 parts by weight of active compound propineb (D)
0.5 to 50 parts by weight, preferably
0.5 to 10 parts by weight of active compound mancozeb (F)
0.5 to 50 parts by weight, preferably
0.5 to 10 parts by weight of active compound TMTD (E)
0.5 to 50 parts by weight, preferably
0.5 to 10 parts by weight of active compound metiram (W)
0.5 to 50 parts by weight, preferably
0.5 to 20 parts by weight of active compound dichlofluanid (A)
0.5 to 50 parts by weight, preferably
0.5 to 20 parts by weight of active compound tolylfluanid (B)
0.5 to 50 parts by weight, preferably
0.5 to 20 parts by weight of active compound phaltan (M)
0.5 to 50 parts by weight, preferably
0.5 to 50 parts by weight of active compound captan (I) -
- 1 to 50 parts by weight, preferably
- 1 to 20 parts by weight of active compound Cu oxychloride (H)
- 1 to 50 parts by weight, preferably
- 1 to 20 parts by weight of active compound sulphur (II)
0.5 to 50 parts by weight, preferably
0.5 to 10 parts by weight of active compound anilazine (G)
0.5 to 50 parts by weight, preferably
0.5 to 10 parts by weight of active compound chlorothalonil (C)
0.5 to 50 parts by weight, preferably
0.5 to 10 parts by weight of active compound dithianon (L)
0.1 to 10 parts by weight, preferably
0.5 to 5 parts by weight of active compound fluazinam (S)
0.1 to 10 parts by weight, preferably
0.5 to 5 parts by weight of active compound pyrimethanil (X)
0.1 to 10 parts by weight, preferably
0.5 to 5 parts by weight of active compound diethofencarb (Y)
0.1 to 10 parts by weight, preferably
0.5 to 5 parts by weight of active compound mepanipyrim (Z)
0.1 to 10 parts by weight, preferably
0.5 to 5 parts by weight of active compound phenylpyrrole (Saphire) (α) - 0.1 20 parts by weight, preferably
0.5 to 10 parts by weight of active compound iprodione (β)
0.1 to 20 parts by weight, preferably
0.5 to 10 parts by weight of active compound vinclozolin (γ)
0.1 to 20 parts by weight, preferably
0.5 to 10 parts by weight of active compound procymidone (δ)
0.1 to 10 parts by weight, preferably
0.25 to 5 parts by weight of active compound benomyl (ε)
0.1 to 10 parts by weight, preferably
0.25 to 5 parts by weight of active compound carbendazim (o)
0.1 to 10 parts by weight, preferably
0.25 to 5 parts by weight of active compound thiophanate-methyl (Q)
0.1 to 10 parts by weight, preferably
0.25 to 5 parts by weight of active compound cymoxanil (N)
0.1 to 10 parts by weight, preferably
0.25 to 5 parts by weight of active compound metalaxyl (Q)
0.1 to 10 parts by weight, preferably
0.25 to 5 parts by weight of active compound oxadixyl (R)
0.1 to 10 parts by weight, preferably
0.2 to 5 parts by weight of active compound dimethomorph (K)
0.1 to 20 parts by weight, preferably
0.2 to 10 parts by weight of active compound Al fosetyl (P)
0.01 to 10 parts by weight, preferably
0.025 to 5 parts by weight of active compound tebuconazole (T)
0.1 to 10 parts by weight, preferably
0.025 to 5 parts by weight of active compound triadimefon (U XIXc)
0.01 to 10 parts by weight, preferably
0.025 to 5 parts by weight of active compound triadimenol (U XIXa)
0.01 to 10 parts by weight, preferably
0.025 to 5 parts by weight of active compound bitertanol (U XIXb)
0.01 to 10 parts by weight, preferably
0.025 to 5 parts by weight of active compound difenconazole (Va)
0.01 to 10 parts by weight, preferably
0.025 to 5 parts by weight of active compound penconazole (Vb)
0.01 to 10 parts by weight, preferably
0.025 to 5 parts by weight of active compound flusilazole (Vc)
0.01 to 10 parts by weight, preferably
0.025 to 5 parts by weight of active compound hexaconazole (Vd)
0.01 to 10 parts by weight, preferably
0.025 to 5 parts by weight of active compound myclobutanil (Ve)
0.01 to 10 parts by weight, preferably
0.025 to 5 parts by weight of active compound prochloraz (Vf)
0.01 to 10 parts by weight, preferably
0.025 to 5 parts by weight of active compound of formula ({acute over (η)}a)
0.01 to 10 parts by weight, preferably
0.025 to 5 parts by weight of active compound of formula ({acute over (η)}b)
- The active compound combinations according to the invention have very good fungicidal properties and can be employed in particular for the control of phytopathogenic fungi, such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes etc.
