CA1064823A - Process for treating seeds - Google Patents
Process for treating seedsInfo
- Publication number
- CA1064823A CA1064823A CA254,104A CA254104A CA1064823A CA 1064823 A CA1064823 A CA 1064823A CA 254104 A CA254104 A CA 254104A CA 1064823 A CA1064823 A CA 1064823A
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- Canada
- Prior art keywords
- active ingredient
- composition according
- compound
- seed
- formula
- 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.)
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Abstract: A process of treating seeds, which process com-prises treating seeds prior to sowing with a fungicidally effective amount of a composition comprising a compound having the formula (I):
Description
~6~8~3 This invention relates to a method of treating seeds to eradicate fungi thereon or therein. In particular the present invention relates to a process of treatin~r seeds to control or eradicate the incidence of fungi of the Pamilies Tilletia and ~ thereon or therein.
The fungi ~ and ~ are diseases which may cause heavy damage to grain crops such as wheat and barley.
It is known in the art that these diseases may be controlled by the appli~ation of seed dressing compositions comprising an effective amount of a suitable fungicidal organo-mercury compound. However toxicity and environmental studies have shown that the use of these compounds is highly undesirable, and in addition some species of the fungus illetia exhibit resistance to certain of them.
We have previously found that aromatic thiosemi-carbazones are highly effective against bunt and smut and which substantially do not suffer the disadvantages of the prior a~t compounds, and which in addition are highly ef~ective against the resistant species of the fungus ~ .
Unfortunately most aromatic thiosemicarbazones are unsuitable for use as a seed dressing because the~ompounds have an extremely unpleasant taste and the small amounts of dust inhaled during manipulation of the treated seed affect the palate. We have now discovered a small ~roup of aromatic Z5 thlosemicarbazones which combine high fungicidal activity with " '~ ' , ~' .
,,,; ~ ,, - - -, , .:
:.. ~ . -, ., ~ :
.. .. . ..
- 3 - ~4~Z3 acceptable taste.
Accordingly we provide a Iprocess of treating seeds~
which process comprises treating seeds prior to sowing wi~h a fungicidally effecti~e amount of a composition comprising a S compound having the formula (I)o R2 4 C=N-NH-c-NH2 Rl S
wherein Rl and R which may be thP same or different are selected from the group consisting of hydrogen, methyl~ ethyl, propyl, isopropyl, iodo, bromo~ chloro, fluoro, alkoxy group 10 containing from 1 to 15carbon atoms, a]kyl group containing from 1 to 3 carbon atoms substituted with halo or alkoxy group - containing from 1 to 3 carbon atoms~ and wherein when R is - hydrogen~ R2 is bromo, iodo~ alkoxy and substituted alkyl and wherein when R is hydrogen Rl is bromo, iodo, chloro, alk~xy~
and substituted alkyl.
In a further embodimeht of the present invention we ;~
provide a fungicidal composition, said~composition comprisin~
as acti~e in~redient present in fungicidally effectiYe amount~
a compound of formula (I) and an inert carrler material therefor.
Examples of typical compounds of general Eormula (I) as described hereinabove are set out below in Table I wherein appropriate substituents for Rl and R2 are indicated.
"
I
., :.,.. : . . .. .. .: .. . . ::
` - 4 ~64823 . TABLE I
r ~
. No _ Rl ~ ~
~ Cl 6 Me Cl .. ___ Ul~ ( C~
In Table II are listed closely related aromatic thiosemicarbazones having good fungicidal activity but wlth an unacceptable palate reaction.
' : ~E
,, ~
. Compound Rl ; R2 ~ S r ~ ¦ N ¦ ~ 1 .~ 13 ; ~H Cl 14 H isopropyl Me H
_ _ H F
. _ _~ ~
. . ~
J
. ~ . ` ' " . ` ', ` .'.' . . ; , ' ~ .
'' ~ ' ` ' ` ' . ` ', ' `
': ' ' ' ~ ' ' ' ' ' ,, ' ~'`'' , ' ~ ', 106~3;Z3 Many other aromatic thiosemicarbazones not of formula I
have been tested and found substantially less active. This demonstrates that the activity found in the compounds of formula I was not predictable. Table III lists the other S compounds tested.
.
. .
:
:
. , .. i '' .
:,.
.. .
. .
, . , :;
, -::: ~ , ... ' :
~''' '', '~" ' " ~ .
. . .
6 ~ 48~3 TABLE III: R3-C-N-N-C,-NHR6 ,, S ~, = ,___ _r _~____ _~
Compound R3 R4 RS R6 .~
17 l-Naphthyl H H H
18 4-HO-3~MeO-Phenyl H H H
19 2-Naphthyl H H H
The fungi ~ and ~ are diseases which may cause heavy damage to grain crops such as wheat and barley.
