CA1064824A - Process for treating seeds - Google Patents
Process for treating seedsInfo
- Publication number
- CA1064824A CA1064824A CA254,105A CA254105A CA1064824A CA 1064824 A CA1064824 A CA 1064824A CA 254105 A CA254105 A CA 254105A CA 1064824 A CA1064824 A CA 1064824A
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- CA
- Canada
- Prior art keywords
- seed
- compound
- formula
- compounds
- composition
- 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
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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 comprises treating seeds prior to sowing with a fungicidally effective amount of a composition comprising a compound hav-ing the formula (I):
I
wherein R1 and R2 which may be the same or different are hydrogen, methyl, ethyl or propyl groups.
I
wherein R1 and R2 which may be the same or different are hydrogen, methyl, ethyl or propyl groups.
Description
~1~6~8Z~
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~ seeds to control or eradicate the incidsnce of fungi of the families ~ and Ustila~o thereon or therein.
The fungi Tilletia and U~ 3~ are diseased 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 application of seed dressing compositions comprlsing 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 Tillebia exhibit resistance to certain of them.
We have now found a olass of organic compounds which are highly effective against bunt and smut and which sub-stantially do not suffer the disadvantages of the prior art compounds, and which in addition are highly effectirz against the resista~t species ~f the fungus ~ .
~ Accordingly we provide a process of trzating seeds, which process comprises treating seeds prior to sowing with a fungicidally effecti~e amount of a composition comprising a ` compound having the formula (I).
tl 9 2 :.................................... .
. ' '~
. ,.
., ;
:,,,. . . , .:
:: . . . :, . .
~: , , - ~ . .
- 3~ 64~2~
wnerein Rl and R2 which may be the ~ame or dif~erent are hydrogen, methyl~ ethyl or propyl ~roups.
E~amples of typical compounds of general formula (I~
as described hereinabove a~e ~et out below in Table I wherein S appropriate substituents for IRl and R2 are indicated.
TABLE I
., _ ~
Compound Rl R2 . _
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~ seeds to control or eradicate the incidsnce of fungi of the families ~ and Ustila~o thereon or therein.
The fungi Tilletia and U~ 3~ are diseased 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 application of seed dressing compositions comprlsing 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 Tillebia exhibit resistance to certain of them.
We have now found a olass of organic compounds which are highly effective against bunt and smut and which sub-stantially do not suffer the disadvantages of the prior art compounds, and which in addition are highly effectirz against the resista~t species ~f the fungus ~ .
~ Accordingly we provide a process of trzating seeds, which process comprises treating seeds prior to sowing with a fungicidally effecti~e amount of a composition comprising a ` compound having the formula (I).
tl 9 2 :.................................... .
. ' '~
. ,.
., ;
:,,,. . . , .:
:: . . . :, . .
~: , , - ~ . .
- 3~ 64~2~
wnerein Rl and R2 which may be the ~ame or dif~erent are hydrogen, methyl~ ethyl or propyl ~roups.
E~amples of typical compounds of general formula (I~
as described hereinabove a~e ~et out below in Table I wherein S appropriate substituents for IRl and R2 are indicated.
TABLE I
., _ ~
Compound Rl R2 . _
2 Me H
3 H Me ' __ _ , .
Other cinnamaldehyde thiosemicarbazones not of formula I
have been tested and found substantially less activeO This demonstrabes that the activit~ found in the compounds of formula I was not predictable. Table II lists the other compounds tested. ~ ~ S / R4 TABLE III: ~ R3 - ~H = N - NH - C ~ N
RS
:. _~ ~ _ 5 : Compound No R ~ R R
Other cinnamaldehyde thiosemicarbazones not of formula I
have been tested and found substantially less activeO This demonstrabes that the activit~ found in the compounds of formula I was not predictable. Table II lists the other compounds tested. ~ ~ S / R4 TABLE III: ~ R3 - ~H = N - NH - C ~ N
RS
:. _~ ~ _ 5 : Compound No R ~ R R
4 Ph~CH=CH~ . H Allyl : S Ph-CH=CH; Me Me ~ ~ (CU3)~ <~4-<W=C~- U _ _ ~, . ~ .
. ! .
'``` `', '' . ::', : ' ',' ' .. : ,. . . ..