- The active compound combinations according to the invention are very particularly suitable for the control of cereal diseases, such as Erysiphe, Cochliobolus, Pyrenophora and Leptosphaeria, and against fungal attack on vegetables, grapes and fruit, for example against Venturia on apples, Botrytis on beans and Phytophthora on tomatoes.
- The good plant tolerability of the active compound combinations in the concentrations to necessary for the control of plant diseases enables a treatment of above-ground parts of plants, of plants and seeds, and of the soil.
- The active compound combinations according to the invention can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine capsules in polymeric substances and in coating compositions for seeds, as well as ULV formulations.
- These formulations are produced in a known manner, for example by mixing the active compounds or the active compound combinations with extenders, that is, liquid solvents, liquefied gases under pressure, and/or solid carriers, optionally with the use of surface-active agents, that is, emulsifying agents and/or dispersing agents, and/or foam-forming agents. In the case of the use of water as an extender, organic solvents can, for example, also be used as auxiliary solvents. As liquid solvents, there are suitable in the main: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example mineral oil fractions, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, as well as water. By liquefied gaseous extenders or carriers are meant liquids which are gaseous at ambient temperature and under atmospheric pressure, for example aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide. As solid carriers there are suitable: for example ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly-disperse silica, alumina and silicates. As solid carriers for granules there are suitable: for example crushed and fractionated natural minerals such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks. As emulsifying- and/or foam-forming agents there are suitable: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates alkyl sulphates, arylsulphonates as well as albumen hydrolysis products. As dispersing agents there are suitable: for example lignin-sulphite waste liquors and methylcellulose.
- Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or lattices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Other additives can be mineral and vegetable oils.
- It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
- The formulations in general contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
- The active compound combinations according to the invention can be present in the formulations as a mixture with other known active compounds, such as fungicides, insecticides, acaricides and herbicides, as well as in mixtures with fertilizers or plant growth regulators.
- The active compound combinations can be used as such or in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions, suspensions wettable powders, soluble powders and granules.
- They are used in the customary manner, for example by watering, spraying, atomizing, scattering, dusting, brushing on, as a powder for dry seed treatment, as a solution for seed treatment, as a water-soluble powder for seed treatment, as a water-dispersible powder for slurry treatment, or seed-coating.
- In the treatment of parts of plants, the active compound concentrations in the use forms can be varied within a substantial range. They are, in general, between 1 and 0.0001% by weight, preferably between 0.5 and 0.001%.
- In the treatment of seed, amounts of active compound of 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, are generally required.
- For the treatment of soil, active compound concentrations of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02% by weight, are required at the site of action.
- The good fungicidal action of the active compound combinations according to the invention can be seen from the following Examples. While the individual active compounds have weaknesses in their fungicidal action, the combinations exhibit an action which extends beyond a simple additive action.
- A synergistic effect is always present with fungicides if the fungicidal action of the active compound combinations is greater than the sum of the actions of the individually applied active compounds.