It is known in the art that these diseases may be controlled by the appli~ation of seed dressing compositions comprising an effective amount of a suitable fungicidal organo-mercury compound. However toxicity and environmental studies have shown that the use of these compounds is highly undesirable, and in addition some species of the fungus illetia exhibit resistance to certain of them.
We have previously found that aromatic thiosemi-carbazones are highly effective against bunt and smut and which substantially do not suffer the disadvantages of the prior a~t compounds, and which in addition are highly ef~ective against the resistant species of the fungus ~ .
Unfortunately most aromatic thiosemicarbazones are unsuitable for use as a seed dressing because the~ompounds have an extremely unpleasant taste and the small amounts of dust inhaled during manipulation of the treated seed affect the palate. We have now discovered a small ~roup of aromatic Z5 thlosemicarbazones which combine high fungicidal activity with " '~ ' , ~' .
,,,; ~ ,, - - -, , .:
:.. ~ . -, ., ~ :
.. .. . ..
- 3 - ~4~Z3 acceptable taste.
Accordingly we provide a Iprocess of treating seeds~
which process comprises treating seeds prior to sowing wi~h a fungicidally effecti~e amount of a composition comprising a S compound having the formula (I)o R2 4 C=N-NH-c-NH2 Rl S
wherein Rl and R which may be thP same or different are selected from the group consisting of hydrogen, methyl~ ethyl, propyl, isopropyl, iodo, bromo~ chloro, fluoro, alkoxy group 10 containing from 1 to 15carbon atoms, a]kyl group containing from 1 to 3 carbon atoms substituted with halo or alkoxy group - containing from 1 to 3 carbon atoms~ and wherein when R is - hydrogen~ R2 is bromo, iodo~ alkoxy and substituted alkyl and wherein when R is hydrogen Rl is bromo, iodo, chloro, alk~xy~
and substituted alkyl.
In a further embodimeht of the present invention we ;~
provide a fungicidal composition, said~composition comprisin~
as acti~e in~redient present in fungicidally effectiYe amount~
a compound of formula (I) and an inert carrler material therefor.
Examples of typical compounds of general Eormula (I) as described hereinabove are set out below in Table I wherein appropriate substituents for Rl and R2 are indicated.
"
I
., :.,.. : . . .. .. .: .. . . ::
` - 4 ~64823 . TABLE I
r ~
. No _ Rl ~ ~
~ Cl 6 Me Cl .. ___ Ul~ ( C~
In Table II are listed closely related aromatic thiosemicarbazones having good fungicidal activity but wlth an unacceptable palate reaction.
' : ~E
,, ~
. Compound Rl ; R2 ~ S r ~ ¦ N ¦ ~ 1 .~ 13 ; ~H Cl 14 H isopropyl Me H
_ _ H F
. _ _~ ~
. . ~
J
. ~ . ` ' " . ` ', ` .'.' . . ; , ' ~ .
'' ~ ' ` ' ` ' . ` ', ' `
': ' ' ' ~ ' ' ' ' ' ,, ' ~'`'' , ' ~ ', 106~3;Z3 Many other aromatic thiosemicarbazones not of formula I
have been tested and found substantially less active. This demonstrates that the activity found in the compounds of formula I was not predictable. Table III lists the other S compounds tested.
.
. .
:
:
. , .. i '' .
:,.
.. .
. .
, . , :;
, -::: ~ , ... ' :
~''' '', '~" ' " ~ .
. . .
6 ~ 48~3 TABLE III: R3-C-N-N-C,-NHR6 ,, S ~, = ,___ _r _~____ _~
Compound R3 R4 RS R6 .~
17 l-Naphthyl H H H
18 4-HO-3~MeO-Phenyl H H H
19 2-Naphthyl H H H
2~4~6-Me3-Phenyl H H H
21 2-HO-l-Naphthyl ~ H H
22 4-N02-Phenyl H H H
23 4-CN-Phenyl H H H
24 4-HOOC-Phenyl H H H
2-MeO-l~Naphthyl H H H
26 4-MeS-Phenyl H H H
27 Phenyl Me H H
28 4-No2-phenyl Me H ~ H
29 4 Cl-Phenyl Et H H ~ ~ :
4-MeO-Phenyl Me H H
31 4-NH2-Phenyl Me H ~ H
32 l-Naphthyl Me H H l -33 Phenyl CH2CObEt H H
34 Phenyl ~ IsoBu . H
35 ~ 4-Me-Phenyl H H 4 ~Me-Benzyl 36 4-iso-Phenyl H HEt 37 4-Me-Phenyl H HEt 38 4-Me-Phenyl H HAllyl 39 : 4-Me-Phenyl H H~ Me 4 ~ rb~O~l U
, .: , ,~ . .: . , .
