CA1170567A - Fungicidal composition for agriculture and horticulture and its use - Google Patents

Fungicidal composition for agriculture and horticulture and its use

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Publication number
CA1170567A
CA1170567A CA000382934A CA382934A CA1170567A CA 1170567 A CA1170567 A CA 1170567A CA 000382934 A CA000382934 A CA 000382934A CA 382934 A CA382934 A CA 382934A CA 1170567 A CA1170567 A CA 1170567A
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CA
Canada
Prior art keywords
salicylamide
trichloroethyl
butoxy
parts
range
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
CA000382934A
Other languages
French (fr)
Inventor
Taizo Nakagawa
Kaoru Ohmori
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Nippon Kayaku Co Ltd
Original Assignee
Nippon Kayaku Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nippon Kayaku Co Ltd filed Critical Nippon Kayaku Co Ltd
Priority to CA000382934A priority Critical patent/CA1170567A/en
Application granted granted Critical
Publication of CA1170567A publication Critical patent/CA1170567A/en
Expired legal-status Critical Current

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Abstract

ABSTRACT OF THE DISCLOSURE
The present invention relates to a fungicidal composition for agriculture and horticulture comprising at least one adjuvants and, as an effective component, in effective amounts, N-(1-n-butoxy-2,2,2-trichloroethyl) salicylamide and one member selected from the group consisting of (1) pentachloronitrobenzene and (2) tetrachloroisophthalonitrile. This composition is useful to control soil borne plant diseases such as clubroot disease of Cruciferae crops, black scurf of potatoes and damping-off of cucumber and tomato seedlings.

Description

I ~7~5fi~

The present invention relates to a fungicidal composition or agriculture and horticulture comprising at least one adjuvants and, as an effective component, in effec~ive amounts, N-(l-n-butoxy-2,2,2-trichloroethyl) salicylamide OH
CONHCHCC13 and one member selected from the OC4Hg(n) ~-~ 1 3 7~567 group consisting of ~1) pentachloronitrobenzene Cl~ Cl Cl and (2) tetrachloroisophthalonitrile ~ C

This composition is useful to control soil borne plant diseases such as clubroot disease of Cruciferae crops, black scurf of potatoes and damping-off of cucumber and tomato seedlings.
N-~l-n-butoxy-2,2,2-trichloroethyl) salicylamide ~hereinafter referred to as "compound A"), one of the effec-tive components of the present invention is a known compound described in the specification of USP 4,200,632. This compound is highly effective for controlling soil borne plant diseases, particularly clubroot disease of Cruciferae crops.
However, when the compound is used at a low concentration, a sufficient fungicidal effect cannot always be obtained on plant diseases caused by Rhizoctonia sp. and the like.
Pentachloronitrobenzene thereinafter referred to as "PCNB") is now available on the market as a fungicide against clubroat disease of Cruciferae crops and black scurf of potatoes. Though the compound is effective against the fungi o Plasmodiophora gp. and Rhizoctonia g~, there is a problem of the residual toxicity since it is used in a large amount.
Tetrachloroisophthalonitrile thereinafter referred to as .

~ ~ 7~67 "TPN") is now available on the market as a fungicide for controll-ing clubroot disease of Cruciferae crops and damping-off of cucumber and tomato seedlings. However, the sufficient controll-ing effect cannot be ob~ained in some cases.
After intensive investigations made for the purpose of developing a fungicide for surely controlling various soil borne plant diseases, the inventors have found that a mixture of compound A with PCNB or TPN shows a synergistic effect without giv-ing any phytotoxicity on crops which i9 unexpected from the effect of the respective components. The present invention has been completed on the basis of this finding.
The weight ratio of compound A to PCNB is generally in the range of 1:5 to 5:1, preferably 1:1 to 5:1.
The weight ratio of compound A to TPN is generally in the range of 1:10 to 10:1, preferably 1:1 to 5:1.
The composition of the present invention may be uset as it is or in the form of a mixture with an agricultural adjuvant which improves the effect or which stabilizes the composition tepenting on the purpose of the use. The composition may be used in the form of, for example, a dustl microgranules, granules, wettable powder or emulsion prepared by a method generally employed in the production of pesticites.
In the practical application, these various types of formulation may be used as they are or after dilution with water into a suitable concentration.