- The action to be expected—for a given combination of two active compounds can be calculated (cf. Colby, S. R., “Calculating Synergistic and Antagonistic Responses of Herbicide Combinations”, Weeds 15, pages 20-22, 1967) as follows:
-
- X denotes the degree of efficacy, expressed in % of the untreated control, on use of the active compound A at a concentration of m ppm,
- Y denotes the degree of efficacy, expressed in % of the untreated control, on use of the active compound B at a concentration of m ppm,
- E denotes the expected degree of efficacy, expressed in % of the untreated control, on use of the active compound A and B at a concentrations of m and n ppm,
then -
- If the actual fungicidal action is larger than calculated, the combination is superadditive in its action, i.e. a synergistic effect is present. In this case, the actually observed degree of efficacy must be greater than the value for the expected degree of efficacy (E) calculated from the abovementioned formula.
- To produce a suitable preparation of active compound, commercially available active compound formulations (individual active compounds or active compound combinations) are diluted with water to the desired concentration in each case.
- To test for protective activity, young plants are sprayed with the preparation of active compound until dripping wet. After the spray coating has dried on, 2 small pieces of agar covered with Botrytis cinerea are placed on each leaf. The inoculated plants are placed in a darkened humid chamber at 20° C.
- 3 days after the inoculation, the size of the infected spots on the leaves is evaluated.
- In order to demonstrate synergism between the active compounds used in this test, the results were assessed by the method described by Colby (see above).
- Active compounds, active compound concentrations and test results can be seen from the following tables.
-
TABLE 1 Botrytis test (bean)/protective Degree of effectiveness Active compound in % of the Active compound concentration in ppm untreated control 5 51 100 32 Mixture according to the invention (I) 5 + {close oversize brace} + {close oversize brace} 89 Dichlofluanid 100 Expected value, calculated by the 67 Colby formula (see above) 5 51 50 44 Mixture according to the invention (I) 5 + {close oversize brace} + {close oversize brace} 91 Procymidone 50 Expected value, calculated by the 73 Colby formula (see above) 5 51 50 0 Mixture according to the invention (I) 5 + {close oversize brace} + {close oversize brace} 73 Phaltan 50 Expected value, calculated by the 51 Colby formula (see above) 5 51 5 20 Mixture according to the invention (I) 5 + {close oversize brace} + {close oversize brace} 99 Fluazinam 5 Expected value, calculated by the 61 Colby formula (see above) 5 51 10 0 Mixture according to the invention (I) 5 + {close oversize brace} + {close oversize brace} 93 Pyrimethanil 10 Expected value, calculated by the 51 Colby formula (see above) 5 51 5 52 Mixture according to the invention (I) 5 + {close oversize brace} + {close oversize brace} 87 Carbendazim 5 Expected value, calculated by the 76 Colby formula (see above) 5 51 50 32 Mixture according to the invention (I) 5 + {close oversize brace} + {close oversize brace} 84 Tolylfluanid 50 Expected value, calculated by the 67 Colby formula (see above) 5 51 200 37 Mixture according to the invention (I) 5 + {close oversize brace} + {close oversize brace} 73 Chlorothalonil 200 Expected value, calculated by the 69 Colby formula (see above) - Solvent: 100 parts by weight of dimethylformamide
Emulsifier: 0.25 parts by weight of alkylaryl polyglycol ether - To produce a suitable preparation of active compound, 1-part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
- To test for protective activity, young plants are sprayed with the preparation of active compound until dew-moist. After the spray coating has dried on, the plants are sprayed with a spore suspension of Leptosphaeria nodorum. The plants remain for 48 hours in an incubation cabin at 20° C. and 100% relative atmospheric humidity.
- The plants are placed in a greenhouse at a temperature of 15° C. and a relative atmospheric humidity of about 80%.
- Evaluation is effected 10 days after the inoculation.
- In this test, a clearly superior activity compared with the prior art is shown, for example, by the compounds according to the following Preparation Examples:
- Solvent: 10 parts by weight N-methylpyrrolidon
Emulsifier: 0.6 parts by weight alkylarylpolyglycolether - To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
- To test for protective activity, young plants are sprayed with the preparation of active compound until dew-moist. After the spray coating has dried on, the plants are dusted with spores of Erysiphe graminis f. sp. hordei.
