JPS6317813A - Herbicide composition - Google Patents

Abstract

PURPOSE:A herbicide composition that contains, as active ingredients, a combination of a 4-substituted-pyridine-3-carboxamide derivative with a known compound with herbicidal activity, thus enabling perfect control against all kinds of weeds by only one application with extremely reduced chemical injury and low toxicity to man and animals. CONSTITUTION:The objective composition contains, as active ingredients, a combination of a compound of the formula (R1 is alkyl, alkenyl, alkinyl, aralkyl, aryl; R2, R3 are alkyl, cycloalkyl aralkyl; n is 0, 1; R4 is H, in case of n=0, or H, halogen, alkyl in case of n=1; A is H, halogen CN, NO2, NH2, alkyl; Z is N, N 0) with another compound selected from 8 compounds including i) 2-chloro-4,6-bis(ethylamino)-1,3,5-triazine, ii) 2-chloro-2',6'-diethyl-N- methoxymethylacetanilide, iii) 3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea and others, at a weight ratio of 1:(0.2-5).

Description

Detailed Description of the Invention (Industrial Application Field) The present invention provides 4-substituted-3-pyridinecarboxamide derivatives, or 4-substituted-3-pyridinecarboxamide 1
- A herbicidal composition characterized by containing as active ingredients at least one kind of oxide derivatives and addition salts thereof and a known compound having herbicidal activity (described in detail below). .

(Prior Art) Until now, there have been no reports of any compounds belonging to the 4-substituted-3-pyridinecarboxamides having herbicidal activity, and furthermore, there have been no reports regarding the herbicidal composition shown in the present invention. This is a new combination that has not been described yet, and of course there is no literature mentioning its unique herbicidal effect.

(Problems to be solved by the invention) Currently, many types of herbicides are used in agriculture.
Widely and commonly used. In addition, corn is an important crop that is cultivated worldwide for large areas and is widely cultivated for food and feed. Many corn herbicides have also been developed as labor-saving alternatives to manual weeding. However, weeds in agricultural land are extremely diverse and of many types, and it can be said that there is no single herbicide that satisfies the conditions of having a wide herbicidal spectrum and being completely free from chemical damage.

The present invention was developed in view of these problems with conventional herbicides, and continues the search for a herbicide that can be used for rotation to completely exterminate all plant species, has extremely minimal phytotoxicity, and has low toxicity to humans and animals. As a result, it was discovered that the above-mentioned problems could be improved by blending and using together two types of herbicides each having a different herbicidal action as described in the present invention, and the present invention was completed.

(Means for Solving the Problems) The present invention comprises at least one compound represented by the following formula (I) and an addition salt thereof, and the following known compound B.
The present invention relates to a herbicidal composition containing as an active ingredient at least one compound selected from compounds B-1 to B-8.

[In the formula, R1 is an alkyl group, a lower alkenyl group, a lower alkynyl group, a halogenated lower alkyl group, a lower alkoxy lower alkyl group, a lower alkylthio lower alkyl group,
A lower alkoxycarbonyl lower alkyl group, a cycloalkyl group, an optionally substituted aralkyl group, an optionally substituted aryl group, or a 5- or 6-membered heterocyclic group, R2
and R3 are the same or different and represent a lower alkyl group, a halogenated lower alkyl group, a lower alkoxy lower alkyl group, a cycloalkyl group, an optionally substituted aralkyl group, or an optionally substituted aryl group, and n is 0 or means an integer of 1, and when n = o, 〇 means a hydrogen atom, and when n = 1, 〇 means a hydrogen atom, a halogen atom, a lower alkyl group, an optionally substituted aralkyl group, or an optionally substituted aralkyl group. The aryl group or R3 and - together represent -(CH2)m-(m
represents 3 or 4), A represents a hydrogen atom, or one or more substituents on the benzene ring, and in the case of two or more, the same or different, a halogen atom, a cyano group, a nitro group , an amino group, a lower alkyl group, a halogenated lower alkyl group, a hydroxy group, a lower alkoxy group, an aryloxy group, a carboxyl group, or a lower alkoxycarbonyl group, and Z means N or N-0, respectively.

