JPS6372607A - Composition for preventing damage of plant by disease and method for preventing said damage - Google Patents

Abstract

PURPOSE:To provide the titled composition effective in protecting a plant from various blights, by using phenylglycines such as phenylglycine, N- phenylglycylphenylglycine, 3,6-diphenyl-2,5-piperazinedione, etc., as active components. CONSTITUTION:The objective composition for preventing a plant from damage by disease contains the phenylglycines of formula I, formula II or formula III [R<1> is OR<11> or N(R<12>)R<13> (R<11> is H or alkyl; R<12> and R<13> are H, alkyl or together with N form a heterocyclic group); R<2> and R<3> are H, alkyl or acyl; R<4> is H, halogen, OH, alkyl or alkoxy] as active components. An effective amount of the phenylglycines is applied to a plant or its growing environment when the disease of the plant breaks out or the outbreak of disease is expected. It is effective against bacterial soft rot, bacterial spot, gray mold, etc., of vegetables, alternaria blotch, scab, etc., of fruit trees, canker of citrus fruit, blast of rice, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to an anti-plant disease composition and an anti-plant disease method. Useful plants for details on length, a3 teeth.

This invention relates to drugs and methods for protecting against various diseases caused by filamentum.

Purpose of the Invention Some of the inventors of the present invention have previously discovered that phenylglycine or a maple phenylglycine-bound conductor derived therefrom promotes the growth of plants useful for plants, and has already proposed it (1981). 5゛ filed on March 13th, 1986-
53574). Therefore, the present inventor conducted further research on the biological activity trap of phenylglycines proposed above for plants, and found that phenylglycine@ protects plants from various diseases and protects plants from the diseases. It has been discovered that it has a truly wonderful effect of regenerating the growth of the plants.

The structure and effects of the invention, that is, the present invention has the following general formula (I) -1L, (
This is an anti-plant disease composition containing phenylglycines represented by I)-su or (I)-c as an active ingredient, and which is effective for plants or the environment in which they grow, where the phenylglycines are effective. This is an anti-plant disease method characterized in that it is applied at the time of occurrence of a disease on a plant or before the disease is transmitted to the offspring.

The present invention will be explained in more detail below.

According to the present invention, such objects and advantages of the present invention are provided by monocapsular phenylglycines represented by the following formula (I) -1 , salts thereof at carboxyl & when R1 is a hydroxyl group, and R1 or When R1 is a group other than an acyl group, the acid addition salt of the 74 group is represented by the following formula (I) -b. Table h Sale6 N-phenylglycylphenylglycine a, its salt in a carboxyl group when R1 is a hydroxyl group, and its acid addition salt in a 7mino group when R3 or R1 is a group other than an acyl group, and at least phenylglycines selected from the group consisting of diketopiperazine compounds represented by the following formula (I) -C as an active ingredient for protection and regeneration of plants against diseases and coupled by an anti-plant disease composition containing °C. be done.

The above formulas (I)-a, (I)b and (I)-
(For the compound represented by !, the compound of the above formula (I)-a is a monomorphic phenylglycine, and the compound of the above formula (I)
The compounds -b and <1) -0 correspond to the 702 compound and are therefore extremely closely related.

The duplex of the above formula (I)-b is linear, and the duplex of the above formula (I)
The doublet of -e is cyclic.

In the above formula (I)-a, R1 is -0R11 or an alkyl group below, R11 and R18 are each independently a hydrogen atom or an alkyl group having 5 or less carbon atoms, or R" and R" are mutually Together with the nitrogen atom to which they are bonded, they may form a 5- or 6-membered heterocycle which may further contain a heteroatom.

The alkyl group having 5 or less carbon atoms in all may be linear or branched, such as methyl.

Ethyl, n-propyl, 1ao-propyl + n-butyl* 5ee-butyl, 1so-butyl, t-
Butyl and n-pentyl.

Also as a furkyl group having 5 or less carbon atoms in R" and R",
The same groups as above for R''K can be exemplified.

The 5- or 6-membered heterocycle formed by bonding R'' and Rlm further includes, for example, a nitrogen atom as a heteroatom.

It can contain oxygen atoms or sulfur atoms.

