WO1992000976A1

WO1992000976A1 - Pyridine derivative and selective herbicide

Info

Publication number: WO1992000976A1
Application number: PCT/JP1991/000918
Authority: WO
Inventors: Hiromi Sano; Soji Sugai; Takeshi Endo; Masahiro Shindo; Toyokuni Honma
Original assignee: Sankyo Company, Limited
Priority date: 1990-07-12
Filing date: 1991-07-10
Publication date: 1992-01-23

Abstract

A novel pyridine derivative represented by general formula (I), which has a significantly potent herbicidal activity and a high selectivity against various crops. In the said formula, Q represents Q-1 or Q-2, wherein X represents oxygen or sulfur and R?5 and R6¿ may be the same or different from each other and each represents C¿1? to C6 alkyl or R?5 and R6¿ may be combined together to represent C¿3? or C4 alkylene; R?1, R2 and R3¿ may be the same or different from one another and each represents hydrogen or halogen; and R4 represents optionally mono- or disubstituted amino, substituted hydroxy or substituted thio, or alternatively R?3 and R4¿ may be combined together to form -CH=CH-CH=CH-.

Description

Description Pyridine derivatives and selective herbicides

[Technical field]

The present invention relates to a novel pyridine derivative having excellent herbicidal activity and a selective herbicide containing the same as an active ingredient.

[Background technology]

As compounds having a pyridine 璟 and imide skeleton, compounds described in U.S. Pat.No. 4072499, U.S. Pat.No.4406690 and German Offenlegungsschrift 3917169 are known.However, U.S. Pat. It only mentions the growth-regulating effect on plants, and the herbicidal effect is not described as being slightly observed in legumes when treated at a high dose (6.0 kg / ha). The herbicidal activity against plants other than legumes, such as various weeds that have a great disadvantage in yield of agricultural products, is completely unknown.

Also, US Patent No. 4,406,690 describes herbicidal activity, but the dosage is described as being high, and its potency> is not mentioned about its selectivity for various crops. Furthermore, German Offenlegungsschrift 3917169 states that the claims are not fully supported by the illustrations and examples of the concrete ligatures, and that the claims do not mention crop selectivity or herbicidal spectrum. It has not been.

[Disclosure of the Invention]

The present inventors have conducted intensive studies and found that the compound of the present invention and the herbicidal composition can be sufficiently treated at a low dose in both the pretreatment for weed development and the treatment during the weed growing period. They have found that they have an extremely strong herbicidal activity and high selectivity for many crops, and have completed the present invention. (Structure of the invention)

The herbicidally active pyridine derivative of the present invention has the general formula (I-:

(I)

_T represented by

—In the general formula (I), Q represents the following (α-1) or (Q-2)!

(Wherein X represents an oxygen atom or a sulfur atom, and R ^s and R ^s are the same or different and represent an alkyl group having 1 to 6 carbon atoms, or R ⁵ and a force ^s —

Shows 3 or 4 alkylene groups. )

R ¹ , R ² and R ³ are the same or different and represent a hydrogen atom or a halogen atom, and R ⁴ is an amino group optionally having one or two substituents selected from the following group A, Represents a substituted oxy group having a selected substituent or a substituted thio group having a substituent selected from the following group B, or R ³ and R ⁴ are linked to form a compound of the formula CH = CH—CH = It may form a group represented by CH—.

[Group A]

An alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, and an alkynyl group having 2 to 6 carbon atoms.

[Group B]

An alkyl group having 1 to 6 carbon atoms which may have a substituent selected from the following group C, an alkenyl group having 2 to 6 carbon atoms which may have a substituent selected from the following group C and It may have a substituent selected from the following group C. Alkyl having 2 to 6 carbon atoms Nyl group.

[Group C]

Alkoxycarbonyl group having 1 to 6 carbon atoms, alkenyloxycarbonyl group having 2 to 6 carbon atoms and alkynyloxycarbonyl group having 2 to 6 carbon atoms

As described above, the “alkyl group having 1 to 6 carbon atoms” in R ⁵ , R ⁶ , group A and group B includes, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, S-butyl, t-butyl -Butyl, n-pentyl, isopentyl, 2-methylbutyl, neopentyl, n-hexyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 3,3-dimethylbutyl, 2,2-dimethylbutyl, A linear or branched alkyl group having 1 to 6 carbon atoms such as 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,3-dimethylbutyl, etc. An alkyl group having 1 to 4 carbon atoms, more preferably an alkyl group having 1 to 2 carbon atoms.

Aforementioned as "R ⁵ and R ⁶ connexion alkylene group having 3 or 4 carbon such together", for example propylene, a straight-chain or branched al Killen group having 3 or 4 carbon atoms, butylene, It is preferably a straight-chain alkylene group having 3 or 4 carbon atoms, and more preferably a straight-chain alkylene group having 4 carbon atoms.

The “halogen atom” in R ¹ , R ² and R ³ described above is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, preferably a fluorine atom or a chlorine atom, and more preferably a fluorine atom. It is.

The “alkenyl group having 2 to 6 carbon atoms” in the groups A and B described above includes, for example, butyl, aryl, 1-methyl-2-bromonyl, 2-methyl-2-bromonyl, Ethyl-2-propenyl, 2-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 1-ethyl-2-butul, 3-butenyl, 1-methyl 3-butenyl, 2-methyl-3-buteni, 1-ethyl-3-buteni, 2-penten, 1-methyl-2-pentene, 2-meth-2-penten, 3- Penteni, 1-Methyl-3-Penchi, 2-Meth--3 -Pente, 4-Pente, i-Methyl-4-Pente, 2-Men A straight-chain or branched alkenyl group having 2 to 6 carbon atoms such as 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl and the like; preferably having 2 to 4 carbon atoms. It is a straight-chain or branched-chain alkenyl group, more preferably a straight-chain alkenyl group having 3 to 4 carbon atoms, and most preferably a straight-chain alkenyl group having 3 carbon atoms.

The “alkynyl group having 2 to 6 carbon atoms” in Groups A and B described above is, for example, ethynyl, 2-propynyl, 1-methyl-2-propynyl, 2-methyl-2-propynyl, 2-ethyl 2-propynyl, 2-butul, 1-methyl-2-butynyl, 2_methyl-2-butynyl, 1-ethyl-2-butynyl, 3-butynyl, 1-methyl-3-butynyl, 2-methyl- 3-butul, 1-ethyl-3-butul, 2-pentynyl, 1-methyl-2-pentynyl, 2-methyl-2-pentynyl, 3-pentynyl, 1-methyl- 3-pentynyl, 2-methyl- 3-pentynyl, 4-penturyl, 1-methyl-4-pentynyl, 2-methyl-4-II. Carbon number 2 such as intinyl, 2-hexyl, 3-hexynyl, 4-hexynyl, 5-hexyl A straight-chain or branched alkynyl group having 3 to 6 carbon atoms, preferably a straight-chain or branched alkynyl group having 3 to 6 carbon atoms. More preferably a straight-chain or branched alkynyl group having 3 to 4 carbon atoms, more preferably a straight-chain alkynyl group having 3 to 4 carbon atoms, most preferably It is a straight-chain alkynyl group having 3 carbon atoms.

The “C1 to C6 alkyloxycarbonyl group” in Group C described above refers to the “C1 to C6 alkyloxycarbonyl group” in which the above “C1 to C6 alkyl group” is bonded to an oxygen atom. A group is a group bonded to an s' carbonyl group. The “alkyl group having 1 to 6 carbon atoms” in this case is preferably an alkylyl group having 1 to 4 carbon atoms, and more preferably an alkyl group having 1 to 2 carbon atoms.

The “alkenyloxycarbonyl group having 2 to 6 carbon atoms” in the aforementioned group C refers to “alkenyl group having 2 to 6 carbon atoms” in which the above “alkenyl group having 2 to 6 carbon atoms” is bonded to an oxygen atom. A group bonded to a carbonyl group. The “alkenyl group having 2 to 6 carbon atoms” in this case is preferably a straight-chain or branched alkenyl group having 2 to 4 carbon atoms, more preferably a straight-chain or branched alkenyl group having 3 to 4 carbon atoms. It is a straight-chain alkenyl group, most preferably a straight-chain alkenyl group having 3 carbon atoms. The “alkynyloxycarbonyl group having 2 to 6 carbon atoms” in the aforementioned group C refers to “alkynyl group having 2 to 6 carbon atoms” in which the above “alkynyl group having 2 to 6 carbon atoms” is bonded to an oxygen atom. Oxy group ”is a group bonded to a carbonyl group. The “alkynyl group having 2 to 6 carbon atoms” in this case is preferably a straight-chain or branched alkynyl group having 3 to 6 carbon atoms, more preferably a straight-chain or branched alkynyl group having 3 to 6 carbon atoms. A straight-chain or branched-chain alkynyl group, more preferably a straight-chain alkynyl group having 3 to 4 carbon atoms, still more preferably a straight-chain alkynyl group having 3 to 4 carbon atoms, most preferably Is a straight-chain alkynyl group having 3 carbon atoms.

The aforementioned “amino group optionally having one or two substituents selected from group A” in R ⁴ is an unsubstituted amino group such as ethylamino, isopropylamino, n-butylamino, t-butylamino. Child amino, 3-methylbutylamino, 3,3-dimethylbutylamino, arylamino, trimethyl 2-propenylamino, 2-methyl-2-provenylamino, 2-butenylamino, 3-butyramino, 3-methyl-2-butenyla Substituent selected from group A such as mino, 2-pentenylamino, 2-propynylamino, 1-methyl-2-propynylamino, 2-butynylamino, 3-butynylamino, 2-pentynylamino, etc. Have amino groups, such as dimethylamino, getylamino, diisopropylamino, di (π-butyl) amino, di (: t-butylamino, di (3-methylbutyl) ) Amino, di (3,3-dimethylbutyl; 'amino, diarylamino, di (1-methyl-2-propenyl) amino, di (2-methyl-2-probenyl) amino, di (2- Butenyl) amino, di (3-butenyl) amino, di (3-methyl ^ -butenyl) amino, di (2-pentenyl) amino, di (2-propynyl) amino, di (1-methyl-2-propyl) An amino group having two identical substituents selected from group の such as amino, di (2-butynyl) amino, di (3-butulyl) amino, di (2-pentynyl) amino, or N-methyl- N-ethylamino, N-ethylisopropylamino, N-ethyl-Ν-Π-propionic amino, '-1-buty' amino ditylamino, N-f3-methylethylamino-N-methylamino, aryl儿--Methylamino, Aryl -N- Ditylamino, N-Aryl-N- Isoprobi; Reamino, '-(. 3-Methyl 2-butul)-Ditylamino, Ν-aryl- ·--Butyamino,'-Nichi; Shi-:--Brobinini) Group A such as aminoamino, N-ethyl-N- (trimethyl 2-propynyl) amino, Ν-η-butyl (2-propynyl) amino, Ν- (t-butyl) N- (2-probutyl) amino An amino group having two different substituents selected from the group consisting of, preferably, an amino group having one substituent selected from the group A or having two identical substituents selected from the group A. An amino group, more preferably an amino group having one substituent selected from the group A. In this case, the substituent in Group A is preferably an alkenyl group having 2 to 6 carbon atoms and an alkynyl group having 2 to 6 carbon atoms, and more preferably an alkynyl group having 2 to 6 carbon atoms. is there.