B-12-Chloro-4-ethylamino-6-itupropylamino-1,3.5-) riazine B-22-(1-cyano-1-methylethylamine)-4-ethylamino-
6-chloro-1,3゜5-triazine B-32-chloro-4,6-bis(ethylamino)-1
゜3.5-) Riazine B-42-chloro-2',6'-diethyl-N-methoxymethylacetanilide B-52-ethyl-6-methyl-N-(3-methoxy-
2-propyl)-chloroacetanilide B-6N-taloloacetyl-N-(2,6-dinitylphenyl)glycinate ethyl B-73-(3,4-dichlorophenyl)-1,1-dimethylurea B-83-(3, 4-dichlorophenyl)-1-methoxy-1-methylurea Among the active ingredients of the herbicide composition of the present invention, compound B-1
Compound B-8 is a substance known as a herbicide for field use. To explain in more detail, Compound B-1, Compound B-2, and Compound B-3 are herbicides belonging to the so-called S-triazine family, and are highly effective against broad-leaved weeds, including corn. It is known that all compounds are highly safe against many gramineous crops, but all of them have the disadvantage of being less effective against weeds of the grass family, such as field weeds and foxtail grass. Compound B-4, Compound B-5, and Compound B-6 are herbicides belonging to the so-called chloracetamide family, and are highly effective against weeds of the grass family, including grasshopper, and are effective against grasses such as corn and soybeans. It is known to be highly safe for major crops. However, both compounds have the disadvantage that they are less effective against broad-leaved weeds. Also, compound B
-7 and Compound B-8 are herbicides belonging to the so-called urea family, and are highly effective against broad-leaved weeds and highly safe against major crops such as corn and cotton.
Are known. However, it has the disadvantage that it is less effective against -year-old grass weeds. .

On the other hand, among the active ingredients of the herbicide composition of the present invention, formula (I
) (hereinafter referred to as compound A) is -
It is highly effective against annual grass weeds and broad-leaved weeds, and has the characteristics of low toxicity and long residual effect on many broad-leaved crops, including corn and other grass crops.

The present inventors have found that by mixing Compound A and Compounds B-1 to B-8, each of which has the above-mentioned drawbacks, in an appropriate ratio, they can compensate for the drawbacks of using each alone, and have extremely significant Due to the synergistic effect, the herbicidal spectrum and the range of suitable periods for use have been greatly expanded.As a result, the herbicidal spectrum and suitable period of use have been greatly expanded. They discovered that spraying has excellent weeding effects over the entire corn growing period, and that there is no chemical damage to the corn.

That is, when compound A is used in combination with compound B-1, compound B-2, compound B-3, and B-7 and B-8, it is effective against grass weeds that are less effective when used alone. Expresses a synergistic herbicidal effect, and Compound A and Compound B-
4. When used in combination with Compound B-5 or Compound B-6, a synergistic herbicidal effect can be exerted on broad-leaved weeds such as Portulaca sinensis and Whiteweed, thereby expanding the herbicidal spectrum. In addition, in either combination, safety for corn is not compromised and no problematic phytotoxicity occurs.

Among the active ingredients of the herbicide composition of the present invention, formula (, I)
The compound represented by is a new substance and can be produced, for example, by the method shown in the following production example.

Production Example (Method A) This method can be advantageously used when n in formula (I) is 1. That is, the compound of formula (II) is reacted with ammonia (III) in a suitable solvent (e.g. ethanol, water, etc.) at a temperature of room temperature to 60°C (reaction formula (a)).
Alternatively, the compound of formula (IV) is obtained by reacting the compound of formula (V) with a halogenating agent (reaction formula (b)). next,
A compound of formula (IV) and a halide (VI) are combined in a suitable solvent (e.g., N,N-dimethylformamide, dimethyl sulfoxide, etc.) in the presence of a base (e.g., potassium carbonate, sodium hydroxide, etc.), Preferably, by reacting under heating (reaction formula (c)), formula (I)
The compound is obtained.

