BRPI0708814B1 - COMPOSITION OF PYRIDAZINONE, ITS USE IN THE CONTROL OF WEEDS, HERBICIDE UNDERSTANDING THE SAME AND METHOD OF CONTROL OF WEEDS - Google Patents

Description

Report of the Invention Patent for "PYRIDAZINONE COMPOUND, ITS USE IN WEED CONTROL, HERBICIDE UNDERSTANDING THE SAME AND WEED HERB CONTROL METHOD".

Technical Field The present invention relates to pyridazinone compounds and herbicides comprising them. Background Art A certain type of pyridazinone compound is known from J. Heterocycl. Chem., Vol. 42, pp. 427-435 (2005).

However, said pyridazinone compound does not have a sufficient weed control effect. The object of the present invention is to provide a compost with an excellent effect on weed control.

Description of the Invention After extensive investigations, the present inventors have found that the pyridazinone compounds represented by formula (I) have excellent effect on weed control, completing the present invention. The present invention is as follows. (1) A pyridazinone compound represented by formula (I) (hereinafter referred to as the present compound), wherein, in the formula, R 1 represents a C 1-6 alkyl group or a (C 1-6 alkyloxy) C 1-6 alkyl group, R 2 represents a hydrogen atom or a C 1-6 alkyl group, G represents a hydrogen atom, a group represented by the formula, a group represented by the formula, or a group represented by the formula (wherein, in the formula, L represents a oxygen or sulfur atom, R3 represents a C1-6 alkyl group, a C3.8 cycloalkyl group, a C2.6 alkenyl group, a C2.8 alkynyl group, a C6-10 aryl group, a group (Ce-10 aryl) C1-6 alkyl, a C1-6 alkyloxy group, a C3.8 cycloalkyloxy group, a C2.6 alkenyloxy group, a C2.6 alkynyloxy group, a C10-10 aryloxy group, a (C6-10 aryl) group C1-6 alkyloxy, an amino group, a C1-6 alkylamino group, a C2-6 alkenylamino group, a C6-10 arylamino group, di (C1-6 alkyl) amino group, di (C2-6 alkenyl) group am C 1-6 alkyl) (C 6-10 aryl) amino group or a three to eight-membered nitrogen-containing heterocyclic ring group, R 4 represents a C 1-6 alkyl group, a C 6-10 aryl group, a C 1-6 alkyl group. Alkylamino or di (C1-6 alkyl) amino group; and R 5 and R 6 may be the same or different and represent a C 1-6 alkyl group, a C 3-8 cycloalkyl group, a C 2-6 alkenyl group, a C 6-10 aryl group, a C 1-6 alkyloxy group, a C 3 group. Cycloalkyloxy, a C10-10 aryloxy group, a (C6-10 aryl) C1-6 alkyloxy group, a C1-6 alkylthio group, C1-6 alkylamino group or di (C1-6 alkyl) amino group, herein any group represented by R3, R4, R5 and R6 may be substituted by at least one halogen atom and a C3.8 cycloalkyl group, a Ce-10 aryl group, an aryl portion of a (C6-10 aryl) C1-6 alkyl group , a C 3-8 cycloalkyloxy group, a C 6-10 aryloxy group, an aryl portion of a (C 6-10 aryl) C 1-6 alkyloxy group, an aryl portion of a C 6-10 arylamino group, an aryl portion of a ( C 1-6 alkyl) (C 6-10 aryl) amino, and a three to eight-membered nitrogen-containing heterocyclic ring group may be substituted with at least one C 1-6 alkyl group), Z 1 represents a C 1-6 alkyl group, Z 2 represents a G C 1-6 alkyl group, n represents 0, 1,2, 3 or 4, and each Z 2 may be the same or different when n represents an integer of 2 or more, and the sum of the number of carbon atoms in the group represented by Z 1 ee in the group represented by Z2 is 2 or more. (2) The pyridazinone compound according to (1), wherein n is an integer equal to 1 or more. (3) The pyridazinone compound according to (1), wherein n is 0, and Z 1 is a C 2-6 alkyl group. (4) The pyridazinone compound according to (1), wherein n is 1 or 2, and Z 2 is (are) (one) substituent (s) at the 4 and / or 6 position of a benzene ring. (5) The pyridazinone compound according to (1), (2) or (4), wherein Z1 is a C1.3 alkyl group, and Z2 is a C1.3 alkyl group. (6) The pyridazinone compound according to any one of (1) to (5), wherein G represents a hydrogen atom, a group represented by the formula, a group represented by the formula, or a group represented by the formula, in which in the formula R3b represents a C1-6 alkyl group, a C3-6 cycloalkyl group, a C2.6 alkenyl group, a C2.6 alkynyl group, a C6-10 aryl group, a (C10-10 aryl) group C 1-6 alkyl, C 1-6 alkyloxy group, C 3-8 cycloalkyloxy group, C 6-10 aryloxy group, (C 6-10 aryl) C 1-6 alkyloxy group, C 1-6 alkylamino group, C6-10 arylamino or di (C1-6 alkyl) amino group, R4b represents a C1-6 alkyl group or a C6-10 aryl group, and R5b and R6b may be the same or different and represent a C1-6 alkyl group, a C1-6 alkyloxy group, a C6-10 aryloxy group or a C1.6 alkylthio group, here any group represented by R3b, R4b, R5b and R6b may be substituted with at least one halogen atom and a C3.8 cycloalkyl group, one C6-10 aryl group, an aryl moiety of a (C6-10 aryl) C1-6 alkyl group, a C3.8 cycloalkyloxy group, a C10-10 aryloxy group, an aryl portion of a (Ce-aryl) C1 group C 1-6 alkyloxy, and an aryl moiety of a C 6-10 arylamino group may be substituted with at least one C 1-6 alkyl group. (7) The pyridazinone compound according to any one of (1) to (5), wherein G represents a hydrogen atom, a group represented by the formula, or a group represented by the formula, wherein in the formula R 33 represents a C 1-6 alkyl group, a C 3-8 cycloalkyl group, a C 6-10 aryl group, a C 1-6 alkyloxy group or di (C 1-6 alkyl) amino group, and R 4a represents a C 1-6 alkyl group herein any group represented by R 3a and R 4a may be substituted with at least one halogen atom and a C 3-8 cycloalkyl group, and a C 6-10 aryl group may be substituted with at least one C 1-6 alkyl group. (8) The pyridazinone compound according to any one of (1) to (7), wherein R 2 is a hydrogen atom or a C 1-3 alkyl group. (9) The pyridazinone compound according to any one of (1) to (7), wherein R2 is a hydrogen atom or a methyl group. (10) The pyridazinone compound according to any one of (1) to (9), wherein R1 is a C1-3 alkyl group or a (C1-3 alkyloxy) C1-3 alkyl group. (11) A herbicide comprising the pyridazinone compound according to any one of (1) to (10) as an active ingredient. (12) A weed control method, comprising a step wherein an effective amount of the pyridazinone compound according to any one of (1) to (10) is applied to weeds or to the soil where weeds grow. (13) Use of the pyridazinone compound according to any one of (1) to (10) for weed control. (14) A compound represented by formula (II): wherein, in the formula, R 7 represents a C 1-6 alkyl group, R 1, R 2, Z 1, Z 2 and n have the same meaning as defined in (1). (15) A compound represented by formula (VI): wherein, in the formula, R 9 represents a C 1 -C 6 alkyl group, R 1, R 2, Z 1, Z 2 and n have the same meaning as defined in (1).

In substituents represented by R1, R2, R3, R4, R5, R6, Z1 and Z2 in the formula (I) of the present invention, a C1-6 alkyl group denotes an alkyl group having the number of carbon atoms from 1 to 6 and includes, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a sec-pentyl group an isopentyl group, a neopentyl group, a hexy-a group, an isoexyl group etc., a C 3-8 cycloalkyl group designates a cycloalkyl group having the number of carbon atoms from 3 to 8 and includes, for example, a group Cyclopropyl, a cyclopentyl group, a cyclohexyl group etc., a C 2-6 alkenyl group designates an alkenyl group of 0 to 6 carbon atoms and includes, for example, an allyl group, a 1-buten group -3-yl, a 3-buten-1-yl group etc., a C 2-6 alkynyl group designates an alkynyl group of 0 to 2 carbon atoms and includes, for example, a In a propargyl group, 2-butynyl group etc., a C6-10 aryl group denotes an aryl group having the number of carbon atoms from 6 to 10 and includes, for example, a phenyl group, a naphthyl group etc., a group (C6-10 aryl) alkyl means a C1-6 alkyl group substituted with a C6-10 aryl group and includes, for example, a benzyl group, a phenethyl group etc., a C1-6 alkyloxy group designates an alkyloxy group having the number of carbon atoms from 1 to 6 and includes, for example, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group etc., a C3.8 cycloalkyloxy group denotes a cycloalkyloxy group having the number of carbon atoms from 3 to 8 and includes, for example, a cyclopropyloxy group, a cyclopentyloxy group etc., a C 2-6 alkenyloxy group designates an alkenyloxy group of carbon atoms from 2 to 6 and includes, for example, a vinyloxy group , an allyloxy group etc., a C2-6 alkynyloxy group designates an alkynyloxy group of 0 carbon atoms from 2 to 6 and includes, for example, a propyloxy group, 2-butynyloxy group etc., a C10-10 aryloxy group denotes an aryloxy group having the number of carbon atoms from 6 to 10 and includes, for example a phenoxy group, a naphthoxy group etc., a (C6-10 aryl) C1-6 alkyloxy group designates a C1-6 alkyloxy group substituted with a C6-10 aryl group and includes, for example, a benzyloxy group, a phenethyloxy group etc., a C 1-6 alkylamino group designates an alkylamino group having a number of carbon atoms from 1 to 6 and includes, for example, a methylamino group, an ethylamino group etc., a C 2-6 alkenylamino group designates an alkenylamino group having the number of carbon atoms from 2 to 6 and includes, for example, an allylamino group, a 3-butenylamino group etc., a C10-10 arylamino group means an arylamino group having the carbon number of 6 to 10 and includes, for example, a phenylamino group, a naphthylamino group etc., the di (C1-6 alkyl) amino group denotes an amino group su It is composed of two same or different C1-6 alkyl groups and includes, for example, a dimethylamino group, a diethylamino group, an N-ethyl-N-methylamino group etc., the di (C2-6 alkenyl) amino group designates a amino substituted with two same or different C 2-6 alkenyl groups and includes, for example, a diallylamino group, a di (3-butenyl) amino group etc., a (C 1-6 alkyl) (C 6-10 aryl) amino group means an amino group substituted with a C1-6 alkyl group and a C6-10 aryl group and includes, for example, a methylphenylamino group, an ethylphenylamino group etc., a C1-6 alkylthio group designates an alkylthio group having the number of carbon atoms from 1 to 6 and includes, for example, a methylthio group, an ethylthio group, a propylthio group, an isopropylthio group etc., a (C1-6 alkyloxy) C1-6 alkyl group designates a C1.6 alkyl group substituted with a C1.6 alkyloxy group and includes, for example, a methoxyethyl group, an ethoxyethyl group etc., and a nitrogen-containing heterocyclic ring group "Three to eight element nio" denotes an aromatic or alicyclic heterocyclic ring group of three to eight elements comprising one to three nitrogen atoms as ring element atom (s) and optionally comprising one to three oxygen and / or oxygen atom (s). sulfur as ring member atom (s) and includes, for example, a 1-pyrazolyl group, a 2-pyridyl group, a 2-pyrimidinyl group, a 2-thiazolyl group, a pyrrolidine group, a piperidino group, a morpholine etc. The group represented by R3, R4, R5 and R6 may be substituted with at least one halogen atom, and such halogen atom includes, for example, a fluorine atom, a chlorine atom, a bromine atom. or an iodine atom.

In the group represented by R3, R4, R5 and R6, a C3- and cycloalkyl group, a C10-10 aryl group, an aryl portion of a C1-6 alkyl (Ce-aryl) group, a C3-8 group cycloalkyloxy, a C6-10 aryloxy group, an aryl portion of a (C6-10 aryl) C1-6 alkyloxy group, an aryl portion of a C6-10 arylamino group, an aryl portion of a (C1-6-alkyl) group (C10-10 aryl) amino and a three to eight-membered nitrogen-containing heterocyclic ring group may be substituted with a C1-6 alkyl group and such a C1-6 alkyl group includes, for example, a methyl group, an ethyl group, a propyl group, a butyl group etc ..

Among the present compounds, the compound represented by the formula (la) of which G is a hydrogen atom may occur as tautomers represented by the formulas (1-a ') and (la "). The compound represented by the formula (la) ) includes all such tautomers and a mixture of any two or more thereof. (I - a) (I-a ') (Ia ”) The salt of the compound represented by formula (la) may also be obtained, for example, by mixing of the compound represented by formula (la) with an inorganic base (for example hydroxide, carbonate, hydrogen carbonate, acetate, hydride or the like of an alkali metal (lithium, sodium, potassium etc.); hydroxide, hydride or the like of a metal alkaline earth (magnesium, calcium, barium, etc.) or ammonia), an organic base (eg, dimethylamine, triethylamine, piperazine, pyrrolidine, piperidine, 2-phenylethylamine, benzylamine, ethanolamine, diethanolamine, pyridine , collidine and others) or a metal alkoxide (for example (sodium methoxide, potassium tert-butoxide, magnesium methoxide, etc.). The present invention includes agriculturally acceptable salts of the compounds represented by formula (1-a).

Where the present compound has one or more asymmetric centers, the present compound occurs as two or more stereoisomers (e.g., enantiomers, diastereomers or the like). The present compound includes all such stereoisomers and a mixture of any two or more thereof.

Where the present compound has a double bond based or similar geometric isomerism, said compound also occurs as two or more geometric isomers (for example, each E / Z or trans / cis isomer, each S-isomer isomer). trans / S-cis or others). The present compound includes all such geometric isomers and a mixture of any two or more of them.

