JP2010502661A5

JP2010502661A5 -

Info

Publication number: JP2010502661A5
Application number: JP2009527047A
Authority: JP
Filing date: 2007-09-04
Publication date: 2010-09-30

Claims

Compounds of general formula I:

Wherein Q ¹ and Q ³ are halogen, and Q ² is hydrogen,
R ¹ is optionally substituted C _1-4 alkyl, optionally substituted C _2-4 alkenyl, optionally substituted C _2-4 alkynyl, or optionally substituted C _3-4 cycloalkyl. Yes,
R ² is hydrogen, C _1-8 alkyl, C _3-4 cycloalkyl, C _2-8 alkenyl, cyano, hydroxy, alkoxy, cyano (C _1-4 ) alkyl, C _1-4 alkoxy (C _1-4 ) Alkyl, C _1-4 alkoxy (C _1-4 ) alkoxy (C _1-4 ) alkyl, or benzyloxy (C _1-4 ) alkyl, wherein the phenyl ring is optionally substituted by C _1-4 alkoxy Has been replaced,
R ³ is — (CR ^a R ^b ) _p (CR ^c R ^d ) _q (X) _r (CR ^e R ^f ) _s R ⁴ , where R ^a , R ^b , R ^c , R ^d , R ^e and R ^f , independently of one another, are hydrogen, C _1-4 alkyl, halogen, cyano, hydroxy, C _1-4 alkoxy, or C _1-4 alkoxycarbonyl, or R ^a R ^b , R ^c R ^d or R ^e R ^f may be combined to form a 3-8 membered carbocyclic ring, or sulfur, oxygen and NR ⁰ , where R ⁰ is hydrogen or optionally substituted C _1-6 alkyl. A heterocyclic ring containing a heteroatom selected from
X is (CO), (CO) O, O (CO), O, S (O) _t , where t is 0, 1 or 2, or X is NH or N (C _1-6 ) is alkyl,
p, r and s are independently of each other 0 or 1,
q is 0, 1 or 2;
R ⁴ is optionally substituted C _1-6 alkyl, optionally substituted C _2-6 alkenyl, —CR ^UU ═NR ^VV , where R ^uu is hydrogen or C _1-6 alkyl; And R ^VV is hydroxy or optionally substituted C _1-6 alkoxy, optionally substituted aryloxy or optionally substituted heteroaryloxy), or —CH ₂ —C≡C—R ^5. And where
R ⁵ is hydrogen, halogen, hydroxy, C _1-6 alkoxy, C _1-3 alkoxy (C _1-3 ) alkoxy, cyano, C _1-4 alkylcarbonyloxy, aminocarbonyloxy, mono- or di (C _1-4 ) -alkylaminocarbonyloxy, tri (C _1-4 ) alkylsilyloxy, or —S (O) _g (C _1-6 ) alkyl (wherein g is 0, 1 or 2) . present) by either a C _1-8 alkyl optionally substituted, or R ⁵ is halogen, hydroxy, C _1-6 alkoxy, C _1-3 alkoxy - (C _1-3) alkoxy, cyano, C _1-4 alkylcarbonyloxy, aminocarbonyloxy, mono- or di (C _1-4 ) alkyl-aminocarbonyloxy, tri (C _1-4 ) alkylsilyloxy, or —S (O) _g (C _1-6 ) Alkyl (wherein g is 0) 1 or 2.) By either a C _3-6 cycloalkyl optionally substituted, or R ^5, C _3-6 cycloalkyl (C _1-4) alkyl, wherein alkyl and / or Cycloalkyl moieties