CA1292942C - Seed disinfectant composition - Google Patents
Seed disinfectant compositionInfo
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- CA1292942C CA1292942C CA000553160A CA553160A CA1292942C CA 1292942 C CA1292942 C CA 1292942C CA 000553160 A CA000553160 A CA 000553160A CA 553160 A CA553160 A CA 553160A CA 1292942 C CA1292942 C CA 1292942C
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Abstract
ABSTRACT OF THE DISCLOSURE
A seed disinfectant composition comprising (A) (E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol containing not less than 50% by weight of (-)-(E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol and (B) At least one benzimidazole thiophanate fungicide and optionally comprising (C) O,O-dimethyl-O-(2,6-dichloro-4-methylphenyl)phosphorothioate and/or (D) 1-Ethyl-1,4-dihydro-6,7-methylenedioxy-4-oxo-3-quinoline carboxylic acid or a salt thereof are disclosed. The seed disinfectant composition of the present invention exhibits a synergistically high preventing effect on various seed born diseases and simultaneously has a wide antifungal spectrum and shows a stable preventing effect on the fungi having resistance to conventional disinfectants.
A seed disinfectant composition comprising (A) (E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol containing not less than 50% by weight of (-)-(E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol and (B) At least one benzimidazole thiophanate fungicide and optionally comprising (C) O,O-dimethyl-O-(2,6-dichloro-4-methylphenyl)phosphorothioate and/or (D) 1-Ethyl-1,4-dihydro-6,7-methylenedioxy-4-oxo-3-quinoline carboxylic acid or a salt thereof are disclosed. The seed disinfectant composition of the present invention exhibits a synergistically high preventing effect on various seed born diseases and simultaneously has a wide antifungal spectrum and shows a stable preventing effect on the fungi having resistance to conventional disinfectants.
Description
?;~
1 The present invention relates to a seed dis- -infectant composition comprising (E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol containing not less than 50% by weight of (-)-(E)-l-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-l-penten-3-ol (hereinafter referred to as Compound A) and at least one benzimidazole thiophanate fungicide (hereinafter referred to as Compound B) and optionally comprising O,O-dimethyl-O-(2,6-dichloro-4-methylphenyl)-phosphorothioate ~hereinafter referred to as Compound C)and/or l-ethyl-1,4-dihydro-6,7-methylenedioxy-4-oxo-3-quinoline carboxylic acid (hereinafter referred to as Compound D) or a salt thereof.
Heretofore, benomyl thiophanate-methyl, thiram, carboxin, PCNB, organic mercury and admixtures thereof have been used to prevent seed born diseases.
However, the commercially available disinfectants mentioned above have effects only on limited diseases, and such a problem arises that these disinfectants lose their ; 20 effects of preYenting seed bor~ diseases on resistant fungi which have appeared a~ong the disease on ~hich these disinfectants had antifungal effects before.
In view of this situation, the present inventor have ~ade extensive research to develop a seed disinfectant having a wide antifungal spectrum and showing a stable -- 1 -- ~
3'~'~
l effect of preventing diseases on the above-mentioned :resistant fungi.
As a result, it has been found that a seed disinfectant composition comprising Compound A and Compound B in a specific weight ratio and optionally comprising Compound C and/or Compound D or a salt thereof in a specific weight ratio have not only all the properties mentioned above but also an excellent synergistic effect.
Thus, according to the present invention, there is provided a seed disinfectant composition comprising effective amount of ~ A) (E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol containing not less than 50% by weight of (-)-(E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-Z-(1,2,4-triazol-l-yl)-l-penten-3-ol and (B) at least one benzimidazole thiophanate fungicide, wherein the weight ratio of (A):(B) is 1-50:1-50.
Compound A, one of the active ingredients of the seed disinfectant composition of the present invention, is a compound.selected from the group consisting of the compounds disclosed in Japanese Patent Application Kokai ~Laid-Open) Nos. 124,771/80.and 99,575/82. In other words, Compound A may be a racemic compound, a racemic mixture containing more than 50% by weight of ~ (E)-1-~2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-l~penten-3-ol and a pure ~-)-(E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penken-3-ol.
.Fxom the viewpoint of exertion of disinfectant -- 2 ~
1 properties, it is preferable that Compound A contains not less than 5Q~ by weight of (-)-(E)-1-(2,4-dichlorophenyl)-~,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol (hereinafter referred to as (-)-enantiomer), and since the more Compound A contains (-)-enantiomer, the greater the disinfectant effect becomes, it is more preferable that Compound A contains not less than 80% by weight of (-)-enantiomer, most preferably, it is substantially pure (-)-enantiomer (purity: 90% by weight or more).
Known benzimidazole thiophanate fungicides can be used in the present invention. However, preferable members are methyl l-(butylcarbamoyl)benzimidazole-2-ylcarbamate (common name: benomyl, hereinafter referred to as Compound I), 2-(4-thiazolyl)benzimidazole ~common name: thiabendazole, hereinafter referred-to as Compound II), methyl benzimidazol-2-ylcarbamate (common name:
carbendazim, hereinafter referred to as Compound III), 2-(2-furyl)benzimidazole lcommon name: fubelidazol, hereinafter referred to as Compound IV), 1,2-bis(3-methoxycarbonyl-2-thioureido)benzene (common name:
: thiophanate-methyl, hereinafter referred to as Compound V), ~; : 1,2-bis:(3-ethoxycarbonyl-2-thioureido)benzene (common name: thiophanate, hereinafter refe~red to as Compound YI~, methyl 1-(2-cyclohexenylcarbamoyl)-2-25~ benzimidazolecarbamate (hereinafter referred to as Compound VII) and the like. Compounds I to.VI are known as fungicides.for.various diseases of fruit trees, vegetables, ba~ley, wheat, oats,.rye and th~ like. Compound VII is 1~2~2 1 disclosed in Japanese Patent Application Kokai (Laid-Open) No. 10,004/87.
The weight ratio of Compound A to Compound B
is usually 1-50:1-50, preferably 1-20:1-20.
Compound C used in the present invention is O,C-dimethyl-O-(2,6-dichloro-4-methylphenyl)-phosphorothioate disclosed in Japanese Patent Publication Kokoku (Post-Exam) No. 20,571/76.
Compound D is l-ethyl-1,4-dihydro-6,7-methylenedioxy-4-oxo-3-quinoline carboxylic acid disclosed in Japanese Patent Application Kokai (Laid-Open) No. 48,042/82.
In the present invention, Compound A, Compound B, Compound C and Compound D are referred to as active ingredients.
The weight ratio of Compound A: Compound B:
Compound C: Compound D is usually 1-50:1-50:0-50:0-50, preferably 1~20:1-20:1-20:1-20. In the present invention, they are mixed together and used.
The mixture of the active ingredients in the present invention can be used as it is, though it is :
usually used ln admixture with an inert carrier. If necessary, various adjuvants for formulation are added such as surface active agents, wetting agents, dispersing agents, sticking agents, thickeners, stabilizers and the like depending upon the use, to formulate the seed disinfectant to a preparation such as a wettablë powder, a dust, a flowable concen~rate, an emulsifiable concentrate l~Z~
l or the like.
The carriers in the above preparation include solid carriers such as a fine powder, a granule and the :Like of kaoline clay, attapulgite clayr bentonite, acid clay, pyrophylite, talc, diatomaceous earth, calcite, walnut shell powder, urea, ammonium sulfate, synthetic hydrous silica, white carbon and the like and liquid carriers such as, for example, xylene, methylnaphthalene and the like; alcohols, for example, isopropanol, ethylene glycol, cellosolve and the like; ketones, for example, acetone, cyclohexanone, isophorone and the like;
vegetable oils such as soy oil, cottonseed oil and the like; dimethyl sulfoxide; acetonitrile; water; etc.
Surace active agents used for emulsifying, dispersing, wetting-spreading and the ~ike include anionic surface active agents such as alkylsulfuric esters, alkyl sulfonates, aryl sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkyl aryl ether phosphoric esters, naphthalene sulfonic acid-formaldehyde condensates and the like and nonionic surface active agents such as polyoxy-ethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene-polyoxypropylene block copolymers, sorbitan fatty acid este~s, polyo~yethylene sorbitan fatty acid ester~ and the like.
Adjuvants other than the abo~e surface active agents for formulation are lignin sulfate, lignin sulfonates alginate, poly(vinyl alcohol), gum arabic, CMC (carboxy-methyl cellulose~, PAP tacid isopropyl phosphate) and the _ 5 _ 1.;2~Z94Z
1 like.
Other disinfectant, if necessary, such as nuarimol, hydroxyisoxazole basic copper chloride, imazalil and the like can be added thereto. Also, when anthraquinone is added thereto, the resulting disinfectant composition has a bird repellent effect, and the seed disinfectant composition of the present invention can be ùsed in admixture with other seed-treating agents.
The content of the active ingredients in these formulations is preferably 0.1-99.9% by weight, more preferably 0.1-80% by weight.
The seed disinfectant composition of the present invention can be used for dust-coating, dipping or spray-ing, In the case of dust-coating or spraying seeds with the seed disinfectant composition of the present invention, the amount of the composition used is prefer-ably from 0.00005 to 1~ as the active ingredients based on the dry weight of seeds, while in the case of dipping or spraying seeds in or with the seed disinfec*ant ~ composition of the present invention, the concentration - of the active ingredients in the composition is preferably from 0.01 ppm to 10~. However, the a~ount of the composi-tion used is va~iable depending on the type of preparation 2S or the kind of seed of crop to be treated.
The seed disinfectant composition of the present invention exhibits a synergistically high preventing effect on various 5eed born diséases and simultaneously Z~2 l has a wide antifungal spectrum and shows a stable prevent-ing effect on the fungi having resistance to conventional disinfectants.
The seed disinfectant composition of the present invention is effective on the seed born diseases such as Erysiphe sp., Puccinia sp., Septoria tritici, Leptosphaerla nodorum, Tilletia caries, Ustilago tritici, Fusarium sp., Cochliobolus sativus, Helminthosporium gramineum, Ustilago nuda, Pyrenophora teres, Rhynchosporium secalis, Septoria sp., Ustilago hordei, Ustilago avenae, Pyrenophora avenae, Fusarium nivale, Pyricularia oryzae, . _ .
Cochliobolus ~yabeanus, Gibberella fujikuroi, Pseudomonas glumae and the like.
The present invention is explained in more detail in the following examples which are by way of illustration and not by way of limitation. In the following examples, "parts" or "%" is by weight.
Formulation Example 1 (A Dust) 0.05 part of Compound A, 0.05 part of Compoumd I, 20 20 parts of hydroxyisoxazole, 66.5 parts of kaoline clay and 13.4 par*s of talc wexe thoxoughly ground and mixed together to obtain a dust of the present invention having :~ an active ingredie~t concentration of 0.1~.
FormuIation Example 2 (A Dust) 2 parts of Compound A, 10 parts of Compound VII, 10 parts of Compound C, 68 parts of kaoline clay and 10 parts of talc were thoroughly ground and mixed together to Z~342 l obtain a dust of the present invention having an active i.ngredient concentration of 22%.
Formulation Example 3 (A Dust) 20 parts of Compound A, 20 parts of Compound II, 20 parts of Compound C, 20 parts of Compound D, 20 parts of kaoline clay and 10 parts of talc were thoroughly ground and mixed together to obtain a dust of the present inven-tion having an active ingredient concentration of 80~.
Formulation Example 4 (A Wettable Powder) 0.2 part of Compound A, 2 parts of Compound III, 0,3 part of imazalil, 42.5 parts of diatomaceous earth, 50 parts of white carbon, 3 parts of sodium lauryl sulfate (a wetting agent) and 2 parts of calcium lignin sulfonate (a dispersant) were thoroughly ground and mixed together to obtain a wettable powder of the present inven-tion having an active ingredient concentration of 2.2%.
Formulation Example 5 (A Wettable Powder) 2 parts of Compound A, Q.l part of Compound IV, 5 parts of Compound C, 42.9 parts of diatomaceous earth, 45 parts of white carbon, 3 parts of sodium lauryl sulfate (a wetting agent) and 2 paxts of calciu~ lignin sulfonate (a dispersant) were thorou,ghl~ grou~d and mixed together to obtai~ a wettable powder of the present in,Vention having an active ingredient concentration of 7.1%.
Formulation Example 6 (A Wettable Powder) 0.5 part of Co~pound A, 5 parts of Compound V, l~Z~2 1 10 parts of Compound C, 10 parts of Compound D, 35 parts of diatomaceous earth, 34.5 parts of white carbon, 3 parts of sodium lauryl sulfate (a wetting agent) and 2 parts of calcium lignin sulfonate (a dispersant) were thoroughly ground and mixed together to obtain a wettable powder of the present invention having an active ingredient concentration of 25.5%.
