WO1999013722A1 - Seed treatment fungicides for control of plant diseases - Google Patents
Seed treatment fungicides for control of plant diseases Download PDFInfo
- Publication number
- WO1999013722A1 WO1999013722A1 PCT/US1998/018221 US9818221W WO9913722A1 WO 1999013722 A1 WO1999013722 A1 WO 1999013722A1 US 9818221 W US9818221 W US 9818221W WO 9913722 A1 WO9913722 A1 WO 9913722A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- methyl
- recited
- compound
- thiophanate
- plant
- Prior art date
Links
- 201000010099 disease Diseases 0.000 title description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 9
- 239000000417 fungicide Substances 0.000 title description 7
- 238000000034 method Methods 0.000 claims abstract description 32
- 239000000203 mixture Substances 0.000 claims abstract description 29
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- -1 thiophanate compound Chemical class 0.000 claims abstract description 19
- 230000000855 fungicidal effect Effects 0.000 claims abstract description 15
- 241000233866 Fungi Species 0.000 claims abstract description 14
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 11
- 239000012990 dithiocarbamate Substances 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 244000061456 Solanum tuberosum Species 0.000 claims description 23
- XERJKGMBORTKEO-VZUCSPMQSA-N (1e)-2-(ethylcarbamoylamino)-n-methoxy-2-oxoethanimidoyl cyanide Chemical compound CCNC(=O)NC(=O)C(\C#N)=N\OC XERJKGMBORTKEO-VZUCSPMQSA-N 0.000 claims description 21
- 239000005756 Cymoxanil Substances 0.000 claims description 19
- 241000196324 Embryophyta Species 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 claims description 17
- 241000233622 Phytophthora infestans Species 0.000 claims description 16
- 239000005842 Thiophanate-methyl Substances 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000005802 Mancozeb Substances 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 150000002431 hydrogen Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 235000002595 Solanum tuberosum Nutrition 0.000 description 20
- 238000009472 formulation Methods 0.000 description 7
- 239000000428 dust Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- 229920001817 Agar Polymers 0.000 description 4
- 239000008272 agar Substances 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 230000010076 replication Effects 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 230000028070 sporulation Effects 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 0 *C(*)(CNCSNS1)NC1=S Chemical compound *C(*)(CNCSNS1)NC1=S 0.000 description 2
- 241000219495 Betulaceae Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
- 235000020679 tap water Nutrition 0.000 description 2
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical class CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 241000233614 Phytophthora Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 238000012750 in vivo screening Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- XXGPGPGUQBISGF-UHFFFAOYSA-N n'-ethyl-2-methoxyiminopropanediamide Chemical compound CCNC(=O)C(C(N)=O)=NOC XXGPGPGUQBISGF-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 230000007918 pathogenicity Effects 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- WZZLDXDUQPOXNW-UHFFFAOYSA-N propamocarb Chemical compound CCCOC(=O)NCCCN(C)C WZZLDXDUQPOXNW-UHFFFAOYSA-N 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- ZEVCJZRMCOYJSP-UHFFFAOYSA-N sodium;2-(dithiocarboxyamino)ethylcarbamodithioic acid Chemical compound [Na+].SC(=S)NCCNC(S)=S ZEVCJZRMCOYJSP-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 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
- 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
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
Definitions
- This invention relates to a method for controlling fungus diseases in plants by applying to the seed or tuber a fungicidally effective amount of a 2-alkoxyiminoacetamide compound such as cymoxanil, optionally in admixture with one or more of an alkylene bis- dithiocarbamate complex salt such as mancozeb, and a thiophanate compound such as thiophanate-methyl .
- This invention also relates to a fungicidal composition comprising, in a fungicidally effective aggregate amount, a 2-alkoxyiminoacetamide compound, an alkylene bis- dithiocarbamate complex salt, and a thiophanate compound.
- Late Blight is the devastating disease that affected the Irish potato crop over 150 years ago.
- the Late Blight fungus Phytophthora in.festa.ns
- New strains of P. infestans have evolved that are fungicide resistant and which are more aggressive with respect to pathogenicity on the potato tuber.
- the disease can now be introduced into potato fields by means of infected seed tubers more efficiently than in the past.
