# US 2013/0252811 A1 · Novel herbicide

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- Number: US 2013/0252811 A1
- Document ID: US20130252811A1
- Status: Published application
- Kind: A1
- Application number: 13/516,681
- Filed: 2010-12-10
- Published: 2013-09-26
- Earliest claimed: 2009-12-17
- Assignees: Syngenta Limited
- Inventors: Jane Elisabeth Corbin; Christopher John Mathews; Glynn Mitchell; Claudio Screpanti
- Web page: https://patentgrep.com/patent/US20130252811A1

## CPC

- A01N 43/16: with oxygen as the ring hetero atom
- A01N 43/54: 1,3-Diazines; Hydrogenated 1,3-diazines
- A01N 43/653: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- A01N 43/66: 1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- A01N 43/80: five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
- A01N 47/06: containing —O—CO—O— groups; Thio analogues thereof
- C07D 309/30: Oxygen atoms, e.g. delta-lactones
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Herbicidal composition comprising a pyrandione herbicide and a co-herbicide The present invention relates to a herbicidal composition comprising as active ingredient a mixture of a) a herbicidally effective amount of a compound of formula (I) wherein: R1 is methyl, ethyl, n-propyl, halogen, difluoromethoxy, trifluoromethoxy or trifluoromethyl, R2 is phenyl or phenyl substituted by C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy or halogen, R4, R5, R6 and R7, independently of each other, are hydrogen or C1-C4 alkyl, Y is O, and G is hydrogen, an alkali metal, alkaline earth metal, sulfonium, or ammonium, or G is a latentiating group which is C(O)—Ra or C(0)-O—Rb; and b) a co-herbicide selected from the group consisting of fenoxasulfone, ipfencarbazone, propyrisulfuron, and N-[2-[(4,6-dimethoxy-1,3,5-triazin-2-yl)carbonyl]-6-fluorophenyl]-1,1-difluoro-N-methylmethanesulfonamide. The herbicidal composition is typically for controlling grasses and weeds in crops of useful plants, especially for controlling Echinochloa and/or Leptochloa weeds in crops of rice.