- 4- ~69~8~
:
- It is to be understood that the seed dressings of this in~ention ~ay comprise~ in addition to the active in-gredient compounds of formula (I), one or more other compounds having fungicidal activity especially compounds active against cereal pathogens other ~han bunt and smut. Such other compo~nds include for example fungicides such as mancozeb, thiram~ 8-hydroxyquinoline and insecticides against grain attacking insects, e.g. lindane, malathion.
Especially useful compositions according to the present invention for use as seed dressing co~positions comprise 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 exa~ple, kaolin, sodium or calcium ~
càrbonate, powdered magnesia~ Fuller~s earth, gypsum, Hewittts earth, diato~aceous earth, china clay~ bentonite, and other colloidal clays. ~ ~
~ZO Alte~natively the seed dressing compositions ma~ be in`
the form of dispersi~le powder or grains comprising, in -- addition to the active ingredient, an inert carrier comprising a wetting agent to facilitate the dispersion of the powder or ~ grains in liquids. Such powder~ or grains may include fillers~
;~ 25 suspending agents and the like. The preferred dispersible .'~ .
.
, ..... .
- s- ~64~;~4 powders comprise the active ingredient mixed with a ~inely ground eolloidal clay together with a dispersing agent. The seed dressing compositions may also be in the form of cols.
Suitable dispersing agents are known from the prior art and may be of the cationic, anionic or non-ionic type~
i Suitable agents of the cationic type include for example quaternary ~mmonium compounds such as cetyltrimethylammonium bromide. Suitable a~ents of the anionic type include ~or example soaps, salts of aliphatic monoesters of sulphuric acid, for example sodium lauryl sulphate, salts of sulphonated aromatic compounds, for example sodium dodecyl-benzené
sulphonate, sodium, calcium or ammonium lignosulphonate~ butyl-naphthalene sulphonate and a mixture of the sodium salts of di-isopropyl and tri-isopropylnaphthalene sulphonic acids.
Suitable agents of the non-ionic type include for example the condensation products of an alkylene oxide such as ethylene oxide or propylene oxide with atty alcohols Quch as oleyl alcohol or cetyl alcohol~ or wi~h alkyIphenols such as octyl-phenol~ nonyl-phenoi and octyl-cresol. Other non-i~nic agents ZO are the partial esters derived ~rom long chain ~atty~acids and hexitol anhydrides, the condensation products of the said partial esters with an alkyléne oxide such as ethylene oxide -or propylene oxide and the lecithins.
, ~ Suitable suspending agents are for example hydrophilic `~ 25 colloids, for example polyvinyl pyrrolidone and sodium carboxy-:` :
;.~ ...
:: .
:, .
. r~ ~, , - ,, ;
;~,', ` i , ' ` ' ' .~' ` ` .' ~CI 6482~
methyl cellulose and ttle vegetable gums~ for example gum ~ acacia and gum tragacan-th.
; The active ingredient compounds of general formula (I) as described hereinabove and included in the compositions S utilised in the process of the present invention are con-t veniently prepared by condensation of the appropriate aldehyde or ketone with thiosemicarbazide according to the equation:
CH = C - C = O
Rl R2 CH = C - C = N - NH - C - NH2 Rl R~
wherein Rl and R2 are each as defined hereinabo~e.
Alternatively active ingredient thiosemicarbazone compounds of general formula tI) may be prepared by reaction o~ an appropriate aldehyde or ketone with hydrazinium thiocyanate salt a¢cording to the equation:
CH = G - C = 0 ~ H N
S
CH = C - C = N - N - C - ~H2 l R
wherein Rl and R2 are ~ach as deflned hereinabove.
.
.
--: ~ : . .:
- 7~ 82~
The seed drcssings of our invention ar~ c~fective in eradicating or controlling Tilletia ~ (stinking smu~ of wheat) includin~ ~trains resistant to HCB.
The amount of active ingredient compound included in S our seed dressing compositions and required Eor effective control of fungi depends amongst other things on the active - ingredient~ the strains of fungi to be treated, the degree of control required, the type of medium infected~ the types of formulation used and the conditions under which it is applied.