- The plants are placed in a greenhouse at a temperature of about 20° C. and a relative atmospheric humidity of about 80%, in order to promote-the development of powdery mildew pustules.
- Evaluation is carried out 7 days after the inoculation.
- In this test, a clearly superior activity compared with the prior art is shown, for example, by the compounds according to the following preparation examples:
- Solvent: 10 parts by weight N-methylpyrrolidone
Emulsifier: 0.6 parts by weight alkylarylpolyglycolether - To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
- To test for protective activity, young plants are sprayed with spores of Erysiphe graminis f. sp. Hordei. 48 hours after the inoculation, the plants are sprayed with the preparation of active compound until dew-moist.
- The plants are placed in a greenhouse at a temperature of about 20° C. and a relative atmospheric humidity of about 80%, in order to promote the development of powdery mildew pustules.
- Evaluation is carried out 7 days after the inoculation.
- In this test, a clearly superior activity compared with the prior art is shown, for example, by the compounds according to the following preparation examples:
- Solvent: 10 parts by weight N-methylpyrrolidon
Emulsifier: 0.6 parts by weight alkylarylpolyglycolether - To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
- To test for curative activity, young plants are dusted with spores of Erysiphe graminis f. sp. hordei. 48 hours after the inoculation, the plants are sprayed with the preparation of active compound until dew-moist.
- The plants are placed in a greenhouse at a temperature of about 20° C. and a relative atmospheric humidity of about 80%, in order to promote the development of powdery mildew pustules.
- Evaluation is carried out 7 days after the inoculation.
- In this test, a clearly superior activity compared with the prior art is shown, for example, by the compounds according to the following preparation examples:
- Solvent: 10 parts by weight of dimethylformamide
Emulsifier: 0.6 parts by weight of alkylaryl polyglycol ether - To produce a suitable preparation of active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
- To test for curative activity, young plants are sprayed with the preparation of active compound until dew-moist. After the spray coating has dried on, the plants are sprayed with a spore suspension of Leptosphaeria nodorum. The plants remain for 48 hours in an incubation cabin at 20° C. and 100% relative atmospheric humidity.
- The plants are placed in a greenhouse at a temperature of 15° C. and a relative atmospheric humidity of about 80%.
- Evaluation is effected 10 days after the inoculation. In this test, a clearly superior activity compared with the prior art is shown, for example, by the compounds according to the following Preparation Examples:
- Solvent: 10 parts by weight of N-methylpyrrolidon
Emulsifier: 0.6 parts by weight of alkylaryl polyglycolether - To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
- To test for protective activity, young plants are sprayed with the preparation of active compound until dew moist. After the spray coating has dried off, the plants are sprayed with a conidia suspension of Pyrenophora teres. The plants then remain in an incubation cabin at 20° C. and 100% relative atmospheric humidity for 48 hours.
- The plants are placed in a greenhouse at a temperature of 20° and a relative atmospheric humidity of about 80%.
- Evaluation is carried 7 days after the inoculation.