The “substituted oxy group having a substituent selected from Group B” in R ⁴ described above includes, for example, methoxy, ethoxy, π-propoxy, isopropoxy, n-butoxy, 1-methylpropoxy, Methylpropoxy, t-butoxy, 3-methylbutoxy, π-pentyloxy, 3,3-dimethylbutoxy, vinyloxy, aryloxy, 1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy 2-butenyloxy, 3-butenyloxy, 3-methyl-2-butenyloxy, 3-pentenyloxy, 2-propynyloxy, 1-methyl-2-propynyloxy, 2-butynyloxy, 1-methyl-2-butynyloxy, 3- Butynyloxy, 4-pentynyloxy, methoxycarbonylmethyloxy, ethoxycarbonylmethyloxy, isopropoxycarbonylmethyloxy n-butoxycarbonylmethyloxy, t-butoxycarbonylmethyloxy, (2-methylpropoxy) carbonylmethyloxy, n-pentyloxycarbonylmethyloxy, 3,3-dimethylbutoxycarbonylmethyloxy, (2- (Propenyloxy) carbonylmethyloxy, (2-methyl-2-propenyloxy) carbonylmethyloxy, (3-butenyloxy) carbonylmethyloxy, (3-methyl-2-butenyloxy) carbonylmethyloxy, ( 2-propynyloxy) carbonylmethyloxy, (1-methyl-2-propynyloxy) carboxymethyloxy, (1-ethyl-2- propyloxy) carbonylmethyloxy, (3-butyroxy) carbonylmethyloxy 1-methoxycarbonylethyloxy, 1-ethoxycarbonyl Ruokishi, 1-I source propoxycarbonyl E chill O carboxymethyl, 1- (n-butoxy) carbonyl E chill O alkoxy, 1 - (t-butoxy ') carbonylation 儿 E Ji -Roxy, 1- (2-methylpropoxy) carbonylethyloxy, 1- (π-pentyloxy) carbonylethyloxy, 1- (3,3-dimethylbutoxy) carboxyleoxy, 1- (2-Brodenyloxy) carbonylethyloxy, 1- (2-methyl-2-bromodioxy) carbonylethyloxy, 1- (3-butenyloxy) carbonylethyloxy, 1- (3-methyl 2-butenyloxy) carbonylethyloxy, 1- (2-propynyloxy) carbonylethyloxy, tri (1-methyl-2-propynyloxy) carbonylethyloxy, 1- (1-ethyl- 2-propynyloxy) force Luponylethyloxy, (3-butynyloxy) carbonylethyloxy, 1-methoxycarbonylpropyloxy, 1-ethoxycarbonylpropyloxy, 1-isopropoxycal Nilbropyroxy, 1- (n-butoxy) carbonylpropyloxy, 1- (t-butoxy) carbonylpropyloxy, 1- (2-methylpropoxy) carbonylpropyloxy, 1- (π-pentyloxy) carbonylpropyloxy 1- (3,3-dimethylbutoxy) carbonylpropyloxy, 1- (2-propenyloxy) carbonylpropyloxy, 1- (2-methyl-2-propenyloxy) carbonylpropyloxy Xy, 1- (3-butenyloxy) carbonylpropyloxy, 1- (3-methyl-2-butyroxy) carbonylpropyloxy, 1- (2-propynyloxy) carbonylpropyl, i- (1-methyl- 2-P-G-Pinyloxy) Carbonylpropyloxy, 1-di-ethyl- 2-Pupuroxy) carbonyl Propoxy, 1- (3-Putinyloxy) carbonyl Ropiroxy, 3- (methoxycarbonyl) 2-propenyloxy, 3- (ethoxycarbonyl) 2-propenyloxy, 3- (isopropoxycarbonyl) 2-propenyloxy, 3- (n-butoxycarbonyl) 2- Propenyloxy, 3_ (t-butoxycarbonyl) 2-propenyloxy, 3-{(2-methylpropoxycarbonyl)} 2-propenyloxy, 3- (n-pentyloxycarbonyl) 2-provenyloxy, 3 -{3,3-Dimethylbutoxycarbonyl)} 2-Brodinoxy, 3-{(2-Propoxycarbonyl) 1.2-Propenyloxy, 3-{(2-methyl-2- Prohexoxycarboxy} 2-provenyloxy, 3-{(3-butenyloxycarbonyl j} 2-propenyloxy, 3-{(3-methyl-2-butenyloxy. Ruhoni λ.;} 2-propenyloxy, 3-{(1-methyl-2-propynyloxycarbonyl)} 2-propenyloxy, 3-{(1-ethyl-2-propynyloxycarbonyl)} 2-prop Nyloxy, 3-{(3-butyroxycarbonyl)} 2-propenyloxy, 3- (methoxycarbonyl) trimethyl-2-propenyloxy, 3- (ethoxycarbonyl) 1-methyl-2-pro Benyloxy, 3- (isopropoxycarbonyl) trimethyl-2-propenyloxy, 3- (π-butoxycarbonyl) 1-methyl-2-propenyloxy, 3- (t-butoxycarbonyl) 1-methyl- 2-propenyloxy, 3-{(2-methylpropoxycarbonyl)} 1-methyl-2-propenyloxy, 3- (n-pentyloxycarbonyl) 1-methyl-2-propenyloxy, 3 -{3,3-dimethylbutoxycarbonyl)} 1 -Methyl-2-brodinoxy, 3-{(2-propenyloxycarbonyl)} 1-methyl-2-propenyloxy, 3-{(2-methyl-2-propenyloxycarbonyl )} 1-methyl-2-propenyloxy, 3-{(3-butyroxycarbonyl)} 1-methyl-2-propenyloxy, 3-{(3-methyl-2-butyroxy Carbonyl)} 1-methyl-2-propenyloxy, 3-{(2-propyloxycarbonyl)} 1-methyl-2-propenyloxy, 3-{(1-methyl-2-propynyl 1-methyl-2-propynyloxy, 3- (1-ethyl-2-propynyloxycarbonyl)} 1-methyl-2-propenyloxy, 3-{(3-butynyloxy Carbonyl) 1-methyl-2-propenyloxy, 3- (methoxycarbonyl) 3-methyl-2-propenyloxy, 3- (ethoxycarbonyl) 3-methyl 2-Provenyloxy, 3_ (isopropoxycarbonyl) 3-methyl-2-propenyloxy, 3- (π-butoxycarbonyl) 3-methyl-2-propenyloxy, 3- (t-butoxycarbonyl ) 3-Methyl-2-propenyloxy, 3-{(2-methylpropoxycarbonyl)} 3-methyl-2-propenyloxy, 3- (π-pentyloxycarbonyl) 3-methyl-2-propenyloxy , 3- {3,3-dimethylbutoxycarbonyl)} 3-methyl-2-propenyloxy, 3-{(2-propenyloxycarbonyl)} 3-methyl-2-propenyloxy, 3_ {( 2-methyl-2-propenyloxycarbonyl)} 3-methyl-2-propenyloxycarbonyl, 3-{(. 3-butenyloxycarbonyl)} 3-methyl-2-propenyloxy , 3- {(3-methyl-2-butenyloxyka Bonyl)} 3-Methyl-2-propenyloxy, 3-{(2-propynyloxycarbonyl)} 3-Methyl-2-propenyloxy, 3-{-methyl-2-brovinyloxyca Rubonyl)} 3-Methyl-2-brodinoxy, 3-{(1-ethyl-2-propynyloxycarbonyl)} 3-methyl-2-propenyloxy, 3-{(3-butyroxyl-proponyl)} 3 -Methyl-2-propenyloxy, 3- (methoxycarbonyl) 2-propynyloxy, 3- (ethoxycarbonyl) 2-brovinyloxy, 3- (isopropoxycarbonyl) 2-propynyloxy, 3- (π- Butoxycarbonyl) 2-propynyloxy, 3- (t-butoxycarbonyl) 2-propynyloxy, 3-{(2-methylpropoxycarbonyl)} 2-propynyloxy, 3- (n-pentyloxycarbonyl) 2-propynyloxy, 3- {3,3-dimethyl Rubutoxycarbonyl)} 2-propynyloxy, 3-{(2-propenyloxycarbonyl)} 2-propynyloxy, 3-{(2-methyl-2-brodinoxycarbonyl).} 2 -Propynyloxy, 3-{(3-butenyloxycarbonyl) 2-bromovinyl, 3-{(3-methyl-2-butyroxycarbonyl)} 2-propynyloxy, 3- {(2 -Brovinyloxycarbonyl)} 2-propynyloxy, 3-{{1-methyl-2-propynyloxycarbonyl)} 2-propynyloxy, 3-{(1-ethyl-2-propynyloxy) 2-bromovinyloxy, 3-{(3-butynyloxycarbonyl)} 2-bromovinyloxy, 3- (methoxycarbonyl) 1-methyl-2-propynyloxy, 3- (ethoxycarbonyl) 1 -Methyl-2-butyroxy, 3-('isopropoxycarbonyl) Trimethyl-2-bromovinyloxy, 3- (n-butoxycarbonyl) trimethyl-'2-bromovinyloxy, 3- (t-butoxycarbonyl) 1-methyl-2-propynyloxy, 3-{(2-methyl 1-methyl-2-propynyloxy, 3- (n-pentyloxycarbonyl) 1-methyl-2-propynyloxy, 3- {3,3-dimethylbutoxycarbonyl)} 1- Methyl-2-propynyloxy, 3-{(2-propenyloxy carboxy ')} 1-methyl-2-propynyloxy, 3-{-methyl-2-propyoxycarbonyl)} 1-Methyl-2-Brovini; Reoxy, 3-{(3-Butini pediatric carbonyl)} 1-Methyl-2-Brobiny xybon, 3-\ (3-Meth-2-butenyl )} 1-Methyl-2-Brobinyoxy Carbonyl)} 1-methyl-2-propynyloxy, 3-{(1-methyl-2-propenyloxycarbonyl)} methyl-2-propynyloxy, 3-{(1-ethyl-2-propynyloxy) Xycarbonyl)} is a substituted oxy group such as 1-methyl-2-propynyloxy or 3-{(3-butynyloxycarbonyl) trimethyl-2-propynyloxy. In this case, the substituent in Group B is preferably an alkenyl group having 2 to 6 carbon atoms and an alkynyl group having 2 to 6 carbon atoms, and more preferably an alkynyl group having 2 to 6 carbon atoms. Group.

The “substituted thio group having a substituent selected from Group B” in R ⁴ described above includes, for example, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, 1-methylpropylthio, 2-methylpropyl Thio, t-butylthio, 3-methylbutylthio, ri-pentylthio, 3,3-dimethylbutylthio, vinylthio, arylthio, 1-methyl-2-bromothiol, 2-methyl-2-propenylthio, 2 -Butenylthio, 3-butenylthio, 3-methyl-2-butenylthio, 3-pentenylthio, 2-propynylthio, 1-methyl-2-propynylthio, 2-butynylthio, 1-methyl-2-butynylthio, 3-butynylthio, 4-pentynylthio, methoxycarbonylmethylthio, ethoxycarbonylmethylthio, isopropoxycarbylmethylthio, n-butoxy 2-methylthio, t-butoxycarbonylmethylthio, (2-methylpropoxy) carbonylmethylthio, n-pentyloxycarbonylmethylthio, 3,3-dimethylbutoxycarbonylmethylthio, (2-propenyloxycarbonyl) carbonylmethylthio, ( 2_methyl-2-propenyloxy) carbonylmethylthio, (3-butenyloxy) carbonylmethylthio, (3-methyl-2-buturoxy) carbonylmethylthio, (2-propynyloxy) carbonylmethylthio, (1-Methyl-2-propynyloxy) carbonylmethylthio, (1-ethyl-2-propynyloxy) carbonylmethylthio, (3-butynyloxy) carbonylmethylthio, 1-methoxycarbenylethylthio, 1-ethoxy Carbonylethylthio, 1-isopropoxycarborethyl Thio, 1- (n-butoxy) carbodiethyl thio, 1- (t-butoxy) carbodilethiol, 1- (2-methylpropoxy) carbodiethyl thiol, 1- (n-pentyloxy) carbonylethyl Lucio, 1- (3,3-dimethylbutoxy) Carbonylethylthio, 1- (2-propenyloxy) Carbonylethylthio, 1-f2-methyl-2-propenyloxy) Carbonirylthiol, 1- (3-butyroxy) Carbonylethylthio, 1- (3- Methyl-2-butenyloxy) carbonylethylthio, 1- (2-propynyloxy) carbonylethylthio, 1- (1-methyl-2-propynyloxy) carbonylethylthio, 1- (1-ethyl-2-propynyl) 1- (3-butynyloxy) carbonylethylthio, 1-methoxycarbonylpropylthio, 1-ethoxycarbonylpropylthio, 1-isopropoxycarbonylpropylthio, 1- (π-butoxy) carbonyl Propylthio, 1- (t-butoxy) carbonylpropylthio, 1- (2-methylpropoxy) carbonylpropylthio, 1- (n-pen Roxy) carbonylpropylthio, 1- (3,3-dimethylbutoxy) carbonylpropylthio, 1- (2-bromodioxy) carbonylpropylthio, 1- (2-methyl-2-propenyloxy) ) Carbonylpropylthio, 1-

(3-butenyloxy) carbonylpropylthio, 1- (3-methyl-2-butenyloxy) carbonylpropylthio, 1- (2-propynyloxy) carbonylpropylthio, 1- (1-methyl-2-propynyl) Oxy) carbonylpropylthio, 1- (toluene-2-bromovinyloxy) carbonylpropylthio, 1- (3-butynoxy) force Luponyl propylthio, 3- (toxoxycarbonyl) 2-fluoro Ruthio, 3- (ethoxycarbonyl) 2-propenylthio, 3- (isopropoxykabonyl) 2-probenylthio, 3- (n-butoxycarbonyl) 2, -bromodithio, 3- (t-butoxycarbonyl) 2-propenylthio, 3- {(2-methylpropoxycarbonyl; T} 2-pro- phenylthio, 3- (π-pentyloxycarbonyl) 2-propenylthio, 3- { 3,3-dimethylbutoxycarbonyl) 2-propenylthio, 3-{(2-propenyloxycarbonyl)} 2-propenylthio, 3-{(2-methyl-2-propenyloxycarbonyl)} 2-propenylthio, 3- {(3-butenyloxycarbonyl)} 2-propenylthio, 3- {(3-methyl-2-butenyloxycarbo)} 2-propenylthio, 3--{

(2-propynyloxycarbonyl)} 2-propenylthio, 3- (1-methyl-2-bromovinyloxycarbonyl)} 2-propenylthio, 3-{(1-ethyl-2- 2-propanoloxycarbonyl)} 2-Buco2, 3-{(3-Butyloxycarbonyl }. 2-Propenylthio, 3- (methoxycarbonyl) trimethyl-2-propenylthio 3- (ethoxycarbonyl) 1-methyl-2-propenylthio, 3- (isopropoxycarbonyl) trimethyl-2- Propenylthio, 3- (n-butoxycarbonyl) 1-methyl-2-propenylthio, 3- (t-butoxycarbonyl) 1-methyl-2-propenylthio, 3-{(2-methylpropoxy Carbonyl)} trimethyl-2-propenylthio, 3-

(n-pentyloxycarbonyl) 1-methyl-2-propenylthio, 3- {3,3-dimethylbutoxycarbonyl)} 1-methyl-2-propenylthio, 3-{(2-propenyloxy 1-methyl-2-propenylthio), 3-{(2-methyl-2-propenyloxycarbonyl)} 1-methyl-2-propenylthio, 3-{(3-butenyloxycarbonyl) } 1-methyl-2-propenylthio, 3-{(3-methyl-2-butenyloxycarbonyl)} 1-methyl-2-propenylthio, 3-{(2-propynyloxycarbonyl)} 1 -Methyl-2-bromodithiol, 3-{(1-methyl-2-propynyloxycarbonyl)} 1-methyl-2-propynylthio, 3-{(1-ethyl-2-propynyloxycarbonyl) } 1-methyl-2-propenylthio, 3-{(3-butynyloxycarbonyl)} 1-methyl-2-propenylthio, 3- ( Bok butoxycarbonyl) 3-methyl-2 - propenyl Niruchio, 3- (ethoxycarbonyl) methyl-2-propenyl Niruchio, 3 -

(Isopropoxycarbonyl) 3-methyl-2-propenylthio, 3- (π-butoxycarbonyl) 3-methyl-2-propenylthio, 3- (t-butoxycarbonyl) 3-methyl. Nylthio, 3-{(2-methylpropoxycarbonyl)} 3-methyl-2-propenylthio, 3- (n-pentyloxycarbonyl) 3-methyl-2-propenylthio 3- {3,3 -Dimethylbutoxycarbonyl)} 3-methyl-2-probenylthio, 3- {

(2-propenyloxycarbonyl)} 3-methyl-2-propenylthio, 3-{(2-methyl-2-propenyloxycarbonyl)} 3-methyl-2-propenylthio, 3-{(3-butenyloxycarbonyl)} 3-methyl-2-probenylthio, 3-{(3-methyl-2-butenyloxycarbonyl)} 3-methyl-2-propenylthio , 3-{(2-propynyloxycarbonyl)} 3-methyl-2-propynylthio, 3-{-methyl-2-propynyloxycarbol)} 3-methyl-2-bromodithiol, 3-{(1-Ethyl-2-bromovinyloxycarbonyl)} 3-methyl-2-fucodzulthio, '3- {(3-Bu ₃ -methyl-2-propynylthio, 3- (methoxycarbonyl) 1-methyl-2-propynylthio, 3- (ethoxycarbonyl) 1-methyl-2-provinylthio, 3 -(Isopropoxycarbonyl) 1-methyl-2-propynylthio, 3- (π-butoxycarbonyl) 1-methyl-2-propynylthio, 3- (t-butoxycarbonyl) 1-methyl-2-propynylthio, 3 -{(2-methylpropoxycarbonyl)} methyl-2-'propynylthio, 3- (n-pentyloxycarbonyl) 1-methyl-2-propynylthio, 3- {3,3-dimethylbutoxycarbonyl)} 1 -Methyl-2-propynylthio, 3-{(2-propenyloxycarbonyl)} 1-methyl-2-propynylthio, 3-{(2-methyl-2-propenyloxycarbonyl)} Methyl-2-propynylthio, 3-{(3-butenyloxy Carbonyl)} 1-methyl-2-bromovinylthio, 3-{(3-methyl-2-butenyloxycarbonyl)} 1-methyl-2-propynylthio, 3-{(2-propynyloxycarbonyl)} 1 -Methyl-2-propynylthio, 3-{(1-methyl-2-propynyloxycarbonyl)} 1-methyl-2-brovinylthio, 3-{(1-ethyl-2-propynyloxycarbonyl)} 1 -Substituted thio groups such as -methyl-2-propynylthio and 3-{(3-butyroxycarbonyl)} 1-methyl-2-propynylthio. In this case, as the substituent of the group B, preferably, an alkyl group having 1 to 6 carbon atoms having an alkyloxycarbonyl group having 1 to 6 carbon atoms as a substituent, or 2 to 6 carbon atoms An alkenyl group and an alkynyl group having 2 to 6 carbon atoms, more preferably an alkenyl group having 2 to 6 carbon atoms and an alkynyl group having 2 to 6 carbon atoms, and most preferably 2 to 6 carbon atoms. Alkynyl groups. The aforementioned Q is preferably (Q-1).

X mentioned above is preferably an oxygen atom.

R ⁵ and R ⁶ described above are preferably a methyl group or an alkylene group having 3 or 4 carbon atoms together, more preferably an alkylene group having 3 or 4 carbon atoms together. And most preferably a butylene group.

R ¹ and R ³ described above are preferably a halogen atom, more preferably a fluorine atom or a chlorine atom, and most preferably a fluorine atom.

R ² described above is preferably a hydrogen atom or a hydrogen atom, and more preferably a hydrogen atom. I am a child.

R ⁴ described above is preferably an alkenylamino group having 2 to 6 carbon atoms, an alkynylamino group having 2 to 6 carbon atoms, an alkyloxy group having 1 to 6 carbon atoms, and an alkyloxy group having 2 to 6 carbon atoms. An alkenyloxy group, an alkynyloxy group having 2 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, an alkenylthio group having 2 to 6 carbon atoms, and an alkynylthio group having 2 to 6 carbon atoms Or R ³ together with R ³ to form a group represented by the formula: CH = CH— CH = CH—, more preferably an alkenyloxy group having 2 to 6 carbon atoms, and 2 to 6 carbon atoms Or an alkynylthio group having 2 to 6 carbon atoms or an alkynylthio group having 2 to 6 carbon atoms, more preferably an alkynyloxy group having 2 to 6 carbon atoms or an alkynyloxy group having 2 to 6 carbon atoms. From 6 to 6 alkynylthio groups, most preferably 2 to 6 carbon atoms Which is the Arukiniruokishi group. In the compound represented by the general formula (I),

(1) Q is - a (Q 1) or (Q-2), X is an oxygen atom, a halogen atom R ¹ and R ³ are identical or different and, R ² force ^s hydrogen atom, An amino group in which R ⁴ may have one or two substituents selected from group A, a substituted oxy group having a substituent selected from group B, or a substituted thio group having a substituent selected from group B; R ³ and R ⁴ may be linked together to form a group of the formula CH-CH—CH = CH—, R ⁵ and R ⁶ A compound which is different from a methyl group or a group wherein R ⁵ and R ⁶ are taken together to form an alkylene group having 3 or 4 carbon atoms;

[Group A]

[Group B]

An alkyl group having 1 to 6 carbon atoms, which may have a substituent selected from the following group C; and 2 to 6 carbon atoms, which may have a substituent selected from the following group C: Kenil And an alkynyl group having 2 to 6 carbon atoms which may have a substituent selected from the group and the following group C.