Wé have found that seed dressing compositions according : to the presen~ invention applied to cereal seeds at a rate sufficient to provide from 30 ppm by weight to 2000 ppm by weight o~ acti~e ingredient on the said seed~ are~effective in controlling Tilletia ~E~
~.
, , .
-~, :, - . : . . . :
.
.. ~ -. ~ .
.. , . ... . , ;
:. . .
8 - ~ ~6~8~4 Our invention is now ]Lllustrated by but in no way limited to the following examples.
~ . .
The compound~ sted i.n Tables I and II were each incorporated illtO a separate seed dressin~ containing 25 active in~redient and 75% chi.na clay.
- Wheat seed t c . v. Mexico 120) was inoculated with a mixed culture of ~ ~ (resi~tant a~d non resistant strains) and with ~ ~ by admlxing 1 g of the mixed spores with 250 g of ~eed and then tumbling the mixture on the rollers of a ball mill for 20 minutes.
The inoculated seed was dressed with a fungicidal : composition by tumbling the mixtures in jars on *he rollers : of a:ball mill until uniform products containing 250 ppm, :~
375 and 500 ppm o acti~e ingredient compound were obtained.
For-èach fungicid~l composition and at each application rate~ dres~ed seed was sown throu~h a ~eed drill in 6 single row plots each lO~feet in length. The~seed was allowed to germinate and the wheat plan~ were allowed to mâ~uré. '~t harvest the seed~heads~were collected and the contro~ of , disease as~essed. The pe~centage of diseased heads is shown in~Table III below~ : ~
', ' - ., : . ;:
::: : .:,:: :, ' . ' ' '' '''' .. .....
, ~
1~6~2~
:
' TABLE III
____ , , . , ... _ _ ,.. _.___ ~
: No 5O ppm 375 ppm 250 ppm .~ .. .~ .. .. . ~ _ ~ _ _ 1 _* _~ O
t 2 0.28 -33 0 : ~ 3 0.70 0.50 0 4 23.37 27.83 6.26 . 16.53 29.17 8.34 6 10.51 6.67 11.81 Control 32.D6 60.D~ Z4 20 not tested at this concentration.
~ ~ .
This example describes the application of a process according to the present invention.
- Wheat seed (c.v. Olympic) was inoculated with ~
foetida spores (HCB susceptible strain) by admixing l~g of ~ -spores with each ~50 g of seed in a sealed container on the rollers of a ball mill for 20 minutes. Samples of the ; 10 inoculated seed was then dressed with a fungicidal composition compri ing 50% w/w of compound 1 of Table I, 5% w/w ethylene glycol, 10% w!w "Celite" 298 and 35~ w/w of china clay by admixt'ure of lg of this composition with each kg of inoculated seed and blending in a'sealed container on the rollers of a mill to obtain a uniform product containing 500 ppm of active in~
gredient.
, i~ :
;
"'' ' ~' " ' ' ' ` ''`'"' ' ., "'.",;~', . .' ' " ' ', . , , ' . ' ' '' ' ~ . ;. ' ~ ' ~ lo ~0~48~4 The dressed ~eed was then sown through a ~eed drill in 6 singls row plots each 10 ~eet in Iength. The seed was then allowed to germinate and the wh~at plants were allowed to mature. At harvest the sleed heads were collected and the control of disease act~essed. The percentage of di~eased : heads and the disease as the percentage of the con~rol i~
presented in Table IV hereinbelow.
The above procedure wa~ sub3tantially repeated exceyt that the wheat seed was inoculated with the fungus ~ (HC~ resistant strain). The re~ult~ obtained are al~o pre~ented in Table IV hereinbelowO ~or purpo~e~ o~
comparison the sowing procedure de6cribed above wa~ sub-stantially repeated except that the dressed sèad was replaced ; by untreated inoculated s~ed. In ad~ition,:and also for the purpose of compari~on, the ~eed inoculation~ dressing and sowing procedure described hereinabove wa~ sub~tantially repeated for each-o~ the ~ungal specie6 ~ ~ .
t~C~ ~usoeptible) and ~ ~ (HCB reSit3tant~ eXcept that in a ~ir~t te~t th~ wheat ~eed was dres~ed with:"~ere~an~
(llcereBan~l i8 a Reg~lstered Trade Mark of E I Du Pont de Nemour6t Inc. for propriet~ ~ ~ungicidal compo6itio~s compri~ing as active ingredient a blend of m`ethyl mercury acetate and methyl mercury 2,3-dihydrox~-propyl-mercap*ide) atnd in a - second te~t the wheat Eteed was dres61ed with "Dithane M45"
~5 ('IDi'chane M45" i_ a R glAtered Trade Mark o~ ~the Roh~A and Haa_ : , ~
-,, .