Formulation~Example 7 (A Flowable Concentrate) 1 part of Compound A, 0.1 part of Compound VI, 3 parts of polyoxyethylene sorbitan monool eate , 3 parts of CMC and 92.9 parts of water were mixed together and wet ground until the grain size of the active ingredients became 5 ~ or less to obtain a flowable concentrate of the present invention having an active,ingredient concentration of 1.1~.
FOJ:IIIUL~ JI ~XLIIII~1C ~ (~ r~'10Wa1~10 COIIC~31l:r~
1 part of Compound A, 10 parts of Compound VII, 10 parts of Compound C, 3 parts of polyoxyethylene monooleate, 3 parts of CMC and 73 parts of water were mixed together and wet ground until the grain size of - the active ing~edients became 5 ~ or less to obtain a flowable concentrate of the present invention having an active ingr~dient concentration of 21%.
Form,ulation Example 9 ~A Flowable Concentrate) 0.5 part of Compound A, 10 parts of Compound II, 10 parts of Compound C, 10 parts of Compound D, 3 parts _ g ~
1~2~'~2 l of polyoxyethylenemonooleate , 3 parts of CMC-and 63.5 parts of,water were mixed together and wet ground until t:he grain size of the active ingredients became 5 ~
ox less to obtain a flowable concentrate of the present invention having an active ingredient concentration of 30.5%.
Formulation Example lO (An Emulsifiable Concentrate) 1 part of Compound A, 2 parts of Compound III, 1.5 parts of imazalil, 3.5 parts of polyoxyethylene alkyl aryl ether (an emulsifying agent), 50 parts of cyclohexane and 42 parts of xylene were mixed together to obtain an emulsifiable concentrate of the present invention having an active ingredient concentration of 3~, , Formulation Example 11 (An Emulsifiable Concentrate) 1 part of Compound A, 4 parts of Compound IV, '4 parts of Compound C, 4 parts of hydroxyisoxazole, 15 parts of polyoxyethylene alkyl aryl ether (an emulsifying , agent), 52 partG of cyclohexane and 20 parts of,xylene were mixed together to obtain an emulsifiable concentrate of the present invention having an active ingredient concentration of 9%.
FormuIation ~xample 12 (An Emulsifiable Concentrate) 0.5 pa~t of Compound A, 4 parts of Compound VII, 2 pa~ts of Co~pou~ld C, 15 parts of polyoxyethylene .alkyl aryl ether (an emulsifying agent), 50 parts of 1~2g4Z
1 cyclohexane and 28.5 parts of xylene were mixed together to obtain an emulsifiable concentrate of the present invention having an active ingredient concentration of 10,5%.
Test Example 1 10 g of wheat seeds (variety: Norin No. 61) inoculated and infected with Tilletia caries were dipped into an aqueous solution containing a prescribed concentration of each of wettable powders of the present invention prepared in the same manner as in Formulation Examples 4 to 6, for 24 hours. Thereafter, they were shown in an upland field and cultivated on.
When the wheat came into ears, they were examined whether they had any symptoms of the disease or not, and the percentage of healthy seedlings was calculated from the following equation.
Number of healthy-seedlings heaClthyage of = n treated plot x 100 gs uninoculated and untreated plot Moreover, the synergistic effect of the seed disinfectant compositio~ of the pxesent invention was studied accoxding to the, following procedure.
The e~fect,' (E) expected from the mixing of a compound X with another compound Y is generally giYen by the following equation:
E = m + n _ m10O
1~2~
1 E: Preventing effect(~) (percentage of healthy seedlings) expected when a mixture of X and Y in respective amounts of p and q is used.
m: Preventing effect (%) (percentage of healthy seedlings) when X is used alone in an amount of p.
n: Preventing effect (%) (percentage of healthy seedlings) when Y is used alone in an amount of q.
The effect (E') expected from the mixing of a compound X', a compound Y' and a compound Z' is generally given by the following equation:
10 0 10, O O O
E': Preventing efect l~) (percentage of healthy seedlings) expected when a mixture of X', Y' and Z' in respective amounts of p', q' and r' is used.
m': Preventing effect (%) (percentage of healthy seedlings) when X' is used alone in an amount of p'.
n': Preventing effect (~) (percentage of healthy seedlings) when Y' is used alone in an amount of q'.
Q': Preventing effect (%) (percentage of healthy seedlings) when Z' is used alone in an amount of r'.
An equation giving the effect expected from the mixing of four compounds can be introduced from the aboYe equation. Needless to say, when any one of four compounds shows no preyenting effect, the effect equals that expected from the mixing of other three compounds [See "Weeds" 15, pp. 20-2 (1967)].
l~Z~4Z
1 If the found effect obtained by mixing the two is larger than the expected one, it can be said that a synergistic effect is obtained. The results are shown in l'able 1.
Table 1 Compound A _ I _ Concentration Ill _ of Compound B IV _ Active Ingredients V _ (ppm) Vll _ Compound C _ Compound D
_ (-)-Enantiomer Content in Compound A (~ by weight) _ ~ Percentage of Found _ : Healthy Seedlings Expected _ - Cont'd -* Inoculation and no treatment.
** No inoculation and no treatment :~ :
Table l [Cont ' d) --1_ 2 3 4 5 6 7 8 9 lO _ o == == =_ S S S S _ _ === =======-_ ===== ~= ==-66.5 90.2 94.7 66.5 90.2 94.7 66.5 90.2 94.7 66.5 _ 80 83 85 81 84 86 79 82 83 80 _ 47 52 54 44 49 52 47 52 55 45 _ - Cont ' d 1~?2~342 Table 1 (Cont'd) ..
_ 12 13 14 15 16 17 18 19 20 _ 0.5 0.~ 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 _ _ _ 5-- _ _ 5 5 5 _ _ === === = = S _ ._ _ _ _ _ _ 5 ---- S- 5 _ _ _ 5 5 5 5 5 _ .. .. _ _ . __ _ 66.5 66,5 66.5 90.2 94.7 66.5 66.5 90.2 94.7 66.5 _ . _ 47 45 47 52 54 52 50 54 57 ---- 53 _ - Cont'd -~Z~ 2 Table 1 (Cont'd) -21- 22 - 23-- -2-4- 25 26 27 28 2930 _ ___ _ 0.5 0.5 0.5 0.5 0.5 O.S O.S O.S 0.50.5 _ ~l~t .= s s--====== = ~
S 5 5 _ _ __ _ 66.5 66,s 66,5 66.5 90.Z 94.7 66.5 66.5 _ 1 _ ... . ._ _ _. _ 92 91 90 93 98 g5 94 99 100 . _ 51 52 Sl 52 56 59 52 50 54 57 _ - Cont'd -~Z5~2 Table 1 (Cont'd) 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 11.5 _ 5 ~
5 5 5 5 5 5--5 55 = _ ~ '1''- i- 1 1 1 1 1 1 _ ._ _.. _ 66.5 90.2 94.7 66.5 66.5 66.5 66.5 90.2 94.7 66.5 .. __ . _ . , _ _ 94 98 100 g4 95 ---- 93 95 98 100 70 _ _53_ 57 59 51 52 51 52 56 59 _ _ - Cont'd -l~Z~ ~2 Table 1 (Cont ' d ) 41 42 1 43 44 45 46 47 48 49 50 _ ,__ I . _ 0_ 11.5 O.S ll.S O.S ll.S S _ 11.5 5 _ ~:=r~
.
66, 5 90 . 2 90 . 2 94 . 7 94, 7 _ _ _ _--=_ = =~
- Cont ' d 2~'~2 Table 1 (Cont ' d) 51 52 53 54 55 56 57 --58 59 60 _ _ ~ ~ _~ _~___ 11.5 5 _ 11.5 _ ====== ===--_ , . _ ._. .. ..__ _ 9 23 16 20 18 18 16 22 18 18 _ - Cont'd -Z~42 Table 1 (Cont'd) 61- 62 63 -0~ 00**
.._ '_-- ._ _, S ====
11.5 5 ==
. . _ 1 Test Example 2 Each of flowable concentrates of the seed disinfectant composition of the present invention prepared according to Formulation Examples 7 to 9 was sprayed onto ~S 10 g of barley seeds (VarietY: New Golden) infected with :~ Helminthos~or_um gramineu~. The~eaftex, the barley seeds were sown in an upland field and cultiyated on. When the barley came into ears, they were examined whether they had any symptoms of the disease or not, percentage of healthy seedlings was calculated in the same manner as in Test Example 1 and a synergistic efect was confirmed by comparing l the found value with the expected value. The results are shown in Table 2.
Table 2 _ . . _ _ Compound A
Amount of Active Ingredients Compound B IV
(gjlOOkg-dry seed) VII _ . _ Compound C
__ _ Compound D
.__ _ (-)-Enantiomer Content in Compound A (~ by weight) .... _ _ _ Percentage of Found Heal*hy Seedlings :Expected . _ - Cont'd -* Inoculation and no treatment ~ ** No inoculation a~nd no treatment :~ :
2~'~2 Table 2 (Cont ' d) - - 2 3 - 4 5 6-- 7 8 lO _ 5 l l l ~l 5 ~ = t = == = = = _ s - s . ...
__ ____ _~_ 66.5 90.2 94.7 66.5 90.2 94.7 66.5 90.2 94.7 66.5 _ . _ _ 32 42 48 32 42 48 32 42 4~3 32 _ - Cont ' d -l~Z9 ~2 Table 2 (Cont ' d) ~ t~l === = == 5 5 5 5 _ _ - 5 5 5 _ ~ --S ___ S -66.5 66,5 66.5 90.2 94.7 66.5 66.5 90.2 94.7 66.5 .. _ _ ,~._ ,. _ 32 32 32 42 48_ 42 42_ 50 55 __ 42_ _ - Cont ' d l~?Zg'~Z
Table 2 (Cont ' d) _ _ 5 _ ===== == S __ S
== =_ __ ====~
. 5 5 5 5 _ ..... _ _ 66.5 66,5 66,5 66.5 90,2 94,7 66,5 66,5 90.2 94.7 _ 87 89 86 88 93 96 g3 96 99100 _ 42 42 42 42 50 55 42 42 _ S055 _ - Cont'd -l~\Z~ ~2 Table 2 (Cont'd) 31 32 33 34 35 36 37 38 39 40 ~~ _ _ 1. 1 1 1 1 1 1 1 1 16 _ _ _ === S ===~ = = _ S
_ === ===__ _= _ _ 5--------- 5 . _ 66.590.2 94.7 66.566.5 66.5 66.5 90.2 g4.7 66.5 . . __ _ 92 97 100 91 9Z 9o --- 93 98 100 72 _ 42 50 55 42 42 42 42 50 55 _ - Cont'd -lZ~29'~
Table 2 (Cont ' d ) 41 42 ~ 43 44 45 46 47 48 49 50 _ 16 1 16 1 = = == _ _ =_ 16 5 16 5 ~ _ ======== 16 _ _ _ ~ _ _ 66.5 90.2 90.2 94.7 94.7 ,_ __ . _ . _ - Cont'd -Z9~Z
Table 2 (Cont ' d) Sl- 52 53 54 55 56 57 58 59 60 _ S === _== ==--16 5 l ~
== __ _ __ 16 5 16 _ 0 _ 0 0 0 0 0 0 0 ~ 0 35 = = ========_ - Cont ' d Table 2 (Cont'd) 61 62 63 0* 00**
_- = = = =
.__ ___ _ ~ ~
.
_ 16 5 ..
====
1 Test Example 3 Each of emulsifiable concentrates of the seed disinfectant composition of the present invention prepared according to Formulation Examples 1~ to 12 was sprayed onto 10 g of barley seeds ~yariety: Yideo) infected with Ustilago nuda. Thereafter, the barley seeds wexe sown in an upland field and cultivated on. When the harley came into ears, they were examined whether they had any symptoms of the disease or not, percentage of healthy seedlings was calculated in the same manner as in Test Example 1 and a synergistic effect was confirmed by comparing the found z 1 value with the expected value. The results are shown in Table 3.
Table 3 .. . . . _ _ .
. Compound A I _ II _ Amount of III
Active Ingredients Compound B IV _ (g/lOOkg-dr ~eed~
Compound C
, ._ _ Compound D
: .__ _ ~-)-Enantiomer Content in Compound A (% by weight) . _ _ ._ _ Percentage of Found _ . Healthy Seedlings Expected _ - Cont'd -* Inoculation and no treatment ** No inoculation and no treatment , ~Z~'~2 Table 3 (Cont'd) 1 2 3 4 5 6 7 8 lO _ _ 0.50.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 '10- 10 10 _ _ == = 10 10 10 == ==~
10 ~__ 10 _ . _ .. , .
_ . . _ . _ _ . .