Preferred embodiments of the present compounds include, for example, the following embodiments among the present compounds. The pyridazinone compound of formula (I), wherein n is an integer of 1 or more. The pyridazinone compound of formula (I), wherein n is 0, and Z 1 is a C 2-6 alkyl group. The pyridazinone compound of formula (I), wherein n is 1 or 2, and Z 2 is attached at the 4 and / or 6 position of the benzene ring. The pyridazinone compound of formula (I), wherein G is a hydrogen atom, a group represented by the formula, a group represented by the formula, or a group represented by the formula, (wherein in the formula R 3b represents a group C 1 -6 alkyl, a C 3-8 cycloalkyl group, a C 2-6 alkenyl group, a C 2-6 alkynyl group, a C 6-10 aryl group, a (C 6-10 aryl) group (C 1-6 alkyl, a C 1 -6 alkyloxy, a C 3-8 cycloalkyloxy group, a C 1-10 aryloxy group, a (C 6-10 aryl) C 1-6 alkyloxy group, a C 1-6 alkylamino group, a C 6-10 arylamino group or a di (C 1-6 alkyl) group. 6) alkyl) amino, R 4b represents a C 1-6 alkyl group or a C 6-10 aryl group, and R 5b and R 6b may be the same or different and represent a C 1-6 alkyl group, a C 1-6 alkyloxy group, a C 1-6 alkyl group. aryloxy or a C1-6 alkylthio group, here any group represented by R3b, R4b, R5b and R6b may be substituted with at least one halogen atom and a C3-8 cycloalkyl group, a C10-10 aryl group a portion aryl of a (C6-10 aryl) C1-6 alkyl group, a C3.8 cycloalkyloxy group, a C6-10 aryloxy group, an aryl portion of a (C6-10 aryl) C1-6 alkyloxy group, and an aryl moiety of a C 6-10 arylamino group may be substituted with at least one C 1-6 alkyl group. The pyridazinone compound of formula (I), wherein G is a hydrogen atom, a group represented by the formula, or a group represented by the formula, (wherein in the formula R33 represents a C1-6 alkyl group, a group C 3-8 cycloalkyl, a C 6-10 aryl group, a C 1-6 alkyloxy group or the di (C 1-6 alkyl) amino group, and R 4a represents a C 1-6 alkyl group, herein any group represented by R 3a and R 4a may be substituted with at least one halogen atom and a C 3-8 cycloalkyl group, and a C 6-10 aryl group may be substituted with at least one C 1-6 alkyl group The pyridazinone compound of formula (I) wherein R 1 is a C1-3 alkyl group or a (C1-3 alkyloxy) (C1-3 alkyl) group. The pyridazinone compound of formula (I), wherein R2 is a hydrogen atom or a C1-3 alkyl group. The pyridazinone compound of formula (I), wherein R2 is a hydrogen atom or a methyl group. The pyridazinone compound of formula (I), wherein Z1 is a C1-3 alkyl group, and Z2 is a C1-3 alkyl group. The pyridazinone compound of formula (I), wherein R1 is a C1-3 alkyl or C1-3 (alkyloxy) C1-3 alkyl group, and R2 is a hydrogen atom or a C1.3 alkyl group. The pyridazinone compound of formula (I), wherein R 1 is a C 1-3 alkyl group or a C (1-3 alkyloxy) C 1-3 alkyl group, and R 2 is a hydrogen atom or a methyl group. The pyridazinone compound of formula (I), wherein R2 is a hydrogen atom or a C1-3 alkyl group, and G is a hydrogen atom, a group represented by the formula, a group represented by the formula, or a group represented by the formula (wherein, in the formula, R3b, R4b, R5b and R6b are the same as above). The pyridazinone compound of formula (I), wherein R2 is a hydrogen atom or a C1.3 alkyl group, and G is a hydrogen atom, a group represented by the formula, or a group represented by the formula, ( wherein, in the formula, R 3a and R 4a are the same as mentioned above). The pyridazinone compound of formula (I) wherein R 2 is a hydrogen atom or a methyl group, G is a hydrogen atom, a group represented by the formula, a group represented by the formula, or a group represented by the formula (wherein, in the formula, R 3b R 4b, R 5b and R 6b are the same as above). The pyridazinone compound of formula (I), wherein R2 is a hydrogen atom or a methyl group, and G is a hydrogen atom, a group represented by the formula, or a group represented by the formula, (wherein, in the formula, R 3a and R 4a are the same as mentioned above). The pyridazinone compound of formula (I), wherein R1 is a C1-3 alkyl group or a (C1.3 alkyloxy) C1-3 alkyl group, R2 is a hydrogen atom or a C1-3 alkyl group, and G is a hydrogen atom, a group represented by the formula, a group represented by the formula, or a group represented by the formula (wherein, in the formula, R 3b, R 4b, R 5b and R 6b are the same as mentioned above). The pyridazinone compound of formula (I), wherein R1 is a C1-3 alkyl group or a (C1-3 alkyloxy) C1-3 alkyl group, and R2 is a hydrogen atom or a C1-3 alkyl group eG is a hydrogen atom, a group represented by the formula, or a group represented by the formula (wherein, in the formula, R 3a and R 43 are the same as mentioned above). The pyridazinone compound of formula (I), wherein R1 is a C1-3 alkyl group or a (C1-3 alkyloxy) C1-3 alkyl group, R2 is a hydrogen atom or a methyl group, and G is a hydrogen atom, a group represented by the formula, a group represented by the formula, or a group represented by the formula (wherein, in the formula, R 3b, R 4b, R 5b and R 6b are the same as mentioned above). The pyridazinone compound of formula (I), wherein R1 is a C1-3 alkyl group or a (C1-3 alkyloxy) C1-3 alkyl group, R2 is a hydrogen atom or a methyl group and G is a carbon atom. hydrogen, a group represented by the formula, or a group represented by the formula, (wherein, in the formula, R 3a and R 4a are the same as mentioned above.) The pyridazinone compound in formula (I), wherein R 1 is a C 1-4 group. 3 alkyl or a (C1-3 alkyloxy) C1.3 alkyl group, R2 is a hydrogen atom or C1.3 alkyl group, n represents 0, 1 or 2, and each Z2 may be the same or different when n represents 2, and when n represents 1 or 2, Z 2 is (are) one (4) substituent (s) at the 4 and / or 6 position of a benzene ring, Z 1 is a C 1-6 alkyl group (preferably a C 1 group). -3 alkyl), and Z2 is a C1-6 alkyl group (preferably a C1-3 alkyl group). The pyridazinone compound of formula (I), wherein R1 is a C1.3 alkyl group or a (C1-3 alkyloxy) C1-3 alkyl group, R2 is a hydrogen atom or C1.3 alkyl, and G is a hydrogen atom, a group represented by the formula, a group represented by the formula, or a group represented by the formula (wherein, in the formula, R 3b, R 4b, R 5b and R 6b are the same as mentioned above), n represents 0, 1 or 2, and each Z 2 may be the same or different when n represents 2, and when n represents 1 or 2, Z 2 is (is) (a) substituent (s) at the 4 and / or 6 position of a benzene ring, Z1 is a C1.6 alkyl group (preferably a C1.3 alkyl group), and Z2 is a C1-6 alkyl group (preferably a C1-3 alkyl group). The pyridazinone compound of formula (I), wherein R1 is a C1.3 alkyl group or a (C1-3 alkyloxy) C1-3 alkyl group, R2 is a hydrogen atom or a C1.3 alkyl group, G is a hydrogen atom, a group represented by the formula, or a group represented by the formula, (wherein, in the formula, R 3a and R 43 are the same as mentioned above), n represents 0, 1 or 2, and each Z 2 may be the same or when n represents 2, and when n represents 1 or 2, Z 2 is (is) (a) substituent (s) at the 4 and / or 6 position of a benzene ring, Z 1 is a C 1-6 alkyl group (preferably a C1-3 alkyl group), and Z2 is a C1-6 alkyl group (preferably a C1.3 alkyl group). The pyridazinone compound of formula (I), wherein R1 is a C1-3 alkyl group or a (C1-3 alkyloxy) C1-3 alkyl group, R2 is a hydrogen atom or a methyl group, n represents 0.1 or 2, and each Z 2 may be the same or different when n represents 2, and when n represents 1 or 2, Z 2 is (are) (a) substituent (s) at the 4 and / or 6 position of a benzene ring Z1 is a C1-6 alkyl group (preferably a C1-3 alkyl group), and Z2 is a C1-6 alkyl group (preferably a C1-3 alkyl group). The pyridazinone compound of formula (I), wherein R1 is a C1-3 alkyl group or a (C1-3 alkyloxy) alkyl group, R2 is a hydrogen atom or a methyl group, G is a hydrogen atom, a group represented by the formula, a group represented by the formula, or a group represented by the formula, (wherein, in the formula, R 3b, R 4b, R 5b and R 6b are the same as mentioned above), n represents 0, 1 or 2, and each Z 2 may be the same or different when n represents 2, and when n represents 1 or 2, Z 2 is (are) (a) substituent (s) at the 4 and / or 6 position of a benzene ring, Z 1 is a C 1 group -6 alkyl (preferably a C1-3 alkyl group), and Z2 is a C1-6 alkyl group (preferably a C1.3 alkyl group). The pyridazinone compound of formula (I), wherein R1 is a C1-3 alkyl group or a (C1.3 alkyloxy) C1.3 alkyl group, R2 is a hydrogen atom or a methyl group, G is a hydrogen, a group represented by the formula, or a group represented by the formula, (wherein, in the formula, R 3a and R 4a are the same as mentioned above), n represents 0, 1 or 2, and each Z 2 may be the same or different when n represents 2, and when n represents 1 or 2, Z 2 is (are) one (4) substituent (s) at the 4 and / or 6 position of a benzene ring, Z 1 is a C 1-6 alkyl group (preferably a C1.3 alkyl group), and Z2 is a C1.6 alkyl group (preferably a C1.3 alkyl group). The pyridazinone compound represented by the formula (1-1), (1-1) (wherein in the formula R2'1 represents a hydrogen atom or a C1-3 alkyl group, G1 represents a hydrogen atom, a group C1.3 alkylcarbonyl optionally substituted by at least one halogen atom, C1.3 alkoxycarbonyl group or C6-10 arylcarbonyl group, Z1'1 represents a C1-3 alkyl group, Z2'1'1 represents a C1 group -3 alkyl, and Z2'1'2 represents a hydrogen atom or a C1-3 alkyl group). The pyridazinone compound of formula (1-1), wherein R2'1 is a hydrogen atom, a methyl group or an ethyl group, G1 is a hydrogen atom, an acetyl group, a propionyl group, a methoxycarbonyl, an ethoxycarbonyl group or a benzoyl group, Z1'1 is a methyl group or an ethyl group, Z2'1'1 is a methyl group or an ethyl group, and Z2 "1'2 is a hydrogen atom, a methyl group or an ethyl group) The pyridazinone compound represented by the formula (1-2), (1-2) (wherein in the formula R2'2 represents a hydrogen atom or a C1.3 alkyl group, G2 represents a hydrogen atom, a C1-3 alkylcarbonyl group optionally substituted by at least one halogen atom or a C1.3 alkoxycarbonyl group, Z2'2'1 represents a hydrogen atom or a C1-3 alkyl group, and Z2'2'2 represents a hydrogen atom or a C1.3 alkyl group) The pyridazinone compound of formula (I-2), wherein R2'2 is a hydrogen atom, a methyl group 1a or an ethyl group, G2 is a hydrogen atom, an acetyl group, a methoxycarbonyl group or an ethoxycarbonyl group, Z2'2'1 is a hydrogen atom, a methyl group or an ethyl group, and Z2'2 '2 is a hydrogen atom, a methyl group or an ethyl group).

The present compounds have excellent weed control activity and can be used as an active ingredient of a herbicide. Some of the present compounds have selectivity between crops and weeds. Examples of weeds that the present compounds can control include the following: Field weeds such as Digitaria adscendens, Eleu-sine indica, Setaria viridis, Setaria faberi, Setaria glauca, Echinochloa crus-galli, Panicum dichotomiflorum, Brachiaria platyphilla, Sorghum hale , Sorghum bicolor, Cynodon dactylon, Avena fatua, Lolium multiflorum, Alopecurus myosuroides, Bromus tectorum, Bromus sterilis, Phalaris minor, Apera spica-ventl, Agropiron repens, Cyperus rotundus, Cyperus esculentus, Amaranthus retraceae, Amaranthus retraceae Abutilon theophrasti, Chenopodium album, Polygonum longisetum, Solanum nigrum, Sida spinosa, Datura stramonium, Ipomoea purpurea, Xantium strumarium, Cassia obtusi-folia, Ambrosia communis, Galium aparine, SteUa-ria media, Brassica chamom. Persian Veronica, Viola ar-vensis, Papaver rhoeas, Convolvuíus arvensis, Erigeron canadensis and the like; weeds in rice fields, such as Echinochloa oryzicola, Echinochloa crus-galli, Cyperus difformis, Cyperus iris, Fimbristilis miliacea, Eocharis acicularis, Scirpus juncoides, Scirpus wallichii, Cyperus serotinus, Eleocharis kuroguwis, Scirpus plani procumbens, Dopatrium junceum, Rotala indica, Am-mannia multiflora, Elatine triandra, Ludwigia prostrata, Sagittaria pygmaea, Alisma canaliculatum, Sagittaria trifolia, Potamogeton distinctus, Oenanthe javanica, Callitriche verna, Vandellia angustifolia, Linderniadata, Linderniadata distichum, Leersia oryzoides and the like. The present compound may be used as an herbicide of an agricultural field, such as a field, paddy field, lawn, similar orchard, or non-agricultural field. Particularly, it is suitable as herbicide in the field. In some cases weeds can be controlled without harming crops by using the present compost in an agricultural field where crops such as wheat, barley, soybeans, corn, cotton and similar crops are grown.