': :: . ' . , ' ~ . .: .
:- .'' : .~ . '~, .
~:, -~' : - : .. . . . ..
. .
;48'~
Co for proprietary fun~idical composition~ comprising as active ingredient a ~inc co~plex of a p~lymeric manganese ethylene-1,2-bisdithiocarbamate)~ The results of these comparative tests are also sho~ in Table IV below.
TABLE IV
~ ~ . . -, .. , ~
Active Concentration Fungal Species ngredient of active (ppm) ~HCB susceptible) (HCB resi~tant) Percentage of Diseased Heads ~ :
- ~ 5 1 500 1.78 0.34 ~
~ 1 250 0. o8 o. ~2 ~::
: 7 1~ Ceresan"
(comparatlve ~:
: composition) 30 o.88 0~00 Dithane M45'l :
(comparative O
~ co~position) ~ 1500 o.63 0~00 ;:
:~ Control . ;
~ (no active ~ ~ .
:~ ingredient Nil : 36.88 ~ `10.47 ___ ~
~' .;
: , : , . . ,. ' . , ~: ' ' ' .. , .' :
. ! .
'``` `', '' . ::', : ' ',' ' .. : ,. . . ..
- 4- ~69~8~
:
- It is to be understood that the seed dressings of this in~ention ~ay comprise~ in addition to the active in-gredient compounds of formula (I), one or more other compounds having fungicidal activity especially compounds active against cereal pathogens other ~han bunt and smut. Such other compo~nds include for example fungicides such as mancozeb, thiram~ 8-hydroxyquinoline and insecticides against grain attacking insects, e.g. lindane, malathion.
Especially useful compositions according to the present invention for use as seed dressing co~positions comprise 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 exa~ple, kaolin, sodium or calcium ~
càrbonate, powdered magnesia~ Fuller~s earth, gypsum, Hewittts earth, diato~aceous earth, china clay~ bentonite, and other colloidal clays. ~ ~
~ZO Alte~natively the seed dressing compositions ma~ be in`
the form of dispersi~le powder or grains comprising, in -- addition to the active ingredient, an inert carrier comprising a wetting agent to facilitate the dispersion of the powder or ~ grains in liquids. Such powder~ or grains may include fillers~
;~ 25 suspending agents and the like. The preferred dispersible .'~ .
.
, ..... .
- s- ~64~;~4 powders comprise the active ingredient mixed with a ~inely ground eolloidal clay together with a dispersing agent. The seed dressing compositions may also be in the form of cols.
Suitable dispersing agents are known from the prior art and may be of the cationic, anionic or non-ionic type~
i Suitable agents of the cationic type include for example quaternary ~mmonium compounds such as cetyltrimethylammonium bromide. Suitable a~ents of the anionic type include ~or example soaps, salts of aliphatic monoesters of sulphuric acid, for example sodium lauryl sulphate, salts of sulphonated aromatic compounds, for example sodium dodecyl-benzené
sulphonate, sodium, calcium or ammonium lignosulphonate~ butyl-naphthalene sulphonate and a mixture of the sodium salts of di-isopropyl and tri-isopropylnaphthalene sulphonic acids.
Suitable agents of the non-ionic type include for example the condensation products of an alkylene oxide such as ethylene oxide or propylene oxide with atty alcohols Quch as oleyl alcohol or cetyl alcohol~ or wi~h alkyIphenols such as octyl-phenol~ nonyl-phenoi and octyl-cresol. Other non-i~nic agents ZO are the partial esters derived ~rom long chain ~atty~acids and hexitol anhydrides, the condensation products of the said partial esters with an alkyléne oxide such as ethylene oxide -or propylene oxide and the lecithins.
, ~ Suitable suspending agents are for example hydrophilic `~ 25 colloids, for example polyvinyl pyrrolidone and sodium carboxy-:` :
;.~ ...