may be halogen, hydroxy, C _1-6 alkoxy, C _1-3 alkoxy (C _1-3 ) alkoxy, cyano, C _1-4 alkylcarbonyloxy, aminocarbonyloxy, mono- or di (C _{1- 4} ) Optional by alkylaminocarbonyloxy, tri (C _1-4 ) alkyl-silyloxy, or —S (O) _g (C _1-6 ) alkyl (wherein g is 0, 1 or 2). Or R ⁵ is optionally substituted aryl, optionally substituted aryl (C _1-4 ) alkyl, optionally substituted aryloxy (C _1-4 ) alkyl, optionally substituted Hetero Is aryl, or optionally substituted heteroaryl (C _1-4 ) alkyl, or optionally substituted heteroaryloxy (C _1-4 ) alkyl, or R ⁴ is optionally substituted C _{3 -6} cycloalkyl, optionally substituted C _5-6 cycloalkenyl, optionally substituted aryl, optionally substituted heteroaryl, or sulfur, oxygen or NR ^{0 where} R ⁰ is hydrogen or optional . have been C _1-6 alkyl substituted) or a 5-～8- membered rings that are optionally substituted, optionally containing a heteroatom chosen from, or R ^3, - (CR ^a R ^b ) _P (CR ^c R ^d ) _q (X) _r (CR ^e R ^f ) _s R ⁴ , R ² and R ³ are combined to form halogen, C _1-4 alkyl, mono- or di- Optionally substituted by (C _1-4 ) alkylaminocarbonyl And sulfur, oxygen and NR ^{00 where} R ⁰⁰ is C _1-4 alkyl optionally substituted with halogen, C _1-6 alkoxy or cyano, or R ⁰⁰ is nitro, C _1-4 It is phenyl optionally substituted by alkyl, halo (C _1-4 ) -alkyl, C _1-4 alkylcarbonyl or heteroaryl. A 5- or 6-membered ring optionally containing a heteroatom selected from: or R ² and R ³ are joined to form an optionally substituted 6,6-membered bicycle You can,
R ³ is — (CR ³⁰ R ⁴⁰ ) C≡CR ⁵⁰ , wherein R ³⁰ and R ⁴⁰ are independently of each other hydrogen, C _1-6 alkyl, halo (C _1-4 ) alkyl, C _1-4 alkoxy (C _1-3 ) alkyl, C _2-3 alkenyl, or C _2-3 alkynyl, or R ³⁰ and R ⁴⁰ are attached to the carbon atom to which they are attached; Forming a six-membered carbocycle or a heterocycle containing a heteroatom selected from sulfur, oxygen or NR ⁰⁰⁰ , wherein R ⁰⁰⁰ is hydrogen or C _1-4 alkyl, wherein the carbocycle Or the heterocycle is optionally substituted with halo or C _1-4 alkyl;
R ⁵⁰ is hydrogen, optionally substituted C _1-4 alkyl, optionally substituted C _3-6 cycloalkyl, optionally substituted aryl, or sulfur, oxygen or NR ⁰⁰⁰ (where R ⁰⁰⁰ is Optionally substituted heteroaryl containing a heteroatom selected from: hydrogen or C _1-6 alkyl;
L is sulfur or oxygen, and n is 0, 1 or 2. And salts and N-oxides of compounds of formula I.