As the group -0R11, according to the definition of all, for example, hydroxyl, methoxy, ethoxy, n-propoxy,
Examples include 13o-poupoyac, n-butoxy, and n-pentoxy.

For example, 7ξ; methylamino, ethyl 7mino, n
-Propyl 7mino + 1so-Propyl 7mino, n-
2-tylamino, l-O-butylamino.

Heptanoalkyl amines such as n-pentyl 7mino; dialkylamines such as dimethylamine, diethylamine and deupropylamine; piperidino, piperazino, morpholino, pyridyl and the like.

In the above formula (I)-a, R2 and RA are each independently a hydrogen atom, a fulkyl group having 5 or less carbon atoms, or a fulkyl group having 5 or less carbon atoms.
These are the following 7 sol groups. Examples of the alkyl group having 5 or less carbon atoms include the same ones as those exemplified for all.

In addition, acyl groups having 5 or less carbon atoms, such as formyl, 7-cetyl, propionyl, and 1110
Examples include -phthyryl, valeryl, and 1so-valeryl.

Moreover, R' is a hydrogen atom, a halogen atom, or a hydroxyl group.

It is a furkyl group having 5 or less carbon atoms or a flukoxy group having 5 or less carbon atoms. Examples of halogen atoms are fluorine, chlorine, bromine, and iodine. As a furkyl group having 5 or less carbon atoms, R
The same substances as those exemplified for No. 11 can be mentioned, and as a flukoxyfluorocarbon having 5 or less carbon atoms, 10
You can cite the same examples as those exemplified for 1.

When the monomeric phenylglycine represented by the above formula (I)-a has a carboxyl group (formula, (I)
-m, when R1 is a water group, the carboxyl group can be in the form of a salt. Examples of such salts include salts of alkali metals such as sodium and potassium, and calcium.

Examples include salts of alkaline earth metals such as magnesium, ammonium salts, and the like.

Furthermore, if it has a monomeric form represented by the above formula (I)-a'''C, and R2 or dRs is a group other than an acyl group, that is, a hydrogen atom or a furkyl group having 5 or less carbon atoms, the amino group can be in the form of its acid addition salts. Examples of such addition salts include mineral acid salts such as hydrochloride and hydrobromide, and lower aliphatic carbon powder salts such as acetate. As monomeric phenylglycines represented by the above formula (I)-a, compounds in which either R8 or aa is a hydrogen atom or a furkyl group having 5 or less carbon atoms are preferred, for example. .

Examples of such monomeric phenylglycines, salts thereof, or acid addition salts thereof include the following compounds.

(a-1) Phenylglycine (a2) 4-hydroxyphenylglycine (a-3) 4
-Methoxyphenylglycine (a-4) 4-chlorophenylglycine (a-5) 4-methylphenylglycine (
a-6) Ferglycine melone ester (a-7
) Phenylglycine ethyl ester (a-8) Phenylglycine-2-methothenth diethyl ester (a-9) 4-hydroxyphenylglycine methyl ester (a-10) 4-methoxyphenylglycine methyl ester (a-11) 4 -Riphenylglycine methyl ester (a-12) 4-methylphenylglycine methyl ester (a-13) N-methylphenylglycine (a-14
) N, N-') methylphenylchrysine (a-1
5) N-formylphenylglycine (a-16)
N-7 Hettylphenylglycine (a-17) N
-) Realoacetylphenylglycine (a-18) N-7 cetyl-4-aryanphenylene/L.

Glycine (a-19) N-7 cetyl-4-methylphenylglycine (a-20) N-7 cetyl phenylglycine methyl ester (a-21) Phenylglycinamide (a-22)
271 no 2-phenyl 7cetylaminoethane (a-23) 2-7 minnow 2-phenyl 7cetylaminoptane-l (&24) phenylglycine methyl ester hydrochloride (a-25) 4-*Droxyphenylglycine methyl Ester hydrochloride (&-26) 4-chlorophenylglycine methyl ester salt (a-27) 4-methylphenylglycine methyl ester hydrochloride (a-28) Phenylglycine salt a salt (a-29)
Phenylglycine sodium salt (a-30) 4-chlorophenylglycine sodium salt (a-31) 4-methylphenylglycine sodium salt (a-32) N-ace+ruphenylglycine sodium salt (a-33) N7 cetyl phenyl Glycine ammonium salt (a-34) N-7 Cetyl phenylglycine imbrobyl ammonium salt Above formula (I) -b K#ite, R', R", R", 1
d! The formula for HR4 is the same as in formula (I)-a above, and specific examples of each will also be clear from the above examples. N-phenylglycylphenylglycines represented by the above formula (I)-b can also take the form of a salt at the carboxyl group when R1 is a hydroxyl group,
In addition, if R1 or R3 is a group other than an acyl group,
It can also take the form of an acid addition salt at the mino group. Examples of such salts and acid addition salts will also be apparent from the above illustrations for formula (I) -&.