When the present compound is used as an active ingredient in herbicides, the present compound is generally formulated in a dosage form suitable for use by dissolving or dispersing in an appropriate liquid carrier or admixing with or absorbing an appropriate solid carrier. Herbicides comprising the present compound are a product formulated, for example, in the form of an emulsifiable concentration, soluble concentrate, oil solution, aerosol, wetting powder, dust, low spread dust, granule, microgranule, microgranule F, fine granule F, water-dispersible granule, water-soluble powder, dry-flow, dry-flow, jumbo tablet, meaning self-fusing powder in pouch, tablets, pastes or the like. Such a formulation may also be prepared, where necessary, by the addition of auxiliary agents, for example emulsifiers, dispersants, spreading agents, penetrating agents, wetting agents, binders, thickeners, preservatives, antioxidants, colorants or the like, according to the invention. with a known method. The liquid carrier used in the formulation includes, for example, water, alcohols (eg, methanol, ethanol, 1-propanol, 2-propanol, ethylene glycol, etc.), ketones (eg, acetone, methyl ethyl ketone, etc.), ethers (e.g. dioxane, tetrahydrofuran, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, etc.), aliphatic hydrocarbons (e.g. hexane, octane, cyclohexane, kerosene, fuel oil, machine oil etc.), aromatic hydrocarbons (eg benzene, toluene, xylene, solvent naphtha, methylnaphthalene etc.), halogenated hydrocarbons (eg dichloromethane, chloroform, carbon tetrachloride etc.), acid amides (eg dimethylformamide, dimethylacetamide, N-methylpyrrolidone etc.), esters (eg ethyl acetate, butyl acetate, glyceryl fatty acid ester etc.), nitriles (eg acetonitrile, propionitrile etc.) and the like . Two or more of these liquid carriers may be mixed for an appropriate ratio to use. The solid carrier used in the formulation includes plant dust (eg soy flour, alfalfa flour, wheat flour, wood flour etc.), mineral powders (eg clays such as kaolin, bentonite, acid clay, clay and etc., talc such as talcum powder, pyrophyllite powder etc., silica such as diatomaceous earth, mica powder etc.), alumina, sulfur powder, active charcoal, saccharides (eg lactose, glucose etc. .), inorganic salts (eg calcium carbonate, sodium bicarbonate etc.), hollow glass bodies (natural glassy materials that are calcined to encapsulate air bubbles within them) and the like. Two or more of these solid carriers may be mixed for an appropriate ratio to use. The amount of the liquid carrier or solid carrier used is generally from 1 to 99% by weight, preferably from about 10 to 99% by weight with respect to the total amount of formulation.

Surfactants are generally used as emulsifiers, dispersants, spreading agents, penetrating agents, wetting agents or others used in the formulation. Surfactants include, for example, anionic surfactants, such as alkyl sulfate ester salts, alkylarylsulfonates, dialkyl sulfosuccinates, polyoxyethylene alkylaryl ether phosphate salts, lignin sulfonate, naphthalenesulfonate-formaldehyde polycondensates etc., and such as polyoxyethylene alkyl ether, polyoxyethylene alkyl ether, polyoxyethylene alkyl polyoxypropylene block copolymer, fatty acid sorbitol ester and the like. Two or more of these surfactants may be used. The amount of surfactant used is generally from 0.1 to 50% by weight, preferably from about 0.1 to 25% by weight with respect to the total amount of the formulation.

Binders and thickeners include, for example, dextrin, carboxymethylcellulose sodium salt, polycarboxylic acid type polymers, polyvinylpyrrolidone, polyvinyl alcohol, sodium lignin sulfonate, calcium lignin sulfonate, arabic gum, sodium alginate, mannitol , sorbitol, bentonite-type mineral materials, polyacrylic acid and its derivatives, white carbon, natural saccharide derivatives (eg xanthan gum, guar gum etc.) or others. The content ratio of the present compound in the formulation is generally from 1 to 90% by weight in the form of emulsifiable concentrate, wetting powder, water dispersible granule, soluble concentrate, water soluble powder, flowable and the like, generally from 0.01 to 10% by weight in the form of oil-miscible liquid, dust, low spread dust etc. and generally from 0.05 to 10% by weight in the form of microgranule, microgranule F, fine granule F, granule and the like, respectively, but the concentration may be appropriately varied according to the purpose of use. The emulsifiable concentrate, wettable powder, water dispersible granule, soluble concentrate, water soluble, flowable or other powder are generally suitably diluted with water or others and generally used after dilution of about 100 to 100,000 times the concentration of the ingredient. The method for applying herbicides comprising the present compound as an active ingredient is similar to a conventional generic application method for known agricultural chemicals and includes, for example, aerial spraying, soil spreading, foliage application or the like.

When herbicides comprising the present compound as active ingredient are used as the herbicide for dry or flooded fields, their amount may vary with the area applied, the time of year of application, the method of application, the target weed species, the crop or similar crop, but generally in the range 1 to 5,000 g, preferably in the range 10 to 1,000 g of the present per hectare of dry or flooded field.

Herbicides comprising the present compound as an active ingredient for dry field weed control are generally used as a treatment agent for preemergence soil incorporation, preemergence soil treatment agent or soil tillage agent. post-emergence foliage. These weed control herbicides in flooded fields are generally used as a pre-emergent soil treatment agent or as a foliage or soil treatment agent. The herbicide comprising the present compound as active ingredient may be simultaneously applied, if necessary, with one or more detecting types. herbicides, plant growth regulators, fungicides, insecticides, acaricides, nematocides and the like, or may be used in combination with one or more detc types. herbicides, plant growth regulators, fungicides, insecticides, acaricides, nematocides and the like.

Active ingredients of the other herbicide which may be simultaneously applied and / or used in combination with the present compound include, for example, the following: (1) phenoxygroxic acid herbicidal compounds [2,4-PA, MCP, MCPB, phenothiol, mecoprop , fluroxipyr, triclopyr, clomeprop, naproanilide and the like], (2) herbicidal compounds of benzoic acid [2,3,6-TBA, dicamba, clopiralid, picloram, aminopiralid, quinclorac, quinmerac and the like], (3) urea herbicidal compounds [diuron, linuron, clortoluron, isoproturon, fluometuron, isouron, tebutiuron, metabenztiazuron, cumiluron, daimuron, methyl daimuron and smilares], (4) triazine herbicidal compounds [atrazine, ametorin, cyanozine, cyanozine, propazine, simetrin, dimetametrin, prometrin, metribuzin, triaziflam and the like], (5) bipyridinium herbicidal compounds [paraquat, diquat and the like], (6) hydroxybenzonitrile herbicidal compounds [bromoxynil, io-xinyl and the like], ( 7) Dinitroaniline herbicidal compounds [ pendimethalin, pro-diamine, trifluralin and the like], (8) organophosphorus herbicidal compounds [amiprofos-methyl, butamiphos, bensulide, piperophos, anilophos, glyphosate, glufosinate, bialaphos and the like], (9) carbamate [dialate, trialate, EPTC, butylate, bentiocarb, esprocarb, molinate, dimepiperate, "swep", chlorprofam, fenmedifam, fenisofam, piributicarb, asulam and the like], (10) acid amide herbicidal compounds [propanyl, propyzamide, bromobutide, etobenzanid and the like] , (11) chloroacetoanilide herbicidal compounds [acetochlor, ala-chlor, butachlor, dimethenamid, propachlor, metazachlor, metolachlor, pretylachlor, tenylchlor, petoxamid and the like], (12) diphenyl ether herbicidal compounds [acifluorfen-sodium, bifenoxy, oxyfluenox , lactofen, fomesafen, clometoxinyl, aclonifen and the like], (13) cyclic imide herbicidal compounds [oxadiazon, cinidon-ethyl, carfentrazone-ethyl, surfentrazone, flumiclorac-pentyl, flumioxazin, piraflu-phenethyl, oxad iargyl, pentoxazone, flutiacet-methyl, butafenacil, benzfendi-zone and the like], (14) pyrazol herbicidal compounds [benzofenap, pyrazolate, pyrazoxifen, topramezone, pirasulfotol and the like], (15) tricetone herbicidal compounds [isoxaflutol, benzobicyclobenz sulcotrione, mesotrione, tembotrione, tefuriltrione and the like], (16) aryloxyphenoxypropionate herbicidal compounds [clodine-fop-propargyl, cyalofop-butyl, diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxifop-methyl-propyl, quiz and (17) triona oxime herbicidal compounds [alloxidim sodium, setoxidim, butroxidim, clethodim, cloproxidim, cycloxidim, tepraloxidim, tralcoxidim, profoxidim and the like], (18) sulfonylurea herbicidal compounds [chlororsulfuron, sulphorsulfuron, meturon-methyl, metsulfuron-methyl, chlorimuron-ethyl, tribenuron-methyl, tria-sulfuron, bensulfuron-methyl, typhensulfuron-methyl, pyrazosulfuron-ethyl, nicosulfuron, amidosulfuron, cinosulfuron, imazosuron furon, rimsulfuron, halosulfuron-methyl, prosulfuron, etametsulfuron-methyl, triflusul-furon-methyl, flazasulfuron, cyclosulfamuron, flupirsulfuron, a-zimsulfuron, ethoxysulfuron, oxasulfuron, iodosulfon-methylsulfonon trifloxysulfuron, tritosulfuron, orthosulfamuron, flu-ketosulfuron and the like], (19) imidazolinone herbicidal compounds [imazametabenz-methyl, imazametapyr, imazamox, imazapir, imazaquin, imazetapir and the like], (20) herbicide compounds sulfetsamide sulam, diclosulam, florasulam, chloransulam-methyl, penoxsulam, piroxsulam and the like], (21) pyrimidinyloxybenzoate herbicidal compounds [pyrithio-bac-sodium, bispyribac-sodium, piriminobac-methyl, piribenzoxim, piriftalid, piri-misulfan and the like] (22) other types of herbicidal compounds [bentazon, bromacil, terbacil, clortiamid, isoxaben, dinoseb, amitrol, cinmethylin, tridifane, dalapon, diflufenzopyr-sodium, dithiopyr, thiazopyr, flucarbaz onasodium, propoxycarbazone-na-sodium, mefenacet, flufenacet, fentrazamide, cafenstrol, indanofan, oxazi-clomefone, benfuresate, ACN, pyridate, chloridazon, flurtamone, diflufenican, picolinfen, beflubutone, clomazazone, clamphenazole pyroxasulfone, thiencarbazone methyl and the like] and the like.

Active ingredients of plant growth regulator include, for example, himexazole, paclobutrazol, uniconazole-P, inabenfide, proexadione-calcium and the like.

Active ingredients of the fungicide include, for example, the following: (1) polyalalkylthio [captan and the like] fungicidal compounds, (2) organophosphorus [IBP, EDDP, tolclo-phosmethyl and the like] fungicidal compounds, (3) compounds benzimidazole fungicides [benomyl, carbendazim, thiophanate methyl and the like], (4) carboxyamide fungicidal compounds [carboxin, mepronyl, flutolanil, tifluzamid, furametpir, boscalid, pentiopirad and the like], (5) dicarboxyimide fungicidal compounds [ procimidone, ipro-dione, vinclozolin and the like], (6) acylalanine fungicidal compounds [metalaxyl and the like], (7) azole fungicidal compounds [triadimefon, triadimenol, pro-piconazole, tebuconazole, cyproconazole, epoxiconazole, ipconazole, triflumizole, prochloraz etc.], (8) morpholine fungicidal compounds [dodemorf, tridemorf, fen-propimorf and the like], (9) strobilurin fungicidal compounds [azoxystrobin, cresom-ximomethyl, metominostrobin, trifloxystrobin, picoxystrobi na, piraclostrobin and the like], (10) antibiotic fungicidal compounds [validamycin A, blasticidin S, kasugamycin, polyoxin and the like], (11) dithiocarbamate fungicidal compounds [mancozeb, maneb and the like], (12) other types of fungicidal compounds [phthalide, probenazole, isoprothiolane, tricyclazole, pyrokylon, ferimzone, acibenzolar S-methyl, carpro-pamid, diclocimet, phenoxanil, thiadinyl, dichlomezine, keyboardophthalam, pencicuron, oxolinic acid, TPN, triforamine, phenorine, triforamine, phenorine imi-noctadine, fenpiclonil, fludioxonil, quinoxyfen, fenhexamid, siltiofam, pro-quinazid, ciflufenamid, bordeaux mix and the like] and the like.

Active ingredients of the insecticide include, for example, the following: (1) organophosphorus insecticidal compounds [fention, fenitrothion, pyrimiphos-methyl, diazinon, quinalfos, isoxation, pyridafention, chlorpyrifos-methyl, vamidotion, malation, phytate, dimethoate, disulfoton, monocrotophos, tetra-chlorvinphos, chlorphenvinphos, propaphos, acephate, trichlorphon, EPN, piraclophos and the like], (2) carbamate insecticidal compounds [carbaryl, metolcarb, isoprocarb, BPMC, propoxur, XMC, carbofuran, carbosulfan, benfurocarbyl, benfur , thiodicarb and the like], (3) synthetic pyrethroid insecticidal compounds [teflutrin, bi-fentrin, cycloprotrin, etofenprox and the like], (4) nereistoxin-based insecticidal compounds [cartap, ben-sultap, thiocyclam and the like], ( 5) neonicotinoid insecticidal compounds [imidacloprid, nitenpi-ram, acetamiprid, thiametoxam, tiacloprid, dinotefuran, clotianidin and the like], (6) benzoylphenylurea insecticidal compounds [chlorfluazuron, flu-phenoxide n, hexaflumuron, lufenuron, novaluron and the like], (7) macrolide insecticidal compounds [emamectin, spinosad and the like], (8) other types of insecticidal compounds [buprofezin, tebufenazide, fipronil, etiprol, pimetrozine, diafentiuron, indoxacarb , tolfenpirad, pyrida-lila, flonicamid, flubendiamide and the like] and the like.

Active ingredients of acaricide include, for example, hexithiazox, pyridaben, fenpyroximate, tebufenpyrad, chlorfenapyr, ethoxazole, pyrimidifen, α-cequinocyl, biphenazate, spirodiclofen and the like.

