JPH03261703A - Phytotoxicity-mitigative agent for crop - Google Patents

Abstract

PURPOSE:To provide the title agent having, for example, selective phytotoxicity- mitigating effects on paddy-rice plants without impairing its herbicidal effects when formulated in a herbicide with high phytotoxicity, containing, as active ingredient, a specific benzylamino-S-triazine derivative. CONSTITUTION:The objective agent containing, as active ingredient, a compound of the formula (R1 and R2 are each H, lower alkyl or lower alkenyl; R3 is lower alkyl, lower alkoxy or halogen; n is 0, 1 or 2; X is halogen; R4 and R5 are each H, alkyl, lower alkenyl, cycloalkyl, etc.). It is preferable that, in the case of granules, 0.1-5wt.% of the present agent be formulated based on sulfonylurea-based herbicides, and 0.1-10wt.% based on the other herbicides; and, for hydrated, emulsified or flowable agent, 1-75wt.% based on any herbicide. The amount of the present agent to be suitably applied is such as to be 5-50g, per 10 a, of the compound of the formula in the case of sulfonylurea-based herbicides, and 5-100g, for the other herbicides.

Description

DETAILED DESCRIPTION OF THE INVENTION Technical Field of the Invention The present invention relates to a phytotoxic agent for crops containing a benzylamino=S-)riazine derivative as an active ingredient,
This phytotoxicity reducer is useful in agriculture, especially in the field of pesticide manufacturing.

Technical Background of the Invention Some benzylamino-8-triazine derivatives are known compounds and are known to have herbicidal activity. As an example, ^grIBio1. Che
Ill, Vol. 51, p. 256 (1987), No. 5
Volume 2, page 1047 (1988), Volume 52, Volume 1
Page 515 (1988), Volume 53, Page 2723 (
1989), JP-A-49-8261, JP-A-4
Publication No. 9-8262, G Gardner ind J
, R, 5anborn X, 11aiurlo+scb
,.

42c, 663 (19B?), etc. However, it has not been reported to date that benzylamino-S-) lyazine derivatives have the effect of reducing the phytotoxicity of useful crops caused by herbicide spraying.

OBJECT OF THE INVENTION Many of the known benzylamino-5-triazine derivatives exhibit excellent herbicidal activity. However, many of those with strong herbicidal activity cause damage to crops such as paddy rice. Therefore, an object of the present invention is to provide a phytotoxic agent for crops containing a novel benzylamino-3-triazine derivative as an active ingredient.

Summary of the Invention In order to achieve the above object, the present inventors have developed a number of S-
We synthesized triazine derivatives and extensively investigated their physiological activities. As a result, when a specific benzylamino-3-) lyazine derivative represented by the following general formula is added to a herbicide that causes strong phytotoxicity to crops, the benzylamino-s-h lyazine can reduce the phytotoxicity. It was found that the effect was shown to be effective. Therefore, the drug harm reducer for the action according to the present invention has the following general formula (1) [wherein R1 and R2 may be the same or different and represent a hydrogen atom, a lower alkyl group, or a lower alkenyl group, R3 may be the same or different and represent a lower alkyl group, a lower alkoxy group or a halogen atom,
n represents 0.1 or 2, X represents a halogen atom,
R4 and R5 may be the same or different and are a hydrogen atom, an alkyl group, a lower alkenyl group, a cycloalkyl group,
Lower alkoxycarbonyl represents a lower alkyl group (however, R and R5 are never hydrogen atoms at the same time). ] It is characterized by containing a benzylamino-3-) lyazine derivative represented by these as an active ingredient.

DETAILED DESCRIPTION OF THE INVENTION The phytotoxicity reducing agent for crops according to the present invention will be specifically described below.

The drug harm reducer according to the present invention contains a benzylamino-s-triazine derivative represented by the general formula CI) as an active ingredient. Specific examples of this benzylamino-s-h riazine derivative are shown in Table 1. show. However, the present invention
The general formula (I
) are useful.

1. Table 1 A also lists the above compound fish 1-2 and 491-1.
Specific light intensity αD of 08 (chloroform measurement (C=1.0
1) is shown.

Reaction Formula Next, the method for producing the benzylamino-s-triazine derivative of the general formula (1) will be explained. The compound of the general formula (1) can be produced, for example, according to the following reaction formula.

R1 As mentioned above, the compound represented by the general formula (I) can be prepared by reacting, for example, cyanuric chloride with a benzylamine derivative in the presence of a suitable deoxidizing agent such as caustic alkali.
, 4-dichloro-6-(benzylamino)-5-triazine, and further reacting this with lower alkylamine, lower alkenylamine, cycloalkylamine, etc.

Next, benzylamino-5- of general formula (1) according to the present invention
A production example of a triazine derivative will be specifically shown.

Production Example 1 Production method 1 of (compound Na9) 36.9 g (0.2 mol) of cyanuric chloride was added to 110 g of cyanuric chloride.
g of acetone and poured into 120 g of ice water to precipitate fine cyanuric chloride.

To this was added 27.0 g of α,α-dimethylbenzylamine (
0.2 mol) and then 17 g (0.2 mol) of sodium hydrogen carbonate dissolved in 25-1 water at 0 to 5°C.
Add dropwise while stirring. After the dropwise addition was completed, the mixture was further stirred at the same temperature for 1 hour, and then secondary-butylamine was added.14.
6 g (0.2 mol) was added dropwise, and 17 g (0.2 mol) of sodium bicarbonate dissolved in 2511 water was added dropwise to 0-5
Add dropwise while stirring at °C. After the addition is complete, the mixture is gradually warmed to 50° C. over 1 hour. After completion, the reaction mixture was cooled to room temperature, and the solid part was filtered, washed with water, and dried.
g (yield 95%).