As the N-phenylglycylphenylglycines represented by the above formula (I)-b, compounds in which R1 is, for example, a hydrogen atom or a furkyl group having 5 or less carbon atoms are preferred.

Examples of such N-phenylphenylglycines, salts thereof, or acidic 270 salts thereof include the following compounds.

(b-1) N-phenylclycylphenylchrycine (b-2) N-(4-hydroxyphenylglycyl) phenylglycine (b-3) N-(4-methoxyphenylglycyl) phenylglycine (b-4 ) N-(4-chlorophenylglycyl) phenylglycine (b-5) N-(4-methylphenylglycyl) phenylglycine (b-6) S-(4-chlorophenylglycyl)-4-
Chlorophenylglycine (b-7) N-7enylglycylphenylglycine methyl ester (b 8) N (4-hydroxyphenylglycyl) phenylglycine methyl ester (b-9) N-(4-methoxyphenylglycyl) phenyl Glycine methyl ester (b-10) N <4-1ao7z=le f+)'
/l) Phenylglycine methyl ester (b-11) N-(4-methylphenylglycyl)phenylglycine methyl ester Cb-12) N-(4-chlorophenylglycyl)-4-chlorophenylglycine methyl ester (b-13 ) N-(N-7 cetyl phenylglycyl) phenylglycine (b -14) N -(N-7 cetyl phenyl glycyl/l/) -4-90 lophenyl chrysine Cb -
15) N-(N-7 cetylpheconruglycyl)-
4-methylphenylchrycine<b-16) N-(N-7 cetyl-4-chloropheny/I/ f!j sil)-4-lyC1 lophenylglycine (b-17) N-(N-7 cetyl phenyl glycyl) phenylglycine methyl nystyl<b -18) N-(N-7 7-tylphenylglycyl)-4-rio0 phenylglycine methyl ester (b -19) N-(N-7 cetyl phenyl glycyl) , L) Phenylglycinamide (b-20) N-(N-7cetylphenylglycyl)phenylglycine sodium salt In the above formula (I) -C, at, R3 and R
The definition of 4 is the same as in the above formula (I)-a, and each specific example will also be clear from the above examples.

As the diketopiperazine compound represented by the above formula (I)-e, a compound in which R8 and am are each independently a hydrogen atom or an alkyl group having 5 or less carbon atoms is preferable, for example.

Examples of such diketopiperazine compounds include the following compounds.

(c 1 ) 3s6-diphenyl 2 e5-piperazinedione (c-2) 3.6-di(4-chlorophenyl)-2
,5-piperazinedione ('c-3) L6-di(4-methoxyphenyl)-
2,5-piperazinedione (c-4) 3,6-di(4-methylphenyl)-2
,5-piperazinedione (c-5)3-phenyl-6-(4-chlorophenyl)
-2,5-piperazinedione (e-6) 3-phenyl-6-(4-methylphenyl) -2,5-piperazinedione (c7) L4-dimethyl-3,6-diphenyl-2,5-piperazine Diones of the above formula (I)-&, (I)-su and (I)-e
The compound can be produced according to a method known per se (Organic 5yntheses Co
11@activeVolume 3 e p, 84 (I
955), Journal of America
Chemical 5ociety, 6 L 26
2 B (I946)).

The anti-plant disease composition of the present invention comprises a monomeric phenylglycine of the above formula (I)-a, a salt thereof or an acid addition salt thereof, N-phenylglycylphenylglycine of the above formula (I)-b. , this salt or its acid addition salt and the above formula (
I) Contains at least phenylglycine selected from the group consisting of diketopiperazine compounds of -c as an active ingredient for protection against plant diseases and regeneration.