_ 66,5 90,2 94.7 66.5 90.2 94.7 66.5 90.2 94.7 66.5 ., _ _ 66 75 76 66 75 77 65 74 76 65 _ - Cont'd -Z
Table 3 (Cont'd) - l2 l3 l4 l5 l6 l7 l8 l9 20 _ 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 ===== 10 = =--= _ =_== =10 10 10 10 ~ _ = 10 10 10 10 ~= = = = _ . _ _ , _ 66,5 66.5 66.5 90.2 94.7 66.5 66.5 90;2 94.7 66.5 _ 79 78 81 87 91 88 89 93 96 85 _ _ _65 64 67 76 77 66 66 75 77 65 _ - Cont'd -l~Z~'~2 Table 3 (Cont ' d) 21- 22 23 ~ 24 25 2627 _ __ _ 0.5 0.5 0.5 0.5 0.5 0.5 30.5 _ _ _ 10 ==== = = _ _ 10 10 10 10' 10 __ ` 10 '-'' 10 10 10 10 10 ~ . _ '=== ====_ 66 . 5 66 . 5 66, 5 66. 5 90 . 2 94 . 7 66 . 5 _ 65 65 64 67 76 77 . _ - Cont ' d Table 3 (Cont'd) 2~3 29 30 31 32 ~ 33 34 35 36 37 _ _ . _ _ 0.5 30.5 0.5 30.5 0.5 _ 30.5 10 _ _ . 30.5 10 _ = = _ = = = = = = 30.5 _ = == ==== === __ _ 66,5 90.2 90,2 94,7 94,7 ,. _ 58 100 69 100 71 25 18 28 Z0 23 _ - Cont'd -l~Z~ ~2 Table 3 (Cont ' d) __ _ - _ _ _ _ _ _ 30.5 10 _ 30.510 _ =~
_ _ _. _ 16 24 17 24 16 19 15 25 21 5 _ ,_ _ ~__ ==== =-- Cont ' d -Table 3 (Cont'd) 48 a* oo**
_ _ _ .
-===
''-'-lo- .
O O '100 ===
1 Test Example 4 10 g of wheet seeds (variety: Norin No. 73) infected with Fusarium nivale was dust-coated with each of wettable powders of the present invention prepared in the 5 ~same manner as in Formulation Examples 4 and 5. Thereafter, : the wheet seeds were sown in an upland field and cultivated on. When the wheet reached the fourth laafing stage, they were exa~ined ~hether they had any symptoms of the disease or not, precentage of healthy seedlings was calculated in the same manner as in Test Example 1. The results are shown in Table 4.
Table 4 . .. _ _ , _ . ~c~ourc A ,_ _ Amount of III _ Active Ingredients Compound B IV _ (g/lOOkg-dr~ seed) ¦
Compound C _ Compound D
. . .__ . . . _ (-)-Enantiomer Content in Compound A (% by weight) ._ ._ _ Percentage of Found _ Healthy Seedlings Expected _ _ - Cont'd -* Inoculation and no treatment ** No inoculation and no treatment l~z~ z Table 4 ~Cont ' d) __ 2 __ 5 _ 7 _ 10 _ ._ . _ 0.5 0.5 0,5 _ 0.5 0.5 == == _ ,~__ ~ _ _ 0.5 0.5 0.5 0.5 _ .._ _ _ _ , ._ _ 66.5 90,2 94.7 66,5 90,2 94,7 66,5 90,2 94,7 66,5 ,, _ _83 88 90 82 87 90 81 86 89 82 _ 51 57 60 52 58 61 50 55 59 50 _ - Cont ' d -1 ~Z5~2 Table 4 (Cont ' d) 2 13 14 ls 16 17 18 19 20 _ ===== 0 . 5 0, 5 0 . 5 0 . 5 =_ 1 1 1 1 - 1 _ = ==== = = ==-66.5 66,5 66.5 90.2 94.7 66,5 66.5 90.2 94.7 66.5 _ _ _ _ 50 49 54 59 62 53 55 60 63_ 52 _ - Cont ' d -l~Z~2 Table 4 (Cont'~) 21 _ 22 23 24 25 26 27 28 29 30 _ _ 0.5 _ 0.5 0.50.5 _ ._ _ --0.5 = ====, _ 0.5 _ _ 0.5 _ 0.5 0.5 0.5 .. _ 1 1 1 1 1 1 1 1 1 _ . 1 1 1 1 _ 66,5 66,5 66,5 66,5 90,2 94,7 66,5 66.5 gO.2 94.7 ~, .. _. . _ ~ __ .. _ 53 52 51 ,56. 61 64 53 55 6063 _ - Cont'd -1~2~ 2 Table 4 (Cont ' d) 31--32 33 34 35 36 37 38 39 40 _ 10 10 10_ ~0 10 10 10 10 10 12.5 _ 1 1 1 ~ ~ l~t . _ 66.5 90.2 94.7 66,5 66.5 66.5 66,5 90.2 94.7 66.5 _ _ 52 5861 53 52 51 56 61 64 _ - Cont'd -Table 4 ~Cont'd) 41 42 43' 44 45 ~- 46 47 48 4950 ~- _ 12.5 lO ~ 12.5 lO _ =~
_ ~ _ _ _ ~ ~ _ ======== =_ . . _ _ 66.5 90.2 90.2 94.7 94.7 _ ............... ... .. _ 38 48 45 52 ~49 58 21 62 23 56 _ = =_ - Cont'd -1~2~'~2 Table 4 (Cont'd) 51 _ 52 53 54 - SS 56 57 58 S9 60 _ __ _ . . _ 12.5 0.5 _ _ 12.5 0.5 _ 12.5 0.5_ 12.5 _ ==========_ ._ _ === =======_ - Cont'd -Table 4 (Cont'd) 61 62 63 0* 00**
== ===
=====
12.5 .,_ 1 Test Example 5 Each of emulsifiable concentrates of the present invention prepared according to Formulation Examples 10 to 12 was sprayed onto 10 g of barley seeds (variety: Sonja) infected with PyrenoPhora teres. Thereafter, the barley seeds were sow,n in an upland field and cultivated on, When the barley came into ears, they were examined whether they had any symptom,s of the disease or not, pércentage of healthy seedlings was calculated in the same manner as in ~est Example 1. The resuIts are shown in Table 5.
2g'~2 Example 5 _ Compound A _.
_ _ I _ II
Amount of III _ Active Ingredient~ Compound B IV _ (g/lOOkg-dry see ) Compound C
. . _ _ _ _ Compound D
.. ._ . . _ (-)-Enantiomer Content in Compound A (~ by weight) . . _ .. _. . ... _ Percentage o Found . . _ Healthy Seedlings Expected _ - Cont'd -* Inoculation and no treatment ** No inoculation and no treatment 1~2~'~2 Table 5 (Cont ' d) --_ 3 _ 5 ~ _ 7 8 9 10 _ _ __ _ O.S 0.5 0.5 0.5 0.5- 0.5 _ _-_ __ _ _-._ ._ _ ._ _ ............... _ _ . . _ 66.5 90,2 94.7 66.5 90.2 94.7 66.5 90.2 94.7 66.5 _ . ._ _ _ 6~ _ 70 73 ----- 65 70 73 65_ 70 73 65 _ - Cont'd -~Z~3~2 Table 5 ~Cont'd) 11 12 13- 14 15-- 16 17 -- 18 19 20 _ ._ .. _ _ _ --0.5 O--S = = === ===-_ _ 0.5 0.5 0.5 __ _ . _ _ === === == =-66.5 66,5 66.5 9~.2 94.7 66.5 66.5 90.2 94.7 66.5 _ _ 91 94---- 89 91 96 97 88 _ 73 74 74 78 80 74 _ - Cont'd -l~?Z~'~2 Table 5 (Cont ' d) 21 122 23 24 25 26 27 _ 0 ~ 10 10 10 10 35 . 5 _ _ _ ~ r _ .... _ _ 66.5 66.5 66.5 66.5 90.2 94.7 66.5 .. _ 87 88 85 91 98 99 100 _ _ 74 74 74 74 78 80 _ - Cont'd -Z~ 2 Table 5 (Cont'd) _ - 29 30 31 32 33 34 35 3637 _ 10 _ 35.5_ 10_ 35.5 10 _ _ 35.5 0.5 = -= = = = = ~ 35.5 O.S 35.5 _ ==== ======-== == ====== _ . _ . -. _ 66.5 90.2 9~,2 94.7 94.7 _ 100 70 100 73 5 0 3 02 _ __ ~ _ - Cont'd -?Z9'~2 Table 5 (cont'd?
_ _ ,_ . _ .. . _ -O.S 35.5 O-S = = = = = = = -= = = 35.5 O.S 35.5O.S = = = _ 35.50.5 _ _ 35.5 _ .... _ .,,_ . _ . . .. _ . . _ _ . ._ _ - Cont'd -l~fZ~2 Table 5 (Con~'d) 48 0* 00**
===
_ == =
= ==
1 Test Example 6 Each of flowable concentrates of the present invention prepared according to Formulation Examples 7 to 9 was sprayed onto 10 g of barley seeds (variety:
Akashinriki) lnfected wi,th Rhynchosporium secalis.
Thereafter, the.seeds were sown in an upland field and cultiyate.d o~. Wh,en, ~he baxle~.reached the internode elongation stage, the~ were exam,ined whether they had any sympto~s of the disease OX not, pexcentage of healthy seedlings was calculated in the same manner as in Test Example 1. The results are shown in Table 6.
g~z Table 6 _ ._ Compound Amount of III _ Active Ingredients Compound BIV _ (g/lOOkg-dry 5 ed) Compound C_ Compound D
. _ t-)-Enantiomer Content in Compound A (% by weight) _ _ Percentage of Found _ Healthy Seedlings Expected - cont'd -* Inoculation and no treatment No iAoculation and ~o treatment ' :
~;29~2 Table 6 (Cont'd) 2 3 4 5 _ 7 8 9 lO _ _ 66.5 90,2 94,7 66.5 90.2 94.7 6-6.5 90.2 94.7 66.5 _ _ . _ 44 49 5l 42 47 48 41 46 48 39 _ - Cont'd -:;
:
, l~Z~2 Table 6 (Con*'d) 12 l3 l4 lS l6 l7 l8 l9 20 _ lo 110 10_10 10 10 10 10 10 10 _ ~ I = ~ ~:~ ~
_ = l l L l = = = = =
_ .__ === = 10 10 10 10 10 66.5 66,5 66,5 90,2 g4,7 66,5 66,5 90,2 94,7 66,5 ..
- Cont'd -Z~ ~2 Table 6 (Cont'd~
211 22 23 24 25 26 27 28 29 30 _ _ __ _ __ ~ 1 ~ 1 1 _ 1 1 1 = = = _ 10 10 10 10 10 10 10 10 10 10 _ ....... ~ _ 66,5 66.5 66.5 66,5 90.2 94.7 66.5 66.5 90.2 94.7 _ ~ ..... ... _ 39 43 41 45 50 52 45 42 47 49 _ - Cont'd -1.;2~2~ ~2 Table 6 (Cont ' d) 31 - 32 33 34 35 36 37 38 39 40 _ lO 10 10 10 lO lO 10 10 26 _ _ 1 1 1 _ _ _ _ 66.5 90.294.7 66.5 66.5 66.5 66.5 90.294.7 66.5 _ 89 97 100 89 91 88 92 99 lO0 61 ~ _ 41 47 48 39 43 41 45 50 52 _ - Cont'd -Z9'~2 Tablç 6 (Cont ' ~) 41 42 43 44 45 46 47 48 49 50 _ == = = = I ===-_ , ._ .._ _ ~ ... _ . . _ 66,5 90,2 90,2 94,7 94,7 . _ = ==== == == _ - Cont'd -1~29'~2 Table 6 ~Cont ' d) 51. 52 53 54 55 56 ~ 57 58 59 60 _ -- = = = = = = = =
1 = === =====_ 26 1 . . _ = = = 26 L 2 6 1= = =--26 1 _ . 26 _ _. _ . ........... ..... ..... ..... .................. ........ .. _ ._ __ . _ L3 SS L0 S9 16 Sl 13 66 19 - Cont ' d 29~2 Table 6 (Co~t'd) 61 62 63 0* 00**
_ __ _ === = =
.
= = ===
26 S = =
, .. .
_ .
1 Test Example 7 Grains of unhulled rice (variety: Kinki No. 33) ; infected with benomyl-sensitive or benomyl-resistant ; Gibberella fujikuxoi we~e dust-coated with a prescribed amount of a dust of the seed disinfectant composition of the prese~t inVention prepared according to Foxmulation Example 1 ox a com~exciall~ ayailable seed disinfectant ~Benlate T ~ J. ~he~eaftex, the u~hulled rice ~as sown in sandy loam in a plastic pot at a rate of 100 grains per pot, covered with 80il and cultivated for 16 day~ in a 1,2~Z9 L~2 1 greenhouse. Then, the symptoms of the disease was examined and the percentage of healthy seedlings ~as calcuIated in the same manner as in Test Example 1. The results are shown in Table 7.