. :-: , , 7 3~6~Ei 23 tcon-tinued) . _ ,__ ~ _ Compound R3 R4 R5R6 ~; 42 4-Me-Phenyl H H ~ecyl 43 l-Naphthyl H H Me : 44 4-Cl-Phenyl H H Et Phenyl Me H Allyl 46 Phenyl Me H Me 47 4-Me-Phenyl H Me H
48 2-Naphthyl - H Me H I :
. 49 4-Cl-Phenyl H Me H
: 50 Phenyl h ~DCN~ ~OCH ~ .
It is to be understood that the seed'dressings of this .
inventlon ~ay comprise, in addition to th~ active ingredient compounds of formula (I)~ one or~more other compounds having S -fungicidal activity especially compounds active against ce~eal pathogens other ~han bunt and smutO Such other compounds in- I
: ~clude for example fungicides such as Mancozeb, Thiram~ 8- 1 -:hydroxyquinoline and insecticides a~ainst gràin attacking : insects~ e.g. Lindane, Malathion ~, " .j ,.
.' ' ,',, . ! ,` , .
'' '~ ' , . ' ' ' ' . , ;' " ' `' ' ' ' ' 8 - ~ 0~;~823 Especially useful compositions accordirlg to -the present i~vention for use as seed dressing compositions com-prise from 1 to 90 w/w preferably from 2.5~ w/w to 75% w/w of a compound of general Formula I.
Our compositions may be formulated in the form of dusting powders or granules wherein the active ingredient is mixed with a solid inert carrier. Suitable solid inert carriers may be, for example~ kaolin, sodium or calcium carbonate, powdered magnesia, Fullerls earth, gypsum, Hewittls earth, diatomaceous earth, china clay, bentonite, and other colloidal clays.
Alternatively the seed dressing compositions may be in the form of dispersible powder or grains comprising, in ~ addition to the active ingredient, an inert carrier comprising - 15 a wetting agent to facilitate the disper~ion of the powder or grains in liquids. Such powders or grains may include fillers~
suspending agents and the like. The preferred dispersible powders comprise the active ingredient mixed with a finely ground colloidal clay to~ether with a dispersing agent. The seed dressing compositions ~ay also be in thP form of cols.
Suitable dispersin~ agents are known from the prior art and may ~e of the ca*ionic, anio~ic or non-ionic type. -Suitable agents of the cationic type include for example quaternary ammonium compounds such as cetyltrimethylam~onium bromide. Suitable agents of the anionic type include ~or . :
_ 9 1064B23 example s~aps, salts of aliphatic monoes-ters of` sulphuric acid, for example sodium lauryl .sulphate9 salts of sulphonated aromatic compounds~ Eor example sodium dodecyl-benzene sulphonate, sodium, calcium or ammonium lignosulphonate, butyl-S naphthalene sulphonate and a mi~ture of the sodium salts of di-isopropyl and tri-isopropylnaphthalene sulphonic acids.
Suitable a~ents of the non-ionic type include for example the condensation products of an alkylene oxide such as ethylene oxide or propylene oxide with fatty alcohols such as oleyl alcohol or cetyl alcohol7 or with alkylphenols such as octyl-cresol. Other non-ionic agents are the partial esters deri~ed from long chain fatty acids and hexitol anhydrides, the con-densation products of the said partial esters with an alkylene oxide such as ethylene oxide or propylene oxide and the lecithins.
Suitable suspending agents are for example hydrophilic colloids~ for example polyvlnyl pyrrolidone and sodium carboxy-; methyl cellulose and the vegetable gums, for example gum acacia and gum tragacanth.
The acti~e ingredient compounds of general formula ~I) as described hereinabove and included in the compositions utilised in the process of the present invention are con-veniently prepared by condensation o~ the appropriate aldehyde with thiosemicarbazide according to the equation:
i ~ .
.
.,,.~ , . . ., ~ .
; ,.
- lo- 1064BZ3 : R ~ CHo+H2N-NH-c-NH2 ~
, ~ .
Rl R2 ~--CH=N-NH-c-NH2 Rl wherein Rl and R are each as defined hereinabove.
Alternatively active ingredient thiosemicarbazone compounds of general fo~mula (I) may be prepared by reaction of an appropriate aldehyde with hydrazinium thiocyanate salt according to the equation:
~2 ~ CH=~+H2N-NH2~HscN
Rl R2 ~ ~CH=N-NHC-NH2 1`~
y ,, I
: : Rl~
wherein Rl~and R2 are each as defined hereinabo~e.
The seed dreesings of our invention are effective in eradicating or controlling ~ 3L~ (stinking smut of wheat) including strains resistant to HCB.
~ .
,. , , ,.' ':
.~ ~' " ' ~,,, ' ` ' ` . , .
The a~ount o` active ingredient compound included in our seed dressing compositions and rcquired for efeective - control of fungi depends amongst other things on the active ingredient, the strains of fungi to be treated, the de~ree of S control required, the type of medium infected, the types of formulation used and the conditiDns under which i* is applied.