[Group C]

(2) Q is (Q-1) or (Q-2), X is an oxygen atom or a sulfur atom, and R ¹ , R ^2, and R ^s are one or different and are a hydrogen atom or a halogen atom , R ⁴ force himself a 'amino group having 1 or two substituents selected from the group of the following B' a substituent selected from substituted Okishi group or lower IXB 'group having a substituent selected from the group R ³ and R ⁴ may be linked to form a group represented by the formula: CH = CH—CH = CH—, wherein R and ^Re are the same or different A compound having 1 to 6 carbon atoms or an alkyl group having 3 or 4 carbon atoms wherein Rs and R ^s are taken together.

[Α 'group]

An alkenyl group having 2 to 6 carbon atoms and an alkynyl group having 2 to 6 carbon atoms.

[Β 'group]

(3) Q is (Q-1) or (Q-2), X is an oxygen atom, R ¹ and R ³ are the same or different and are halogen atoms, R ² is a hydrogen atom, R ⁴ has an amino group having one or two substituents selected from the group A ', a substituted oxy group having a substituent selected from the group B' or a substituent selected from the group A ' Or P, ^s and R ⁴ may together form a group of the formula CH = CH—CH—CH—, and R ^s Differently A compound which is a tyl group or an alkylene group having 3 or 4 carbon atoms where R ⁵ and R ⁶ are linked to each other;

(4) Q is (Q-1) or (Q-2), X is an oxygen atom, R ¹ , R ² and R ^{3 are the} same or different and are a hydrogen atom or a halogen atom, and R ^{4 is} serial B is a substituted Chio group having location換分selected from "substituent Okishi group or the following B having a substituent selected from group" group, R ⁵ and R ^e is C 1 to carbon atoms the same or different 6 Compounds which are an alkyl group of 3 or 4 or an alkylene group having 3 or 4 carbon atoms in connection with R ⁵ and R ⁶ ;

[B "

(5) Q is (Q-1) or (Q-2), X is an oxygen atom, R ¹ and R ³ are the same or different and are halogen atoms, R ² is a hydrogen atom, R ⁴ is a substituted Chio group having substituents that will be selected from the "substituent Okishi or a group B having a substituent selected from group" group wherein B, R ⁵ and R ^s force ^s the same or different carbon atoms by 1 or a 6 alkyl groups or R ⁵ and R ⁶ force ^s' - compounds connexion is the number 3 or 4 alkylene group having a carbon to cord;

(6) is (Q-1) or (Q-2), X is an oxygen atom, R ¹ and R ^{3 are} independently or differently a fluorine atom or a chlorine atom, and R ² is a hydrogen atom R ⁴ is a substituted oxy group having a substituent selected from the group B "or a substituted thio group having a substituent selected from the group B", and R ⁵ and R ⁶ are the same or different methyl A compound which is an alkylene group having 3 or 4 carbon atoms in connection with the group or the group R or the group R ^s ;

(7) is (Q-1), R ¹ and R ³ are a fluorine atom, R ² is a hydrogen atom, and R ⁴ is a substituted oxy group having a substituent selected from the group B "or A compound which is a substituted thio group having a substituent selected from the group B "and is a butylene group together with R ⁵ and R ^s ; (8) Q is -1) or (Cl-2), X is an oxygen atom, FT, R ² and R ³ are the same or different and are a hydrogen atom or a halogen atom, and R ⁴ has 2 carbon atoms. From 6 to 6 alkynyloxy groups; R ⁵ and R ^6, or different alkyl groups having 1 to 6 carbon atoms; or R ^s and R ⁶ are linked together to reduce the number of carbon atoms to 3 Or a compound which is four alkylene groups;

(9) Q is - a (Q 1) or (Q-2), X is an oxygen atom, R ¹ and R ³ force ^s identical or different halogen atoms, R ² forces a hydrogen atom, R ^{4 is} a alkynyloxy group having 2 to 6 carbon atoms, and RS or RS is a single or different alkyl group having 1 to 6 carbon atoms or R ^s and R ⁶ are taken together. A compound which is an alkylene group having 3 or 4 carbon atoms;

(10) Q is (Q-1), X is an oxygen atom, R ¹ and R ³ are the same or different and are a fluorine atom or a chlorine atom, R ² is a hydrogen atom, and R ⁴ is a carbon atom. R ⁵ and R ^s are the same or different and are methyl groups, or R ^s and R ⁶ are together and are an alkylene group having 3 or 4 carbon atoms. Compound;

(11) Q is (Q-1), R ¹ and R ^s are fluorine atoms, R ² is a hydrogen atom, R ⁴ is an alkynyloxy group having 2 to 6 carbon atoms. , R ⁵ and a force; and a compound which is a butylene group together. Examples of the compound of the present invention include the compounds described in Table 11, but the present invention is not limited to these compounds.

In Table 1, (Q-la) and (Q-lb) represent a structure represented by the following formula, (Q-2) has the same meaning as described above, "" represents a methyl group, “EtJ represents a dityl group,“ nPr J represents a maltopropyl group, “iPr” represents an isopropyl group, “11” represents an aryl group, and “Prg” represents a 2-propyl group.

Table 1

Nore

匕

{Shi} 丄 Q-la 11

Jin -CH = CH-CH = CH-ιϊ) 3 丄 o Δ Q-lacr ri -CH = CH-CH = CH-

3 Q-la CI H -CH = CH-CH = CH-

4 Q-la F H F OMe 120-122

5 Q-la F H CI OMe

6 Q-la F H Br OMe

7 Q-la H H F OMe

8 H H CI OMe

9 Q-la F H F OEt 105-106

10 Q-la F H CI OEt

1 1 Q-la F H Br OEt

12 Q-la CI H F OEt

13 Q-la CI H CI OEt

14 Q-la CI H Br OEt

15 Q-la H H CI OEt.

16 Q-la HH Br OEt β

73 Q-la ― C1 H Br S-nPr

74 Q-la ― H H F S-nPr

75 Q-la ― H H C1 S-nPr

76 Q-la ― H H F S-iPr

77 Q-la ― F H C1 S-iPr

78 Q-la ― F H Br S-iPr

79 Q-la ― C1 H F S-iPr

80 Q-la ― C1 H CI S-iPr

81 Q-la ― H H F S-iPr

82 Q-la ― H H CI S-iPr

83 Q-la-F H F S-All

84 Q-la ― F H CI. S-All

85 Q-la ― F H Br S-All

86 Q-la one C1 H F S-All

87 Q-la ― C1 H CI S-All

88 Q-la ― C] H Br S-All 36

89 Q-la ― H H F S-All 4

90 Q-la ― H H C'l S-All

91 Q-la one F H F S-Prg

92 Q-la ― F H CI S-Prg

93 Q-la one C1 H F S-Prg

94 Q-la ― C1 H CI S-Prg

95 Q-la ― C1 H Br S-Prg

96 Q-la ― H H F S-Prg

97 Q-la H H CI S-Prg

_{98 Q-la FHF OCH 2 CO} :: Et

99 Q-la FH CI OCH ₂ CO _{: s} Et

_{00 Q-la C1 HF OCK 2} CO:: Et 〇 1 Q- -la-CI H CI OCH ₂ e0 ₂ Et

〇 2 a- -la one HHF OCH ₂ C0 ₂ Et

03 Q- -la-HH CI OCH ₂ C0 ₂ Et

04--la one FHF OCH (Me) C0 ₂ Et

05 a--la — F. H CI OCH (Me) C0 ₂ Et

06 Q- -la-CI HF OCH (Me) C0 ₂ Et

07 Q--la — CI H CI OCH (Me) C0 ₂ Et

08 Q- -la one HHF OCH (Me) C0 ₂ Et

09 a- -la one H H ci-OCH (Me) COaEt

10 Q- -la-FHF-OCH ₂ C0 ₂ -All

1 1 Q- -la one FH CI OCH ₂ C0 ₂ -All

12 a- -la one CI H F

13 Q- -la one CI H CI

14 Q- -la one FHF OCH (Me) C0 ₂ -Prg

15 Q- -la-FH CI OCH (Me) CO ₂ -Prg

16 Q- -la-F H Br OCH (Me) CO 2 -Prg

17 Q- -la i CI H F OCH (Me) CO 2 -Prg

18 a- -la I CI H CI OCH (Me) C0 ₂ -Prg

19 Q- -la one FHF SCH ₂ C0 ₂ Et 100-102 20 Q- -la one FH CI SCH ₂ C0 ₂ Et

21 Q- -la one CI HF SCH ₂ C0 ₂ Et

22 Q--la — CI H CI SCH ₂ CO _z Et

23 a- -la one CI H Br SCH ₂ C0 ₂ Et

24 Q- -la one HH CI SCH ₂ C0 ₂ Et

25 -la one FHF SCH (Me) C0 ₂ -All

26 a- -la ― FH-CI SCH (Me! CO ₂ -All

27 -la-CI HF SCH (Me) CO ₂ -All

2 S Q- -la one CI H CI SCH (Me) CO ₂ -All 129 Q-la I FHF SCH ₂ C0 ₂ -Prg

130 Q-, 1a — FH CI SCH ₂ C0 ₂ -Prg

131 Q-la la CI HF SCH ₂ C0 _E -Prg

132 Q-la la CI H CI SCH ₂ C0 ₂ -Prg

133 Q-■ la one HHF SCH _₂ C0 ₂ -Prg

134 Q- ■ la I HH CI SCH ₂ C0 ₂ -Prg

135 Q-la I FHF NH ₂ 180-181

136 α- la one FH CI NH ₂

137 Q- la one FH Br NH ₂

138 Q-la one CI HF NH ₂

139 Q- la-CI H CI NH ₂

140 Q- la one HHF NH ₂

141 Q- la one HH CI NH ₂

142 Q- la one F H F ring e

143 Q- la one F H CI 腳 e

144 Q- la one CI H F 删 e

14 δ Q- la one CI H Ci NEIe

146 Q- la one H H F 删 e

147 Q- la — H H-CI NHMe

148 Q- la one F H F NH-All

149 Q- la one F H CI NH-All

150 Q- la one CI H F NH-All

151 Q- la one CI H CI NH-All

152-la one FHFN (A11J ₂

1 δ 3 Q-la — F H CI NfAlli 2

1 δ 4 Q- la-F H Br iAll a

15 δ Q- la one CI H F NiAlIi,

156 α-l one Ci H Ci iAll) ₂ Q- la FHF NH-Prg

Q- la ― F H C1 NH-Prg

Q-la ― C1 H F NH-Prg

Q- la ― C1 H C1 NH-Prg

Q- la ― H H F NH-Prg

Q- la ― H H C1 NH-Prg

a- lb ― F H F O e

a- lb one F H C1 OMe

Q-lb ― C1 H F OMe

Q-lb ― C1 H C1 OMe

Q-lb-F H F OEt

QL—lb one F H C1 OEt

Q-lb ― F H F 0-iPr

Q-lb ― F H C1 0-iPr

Q-lb one F H F 0- All

Q-lb one F H C1 0-All

Q-lb 11 F H F O-Prg

Q-lb one F H C1 O-Prg

Q-lb ― F H F 0- (1-Me-Prg)

Q-lb ― F H C1 O- (l-Me-Prg)

Q-lb ― FHF SCH ₂ C0 ₂ Et 109-110

Q-lb ― FH C1 SCH ₂ C0 ₂ Et

Q-lb ― F H F SCHsCOz- All

Q— lb FH C1 SCH ₂ C0 ₂ -All

Q-lb F H F Hz

Q- lb FH C1 NH ₂

Q- lb F H F NH-Prg

Q- lb FH C1 NH-Prg Ϊ3 Η i · 0 1 Ό G ΐ G ΐ3 ^ε 00 ³ Η30 ί Η 0 6 1 Ό ΐ ΐ 6

Ώ Η Η s 6 -Ό 0 I ζ

SJd-0 i Η Η s 6 — Ό 602

Ώ Η Τ3 s 6 — Ό 802

° -0 ά Η 13 s z Ό L Z

Η Η i s z-Ό 90 S i Η i s z-Ό 90 S

(SJ (j-a | Ht 0 U Η Η 0 6 1 Ό VO Z

1 ΐ: 1-0 ά Η Η 0 z one Ό ε ο s

D Η 13 0 z1 Ό ζ ο ζ i Η Τ3 0 G1 Ό ΐ 0 ζ

-0 Ώ Η i 0 6 1 Ό 00 δ

i Η ί 0 z one Ό 66 ΐ

Ό Η Η 〇 z-one Ό 86 Τ ά Η 〇〇 z-one Ό L 6 I

TO Τ Τ3 0 z one Ό 96 ΐ

§Jd-0 Η ID 0 o 一 Ό 96 Τ

§Jd-0 T3 Η 0 6 Ό Ό Ρ 6 Τ

HZ ά Η i 0 z one Ό ε 6 ΐ

¾ -0 Η Η Η z 〇 Ό Ζ 6 Τ

¾ΐ-0 ί Η Η 0 z one Ό ΐ 6 I

¾T-0 Ώ Η i 0 z 06 ΐ

i Η i 0 z one Ό 68 ΐ

Η Η 0 G -Ό 88

■ ά Η Η 0 6 — Ό L 8 ΐ

Η Η J 〇 z -Ό 98 ΐ a «0 A Η i 〇 z one Ό 98 ΐ g ζ df / JDd 9.600 / Ζ6 OAV 213 Q- 20 CI HF 0CH ₂ C0 ₂ Et

214 Q- 20 CI H CI 0CH ₂ C0 ₂ Et

215 Q- 2 〇 FHF 0CH ₂ C0 ₂ -All

216 a- 2 0 FH CI 0CH ₂ C0 ₂ -All

_{217 2 0 CI HF 0CH 2 C0} 2 -A11

218 a- 2 0 CI H CI 0CH ₂ C0 ₂ -A11

219 Q- 20 FHF SCH ₂ G0 ₂ Et 164-165

220 Q- 20 FH Gl SCH ₂ C0 ₂ Et

221 Q- 2 〇 CI HF SCH ₂ C0 ₂ Et

222 Q- 20 CI H CI SCH ₂ C0 ₂ Et

223 Q- 2 〇 HHF SCH ₂ C0 ₂ Et

224 Q- 20 HH CI SCH ₂ C0 ₂ Et

225 Q- 2 SFHF SCH ₂ C0 ₂ Et

226 Q—2 SFH CI SCH ₂ C0 ₂ Et

227 Q- 2 S CI HF SCH _z C0 ₂ Et

228 a- 2 s CI H CI SCH ₂ C0 ₂ Et

229 Q- 2 s FHF SCH ₂ C0 ₂ -Prg

230 Q- 2 s FH CI SCH ₂ C0 ₂ -Prg

231 Q- 2 〇 FHF NH ₂

232 Q- 20 FH CI NH ₂

233 a- 2 〇 F H F NH-All

234 a- 2 〇 F H CI NH-All

235 Q- 2 〇 CI H F NH-All

236 Q- 2 〇 CI H CI NH-All

237 Q- 2 s FHF NH ₂

238 Q- 2 s FH CI NH ₂

239 Q- 2 s F H F NH-Prg

240 Q- 2 s FH CI NH-Prg Two

24 1 Q- 2 S CI H F NH-Prg

242 Q- 2 S CI H CI NH-Prg

243 Q-2 s H H F NH-Prg

244 Q- 2 s H H CI NH-Prg

Among the above exemplified compounds, preferred compounds include

1,2,3,4,5,6,7.8,9,10,11,12,13,14,15,16,17,18,19,20,2,1,1 22, 23, 24, 2 δ. 26, 27

28, 29, 3〇, 3 1, 32, 33, 34.35, 36

37, 38, 39, 40, 4 1, 42, 43.44, 45

46, 47, 48, 49, 50, 5 1, 52, 53, 54

55, 56, 57, 58, 59, 60, 6 1.62, 63

64, 65, 66, 67, 68, 69, 70-7 1, 72

73, 74, 75, 76, 77, 7 &, 79, 80, 8 1

82, 83, 84, 85, 86, 87, 88, 89, 90 91, 92, 93, 94, 95, 96, 97, 148, 1 4950, 151, 1 52, 1 53, 1 54 , 1 55, 1 56 1 57, 1 58 59, 1 60, 1 6 1 1 62, 1 63, 1 64, 1 65 1 66, 1 67 68, 1 69, 1 70 1 7 1, 1 72, 1 73, 1 74 1 75, 1 7683, 184, 185, 186, 187, 188, 189 1 90, 19 192, 193, 194, 195, 196, 197, 1 98 199, 20001, 202, 203, 204, 205, 206, 207 208, 20910, 233, 234, 235, 236, 239, 240 241, 、 4, 43, 244.