In addition, the 1-oxide compound (I'') in which 2 in formula (I) is N-0 can be produced by the method shown in reaction formula (d) (however, in this case, the formula (') and the formula (n in I' is 1.) That is, a 4-substituted oxy-3-pyridine carboxamide derivative (I') in a suitable solvent,
hydrogen peroxide, hydroperoxides such as tert-butyl hydroperoxide, or peracetic acid, perbenzoic acid, m
- by treatment with an oxidizing agent such as an organic peracid such as chloroperbenzoic acid.

(II) In addition, each symbol in each formula above represents the formula (I) unless otherwise specified.
It has the same meaning as the symbol inside.

(Method B) This method can be advantageously used when n in formula (I) is O. That is, the compound of formula (■) is oxidized by a known method,
For example, by heating in the presence of an oxidizing agent such as nitrous acid, chromic acid, iodine or sulfur, or a dehydrogenation catalyst such as palladium, a compound of formula (■) is obtained (reaction formula (e)), which is hydrolyzed. The compound of formula (IX) is obtained by thermal decomposition or reductive decomposition (reaction formula (v)). Sara (however, in this case, the formula (
R4 in IV) is a halogen atom. ) N respectively. ) By thermally decomposing the compound of formula (IX) at a temperature higher than its melting point (reaction formula (g)), formula (I) is obtained.
can be obtained.

The above order of oxidation - decomposition - thermal decomposition can be changed to the order of decomposition - thermal decomposition monoxidation as shown in reaction formula (H) or the order of decomposition - oxidation - thermal decomposition as shown in reaction formula (su). Compounds of formula (I) can also be obtained.

In addition, the 1-oxide compound (P') in which 2 in formula (I) is N-0 can be similarly produced by the method shown in the above-mentioned reaction formula (d) (however, in this case, the formula ( n in formula (I'') is 0).

(However, n means O and Z means N.) Of the above formulas, R5 in formula (■) and formula (■) is a group that is It is an ester residue that can be removed without affecting the
-butyl group, tetrahydropyranyl group, benzyl group, p
-Means a methoxybenzyl group or a benzhydryl group. Note that other symbols have the same meanings as those in formula (I) unless otherwise specified.

Examples of Compound A obtained by the above method are shown in Tables 1 and 2.
(Hereinafter, specific examples of compound A are indicated by compound numbers in Tables 1 and 2.)

The unique herbicidal effect related to the present invention is observed in a fairly wide range of mixing ratios, but the weight ratio of Compound A and Compounds B-1 to B-8 is 1:0.1 to 10 (more preferably 1:1). It is preferable to mix it so that it becomes 0.2-5). The herbicide composition of the present invention comprises compound A and compound B.
Although the active ingredient compounds of Compounds -1 to Compound B-8 may be used as they are, they are generally mixed with solid carriers, liquid carriers, surfactants, and other formulation auxiliaries, such as water use agents, hydration agents, etc. Formulated into.

These preparations contain the herbicidal composition of the present invention in an amount of 10 to 80% as a total of the active ingredients of Compound A and Compounds B-1 to B-8, and 10 to 5% as an emulsion.
It is preferable that the content is 0% (all percentages are by weight).

Solid carriers used in formulations include fine powders or granules such as kaolin, bentonite, clays, talc, diatomaceous earth, gicrite, zeolite, pyrophyllite, synthetic silicon oxides, and calcium carbonate, and liquid carriers. for,
Aromatic hydrocarbons such as xylene and methylnaphthalene, alcohols such as ethanol, isopropanol, ethylene glycol, and methyl cellosolve, ketones such as acetone, isophorone, and cyclohexanone, vegetable oils such as soybean oil and cottonseed oil, dimethylformamide, dimethyl Examples include sulfoxide, acetonitrile, water, etc.

Surfactants used for dispersion, emulsification, etc. include polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene polyoxy Examples include nonionic surfactants such as propylene block polymers, anionic surfactants such as alkyl sulfate salts, alkyl sulfonate salts, alkylaryl sulfonate salts, and polyoxyethylene alkyl sulfate salts.

Formulation auxiliaries include lignin sulfonate, alginate, polyacrylates, polyvinyla/L, cole,
Plant? 1 page of gum, carboxymethyl cellulose (HEC), etc. (Example) Next, formulation examples are shown, but the present invention is not limited to these. 4 In addition, parts indicate tff and parts.