The compound according to claim 1, wherein Q ¹ is bromo.

The compound of claim 1, wherein Q ¹ is iodo.

The compound according to claim 1, wherein Q ¹ is chloro.

The compound of claim 1, wherein Q ¹ is fluoro.

Q ³ is a halogen compound of claim 1, wherein.

The compound according to claim 1, wherein Q ³ is fluorine.

The compound of claim 1, wherein Q ¹ is bromo, Q ² is hydrogen, and Q ³ is fluoro.

The compound of claim 1, wherein Q ¹ is bromo, Q ² is hydrogen, and Q ³ is chloro.

The compound of claim 1, wherein Q ¹ is iodo, Q ² is hydrogen, and Q ³ is fluoro.

The compound of claim 1, wherein Q ¹ is iodo, Q ² is hydrogen, and Q ³ is chloro.

The compound according to claim 1, wherein R ¹ is C _1-4 alkyl or halo (C _1-4 ) alkyl.

The compound according to claim 1, wherein R ¹ is methyl.

2. A compound according to claim ^{1 wherein} R < ¹ > is ethyl.

The compound according to claim 1, wherein R ² is hydrogen or methyl.

The compound of claim 1, wherein R ² is hydrogen.

R ³ is tert-butyl, 1-halo-2-methylprop-2-yl, 1,1-dihalo-2-methylprop-2-yl, 1,1,1-trihalo-2-methylprop-2-yl, 1-alkoxy-2-methylprop-2-yl, 1-alkenyloxy-2-methylprop-2-yl, 1-alkynyloxy-2-methylprop-2-yl, 1-cyano-2-methyl-prop-2-yl Yl, 1-alkoxyalkoxy-2-methyl-prop-2-yl, 1-halo-3-methylbut-3-yl, 1,1-dihalo-3-methylbut-3-yl, 1,1,1-trihalo -3-methylbut-3-yl, 1-alkoxy-3-methylbut-3-yl, 1-alkenyloxy-3-methylbut-3-yl, 1-alkynyloxy-3-methylbut-3-yl, 1 Cyano-3-methylbut-3-yl, 2-cyanoprop-2-yl, 2-methoxycarbonylprop-2-yl or 2-methylaminocarbonylprop-2-yl, 1-alkylthio-2-methylprop-2-yl 1-alkylsulfinyl-2-methylprop-2-yl, 1-alkylsulfonyl-2-methylprop-2-yl, 2-cyano-1-alkoxyprop-2-yl, 2-methyl-1-[(E and / Or Z) -hydroxyimino] -prop-2-yl, 2-methyl-1-[(E and / or Z) -alkoxyimino] -prop-2-yl, 2-methyl-1-[(E and / Or Z) -aryloxyimino] -prop-2-yl, 2-methyl-1-[(E and / or Z) -heteroaryloxyimino] -prop-2-yl, 1- Alkoxy-prop-2-yl, 1-halo-prop-2-yl, 3-methyl-but-1-yn-3-yl, 1-alkyl-3-methyl-but-1-yn-3-yl, 4-methyl-pent-2-yn-4-yl, 1-hydroxy-4-methyl-pent-2-in-4-yl, 1-alkoxy-4-methyl-pent-2-yn-4-yl, 1-alkoxyalkoxy-4-methyl-pent-2-yn-4-yl, 1-alkoxyalkoxyalkyl-4-methyl-pent-2-in-4-yl, 1-cyanoalkyl-3-methylbut-3- The compound of claim 1, which is yl, 1-haloalkyl-3-methylbut-3-yl.

R ³ is tert-butyl, 1-halo-2-methylprop-2-yl, 1-fluoro-2-methylprop-2-yl, 1-methoxy-2-methylprop-2-yl, 1-ethoxy-2- Methylprop-2-yl, 1-allyloxy-2-methylprop-2-yl, 1- (prop-2-ynyloxy) -2-methylprop-2-yl, 2-cyano-1-ethoxy-prop-2-yl, 2-cyano-1-methoxyprop-2-yl, 1-halo-3-methylbut-3-yl, 1-fluoro-3-methylbut-3-yl, 3-methylbut-1-in-3-yl, 4 -Methylpent-2-yn-4-yl, 5-methyl-hex-3-in-5-yl, 1-methoxy-4-methyl-pent-2-yn-4-yl, 1-allyloxy-4-methyl -Pent- - in-4-yl, 1-propargyloxy-4-methyl - pent-2-yn-4-yl, 1-ethoxy-4-methyl - pent-2-yn-4-yl, according to claim 17 Compound.

R ⁴ is C _1-6 alkyl optionally substituted by C _1-4 alkoxy- (C _1-4 ) alkoxy (C _1-4 ) alkyl, wherein the alkyl group is halo, mono- or di- C _1- optionally substituted _by- (C _1-6 ) alkylamino or tri (C _1-4 ) alkylsilyl, or R ⁴ optionally substituted by benzyloxy (C _1-4 ) alkyl. ₆ alkyl, wherein the alkyl group is optionally substituted by halo, mono- or di- (C _1-6 ) alkylamino or tri (C _1-4 ) alkylsilyl, or R ⁴ is C _2-6 alkenyloxy or _{_{-S (O) x (C 1-6}} ) C 1-6 alkyl optionally substituted by alkyl, wherein x is 0, 1 or 2, and the alkyl group , halo, mono- - or di - (C _1-6) alkylamino, -N (C _1-4) it is optionally substituted with alkyl = NOR, wherein R is a hydrogen or C _1-4 alkyl, or wherein the alkyl group, the tri (C _1-4) alkylsilyl Optionally substituted or R ⁴ is —CR ^UU ═NR ^VV where R ^UU is hydrogen or C _1-6 alkyl and R ^VV is hydroxy or optionally substituted C _2. A compound according to claim 1 which is _1-6 alkoxy.