Among the above exemplified compounds, more preferred compounds include

1, 2, 3, 34, 35, 36, 37.3 S, 39 40, 4 1, 42, 43, 44, 45, 46, 47, 48,

49, 50, 51, 53, 54, 55, 56, 57,

58, 59, 83, 84, 85, 86, 87, 88, 89,

90, 91, 92, 93, 94, 95, 96, 97, 171,

172, 173, 174, 175, 176, 193, 194, 195, 196, 197, 198, 199, 200, 201, 202, 203, 204 .

Among the above exemplified compounds, more preferred compounds include

42, 43, 44, 45, 46, "47, 48, 49, 5〇, 51, 52, 53, 54, 55, 56, 57, 58, 59,

173, 174, 175, 176, 193, 194, 195, 196, 197, .198, 199, 200, 201, 202, 203, 204.

Among the above exemplified compounds, more preferred compounds include:

42, 43, 45, 46, 51, 52, 54, 55, 173, 174, 175, 176.

Among the above exemplified compounds, the most preferred compounds are

42, 51, 173 and 175. NMR spectrum of compound No. 83

270MHz (CDCla) δ: 7.27 (t, J = 7.8Hz, lH), 5.95 (t, d, d, J = 6.8Hz, 16.9Hz, 10.0Ηζ, ΙΗ), 5.27 (d, d, J = 16.9Hz , 0.8Hz, lH), 5.12 (d, d, J = 10.0Hz, 0.8Hz, 1H), 3.79 (d, J = 6.8Hz, 2H), 2.48-2.43 (m, 4H), 1.86-1.82 (m , 4H) The compound of the present invention is produced by the following process;

(Wherein, R ¹ , R ² and R ³ have the same meanings as above, and Y ¹ and Y ² are the same or different and represent a halogen atom. Y ¹ and Y ² are preferably the same or different and are fluorine Atom or chlorine atom.)

This step is a step for producing a compound represented by the general formula (IV) (intermediate of the compound of the present invention) by reacting the compound represented by the general formula (III) with ammonia.

The compound of formula (III), which is a raw material of this step, can be easily obtained as a reagent such as 2,6-dichloropyridine, 2,6-dibromopyridine, or 2,6-difluoropyridine. Chemistry of Heterocyclic Comoounds .: Pyrizine and Its Derivatives; RA Abramoritch Ed .; John Wiely I Sons: New York, 1974;

Academic Press, Inc .: California, 1990; vol. 49 pll7 Comprehensive Hetreocyclic Chemistry; AR Katritzky Ed .; Pergamon: Oxford, Advance compound in Heterocyclic Chemistry; AR Katritzky, FRS EQ. 1984; vol.2 ρ16δ -315 According to the method described in J. Chem. Soc., (1965) 5040, the corresponding 2,6-dihalopyridine was placed in a sealed tube with an ammonia solution of ammonia or aqueous ammonia. It is obtained by heating at.

When an alcohol solution is used, the alcohol to be used is a lower alcohol such as methanol, ethanol, or isoblovanol.

The reaction temperature is 50 to 300 ° C., preferably 90 to 200 ° C.

The reaction time depends mainly on the reaction temperature, the starting compound and the type of solvent used. However, it is usually 3 to 70 hours, preferably 10 to 30 hours <(second step)

Η

(IV) (V) (Vi a)

(Wherein, R ¹ , R ² , R ³ and Y ² have the same meanings as above, and R ⁹ is an amino group optionally having one or two substituents selected from the following group A, A substituted oxy group having a substituent selected from the group or a substituted thio group having a substituent selected from the following group B.)

[Group A]

[Group B]

An alkyl group having 1 to 6 carbon atoms which may have a substituent selected from the following group C, an alkenyl group having 2 to 6 carbon atoms which may have a substituent selected from the following group C and An alkynyl group having 2 to 6 carbon atoms which may have a substituent selected from the following group C.

[Group C]

Alkoxycarbonyl group having 1 to 6 carbon atoms, alkenyloxycarbonyl group having 2 to 6 carbon atoms, and alkenyloxycarbonyl group having 2 to 6 carbon atoms

In this step, a compound represented by the general formula 'Λ') is subjected to a nucleophilic substitution reaction in the presence of a base using the compound of the formula (IV) produced in the first step as a raw material; This is a step of producing a compound represented by I a! (An intermediate of the compound of the present invention). This step is performed in Hetrocycles, (1986) 24, 3213 Yakugaku Zasshi (1968) 88, 1610 Chem. Soc, (1964) 3736 Advances in Heterocyclic Chemistry; AR Katritzk, FRS Ed .; Academic press, Inc .: California, 1988; vol. 43 p301 Comprehensive Heterocyclic Chemistry; AR Katritzky Ed .; Pergamon: Oxford, 1984; vol. 2 pl65-315 and the like.

As the base to be used, aqueous ammonia, for example, alkali metals such as sodium hydroxide and potassium hydroxide, for example, alkali metal carbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate, and potassium carbonate, for example, hydrogen Alkali metal hydrides such as sodium and potassium hydrides; organic metal salts such as lithium diisopropylamide, lithium hexamethyldisilazane and potassium hexamethyldisilazane; Salts such as 1,4-diazabicyclo [2,2,2] octane, 1,8-diazabicyclo [5,4,0] cycloaliphatic tertiary amines such as pendene, such as pyridine, 4-dimethylaminopyridine Aromatic tertiary amines, etc .; Salts, alkali metal hydrides, organometallic salts, Ru cycloaliphatic tertiary Amin class der.

The solvent used is not limited as long as it does not participate in anti-s, but aromatic hydrocarbons such as benzene, toluene and xylene, for example, acetyl ether, tetrahydrofuran, dimethoxyethane Ethers, for example, alcohols such as methanol and ethanol, for example, nitriles such as acetate and propionyl nitrile, for example, amides such as dimethylformamide and dimethylacetamide, for example, dimethyl sulfoxide Sulfoxides, water, etc., preferably aromatic hydrocarbons, ethers, amides, and sulfoxides.

The reaction temperature is from 120 to 15 ° C, preferably from 20 to 10 CTC.

The reaction time depends mainly on the reaction temperature, the starting compound and the type of the solvent used; it varies depending on the type of the solvent, but is usually 30 minutes to 70 hours, preferably 3 hours to 30 hours. Some of the compounds represented by the formula (\ 'I a) are 2-aminoquinoline. Some are easily available as reagents,

(3rd step)

^{^{(Wherein, R 1, R 2, R}} 3, Υ 1 and Upsilon ² are as defined above.)

In this step, the compound represented by the general formula (VIb) is heated by heating an ammonia solution or an alcohol solution obtained by dissolving ammonia in the compound represented by the general formula (III) in a sealed tube. This is a process for producing an intermediate of the compound of the formula (1), which is carried out according to the first step.

When an alcohol solution is used, the alcohol used is a lower alkyl alcohol such as methanol, ethanol, or isopropanol.

The reaction temperature is from 90 to 350 ° C, preferably from 120 to 250 ° C.

The reaction time varies depending on the reaction temperature, the starting compound or the type of the solvent used.The reaction time is generally 10 to 100 hours, preferably 15 to 50 hours.

(4th step)

(Wherein, R ¹ , R ² , R ³ and R ⁴ have the same meanings as described above.)

This step is performed using the force produced in the second and third steps or a commercially available lig compound represented by the general formula (VI), Med. Chem., (1979) 22, 31; Reaction of thiophosgene in the presence of solvent O according to the method described in Cheni. Acta., (198 3) 6148. Is a step of producing a compound represented by the general formula (\ 'II) (intermediate of the compound of the present invention).

The reaction in this step can be completed in a short time by being carried out in the presence of an acid or a base. Examples of the acid used include mineral acids such as hydrochloric acid, sulfuric acid, and phosphoric acid.

Examples of the base to be used include alkali metals such as sodium hydroxide and hydroxylated lime; alkali metal carbonates such as sodium hydrogen carbonate, sodium carbonate and carbonated lime; Aliphatic tertiary amines such as diazabicyclo [2,2,2] octane, 1, diazabicyclo [5,4,0] indene, for example, aliphatic tertiary amines such as trimethylamine, triethylamine, etc. For example, aromatic tertiary amines such as pyridine, and preferred are alkali metals and alkali metal carbonates. -The solvents used are not limited, as long as they do not participate in the reaction, but include, for example, aromatic hydrocarbons such as benzene, toluene and xylene, for example esters such as ethyl acetate and propyl acetate, for example Halogenated hydrocarbons such as dichloromethane, chloroform and 1,2-dichloroethane, and water, and a mixed solvent such as chloroform-water and toluene-water may be used.

The reaction temperature is from 120 to 150 ° C, preferably from 0 to 100 ° C.

The reaction time is usually 30 minutes to 30 hours, preferably 2 hours to 20 hours, depending on the reaction temperature, the starting compound or the type of solvent used. (Fifth step)

S

(VI I) (VI I I) (I)

In this step, the azothiocyanate of the formula (VII) produced in the fourth step is used as a raw material. By reacting with hexahydropyridazine obtained according to the method of U.S. Pat. No. 2,841,584 in the presence or absence of a solvent, a compound represented by the general formula (IX) (intermediate of the compound of the present invention) is produced. This is the step of performing The reaction can be completed in a short time by adding a base as a catalyst.

Examples of the base used include alkali metal hydrides such as sodium hydrogen hydride and potassium hydrogen hydride, and organic metal salts such as lithium diisopropylamide, lithium hexamethyldisilazane, and potassium hexamethyldisilazane. Trialkylamines such as ethylamine and ethyldiisopropylamine, for example, cyclic fats such as 1,4-diazabicyclo [2,2,2] octane and 1,8-diazabicyclo [5,4,0] ndene Aromatic tertiary amines, for example, aromatic tertiary amines such as pyridine and 4-dimethylaminopyridine, and preferably trialkylamines and cycloaliphatic amines.

The solvent used is not limited as long as it does not participate in the reaction. For example, aromatic hydrocarbons such as benzene, toluene, and xylene, for example, dichloromethane, tetrachloroethane, and 1,2-dichloroethane Such halogenated hydrocarbons, for example, ethers such as diethyl ether, tetrahydrofuran, and dimethyloxetane; and nitriles such as acetonitrile and propionylnitrile; preferably, aromatic hydrocarbons, Ethers.

The reaction temperature is from 0 to 150 ° C, preferably from 20 to 100 ° C.

The reaction time varies depending on the reaction temperature, the starting compound and the type of the solvent used, but is usually 30 minutes to 70 hours, preferably 3 hours to 30 hours. (Step 6)

(Wherein, R ¹ , R ² , R ′ ³ , R ⁴ , R ⁵ and R ⁶ are as defined above), In this step, the compound of the formula VI〗 produced in the second and third steps is condensed with a commercially available compound of the formula (X) to give a compound of the general formula (Ia) This is a step of producing a compound represented by the formula (a compound in which Q is (Q-1) in the general formula (I) of the present invention).

The reaction is achieved by heating the compound of formula (X) and the compound of formula (\ '1) in the presence or absence of a solvent. The reaction can be completed in a short time by adding a catalyst.

The catalyst used is, for example, a mineral acid such as sulfuric acid or phosphoric acid, a fatty acid such as acetic acid, or a sulfonic acid such as paratonin sulfonic acid. The solvent to be used is not limited as long as it does not participate in the reaction. Examples thereof include aromatic hydrocarbons such as benzene, toluene and xylene, for example, dichloromethane, tetrachloroethane, trichloroethane, 1 Halogenated hydrocarbons such as 1,2-dichlorobenzene, for example ketones such as methylethyl ketone, getyl ketone and methyl isobutyl ketone, for example esters such as diacetyl acetate and ethyl propionate, for example acetic acid And carboxylic acids such as brobionic acid. The reaction temperature is usually 70-250 ° C, preferably 90-20 CTC. The reaction time varies depending mainly on the reaction temperature, the starting compound and the type of the solvent used, but is usually 2 to 72 hours, preferably 3 hours to 50 hours.

:

(Wherein, R ¹ , R ² , R ^s , R ⁴ and X are as defined above.

In this step, the compound represented by the general formula produced in the fifth step: Ι Χ 'and phosgene Alternatively, by reacting thiophosgene with a base in the presence or absence of a solvent in the presence of a base, the compound represented by the general formula (lb) (in the general formula (I) of the present invention, 0 · )).

The solvent used is not limited as long as it does not participate in the reaction.Examples include halogenated hydrocarbons such as dichloromethane, chloroform, and tetrachloromethane, for example, dimethyl ether, tetrahydrofuran, and dioxane. Ethers, for example, aromatic hydrocarbons such as benzene and toluene; sulfoxides, for example, dimethyl sulfoxide; and amides, for example, N, N-dimethylformamide.

Examples of the base used include aliphatic tertiary amines such as small methylamine and triethylamine; aromatics such as pyridine and quinoline; tertiary amines such as sodium hydroxide and carbonic acid. Organic bases such as lime and sodium carbonate, for example, alkali metal hydrides such as sodium hydride, potassium hydride and lithium hydride.

The reaction is carried out usually at a temperature of from 20 to 40 ° C, preferably from 0 to 25 ° C. The reaction time is mainly 15 minutes to 5 hours, and preferably 30 minutes to 3 hours, depending on the reaction temperature, the starting compound or the type of the solvent used.

(8th process)

(Wherein, R ¹ , R ² , R ³ and Q have the same meanings as above, R ⁷ is an amino group having one or two substituents selected from Group A, a substituent selected from Group B Or a substituted thio group having a substituent selected from the group B, Z ¹ represents a halogen atom, .Z ¹ preferably represents a fluorine atom or a chlorine atom.

In this step, the compound represented by the general formula (XIIa) and the compound represented by the general formula (XIII ′) The compound in the presence or absence of a solvent selected, by the presence of a base reaction, the compound represented by the general formula (I c) (compounds of general formula (I), wherein the R ⁴ forces group A substituted or unsubstituted amino group having one or two substituents selected from the group B, or a substituted thio group having a substituted moiety selected from the group B). .

The compound represented by the general formula (XIla), which is a starting compound in this step, can be produced by a method according to the sixth step or the seventh step.

The solvent used in this step is not limited as long as it does not take part in the reaction. For example, aromatic hydrocarbons such as benzene, toluene, and xylene, for example, dimethyl ether, tetrahydrofuran, dimethoxyethane Ethers such as methanol, alcohols such as ethanol, acetonitrile, nitriles such as propionylnitrile, amides such as dimethylformamide, dimethylacetamide, and dimethyl sulfoxide Sulfoxides and the like, and preferred are aromatic hydrocarbons, nitrels, amides, and sulfoxides.

The base used is, for example, aqueous ammonia. Alkali metals such as sodium hydroxide and potassium hydroxide, for example, alkali metal carbonates such as sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate, and potassium carbonate, for example, hydrogen Alkali metal hydrides such as sodium hydride and potassium hydride, for example, organic metal salts such as lithium diisopropylamide, lithium hexamethyldisilazane, and potassium bexamethyldisilazane, lower metal salts such as butyllithium Cycloaliphatic tertiary amines such as 1,4-diazabicyclo [2,2,2] octane and 1,8-diazabicyclo [5,4,0] ndene, such as pyridine and 4-dimethylaminopyridine Aromatic tertiary amines and the like, preferably alkali metal carbonates , Alkali metal hydrides, organic metal salts, and cycloaliphatic tertiary amines

-o

The reaction temperature is from 120 to 15 (TC, preferably from 0 to 100).