- In this test, a clearly superior activity compared with the prior art is shown, for example, by the compounds according to the following preparation examples:
Claims (6)
1-3. (canceled)
4. A synergistic fungicidal composition comprising synergistic fungicidally effective amounts of the combination of a compound of the formula
and/or
(V) an azole derivative from the group consisting of
a) difenconazole
b) penconazole
c) flusilazole
d) hexaconazole
e) myclobutanil
f) prochloraz
g) fluquinconazole
h) epoxiconazole
i) fenpropidin
j) perifenox
k) 8-t-butyl-2-(N-ethyl-N-n-propylamino)-methyl-1-4-dioxaspiro[4,5]decane
and/or
(W) metiram
and/or
(X) pyrimethanil
and/or
(Y) diethofencarb
and/or
(Z) mepanipyrim and/or
cyprodinyl
and/or
(α) phenylpyrrole
and/or
(β) iprodione
and/or
(Γ) vinclozolin
and/or
(ε) benomyl
and/or
(θ) thiophanate and/or
thiophanate-methyl
and/or
(II) sulphur
and/or
(n) compounds of the formula
5. A composition according to claim 4 , wherein the weight ratio of the compound of the formula (I)
to active compound of the group (D) is between 1:0.5 and 1:50,
to active compound of the group (E) is between 1:0.5 and 1:50,
to active compound of the group (F) is between 1:0.5 and 1:50,
to active compound of the group (G) is between 1:0.5 and 1:50,
to active compound of the group (H) is between 1:1 and 1:50,
to active compound of the group (K) is between 1:0.1 and 1:10,
to active compound of the group (L) is between 1:0.5 and 1:50,
to active compound of the group (N) is between 1:0.1 and 1:10,
to active compound of the group (P) is between 1:0.1 and 1:20,
to active compound of the group (Q) is between 1:0.1 and 1:10,
to active compound of the group (R) is between 1:0.1 and 1:10,
to active compound of the group (U) is between 1:0.01 and 1:10,
to active compound of the group (V) is between 1:0.01 and 1:10,
to active compound of the group (W) is between 1:0.5 and 1:50,
to active compound of the group (X) is between 1:0.1 and 1:10,
to active compound of the group (Y) is between 1:0.1 and 1:10,
to active compound of the group (Z) is between 1:0.1 and 1:10,
to active compound of the group (α) is between 1:0.1 and 1:10,
to active compound of the group (β) is between 1:0.1 and 1:20,
to active compound of the group (Γ) is between 1:0.1 and 1:20,
to active compound of the group (ε) is between 1:0.1 and 1:10,
to active compound of the group (θ) is between 1:0.1 and 1:150,
to active compound of the group (II) is between 1:1 and 1:50,
to active compound of the group (n) is between 1:0.025 and 1:10.
6. A method of combating fungi which comprises administering to such fungi or to a fungus habitat a synergistic fungicidally effective amount of a composition according to claim 4 .
7. The synergistic fungicidal composition according to claim 4 , wherein the second compound is (β) iprodione or (γ) vinclozolin.
8. A method of combating fungi which comprises administering to such fungi or to a fungus habitat a synergistic fungicidally effective amount of a composition according to claim 7 .
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US23292394A | 1994-04-25 | 1994-04-25 | |
US08/462,408 US5532262A (en) | 1993-04-28 | 1995-06-05 | Fungicidal active compound combinations |
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US08/846,872 US5922762A (en) | 1993-04-28 | 1997-05-01 | Fungicidal active compound combinations |
US09/249,690 US6071940A (en) | 1993-04-28 | 1999-02-12 | Fungicidal active compound combinations |
US09/541,950 US6235744B1 (en) | 1993-04-28 | 2000-04-03 | Fungicidal active compound combinations |
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US09/249,690 Expired - Fee Related US6071940A (en) | 1993-04-28 | 1999-02-12 | Fungicidal active compound combinations |
