Substituted benzene fungicides

Patent metadata

Field	Value
Publication number	US-9743667-B2
Application number	US-201514812083-A
Country	US
Kind code	B2
Filing date	Jul 29, 2015
Priority date	Apr 3, 2007
Publication date	Aug 29, 2017
Grant date	Aug 29, 2017

Abstract

Disclosed are compounds of Formula 1, including all geometric and stereoisomers, N-oxides, and salts thereof,

wherein
W is O or S; V is a direct bond or NR 3 ; Q is or CR 6a R 6b , O, NR 7 , C═N—O—R 7 or C(═O); Y is —C(R 5 )═N—O—(CR 8a R 8b ) p —X—(CR 9a R 9b ) q —SiR 10a R 10b R 10c ; or a phenyl ring substituted as defined in the disclosure; or Z; and R 1 , R 2 , R 3 , R 4 , R 5 , R 6a , R 6b , R 7 , R 8a , R 8b , R 9a , R 9b , R 10a , R 10b , R 10c , Z, p and q are as defined in the disclosure.

Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling plant disease caused by a fungal pathogen comprising applying an effective amount of a compound or a composition of the invention.

First claim

What is claimed is:

1. A compound selected from Formula 1, N-oxides and salts thereof,

wherein
each R 1 and R 2 is independently H, halogen, CN, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkoxy, C 3 -C 6 cycloalkyl, C 3 -C 15 trialkylsilyl or C 3 -C 15 halotrialkylsilyl;
V is a direct bond or NR 3 ;
R 3 is H, C 1 -C 3 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 3 haloalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl, C 2 -C 6 alkoxycarbonyl or C 2 -C 6 haloalkoxycarbonyl;
R 4 is H, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 6 cycloalkoxy, C 1 -C 6 alkylamino, C 1 -C 6 haloalkylamino, C 2 -C 8 dialkylamino, C 2 -C 8 halodialkylamino or C 3 -C 6 cycloalkylamino;
W is O or S;
Q is CR 6a R 6b or NR 7 ;
Y is —C(R 5 )═N—O—(CR 8a R 8b ) p —X—(CR 9a R 9b ) q —SiR 10a R 10b R 10c ;
R 5 is H, CN, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, C 3 -C 6 halocycloalkyl, C 3 -C 15 trialkylsilyl or C 3 -C 15 halotrialkylsilyl;
R 6a is H, OH, halogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkoxyalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy or C 1 -C 6 alkylsulfonyl;
R 6b is H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkoxyalkyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy; or
R 6a and R 6b are taken together with the carbon atom to which they are attached to form a C 3 -C 6 cycloalkyl ring or C 3 -C 6 halocycloalkyl ring;
R 7 is H, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 3 alkylcarbonyl or C 2 -C 3 haloalkylcarbonyl;
each R 8a and R 9a is independently H, OH, CN, halogen, C 1 -C 5 alkyl, C 1 -C 5 haloalkyl or C 1 -C 5 alkoxy;
each R 8b and R 9b is independently H, CN, halogen, C 1 -C 5 alkyl, C 1 -C 5 haloalkyl or C 1 -C 5 alkoxy; or
each pair of R 8a and R 8b or R 9a and R 9b attached to the same carbon atom can be independently taken together with the carbon atom to which they are attached to form a C 3 -C 6 cycloalkyl or C 3 -C 6 halocycloalkyl ring; or
each R 8a , R 8b , R 9a or R 9b can be independently taken together with a R 8a , R 8b , R 9a or R 9b attached to an adjacent carbon atom and the carbon atoms to which they are attached to form a C 3 -C 6 cycloalkyl or C 3 -C 6 halocycloalkyl ring;
each R 10a , R 10b and R 10c is independently C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 2 -C 8 alkoxyalkyl, C 2 -C 8 haloalkoxyalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 4 -C 7 alkylcycloalkyl, C 5 -C 10 alkylcycloalkylalkyl, C 2 -C 6 haloalkenyl, C 1 -C 6 alkylthio, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 4 -C 12 trialkylsilylalkyl or J;
each J is independently a phenyl ring; a 5- or 6-membered heteroaromatic ring; or an 8-, 9- or 10-membered fused bicyclic ring system, or 3- to 6-membered nonaromatic carbocyclic or heterocyclic ring, said ring or ring system optionally including ring members selected from the group consisting of C(═O), C(═S), C(═NR 11 ), NR 11 , SiR 12a R 12b and S(═o) u (═NR 11 ) z , and each ring or ring system optionally substituted with up to 5 substituents independently selected from R 13 ; or
two of R 10a , R 10b or R 10c are taken together with the silicon atom to which they are attached to form a saturated ring containing from 3 to 6 carbon atoms in addition to the silicon atom as ring members, the ring optionally substituted on carbon atoms with halogen;
X is a direct bond, O, NR 11 , C(═O), C(═S) or C(═NR 11 ); or a phenyl ring, a 5- or 6-membered heteroaromatic ring or a 3- to 8-membered nonaromatic carbocyclic or heterocyclic ring, said ring optionally including ring members selected from the group consisting of C(═O), C(═S), C(═NR 11 ), NR 11 , SiR 12a R 12b and S(═O) u (═NR 11 ) z , and optionally substituted with up to 5 substituents independently selected from R 13 ;
each R 11 is independently H, CN, NH 2 , OH, C 1 -C 6 alkyl, C 3 -C 8 cycloalkyl, C 2 -C 6 alkylcarbonyl, C 2 -C 6 haloalkylcarbonyl or C 1 -C 6 alkoxy;
each R 12a and R 12b is independently C 1 -C 5 alkyl, C 2 -C 5 alkenyl, C 2 -C 5 alkynyl, C 3 -C 8 cycloalkyl, C 3 -C 6 halocycloalkyl, C 4 -C 10 cycloalkylalkyl, C 4 -C 7 alkylcycloalkyl, C 5 -C 8 alkylcycloalkylalkyl, C 1 -C 5 haloalkyl, C 1 -C 5 alkoxy or C 1 -C 5 haloalkoxy;
each R 13 is independently halogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, C 4 -C 7 alkylcycloalkyl, C 1 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, cyano, nitro, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylthio, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 haloalkylsulfonyl, C 1 -C 6 alkylamino, C 2 -C 6 dialkylamino, C 2 -C 6 alkylcarbonyl, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylaminocarbonyl, C 3 -C 6 dialkylaminocarbonyl, C 3 -C 15 trialkylsilyl or C 3 -C 15 halotrialkylsilyl;
p and q are independently an integer from 0 to 5; provided that when p is 0, then X is other than O or NR 11 ; and
u and z in each instance of S(═O) u (═NR 11 ) z are independently 0, 1 or 2, provided that the sum of u and z in each instance of S(═O) u (═NR 11 ) z is 0, 1 or 2.