## Claims

### Claim 1

A herbicidal composition comprising as active ingredient a mixture of:
a) a herbicidally effective amount of a compound of formula (I)
wherein:
R1 is methyl, ethyl, n-propyl, halogen, difluoromethoxy, trifluoromethoxy or trifluoromethyl,
R2 is phenyl or phenyl substituted by C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy or halogen,
R4, R5, R6 and R7, independently of each other, are hydrogen or C1-C4 alkyl,
Y is O, and
G is hydrogen, an alkali metal, alkaline earth metal, sulfonium, or ammonium, or G is a latentiating group which is C(O)—Ra or C(O)—O—Rb;
wherein Ra is H, C1-C18alkyl, C2-C18alkenyl, C2-C18alkynyl, C1-C10haloalkyl, C1-C10cyanoalkyl, C1-C10nitroalkyl, C1-C10aminoalkyl, C1-C5alkylaminoC1-C5alkyl, C2-C8dialkylaminoC1-C5alkyl, C3-C7cycloalkylC1-C5alkyl, C1-C5alkoxyC1-C5alkyl, C3-C5alkenyloxyC1-C5alkyl, C3-C5alkynyloxyC1-C5alkyl, C1-C5alkylthioC1-C5alkyl, C1-C5alkylsulfinylC1-C5alkyl, C1-C5alkylsulfonylC1-C5alkyl, C2-C8alkylideneaminoxyC1-C5alkyl, C1-C5alkylcarbonylC1-C5alkyl, C1-C5alkoxycarbonylC1-C5alkyl, aminocarbonylC1-C5alkyl, C1-C5alkylaminocarbonylC1-C5alkyl, C2-C8dialkylaminocarbonylC1-C5alkyl, C1-C5alkylcarbonylaminoC1-C5alkyl, N—C1-C5alkylcarbonyl-N—C1-C5alkylaminoC1-C5alkyl, C3-C6-trialkylsilylC1-C5alkyl, phenylC1-C5alkyl (wherein the phenyl is optionally substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, halogen, cyano, or by nitro), heteroarylC1-C5alkyl (wherein the heteroaryl is optionally substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, halogen, cyano, or by nitro), C2-C5haloalkenyl, C3-C8cycloalkyl, phenyl or phenyl substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro, heteroaryl or heteroaryl substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro; and
Rb is C1-C18alkyl, C3-C18alkenyl, C3-C18alkynyl, C2-C10haloalkyl, C1-C10cyanoalkyl, C1-C10nitroalkyl, C2-C10aminoalkyl, C1-C5alkylaminoC1-C5alkyl, C2-C8dialkylaminoC1-C5alkyl, C3-C7cycloalkylC1-C5alkyl, C1-C5alkoxyC1-C5alkyl, C3-C5alkenyloxyC1-C5alkyl, C3-C5alkynyloxyC1-C5alkyl, C1-C5alkylthioC1-C5alkyl, C1-C5alkylsulfinylC1-C5alkyl, C1-C5alkylsulfonylC1-C5alkyl, C2-C8alkylideneaminoxyC1-C5alkyl, C1-C5alkylcarbonylC1-C5alkyl, C1-C5alkoxycarbonylC1-C5alkyl, aminocarbonylC1-C5alkyl, C1-C5alkylaminocarbonylC1-C5alkyl, C2-C8dialkylaminocarbonylC1-C5alkyl, C1-C5alkylcarbonylaminoC1-C5alkyl, N—C1-C5alkylcarbonyl-N—C1-C5alkylaminoC1-C5alkyl, C3-C6-trialkylsilylC1-C5alkyl, phenylC1-C5alkyl (wherein the phenyl is optionally substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, halogen, cyano, or by nitro), heteroarylC1-C5alkyl (wherein the heteroaryl is optionally substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, C1-C3alkylthio, C1-C3alkylsulfinyl, C1-C3alkylsulfonyl, halogen, cyano, or by nitro), C3-C5haloalkenyl, C3-C8cycloalkyl, phenyl or phenyl substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro, heteroaryl or heteroaryl substituted by C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C1-C3haloalkoxy, halogen, cyano or nitro;
and
b) a co-herbicide selected from the group consisting of fenoxasulfone, ipfencarbazone, propyrisulfuron, and N-[2-[(4,6-dimethoxy-1,3,5-triazin-2-yl)carbonyl]-6-fluorophenyl]-1,1-difluoro-N-methylmethanesulfonamide.

### Claim 2 (depends on 1)

A herbicidal composition as claimed in claim 1, wherein R1 is ethyl.

### Claim 3 (depends on 1)

A herbicidal composition as claimed in claim 1, wherein R2 is phenyl substituted by methyl, methoxy, or halogen.

### Claim 4 (depends on 3)

A herbicidal composition as claimed in claim 3, wherein R2 is phenyl substituted by fluorine or chlorine.

### Claim 5 (depends on 1)

A herbicidal composition as claimed in claim 1, wherein R4, R5, R6 and R7, independently of each other, are hydrogen or C1-C2 alkyl.

### Claim 6 (depends on 5)

A herbicidal composition as claimed in claim 5, wherein R4, R5, R6 and R7 are methyl.

### Claim 7 (depends on 1)

A herbicidal composition as claimed in claim 1, wherein G is hydrogen, C(O)—Ra or C(O)—O—Rb; wherein Ra and Rb are C1-C6alkyl.

### Claim 8 (depends on 7)

A herbicidal composition as claimed in claim 7, wherein G is hydrogen, C(O)—Ra or C(O)—O—Rb; wherein Ra and Rb are methyl, ethyl, n-propyl, isopropyl or t-butyl.

### Claim 9 (depends on 8)

A herbicidal composition as claimed in claim 8, wherein G is hydrogen.

### Claim 10 (depends on 1)

A herbicidal composition as claimed in claim 1, wherein the compound of formula (I) is:

### Claim 11 (depends on 10)

A herbicidal composition as claimed in claim 10, wherein the compound of formula (I) is compound A-4, A-7 or A-9.

### Claim 12 (depends on 1)

A herbicidal composition as claimed in claim 1, wherein the co-herbicide is fenoxasulfone or ipfencarbazone.

### Claim 13 (depends on 1)

A herbicidal composition as claimed in claim 1, wherein the co-herbicide is fenoxasulfone.

### Claim 14 (depends on 1)

A herbicidal composition as claimed in claim 1, wherein the co-herbicide is ipfencarbazone.