Active ingredients of nematocide include, for example, fostia-zato, cadusafos and the like. The herbicide containing the present compound as an active ingredient may, if necessary, be additionally mixed with a safety agent (eg furilazole, diclormid, benoxacor, alidochlor, isoxa-diphenethyl, phenclorazol-ethyl, mefenpir-diethyl, cloquintocet). -methyl, phenlorim, cyprosulfamide, cymetrinyl, oxabetrinyl, fluxophenim, flurazole, 1,8-naphthalic anhydride and the like), coloring agent, fertilizer (e.g., urea and the like) and the like. The present compound may be used as an active ingredient in herbicides for cropland, such as a field, paddy field, lawn, orchard, or non-cropland. The present compost can control weeds without causing any damage to the "crops" in a location that cultivates the "crops" listed below. "Crops" Corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybean, peanuts, buckwheat, beet, rapeseed, sunflower, sugar cane, tobacco and the like; solanaceous vegetables (eggplant, tomato, green pepper, red pepper, potato and the like), cucurbit vegetables (cucumber, pumpkin, zucchini, watermelon, melon and the like), brassicaceous vegetables (Japanese radish, turnip, horseradish, kale) horseradish, chinese cabbage, cabbage, mustard, broccoli, cauliflower and the like), compound vegetables (burdock, chrysanthemum, artichoke, lettuce and the like), lily vegetables (leeks, onions, garlic, asparagus and the like), umbelifers (carrots, parsley, celery, wild parsnips and the like), kenopodiac vegetables (spinach, swiss chard and the like), labiaceous vegetables (perilla, mint, basil and the like), strawberry, sweet potato, yam, taioba and the like; ornamental flowers; domestic plants; fruit (apple, pear, japanese pear, chinese quince, quince and the like), stone fruits (peach, plum, nectarine, japanese plum, mahaleb cherry, apricot, plum raisin and the like), citrus (tangerine, orange, lemon , lime, grapefruit and the like), walnuts (chestnut, walnut, hazelnut, almond, pistachio, cashews, macadamia and others), fruits with fluid (mulberry, blueberry, blackberry, raspberry and the like), grapes persimmon, olive, yellow plum, banana, coffee, dates, coconut trees and the like; and tea, blackberry, flowering plants, roadside trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, stag oak, poplar, cercis, liquidambar, plastane, zelkova, Thuja stan-dishii, Abies, spruce, juniper, pine, spruce, yew) and the like.

Crops that have received herbicide resistance by classical breeding techniques, gene recombination technology or the like are included in these "crops". There is no damage to crops that have received herbicide resistance when herbicides as HPPD inhibitors such as isoxaflutol; ALS inhibitors such as imazethapyr, thiphensulfuron methyl; EPSP synthetase inhibitors; glutamine synthetase inhibitors; acetyl CoA carboxylase inhibitors; or bromoxynil and the like; are applied.

Crops receiving herbicide resistance by classical breeding techniques include, for example, Clearfield (trademark) canola with herbicide resistance of imidazolinone, STS with herbicide resistance to sulfonylurea, SR corn with resistance to acetyl CoA carboxylase inhibitors. Crops receiving resistance to acetyl CoA carboxylase inhibitors are described, for example, in Proc. Natl. Acad. Know. USA, vol. 87, pp. 7175 (1990).

In addition, mutant acetyl CoA carboxylase conferring resistance to acetyl CoA carboxylase inhibitors is described, for example, in Weed Science vol. 53, pp. 728-746 (2005). Resistance to acetyl CoA carboxylase inhibitors may be conferred to crops when the gene encoding such mutant acetyl CoA carboxylase is introduced by recombinant gene technology, or when mutations related to resistance to acetyl CoA carboxylase inhibitors are introduced into the gene encoding the acetyl CoA carboxylase.

"Crops" to which herbicide resistance is conferred by gene recombination technology are known (for example, maize varieties to which glyphosate or glufosinate resistance is added). These varieties of corn are commercially available as a product under the name of Roundup Ready (trademark) or Liberty Link (trademark).

"Crops" include crops that are capable of producing insecticidal toxins by gene recombination technology.

Such insecticidal toxins include, for example, insecticidal proteins produced by Bacillus cereus or Bacillus popilliae; δ-endotoxins such as CrilAb, GrilAc, CrilF, CrilFa2, Cry2Ab, Cry3A, Cry3Bb1 and Cry9C produced by Bacillus thuringiensis; insecticidal proteins such as VIP1, VIP2, VIP3 and VIP3A; insecticidal proteins produced by nematodes; animal-produced toxins such as scorpion toxin, spider toxin, bee toxin and an insect-specific nervous system toxin; filamentous fungal toxins; plant lectins; agglutinins; protease inhibitors such as trypsin inhibitors, serine protease inhibitors, patathin, cystatin and papain inhibitors; ribosome inactivation proteins (RIPs), such as ricins, corn RIPs, aprins, saporins, brydine; steroid metabolism enzymes such as 3-hydroxysteroid oxidase, ecdiesteroid UDP-glucosyl transferase, cholesterol oxidase; ecdisone inhibitors; HMG-CoA reductase; ion channel inhibitors, such as sodium channel or calcium channel inhibitors; juvenile hormone esterase; diuretic hormone receptors; stilbene synthetase; bibenzyl synthetase; chitinase; and glucanases.

Insecticidal toxins include hybrid proteins of said insecticidal proteins, insecticidal proteins in which a portion of the amino acids that make up the proteins are deleted or replaced. Hybrid proteins are created by putting different domains of these insecticidal proteins together by gene recombination technology. For example, CrilAb, in which a portion of amino acids is deleted, is known as the above insecticidal protein in which a portion of the amino acids that make up the protein is deleted.

For example, insecticidal toxins and "crops" that have been able to produce insecticidal toxins by gene recombination technology are described in EP-A-0 374 753, WO 93 / 07.278, WO 95 / 34,656, EP-A-0 427,529, EP-A-451,878 and WO 03 / 052,073.

For example, "crops" that have been able to produce insecticidal toxins by gene recombination technology have resistance to attack by Coleoptera pests, Diptera silver and / or Lepidopteran pests.

Examples of commercially available "crops" that have been able to produce insecticidal toxins by gene recombination technology include YieldGard (trademark) (CrilAb toxin expressing maize variety), YieldGard Rootworm (trademark) (expressing maize variety) toxin Cry3Bb1), YieldGard Plus (trademark) (maize variety expressing CrilAb and Cry3Bb1), Herculex I (trademark) (maize variety expressing CrilFa2 toxin and phosphinothricin / V-acetyltransferase (PAT) to confer resistance to glufosinate), NuCOTN33B (trademark) (cotton variety expressing CrilAc toxin), Bollgard I (trademark) (cotton variety expressing CrilAc toxin), Bollgard M (trademark) (cotton variety expressing CrilAc and Cry2Ab), VIPCOT (trademark) (VIP toxin-expressing cotton variety), NewLeaf (trademark) (toxin-expressing potato variety) ina Cry3A), NatureGard (trademark) Agrisure (trademark) GT Advantage (GA21 glyphosate resistance trait), Agrisure (trademark) CB Advantage (Bt11 corn borer trait (CB)) and Protecta (trademark).

"Crops" also include crops that have been able to produce antipathogenic substances by gene recombination technology.

Antipathogenic substances include, for example, PR proteins (PRPs, described in EP-A-0 392 225); ion channel inhibitors such as sodium channel inhibitors, calcium channel inhibitors (KP1, KP4 and KP6 toxins and the like produced by viruses are known); stilbene synthetase; bibenzyl synthetase; chitinase; glucanase; substances produced by microorganisms, such as peptide antibiotics, heterocycle antibiotics; and protein factors related to resistance against plant pathogens (described in WO 03 / 000.906) and the like.

Crops which have been given the ability to produce an antipathogen by gene recombination technology are described, for example, in EP-A-0 392 225, WO 95 / 33,818 and EP-A-0 353 191.

When the present compound is mixed with flumioxazine, the mixing ratio is preferably from 0.1 to 10 weight percent flumioxazine based on 1 weight of the present compound. The composition comprising the present compound and flumioxazine may be used for soil treatment or foliage treatment. The composition comprising the present compound and flumioxazine can control weeds without causing any crop damage at the place of cultivation of maize, rice, wheat, barley, rye, oats, sorghum, cotton, soybean, peanut, beet, rapeseed, sunflower, cane. sugar cane and the like. And the composition comprising the present compound and flumioxazine may be used for cropland, such as a lawn, an orchard, or non-cropland.

When the present compound is mixed with glyphosate, the mixing ratio is preferably from 1 to 100 by weight glyphosate based on 1 weight of the present compound. The composition comprising the present compound and glyphosate may be used for foliage treatment. The composition comprising the present compound and glyphosate can control weeds without causing any damage to the crop at the place of cultivation of corn, rice, deer, rye, oats, sorghum, cotton, soybean, peanuts, beet, rapeseed, sunflower, cane. sugarcane and the like, and the composition comprising the present compound and glyphosate may be used for cropland, such as a lawn, an orchard, or non-cropland. The present compound may be produced, for example, by the following methods of preparation. Method of Preparation 1 Among the present compounds, the compound represented by the formula (la), wherein G is a hydrogen atom, may be produced by reacting the compound represented by the formula (II) with a metal hydroxide, (Π) ( 1a) (wherein, in the formula, R 7 represents a C 1-6 alkyl group (e.g., a methyl group, an ethyl group and the like) and R 1, R 2, Z 1, Z 2en are the same as mentioned above). The reaction is generally performed in a solvent. The solvent used in the reaction includes, for example, water, ethers such as tetrahydrofuran, dioxane or a mixture of such solvents. The metal hydroxide used in the reaction includes, for example, an alkali metal hydroxide such as sodium hydroxide, potassium hydroxide etc. The amount of the metal hydroxide used in the reaction is generally from 1 to 120 molar equivalents, preferably 1 to 40 molar equivalents with respect to the compound represented by formula (II). The reaction temperature is generally in the range of ambient temperature to the boiling point of the solvent, preferably to the boiling point of the solvent. The reaction may be performed by heating in a sealed tube or a closed container resistant to high pressure. Reaction time is generally in the range of 5 minutes to a few weeks. The termination of the reaction can be confirmed using analytical means such as thin layer chromatography, high performance liquid chromatography or the like after sampling a portion of the reaction mixture. Upon completion of the reaction, the compound represented by formula (1a) may be isolated, for example, by the following operation: adding an acid to the reaction mixture to which water is added to mix, followed by extraction with an organic solvent to form an organic layer, which is dried and concentrated. Method of Preparation 2 Among the present compounds, the compounds represented by formula (1b), wherein G is a group other than a hydrogen atom, may be produced from the compound represented by formula (la) and the compound represented by (wherein, in the formula, G3 of the defined G represents a group other than a hydrogen atom, X represents a halogen atom (for example, a chlorine atom, a bromine atom, an atom iodine, etc.) or a group represented by the formula OG3, and R1, R2, Z1, Z2 and n are the same as mentioned above). The reaction may be performed in a solvent. The solvent used in the reaction includes, for example, aromatic hydrocarbons such as benzene, toluene etc., ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, dimethoxyethane etc., halogenated hydrocarbons such as dichloromethane, chloroform, 1,2- dichloroethane etc., amides such as dimethylformamide, dimethylacetamide etc., sulfoxides such as dimethyl sulfoxide etc., sulfones such as sulfurane and the like or a mixture of these solvents. The compound represented by the formula (III) used in the reaction includes, for example, carboxylic acid halides such as acetyl chloride, propionyl chloride, isobutyryl chloride, pivaloyl chloride, benzoyl chloride, cyclohexanecarbonyl chloride etc., anhydrides carboxylic acid such as acetic anhydride, trifluoroacetic anhydride etc., carbonate half ester halides such as methyl chloroformate, ethyl chloroformate, phenyl chloroformate etc., carbamoyl halides such as dimethylcarbamoyl chloride etc., sulfonyl halides such as methanesulfonyl, p-toluenesulfonyl chloride etc., sulfonic acid anhydrides such as methanesulfonic anhydride, trifluoromethanesulfonic anhydride etc., or halogenated phosphate esters such as dimethyl chlorophosphate etc. The amount of the compound represented by the formula (III) used in the reaction is generally one molar equivalent or more, preferably 1 to 3 molar equivalents with respect to co compound represented by formula (1-a). The reaction is generally performed in the presence of a base. The base used in the reaction includes, for example, organic bases such as triethylamine, tripropylamine, pyridine, dimethylaminopyridine, 1,8-diazabi-cyclo [5.4.0] undecene and etc., and inorganic bases such as sodium hydroxide, hydroxide potassium, calcium hydroxide, sodium carbonate, potassium carbonate, hydrogen sodium carbonate, calcium carbonate, sodium hydride and others. The amount of the base used in the reaction is generally 0.5 to 10 molar equivalents, preferably 1 to 5 molar equivalents with respect to the compound represented by formula (1-a). The reaction temperature is generally from -30 to 180 ° C, preferably from -10 to 50 ° C. The reaction time is generally 10 minutes to 30 hours. The termination of the reaction can be confirmed using analytical means such as thin layer chromatography, high performance liquid chromatography or the like after sampling a portion of the reaction mixture. Upon completion of the reaction, the compound represented by formula (1b) may be isolated, for example, by the following operation: mixing the reaction mixture with water followed by extraction with an organic solvent to form an organic layer, which is dried. and concentrated. The compound represented by formula (III) is a known compound or may be produced from a known compound. Preparation Method Among the present compounds, the compound represented by formula (1-a), wherein G is a hydrogen atom, may also be produced by the following preparation method. The compound represented by the formula (la) may be produced by reacting the compound represented by the formula (VI) with a base, (VI) (la) (wherein in the formula R 9 represents a C 1-6 alkyl group (e.g. a methyl group, an ethyl group etc.) and R1, R2, Z1, Z2 and n are the same as above). The reaction is generally performed in a solvent. The solvent used in the reaction includes, for example, aromatic hydrocarbons such as benzene, toluene, xylene etc., ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, dimethoxyethane etc., halogenated hydrocarbons such as dichloromethane, chloroform, 1,2- dichloroethane etc., amides such as dimethylformamide, dimethylacetamide etc., sulfones such as sulphorane etc., or a mixture of such solvents. The base used in the reaction includes, for example, metal alkoxides such as potassium tert-butoxide etc., alkali metal hydrides such as sodium hydride etc., and organic bases such as triethylamine, tributylamine, N, N-diisopropylethylamine and tec. . The amount of the base used in the reaction is generally 1 to 10 molar equivalents, preferably 2 to 5 molar equivalents with respect to the compound represented by formula (VI). The reaction temperature is generally from -60 to 180 ° C, preferably from -10 to 100 ° C. The reaction time is generally 10 minutes to 30 hours. The termination of the reaction can be confirmed using analytical means such as thin layer chromatography, high performance liquid chromatography or the like after sampling a portion of the reaction mixture. Upon completion of the reaction, the compound represented by formula (1a) may be isolated, for example, by the following operation: adding an acid to the reaction mixture to which water is added to mix, followed by extraction with an organic solvent to form an organic layer, which is dried and concentrated. Reference Preparation Method 1 The compound represented by formula (II) may be produced, for example, by the following preparation method, (wherein, in formula, X1 represents a leaving group (for example, a halogen atom as an atom). chlorine atom, a bromine atom, an iodine atom, etc.), X 2 represents a halogen atom (for example, a chlorine atom, a bromine atom, an iodine atom, etc.), R 8 represents a C 1-6 group. 6 is alkyl (for example a methyl group, a butyl group etc.) and R 1, R 2, R 7, Z 1, Z 2 and n are the same as above). The compound represented by formula (II) may be produced by a coupling reaction of the compound represented by formula (IV) with an organometallic reagent represented by formulas (Va), (Vb) or (Vc) (generally one molar equivalent or more, preferably 1 to 3 molar equivalents with respect to the compound represented by formula (IV)).