The reaction time depends mainly on the temperature, the starting compounds and the type of solvent used. Power is usually 30 minutes to 30 hours, preferably 2 to 15 hours.

(Step 9)-

(I I b) (IV) (Id)

(Wherein, R ¹ , R ² , R ³ , R ⁷ and Q have the same meanings as described above, Z ² represents an OH group, an SH group, or an NH ₂ group, and R ⁸ is a substituent selected from Group C. An alkyl group having 1 to 6 carbon atoms which may have a substituent, an alkenyl group having 2 to 6 carbon atoms which may have a substituent selected from the group C and a substituent selected from the group C. Represents an alkynyl group having 2 to 6 carbon atoms which may be possessed, Y represents a halogen atom, and Y preferably represents a fluorine atom or a chlorine atom.

In this step, the compound represented by the general formula (XI lb) is reacted with the compound represented by the general formula (XIV) in the presence or absence of a solvent in the presence of a base to obtain a compound represented by the general formula (XI A compound represented by Id) (in the general formula (I) of the present invention, an amino group having one or two substituents selected from the group R ⁴ , a substituent having a substituent selected from the group B) Or a substituted thio group having a substituent selected from Group B).

The compound represented by the general formula (XIlb) as a starting compound in this step can be produced by a method according to the sixth step or the seventh step.

The solvent used in this step is not limited as long as it does not take part in the reaction.For example, aromatic hydrocarbons such as benzene, toluene, and xylene, such as dimethyl ether, tetrahydrofuran, and dimethoxyethane Ethers such as alcohols such as methanol and ethanol, nitriles such as acetonitrile and propionylnitrile, amides such as dimethylformamide and dimethylacetamide, and sulfoxides such as dimethylsulfoxide And the like, preferably aromatic hydrocarbons, neethers, amides, sulfones, etc. It is a foxide.

Examples of the base used include alkali metals such as ammonia water, sodium hydroxide and potassium hydroxide, and alkali metal carbonates such as sodium hydrogencarbonate, potassium hydrogencarbonate, sodium carbonate and carbonated lime. Alkali metal hydrides such as sodium hydride and potassium hydride; organic metal salts such as lithium diisopropylamide, lithium hexamethyldisilazane and potassium hexamethyldisilazane; lower alkyl salts such as butyllithium Metal salts, such as 1,4-diazabicyclo [2,2,2] octane and 1,8-diazabicyclo [5,4,0] cycloaliphatic tertiary amines such as pendene, for example, pyridine, 4-dimethylaminopyridine And aromatic tertiary amines such as S, alkali metal hydrides, organometallic salts, Ru cycloaliphatic tertiary Amin class der.

The reaction time varies depending mainly on the reaction temperature, the starting compound and the type of the solvent used, but is usually 30 minutes to 30 hours, preferably 2 to 15 hours. After the reaction in each step described above, each target compound is isolated by filtration according to a conventional method, or by filtering out a precipitated crystal or diluting with water and extracting with a water-immiscible solvent. If necessary, it can be purified by recrystallization or column chromatography.

[Best Mode for Carrying Out the Invention]

Hereinafter, the present invention will be described more specifically with reference to Examples and Preparation Examples.

(Example 1)

N-2-quinolyl-3,4,5,6-tetrahydrophthalimide

A solution of 0.20 g of tetrahydrophthalic anhydride and 0.19 g of 2-aminoquinoline in 1,2-dichlorobenzene (5 ml) was heated at 200 ° C. for 30 hours in the presence of a catalytic amount of paratoluenesulfonic acid. After cooling to room temperature, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography to obtain 0.256 g of the title compound as crystals having a melting point of 159 to 161 ° C. (Example 2).

N-3,5-difluoro-6-methoxypyridine-2-yl-3,4,5,6-tetrahydrophthalimid

A solution of 8111 ^ in 3,4,5,6-tetrahydrophthalic anhydride and 84 mg of 2-amino-3,5-difluoro-6-methoxypyridine in toluene (5 ml) was added to a paratoluene medium Heated at 120 ° C for 2 days in the presence of sulfonic acid. After cooling to room temperature, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel gel chromatography to obtain 0.13 g of the title compound as a solid having a melting point of 120 to 122 ° C.

(Example 3)

N- 3,5-difluoro mouth-6- (ethoxycarbonylmethylthio) pyridine-2-yl-2,3-dimethylmaleimide

A solution of 0.10 g of 2,3-dimethylmaleic anhydride and 0.18 g of 2-amino-3,5-difluoro U-6-ethoxycarbonylmethylthiopyridine in 1,2-dichlorobenzene (5 ml) was catalyzed. Heated at 180 ° C for 12 hours in the presence of an amount of paratoluenesulfonic acid. After cooling to room temperature, the solvent was distilled off under reduced pressure, and the reaction solution was purified by silica gel column chromatography to obtain 0.17 g of the title compound as crystals having a melting point of 109 to 110 ° C.

(Example 4)

9- {3,5-difluoro mouth-6-! 2-propynyloxy) pyridin-2-yl} imino-8_thia-1,6-diazabicyclo Ώ [4,3,0] nonan-7-one

0.25 g of 1-N- {3,5-difluoro-S- (2-brovini To a solution of thiocarbamoyl-hexahydro-pyridazine and 0.19 ml of pyridine in dichloromethane (5 ml) was added dropwise, under a nitrogen atmosphere at 0 ° C., 1.2 ml of a phosgene U-tolunin solution. After stirring at room temperature for 90 minutes, the reaction solution was poured into ice water and extracted with dichloromethane. After the extract was concentrated under reduced pressure, the residue was purified by silica gel column chromatography to obtain 0.26 g of the title compound as crystals having a melting point of 214 ° C.

(Example 6)

N-3,5-difluo-6-isopropylthiopyridine-2-yl -_3,4,5-tetrahydro_phthalimid

To a solution of 571 isopropylthiol in tetrahydrofuran was added 23 mg of sodium hydride under a nitrogen atmosphere at 0 ° C, and the mixture was stirred for 15 minutes. Thereafter, 150 mg of a solution of N-3,5,6-trifluoropyridine-2-yl-3,4,5,6-tetrahydrophthalimid in tetrahydrofuran was added, and the mixture was stirred for 30 minutes. The reaction solution was poured into water, extracted with ethyl acetate, concentrated, and the residue was purified by silica gel column chromatography to obtain 74.lmg of the title compound as crystals having a melting point of 136 to 140.

(Reference example 1)

2-amino-3,5,6-trifluoropyridine

23 g of 2,3,5,6-tetrafluoropyridine and 70 ml of 30% aqueous ammonia were heated at 130 in a sealed tube for 40 hours. After cooling to room temperature, the reaction mixture was poured into water, beaten with dichloromethane, and the organic phase was concentrated to obtain 14.5 g of the title compound.

'H-NMR spectrum (270 MHz CDC1 ₃₎

δ: 7.27 (t, d, J = 7.2,8.5Hz, 1H), 4.70-4.51 (br, 2H)

(Reference example 2)

2-Amino-3,5-difluoro-6- (2-propynyloxy) pyridine

To a solution of 501 2-amino-3,5,6-trifluoropyridine and 0.24 ml of propargyl alcohol in) -dimethylformamide (20 ml) was added 162 mg of 60 wt% oily hydrogenated stream at 0 °. C slowly added. After stirring at the same temperature for 1 hour under a nitrogen atmosphere and then at room temperature for 16 hours, the reaction solution was poured into water and extracted with ethyl acetate. After drying and concentration, the residue was purified by silica gel column chromatography to give 547 mg of the title compound as crystals with a melting point of ~ 57 ° C. Obtained.

(Reference example 3)

2-Amino-3,5-difluoro mouth-6-ethoxycarbonylmethylthiopyridine

0.96 ml of ethyl 2-mercaptoacetate was added dropwise to a suspension (10 ml) of 0.21 mg of sodium hydride in tetrahydrofuran under a nitrogen atmosphere at 0 ° C. After stirring for 10 minutes, a solution of 2-amino-3,5,6-trifluorofluoropyridine in tetrahydrofuran (5 ml) was added dropwise, and the mixture was stirred at room temperature for 12 hours and then heated at 70 ° C for 11 hours. The reaction solution was cooled to room temperature, poured into ice water and extracted with ether. The organic phase was concentrated, and the residue was purified by silica gel column chromatography to obtain 707 mg of the title compound as an oil having a refractive index of n _D 1.547. (Reference Example 4)

2,6-diamino-3,5-difluoropyridine

A mixture of 1.3 g of 2-amino-3,5,6-trifluoropyridine and 4 ml of 30% aqueous ammonia was heated in a sealed tube at 140 ° C. for 20 hours. After cooling to room temperature, the reaction mixture was poured into water, extracted with dichloromethane, the organic phase was concentrated, and the residue was purified by silica gel gel chromatography to obtain 105 mg of the title compound. g raw material was spun.

'Η- Mffi scan Bae spectrum (2Q0fflz CDC1 ₃₎

δ: 7.04 (t, J = 9.3Hz, 1H), 4.07-3.65 (br, 4H)

(Reference Example 5)-3,5-difluoro mouth-6- (2-bromovinyloxy) pyridyl-2-isothiocyanate

To a mixture of 0.13 ml of tiophosgene and 196 mg of sodium bicarbonate in a mixed solution of formaldehyde (4 ml) and water (3 ml) was added 253 mg of 2-amino-3,5-difluoro-6- (2-propynyloxy) pyridine. Mouth form solution (4 ml) was added dropwise. The reaction solution was vigorously stirred at room temperature for 2 hours and then left for 20 hours. The reaction solution was poured into water and extracted with chloroform. The organic phase was dried and purified by silica gel column chromatography to obtain 212 mg of the title compound.

-NMR spectrum (270 books z CDCla)

δ: 7.33 (t, J = 7.8Hz, 1H), 4.98 (d, 2.4Hz, 2H), 2.51 (t, J = 2.4Hz, 1H!

(Reference ί Row 6, i / 6drh> d: / 0z6 OAV,

(Formulation Example 5) (Wettable powder)

25% of the compound obtained in Example 3, 2.5% of sodium dodecylbenzenesulfonate, 2.5% of calcium ligninsulfonate and 70% of diatomaceous earth were mixed and ground to obtain a wettable powder.

(Formulation Example 6) (Emulsion)

15% of the compound obtained in Example 2, cyclohexanone 35%, calcium salt of dodecylbenzenesulfonate 2.61%, polyoxyethylene distyrenated methylphenol ether 3.96%, polyoxyethylene alkyl ether 1.87 %, 0.26% of polyoxyethylene nonylphenyl ether phosphate calcium salt, 1.3% of xylene and 40% of mesitylene were uniformly dissolved to obtain an emulsion.

(Formulation Example 7) (Emulsion)

30% of the compound obtained in Example 1, 2.61% of calcium salt of dodecylbenzenesulfonic acid, 3.96% of polyoxyethylene distyrenated methylphenol ether, 1.87% of polyoxyethylene alkyl ether, 1.87% of polyoxyethylene Emulsion was obtained by mixing 0.26% of nonyl-funinyl ether calcium phosphate and 61.3% of xylene well.

(Formulation Example 8) (Granules)

5% of the compound obtained in Example 4, lauryl alcohol sulfate sodium salt 2%, ligninsulfonic acid sodium salt 5%, carboxymethylcellulose sodium salt 2%, calcium carbonate 66% and bentonite 20% The mixture was uniformly mixed and pulverized. 20 parts by weight of water was added to 100 parts by weight of this mixture, kneaded, processed into granules of 14 to 32 mesh using an extrusion granulator, and dried to obtain granules.

(Formulation Example 9) (Granules)

5% of the compound obtained in Example 2, 30% of bentonite, 62.5% of talc, 2% of sodium ligninsulfonate, 0.35% of sodium dioctyl sulfosuccinate, 0.35% of propylene glycol. 075% and water 0.075% were uniformly mixed and pulverized. 20 parts by weight of water was added to 100 parts by weight of this mixture, kneaded, processed into granules of 14 to 32 mesh using an extrusion granulator, and dried to obtain granules. (Formulation Example 10) (Granules)

4% of the compound obtained in Example 4, 30% of bentonite, 63% of clay, 1% of polybutyl alcohol and 2% of sodium benzenesulfonic acid sodium salt were uniformly mixed and pulverized. 20 parts by weight of water was added to 100 parts by weight of this mixture and kneaded. The mixture was processed into granules of 14 to 32 mesh using two extruding granulators, and then dried to obtain granules.

(Formulation Example 11) (Granules)

4% of the compound obtained in Example 3, 35% of bentonite, 58% of talc, 2% of sodium alkylnaphthalenesulfonate and 1% of sodium sodium dioctyl sulfosuccinate were uniformly mixed and pulverized. 100 parts by weight of this mixture was mixed with 20 parts by weight of water, kneaded, processed into granules of 14 to 32 mesh using an extrusion granulator, and dried to obtain granules.

(Formulation Example 12) (Granules)-5% of the compound obtained in Example 4, white powder 1%, ligninsulfonic acid calcium salt 5%, clay 84%, and carboxymethylcellulose sodium salt 5% After pulverizing and mixing, water was added and kneaded well, followed by granulation and drying to obtain granules. (Formulation Example 13) (Wettable powder)

80% of the compound obtained in Example 2, sodium dodecyl pencene sulfonate 3%, sodium alkyl naphthalene sulfonate 2%, sodium lignin sulfonate 2%, synthetic amorphous silica 3%, strength 10% of the oligin was mixed, pulverized by an air-mill, mixed again, and packed.

(Formulation Example 14) (Granules)

The wettable powder of Formulation Example 13 (15%), kaolin clay (50%), talc (25%) and ligninsulfonic acid sodium salt (10%) were mixed in a rotary mixer or a fluidized-bed mixer, and were granulated by spraying water. When most became 1.0-0.15 mm, the condyles were removed, dried and sieved. The oversized material was crushed to give granules of 1.0-0.15 mm.

(Formulation example 15) (Hydrated granules)

80% of the compound obtained in Example 3, special holica hongjun polymer sodium salt 1.2 5%, 3.75% water, 3% sodium dodecylbenzenesulfonate, 7% dextrin and 5% titanium oxide, then pulverize with an air mill and add to a rotary mixer or fluid bed mixer, Water was sprayed to granulate. When most of them became 1.0-0.15 mm, the granules were taken out, dried and sieved. The oversized material was crushed to obtain granules of 1.0-0.15 mm.

(Formulation Example 16) (Aqueous suspension)

25 parts of the compound obtained in Example 1, sodium octyl sulfosuccinate 0.

7 parts, 0.15 parts of propylene glycol, 10 parts of calcium ligninsulfonate, 44.15 parts of water and 10 parts of propylene glycol until ball particles, sand mill or roller until solid particles are reduced to a diameter of 5 microns or less. Milled together in one mill. To 90 parts of this milled slurry, 10 parts of a 0.05% (W / W) xanthan gum aqueous solution was added and mixed to obtain an aqueous suspension.

(Formulation Example 17) (Solution)

30% of the compound obtained in Example 4, 30% of dimethylformamide and 40% of 3-methyl-3-methoxybutanol were combined and stirred to obtain a solution.

[The invention's effect]

(Test Example 1)

Filling the field soil with a 150 cm ² area made of plastic made of plastic, the annual weeds Akinoenokorogusa, Inubie, Seibanmorokoshi, Ichibi, Onamimomi, Inuhozuki, Noharagarashi, and various crops of wheat, soybean and maize are sown. Seeds were then covered with the same soil. The next day, the compound of the present invention was prepared in a wettable powder of a predetermined concentration, and 15 ml of the powder was uniformly treated per pot. The pots after the treatment were placed in a glass greenhouse, and after 3 weeks, the growth state of the plants was observed, and the herbicidal efficacy was determined according to the following criteria.

(Judgment criteria)

For untreated pot plants

Growth inhibition [! ~ 5% Effect 0

6-30% "1

Nono 31-50%) 1 2

Nono 51-70%)! 3

) 1 71 〜 95% ■ n 4

NONO 96 -1D0% NONO

Table 2 shows the results of Test Example 1

(Test Example 2)

After sowing and covering the plants as in Test Example 1, the plants were grown for 12 days in a glass greenhouse. '' Thereafter, Gramine S (manufactured by Sankyo Co., Ltd.) was added to the wettable powder of the compound of the present invention prepared at a predetermined concentration so as to have a concentration of 0.05%, and 100 ml per lm ² was uniformly sprayed (spray water amount 1000 Liters ha). Twelve days after spraying, the growth state of the plants was observed, and the herbicidal efficacy was determined according to the same criteria as in Test Example 1.