When reconsolidated from ethanol, this compound Garden, p.

is 156.5-157.0°C.

Production Example 2 Production method 1 of (compound Na1) CH6 Cyanuric chloride 36.9g (0.2 mol) was dissolved in (PH
-2) 2.4-Dichlorophenoxyacetic acid or its salt, ester or amide derivative (PH-3) 2-Methyl-4-chlorophenoxybutyric acid or its salt, ester or amide derivative (PI(-4) S-ethyl- 4-Chloro-〇-trisyloxythioacetate Organophosphorus herbicide Herbicide blood Chemical name (P-1)
0-ethyl-〇-6-nitrometadryl secondary butyl phosphoramidothioate (P-2) 5-2-methylpiperidinocarbonylmethyl-0,0-dipropylphosphorodithioate (P-3) 5-2-Benzenesulfonamide ethyl 0, O-diisopropyl phosphorodithioate and other herbicides Herbicide chemical name (M-1)
2-amino-3-chloro-1,4-naphthoquinone (M-2) 3.7-dichloro-8-carboxy-quinoline (M-3) S S-dimethyl-2-(difluoromethyl)4-(2- Exo-1-methyl-4-(1-methylethyl)2-((2-methylphenyl) methoxy]7
-Oxabicyclo[2,2,11hebutane When formulating the herbicide by mixing the herbicide with the herbicide according to the present invention, the additives used when formulating the herbicide can be used. .

Next, an example of formulation of a herbicide containing the phytotoxicity reducer of the present invention will be shown.

Example 1 Sulfonylurea herbicide (hydrating powder) 50 parts of compound NcL1, 15 parts of herbicide &S-, 5 parts of polyoxyethylene alkylaryl ether, 3 parts of calcium lignin sulfonate, and 37 parts of diatom were mixed and thoroughly ground. A wettable powder containing 5% of the active ingredient is obtained.

Example 2 Sulfonylurea herbicide (granules) Compound NCL50 3 parts, herbicide size 5-20.1 parts, lauryl sulfate 1 part, calcium lignosulfonate 1 part, bentonite 30 parts and white clay 64.9 parts
After adding 15 parts of water to the mixture and kneading it with a kneader, it is granulated with a granulator and dried with a fluidized fluidized dryer to obtain granules containing 0.1% of the active ingredient.

Example 3 Sulfonylurea herbicide (granules) Compound Arashi 642 parts, herbicide! Add 15 parts of water to 1hs-30.2 parts, 1 part of lauryl sulfate, 1 part of calcium lignylsulfonate, 30 parts of bentonite, and 65.8 parts of clay, knead with a kneader, and then granulate with a granulator. , and dried in a fluidized fluid dryer to obtain granules containing 0.2% of the active ingredient.

Example 4 Amide herbicide (granules) 912 parts of Compound Magnolia, 12.5 parts of herbicide NCLA-1, 1 part of lauryl sulfate, 1 part of calcium lignosulfonate, 30 parts of bentonite, and 63.5 parts of white clay, and 15 parts of water. In addition, the mixture is kneaded in a mixer, granulated in a granulator, and dried in a fluidized fluid dryer to obtain granules containing 2.5% of the active ingredient.

Effects of the Invention When the benzylamino-S-triazine derivative of the general formula (I) of the present invention is used in combination with a herbicide that exhibits strong phytotoxicity, it can be used on rice, for example, without impairing the herbicide's inherent herbicidal effect. It can selectively bring about the effect of reducing drug damage.

Next, the usefulness of the benzylamino-S-triazine derivative of general formula (I) of the present invention will be shown by test examples.

Test Example 1 Test on the effect of reducing chemical damage to paddy rice (chemical treatment 5 days after transplanting paddy rice) Paddy soil was filled into a Wagnerbot with a size of 1/10.000 are, and chemical fertilizer (N: P: K = 17)
:17 :17) was added, water was added, and after raking, paddy rice seedlings (variety: Nipponbare) in the second leaf stage were transplanted.

The subsequent management was carried out in a glass room at 17°C to 28°C, and 5 days after transplanting the paddy rice, a wettable powder prepared according to Example 1 was diluted with water to a predetermined dose and dropped. Twenty-eight days after the chemical treatment, the dry weights of the stems, leaves, and roots of the paddy rice were measured, and the ratio to that of the untreated plot was determined.

This test was conducted three times per drug concentration group.

The results are shown in Table 2.

Table 2-2 Table 2-1 Table 2-3 Table 2-4 Table 2-6 Table 2-5 Table 2 Table 2-8 Table 2-10 note) ( The numbers in parentheses indicate the dry amount (g/plant) of the untreated plot.

Table 2-9 Also, Herbicides in Table 2 (5-1 ) cause drug damage Tested in the same manner as Test Example 1 instead of other herbicides. death The results are shown in Table 3.

Table 3-1 Table 3-3 Table 3-2 Table 3-4 Table 3-5 Table 3-7 Table 3-6 Table 3-8 note) ( The numbers in parentheses indicate the dry amount (g/plant) of the untreated plot.

Claims (1)

[Claims] General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, R_1 and R_2 may be the same or different and represent a hydrogen atom, a lower alkyl group, or a lower alkenyl group, and R_3 is may be the same or different, and represent a lower alkyl group, a lower alkoxy group, or a halogen atom, n represents 0.1 or 2, x represents a halogen atom, R_4 and R_5 may be the same or different, Indicates a hydrogen atom, an alkyl group, a lower alkenyl group, a cycloalkyl group, a lower alkoxycarbonyl lower alkyl group (however, R_4 and R_5 are never hydrogen atoms at the same time). ] A phytotoxicity reducing agent for crops, characterized by containing a benzylamino-S-triazine derivative represented by the following as an active ingredient.