When the compound represented by formula (V-a) is used, said coupling reaction is performed in a solvent. The solvent used in the reaction includes, for example, aromatic hydrocarbons such as benzene, toluene etc., alcohols such as methanol, ethanol, propanol etc., ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, dimethoxyethane etc., ketones such as acetone , methyl ethyl ketone etc., amides such as dimethylformamide, dimethylacetamide etc., sulfoxides such as dimethyl sulfoxide etc., sulfones such as sulfolane etc., water or a mixture of these solvents.

When the compound represented by the formula (V-a) is used, said coupling reaction is performed in the presence of a base. The base used in the reaction includes, for example, organic bases such as triethylamine, tripropylamine, pyridine, dimethylaniline, dimethylaminopyridine, 1,8-diazabicyclo [5.4.0] -7-undecene and others, and inorganic bases such as sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, hydrogen sodium carbonate, calcium carbonate, cesium carbonate, potassium fosphate etc. The amount of base used in the reaction is generally 0.5 to 10 molar equivalents. preferably 1 to 5 molar equivalents with respect to the compound represented by formula (IV).

Furthermore, when the compound represented by the formula (V-a) is used, said coupling reaction is performed in the presence of a catalyst. The catalyst used in the reaction includes, for example, a palladium catalyst such as tetrakis (triphenylphosphine) palladium, dichlorobis (triphenylphosphine) palladium etc. The amount of catalyst used in the reaction is generally from 0.001 to 0.5 molar equivalents, preferably 0 .01 to 0.2 molar equivalents with respect to the compound represented by formula (IV). When the compound represented by the formula (V-a) is used, a quaternary ammonium salt is preferably added in said coupling reaction. Quaternary ammonium salt used includes, for example, tetrabutylammonium bromide, etc.

When the compound represented by formula (V-a) is used, the reaction temperature of said coupling reaction is generally from 20 to 180 ° C, preferably from 60 to 150 ° C. The reaction time is generally from 30 minutes to 100 hours. The termination of the reaction can be confirmed using analytical means such as thin layer chromatography, high performance liquid chromatography or the like after sampling a portion of the reaction mixture. Upon completion of the reaction, the compound represented by formula (II) may be isolated, for example, by the following operation: mixing the reaction mixture with water, followed by extraction with an organic solvent to form an organic layer, which is dried and concentrated.

When the compound represented by formula (V-b) is used, said coupling reaction is performed in a solvent. The solvent used in the reaction includes, for example, aromatic hydrocarbons such as benzene, toluene etc., ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, dimethoxyethane etc., or a mixture of such solvents.

When the compound represented by the formula (V-b) is used, said coupling reaction is performed in the presence of a catalyst. The catalyst used in the reaction includes, for example, a nickel catalyst such as dichlorobis (1,3-diphenylphosphine) propane nickel, dichlorobis (triphenylphosphine) nickel etc., and a palladium catalyst such as tetrakis (triphenylphosphine) palladium, dichlorobis (triphenylphosphine) palladium etc. The amount of catalyst used in the reaction is generally from 0.001 to 0.5 molar equivalents, preferably 0.01 to 0.2 molar equivalents with respect to the compound represented by formula (IV).

When the compound represented by the formula (V-b) is used, the reaction temperature of said coupling reaction is generally from -80 to 180 ° C, preferably from -30 to 150 ° C. The reaction time is generally from 30 minutes to 100 hours. The termination of the reaction can be confirmed using analytical means such as thin layer chromatography, high performance liquid chromatography or others after sampling a portion of the reaction mixture. Upon completion of the reaction, the compound represented by formula (II) may be isolated, for example, by the following operation: mixing the reaction mixture with water, followed by extraction with an organic solvent to form an organic layer, which is dried and concentrated.

When the compound represented by the formula (V-c) is used, said coupling reaction is carried out in a solvent. The solvent used in the reaction includes, for example, aromatic hydrocarbons such as benzene, toluene etc., ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, dimethoxyethane etc., halogenated hydrocarbons such as chloroform, 1,2-dichloroethane etc., amides such as dimethylformamide, dimethylacetamide etc., or a mixture of such solvents.

When the compound represented by formula (V-c) is used, said coupling reaction is performed in the presence of a catalyst. The catalyst used in the reaction includes, for example, a palladium catalyst such as tetrakis (triphenylphosphine) palladium, dichlorobis (triphenylphosphine) palladium etc. The amount of catalyst used in the reaction is generally from 0.001 to 0.5 molar equivalents, preferably 0 .01 to 0.2 molar equivalents with respect to the compound represented by formula (IV).

When the compound represented by the formula (V-c) is used, the reaction temperature of said coupling reaction is generally from -80 to 180 ° C, preferably from -30 to 150 ° C. The reaction time is generally from 30 minutes to 100 hours. The termination of the reaction can be confirmed using analytical means such as thin layer chromatography, high performance liquid chromatography or others after sampling a portion of the reaction mixture. Upon completion of the reaction, the compound represented by formula (II) may be isolated, for example, by the following operation: mixing the reaction mixture with water, followed by extraction with an organic solvent to form an organic layer, which is dried and concentrated. The compound represented by formula (II) may be produced, for example, by a method according to that described in Tetrahedron vol. 57, pp 1323-1330 (2001), etc.

Organometallic reagents represented by formulas (V-a), (V-b) and (V-c) are known compounds or may be produced by methods according to known methods using known compounds. The compound represented by formula (IV) is a known compound or may be produced using known compounds. The compound may be produced, for example, by a method described in J. Hete-rocycl. Chem., Vol. 33, pp 1579-1582 (1996) and the like, or a method according to one of these. Reference Preparation Method 2 The compound represented by formula (VI) may be produced, for example, by the following preparation method, (wherein in formula X3 represents a halogen atom (e.g. a chlorine atom, a bromine, an iodine atom, etc.) and R1, R2, R9, Z1, Z2 and n are the same as mentioned above). The reaction is generally performed in a solvent. The solvent used in the reaction includes, for example, nitriles such as acetonitrile etc., ketones such as acetone etc., aromatic hydrocarbons such as benzene, toluene etc., ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, dimeoxyethane etc., hydrocarbons halogenates such as dichloromethane, chloroform, 1,2-dichloroethane etc., amides such as dimethylformamide, dimethylacetamide etc., sulfones such as sulfolane etc. or a mixture of such solvents. The reaction of the compound represented by the formula (VII) with the compound represented by the formula (VIII) is generally carried out in the presence of a base. The base used in the reaction includes, for example, organic bases such as triethylamine, tripropylamine, pyridine, dimethylaminopyridine, 1,8-diazabicyclo [5.4.0] -7-undecene, 1,4-diazabicyclo [2.2.2] octane etc., and inorganic bases such as sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, calcium carbonate, sodium hydride and etc. The amount of the compound represented by the formula ( VIII) used in the reaction is generally 1 molar equivalent or more, preferably 1 to 3 molar equivalents with respect to the compound represented by formula (VII). The amount of base used in the reaction is generally 0.5 to 10 molar equivalents, preferably 1 to 5 molar equivalents with respect to the compound represented by formula (VII). The reaction temperature is generally from -30 to 180 ° C, preferably from -10 to 50 ° C. The reaction time is generally 10 minutes to 30 hours. The termination of the reaction can be confirmed using analytical means such as thin layer chromatography, high performance liquid chromatography or the like after sampling a portion of the reaction mixture. Upon completion of the reaction, the compound represented by formula (VI) may be isolated, for example, by the following operation: mixing the reaction mixture with water, followed by extraction with an organic solvent to form an organic layer, which is dried and concentrated. The compound represented by formula (VII) may be produced by reacting the compound represented by formula (IX) (IX) (wherein, in the formula, Z1, Z2 and n are the same as above) with a halogenation reagent (e.g. thionyl chloride, thionyl bromide, phosphorus oxychloride, oxalyl chloride etc.). The compound represented by formula (IX) is a known compound or may be produced from known compounds. The compound may be produced, for example, according to methods described in Organic Syntheses Collective Volume 3, pp 557-560 (1955), J. Am. Chem. Soc. Vol. 63, pp 2643-2644 (1941) and WO 2006/056282 etc., and similar methods. The compound represented by formula (IX) includes, for example, 2,4,6-trimethylphenyl acetic acid, 2,4,6-triethylphenylacetic acid, 2,6-diethyl-4-methylphenylacetic acid, 2-ethylphenyl acetic acid, 2-ethyl-4-methylphenylacetic acid, 2-ethyl-4,6-dimethylphenylacetic acid, 2,4-diethylphenyl acetic acid, 2,6-diethylphenylacetic acid, 2,6-diethyl-6-methylphenylacetic acid, etc. The compound represented by formula (VIII) is a known compound or may be produced from known compounds.

Each compound produced by the aforementioned Preparation Methods 1-3 or Reference Preparation Methods 1-2 may be isolated and / or purified by known procedures, for example concentration, concentration under reduced pressure, extraction, transfer dissolution, crystallization, recrystallization, chromatography, and the like. The following specific examples of the present compound are shown below. (i1) (I2) (I3) (I4) (I5) (I6) (1) The pyridazinone compound wherein Ar is a 2-ethylphenyl group, and G is a hydrogen atom, an acetyl group, a triflu group -oroacetyl, a propionyl group, a butyryl group, an isobutyryl group, an isovaleryl group, a pivaloyl group, a cyclohexylcarbonyl group, a benzoyl group, a benzylcarbonyl group, an ethoxycarbonyl group, a phenoxycarbonyl group, a dimethylaminocarbon group a methanesulfonyl group, a trifluoromethanesulfonyl group, a benzenesulfonyl group or a p-toluenesulfonyl group in any of formulas (I1) to (I30). (2) The pyridazinone compound wherein Ar is a 2-propylphenyl group, and G is a hydrogen atom, an acetyl group, a trifluoroacetyl group, a propionyl group, a butyryl group, an isobutyryl group, an isovaleryl group, a pivaloyl group, a cyclohexylcarbonyl group, a benzoyl group, a benzylcarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a phenoxycarbonyl group, a dimethylaminocarbonyl group, a trifluoromethanesulfonyl group, a benzenesulfonyl group or a penesulfonyl tolensulfonyl group one of formulas (I1) to (I30). (3) The pyridazinone compound wherein Ar is a 2,4-dimethylphenyl group, and G is a hydrogen atom, an acetyl group, a trifluoroacetyl group, a propionyl group, a butyryl group, an isobutyryl group, an isovaleryl group , a pivaloyl group, a cyclohexylcarbonyl group, a benzoyl group, a benzylcarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a phenoxycarbonyl group, a dimethylaminocarbonyl group, a methanesulfonyl group, a trifluoromethanesulfonyl group or a benzenesulfonyl group -toluenesulfonyl in any of formulas (I1) to (I30). (4) The pyridazinone compound wherein Ar is a 2,6-dimethylphenyl group, and G is a hydrogen atom, an acetyl group, a trifluoroacetyl group, a propionyl group, a butyryl group, an isobutyryl group, an isovaleryl group , a pivaloyl group, a cyclohexylcarbonyl group, a benzoyl group, a benzylcarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a phenoxycarbonyl group, a dimethylaminocarbonyl group, a methanesulfonyl group, a trifluoromethanesulfonyl group or a benzenesulfonyl group -toluenesulfonyl in any of formulas (I1) to (I30). (5) The pyridazinone compound wherein Ar is a 2-ethyl-4-methylphenyl group, and G is a hydrogen atom, an acetyl group, a trifluoroacetyl group, a propionyl group, a butyryl group, an isobutyryl group, a isovaleryl group, a pivaloyl group, a cyclohexylcarbonyl group, a benzoyl group, a benzylcarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a phenoxycarbonyl group, a dimethylaminocarbonyl group, a methanesulfonyl group, a trifluoromethanesulfonyl group or a benzenesulfonyl group p-toluenesulfonyl group in any of formulas (I1) to (I30). (6) The pyridazinone compound wherein Ar is a 2-ethyl-6-methylphenyl group, and G is a hydrogen atom, an acetyl group, a trifluoroacetyl group, a propionyl group, a butyryl group, an isobutyryl group, a isovaleryl group, a pivaloyl group, a cyclohexylcarbonyl group, a benzoyl group, a benzylcarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a phenoxycarbonyl group, a dimethylaminocarbonyl group, a methanesulfonyl group, a trifluoromethanesulfonyl group or a benzenesulfonyl group p-toluenesulfonyl group in any of formulas (I1) to (I30). (7) The pyridazinone compound wherein Ar is a 2,6-diethylphenyl group, and G is a hydrogen atom, an acetyl group, a trifluoroacetyl group, a propionyl group, a butyryl group, an isobutyryl group, an isovaleryl group, a pivaloyl group, cyclohexylcarbonyl group, benzoyl group, benzylcarbonyl group, methoxycarbonyl group, ethoxycarbonyl group, phenoxycarbonyl group, dimethylaminocarbonyl group, methanesulfonyl group, trifluoromethanesulfonyl group or benzenesulfonyl group in any of formulas (I1) to (I30). (8) The pyridazinone compound wherein Ar is a 2,4,6-trimethylphenyl group, and G is a hydrogen atom, an acetyl group, a trifluoroacetyl group, a propionyl group, a butyryl group, an iso-butyryl group, a isovaleryl group, a pivaloyl group, a cyclohexylcarbonyl group, a benzoyl group, a benzylcarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a phenoxycarbonyl group, a dimethylaminocarbonyl group, a methanesulfonyl group, a trifluoromethanesulfonyl group or a benzenesulfonyl group p-toluenesulfonyl group in any of formulas (I1) to (I30). (9) The pyridazinone compound wherein Ar is a 2-ethyl-4,6-dimethylphenyl group, and G is a hydrogen atom, an acetyl group, a trifluoroacetyl group, a propionyl group, a butyryl group, an isobutyryl group , an isovaleryl group, a pivaloyl group, a cyclohexylcarbonyl group, a benzoyl group, a benzylcarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a phenoxycarbonyl group, a dimethylaminocarbonyl group, a methanesulfonyl group, a trifluoromethanesulfonyl group, a sulfonyl group or a p-toluenesulfonyl group in any of formulas (I1) to (I30). (10) The pyridazinone compound wherein Ar is a 2,6-diethyl-4-methylphenyl group, and G is a hydrogen atom, an acetyl group, a trifluoroacetyl group, a propionyl group, a butyryl group, an iso-butyryl group , an isovaleryl group, a pivaloyl group, a cyclohexylcarbonyl group, a benzoyl group, a benzylcarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a phenoxycarbonyl group, a dimethylaminocarbonyl group, a methanesulfonyl group, a trifluoromethanesulfonyl group, a sulfonyl group or a p-toluenesulfonyl group in any of formulas (I1) to (I30). (11) The pyridazinone compound wherein Ar is a 2,4,6-triethylphenyl group, and G is a hydrogen atom, an acetyl group, a trifluoroacetyl group, a propionyl group, a butyryl group, an isobutyryl group, an isovaleryl group , a pivaloyl group, a cyclohexylcarbonyl group, a benzoyl group, a benzylcarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a phenoxycarbonyl group, a dimethylaminocarbonyl group, a methanesulfonyl group, a trifluoromethanesulfonyl group or a benzenesulfonyl group -toluenesulfonyl in any of formulas (I1) to (I30). (12) The pyridazinone compound wherein Ar is a 2,4-diethylphenyl group, and G is a hydrogen atom, an acetyl group, a trifluoroacetyl group, a propionyl group, a butyryl group, an isobutyryl group, an isovaleryl group , a pivaloyl group, a cyclohexylcarbonyl group, a benzoyl group, a benzylcarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a phenoxycarbonyl group, a dimethylaminocarbonyl group, a methanesulfonyl group, a trifluoromethanesulfonyl group or a benzenesulfonyl group -toluenesulfonyl in any of formulas (I1) to (I30). (13) The pyridazinone compound wherein Ar is a 2,4-diethyl-6-methylphenyl group, and G is a hydrogen atom, an acetyl group, a trifluoroacetyl group, a propionyl group, a butyryl group, an iso group -butyryl, an isovaleryl group, a pivaloyl group, a cyclohexylcarbonyl group, a benzoyl group, a benzylcarbonyl group, a methoxycarbonyl group, an ethoxycarbonyl group, a phenoxycarbonyl group, a dimethylaminocarbonyl group, a methanesulfonyl group, a trifluoromethanesulfonyl group benzenesulfonyl group or a p-toluenesulfonyl group in any of formulas (I1) to (I30).