US09/541,950 Expired - Fee Related US6235744B1 (en) | 1993-04-28 | 2000-04-03 | Fungicidal active compound combinations |
US09/736,917 Expired - Fee Related US6365195B2 (en) | 1993-04-28 | 2000-12-14 | Fungicidal active compound combinations |
US10/022,136 Expired - Fee Related US6776994B2 (en) | 1993-04-28 | 2001-12-13 | Fungicidal active compound combinations |
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US12/118,212 Abandoned US20090074887A1 (en) | 1993-04-28 | 2008-05-09 | Fungicidal active compound combinations |
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Application Number | Title | Priority Date | Filing Date |
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US08/462,408 Expired - Lifetime US5532262A (en) | 1993-04-28 | 1995-06-05 | Fungicidal active compound combinations |
US08/629,245 Expired - Lifetime US5672619A (en) | 1993-04-28 | 1996-04-08 | Fungicidal active compound combinations |
US08/846,872 Expired - Lifetime US5922762A (en) | 1993-04-28 | 1997-05-01 | Fungicidal active compound combinations |
US09/249,690 Expired - Fee Related US6071940A (en) | 1993-04-28 | 1999-02-12 | Fungicidal active compound combinations |
US09/541,950 Expired - Fee Related US6235744B1 (en) | 1993-04-28 | 2000-04-03 | Fungicidal active compound combinations |
US09/736,917 Expired - Fee Related US6365195B2 (en) | 1993-04-28 | 2000-12-14 | Fungicidal active compound combinations |
US10/022,136 Expired - Fee Related US6776994B2 (en) | 1993-04-28 | 2001-12-13 | Fungicidal active compound combinations |
US10/860,868 Expired - Fee Related US7776906B2 (en) | 1993-04-28 | 2004-06-03 | Fungicidal active compound combinations |
US12/118,212 Abandoned US20090074887A1 (en) | 1993-04-28 | 2008-05-09 | Fungicidal active compound combinations |
Country Status (11)
Country | Link |
---|---|
US (10) | US5532262A (en) |
EP (1) | EP0626135B1 (en) |
JP (1) | JP3491845B2 (en) |
KR (1) | KR100327775B1 (en) |
CN (3) | CN1074902C (en) |
DE (2) | DE4313867A1 (en) |
ES (1) | ES2099501T3 (en) |
HK (2) | HK1034645A1 (en) |
TR (1) | TR27417A (en) |
TW (1) | TW272111B (en) |
ZA (1) | ZA942887B (en) |
Cited By (1)
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US20170290379A1 (en) * | 2016-04-06 | 2017-10-12 | Douglas L. Allen | Vertical lift harness and turnout gear |
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DE4313867A1 (en) * | 1993-04-28 | 1994-11-03 | Bayer Ag | Fungicidal active ingredient combinations |
DE4437048A1 (en) * | 1994-10-17 | 1996-04-18 | Bayer Ag | Fungicidal active ingredient combinations |
DE19543746A1 (en) * | 1995-11-24 | 1997-05-28 | Basf Ag | Fungicidal agents |
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EP1563733A1 (en) * | 2004-02-12 | 2005-08-17 | Bayer CropScience S.A. | Fungicidal composition comprising a pyridylethylbenzamide derivative and a compound capable of inhibiting mitosis and cell division |
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CN102057907B (en) * | 2010-11-26 | 2013-06-26 | 广东中迅农科股份有限公司 | Sterilization composite containing dithianon and chlorothalonil and application thereof |
EP2499911A1 (en) * | 2011-03-11 | 2012-09-19 | Bayer Cropscience AG | Active compound combinations comprising fenhexamid |
CN103300004B (en) * | 2012-03-16 | 2016-02-17 | 陕西韦尔奇作物保护有限公司 | A kind of bactericidal composition containing fenhexamid and methoxy acrylic |
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CN103314967B (en) * | 2012-03-21 | 2016-02-17 | 陕西韦尔奇作物保护有限公司 | A kind of bactericidal composition containing fenhexamid |
CN103314989B (en) * | 2012-03-23 | 2016-08-03 | 陕西韦尔奇作物保护有限公司 | A kind of bactericidal composition containing fenhexamid Yu triazole class compounds |
CN103355298B (en) * | 2012-03-29 | 2016-04-06 | 陕西韦尔奇作物保护有限公司 | A kind of bactericidal composition containing fenhexamid and antibiotics |