Formulation Example 1 Wettable powder Compound No. A-15 20 parts, compound No. B-7
20 parts, talc 40 parts, bentonite 15 parts, Tsurupol-9047 (manufactured by Toho Chemical) 2 parts, Tsurupol 5039
(Same as above) Three parts were thoroughly ground and mixed to obtain a wettable powder.

Formulation Example 21 Agent Compound No. A-14 15 parts, compound No. B-6
15 parts, xylene 20 parts, dimethylformamide 42 parts
1 part and 8 parts of polyoxyethylene alkyl phenyl ether are thoroughly mixed to obtain an emulsion.

The wettable powders prepared as described above are usually diluted with water, and the granules are used as they are by spraying on the soil or on foliage and on the soil.

Furthermore, the herbicidal composition of the present invention may be used in combination with other insecticides, acaricides, nematicides, fungicides, herbicides, plant growth regulators, fertilizers, or soil conditioners as necessary. can.

Next, the usefulness of the herbicide composition of the present invention will be shown in Examples.

Example: Herbicidal effect and phytotoxicity test 3 A plastic case measuring 26 cm x 26 cm and 3 cm deep was filled with field soil, and weed seeds (wildweed, foxtail grass, crabgrass, purslane, white grass) and crop seeds (corn) were sown to a depth of 1 to 2 cm. The plants were covered with soil and grown for 14 days.

Thereafter, the herbicide composition of the present invention made into an emulsion according to Formulation Example 2 is diluted with a predetermined amount of water, and sprayed uniformly over the entire foliage from above the plant body using a small sprayer to achieve a predetermined dose. did.

Fifteen days after the chemical treatment, the herbicidal effect and phytotoxicity were evaluated according to the following criteria, and the results are shown in Tables 3 and 4.

Claims (1)

[Claims] Formula (I): ▲ Numerical formula, chemical formula, table, etc. ▼ [In the formula, R_1 is an alkyl group, a lower alkenyl group, a lower alkynyl group, a halogenated lower alkyl group, a lower alkoxy lower alkyl group, A lower alkylthio lower alkyl group, a lower alkoxycarbonyl lower alkyl group, a cycloalkyl group, an optionally substituted aralkyl group, an optionally substituted aryl group, or a 5- or 6-membered heterocyclic group, R
_2 and R_3 are the same or different and represent a lower alkyl group, a halogenated lower alkyl group, a lower alkoxy lower alkyl group, a cycloalkyl group, an optionally substituted aralkyl group, or an optionally substituted aryl group, and n is 0 or means an integer of 1, if n=0, R_4 is a hydrogen atom, n=
In the case of 1, R_4 is a hydrogen atom, a halogen atom, a lower alkyl group, an optionally substituted aralkyl group, or an optionally substituted aryl group, or R_3 and R_4 together are -(CH_2)m- (m is 3 or 4), A represents a hydrogen atom, or one or more substituents on the benzene ring, and if two or more are the same or different, they are a halogen atom, a cyano group, a nitro group, an amino group , a lower alkyl group, a halogenated lower alkyl group, a hydroxy group, a lower alkoxy group, an aryloxy group, a carboxy group or a lower alkoxycarbonyl group, and Z means N or N-O, respectively. ] 4-substituted-3-pyridinecarboxamide derivatives, or 4-substituted-3-pyridinecarboxamide 1-oxide derivatives, and at least one kind of addition salt thereof, and from the following known compounds B__1 to B__8 A herbicidal composition comprising at least one selected compound as an active ingredient. B__1 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazineB__2 2-(1-cyano-1-methylethylamino)-4-ethylamino-6-chloro-1,3, 5-triazine B__3 2-chloro-4,6-bis(ethylamino)
-1,3,5-triazine B__4 2-chloro-2',6'-diethyl-N-methoxymethylacetanilide B__5 2-ethyl-6-methyl-N-(3-methoxy-2-propyl)-chloroacetanilide B__6 N-chloroacetyl-N-(2,6-diethylphenyl)glycinate ethyl B__7 3-(3,4-dichlorophenyl)-1,1
-Dimethylurea B__8 3-(3,4-dichlorophenyl)-1-methoxy-1-methylurea