Embodiments of the compound represented by formula (II) include, for example, the following embodiments as defined above for the compound represented by formula (II). The compound of formula (II), wherein n is an integer of 1 or more. The compound of formula (II), wherein n is 0, and Z 1 is a C 2-6 alkyl group. The compound of formula (II), wherein n is 1 or 2 and Z 2 is (are) one (4) substituent (s) at the 4 and / or 6 position of the benzene ring. The compound of formula (II), wherein R1 is a C1-3 alkyl group or a (C1 -C4 alkyloxy) C1-3 alkyl group. The compound in formula (II), wherein R2 is a hydrogen atom or a C1-3 alkyl group. The compound of formula (II), wherein R2 is a hydrogen atom or a methyl group. The compound in formula (II), wherein Z1 is a C1-3 alkyl group, and Z2 is a C1-3 alkyl group. The compound of formula (II), wherein R1 is a C1-3 alkyl group or a C1-3 alkyloxy) C1.3 alkyl group, and R2 is a hydrogen atom or a methyl group. The compound in formula (II), wherein R1 is a C1-3 alkyl group or a C (1-3 alkyloxy) C1.3 alkyl group, and R2 is a hydrogen atom or a C1-3 alkyl group, n represents Ο , 1, or 2, and each Z2 may be the same or different when n represents 2, and when n represents 1 or 2, Z2 is (is) a (s) substituent (s) at position 4 and / or 6 of a benzene ring, Z1 is a C1-6 alkyl group (preferably a C1-3 alkyl group), and Z2 is a C1-6 alkyl group (preferably a C1-3 alkyl group). The compound in formula (II), wherein R1 is a C1-3 alkyl group or a C (1-3 alkyloxy) C1.3 alkyl group, and R2 is a hydrogen atom or a methyl group, n represents 0.1, or 2, and each Z 2 may be the same or different when n represents 2, and when n represents 1 or 2, Z 2 is (are) (a) substituent (s) at the 4 and / or 6 position of a benzene ring Z1 is a C1-6 alkyl group (preferably a C1-3 alkyl group), and Z2 is a C1-6 alkyl group (preferably a C1.3 alkyl group).

Embodiments of the compound represented by formula (VI) include, for example, the following embodiments as defined above for the compound represented by formula (VI). The compound of formula (VI), wherein n is an integer of 1 or more. The compound in formula (VI), wherein n is 0, and Z 1 is a C 2-6 alkyl group. The compound in formula (VI), wherein n is 1 or 2 and Z 2 is (are) one substituent (s) at the 4 and / or 6 position of the benzene ring. The compound in formula (VI), wherein R1 is a C1-3 alkyl group or a (C1-3 alkyloxy) C1.3 alkyl group. The compound in formula (VI), wherein R2 is a C1-6 alkyl group. The compound in formula (VI), wherein R2 is a hydrogen atom or a C1.3 alkyl group. The compound in formula (VI) wherein R2 is a C1.3 alkyl group. The compound in formula (VI), wherein R2 is a hydrogen atom or a methyl group. The compound in formula (VI) wherein R2 is a methyl group. The compound in formula (VI), wherein Z1 is a C1-3 alkyl group, and Z2 is a C1.3 alkyl group. The compound in formula (VI) wherein R1 is a C1-3 alkyl group or a (C1.3 alkyloxy) C1-3 alkyl group and R2 is a hydrogen atom or a methyl group. The compound in formula (VI), wherein R1 is a C1-3 alkyl group or a C1-3 alkyloxy) C1.3 alkyl group, and R2 is a hydrogen atom or a C1-3 alkyl group, n represents 0 , 1, or 2, and each Z2 may be the same or different when n represents 2, and when n represents 1 or 2, Z2 is (is) a (s) substituent (s) at position 4 and / or 6 of a benzene ring, Z1 is a C1-6 alkyl group (preferably a C1-3 alkyl group), and Z2 is a C1-3 alkyl group (preferably a C1-3 alkyl group). The compound in formula (VI), wherein R1 is a C1-3 alkyl group or a C1-3 alkyloxy) C1.3 alkyl group, and R2 is a hydrogen atom or a methyl group, n represents 0.1, or 2, and each Z 2 may be the same or different when n represents 2, and when n represents 1 or 2, Z 2 is (are) (a) substituent (s) at the 4 and / or 6 position of a benzene ring Z1 is a C1-6 alkyl group (preferably a C1-3 alkyl group), and Z2 is a C1-4 alkyl group (preferably a C1-3 alkyl group). The present invention will be further illustrated by the following Examples, Reference Examples, Formulation Examples and Test Examples; however, the present invention is not limited to these examples.

In the Examples and Reference Examples, ambient temperature usually means from 10 to 30 ° C. 1H-NMR means proton nuclear magnetic resonance. It is measured with tetramethyl silane as the internal standard, and the chemical shift (δ) is shown by ppm.

The abbreviations used in the Examples and Reference Examples have the following meanings: CDCl3: Chloroform-d, s: singlet, d: doublet, t: triplet, q: quartet, dt: double triplet, dq: double quartet, m: multiplet, br .: broad, J: coupling constant, Me: methyl group, Et: ethyl group, Pr: propyl group, i-Pr: isopropyl group, t-Bu: tert-butyl group, c-Hex: cyclohexyl and Ph: phenyl group.

Example 1 4- (2-Ethylphenyl) -5-hydroxy-2-methyl-3 (2H) -pyridazinone (Compound la-1) After 50 mL of water, 4.657 g of potassium hydroxide (content, 85%) and 5 mL of 1,4-dioxane was added to 3.193 g of 4- (2-ethylphenyl) -5-methoxy-2-methyl-3 (2H) -pyridazinone (Compound 11-1), the mixture was stirred and heated under reflux for 36 hours. After cooling, concentrated hydrochloric acid was added to the reaction mixture to acidify, to which 10 mL of water and 100 mL of ethyl acetate were added. The resulting mixture was filtered to remove insoluble substances, and the filtrate was separated into two phases. The organic layer was washed with water and then a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The obtained solid was washed with a mixed solvent of ethyl acetate and hexane (1: 2) to afford 2.050 g of the title compound as colorless crystals. The present compound which was produced according to Example 1 will be shown in Table 1. The compound represented by the formula (la): (Ia) Table 2 Example 2- (2,6-Diethyl-4-methylphenyl) -5-hydroxy -2,6-dimethyl-3 (2H) -pyridazinone (Compound la-14) Under a nitrogen atmosphere, 13 mL of a tetrahydrofuran solution of potassium tert-butoxide (1 mol / L) was stirred at room temperature, to which a solution of ethyl 2- [2- (2,6-diethyl-4-methylphenylacetyl) -2-methylhydrazono] propanoate (Compound VI-2) in 55 mL of toluene was added dropwise. for about 1 hour. The mixture was further stirred at room temperature for 30 minutes. Then, the reaction mixture was concentrated under reduced pressure. To the obtained residue was added 30 mL of ice water which was extracted with tert-butyl methyl ether (20 mL x 2). To the aqueous layer was then added 1.6 g of 35% hydrochloric acid, which was extracted with ethyl acetate (20 mL x 3). The ethyl acetate extracts were combined, washed with brine (20 mL x 2), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate: hexane = 1: 3 as eluent) to afford 0.76 g of a solid. The solid was washed with cold hexane and air dried to afford 0.59 g of the title compound as a white powder. The present compound which was produced according to Example 2 will be shown in Table 2. The compound represented by the formula (la): (Ia) Table 2 Example 3 5-Benzoyloxy-4- (2-ethylphenyl) -2-methyl-2 (2H) -pyridazinone (Compound 1b-1) To 0.326 g of Compound 1a-1, 12 mL of tetrahydrofuran and 0.40 mL of triethylamine were added. The obtained mixture was cooled with ice, to which 0.25 mL of benzoyl chloride was also added. The mixture was stirred for 10 minutes under ice cooling and then at room temperature for 3 hours. 30 mL of water was added to the reaction mixture, which was extracted with 30 mL of ethyl acetate twice. The extracts were combined, washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was subjected to silica gel column chromatography (as eluent, ethyl acetate: hexane = 1: 2 and then 2: 1) to afford 0.463 g of the title compound as a colorless oil. The present compound which was produced according to Example 3 will be shown in Table 3. The compound represented by the formula (1b): (Ib) Table 3 - Continuation - With respect to the compound which is marked with * in column mp of Table 3, 1H-NMR data are shown below.

Compound 1b-1: 1H-NMR (CDCl3) δ ppm: 1.14 (3H, t, J = 7.7Hz), 2.45 - 2.62 (2H, m), 3.88 (3H, s) , 7.09 - 7.12 (1H, m), 7.15 - 7.20 (1H, m), 7.28 - 7.30 (2H, m), 7.37 - 7.42 (2H, m), 7.55 - 7.60 (1H, m), 7.81 - 7.84 (2H, m), 7.95 (1H, s).

Compound 1b-3: 1H-NMR (CDCl3) δ ppm: 0.94 (3H, t, J = 7.6Hz), 1.13 (3H, t, J = 7.7Hz), 2.27 (2H, dq, J = 1.4.7.6 Hz), 2.38 - 2.56 (2H, m), 3.84 (3H, s), 7.00 - 7.03 (1H, m), 7, 18 - 7.23 (1H, m), 7.30 - 7.35 (2H, m), 7.75 (1H, s).

Compound 1b-6: 1 H-NMR (CDCl 3) δ ppm: 1.13 (3H, t, J = 7.7Hz), 1.10 - 1.22 (5H, m), 1.5-1.7 ( 5H, m), 2.28 (1H, br.), 2.38 - 2.55 (2H, m), 3.84 (3H, s), 6.99 - 7.02 (1H, m), 7.17 - 7.22 (1H, m), 7.29 - 7.36 (2H, m), 7.72 (1H, s).

Compound 1b-8: 1H-NMR (CDCl3) δ ppm: 1.11 (3H, t, J = 7.7Hz), 2.40 - 2.57 (2H, m), 2.64 (3H, s) , 2.85 (3H, s), 3.83 (3H, s), 7.05 - 7.08 (1H, m), 7.19 - 7.24 (1H, m), 7.30-7 , 36 (2H, m), 7.95 (1H, s).

Compound 1b-9: 1H-NMR (CDCl3) δ ppm: 1.18 (3H, t, J = 7.6Hz), 2.43 - 2.57 (2H, m), 2.58 (3H, s) , 3.85 (3H, s), 7.16 - 7.19 (1H, m), 7.25 - 7.30 (1H, m), 7.36 - 7.43 (2H, m), 7 , 96 (1H, s).

A typical example of the preparation of the compound represented by formula (II) is shown in Reference Example 1.

Reference Example 1 4- (2-Ethylphenyl) -5-methoxy-2-methyl-3 (2H) -pyridazinone (Compound 11-1) To a mixture of 2.516 g of 4-chloro-5-methoxy-2-methyl -3 (2H) -pyridazinone, 2.575 g of 2-ethylphenylboronic acid and 3.333 g of sodium carbonate, 30 mL of 1,4-dioxane and 20 mL of water were added. To the mixture were added 2.417 g of tetrabutylammonium bromide and 0.657 g of tetrakis (triphenylphosphine) palladium, and then, under a nitrogen atmosphere, the resulting mixture was stirred and heated at reflux for 17 hours. After cooling, 50 ml of water was added to the reaction mixture, which was extracted with 100 ml of ethyl acetate and then 30 ml of ethyl acetate. The extracts were combined, washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The obtained solid was washed with a mixed solvent of ethyl acetate and hexane (1: 2) to afford 3.238 g of the title compound as yellow crystals. The compound that was produced according to Reference Example 1 will be shown in Table 4. The compound represented by formula (II): (n) Table 4 With respect to the compound that is marked with * in column mp of Table 4, 1H-NMR data will be shown below.