We have found that seed dressing compositions according to the present invention applied to cereal seeds at a rats sufficient to provide from 30 ppm by weight to 2000 ppm by weight of active ingredient on the said seeds are effective in controlling Tilletia ~
.. ~ .. . . . . . .
: :
,'':, ~ ' : -. .
- 12 _ 106~8~3 Our invention is now illustrated by but in no way limited to the following examples.
Example 1 Thi~s example describes -the fungicidal action of comparative compositions not according to the present in-vention in the field under natural conditions.
Wheat seed (c.v. Olympic) was inoculated with Tilletia foetida spores (HCB resistant strain) by admixing 1 g of spores with each 250 g of seed and then ball milling the mixture for 20 minutes. The inoculated seed was then dressed with a fungicidal composition according to the present invention by adding a powder comprising 50% w/w of china clay and 50% w/w of an active ingredient compound selected from those listed in Table (I) and presented in Table III below, at rates of 0.01 g per 20 g of inoculated seed and 0.01 g per 10 g of inoculated seed and tumbling the mixtures in jars on the~
rollers of a ball mill until uniform products containing 250 ppm of acti~e ingredient compound and 500 ppm of active ingredient compound respectively were obtained.
For each fungicidal composition and at each applica*ion rate, dressed seed was then sown through a seed driIl in 6 single row plo~s each 10 feet in length. The seed was then allowed to germinate and the wheat plants were allowed to mature. At har~est the seed heads were collected and the control of disease assessed. The percentage of diseased heads .. ,, ,. . . . .................. , , - .
. ~ , :
: . :
- 13 _ ~6~Z3 and the disease as the percentage of the control is presented in Table III below.
For purposes of comparison the sowing procedure described above was substantially repeated except that the dressed seed was replaced by untreated inoculated seed.
TABLB IV
:
. . . __ ~__ __ Compound Concentration Total % Disease as %
No (ppm) diseased heads of control -: ~ ~ . ~ _~
250 0~05 1.6 lZ 500 _~ _ 250 0.07 2.3 ` 14 500 _* _ ~50 O O
Inoculated control ~ ~ 3.1 100.0 . _._ ~ ~ ~ .
~* No test was carried out at this concentration The compounds list~d in Tables I and II were each `incorporated into a separate seed dressing containing 25%
~acbive ingredient and ~5% china clay.
A serles~of experiments were carried out following *he procedure of ~xample 1 except that in place of the 50%
formulation of active ingredient each of the 25~ seed dress~
inga prepared above waa uaed to gl~e 500~ 375 and 250 ppm :,' -.
: ~ : : ;
. . ~ -.
. . ~ .
- 14~ 4~3Z3 of activc ~gredient on wheat seed (c.v. Mexico 120) treate~
it~l a mixed culture of resistan-t ~nd non resistant Tilleti~
foetida and of Tilletia caries. ~he field trials were carried out during 1975; each le~el of treatment was tested in a different part of Victoria.
The seed germinated satisfactorily an~ no signs of disease could be see~ 10 days after ~ermination on any of the treatments.
The full results after harvesting and assessment accordin~ to Example 1 are shown in Tables IV and V below in which the % of diseased heads is shown for each treatment level.
TABLE V
I . ,~ . ,~ ~.
Compound 500 ppm 250 ppm~ 375 ppm . . ... ~_~ ~
1 1.01 2.~4 0.13 2 0.26 8.16 ~.67
21 2-HO-l-Naphthyl ~ H H
22 4-N02-Phenyl H H H
23 4-CN-Phenyl H H H
24 4-HOOC-Phenyl H H H
2-MeO-l~Naphthyl H H H
26 4-MeS-Phenyl H H H
27 Phenyl Me H H
28 4-No2-phenyl Me H ~ H
29 4 Cl-Phenyl Et H H ~ ~ :
4-MeO-Phenyl Me H H
31 4-NH2-Phenyl Me H ~ H
32 l-Naphthyl Me H H l -33 Phenyl CH2CObEt H H
34 Phenyl ~ IsoBu . H
35 ~ 4-Me-Phenyl H H 4 ~Me-Benzyl 36 4-iso-Phenyl H HEt 37 4-Me-Phenyl H HEt 38 4-Me-Phenyl H HAllyl 39 : 4-Me-Phenyl H H~ Me 4 ~ rb~O~l U
, .: , ,~ . .: . , .
. :-: , , 7 3~6~Ei 23 tcon-tinued) . _ ,__ ~ _ Compound R3 R4 R5R6 ~; 42 4-Me-Phenyl H H ~ecyl 43 l-Naphthyl H H Me : 44 4-Cl-Phenyl H H Et Phenyl Me H Allyl 46 Phenyl Me H Me 47 4-Me-Phenyl H Me H
48 2-Naphthyl - H Me H I :
. 49 4-Cl-Phenyl H Me H
: 50 Phenyl h ~DCN~ ~OCH ~ .