:: .
:, .
. r~ ~, , - ,, ;
;~,', ` i , ' ` ' ' .~' ` ` .' ~CI 6482~
methyl cellulose and ttle vegetable gums~ for example gum ~ acacia and gum tragacan-th.
; The active ingredient compounds of general formula (I) as described hereinabove and included in the compositions S utilised in the process of the present invention are con-t veniently prepared by condensation of the appropriate aldehyde or ketone with thiosemicarbazide according to the equation:
CH = C - C = O
Rl R2 CH = C - C = N - NH - C - NH2 Rl R~
wherein Rl and R2 are each as defined hereinabo~e.
Alternatively active ingredient thiosemicarbazone compounds of general formula tI) may be prepared by reaction o~ an appropriate aldehyde or ketone with hydrazinium thiocyanate salt a¢cording to the equation:
CH = G - C = 0 ~ H N
S
CH = C - C = N - N - C - ~H2 l R
wherein Rl and R2 are ~ach as deflned hereinabove.
.
.
--: ~ : . .:
- 7~ 82~
The seed drcssings of our invention ar~ c~fective in eradicating or controlling Tilletia ~ (stinking smu~ of wheat) includin~ ~trains resistant to HCB.
The amount of active ingredient compound included in S our seed dressing compositions and required Eor effective control of fungi depends amongst other things on the active - ingredient~ the strains of fungi to be treated, the degree of control required, the type of medium infected~ the types of formulation used and the conditions under which it is applied.
Wé have found that seed dressing compositions according : to the presen~ invention applied to cereal seeds at a rate sufficient to provide from 30 ppm by weight to 2000 ppm by weight o~ acti~e ingredient on the said seed~ are~effective in controlling Tilletia ~E~
~.
, , .
-~, :, - . : . . . :
.
.. ~ -. ~ .
.. , . ... . , ;
:. . .
8 - ~ ~6~8~4 Our invention is now ]Lllustrated by but in no way limited to the following examples.
~ . .
The compound~ sted i.n Tables I and II were each incorporated illtO a separate seed dressin~ containing 25 active in~redient and 75% chi.na clay.
- Wheat seed t c . v. Mexico 120) was inoculated with a mixed culture of ~ ~ (resi~tant a~d non resistant strains) and with ~ ~ by admlxing 1 g of the mixed spores with 250 g of ~eed and then tumbling the mixture on the rollers of a ball mill for 20 minutes.
The inoculated seed was dressed with a fungicidal : composition by tumbling the mixtures in jars on *he rollers : of a:ball mill until uniform products containing 250 ppm, :~
375 and 500 ppm o acti~e ingredient compound were obtained.
For-èach fungicid~l composition and at each application rate~ dres~ed seed was sown throu~h a ~eed drill in 6 single row plots each lO~feet in length. The~seed was allowed to germinate and the wheat plan~ were allowed to mâ~uré. '~t harvest the seed~heads~were collected and the contro~ of , disease as~essed. The pe~centage of diseased heads is shown in~Table III below~ : ~
', ' - ., : . ;:
::: : .:,:: :, ' . ' ' '' '''' .. .....
, ~
1~6~2~
:
' TABLE III
____ , , . , ... _ _ ,.. _.___ ~
: No 5O ppm 375 ppm 250 ppm .~ .. .~ .. .. . ~ _ ~ _ _ 1 _* _~ O
t 2 0.28 -33 0 : ~ 3 0.70 0.50 0 4 23.37 27.83 6.26 . 16.53 29.17 8.34 6 10.51 6.67 11.81 Control 32.D6 60.D~ Z4 20 not tested at this concentration.
~ ~ .
This example describes the application of a process according to the present invention.
- Wheat seed (c.v. Olympic) was inoculated with ~
foetida spores (HCB susceptible strain) by admixing l~g of ~ -spores with each ~50 g of seed in a sealed container on the rollers of a ball mill for 20 minutes. Samples of the ; 10 inoculated seed was then dressed with a fungicidal composition compri ing 50% w/w of compound 1 of Table I, 5% w/w ethylene glycol, 10% w!w "Celite" 298 and 35~ w/w of china clay by admixt'ure of lg of this composition with each kg of inoculated seed and blending in a'sealed container on the rollers of a mill to obtain a uniform product containing 500 ppm of active in~
gredient.