Compound II-2: 1H-NMR (CDCl3) δ ppm: 1.12 (3H, t, J = 7.7Hz), 1.39 (3H, t, J = 7.3Hz), 2.40-2 , 53 (2H, m), 3.81 (3H, s), 4.19 - 4.30 (2H, m), 7.10 (1H, d, J = 7.6 Hz), 7.21-7 , 26 (1H, m), 7.30 - 7.33 (2H, m), 7.88 (1H, s).

Compound II-4: 1H-NMR (CDCl3) δ ppm: 1.12 (3H, t, J = 7.7Hz), 2.38 - 2.52 (2H, m), 3.38 (3H, s) , 3.82 (3H, s), 3.77 - 3.84 (2H, m), 4.40 (2H, t, J = 5.6Hz), 7.11 (1H, d, J = 7, 6Hz), 7.21 - 7.26 (1H, m), 7.30 - 7.34 (2H, m), 7.90 (1H, s).

Compound II-7: 1 H-NMR (CDCl 3) δ ppm: 1.08 (3H, t, J = 7.7Hz), 2.07 (3H, s), 2.30 - 2.45 (2H, m) , 3.81 (3H, s), 3.82 (3H, s), 7.10 (1H, d, J = 7.6Hz), 7.13 (1H, d, J = 7.6Hz), 7 , 24 (1H, t, J = 7.6 Hz), 7.85 (1H, s).

A typical example of the preparation of the compound represented by formula (V-a) is shown in Reference Example 2.

Reference Example 2 2-Propylphenylboronic acid 15.5 mL of butyl lithium (1.6 mol / L hexane solution) was placed in a reaction vessel, which was cooled in a dry-acetone ice bath. To this was added a solution of 2-propylbromobenzene (4.412 g) in tetrahydrofuran (45 ml) at -70Â ° C dropwise over 85 minutes under a nitrogen atmosphere. The mixture was stirred at -70 ° C for 30 minutes, to which was then added 3.75 mL of trimethyl borate at -70 ° C dropwise over 15 minutes. The mixture was stirred at -70 ° C for one hour and then at room temperature for 18 hours. To the reaction mixture was added 33 mL of 2N hydrochloric acid dropwise over 10 minutes and then the mixture was stirred at room temperature for 4 hours. To the mixture was added 20 mL of water, which was extracted with 70 mL of ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off. The residue was subjected to silica gel column chromatography (as eluent, ethyl acetate: hexane = 1: 2, then 2: 1) to afford 1.641 g of the title compound as colorless crystals. 1H-NMR (CDCl3) δ ppm: 1.01 (3H, t, J = 7.4 Hz), 1.69 - 1.79 (2H, m), 3.15 - 3.20 (2H, m), 4, 0 - 6.0 (2H, br.), 7.28 - 7.33 (2H, m), 7.47 (1H, dt, J = 1.5.7.6Hz), 8.20 - 8.23 (1H, m).

Among the compounds represented by formula (Va), the following were produced similarly to Reference Example 2. 2-Ethyl-6-methylphenylboronic acid mp: 90-91 ° C 1H-NMR (CDCl3) δ ppm: 1.22 (3H, t, J = 7.6Hz), 2.35 (3H, s), 2.64 (2H, q, J = 7.6Hz), 4.0 - 5.5 (2H, br.), 6.98 (1H, d, J = 7.7Hz), 7.01 (1H, d, J = 7.7Hz), 7.18 (1H, t, J = 7.7Hz).

2,6-Diethyl-4-methylphenylboronic acid mp: 111-113 ° C 1H-NMR (CDCl3) δ ppm: 1.23 (6H, t, J = 7.7Hz), 2.31 (3H, s), 2.63 (4H, q, J = 7.7 Hz), 4.0 - 5.0 (2H, br.), 6.88 (2H, s).

A typical example of the preparation of the compound represented by formula (VI) is shown in Reference Example 3.

Reference Example 3 Ethyl 2- [2- (2,6-Diethyl-4-methylphenylacetyl) -2-methylhydrazono] propanoate (Compound VI-2) 1.5 g of potassium carbonate was added to a solution of 2, 0 g of ethyl 2- (methylhydrazono) propanoate in 35 ml of acetonitrile. The mixture was stirred under ice cooling, to which a solution of 2.6 g of acetyl 2,6-diethyl-4-methylphenyl chloride in 10 mL of acetonitrile was added dropwise over about 20 minutes. The resulting mixture was further stirred for 3.5 hours at room temperature, and then concentrated under reduced pressure. To the obtained residue was added 20 mL of ice water which was extracted with ethyl acetate (20 mL x 3). The extracts were combined, washed with a saturated aqueous sodium chloride solution (20 mL x 2), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was subjected to basic alumina column chromatography (ethyl acetate: hexane = 1: 3 as eluent) to afford 1.9 g of the title compound as white crystals. The compound that was produced according to Reference Example 3 will be shown in Table 5. The compound represented by formula (VI):> (VI) Table 5 - Continued - With respect to the compound that is marked with * in the column Table 5, 1H-NMR data will be shown below.

Compound VI-3: 1 H-NMR (CDCl 3) δ ppm: 1.1.9 (3H, t, J = 7.6Hz), 1.37 (3H, t, J = 7.2Hz), 2.20 (3H, 2.67 (2H, q, J = 7.7Hz), 3.37 (3H, br.s), 4.03 (2H, br.s), 4.33 (2H, q, J = 7.0 Hz), 7.06 - 7.30 (4H, m).

Compound VI-4: 1 H-NMR (CDCl 3) δ ppm: 1.18 (3H, t, J = 7.6Hz), 1.37 (3H, t, J = 7.2Hz), 2.20 (3H, 2.30 (3H, s), 2.63 (2H, q, J = 7.7Hz), 3.36 (3H, br.s), 3.99 (2H, br.s) , 4.33 (2H, q, J = 7.1 Hz), 6.93 (1H, br.d, J = 7.1 Hz), 7.00 (1H, br.s), 7.12 ( 1H, br.d., J = 7.8 Hz).

VI-6: 1H-NMR (CDCl3) δ ppm: 1.16 (3H, t, J = 7.7Hz), 1.36 (3H, t, J = 7.2Hz), 2.22 (3H, s), 2.27 (3H, s), 2.30 (3H, br.s), 2.56 (2H, q, J = 7.7Hz), 3.39 (3H, br.s), 4 .02 (2H, br.s), 4.32 (2H, q, J = 7.1 Hz), 6.86 (2H, br.s).

Compound VI-7 (E / Z mixture): 1H-NMR (CDCl3) δ ppm: 1.13-1.25 (9H, m), 1.31-1.41 (3H, m), 2.29 ( 3H, s), 2.50 - 2.81 (6H, m), 3.23, 43 (3H, each br.s), 4.05 (2H, br.s), 4.27 - 4 , 39 (2H, m); 6.89 (2H, s).

Compound VI-8 (E / Z mixture): 1 H-NMR (CDCl 3) δ ppm: 1.06 - 1.22 (6H, m), 1.31 - 1.40 (3H, m), 2.30, 2.31 (3H, each s), 2.50 - 2.70 (4H, m), 3.22,3,38 (3H, each s), 4.00 (2H, br.s), 4.27 - 4.37 (2Η, m), 6.90 - 6.98 (1H, m), 6.98 - 7.02 (1H, m), 7.02 - 7.14 (1, m).

Compound VI-9 (E / Z mixture): 1 H-NMR (CDCl3) δ ppm: 1.12 -1.25 (6H, m), 1.31 - 1.41 (3H, m), 2.22 ( 3H, s), 2.27 (3H, s), 2.50 - 2.81 (4H, m), 3.23.43 (3H, each br.s), 4.02 (2H, br.s ), 4.26 - 4.37 (2H, m), 6.87 (2H, br.s).

Compound VI-10 (E / Z mixture): 1 H-NMR (CDCl 3) δ ppm: 1.16-1.24 (3H, m), 1.32 - 1.40 (3H, m), 2.22 ( 6H, s), 2.25 (3H, s), 2.55 - 2.80 (2H, m), 3.23, 43 (3H, each br.s), 4.00 (2H, br s), 4.27 - 4.38 (2H, m), 6.85 (2H, s).

Compound VI-11: 1H-NMR (CDCl3) δ ppm: 1.18 (6H, t, J = 7.6Hz), 1.24 (6H, d, J = 6.8Hz), 1.37 (3H, t, J = 7.1 Hz), 2.29 (3H, s), 2.55 (4H, q, J = 7.6 Hz), 2.85 (1H, septet, J = 6.8 Hz), 3 .22 (3H, s), 4.04 (2H, s), 4.34 (2H, q, J = 7.2 Hz), 6.88 (2H, s). Compound VI-12 (E / Z mixture): 1H-NMR (CDCl3) δ ppm: 1.01 (3H, t, J = 7.4Hz), 1.17 (6H, t, J = 7.6Hz), 1.31 - 1.40 (3H, m), 1.57 - 1.74 (2H, m), 2.30 (3H, s), 2.50 -2.76 (6H, m), 3.22, 3.42 (3H, each s), 4.03.0.05 (2H, each br.s), 4.26 - 4.36 (2H, m), 6.89 (2H, s). Compound VI-13 (E / Z mixture): 1 H-NMR (CDCl 3) δ ppm: 1.13 -1.28 (12H, m), 1.30 - 1.40 (3H, m), 2.50 - 2.80 (8H, m), 3.23, 3.44 (3H, each s), 4.06 (2H, br.s), 4.28 - 4.39 (2H, m), 6.91 (2H, s).

Compound VI-14 (E / Z mixture): 1H NMR (CDCl3) δ ppm: 1.01 (3H, br.t, J = 7.2 Hz), 1.13 - 1.26 (9H, m) 1.30 - 1.40 (3H, m), 1.56 - 1.73 (2H, m), 2.50 - 2.76 (8H, m), 3.22, 3.42 (3H, each ), 4.03, 4.06 (2H, each br.s), 4.26 - 4.37 (2H, m), 6.91 (2H, s).

VI-15: 1 H-NMR (CDCl 3) δ ppm: 1.15 -1.25 (6H, m), 1.37 (3H, t, J = 7.2 Hz), 2.20 (3H, br s), 2.55 - 2.70 (4H, m), 3.36 (3H, br.s), 3.99 (2H, br.s), 4.33 (2H, q, J = 7 , 1 Hz), 6.96 (1H, br.d, J = 7.3 Hz), 7.02 (1H, br.s), 7.15 (1H, br.d, J = 7.8 Hz).

Compound VI-16 (E / Z mixture): 1 H-NMR (CDCl 3) δ ppm: 1.05 -1.25 (9H, m), 1.32 - 1.40 (3H, m), 2.50 - 2.69 (6H, m), 3.22, 3.38 (3H, each s), 4.00 (2H, br.s), 4.26 - 4.36 (2H, m), 6.93 - 7.00 (1H, m), 7.00 - 7.04 (1H, m), 7.06 - 7.18 (1H, m).

Compound VI-17: 1H-NMR (CDCl3) δ ppm: 1.17 (3H, t, J = 7.6Hz), 1.22 (3H, t, J = 7.6Hz), 1.36 (3H, t, J = 7.1 Hz), 2.24 (3H, s), 2.30 (3H, br.s), 2.58 (4H, q, J = 7.6 Hz), 3.40 (3H, br.s), 4.03 (2H, br.s), 4.32 (2H, q, J = 7.2 Hz), 6.89 (2H, s).

Compound VI-18: 1H-NMR (CDCl3) δ ppm: 1.19 (6H, t, J = 7.6Hz), 1.36 (3H, t, J = 7.2Hz), 2.32 (3H, 2.60 (4H, q, J = 7.7Hz), 3.40 (3H, br.s), 4.09 (2H, br.s), 4.33 (2H, q, J = 7.2 Hz), 7.07 (2H, d, J = 7.6 Hz), 7.18 (1H, t, J = 7.6 Hz).

Formulation Example 1 Emulsifiable Concentrate Compound 1-to-1 20 wt% polyoxyethylene alkyl ether 5 wt% dimethylformamide 18 wt%; and 57% by weight xylene are mixed to provide an emulsifiable concentrate. The prepared emulsifiable concentrate is used after being properly diluted with water.

Compounds 1-a-2 to 1-a-23 and 1-b-1 to 1-b-23, instead of Compound 1-a-1, are also formulated to provide the emulsifiable concentrate for each compound.

Formulation Example 2 Wetting powder Compound 1-b-2 50 wt% sodium lignin sulfonate 5 wt% polyoxyethylene alkyl ether 5 wt% white carbon 5 wt%; and 35% by weight clay are pulverized and mixed to provide a wettable powder. The prepared wettable powder is used after being properly diluted with water. Formulation Example 3 Granule Compound I-a-12 1.5 wt% sodium lignin sulfonate 2 wt% talc 40 wt%; and 56.5 wt% bentonite are mixed, kneaded with water and pelletized to provide granules.

Formulation Example 4 Ten parts of Compound (la-12), 10 parts of any of the following Group A selected compounds, 4 parts sodium lauryl sulfate, 2 parts calcium lignin sulfonate, 20 parts synthetic hydrated silica and 54 parts of diatomaceous earth are pulverized and well mixed to provide wetting powder.