### Claim 15 (depends on 1)

A herbicidal composition as claimed in claim 1, wherein the co-herbicide is propyrisulfuron.

### Claim 16 (depends on 1)

A herbicidal composition as claimed in claim 1, wherein the co-herbicide is N-[2-[(4,6-dimethoxy-1,3,5-triazin-2-yl)carbonyl]-6-fluorophenyl]-1,1-difluoro-N-methylmethanesulfonamide.

### Claim 17 (depends on 11)

A herbicidal composition as claimed in claim 11, wherein the co-herbicide is fenoxasulfone or ipfencarbazone.

### Claim 18 (depends on 11)

A herbicidal composition as claimed in claim 11, wherein the co-herbicide is fenoxasulfone.

### Claim 19 (depends on 18)

A herbicidal composition as claimed in claim 18, wherein the compound of formula (I) is compound A-4, and the co-herbicide is fenoxasulfone.

### Claim 20 (depends on 18)

A herbicidal composition as claimed in claim 18, wherein the compound of formula (I) is compound A-7, and the co-herbicide is fenoxasulfone.

### Claim 21 (depends on 18)

A herbicidal composition as claimed in claim 18, wherein the compound of formula (I) is compound A-9, and the co-herbicide is fenoxasulfone.

### Claim 22 (depends on 1)

A herbicidal composition as claimed in claim 1, wherein the weight ratio of the compound of formula (I) to the fenoxasulfone is from 1:6 to 3:2.

### Claim 23 (depends on 22)

A herbicidal composition as claimed in any claim 22, wherein the weight ratio of the compound of formula (I) to the fenoxasulfone is from 1:4 to 4:5.

### Claim 24 (depends on 23)

A herbicidal composition as claimed in claim 23, wherein the weight ratio of the compound of formula (I) to the fenoxasulfone is from 3:10 to 7:10.

### Claim 25 (depends on 24)

A herbicidal composition as claimed in claim 24, wherein the weight ratio of the compound of formula (I) to the fenoxasulfone is from 2:5 to 7:10.

### Claim 26 (depends on 25)

A herbicidal composition as claimed in claim 25, wherein the weight ratio of the compound of formula (I) to the fenoxasulfone is from 1:2 to 7:10.

### Claim 27 (depends on 11)

A herbicidal composition as claimed in claim 11, wherein the co-herbicide is ipfencarbazone.

### Claim 28 (depends on 1)

A herbicidal composition as claimed in claim 1, wherein the weight ratio of the compound of formula (I) to the ipfencarbazone is from 1:7 to 1:1.

### Claim 29 (depends on 28)

A herbicidal composition as claimed in claim 28, wherein the weight ratio of the compound of formula (I) to the ipfencarbazone is from 6:25 to 1:2.

### Claim 30 (depends on 11)

A herbicidal composition as claimed in claim 11, wherein the co-herbicide is propyrisulfuron.

### Claim 31 (depends on 1)

A herbicidal composition as claimed in claim 1, wherein the weight ratio of the compound of formula (I) to the propyrisulfuron is from 1:2 to 3:1.

### Claim 32 (depends on 31)

A herbicidal composition as claimed in claim 31, wherein the weight ratio of the compound of formula (I) to the propyrisulfuron is from 3:4 to 3:2.

### Claim 33 (depends on 11)

A herbicidal composition as claimed in claim 11, wherein the co-herbicide is N-[2-[(4,6-dimethoxy-1,3,5-triazin-2-yl)carbonyl]-6-fluorophenyl]-1,1-difluoro-N-methylmethanesulfonamide.

### Claim 34 (depends on 1)

A herbicidal composition as claimed in claim 1, wherein the weight ratio of the compound of formula (I) to the N-[2-[(4,6-dimethoxy-1,3,5-triazin-2-yl)carbonyl]-6-fluorophenyl]-1,1-difluoro-N-methylmethanesulfonamide is from 1:20 to 20:1.

### Claim 35 (depends on 1)

A herbicidal composition as claimed in claim 1, which is a formulation comprising a carrier, a solvent and/or a surface-active substance.