Table 7 . . .... _ _ Compound A
Amount of ~II
Active Ingredients Compound B IV _ (g/lOOkg-dry eed) Compound C
_ Compound D
_ Benlate T ~ 1 . _.
: ~-)-Enantiomer Content in Compound A (% by weight)¦
Percentage of a Healthy Seedlings *3 1, - Cont'd -* Inoculation and no treatment ** No inoculation and no treatment *l Com~ercially available seed disinfectant ~a mixture of benomyl and thiram) *2 The case where unhulled rice infected with benomyl-sensitive fungi was used.
*3 The case where unhulled rice infected with benomyl-resistant fungi was used.
Table 7 (Cont'd) . .
1 1 1 1 1 6 1 8 1 10 _ 10 10 10 10 10 10 == ==-r~
. ..
. .
. . .
.. .. .
.
66,5 90.2 g4.7 66.5 90.2 94.7 66.5 90.2 66.5 66.5 .. . _ .. . . . _ ~ 100 100 100 100 100 100 100 100 100 100- _ - Cont'd -~ 60 -Table 7 (Cont' d) _ 12 13 14 1516 _ 17 18 19 20 _ _ 1 1 1 1 1 1 1 1 1 _ . 10 10 10 - _ .... 10 _ __ _ `10 . _ 0 ~ = = =====-. _ _ _ ..... . . _ 66.5 66,5 66,5 90,2 94.7 66.5 66.5 90.2 94.7 66.5 . . . . _ 100 100 100 100 100 100 100 100 100 100 _ 1~0 100 100 100 100 100 100 100 100 100 _ - Cont'd -9~2 Table 7 (Con~t ' d~) t~~ t 10 = ====== ==
= 10 10 ==== ===
== 10 10 10 = ===
10 10 10 10 10 10 10 10 10 10 _ .
. . . .
66.5 66,5 66,5 66,5 gO,2 g4,7 66,5 66,5 90.2 94.7 _ __ _ 100 100 100 100 100 100 100 100 100 100 _ - Cont'd -~ 62 --9~2 Table 7 (Cont'd) . .__ _ _ 31 32 33 34 35 36 37 38 39 40_ _ 10 10 10 == =====-=== 10 10 === = =~
_~ ~ ~ 10 10 10 10 _-. _ - 5 5 --- 5 5 5 5 5 5 __ _ _. . .. . ._ . .. _ _ _ 66.5 90.2 94,7 66.5 66.5 66.5 66.5 90.2 94.7 66.5 _ .... .. . _ 100 100 100 100 100 100 100 100 100 90 _ - Cont'd -2~'~Z
Table 7 (Co~t'd~
41 142 43 44 45 46 47 48 4950 _ L 126 l 26 1 _ _ .. 26 lO _ _ 26lO _ _ _ __ 26 _ _ _ _ _ _ _ - ._ _ _. , _ 66.5 90.2 90.2 94.7 94.7 ._ . _ ~_ 36 92 41 95 44 43 25 40 21 38 _ - Cont'd -: :
Table 7 (Cont ' d) 51 52 53 54 55 56 57 58 59 60 _ =_ =========_ _ _ _ = == == == Z6 lO 26 _ _ . _. _ ___ _~____ _ 40 93 43 g4 41 89 38 98 44 0 -.. _ _ 19 40 21 43 23 37 20 65 38 0 _ - Cont ' d Table 7 (Cont'd~
_ _ _ ~ . ~ ~; D' __ _~___ __ ~' lO26 -5 100 50 ~ _ = = ====
.
_~ _ O O 70 48 O 100 .
1 Test Example 8 Grains of unhulled rice (variety: Nipponbare) infected with Cochliobolus miyabeanus were dust-coated with a prescribed amount of each of dusts of the present invention pxe~axed according to Foxmulation Examples 4 ~ to 6. Thexeaftex, the unhulled rice was sown in sandy ; loam in a pl~stiç pot at a Xate of 50 gxain~ per pot, covered with soil and cultivated for 21 days in a gréen-house. Then, the symptoms of the disease was examined - 66 ~
9 ~ Z
1 and the percentage of healthy seedlings was calculated in the same manner as in Test Example 1. The results are showrl in Table 8.
Table 8 . Compound A
II _ Amount of III _ Active Ingredients Compound B IV
(g/L O Olcg-dr seed ) y _ _ Compound C
_ _ : Compound D
... . , (-~-Enantiomer Content in Compound A (% by weight) . ~
Percentage of Found _ . Healthy SeedlingsExpected - Cont'd -* Inoculation and no treatment ** No inoculation and no treatment 1~?2~2 Table 8 ~Cont ' d~
===== = 10 10 10 -10 . ._ ._ .
66.5 90.2 94.7 66.5 90.2 94,7 6~.5 90.2 94.7 66.5 61 68 _ 70 62 67 69 59 68 69 58 - - Cont ' d -~z~z Table 8 ~Cont' d) 12 13 14 15 16 17 18 19--20- _ ~,_ ~ 10 ~
_ _ 66.5 66,5 66,5 90,2 94.7 66.5 66.5 90,2 94.7 6~.5 .__ .,. . _ _59' 56 62 69 71 85 88 91 93 82 16 15 17 19 2l 33 32 33 35 - Cont ' d -- 6g --;29~2 Table 8 (Cont'd) . _ _ . _ 1 1 1 1 1_ 10 1 1 1 _ __ 1010--- 10---_ _ 10 10 10 ~ ~ ~
_ = = 10 10 10 ====~
_ 5 5 5 5 _ _ . . ._ _ 66.5 66.5 ~6.5 66.5 90.2 g4.7 66.5 66.5 90,2 94.7 .. . . _ 84 ~1 84 93 95 91 93 98 100 _ 32 _ 31 30 32 34 35 33 32 33 35 _ - Cont'd -.2 Table 8 (Cont ' d?
3~ 32 33 34 35 36 37 38 39 40 _ _ ._ _ ~. l 1 1 l 1 1 l l 21 _ ... _ ... _ _ 5~_ 5 5 5 5 5 5 5 5 _ ; ._ _ 66 . 5 90 . 2 94 . 7 66 . 5 66 . 5 66 . 5 66 . 5 gO . 2 94 . 7 66 . 5 _ 97 100 92 91 90 92 99 100 20 _ 31 32 34 32 31 _ 30 32 34------ 35 _ - Cont'd -Table 8 ~Cont ' d?
l- 21~ l 21 1 2l 10 =~ =-=~ ===~= 2l lO 2l _ . _ ~-===== = = __ _ _ _ 66,~ 1 90.2 90.2 94.7 94.7 __ j. _ == === = ==-- Cont'd -Z
Ta~le 8 (Cont ' d) , _ j , . . . . .
51 ~ 52 53 54 1 55 56 j 57 1 58 59 1 60 ll ~ l l r 21,10 1 21110, 1 I 1 _ 21 1 10 21 10 1 _ i -~ 21 , _ i _ __ _ -~~~-T---. _ . _ . _ ~
=== ======
- Cont ' d -~ :
~ 73 --Table 8 ~Cont'd~
-61~-_63 _ ~ 00~*
= ===--' S' .
.21 5 =
..
18 O O O 100 .
.
1 Test Example 9 Grains of unhulled rice (variety: Nipponbare) infected with Pseudomonas glumae were dust-coated with a prescribed amount of each of dusts of the pxe5ent invention prepaxed accoxdin~ ~o Fo~ulati~ Examples 1 to 3. Thereafter, the unhulled rice was sown in sandy loam in a plastic pot at a rate of 50 grains pe~ pot, covered with soil and cultivated for 21 days in a greenhouse.
Then, the symptoms of the disease was examined and the l;~~ ~Z
1 percentage of healthy seedlings was calculated in the same manner as in Test E~ample 1. The results are shown in Table 9.
Table 9 _ Co~a~d A II _ Amount of III _ Active Ingredients Compound B IV
~g/lOOkg-dry :eed) I :
_.___ _ Compound C
, ,,, ,_. _ _ Compound D
_ ..
(-)-Enantiomer Content in Compound A (% by weight) , _ Percentage of ¦ Found Healthy Seedlings ¦ Expected _ I _ - Cont'd -* Inoculation and no treatment ** No inoculation and no treatment 9~2 Table 9 (Cont'd~
2 3' 4 5 6 7 8 _ 10 ~- _ _ __ _ ~ ... _ 5 - 5 5 _ _ _ ~ _ ... ._ . ~ 5 5 5 _ ----~ 5------ _ .. ... . ._ . _ _ _ . _ . .. . . _. . _ ,. .. _ -. _ . . _ _ 66.5 90.2 94.7 66.5 90.2 94.7 66.5 90,2 94.7 66,5 ... _ _ ._ _ __ O O O O O O O O O O
_ - Cont'd -Z~2 Table 9 ~Cont'd~
_ _ 12 13 14 15 16 17 18 19 120 _ _ 5 ~ - _ ===== =_ S ~ S _ . _ .._ _ ~=~t~ t 5-- 5 55 _ ._ _ ._ .. _ .. l _ 66.5 66.5 66.5 90.2 94.7 66.5 6~.5 90.2 94.7 66.5 .. _ _ _ .. _ ._ _ 23_ 19 26 1 29 _ 33 29 31 _ 33 34 25 _ O O O_ O O O O O_ -o O
. _ .
- Cont'd -29~2 Table 9 (Cont'd) 21 22 123 1 24 25 26 127 128 ~29 30 _ ~. 1 1 1 1 1 1 1 1 1 1 1 1 1 1 = 1~ = l l 5 5 _ _._ i I l l 5 ~ _ ~ 5 5 5~ ~
51 5 ! 5 55 1 5 5 ~ 55 _ _ i 1 10 10 10 10 , .. _ 66,5 66.5 66,5 66.5 90,2 94.7 66.5 66.5 90.2 94.7 _ .__ .. __ _ 23 26 22 29 32 33 9S g4 98 00 ~ .. ._ _.. _ . _ 0 0 0 0 ~ 0 43 43 43 43 .__ . .. _ _ - Cont'd -~Z9'~2 Table 9 (Cont'd~
31 _ 32 33 34 35 36 37 38 39 40 _ 1 1 1 1 1 _ 1 1 1 _ 21 _ S S S s ~
_ _ ,= ~_ 5 _ _ 5- _ _ 5 _ 5 5 _ 5 5 5 5 5 5 _ .. . ._ _ 66.5 90.2 94.7 66.5 66.5 66.5 66.5 90.2 94.7 66.5 . . .. _ , . _ . .. ._ . . _ 43 43 --- 43 _ 43----- 43 43--- 43 43 43 _ - Cont'd -Table 9 (Cont ' d) 41 42 43 44 45 46--- 47 ~ 48 49--- 50 _ --1_ 21 _ 21 1 21 5 = ==-_ _ .21 5 _ ___ ~ _~ 21 _ _ _ . _ ... _ _ . ... ._ _66 . 5 90 . 2 90, 2 9 4 . 7 9 4 . 7 _ 0 6 0 7 0 9 0 4 0 2 _ - Cont'd -1~2~2 Table 9 ~Cont ' d) _ i I ___ _ ~ t.
_ 215 _ _ 21 5 _ = == ==== 21 5 21 _ .. _ ...._ _ __ . . . . ,, _ . . .. _ __ ._ . . _ . .. _ __ _ - Cont'd -z Table 9 (Cont ' d) 61 62 63 0~ 00*~
_ __ ,_== ==' =====.
21 10 ~ .
O 58 43 O lOO
== = ~
1 The present invention relates to a seed dis- -infectant composition comprising (E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol containing not less than 50% by weight of (-)-(E)-l-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-l-penten-3-ol (hereinafter referred to as Compound A) and at least one benzimidazole thiophanate fungicide (hereinafter referred to as Compound B) and optionally comprising O,O-dimethyl-O-(2,6-dichloro-4-methylphenyl)-phosphorothioate ~hereinafter referred to as Compound C)and/or l-ethyl-1,4-dihydro-6,7-methylenedioxy-4-oxo-3-quinoline carboxylic acid (hereinafter referred to as Compound D) or a salt thereof.
Heretofore, benomyl thiophanate-methyl, thiram, carboxin, PCNB, organic mercury and admixtures thereof have been used to prevent seed born diseases.
However, the commercially available disinfectants mentioned above have effects only on limited diseases, and such a problem arises that these disinfectants lose their ; 20 effects of preYenting seed bor~ diseases on resistant fungi which have appeared a~ong the disease on ~hich these disinfectants had antifungal effects before.