It is to be understood that the seed'dressings of this .
inventlon ~ay comprise, in addition to th~ active ingredient compounds of formula (I)~ one or~more other compounds having S -fungicidal activity especially compounds active against ce~eal pathogens other ~han bunt and smutO Such other compounds in- I
: ~clude for example fungicides such as Mancozeb, Thiram~ 8- 1 -:hydroxyquinoline and insecticides a~ainst gràin attacking : insects~ e.g. Lindane, Malathion ~, " .j ,.
.' ' ,',, . ! ,` , .
'' '~ ' , . ' ' ' ' . , ;' " ' `' ' ' ' ' 8 - ~ 0~;~823 Especially useful compositions accordirlg to -the present i~vention for use as seed dressing compositions com-prise from 1 to 90 w/w preferably from 2.5~ w/w to 75% w/w of a compound of general Formula I.
Our compositions may be formulated in the form of dusting powders or granules wherein the active ingredient is mixed with a solid inert carrier. Suitable solid inert carriers may be, for example~ kaolin, sodium or calcium carbonate, powdered magnesia, Fullerls earth, gypsum, Hewittls earth, diatomaceous earth, china clay, bentonite, and other colloidal clays.
Alternatively the seed dressing compositions may be in the form of dispersible powder or grains comprising, in ~ addition to the active ingredient, an inert carrier comprising - 15 a wetting agent to facilitate the disper~ion of the powder or grains in liquids. Such powders or grains may include fillers~
suspending agents and the like. The preferred dispersible powders comprise the active ingredient mixed with a finely ground colloidal clay to~ether with a dispersing agent. The seed dressing compositions ~ay also be in thP form of cols.
Suitable dispersin~ agents are known from the prior art and may ~e of the ca*ionic, anio~ic or non-ionic type. -Suitable agents of the cationic type include for example quaternary ammonium compounds such as cetyltrimethylam~onium bromide. Suitable agents of the anionic type include ~or . :
_ 9 1064B23 example s~aps, salts of aliphatic monoes-ters of` sulphuric acid, for example sodium lauryl .sulphate9 salts of sulphonated aromatic compounds~ Eor example sodium dodecyl-benzene sulphonate, sodium, calcium or ammonium lignosulphonate, butyl-S naphthalene sulphonate and a mi~ture of the sodium salts of di-isopropyl and tri-isopropylnaphthalene sulphonic acids.
Suitable a~ents of the non-ionic type include for example the condensation products of an alkylene oxide such as ethylene oxide or propylene oxide with fatty alcohols such as oleyl alcohol or cetyl alcohol7 or with alkylphenols such as octyl-cresol. Other non-ionic agents are the partial esters deri~ed from long chain fatty acids and hexitol anhydrides, the con-densation products of the said partial esters with an alkylene oxide such as ethylene oxide or propylene oxide and the lecithins.
Suitable suspending agents are for example hydrophilic colloids~ for example polyvlnyl pyrrolidone and sodium carboxy-; methyl cellulose and the vegetable gums, for example gum acacia and gum tragacanth.
The acti~e ingredient compounds of general formula ~I) as described hereinabove and included in the compositions utilised in the process of the present invention are con-veniently prepared by condensation o~ the appropriate aldehyde with thiosemicarbazide according to the equation:
i ~ .
.
.,,.~ , . . ., ~ .
; ,.
- lo- 1064BZ3 : R ~ CHo+H2N-NH-c-NH2 ~
, ~ .
Rl R2 ~--CH=N-NH-c-NH2 Rl wherein Rl and R are each as defined hereinabove.
Alternatively active ingredient thiosemicarbazone compounds of general fo~mula (I) may be prepared by reaction of an appropriate aldehyde with hydrazinium thiocyanate salt according to the equation:
~2 ~ CH=~+H2N-NH2~HscN
Rl R2 ~ ~CH=N-NHC-NH2 1`~
y ,, I
: : Rl~
wherein Rl~and R2 are each as defined hereinabo~e.
The seed dreesings of our invention are effective in eradicating or controlling ~ 3L~ (stinking smut of wheat) including strains resistant to HCB.
~ .
,. , , ,.' ':
.~ ~' " ' ~,,, ' ` ' ` . , .
The a~ount o` active ingredient compound included in our seed dressing compositions and rcquired for efeective - control of fungi depends amongst other things on the active ingredient, the strains of fungi to be treated, the de~ree of S control required, the type of medium infected, the types of formulation used and the conditiDns under which i* is applied.
We have found that seed dressing compositions according to the present invention applied to cereal seeds at a rats sufficient to provide from 30 ppm by weight to 2000 ppm by weight of active ingredient on the said seeds are effective in controlling Tilletia ~
.. ~ .. . . . . . .
: :
,'':, ~ ' : -. .