Optionally substituted aryl and optionally substituted heteroaryl rings or moieties of the meaning R ⁵ are halogen, cyano, nitro, azide, C _1-6 alkyl, halo (C _1-6 ) Alkyl, C _3-6 cycloalkyl, C _3-6 cycloalkyl (C _1-4 ) alkyl, C _2-6 alkenyl, halo (C _2-6 ) alkenyl, C _2-6 alkynyl, halo (C _2-6 ) Alkynyl, C _1-6 alkoxy, halo (C _1-6 ) alkoxy, C _2-6 alkenyloxy, halo (C _2-6 ) alkenyloxy, C _2-6 alkynyloxy, halo (C _2-6 ) alkynyl Oxy, aryl, aryloxy, aryl (C _1-6 ) alkyl, aryl (C _1-6 ) alkoxy, heteroaryl, heteroaryloxy, heteroaryl (C _1-6 ) alkyl, heteroaryl (C _1-6 ) alkoxy, -SF _5, -S (O) _g (C _1-4 ) alkyl optionally substituted, where g is 0, 1 or 2, and alkyl is optionally substituted with halo, or R ⁵ is Optionally substituted with —OSO ₂ (C _1-4 ) alkyl, wherein the alkyl group is optionally substituted with halo, or R ⁵ is —CONR ^g R ^h , —COR ^g , —CO ₂ R ^g , —R ^g = NR ^h , —NR ^g R ^h , —NR ^g COR ^h , —NR ^g CO ₂ R ^h , —SO ₂ NR ^g R ^h , or —NR ^g SO ₂ R ⁱ optionally Substituted, wherein R ⁱ is C _1-6 alkyl optionally substituted with halogen, and R ^g and R ^h , independently of one another, are hydrogen or C optionally substituted with halogen. _1-6 alkyl or —CONR ^g R ^h or —SO ₂ NR ^g R ^h Where R ^g R ^h is bonded to a 5- or 6-membered carbocycle, or sulfur, oxygen or NR ⁰ , where R ⁰ is hydrogen or optionally substituted C _1-6 alkyl. The compound of claim 1, which may form a heterocycle containing a heteroatom selected from:

In an optionally substituted aryl, optionally substituted heteroaryl or optionally substituted 5- to 8-membered ring, R ⁴ is halogen, cyano, nitro, azide, C _1-6 alkyl, halo ( C _1-6 ) alkyl, C _3-6 cycloalkyl, C _3-6 cycloalkyl (C _1-4 ) alkyl, C _2-6 alkenyl, halo (C _2-6 ) alkenyl, C _2-6 alkynyl, halo (C _2-6 ) alkynyl, C _1-6 alkoxy, halo (C _1-6 ) alkoxy, C _2-6 alkenyloxy, halo (C _2-6 ) alkenyloxy, C _2-6 alkynyloxy, halo (C _2-6 ) Alkynyloxy, —SF ₅ , —S (O) _x (C _1-6 ) alkyl, optionally substituted, where x is 0, 1 or 2, and the alkyl group is or optionally substituted by halo, or R ^4, -OSO ₂ (C _1-4) alkyl It is optionally substituted with, wherein the alkyl group, ^{^{halogen, -CONR x R y, -CON (}} OR x) R y, -COR x, -CO 2 R x, -CR x = NR y, -NR ^{^{^{^{x R y, -NR x COR y}}}} , -NR x CO 2 R y, which is optionally substituted by -SO ₂ NR ^x R ^y or -NR ^X SO ₂ R ^Z,, wherein R ^z is a halogen a C _1-8 alkyl optionally substituted, and R ^x and R ^y are independently of each other, it is C _1-6 alkyl optionally substituted by hydrogen or halogen, a compound according to claim 1.