In view of this situation, the present inventor have ~ade extensive research to develop a seed disinfectant having a wide antifungal spectrum and showing a stable -- 1 -- ~
3'~'~
l effect of preventing diseases on the above-mentioned :resistant fungi.
As a result, it has been found that a seed disinfectant composition comprising Compound A and Compound B in a specific weight ratio and optionally comprising Compound C and/or Compound D or a salt thereof in a specific weight ratio have not only all the properties mentioned above but also an excellent synergistic effect.
Thus, according to the present invention, there is provided a seed disinfectant composition comprising effective amount of ~ A) (E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol containing not less than 50% by weight of (-)-(E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-Z-(1,2,4-triazol-l-yl)-l-penten-3-ol and (B) at least one benzimidazole thiophanate fungicide, wherein the weight ratio of (A):(B) is 1-50:1-50.
Compound A, one of the active ingredients of the seed disinfectant composition of the present invention, is a compound.selected from the group consisting of the compounds disclosed in Japanese Patent Application Kokai ~Laid-Open) Nos. 124,771/80.and 99,575/82. In other words, Compound A may be a racemic compound, a racemic mixture containing more than 50% by weight of ~ (E)-1-~2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-l~penten-3-ol and a pure ~-)-(E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penken-3-ol.
.Fxom the viewpoint of exertion of disinfectant -- 2 ~
1 properties, it is preferable that Compound A contains not less than 5Q~ by weight of (-)-(E)-1-(2,4-dichlorophenyl)-~,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol (hereinafter referred to as (-)-enantiomer), and since the more Compound A contains (-)-enantiomer, the greater the disinfectant effect becomes, it is more preferable that Compound A contains not less than 80% by weight of (-)-enantiomer, most preferably, it is substantially pure (-)-enantiomer (purity: 90% by weight or more).
Known benzimidazole thiophanate fungicides can be used in the present invention. However, preferable members are methyl l-(butylcarbamoyl)benzimidazole-2-ylcarbamate (common name: benomyl, hereinafter referred to as Compound I), 2-(4-thiazolyl)benzimidazole ~common name: thiabendazole, hereinafter referred-to as Compound II), methyl benzimidazol-2-ylcarbamate (common name:
carbendazim, hereinafter referred to as Compound III), 2-(2-furyl)benzimidazole lcommon name: fubelidazol, hereinafter referred to as Compound IV), 1,2-bis(3-methoxycarbonyl-2-thioureido)benzene (common name:
: thiophanate-methyl, hereinafter referred to as Compound V), ~; : 1,2-bis:(3-ethoxycarbonyl-2-thioureido)benzene (common name: thiophanate, hereinafter refe~red to as Compound YI~, methyl 1-(2-cyclohexenylcarbamoyl)-2-25~ benzimidazolecarbamate (hereinafter referred to as Compound VII) and the like. Compounds I to.VI are known as fungicides.for.various diseases of fruit trees, vegetables, ba~ley, wheat, oats,.rye and th~ like. Compound VII is 1~2~2 1 disclosed in Japanese Patent Application Kokai (Laid-Open) No. 10,004/87.
The weight ratio of Compound A to Compound B
is usually 1-50:1-50, preferably 1-20:1-20.
Compound C used in the present invention is O,C-dimethyl-O-(2,6-dichloro-4-methylphenyl)-phosphorothioate disclosed in Japanese Patent Publication Kokoku (Post-Exam) No. 20,571/76.
Compound D is l-ethyl-1,4-dihydro-6,7-methylenedioxy-4-oxo-3-quinoline carboxylic acid disclosed in Japanese Patent Application Kokai (Laid-Open) No. 48,042/82.
In the present invention, Compound A, Compound B, Compound C and Compound D are referred to as active ingredients.
The weight ratio of Compound A: Compound B:
Compound C: Compound D is usually 1-50:1-50:0-50:0-50, preferably 1~20:1-20:1-20:1-20. In the present invention, they are mixed together and used.
The mixture of the active ingredients in the present invention can be used as it is, though it is :
usually used ln admixture with an inert carrier. If necessary, various adjuvants for formulation are added such as surface active agents, wetting agents, dispersing agents, sticking agents, thickeners, stabilizers and the like depending upon the use, to formulate the seed disinfectant to a preparation such as a wettablë powder, a dust, a flowable concen~rate, an emulsifiable concentrate l~Z~
l or the like.
The carriers in the above preparation include solid carriers such as a fine powder, a granule and the :Like of kaoline clay, attapulgite clayr bentonite, acid clay, pyrophylite, talc, diatomaceous earth, calcite, walnut shell powder, urea, ammonium sulfate, synthetic hydrous silica, white carbon and the like and liquid carriers such as, for example, xylene, methylnaphthalene and the like; alcohols, for example, isopropanol, ethylene glycol, cellosolve and the like; ketones, for example, acetone, cyclohexanone, isophorone and the like;
vegetable oils such as soy oil, cottonseed oil and the like; dimethyl sulfoxide; acetonitrile; water; etc.
Surace active agents used for emulsifying, dispersing, wetting-spreading and the ~ike include anionic surface active agents such as alkylsulfuric esters, alkyl sulfonates, aryl sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkyl aryl ether phosphoric esters, naphthalene sulfonic acid-formaldehyde condensates and the like and nonionic surface active agents such as polyoxy-ethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene-polyoxypropylene block copolymers, sorbitan fatty acid este~s, polyo~yethylene sorbitan fatty acid ester~ and the like.
Adjuvants other than the abo~e surface active agents for formulation are lignin sulfate, lignin sulfonates alginate, poly(vinyl alcohol), gum arabic, CMC (carboxy-methyl cellulose~, PAP tacid isopropyl phosphate) and the _ 5 _ 1.;2~Z94Z
1 like.
Other disinfectant, if necessary, such as nuarimol, hydroxyisoxazole basic copper chloride, imazalil and the like can be added thereto. Also, when anthraquinone is added thereto, the resulting disinfectant composition has a bird repellent effect, and the seed disinfectant composition of the present invention can be ùsed in admixture with other seed-treating agents.
The content of the active ingredients in these formulations is preferably 0.1-99.9% by weight, more preferably 0.1-80% by weight.
The seed disinfectant composition of the present invention can be used for dust-coating, dipping or spray-ing, In the case of dust-coating or spraying seeds with the seed disinfectant composition of the present invention, the amount of the composition used is prefer-ably from 0.00005 to 1~ as the active ingredients based on the dry weight of seeds, while in the case of dipping or spraying seeds in or with the seed disinfec*ant ~ composition of the present invention, the concentration - of the active ingredients in the composition is preferably from 0.01 ppm to 10~. However, the a~ount of the composi-tion used is va~iable depending on the type of preparation 2S or the kind of seed of crop to be treated.
The seed disinfectant composition of the present invention exhibits a synergistically high preventing effect on various 5eed born diséases and simultaneously Z~2 l has a wide antifungal spectrum and shows a stable prevent-ing effect on the fungi having resistance to conventional disinfectants.
The seed disinfectant composition of the present invention is effective on the seed born diseases such as Erysiphe sp., Puccinia sp., Septoria tritici, Leptosphaerla nodorum, Tilletia caries, Ustilago tritici, Fusarium sp., Cochliobolus sativus, Helminthosporium gramineum, Ustilago nuda, Pyrenophora teres, Rhynchosporium secalis, Septoria sp., Ustilago hordei, Ustilago avenae, Pyrenophora avenae, Fusarium nivale, Pyricularia oryzae, . _ .
Cochliobolus ~yabeanus, Gibberella fujikuroi, Pseudomonas glumae and the like.
The present invention is explained in more detail in the following examples which are by way of illustration and not by way of limitation. In the following examples, "parts" or "%" is by weight.
Formulation Example 1 (A Dust) 0.05 part of Compound A, 0.05 part of Compoumd I, 20 20 parts of hydroxyisoxazole, 66.5 parts of kaoline clay and 13.4 par*s of talc wexe thoxoughly ground and mixed together to obtain a dust of the present invention having :~ an active ingredie~t concentration of 0.1~.
FormuIation Example 2 (A Dust) 2 parts of Compound A, 10 parts of Compound VII, 10 parts of Compound C, 68 parts of kaoline clay and 10 parts of talc were thoroughly ground and mixed together to Z~342 l obtain a dust of the present invention having an active i.ngredient concentration of 22%.
Formulation Example 3 (A Dust) 20 parts of Compound A, 20 parts of Compound II, 20 parts of Compound C, 20 parts of Compound D, 20 parts of kaoline clay and 10 parts of talc were thoroughly ground and mixed together to obtain a dust of the present inven-tion having an active ingredient concentration of 80~.
Formulation Example 4 (A Wettable Powder) 0.2 part of Compound A, 2 parts of Compound III, 0,3 part of imazalil, 42.5 parts of diatomaceous earth, 50 parts of white carbon, 3 parts of sodium lauryl sulfate (a wetting agent) and 2 parts of calcium lignin sulfonate (a dispersant) were thoroughly ground and mixed together to obtain a wettable powder of the present inven-tion having an active ingredient concentration of 2.2%.
Formulation Example 5 (A Wettable Powder) 2 parts of Compound A, Q.l part of Compound IV, 5 parts of Compound C, 42.9 parts of diatomaceous earth, 45 parts of white carbon, 3 parts of sodium lauryl sulfate (a wetting agent) and 2 paxts of calciu~ lignin sulfonate (a dispersant) were thorou,ghl~ grou~d and mixed together to obtai~ a wettable powder of the present in,Vention having an active ingredient concentration of 7.1%.
Formulation Example 6 (A Wettable Powder) 0.5 part of Co~pound A, 5 parts of Compound V, l~Z~2 1 10 parts of Compound C, 10 parts of Compound D, 35 parts of diatomaceous earth, 34.5 parts of white carbon, 3 parts of sodium lauryl sulfate (a wetting agent) and 2 parts of calcium lignin sulfonate (a dispersant) were thoroughly ground and mixed together to obtain a wettable powder of the present invention having an active ingredient concentration of 25.5%.
Formulation~Example 7 (A Flowable Concentrate) 1 part of Compound A, 0.1 part of Compound VI, 3 parts of polyoxyethylene sorbitan monool eate , 3 parts of CMC and 92.9 parts of water were mixed together and wet ground until the grain size of the active ingredients became 5 ~ or less to obtain a flowable concentrate of the present invention having an active,ingredient concentration of 1.1~.
FOJ:IIIUL~ JI ~XLIIII~1C ~ (~ r~'10Wa1~10 COIIC~31l:r~
1 part of Compound A, 10 parts of Compound VII, 10 parts of Compound C, 3 parts of polyoxyethylene monooleate, 3 parts of CMC and 73 parts of water were mixed together and wet ground until the grain size of - the active ing~edients became 5 ~ or less to obtain a flowable concentrate of the present invention having an active ingr~dient concentration of 21%.
Form,ulation Example 9 ~A Flowable Concentrate) 0.5 part of Compound A, 10 parts of Compound II, 10 parts of Compound C, 10 parts of Compound D, 3 parts _ g ~
1~2~'~2 l of polyoxyethylenemonooleate , 3 parts of CMC-and 63.5 parts of,water were mixed together and wet ground until t:he grain size of the active ingredients became 5 ~
ox less to obtain a flowable concentrate of the present invention having an active ingredient concentration of 30.5%.
Formulation Example lO (An Emulsifiable Concentrate) 1 part of Compound A, 2 parts of Compound III, 1.5 parts of imazalil, 3.5 parts of polyoxyethylene alkyl aryl ether (an emulsifying agent), 50 parts of cyclohexane and 42 parts of xylene were mixed together to obtain an emulsifiable concentrate of the present invention having an active ingredient concentration of 3~, , Formulation Example 11 (An Emulsifiable Concentrate) 1 part of Compound A, 4 parts of Compound IV, '4 parts of Compound C, 4 parts of hydroxyisoxazole, 15 parts of polyoxyethylene alkyl aryl ether (an emulsifying , agent), 52 partG of cyclohexane and 20 parts of,xylene were mixed together to obtain an emulsifiable concentrate of the present invention having an active ingredient concentration of 9%.
FormuIation ~xample 12 (An Emulsifiable Concentrate) 0.5 pa~t of Compound A, 4 parts of Compound VII, 2 pa~ts of Co~pou~ld C, 15 parts of polyoxyethylene .alkyl aryl ether (an emulsifying agent), 50 parts of 1~2g4Z
1 cyclohexane and 28.5 parts of xylene were mixed together to obtain an emulsifiable concentrate of the present invention having an active ingredient concentration of 10,5%.
Test Example 1 10 g of wheat seeds (variety: Norin No. 61) inoculated and infected with Tilletia caries were dipped into an aqueous solution containing a prescribed concentration of each of wettable powders of the present invention prepared in the same manner as in Formulation Examples 4 to 6, for 24 hours. Thereafter, they were shown in an upland field and cultivated on.