Table 13 shows the results of Test Example 2.

In addition, the comparative compound (Aj) in Test Example 1 and Test Example 2 Is,

2 (Test example 1) Pre-emergence and destruction of the germination process No. 3 'ビビビララ 3 3 3 3

Kg / a Drum α J

No. Kozura

Sachyan

1 5 δ 4 4 5 o 5 1 0 0

4 0.5 4 5 4 4 3 δ o 0 0 0

0.2D ό 4 3 m ο o u u π υ

1 5 5 5 o 4 ο o 1 0 0

9 0.5 D 5 5 ό 1 5 Ό 0 0 0

0.25 4 5 4 5 0 5 o 0 0 0

1 5 5 5 5 4 ο 5 1 "1 0

42 Ο.δ 5 5 5 D 3 D δ 0 0 0

0.25 4 5 4 δ 2 5 5 0 0 0

1 4 5 4 4 0 ο o 0 0 0

1 93 Ο.δ 3 4 4 3 0 4 o 0 0 0

0.25 1 3 9 0 0 3 0 0 0 Compare 1 0 1 1 0 0 0 0 0 0 0 Compound 0.5 0 0 0 0 0 0 0 0 0 0

(A) 0.25 0 0 0 0 0 0 0 0 0 0 I 3 (Test Example 2) 杂杂杂杂杂杂杂試験試験試験試験 3 3 試験試験試験試験試験試験試験 3 試験 3 試験 3 試験試験/ MQ line D, ゥ ga D

Gu Ko Zula

Sanctuary

1 □ c

O Ό ο O ο ο Δ ο

4 Ο.δ r-1

D b D ό o Ο ο 1 Δ 1

4 3 3 D 4 ο ο 1 1 0

1 b o o o o D ΰ 4

9 0.5 rr

O 5 o d D Ο ο Δ 1

U .D 4 5 4 D 5 D D 0 1 0

1 ό o Ό O Ό Ο 4 3

42 Ο.δ 5 O δ ο Ό Ο 2 3 1

00 υ .00 η 5 D Ο ο 〇 20

1 4 4 4 D 0 1 0

1 1 9 0.5 o 5 δ 4 0 0 0

U.ώθ 1 1 1 δ 4 4 0 0 0

1 2 3 4 δ 5 ο ο 1 4 1

1 93 Ο.δ 2 2 3 5 4 ο 5 0 3 0

0.25 0 1 1 4 2 ο 4 0 0 Compare 1 2 2 O 5 4 ο 4 1 4 1 Compound 0.5 1 1 9 4 4 0 3 1

(A) 0.25 0 0 0 2 4 1 0 1 [Industrial applicability]

The compound of the present invention shows an excellent herbicidal effect against various weeds by both pre-emergence and post-emergence treatment methods, and also shows excellent selectivity between crops and weeds. In particular, as a herbicide for foliage treatment and soil treatment of upland crops, various weeds growing in the field, for example, Soba kazula, Sanae yude, Suberihu, Hakobe, Shiroza, Agaei tou, Noharagarashi, Nazuna, Ichibi, American dragonfly Broadleaf weeds such as mosquitoes, field panjis, yaemgras, balsam pears, balsam pears, pygmy pygmy moss, pygmy moss, shirobana kosemasagao, yinhozuki, ooinu nofuguri, linu camouflage, corn marii gold, corn marigold, sylvanus Grass weeds, such as cedar, oats, oats, sylvanmo, sorghum, shibamugi, ゥ manochiyahiki, and giant foragegrass; It shows herbicidal activity against various weeds, such as weeds, and does not show any phytotoxicity that causes problems for major crops such as corn, wheat, rice, and soybean. As a herbicide for paddy fields, various kinds of weeds that occur in paddy fields, for example, grass weeds such as porpoise; broadleaf weeds such as oak, azaena, kikasigusa, and mizohakobe; tamagayari, firefly, matsubayashi, and mizugayari It shows herbicidal activity against grasses and does not show problematic phytotoxicity against rice.In addition, it can be used not only in fields and paddy fields, but also in orchards, mulberry fields, and non-agricultural lands. Can be.

The compound of the present invention also has an action of suppressing the growth of the plant without killing the plant. Therefore, for example, various methods such as prevention of lodging due to short rice paddy rice, reduction of the number of times of cutting by suppressing growth of the lawn, etc. Expected to be useful.

To prepare herbicides and plant growth regulators, powders are prepared by diluting with a carrier such as a solid carrier or a liquid carrier and, if necessary, adding other preparations such as surfactants and auxiliary agents. , Coarse powders, granules, fine granules, emulsions, suspensions, wettable powders, flowables , Water solvents, liquid preparations and the like. Of course, the purification can be stopped at any stage of the purification, and the crude product can be used as the active ingredient.

Carriers are synthetic or natural, inorganic, which are mixed with herbicides and plant growth regulators to help the active ingredient reach the plant or to facilitate storage, transport or handling of the active ingredient. Or an organic substance.

Suitable solid carriers include, for example, clay, talc, dikryte, bamiki ureite, slaked lime, silica sand, diatomaceous earth, kaolin, attapulgite clay, bentonite, calcium carbonate, ammonium sulfate, acid clay, hydrous clay Inorganic substances such as amorphous silicon dioxide, calcite, dolomite, phosphorous lime, and zeolite; resins such as coumarone resin, alkyd resin, petroleum resin, polychlorinated vinyl, coal balgam, dammar gum, and stergel; carnapalow, Waxes such as paraffin wax; nut shells such as walnuts and nuts; tobacco flour, flour, wood flour, kinako flour, starch, soy flour; urea.

Suitable liquid carriers include, for example, water; aromatic hydrocarbons such as xylene and methylnaphthalene; alcohols such as methanol, ethanol, isopropanol, ethylene glycol and cerolylbu; acetone, cyclohexanone and isophorone. Ketones; vegetable oils such as soybean oil and cottonseed oil; polar solvents such as dimethyl sulfoxide, Ν, Ν-dimethylformamide, and acetonitrile.

Surfactants used for dispersion, emulsification, wetting, spreading, etc. may be ionic or non-ionic.

Suitable anionic surfactants include, for example, alkyl sulfates such as sodium salt of lauryl sulfate; alkyl sulfonates such as sodium salt of paraffinsulfonic acid; sodium salt of dodecylbenzenesulfonic acid

Alkyl aryl sulfonates such as sodium salt of naphthalenesulfonic acid; dialkyl sulfosuccinates such as sodium salt of getylhexylsuccinic acid; phosphorus of polyoxynitylene nonylphenyl ether Esthetics and their salts, such as polyethylene ethylene; Monoteryl phosphates; poly (or alkylaryl) ether sulfates, such as sulfates and salts thereof, and lignin sulfonates, such as sodium or calcium salts of ligninsulfonic acid. Salts of higher fatty acids, such as sodium oleate, and the like. .

Suitable cationic surfactants include, for example, salts of higher fatty acid amines such as laurylamine acetate; higher fatty acid amine oxidized ethylene condensates such as polyoxetylene stearylamine.

Suitable nonionic surfactants include, for example, glycerides of fatty acids; sucrose esters of fatty acids; polyoxyethylene alkyl esters such as polyoxyethylene oleate; ethylene oxide condensates of higher fatty alcohols. Polyoxyethylene alkyl ethers; polyoxyethylene alkylaryl ethers, such as alkylphenol or alkyl naphthalene ethylene oxide condensates; polyoxyethylene polyoxypropylene block copolymers; And sorbitan fatty acid esters such as monoalkylates and their ethylenoxide adducts, and polyoxyxylene sorbin fatty acid esters. When used as a herbicide, other ingredients such as gelatin, casein, arabia gum, sodium salt of carboxymethylcellulose (CMC), polyvinyl alcohol, protective colloids such as methylcellulose; dispersions such as sodium triribolyphosphate Agents; thickeners such as penite; ligninsulfonic acid. Salts; alginates; and isopropyl propyl phosphate (PAP).

Also, when used as a herbicide, the range of application is expanded by mixing with other fungicides, insecticides, acaricides, nematicides, herbicides, plant growth regulators, fertilizers, soil conditioners, etc. And save labor.

The treatment method is usually to formulate a preparation and treat it with soil, foliage or flooding before or within about one month after germination of the weed. Soil treatment includes soil surface treatment and soil admixture treatment.Stalk and foliage treatment includes local treatment that treats only weeds so that they do not adhere to crops. The spray of granules and the water surface And irrigation treatment.

The compound of the present invention can be used as a herbicide for paddy fields, fields, orchards, pastures, turf lands, forests or non-agricultural lands.

The amount of treatment varies depending on the weather conditions, formulation, treatment time, treatment method, location, target weeds, target crops, etc. Usually, the active ingredient is 1 g to 100 g per are, preferably 2 g. Emulsions, wettable powders, suspending agents, etc. are usually prepared in a predetermined amount of 1 to 10 liters of water per are (surfactant, polyoxyethylene resin if desired). Spreading agents such as acid, lignin sulfonate, abietic acid salt, dinaphthyl methane disulfonate, and paraffin can be added.) Dilute and treat, and granules are usually treated without any dilution I do.

Claims

General formula

(Where Q-n-one

(Box -2)

(In the formula, X represents an oxygen atom or a sulfur atom, R ⁵ and R ⁶ are the same or different and represent an alkyl group having 1 to 6 carbon atoms, or R ⁵ and R ⁵ together have 3 or more carbon atoms. Represents 4 alkylene groups.)

R ¹ , R ² and R ³ are the same or different and represent a hydrogen atom or a halogen atom; R ⁴ is an amino group optionally having one or two substituents selected from the following group A, Represents a substituted oxy group having a selected substituent or a substituted thio group having a substituent selected from the following group B, or R ³ and R ⁴ are taken together to form CH = 'CH—CH = It may form a group represented by CH—. ) The compound represented by these.

[Group A]

[Group B]

An alkyl group having 1 to 6 carbon atoms which may have a substituent selected from the following group C, and an alkenyl group having 2 to 6 carbon atoms which may have a substituent selected from the following group C And an alkynyl group having 2 to 6 carbon atoms which may have a substituent selected from Group C below. 5 δ

[Group C]

2. Q represents (Q-1) or (Q-2), X represents an oxygen atom, R ¹ and R ³ are the same or different and represent a halogen atom, R ² represents a hydrogen atom, R ⁴ Represents an amino group which may have two or more substituents selected from Group A, a substituted oxy group having a substituent selected from Group B, or a substituted thio group having a substituent selected from Group B. Or R ³ and R ⁴ may together form a group of the formula —CH 2 CH—CH = CH—, wherein R ⁵ and R ⁶ are methyl groups or R ⁵ and R ⁶ is the compound according to claim 1 showing a together a connexion number 3 or 4 alkylene group with a carbon.

3. Q represents (Q-1) or (Q-2); X represents an oxygen atom or a sulfur atom; R ¹ , R ² and R ³ are the same or different and represent a hydrogen atom or a halogen atom; ⁴ is an amino group having one or two substituents selected from the following group A ', a substituted oxy group having a substituent selected from the following group B *, or a substitution having a substituent selected from the following group B' R ³ and R ⁴ may together form a group of the formula —CH = CH—CH—CH—, wherein R ⁵ and R ^e may be the same or different or indicating the number 1 to 6 alkyl groups R ⁵ and R ^s is a compound according to claim 1 showing a together a connexion number 3 or 4 alkylene group with a carbon.

[Α 'group]

[Β 'group]

An alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms and an alkynyl group having 2 to 6 carbon atoms.

4. Q represents (Q-1) or (Q-2), X represents an oxygen atom, and R ³ represents the same or different halogen atom, R ² represents a hydrogen atom, R ⁴ represents A An amino group having one or two substituents selected from group B, a substituted oxy group having a substituent selected from group B ', or a substituted thio group having a substituent selected from group B'; Alternatively, R ³ and R ⁴ may together form a group of the formula CH = CH—CH = CH—, wherein R ⁵ and R ⁶ represent a methyl group or are together with R ⁵ 2. The compound according to claim 1, wherein the compound represents an alkylene group having 3 or 4 carbon atoms.

5. Q represents (Q-1) or (Q-2), X represents an oxygen atom, R ¹ , R ² and R ³ are the same or different and represent a hydrogen atom or a halogen atom, and R ⁴ represents saying a substituted Chio group having location換分selected from "substituent Okishi group or the following B having a substituent selected from group" group yourself B, R ⁵ and R ⁶ are C 1 to carbon atoms the same or different 2. The compound according to claim 1, wherein the compound represents 6 alkyl groups or R ⁵ and R ⁶ together represent an alkylene group having 3 or 4 carbon atoms.

[Group B]

6. Q represents (Q-1) or (C12), X represents an oxygen atom, R ¹ and R ³ are the same or different and represent a halogen atom, R ² represents a hydrogen atom, R ⁴ Represents a substituted oxy group having a substituent selected from the group B "or a substituted thio group having a substituent selected from the group B", and R ⁵ and R ^s are the same or different and each have 1 to 6 carbon atoms. Represents an alkyl group, or R ⁵ and R ⁶ are taken together to form a C ³ or C 4

2. The compound according to claim 1, which represents a group.

7. Q represents (Q-1) or (Q-2), X represents an oxygen atom, R ¹ and R ³ is the same or different and represents a fluorine atom or a chlorine atom; R ² represents a hydrogen atom; and R ⁴ represents a substituted oxy group having a substituent selected from the group B ”or a substituent selected from the group B”. The compound according to claim 1, wherein the compound has a substituted thio group, and R ⁵ and R ^{6 each} represent a methyl group or R ⁵ and R ⁶ together represent an alkylene group having 3 or 4 carbon atoms.

8. Q represents (Q-1), R ¹ and R ³ represent a fluorine atom, R ² represents a hydrogen atom, and R ⁴ represents a substituted oxy group or B having a substituent selected from the group B " The compound according to claim 1, wherein the compound represents a substituted thio group having a substituent selected from the group, and R ⁵ and R ⁵ together represent a butylene group.

9. Q represents a (Q-1) or (Q-2), X represents an oxygen atom, R ', R ² and R ³ are the same or different and each represents a hydrogen atom or a halogen atom, IV the number of carbon atoms Represents 2 to 6 alkynyloxy groups, R ⁵ and R ⁶ are the same or different and represent an alkyl group having 1 to 6 carbon atoms, or R ⁵ and? The compound according to claim 1, wherein ⁶ and ⁶ together represent an alkylene group having 3 or 4 carbon atoms.

10. Q represents (Q-1) or (Q-2), X represents an oxygen atom, R ¹ and R ³ are the same or different and represent a halogen atom, R ² represents a hydrogen atom, R ⁴ represents an alkynyloxy group having 2 to ⁶ carbon atoms, R ⁵ and R ⁶ are the same or different and represent an alkyl group having 1 to 6 carbon atoms, or R ⁵ and R ⁶ are 2. The compound according to claim 1, wherein the compound has 3 or 4 alkylene groups.

1 1. Q represents (Q-1), R ¹ and R ^s represent the same or different and represent a fluorine atom or a chlorine atom, R ² represents a hydrogen atom, and R ⁴ represents an alkynyl having 2 to 6 carbon atoms. 12. The compound according to claim 11, wherein R ⁵ and R ^s represent a methyl group or R ^s and R ^s together represent an alkylene group having 3 or 4 carbon atoms.

12. Q represents (Q-1), R ¹ and R ³ represent a fluorine atom, R ² represents a hydrogen atom, R ⁴ represents an alkynyloxy group having 2 to 6 carbon atoms, R ⁵ and R ^s is a compound according to claim 1 showing a together a connexion butylene.

