CA1036491A - Heterocyclic compounds and their use as pesticides - Google Patents

Abstract

ABSTRACT OF THE DISCLOSURE

Plant fungicidal and bactericidal compositions containing a triazinedione of the formula:

Description

~Q3f~491 This invention relates to a method of combating f'ungal and bacterial in~ections of~ plants by the use of certain triazine derivatives; and to plant anti-f'ungal and anti-bacterial compositions, and to certain novel, specific, triazine derivatives.

The pre~ent invention provides a proce~s for combating fungal and bacterial diseases of plants ~Ihich compri~es applying to plants, or to the locus of plants, a fungicidally or hactericidally effective, but non-phy~otoxic, amount of a triazine derivative of the general formula:-Rl `f 'I /N ~ N
! R4 ~ ~

~' ~
Wherein Rl is alkyl, alkenyl, cycloalkyl, phenyl, ' halophenyl or adamantyl; R2 is alkyl or together with ; R3 and th~ adjacent N- atom f'orms a pyrrolidine:ring, R3 is hydrogen, alkyl, alkoxy, phenyl or amino; and R4 ig hydrogen or alkyl; or a salt thereof.

Preferred compounds o~ the invention for use as plant 1036~91 ~ungicides and bactericides are those in which Rl is an alkyl radical of from 1 to 6 carbon atoms or a cycloalkyl radical; R2 is an alkyl radical oP from 1 to 4 carbon atoms; R3 is hydroge~ an alkyl radical of from 1 to 4 carbon atoms,an alkoxy radical of from 1 to 4 carbon atoms, phenyl or amino; and R4 is hydrs~en, or an alkyl radical of from 1 to 4 carbon atoms.

Even more preferred compounds are those wherein, in the general formula,Rl i~ an alkyl radical of from 1 to 6 carbon àtoms,or cycloalkyl; R is an alkyl radical of from 1 to 4 carbon atoms; R~ is hydrogen; and R is hydroger~ or an alkyl radical of from 1 to 4 carbon atoms.

When R is a hydrogen atom, the hydrogen is acidic, and the compounds will form salts with bases. Examples of such salts include alkali metal salts, for example lithiu~, sodium and potassium salts, alkaIine earth metal salts, for example calcium and magnesium salts, ~ ammonium salts, and salts formed from primary, secondary3 or tertiary amines, for example primary, secondary and tertiary aliphatic amines in which the one, two or three aliphatic radicals each contain from one to six carbon atoms. Salts of compounds wherein R4 represents a hydrogen atom may in general be conveniently ' ~ - 2 -~ ~ .
.

~)364~

prepared simply by mixing the triazinedione compound ; with the stoichiometric proportions of an alkali rnetalhydroxide, alkaline earth metal hydroxide~, amm~niaJ or amine, in a solvent or diluent. Water is generally the most convenient solvent or diluent for this purpose.

In a further aspect the invention provides plant anti-fungal and anti-bacterial compositions comprising as an active ingredient a triazine derivative, or a salt thereof, as defined in any of the preceding paragraphs;
I0 together with a carrier for the active ingredient; and, optionally, a surface-active agent.

Particular examples of triazine derivatives useful in the practice of the invention are set forth in Table 1 below.

The compounds of Table l have the general formula:-~

4 ~ N ~ N

R2 ,~N~ R3 .
.

~036~93~
~ , . _=

C~ ~ ~ o t ~ , ~; ~ O
H ~1 ~J H t~
E~ ~ O I ~1 ~ 3 tl:l ~ O ~U GO OC) C-- r~ O CO J
~ ~ J
.
~t~ p~ X