i I ~ 7~

As the agricultural adjuvants herein used, there may be mentioned a carrier (diluent) as well as spreaders, emulsifiers, wetting agents, dispersing agents, binders and disinte~rators etc.
As the liquid carriers, there may be mentioned aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol and glycol, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as dimethylsulfoxide, methylnaphthalene, cyclohexane, animal and vegetable oils, fatty acids ant fatty acid esters, etc.
As the solid carriers, there may be mentioned clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz alumina and sawdust.
As the emulsifiers or dispersing agents, surfactants are generally used. They include anionic surfactants, cationic surfactants, nonionic surfactants and amphoteric surfactants such as sodium salts of higher alcohol sulfate, stearyltrimethylammonium chloride, polyoxyethylenealkylphenylethers and laurylbetaine, etc.
These formulations may be used either alone or in the form of a mixture with herbicides, insecticides, plant growth regulators, acaricides, germicides, soil disinfectants, soil modifying agents or nematocides. Purther, they may be applied to the soil or locus thereof in the form of a mixture with a fertilizer or another agricultural and horticultural disinfectant.

. ~ ~ 7~5~7 When they are used in the above described forms, the concentrations of the compounds used as the effective components in the formulations are varied depending on the forms of the formulations and the agricultural adjuvants used. The concentration is, however, generally in the range of 2~95 wt. %.
And preferable content can be given differently for respec-tive types of formulation. For example, in the case of dust, the content of effective components is 2 to 20 %, that of adjuvants being 80 to 98 %; in emulsion, the content of effec-tive components is 5 to 40 %, that of adjuvants being 60 to 95 %;
in flowable~suspension concentrates, the content of effective components is S to 40 %, that of adjuvants being 60 to 95 %, while in wettable powder, the content of effective components is 20 to 80 %, that of adjuvants being 20 to 80 % and in granules and microgranules, the content of the effective components is 2 to 10 %, that of adjuvants being 90 to 98 %.
Then, detailed formulation examples of the present invention will be given below. The kinds of the adjuvants and the mixing ratios should not be limited to the ranges given in the examples but may extend over the ranges.
In the following examples, parts are given by weight.

Pormulation Example 1 Dust 7 Parts of compound A, 3 parts of PCNB, 40 parts of talc and 50 parts of clay were mixed together and pulveri~ed to obtain a dust.

I ~ 7~67 Formulation Example 2 Dust 6 Parts of compound A, 4 parts of TPN, 40 parts of talc and 50 parts of clay were mixed together and pulverized to obtain a dust.

Formulation Example 3 Wettable powder 50 Parts of compound A and 30 parts of PCNB were mixed with lS parts of kaolin, 3 parts of sodium salts of higher alcohol sulfate and 2 parts of sodium polyacrylate and the mixture was finely pulveri7ed to obtain a wettable powder.

Formulation Example 4 Wettable powder 40 Parts of compound A and 30 parts of TPN were mixed with 25 parts of kaolin, 3 parts of sodium salts of higher alcohol sulfate and 2 parts of sodium polyacrylate and the mixture was ~inely pulverized to obtain a wettable powder.

Pormulation Example S Granules 3 Parts of previously finely pulverized compound A and
2 parts of previously finely pulverized PCNB were mixed with 93 parts of clay and 2 parts of polyvinyl alcohol. 15 Parts of water were added to moisten the mixture homogeneously.
Then, the mixture was extrusion-molded into granules by means o a granulator. Ater dressing the granules in a dressing machine, granules having a diameter of 0.6-1 mm were obtained.

1 :~ 7~)r~i7 Formulation Example 6 Granules
3 Parts of previously finely pulverized compound A and 2 parts of previously finely pulverized TPN were mixed with 93 parts of clay and 2 parts of polyvinyl alcohol. 15 Parts of water were added to moisten the mixture homogeneously.
Then, the mixture was extrusion-molded into granules by means of a granulating machine. After dressing the granules in a dressing machine, granules having a diameter of 0.6-1 mm were obtained.

Formulation Example 7 Microgranules
4 Parts of previously finely pulverized compound A and 4 parts of previously finely pulverized PCNB were homogeneously mixed with 11 parts of clay and 1 part of polyvinyl alcohol to obtain a concentrated powder mixture of the active ingredients.
Separately, 80 parts of a non-absorbent coarse mineral powder of 74 to 105 micron size were placed in a proper mixer and then 20 parts of water were added thereto under rotation to moisten the former. The above powder mixture wa~ added thereto to coat the latter with the former.
The product was dried to obtain microgranules.