13. N- {3,5-difluoro mouth-6- (2-propynyloxy) pyridine-2-yl 3,4,5,6-tetrahydrophthalimide

14. N- {5-chloro-1-fluoro-6- (2-propynyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimide-

1 5. N- {3-chloro-5-fluoro-6- (2-propynyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimide

1 6. N- {3,5-dichloro-6- (2-bromovinyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimide

1 7. {3,5-Difluoro-6-U-methyl-2-propynyloxy) pyridine-2-yl} 3,4,5,6-tetrahydrophthalimide

18. N- {5-chloro-1-6-fluoro-2-methyl-2-propynyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimide

19. {3-chloro-1-fluoro-6- (1-methyl-2-propynyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimide

20. N- {3,5-Dichloro-6-methyl-2-bropinyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimide

21. N- {3,5-difluoro-6- (2-bromovinyloxy) pyridin-2-yl} 2,3-dimethylmaleimide

22. N- {5-chloro-1-fluoro-6- (2-propynyloxy) pyridin_2-yl} 2,3-dimethylmaleimide

23. N- {3,5-difluoro-6- (1-methyl-2-propynyloxy) pyridin-2-yl} 2,3_dimethylmaleimide

24. N- {5-chloro-1-fluoro-6- (1-methyl-2-propynyloxy) pyridin-2- 2-diene}} 2,3-dimethylmaleimide

25. A herbicidal composition comprising an effective amount of a compound selected from the compounds defined in claim 1 together with a carrier or excipient.

26. A chiasmetic composition comprising an effective amount of a compound selected from the compounds defined in claim 3 together with a carrier or excipient.

27. A herbicidal composition comprising an effective amount of a compound selected from the compounds defined in claim 5 together with a carrier or excipient.

28. A herbicidal composition comprising an effective amount of a compound selected from the compounds defined in claim 9 together with a carrier or excipient.

29. A herbicidal composition II comprising an effective amount of a compound selected from the compounds defined in claim 11 together with a carrier or excipient.

30. Transfer an effective amount of a compound selected from the compounds specified in claim 12 to a carrier or Is a herbicidal composition containing an excipient.

31. A herbicidal composition comprising an effective amount of a compound selected from the following compounds together with a carrier or excipient.

N- {3,5-difluoro-6- (2-propynyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimide

N- {5-chloro-1-fluoro-6- (2-propynyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimide

N- {3-chloro-5-fluoro-6- (2-bromovinyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimide

N- {3,5-dichloro-6- (2-propynyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimide

N- {3,5-diflu-l-6- (1-methyl-2-propynyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimide

N- {5-chloro-1-fluoro-6- (1-methyl-2-propynyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimide

{3-chloro-1-fluoro-6- (1-methyl-2-propynyloxy) pyridine-2-yl} 3,4,5,6-tetrahydrophthalimide

{3,5-dichloro-6- (1-methyl-2-propynyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimide

N- {3,5-Difluoro-6- (2-propynyloxy) pyridin-2-yl} 2,3-dimethylmaleimide

-{5-Chloro-3-fluoro-6- (2-propynyloxy) pyridin-2-yl} 2,3-dimethylmaleimide

N- {3,5-difluoro-6- (1-methyl-2-provinyloxy) pyridin-2-yl} 2,3-dimethylmaleide

'-{5-Chloro-3-fluoro-6- (1-methyl-2-brovinyloxy) pyridine -2 -Yl} 2,3-dimethylmaleide

3 2. A herbicidal method comprising treating an effective amount of a compound selected from the compounds defined in claim 1.

33. A herbicidal method comprising treating an effective amount of a compound selected from the compounds defined in claim 3.

34. A herbicidal method comprising treating an effective amount of a compound selected from the compounds defined in claim 5.

35. A herbicidal method comprising treating an effective amount of a compound selected from the compounds defined in claim 9.

36. A herbicidal method comprising treating an effective amount of a compound selected from the compounds defined in claim 11.

37. A herbicidal method, wherein an effective amount of a compound selected from the compounds defined in claim 12 is treated.

38. A herbicidal method comprising treating an effective amount of a compound selected from the following compounds.

N- {3,5-difluoro-6- (2-bromovinyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimid

N- {5-chloro-1-fluoro-6- (2-fluorohynoxy: pyridin-2-y} 3,4,5,6-tetrahydrophthalimid

N- {3-chloro-5-fluoro-6- 2-diphenyloxy: 'pyridine-2-di} 3, 4, 5, 6-tetrahydrophthalimid N- {3,5-dichloro-6- (2-bromovinyloxy) pyridine-2-yl 3,4,5,6-tetrahydrophthalimide-

N- {3,5-difluoro-6- (1-methyl-2-propynyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimide

{5-chloro-1-fluoro-6- (1-methyl-2-propynyloxy) pyridine-2-yl} 3,4,5,6-tetrahydrophthalimide

N- {3-Chloro-5-fluoro-6- (1-methyl-2-propynyloxy) pyridine-2-yl} 3,4,5,6-tetrahydrophthalimide

N- {3,5-dichloro-6- (1-methyl-2-brovinyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimide

N- {3,5-difluoro-6- (2-propynyloxy) pyridin-2-yl} 2,3-dimethylmaleimide

{5-chloro-3-fluoro-6- (2-propynyloxy) pyridine-2-yl} 2,3-dimethylmaleimide

N- {3,5-difluoro-6- (trimethyl-2-propynyloxy) pyridine-2-yl} 2,3-dimethylmaleimide

: \:-{5-Chloro-3-fluoro-6- (1-methyl-2-propynyloxy) pyridin-2-yl} 2,3-dimethylmaleimide

39. —General formula

(Wherein, R ⁵ and R ⁵ are the same or different and have the same number of carbon atoms: an alkyl group having L to 6 or R ⁵ and R ^s together represent an alkylene group having 3 or 4 carbon atoms. Compound represented and general formula

(Wherein, R ¹ , R ² and R ³ are the same or different and represent a hydrogen atom or a halogen atom, and R ⁴ is an amino group optionally having one or two substituents selected from the following group A) Represents a substituted oxy group having a substituent selected from the following group B or a substituted thio group having a substituent selected from the following group B, or R ³ and R ⁴ are taken together to form the formula 1 CH = CH — May form a group represented by —CH—CH—.

A compound represented by the general formula:

(Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ^s are as defined above).

[Group A]

[Group B]

L ', which may have a substituent selected from Group C below, an alkyl group having 1 to 6 carbon atoms, and C2 to 6 carbon atoms which may have a substituent selected from Group C below. An alkenyl group and an alkynyl group having 2 to 6 carbon atoms which may have a substituent selected from the following group C;

[Group C]

Alkyloxy group with 1 to 6 carbon atoms / Lefonyl group, alkenyloxy group with 2 to 6 carbon atoms, and alkynyloxy group with 2 to 6 carbon atoms

40.-General formula

(Wherein, R 5 and R 6 represent a methyl group, or R ⁵ and R ^{6 taken} together represent an alkylene group having 3 or 4 carbon atoms.)

A compound represented by the general formula

(Wherein, R ¹ and R ³ are the same or different and represent a halogen atom, R ² represents a hydrogen atom, and R ⁴ may have one or two substituents selected from the following group A) A amino group, a substituted oxy group having a substituent selected from the following group B or a substituted thio group having a substituent selected from the following group B; or together with R ³ , a group represented by the formula —CH = A group represented by CH-CH = CH- may be formed.)

Wherein the compound represented by the general formula is condensed.

(Wherein, R ¹ , R ² , R ³ , FT, R ⁵ and R ⁵ have the same meanings as described above.).

[Group A] An alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, and an alkynyl group having 2 to 6 carbon atoms.

[Group B]

[Group C]

Alkyloxycarbonyl group having 1 to 6 carbon atoms, alkenyloxycarbonyl group having 2 to 6 carbon atoms, and alkynyloxycarbonyl group having 2 to 6 carbon atoms

41. General formula

(In the formula, R ⁵ and R ⁶ are the same or different and represent an alkyl group having 1 to 6 carbon atoms, or R ⁵ and R ⁶ together represent an alkylene group having 3 or 4 carbon atoms.)

A compound represented by the general formula

(In the formula, R ¹ , R ² and R ³ are the same or different and each represent a hydrogen atom or a halogen atom, and R ⁴ is an amino group having one or two substituents selected from the following A ′ group. A substituted oxy group having a substituent selected from group B ', or selected from group B'

.

/ 00976 PCT / JP91 / 00918

And may represent a substituted thio group having a substituted moiety, or together with R ³ may form a group represented by the formula —CH—CH—CH = CH—. )

A compound represented by the general formula:

(Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁵ have the same meanings as described above).

[Α 'group]

[Β 'group]

42. General formula

(Wherein, R ⁵ and R ^s represent a methyl group, or R ^s and R ^s together represent an alkylene group having 3 or 4 carbon atoms.)

A compound represented by the general formula

(Wherein R ¹ and R ³ are the same or different and represent a halogen atom, R ² represents a hydrogen atom, R ⁴ is an amino group having one or two substituents selected from the following A ′ group, Represents a substituted oxy group having a substituent selected from the group B 'or a substituted thio group having a substituent selected from the following group B', or R ³ and R ⁴ together form a formula -CH- A group represented by CH—CH = CH— may be formed.)

A compound represented by the general formula:

(Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ have the same meaning as described above, and are represented by _c.

[Α 'Group〗

[Β 'group]

An alkenyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, and an alkynyl group having 2 to 6 carbon atoms.

43.-General formula

(Wherein, R ⁵ and R ^s are the same or different and each represent an alkyl group having 1 to 6 carbon atoms; orR ⁵ and R ⁶ together represent a 3 or 4 carbon alkylene group.

^: Represented compound and general formula 6S

(Wherein, R ^1, R ² and 1¾ ³ is shows the same or different and each represents a hydrogen atom or a halogen atom, R ⁴ is a "substituent Okishi group or the following B having a substituent selected from Group" group B below A substituted thio group having a selected substituent is shown.)

A compound represented by the general formula:

(Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ^s have the same meanings as described above.).

[Group B]

44.-General formula

(Wherein, R ⁵ and R ^s are the same or different and represent an alkyl group having 1 to 6 carbon atoms, or R ⁵ and R ⁶ are taken together to represent an alkylene group having 3 or 4 carbon atoms. Compound represented and general formula

(Wherein, R ¹ and R ³ are the same or different and represent a halogen atom, R ² represents a hydrogen atom, and R ⁴ is a substituted oxy group having a substituent selected from the following B "group or the following B" group Represents a substituted thio group having a substituent selected from:

A compound represented by the general formula:

(Wherein Ri, R ² , R ³ , FT, R ⁵ and ^Re have the same meanings as described above).

[Group B]

An alkenyl group having 2 to 6 carbon atoms and an Oalkini group having 2 to 6 carbon atoms.

45 General formula

(In the formula, R ⁵ and R ⁶ represent a methyl group, or R ⁵ and R ⁶ together represent an alkylene group having 3 or 4 carbon atoms.)

A compound represented by the general formula

(Wherein, R ¹ and R ³ are the same or different and represent a fluorine atom or a chlorine atom, R ² represents a hydrogen atom, and R ⁴ is a substituted oxy group having a substituent selected from the following B "group or B "represents a substituted thio group having a substituent selected from the group.)

A compound represented by the general formula:

(Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁵ have the same meanings as described above.) A method for producing a compound represented by the following formula:

[B ', group]

An alkenyl group having 2 to 6 carbon atoms and an alkynyl group having 2 to 6 carbon atoms c 46.

(In the formula, R ⁵ and R ⁶ together represent a butylene group.)

A compound represented by the general formula

(Wherein R ¹ and R ³ represent a fluorine atom, R ² represents a hydrogen atom, and R ⁴ is selected from a substituted oxy group having a substituent selected from the following B "group or the following B" group And represents a substituted thio group having a substituent.

A compound represented by the general formula:

(Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁵⁵ have the same meanings as described above.).

[Group B]

47-General formula

(Wherein, R ⁵ and R ⁶ are the same or different and represent an alkyl group having 1 to 6 carbon atoms, or together with and represent an alkynyl group having 3 or 4 carbon atoms. Compound and general formula

(In the formula, R ¹ , R ² and R ³ are the same or different and each represent a hydrogen atom or a halogen atom, and R ⁴ represents an alkynyloxy group having 2 to 6 carbon atoms.)

A compound represented by the general formula:

(Wherein, R ¹ , R ² , R ³ , R ⁴ , R ^5, and FT have the same meanings as described above.)

48. General Formula

(In the formula, R ⁵ and R ^s are the same or different and each represent an alkyl group having 1 to 6 carbon atoms, or R ⁵ and R ⁶ together represent an alkylene group having 3 or 4 carbon atoms.)

A compound represented by the general formula

(Wherein R ¹ and R ³ are the same or different and represent a halogen atom, and R ² is a hydrogen atom R ⁴ represents an alkynyl-T xy group having 2 to 6 carbon atoms. )

A compound represented by the general formula:

(Wherein, R ¹ , R ² , R ³ , R ⁵ and R ⁶ have the same meaning as described above.)

49. General formula

(Wherein, R ⁵ and R ^s represent a methyl group, or R ⁵ and R ^e together represent an alkylene group having 3 or 4 carbon atoms.)

A compound represented by the general formula

(In the formula, R ¹ and R ³ are the same or different and each represents a fluorine atom or a chlorine atom, R ² represents a hydrogen atom, and R ⁴ represents an alkynyloxy group having 2 to 6 carbon atoms.) A compound represented by the general formula:

(Wherein, R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ have the same meanings as described above.) .

50. Expression

(In the formula, R ⁵ and R ⁶ are taken together to represent a butylene group.)

A compound represented by the general formula

(In the formula, R ¹ and R ³ represent a fluorine atom, R ² represents a hydrogen atom, and R ⁴ represents an alkynyloxy group having 2 to 6 carbon atoms.)

A compound represented by the general formula:

51 · A method for producing the following compound produced by the method of claim 39.

N- {3,5-difluoro-6- (2-propynyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimid

N- {5-chlorofluoro-6- (2-provinyloxy) pyridin-2-yl} 3, 4,5,6-tetrahydrophthalimide

N- {3-chloro-5-fluoro-6- (2-prohynyroxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimide

{3,5-dichloro-6- (2-propynyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimide

N- {3,5-difluoro-mouth 6-methyl-2-propynyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimide

N- {3-chloro-5-fluoro-6- (1-methyl-2-propynyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimide

N- {3,5-dichloro-6- (1-methyl-2-prodenyloxy) pyridine-2-yl 3,4,5,6-tetrahydrophthalimide

N- {3,5-Difluoro-6- (2-propynyloxy) pyridin-2-yl} 2,3-dimethylmaleimide

N- {5-Chloro-3-fluoro-6- (2-proburoxy) pyridin-2-yl} 2,3-dimethylmaleimide

-{3,5-difluoro-6- (1-methyl-2-propynyloxypyridin-2- 2-dimention) 2,3-dimethylmaleimide

-{5-chloro-1-fluoro-6- (1-methyl-2-bromovinyloxy) 'pyridine-2-yl} 2,3-dimethylmaleimide

52. —General formula

(In the formula, R ¹ , R ^{2 and} 'R ³ are the same or different and each represents hydrogen or a halogen atom. And R ⁴ is an amino group optionally having one or two substituents selected from Group A, a substituted oxy group having a substituent selected from Group B below, or a group B below. Ru te formula i CH

And the features and

(Where

Represents an S m yellow atom. )

A method for producing a compound represented by the formula:

[Group A]

[Group B]

An alkyl group having 1 to 6 carbon atoms which may have a substituent selected from Group C, and an alkenyl having 2 to 6 carbon atoms which may have a substituent selected from the following Group C And an alkynyl group having 2 to 6 carbon atoms which may have a substituent selected from the following group C

[Group C]

5 3. General formula 7

(Wherein R ¹ , R ^{2 and} R ³ are the same or different and each represent a hydrogen atom or a halogen atom, and R ⁴ is an amino group having one or two substituents selected from the following A ′ group; 'Represents a substituted oxy group having a substituent selected from the group B or a substituted thio group having a substituent selected from the following group B'; or R ³ and R ⁴ together form the formula 1 CH = CH— A group represented by CH-CH— may be formed.)

Characterized by reacting a ligated compound represented by the formula with phosgene or thiophosgene in the presence of a base,

(Wherein, R ¹ , R ² , R ³ and R have the same meanings as described above, and X represents an oxygen atom or a sulfur atom. :)

A method for producing a compound represented by the formula:

[Α 'group]

[Β 'group]

54. General Formula 2/00976 PC / JP91 / 00918

78

(Wherein R ¹ , R ² and R ³ are the same or different and represent a hydrogen atom or a halogen atom, and R ⁴ is a substituted oxy group having a substituent selected from the following B "group or the following B" group A substituted thio group having a selected substituent is shown.)