__ ~ ~ L
~ ~ rr~ ~ ~ ~ ~ ~ ~
~J N ~I X ~ ~ m ~:
X
~ _ _ _ , _ U~
~`J ~ ~ J N ~ ~ ~ ~ ~{ N
0:; C~ C) V
.
_ :~
,, 1 t P; O ~~ S t- S ' ~ o p~ o v ~ ~ ~
~ ~ 3 IS~ ~ ~1~ ~1 3 ~I 3 ~ C) C~ C) O ~ X V
I N I ~1 I p~I P~ U1 I C~ I
3 C~ ~ 1 C) ~1 J~
.
_ , __ _ ~ _ ~P .
O ~ 3 Ir\ ~ O~ l ~O~Oz .
_ . . ,~ _ _ .
`~

,~

~.~)36~

æ
o :4 o co ~ o O~ q~
~Z ~ J O O ~ J ~ ~D rd H ~J N ~1 1~ N 1~ 1~
. I , _ -- ,,__, ,___ ~ ~ _ ~P~ X ~ X ~ ~ X $ ~

~ _ , _~
O O p, r~
r; ~ m h h :5 h h _ __ _ _~ .
r1 11~ ~ , ' O`.
~ ~ r~
O ~ r~ ~ ~ ~ ~ c~ r~ ~.
C:~ t~J ~ 5 ~ ~ N I ~C X
~S C) ~ V I
1_1 ~ _ , r-l r~ I
C-' X~ X
~ S ~ .~ ~~ S .~ u ~ C~ O t~ O ~ V
1~; I ~ I ~ ~D 3 ~ `.
~ ¦ h ¦ ~ l ¦ C) ~ X :c: X
_ , _ ~ r~ ) ~\ O -1 N 1~ ~ . ~ L
,~ P-l r-l r-l r-l r~ I r~l t~
~:

~Z
~ l -5- ~

1036~91 _ . . .. _ .~, H ~

H ~ l N ,_~ O r ~:1 o~ O ~ ~O t~l O
r l U:~ ~ rJ O tU r,~ N
!~ ~ N ~-1 N N N N ~~ l ~I N
:, _ _ ,_ _ r~ rt~ r~
3~ r ~ X ~ r r.
. ~ _ _ r~
r~ r~
r~ 5 sr ~ O P, ~ C , ~ _ ~\z C ~ . Ir~ ~ U~
H ~ ~ ~j~ ~,r. r~J ~ ~~r~ ~ ,~ ~ ~N ,;~ ~ X
~3 ~ _ _ I
E~ ~

~ d ~d ~ cl~cll ~cl d ~cl l ~

a Z ~o ~ ~ O
:' ~E o C~Z _~_ _____ ~ I
~ \
--6~

i -' .
j 1~36~9~
The above listed derivatives are all novel.
In a yet further aspect, therefore, this invention includes the specific triazine derivatives set out in ; Table 1, herein above The compounds of formula 1 above, in genexal terms, may be prepared by methods described in our copendiny Canadian application No. 211730, filed October 18, 1974.
Thus, in one method, a guanidine derivative o~ ~ormula R~ R (II) wherein R6 and R7 may each be a hydrogen atom or an aliphatic radical, is reacted with a chloroformic ester ClCO2R8, wherein R8 is a hydrocarbyl group, preferably an alkyl group of 1 to 6 carbon atoms, for example methyl or ethyl, or preferably with a dialkylcarbonate (R80)2CO to give an intermediate ~III). This is then further reacted with an isocyanate RlNCO wherein Rl has any of the meanings hereinbefore assigned to it. The .

.
: - 7 -49~
reaction product so obtained cyclise3 to a triazinedione compound, as shown in the scheme below:~

; ~C/ ClC02R I 2 NR6R7 or ~R80)2CO ~ /

(III) ~R lNC o Rl N

(IV) The conversion of (III) to (IV) may be carried out in the presence of a catalytic amount of a tertiary amine, preferably a trialkylamine in which each of the three alkyl groups contains 1 to 6 carbon atoms.
.

The reaction of the chloro~ormic ester ClC02R8 with the guanidine may be carried out in water. Alternatively - the preparation of the ethoxycarbonyl guanidine may be ~arried out by reacting diethylcarbonate with the ~ree guanidine base in ethanol solution. In this method the ~C~36491 free guanidine i8 preferably prepared in ethanol b~J
adding 1 molar proportion of ~odium ethoxide to a guanidine salt in ethanol.