- 12 _ 106~8~3 Our invention is now illustrated by but in no way limited to the following examples.
Example 1 Thi~s example describes -the fungicidal action of comparative compositions not according to the present in-vention in the field under natural conditions.
Wheat seed (c.v. Olympic) was inoculated with Tilletia foetida spores (HCB resistant strain) by admixing 1 g of spores with each 250 g of seed and then ball milling the mixture for 20 minutes. The inoculated seed was then dressed with a fungicidal composition according to the present invention by adding a powder comprising 50% w/w of china clay and 50% w/w of an active ingredient compound selected from those listed in Table (I) and presented in Table III below, at rates of 0.01 g per 20 g of inoculated seed and 0.01 g per 10 g of inoculated seed and tumbling the mixtures in jars on the~
rollers of a ball mill until uniform products containing 250 ppm of acti~e ingredient compound and 500 ppm of active ingredient compound respectively were obtained.
For each fungicidal composition and at each applica*ion rate, dressed seed was then sown through a seed driIl in 6 single row plo~s each 10 feet in length. The seed was then allowed to germinate and the wheat plants were allowed to mature. At har~est the seed heads were collected and the control of disease assessed. The percentage of diseased heads .. ,, ,. . . . .................. , , - .
. ~ , :
: . :
- 13 _ ~6~Z3 and the disease as the percentage of the control is presented in Table III below.
For purposes of comparison the sowing procedure described above was substantially repeated except that the dressed seed was replaced by untreated inoculated seed.
TABLB IV
:
. . . __ ~__ __ Compound Concentration Total % Disease as %
No (ppm) diseased heads of control -: ~ ~ . ~ _~
250 0~05 1.6 lZ 500 _~ _ 250 0.07 2.3 ` 14 500 _* _ ~50 O O
Inoculated control ~ ~ 3.1 100.0 . _._ ~ ~ ~ .
~* No test was carried out at this concentration The compounds list~d in Tables I and II were each `incorporated into a separate seed dressing containing 25%
~acbive ingredient and ~5% china clay.
A serles~of experiments were carried out following *he procedure of ~xample 1 except that in place of the 50%
formulation of active ingredient each of the 25~ seed dress~
inga prepared above waa uaed to gl~e 500~ 375 and 250 ppm :,' -.
: ~ : : ;
. . ~ -.
. . ~ .
- 14~ 4~3Z3 of activc ~gredient on wheat seed (c.v. Mexico 120) treate~
it~l a mixed culture of resistan-t ~nd non resistant Tilleti~
foetida and of Tilletia caries. ~he field trials were carried out during 1975; each le~el of treatment was tested in a different part of Victoria.
The seed germinated satisfactorily an~ no signs of disease could be see~ 10 days after ~ermination on any of the treatments.
The full results after harvesting and assessment accordin~ to Example 1 are shown in Tables IV and V below in which the % of diseased heads is shown for each treatment level.
TABLE V
I . ,~ . ,~ ~.
Compound 500 ppm 250 ppm~ 375 ppm . . ... ~_~ ~
1 1.01 2.~4 0.13 2 0.26 8.16 ~.67
3 1.42 0 1.67
4 ` 0.73 1.96 0 0.37 2.44 0.90 6 1.16 O94 1.93 7 2.32 0.54 1.40 8 8.04 1.33 1.93 ! 9 _~ _~ 2.73 _* _~ 1.96 , ~ 0.~1~ _ _ _ :
, .
.
'.'. ~ '' '~ ': , ,, : ~ - : . . , -: ... . ...
- 15~ 64~
TABLE V (Continued) __ ~ Compound 500 ppm250 ppm375 ppm ~: ~_ __ 12 0.35 0.17 1.33 . 13 0.16 o.87 2.03 16 1.80 ~59 0 Control 32.06 _ _ _ 60.03 No treatment was carried out at the~e levels.
TABLE VI
. - . . . _ _ ~_ Compound 5O ppm250 ppm 375 ppm 17 84.og 19.22 21.87 1~ 18.50 19.48 33.20 19 5.22 7.21 4.7 25.03 16.09 58.50 21 37.12 33.10 40.2 22 7.45 4.84 6.17 23 10.62 4.35 3-13 24 35.3 24.92 28.70 24.84 33~57 35.67 26 4-49 6.31 2.07 27 9.57 4.63 10.87 28 33.64 14.65 43.60 29 8.93 5~19 9.77 9.88 5.62 8-53 31 22.14 5.63 Z7.~3 32 4.18 5.11 12.57 33 ,_ _ _ ~ 36 07 -:; :
, .
....
' ~'." ' ` ` `. ;' ' .' ~ ' '' 16 1~6~823 ~ TABLE VI (Continued) ;, ~ ,. ~ . . . ~
No 5O ppm 250 ppm 375 ppm ___ _ . ... ; ~ ~ .