2. A compound of claim 1 wherein:
R 1 is halogen, CN, C 1 -C 2 alkyl, C 1 -C 2 alkoxy, C 1 -C 2 haloalkyl, or C 1 -C 2 haloalkoxy;
R 2 is H, halogen, CN, methyl or trifluoromethyl;
V is NR 3 ;
R 3 is H, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C 2 -C 3 alkylcarbonyl or C 2 -C 3 haloalkylcarbonyl;
R 4 is C 1 -C 2 alkoxy, C 1 -C 2 haloalkoxy, C 1 -C 2 alkylamino or C 2 -C 4 dialkylamino;
W is O; and
R 5 is C 1 -C 3 alkyl or C 1 -C 3 haloalkyl.

3. A compound of claim 2 wherein:
R 1 is F, Cl, Br, CN, methyl or C 1 haloalkyl;
R 2 is H, F or Cl;
R 3 is H, C 1 -C 2 alkyl or C 1 -C 2 haloalkyl;
R 4 is C 1 -C 2 alkoxy or C 1 -C 2 haloalkoxy;
R 5 is C 1 -C 3 alkyl;
p is 0; and
X is direct bond.

4. A compound of claim 1 which is selected from the group consisting of:
methyl N-[[2-chloro-5-[1-[[2-(trimethylsilyl)ethoxy]imino]ethyl]phenyl]-methyl]carbamate;
methyl N-[[2-chloro-5-[1-[[2-(trimethylsilyl)propoxy]imino]ethyl]phenyl]-methyl]carbamate;
methyl N-[[2-chloro-5-[1-[[(trimethylsilyl)methoxy]imino]ethyl]phenyl]-methyl]carbamate; and
methyl N-[[2-chloro-5-[1-[[(ethyldimethylsilyl)methoxy]imino]ethyl]phenyl]-methyl]carbamate.

5. A fungicidal composition comprising (a) a compound of claim 1 ; and (b) at least one fungicide.

6. A fungicidal composition comprising (1) a fungicidally effective amount of a compound of claim 1 ; and (2) at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents.

7. A method for controlling plant diseases caused by fungal plant pathogens comprising applying to the plant or portion thereof, or to the plant seed, a fungicidally effective amount of a compound of claim 1 .

8. The fungicidal composition of claim 5 wherein component (b) comprises at least one compound selected from the group consisting of acibenzolar-S-methyl, aldimorph, amisulbrom, anilazine, azaconazole, azoxystrobin, benalaxyl, benalaxyl-M, benodanil, benomyl, benthiavalicarb, benthiavalicarb-isopropyl, bethoxazin, binapacryl, biphenyl, bitertanol, bixafen, blasticidin-S, Bordeaux mixture (tribasic copper sulfate), boscalid, bromuconazole, bupirimate, captafol, captan, carbendazim, carboxin, carpropamid, chloroneb, chlorothalonil, chlozolinate, clotrimazole, copper oxychloride, copper salts such as copper s

Assignees

• Du Pont

Inventors

• Taggi Andrew Edmund

Classifications

• A01N55/00 Primary

  Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur (containing organo-phosphorus compounds A01N57/00) · CPC title

• A61K31/415

  1,2-Diazoles · CPC title

• C07D239/26

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title

• A01N47/10

  Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof · CPC title

• C07F7/10

  containing nitrogen {having a Si-N linkage} · CPC title