Es.~.edially preferred compounds include those numbered 3~ and 40 in Table I above.

In fungicide tests compound number 40 of ~able 1 gave good control of Wheat Rust, Puccinia recondita at an application rate of 50 parts per million, both in an eradicant, and in a protectant test.

:10 Compound No. 30 of Table I gave good control at the low application rate of 3 parts per million is a translocation (systemic) test (that is a test in which the soil surrounding the roots of the plants was drenched with a solution of the compound) against the oat Rust Puccinia hordei and against Crown Rust of oats Puccinia doronata.
Against Wheat Rust, Puccinia recondita, this compound also gave good disease control at the low application rate o~ 5 parts per million.

he triazine derivative~ may be used as fungicides or bactericides alone, but are.-preferably incorporated in a composition comprising a diluent in addition to the triazine derivative~ and may be used for a~ricultural ~', .

: .

and herbicidal purposes. The triazine derivative~
and compositions containing them, are variously active against a variety of fungal pathogens of plants.and seeds including, for example, the following:s Erysiphe ~ram is (Powdery Mildew) on barley Puooinia recondita (Rust) on wheat Puccinia hordei ~Rust) on oats Pytophthora _nfestans (Late Blight) on tomatoes Pucoinia Coronata (Brown Rust) on oats Plasmopara viticola (Downy Mildew) on vines Unoinula necator (Powdery Mildew) on vines Podosphaera leucotricha (Powdery Mildew) on apples The triazine compounds, and compositions containing .
them, are also variously active against a variety of foliage-borne bacterial plant diseases, including for example, the following:-Xanthomonas oryzae - (bacterial blight of rice) Erwinia am~lovora (fireblight of pears) :
Pseudomonas tomato (bacterial speck of tomato) Xanthomonas vesioatoria (bacterial spot of peppers) Pseudomonas tabaci (wildfire of tobacco) ~: ' . ~ .

, ~ ;49~
For the control of both fungal and bacterial in~ection3 of plants the rate at which the triazine compound~ o~
the invention are applied will vary, depending upon the particular compound chosen for use, the disea~e to be controlled and on the particular species of plant acting as host to the disease. However, a non-phytotoxic rate of application is neces~ary, as exemplified, hereinafter, with specific re~erence to Example~ ll and 12.

In carrying the invention process into practical effect the growing crops, plantæ, seeds, or soil may be treated ~ . by any of the well known and established procedures used in agriculture and crop protection. Thus, for example, the active compound may be applied as solids, liquids, solutions, dispersions, emulsions and these may comprise, 1n addition to the active substance, any other adjuvant useful for formulation purposes, or any other biologically active substance, for example to increase ` the number of diseases combated.

Such so1id or liquid substances and formulations may be applied, ~or example, by any conventional technique, for example~ by dusting, or btherwise applying the solid .substances and formulations to the surfaces of growing crops, harvested produce, plants, seeds or soil, or to ~364~

any part, or combination of parts thereof, or, for example, applying liquids or solutions for example, by dippin~, spraying, mist-blowing or ~oakin~ techniques.

The invention process is therefore useful for treatin~
plants, seeds, harve3ted ~ruits, vegetables, or cut flower~ infested with, or liable to infestation with any of the aforementioned specific fungal or bacterial diseases.

The term "seeds" is intended to include propagative plant forms generally and therefore includes, for example, cut stems3 corms, tubers, rhizomes and the like.

As previously noted the triazine compounds are preferably used in admixture with a.solid or liquid diluent. The I admixtures so obtained are hereinafter referred to as compositions. Preferably the compositions comprise a surface-active agent.
.
The solid compositions may be, for example, in the form of dusting powders, or may take the form of granules.
Suitable solid diluents include, for example3 kaolin, bentonite, kieselguhr, dolomite, calcium carbonate, talc, powdered magnesia and Fuller's earth.
.