The anti-plant disease composition of the present invention is usually used in a form combined with an inert carrier or adjuvant.

Is it that bad? as carriers or adjuvants, such as talc, bentonite, clay, kaolin.

Diatomaceous earth, white carbon, vermiculite.

Solid carriers such as slaked lime, ammonium sulfate, and urine

Surfactants, emulsifiers such as furkylsulfone salts, lignin sulfonates, polyoxyethylene glycol ethers, polyoxyethylene furkylaryl ether, polyoxyethylene sorbitan monoalkynate, cinnatylmethane disulfonate, or Dispersants or various types such as carboxymethyl cellulose, 7 Ravi 7 rubber, etc.'
, adjuvants, etc. Two or more of these inert carriers and adjuvants can be used in combination.

The anti-plant disease composition of the invention is prepared by mixing the active ingredient as described above with an inert carrier and/or auxiliary agent as described above, such as a solution.
It is prepared in conventional forms such as emulsions, suspensions, dressings, pastes or granules.

The anti-plant disease composition of the present invention, in the form of a preparation as described above, usually contains the active ingredient in an amount of 0.01 to 99% by weight, more preferably 0.1 to 96% by weight.

The anti-plant disease composition of the present invention protects living plants or their living environments from various N-infestations, and regenerates the growth of damaged plants. It protects plants against various diseases and regenerates the growth of plants affected by the diseases by applying it with a spear that is effective against.

The application to a living plant can be the whole organism or a part of the living plant, for example, one leaf of the plant,
There are 9 types of stems and buds, and in plants grown in tissue culture, it is most likely a callus.

The anti-plant disease composition of the present invention contains the above-mentioned active compound as a violet which is effective for protecting plants against diseases and regenerating the growth of plants that have been affected by the diseases. The active compound is preferably applied in an amount of 0.001 to 500 g, more preferably 1 to 200.9 g per 10 are of the area inhabited by plants.

Application can be carried out by conventional methods such as, for example, spraying, spraying, dusting.

When applied to seeds or callus, it is preferable to contact the seeds or callus as a solution containing 1% to 10%, more preferably 1% to 1% of the active ingredient.

The anti-plant disease composition of the present invention protects plants against diseases and regenerates the growth of plants affected by the diseases.

The anti-plant disease composition of the present invention targets diseases caused by bacteria and filamentous fungi of various plants such as vegetables such as Chinese cabbage, lettuce, and mizuna, grains such as soybeans, corn, and rice, citrus fruits, and fruit trees. Gives needles against diseases,
It benefits the regeneration of plants.

An example of such a disease is CF'i, soft rot of vegetables.

Bacterial diseases such as Spot+11 disease, Botrytis blight.

5 Diseases caused by filamentous fungi such as powdery mildew, downy mildew, sclerotia, tuberculosis, and rust, as well as diseases of fruit trees such as leaf spot, scab, scab, green mold, green mold, etc. , as well as citrus fruit, rice blast, and sheath blight.

The anti-plant disease composition of the present invention exhibits a unique effect on vegetable diseases, especially Chinese cabbage soft rot among the above-mentioned diseases.
Shows regeneration effect.

The timing of treatment with the anti-plant disease composition of the present invention varies depending on the type 81 of the crop, the treatment method, and the target disease, but in the case of spray treatment, it is preferably 20 days before the expected onset of the disease, preferably 10 days before the expected onset of the disease.
the day before, or within 5 days, preferably 3 days after the onset of illness.
Valid within days.

The present invention will be explained in further detail with reference to Examples below.

Add 1 part of phenylglycine fAO,001mk to 14 parts of a water-soluble solution containing 0.1% of the surfactant ORPOL 2680 (Toho Kagakuten) and use it as a homogeneous solution or suspension.

Preparation Example 2 Phenylglycine M19. talc and bentonite )(
7) @fi mixture 8.7 E'11.
5ORPOL 5060 (Toho Chemical Exhibition) and 5OR
POL 800A (Toho Chemical Exhibition) violet mixture 0.3
Thoroughly grind and mix the two parts to make a wettable powder. The hydration M O,0
Add 9'-is to an aqueous Q14 solution containing 0.1% of 5ORPQL 2680 (manufactured by Jho Kagaku) and use it as a suspension.