R ⁵⁰ is halogen, hydroxy, C _1-6 alkoxy, C _2-6 alkenyl, C _2-6 alkynyl, C _1-4 alkoxy (C _1-4 ) alkoxy, cyano, C _1-4 alkylcarbonyloxy, amino Carbonyloxy, mono- or di (C _1-4 ) alkylamino-carbonyloxy, S (O) _p (C _1-6 ) -alkyl (wherein p is 0, 1 or 2), triazolyl , Pyrazolyl, imidazolyl, tri (C _1-4 ) -alkylsilyloxy, optionally substituted phenoxy, optionally substituted thienyloxy, optionally substituted benzyloxy, or optionally substituted thienylmethoxy The compound of claim 1, which is C _1-4 alkyl substituted.

R ⁵⁰ is halogen, hydroxy, C _1-6 alkoxy, C _1-4 alkoxy (C _1-4 ) alkoxy, cyano, C _1-4 alkylcarbonyloxy, aminocarbonyloxy, mono- or di (C _1-4 ) Alkylamino-carbonyloxy, S (O) _p (C _1-6 ) -alkyl (wherein p is 0, 1 or 2), triazolyl, pyrazolyl, imidazolyl, tri (C _1-4 ) -Alkylsilyloxy, optionally substituted phenoxy, optionally substituted thienyloxy, optionally substituted benzyloxy, or optionally substituted thienylmethoxy is C _3-6 cycloalkyl. The compound of claim 1.

In optionally substituted aryl or optionally substituted heteroaryl, R ⁵⁰ is halogen, hydroxy, mercapto, C _1-4 alkyl, C _2-4 alkenyl, C _2-4 alkynyl, C _1-4 alkoxy, C _2-4 alkenyloxy, C _2-4 alkynyloxy, halo (C _1-4 ) alkyl, halo (C _1-4 ) alkoxy, C _1-4 alkylthio, halo (C _1-4 ) -alkylthio, hydroxy ( C _1-4 ) alkyl, C _1-4 alkoxy (C _1-4 ) alkyl, C _3-6 cycloalkyl, C _3-6 cycloalkyl- (C _1-4 ) alkyl, phenoxy, benzyloxy, benzoyloxy, cyano, isocyano, thiocyanato, isothiocyanato, ^{^{^{nitro, NR p R q, NHCOR P}}} , -NHCONR p R q, CONR p R q, -SO 2 R 0, OSO 2 R 0, COR P, CR p = NR q or = CR ^p R being optionally substituted by ^q, wherein R ⁰ is, C _1-4 alkyl, halo (C _1-4) alkyl, C _1-4 alkoxy, halo (C _1-4) alkoxy, C _1-4 alkylthio, C _3-6 cycloalkyl, C _3-6 cycloalkyl (C _1-4 ) alkyl, phenyl or benzyl, and the phenyl and benzyl groups are halogen, C _1-4 alkyl or C _1. Optionally substituted by _-4 alkoxy, and R ^p and R ^q are independently hydrogen, C _1-4 alkyl, halo (C _1-4 ) alkyl, C _1-4 alkoxy, halo (C _{1 -4} ) alkoxy, C _1-4 alkylthio, C _3-6 cycloalkyl, C _3-6 cycloalkyl (C _1-4 ) alkyl, phenyl or benzyl, the phenyl group and benzyl group being halogen, C ₁ optionally substituted by _-4 alkyl or C _1-4 alkoxy,請The compound of claim 1.

The compound of claim 1, wherein L is oxygen.

The compound according to claim 1, wherein n is 0.

A fungicidal composition comprising a fungicidally effective amount of a compound according to claim 1 and a carrier or diluent suitable therefor.

Applying a fungicidally effective amount of the compound according to claim 1 to the plant, to the seed of the plant, to the plant or the place of growth of the seed, or to the soil or to any other plant growth medium. , A method for controlling or controlling phytopathogenic fungi.