When the wheat came into ears, they were examined whether they had any symptoms of the disease or not, and the percentage of healthy seedlings was calculated from the following equation.
Number of healthy-seedlings heaClthyage of = n treated plot x 100 gs uninoculated and untreated plot Moreover, the synergistic effect of the seed disinfectant compositio~ of the pxesent invention was studied accoxding to the, following procedure.
The e~fect,' (E) expected from the mixing of a compound X with another compound Y is generally giYen by the following equation:
E = m + n _ m10O
1~2~
1 E: Preventing effect(~) (percentage of healthy seedlings) expected when a mixture of X and Y in respective amounts of p and q is used.
m: Preventing effect (%) (percentage of healthy seedlings) when X is used alone in an amount of p.
n: Preventing effect (%) (percentage of healthy seedlings) when Y is used alone in an amount of q.
The effect (E') expected from the mixing of a compound X', a compound Y' and a compound Z' is generally given by the following equation:
10 0 10, O O O
E': Preventing efect l~) (percentage of healthy seedlings) expected when a mixture of X', Y' and Z' in respective amounts of p', q' and r' is used.
m': Preventing effect (%) (percentage of healthy seedlings) when X' is used alone in an amount of p'.
n': Preventing effect (~) (percentage of healthy seedlings) when Y' is used alone in an amount of q'.
Q': Preventing effect (%) (percentage of healthy seedlings) when Z' is used alone in an amount of r'.
An equation giving the effect expected from the mixing of four compounds can be introduced from the aboYe equation. Needless to say, when any one of four compounds shows no preyenting effect, the effect equals that expected from the mixing of other three compounds [See "Weeds" 15, pp. 20-2 (1967)].
l~Z~4Z
1 If the found effect obtained by mixing the two is larger than the expected one, it can be said that a synergistic effect is obtained. The results are shown in l'able 1.
Table 1 Compound A _ I _ Concentration Ill _ of Compound B IV _ Active Ingredients V _ (ppm) Vll _ Compound C _ Compound D
_ (-)-Enantiomer Content in Compound A (~ by weight) _ ~ Percentage of Found _ : Healthy Seedlings Expected _ - Cont'd -* Inoculation and no treatment.
** No inoculation and no treatment :~ :
Table l [Cont ' d) --1_ 2 3 4 5 6 7 8 9 lO _ o == == =_ S S S S _ _ === =======-_ ===== ~= ==-66.5 90.2 94.7 66.5 90.2 94.7 66.5 90.2 94.7 66.5 _ 80 83 85 81 84 86 79 82 83 80 _ 47 52 54 44 49 52 47 52 55 45 _ - Cont ' d 1~?2~342 Table 1 (Cont'd) ..
_ 12 13 14 15 16 17 18 19 20 _ 0.5 0.~ 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 _ _ _ 5-- _ _ 5 5 5 _ _ === === = = S _ ._ _ _ _ _ _ 5 ---- S- 5 _ _ _ 5 5 5 5 5 _ .. .. _ _ . __ _ 66.5 66,5 66.5 90.2 94.7 66.5 66.5 90.2 94.7 66.5 _ . _ 47 45 47 52 54 52 50 54 57 ---- 53 _ - Cont'd -~Z~ 2 Table 1 (Cont'd) -21- 22 - 23-- -2-4- 25 26 27 28 2930 _ ___ _ 0.5 0.5 0.5 0.5 0.5 O.S O.S O.S 0.50.5 _ ~l~t .= s s--====== = ~
S 5 5 _ _ __ _ 66.5 66,s 66,5 66.5 90.Z 94.7 66.5 66.5 _ 1 _ ... . ._ _ _. _ 92 91 90 93 98 g5 94 99 100 . _ 51 52 Sl 52 56 59 52 50 54 57 _ - Cont'd -~Z5~2 Table 1 (Cont'd) 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 11.5 _ 5 ~
5 5 5 5 5 5--5 55 = _ ~ '1''- i- 1 1 1 1 1 1 _ ._ _.. _ 66.5 90.2 94.7 66.5 66.5 66.5 66.5 90.2 94.7 66.5 .. __ . _ . , _ _ 94 98 100 g4 95 ---- 93 95 98 100 70 _ _53_ 57 59 51 52 51 52 56 59 _ _ - Cont'd -l~Z~ ~2 Table 1 (Cont ' d ) 41 42 1 43 44 45 46 47 48 49 50 _ ,__ I . _ 0_ 11.5 O.S ll.S O.S ll.S S _ 11.5 5 _ ~:=r~
.
66, 5 90 . 2 90 . 2 94 . 7 94, 7 _ _ _ _--=_ = =~
- Cont ' d 2~'~2 Table 1 (Cont ' d) 51 52 53 54 55 56 57 --58 59 60 _ _ ~ ~ _~ _~___ 11.5 5 _ 11.5 _ ====== ===--_ , . _ ._. .. ..__ _ 9 23 16 20 18 18 16 22 18 18 _ - Cont'd -Z~42 Table 1 (Cont'd) 61- 62 63 -0~ 00**
.._ '_-- ._ _, S ====
11.5 5 ==
. . _ 1 Test Example 2 Each of flowable concentrates of the seed disinfectant composition of the present invention prepared according to Formulation Examples 7 to 9 was sprayed onto ~S 10 g of barley seeds (VarietY: New Golden) infected with :~ Helminthos~or_um gramineu~. The~eaftex, the barley seeds were sown in an upland field and cultiyated on. When the barley came into ears, they were examined whether they had any symptoms of the disease or not, percentage of healthy seedlings was calculated in the same manner as in Test Example 1 and a synergistic efect was confirmed by comparing l the found value with the expected value. The results are shown in Table 2.
Table 2 _ . . _ _ Compound A
Amount of Active Ingredients Compound B IV
(gjlOOkg-dry seed) VII _ . _ Compound C
__ _ Compound D
.__ _ (-)-Enantiomer Content in Compound A (~ by weight) .... _ _ _ Percentage of Found Heal*hy Seedlings :Expected . _ - Cont'd -* Inoculation and no treatment ~ ** No inoculation a~nd no treatment :~ :
2~'~2 Table 2 (Cont ' d) - - 2 3 - 4 5 6-- 7 8 lO _ 5 l l l ~l 5 ~ = t = == = = = _ s - s . ...
__ ____ _~_ 66.5 90.2 94.7 66.5 90.2 94.7 66.5 90.2 94.7 66.5 _ . _ _ 32 42 48 32 42 48 32 42 4~3 32 _ - Cont ' d -l~Z9 ~2 Table 2 (Cont ' d) ~ t~l === = == 5 5 5 5 _ _ - 5 5 5 _ ~ --S ___ S -66.5 66,5 66.5 90.2 94.7 66.5 66.5 90.2 94.7 66.5 .. _ _ ,~._ ,. _ 32 32 32 42 48_ 42 42_ 50 55 __ 42_ _ - Cont ' d l~?Zg'~Z
Table 2 (Cont ' d) _ _ 5 _ ===== == S __ S
== =_ __ ====~
. 5 5 5 5 _ ..... _ _ 66.5 66,5 66,5 66.5 90,2 94,7 66,5 66,5 90.2 94.7 _ 87 89 86 88 93 96 g3 96 99100 _ 42 42 42 42 50 55 42 42 _ S055 _ - Cont'd -l~\Z~ ~2 Table 2 (Cont'd) 31 32 33 34 35 36 37 38 39 40 ~~ _ _ 1. 1 1 1 1 1 1 1 1 16 _ _ _ === S ===~ = = _ S
_ === ===__ _= _ _ 5--------- 5 . _ 66.590.2 94.7 66.566.5 66.5 66.5 90.2 g4.7 66.5 . . __ _ 92 97 100 91 9Z 9o --- 93 98 100 72 _ 42 50 55 42 42 42 42 50 55 _ - Cont'd -lZ~29'~
Table 2 (Cont ' d ) 41 42 ~ 43 44 45 46 47 48 49 50 _ 16 1 16 1 = = == _ _ =_ 16 5 16 5 ~ _ ======== 16 _ _ _ ~ _ _ 66.5 90.2 90.2 94.7 94.7 ,_ __ . _ . _ - Cont'd -Z9~Z
Table 2 (Cont ' d) Sl- 52 53 54 55 56 57 58 59 60 _ S === _== ==--16 5 l ~
== __ _ __ 16 5 16 _ 0 _ 0 0 0 0 0 0 0 ~ 0 35 = = ========_ - Cont ' d Table 2 (Cont'd) 61 62 63 0* 00**
_- = = = =
.__ ___ _ ~ ~
.
_ 16 5 ..
====
1 Test Example 3 Each of emulsifiable concentrates of the seed disinfectant composition of the present invention prepared according to Formulation Examples 1~ to 12 was sprayed onto 10 g of barley seeds ~yariety: Yideo) infected with Ustilago nuda. Thereafter, the barley seeds wexe sown in an upland field and cultivated on. When the harley came into ears, they were examined whether they had any symptoms of the disease or not, percentage of healthy seedlings was calculated in the same manner as in Test Example 1 and a synergistic effect was confirmed by comparing the found z 1 value with the expected value. The results are shown in Table 3.
Table 3 .. . . . _ _ .
. Compound A I _ II _ Amount of III
Active Ingredients Compound B IV _ (g/lOOkg-dr ~eed~
Compound C
, ._ _ Compound D
: .__ _ ~-)-Enantiomer Content in Compound A (% by weight) . _ _ ._ _ Percentage of Found _ . Healthy Seedlings Expected _ - Cont'd -* Inoculation and no treatment ** No inoculation and no treatment , ~Z~'~2 Table 3 (Cont'd) 1 2 3 4 5 6 7 8 lO _ _ 0.50.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 '10- 10 10 _ _ == = 10 10 10 == ==~
10 ~__ 10 _ . _ .. , .
_ . . _ . _ _ . .
_ 66,5 90,2 94.7 66.5 90.2 94.7 66.5 90.2 94.7 66.5 ., _ _ 66 75 76 66 75 77 65 74 76 65 _ - Cont'd -Z
Table 3 (Cont'd) - l2 l3 l4 l5 l6 l7 l8 l9 20 _ 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 0.5 ===== 10 = =--= _ =_== =10 10 10 10 ~ _ = 10 10 10 10 ~= = = = _ . _ _ , _ 66,5 66.5 66.5 90.2 94.7 66.5 66.5 90;2 94.7 66.5 _ 79 78 81 87 91 88 89 93 96 85 _ _ _65 64 67 76 77 66 66 75 77 65 _ - Cont'd -l~Z~'~2 Table 3 (Cont ' d) 21- 22 23 ~ 24 25 2627 _ __ _ 0.5 0.5 0.5 0.5 0.5 0.5 30.5 _ _ _ 10 ==== = = _ _ 10 10 10 10' 10 __ ` 10 '-'' 10 10 10 10 10 ~ . _ '=== ====_ 66 . 5 66 . 5 66, 5 66. 5 90 . 2 94 . 7 66 . 5 _ 65 65 64 67 76 77 . _ - Cont ' d Table 3 (Cont'd) 2~3 29 30 31 32 ~ 33 34 35 36 37 _ _ . _ _ 0.5 30.5 0.5 30.5 0.5 _ 30.5 10 _ _ . 30.5 10 _ = = _ = = = = = = 30.5 _ = == ==== === __ _ 66,5 90.2 90,2 94,7 94,7 ,. _ 58 100 69 100 71 25 18 28 Z0 23 _ - Cont'd -l~Z~ ~2 Table 3 (Cont ' d) __ _ - _ _ _ _ _ _ 30.5 10 _ 30.510 _ =~
_ _ _. _ 16 24 17 24 16 19 15 25 21 5 _ ,_ _ ~__ ==== =-- Cont ' d -Table 3 (Cont'd) 48 a* oo**
_ _ _ .
-===
''-'-lo- .
O O '100 ===
1 Test Example 4 10 g of wheet seeds (variety: Norin No. 73) infected with Fusarium nivale was dust-coated with each of wettable powders of the present invention prepared in the 5 ~same manner as in Formulation Examples 4 and 5. Thereafter, : the wheet seeds were sown in an upland field and cultivated on. When the wheet reached the fourth laafing stage, they were exa~ined ~hether they had any symptoms of the disease or not, precentage of healthy seedlings was calculated in the same manner as in Test Example 1. The results are shown in Table 4.