- This invention relates to a method for combatting plant fungi in a plant, which comprises applying to the seeds or tubers of the plant, a fungicidally effective amount of :
- R -0 -N C -C -NH -C -NH -R '
- R is methyl or ethyl and R 1 hydrogen, C ⁇ d alkyl or allyl, preferably, C ⁇ alkyl, more preferably, methyl or ethyl ; or
- R 4 and R 5 are each, independently, hydrogen or Ci-Cg alkyl, preferably, hydrogen or C x -C 4 alkyl, more preferably, hydrogen, methyl or ethyl;
- Q is Zn, Fe, or
- Cu preferably, Zn; and the ratio of x to y is from about 3:1 to about 100:1, preferably, about 5:1 to about 20:1, more preferably, about 6:1 to about 10:1
- R and R are each, independently, Ci-Cg alkyl, preferably, -Cj alkyl, more preferably, methyl or ethyl .
- This invention further relates to a fungicidal composition
- a fungicidal composition comprising:
- NC o o R -0 -N C -C -NH -C -NH -7
- R is methyl or ethyl and R 1 hydrogen, O alkyl or allyl, preferably, OC 4 alkyl, more preferably, methyl or ethyl ;
- R 4 and R 5 are each, independently, hydrogen or Ci-Cg alkyl, preferably, hydrogen or C x -C 4 alkyl, more preferably, hydrogen, methyl or ethyl;
- Q is Zn, Fe, or Cu, preferably, Zn; and the ratio of x to y is from about 3:1 to about 100:1, preferably, about 5:1 to about 20:1, more preferably, about 6:1 to about 10:1;
- R 2 and R 3 are each, independently, OCg alkyl, preferably, OC 4 alkyl, more preferably, methyl or ethyl,
- the 2-alkoxyiminoacetamide compounds, alkylene bis- dithiocarbamate complex salts, and thiophanate compounds useful in the method and composition of this invention are known in the art, as are methods for their preparation. See, e.g., U. S. Patents Nos . 3,957,847; 3,379,610; and 5,571,443, respectively.
- the method and composition of this invention are particularly suitable for use against Phytophthora infestans on or in potato plants and tubers.
- composition of this invention and the compounds useful in the method of this invention can be formulated in conventional ways.
- useful formulations include slurries, solid seed coatings, soaks, dusts on the surface of the seed or tuber, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates, and the like.
- the formulations in general, comprise about 1% to 99% by weight of active ingredient.
- the formulations can additionally comprise additional additives such as surfactants, solid or liquid diluents, pigments, thickeners, and the like.
- the method of application of the formulations to the seeds or tubers can vary depending, e.g., on the compounds and/or the formulation used.
- the seed or tuber should be treated with about 50 to about 1200 ppm, preferably between about 300 to about 900 ppm, most preferably, about 700 ppm, per 100 pounds ("cwt") of seed or tuber, of the composition of this invention or of the compounds useful in the method of this invention.
- This invention preferably relates to a method for combatting plant fungi in a plant, which comprises applying to the seeds or tubers of the plant, an effective amount of a fungicidal composition comprising a fungicidally effective amount of: a) cymoxanil ; or b) cymoxanil in admixture with one or more of the group consisting of mancozeb and thiophanate-methyl.
- This invention further preferably relates to a fungicidal composition
- a fungicidal composition comprising cymoxanil, mancozeb and thiophanate-methyl, in an effective aggregate amount.
- Cymoxanil, mancozeb and thiophanate-methyl are all known compounds.
- Cymoxanil (a foliar fungicide sold under the trademarks CURZATE and DPX-3217) is 2-cyano-N-
- Mancozeb (a fungicide sold under the trademarks MANZATE-200 and DITHANE M-45) is a mixture of [[1,2- ethanediylbis- (carba odithioato) ] (2- )] manganese and [ [1, 2-ethanediylbis (carbamothioato) ] (2) -] zinc .
- Thiophanate-methyl (a systemic fungicide sold under the trademarks TOPSIN M and NF-44) is dimethyl [1, 2- phenylene-bis- (iminocarbono-thioyl) -bis- [carbamate] .
- composition of this invention in general, satisfactory results can be obtained when the weight ratio of cymoxanil :mancozeb : thiophanate-methyl is from about 3:1:1 to about 1:16:6, preferably, about
- the formulations can comprise from 0 to about 20% of an agriculturally acceptable surfactant such as wetting and dispersing agents, e.g., the condensation product of formaldehyde with naphthalene sulphonate, an alkylarylsulphonate , a lignin sulphonate, a fatty sulphate, an ethoxylated alkylphenol and an ethoxylated fatty alcohol .
- the formulations can additionally comprise from about 10 to about 99% of an agriculturally acceptable solid or liquid diluent, including carriers, such as talc, zeolites, Alder bark, kaolin, diatomaceous earth, mineral oil, water, and the like.
- a potato dust inert system was prepared by blending the following three inert diluents in a ribbon blender: talc (Cyprus BT-200) (48.39% w/w) , zeolite (16.12% w/w), and Alder bark (35.49% w/w).