Group A 2,4-PA, MCP, MCPB, phenothiol, mecoprop, fluroxipir, triclopyr, clomeprop, naproanilide, 2,3,6-TBA, dicamba, clopiralid, picloram, quinclorac, quinmerac, diuron, linuron, chlortoluron, isoproturon, fluometuron, isouron, tebutiuron, metabenztiazuron, cumiluron, daimuron, methyl-daimuron, atrazine, ametorin, cyanazine, simazine, propazine, symmetrin, dimetamethrin, promethrin, metribuzin, triaziflam, paraquatoxin, paraquatoxin, paraquinatine trifluralin, amiprofos-methyl, butamiphos, bensulide, piperofos, anilofos, glyphosate, glufosinate, bialaphos, dialate, trialate, EPTC, butylate, bentiocarb, esprocarb, molinate, dimepiperate, swep, chlorprofam, fenmedifam, pirate, fenisamam propanyl, propyzamide, bromobutide, etobenzanid, acetochlor, alachlor, butachlor, dimethenamid, propachlor, metazachlor, metolachlor, pretylachlor, tenylchlor, petoxamid, acifluorfen-sodium, bifenox, oxyfluorfen, lactofen, fomesalonin, oxo-propylene oxo on, cinidon-ethyl, carfentrazone-ethyl, surfentrazone, flu-michlorac-pentyl, flumioxazin, piraflufen-ethyl, oxadiargyl, pentoxazone, flutia-ket-methyl, butafenacil, benzfendizone, benzofenap, pyrazolate, pyrazoxifen, topazole benzobicyclon, sulcotrione, mesotrione, tembotrione, tefuriltrione, clodinafop-propargyl, cyalofop-butyl, diclofop-methyl, phenoxa-prop-ethyl, fluazifop-methyl, quizalofop-ethyl, metamifop, aloxydimide, soxidimide, aloxydimide, soxidimide, clethodim, cloproxidim, cycloxidim, tepraloxidim, tralcoxidim, profoxidim, clorsulfuron, sulfometuron-methyl, metsulfuron-methyl, chlorimu-ron-methyl, trienulfuron, bensulfuron-methyl-sulfonyl, tifensyl-sulfonyl primisulfuron-methyl, nicosulfuron, amidosul-furon, cinosulfuron, imazosulfuron, rimsulfuron, halosulfuron-methyl, prosul-furon, etametsulfuron-methyl, flazasulfuron, cyclosulfamuron, flupirsulfuron, azuphosulfuron ulfuron, ethoxysulfuron, oxasulfuron, iodosulfuron-methyl sodium, foramsulfuron, mesosulfuron-methyl, trifloxysulfuron, tritosulfuron, imazametapyr, imazamox, imazapir, i-mazaquin, flasulurulamulululfuramulamulamulamulamulamulamuron chloransu-lam-methyl, penoxsulam, pyroxsulam, pyrithiobac-sodium, bispyribac-sodium, pyriminobac-methyl, pyribenzoxim, piriftalid, pirimisulfan, bentazon, bromacil, terbacil, chlortiamid, isoxaben, dinoseb, aminitrin cintrin, dalapon, diflufenzopyr-sodium, dithiopyr, thiazopyr, flucar-bazone-sodium, propoxycarbazone-sodium, mefenacet, flufenacet, fentrazamide, cafenstrol, indanofan, oxaziclomefone, benfuresate, ACN, pyridate, chloridazon, norflamuron, piperidazone clomazone, amicarbazone, pinoxaden, piraclonyl, pyroxasulfone, thiencarbazone-methyl, furilazole, diclormid, benoxacor, alidochlor, isoxadifen-ethyl, fenclo-razol-ethyl, mefenpir-diethyl, cloquintocet-methyl, phenlorim, cyprosulfamide, cytometrinyl, oxabetrinyl, fluxophenim, flurazole and 1,8-naphthalic anhydride.

Formulation Example 5 Ten parts Compound (la-13), 10 parts any of the above selected Group A compounds, 4 parts sodium lauryl sulfate, 2 parts calcium lignin sulfonate, 20 parts hydrated silica Synthetic and 54 parts of diatomaceous earth are pulverized and well mixed to provide wetting powders.

Formulation Example 6 Ten parts Compound (la-14), 10 parts any of the above selected Group A compounds, 4 parts sodium lauryl sulfate, 2 parts calcium lignin sulfonate, 20 parts hydrated silica Synthetic and 54 parts of diatomaceous earth are pulverized and well mixed to provide wetting powders.

Formulation Example 7 Ten parts of Compound (1a-15), 10 parts of any of the above selected Group A compounds, 4 parts sodium lauryl sulfate, 2 parts calcium lignin sulfonate, 20 parts hydrated silica Synthetic and 54 parts of diatomaceous earth are pulverized and well mixed to provide wetting powders.

Formulation Example 8 Ten parts Compound (la-16), 10 parts any of the above selected Group A compounds, 4 parts sodium lauryl sulfate, 2 parts calcium lignin sulfonate, 20 parts hydrated silica Synthetic and 54 parts of diatomaceous earth are pulverized and well mixed to provide wetting powders.

Formulation Example 9 Ten parts of Compound (la-17), 10 parts of any of the above-selected Group A compounds, 4 parts sodium lauryl sulfate, 2 parts calcium lignin sulfonate, 20 parts hydrated silica Synthetic and 54 parts of diatomaceous earth are pulverized and well mixed to provide wetting powders.

Formulation Example 10 Ten parts of Compound (la-18), 10 parts of any of the above selected Group A compounds, 4 parts sodium lauryl sulfate, 2 parts calcium lignin sulfonate, 20 parts hydrated silica Synthetic and 54 parts of diatomaceous earth are pulverized and well mixed to provide wetting powders.

Formulation Example 11 Ten parts of Compound (la-19), 10 parts of any of the above selected Group A compounds, 4 parts sodium lauryl sulfate, 2 parts calcium lignin sulfonate, 20 parts hydrated silica Synthetic and 54 parts of diatomaceous earth are pulverized and well mixed to provide wetting powders.

Formulation Example 12 Ten parts Compound (1b-12), 10 parts any of the above selected Group A compounds, 4 parts sodium lauryl sulfate, 2 parts calcium lignin sulfonate, 20 parts hydrated silica Synthetic and 54 parts of diatomaceous earth are pulverized and well mixed to provide wetting powders.

Formulation Example 13 Ten parts Compound (1b-14), 10 parts any of the above selected Group A compounds, 4 parts sodium lauryl sulfate, 2 parts calcium lignin sulfonate, 20 parts hydrated silica Synthetic and 54 parts of diatomaceous earth are pulverized and well mixed to provide wetting powders.

Formulation Example 14 Ten parts Compound (1b-16), 10 parts any of the above selected Group A compounds, 4 parts sodium lauryl sulfate, 2 parts calcium lignin sulfonate, 20 parts hydrated silica Synthetic and 54 parts of diatomaceous earth are pulverized and well mixed to provide wetting powders.

Formulation Example 15 Ten parts Compound (1b-18), 10 parts any of the above selected Group A compounds, 4 parts sodium lauryl sulfate, 2 parts calcium lignin sulfonate, 20 parts hydrated silica Synthetic and 54 parts of diatomaceous earth are pulverized and well mixed to provide wetting powders.

Formulation Example 16 Ten parts Compound (1b-19), 10 parts any of the above selected Group A compounds, 4 parts sodium lauryl sulfate, 2 parts calcium lignin sulfonate, 20 parts hydrated silica Synthetic and 54 parts of diatomaceous earth are pulverized and well mixed to provide wetting powders.

Formulation Example 17 Ten parts Compound (1b-20), 10 parts any of the above selected Group A compounds, 4 parts sodium lauryl sulfate, 2 parts calcium lignin sulfonate, 20 parts hydrated silica Synthetic and 54 parts of diatomaceous earth are pulverized and well mixed to provide wetting powders.

Formulation Example 18 Ten parts Compound (1b-21), 10 parts any of the above selected Group A compounds, 4 parts sodium lauryl sulfate, 2 parts calcium lignin sulfonate, 20 parts hydrated silica Synthetic and 54 parts of diatomaceous earth are pulverized and well mixed to provide wetting powders.

Formulation Example 19 Ten parts of each of Compounds (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), 18), (1a-19), (1b-12), (1b-14), (1b-16), (1b-18), (1b-19), (1b-20) or (1b-21) ; 10 parts flumioxazine; 4 parts of sodium lauryl sulfate; 2 parts calcium lignin sulfonate; 20 parts synthetic hydrated silica and 54 parts diatomaceous earth are pulverized and well mixed to provide wetting powders.

Formulation Example 20 Five parts of each of Compounds (la-12), (la-13), (la-14), (la-15), (la-16), (la-17), 18), (1a-19), (1b-12), (1b-14), (1b-16), (1b-18), (1b-19), (1b-20) or (1b-21) ; 25 parts glyphosate; 4 parts sodium lauryl sulphate; 2 parts calcium lignin sulfonate; 20 parts synthetic hydrated silica and 44 parts diatomaceous earth are pulverized and well mixed to provide wetting powders.

Test Example 1: Dry Field Post-Emergency Treatment Test An 8 cm diameter plastic beaker 6.5 cm deep was filled with commercially available soil from which seeds of Lolium multiflorum were sown, covered with soil about 0.5 cm high and then grown in a greenhouse. When the plants had grown to the first to second leaf stage, a prescribed dosage of a diluted liquid formulation comprising Compound 1-a-1 was uniformly sprayed onto the whole plants. The diluted liquid formulation was prepared by dissolving a prescribed amount of Compound la-1 in a solution in dimethylformamide (2%) of Tween 20 (polyoxyethylene sorbitan fatty acid ester from MP Biomedical, Inc.) and then , dilution with deionized water. Plants after treatment with the liquid formulation were grown in a greenhouse, and 20 days after treatment the efficacy of the compound against Lolium multiflorum was visually assessed by grading at eleven levels from 0 to 10 (assigned 0 for no effect and 10 for complete death, whereas values between these values were appropriately rated from 1 to 9 levels).

The other present compounds and Compound A are described in J. Heterocycl. Chem., Vol. 42, pp. 427-435 (2005) as a comparative example were also tested.

Comparative Example (Compound A) As a result, Compounds la-1, la-5, la-6, la-7, la-8, la-9, la-12, lb-1, lb-2, lb-4 , lb-5, lb-7, lb-10 and lb-11 showed an egress of 7 or more at a treatment dosage of 500 g / ha, whereas Compounds la-13, la-14, la-15, la-16, la-17, la-18, la-19, la-20, la-21, la-22, la-27, lb-12, lb-13, lb-14, lb- 16.1b-17, 1b-18, 1b-20, 1b-21, 1b-22, 1b-23 and 1b-25 showed an effect equal to 7 or more at a treatment dosage of 250 g / ha. In contrast, Compound A showed an effect of 1 at a treatment dosage of 500 g / ha.

Test Example 2: Dry Field Preemergence Treatment Test A plastic container (32 cm x 22 cm x 8 cm high) was filled with steam-sterilized soil on which seeds of Apera spica-venti were sown. and covered with soil about 0.5 cm high. A prescribed dosage of a diluted liquid formulation comprising Compound 1-a-1 was uniformly sprayed onto the soil surface. The diluted liquid formulation was prepared by a method similar to Test Example 1. Plants, after treatment with the liquid formulation, were grown in a greenhouse and, three weeks after treatment, the efficacy of the compound against Apera spica-venti. was visually assessed by grading at eleven levels from 0 to 10, similar to Test Example 1.

The other present compounds and Compound A as a comparative example were also tested.

As a result, Compounds la-1, la-2, la-4, la-5, la-6, la-8, la-9, la-10, lb-1, lb-5, lb-6, lb -7 and 1b-11 showed an effect of 8 or more at a treatment dosage of 500 g / ha, whereas Compounds la-12, la-13, la-14, la-15, la-16, la-17, la-18, la-19, la-20, la-21, la-22, la-23, lb-13, lb-14, lb-16, lb-18, lb-19, lb- 20, lb-21, lb-22, and lb-23 showed an effect of 8 or more at a treatment dosage of 250 g / ha. In contrast, Compound A showed an effect of 1 at a treatment dosage of 500 g / ha.

Industrial Applicability This compound has an excellent effect on weed control and is usable as an active herbicide ingredient.

Claims (13)

Pyridazinone compound, characterized in that it is represented by formula (I): wherein, in the formula, R1 represents a C1-6 alkyl group or a C1-6 alkyl (C1-5 alkyloxy) group, R2 represents a hydrogen atom or a C1-6 alkyl group, G represents a hydrogen atom, a group represented by the formula, or a group represented by the formula, (wherein, in the formula, L represents an oxygen or sulfur atom, R3 represents a C1-6 alkyl group, a Cs-β cycloalkyl group, a C% 6 alkyloxy group, a C3-8 cycloalkyloxy group, a C2-6 alkenyloxy group, a C2-6 alkynyloxy group, a C10-10 aryloxy group, a (C10-10 aryl) C1-6 alkyloxy, an amino group, or a C1-6 alkylamino group, R4 represents a C1-6 alkyl group, and Z1 represents a C1-6 alkyl group, Z2 represents a C1-6 alkyl group, n represents 0, 1 or 2, and each Z 2 may be the same or different when n represents an integer of 2, and the sum of the number of carbon atoms in the group re represented by Z1 and in the group represented by Z2 is equal to 2. Pyridazinone compound according to claim 1, characterized in that n is an integer equal to 1 or more. Pyridazinone compound according to claim 1, characterized in that n is 0, and Z 1 is a C 2-6 alkyl group. Pyridazinone compound according to claim 1, characterized in that n is 1 or 2 and Z 2 is (are) one (4) substituent (s) at the 4 and / or 6 position of a benzene ring. Pyridazinone compound according to claim 1, characterized in that Z1 is a C1-3 alkyl group, and Z2 is a C1-3 alkyl group. Pyridazinone compound according to claim 1, characterized in that R2 is a hydrogen atom or a C1-3 alkyl group. Pyridazinone compound according to claim 1, characterized in that R2 is a hydrogen atom or a methyl group. Pyridazinone compound according to claim 1, characterized in that R1 is a C1-3 alkyl group or a (C1-3 alkyloxy) C1-3 alkyl group. Herbicide, characterized in that it comprises the pyridazinone compound as defined in claim 1 as an active ingredient. Weed control method, characterized in that it comprises a step wherein an effective amount of the pyridazinone compound as defined in claim 1 is applied to weeds or the soil where weeds grow. Use of the pyridazinone compound as defined in claim 1, characterized in that it is for weed control. Compound, characterized in that it is represented by formula (II): (n) wherein, in the formula, R7 represents a C1-6 alkyl group, R1, R2, Z1, Z2 and n have the same meaning as defined in claim 1. 13. A compound characterized by the fact that it is represented by formula (VI): wherein, in the formula, R 9 represents a C 1-6 alkyl group, R 1, R 2, Z 1, Z 2 and n have the same meaning as defined in claim 1.