Test Example 1 The stems and leaves of Chinese cabbage infected with Chinese cabbage soft rot and soil 150.9 were mixed with water 200ml/(0.1% 5ORPOL
2680), as well as mixed and crushed mata, f3. The P solution was sown in 7 Chinese cabbage traps in porcelain pots with an area of 150 cm after 2 weeks (3rd to 4th period).
4all pots were sprayed. Thirty-one days after infection, phenylglycine and phenylglycine methyl ester hydrochloride, each prepared by the method in Preparation Example 1, and 3,6-diphenyl-2,5-piperazinedione, which had been cleaved into v4 by the method in Preparation Example 2, were activated. Each of the compositions contained as components was sprayed in a predetermined treatment amount. On the 24th day after the 4th treatment, the industrial section was cut out, and the total fresh x amount thereof was compared with that of the untreated control plot, and the control effect is shown in Table 1 based on the weight ratio.

Test Example 2 - Phenylglycine methyl ester salt prepared by the method of Preparation Example 1, and a preparation were added to 7 Japanese cabbage plants two weeks after sowing (3-4 leaf stage) [in a 150 cd porcelain pot]. A composition containing 2,5-piperazinedione as an active ingredient, which was IA-extended by the method of Example 2, was sprayed onto each lid to form a predetermined lid. On the third day thereafter, the Chinese cabbage soft rot fungus was treated in the same manner as in Test Example 1. On the 24th day after the treatment, the # part of the stem was cut, and the M amount ratio was determined in the same manner as in Test Example 1, and the control effect is shown in Table 2.

Table 1 Table 2

Claims (1)

[Claims] 1. The following general formula (I)-a, (I)-b or (I)
)▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・・・・
・(I)-a ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・(I
)-b ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(I)-c [However, in each of the above formulas, R^1 is -OR^1^1 or ▲There are mathematical formulas, chemical formulas, tables, etc.▼ Yes, R^1
^1 is a hydrogen atom or an alkyl group having 5 or less carbon atoms, and R^1^2 and R^1^3 are each independently a hydrogen atom or an alkyl group having 5 or less carbon atoms, or R^1 ^2 and R^1^3 may be bonded to each other and together with the nitrogen atom to which they are bonded, form a 5- or 6-membered heterocycle which may further contain a heteroatom. , R^2 and R^3 are each independently a hydrogen atom, an alkyl group having 5 or less carbon atoms, or an acyl group having 5 or less carbon atoms, and R^4 is a hydrogen atom, a halogen atom, a hydroxyl group, or a hydroxyl group having 5 or less carbon atoms. is an alkyl group or an alkoxy group having 5 or less carbon atoms. ] An anti-plant disease composition containing phenylglycines represented by the following as an active ingredient. 2. The following general formula (I)-a, (I)-b or (I
)-c ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・・・・
(I)-a ▲There are mathematical formulas, chemical formulas, tables, etc.▼・・・・・・(I
)-b ▲There are mathematical formulas, chemical formulas, tables, etc.▼...(I)-c [However, in each of the above formulas, R^1 is -OR^1^1 or ▲There are mathematical formulas, chemical formulas, tables, etc.▼ Yes, R^1
^1 is a hydrogen atom or an alkyl group having 5 or less carbon atoms, and R^1^2 and R^1^3 are each independently a hydrogen atom or an alkyl group having 5 or less carbon atoms, or R^1 ^2 and R^1^3 may be bonded to each other and together with the nitrogen atom to which they are bonded, form a 5- or 6-membered heterocycle which may further contain a heteroatom. , R^2 and R^3 are each independently a hydrogen atom, an alkyl group having 5 or less carbon atoms, or an acyl group having 5 or less carbon atoms, and R^4 is a hydrogen atom, a halogen atom, a hydroxyl group, or a hydroxyl group having 5 or less carbon atoms. is an alkyl group or an alkoxy group having 5 or less carbon atoms. ] An anti-plant disease method characterized by applying an effective amount of phenylglycine represented by the following to a plant or the environment in which it grows, at the time of occurrence of disease damage to the plant or before it is predicted.