- Potato tubers were removed from 5°C storage and allowed to come to room temperature. The tubers were then washed with tap water and sterilized in 5% commercial bleach (Clorox) for 10 minutes. The tubers were then rinsed in sterile distilled water and dried.
- Chlorox commercial bleach
- Phytophthora infestans was grown on agar plates at
- Tubers were cut into uniform sized slices (1 cm thick) . Each dust was applied to 20 slices at 0.5 lb/cwt . Two sets of 20 potato slices were left untreated with dust and used as controls. Each dusted potato slice was then placed on sterile moistened filter paper in a sterile petri dish.
- a zoospore suspension was quantified to a concentration of 20,000 spores/ml. 100 ml of this spore suspension was then applied to a sterile filter paper disk. One such treated disk was placed in the center of each potato slice. One set of 20 undusted potato slices were not inoculated and used as a sterile control .
- Each potato slice was then placed in the dark at 18°C for 7 days. After the 7 days, the disease state of each potato slice was assessed.
- Potato tubers were removed from 5°C storage and allowed to come to room temperature. The tubers were then washed with tap water and sterilized in 5% commercial bleach (Clorox) for 10 minutes. The tubers were then rinsed in sterile distilled water and dried.
- Chlorox commercial bleach
- Phytophthora infestans was grown on agar plates at
- Potatoes not dipped in the zoospores were also cut into 2-4 oz . pieces and one set of 15 uninoculated potato pieces was used as a sterile control .
- the potato pieces were then placed in sandy soil and incubated at 17°C days and 13 °C nights for 32 days. Growth after emergence was monitored for 14-28 days. Disease symptoms were visually rated. Stem/leaf tissue was assayed for P . infestans on appropriate media.
- potato seed pieces were then removed and cut in half and disease presence was visually assessed.
- Blighted tuber No emergence Blighted tuber; Small-sized infected stems Blighted tuber; Average-sized infected stems Clean tubers; Healthy uninfected stems
- Shepody potato tubers were contaminated/inoculated with Phytophthora infestans and set aside ("source tubers") . After two weeks, one (1) source tuber was cut into quarters through the diseased area with a cutting knife. Without cleaning or changing the knife, five (5) uninoculated Shepody potato tubers were then cut into quarters. This process (1 source tuber/5 uninfected tubers) was repeated to provide enough tubers for 30 replications per treatment (Table 10 below) .
- the cut tubers (source and uninoculated) were weighed and the appropriate amount of each dust listed in Table 10 below was applied to the tubers by placing the tubers in a double paper bag with dust and then shaking the bag.
- the treated tubers were then placed in an unsealed plastic bag (one bag per treatment) and incubated at 10°C, 80-90% RH, for two (2) weeks. After two (2) weeks, the bagged tubers were removed from the 10°C, 80-90% RH environment. The bags were then rolled or shaken to simulate movement from storage to planting areas. The tubers were removed and the spread of P . infestans was determined - % infected tubers . The tubers were warmed to room temperature and planted. The source tubers were not planted. Emergence and infection data were obtained as described above in Example 2 (30 replications/treatment) .
- Example 6 The procedure described above in Example 6 was repeated using Red Nordland potato tubers. The results of this test are present below in Table 11.