.
" ' 1~)36~9~, Solid compositions may also be in the form of dispersible powders or grains comprising in addition to the active ingredient, a wetting agent to facilitate the dispersion of the powder or grains in liquid~.
Such powders or grains may include ~illers, su~pending agents and the like.
, Liquid compositions include aqueous solutlons, dispersions and emulsions containing the active ingredient preferably in the presence of one or more surface-active agents. Water or organic liquids may be used to prepare solutions, dispersions, or emulsions of the active ingredient. The liquid compositions of the invention may also contain one or more corrosion inhibitors for example, lauryl isoquinolinium bromide.

Surface-active agents may be of the cationic, anionic or non-i~nic type. Suitable agents of the cationic type include, for example, cetyltrimethyl ammonium bromide Suitable agents of the anionic type include, for example, soap~, salts of aliphatic monoesters of ; 20 sulphuric acid, for example, sodium lauryl sulphate;
and salts of sulphonated aromatic compounds, for example, dodecylbenzenesulphonate, sodium, calcium and ammonium .

~3~
lignosulphonate, butylnaphthalene sulphonate, and a mixture of the sodium salt~ of diisopropyl- and triisopropyl-naphthalenesulphonic acid. Suitable agents o~ the non-ionic type include, f'or example, the condensation products of ethylene oxide with ~attlJ
alcohols ~uch as oleyl alcohol and ce~yl alcohol, or with alkyl phenols such a~ octyl-phenol, nonylphenol and octylcresol. Other non-ionic agents are the partial esters derived from long chain fatty acids and hexitol anhydrides, for example, sorbitol monolaurate, and the ; condensation products of the said partial esters with ethylene oxide and the lecithins.

The compositions which are to be used in the form of aqueous solutions, dispersions or emulsions are generally supplied in the form of a concentrate containing a high proportion of the active ingredient, the concentrate being diluted with water before use. These concentrates are usually required to withstana storage for prolonged periods and after such storage to be capable of dilution with water in order to form aqueous preparations which remain homogenous for a sufficient , time to enable them to be applied by conventional spray equipment. In general concentrates may conven;ently contain from 10 to 85% and preferably from 25 to 60~
by wéight of active ingredient. A particul~rly preferred form of concentrate is an emulsifiable concentrate compri~ing a solution of a triazine derivative, as defined above, in an organic ~olvent containing a aur~ace-active a~ent. When required for use, the concentrate can readily be dispersed in water by agitation to provide a dilute emulsion auitable ~or sprayin~. Dilute preparations ready for use may contain varying amounta of the active ingredient, depending , upon the purpose for which they are to be used; however, dilute preparations may contain between 0.0005% and 0.1% by weight of the active ingredient.

It is to be understood that the fungicidal compositions used in this învention may comprise, in addition to one or more triazine derlvatives, one or more other compounds having biological activity.

The invention is illustrated, but not limitedg by the following Examples.

.

~36~9JJ

This example illustrates the preparation of compounds according to the invention and as listed in Table I.

(a) Preparation Or carbamate intermediate.
N,N~dimethy~guanidine hydrochloride (123.5 g; lM) was added to a solution of potassium hydroxide (112.2 g;
2M) in water (ca. 300 ml.). The solution was stirred and kept at -10C to -5C by cooling while ethyl chloroformate (108.5 g; lM) was added over a period of 45 minutes~ A~ter addition was complete, the solution was allowed to warm to room temperature, the ~ water was evaporated in a vacuum, and the residue was ; extracted with boiling chloroform (300ml.). Theextracts were cooled, dried, and evaporated to yield j a yellow oily solid. Recrystallisation from a 2:1 mixture of toluene and petroleum (b.p. 40-60C) gave the white crystalline carbamate derivative (formula III, R8=C2H5, R6=R7=CH3) having a melting point of 73-76C.