Reacting a compound represented by the formula with phosgene in the presence of a base;

(Where

Has the same meaning as described above, and X represents an oxygen atom. CB "group

55.-General formula

(In the formula, R ′, R ² and R ³ are the same or different and represent a hydrogen atom or a halogen atom, and R ⁴ represents an alkynyloxy group having 2 to 6 carbon atoms.)

And phosgene in the presence of a base in the presence of a base.

(Wherein, R ¹ , R ² , R ³ and R ⁴ have the same meanings as described above, and X represents an oxygen atom.)

56. General formula

(In the formula, R ¹ and R ³ are the same or different and each represent a nitrogen atom or a chlorine atom, R ² represents a hydrogen atom, and R ⁴ represents an alkenyloxy group having 2 to 6 carbon atoms.) Characterized by reacting the compound represented by the formula with phosgene in the lower left base,

(Wherein, R ¹ , R ² , R ³ and R ⁴ have the same meanings as described above, and X represents an oxygen atom

. )

A method for producing a compound represented by the formula:

D-general formula SO

(Wherein, R ¹ and R ² represent a fluorine atom, R ² represents a hydrogen atom, and R ⁴ represents an alkynyloxy group having 2 to 6 carbon atoms.)

Characterized by reacting in the presence of a base represented by the general formula

(Where

Represents the same meaning as described above, and X represents an oxygen atom.o)

A method for producing a compound represented by the formula:

58. A process for producing the following compound produced by the process of claim 52.

N- {3,5-difluoro-S- (2-propynyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimide

N- {5-chloro-1-fluoro-6- (2-propynyloxy) pyridine: 2-yl 3,4,5,6-tetrahydrophthalimide

N- {3-chloro-1-fluoro-6- (2-propynyloxy) pyridine-2-yl 3,4,5,6-tetrahydrophthalimide

N- {3,5-dichloro-6- (2-proburoxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimide

-{3,5-difluoro-6-methyl-2-propynyloxypyridin-2-yl} 3,4,5,6-tetrahydrophthalimide

N- 5-Chloro-3-fluoro-6-ke-methyl-2-propynyloxy.) Pyridine-2 -Yl} 3,4,5,6-tetrahydrophthalimide

N- {3-chloro-1-fluoro-6- (1-methyl-2-propyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimid

N- {3,5-dichloro-6- (trimethyl-2-propynyloxy) pyridin-2-yl 3,4,5,6-tetrahydrophthalimid

{3,5-difluoro-6- (2-propynyloxy) pyridine-2-yl 2,3_dimethylmaleimide

N- {5-chloro-3-fluoro-6- (2-propynyloxy) pyridin-2-yl} 2,3-dimethylmaleide

N- {3,5-difluoro-6- (1-methyl-2-provinyloxy) pyridin-2-yl} 2,3-dimethylmaleide

N- {5-chloro-1-fluoro-6- (1-methyl-2-propynyloxy) pyridin-2-yl} 2,3-dimethylmaleide

59. · General formula

(Wherein, R ¹ , R ² and R ³ are the same or different and represent a hydrogen atom, a hydrogen atom or a logen atom, Z ¹ represents a halogen atom, and Q represents the following (Q-1) or (Q-2) (Wherein, R ⁵ and R ⁶ are the same or different and represent an alkyl group having 1 to 6 carbon atoms, or R ⁵ and R ⁶ together represent an alkylene group having 3 or 4 carbon atoms) And X represents an oxygen atom or a sulfur atom.

And a compound represented by the general formula R to H

(Wherein, R ⁷ is an amino group having one or two substituents selected from the following group A, a substituted oxy group having a substituent selected from the following group B, or a substituent selected from the following group B) And a substituted thio group having the formula: ^A general formula characterized by reacting the represented compound with a base in the presence of a base.

(In the formula, R ¹ , R ² , R ³ , R ⁷ and Q have the same meanings as described above.)

A method for producing a compound represented by the formula:

[Group A]

[Group B]

An alkyl group having 1 to 6 carbon atoms which may have a substituent selected from the following group C, an alkenyl group having 2 to 6 carbon atoms which may have a substituent selected from the following group C and An alkynyl group having 2 to 6 carbon atoms which may have a substituent selected from the following group C. .: '

[. Group]

6 0. General formula

(Wherein, R ¹ , R ² and R ³ are the same or different and represent a hydrogen atom or a halogen atom, Z ¹ represents a halogen atom, and Q represents the following (Q-1) or (Q-2) (Wherein, R ⁵ and R ⁶ are the same or different and each represent an alkyl group having 1 to 6 carbon atoms, or R ⁵ and R ⁶ represent an alkylene group having 3 or 4 carbon atoms in conjunction with R ⁵ and R ⁶ , X represents an oxygen atom or a sulfur atom.

And a compound represented by the general formula R ⁷ H

(In the formula, R ⁷ is an amino group having one or two substituents selected from the following group A ′, a substituted amino group having a substituent selected from the following group B ′, or a group selected from the following group B ′ Represents a substituted thio group having a substituent.)

Wherein the compound represented by the general formula is reacted in the presence of a base.

A method for producing a compound represented by the formula:

[Α 'group]

Carbon ¾ 2 to 6 alkenyl groups and carbon ¾ 2 to 6 alkenyl groups _c [Β 'group] An alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, and an alkynyl group having 2 to 6 carbon atoms.

61-General formula

(Wherein, R ¹ , R ² and R ³ are the same or different and represent a hydrogen atom or a halogen atom, Z ¹ represents a halogen atom, and Q represents the following (Q-1) or (Q-2) (Wherein, R ⁵ and R ^s are the same or different and represent an alkyl group having 1 to 6 carbon atoms, or R ⁵ and R ⁶ together represent an alkylene group having 3 or 4 carbon atoms; Represents an oxygen atom.

And a compound represented by the general formula R ⁷ H

(In the formula, R ⁷ represents a substituted oxy group having a substituent selected from the following B "group or a substituted thio group having a substituent selected from the following B" group.)

A method for producing a compound represented by the formula:

Q-2)

8δ

[Group B]

An alkenyl group having 2 to 6 carbon atoms and carbon atoms 2 to 6 carbon alkynyl groups _c

62-General formula

(Wherein, R ¹ , R ² and R ³ are the same or different and each represent a hydrogen atom or a halogen atom, Z ¹ represents a halogen atom, and CL represents the following (Q-1) or (Q-2) (Wherein, R ⁵ and R ⁶ are the same or different and each represent an alkyl group having 1 to 6 carbon atoms, or R ⁵ and R ⁵ represent an alkylene group having 3 or 4 carbon atoms, and X represents an oxygen atom. Shown.

And a compound represented by the general formula R ⁷ H

(Wherein, R ⁷ represents a C 2 -C 6 alkoxy) oxy group. ,

A compound represented by the general formula:

^{^{(Wherein, R 1, R 2, R}} 3, R 7 and Q are as defined above _c

A method for producing a compound represented by the formula:

63. General Formula

(Wherein R ¹ and R ³ are the same or different and represent a fluorine atom or a chlorine atom, R ² represents a hydrogen atom, Z ¹ represents a halogen atom, and Q represents the following (Q-1) (Formula Wherein R ⁵ and R ^{6 each} represent a methyl group or an alkylene group having 3 or 4 carbon atoms in conjunction with R ⁵ and R ^6. ))

And a compound represented by the formula R ⁷ H

(In the formula, R ⁷ represents an alkynyloxy group having 2 to 6 carbon atoms.)

(Wherein, R ¹ , R ² , R ³ , R ⁷ and Q are as defined above.

A method for producing a compound represented by the formula:

64. General Formula

(Wherein R ¹ and R ³ represent a fluorine atom, R ² represents a hydrogen atom, and Z; Represents a sulfur atom, and Q represents the following (Q-1) (wherein, R ⁵ and RS represent a 'butylene group together. J. :)

And a compound represented by the general formula R ⁷ H

(Wherein, R ⁷ represents an alkynyloxy group having 2 to 6 carbon atoms.)

(Wherein, R ¹ , R ² , R ³ , R ⁷ and Q are as defined above.

A method for producing a compound represented by the formula:

·

65. A process for producing the following compound produced by the process of claim 59:

N- {3,5-difluoro-6- (2-bromovinyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimide

N- {5-chloro-3-fluoro-6- (2-propynyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimid

N- {3-chloro-5-fluoro-6- (2-propynyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimid

X- (3,5-dichloro-6- (2-propini-dioxy-pyridin-2--2-di): '3,4,5,6-r

X- {3,5-difluoro-6-(]-meth-2--2-buhynyroxy) pyridine-2-yl} 3,4,5,6- phthalimid {5-chloro-3-fluoro-6- (1-methyl-2-pucopinyl) pyridine-2-yl} 3,4,5,6-tetrahydrophthalimide —

N- {3-chloro-1-fluoro-6_ (1-methyl-2-bromovinyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrofurimide

N-3,5-dichloro-6- (1-methyl-2-propynyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimide

N- {3,5-Difluoro-6- (2-propynyloxy) pyridin-2-yl} 2,3-dimethylmaleimide

N- {5-Chloro-3-fluoro-6- (2-brovinyloxy) pyridine-2-yl} 2,3-dimethylmaleimide

N- {3,5-difluoro-6- (1-methyl-2-propynyloxy) pyridin-2-yl} 2,3-dimethylmaleimide

N- {5-chloro-1-fluoro-6- (1-methyl-2-propynyloxy) pyridine-2-yl} 2,3-dimethylmaleimide

66. General Formula

(Wherein, R ¹ , R ² and R ³ are the same or different and represent a hydrogen atom or a halogen atom, Z ² represents an OH group, an SH group or an NH ₂ group, and Q represents the following (Q-1) or (Q-2) shows a (wherein, R ⁵ and R ⁶ are the same or different or indicating the number 1 to 6 § alkyl group having a carbon R ⁵ and R ⁶ force s- cord such a connexion carbons 3 Or X represents an alkylene group, and X represents an oxygen atom or a sulfur atom.

And a compound represented by the general formula R ⁸ -Y ′

(Wherein, Y represents a halogen atom, ^Ra is an alkyl group having 1 to carbon atoms which may have a substituent selected from the following group C, and has a substituent selected from the following group C) A alkenyl group having 2 to 6 carbon atoms which may be substituted and an alkynyl group having 2 to 6 carbon atoms which may have a substituent selected from the following group C. )

A compound represented by the general formula:

(Wherein, R ¹ , R ² , R ³ and Q have the same meanings as described above, R ⁷ is an amino group having one or two substituents selected from the following group A, and is selected from the following group B Represents a substituted oxy group having a substituted moiety or a substituted thio group having a substituted moiety selected from the following group B.)

A method for producing a compound represented by the formula:

[Group A]

[Group B]

[Group C]

Alkoxycarbonyl group having 1 to 6 carbon atoms, alkenylcarbonyl group having 2 to 6 carbon atoms and alkoxycarbonyl group having 2 to 6 carbon atoms

67. General Formula

(Wherein, R ¹ , R ² and R ³ are the same or different and represent a hydrogen atom or a halogen atom, Z ² represents an OH group, an SH group or an NH ₂ group, and Q represents the following (Q-1) or (Wherein, R ⁵ and R ⁶ are the same or different and represent an alkyl group having 1 to 6 carbon atoms, or R ⁵ and R ⁶ together form a C 3 or 4 X represents an alkylene group, and X represents an oxygen atom or a sulfur atom.

And a compound represented by the general formula R ⁸ — Υ

(Wherein, Υ represents a halogen atom, R ⁸ represents an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, and an alkynyl group having 2 to 6 carbon atoms.) A compound represented by the general formula:

(Wherein, R ¹ , R ² , R ³ and CI have the same meanings as described above, R ⁷ is an amino group having one or two substituents selected from the following group A ′, and selected from the following group B ′ Represents a substituted oxy group having a substituted moiety or a substituted thio group having a substituted moiety selected from the following group Β):

A method for producing a compound represented by the formula:

[Group A ']

[Group B *]

68. General Formula

(Formula, R ¹ , R ² and R ³ are the same or different and represent a hydrogen atom or a halogen atom, Z ² represents an OH group, an SH group or a Γ \ 'Η ₂ group, and Q represents the following (Q— (1) or (Q-2), wherein R ⁵ and R ^s are the same or different and represent an alkyl group having 1 to 6 carbon atoms, or R ⁵ and R ⁶ are linked together. If it has 3 or 4 carbon atoms, it represents an alkylene group, and X represents an oxygen atom.

And a compound represented by the general formula R ⁸ — Υ

(In the formula, Υ represents a halogen atom, and R ⁸ represents an alkenyl group having 2 to 6 carbon atoms or an alkynyl group having 2 to 6 carbon atoms.)

Wherein the compound represented by the general formula is reacted in the presence of a base. Q with N eight R '

(Wherein, R ¹ , R ² , R ³ and Q have the same meanings as described above, and R ⁷ is a substituted oxy group having a substituent selected from the following B "group or a substituent selected from the following B" group Represents a substituted thio group having a moiety.)

A method for producing a compound represented by the formula:

[Group B]

An alkenyl group having 2 to 6 carbon atoms and an alkynyl group having 2 to 6 carbon atoms _c 69. General formula

(Wherein, R ¹ , R ² and R ³ are the same or different and represent a hydrogen atom or a halogen atom, Z ² represents an OH group, an SH group or an NH ₂ group, and Q represents the following (Q-1) or Wherein R ⁵ and R ⁶ are the same or different and represent an alkyl group having 1 to 6 carbon atoms, or R ⁵ and R ⁶ are taken together to form an alkyl group having 3 or 4 carbon atoms. X represents an alkylene group, and X represents an oxygen atom. )

And a compound represented by the general formula R ⁸ -Y

(In the formula, Y represents a halogen atom, and R ⁸ represents an alkynyl group having 2 to 6 carbon atoms. You. )

(In the formula, R ¹ , R ² , R ³ and Q have the same meanings as described above, and R ⁷ represents an alkynyloxy group having 2 to 6 carbon atoms.)

A method for producing a compound represented by the formula:

70-General formula

(Wherein R ¹ and R ³ are the same or different and represent a fluorine atom or a chlorine atom, R ² represents a hydrogen atom, Z ² represents a 0H group, an SH group or an NH ₂ group, and Q represents the following (Q — In the formula, R ⁵ and R ⁶ represent a methyl group or an alkylene group having 3 or 4 carbon atoms together with R ⁵ .

And a compound represented by the general formula R ⁸ — Y

(In the formula, Y represents a halogen atom, and R ⁸ represents an alkynyl group having 2 to 6 carbon atoms.)

A method for producing a compound represented by the formula:

71.-General formula

(Wherein R ¹ and R ³ represent a fluorine atom, Ζ ² represents a 0Η group, an SH group or a ΝΗ ₂ group, and Q represents the following (Q-1) (where R ⁵ and R ⁶ represent And a butylene group.))) A compound represented by-and a compound represented by the formula R ⁸ — Υ

(In the formula, Υ represents a halogen atom, and R ⁸ represents an alkynyl group having 2 to 6 carbon atoms.)

A method for producing a compound represented by the formula:

72. A process for producing the following compound produced by the process of claim 66.

N- {3,5-difluoro-6- (2-bromovinyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrofurimide

N- {5-chloro-3-fluoro-6- (2-propynyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimide

N- {3-chloro-5-fluoro-6- (2-propynyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimide

N- {3,5-dichloro-6- (2-propynyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimide

N- {3,5-Difluoro-6- (1-methyl-2-propynyloxy) pyridine-2- 2-di} 3,4,5,6-tetrahydrophthalimide

N- {5-chloro-1-fluoro-6- (1-methyl-2-bromovinyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimide

N- {3-chloro-1-fluoro-6- (1-methyl-2-propynyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimide

N- {3,5-dichloro-6- (1-methyl-2-propynyloxy) pyridin-2-yl} 3,4,5,6-tetrahydrophthalimide

N- {3,5-difluoro-6- (2-propynyloxy ') pyridin-2-yl} 2,3-dimethyl, Γί- {5-chloro-3-fluoro-6- (2-propynyloxy) pyridin-2-yl 2,3-dimethylmaleimide

Ν- · {3,5-difluoro mouth-6- (trimethyl-2-propynyloxy) pyridin-2-yl} 2,3-dimethylmaleimide

{-{5-chloro-1-fluoro-6-methyl-2-bromovinyloxy) pyridin-2-yl} 2,3-dimethylmaleimide