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT98943518T ATE273618T1 (en) | 1997-09-18 | 1998-09-01 | SEED TREATMENT FUNGICIDE FOR CONTROLLING PLANT DISEASES |
EP98943518A EP1017280B1 (en) | 1997-09-18 | 1998-09-01 | Seed treatment fungicides for control of plant diseases |
CA002304153A CA2304153C (en) | 1997-09-18 | 1998-09-01 | Seed treatment fungicides for control of plant diseases |
DE69825766T DE69825766T2 (en) | 1997-09-18 | 1998-09-01 | SEED TREATMENT FUNGICIDE FOR COMBATING PLANT DISEASES |
EA200000333A EA004531B1 (en) | 1997-09-18 | 1998-09-01 | Seed treatment fungicides for control of plant diseases |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US5929397P | 1997-09-18 | 1997-09-18 | |
US60/059,293 | 1997-09-18 | ||
US09/132,927 US6228883B1 (en) | 1997-09-18 | 1998-08-12 | Seed treatment fungicides for control of plant diseases |
US09/132,927 | 1998-08-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1999013722A1 true WO1999013722A1 (en) | 1999-03-25 |
Family
ID=26738589
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1998/018221 WO1999013722A1 (en) | 1997-09-18 | 1998-09-01 | Seed treatment fungicides for control of plant diseases |
Country Status (7)
Country | Link |
---|---|
US (2) | US6228883B1 (en) |
EP (1) | EP1017280B1 (en) |
AT (1) | ATE273618T1 (en) |
CA (1) | CA2304153C (en) |
DE (1) | DE69825766T2 (en) |
EA (1) | EA004531B1 (en) |
WO (1) | WO1999013722A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1077029A1 (en) * | 1999-08-11 | 2001-02-21 | Rohm And Haas Company | Oil in water flowable pesticide formulation |
CN101983566A (en) * | 2010-11-18 | 2011-03-09 | 利民化工股份有限公司 | Ternary compound wettable powder and preparation method and application thereof |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8084393B1 (en) | 2006-02-06 | 2011-12-27 | Kresge Paul O | Potato treatment composition |
AR075573A1 (en) | 2009-02-11 | 2011-04-20 | Basf Se | DIMETHOMORPH AS A PESTICIDE PROTECTOR WITH PHYTO-TOXIC EFFECTS |
US8209902B2 (en) * | 2009-07-02 | 2012-07-03 | Nanotech Industries, Inc. | Biologically active multifunctional nanochips and method of application thereof for production of high-quality seed |
CN102657202A (en) * | 2012-04-23 | 2012-09-12 | 赵国彬 | Germicide for preventing and treating downy mildew and epidemic disease |
US20150101245A1 (en) * | 2013-10-15 | 2015-04-16 | Stuart Barclay | Seed coating compositions |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1470740A (en) * | 1975-11-18 | 1977-04-21 | Du Pont | Fungicides |
RO80510A2 (en) * | 1979-07-30 | 1983-02-15 | Institutul De Cercetari Pentru Protectia Plantelor,Ro | PREPARED FOR COMBATING THE TREATMENT OF TUBERS, BULB AND TUBEROBULES |
US5007953A (en) * | 1986-05-07 | 1991-04-16 | Snake River Chemicals, Inc. | Seed treatment compositions |
DD298340A5 (en) * | 1989-12-28 | 1992-02-20 | Berlin-Chemie Ag,De | MEANS FOR CONTROLLING FUSARIUM DRY FIELDS IN POTATOES |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL277376A (en) | 1961-05-09 | |||
GB1407330A (en) | 1972-12-25 | 1975-09-24 | Nippon Soda Co | Process for the production of thiophane derivatives |
US3957847A (en) | 1974-03-21 | 1976-05-18 | E. I. Du Pont De Nemours And Company | 2-cyano-2-hydroxyiminoacetamides as plant disease control agents |
US4742079A (en) | 1982-01-26 | 1988-05-03 | Sandoz Ltd. | Fungicides containing cymoxanil and metalaxyl |
DE4304172A1 (en) | 1993-02-12 | 1994-08-25 | Bayer Ag | Fungicidal active ingredient combinations |
-
1998
- 1998-08-12 US US09/132,927 patent/US6228883B1/en not_active Expired - Lifetime
- 1998-09-01 EA EA200000333A patent/EA004531B1/en not_active IP Right Cessation
- 1998-09-01 DE DE69825766T patent/DE69825766T2/en not_active Expired - Lifetime
- 1998-09-01 EP EP98943518A patent/EP1017280B1/en not_active Expired - Lifetime
- 1998-09-01 WO PCT/US1998/018221 patent/WO1999013722A1/en active IP Right Grant
- 1998-09-01 AT AT98943518T patent/ATE273618T1/en not_active IP Right Cessation
- 1998-09-01 CA CA002304153A patent/CA2304153C/en not_active Expired - Lifetime
-
1999
- 1999-06-25 US US09/340,104 patent/US6127411A/en not_active Expired - Lifetime
Patent Citations (4)
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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EP1077029A1 (en) * | 1999-08-11 | 2001-02-21 | Rohm And Haas Company | Oil in water flowable pesticide formulation |
CN101983566A (en) * | 2010-11-18 | 2011-03-09 | 利民化工股份有限公司 | Ternary compound wettable powder and preparation method and application thereof |
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US6228883B1 (en) | 2001-05-08 |
EP1017280A1 (en) | 2000-07-12 |
ATE273618T1 (en) | 2004-09-15 |
EP1017280B1 (en) | 2004-08-18 |
CA2304153C (en) | 2008-12-02 |
DE69825766T2 (en) | 2005-08-25 |
EA200000333A1 (en) | 2000-10-30 |
DE69825766D1 (en) | 2004-09-23 |
CA2304153A1 (en) | 1999-03-25 |
EA004531B1 (en) | 2004-06-24 |
US6127411A (en) | 2000-10-03 |
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