Table 4 . .. _ _ , _ . ~c~ourc A ,_ _ Amount of III _ Active Ingredients Compound B IV _ (g/lOOkg-dr~ seed) ¦
Compound C _ Compound D
. . .__ . . . _ (-)-Enantiomer Content in Compound A (% by weight) ._ ._ _ Percentage of Found _ Healthy Seedlings Expected _ _ - Cont'd -* Inoculation and no treatment ** No inoculation and no treatment l~z~ z Table 4 ~Cont ' d) __ 2 __ 5 _ 7 _ 10 _ ._ . _ 0.5 0.5 0,5 _ 0.5 0.5 == == _ ,~__ ~ _ _ 0.5 0.5 0.5 0.5 _ .._ _ _ _ , ._ _ 66.5 90,2 94.7 66,5 90,2 94,7 66,5 90,2 94,7 66,5 ,, _ _83 88 90 82 87 90 81 86 89 82 _ 51 57 60 52 58 61 50 55 59 50 _ - Cont ' d -1 ~Z5~2 Table 4 (Cont ' d) 2 13 14 ls 16 17 18 19 20 _ ===== 0 . 5 0, 5 0 . 5 0 . 5 =_ 1 1 1 1 - 1 _ = ==== = = ==-66.5 66,5 66.5 90.2 94.7 66,5 66.5 90.2 94.7 66.5 _ _ _ _ 50 49 54 59 62 53 55 60 63_ 52 _ - Cont ' d -l~Z~2 Table 4 (Cont'~) 21 _ 22 23 24 25 26 27 28 29 30 _ _ 0.5 _ 0.5 0.50.5 _ ._ _ --0.5 = ====, _ 0.5 _ _ 0.5 _ 0.5 0.5 0.5 .. _ 1 1 1 1 1 1 1 1 1 _ . 1 1 1 1 _ 66,5 66,5 66,5 66,5 90,2 94,7 66,5 66.5 gO.2 94.7 ~, .. _. . _ ~ __ .. _ 53 52 51 ,56. 61 64 53 55 6063 _ - Cont'd -1~2~ 2 Table 4 (Cont ' d) 31--32 33 34 35 36 37 38 39 40 _ 10 10 10_ ~0 10 10 10 10 10 12.5 _ 1 1 1 ~ ~ l~t . _ 66.5 90.2 94.7 66,5 66.5 66.5 66,5 90.2 94.7 66.5 _ _ 52 5861 53 52 51 56 61 64 _ - Cont'd -Table 4 ~Cont'd) 41 42 43' 44 45 ~- 46 47 48 4950 ~- _ 12.5 lO ~ 12.5 lO _ =~
_ ~ _ _ _ ~ ~ _ ======== =_ . . _ _ 66.5 90.2 90.2 94.7 94.7 _ ............... ... .. _ 38 48 45 52 ~49 58 21 62 23 56 _ = =_ - Cont'd -1~2~'~2 Table 4 (Cont'd) 51 _ 52 53 54 - SS 56 57 58 S9 60 _ __ _ . . _ 12.5 0.5 _ _ 12.5 0.5 _ 12.5 0.5_ 12.5 _ ==========_ ._ _ === =======_ - Cont'd -Table 4 (Cont'd) 61 62 63 0* 00**
== ===
=====
12.5 .,_ 1 Test Example 5 Each of emulsifiable concentrates of the present invention prepared according to Formulation Examples 10 to 12 was sprayed onto 10 g of barley seeds (variety: Sonja) infected with PyrenoPhora teres. Thereafter, the barley seeds were sow,n in an upland field and cultivated on, When the barley came into ears, they were examined whether they had any symptom,s of the disease or not, pércentage of healthy seedlings was calculated in the same manner as in ~est Example 1. The resuIts are shown in Table 5.
2g'~2 Example 5 _ Compound A _.
_ _ I _ II
Amount of III _ Active Ingredient~ Compound B IV _ (g/lOOkg-dry see ) Compound C
. . _ _ _ _ Compound D
.. ._ . . _ (-)-Enantiomer Content in Compound A (~ by weight) . . _ .. _. . ... _ Percentage o Found . . _ Healthy Seedlings Expected _ - Cont'd -* Inoculation and no treatment ** No inoculation and no treatment 1~2~'~2 Table 5 (Cont ' d) --_ 3 _ 5 ~ _ 7 8 9 10 _ _ __ _ O.S 0.5 0.5 0.5 0.5- 0.5 _ _-_ __ _ _-._ ._ _ ._ _ ............... _ _ . . _ 66.5 90,2 94.7 66.5 90.2 94.7 66.5 90.2 94.7 66.5 _ . ._ _ _ 6~ _ 70 73 ----- 65 70 73 65_ 70 73 65 _ - Cont'd -~Z~3~2 Table 5 ~Cont'd) 11 12 13- 14 15-- 16 17 -- 18 19 20 _ ._ .. _ _ _ --0.5 O--S = = === ===-_ _ 0.5 0.5 0.5 __ _ . _ _ === === == =-66.5 66,5 66.5 9~.2 94.7 66.5 66.5 90.2 94.7 66.5 _ _ 91 94---- 89 91 96 97 88 _ 73 74 74 78 80 74 _ - Cont'd -l~?Z~'~2 Table 5 (Cont ' d) 21 122 23 24 25 26 27 _ 0 ~ 10 10 10 10 35 . 5 _ _ _ ~ r _ .... _ _ 66.5 66.5 66.5 66.5 90.2 94.7 66.5 .. _ 87 88 85 91 98 99 100 _ _ 74 74 74 74 78 80 _ - Cont'd -Z~ 2 Table 5 (Cont'd) _ - 29 30 31 32 33 34 35 3637 _ 10 _ 35.5_ 10_ 35.5 10 _ _ 35.5 0.5 = -= = = = = ~ 35.5 O.S 35.5 _ ==== ======-== == ====== _ . _ . -. _ 66.5 90.2 9~,2 94.7 94.7 _ 100 70 100 73 5 0 3 02 _ __ ~ _ - Cont'd -?Z9'~2 Table 5 (cont'd?
_ _ ,_ . _ .. . _ -O.S 35.5 O-S = = = = = = = -= = = 35.5 O.S 35.5O.S = = = _ 35.50.5 _ _ 35.5 _ .... _ .,,_ . _ . . .. _ . . _ _ . ._ _ - Cont'd -l~fZ~2 Table 5 (Con~'d) 48 0* 00**
===
_ == =
= ==
1 Test Example 6 Each of flowable concentrates of the present invention prepared according to Formulation Examples 7 to 9 was sprayed onto 10 g of barley seeds (variety:
Akashinriki) lnfected wi,th Rhynchosporium secalis.
Thereafter, the.seeds were sown in an upland field and cultiyate.d o~. Wh,en, ~he baxle~.reached the internode elongation stage, the~ were exam,ined whether they had any sympto~s of the disease OX not, pexcentage of healthy seedlings was calculated in the same manner as in Test Example 1. The results are shown in Table 6.
g~z Table 6 _ ._ Compound Amount of III _ Active Ingredients Compound BIV _ (g/lOOkg-dry 5 ed) Compound C_ Compound D
. _ t-)-Enantiomer Content in Compound A (% by weight) _ _ Percentage of Found _ Healthy Seedlings Expected - cont'd -* Inoculation and no treatment No iAoculation and ~o treatment ' :
~;29~2 Table 6 (Cont'd) 2 3 4 5 _ 7 8 9 lO _ _ 66.5 90,2 94,7 66.5 90.2 94.7 6-6.5 90.2 94.7 66.5 _ _ . _ 44 49 5l 42 47 48 41 46 48 39 _ - Cont'd -:;
:
, l~Z~2 Table 6 (Con*'d) 12 l3 l4 lS l6 l7 l8 l9 20 _ lo 110 10_10 10 10 10 10 10 10 _ ~ I = ~ ~:~ ~
_ = l l L l = = = = =
_ .__ === = 10 10 10 10 10 66.5 66,5 66,5 90,2 g4,7 66,5 66,5 90,2 94,7 66,5 ..
- Cont'd -Z~ ~2 Table 6 (Cont'd~
211 22 23 24 25 26 27 28 29 30 _ _ __ _ __ ~ 1 ~ 1 1 _ 1 1 1 = = = _ 10 10 10 10 10 10 10 10 10 10 _ ....... ~ _ 66,5 66.5 66.5 66,5 90.2 94.7 66.5 66.5 90.2 94.7 _ ~ ..... ... _ 39 43 41 45 50 52 45 42 47 49 _ - Cont'd -1.;2~2~ ~2 Table 6 (Cont ' d) 31 - 32 33 34 35 36 37 38 39 40 _ lO 10 10 10 lO lO 10 10 26 _ _ 1 1 1 _ _ _ _ 66.5 90.294.7 66.5 66.5 66.5 66.5 90.294.7 66.5 _ 89 97 100 89 91 88 92 99 lO0 61 ~ _ 41 47 48 39 43 41 45 50 52 _ - Cont'd -Z9'~2 Tablç 6 (Cont ' ~) 41 42 43 44 45 46 47 48 49 50 _ == = = = I ===-_ , ._ .._ _ ~ ... _ . . _ 66,5 90,2 90,2 94,7 94,7 . _ = ==== == == _ - Cont'd -1~29'~2 Table 6 ~Cont ' d) 51. 52 53 54 55 56 ~ 57 58 59 60 _ -- = = = = = = = =
1 = === =====_ 26 1 . . _ = = = 26 L 2 6 1= = =--26 1 _ . 26 _ _. _ . ........... ..... ..... ..... .................. ........ .. _ ._ __ . _ L3 SS L0 S9 16 Sl 13 66 19 - Cont ' d 29~2 Table 6 (Co~t'd) 61 62 63 0* 00**
_ __ _ === = =
.
= = ===
26 S = =
, .. .
_ .
1 Test Example 7 Grains of unhulled rice (variety: Kinki No. 33) ; infected with benomyl-sensitive or benomyl-resistant ; Gibberella fujikuxoi we~e dust-coated with a prescribed amount of a dust of the seed disinfectant composition of the prese~t inVention prepared according to Foxmulation Example 1 ox a com~exciall~ ayailable seed disinfectant ~Benlate T ~ J. ~he~eaftex, the u~hulled rice ~as sown in sandy loam in a plastic pot at a rate of 100 grains per pot, covered with 80il and cultivated for 16 day~ in a 1,2~Z9 L~2 1 greenhouse. Then, the symptoms of the disease was examined and the percentage of healthy seedlings ~as calcuIated in the same manner as in Test Example 1. The results are shown in Table 7.
Table 7 . . .... _ _ Compound A
Amount of ~II
Active Ingredients Compound B IV _ (g/lOOkg-dry eed) Compound C
_ Compound D
_ Benlate T ~ 1 . _.
: ~-)-Enantiomer Content in Compound A (% by weight)¦
Percentage of a Healthy Seedlings *3 1, - Cont'd -* Inoculation and no treatment ** No inoculation and no treatment *l Com~ercially available seed disinfectant ~a mixture of benomyl and thiram) *2 The case where unhulled rice infected with benomyl-sensitive fungi was used.
*3 The case where unhulled rice infected with benomyl-resistant fungi was used.
Table 7 (Cont'd) . .
1 1 1 1 1 6 1 8 1 10 _ 10 10 10 10 10 10 == ==-r~
. ..
. .
. . .
.. .. .
.
66,5 90.2 g4.7 66.5 90.2 94.7 66.5 90.2 66.5 66.5 .. . _ .. . . . _ ~ 100 100 100 100 100 100 100 100 100 100- _ - Cont'd -~ 60 -Table 7 (Cont' d) _ 12 13 14 1516 _ 17 18 19 20 _ _ 1 1 1 1 1 1 1 1 1 _ . 10 10 10 - _ .... 10 _ __ _ `10 . _ 0 ~ = = =====-. _ _ _ ..... . . _ 66.5 66,5 66,5 90,2 94.7 66.5 66.5 90.2 94.7 66.5 . . . . _ 100 100 100 100 100 100 100 100 100 100 _ 1~0 100 100 100 100 100 100 100 100 100 _ - Cont'd -9~2 Table 7 (Con~t ' d~) t~~ t 10 = ====== ==
= 10 10 ==== ===
== 10 10 10 = ===
10 10 10 10 10 10 10 10 10 10 _ .
. . . .
66.5 66,5 66,5 66,5 gO,2 g4,7 66,5 66,5 90.2 94.7 _ __ _ 100 100 100 100 100 100 100 100 100 100 _ - Cont'd -~ 62 --9~2 Table 7 (Cont'd) . .__ _ _ 31 32 33 34 35 36 37 38 39 40_ _ 10 10 10 == =====-=== 10 10 === = =~
_~ ~ ~ 10 10 10 10 _-. _ - 5 5 --- 5 5 5 5 5 5 __ _ _. . .. . ._ . .. _ _ _ 66.5 90.2 94,7 66.5 66.5 66.5 66.5 90.2 94.7 66.5 _ .... .. . _ 100 100 100 100 100 100 100 100 100 90 _ - Cont'd -2~'~Z
Table 7 (Co~t'd~
41 142 43 44 45 46 47 48 4950 _ L 126 l 26 1 _ _ .. 26 lO _ _ 26lO _ _ _ __ 26 _ _ _ _ _ _ _ - ._ _ _. , _ 66.5 90.2 90.2 94.7 94.7 ._ . _ ~_ 36 92 41 95 44 43 25 40 21 38 _ - Cont'd -: :
Table 7 (Cont ' d) 51 52 53 54 55 56 57 58 59 60 _ =_ =========_ _ _ _ = == == == Z6 lO 26 _ _ . _. _ ___ _~____ _ 40 93 43 g4 41 89 38 98 44 0 -.. _ _ 19 40 21 43 23 37 20 65 38 0 _ - Cont ' d Table 7 (Cont'd~
_ _ _ ~ . ~ ~; D' __ _~___ __ ~' lO26 -5 100 50 ~ _ = = ====
.