(b) Preparation of triazinedione.
The carbamate derivative so obtained wa~ dissolved in dry toluene (ca. lOOml. per 15 g. of carbamate) ~ - 16 -3649~
and heated under reflux with ethyl isocyanate (1 molar proportion) and a little dry triethylamine as catalyst ~or 16 hours. The toluene was then removed in a vacuum and the residue recrystallised from ethanol, giving the triazine dione as a white fibrous solid of melting point 236~238QC.

Using the appropriate guanidine starting material and aliphatic isocyanate the following 4-aminotriazine-diones ~Table II below) were prepared by the above procedure, ~0369~9~
TABLE II

N ~ O

NH

H~T~R

. _ I
Rl R MELTING POINT C
~ .. _ _ C4Hg C2H5 244 . ~Q C3H7 C2H5 228 I (} ,~ : ~ iso C3H7 3 ~ 280-282 n hexyl 2 5 21~-220 n C4Hg n C4Hg . 247-248 1, iso C3H7 iso C3H7 235-237 ¦ ~ CH3 241-242 ':~

An emulsi~iable concentrate was made up by mixing together the ingredients set out below in the proportions stated and stirring the mixture until all the constituents were dissolved.

~(~3~9~l Compound No. 30 of Table I 10%

Ethylene Dichloride 40%

Calcium dodecylbenzene-sulphonate 5%

; "Lubrol" L 10%

"Aromasol" H 35%

,:
~; A composition in the form of grains readily dispersible in a liquid, e.g. water, was prepared by grinding together the first three of the in~redients listed belowt in the presence of added water and then mixing in the sodium acetate. The resultant mixture was dried and passed through a British Standard mesh sieve, size 44-100, to .
obtain the desired size of grains.

Compound No. 40 (Table I) 50%

"Dispersol" T 25%

"Lubrol" AP~ 5 1.5%

Sodium Acetate 23.5%

' - The ingredients listed below were all ground to~ether in the proportions stated to produce a powder formulation ~Q360~
~ readily dispersible in liquids.

: Compound No. 30 (Table I) 45%

"Di~per~ol" T 5~

"Lissapol" NX 0.5%

"Cellofas" B600 2%

Sodium acetate 47.5%

, The active ingredient (Compound No. 40 of Table I) was dissolved in a solvent and the resultant liquid was ~prayed on to the granules of Fuller's earth. The solvent wa~ then allowed to evaporate to produce a granular I0 composition.

Compound No. 40 (Table I) 5%

Fuller~s earth or China clay granules 95%

A dusting powder was prepared by mixing, in the proporkions stated, the active ingredient with kalc.
"
Compound No. 30 (Table I) 5%

Talc 95%

, ~o -- .

~V3649~

A Col formulation was prepared by ball-milling the constituents set out below and then ~ormin~ an aqueous ~uspension of the ground mixture with water.

Compound No. 40 ~able I) 40%
"Disper~oll' 10%
"Lubrol" 1%
Water 49%

: ' .

1. A dispersible powder formula~ion was made by miXing to~ether the ingredients set out below and then grinding the mixture until all the constituents were thoroughly mixed.

Compound No. 30 o~ Table I 25%
; ~ "Aerosol" OT/B 2%
"Dispersol" A.c. 5%
China Clay 28%
Silica 40%

.

~03649~

This example illustrate~ the preparation of two dispersible powder ~ormulations. In ea¢h in~tan¢e all the ingredients are mixed in the proportions ~tated and the mixture then ground in a comminution mill.

Compound No. 40 of Table I 25%
"PERMINAL" BX 1%
"Di~persol" ~ 5%

PoIyvinyl~rrolidonë 10%

Silica 25%

China Clay 34%
., .
~` Exactly the same formulation was made using Compound No 30. of Table I.
.

The ingredients set out below were formulated into a disper3ible powder by mixing and grindin~ the ingredients in the proportions stated.
' Compound No. 40 of Table 25%

"AEROSOL" OT~ 2%

"Dispersol" A 5%

China Clay 68%

-~03649~

Exactly the same formulation was prepared u~ing Compound No. 30 of Table I instead o~ Compound No. 40 In Examples 2-10 above percentage amounts are on a weight basis.