Formulation Example 8 Microgranules
5 Parts of previously finely pulverized compound A and 5 parts of previously finely pulverized TPN were homogeneously mixed with 11 parts of clay and 1 part of polyvinyl alcohol to 1 ~ 7~567 obtain a concentrated powder mixture of the active ingredients.
Separately, 78 parts of a non-absorbent coarse mineral powder of 74 to 105 micron size were placed in a proper mixer and then 20 parts of water were added thereto under rotation to moisten the former. The above powder mixture was added thereto to coat the latter with the former. The product was dried to obtain microgranules.

xperimental Example 1 Control test for clubroot of Chinese cabbage (caused by Plasmodiophora sp.) Soil infested with Plasmodiophora brassicae was filled in biscuit pots having a diameter of 15 cm. Then, 10 % dust containing the compounds of the present invention as prepared in the same manner as in Formulation Example 1 was added thereto in a predetermined amount and uniformly mixed with the soil.
15 Seets of Chinese cabbage ~variety: Taibyo 60-nichi) per pot were sowed. Four weeks thereafter, the seedlings of Chinese cabbage were grubbed out and the conditions thereof were examined.
The test results aTe shown in Table 1 in terms of a control value which is determined as follows:

Control value =

Percentage of healthy Percentage of healthy seedlings in treated plots seedlings in untreated plots 100 x Percentage of healthy seedlings in treated plots ! 1 7~567 Percentage of healthy seedling =

Number of healthy seedlings x 100 Number of total seedlings checked Table 1 _ Amount of Compounds . effective Control . .
tested - component value Phytotoxlclty (g/pot) __ Compound A 1.0 75 nil Reference Compound A 0.5 42 nil , PCNB 1.0 54 nil Reference - _ PCNB 0.5 20 nil Compound A 0.5 + 0.5 92 nil Present + 0.25~0.25 63 nil invention PCNB 1.0 ~0.25 98 nil . _ 0.5 + 0.25 80 nil Experimental Example 2 Control test for clubroot of cabbage (caused by Plas_odiophora sp.) __ Soil infested with Plasmodiophora brassicae was filled in biscuit pots having a diameter of 15 cm. Then, 10 % dust containing the compounds of the present invention prepared in the same manner as in Formulation Example 2 was added thereto :

5 6 ~

in a predetermined amount and uniformly mixed with the soil.
lS seeds of cabbage (variety: Kinshu) were sowed per pot.
Six weeks thereafter, the seedlings of cabbage were grubbed out and the conditions thereof were examined.
The test results are shown ~n Table 2 in terms of a control value which was determined in the same manner as in Experimental Example 1.

Table 2 . Amount of Compoundseffective ControlPhytotoxicity tested component value . ~g/pot) Compound A 1.0 75 nil Reference Compound A O.S 42 nil TPN 1.0 S0 nil Reference TPN O.S 18 nil Compound AO.S + O.S 88 nil Present + 0.25 + 0.25 60 nil invention TPN 1 + 0.25 96 nil O.S + 0.25 74 nil Experimental Example 3 Control test for damping-off of cucumber tcaused by Rhizoctonia sp.) Field soil was filled in pots having a diameter of 12 cm and then S g of infested soil in which Rhizoctonia solani had . .

1 ~ 7~5~7 been cultured was uniformly inoculated on the soil surface in each pot. The dust of the composition of the present invention prepared in the same manner as in Formulation Example 1 was added thereto in a predetermined amount and uniformly mixed - with the soil. Then, 10 seeds of cucumber ~variety: Oyashima) we,re sowed in each pot. They were allowed to grow in a green-house. Ten days after the sowing, the conditions were examined to determine the percentage of healthy seedlings.

Percentage of healthy seedlings =

Number of healthy seedlings in each treated plot x 100 Number of germination in untreated and uninoculated plot The test results are shown in Table 3 in terms of a control value which was determined in the same manner as in Experimental Example 1.

Table 3 _ Amount of Compound component Control Phytotoxicity , (g/pot) . .._ .. ~ ._ _ Reference Compound A0.04 60 nil Compound A0.02 35 nil .. ._ ._ PCNB 0.04 78 nil Reference PCNB 0.02 52 nil . ._ . . _ . ._ ._ 0.02+ 0.02 94 nil Present Compound A
invention PCNB 0.01+ 0.01 74 nil 0.02+0.01 88 nil _ , . _ ,_ ~ ~ 7~567 Experimental Example 4 Control test for damping-off of watermelon ~caused by Rhizoctonia sp.) Field soil was filled in pots having a diameter of 12 cm and then 5 g of infest~d soil in which Rhizoctonia solani had been cultured was uniformly inoculated on the soil surface in each pot. The dust of the composition of the present invention prepared in the same manner as in Formulation Example 2 was added thereto in a predetermined amount and uniformly mixed with the soil. Then, lO seeds of watermelon Cvariety; Otome~
were sowed in each pot. They were allowed to grow in a green-house. Fifteen ta~s after the sowing, the conditions were examined to determine the percentage of healthy seedlings.
The percentage of seetlings were determined in the same manner as in Experimental Example 3.
The result~ are shown in Table 4 in terms of a control value which was determined in the same manner a~ in Experimental Example 1.
Table 4 . . . .. _ Amount of effective Control . .
Compound Phytotoxlclty component value ~g/pot) Compound A 0.04 60 nil Reference Compound A 0.02 35 nil Reference TPN 0.04 52 nil TPN 0.02 30 nil _ 0.02l 0.02 84 nil PresentCompound A 0.01~ 0.01 65 nil invention TPN
_ 0.02~ 0.0l 75 nil '

Claims (11)

WHAT IS CLAIMED IS:
1. A fungicidal composition for agriculture and horticulture comprising at least one adjuvants and, as an effective component, in effective amounts, N-(1-n-butoxy-2,2,2-trichloroethyl) salicylamide and one member selected from the group consisting of (1) pentachloronitrobenzene and (2) tetrachloroisophthalonitrile.
2. The fungicidal composition according to claim 1, wherein the effective amounts in said composition is in the range of 2-95 % on the weight basis.
3. The fungicidal composition according to claim 2, wherein the ratio by weight of N-(1-n-butoxy-2,2,2-trichloroethyl) salicylamide to pentachloronitrobenzene is in the range of 1:5 - 5:1.
4. The fungicidal composition according to claim 3, wherein the ratio by weight of N-(1-n-butoxy-2,2,2-trichloroethyl) salicylamide to pentachloronitrobenzene is in the range of 1:1 - 5:1.
5. The fungicidal composition according to claim 2, wherein the ratio by weight of N-(1-n-butoxy-2,2,2-trichloroethyl) salicylamide to tetrachloroisophthalonitrile is in the range of 1:10 - 10: 1
6. The fungicidal composition according to claim 5, wherein the ratio by weight of N-(1-n-butoxy-2,2,2-trichloroethyl) salicylamide to tetrachloroisophthalonitrile is in the range of 1:1 - 5:1.
7. A method for controlling soil borne plant diseases caused by fungi which comprises applying to said fungi or locus thereof an effective amount of a mixture of N-(1-n-butoxy-2,2,2-trichloroethyl) salicylamide and one compound selected from the group consisting of (1) pentachloronitro-benzene and (2) tetrachloroisophthalonitrile.
8. A method according to claim 7, wherein the ratio by weight of N-(1-n-butoxy-2,2,2-trichloroethyl) salicylamide to pentachloronitrobenzene is in the range of 1:5 - 5:1.
9. A method according to claim 8, wherein the ratio by weight of N-(1-n-butoxy-2,2,2-trichloroethyl) salicylamide to pentachloronitrobenzene is in the range of 1:1 - 5:1.
10. A method according to clam 7, wherein the ratio by weight of N-(1-n-butoxy-2,2,2-trichloroethyl) salicylamide to tetrachloroisophthalonitrile is in the range of 1:10 - 10:1.
11. A method according to claim 10, wherein the ratio by weight of N-(1-n-butoxy-trichloroethyl) salicylamide to tetra-chloroisophthalonitrile is in the range of 1:1 - 5:1.
CA000382934A 1981-07-31 1981-07-31 Fungicidal composition for agriculture and horticulture and its use Expired CA1170567A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA000382934A CA1170567A (en) 1981-07-31 1981-07-31 Fungicidal composition for agriculture and horticulture and its use

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CA000382934A CA1170567A (en) 1981-07-31 1981-07-31 Fungicidal composition for agriculture and horticulture and its use

Publications (1)

Publication Number Publication Date
CA1170567A true CA1170567A (en) 1984-07-10

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Family Applications (1)

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Country Status (1)

Country Link
CA (1) CA1170567A (en)

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