_~ _ O O 70 48 O 100 .
1 Test Example 8 Grains of unhulled rice (variety: Nipponbare) infected with Cochliobolus miyabeanus were dust-coated with a prescribed amount of each of dusts of the present invention pxe~axed according to Foxmulation Examples 4 ~ to 6. Thexeaftex, the unhulled rice was sown in sandy ; loam in a pl~stiç pot at a Xate of 50 gxain~ per pot, covered with soil and cultivated for 21 days in a gréen-house. Then, the symptoms of the disease was examined - 66 ~
9 ~ Z
1 and the percentage of healthy seedlings was calculated in the same manner as in Test Example 1. The results are showrl in Table 8.
Table 8 . Compound A
II _ Amount of III _ Active Ingredients Compound B IV
(g/L O Olcg-dr seed ) y _ _ Compound C
_ _ : Compound D
... . , (-~-Enantiomer Content in Compound A (% by weight) . ~
Percentage of Found _ . Healthy SeedlingsExpected - Cont'd -* Inoculation and no treatment ** No inoculation and no treatment 1~?2~2 Table 8 ~Cont ' d~
===== = 10 10 10 -10 . ._ ._ .
66.5 90.2 94.7 66.5 90.2 94,7 6~.5 90.2 94.7 66.5 61 68 _ 70 62 67 69 59 68 69 58 - - Cont ' d -~z~z Table 8 ~Cont' d) 12 13 14 15 16 17 18 19--20- _ ~,_ ~ 10 ~
_ _ 66.5 66,5 66,5 90,2 94.7 66.5 66.5 90,2 94.7 6~.5 .__ .,. . _ _59' 56 62 69 71 85 88 91 93 82 16 15 17 19 2l 33 32 33 35 - Cont ' d -- 6g --;29~2 Table 8 (Cont'd) . _ _ . _ 1 1 1 1 1_ 10 1 1 1 _ __ 1010--- 10---_ _ 10 10 10 ~ ~ ~
_ = = 10 10 10 ====~
_ 5 5 5 5 _ _ . . ._ _ 66.5 66.5 ~6.5 66.5 90.2 g4.7 66.5 66.5 90,2 94.7 .. . . _ 84 ~1 84 93 95 91 93 98 100 _ 32 _ 31 30 32 34 35 33 32 33 35 _ - Cont'd -.2 Table 8 (Cont ' d?
3~ 32 33 34 35 36 37 38 39 40 _ _ ._ _ ~. l 1 1 l 1 1 l l 21 _ ... _ ... _ _ 5~_ 5 5 5 5 5 5 5 5 _ ; ._ _ 66 . 5 90 . 2 94 . 7 66 . 5 66 . 5 66 . 5 66 . 5 gO . 2 94 . 7 66 . 5 _ 97 100 92 91 90 92 99 100 20 _ 31 32 34 32 31 _ 30 32 34------ 35 _ - Cont'd -Table 8 ~Cont ' d?
l- 21~ l 21 1 2l 10 =~ =-=~ ===~= 2l lO 2l _ . _ ~-===== = = __ _ _ _ 66,~ 1 90.2 90.2 94.7 94.7 __ j. _ == === = ==-- Cont'd -Z
Ta~le 8 (Cont ' d) , _ j , . . . . .
51 ~ 52 53 54 1 55 56 j 57 1 58 59 1 60 ll ~ l l r 21,10 1 21110, 1 I 1 _ 21 1 10 21 10 1 _ i -~ 21 , _ i _ __ _ -~~~-T---. _ . _ . _ ~
=== ======
- Cont ' d -~ :
~ 73 --Table 8 ~Cont'd~
-61~-_63 _ ~ 00~*
= ===--' S' .
.21 5 =
..
18 O O O 100 .
.
1 Test Example 9 Grains of unhulled rice (variety: Nipponbare) infected with Pseudomonas glumae were dust-coated with a prescribed amount of each of dusts of the pxe5ent invention prepaxed accoxdin~ ~o Fo~ulati~ Examples 1 to 3. Thereafter, the unhulled rice was sown in sandy loam in a plastic pot at a rate of 50 grains pe~ pot, covered with soil and cultivated for 21 days in a greenhouse.
Then, the symptoms of the disease was examined and the l;~~ ~Z
1 percentage of healthy seedlings was calculated in the same manner as in Test E~ample 1. The results are shown in Table 9.
Table 9 _ Co~a~d A II _ Amount of III _ Active Ingredients Compound B IV
~g/lOOkg-dry :eed) I :
_.___ _ Compound C
, ,,, ,_. _ _ Compound D
_ ..
(-)-Enantiomer Content in Compound A (% by weight) , _ Percentage of ¦ Found Healthy Seedlings ¦ Expected _ I _ - Cont'd -* Inoculation and no treatment ** No inoculation and no treatment 9~2 Table 9 (Cont'd~
2 3' 4 5 6 7 8 _ 10 ~- _ _ __ _ ~ ... _ 5 - 5 5 _ _ _ ~ _ ... ._ . ~ 5 5 5 _ ----~ 5------ _ .. ... . ._ . _ _ _ . _ . .. . . _. . _ ,. .. _ -. _ . . _ _ 66.5 90.2 94.7 66.5 90.2 94.7 66.5 90,2 94.7 66,5 ... _ _ ._ _ __ O O O O O O O O O O
_ - Cont'd -Z~2 Table 9 ~Cont'd~
_ _ 12 13 14 15 16 17 18 19 120 _ _ 5 ~ - _ ===== =_ S ~ S _ . _ .._ _ ~=~t~ t 5-- 5 55 _ ._ _ ._ .. _ .. l _ 66.5 66.5 66.5 90.2 94.7 66.5 6~.5 90.2 94.7 66.5 .. _ _ _ .. _ ._ _ 23_ 19 26 1 29 _ 33 29 31 _ 33 34 25 _ O O O_ O O O O O_ -o O
. _ .
- Cont'd -29~2 Table 9 (Cont'd) 21 22 123 1 24 25 26 127 128 ~29 30 _ ~. 1 1 1 1 1 1 1 1 1 1 1 1 1 1 = 1~ = l l 5 5 _ _._ i I l l 5 ~ _ ~ 5 5 5~ ~
51 5 ! 5 55 1 5 5 ~ 55 _ _ i 1 10 10 10 10 , .. _ 66,5 66.5 66,5 66.5 90,2 94.7 66.5 66.5 90.2 94.7 _ .__ .. __ _ 23 26 22 29 32 33 9S g4 98 00 ~ .. ._ _.. _ . _ 0 0 0 0 ~ 0 43 43 43 43 .__ . .. _ _ - Cont'd -~Z9'~2 Table 9 (Cont'd~
31 _ 32 33 34 35 36 37 38 39 40 _ 1 1 1 1 1 _ 1 1 1 _ 21 _ S S S s ~
_ _ ,= ~_ 5 _ _ 5- _ _ 5 _ 5 5 _ 5 5 5 5 5 5 _ .. . ._ _ 66.5 90.2 94.7 66.5 66.5 66.5 66.5 90.2 94.7 66.5 . . .. _ , . _ . .. ._ . . _ 43 43 --- 43 _ 43----- 43 43--- 43 43 43 _ - Cont'd -Table 9 (Cont ' d) 41 42 43 44 45 46--- 47 ~ 48 49--- 50 _ --1_ 21 _ 21 1 21 5 = ==-_ _ .21 5 _ ___ ~ _~ 21 _ _ _ . _ ... _ _ . ... ._ _66 . 5 90 . 2 90, 2 9 4 . 7 9 4 . 7 _ 0 6 0 7 0 9 0 4 0 2 _ - Cont'd -1~2~2 Table 9 ~Cont ' d) _ i I ___ _ ~ t.
_ 215 _ _ 21 5 _ = == ==== 21 5 21 _ .. _ ...._ _ __ . . . . ,, _ . . .. _ __ ._ . . _ . .. _ __ _ - Cont'd -z Table 9 (Cont ' d) 61 62 63 0~ 00*~
_ __ ,_== ==' =====.
21 10 ~ .
O 58 43 O lOO
== = ~
Claims (18)
1. A seed disinfectant composition comprising effective amounts of (A) (E)-1-2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol containing not less than 50% by weight of (-)-(E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol and (B) at least one benzimidazole thiophanate fungicide, wherein the weight ratio of (A):(B) is 1-50:1-50.
2. A seed disinfectant composition according to Claim 1, wherein the content of (-)-(E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol in (A) is not less than 80% by weight.
3. A seed disinfectant composition according to Claim 1, wherein (A) is substantially pure (-)-(E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol.
4. A seed disinfectant composition according to Claim 1, wherein Compound B is at least one member selected from the group consisting of methyl 1-(butylcarbamoyl)-benzimidazol-2-ylcarbamate, 2-(4-thiazolyl)benzimidazole, methyl benzimidazol-2-ylcarbamate, 2-(2-furyl)benzimidazole, 1,2-bis-3-methoxycarbonyl-2-thioureido)benzene, 1,2-bis-3-ethoxycarbonyl-2-thioureido)benzene and methyl 1-(2-cyclohexenylcarbamoyl)-2-benzimidazolecarbamate.
5. A seed disinfectant composition according to Claim 1, wherein the weight ratio of (A):(B) is 1-20:1-20.
6. A seed disinfectant composition according to Claim 1, which further comprises (C) O,O-dimethyl-O-(2,6-dichloro-4-methylphenyl)phosphorothioate.
7. A seed disinfectant composition according to Claim 1, which further comprises (C) O,O-dimethyl-O-(2,6-dichloro-4-methylphenyl)phosphorothioate and/or (D) 1-Ethyl-1,4-dihydro-6,7-methylenedioxy-4-oxo-3-quinoline carboxylic acid or a salt thereof.
8. A seed disinfectant composition according to Claim 6, wherein the weight ratio of (A):(B):(C) is 1-50:1-50:0-50.
9. A seed disinfectant composition according to Claim 7, wherein the weight ratio of (A):(B):(C):(D) is 1-50:1-50:0-50:0-50.
10. A seed disinfectant composition according to Claim 7, wherein the weight ratio of (A):(B):(C):(D) is 1-20:1-20:1-20:1-20.
11. A seed disinfectant composition according to Claim 1, 6 or 7, which further comprises at least one inert carrier.
12. A seed disinfectant dust comprising active ingredients according to Claim 1, 6 or 7, at least one solid inert carrier and optionally hydroxyisoxazole or imazalil.
13. A seed disinfectant wettable powder comprising active ingredients according to Claim 1, 6 or 7, a wetting agent, a dispersant, at least one solid carrier and optionally hydroxyisoxazole or imazalil.
14. A seed disinfectant flowable concentrate comprising active ingredients according to Claim 1, 6 or 7, surface active agents, at least one liquid carrier and optionally hydroxyisoxazole or imazalil.
15. A seed disinfectant emulsifiable concentrate comprising active ingredients according to Claim 1 or 6, at least one surface active agent, at least one liquid carrier and optionally hydroxyisoxazole or imazalil.
16. A seed disinfectant composition according to Claim 10, wherein the active ingredient concentration is 0.1-99.9% by weight based on the total weight of the composition.
17. A seed disinfectant composition according to Claim 10, wherein the active ingredient concentration is 0.1-80% by weight based on the total weight of the composition.
18. A method for controlling a seed born diseases which comprises applying an effective amount of the seed disinfectant composition according to Claim 1, 6 or 7 to seed born diseases.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000553160A CA1292942C (en) | 1987-11-30 | 1987-11-30 | Seed disinfectant composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000553160A CA1292942C (en) | 1987-11-30 | 1987-11-30 | Seed disinfectant composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1292942C true CA1292942C (en) | 1991-12-10 |
Family
ID=4136972
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000553160A Expired - Fee Related CA1292942C (en) | 1987-11-30 | 1987-11-30 | Seed disinfectant composition |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1292942C (en) |
-
1987
- 1987-11-30 CA CA000553160A patent/CA1292942C/en not_active Expired - Fee Related
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