34 22.42 15.5Z 26.43 23.84 23.26 34~5~
36 4.93 23.21 27.73 37 27.66 17.33 40.00 38 19.91 15.16 34.67 39 8.46 11.41 15.00 4 4.9 13.94 3.27 41 1.45 10.12 3.3 42 34.84 3.43 ~7.70 43 18.22 32.05 37.80 44 21.84 21.60 35.60 11.52 6.11 15.6~
46 7.91 1~.26 6.90 47 13.42 14.12 22.83 48 18.84 18.72 25.80 49 13.39 12.~3 29.53 36.79 2~.39 40.23 Control 32.06 24.20 60.03 ,: ,, , ~ ~___ , . .
. ~ ~ .
The effect on the palate of seed dressings comprising the compounds of Tables I and II was tested in ~he following general manner.
:~ , - Each compound was incorporated into a separate seed dressing containing 25% active ingredient and 75~ china clay.
:
:
' .:
:''' ' ' '' ` . ,' '' ' `" .-~'.`' ' " ': . ' " ' ' -. ' :
: ';', ' '- ' ' ' ' . , ,: . ~ :
:' '.:' :: :: ' :.':. '~: ' -:'' ' ~. .: . ' '~,.: .- ,' , :
17 ~ 64823 :
On separate mornings a 100 g of a .seed dressing~ sample was tumble mixe~ with 100 kg of whea-i; seed in a commercial mixer in the presence of three operators. The treated seed was placed into a bag and the bag handled by the three operators in simulation of normal commercial practice. Xmmediately after this procedure the operators rated the e~fect on the palate on a scale from 1 to 6. (1 ~ no taste and 6 - highly bitter). The accumulated scores of the three operators are shown in the table below. Scores of 10 or under are con-sidered acceptable for a commercial ~eed dressing. Scores of 12 or above are definitely unacceptable for a commercial seed dressing.
'. ,, ...
Compound No _ Accumulated Score . 1~
~
;:: -: - : . :
. : :. : . .
, .
.
'.'. ~ '' '~ ': , ,, : ~ - : . . , -: ... . ...
- 15~ 64~
TABLE V (Continued) __ ~ Compound 500 ppm250 ppm375 ppm ~: ~_ __ 12 0.35 0.17 1.33 . 13 0.16 o.87 2.03 16 1.80 ~59 0 Control 32.06 _ _ _ 60.03 No treatment was carried out at the~e levels.
TABLE VI
. - . . . _ _ ~_ Compound 5O ppm250 ppm 375 ppm 17 84.og 19.22 21.87 1~ 18.50 19.48 33.20 19 5.22 7.21 4.7 25.03 16.09 58.50 21 37.12 33.10 40.2 22 7.45 4.84 6.17 23 10.62 4.35 3-13 24 35.3 24.92 28.70 24.84 33~57 35.67 26 4-49 6.31 2.07 27 9.57 4.63 10.87 28 33.64 14.65 43.60 29 8.93 5~19 9.77 9.88 5.62 8-53 31 22.14 5.63 Z7.~3 32 4.18 5.11 12.57 33 ,_ _ _ ~ 36 07 -:; :
, .
....
' ~'." ' ` ` `. ;' ' .' ~ ' '' 16 1~6~823 ~ TABLE VI (Continued) ;, ~ ,. ~ . . . ~
No 5O ppm 250 ppm 375 ppm ___ _ . ... ; ~ ~ .
34 22.42 15.5Z 26.43 23.84 23.26 34~5~
36 4.93 23.21 27.73 37 27.66 17.33 40.00 38 19.91 15.16 34.67 39 8.46 11.41 15.00 4 4.9 13.94 3.27 41 1.45 10.12 3.3 42 34.84 3.43 ~7.70 43 18.22 32.05 37.80 44 21.84 21.60 35.60 11.52 6.11 15.6~
46 7.91 1~.26 6.90 47 13.42 14.12 22.83 48 18.84 18.72 25.80 49 13.39 12.~3 29.53 36.79 2~.39 40.23 Control 32.06 24.20 60.03 ,: ,, , ~ ~___ , . .
. ~ ~ .
The effect on the palate of seed dressings comprising the compounds of Tables I and II was tested in ~he following general manner.
:~ , - Each compound was incorporated into a separate seed dressing containing 25% active ingredient and 75~ china clay.
:
:
' .:
:''' ' ' '' ` . ,' '' ' `" .-~'.`' ' " ': . ' " ' ' -. ' :
: ';', ' '- ' ' ' ' . , ,: . ~ :
:' '.:' :: :: ' :.':. '~: ' -:'' ' ~. .: . ' '~,.: .- ,' , :
17 ~ 64823 :
On separate mornings a 100 g of a .seed dressing~ sample was tumble mixe~ with 100 kg of whea-i; seed in a commercial mixer in the presence of three operators. The treated seed was placed into a bag and the bag handled by the three operators in simulation of normal commercial practice. Xmmediately after this procedure the operators rated the e~fect on the palate on a scale from 1 to 6. (1 ~ no taste and 6 - highly bitter). The accumulated scores of the three operators are shown in the table below. Scores of 10 or under are con-sidered acceptable for a commercial ~eed dressing. Scores of 12 or above are definitely unacceptable for a commercial seed dressing.