### Claim 36 (depends on 35)

A herbicidal composition as claimed in claim 35, wherein the formulation is in the form of a wettable powder, a water-dispersible granule, an emulsifiable concentrate, a microemulsifiable concentrate, an oil-in-water emulsion, an oil flowable, an aqueous dispersion, an oily dispersion, a soluble liquid, or a water-soluble concentrate wherein the water-soluble concentrate is with water or a water-miscible organic solvent as carrier.

### Claim 37 (depends on 36)

A herbicidal composition as claimed in claim 36, wherein the formulation is in the form of an emulsifiable concentrate.

### Claim 38 (depends on 1)

A herbicidal composition as claimed in claim 1, comprising c) a safener and, optionally, d) an oil additive.

### Claim 39 (depends on 38)

A herbicidal composition as claimed in to claim 38 comprising c) a safener selected from cloquintocet-mexyl and mefenpyr-diethyl.

### Claim 40 (depends on 1)

A herbicidal composition as claimed in claim 1, which is for controlling grasses and weeds in crops of useful plants.

### Claim 41 (depends on 40)

A herbicidal composition as claimed in claim 40, which is for controlling grasses and weeds in crops of rice.

### Claim 42 (depends on 1)

A method of controlling grasses and weeds in crops of useful plants, which comprises applying a herbicidal composition as defined in claim 1 to the plants or to the locus thereof.

### Claim 43 (depends on 42)

A method as claimed in claim 42, wherein the crops of useful plants are crops of rice.

### Claim 44 (depends on 43)

A method as claimed in claim 43, wherein the crops of useful plants are crops of flooded transplanted rice.

### Claim 45 (depends on 42)

A method as claimed in claim 42, wherein the grasses and weeds controlled comprise Echinochloa and/or Leptochloa.

### Claim 46 (depends on 42)

A method as claimed in claim 42, wherein the herbicidal composition is applied to the plants or to the locus thereof at an application rate of 30 to 240 g of the compound of formula (I) per hectare, calculated as the weight of the compound of formula (I) excluding the weight of any optional counterions thereof.

### Claim 47 (depends on 46)

A method as claimed in claim 46, wherein the herbicidal composition is applied to the plants or to the locus thereof at an application rate of 50 to 150 g of the compound of formula (I) per hectare, calculated as the weight of the compound of formula (I) excluding the weight of any optional counterions thereof.

### Claim 48 (depends on 42)

A method as claimed in claim 42, wherein the co-herbicide is fenoxasulfone, ipfencarbazone, or propyrisulfuron; and
when the co-herbicide is fenoxasulfone, then the herbicidal composition is applied to the plants or to the locus thereof at an application rate of 100 to 400 g of fenoxasulfone per hectare, calculated as the weight of fenoxasulfone excluding the weight of any optional counterions thereof; and
when the co-herbicide is ipfencarbazone, then the herbicidal composition is applied to the plants or to the locus thereof at an application rate of 100 to 500 g of ipfencarbazone per hectare, calculated as the weight of ipfencarbazone excluding the weight of any optional counterions thereof; and
when the co-herbicide is propyrisulfuron, then the herbicidal composition is applied to the plants or to the locus thereof at an application rate of 40 to 160 g of propyrisulfuron per hectare, calculated as the weight of propyrisulfuron excluding the weight of any optional counterions thereof.

### Claim 49 (depends on 48)

A method as claimed in claim 48, wherein the co-herbicide is fenoxasulfone, ipfencarbazone, or propyrisulfuron; and
when the co-herbicide is fenoxasulfone, then the herbicidal composition is applied to the plants or to the locus thereof at an application rate of 200 g of fenoxasulfone per hectare, calculated as the weight of fenoxasulfone excluding the weight of any optional counterions thereof; and
when the co-herbicide is ipfencarbazone, then the herbicidal composition is applied to the plants or to the locus thereof at an application rate of 250 g of ipfencarbazone per hectare, calculated as the weight of ipfencarbazone excluding the weight of any optional counterions thereof; and
when the co-herbicide is propyrisulfuron, then the herbicidal composition is applied to the plants or to the locus thereof at an application rate of 80 g of propyrisulfuron per hectare, calculated as the weight of propyrisulfuron excluding the weight of any optional counterions thereof.

### Claim 50

A method of controlling Leptochloa weeds in crops of useful plants, which comprises applying compound A-9, whose structure is
to the plants or to the locus thereof.