, i~ :
;
"'' ' ~' " ' ' ' ` ''`'"' ' ., "'.",;~', . .' ' " ' ', . , , ' . ' ' '' ' ~ . ;. ' ~ ' ~ lo ~0~48~4 The dressed ~eed was then sown through a ~eed drill in 6 singls row plots each 10 ~eet in Iength. The seed was then allowed to germinate and the wh~at plants were allowed to mature. At harvest the sleed heads were collected and the control of disease act~essed. The percentage of di~eased : heads and the disease as the percentage of the con~rol i~
presented in Table IV hereinbelow.
The above procedure wa~ sub3tantially repeated exceyt that the wheat seed was inoculated with the fungus ~ (HC~ resistant strain). The re~ult~ obtained are al~o pre~ented in Table IV hereinbelowO ~or purpo~e~ o~
comparison the sowing procedure de6cribed above wa~ sub-stantially repeated except that the dressed sèad was replaced ; by untreated inoculated s~ed. In ad~ition,:and also for the purpose of compari~on, the ~eed inoculation~ dressing and sowing procedure described hereinabove wa~ sub~tantially repeated for each-o~ the ~ungal specie6 ~ ~ .
t~C~ ~usoeptible) and ~ ~ (HCB reSit3tant~ eXcept that in a ~ir~t te~t th~ wheat ~eed was dres~ed with:"~ere~an~
(llcereBan~l i8 a Reg~lstered Trade Mark of E I Du Pont de Nemour6t Inc. for propriet~ ~ ~ungicidal compo6itio~s compri~ing as active ingredient a blend of m`ethyl mercury acetate and methyl mercury 2,3-dihydrox~-propyl-mercap*ide) atnd in a - second te~t the wheat Eteed was dres61ed with "Dithane M45"
~5 ('IDi'chane M45" i_ a R glAtered Trade Mark o~ ~the Roh~A and Haa_ : , ~
-,, .
': :: . ' . , ' ~ . .: .
:- .'' : .~ . '~, .
~:, -~' : - : .. . . . ..
. .
;48'~
Co for proprietary fun~idical composition~ comprising as active ingredient a ~inc co~plex of a p~lymeric manganese ethylene-1,2-bisdithiocarbamate)~ The results of these comparative tests are also sho~ in Table IV below.
TABLE IV
~ ~ . . -, .. , ~
Active Concentration Fungal Species ngredient of active (ppm) ~HCB susceptible) (HCB resi~tant) Percentage of Diseased Heads ~ :
- ~ 5 1 500 1.78 0.34 ~
~ 1 250 0. o8 o. ~2 ~::
: 7 1~ Ceresan"
(comparatlve ~:
: composition) 30 o.88 0~00 Dithane M45'l :
(comparative O
~ co~position) ~ 1500 o.63 0~00 ;:
:~ Control . ;
~ (no active ~ ~ .
:~ ingredient Nil : 36.88 ~ `10.47 ___ ~
~' .;
: , : , . . ,. ' . , ~: ' ' ' .. , .' :
Claims (4)
1. A process of treating cereal seed comprising treat-ing cereal seed with an effective amount of a composition comprising a composition of formula I
I
wherein R1 and R2 which may be the same or different are hydrogen, methyl, ethyl or propyl.
I
wherein R1 and R2 which may be the same or different are hydrogen, methyl, ethyl or propyl.
2. A process according to Claim 1 wherein the compound of formula I is .
3. A process according to Claim 1 wherein the compound of formula I is .
4. A process according to Claim 1 wherein the compound of formula I is .
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 |
|---|---|
| CA1064824A true CA1064824A (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 Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA254,104A Expired CA1064823A (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 (2)
| 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 |
| CN104351231A (en) * | 2014-10-11 | 2015-02-18 | 中国农业大学 | Application of 4-chlorocinnamaldehyde thiosemicarbazone in plant disease control |
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 (2)
| 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 |
| 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 |
|---|---|
| CA1064823A (en) | 1979-10-23 |
| FR2312957B1 (en) | 1980-08-29 |
| FR2312957A1 (en) | 1976-12-31 |
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