, ; 5 The following constitutes an explanation o~ the composition~
or ~ubstancefi represented by the various Trade Marks and Trade ~ames referred to in the foregoing Examples.

"LUBROL" L is a condensate of 1 mole of nonyl phenol with 13 molar proportions of ethylene oxide.
"AROMASOL" H is a solvent mixture of alkylbenzenes "DISPERSOL" T AND is a mixture of sodium sulphate and a ~ AC condensate of formaldehyde with the i sodium salt of naphthalene sulphonic acid.
"LUBROL" APN 5 is a condensate of 1 mole of nonyl phenol with 5~ moles of naphthalene oxide.
"CELLOFAS" B 600 is a sodium carboxymethyl cellulose thickener.
"LISSAPOL" NX is a condensate of 1 mole of nonyl phenol with 8 moles of ethylene oxide.
"AEROæOL OT/B is dioctyl sodium sulphosuccinate.
"PERMINAL" ~X is an alkyl naphthalene sulphonate (sodium salt) .

The triazine derivatives were tested against a wide - 23 - ~

,' ' ' ' ' " "

49~

variety of foliar ~ungal diseases of plant~. In the test, a composition comprising an aqueous solution or suspension of the test compound was sprayed on to the foliage Or uninfected plants; the soil in whi¢h the planta were growing was also drenched with the ¢ompo~ition.
The compositions used for spraying and drenching contained 100 parts per million (ppm.) (unless otherwlse expres~ly stated) of the test compound. After spraying and drenching, the plants were then exposed to infection with the di~ aaes it was desired to control, along with control plants not treated with the compound. After a ' period of days, depending upon the particular disease, ; the extent of the disease was visually assessedg as a percentage of the disease established upon the control plants which had not been treated with the compound under test, according to the grading scheme below.
'' Gradin~Amount of disease as a percentage of disease on contr_l plants _ 0 61 to 100 l 26 to 60 ' 2 6 to 25 3 O to 5 4 No disease :~

~(~36491 In Table III and Table V below the names Or the diseaaes aregiven in the rirst column, and in the second column is given the time which elapsed between expo~ing the plants to infe¢tion and assessing the amoun~ of di~ease.
Tables IV and VI give the te~t results.

TABLE III
_ _ TIME INTERVAL DISEASE CODE
DISEASE AND PLANT (DAYS) LE~T~R (TABLE IV) _ PLASMOPA~A VITICOLA 7 . A
(Vine) . .

(Vine) PODOSPHAERA LEUCOTRICHA
_ __ 10 , C
(Apple) . i _ .

',' ' '

- 2~ -.

.

TABLE IV 1~36~9~
. .
COMPOUND NO. DISEASE CODE LE~TER
(Table I) A B C
~P 1~l3 9 3 P . 3 : 10 3 P P
O 1 3 1 ~

22o O 33 43 . 22 : O 4 4 34 4 3 P .

: ~ ~ ~ 3 ~ ~

"P" denotes too much phytotoxicity to get a meaningful a~sessment of anti-fungal activity "-" denotes not te~ted.

V36~
TABLE V
_ _ , l . DISEASE AND PLANT TIME INTERVAL LETTER (TABLE ~I) _ _ _ _ , Puccinia recondita 10 D
(-heat) (Barley) -- ~

, .

, .
. - 27 - .

, ~36~g~ /
TABLE VI

COMPOUND NO. DISEASE CODE LETTERS
_ (TABLE I) D E
; APPLICATION RATE APPLICATION RATE
. . OF 100 ppm OF lOO ppm . 3 ~ ~

22 O . 3 .
9 . : APPLICATION RATE

: 10 3 1

3 P 43 . 15 3 . 1 .
6 o3 4 18 3 ~ . O

23 O . 4 24 ~ 4 ~, . _ ~ 28 -1~)36~9~
.TABLE_VI Continued . _.
' COMPOUND NO. DISEASE CODE LETTERS
~ I
(TABLE I) D E
APPLICATION RATE APPLICATION RA~E
OF 100 ppm 0~ 50 ppm _ _ .