CN103828811A (en) * | 2013-11-28 | 2014-06-04 | 广东中迅农科股份有限公司 | Pesticide composition containing fenhexamid and fluazinam |
CN105123735A (en) * | 2015-09-02 | 2015-12-09 | 陕西上格之路生物科学有限公司 | Sterilization composite containing fenhexamid |
KR102095352B1 (en) * | 2018-09-05 | 2020-03-31 | 주식회사 드림테크 | Cervical correction device |
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1993
- 1993-04-28 DE DE4313867A patent/DE4313867A1/en not_active Withdrawn
-
1994
- 1994-04-07 TR TR00334/94A patent/TR27417A/en unknown
- 1994-04-12 TW TW083103201A patent/TW272111B/zh not_active IP Right Cessation
- 1994-04-15 EP EP94105879A patent/EP0626135B1/en not_active Expired - Lifetime
- 1994-04-15 ES ES94105879T patent/ES2099501T3/en not_active Expired - Lifetime
- 1994-04-15 DE DE59402194T patent/DE59402194D1/en not_active Expired - Lifetime
- 1994-04-22 JP JP10615694A patent/JP3491845B2/en not_active Expired - Fee Related
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- 1994-04-26 ZA ZA942887A patent/ZA942887B/en unknown
- 1994-04-28 CN CN94104652A patent/CN1074902C/en not_active Expired - Fee Related
- 1994-04-28 CN CNB001270753A patent/CN1157115C/en not_active Expired - Fee Related
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1995
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1996
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-
1997
- 1997-05-01 US US08/846,872 patent/US5922762A/en not_active Expired - Lifetime
-
1999
- 1999-02-12 US US09/249,690 patent/US6071940A/en not_active Expired - Fee Related
-
2000
- 2000-04-03 US US09/541,950 patent/US6235744B1/en not_active Expired - Fee Related
- 2000-09-14 CN CN00127076A patent/CN1131670C/en not_active Expired - Fee Related
- 2000-12-14 US US09/736,917 patent/US6365195B2/en not_active Expired - Fee Related
-
2001
- 2001-08-03 HK HK01105410A patent/HK1034645A1/en not_active IP Right Cessation
- 2001-08-03 HK HK01105416A patent/HK1034646A1/en not_active IP Right Cessation
- 2001-12-13 US US10/022,136 patent/US6776994B2/en not_active Expired - Fee Related
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2004
- 2004-06-03 US US10/860,868 patent/US7776906B2/en not_active Expired - Fee Related
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2008
- 2008-05-09 US US12/118,212 patent/US20090074887A1/en not_active Abandoned
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2010
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20170290379A1 (en) * | 2016-04-06 | 2017-10-12 | Douglas L. Allen | Vertical lift harness and turnout gear |
Also Published As
Publication number | Publication date |
---|---|
CN1074902C (en) | 2001-11-21 |
US20010044443A1 (en) | 2001-11-22 |
US6071940A (en) | 2000-06-06 |
EP0626135A2 (en) | 1994-11-30 |
ES2099501T3 (en) | 1997-05-16 |
KR940023360A (en) | 1994-11-17 |
DE59402194D1 (en) | 1997-04-30 |
CN1157115C (en) | 2004-07-14 |
KR100327775B1 (en) | 2004-12-17 |
EP0626135A3 (en) | 1995-02-01 |
JP3491845B2 (en) | 2004-01-26 |
EP0626135B1 (en) | 1997-03-26 |
US6776994B2 (en) | 2004-08-17 |
US7776906B2 (en) | 2010-08-17 |
TW272111B (en) | 1996-03-11 |
TR27417A (en) | 1995-04-14 |
US5922762A (en) | 1999-07-13 |
DE4313867A1 (en) | 1994-11-03 |
HK1034646A1 (en) | 2001-11-02 |
US6365195B2 (en) | 2002-04-02 |
CN1094221A (en) | 1994-11-02 |
HK1034645A1 (en) | 2001-11-02 |
US20020111385A1 (en) | 2002-08-15 |
ZA942887B (en) | 1995-01-04 |
US20090074887A1 (en) | 2009-03-19 |
CN1293893A (en) | 2001-05-09 |
US6235744B1 (en) | 2001-05-22 |
CN1293896A (en) | 2001-05-09 |
JPH06329505A (en) | 1994-11-29 |
US5672619A (en) | 1997-09-30 |
US5532262A (en) | 1996-07-02 |
US20040220271A1 (en) | 2004-11-04 |
CN1131670C (en) | 2003-12-24 |
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STCB | Information on status: application discontinuation |
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