'. ,, ...
Compound No _ Accumulated Score . 1~
~
;:: -: - : . :
. : :. : . .
Claims (15)
1. A process of treating seeds, which process comprises treating seeds prior to sowing with a fungicidally effective amount of a composition comprising a compound having the formula (I):
I
wherein R1 and R2 which may be the same or different are selected from the group consisting of hydrogen methyl, ethyl, propyl, isopropyl, iodo, bromo, chloro, fluoro, alkoxy group containing from 1 to 15 carbon atoms, alkyl group containing from 1 to 3 carbon atoms substituted with halo or alkoxy group containing from 1 to 3 carbon atoms, and wherein when R1 is hydrogen, R2 is bromo, iodo, alkoxy, and substituted alkyl and wherein when R2 is hydrogen R1 is bromo, iodo, chloro, alkoxy, and substituted alkyl.
I
wherein R1 and R2 which may be the same or different are selected from the group consisting of hydrogen methyl, ethyl, propyl, isopropyl, iodo, bromo, chloro, fluoro, alkoxy group containing from 1 to 15 carbon atoms, alkyl group containing from 1 to 3 carbon atoms substituted with halo or alkoxy group containing from 1 to 3 carbon atoms, and wherein when R1 is hydrogen, R2 is bromo, iodo, alkoxy, and substituted alkyl and wherein when R2 is hydrogen R1 is bromo, iodo, chloro, alkoxy, and substituted alkyl.
2. A process according to Claim 1 wherein the active ingredient is applied to the seed in amounts sufficient to provide from 30 ppm by weight to 2000 ppm by weight of active ingredient on the seeds.
.
.
3. A fungidical composition, said composition comprising as active ingredient present in fungicidally effective amount, a compound of formula (I) as defined in Claim 1, and an inert carrier therefor.
4. A composition according to Claim 3 wherein the active ingredient is .
5. A composition according to Claim 3 wherein the active ingredient is .
6. A composition according to Claim 3 wherein the active ingredient is
7. A composition according to Claim 3 wherein the active ingredient is .
8. A composition according to Claim 3 wherein the active ingredient is .
9. A composition according to Claim 3 wherein the active ingredient is
10. A composition according to Claim 3 wherein the active ingredient is .
11. A composition according to Claim 3 wherein the active ingredient is .
12. A composition according to Claim 3 wherein the active ingredient is .
13. A process according to Claim 1 using a fungicidal composition according to any one of Claims 3 to 12 inclusive.
14. A composition according to claim 3 comprising from 1 to 90% w/w of a compound of formula I.
15. A composition according to Claim 14 comprising from 2.5 to 75% w/w of a compound of formula I.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPC190875 | 1975-06-06 | ||
| AUPC299275 | 1975-08-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1064823A true CA1064823A (en) | 1979-10-23 |
Family
ID=25642087
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA254,104A Expired CA1064823A (en) | 1975-06-06 | 1976-06-04 | Process for treating seeds |
| CA254,105A Expired CA1064824A (en) | 1975-06-06 | 1976-06-04 | Process for treating seeds |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA254,105A Expired CA1064824A (en) | 1975-06-06 | 1976-06-04 | Process for treating seeds |
Country Status (2)
| Country | Link |
|---|---|
| CA (2) | CA1064823A (en) |
| FR (1) | FR2312957A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104351231A (en) * | 2014-10-11 | 2015-02-18 | 中国农业大学 | Application of 4-chlorocinnamaldehyde thiosemicarbazone in plant disease control |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103694155A (en) * | 2012-09-27 | 2014-04-02 | 中国农业大学 | Novel substituted phenylpropionaldehyde (benzylideneacetaldehyde) thiosemicarbazone compounds and applications of the compounds as agricultural bactericides |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE874904C (en) * | 1944-07-14 | 1953-04-27 | Bayer Ag | Process for the production of thiosemicarbazones |
-
1976
- 1976-06-04 FR FR7617154A patent/FR2312957A1/en active Granted
- 1976-06-04 CA CA254,104A patent/CA1064823A/en not_active Expired
- 1976-06-04 CA CA254,105A patent/CA1064824A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104351231A (en) * | 2014-10-11 | 2015-02-18 | 中国农业大学 | Application of 4-chlorocinnamaldehyde thiosemicarbazone in plant disease control |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2312957B1 (en) | 1980-08-29 |
| CA1064824A (en) | 1979-10-23 |
| FR2312957A1 (en) | 1976-12-31 |
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