~ 27 3 2 : 28 3 4 3324 . 33 .

: RESULTS BELOW ARE AT
. . AN APPLICATION RATE
3 3 OF 25 ppm . 7 O 2 . O 4 _ . _._ .

~ - 29 - .
.

1036~9~
TABLE VI Continued . . , _ _ _ . COMPOUND NO. DISEASE CODE LETTERS
,1 tTABLE I) D E
_. _ ~
APPLICATION RATE APPLICATION RATE
OF 100 ppm 0~ lO ppm 'L, ~ _ 1 3 ~ 4 ' The triazine oo~pound~ were tested against a variety of ~oliage-borne bacterial plant diseases in the glasshouse.
The anti-bacterial screening method employed a mist propagator to aid infection of treated p~ants by providing conditions o~ high humidity.
, .

The plants were sprayed and/or root drenched with an aqueous solution containing various concentrations of the test chemical. After 48 hours they were inoculated with the appropriate disease organism. Inoculations were accompanied by wounding the plants, which was neceæsary ~or bacterial in~ection to take place. Immediately a~ter-wards the plants were placed under high humidity. Agrimycin (17% Streptomycin sulphate) at 2000 ppm and lOOO ppm. was ~, -- ~O -~036~9~

applied a~ a standard treatment and with water a~ a control.
After eight days, the symptoms were as~essed on a 0-4 scale given in Table VII below, wherein the extent of the disease is given in the ~orm of a grading as ~ollows:-.
Grading Perc ntage Amount Or Disease 3 . 0 - 5

4 No disease and the disease code of Table VII is given below:-Disease and Plant .Dieea~e Code Xanthomonas oryzae A
(bacterial blight of rice) Erwinia amylovora B
(fireblight on pears) Pseudomonas tomato C
(baoterial speck of tomato) :
~ .

~036491 TABLE VII

, _ . . . , RATE OF DISEASF, CODE
COMPOUND NO. APPLICATION
TABLE I (ppm) A B C
_ ll 200 2 0 3 Ris 18 . lOO l 3 ~ R/S
2 lOO ~ 0 3 R and S
: . ~ - 2* 3 3 R and S
;, .

R/S denote~ a combined root drench and foliar spray test.
R and S denote individual root drench and ~oliar spray tests .
* denote~ a result obtained by a foliar spray test alone.
.

.

:
. ~

~ -32- .
- .

Claims (4)

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:

1. A process for combating fungal and bacterial diseases of plants which comprises applying to plants, or to the locus of plants, a fungicidally or bactericidally effective, but non-phytotoxic, amount of a triazine derivative of the general formula:- Wherein R1 is alkyl, alkenyl, cycloalkyl, phenyl, halophenyl or adamantyl R2 is alkyl or together with R3 and the adjacent N-atom forms a pyrrolidine ring; R3 is hydrogen, alkyl, alkoxy, phenyl or amino ; and R4 is hydrogen or alkyl; or a salt thereof.

2. A process according to Claim 1 wherein, in general formula, R1 is an alkyl radical of from 1 to 6 carbon atoms or a cycloalkyl radical; R2 is an alkyl radical of from 1 to 4 carbon atoms; R3 is hydrogen, an alkyl radical of from 1 to 4 carbon atoms, an alkoxy radical of from 1 to 4 carbon atoms, phenyl or amino;

and R4 is hydrogen, or an alkyl radical of from 1 to 4 carbon atoms.

3. A process according to Claim 2 wherein in the general formula, R1 is an alkyl radical of from 1 to 6 carbon atoms, or cycloalkyl; R2 is an alkyl radical of from 1 to 4 carbon atoms; R3 is hydrogen; and R4 is hydrogen, or an alkyl radical of from 1 to 4 carbon atoms.

4. A process according to Claim 1 wherein, the triazine derivative is selected from compounds of the general formula wherein R1, R2, R3 and R4 have the following definitions: